TWI538274B - Organic light field components - Google Patents
Organic light field components Download PDFInfo
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- TWI538274B TWI538274B TW101127787A TW101127787A TWI538274B TW I538274 B TWI538274 B TW I538274B TW 101127787 A TW101127787 A TW 101127787A TW 101127787 A TW101127787 A TW 101127787A TW I538274 B TWI538274 B TW I538274B
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- carbon atoms
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- 239000010410 layer Substances 0.000 claims description 139
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 55
- -1 carbazole compound Chemical class 0.000 claims description 51
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 27
- 230000000903 blocking effect Effects 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 23
- 239000012044 organic layer Substances 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 230000005525 hole transport Effects 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 238000005401 electroluminescence Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000010030 laminating Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 239000000463 material Substances 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 40
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
- 238000002347 injection Methods 0.000 description 20
- 239000007924 injection Substances 0.000 description 20
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000556 agonist Substances 0.000 description 7
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 239000007772 electrode material Substances 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 150000004866 oxadiazoles Chemical class 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000008425 anthrones Chemical class 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- ATBKVKDEMSGMTQ-UHFFFAOYSA-N hydrazine triphenylphosphane Chemical compound NN.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 ATBKVKDEMSGMTQ-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000007978 oxazole derivatives Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- RGXAPHRWCPNLDR-UHFFFAOYSA-N 2-(2-phenylethenyl)-7H-purine Chemical class C(=Cc1ncc2[nH]cnc2n1)c1ccccc1 RGXAPHRWCPNLDR-UHFFFAOYSA-N 0.000 description 2
