TW201407853A - 有機電子材料 - Google Patents
有機電子材料 Download PDFInfo
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- TW201407853A TW201407853A TW102118959A TW102118959A TW201407853A TW 201407853 A TW201407853 A TW 201407853A TW 102118959 A TW102118959 A TW 102118959A TW 102118959 A TW102118959 A TW 102118959A TW 201407853 A TW201407853 A TW 201407853A
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- TW
- Taiwan
- Prior art keywords
- group
- substituted
- unsubstituted
- phenyl
- alkyl
- Prior art date
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- 239000012776 electronic material Substances 0.000 title claims abstract description 17
- -1 dibenzofuranyl Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 10
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 10
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical class 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 21
- 230000003287 optical effect Effects 0.000 abstract 1
- 238000001771 vacuum deposition Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- 239000000543 intermediate Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 150000003505 terpenes Chemical class 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 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
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 3
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000010953 base metal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- MRBZYVMZUBUDAX-UHFFFAOYSA-N (3,5-diphenylphenyl)boronic acid Chemical compound C=1C(B(O)O)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 MRBZYVMZUBUDAX-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical class C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- ZMLPKJYZRQZLDA-UHFFFAOYSA-N 1-(2-phenylethenyl)-4-[4-(2-phenylethenyl)phenyl]benzene Chemical group C=1C=CC=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC1=CC=CC=C1 ZMLPKJYZRQZLDA-UHFFFAOYSA-N 0.000 description 1
- YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical class NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- 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
