CN105884623A - 胺衍生物以及包含该胺衍生物的有机电致发光装置 - Google Patents
胺衍生物以及包含该胺衍生物的有机电致发光装置 Download PDFInfo
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- CN105884623A CN105884623A CN201510216576.6A CN201510216576A CN105884623A CN 105884623 A CN105884623 A CN 105884623A CN 201510216576 A CN201510216576 A CN 201510216576A CN 105884623 A CN105884623 A CN 105884623A
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- 150000001412 amines Chemical class 0.000 title claims abstract description 26
- VEWQKVPMDURAQC-UHFFFAOYSA-N hexacyclo[12.11.0.02,7.08,13.015,23.017,22]pentacosa-1(14),2,4,6,8,10,12,15(23),17,19,21,24-dodecaene Chemical group C1=CC=C2C3=C4CC5=CC=CC=C5C4=CC=C3C3=CC=CC=C3C2=C1 VEWQKVPMDURAQC-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 230000005611 electricity Effects 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 230000004888 barrier function Effects 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 5
- 230000005525 hole transport Effects 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 26
- 230000005540 biological transmission Effects 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000010410 layer Substances 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000011799 hole material Substances 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-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 11
- 239000002904 solvent Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 238000003809 water extraction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000945 filler Substances 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- ZAHFNCCKZJRSNY-UHFFFAOYSA-N 12-bromo-10,10-dimethyl-10h-indeno[1,2-b]triphenylene Chemical group C1=CC=C2C3=CC4=C5C(C)(C)C=C(Br)C=C5C=C4C=C3C3=CC=CC=C3C2=C1 ZAHFNCCKZJRSNY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- 241001597008 Nomeidae Species 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000012264 purified product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- 238000003810 ethyl acetate extraction Methods 0.000 description 5
- 150000002220 fluorenes Chemical class 0.000 description 5