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 2
- LONQTZORWVBHMK-UHFFFAOYSA-N [N].NN Chemical class [N].NN LONQTZORWVBHMK-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 150000001788 chalcone derivatives Chemical class 0.000 description 2
- 229940127271 compound 49 Drugs 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005266 diarylamine group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 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 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- HRZTZLCMURHWFY-UHFFFAOYSA-N 2-bromo-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1Br HRZTZLCMURHWFY-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical class C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910000799 K alloy Inorganic materials 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- SIAPVDLXYGWEEF-UHFFFAOYSA-N [Ru].c1ccc(cc1)-c1ccccn1 Chemical compound [Ru].c1ccc(cc1)-c1ccccn1 SIAPVDLXYGWEEF-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical class C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 230000009477 glass transition Effects 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
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical class C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical compound C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
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Description
本發明係關於使用新穎有機電場發光元件用材料的有機電場發光元件者,更詳細為於由有機化合物所成之發光層上賦予電場,釋出光之薄膜型裝置者。
一般的有機電場發光元件(以下稱為有機EL元件)中,作為最簡單結構,係由發光層及夾住該層的一對對向電極所構成。即,利用在有機EL元件中,若於兩電極間輸入電場,由陰極注入電子,由陽極注入電洞,這些於發光層再結合而釋出光的現象。
近年來,使用有機薄膜的有機EL元件之開發正在進行者。特別對了提高發光效率,將提高由電極之載體注入的效率作為目的,進行電極種類之最適化,藉由將由芳香族二胺所成之電洞輸送層與8-羥基喹啉鋁錯體(以下稱為Alq3)所成之發光層作為薄膜設置於電極間的元件開發,與使用過去蒽等單結晶的元件作為比較,可大幅度改善發光效率,故將具有自發光.高速應答性之特徵的對高性能平板之實用化作為目標前進。
又,作為提高元件發光效率之嘗試,非使用螢光而使用磷光者被檢討。以設置由上述的芳香族二胺所成的電洞輸送層與由Alq3所成的發光層之元件為始的多數元件為利用螢光發光者,但使用磷光發光,即藉由利用由三重態
激起狀態之發光,與使用過去螢光(一重態)的元件相比較,期待3~4倍程度之效率提高。欲達成該目的,將香豆素衍生物或二苯基甲酮衍生物作為發光層者正被檢討者,但僅得到極低之亮度。又,作為利用三重態狀態之嘗試,使用銪錯體正被檢討者,此亦無法達到高效率之發光。近年來,將如專利文獻1所舉出的發光高效率化或長壽命化作為目的,將銥錯體等有機金屬錯體為中心的研究正多數被進行。
