WO2010107244A2 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
- Publication number
- WO2010107244A2 WO2010107244A2 PCT/KR2010/001647 KR2010001647W WO2010107244A2 WO 2010107244 A2 WO2010107244 A2 WO 2010107244A2 KR 2010001647 W KR2010001647 W KR 2010001647W WO 2010107244 A2 WO2010107244 A2 WO 2010107244A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- organic electroluminescent
- compound
- alkyl
- mmol
- mono
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 162
- 239000000126 substance Substances 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 239000010410 layer Substances 0.000 claims description 15
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 13
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 13
- -1 amine compound Chemical class 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 7
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 6
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 5
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 4
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 4
- 125000006820 (C1-C60) alkylthio group Chemical group 0.000 claims description 4
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 4
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 37
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 0 Cc1ccc(*c2c-3nnnn2)c-3c1C(*=NN)=C(*)* Chemical compound Cc1ccc(*c2c-3nnnn2)c-3c1C(*=NN)=C(*)* 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 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 4
- 239000003960 organic solvent Substances 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011369 resultant mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 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 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- JKATVFUXWHHCFA-UHFFFAOYSA-N 1,4-dibromo-2,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=C(Br)C=CC(Br)=C1[N+]([O-])=O JKATVFUXWHHCFA-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- JNGKNTZYAKKNLQ-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1h-triazine Chemical compound N=1N(Cl)NC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 JNGKNTZYAKKNLQ-UHFFFAOYSA-N 0.000 description 1
- FRNLBIWVMVNNAZ-UHFFFAOYSA-N 2-iodonaphthalene Chemical compound C1=CC=CC2=CC(I)=CC=C21 FRNLBIWVMVNNAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- KOAYJGBVKMFCPY-UHFFFAOYSA-N 3-chloro-1,5-diphenyl-2h-pyridine Chemical compound C1C(Cl)=CC(C=2C=CC=CC=2)=CN1C1=CC=CC=C1 KOAYJGBVKMFCPY-UHFFFAOYSA-N 0.000 description 1
- KUBSCXXKQGDPPD-UHFFFAOYSA-N Brc(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 Chemical compound Brc(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 1
- JHPAYDLFJOQCBT-UHFFFAOYSA-N C(C1)C=CC=C1c1nc(-c2ccccc2)nc(-[n]2c(c(c3ccccc33)c(cc4)[n]3-c3ccccc3)c4c3ncccc23)n1 Chemical compound C(C1)C=CC=C1c1nc(-c2ccccc2)nc(-[n]2c(c(c3ccccc33)c(cc4)[n]3-c3ccccc3)c4c3ncccc23)n1 JHPAYDLFJOQCBT-UHFFFAOYSA-N 0.000 description 1
- WEZITOJAOYJYLO-UHFFFAOYSA-N CC(c1ccccc1)/N=C(/c1ccccc1)\N=C(/N)\[n]1c2cc(N(C3C=CC=CC33)c4ccccc4)c3cc2c2ncccc12 Chemical compound CC(c1ccccc1)/N=C(/c1ccccc1)\N=C(/N)\[n]1c2cc(N(C3C=CC=CC33)c4ccccc4)c3cc2c2ncccc12 WEZITOJAOYJYLO-UHFFFAOYSA-N 0.000 description 1
- KAUZKVFNGDSDHL-UHFFFAOYSA-N CC1(C=C2c(nccc3)c3NC2=CC11)c2ccccc2N1c1ccccc1 Chemical compound CC1(C=C2c(nccc3)c3NC2=CC11)c2ccccc2N1c1ccccc1 KAUZKVFNGDSDHL-UHFFFAOYSA-N 0.000 description 1
- WRABSKRHKLGKBY-UHFFFAOYSA-N CC1(C=CC=CC11)c(cccc2)c2N1c1ccccc1 Chemical compound CC1(C=CC=CC11)c(cccc2)c2N1c1ccccc1 WRABSKRHKLGKBY-UHFFFAOYSA-N 0.000 description 1
- DSGFBJIKYSWMPG-UHFFFAOYSA-N C[n](c1c2c3ccccc33)c(c4cc(cccc5)c5cc4cc4)c4c1ccc2[n]3[AlH2] Chemical compound C[n](c1c2c3ccccc33)c(c4cc(cccc5)c5cc4cc4)c4c1ccc2[n]3[AlH2] DSGFBJIKYSWMPG-UHFFFAOYSA-N 0.000 description 1
- KWBXMKFBLPHVQL-UHFFFAOYSA-N C[n]1c2c(c3ccccc3[n]3[AlH2])c3ccc2c2c1ccc1cc3ccccc3cc21 Chemical compound C[n]1c2c(c3ccccc3[n]3[AlH2])c3ccc2c2c1ccc1cc3ccccc3cc21 KWBXMKFBLPHVQL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- MSPRXSOJZDDAKD-UHFFFAOYSA-N [O-][N+](c1c(-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)nccc1)=O Chemical compound [O-][N+](c1c(-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)nccc1)=O MSPRXSOJZDDAKD-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- WNTSLQVYCJSQCI-UHFFFAOYSA-N c(cc1)ccc1-[n](c1ccccc11)c(cc2)c1c1c2c2ncccc2[nH]1 Chemical compound c(cc1)ccc1-[n](c1ccccc11)c(cc2)c1c1c2c2ncccc2[nH]1 WNTSLQVYCJSQCI-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- VNICRWVQYFRWDK-UHFFFAOYSA-N naphthalen-2-ylhydrazine Chemical compound C1=CC=CC2=CC(NN)=CC=C21 VNICRWVQYFRWDK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 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 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Definitions