- 230000027756 respiratory electron transport chain Effects 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- LCSNDSFWVKMJCT-UHFFFAOYSA-N dicyclohexyl-(2-phenylphenyl)phosphane Chemical group C1CCCCC1P(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1CCCCC1 LCSNDSFWVKMJCT-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WEHQTWMFKLIGEJ-UHFFFAOYSA-N triphenylen-1-amine Chemical compound C1=CC=CC2=C3C(N)=CC=CC3=C(C=CC=C3)C3=C21 WEHQTWMFKLIGEJ-UHFFFAOYSA-N 0.000 description 4
- 208000032825 Ring chromosome 2 syndrome Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound 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 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000004776 molecular orbital Methods 0.000 description 3
- 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 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 2
- 0 C*=C*=CC=CC=NC Chemical compound C*=C*=CC=CC=NC 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N acetic acid;palladium Chemical compound [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- -1 amine derivative of benzene Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- RDSXVQDXXSPFHG-UHFFFAOYSA-N n-(4-bromophenyl)-4-phenylaniline Chemical compound C1=CC(Br)=CC=C1NC1=CC=C(C=2C=CC=CC=2)C=C1 RDSXVQDXXSPFHG-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- KMZUUSFWPQLMQE-UHFFFAOYSA-N 1-bromo-9,9-dimethylfluorene Chemical class C1=CC(Br)=C2C(C)(C)C3=CC=CC=C3C2=C1 KMZUUSFWPQLMQE-UHFFFAOYSA-N 0.000 description 1
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- LUSVTGRAKXEJHX-UHFFFAOYSA-N 21-bromo-18,18-dimethylhexacyclo[12.11.0.02,7.08,13.016,24.017,22]pentacosa-1(25),2,4,6,8,10,12,14,16,19,21,23-dodecaene Chemical group BrC1=C2C=C3C(C=C4C5=CC=CC=C5C5=CC=CC=C5C4=C3)=C2C(C=C1)(C)C LUSVTGRAKXEJHX-UHFFFAOYSA-N 0.000 description 1
- FZYOAXSSNIJFCY-UHFFFAOYSA-N 3-(4-bromophenyl)aniline Chemical compound NC1=CC=CC(C=2C=CC(Br)=CC=2)=C1 FZYOAXSSNIJFCY-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- FTAKLROZLRXAJV-UHFFFAOYSA-N BrC=1C=C(NC2=CC=C(C=C2)Br)C=CC=1 Chemical compound BrC=1C=C(NC2=CC=C(C=C2)Br)C=CC=1 FTAKLROZLRXAJV-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical group 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明揭示一种胺衍生物以及包含该胺衍生物的有机电致发光装置。该胺衍生物由下式(A)表示的基于茚并三亚苯的胺衍生物。采用所述化合物作为电洞传输材料、电子阻挡材料的有机EL装置,本发明可以降低驱动电压和功率消耗,增加效率和半衰期时间:其中R1到R5、m、n、p、L和Ar具有与本发明中所描述相同的定义。