〔專利文獻1〕特表2003-515897號公報
〔專利文獻2〕特開2001-313178號公報
〔專利文獻3〕WO2009/008100
〔專利文獻4〕特表2011-509247號公報
〔專利文獻5〕WO2011/057706
欲得到較高發光效率,與前述摻合物材料之同時,所使用之主材料成為重要。作為主材料被提案的代表性者,可舉出在專利文獻2所介紹的咔唑化合物之4,4'-雙(9-咔唑基)聯苯基(以下稱為CBP)。CBP係以參(2-苯基吡啶)銥錯體(以下稱為Ir(ppy)3)作為代表的綠色磷光發光材料之主材料使用時,因CBP為容易流動電洞,不容易流動電子的特性上,電荷注入失去平衡,過剩之電洞於電子輸送層側流出,作為結果降低由Ir(ppy)3之發光效率。
如前述所示,欲在有機EL元件得到高發光效率,具有高三重態激起能量,且對於兩電荷(電洞.電子)注入
輸送特性取得平衡之主材料為必要。且,期待電氣化學性安定,具備高耐熱性之同時具備優良無定形安定性之化合物,並要求進一步改良。
於專利文獻3中作為有機EL元件之主材料揭示如以下所示咔唑化合物。
然而,該咔唑衍生物為於二苯並呋喃之第3、7位上因具有苯基,被推定無法得到充分發光效率。
專利文獻4中作為有機EL元件之主材料揭示如以下所示之咔唑化合物。
然而,僅揭示上述化合物為於二苯並噻吩的第2位上導入咔唑的化合物,但未揭示使用於二苯並噻吩或二苯並呋喃的第1位導入咔唑之本發明的化合物之有機EL元件
的有用性。
專利文獻4中作為有機EL元件之主材料揭示如以下所示咔唑化合物。
然而,僅揭示上述化合物為於二苯並噻吩的第4位導入咔唑之化合物,並無揭示於二苯並噻吩或二苯並呋喃的第1位導入咔唑之化合物的有機EL元件的有用性。
專利文獻5中作為有機EL元件之主材料揭示如以下所示咔唑化合物。
然而,上述化合物為導入含氮6員環與咔唑之化合物作為特徵者,雖揭示於二苯並噻吩的第3位進行取代之化合物,但並未揭示使用於二苯並噻吩或二苯並呋喃的第1
位導入咔唑之化合物的有機EL元件的有用性。
欲將有機EL元件應用於平板顯示器等顯示元件時,改善元件之發光效率的同時,必須充分確保驅動時的安定性。本發明有鑑於上述現狀,以提供具有高效率且高驅動安定性之實用上有用的有機EL元件及適用此的化合物為目的。
本發明者們經詳細檢討結果,發現將於二苯並噻吩或二苯並呋喃的第1位具有咔唑基,且於該咔唑基的第2位~7位之位置上具有特定取代基的化合物作為有機EL元件使用時,可顯示優良特性,而完成本發明。
本發明係關於在基板上,層合陽極、有機層及陰極所成之有機電場發光元件中,於選自發光層、電洞輸送層、電子輸送層、電洞阻止層、及電子阻止層所成群的至少一層使用一般式(1)所示咔唑化合物的有機電場發光元件。
一般式(1)中,R1~R6各獨立表示氫、碳數1~10的烷基、碳數3~11的環烷基、或一般式(2)所示芳香族基,R1~R6的至少1個為一般式(2)所示芳香族基。X各獨立表示CR9或氮。R7~R9各獨立表示氫、碳數1~10的烷基、碳數3~11的環烷基、碳數6~18的芳香族烴基、或碳數3~17的芳香族雜環基,但上述芳香族烴基、及芳香族雜環基可具有取代基。E表示氧或硫。
一般式(1)中,R1~R6的至少1個為一般式(2)所示1價芳香族基,但R2為一般式(2)所示芳香族基者為佳。
又,一般式(1)所示咔唑化合物以一般式(3)所示咔唑化合物為佳,以一般式(4)所示咔唑化合物為較佳。
一般式(1)~(4)中,相同符號具有相同意思。因此,X、R7~R9、及E之意思如一般式(1)~(2)中所說明。且,一般式(4)中,複數R9可相同或相異。
一般式(4)中,R7~R9雖如上述,但R7~R9各獨立表示氫、碳數1~10的烷基、碳數3~11的環烷基、未取代的碳數6~18的芳香族烴基或未取代之碳數3~17的芳
香族雜環基者為佳,這些芳香族烴基或芳香族雜環基具有取代基之取代芳香族烴基或取代芳香族雜環基者為佳。作為上述取代基,以碳數1~6的烷基、碳數3~10的環烷基、碳數1~6的烷氧基、碳數2~7的醯基、碳數6~12的芳香族烴基或碳數12~24的二芳基胺基為佳。又,芳香族雜環基以非含氮6員環,其為未取代之碳數3~17的芳香族雜環基為佳,該芳香族雜環基可具有取代基。對於碳數之計算,其為取代芳香族烴基或取代芳香族雜環基時,取代基之碳數為外數。但若含有取代基之碳數的數係為上述範圍內時為佳。
又,本發明的有機電場發光元件具有含有一般式(1)所示咔唑化合物與磷光發光摻合物之發光層者為佳。
本發明的有機電場發光元件為在特定層上含有前述一般式(1)所示咔唑化合物。於一般式(1)所示咔唑化合物具有一般式(3)或(4)所示咔唑化合物。一般式(1)中,R1~R6的至少1個為一般式(2)所示芳香族基。
一般式(1)中,R1~R6各獨立表示氫、碳數1~10的烷基、碳數3~11的環烷基、一般式(2)所示1價芳香族基,至少1個為一般式(2)所示芳香族。較佳為R2可為一般式(2)所示芳香族基者。
一般式(2)~(3)中,X各獨立表示CR9或氮。又,一般式(2)~(4)中,R7~R9各獨立表示氫、碳數1~10的烷基、碳數3~11的環烷基、碳數6~18的芳香族烴基、或碳數3~17的芳香族雜環基。其中,碳數6~18的芳香族烴基、或碳數3~17的芳香族雜環基可具有取代基。
