CN102911162B - 有机化合物及包含其的有机电激发光装置 - Google Patents
有机化合物及包含其的有机电激发光装置 Download PDFInfo
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- CN102911162B CN102911162B CN201110235841.7A CN201110235841A CN102911162B CN 102911162 B CN102911162 B CN 102911162B CN 201110235841 A CN201110235841 A CN 201110235841A CN 102911162 B CN102911162 B CN 102911162B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 63
- 239000000463 material Substances 0.000 claims description 36
- -1 sec.-propyl Chemical group 0.000 claims description 16
- 239000002019 doping agent Substances 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 42
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- 239000010410 layer Substances 0.000 description 21
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 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 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- KCOYLRXCNKJSSC-UHFFFAOYSA-N 9h-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 KCOYLRXCNKJSSC-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 235000015320 potassium carbonate Nutrition 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical group CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
- RIKNNBBGYSDYAX-UHFFFAOYSA-N 2-[1-[2-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]-n,n-bis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C(=CC=CC=1)C1(CCCCC1)C=1C(=CC=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 RIKNNBBGYSDYAX-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- WXDCSIVHLPQGLF-UHFFFAOYSA-N 3,6-ditert-butyl-9-[3-(3,5-diphenyl-1,2,4-triazol-4-yl)phenyl]carbazole Chemical compound C12=CC=C(C(C)(C)C)C=C2C2=CC(C(C)(C)C)=CC=C2N1C(C=1)=CC=CC=1N1C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 WXDCSIVHLPQGLF-UHFFFAOYSA-N 0.000 description 1
- IXYBGNVNMUZSPL-UHFFFAOYSA-N 3,6-ditert-butyl-9-[3-(3,6-ditert-butylcarbazol-9-yl)-5-(3,5-diphenyl-1,2,4-triazol-4-yl)phenyl]carbazole Chemical compound C12=CC=C(C(C)(C)C)C=C2C2=CC(C(C)(C)C)=CC=C2N1C(C=C(C=1)N2C3=CC=C(C=C3C3=CC(=CC=C32)C(C)(C)C)C(C)(C)C)=CC=1N1C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 IXYBGNVNMUZSPL-UHFFFAOYSA-N 0.000 description 1