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- IDBFBDSKYCUNPW-UHFFFAOYSA-N lithium nitride Chemical compound [Li]N([Li])[Li] IDBFBDSKYCUNPW-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 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 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-O quinolin-8-yloxidanium Chemical compound C1=C[NH+]=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-O 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/573—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with three six-membered rings
- C07C13/58—Completely or partially hydrogenated anthracenes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
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Abstract
本發明涉及“有機電子材料”,屬于有機電致發光器件顯示材料技術領域。本發明所述的有機電子材料具有式(I)所述的結構式,具有較好熱穩定性,高發光效率,高發光純度。采用該有機發光材料制作的有機電致發光器件具有電致發光效率良好和色純度優異以及壽命長的優點。
Description
本發明涉及新型的有機電致發光材料通過真空蒸渡沈積成薄膜,作為藍光電致發光材料應用在有機電致發光二極管上,屬于有機電致發光器件顯示技術領域。
有機電致發光器件作為一種新型的顯示技術,具有自發光、寬視角、低能耗、效率高、薄、色彩豐富、響應速度快、適用溫度範圍廣、低驅動電壓、可制作柔性可彎曲與透明的顯示面板以及環境友好等獨特優點,因此,有機電致發光器件技術可以應用在平板顯示器和新一代照明上,也可以作為LCD的背光源。
有機電子發光器件為在兩個金屬電極之間通過旋塗或者沈積一層有機材料而制備的器件,一個經典的三層有機電致發光器件包含空穴傳輸層,發光層和電子傳輸層。由陽極產生的空穴經空穴傳輸層跟由陰極產生的電子經電子傳輸層結合在發光層形成激子,而後發光。有機電致發光器件可以通過改變發光層的材料來發射紅光,綠光和藍光。因而,穩定的,高效的和色彩純的有機電致發光材料對有機電致發光器件的應用和推廣具有重要作用,同時也是OLEDs大面積面板顯示的應用推廣的迫切需求。
在三原色(紅,藍,綠)當中,紅光和綠光材料最近已經取得了很大的發展,也符合面板的市場需求。對于藍光材料,也有一系列的商品化的材料,其中早期用得比較多的為出光興產的二苯乙烯基聯苯(DPVBi)類化合物,以這類化合物制備的器件具有較高的效率,但是往往這些材料的穩定性比較差,更有甚地,這類化合物的發光的顏色屬于天藍光,往往CIE值中的y>0.15。所以由于其不好的溫度性和不純的顏色很大
程度地限制了這類化合物在全彩顯示器件中的應用。另外一類藍光材料為柯達公司的ADN和四叔丁基苝,但是這些化合物的發光效率比較差,而且穩定性也不好,從而無法大量使用。
本發明就是克服上面化合物的缺陷提供一系列具有較好熱穩定性,高發光效率,高發光純度的有機電致藍光材料,由它制備的有機電致發光器件具有電致發光效率良好和色純度優異以及壽命長的優點。
本發明所述的有機電子材料具有式(I)所述的結構式:
其中,R1-R8獨立地表示為氫,氘原子,鹵素,氰基,硝基,C1-C8烷基、C1-C8烷氧基,C6-C30的取代或者未取代的芳基,C3-C30的取代或者未取代的含有一個或者多個的雜原子芳基,C2-C8取代或者未取代的烯烷基,C2-C8取代或者未取代的炔烷基,其中,Ar1-Ar4獨立地表示C6-C60取代或者未取代的芳基,C3-C60的取代或者未取代的帶有一個或者多個雜原子的雜芳基,三芳香(C6-C30)胺基。
優選:其中,R1-R8獨立地表示為氫,鹵素,氰基,硝基,C1-C8烷基、C1-C8烷氧基,C2-C8取代或者未取代的烯烷基,C2-C8取代
或者未取代的炔烷基,C1-C4烷基取代或未取代的苯基,C1-C4烷基取代或未取代的萘基;Ar1-Ar4獨立地表示C1-C4烷基或者C6-C30芳基取代的苯基,C1-C4烷基或者C6-C30芳基取代的萘基,苯基,萘基,N-芳基(C6-C30)或者C1-C4的烷基取代的哢唑基,二苯並噻吩基,二苯並呋喃基,蒽基,菲基,芘基,苝基,熒蒽基,(9,9-二烷基)芴基,(9,9-二烷基取代或未取代芳基)芴基,9,9-螺芴基。