- the present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices comprising the same. Specifically, it relates to novel organic electroluminescent compounds employed as electroluminescent material, and organic electroluminescent devices using them as a host.
- OLED organic light-emitting diode
- electroluminescent material The most important factor to determine luminous efficiency of an OLED (organic light-emitting diode) is the type of electroluminescent material. Though fluorescent materials has been widely used as an electroluminescent material up to the present, development of phosphorescent materials is one of the best methods to improve the luminous efficiency theoretically up to four(4) times, in view of electroluminescent mechanism.
- iridium (III) complexes are widely known as phosphorescent material, including (acac)Ir(btp) 2 , Ir(ppy) 3 and Firpic, as the red, green and blue one, respectively.
- phosphorescent material including (acac)Ir(btp) 2 , Ir(ppy) 3 and Firpic, as the red, green and blue one, respectively.
- a lot of phosphorescent materials have been recently investigated in Japan, Europe and America.
- CBP 4,4'-N,N'-dicarbazole-biphenyl
- the materials in prior art are advantageous in view of light emitting property, they have low glass transition temperature and very poor thermal stability, so that the materials tend to be changed during the process vapor-deposition in vacuo at high temperature.
- power efficiency ( ⁇ /voltage) x current efficiency.
- the power efficiency is inversely proportional to the voltage, and the power efficiency should be higher in order to obtain lower power consumption of an OLED.
- an OLED employing phosphorescent electroluminescent material shows significantly higher current efficiency (cd/A) than an OLED employing fluorescent EL material.
- the present inventors endeavored to overcome the problems of conventional techniques, and consequently invented novel electroluminescent compounds to realize organic electroluminescent devices having excellent luminous efficiency and remarkably lengthened device life.
- the object of the invention is to overcome those problems and to provide organic electroluminescent compounds comprising a backbone to result in better luminous efficiency, improved device life, and appropriate color coordinate, as compared to conventional host materials.
- Another object of the invention is to provide organic electroluminescent devices having high efficiency and long life, which employ such organic electroluminescent compounds as electroluminescent material.
- the present invention relates to organic electroluminescent compounds represented by one of Chemical Formulas (1) to (5), and organic electroluminescent devices comprising the same. Since the organic electroluminescent compounds according to the present invention provide better luminous efficiency and excellent life property as compared to conventional host material, OLED's having excellent operation life can be obtained therefrom.
- X and Y are independently selected from N(Ar 1 ), O and S, wherein Ar 1 may be different from one another, and Ar 1 may be represented as Ar 1 or Ar 2 where there are two or more Ar 1 groups;
- Z 1 through Z 8 are independently selected from C(Ar 3 ) and N, wherein Ar 3 may be different from one another, and adjacent Ar 3 groups may be linked together to form a ring;
- Ar 1 and Ar 2 are independently selected from (C1-C60)alkyl, (C3-C60)cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O, S, Si and P, (C7-C60)bicycloalkyl, adamantyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C6-C60)aryl and (C3-C60)heteroaryl;
- Ar 3 are independently selected from hydrogen, (C1-C60)alkyl, halogen, cyano, (C3-C60)cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O, S, Si and P, (C7-C60)bicycloalkyl, adamantyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C6-C60)aryl, (C1-C60)alkoxy, (C6-C60)aryloxy, (C3-C60)heteroaryl, (C6-C60)arylthio, (C1-C60)alkylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)
- alkyl, cycloalkyl, heterocycloalkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl, triarylsilyl, arylboranyl or alkylboranyl of Ar 1 through Ar 3 may be further substituted by one or more substituent(s) selected from a group consisting of (C1-C60)alkyl, halogen, cyano, (C3-C60)cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O, S, Si and P, (C7-C60)bicycloalkyl, adamantyl, (C2-C60)alkenyl, (C2-C60)alkyn
- the substituents, as described here, which comprises "(C1-C60)alkyl” moiety may contain from 1 to 60 carbon atoms, from 1 to 20 carbon atoms, or from 1 to 10 carbon atoms.