Description
技术领域
本发明一般涉及一种基于茚并三亚苯的胺衍生物和使用所述衍生物的有机电致发光(本文中称为「有机EL」)装置。更确切地说,本发明涉及具有通式(A)的衍生物,使用所述衍生物作为电洞传输材料,电子阻挡材料的有机EL装置。
背景技术
有机电致发光(有机EL)是一种发光二极管(LED),其中发射层是由有机化合物制成的膜,其回应于电流发光。有机化合物的发射层夹在两个电极之间。有机EL由于其高照明、低重量、超薄外形、自照明而无须背光、低功耗、宽视角、高对比度、制造方法简单以及响应时间快速而应用于平板显示器中。
有机材料电致发光的第一次观察是在1950年代早期由安德烈贝纳诺斯(AndreBernanose)和同事在法国南锡大学(Nancy-University)进行的。纽约大学(New YorkUniversity)的马丁蒲伯(Martin Pope)和其同事在1963年第一次在真空下于掺杂有并四苯的蒽的单一纯晶体上观察直流电(DC)电致发光。
第一个二极管装置在1987年由伊士曼柯达(Eastman Kodak)的秦W.唐(Ching W.Tang)和史蒂文凡斯莱克(Steven Van Slyke)所报告。所述装置使用具有单独电洞传输和电子传输层的双层结构,使得工作电压降低并且改进效率,导致当今时代的有机EL研究和装置生产。
有机EL装置典型地由位于两个电极之间的有机材料层构成,其包括电洞传输层(HTL)、发射层(EML)、电子传输层(ETL)。有机EL的基本机制涉及注入载流子、传输、重组载流子和形成激子以发光。当外部电压应用到有机EL装置时,电子和电洞分别从阴极和阳极注入,电子将从阴极注入到LUMO(最低未占用分子轨域)中并且电洞将从阳极注入到HOMO(最高占用分子轨域)中。当电子与电洞在发射层中重组时,形成激子并且随后发光。当发光分子吸收能量以达到激发态时,取决于电子和电洞的自旋怎样组合,激子可以呈单重态或三重态。75%激子通过电子和电洞的重组形成以达到三重激发态。从三重态衰减是自旋禁止的。因此,荧光电致发光装置仅具有25%内部量子效率。相比于荧光电致发光装置,磷光有机EL装置利用自旋-轨道相互作用可促进单重态与三重态之间的***间穿越(intersystem crossing),因此获得从单重态和三重态的发射和25%到100%的电致发光装置内部量子效率。
最近,阿达奇(Adachi)和同事研发一种并入热启动延迟荧光(TADF)机制的新颖荧光有机EL装置,其是通过用反向***间穿越(RISC)机制将自旋禁止三重态激子转化至单重态能阶获得激子形成的高效率的有前景的方式。
有机EL利用三重态和单重态激子。由于与单重态激子相比,三重态激子具有较长生命期及扩散长度,磷光有机EL一般需要在发射层(EML)与电子传输层(ETL)之间的额外电洞阻挡层(HBL),或需要在发射层(EML)与电洞传输层(HTL)之间的额外电子阻挡层(EBL)。使用HBL或EBL的目的是限制注入的电洞和电子的重组和使EML内所产生激子弛豫,因此可以改进装置的效率。为了满足这些作用,电洞阻挡材料或电子阻挡材料必须具有适合于阻断电洞或电子从EML传输到ETL或到HTL的HOMO(最高占用分子轨域)和LUMO(最低未占用分子轨域)能阶。
持续存在对于可有效率地传输电子或电洞,阻挡电子或电洞,具有良好热稳定性的有机EL材料之需求,以及对可以降低驱动电压和功耗,增加效率和半衰期之更有效率的电洞传输材料(HTM)及电子阻挡材料(EBM)之需求。根据上文所述的原因,本发明的目的在于解决诸如EP2313362A1,US20130048975A1,WO20080672636A1,WO2012091471A2之现有技术的这些问题。本发明中使用二芳胺基连接至茚并三亚苯核,并提供一种发光装置,其具有良好的热稳定性,高发光效率,高亮度和长半衰期的时间,以改善现有的材料和现有的有机EL装置。
发明内容
所提供的基于茚并三亚苯的胺衍生物可以用作有机EL装置的电洞传输材料、电子阻挡材料。化合物可以解决例如EP2313362A1、US20130048975A1、WO20080672636A1、WO2012091471A2的先前材料的缺点,如较低的效率、半衰期时间和较高的功率消耗。
本发明的一个目标是提供所述基于茚并三亚苯的胺衍生物,其可以用作有机EL装置的电洞输送层、电子阻挡层。
本发明在工业实践中具有经济优势。因此,本发明揭示基于茚并三亚苯的胺衍生物,其可以用作有机EL装置的电洞传输材料、电子阻挡材料。所提及的基于茚并三亚苯的胺衍生物由下式(A)表示:
其中L表示单键、经取代或未经取代的具有6到30个碳原子的二价亚芳基;m表示0到10的整数;n表示0到3的整数;p表示0到7的整数;X表示选自由O、S、C(R6)(R7)、NR8组成的原子或基团的二价桥,或表示非桥并且形成为经取代或未经取代的联苯基;R1到R8独立地选自由以下组成的群组:氢原子、经取代或未经取代的具有1到20个碳原子的烷基、经取代或未经取代的具有6到30个碳原子的芳基、经取代或未经取代的具有3到30个碳原子的杂芳基;Ar选自由以下组成的群组:经取代或未经取代的具有6到50个碳原子的芳基、经取代或未经取代的具有3到50个碳原子的杂芳基。
附图说明
图1显示本发明中的有机EL装置的一个实例。6是透明电极,13是金属电极,7是沉积到6上的电洞注入层,8是沉积到7上的电洞传输层,9是沉积到8上的电子阻挡层,10是沉积到9上的荧光或磷光发射层,11是沉积到10上的电子传输层,12是沉积到11上的电子注入层。
具体实施方式
本发明探索所述基于茚并三亚苯的胺衍生物和使用所述基于茚并三亚苯的胺衍生物的有机EL装置。在下文中将提供生产、结构以及要素的详细描述以充分理解本发明。明显地,本发明的应用不限于本领域的普通技术人员所熟悉的特定细节。另一方面,已知的常见要素和程序并未详细描述于本发明中,且不应对本发明产生不必要的限制。现将在下文中更详细地描述本发明的一些优选实施例。但是,应认识到本发明可以在除明确描述的实施例之外的广泛多种其它实施例中实践,即,本发明还可以广泛应用于其它实施例,并且除了如所附权利要求书中所指定外,本发明的范围不受明确限制。
在本发明的第一实施例中,揭示基于茚并三亚苯的胺衍生物,其可以用作有机EL装置的电洞传输材料、电子阻挡材料。所提及的衍生物由下式(A)表示:
其中L表示单键、经取代或未经取代的具有6到30个碳原子的二价亚芳基;m表示0到10的整数;n表示0到3的整数;p表示0到7的整数;X表示选自由O、S、C(R6)(R7)、NR8组成的原子或基团的二价桥,或表示非桥并且形成为经取代或未经取代的联苯基;R1到R8独立地选自由以下组成的群组:氢原子、经取代或未经取代的具有1到20个碳原子的烷基、经取代或未经取代的具有6到30个碳原子的芳基、经取代或未经取代的具有3到30个碳原子的杂芳基;Ar选自由以下组成的群组:经取代或未经取代的具有6到50个碳原子的芳基、经取代或未经取代的具有3到50个碳原子的杂芳基。
根据上文提及的式(A),其中L由以下表示:
根据上文提及的式(A),其中Ar由以下表示:
在此实施例中,以下展示一些具体衍生物:
本发明中的基于茚并三亚苯的胺衍生物的详细制备可以通过例示性实施例阐明,但本发明不限于例示性实施例。实例1到6显示本发明中的衍生物的一些实例的制备。实例7到8显示有机EL装置的制造和有机EL装置测试报告的I-V-B、半衰期时间。
实例1
合成衍生物A1
合成2-(联苯-2-基)-7-溴-9,9-二甲基-9H-芴
将35.2g(100mmol)2,7-二溴-9,9-二甲基-9H-芴、21.8g(110mmol)联苯-2-基硼酸、2.31g(2mmol)Pd(PPh3)4、75ml 2M Na2CO3、150ml EtOH以及300ml甲苯的混合物脱气并且放置在氮气下,并且随后在100℃下加热12小时。在完成反应之后,使混合物冷却到室温。有机层用乙酸乙酯和水萃取,用无水硫酸镁干燥,去除溶剂且通过以硅胶填充之管柱色谱来纯化残余物,得到呈白色固体状的产物(26.8g,63.0mmol,63%)。
合成12-溴-10,10-二甲基-10H-茚并[2,1-b]三亚苯
在被脱气并且填充氮气的3000ml三颈烧瓶中,26.8g(60mmol)2-(联苯-2-基)-7-溴-9,9-二甲基-9H-芴溶解于无水二氯甲烷(1500ml)中,随后添加97.5g(600mmol)氯化铁(III)并且搅拌混合物一小时。向混合物中添加500ml甲醇并且分离有机层并且在真空中去除溶剂。通过以硅胶填充之管柱色谱(己烷-二氯甲烷)来纯化残余物,得到白色固体(10.7g,25.3mmol,40%)。1H NMR(CDCl3,400MHz):化学位移(ppm)8.95(s,1H),8.79~8.74(m,2H),8.69~8.68(m,3H),7.84(d,J=8.0Hz,1H),7.72~7.65(m,5H),7.57(d,J=8.0Hz,1H),1.66(s,6H)。
合成N-(联苯-4-基)-9,9'-螺二芴-2-胺
将30g(75.8mmol)2-溴-9,9'-螺二芴、15.3g(90.9mmol)联苯-4-胺、0.17g(0.76mmol)乙酸钯(II)、0.26g(0.76mmol)2-(二环己基膦基)联苯、9.5g(98.5mmol)叔丁醇钠和300ml甲苯的混合物在氮气下回流隔夜。在结束反应之后,随后冷却到室温。有机层用二氯甲烷和水萃取,用无水硫酸镁干燥,去除溶剂并且通过以硅胶填充之管柱色谱(己烷-二氯甲烷)来纯化残余物,得到呈白色固体状的21.9g(产率60%)产物。
合成N-(联苯-4-基)-N-(4-溴苯基)-9,9'-螺二芴-2-胺
将20g(41.3mmol)N-(联苯-4-基)-9,9'-螺二芴-2-胺、14g(49.5mmol)1-溴-4-碘苯、2.4g(12.4mmol)碘化铜、17.1g(123.9mmol)碳酸钾和300ml DMF的混合物在氮气下回流隔夜。在结束反应之后,随后冷却到室温。有机层用乙酸乙酯和水萃取,用无水硫酸镁干燥,去除溶剂并且通过以硅胶填充之管柱色谱(己烷-二氯甲烷)来纯化残余物,得到呈白色固体状的26.3g(产率43%)产物。