優選:其中,R1-R8可以獨立地優選表示為氫,鹵素,C1-C4的烷基,C1-C4烷基取代或未取代的苯基,C1-C4烷基取代或未取代的萘基;優選Ar1-Ar4為獨立地表示苯基,甲苯基,叔丁基苯基,萘基,甲基萘,聯苯基,二苯基苯基,萘基苯基,二苯基聯苯基,二芳香胺基苯基,N-苯基哢唑基,(9,9-二烷基)芴基,(9,9-二烷基取代或未取代苯基)芴基,9,9-螺芴基。
優選:其中,R1,R4,R5,R8,優選為氫,R2,R3,R6,R7可以獨立優選表示為氫,氟,甲基,乙基,丙基,異丙基,叔丁基,苯基,萘基;Ar1-Ar4為獨立地表示苯基,甲苯基,萘基,甲基萘,聯苯基,二苯基苯基,萘基苯基,二苯基聯苯基,(9,9-二烷基)芴基,(9,9-二甲基取代或未取代苯基)芴基,9,9-螺芴基。
優選Ar2,Ar3,Ar4為獨立地表示苯基,萘基,聯苯基,Ar1為苯基,萘基,聯苯基,二苯基苯基,萘基苯基,二苯基聯苯基,(9,9-二烷基)芴基,(9-甲苯基,9’-苯基)芴基,9,9-螺芴基。
優選:R2,R3,R6,R7為氫,Ar2,Ar3,Ar4為獨立地表示苯基,萘基。
優選:
上述有機電子材料在有機電致發光器件,有機太陽能電池,有機薄膜晶體管或有機光感受器領域的應用。
如上面提到的,本發明的具體實施例如下,但不限于所列舉的結構:
本發明提供的有機電子材料可以制成有機電致發光器件,該器件包含陽極,陰極和一層或多層有機層,所述有機層中至少有一層含有如結構式I所述的有機電子材料。
所述多層有機層分別為空穴注入層,空穴傳輸層,發光層,空穴阻擋層和電子傳輸層,需要特別指出,上述有機層可以根據需要,這些有機層不必每層都存在。
所述空穴傳輸層,電子傳輸層和發光層中含有如結構式1所述的有機材料。
結構式I化合物作為無摻雜單一發光層或摻雜發光層。
所述摻雜發光層包括主體材料和客體材料,結構式(I)化合物作為主體材料時,其濃度為整個發光層重量的20-99.9%,優選80-99%,更優選為90-99%。結構式(I)化合物作為客體材料時,其濃度為這個發光層重量的0.01-80%,優選1-20%,更優選為1-10%。
包括同時使用結構式I的兩個化合物分別作主體材料和客體材料。
本發明的電子器件有機層的總厚度為1-1000 nm,優選1-500 nm,更優選50-300 nm。
本發明中的空穴傳輸層和空穴注入層,所需材料具有很好的空穴傳輸性能,能夠有效地把空穴從陽極傳輸到有機發光層上。可以包括小分子和高分子有機材料,可以包含如下,但是不限于這些,三芳香胺化合物,聯苯二胺化合物,噻唑化合物,惡唑化合物,咪唑類化合物,芴類化合物,酞菁類化合物,六氰基六雜三苯(hexanitrile hexaazatriphenylene),2,3,5,6-四氟-7,7',8,8'-四氰二甲基對苯醌(F4-TCNQ),聚乙烯基哢唑,聚噻吩,聚乙烯,聚苯磺酸。
本發明的有機電致發光層,除含有本發明的蒽乙烯基化合物外,還可以含有如下化合物,但是不限于此,萘類化合物,芘類化合物,芴類化合物,菲類化合物,屈類化合物,熒蒽類化合物,蒽類化合物,並五苯類化合物,苝類化合物,二芳乙烯類化合物,三苯胺乙烯類化合物,胺類化合物,苯並咪唑類化合物,呋喃類化合物,有機金屬螯合物。
本發明的有機電子器件使用的有機電子傳輸材料要求具有很好的電子傳輸性能,能夠有效地把電子從陰極傳輸到發光層中,可以選擇如下化合物,但是不限于此,氧雜惡唑,噻唑類化合物,三氮唑類化合物,三氮嗪類化合物,三氮雜苯類化合物,喔啉類化合物,二氮蒽類化合物,含矽雜環類化合物,喹啉類化合物,菲囉啉類化合物,金屬螯合物,氟取代苯類
化合物。
本發明的有機電子器件根據需要,可以加入一層電子注入層,該電子注入層可以有效的把電子從陰極注入到有機層中,主要選自堿金屬或者堿金屬的化合物,或選自堿土金屬或者堿土金屬的化合物,可以選擇如下化合物,但是不限于此,鋰,氟化鋰,氧化鋰,氮化鋰,8-羥基喹啉鋰,銫,碳酸銫,8-羥基喹啉銫,鈣,氟化鈣,氧化鈣,鎂,氟化鎂,碳酸鎂,氧化鎂。
器件實驗表明,本發明如式(I)所述的有機電子材料,具有較好熱穩定性,高發光效率,高發光純度。采用該有機發光材料制作的有機電致發光器件具有電致發光效率良好和色純度優異以及壽命長的優點。
10‧‧‧玻璃基板
20‧‧‧陽極
30‧‧‧空穴注入層
40‧‧‧空穴傳輸層
50‧‧‧發光層
60‧‧‧電子傳輸層
70‧‧‧電子注入層
80‧‧‧陰極
圖1為本發明的器件結構圖。
圖2為化合物110的1H NMR圖。
為了更詳細敘述本發明,特舉以下例子,但是不限于此。
在1 L的單口燒瓶中,加入25.5 g1-萘硼酸和25 g對溴苯甲醛,400 ml二氧六環,80 ml 2 M碳酸鉀水溶液,在氮氣保護下,加入1.0 g四三苯基磷鈀,加熱回流12小時,冷卻,用乙酸乙酯萃取三遍,有機相用無水硫酸鈉幹燥,濃縮,粗品用乙醇重結晶,得到固體29 g,產率為92%。