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 1
- SNYPVLOGKIAGQV-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1.NC1=CC=CC(Br)=C1 SNYPVLOGKIAGQV-UHFFFAOYSA-N 0.000 description 1
- ADUZRTUPGUPPGG-UHFFFAOYSA-N 9-[3-(3,5-diphenyl-1,2,4-triazol-4-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(N1C=2C=C(C=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)=NN=C1C1=CC=CC=C1 ADUZRTUPGUPPGG-UHFFFAOYSA-N 0.000 description 1
- NJGVYXYJWJKPLH-UHFFFAOYSA-N 9-[3-carbazol-9-yl-5-(3,5-diphenyl-1,2,4-triazol-4-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(N1C=2C=C(C=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)N2C3=CC=CC=C3C3=CC=CC=C32)=NN=C1C1=CC=CC=C1 NJGVYXYJWJKPLH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000611 Zinc aluminium Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- HXFVOUUOTHJFPX-UHFFFAOYSA-N alumane;zinc Chemical compound [AlH3].[Zn] HXFVOUUOTHJFPX-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- DYJFXZAVYGPICR-UHFFFAOYSA-N benzene;silicon Chemical compound [Si].C1=CC=CC=C1 DYJFXZAVYGPICR-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 230000001795 light effect Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 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
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- BHAROVLESINHSM-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1 BHAROVLESINHSM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
本发明提供有机化合物及包含其的有机电激发光装置。该有机化合物具以下所示之化学式:其中,R1系各自独立且分别为相同或不同之取代基,包含氢或C1-8烷基;以及R2及R3系各自独立且分别为相同或不同之取代基,包含氢、羟基、C1-8烷基、C1-8烷氧基、C5-10芳基及其衍生物、或C2-8杂芳基及其衍生物。
Description
【技术领域】
本发明关于一种有机化合物及包含其的有机电激发光装置,特别关于一种作为主体材料之有机化合物及包含其的磷光有机电激发光装置。
【背景技术】
有机电致发光装置(organic electroluminescent device),亦称作有机发光二极体(organic light-emitting diode;OLED),是以有机层作为主动层的一种发光二极体(LED)。由于有机电致发光装置具有低电压操作、高亮度、重量轻、广视角、以及高对比值等优点,近年来已渐渐使用于平面面板显示器(flatpanel display)上。与液晶显示器不同,有机电激发光显示器所包含的有机发光二极体画素阵列具有自发光的特性,因此不需外加背光源。
一般而言,有机发光二极体元件包括一对电极,以及在电极之间的有机发光介质层。发光是导因于以下的现象。当电场施于两电极时,阴极射出电子到有机发光介质层,阳极射出空穴到有机发光介质层。当电子与空穴在有机发光介质层内结合时,会产生激子(excitons)。电子和空穴的再结合就伴随着发光。