合成中间物N-(联苯-4-基)-N-(4-(4,4,5,5-四甲基-1,3,2-二氧杂硼戊环-2-基)苯基)-9,9'-螺二[芴]-2-胺
使10g(15.6mmol)N-(联苯-4-基)-N-(4-溴-苯基)-9,9'-螺二[芴]-2-胺、4.75g(18.72mmol)双(频哪醇根基)二硼、0.18g(0.156mmol)四(三苯基膦)钯、2g(20.28mmol)乙酸钾和300ml 1,4-二恶烷的混合物脱气并放置在氮气下,并且随后在90℃下加热16h。在结束反应之后,使混合物冷却到室温。有机层用乙酸乙酯和水萃取,用无水硫酸镁干燥,去除溶剂并且通过管柱使用己烷和乙基的混合物作为洗脱剂来纯化产物,得到8.77g浅黄色产物(产率82%)。
合成N-(联苯-4-基)-N-(4-(10,10-二甲基-10H-茚并[1,2-b]三亚苯-12-基)苯基)-9,9'-螺二[芴]-2-胺
使15g(35.43mmol)12-溴-10,10-二甲基-10H-茚并[1,2-b]三亚苯、29.1g(42.51mmol)N-(联苯-4-基)-N-(4-(4,4,5,5-四甲基-1,3,2-二氧杂硼戊环-2-基)苯基)-9,9'-螺二芴-2-胺、0.41g(0.35mmol)四(三苯基膦)钯、23ml 2M Na2CO3、100ml EtOH和200ml甲苯的混合物脱气并放置在氮气下,并且随后在100℃下加热8小时。在结束反应之后,使混合物冷却到室温。有机层用二氯甲烷和水萃取,用无水硫酸镁干燥,去除溶剂并且通过以硅胶填充之管柱色谱(己烷-二氯甲烷)来纯化残余物,得到呈黄色固体状的17.5g(产率55%)产物。MS(m/z,FAB+):902.3;1H NMR(CDCl3,500MHz):化学位移(ppm)8.97(s,1H),8.80(d,J=8.0Hz,1H),8.75(d,J=8.0Hz,1H),8.68(s,1H),8.67(d,J=8.0Hz,2H),7.98(d,J=8.0Hz,1H),7.77~7.63(m,9H),7.59(d,J=8Hz,1H),7.52(d,J=7.5Hz,2H),7.47~7.41(d,2H),7.41~7.28(m,8H),7.16~7.05(m,8H),6.84(d,J=7.5Hz,2H),6.68(d,J=7.5Hz,2H),1.59(s,6H)
实例2
合成衍生物A8
合成N-(9,9'-螺二芴-2-基)-N-(联苯-4-基)-10,10-二甲基-10H-茚并[1,2-b]三亚苯-12-胺
将5g(11.8mmol)12-溴-10,10-二甲基-10H-茚并[1,2-b]三亚苯、6.8g(14.1mmol)N-(联苯-4-基)-9,9'-螺二芴-2-胺、0.03g(0.11mmol)乙酸钯(II)、0.04g(0.11mmol)2-(二环己基膦基)联苯、1.7g(17.7mmol)叔丁醇钠和100ml甲苯的混合物在氮气下回流隔夜。在结束反应之后,随后冷却到室温。有机层用二氯甲烷和水萃取,用无水硫酸镁干燥,去除溶剂并且通过以硅胶填充之管柱色谱(己烷-二氯甲烷)来纯化残余物,得到呈黄色固体状的5.8g(产率60%)产物。MS(m/z,FAB+):826.3;1H NMR(CDCl3,500MHz):化学位移(ppm)8.78(s,1H),8.73(d,J=8.0Hz,2H),8.70(d,J=8.0Hz,2H),8.78(s,1H),7.77~7.61(m,9H),7.56(d,J=7.5Hz,2H),7.44~7.39(m,4H),7.34~7.26(m,4H),7.15~6.97(m,8H),6.85(d,J=7.5Hz,2H),6.67~6.64(m,2H),1.35(s,6H)
实例3
合成衍生物A14
合成N-(联苯-4-基)-9,9'-螺二芴-4-胺
将30g(75.8mmol)4-溴-9,9'-螺二[芴]、15.3g(90.9mmol)联苯-4-胺、0.17g(0.76mmol)乙酸钯(II)、0.26g(0.76mmol)2-(二环己基膦基)联苯、9.5g(98.5mmol)叔丁醇钠和300ml甲苯的混合物在氮气下回流隔夜。在结束反应之后,随后冷却到室温。有机层用二氯甲烷和水萃取,用无水硫酸镁干燥,去除溶剂并且通过以硅胶填充之管柱色谱(己烷-二氯甲烷)来纯化残余物,得到呈白色固体状的19.0g(产率52%)产物。
合成N-(9,9'-螺二芴-4-基)-N-(联苯-4-基)-10,10-二甲基-10H-茚并[1,2-b]三亚苯-13-胺