R1~R9為碳數1~10的烷基或碳數3~11的環烷基時,作為這些具體例,可舉出甲基、乙基、丙基、丁基、己基、庚基、辛基、壬基、癸基、環己基、甲基環己基等,可為直鏈或分支。較佳為碳數1~6的烷基、碳數3~8的環烷基。具體為甲基、乙基、丙基、丁基、戊基、己基、環己基。
其次,對於R7~R9為芳香族烴基、或芳香族雜環基時做說明。
芳香族烴基或芳香族雜環基為碳數6~18的芳香族烴基或碳數3~17的芳香族雜環基。作為該具體例,可舉出由選自苯、萘、芴、蒽、菲、苯並苊、芘、、吡啶、嘧啶、三嗪、吲哚、喹啉、異喹啉、喹喔啉、酞嗪、咔唑、吖啶、鄰二氮菲、吩嗪、苯並呋喃、二苯並呋喃、呫噸、Oxanthrene、吩噁嗪、苯並噻吩、二苯並噻吩、噻呫噸、噻蒽、吩噁噻、及酚噻嗪的芳香族化合物除去1個氫所產生的1價基,較佳為由選自苯、吲哚、咔唑、苯並呋喃、二苯並呋喃、苯並噻吩、及二苯並噻吩的芳香族化合物除去1個氫所產生的1價基,較佳為由選自苯、及咔唑之芳
香族化合物除去1個氫所產生的1價基。
上述芳香族烴基或芳香族雜環基可具有取代基,具有取代基時,取代基總數為1~10。較佳為1~6,較佳為1~4。又,上述芳香族烴基或芳香族雜環基具有2個以上取代基時,彼等可相同或相異。又,對於上述芳香族烴基或芳香族雜環基之碳數計算,具有取代基時,未含該取代基之碳數。若以含有取代基之碳數進行計算時,碳數為芳香族烴基時,以6~50之範圍為佳,較佳為6~30,芳香族雜環基時,以3~50的範圍為佳,較佳為5~30。
作為這些較佳取代基,可舉出碳數1~6的烷基、碳數3~10的環烷基、碳數1~6的烷氧基、碳數2~7的醯基、碳數6~12的芳香族烴基或碳數12~24的二芳基胺基。較佳為可舉出碳數1~4的烷基、碳數3~8的環烷基、碳數1~4的烷氧基、碳數2~5的醯基、碳數6~10的芳香族烴基或碳數12~20的二芳基胺基,作為具體例可舉出甲基、乙基、丙基、丁基、環戊基、環己基、甲基環己基、甲氧基、乙氧基、丙氧基、丁氧基、己氧基、乙醯基、丙醯基、苯基、甲苯基、萘基、二苯基胺基、二萘基胺基等。
前述一般式(1)所示化合物較佳為上述一般式(3)或(4)所示。一般式(1)、(3)及(4)中,E表示氧或硫。對於一般式(3)及(4),R7~R9如上述所說明者。
一般式(4)中,R7~R9各獨立為氫、碳數1~10的
烷基、碳數3~11的環烷基、碳數6~18的芳香族烴基、或碳數3~17的芳香族雜環基,但碳數3~17的芳香族雜環基之情況時,非含氮6員環者為佳。
其中,作為非含氮6員環的取代或未取代之碳數3~17的芳香族雜環基,以取代或未取代之碳數6~17的縮合芳香族雜環基者為佳。該芳香族雜環基除去非含氮6員環時,與上述說明之芳香族雜環基相同。
一般式(1)所示化合物之具體例如以下所示,並未限定於彼等例示化合物。
藉由將上述一般式(1)所示咔唑化合物含於在基板上層合陽極、複數的有機層及陰極所成的有機EL元件之至少1個有機層中,可賦予優良有機電場發光元件。有機
層至少具有發光層者為佳,其他具有電洞輸送層、電子輸送層、電洞阻止層、或電子阻止層者為佳。作為含有咔唑化合物之有機層,可舉出發光層、電洞輸送層、電子輸送層、電洞阻止層、或電子阻止層。較佳為作為含有磷光發光摻合物之發光層的主材料者為佳。
本發明的有機EL元件為於層合於基板上之陽極與陰極之間,具有至少具有1個發光層之有機層,且至少一個有機層含有上述咔唑化合物。較佳為與磷光發光摻合物同時將一般式(1)所示咔唑化合物含於發光層中。
其次對於本發明的有機EL元件之結構,一邊參照圖面一邊說明,但本發明的有機EL元件之結構並未受到這些圖示者之限定。
圖1表示一般有機EL元件之結構例的截面圖,1表示基板,2表示陽極,3表示電洞注入層,4表示電洞輸送層,5表示發光層,6表示電子輸送層,7表示陰極。本發明的有機EL元件中,可具有與發光層鄰接的激動子阻止層,又於發光層與電洞注入層之間可具有電子阻止層。激動子阻止層可插入發光層之陽極側、陰極側中任一,亦可插入於雙方。本發明的有機EL元件中,具有作為必須層的基板、陽極、發光層及陰極,除必須層以外的層,可具有電洞注入輸送層、電子注入輸送層,於發光層與電子注入輸送層之間可進一步具有電洞阻止層。且,電洞注入輸送層表示電洞注入層與電洞輸送層之任一層或兩者,電子注入輸送層表示電子注入層與電子輸送層之任一層或兩
者。
且,亦可以與圖1相反的結構,即於基板1上以陰極7、電子輸送層6、發光層5、電洞輸送層4、陽極2之順序層合,此時視必要可追加層,或可省略。
本發明的有機EL元件以可由基板支持者為佳。對於該基板,並無特別限制,可為自過去至有機EL元件慣用者,例如可使用玻璃、透明塑質、石英等所成者。
作為有機EL元件中之陽極,使用將功函數較大的(4eV以上)金屬、合金、電傳導性化合物及這些混合物作為電極物質者為佳。作為如此電極物質之具體例,可舉出Au等金屬、CuI、銦錫氧化物(ITO)、SnO2、ZnO等導電性透明材料。又,亦可使用可由IDIXO(In2O3-ZnO)等非晶質製作透明導電膜之材料。陽極為這些電極物質藉由蒸鍍或濺鍍等方法使其形成薄膜,以光微影法形成所望形狀之圖型亦可,或若不需要過度圖型精度時(100μm以上程度),於上述電極物質之蒸鍍或濺鍍時介著所望形狀之光罩形成圖型。或如有機導電性化合物,使用可塗佈的物質時,可使用印刷方式、塗佈方式等濕式成膜法。使用藉由該陽極之發光時,使透過率超過10%者為佳,又作為陽極之薄片電阻以數百Ω/□以下為佳。且膜厚
