CN112745285A - Aminodibenzofuran compound and organic electroluminescent device thereof - Google Patents
Aminodibenzofuran compound and organic electroluminescent device thereof Download PDFInfo
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- CN112745285A CN112745285A CN201911053140.4A CN201911053140A CN112745285A CN 112745285 A CN112745285 A CN 112745285A CN 201911053140 A CN201911053140 A CN 201911053140A CN 112745285 A CN112745285 A CN 112745285A
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- Prior art keywords
- compound
- formula
- aminodibenzofuran
- organic electroluminescent
- substituted
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- -1 Aminodibenzofuran compound Chemical class 0.000 title claims abstract description 59
- 239000010410 layer Substances 0.000 claims description 172
- 150000001875 compounds Chemical class 0.000 claims description 94
- 230000005525 hole transport Effects 0.000 claims description 51
- 238000002347 injection Methods 0.000 claims description 37
- 239000007924 injection Substances 0.000 claims description 37
- 239000012044 organic layer Substances 0.000 claims description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000002019 doping agent Substances 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 81
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 230000015572 biosynthetic process Effects 0.000 description 62
- 238000003786 synthesis reaction Methods 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000008367 deionised water Substances 0.000 description 18
- 229910021641 deionized water Inorganic materials 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 18
- 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 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000012265 solid product Substances 0.000 description 17
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000000151 deposition Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 230000008021 deposition Effects 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229910052705 radium Inorganic materials 0.000 description 8
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 230000005622 photoelectricity Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- BQHVXFQXTOIMQM-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=CC=CC=C12 BQHVXFQXTOIMQM-UHFFFAOYSA-N 0.000 description 3
- ICQAKBYFBIWELX-UHFFFAOYSA-N (4-naphthalen-2-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=C(C=CC=C2)C2=C1 ICQAKBYFBIWELX-UHFFFAOYSA-N 0.000 description 3
- OBARUOOPPWHZRQ-UHFFFAOYSA-N 9,9-dimethyl-n-(2-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1NC1=CC=CC=C1C1=CC=CC=C1 OBARUOOPPWHZRQ-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000005238 degreasing Methods 0.000 description 3
- RCDMUNHSQCVVBJ-UHFFFAOYSA-N dibenzofuran-1-amine Chemical class O1C2=CC=CC=C2C2=C1C=CC=C2N RCDMUNHSQCVVBJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004227 thermal cracking Methods 0.000 description 3
- MRBZYVMZUBUDAX-UHFFFAOYSA-N (3,5-diphenylphenyl)boronic acid Chemical compound C=1C(B(O)O)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 MRBZYVMZUBUDAX-UHFFFAOYSA-N 0.000 description 2
- WUYYVOWEBMOELQ-UHFFFAOYSA-N 1-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2Br WUYYVOWEBMOELQ-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- DYTYBRPMNQQFFL-UHFFFAOYSA-N 4-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(Br)=CC=C2 DYTYBRPMNQQFFL-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- TWWQCBRELPOMER-UHFFFAOYSA-N [4-(n-phenylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 TWWQCBRELPOMER-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-UHFFFAOYSA-N 0.000 description 1
- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 1
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
- DMDPAJOXRYGXCB-UHFFFAOYSA-N (9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DMDPAJOXRYGXCB-UHFFFAOYSA-N 0.000 description 1
- CPFALCJMNUHBHP-UHFFFAOYSA-N (9,9-diphenylfluoren-2-yl)boronic acid Chemical compound C12=CC(B(O)O)=CC=C2C2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 CPFALCJMNUHBHP-UHFFFAOYSA-N 0.000 description 1
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UKSZBOKPHAQOMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 UKSZBOKPHAQOMP-UHFFFAOYSA-N 0.000 description 1
- AJZDHLHTTJRNQJ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[2-(tetrazol-1-yl)ethyl]benzamide Chemical compound N1(N=NN=C1)CCNC(C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)=O AJZDHLHTTJRNQJ-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 1
- WDDLHUWVLROJLA-UHFFFAOYSA-N 9,9'-spirobi[fluorene]-2-ylboronic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=C(B(O)O)C=C12 WDDLHUWVLROJLA-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910000316 alkaline earth metal phosphate Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 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
- JCDAUYWOHOLVMH-UHFFFAOYSA-N phenanthren-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC3=CC=CC=C3C2=C1 JCDAUYWOHOLVMH-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
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- 239000011241 protective layer Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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
- H10K85/60—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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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- 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
- H10K85/60—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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- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
An aminodibenzofuran compound having the structure of formula (I) and an organic electroluminescent device using the same, wherein A1、R1And R2As defined in the specification.
Description
Technical Field
The present invention relates to a material for an organic electroluminescent device and an organic electroluminescent device using the same, and more particularly, to a material for various colors of light, which can increase device efficiency and extend the lifetime of an organic electroluminescent device, and an organic electroluminescent device using the same.
Background
Organic electroluminescent devices (OLEDs) are expected to be applied to full-color displays and portable electronic devices because of their features of lightness, thinness, wide viewing angle, high contrast, low power consumption, high response speed, full-color image, and flexibility.
Typically, the OLED is a multi-layer thin film structure formed by sequentially depositing an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode by vacuum deposition or coating. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer or layers, and the injected holes and electrons each migrate to the oppositely charged electrode. When electrons and holes are confined to the same molecule, an "exciton (exiton)" is formed, which has a confined electron-hole pair in an excited energy state, which relaxes by a light-emitting mechanism to emit light.
In order to reduce the driving voltage of the conventional OLED, a hole or electron injection layer is further disposed, and a hole or electron blocking layer is added to improve the light emitting efficiency, so that the OLED has a multi-layer thin film structure to provide a good charge transport capability for the device, and thus, the important consideration of the device also includes the stable interface between the electrodes and the organic layer and the matching between the organic materials. If appropriate organic materials are used in combination with the light-emitting layer as the hole and electron auxiliary layers, carrier transport can be facilitated by energy level adjustment of the organic materials, so that holes and electrons can be effectively transported to the light-emitting layer, the density of the electrons and holes in the light-emitting layer is balanced, and the light-emitting efficiency is increased. However, when different light-emitting layer materials are used, the properties of the organic electroluminescent device, such as light-emitting efficiency and driving voltage, cannot meet the requirements of practical display applications, and particularly, the organic material used for the illumination light source needs to have high temperature resistance and long lifetime.
Therefore, there is a need to develop an organic material that can significantly improve the performance of the organic electroluminescent device, so as to meet the practical requirements of the current display illumination industry.
Disclosure of Invention
The invention aims to provide a material which has long service life, high carrier mobility and good heat resistance and can be widely used for various photochromic organic electroluminescent devices.
The invention provides an aminodibenzofuran compound with a structure shown as a formula (I):
wherein A is1As shown in formula (I-A) or formula (I-B):
wherein R is1To R5Identical or different and are independently selected from substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O, and S5-30A heteroaryl group;
m represents an integer of 0 or 1; and
p and q independently represent an integer of 0,1 or 2.
In some embodiments of the present invention, the aminodibenzofuran compound having the structure of formula (I) is represented by the structure of formula (I-1) or the structure of formula (I-2):
in some embodiments of the invention, R is1And R2Are different from each other and are independently selected from substituted or unsubstituted C6-30An aryl group; wherein R is1And R2Independently selected from substituted or unsubstituted fluorenyl, naphthyl, or biphenyl.
In still other embodiments of the present invention, R as described above1And R2Wherein R is1And R2Biphenyl is also preferred.
In some embodiments of the invention, when A is1When it is of the formula (I-A), the R1To R4Independently selected from substituted or unsubstituted C6-30Aryl, wherein the R1To R4Independently selected from the group consisting of phenyl, biphenyl, naphthyl, substituted or unsubstituted fluorenyl.
In other embodiments of the invention, when A is1When it is of the formula (I-A), the R1To R4Independently selected from substituted or unsubstituted C6-30Aryl, and the R1、R2Are each independently of R3、R4The same is true.