- the substituents comprising "(C6-C60)aryl” moiety may contain from 6 to 60 carbon atoms, from 6 to 20 carbon atoms, or from 6 to 12 carbon atoms.
- Those comprising "(C3-C60)heteroaryl” moiety may contain from 3 to 60 carbon atoms, from 4 to 20 carbon atoms, or from 4 to 12 carbon atoms.
- Those comprising "(C3-C60)cycloalkyl” moiety may contain from 3 to 60 carbon atoms, from 3 to 20 carbon atoms, or from 3 to 7 carbon atoms.
- the substituents comprising "(C2-C60)alkenyl or alkynyl” moiety may contain from 2 to 60 carbon atoms, from 2 to 20 carbon atoms, or from 2 to 10 carbon atoms.
- alkyl' of the present invention include linear or branched saturated monovalent hydrocarbon radicals or combinations thereof, which are composed only of carbon atoms and hydrogen atoms.
- 'alkoxy' means -O-alkyl group, in which alkyl is defined as above.
- aryl represents an organic radical derived from aromatic hydrocarbon by deleting one hydrogen atom therefrom.
- Aryl groups include monocyclic and fused ring system, each ring of which suitably contains from 4 to 7, preferably from 5 or 6 cyclic atoms. Structures wherein two or more aryl groups are combined through chemical bond(s) are also included. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphtacenyl, fluoranthenyl and the like, but are not restricted thereto.
- heteroaryl means an aryl group containing from 1 to 4 heteroatom(s) selected from N, O and S for the aromatic cyclic backbone atoms, and carbon atom(s) for remaining aromatic cyclic backbone atoms.
- the heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated.
- the structures having one or more heteroaryl groups bonded through chemical bond(s) are also included.
- the heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like.
- monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuryl, benzothienyl, isobenzofuryl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cin
- organic electroluminescent compounds according to the invention can be exemplified by the compounds represented by one of the following chemical formulas:
- Ar 1 and Ar 2 are defined as in Chemical Formulas (1) to (5).
- organic electroluminescent compounds according to the present invention can be exemplified by the compounds represented by one of the following chemical formulas:
- Ar 1 and Ar 2 are defined as in Chemical Formulas (1) to (5).
- organic electroluminescent compounds according to the present invention can be specifically exemplified by the compounds represented by one of the following chemical formulas:
- Ar 1 is defined as in Chemical Formulas (1) to (5).
- Ar 1 and Ar 2 independently represent phenyl, 1-naphthyl or 2-naphthyl, or a substituent represented by one of the following chemical formulas, but they are not restricted thereto.
- the present invention also provides an organic electroluminescent device which is comprised of a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode; wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by one of Chemical Formulas (1) to (5).
- the organic electroluminescent device is characterized in that the organic layer comprises an electroluminescent layer, which comprises one or more compound(s) represented by one of Chemical Formulas (1) to (5) as electroluminescent host, and one or more phosphorescent dopant(s).
- the dopant is not particularly restricted.
- the organic electroluminescent device according to the invention may further comprise one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, as well as one or more organic electroluminescent compound(s) represented by one of Chemical Formulas (1) to (5).
- the organic layer may further comprise one or more metal(s) selected from a group consisting of organic metals of Group 1, Group 2, 4 th period and 5 th period transition metals, lanthanide metals and d-transition elements, or complex(es) thereof, as well as one or more organic electroluminescent compound(s) represented by one of Chemical Formulas (1) to (5).
- the organic layer may comprise an electroluminescent layer and a charge generating layer.
- the organic electroluminescent device may also comprise one or more organic electroluminescent layer(s) emitting blue, green or red light, in addition to the organic electroluminescent compound(s) as described above, to form an organic electroluminescent device emitting white light.