雖依材料而不同,一般為10~1000nm,較佳為10~200nm之範圍中選出。
一方面,作為陰極,使用將功函數較小者(4eV以下)金屬(稱為電子注入性金屬)、合金、電傳導性化合物及這些混合物作為電極物質者。作為如此電極物質之具體例,可舉出鈉、鈉-鉀合金、鎂、鋰、鎂/銅混合物、鎂/銀混合物、鎂/鋁混合物、鎂/銦混合物、鋁/氧化鋁(Al2O3)混合物、銦、鋰/鋁混合物、稀土類金屬等。這些中,由對於電子注入性及氧化等之耐久性的觀點來看,電子注入性金屬與藉此功函數值較為穩定之金屬的第二金屬之混合物,例如以鎂/銀混合物、鎂/鋁混合物、鎂/銦混合物、鋁/氧化鋁(Al2O3)混合物、鋰/鋁混合物、鋁等為佳。陰極為可藉由將這些電極物質經蒸鍍或濺鍍等方法而形成薄膜而製作。又,作為陰極之薄片電阻以數百Ω/□以下為佳,膜厚一般為10nm~5μm,較佳為50~200nm之範圍中選出。且,欲透過發出的光,有機EL元件之陽極或陰極中任一方若為透明或半透明時可提高發光亮度故較佳。
又,於陰極將上述金屬至做出1~20nm之膜厚後,將陽極之說明所舉出的導電性透明材料製作於其上後,可至做出透明或半透明之陰極,藉由應用此,可製作出陽極與陰極雙方具有透過性之元件。
發光層為磷光發光層,含有磷光發光摻合物與主材料。作為磷光發光摻合物材料,含有包含選自釕、銠、鈀、銀、錸、鋨、銥、鉑及金的至少一種金屬之有機金屬錯體者為佳。具體可舉出以下專利公報所記載之化合物,但並未限定於此等化合物。以下為專利公報等號碼。
WO2009-073245號公報、WO2009-046266號公報、WO2007-095118號公報、WO2008-156879號公報、WO2008-140657號公報、US2008-261076號公報、特表2008-542203號公報、WO2008-054584號公報、特表2008-505925號公報、特表2007-522126號公報、特表2004-506305號公報、特表2006-513278號公報、特表2006-50596號公報、WO2006-046980號公報、WO2005113704號公報、US2005-260449號公報、US2005-2260448號公報、US2005-214576號公報、WO2005-076380號公報、US2005-119485號公報、WO2004-045001號公報、WO2004-045000號公報、WO2006-100888號公報、WO2007-004380號公報、WO2007-023659號公報、WO2008-035664號公報、特開2003-272861號公報、特開2004-111193號公報、特開2004-319438號公報、特開2007-2080號公報、特開2007-9009號公報、特開2007-227948號公報、特開2008-91906號公報、特開2008-311607號公報、特開2009-19121號公報、特開2009-
46601號公報、特開2009-114369號公報、特開2003-253128號公報、特開2003-253129號公報、特開2003-253145號公報、特開2005-38847號公報、特開2005-82598號公報、特開2005-139185號公報、特開2005-187473號公報、特開2005-220136號公報、特開2006-63080號公報、特開2006-104201號公報、特開2006-111623號公報、特開2006-213720號公報、特開2006-290891號公報、特開2006-298899號公報、特開2006-298900號公報、WO2007-018067號公報、WO2007/058080號公報、WO2007-058104號公報、特開2006-131561號公報、特開2008-239565號公報、特開2008-266163號公報、特開2009-57367號公報、特開2002-117978號公報、特開2003-123982號公報、特開2003-133074號公報、特開2006-93542號公報、特開2006-131524號公報、特開2006-261623號公報、特開2006-303383號公報、特開2006-303394號公報、特開2006-310479號公報、特開2007-88105號公報、特開2007-258550號公報、特開2007-324309號公報、特開2008-270737號公報、特開2009-96800號公報、特開2009-161524號公報、WO2008-050733號公報、特開2003-73387號公報、特開2004-59433號公報、特開2004-155709號公報、特開2006-104132號公報、特開2008-37848號公報、特開2008-133212號公報、特開2009-57304號公報、特開2009-286716號公報、特開2010-83852號公報、特表2009-