In other embodiments of the invention, when A is1Is of the formula (I-A) and when m is 0, the R1、R2Are each independently of R3、R4Is the same as, and is independently selected from substituted or unsubstituted C6-30An aryl group; wherein the aminodibenzofuran compound is shown as a compound (1-1):
in some embodiments of the invention, when A is1When m is 1, the R is of the formula (I-A)3And R4Independently selected from substituted or unsubstituted C6-30And (4) an aryl group.
In other embodiments of the invention, when A is1When m is 1, the R is of the formula (I-A)3And R4Are all the same, wherein R is3And R4Phenyl is also preferred.
In some embodiments of the invention, when A is1Is represented by the formula (I)When q is 0 in the case of-B), p is not 0.
In other embodiments of the invention, when A is1In the formula (I-B), when p is 0, q is not 0.
In some embodiments of the invention, when A is1When it is of the formula (I-B), the R5Selected from substituted or unsubstituted C6-30Aryl, wherein the R5One selected from the group consisting of phenyl, naphthyl, phenanthryl, substituted or unsubstituted anthracyl, substituted or unsubstituted fluorenyl and spirobifluorenyl is preferable.
In other embodiments of the invention, when A is1When it is of the formula (I-B), the R1、R2、R5Independently selected from substituted or unsubstituted C6-30Aryl, and the R5And the R is1、R2The same as the above.
In still other embodiments of the present invention, when A is1Is of the formula (I-B) and p is 0, the R5And the R is1、R2The same as the above.
In some embodiments of the invention, when A is1When it is of the formula (I-B), the R5C selected from substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O, and S5-30Heteroaryl, wherein, the R5Also preferred are substituted or unsubstituted carbazolyl groups. In other embodiments of the invention, when R is5In the case of substituted or unsubstituted carbazolyl, p is 0.
In some embodiments of the present invention, when the structure of formula (I) is a structure of formula (I-1) and A is1When the compound is represented by the formula (I-A), it is represented by the compound (1-2) or (1-3).
In other embodiments of the present invention, when the structure of formula (I) is a structure of formula (I-1) and A is1When it is of the formula (I-B), a compound selected from the following compounds (1-4) to (1-16)The following steps:
in still other embodiments of the present invention, when the structure of formula (I) is a structure of formula (I-2) and A is1When the compound is represented by the formula (I-A), it is represented by the formula (2-1).
In still other embodiments of the present invention, when the structure of formula (I) is a structure of formula (I-2) and A is1Is of the formula (I-B), is selected from one of the following compounds (2-2) to (2-8):
the present invention also provides an organic electroluminescent device comprising: a cathode; an anode; and an organic layer interposed between the cathode and the anode, and the organic layer includes the above aminodibenzofuran compound having the structure of formula (I).
In some embodiments of the present invention, the organic layer comprises a plurality of hole assist layers formed on the anode, and at least one of the plurality of hole assist layers comprises the aminodibenzofuran compound having the structure of formula (I).
In some embodiments of the present invention, the organic layer comprises a hole injection layer, a first hole transport layer and a second hole transport layer sequentially formed on the anode, and the hole injection layer and the first hole transport layer comprise the aminodibenzofuran compound having the structure of formula (I), wherein the hole injection layer further comprises a p-type conductive dopant.
In other embodiments of the present invention, the first hole transporting layer has a thickness of 120 to 180 nm.
In some embodiments of the present invention, the organic layer includes a hole injection layer, a first hole transport layer and a second hole transport layer sequentially formed on the anode, and the second hole transport layer includes the aminodibenzofuran compound having the structure of formula (I).
According to the invention, the aminodibenzofuran compound with the structure of formula (I) provided by the invention has a flat structure at the core, so that good thermal stability and excellent carrier transport property are provided, and the prepared organic electroluminescent device has the performances of low driving voltage, high device efficiency, prolonged device operation life and the like, and has industrial value and application prospect.
Drawings
Embodiments of the invention are described by way of example with reference to the accompanying drawings:
FIG. 1 is a schematic cross-sectional view of one embodiment of an organic electroluminescent device of the present invention;
FIG. 2 is a schematic cross-sectional view of another embodiment of an organic electroluminescent device of the present invention; and
fig. 3 is a schematic cross-sectional view of yet another embodiment of the organic electroluminescent device of the present invention.
Wherein the reference numerals are as follows:
100. 200, 300 organic electroluminescent device
110 substrate
120 anode
130 hole injection layer
140 first hole transport layer
145 second hole transport layer
150 light emitting layer
155 hole blocking layer
160 electron transport layer
170 electron injection layer
180 cathode.
Detailed Description
The embodiments of the present invention are described below with reference to specific embodiments, and those skilled in the art can easily understand the advantages and effects of the present invention from the disclosure of the present specification. The invention is capable of other and different embodiments and its several details are capable of modification in various other respects, all without departing from the spirit and scope of the present disclosure. Moreover, all ranges and values herein are inclusive and combinable. Any number or point within the ranges set forth herein, e.g., any integer, may be treated as the minimum or maximum value to derive a lower range, etc.
The present invention provides aminodibenzofuran compounds having the structure of formula (I):
wherein A is1As shown in formula (I-A) or formula (I-B):
wherein R is1To R5Identical or different and are independently selected from substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O, and S5-30A heteroaryl group;
m represents an integer of 0 or 1; and
p and q independently represent an integer of 0,1 or 2.
In this context, "aryl group"Represents an aryl group or an (arylene) group, the aryl group means a monocyclic or condensed polycyclic group derived from an aromatic hydrocarbon, and includes a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a binaphthyl group, a phenylnaphthyl group, a naphthylphenyl group, a fluorenyl group, a phenylfluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a spirobifluorenyl group, a phenanthryl group, a phenylphenanthryl group, an anthryl group, an indenyl group, a benzophenanthrenyl group, a pyrenyl group, a condensed tetraphenyl group, a perylenyl group,
mesityl, naphthonaphthyl, fluoranthenyl, and the like.
As used herein, "heteroaryl" means heteroaryl or (arylene) heteroaryl, which means an aryl group containing a ring backbone atom containing at least one heteroatom selected from the group consisting of N, O, and S, and may be a monocyclic ring such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, or a condensed ring condensed with at least one benzene ring such as benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, oxazolyl, phenoxazolyl, etc, Phenanthridinyl, benzodioxolyl, dihydroacridinyl and the like.
Herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or group (i.e., substituent). Each of the substituents is independently selected from at least one of the group consisting of: deuterium, halogen, C1-C30Alkyl radical, C1-C30Alkoxy radical, C6-C30Aryl radical, C5-C30Heteroaryl, Via C6-C30Aryl substituted C5-C30Heteroaryl, benzimidazolyl, C3-C30Cycloalkyl radical, C5-C7Heterocycloalkyl, tri- (C)1-C30) Alkane (I) and its preparation methodSilyl radical, tri- (C)1-C30) Aryl silyl, di- (C)1-C30) Alkyl radical- (C)6-C30) Aryl silane radical, C1-C30Alkyl di- (C)6-C30) Aryl silane radical, C2-C30Alkenyl radical, C2-C30Alkynyl, cyano, di- (C)1-C30) Alkylamino radical, di- (C)6-C30) Arylboron radical, di- (C)1-C30) Alkyl boron radical, C1-C30Alkyl radical, C6-C30Aryl radical C1-C30Alkyl radical, C1-C30Alkyl radical C6-C30Aryl, carboxyl, nitro and hydroxyl. Furthermore, the number of carbon atoms in the present context may extend from a lower value to an upper value, e.g. C6-C20Means that the number of carbon atoms can be 6,7, 8,9, 10,11, 12, 13, 14, 15, 16, 17, 18, 19 or 20.
In one embodiment, the C6-30Aryl radicals derived from C1-5Alkyl or C6-12Aryl substituents.
In another embodiment, the C contains at least one heteroatom selected from the group consisting of N, O, and S5-30Heteroaryl is substituted by C6-30Aryl substituents.
Preferred examples of the aforementioned aminodibenzofuran compounds having the structure of formula (I) are selected from table 1, but not limited thereto.