将4.5g(10.6mmol)13-溴-10,10-二甲基-10H-茚并[1,2-b]三亚苯、6.1g(12.7mmol)N-(联苯-4-基)-9,9'-螺二芴-4-胺、0.03g(0.11mmol)乙酸钯(II)、0.04g(0.11mmol)2-(二环己基膦基)联苯、1.3g(13.8mmol)叔丁醇钠和100ml甲苯的混合物在氮气下回流隔夜。在结束反应之后,随后冷却到室温。有机层用二氯甲烷和水萃取,用无水硫酸镁干燥,去除溶剂并且通过以硅胶填充之管柱色谱(己烷-二氯甲烷)来纯化残余物,得到呈黄色固体状的4.8g(产率55%)产物。MS(m/z,FAB+):826.5;1H NMR(CDCl3,500MHz):化学位移(ppm)8.81(s,1H),8.75(d,J=8.0Hz,1H),8.67~8.65(m,3H),7.89~7.83(m,4H),7.67~7.54(m,8H),7.44~7.25(m,8H),7.21~7.10(m,6H),7.01(t,1H),6.83(b,2H),6.69(d,J=7.0Hz,1H),1.65(s,6H)
实例4
合成衍生物A18
合成N,N-二(联苯-4-基)-10,10-二甲基-10H-茚并[2,1-b]三亚苯-12-胺
将4.3g(10.1mmol)12-溴-10,10-二甲基-10H-茚并[2,1-b]三亚苯、3.9g(12.1mmol)二联苯-4-基胺、0.05g(0.2mmol)乙酸钯(II)、0.15g(0.4mmol)2-(二环己基膦)联苯、2g(20mmol)叔丁醇钠和50ml邻二甲苯的混合物在氮气下回流隔夜。在结束反应之后,在100℃下过滤溶液,接收滤液,并且在搅拌的同时将滤液添加到500ml MeOH中,并且用抽吸过滤出沉淀的产物。通过升华来纯化产物,得到2.9g产物(产率37%)。MS(m/z,FAB+):663.1;1H NMR(CDCl3,500MHz):化学位移(ppm)8.88(s,1H),8.79(d,J=8.0Hz,1H),8.72(d,J=8.0Hz,1H),8.66(d,J=5.0Hz,2H),8.63(s,1H),7.85(d,J=8.0Hz,1H),7.69~7.63(m,4H),7.61(d,J=7.5Hz,4H),7.54(d,J=8.5Hz,4H),7.44~7.41(t,4H),7.33~7.26(m,7H),7.20(d,J=8.0Hz,1H),1.59(s,6H)
实例5
合成衍生物A19
合成3-溴-N-(4-溴苯基)苯胺
将32.5g(114.9mmol)1-溴-3-碘苯、14.1g(81.9mmol)4-溴苯胺、23.6g(245.8mmol)叔丁醇钠和2ml(8.2mmol)三叔丁基膦的混合物溶解于400ml甲苯中,向其中添加1.5g(1.64mmol)Pd2(dba)3,并且随后在回流的同时搅拌混合物隔夜。在结束反应之后,使混合物冷却到室温。有机层用乙酸乙酯和水萃取,用无水硫酸镁干燥,去除溶剂并且通过管柱使用己烷和乙酸乙酯的混合物作为洗脱剂来纯化产物,得到12.6g(产率47%)产物。
合成3-二苯并[b,d]呋喃-4-基)-N-(4-(二苯并[b,d]呋喃-4-基)苯基)苯胺
使9.8g(30mmol)3-溴-N-(4-溴苯基)苯胺、14g(66mmol)二苯并[b,d]呋喃-4-基硼酸、0.69g(0.6mmol)四(三苯基膦)钯、60ml 2M Na2CO3、60ml EtOH和150ml甲苯的混合物脱气并放置在氮气下,并且随后在110℃下加热隔夜。在结束反应之后,使混合物冷却到室温。随后在搅拌的同时添加100ml MeOH,并且通过抽吸过滤出沉淀的产物。使其从乙酸乙酯中再结晶后得到9.8g(产率65%)黄色产物。
合成N-(3-(二苯并[b,d]呋喃-4-基)苯基)-N-(4-(二苯并[b,d]呋喃-4-基)苯基)-10,10-二甲基-10H-茚并[2,1-b]三亚苯-12-胺
将4.3g(10.1mmol)12-溴-10,10-二甲基-10H-茚并[2,1-b]三亚苯、6.1g(12.1mmol)3-(二苯并[b,d]呋喃-4-基)-N-(4-(二苯并[b,d]呋喃-4-基)苯基)苯胺、0.05g(0.2mmol)乙酸钯(II)、0.15g(0.4mmol)2-(二环己基膦基)联苯、2g(20mmol)叔丁醇钠和50ml邻二甲苯的混合物在氮气下回流隔夜。在结束反应之后,在100℃下过滤溶液,接收滤液,并且在搅拌的同时将滤液添加到500ml MeOH中,并且用抽吸过滤出沉淀的产物。通过升华来纯化产物,得到4.0g产物(产率47%)。MS(m/z,FAB+):843.3;1H NMR(CDCl3,500MHz):化学位移(ppm)8.90(s,1H),8.81(d,J=8.0Hz,1H),8.74(d,J=8.0Hz,1H),8.68(d,J=5.0Hz,2H),8.61(s,1H),8.1~7.94(m,3H),7.69~7.54(m,12H),7.44~7.38(m,6H),7.33~7.26(m,7H),7.20(d,J=8.0Hz,1H),1.61(s,6H)
实例6
合成衍生物A21
合成N-(4-溴苯基)联苯-4-胺
使14.7g(45mmol)双(4-溴苯基)胺、5.5g(45mmol)苯基硼酸、0.51g(0.45mmol)四(三苯基-膦)钯、45ml 2M Na2CO3、45ml EtOH和90ml甲苯的混合物脱气并放置在氮气下,并且随后在90℃下加热隔夜。在结束反应之后,使混合物冷却到室温。有机层用乙酸乙酯和水萃取,用无水硫酸镁干燥,去除溶剂并且通过管柱使用己烷和乙酸乙酯的混合物作为洗脱剂来纯化产物,得到5.2g(产率36%)产物。