532546號公報、特表2009-536681號公報、特表2009-542026號公報等。
作為較佳磷光發光摻合物,可舉出具有將Ir等貴金屬元素作為中心金屬之Ir(ppy)3等錯體類、Ir(bt)2.acac3等錯體類、PtOEt3等錯體類。這些錯體類之具體例如以下所示,但並未限定於下述化合物。
前述磷光發光摻合物含於發光層中之量以0.1~50重量%為佳,以1~30重量%的範圍為較佳。
作為發光層中之主材料,使用前述一般式(1)所示咔唑化合物為佳。但將該咔唑化合物使用於發光層以外之其他任意有機層時,使用於發光層之材料可為除咔唑化合物以外之其他主材料。又,可併用咔唑化合物與其他主材料。且可併用複數種類的公知主材料。
作為可使用的公知主化合物,以具有電洞輸送能、電子輸送能,且防止發光之長波長化,且具有高玻璃轉移溫度之化合物為佳。
如此其他主材料已可由多數專利文獻等得知,故可選自彼等。作為主材料之具體例,並無特別限定,可舉出吲哚衍生物、咔唑衍生物、吲哚咔唑衍生物、三唑衍生物、噁唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳基烷烴衍生物、吡唑啉衍生物、吡唑哢衍生物、伸苯基二胺衍生物、芳基胺衍生物、胺基取代查耳酮衍生物、苯乙烯基蒽衍生物、芴酮衍生物、腙衍生物、二苯乙烯衍生物、矽氮衍生物、芳香族第三胺化合物、苯乙烯基胺化合物、芳香族二次甲基系化合物、紫質系化合物、蒽醌二甲烷衍生物、蒽酮衍生物、二苯基醌衍生物、噻吡喃二氧化物衍生物、萘苝等雜環四羧酸酐、酞菁衍生物、8-羥喹啉衍生物之金屬錯體或金屬酞菁、苯並噁唑或苯並噻唑衍生物之金屬錯體作為代表的各種金屬錯體、聚矽烷系化合物、聚(N-乙烯基咔唑)衍生物、苯胺系共聚物、噻吩寡聚物、聚噻吩衍生物、聚伸苯基衍生物、聚伸苯基伸乙烯衍生物、聚芴衍生物等高分子化合物等。
所謂注入層為,欲降低驅動電壓或提高發光亮度,設置於電極與有機層間的層,具有電洞注入層與電子注入層,亦可存在於陽極與發光層或電洞輸送層之間、及陰極與發光層或電子輸送層之間。注入層可視必要設置。
電洞阻止層在廣泛意義中表示具有電子輸送層之功能,係由具有輸入電子的功能且輸送電洞的能力顯著小的電洞阻止材料所成,藉由輸送電子且阻止電洞,可提高電子與電洞之再結合確率。
於電洞阻止層中,使用一般式(1)所示咔唑化合物為佳,將咔唑化合物使用於其他任意有機層時,可使用公知電洞阻止層材料。又,作為電洞阻止層材料,視必要可使用後述電子輸送層之材料。
所謂電子阻止層,係由具有輸送電洞之功能且輸送電子的能力顯著小之材料所成,輸送電洞且阻止電子,可提高電子與電洞之再結合的確定。
作為電子阻止層之材料,視必要可使用後述電洞輸送層之材料。電子阻止層之膜厚以3~100nm為佳,較佳為5~30nm。
所謂激動子阻止層為,使用於阻止在發光層內電洞與電子再結合所產生的激動子擴散於電荷輸送層之層,藉由本層之挿入,可將激動子有效率地封鎖於發光層內,可提高元件之發光效率。激動子阻止層可插入鄰接於發光層之陽極側、陰極側中任一者,亦可同時插入於雙方。
作為激動子阻止層之材料,例如可舉出1,3-二咔唑基
苯(mCP)或雙(2-甲基-8-羥基喹啉)-4-苯基酚鋁鹽(III)(BAlq)。
所謂電洞輸送層係由具有輸送電洞之功能的電洞輸送材料所成,電洞輸送層可設置單層或複數層。
作為電洞輸送材料,具有電洞的注入或輸送、電子之障壁性中任一者,亦可為有機物、無機物中任一者。於電洞輸送層使用一般式(1)所示咔唑化合物者為佳,可選自過去公知化合物中任意者。作為可使用之公知電洞輸送材料,例如可舉出三唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳基烷烴衍生物、吡唑啉衍生物及吡唑哢衍生物、伸苯基二胺衍生物、芳基胺衍生物、胺基取代查耳酮衍生物、噁唑衍生物、苯乙烯基蒽衍生物、芴酮衍生物、腙衍生物、二苯乙烯衍生物、矽氮衍生物、苯胺系共聚物,又可舉出導電性高分子寡聚物,特別可舉出噻吩寡聚物等,但使用三唑衍生物、噁二唑衍生物、咪唑衍生物、芳基胺衍生物、噁唑衍生物為佳,使用芳基胺衍生物為較佳。
所謂電子輸送層為係由具有輸送電子之功能的材料所成,電子輸送層可設置單層或複數層。
作為電子輸送材料(亦有兼具電洞阻止材料之情況),僅具有將由陰極注入之電子傳達至發光層的功能即
可。於電子輸送層使用本發明的一般式(1)所示咔唑化合物時為佳,可使用選自過去公知化合物中任意者,例如可舉出硝基取代芴衍生物、二苯基醌衍生物、噻吡喃二氧化物衍生物、碳二醯亞胺、亞茀基甲烷衍生物、蒽醌二甲烷及蒽酮衍生物、噁二唑衍生物等。且對於上述噁二唑衍生物,將噁二唑環的氧原子由硫原子取代之噻二唑衍生物、具有已知作為電子吸引基之喹喔啉環的喹喔啉衍生物亦可作為電子輸送材料使用。且亦可使用將這些材料導入高分子鏈中,或將這些材料作為高分子之主鏈的高分子材料。
以下本發明藉由實施例做更詳細說明,但本發明無庸置疑地並未限定於這些實施例中,若不超過該要旨下可在種種形態下實施。
藉由以下所示流程合成成為磷光發光元件用材料之咔唑化合物。且化合物號碼則對應上述例示化合物之號碼。