TABLE 1
In another embodiment, the aminodibenzofuran compound having the structure of formula (I) above is preferably one of the following compounds:
the following describes the synthesis route of aminodibenzofuran compounds of formula (I), obtained by bromination and Suzuki coupling (Suzuki coupling):
the aminodibenzofuran compound with the structure of formula (I) provided by the invention has the glass transition temperature of 113-171 ℃, has high temperature resistance, can bear the evaporation environment for preparing devices, and the device performance is not influenced by long-time high-temperature environment, so that the prepared organic electroluminescent device can be suitable for illumination light sources and other purposes.
The present invention also provides an organic electroluminescent device comprising: a cathode; an anode; and an organic layer interposed between the cathode and the anode, and the organic layer includes the above aminodibenzofuran compound having the structure of formula (I).
In one embodiment, the organic layer includes a plurality of hole assist layers formed on the anode, and at least one of the plurality of hole assist layers includes the aminodibenzofuran compound having the structure of formula (I).
Herein, the "hole assist layer" may be a hole injection layer, a hole transport layer, or an electron blocking layer.
In addition to the above organic layer, the organic electroluminescent device may further include at least one layer selected from the group consisting of 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, different from the organic layer, wherein the light emitting layer further includes a fluorescent or phosphorescent dopant, and a host material corresponding to the fluorescent or phosphorescent dopant, respectively. In the organic electroluminescent device of the present invention, the content of the fluorescent or phosphorescent dopant of the light emitting layer is 1 to 10% by weight.
The structure of the organic electroluminescent device of the present invention will be described with reference to the drawings.
Fig. 1 is a schematic cross-sectional view of an embodiment of an organic electroluminescent device 100 of the present invention, the organic electroluminescent device 100 comprising: a substrate 110; an anode 120; a hole injection layer 130 and a first hole transport layer 140 formed on the anode 120, wherein at least one of the hole injection layer 130 or the first hole transport layer 140 contains an aminodibenzofuran compound having the structure of formula (I); a light emitting layer 150 formed on the first hole transport layer 140; an electron transport layer 160 and an electron injection layer 170 sequentially formed on the light emitting layer; and a cathode 180 formed on the electron transport layer.
Fig. 2 is a schematic cross-sectional view of another embodiment of the organic electroluminescent device 200 of the present invention, further comprising a hole blocking layer 155 formed on the light-emitting layer 150 such that the hole blocking layer 155 is located between the electron transport layer 160 and the light-emitting layer 150.
Fig. 3 is a schematic cross-sectional view of another embodiment of the organic electroluminescent device 300 according to the present invention, wherein the hole auxiliary layer has a three-layer structure, which is sequentially formed on the anode 120 and includes a hole injection layer 130, a first hole transport layer 140 and a second hole transport layer 145, wherein at least one of the hole injection layer 130, the first hole transport layer 140 and the second hole transport layer 145 contains an aminodibenzofuran compound having formula (I).
The organic electroluminescent device of the structure shown in the above figures can be fabricated in reverse, in which one or more layers can be optionally added or removed.
In another embodiment, the organic electroluminescent device has a structure as shown in fig. 3, wherein the hole injection layer 130 may further include a P-type conductive dopant, such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN) and 2,3,5, 6-tetrafluoro-7, 7,8, 8-tetracyanoquinodimethane (F4-TCNQ), so that holes can be more easily injected from the cathode into the first hole transport layer, which effectively improves the hole transport efficiency of the first hole transport layer.
In another embodiment, the organic electroluminescent device has a structure as shown in fig. 3, wherein the hole injection layer 130 and the first hole transport layer 140 have an aminodibenzofuran compound with a structure of formula (I), and the thicknesses of the hole injection layer, the first hole transport layer and the second hole transport layer are respectively in the range of 10 to 20 nm, 120 to 180 nm and 10 to 30 nm.
In still another embodiment, the organic electroluminescent device has a structure as shown in fig. 3, wherein the second hole transport layer 150 has an aminodibenzofuran compound having the structure of formula (I).
According to the invention, by means of the technical means of arranging at least one hole auxiliary layer containing the aminodibenzofuran compound with the structure shown in the formula (I), the driving voltage of the organic electroluminescent device can be obviously reduced, and the device performance of the luminous efficiency of the organic electroluminescent device can be improved. The organic electroluminescent device material has good heat resistance, has longer service life than the traditional device, and can be applied to a vehicle display, wherein the organic electroluminescent device can emit red light, green light or blue light, and particularly preferably emits blue light.
The materials used for the hole assist layer of the present invention can also be selected from common materials, and the materials commonly used for the hole assist layer include at least one selected from the group consisting of triazole derivatives, oxadiazole derivatives, imidazole derivatives, phenylenediamine derivatives, star polyamine derivatives, spiro-linked molecule derivatives, and arylamine derivatives.
The materials used in the electron auxiliary layer of the present invention can be selected from commonly used materials, and commonly used materials for the electron injection layer include alkali metal halides or alkali metal chelates containing nitrogen and oxygen, such as: LiF, 8-quinolinolato lithium (8-quinolinolato lithium, Liq); the material of the known electron transport layer includes one selected from the group consisting of organic alkali metal/alkaline earth metal complexes, oxides, halides, carbonates, and alkali metal/alkaline earth metal phosphate salts containing at least one metal selected from lithium and cesium.
The anode is a metal or conductive compound with a high work function, and common materials can be selected to include transparent metal oxides such as: ITO, IZO, SnO2ZnO, or substrates such as poly-Si, a-Si, etc., US5844363 describes a flexible transparent substrate incorporating an anode, the entire contents of which are incorporated herein by reference.
The cathode is a metal or conductive compound with low work function, and can be selected from commonly used materials including Au, Al, In, Mg, Ca or similar metals, alloys, etc., and the cathodes exemplified In US5703436 and US5707745 are incorporated herein In their entirety, and have a thin metal layer, such as: magnesium/silver (Mg: Ag), and a transparent conductive Layer (ITO Layer) covering the metal thin Layer by sputter deposition.
In addition, at least one of the electrodes is transparent or translucent to facilitate transmission of the emitted light.
Structures and materials not specifically described may also be applied in the present invention, such as organic electroluminescent devices comprising polymer materials (PLEDs) as disclosed in US5247190, the entire content of which is incorporated herein by reference. The n-type doped electron transport layer as exemplified in US20030230980 is doped with a molar ratio of 1: doping of lithium in BPhen, the entire contents of which are incorporated herein by reference. The application and principle of each barrier layer is described in US6097147 and US20030230980, the entire contents of which are incorporated herein by reference. The implant layer exemplified by US20040174116 and the protective layer described in the same case are incorporated herein in their entirety.
Any of the layers in the various embodiments may be deposited using any suitable method, unless otherwise specified. Preferred methods for the organic layer include thermal evaporation and jet printing as described in US6013982 and US6087196, the entire contents of which are incorporated herein by reference; organic Vapor Phase Deposition (OVPD) as described in US6337102, the entire contents of which are incorporated herein by reference; the organic vapor phase inkjet printing (OVJP) method described in US10/233470, the entire contents of which are incorporated herein by reference. Other suitable methods include spin coating and solution-based processes. The solution-based process is preferably carried out in a nitrogen or inert gas environment. For the other layers, a preferred method includes a thermal evaporation method. Preferred patterning methods include processes of cold welding by shadow mask deposition as described in US6294398 and US6468819, and processes that integrate jet printing or organic vapor jet printing deposition and patterning, the entire contents of which are incorporated herein by reference. Of course, other methods may be used. The materials used for deposition may be tailored to the particular deposition process employed.
The organic electroluminescent device can be applied to a single device, and the structure of the organic electroluminescent device is an array configuration or a device with a cathode and an anode arranged in an array X-Y coordinate. Compared with the known device, the invention can obviously improve the service life and the driving stability of the organic electroluminescent device.
The following examples are provided to illustrate the various features and effects of the present invention. The detailed description is merely illustrative of the nature of the invention and the invention is not limited to the specific embodiments illustrated.