依据空穴和电子的自旋态(spin state),由空穴和电子再结合而产生的激子可具有三重态(triplet)或单重态(singlet)的自旋态。由单重态激子(singletexciton)所产生的发光为荧光(fluorescence),而由三重态激子(triplet exciton)所产生的发光为磷光(phosphorescence)。磷光的发光效率是荧光的三倍。因此,发展高效率的磷光材料以增进有机发光二极体元件的发光效率是非常重要的。
现今磷光材料在有机发光二极体元件的应用上,其放光机制须搭配能量相符的各种主体(host)材料才能达到最佳的放光效果与量子效率,而其中蓝光的主体材料需要有较大的能阶差值,而须符合这类要件的分子须有较短的共轭体系(conjugated system)。另外,还必须考虑主发光体材料所具备的热稳定性,因此对于主发光体材料结构设计上将有相对的难度。
传统市售或学术上发表的磷光OLED元件用主发光层材料多属于单单只有咔唑(carbazole)片段或是多苯硅取代基的衍生物,然而这些已知的材料有着热稳定性不佳或运用在元件上产生低电流密度,导致电压过高等问题。
已有一些有机化合物被报导出来应用于蓝色、绿光磷光发光二极体(PHOLED)元件上,如美国专利20080286607所揭露具有以下结构的化合物:
其中Ar1及Ar2代表苯环或是吡啶,而R11及R12代表氢、烷基、氧基、或芳基。然而上述化合物其三唑(trizole)基团及咔唑(carbazole)基团系以对位方式配置于苯环上,使得共轭体系加长,如此一来高的共振效果使得发光能隙降低,不适合于绿光磷光发光二极体。此外,该对位配置的三唑(trizole)基团及咔唑(carbazole)基团,也增加了该化合物的结构对称,使得该化合物易形成结晶,较不适合蒸镀成膜。
因此开发适用于蓝色、绿光磷光材料的主发光层材料是一个很重要的课题。
【发明内容】
本发明提出一种有机化合物,具有高三重态能阶(T1),可应用在有机电激发光装置,作为有机发光单元的材料。此外,由于该有机化合物可增加传递能量到发光客体(guest emitter)的效率,因此可进一步作为蓝光及绿光磷光有机电激发光装置的发光层主体材料,可以达到提升磷光有机电激发光装置的元件效率。
根据本发明一较佳实施例,该有机化合物,具有如式(I)所示之化学结构:
式(I)
其中,
R1系各自独立且分别为相同或不同的取代基,包括氢或C1-8烷基;以及
R2及R3系各自独立且分别为相同或不同的取代基,包括氢、羟基、C1-8烷基、C1-8烷氧基、C5-10芳基及其衍生物、或C2-8杂芳基及其衍生物。
根据本发明另一较佳实施例,本发明提供一种有机电激发光装置,该装置包含一对电极;以及有机发光单元,配置于该对电极之间,其中该有机发光单元包含上述之有机化合物。
此外,根据本发明其他较佳实施例,该有机电激发光装置之有机发光单元可包含发光层,该发光层包含主体(host)材料及磷光掺杂材料,而该主体(host)材料包含上述之有机化合物,且该发光层系发出蓝光或绿光。
以下藉由数个实施例及比较实施例,以更进一步说明本发明之方法、特征及优点,但并非用来限制本发明之范围,本发明之范围应以所附权利要求书为准。
【附图说明】
图1系为本发明一较佳实施例所述之有机电激发光装置的剖面结构图。
【主要元件符号说明】
有机电激发光装置~10;
基底~12;
下电极~14;
有机发光单元~16;以及
上电极~18。
【具体实施方式】
有机化合物
本发明系揭露一种有机化合物,为具有式(I)所示的化学式:
式(I)
其中,
R1系各自独立且分别为相同或不同的取代基,包括氢或C1-8烷基;以及
R2及R3系各自独立且分别为相同或不同的取代基,包括氢、羟基、C1-8烷基、C1-8烷氧基、C5-10芳基及其衍生物、或C2-8杂芳基及其衍生物。
在式(I)结构中系表示R1可在所在苯环上可具有取代基的四个位置的任一位置,而该R1系彼此独立的。举例来说,R1可分别为相同或不同之取代基,包含甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、或己基。
此外,R2及R3可分别为相同或不同之取代基,包含甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、或己基、甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、或异丁氧基、苯基(phenyl)、联苯基(biphenyl)、吡啶基(pyridyl)、呋喃基(furyl)、咔唑基(carbazole)、萘基(naphthyl)、蒽基(anthryl)、菲基(phenanthrenyl)、咪唑基(imidazolyl)、嘧啶基(pyrimidinyl)、奎啉基(quinolinyl)、吲哚基(indolyl),或噻唑基(thiazolyl)。
根据本发明其他实施例,本发明所述之有机化合物可具有如式(II)或式(III)所示之结构:
式(II)
式(III)
其中,R1系各自独立且分别为相同或不同之取代基,包含氢或C1-8烷基:以及R2系为氢、羟基、C1-8烷基、C1-8烷氧基。