- organic electroluminescent compounds according to the invention exhibit excellent luminous efficiency and very good life property of material when they are employed as host material of organic electroluminescent material of an OLED, so that OLED's having very good operation life can be manufactured therefrom.
- Compound (A-6) (7 g, 12.33 mmol) was mixed with triethylphosphite (100 mL), and the same procedure as for synthesis of Compound (A-2) was carried out to give Compound (A-7) (4 g, 7.46 mmol, 58.33%).
- Organic electroluminescent compounds (TA, TB and TC) were prepared according to the procedures of Preparation Examples (1)-(6).
- the substituents (Ar 1 , Ar 2 ) of those organic electroluminescent compounds thus prepared, and 1 H NMR and MS/FAB data of the compounds are listed in Tables 1 and 2.
- OLED devices were manufactured by using the electroluminescent compounds according to the invention.
- a transparent electrode ITO thin film (15 ⁇ / ⁇ ) prepared from glass for OLED (produced by Samsung-Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
- an ITO substrate was equipped in a substrate folder of a vacuum vapor-deposit device, and 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)(of which the chemical structure is shown below) was placed in a cell of the vacuum vapor-deposit device, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Electric current was applied to the cell to evaporate 2-TNATA, thereby providing vapor-deposit of a hole injection layer having 60 nm of thickness on the ITO substrate.
- 2-TNATA 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
- NPB N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine
- a compound according to the present invention which had been purified via vacuum sublimation under 10 -6 torr (for example, Compound TA8-H4-H2), and an electroluminescent dopant (for example, compound (piq) 2 Ir(acac)) to another cell, respectively.
- the two materials were evaporated at different rates to carry out doping in a concentration from 4 to 10 mol%, thereby vapor-depositing an electroluminescent layer having 30 nm of thickness on the hole transport layer.
- tris(8-hydroxyquinoline)aluminum (III) (Alq) [of which the structure is shown below] was vapor-deposited as an electron transport layer with a thickness of 20 nm, and lithium quinolate (Liq) was vapor-deposited as an electron injection layer with a thickness of 1 to 2 nm. Thereafter, an Al cathode was vapor-deposited with a thickness of 150 nm by using another vacuum vapor-deposit device to manufacture an OLED.
- OLED's were manufactured according to the same procedure as for OLED s of Examples 1 to 10, but using compounds according to the present invention (for example: Compound TA4-H4-H4) as host material, and organic iridium complex (Ir(ppy) 3 ) represented by the chemical formula below as electroluminescent dopant.
- compounds according to the present invention for example: Compound TA4-H4-H4
- organic iridium complex Ir(ppy) 3
- OLED's were manufactured according to the same procedure described in Examples 1 and 11, but another cell of the vacuum vapor-deposition device was charged with bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum (III) (BAlq), instead of the electroluminescent compound according to the invention, as host material.
- BAlq bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum (III)
- the organic electroluminescent compounds developed by the present invention exhibited superior properties in terms of device performances as compared to conventional materials.
- the compounds developed by the present invention showed excellent properties in terms of luminescent properties as compared to the conventional materials.
- the devices manufactured according to the present invention showed excellent current properties as compared to the device of Comparative Example 1 which was manufactured with conventional material, thereby providing operation voltage lowered by 1 V or more. They also showed higher current efficiency properties of at least 1.4 folds as compared to the device of Comparative Example 1, due to the remarkably improved luminous properties.
- the device when the compounds developed by the present invention were used as host for green electroluminescence, the device showed, due to their excellent luminous properties, far higher power efficiency of at least 1.6 folds as compared to the device of Comparative Example 2. Excellent luminous properties were confirmed as compared to the conventional materials. Particularly, the device of Example 14 was operated at a lower voltage by 2.7 V as compared to that of Comparative Example 1, and the device of Example 17 showed 5.5 V of operation voltage and 15.9 lm/W of power efficiency at 1000 cd/m 2 .
- the devices employing the electroluminescent compounds according to the present invention as host material for emitting red or green light exhibited excellent luminous properties, with lowering the operation voltage, so that the device for emitting green light, in particular, induces increase of power efficiency by 5.1 to 7.7 lm/W to result in improvement in power consumption.