Synthesis example 1: synthesis of Compound 1-1
Taking N- [1,1'N- [1,1' -biphenyl]-2-yl-9,9-dimethyl-9H-fluoren-2-amine (N- [1,1' -Biphenyl)]200.0 g of (2-yl) -9,9-dimethyl-9H-fluoren-2-amine, 150.4 g of 4-bromodibenzofuran and Sodium tert-butoxide (106.4 g) were placed in a reaction flask, 2.4L of toluene was added, the temperature was raised to 60 ℃ with stirring, and palladium bis (dibenzylideneacetone) (Pd (d) was addedba)215.9 g) with tri-tert-butylphosphine (P (t-Bu)313.4 g), heating to 110 ℃, reacting for 24 hours, cooling, adding deionized water, stirring for 30 minutes, washing the reaction solution to be neutral, removing residual metal catalytic reagent by using silica gel and diatomite, concentrating, adding toluene and hexane, stirring for 1 hour, filtering the solid to obtain an off-white solid compound 1-1-a (189.0 g), wherein the yield is 60%.
Taking the compound 1-1-a (38.0 g) in a reaction bottle, adding dichloromethane (720 ml) into the reaction bottle, stirring the mixture in ice bath, taking N-bromosuccinimide (NBS, 13.2 g) to dissolve the N-bromosuccinimide in acetonitrile, slowly dropping the N-bromosuccinimide into the reaction bottle by using a feeding tube, tracking the reaction bottle on line until the reaction end point, and adding a saturated sodium bicarbonate solution (NaHCO) into the reaction bottle in ice bath3) The reaction was terminated, and washed with water to neutrality, the solution was concentrated to a foamy state, 250 ml of tetrahydrofuran was added to dissolve the foamy state, and the solid was back-titrated out with about 1600 ml of methanol and filtered to obtain the compound 1-1-b (37.0 g) as a white solid in 85% yield.
Taking the compound 1-1-b (10.0 g), N- [1,1'N- [1,1' -biphenyl]-2-yl-9,9-dimethyl-9H-fluoren-2-amine (N- [1,1' -Biphenyl)]-2-yl-9,9-dimethyl-9H-fluoren-2-amine, 6.6 g) and Sodium tert-butoxide (4.0 g) in a reaction flask, 160 ml of toluene are added, the temperature is raised to 60 ℃ with stirring, and then bis (dibenzylideneacetone) palladium (Pd (dba) is added20.48 g) with tri-tert-butylphosphine (P (t-Bu)30.37 g), heating to 110 ℃, reacting for 24 hours, cooling, adding deionized water, stirring for 30 minutes, washing the reaction solution to be neutral, removing residual metal catalytic reagent by using silica gel and diatomite, concentrating, adding toluene and hexane, stirring for 1 hour, crystallizing the solid by using tetrahydrofuran and methanol, filtering to obtain a light yellow solid product 1-1(12.2 g), and obtaining the productThe rate was 85%.
Synthesis example 2: synthesis of Compound 1-2
Taking the compound 1-1-b (10.0 g), N-phenyl-1-naphthylamine (4.0 g) and Sodium tert-butoxide (4.0 g) in a reaction bottle, adding 160 ml of toluene, stirring and heating to 60 ℃, adding bis (dibenzylideneacetone) palladium (Pd (dba)20.48 g) with tri-tert-butylphosphine (P (t-Bu)30.37 g) and heated to 110 ℃, reacted for 24 hours, cooled, added with deionized water and stirred for 30 minutes, the reaction solution is washed to be neutral, then the residual metal catalytic reagent is removed by silica gel and diatomite, concentrated, added with toluene and hexane and stirred for 1 hour, the solid is crystallized by tetrahydrofuran and methanol, filtered to obtain a light yellow solid product 1-2(7.5 g), and the yield is 60%.
Synthesis example 3: synthesis of Compounds 1-3
Placing the compound 1-1-b (10.0 g) and 4-triphenylamine borate (4- (Diphenylamino) phenylboronic acid, 7.0 g) in a reaction bottle, adding 160 ml of toluene, 40 ml of ethanol and 25 ml of 2.0M potassium carbonate aqueous solution, stirring and heating to 60 ℃, and adding tetrakis (triphenylphosphine) palladium (Pd (PPh)3)40.95 g), heating to 100 ℃, reacting for 16 hours, cooling, adding deionized water, stirring for 30 minutes, washing the reaction solution to be neutral, removing residual metal catalytic reagent by using silica gel and diatomite, concentrating, adding toluene and hexane, stirring for 1 hour, crystallizing the solid by using tetrahydrofuran and methanol, and filtering to obtain a yellow solid product 1-3(10.2 g), wherein the yield is 79%.
1H NMR(400MHz,CDCl3)δ7.62(d,1H),7.58(d,1H),7.43-7.47(m,4H),7.28-7.34(m,12H),7.19-7.21(m,7H),7.11(t,1H),7.06(t,2H),7.00(br,2H),6.91(t,3H),6.85(br,2H),6.78(t,1H),1.28(s,6H).
Synthesis example 4: synthesis of Compounds 1-4
The reaction conditions were the same as in Synthesis example 3, except that 4-triphenylamine borate was changed to phenylboronic acid, and the reaction was carried out to obtain products 1 to 4(8.4 g) as off-white solids in a yield of 79%.
Synthesis example 5: synthesis of Compounds 1-5
The reaction conditions were the same as in Synthesis example 3 except that 4-triphenylamine borate was changed to 4- (1-naphthyl) phenylboronic acid, and the reaction was carried out to give 1-5(9.7 g) as a pale yellow solid product in 81% yield.
1H NMR(400MHz,CDCl3)δ8.07(d,1H),7.95(d,1H),7.91(d,1H),7.71(d,2H),7.64-7.66(m,3H),7.57-7.59(m,3H),7.52(t,2H),7.45-7.47(m,2H),7.22-7.37(m,10H),7.09-7.14(m,3H),6.94(t,2H),6.89-6.92(m,2H),6.81(t,1H),1.30(s,6H).
Synthesis example 6: synthesis of Compounds 1-6
The reaction conditions were the same as in Synthesis example 3 except that 4-triphenylamine borate was changed to 4- (2-naphthyl) phenylboronic acid, and the reaction was carried out to give 1-6(10.4 g) as a pale yellow solid product in 87% yield.
1H NMR(400MHz,CDCl3)δ8.18(s,1H),7.97(t,1H),7.88-7.90(m,4H),7.71(d,2H),7.61(t,3H),7.53(t,2H),7.46(t,2H),7.22-7.38(m,10H),7.05-7.10(m,3H),6.94(t,2H),6.88-6.90(m,2H),6.81(t,1H),1.30(s,6H).
Synthesis example 7: synthesis of Compounds 1-7
The reaction conditions were the same as in Synthesis example 3, except that triphenylamine-4-borate was changed to 2-biphenylboronic acid, and the reaction was carried out to obtain off-white solid products 1 to 7(7.4 g) in a yield of 65%.
1H NMR(400MHz,CDCl3)δ7.82(s,1H),7.68-7.69(m,3H),7.57-7.59(m,3H),7.53(d,2H),7.44-7.47(m,4H),7.22-7.38(m,11H),7.05-7.09(m,3H),6.94(t,2H),6.87-6.90(m,2H),6.80(t,1H),1.29(s,6H).
Synthesis example 8: synthesis of Compounds 1-8
The reaction conditions were the same as in Synthesis example 3 except that triphenylamine-4-borate was changed to N-phenyl-3-carbazolboronic acid, and the reaction was carried out to give 1 to 8(10.6 g) as a yellow solid product in 83% yield.
Synthesis example 9: synthesis of Compounds 1-9
The reaction conditions were the same as in Synthesis example 3 except that triphenylamine-4-borate was changed to 3, 5-diphenylphenylboronic acid, and the reaction was carried out to give 1 to 9(7.9 g) as pale yellow solid products in 64% yield.
Synthesis example 10: synthesis of Compounds 1-10
The reaction conditions were the same as in Synthesis example 3 except that triphenylamine-4-borate was changed to 10-phenyl-9-anthraceneboronic acid, and the reaction was carried out to obtain 1 to 10(10.2 g) as a yellowish green solid product in a yield of 80%.
Synthesis example 11: synthesis of Compounds 1-11
The reaction conditions were the same as in Synthesis example 3 except that triphenylamine-4-borate was changed to 9-phenanthreneboronic acid, and the reaction was carried out to obtain 1 to 11(7.9 g) as a yellow solid product in 69% yield.