整体而言,本发明所述之具有式(I)的有机化合物,具有高三重态能阶(T1),可以改善主体材料传递能量到发光客体(guest emitter)的效率。此外,与习知技术相比(其中Ar1及Ar2代表苯环或是吡啶,而R11及R12代表氢、烷基、氧基、或芳基),本发明所述之具有式(I)的有机化合物其三氮唑(trizole)基团及咔唑(carbazole)基团系以间位方式配置于苯环上,使得其具有较短的共轭体系,因此除了适合作为蓝光磷光有机电激发光装置之发光层主体材料,亦适合作为绿光磷光有机电激发光装置之发光层主体材料。再者,本发明所述之具有式(I)的有机化合物,与习知技术相比,由于在结构上较不对称,因此具有较低的结晶度,在以蒸镀成膜后,分子间较不易团聚而结晶。
表1系列举出本发明一系列较佳实施例所得之具有公式(I)之有机化合物,其各自之化学结构均详列于表中,因此可清楚辨识其不同取代基所分别代表的官能基。
表1
为进一步说明本发明有机化合物的制备方法,以下特别详述实施例1-4所示之化合物其制备流程。
实施例1
化合物m-TAZCz之合成
取化合物1(Benzoyl chloride)(71.42mmol.10g)置入250mL反应瓶中,并加入四氢呋喃(THF)(100mL)于该反应瓶中。接着,于0℃环境下,将联氨(N2H4,32.46mmol.1.62g)加入该反应瓶中,并反应4小时,得到化合物(II),产率为92%。上述反应之反应式如下所示:
化合物(I) 化合物(II)
接着,将化合物(II)(41.66mmol.10g)及PCl5(91.51mmol.18.76g)置入250mL反应瓶中,并加入经除水过的溶剂甲苯Toluene(100mL)。接着,加热到120℃。待反应3小时后,将所得之产物以管柱层析法纯化,得到化合物(III),产率为90%。上述反应之反应式如下所示:
化合物(II) 化合物(III)
接着,将化合物(III)(18.11mmol.5g)置入100ml反应瓶中,并将3-溴苯胺(3-bromoaniline)(21.73mmol、3.69g)、及N,N-二甲基苯胺(N,N-dimethylaniline)(25mL)加入反应瓶内。接着,加热至130℃,反应12小时后。反应完成后,得到化合物(IV),产率为50%。上述反应之反应式如下所示:
化合物(IV)
接着,将化合物(IV)(8mmol.3g)、咔唑(carbazole、9.6mmol.1.61g)及碳酸钾(K2CO3、40mmol.5.52g)置入50ml反应瓶中,加入二甲基亚砜(DMSO、30mL)作为溶剂,加热至180℃并反应36小时。待冷却后,让反应回到室温并以水洗净,得到产物m-TAZCz。上述反应之反应式如下所示:
化合物(IV)
利用核磁共振光谱分析化合物m-TAZCz(9-(3-(3,5-二苯基-4H-1,2,4-三唑-4-基)苯基)-9H-咔唑,9-(3-(3,5-diphenyl-4H-1,2,4-triazol-4-yl)phenyl)-9H-carbazole),所得之光谱资讯如下:
1H-NMR(400MHz,CDCl3,δ):8.07(m,4H),7.72-7.21(m,20H),6.85(m,4H)。
13C-NMR(100MHz,CDCl3,δ):154.70,139.98,139.38,136.38,131.22,129.92,129.17,128.77,127.42,126.73,126.15,125.93,123.68,120.60,120.44,109.10。
利用高解析质谱仪(HIGH RESOLUTION MASS SPECTROMETER)分析化合物m-TAZCz,所得之资讯如下:
HRMS(EI)Calcd for C32H22N4(M+):462.1844.Found:462.1844。
元素比例分析:C 83.09,H 4.79,N 12.11;Found:C 83.33,H 4.69,N12.22。
实施例2
化合物m-TAZtCz之合成
将化合物(IV)(13.33mmol.5g)、化合物(V)(16mmol、4.46g)及碳酸钾(K2CO3、66.66mmol.9.2g)置入50ml反应瓶中,加入二甲基亚砜(DMSO、30mL)作为溶剂,加热至180℃并反应36小时。待冷却后,让反应回到室温并以水洗净,得到产物m-TAZtCz。上述反应之反应式如下所示:
化合物(IV) 化合物(V)
利用核磁共振光谱分析化合物m-TAZtCz(3,6-二叔丁基-9-(3-(3,5-二苯基-4H-1,2,4-三唑-4-基)苯基)-9H-咔唑,3,6-di-tert-butyl-9-(3-(3,5-diphenyl-4H-1,2,4-triazol-4-yl)phenyl)-9H-carbazole),所得之光谱资讯如下:
1H-NMR(400MHz,CDCl3,δ):8.07(s,2H),7.71-7.16(m,16H),6.84(d,J=8,2H),1.44(s,18H)。
13C-NMR(100MHz,CDCl3,δ):143.69,138.28,131.21,130.06,129.12,128.80,125.38,123.76,116.43,108.58,34.69,31.89。