在500 ml的單口燒瓶中,25 g對溴苄溴跟49.8 ml亞磷酸三乙酯(1-2)加熱回流2個小時,除去多余的亞磷酸三乙酯,加入23.4 g中間體1-1和250 ml DMF,在冰浴下,加入16.8 g叔丁醇鉀,升至室溫,攪拌過夜,把反應液倒入蒸餾水裏面,過濾,濾餅用乙醇重結晶,得到31.8 g,產率83%。
在1 L的單口燒瓶中,加入45 g3,5-二苯基苯硼酸和42.5 g對溴碘苯,450 ml二氧六環,150 ml 2M碳酸鉀水溶液,在氮氣保護下,加入1.7 g四三苯基磷鈀,加熱回流12小時,冷卻,用乙酸乙酯萃取三遍,有機相用無水硫酸鈉幹燥,濃縮,粗品用乙醇重結晶,得到固體54.6 g,產率為95%。
在氮氣保護下,把20 g中間體1-4和300 ml THF加入到1 L的三口燒瓶中,冷卻到-78度,滴加21 ml 2.5M的正丁基鋰,在此溫度下,保持2小時,加入16.6 g硼酸三異丙酯,在此溫度下保持1個小時,升至室溫,反應12小時,往反應液加入2N的稀鹽酸,調節到中性,用乙酸乙酯萃取三次,有機相用無水硫酸鈉幹燥,濃縮,粗品用乙酸乙酯和正己烷重結晶,得到固體14 g,產率為78%。
在500 ml的單口燒瓶中,加入20 g中間體1-3和14 g 9-蒽硼酸,350 ml二氧六環,70 ml碳酸鉀水溶液,在氮氣保護下,加入0.6 g四三苯基磷鈀,加熱回流12小時,冷卻,用乙酸乙酯萃取三遍,有機相用無水硫酸鈉幹燥,濃縮,粗品用THF加熱回流,冷卻過濾,得到固體20 g,產率為80%。
在500 ml的單口燒瓶中,加入20 g中間體1-6,10.4 g NBS和400 ml氯仿,
25度下攪拌12小時,除去二氯甲烷,用THF和乙醇重結晶得到17 g,產率73.3%。
在250 ml的單口燒瓶中,加入5.5 g中間體1-5和7.3 g中間體1-7,75 ml二氧六環,20 ml 2M碳酸鉀水溶液,在氮氣保護下,加入0.15 g四三苯基磷鈀,加熱回流12小時,冷卻,用乙酸乙酯萃取三遍,有機相用無水硫酸鈉幹燥,濃縮,粗品用THF加熱回流,冷卻過濾,得到固體7.7 g,產率為75.5%。1H NMR(400 MHz,CD2Cl2,δ):7.99-8.02(m,5 H),7.88-7.95(m,3 H),7.76-7.86(m,12 H),7.38-7.63(m,22 H).MALDI-TOF-MS m/s計算值C62H42:786.3,實測值[M+]:786.5。化合物110的1H NMR如圖2。
在氮氣保護下,把36.3g中間體(2-1)和400 ml THF加入到1L的三口燒瓶中,冷卻到-78度,滴加50 ml 2.5M的正丁基鋰,在此溫度下,保持2
小時,加入30 g硼酸三異丙酯,在此溫度下保持1個小時,升至室溫,反應12小時,往反應液加入2N的稀鹽酸,用乙酸乙酯萃取三次,有機相用無水硫酸鈉幹燥,濃縮,粗品用乙酸乙酯和正己烷重結晶,得到固體27 g,產率為90%。
在500 ml的單口燒瓶中,加入25 g中間體2-2和14.5 g對溴碘苯,300 ml二氧六環,60 ml 2M碳酸鉀水溶液,在氮氣保護下,加入0.6 g四三苯基磷鈀,加熱回流12小時,冷卻,用乙酸乙酯萃取三遍,有機相用無水硫酸鈉幹燥,濃縮,粗品用THF加熱回流,冷卻過濾,得到固體22 g,產率為70%。
在氮氣保護下,把15.5 g中間體2-3和300 ml THF加入到250 ml的三口燒瓶中,冷卻到-78度,滴加17 ml 2.5M的正丁基鋰,在此溫度下,保持2小時,加入10.2 g硼酸三異丙酯,在此溫度下保持1個小時,升至室溫,反應12小時,往反應液加入2N的稀鹽酸,用乙酸乙酯萃取三次,有機相用無水硫酸鈉幹燥,濃縮,粗品用乙酸乙酯和正己烷重結晶,得到固體14 g,產率為90%。
在250 ml的單口燒瓶中,加入7 g中間體2-5和8 g中間體1-7,120 ml二氧六環,24 ml 2M碳酸鉀水溶液,在氮氣保護下,加入0.16g四三苯基磷鈀,加熱回流12小時,冷卻,用乙酸乙酯萃取三遍,有機相用無水硫酸鈉幹燥,濃縮,粗品用THF加熱回流,冷卻過濾,得到固體10g,產率為79%。1H NMR(400 MHz,CD2Cl2,δ):7.98-8.00(d,J=8.4 Hz,2 H),7.94-7.96(d,J=7.6 Hz,2 H),7.89-7.91(d,J=8.0 Hz,2 H),7.76-7.86(m,12 H),7.65-7.67(d,
J=8.4 Hz,2 H),7.48-7.58(m,11 H),7.32-7.43(m,11 H),7.09-7.17(m,6 H)2.32(s,3 H).MALDI-TOF-MS m/s計算值C70H48:888.4,實測值[M+]:888.7。
首先,將透明導電ITO玻璃基板10(上面帶有陽極20)依次經:洗滌劑溶液和去離子水,乙醇,丙酮,去離子水洗淨,再用氧等離子處理30秒,接著用等離子處理的CFx處理。
然後,在ITO上蒸渡5 nm厚的MoO3作為空穴注入層30。
然後,蒸渡P1,形成50 nm厚的空穴傳輸層40。
然後,在空穴傳輸層上蒸渡20 nm厚的化合物110作為發光層50。
然後,在發光層上蒸渡40 nm厚的P2作為電子傳輸層60。