Synthesis example 12: synthesis of Compounds 1-12
The reaction conditions were the same as in Synthesis example 3 except that triphenylamine-4-borate was changed to 9, 9-diphenylfluorene-2-boronic acid, and the reaction was carried out to obtain 1 to 12(11.0 g) as a yellow solid product in a yield of 80%.
Synthesis example 13: synthesis of Compounds 1-13
The reaction conditions were the same as in Synthesis example 3 except that triphenylamine-4-borate was changed to 2-naphthalene boronic acid, and the reaction was carried out to obtain 1 to 13(7.5 g) as a pale yellow solid product in a yield of 70%.
1H NMR(400MHz,CDCl3)δ8.04(s,1H),7.98(d,1H),7.95(td,1H),7.91(td,1H),7.72(d,1H),7.59(d,1H),7.54-7.56(m,2H),7.44-7.46(m,3H),7.33-7.36(m,3H),7.26-7.30(m,7H),7.23(t,1H),7.01-7.11(m,3H),6.94(t,2H),6.88(br,2H),6.82(t,1H),1.29(s,6H).
Synthesis example 14: synthesis of Compounds 1-14
The reaction conditions were the same as in Synthesis example 3 except that triphenylamine-4-borate was changed to 9,9' -spirobifluorene-2-boronic acid, and the reaction was carried out to obtain yellow solid products 1 to 14(10.4 g) in a yield of 75%.
Synthesis example 15: synthesis of Compounds 1-15
The reaction conditions were the same as in Synthesis example 3 except that triphenylamine-4-borate was changed to 1-naphthalene boronic acid, and the reaction was carried out to obtain the compound 1-15(9.4 g) as a yellow solid in a yield of 87%.
Synthesis example 16: synthesis of Compounds 1-16
The reaction conditions were the same as in Synthesis example 3 except that triphenylamine-4-borate was changed to 9, 9-dimethylfluorene-2-boronic acid, and the reaction was carried out to obtain yellow solid products 1 to 16(10.6 g) in a yield of 90%.
Synthesis example 17: synthesis of Compound 2-1
Taking N- [1,1'N- [1,1' -biphenyl]-2-yl-9,9-dimethyl-9H-fluoren-2-amine (N- [1,1' -Biphenyl)]200.0 g of (2-yl) -9,9-dimethyl-9H-fluoren-2-amine, 200.0 g of 1-bromodibenzofuran (4-Bromo-dibenzofuran, 150.4 g) and Sodium tert-butoxide (Sodium tert-butoxide, 106.4 g) were placed in a reaction flask, 2.4 l of toluene were added, the temperature was raised to 60 ℃ with stirring, and bis (dibenzylideneacetone) palladium (Pd (dba) was added215.9 g) with tri-tert-butylphosphine (P (t-Bu)313.4 g), heating to 110 ℃, reacting for 24 hours, cooling, adding deionized water, stirring for 30 minutes, washing the reaction solution to be neutral, removing residual metal catalytic reagent by using silica gel and diatomite, concentrating, adding toluene and hexane, stirring for 1 hour, filtering the solid to obtain a white-like solid compound 2-1-a (172.0 g), wherein the yield is 55%.
Taking the compound 2-1-a (20.0 g) into a reaction bottle, adding dichloromethane (380 ml) into the reaction bottle, stirring the mixture in ice bath, taking N-bromosuccinimide (NBS, 6.9 g) to dissolve the N-bromosuccinimide into acetonitrile, slowly dropping the N-bromosuccinimide into the reaction bottle by using a feeding pipe, tracking the reaction bottle on line until the reaction end point, and adding a saturated sodium bicarbonate solution (NaHCO) into the reaction bottle in ice bath3) The reaction was terminated, and washed with water to neutrality, the solution was concentrated to a foamy state, 150 ml of tetrahydrofuran was added to dissolve the foamy state, and the solid was back-titrated out with about 800 ml of methanol and filtered to obtain the white-like solid compound 2-1-b (34.1 g) with a yield of 80%.
Placing the compound 2-1-b (10.0 g) and 4-triphenylamine borate (4- (Diphenylamino) phenylboronic acid, 7.0 g) in a reaction bottle, adding 160 ml of toluene, 40 ml of ethanol and 25 ml of 2.0M potassium carbonate aqueous solution, stirring and heating to 60 ℃, and adding tetrakis (triphenylphosphine) palladium (Pd (PPh)3)40.95 g), heating to 100 ℃, reacting for 16 hours, cooling, adding deionized water, stirring for 30 minutes, washing the reaction solution to be neutral, removing residual metal catalytic reagent by using silica gel and diatomite, concentrating, adding toluene and hexane, stirring for 1 hour, crystallizing the solid by using tetrahydrofuran and methanol, and filtering to obtain a yellow solid product 2-1(8.4 g), wherein the yield is 65%.
Synthesis example 18: synthesis of Compound 2-2
1-bromodibenzofuran (10.0 g), bis (4-biphenylyl) amine (12.4 g) and sodium tert-butoxide (9.7 g) were placed in a 250 ml reaction flask, 100 ml of toluene was added, and bis (dibenzylideneacetone) palladium (Pd (dba)20.93 g) with tri-tert-butylphosphine (P (t-Bu)30.66 g) was prepared into a 20 ml toluene solution, which was slowly added to the aforementioned reaction flask, warmed to 110 ℃ and reacted for 12 hours. By on-line tracingAfter completion of the reaction, the reaction mixture was cooled, 300 ml of deionized water was added thereto and stirred for 30 minutes, the mixture was allowed to stand for separation, extraction was performed with ethyl acetate, and magnesium sulfate (MgSO 2) was added to the resulting organic layer solution4) The crude product was purified by silica gel column chromatography using ethyl acetate and hexane (1:10) as eluents to obtain 2-2-a (16.7 g) as a white solid with a yield of 85%.
Compound 2-2-a (10 g) was placed in a 500 ml reaction flask, followed by addition of 200 ml of dichloromethane, the reaction was transferred to an ice bath at 0 ℃, and then N-bromosuccinimide (3.83 g) was dissolved in 40 ml of acetonitrile and placed in an addition funnel, dropwise added to the reaction flask at a rate of 2 drops/sec, and allowed to stand at 0 ℃ for 1 hour. After confirming the completion of the reaction by on-line tracing, 200 ml of a saturated aqueous sodium bicarbonate solution was added and stirred for 30 minutes, the mixture was allowed to stand for separation, extraction was performed with dichloromethane, and magnesium sulfate (MgSO 2) was added to the obtained organic layer solution4) The crude product was purified by silica gel column chromatography using ethyl acetate and hexane (1:20) as eluents to obtain compound 2-2-b (10.4 g) in 90% yield.
Compound 2-2-b (10 g) and 3-biphenylboronic acid (3.9 g) were placed in a 250 ml reaction flask, followed by addition of 120 ml of toluene. Potassium carbonate (6.1 g) was then dissolved in 65 ml of deionized water and added to a reaction flask, and tetrakis (triphenylphosphine) palladium (Pd (PPh) was added under a nitrogen system3)40.61g, 0.53mmole) and 22 ml of ethanol, the reaction was heated to 76 ℃ and reacted for 16 hours. After the completion of the reaction was confirmed by on-line tracing, 300 ml of deionized water was added and stirred for 30 minutes, and the mixture was allowed to stand for separation and fed with ethyl acetateThe organic layer solution was extracted with magnesium sulfate (MgSO)4) The crude product was purified by silica gel column chromatography using ethyl acetate and hexane (1:10) as eluent to give 2-2(9.9 g) as a pale yellow product in 88% yield.