利用高解析质谱仪(HIGH RESOLUTION MASS SPECTROMETER)分析化合物m-TAZtCz,所得之资讯如下:
HRMS(EI)Calcd for C32H22N4(M+):462.1844.Found:462.1844。
HRMS(EI)Calcd for C40H38N4(M+):574.3096.Found:574.3100。元素比例分析:C 83.59,H 6.66,N 9.75;Found:C 83.69,H 6.74,N 9.78。
实施例3
化合物m-TAZDCz之合成
将化合物(III)(36.22mmol.10g)置入100ml反应瓶中,并加入化合物(VI)(39.85mmol.5.14g)、及N,N-二甲基苯胺(N,N-dimethylaniline)(30mL)于反应瓶内。接着,加热至135℃,反应12小时后。反应完成后,得到化合物(VII),产率为50%。上述反应之反应式如下所示:
化合物(III) 化合物(VI)
化合物(VII)
接着,将化合物(VII)(15.01mmol.5g)、咔唑(carbazole、33.03mmol.5.54g)及碳酸钾(K2CO3、75.05mmol、10.35g)置入50ml反应瓶中,加入二甲基亚砜(DMSO、30mL)作为溶剂,加热至180℃并反应36小时。待冷却后,让反应回到室温并以水洗净,得到产物m-TAZDCz,产率为82%。上述反应之反应式如下所示:
化合物(VII)
利用核磁共振光谱分析化合物m-TAZDCz(9,9′-(5-(3,5-二苯基-4H-1,2,4-三唑-4-基)-1,3-亚苯基)双(9H-咔唑),9,9′-(5-(3,5-diphenyl-4H-1,2,4-triazol-4-yl)-1,3-phenylene)bis(9H-carbazole)),所得之光谱资讯如下:
1H-NMR(400MHz,CDCl3,δ):8.07(d,J=8Hz,4H),7.97(s,1H),7.68-7.55(m,11H),7.34(s,2H),7.29-7.23(m,7H),6.92(m,4H)。
13C-NMR(100MHz,CDCl3,δ):154.55,140.64,139.66,130.17,129.57,129.15,126.59,126.35,124.00,123.87,123.56,120.99,120.57,109.14。
利用高解析质谱仪(HIGH RESOLUTION MAS S SPECTROMETER)分析化合物m-TAZDCz,所得之资讯如下:
HRMS(EI)Calcd for C44H29N5(M+):627.2523.Found:627.2428。
元素比例分析:C 84.19,H 4.66,N 11.16;Found:C 84.06,H 4.69,N11.15。
实施例4
化合物m-TAZDtCz之合成
将化合物(VII)(15.01mmol.5g)、化合物(V)33.03mmol.9.22g)及碳酸钾(K2CO3、75.07mmol.10.36g)置入50ml反应瓶中,加入二甲基亚砜(DMSO、30mL)作为溶剂,加热至180℃并反应36小时。待冷却后,让反应回到室温并以水洗净,得到产物m-TAZDtCz。上述反应之反应式如下所示:
化合物(VII) 化合物(V)
利用核磁共振光谱分析化合物m-TAZDtCz(9,9′-(5-(3,5-二苯基-4H-1,2,4-三唑-4-基)-1,3-亚苯基)双(3,6-二叔丁基-9H-咔唑),9,9′-(5-(3,5-diphenyl-4H-1,2,4-triazol-4-yl)-1,3-phenylene)bis(3,6-di-tert-butyl-9H-carbazole)),所得之光谱资讯如下:
1H-NMR(400MHz,CDCl3,δ):8.10(s,4H),8.09(s,1H),7.66-7.28(m,16H),6.89(m,4H),1.47(s,36H)。
13C-NMR(100MHz,CDCl3,δ):154.71,144.04,141.07,138.02,137.21,130.03,129.49,129.08,126.88,123.97,123.88,123.14,122.58,116.55,108.68,34.71,31.88.
元素比例分析:C 84.57,H 7.22,N 8.22;Found:C 84.70,H 7.60,N 8.29。
实施例5
化合物m-TAZDCz-nH之合成
将化合物(III)(36.23mmol、10g)置入100ml反应瓶中,并加入化合物(VIII)(43.47mmol、6.30g)、及N,N-二甲基苯胺(N,N-dimethylaniline)于反应瓶内。接着,加热至135℃,反应12小时后。反应完成后,得到化合物(VII),产率为50%。上述反应之反应式如下所示:
化合物(III) 化合物(VIII)
化合物(IX)