最後,蒸渡1.2 nm LiF為電子注入層70和150 nm Al作為器件陰極80。
所制備的器件在7V的工作電壓下的亮度為980cd/m2,電流效率達到4.3 cd/A,功率效率為2.1 lm/W,發射藍光。
器件中所述結構式
將化合物110,換成化合物122,制作有機電致發光器件。
所制備的器件在7V的工作電壓下的亮度為470 cd/m2,電流效率達到4.6 cd/A,功率效率為1.95 lm/W,發射藍光。
方法同實施例3,將化合物110替換成下列化合物P3,制作對比用有機電致發光器件。
所制備的器件在7V的工作電壓下的亮度為289 cd/m2,電流效率達到2.4 cd/A,功率效率為1.1 lm/W,發射藍光。
實施例3和4是本發明材料的具體應用,所制備的器件,本發明發射藍光,效率和亮度都高于對比例。如上所述,本發明的材料具有高的穩定性,本發明制備的有機電致發光器件具有高的效率和光純度。
Claims (9)
- 一種有機電子材料具有式(I)所述的結構式:
- 根據權利要求1所述的有機電子材料,其中,R1-R8獨立地表示為氫,鹵素,氰基,硝基,C1-C8烷基、C1-C8烷氧基,C2-C8取代或者未取代的烯烷基,C2-C8取代或者未取代的炔烷基,C1-C4烷基取代或未取代的苯基,C1-C4烷基取代或未取代的萘基;Ar1-Ar4獨立地表示C1-C4烷基或者C6-C30芳基取代的苯基,C1-C4烷基或者C6-C30芳基取代的萘基,苯基,萘基,N-芳基(C6-C30)或者C1-C4的烷基取代的哢唑基,二苯並噻吩基,二苯並呋喃基,蒽基,菲基,芘基,苝基,熒蒽基,(9,9-二烷基)芴基,(9,9-二烷基取代或未取代芳基)芴基,9,9-螺芴基。
- 根據權利要求2所述的有機電子材料,其中,R1-R8可以獨立地表示為氫,鹵素,C1-C4的烷基,C1-C4烷基取代或未取代的苯基,C1-C4烷基取代或未取代的萘基;Ar1-Ar4為獨立地表示苯基,甲苯基,叔丁基苯基,萘基,甲基萘,聯苯基,二苯基苯基,萘基苯基,二苯基聯苯基,二芳香胺基苯基,N-苯基哢唑基,(9,9-二烷基)芴基,(9,9-二烷基取代或未取代苯基)芴基,9,9-螺芴基。
- 根據權利要求3所述的有機電子材料,其中,R1,R4,R5,R8,為氫,R2,R3,R6,R7可以獨立表示為氫,氟,甲基,乙基,丙基,異丙基,叔丁基,苯基,萘基;Ar1-Ar4為獨立地表示苯基,甲苯基,萘基,甲基萘,聯苯基,二苯基苯基,萘基苯基,二苯基聯苯基,(9,9-二烷基)芴基,(9,9-二甲基取代或未取代苯基)芴基,9,9-螺芴基。
- 根據權利要求4所述的有機電子材料,其中Ar2,Ar3,Ar4為獨立地表示苯基,萘基,聯苯基,Ar1為苯基,萘基,聯苯基,二苯基苯基,萘基苯基,二苯基聯苯基,(9,9-二烷基)芴基,(9-甲苯基,9’-苯基)芴基,9,9-螺芴基。
- 根據權利要求5所述的有機電子材料,其中:R2,R3,R6,R7為氫,Ar2,Ar3,Ar4為獨立地表示苯基,萘基。
- 根據權利要求2所述的有機電子材料,為下列結構化合物:
- 根據權利要求7所述的有機電子材料,為下列結構化合物,
- 權利要求1-8任一所述有機電子材料在有機電致發光器件,有機太陽能電池,有機薄膜晶體管或有機光感受器領域的應用。
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- 2013-05-26 US US14/404,604 patent/US9905774B2/en active Active
- 2013-05-26 KR KR1020147031149A patent/KR101775519B1/ko active IP Right Grant
- 2013-05-26 WO PCT/CN2013/076236 patent/WO2013178041A1/zh active Application Filing
- 2013-05-29 TW TW102118959A patent/TWI570984B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
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WO2013178041A1 (zh) | 2013-12-05 |
KR101775519B1 (ko) | 2017-09-07 |
KR20150022758A (ko) | 2015-03-04 |
CN103450883A (zh) | 2013-12-18 |
CN103450883B (zh) | 2016-03-02 |
US9905774B2 (en) | 2018-02-27 |
US20150108448A1 (en) | 2015-04-23 |
TWI570984B (zh) | 2017-02-11 |
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