合成N-(4-(9-苯基-9H-咔唑-3-基)苯基)联苯-4-胺
使5.2g(16mmol)N-(4-溴苯基)联苯-4-胺、6.6g(18mmol)9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧杂硼戊环-2-基)-9H-咔唑、0.37g(0.32mmol)四(三苯基-膦)钯、16ml 2MNa2CO3、20ml EtOH和50ml甲苯的混合物脱气并放置在氮气下,并且随后在90℃下加热隔夜。在结束反应之后,使混合物冷却到室温。有机层用乙酸乙酯和水萃取,用无水硫酸镁干燥,去除溶剂并且通过管柱使用己烷和乙酸乙酯的混合物作为洗脱剂来纯化产物,得到5.0g(产率64%)产物。
合成N-(联苯-4-基)-10,10-二甲基-N-(4-(9-苯基-9H-咔唑-3-基)苯基)-10H-茚并[2,1-b]三亚苯-12-胺
将4.3g(10.1mmol)12-溴-10,10-二甲基-10H-茚并[2,1-b]三亚苯、5.0g(10.2mmol)3-(二苯并[b,d]呋喃-4-基)-N-(4-(二苯并[b,d]呋喃-4-基)苯基)苯胺、0.05g(0.2mmol)乙酸钯(II)、0.15g(0.4mmol)2-(二环己基膦基)联苯、2g(20mmol)叔丁醇钠和50ml邻二甲苯的混合物在氮气下回流隔夜。在结束反应之后,在搅拌的同时添加500ml MeOH,并且通过抽吸过滤出沉淀的产物。通过升华来纯化产物,得到5.1g产物(产率61%)。MS(m/z,FAB+):828.6;1H NMR(CDCl3,500MHz):化学位移(ppm)8.86(s,1H),8.81(d,J=8.0Hz,1H),8.72(d,J=8.0Hz,1H),8.66(d,J=5.0Hz,2H),8.59(s,1H),8.37(s,1H),8.11~7.94(m,4H),7.74~7.47(m,12H),7.44~7.38(m,6H),7.31~7.23(m,8H),7.20(d,J=8.0Hz,1H),1.61(s,6H)
产生有机EL装置的一般方法
提供电阻是9奥姆/平方到12奥姆/平方并且厚度是120nm到160nm的经ITO涂布玻璃(下文ITO衬底)并且在多个清洁步骤中于超声波浴(例如清洁剂、去离子水)中清洁。在气相沉积有机层之前,通过UV和臭氧进一步处理经清洁的ITO衬底。用于ITO衬底的所有预处理过程是在洁净室(100级)下进行。
通过气相沉积在高真空单元(10-7托)(例如电阻加热石英舟)中将这些有机层依序应用到ITO衬底上。借助于石英晶体监控器精确监控或设定对应层的厚度和气相沉积速率(0.1nm/sec到0.3nm/sec)。如上所述,个别层还可能由一种以上化合物组成,也就是一般来说掺杂有掺杂剂材料的主体材料。这可通过从两种或两种以上来源共气化来实现。
二吡嗪并[2,3-f:2,3-]喹喔啉-2,3,6,7,10,11-六甲腈(HAT-CN)在这一有机EL装置中用作电洞注入层。N,N-双(萘-1-基)-N,N-双(苯基)-联苯胺(NPB)最广泛用作电洞传输层。10,10-二甲基-12-(4-(芘-1-基)苯基)-10H-茚并[1,2-b]三亚苯(PT-312,US20140175384)在有机EL装置中用作蓝光发射主体,并且N1,N1,N6,N6-四间甲苯基芘-1,6-二胺(D1)用作蓝光客体。在有机EL装置中2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-13-基)-4,6-双-5-苯基联苯基-3-基)-1,3,5-三嗪(ET3)用作电子传输材料以与8-羟基喹啉基-锂(LiQ)共沉积。三(2-苯基吡啶根基)铱(III)(D2)用作磷光掺杂剂。H2(US 20140166988A1,见如下之化学结构)用作有机EL装置之磷光主体。用于产生标准有机EL装置控制组的现有技术的OLED材料和本发明中的比较性材料的化学结构如下:
典型有机EL装置由低功函数金属(例如Al、Mg、Ca、Li以及K)组成,藉由热蒸镀作为阴极,低功函数金属可以说明电子从阴极注入电子传输层。此外,为了减少电子注入阻障并且改进有机EL装置性能,在阴极与电子传输层之间引入薄膜电子注入层。电子注入层的常规材料是具有低功函数的金属卤化物或金属氧化物,例如:LiF、LiQ、MgO或Li2O。另一方面,在有机EL装置制造之后,通过使用PR650光谱扫描光谱仪测量EL光谱和CIE坐标。此外,用吉时利(Keithley)2400可程序设计电压-电流源获得电流/电压、发光/电压以及良品率/电压特征。以上所提到的设备在室温(约25℃)下并且在大气压下操作。
实例7
使用类似于上述一般方法的程序,产生具有以下装置结构I的发射蓝色荧光的有机EL装置(参见图1)。装置I:ITO/HAT-CN(20nm)/电洞传输材料(HTM)(110nm)/电子阻挡材料(EBM)(5nm)/掺杂5%D1的PT-312(30nm)/共沉积50%LiQ的ET3(40nm)/LiF(0.5nm)/Al(160nm)。发射蓝色荧光的有机EL装置测试报告的I-V-B(1000尼特(nit)下)和半衰期时间如表1所报导。半衰期时间被定义为1000cd/m2的初始亮度降到一半的时间。