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Abstract
Description
Claims (10)
- An organic electroluminescent compound represented by one of Chemical Formulas 1 to 5:[Chemical Formula 1][Chemical Formula 2][Chemical Formula 3][Chemical Formula 4][Chemical Formula 5]wherein,X and Y are independently selected from N(Ar1), O and S, wherein Ar1 may be different from one another, and Ar1 may be represented as Ar1 or Ar2 where there are two or more Ar1 groups;Z1 through Z8 are independently selected from C(Ar3) and N, wherein Ar3 may be different from one another, and adjacent Ar3 groups may be linked together to form a ring;Ar1 and Ar2 are independently selected from (C1-C60)alkyl, (C3-C60)cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O, S, Si and P, (C7-C60)bicycloalkyl, adamantyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C6-C60)aryl and (C3-C60)heteroaryl;Ar3 are independently selected from hydrogen, (C1-C60)alkyl, halogen, cyano, (C3-C60)cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O, S, Si and P, (C7-C60)bicycloalkyl, adamantyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C6-C60)aryl, (C1-C60)alkoxy, (C6-C60)aryloxy, (C3-C60)heteroaryl, (C6-C60)arylthio, (C1-C60)alkylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, mono- or di(C6-C30)arylboranyl, mono- or di(C1-C60)alkylboranyl, nitro and hydroxyl; andthe alkyl, cycloalkyl, heterocycloalkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl, triarylsilyl, arylboranyl or alkylboranyl of Ar1 through Ar3 may be further substituted by one or more substituent(s) selected from a group consisting of (C1-C60)alkyl, halogen, cyano, (C3-C60)cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O, S, Si and P, (C7-C60)bicycloalkyl, adamantyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C6-C60)aryl, (C1-C60)alkoxy, (C6-C60)aryloxy, (C6-C60)aryl substituted by P(=O)RaRb [Ra and Rb independently represent (C1-C60)alkyl or (C6-C60)aryl], (C3-C60)heteroaryl, (C3-C60)heteroaryl subsitituted by (C6-C60)aryl, (C3-C60)heteroaryl substituted by (C1-C60)alkyl, (C6-C60)ar(C1-C60)alkyl, (C6-C60)arylthio, (C1-C60)alkylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, mono- or di(C6-C30)arylboranyl, mono- or di(C1-C60)alkylboranyl, nitro and hydroxyl,excluding the case where both X and Y are N(Ar1) and all of Z1 through Z8 are C(Ar3).
- An organic electroluminescent device comprising the organic electroluminescent compound according to any one of claims 1 to 4.
- The organic electroluminescent device according to claim 5, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) according to any one of claims 1 to 4 and one or more phosphorescent dopant(s).
- The organic electroluminescent device according to claim 6, wherein the organic layer further comprises one or more amine compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds.
- The organic electroluminescent device according to claim 6, wherein the organic layer further comprises one or more metal(s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements, or complex(es) formed therefrom.
- The organic electroluminescent device according to claim 6, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
- The organic electroluminescent device according to claim 6, which is a white light-emitting organic electroluminescent device wherein the organic layer simultaneously comprises one or more organic electroluminescent layer(s) emitting blue, red or green light.
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JP6073933B2 (en) | 2017-02-01 |
JP2012520872A (en) | 2012-09-10 |
KR101511072B1 (en) | 2015-04-10 |
CN105294712A (en) | 2016-02-03 |
WO2010107244A3 (en) | 2010-12-09 |
JP6153976B2 (en) | 2017-06-28 |
CN103555322B (en) | 2016-08-17 |
CN105176523B (en) | 2017-10-10 |
JP2017008061A (en) | 2017-01-12 |
JP2015122508A (en) | 2015-07-02 |
CN102482571A (en) | 2012-05-30 |
CN103524510B (en) | 2016-02-10 |
CN103641830A (en) | 2014-03-19 |
CN105176523A (en) | 2015-12-23 |
KR20100105099A (en) | 2010-09-29 |
CN103641831A (en) | 2014-03-19 |
JP6356183B2 (en) | 2018-07-11 |
CN103641830B (en) | 2017-04-12 |
JP6114763B2 (en) | 2017-04-12 |
CN105001224A (en) | 2015-10-28 |
JP2016001749A (en) | 2016-01-07 |
CN103555322A (en) | 2014-02-05 |
CN103641832A (en) | 2014-03-19 |
JP2015120702A (en) | 2015-07-02 |
CN103524510A (en) | 2014-01-22 |
TW201105768A (en) | 2011-02-16 |
TW201522570A (en) | 2015-06-16 |
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