氮氣環境下加入2-甲氧基苯基亞硼酸18.84 g(0.124 mol)、1-溴-2,6-二氟苯24.00 g(0.124 mol)、肆(三苯基膦)鈀(0)7.72 g(0.00496 mol)、甲苯600 ml、乙醇100 ml,在室溫一邊攪拌,一邊加入2M氫氧化鈉水溶液200 ml。在90℃進行5小時攪拌後,冷卻至室溫,將有機層以蒸餾水(300 ml×3)洗淨。將有機層以無水硫酸鎂乾燥後,過濾分離硫酸鎂,將溶劑減壓餾去。將所得之殘渣以矽膠管柱層析法進行純化後得到白色固體之中間體(A1)10.01 g(0.0455 mol,產率38%)。
氮氣環境下,加入中間體(1)10.00 g(0.0454 mol)、二氯甲烷100 ml,在0℃下一邊攪拌,一邊加入三溴化硼之二氯甲烷溶液20 ml。在室溫下進行6小時攪拌後,加入水。將有機層以蒸餾水(30 ml×3)洗淨。將有機層以無水硫酸鎂乾燥後,過濾分離硫酸鎂,將溶劑減壓餾去。將所得之殘渣以矽膠管柱層析法進行純化後得到無
色液體之中間體(A2)8.62 g(0.0418 mol,產率92%)。
氮氣環境下,加入中間體(A2)8.62 g(0.0418 mol)、N-甲基-吡咯烷酮230 ml,在室溫一邊攪拌,一邊加入碳酸鉀11.56 g(0.0836 mol)。在180℃進行3小時攪拌後,冷卻至室溫,將碳酸鉀過濾分離。於濾液中加入蒸餾水900 ml,在室溫下攪拌後,將析出之固體過濾分離。將所得之固體溶解於二氯甲烷,將有機層以蒸餾水(30 ml×3)洗淨。將有機層以無水硫酸鎂乾燥後,過濾分離硫酸鎂,將溶劑減壓餾去。將所得之殘渣以矽膠管柱層析法進行純化後得到白色固體之中間體(A3)7.02 g(0.0377 mol,產率90%)。
氮氣環境下,加入咔唑35 g(0.209 mol)、乙酸300 ml,在室溫一邊攪拌,一邊加入碘化鉀24.24 g(0.146 mol)、碘酸鉀31.24 g(0.146 mol)。在80℃進行2小時攪拌後,冷卻至室溫。加入亞硫酸氫鈉水溶液300 ml、四氫呋喃300 ml,在室溫攪拌。加入甲苯300 ml,將有機層以蒸餾水(200 ml×2)洗淨。將有機層以無水硫酸鎂乾燥後,過濾分離硫酸鎂,將溶劑減壓餾去。將所得之殘渣藉由再結晶使其純化後得到白色固體之中間體(A4)20.75 g(0.0708 mol)。
氮氣環境下,加入氫化鈉3.03 g(0.0752 mol)、二甲基甲醯胺(DMF)20 ml,在室溫下一邊攪拌,一邊加入溶解中間體(A4)20.00 g(0.0682 mol)之DMF溶液20 ml。在室溫進行30分鐘攪拌,加入溶解中間體(A3)7.00 g(0.0376 mol)之DMF溶液20 ml。在120℃進行7小時攪拌後,冷卻至室溫。加入蒸餾水300 ml並在室溫下攪拌。將析出之固體進行過濾分離。將所得之固體溶解於四氫呋喃,加入蒸餾水200 ml。以甲苯(100 ml×3)萃取後,將有機層以無水硫酸鎂乾燥後,過濾分離硫酸鎂,
將溶劑減壓餾去。將所得之殘渣以矽膠管柱層析法進行純化後得到白色固體之中間體(A5)16.74 g(0.0364 mol,產率97%)。
氮氣環境下,加入中間體(A5)10.00 g(0.0218 mol)、中間體(A6)8.13 g(0.0283 mol)、肆(三苯基膦)鈀(0)1.36 g(0.000872 mol)、甲苯300 ml、乙醇50 ml,在室溫一邊攪拌,一邊加入2M氫氧化鈉水溶液40 ml。在90℃下進行2小時攪拌後,冷卻至室溫,將有機層以蒸餾水(100 ml×2)洗淨。將有機層以無水硫酸鎂乾燥後,過濾分離硫酸鎂,將溶劑減壓餾去。將所得之殘渣以矽膠管柱層析法、再結晶進行純化後,得到白色固體之(化合物8)8.70 g(0.0151 mol,產率69%)。
APCI-TOFMS,m/z 575〔M+1〕、1H-NMR測定結果(測定溶劑:THF-d8)如圖2所示。
氮氣環境下加入中間體(A5)9.00 g(0.0196 mol)、中間體(A7)10.63 g(0.0235 mol)、肆(三苯基膦)鈀(0)1.22 g(0.000784 mol)、甲苯300 ml、乙醇50 ml,在室溫一邊攪拌,一邊加入2M氫氧化鈉水溶液35 ml。在70℃進行7小時攪拌後,冷卻至室溫,將有機層以蒸餾水(100 ml×2)洗淨。將有機層以無水硫酸鎂乾燥後,過濾分離硫酸鎂,將溶劑減壓餾去。將所得之殘渣以矽膠管柱層析法、再結晶進行純化,得到白色固體之(化合物49)1.61 g(0.00218 mol,產率9%)。
APCI-TOFMS,m/z 740〔M+1〕、1H-NMR測定結果(測定溶劑:THF-d8)如圖3所示。
形成由膜厚110nm的ITO基板所成之陽極的玻璃基板上,將各薄膜藉由真空蒸鍍法,在真空度4.0×10-5Pa進行層合。首先,於ITO上將CuPc形成20 nm之厚度。其次作為電洞輸送層將NPB形成20 nm之厚度。其次於電洞輸送層上將作為主材料之(化合物8)與作為摻合物之Ir(ppy)3自相異蒸鍍源進行共蒸鍍,形成30 nm厚度之發光層。此時Ir(ppy)3的濃度為10 wt%。其次作為電子輸送層形成40 nm厚度之Alq3。且於電子輸送層上形成作為電子注入層之氟化鋰(LiF)1nm厚度。最後於電子注入層上作為電極形成鋁(Al)之70nm厚度,製作出有機EL元件。