Synthesis example 19: synthesis of Compounds 2-3
Compound 2-2-b (10 g) and 4- (1-naphthyl) phenylboronic acid (4.8 g) were placed in a 250 ml reaction flask, and 150 ml of toluene was added. Potassium carbonate (6.10 g) was then dissolved in 65 ml of deionized water and added to a reaction flask, and tetrakis (triphenylphosphine) palladium (Pd (PPh) was added under a nitrogen system3)40.61 g) and 22 ml of ethanol, the reaction was heated to 76 ℃ and reacted for 16 hours. After confirming the completion of the reaction by TLC plate, 300 ml of deionized water was added and stirred for 30 minutes, and the mixture was allowed to stand for separation, extracted with ethyl acetate, and magnesium sulfate (MgSO 2) was added to the resulting organic layer solution4) The crude product was obtained by filtration after removal of water and concentration of the filtrate, and the product was purified by silica gel tube chromatography using ethyl acetate and hexane (1:10) as eluents to obtain 2-3(9.9 g) in 81% yield.
Synthesis example 20: synthesis of Compounds 2-4
Compound 2-2-b (10 g) and 4- (2-naphthyl) phenylboronic acid (4.8 g) were placed in a 250 ml reaction flask, and 150 ml of toluene was added. Potassium carbonate (6.10 g) was then dissolved in 65 ml of deionized water and added to a reaction flask, and tetrakis (triphenylphosphine) palladium (Pd (PPh) was added under a nitrogen system3)40.61 g) and 22 ml of ethanol, the reaction was heated to 76 ℃ and reacted for 16 hours. After confirming the completion of the reaction by TLC plate, 300 ml of deionized water was added and stirred for 30 minutes, and then allowed to standThe mixture was separated into layers, extracted with ethyl acetate, and magnesium sulfate (MgSO) was added to the resulting organic layer solution4) The crude product was obtained by concentrating the filtrate after water removal and filtration, and the product was purified by silica gel column chromatography using ethyl acetate and hexane (1:10) as eluents to obtain 2-4(10.9 g) in 89% yield.
Synthesis example 21: synthesis of Compounds 2-5
Compound 2-2-b (10 g) and 3, 5-diphenylphenylboronic acid (5.3 g) were placed in a 250 ml reaction flask, and 150 ml of toluene was added. Potassium carbonate (6.10 g) was then dissolved in 65 ml of deionized water and added to a reaction flask, and tetrakis (triphenylphosphine) palladium (Pd (PPh) was added under a nitrogen system3)40.61 g) and 22 ml of ethanol, the reaction was heated to 76 ℃ and reacted for 16 hours. After confirming the completion of the reaction by TLC plate, 300 ml of deionized water was added and stirred for 30 minutes, and the mixture was allowed to stand for separation, extracted with ethyl acetate, and magnesium sulfate (MgSO 2) was added to the resulting organic layer solution4) The crude product was obtained by concentrating the filtrate after water removal and filtration, and the product was purified by silica gel column chromatography using ethyl acetate and hexane (1:10) as eluent to obtain 2-5(11.1 g) in 88% yield.
Synthesis example 22: synthesis of Compounds 2-6
Placing a compound 2-1-b (10.0 g) and 4- (1-naphthyl) phenylboronic acid (4.5 g) in a reaction bottle, adding 160 ml of toluene, 40 ml of ethanol and 25 ml of 2.0M potassium carbonate aqueous solution, stirring and heating to 60 ℃, and adding tetrakis (triphenylphosphine) palladium (Pd (PPh)3)40.95 g), heating to 100 ℃, reacting for 16 hours, cooling, adding deionized water, stirring for 30 minutes, washing the reaction solution to be neutral, and then utilizing silica gel and diatomiteThe residual metal catalyst was removed, concentrated, added toluene and hexane and stirred for 1 hour, the solid was crystallized from tetrahydrofuran and methanol and filtered to give the product 2-6(8.4 g) as a yellow solid in 70% yield.
Synthesis example 23: synthesis of Compounds 2-7
Placing the compound 2-1-b (10.0 g) and 4- (2-naphthyl) phenylboronic acid (4.5 g) in a reaction bottle, adding 160 ml of toluene, 40 ml of ethanol and 25 ml of 2.0M potassium carbonate aqueous solution, stirring and heating to 60 ℃, and adding tetrakis (triphenylphosphine) palladium (Pd (PPh)3)40.95 g), heated to 100 ℃, reacted for 16 hours, cooled, added with deionized water and stirred for 30 minutes, the reaction solution is washed to be neutral, then the residual metal catalytic reagent is removed by silica gel and diatomite, concentrated, added with toluene and hexane and stirred for 1 hour, the solid is crystallized by tetrahydrofuran and methanol, filtered to obtain yellow solid products 2-7(8.1 g), and the yield is 67%.
Synthesis example 24: synthesis of Compounds 2 to 8
Placing the compound 2-1-b (10.0 g) and 2-naphthalene boric acid (4.0 g) in a reaction bottle, adding 160 ml of toluene, 40 ml of ethanol and 25 ml of 2.0M potassium carbonate aqueous solution, stirring and heating to 60 ℃, and adding tetrakis (triphenylphosphine) palladium (Pd (PPh)3)40.95 g), heating to 100 ℃, reacting for 16 hours, cooling, adding deionized water, stirring for 30 minutes, washing a reaction solution to be neutral, removing residual metal catalytic reagent by using silica gel and diatomite, concentrating, adding toluene and hexane, stirring for 1 hour, crystallizing a solid by using tetrahydrofuran and methanol, and filtering to obtain a light yellow solid product 2-8(7.0 g), wherein the yield is 65%.
The physical properties of the above-mentioned materials were analyzed and reported in Table 2, and the measurement methods thereof are shown below.
(1) Temperature of thermal cracking (T)d)
Thermal cracking properties of the resulting compound were measured using a thermogravimetric analyzer (Perkin Elmer, TGA 8000) at a temperature programmed rate of 20 ℃/min under normal pressure and nitrogen atmosphere, and the temperature at which the weight decreased to 95% of the initial weight was the thermal cracking temperature (T;)d)。
(2) Glass transition temperature (T)g) And melting point (T)m)
The resulting compound was measured using a differential scanning thermal analyzer (DSC; Perkin Elmer, DSC 8000) at a temperature programmed rate of 20 deg.C/min.
(3) Energy level of Highest Occupied Molecular Orbital (HOMO)
In addition, the compound was formed into a thin film, and the ionization potential value thereof was measured using a photoelectron spectrophotometer (Riken Keiki, Surface Analyzer) under the atmospheric air, and the value was further converted to obtain the HOMO level.
(4) Energy gap value (E)g) And the energy level of the Lowest Unoccupied Molecular Orbital (LUMO)
A thin film of the above compound was measured for the boundary value (. lamda.) of the absorption wavelength by a UV/VIS spectrophotometer (Perkin Elmer, Lambda 365)onset) The value is converted into a band gap value (E)g) And subtracting the value of the HOMO energy level from the value of the energy gap to obtain the LUMO energy level.
(5) Triplet energy value (E)T)
The luminescence spectrum was measured at 77K using a fluorescence spectrometer (Perkin Elmer, LS 55) and calculated to obtain ET。
TABLE 2
Example 1-1: fabrication of blue fluorescent organic electroluminescent devices
Before the substrate is loaded into the evaporation system for use, the substrate is cleaned by a solvent and ultraviolet ozone for degreasing. Then, the substrate is placedTransferred to a vacuum deposition chamber where all layers are deposited on top of the substrate. The layers shown in FIG. 3 were deposited by a heated boat (boat) at about 10 deg.f-6Vacuum degree of the tray is sequentially deposited:
a) an indium tin oxide layer (ITO) having a thickness of 150 nanometers (nm);
b) a hole injection layer having a thickness of 20 nanometers (nm) comprising compound 1-5 doped with 9% by weight of PD-01, wherein the PD-01 is manufactured by Yi radium photoelectricity;
c) a first hole transport layer having a thickness of 170 nanometers (nm), compounds 1-5;
d) second hole transport layer: a thickness of 10 nanometers (nm), a compound HT-01, wherein HT-01 is prepared electro-optically by Yi radium;
e) a light-emitting layer having a thickness of 25 nanometers (nm) and comprising a host material BH-01 doped with 1.5% of a guest emitter BD01, wherein the BD-01 and BH-01 are produced by Yi radium photoelectricity;
f) an electron transport layer having a thickness of 20 nanometers (nm) and comprising Liq doped with 50% by weight of ET-01, wherein ET-01 is produced by Yi radium photoelectricity;
g) an electron injection layer, 1.5 nanometers (nm) thick, lithium quinolate (Liq); and
h) cathode, approximately 150 nanometers (nm) thick, aluminum (a 1).