表1
HTM | EBM | 电压(V) | 效率(cd/A) | CIE(y) | 半衰期时间(小时) |
NPB | ----- | 5.0 | 4.3 | 0.172 | 180 |
A21 | ----- | 5.0 | 4.8 | 0.175 | 260 |
NPB | A1 | 5.2 | 4.9 | 0.175 | 350 |
NPB | A8 | 5.2 | 5.3 | 0.175 | 380 |
NPB | A14 | 5.0 | 5.0 | 0.174 | 350 |
A21 | A18 | 4.8 | 5.4 | 0.175 | 280 |
NPB | A19 | 4.8 | 5.1 | 0.174 | 450 |
实例8
使用类似于上述一般方法的程序,产生具有以下装置结构的发射磷光的有机EL装置(参见图1):装置I:ITO/HAT-CN(20nm)/电洞传输材料(HTM)(110nm)/电子阻挡材料(EBM)(5nm)/掺杂12%D2的H2(35nm)/共沉积50%LiQ的ET3(40nm)/LiF(0.5nm)/Al(160nm)。发射磷光的有机EL装置测试报告的I-V-B(1000尼特(nit)下)和半衰期时间如表2所报导。半衰期时间被定义为3000cd/m2的初始亮度降到一半的时间。
表2
HTM | EBM | 电压(V) | 效率(cd/A) | CIE(x,y) | 半衰期时间(小时) |
NPB | ---- | 3.8 | 42 | 0.352,0.612 | 620 |
A21 | ---- | 3.2 | 48 | 0.353,0.613 | 810 |
NPB | A1 | 3.2 | 49 | 0.352,0.613 | 850 |
NPB | A8 | 3.2 | 53 | 0.352,0.613 | 880 |
NPB | A14 | 3.5 | 50 | 0.353,0.612 | 860 |
NPB | A18 | 3.0 | 48 | 0.353,0.612 | 700 |
NPB | A19 | 3.2 | 51 | 0.353,0.612 | 715 |
NPB | A21 | 3.3 | 46 | 0.352,0.613 | 960 |
在以上有机EL装置测试报告(参见表1和表2)的较佳实施例中,我们展示,使用本发明中的通式(A)胺衍生物显示良好性能并展示较低功率消耗、较高效率和较长半衰期时间。
总而言之,本发明揭示一种基于茚并三亚苯的胺衍生物,其可以用于有机EL装置。更具体地说,采用所述衍生物作为电洞传输材料、电子阻挡材料的有机EL装置。所提及的化合物由下式(A)表示:
其中L表示单键、经取代或未经取代的具有6到30个碳原子的二价亚芳基;m表示0到10的整数;n表示0到3的整数;p表示0到7的整数;X表示选自由O、S、C(R6)(R7)、NR8组成的原子或基团的二价桥,或表示非桥并且形成为经取代或未经取代的联苯基;R1到R8独立地选自由以下组成的群组:氢原子、经取代或未经取代的具有1到20个碳原子的烷基、经取代或未经取代的具有6到30个碳原子的芳基、经取代或未经取代的具有3到30个碳原子的杂芳基;Ar选自由以下组成的群组:经取代或未经取代的具有6到50个碳原子的芳基、经取代或未经取代的具有3到50个碳原子的杂芳基。
Claims (7)
1.一种基于茚并三亚苯的胺衍生物,其具有如下通式(A):
其中L表示单键、经取代或未经取代的具有6到30个碳原子的二价亚芳基;m表示0到10的整数;n表示0到3的整数;p表示0到7的整数;X表示选自由O、S、C(R6)(R7)、NR8组成的原子或基团的二价桥,或表示非桥并且形成为经取代或未经取代的联苯基;R1到R8独立地选自由以下组成的群组:氢原子、经取代或未经取代的具有1到20个碳原子的烷基、经取代或未经取代的具有6到30个碳原子的芳基、经取代或未经取代的具有3到30个碳原子的杂芳基;Ar选自由以下组成的群组:经取代或未经取代的具有6到50个碳原子的芳基、经取代或未经取代的具有3到50个碳原子的杂芳基。
2.根据权利要求1所述的基于茚并三亚苯的胺衍生物,其中L选自由以下组成的群组:
3.根据权利要求1所述的基于茚并三亚苯的胺衍生物,其中Ar选自由以下组成的群组:
4.根据权利要求1所述的基于茚并三亚苯的胺衍生物,所述具有通式(A)的胺衍生物是选自由以下组成的群组:
5.一种有机电致发光装置,其包含由阴极和阳极组成的一对电极,所述电极对之间包含至少一含有根据权利要求1所述的胺衍生物的层。
6.根据权利要求5所述的有机电致发光装置,其中所述至少一含有根据权利要求1所述的胺衍生物的层为电洞传输层。
7.根据权利要求5所述的有机电致发光装置,其中所述至少一含有根据权利要求1所述的胺衍生物的层为电子阻挡层。
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