於所得之有機EL元件連接外部電源,輸入直流電壓後,確認具有如表1所示發光特性。
與實施例1同樣下,合成化合物1、5、6、7、24、25、及28,作為實施例3之發光層的主材料,取代化合物8使用化合物1、5、6、7、24、25、28或實施例2所得之化合物49以外,與實施例3同樣下作成有機EL元件。
作為實施例3中之發光層的主材料使用CBP以外,與實施例3同樣下作成有機EL元件。
作為實施例3中之發光層的主材料使用化合物H-1以外,與實施例3同樣下作成有機EL元件。
得知在實施例3~11、比較例1~2所得之各元件發光光譜的極大波長皆為540 nm,其係由Ir(ppy)3之發光。各發光特性如表1所示。表1中,亮度、電壓及發光效率以
20 mA/cm2的驅動時之值(初期特性)表示。
實施例3與比較例1及比較例2比較顯示提高初期特性。藉此得知於二苯並噻吩或二苯並呋喃之第1位上具有咔唑,且咔唑的第2位~7位之位置上具有特定取代基之化合物使用於有機EL元件時,可改善有機EL元件特性。同樣地實施例4~11之EL元件特性顯示良好,於此亦顯示一般式(1)所示咔唑化合物之優位性。
使用於本發明的有機電場發光元件之一般式(1)所示咔唑化合物為,在二苯並噻吩或二苯並呋喃的第1位上與咔唑環之N結合,且在咔唑環之第2位~第7位的位置
上具有特定取代基時,可達到電洞、電子移動度之微調整、以及可控制電離電位(IP)、電子親和力(EA)、三重態能量(T1)之各種能量值。又,該咔唑化合物可在氧化、還原、激起之各活性狀態下提高安定性,同時具有良好無定形特性。由以上得知,本發明可實現驅動壽命長,耐久性高之有機EL元件。
藉由本發明之有機EL元件對於發光特性、驅動壽命以及耐久性,在實用上達到令人滿足的水準、對於平板顯示器(行動電話顯示元件、車載顯示元件、OA電腦顯示元件或電視等)、發揮作為面發光體之特徵的光源(照明、影印機之光源、液晶顯示器或計器類之背光光源)、顯示板或標識燈等應用,其為技術價值非常大者。
1‧‧‧基板
2‧‧‧陽極
3‧‧‧電洞注入層
4‧‧‧電洞輸送層
5‧‧‧發光層
6‧‧‧電子輸送層
7‧‧‧陰極
[圖1〕表示有機EL元件之一結構例截面圖。
[圖2〕表示咔唑化合物8的1H-NMR柱狀圖。
〔圖3〕表示咔唑化合物49的1H-NMR柱狀圖。
1‧‧‧基板
2‧‧‧陽極
3‧‧‧電洞注入層
4‧‧‧電洞輸送層
5‧‧‧發光層
6‧‧‧電子輸送層
7‧‧‧陰極
Claims (6)
- 一種有機電場發光元件,其為於基板上層合陽極、有機層及陰極所成之有機電場發光元件,其特徵為於選自發光層、電洞輸送層、電子輸送層、電洞阻止層、及電子阻止層所成群的至少一層上含有一般式(1)所示咔唑化合物者;
- 如申請專利範圍第1項之有機電場發光元件,其 中一般式(1)中,R2為一般式(2)所示芳香族基。
- 如申請專利範圍第1項之有機電場發光元件,其中咔唑化合物為一般式(3)所示咔唑化合物;
- 如申請專利範圍第3項之有機電場發光元件,其中咔唑化合物為一般式(4)所示咔唑化合物;
- 如申請專利範圍第4項之有機電場發光元件,其中一般式(4)中,R7~R9各獨立為氫、碳數1~10的烷基、碳數3~11的環烷基、碳數6~18的未取代的芳香族烴基、碳數3~17的未取代的芳香族雜環基,或於該未取代的芳香族烴基或該未取代的芳香族雜環基具有取代基之取代芳香族烴基或取代芳香族雜環基,該取代基為選自碳數1~6的烷基、碳數3~10的環烷基、碳數1~6的烷氧基、碳數2~7的醯基、碳數6~12的芳香族烴基或碳數12~24的二芳基胺基之一種。
- 如申請專利範圍第1項至第5項中任一項之有機電場發光元件,其中含有咔唑化合物之層係為含有磷光發光摻合物之發光層。
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CN103797602A (zh) | 2014-05-14 |
CN103797602B (zh) | 2016-03-23 |
KR101891308B1 (ko) | 2018-08-23 |
EP2757607A4 (en) | 2015-04-22 |
US20140209885A1 (en) | 2014-07-31 |
KR20140074925A (ko) | 2014-06-18 |
JP5914500B2 (ja) | 2016-05-11 |
TW201327959A (zh) | 2013-07-01 |
WO2013038804A1 (ja) | 2013-03-21 |
EP2757607B1 (en) | 2016-02-10 |
EP2757607A1 (en) | 2014-07-23 |
JPWO2013038804A1 (ja) | 2015-03-26 |
US9466802B2 (en) | 2016-10-11 |
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