The device structure may be represented as: ITO (150 nm)/PD-01: compound 1-5(20 nm)/compound 1-5(170 nm)/compound HT-01(10 nm)/BD-01: BH-01(25 nm)/ET-01: Liq (20 nm)/Liq (1.5 nm)/Al (150 nm).
After deposition to form the layers, the device is transferred from the deposition chamber to a dry box and then encapsulated with a UV curable epoxy resin and a glass cover plate containing a moisture absorber. The organic electroluminescent device had a light-emitting region of 0.09 square mm.
The electroluminescent properties of the organic electroluminescent devices prepared as described above were all measured using a constant current Source (KEITHLEY 2400Source meters, made by KEITHLEY Instruments, inc., Cleveland, Ohio) and photometer (PHOTO RESEARCH spectrum PR 650, made by PHOTO RESEARCH, inc., Chatsworth, Calif.) the luminescence properties were measured at room temperature, including a current density of 10 milliamps per square centimeter (mA/cm)2) Device drive voltage (V) ofd) The performance results of Current Efficiency (CE), color space coordinates (CIE (x, y)), and LT95 for the organic electroluminescent device to operate at 4000 nits (nits) are shown in Table 3; where the LT95 value is defined as the time taken for the luminance level to drop to a level of 95% relative to the initial luminance as a measure for evaluating the lifetime or stability of the organic electroluminescent device.
Examples 1-2 to 1-15: fabrication of blue fluorescent organic electroluminescent devices
Organic electroluminescent devices of examples 1-2 to 1-15 were fabricated using the same layer structure and fabrication method as in example 1-1, except that the compounds 1-5 of the hole injection layer and the first hole transport layer of example 1-1 were replaced with the compounds 1-1, 1-6, 1-7, 1-8 and 1-13, respectively, and the thickness of the first hole transport layer was changed as shown in table 3.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of example 1-1, and the test results are shown in Table 3.
Comparative example 1-1: fabrication of blue fluorescent organic electroluminescent devices
Prepared by the same layer structure and preparation method as in example 1-1, except that the compound 1-5 of the hole injection layer and the first hole transport layer in example 1-1 was changed to compound EHT-01, where EHT-01 was prepared electro-optically by Yi radium, as shown in Table 3.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of example 1-1, and the test results are shown in Table 3.
TABLE 3
Examples 1-16 to 1-18: fabrication of blue fluorescent organic electroluminescent devices
Organic electroluminescent devices of examples 1-16 to 1-18 were fabricated using the same layer structure and fabrication method as in example 1-1, except that the compound HT-01 of the second hole transport layer in example 1-1 was changed to the compound HT305, and the thickness of the first hole transport layer was changed as shown in table 4.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of example 1-1, and the test results are shown in Table 4.
Examples 1-19 to 1-25: fabrication of blue fluorescent organic electroluminescent devices
Organic electroluminescent devices of examples 1-19 to 1-25 were fabricated using the same layer structures and fabrication methods as in examples 1-16, except that the compounds 1-5 of the hole injection layer and the first hole transport layer in examples 1-16 were changed to the compounds 1-3, 1-6, 1-7, 1-9, 1-10, 1-11 and 1-12, respectively, as shown in table 4.
The properties of the organic electroluminescent devices produced were measured by the method for analyzing the electroluminescent properties of examples 1 to 16, and the test results are shown in Table 4.
Comparative examples 1 to 2: fabrication of blue fluorescent organic electroluminescent devices
Prepared by the same layer structure and preparation method as in examples 1 to 16 except that the compounds 1 to 5 of the hole injection layer and the first hole transport layer in examples 1 to 16 were changed to the compound EHT-01, as shown in table 4.
The properties of the organic electroluminescent devices produced were measured by the method for analyzing the electroluminescent properties of examples 1 to 16, and the test results are shown in Table 4.
TABLE 4
Examples 1-26 to 1-34: fabrication of blue fluorescent organic electroluminescent devices
Organic electroluminescent devices of examples 1-26 to 1-34 were prepared using the same layer structure and preparation method as in comparative example 1-1, except that the compound HT-01 of the second hole transport layer in comparative example 1-1 was changed to compounds 1-3, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12 and 1-13, as shown in table 5.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of comparative example 1-1, and the test results are shown in Table 5.
TABLE 5
Example 2-1: fabrication of green phosphorescent organic electroluminescent devices
Before the substrate is loaded into the evaporation system for use, the substrate is cleaned by a solvent and ultraviolet ozone for degreasing. The substrate is then transferred to a vacuum deposition chamber where all layers are deposited on top of the substrate. The layers shown in FIG. 3 were deposited by a heated boat (boat) at about 10 deg.f-6Vacuum degree of the tray is sequentially deposited:
a) an indium tin oxide layer (ITO) having a thickness of 150 nanometers (nm);
b) a hole injection layer having a thickness of 20 nanometers (nm) comprising compounds 1-5 doped with 9% by weight of PD-01;
c) a first hole transport layer having a thickness of 100 nanometers (nm), compound 1-5;
d) second hole transport layer: a compound HT-02 having a thickness of 20 nanometers (nm), wherein HT-02 is made by Yi radium photoelectricity;
e) a light emitting layer, 30 nanometers (nm) thick, comprising a host material GH-01 doped with 10% guest emitter PGD-01, wherein PGD-01 and GH01 were produced by Yi radium photoelectricity;
f) an electron transport layer having a thickness of 30 nanometers (nm) comprising Liq doped with 50% by weight of ET-01;
g) an electron injection layer, 2 nanometers (nm) thick, lithium quinolinate (Liq); and
h) cathode, approximately 150 nanometers (nm) thick, aluminum (a 1).
The device structure may be represented as: ITO (150 nm)/PD-01: compound 1-5(20 nm)/compound 1-5(100 nm)/compound HT-02(20 nm)/PGD-01: GH-01(30 nm)/ET-01: Liq (30 nm)/Liq (2 nm)/Al (150 nm).
After deposition to form the layers, the device is transferred from the deposition chamber to a dry box and then encapsulated with a UV curable epoxy resin and a glass cover plate containing a moisture absorber. The organic electroluminescent device had a light-emitting region of 0.09 square mm.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of example 1-1, and the test results are shown in Table 6.
Examples 2-2 to 2-4: fabrication of green phosphorescent organic electroluminescent devices
Organic electroluminescent devices of examples 2-2 to 2-4 were prepared by the same layer structure and preparation method as in example 2-1, except that the compounds 1-5 of the hole injection layer and the first hole transport layer in example 2-1 were changed to the compounds 1-6, 1-7 and 1-13, respectively, as shown in table 6.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of example 2-1, and the test results are shown in Table 6.
Comparative example 2-1: fabrication of green phosphorescent organic electroluminescent devices
The same layer structure and preparation method as in example 2-1 were used to prepare a hole injection layer and a first hole transport layer, except that compound 1-5 in example 2-1 was changed to compound EHT-01, as shown in Table 6.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of example 2-1, and the test results are shown in Table 6.
TABLE 6
Examples 2 to 5: fabrication of green phosphorescent organic electroluminescent devices
The organic electroluminescent devices of examples 2 to 5 were prepared using the same layer structure and preparation method as in comparative example 2-1, except that the compound HT-02 of the second hole transport layer in comparative example 2-1 was changed to compound 1-3, as shown in table 7.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of comparative example 2-1, and the test results are shown in Table 7.