接着,将化合物(IX)(14.32mmol.5g)、咔唑(carbazole、31.51mmol、5.29g)及碳酸钾(K2CO3、71.6mmol.9.8g)置入50ml反应瓶中,加入二甲基亚砜(DMSO、30mL)作为溶剂,加热至180℃并反应36小时。待冷却后,让反应回到室温并以水洗净,得到产物化合物(X),产率为90%。上述反应之反应式如下所示:
化合物(IX)
化合物(X)
接着,将化合物(X)(3.1mmol、2g)、溴己烷(1-Bromohexane、3.73mmol、0.61g)及氢氧化钾(4.04mmol、0.22g)溶于乙醇(30ml),加热到回流并反应3小时。完应完成后得到产物m-TAZDCz-nH,产率为98%。上述反应之反应式如下所示:
利用核磁共振光谱分析化合物m-TAZDCz-nH,所得之光谱资讯如下:
1H-NMR(400MHz,CDCl3,δ):8.06(d,J=8Hz,2H),7.87(d,1H),7.52-7.20(m,11H),6.93(d,J=8Hz,1H),6.68(d,J=8Hz,2H),3.93(t,J1=4Hz,J2=12Hz,2H),1.42(m,2H),1.03-0.98(m,6H),0.73-0.70(t,J1=8Hz,J2=12Hz)。
13C-NMR(100MHz,CDCl3,δ):155.73,154.73,140.55,129.69,128.98,128.58,128.09,127.04,127.06,126.80,125.58,123.29,120.03,119.82,114.11,109.73,68.91,31.06,28.53,25.16,22.20,13.75。
化合物之物理性质测定
对化合物m-TAZCz、m-TAZtCz及m-TAZDCz之玻璃转化温度(Tg)、结晶融点(Tm)、热裂解温度(Td)、能隙(Es)、三重态能阶(ET)、最高键结电子能阶(HOMO)、及最低未键结能阶(LUMO),其量测结果请参照表2:
表2
化合物 | m-TAZCz | m-TAZtCz | m-TAZDCz | m-TAZDtCz |
Tg | ----- | 120.6℃ | 159℃ | ------- |
Tm | 312.4℃ | 288.7℃ | 301.06℃ | ------- |
Td(5%) | 358℃ | 367℃ | 432℃ | 421℃ |
LUMO | 2.31 | 1.92 | 2.03 | 2.13 |
HOMO | 5.99 | 5.54 | 5.6 | 5.68 |
ET | 3.0 | 2.99 | 3.01 | 2.97 |
Es | 3.68 | 3.62 | 3.57 | 3.54 |
由表2可以发现本发明所述之化合物m-TAZCz、m-TAZtCz及m-TAZDCz其热裂解温度(Td)皆大于350℃(m-TAZDCz甚至大于430℃),玻璃转换温度(Tg)大于120℃,显示这类型材料在热稳定性质上有优秀的表现。而HOMO、LUMO也落在适合的位置,因此电子注入非常容易。
有机电激发光装置
请参照图1,显示符合本发明所述之有机电激发光装置10的剖面结构示意图,该有机电激发光装置10包括基底12、下电极14、有机发光单元16及上电极18。该有机电激发光装置10可为上发光、下发光、或双面发光有机电激发光装置。该基底可例如为玻璃、塑胶基板、或半导体基板。该下电极14及上电极18之材质可例如为锂、镁、钙、铝、银、铟、金、钨、镍、铂、铜、铟锡氧化物(ITO)、铟锌氧化物(IZO)、锌铝氧化物(AZO)、氧化锌(ZnO)或其结合,而其形成方式可为热蒸镀、溅射或电浆强化式化学气相沉积方式。此外,该下电极14及上电极18至少一者需具有透光的性质。
该有机发光单元16至少包含发光层,可更包含空穴注入层、空穴传输层、电子传输层、电子注入层或其他膜层。值得注意的是,根据本发明较佳实施例,该有机发光单元16必需包含本发明所述具有公式(I)之有机化合物。换言之,在该有机发光单元16中,至少有一膜层包含该有机化合物。
根据本发明另一较佳实施例,该有机电激发光装置可为一磷光有机电激发光装置,而该磷光有机发光单元之发光层包含主体(host)材料及磷光掺杂材料,而该主体(host)材料包含本发明所述具有公式(I)所示结构之有机化合物。熟悉本技术者可视所使用之有机电激发光材料及所需之元件特性,将本发明所述之有机化合物与所需的磷光掺杂材料掺杂,并改变所搭配的掺杂物之掺杂量。因此,掺杂物之掺杂量之多寡非关本发明之特征,非为限制本发明范围之依据。
为进一步说明本发明有机电激发光装置,以下实施例系将由实施例1所得之有机化合物m-TAZCz作为发光层材料,分别搭配蓝光或绿光的掺杂材料,来验证本发明所述之有机化合物可提升有机电激发光装置的效率。
实施例6:
绿色磷光电激发光装置
使用中性清洁剂、丙酮、及乙醇以超音波振荡将已制作图样的ITO(厚度为100nm)玻璃基底洗净。