TABLE 7
Example 3-1: fabrication of red phosphorescent organic electroluminescent devices
Before the substrate is loaded into the evaporation system for use, the substrate is cleaned by a solvent and ultraviolet ozone for degreasing. The substrate is then transferred to a vacuum deposition chamber where all layers are deposited on top of the substrate. The layers shown in FIG. 3 were deposited by a heated boat (boat) at about 10 deg.f-6Vacuum degree of the tray is sequentially deposited:
a) an indium tin oxide layer (ITO) having a thickness of 150 nanometers (nm);
b) a hole injection layer having a thickness of 10 nanometers (nm) and comprising a compound 1-3 doped with 9% by weight of PD-01;
c) a first hole transport layer having a thickness of 100 nanometers (nm), compounds 1-3;
d) second hole transport layer: 70 nanometers (nm) in thickness, compound HT-03;
e) a light-emitting layer having a thickness of 30 nanometers (nm) and comprising a host material RH-01 doped with 3% of a guest emitter PRD-01, wherein the PRD-01 and RH-01 are produced by Yi radium electro-optically;
f) an electron transport layer having a thickness of 30 nanometers (nm) comprising Liq doped with 50% by weight of ET-01;
g) an electron injection layer, 2 nanometers (nm) thick, lithium quinolinate (Liq); and
h) cathode, approximately 150 nanometers (nm) thick, aluminum (a 1).
The device structure may be represented as: ITO (150 nm)/PD-01: compound 1-3(10 nm)/compound 1-3(100 nm)/compound HT-03(70 nm)/PRD-01: RH-01(30 nm)/ET-01: Liq (30 nm)/Liq (2 nm)/Al (150 nm).
After deposition to form the layers, the device is transferred from the deposition chamber to a dry box and then encapsulated with a UV curable epoxy resin and a glass cover plate containing a moisture absorber. The organic electroluminescent device had a light-emitting region of 0.09 square mm.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of example 1-1, and the test results are shown in Table 8.
Examples 3-2 to 3-3: fabrication of red phosphorescent organic electroluminescent devices
Organic electroluminescent devices of examples 3-2 to 3-3 were prepared by the same layer structure and preparation method as in example 3-1, except that the compounds 1-3 of the hole injection layer and the first hole transport layer in example 3-1 were changed to the compounds 1-7 and 1-13, respectively, as shown in table 8.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of example 3-1, and the test results are shown in Table 8.
Comparative example 3-1: fabrication of red phosphorescent organic electroluminescent devices
Prepared by the same layer structure and preparation method as in example 3-1, except that compound 1-3 of the hole injection layer and the first hole transport layer in example 3-1 was changed to compound EHT-01, as shown in table 8.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of example 3-1, and the test results are shown in Table 8.
TABLE 8
Examples 3 to 4: fabrication of red phosphorescent organic electroluminescent devices
The organic electroluminescent devices of examples 3-4 were prepared using the same layer structure and preparation method as in comparative example 3-1, except that the compound HT-03 of the second hole transport layer in comparative example 3-1 was changed to compound 1-3, as shown in table 9.
The properties of the organic electroluminescent device produced were measured by the method for analyzing electroluminescent properties of comparative example 3-1, and the test results are shown in Table 9.
TABLE 9
As mentioned above, the organic electroluminescent device has the aminodibenzofuran compound with the structure of formula (I), so that the organic electroluminescent device has the performances of low driving voltage, high device efficiency, prolonged device operation life and the like, and has industrial value and application prospect.
The above embodiments are merely illustrative, and not restrictive, of the invention. Modifications and variations can be made to the above-described embodiments by those skilled in the art without departing from the spirit and scope of the present invention. Therefore, the scope of the invention is defined by the appended claims, and is covered by the disclosure unless it does not affect the effect and the implementation of the invention.
Claims (24)
1. An aminodibenzofuran compound having the structure of formula (I):
wherein the content of the first and second substances,A1as shown in formula (I-A) or formula (I-B):
wherein R is1To R5Identical or different and are independently selected from substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O, and S5-30A heteroaryl group;
m represents an integer of 0 or 1; and
p and q independently represent an integer of 0,1 or 2.
2. The aminodibenzofuran compound of claim 1, wherein the structure of formula (I) is represented by one of the structures of formulae (I-1) or (I-2):
3. the aminodibenzofuran compound of claim 1, wherein R is as defined in claim 11And R2Are different from each other and are independently selected from substituted or unsubstituted C6-30And (4) an aryl group.
4. The aminodibenzofuran compound of claim 3, wherein R is as defined in claim 31And R2Independently selected from substituted or unsubstituted fluorenyl, naphthyl, or biphenyl.
5. The aminodibenzofuran compound of claim 1, wherein R is as defined in claim 11And R2The same is true.
6. The aminodibenzofuran compound of claim 5, wherein R is1And R2Are all biphenyl groups.
7. The aminodibenzofuran compound of claim 1, wherein A is as defined in claim 11When it is of the formula (I-A), said R1To R4Independently selected from substituted or unsubstituted C6-30And (4) an aryl group.
8. The aminodibenzofuran compound of claim 7, wherein R is as defined in claim 71To R4Independently selected from the group consisting of phenyl, biphenyl, naphthyl, substituted or unsubstituted fluorenyl.
9. The aminodibenzofuran compound of claim 7, wherein when m is 0, R is1、R2Are each independently of R3、R4The same is true.
10. The aminodibenzofuran compound of claim 9, as represented by compound (1-1):
11. the aminodibenzofuran compound of claim 7, wherein when m is 1, R is3And R4Are all phenyl groups.
12. The aminodibenzofuran compound of claim 1, wherein A is as defined in claim 11When it is of the formula (I-B), said R5Selected from substituted or unsubstituted C6-30And (4) an aryl group.
13. The aminodibenzofuran compound of claim 12, wherein R is as defined in claim 125One selected from the group consisting of phenyl, naphthyl, phenanthryl, substituted or unsubstituted anthracyl, substituted or unsubstituted fluorenyl, and spirobifluorenyl.
14. The aminodibenzofuran compound of claim 1, wherein A is as defined in claim 11When it is of the formula (I-B), said R5C selected from substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O, and S5-30A heteroaryl group.
15. The aminodibenzofuran compound of claim 14, wherein R is an alkyl group5When it is a substituted or unsubstituted carbazolyl group, said p is 0.
16. The aminodibenzofuran compound of claim 2, wherein when the structure of formula (I) is a structure of formula (I-1) and A is1When the compound is represented by the formula (I-A), it is represented by the formula (1-2) or (1-3)
17. The aminodibenzofuran compound of claim 2, wherein when the structure of formula (I) is a structure of formula (I-1) and A is1Is of the formula (I-B), is selected from one of the following compounds (1-4) to (1-16):
18. the aminodibenzofuran compound of claim 2, wherein when the structure of formula (I) is a structure of formula (I-2) and A is1When the compound is represented by the formula (I-A), it is represented by the formula (2-1)
19. The aminodibenzofuran compound of claim 2, wherein when the structure of formula (I) is a structure of formula (I-2) and A is1Is of the formula (I-B), is selected from one of the following compounds (2-2) to (2-8):
20. an organic electroluminescent device comprising:
a cathode;
an anode; and
an organic layer interposed between the cathode and the anode, and comprising the aminodibenzofuran compound having the structure of formula (I) as claimed in claim 1.
21. The organic electroluminescent device according to claim 20, wherein the organic layer comprises a plurality of hole assist layers formed on the anode, and at least one of the plurality of hole assist layers comprises the aminodibenzofuran compound having the structure of formula (I).
22. The organic electroluminescent device according to claim 20, wherein the organic layer comprises a hole injection layer, a first hole transport layer and a second hole transport layer sequentially formed on the anode, and the hole injection layer and the first hole transport layer comprise the aminodibenzofuran compound having the structure of formula (I).
23. The organic electroluminescent device of claim 22, wherein the hole injection layer further comprises a p-type conductivity dopant.
24. The organic electroluminescent device according to claim 20, wherein the organic layer comprises a hole injection layer, a first hole transport layer and a second hole transport layer sequentially formed on the anode, and the second hole transport layer comprises the aminodibenzofuran compound having the structure of formula (I).
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| US20150322337A1 (en) * | 2012-12-10 | 2015-11-12 | Konica Minolta, Inc. | Material for organic electroluminescent element, organic electroluminescent element, illumination device, and display device |
| CN107973722A (en) * | 2016-10-21 | 2018-05-01 | 三星显示有限公司 | Mono-amine compound |
| CN109942548A (en) * | 2017-12-21 | 2019-06-28 | 昱镭光电科技股份有限公司 | The diphenylpyrimidin compound and its organic electroluminescent device replaced through quinoline |
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