接着,以氮气将基材吹干,然后UV-OZONE 30分钟,接着于10-6torr的压力下依序沉积TAPC(1,1-bis(di-4-tolylaminophenyl)cyclohexane、厚度为40nm)、m-TAZCz掺杂Irppy3((tris(2-phenylpyridine)iridium)(m-TAZCz与Irppy3的比例为100∶15、厚度为30nm)、BPhen(4,7-diphenyl-1,10-phenanthroline、厚度为30nm)、LiF(厚度为0.5nm)、及Al(厚度为110nm),封装后获致该电激发光装置(1)。该电激发光装置(1)之结构可表示为:
ITO(100nm)/TAPC(40nm)/Irppy3(15%):m-TAZCz(30nm)/BPhen(30nm)/LiF(0.5nm)/Al(110nm)
接着,量测该电激发光装置(1)之光学特性,其量测结果如下:
最佳元件效率在31.9cd/A,及22.7lm/W左右;
元件效率在31.8cd/A,及22.2lm/W(1000cd/m2);
发光波长CIE座标:(0.30,0.63)。
实施例7:
蓝色磷光电激发光装置
使用中性清洁剂、丙酮、及乙醇以超音波振荡将已制作图样的ITO(厚度为100nm)玻璃基底洗净。
接着,以氮气将基材吹干,然后UV-OZONE 30分钟,接着于10-6torr的压力下依序沉积。
NPB(N,N′-di(naphthalene-l-yl)-N,N′-diphenyl-benzidine、厚度为50nm)、TAPC(1,1-bis(di-4-tolylaminophenyl)cyclohexane、厚度为15nm)、m-TAZCz掺杂Firpic(Iridium-bis(4,6difluorophenyl-pyridinato-N,C2)-picolinate)(m-TAZCz与Firpic的比例为100∶11、厚度为40nm)、m-TPhOXD厚度为12.5nm)、BPhen(4,7-diphenyl-1,10-phenanthroline)、厚度为12.5nm)、LiF(厚度为1nm)、及Al(厚度为100nm),封装后获致该电激发光装置(2)。该电激发光装置(2)之结构可表示为:
NPB(50nm)/TAPC(15nm)/m-TAZCz:Firpic 11%(40nm)/m-TPhOXD(12.5nm)/BPhen(12.5nm)/LiF(1nm)/Al(100nm)
接着,量测该电激发光装置(2)之光学特性,其量测结果如下:
最佳元件效率在21.43cd/A,11.99lm/W;
元件效率在20cd/A,7.2lm/W(1000cd/m2);
发光波长CIE座标:(0.16,0.35)。
如上所述,本发明所述具有式(I)之化合物作为主发光体材料的电激发光装置,经过进一步调整后,在1000Cd/m2亮度下,元件效率可提升至7lm/W(蓝光磷光有机电激发光装置),甚至达到22lm/W以上(绿光磷光有机电激发光装置),此在磷光有机电激发光装置技术领域中,实属相当优秀的表现。本发明所述之具有式(I)的有机化合物,其三氮唑(trizole)基团及咔唑(carbazole)基团系以间位方式配置于苯环上,使得其具有较短的共轭体系,因此除了适合作为蓝光磷光有机电激发光装置之发光层主体材料,亦适合作为绿光磷光有机电激发光装置之发光层主体材料。
虽然本发明已以较佳实施例揭露如上,然其并非用以限定本发明,任何熟习此技艺者,在不脱离本发明之精神和范围内,当可作些许之更动与润饰,因此本发明之保护范围当视后附权利要求书所界定者为准。
Claims (7)
1.一种有机化合物,其具有如式(III)所示的结构:
其中,R1各自独立且分别为相同或不同的取代基,为氢或C1-8烷基;以及
R3为氢、羟基、C1-8烷基、或C1-8烷氧基。
2.如权利要求1的有机化合物,其中R1、及R3分别为相同或不同的取代基,为甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、或己基。
3.如权利要求1的有机化合物,其中R3为甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、或异丁氧基。
4.如权利要求1的有机化合物,其中该有机化合物系为
5.一种有机电激发光装置,包括:
一对电极;以及
有机发光单元,配置于该对电极之间,其中该有机发光单元包含具有式(III)所示结构的化合物:
其中,R1各自独立且分别为相同或不同的取代基,为C1-8烷基;以及
R3为氢、羟基、C1-8烷基、或C1-8烷氧基。
6.一种有机电激发光装置,包括:
一对电极;以及
有机发光单元,配置于该对电极之间,
其中,该有机发光单元包含发光层,该发光层包含主体材料及磷光掺杂材料,而该主体材料包含具有式(III)所示结构的化合物:
其中,R1各自独立且分别为相同或不同之取代基,为C1-8烷基;以及
R3为氢、羟基、C1-8烷基、或C1-8烷氧基。
7.如权利要求6的有机电激发光装置,其中该发光层系发出蓝光、或绿光。
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