CN102741265A - 杂配卡宾配合物及其在有机电子品中的用途 - Google Patents
杂配卡宾配合物及其在有机电子品中的用途 Download PDFInfo
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- CN102741265A CN102741265A CN2010800594616A CN201080059461A CN102741265A CN 102741265 A CN102741265 A CN 102741265A CN 2010800594616 A CN2010800594616 A CN 2010800594616A CN 201080059461 A CN201080059461 A CN 201080059461A CN 102741265 A CN102741265 A CN 102741265A
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- carbon atom
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- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 title 1
- 239000000463 material Substances 0.000 claims abstract description 107
- 229910052751 metal Inorganic materials 0.000 claims abstract description 31
- 239000002184 metal Substances 0.000 claims abstract description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 239000003446 ligand Substances 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 227
- 125000004432 carbon atom Chemical group C* 0.000 claims description 224
- 229910052739 hydrogen Inorganic materials 0.000 claims description 188
- 125000003118 aryl group Chemical group 0.000 claims description 183
- 125000001072 heteroaryl group Chemical group 0.000 claims description 110
- 150000001875 compounds Chemical class 0.000 claims description 101
- -1 carbazyl Chemical group 0.000 claims description 98
- 125000005842 heteroatom Chemical group 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- 125000000524 functional group Chemical group 0.000 claims description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 41
- 238000005304 joining Methods 0.000 claims description 40
- 229920006395 saturated elastomer Polymers 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 21
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 16
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 15
- 239000002243 precursor Substances 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 229910052741 iridium Inorganic materials 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 238000012546 transfer Methods 0.000 claims description 10
- 229910052728 basic metal Inorganic materials 0.000 claims description 9
- 150000002460 imidazoles Chemical class 0.000 claims description 9
- 150000003818 basic metals Chemical class 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 8
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 claims description 6
- 238000005286 illumination Methods 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 abstract description 3
- LUEYUHCBBXWTQT-UHFFFAOYSA-N 4-phenyl-2h-triazole Chemical group C1=NNN=C1C1=CC=CC=C1 LUEYUHCBBXWTQT-UHFFFAOYSA-N 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 112
- 239000002585 base Substances 0.000 description 74
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000460 chlorine Substances 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 20
- 239000004926 polymethyl methacrylate Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 229910052801 chlorine Inorganic materials 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 230000005540 biological transmission Effects 0.000 description 16
- 238000001035 drying Methods 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 238000006862 quantum yield reaction Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 0 CC1C(C=CC(C)(CC2=C*2)C=C2)=C2C2=C[*@](C=CN(C3)*3=N)C=CC=C2CC1 Chemical compound CC1C(C=CC(C)(CC2=C*2)C=C2)=C2C2=C[*@](C=CN(C3)*3=N)C=CC=C2CC1 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229910003849 O-Si Inorganic materials 0.000 description 10
- 229910003872 O—Si Inorganic materials 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000011532 electronic conductor Substances 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical group C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000003852 triazoles Chemical class 0.000 description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
- KJLPWIOVCYTBQS-UHFFFAOYSA-N [NH+]1=CNC=C1.I(=O)(=O)[O-] Chemical class [NH+]1=CNC=C1.I(=O)(=O)[O-] KJLPWIOVCYTBQS-UHFFFAOYSA-N 0.000 description 5
- 239000002981 blocking agent Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
- OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000002577 pseudohalo group Chemical group 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 101100257127 Caenorhabditis elegans sma-2 gene Proteins 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 3
- 150000003851 azoles Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 150000005053 phenanthridines Chemical class 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 238000012982 x-ray structure analysis Methods 0.000 description 3
- SCZGZDLUGUYLRV-UHFFFAOYSA-N (2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NN SCZGZDLUGUYLRV-UHFFFAOYSA-N 0.000 description 2
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 2
- OQJQPIWVCBJVAZ-UHFFFAOYSA-N 1-methyl-2-phenylimidazole Chemical class CN1C=CN=C1C1=CC=CC=C1 OQJQPIWVCBJVAZ-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 101100257133 Caenorhabditis elegans sma-3 gene Proteins 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910052772 Samarium Inorganic materials 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 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 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
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- 238000010537 deprotonation reaction Methods 0.000 description 2
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
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- 239000000284 extract Substances 0.000 description 2
- 230000001815 facial effect Effects 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- DFOLZSTWYAQVDC-UHFFFAOYSA-N phthalic acid;potassium Chemical compound [K].[K].OC(=O)C1=CC=CC=C1C(O)=O DFOLZSTWYAQVDC-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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
- 150000003053 piperidines Chemical class 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical compound N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Images
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- High Energy & Nuclear Physics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Nr. | R70 | R71 | R72 | R87 | R88 | R89 | U |
303 | 甲基 | R86 | R86 | 甲基 | R5 | R86 | -CH2- |
304 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -CH2- |
305 | R86 | R86 | R86 | R86 | R86 | R86 | -CH2- |
306 | 甲基 | R86 | R86 | 甲基 | R5 | R86 | -C2H4- |
307 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -C2H4- |
308 | R86 | R86 | R86 | R86 | R86 | R86 | -C2H4- |
309 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -C3H6- |
310 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -C3H6- |
311 | R86 | R86 | R86 | R86 | R86 | R86 | -C3H6- |
312 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -C4H8- |
313 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -C4H8- |
314 | R86 | R86 | R86 | R86 | R86 | R86 | -C4H8- |
315 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -C6H12- |
316 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -C6H12- |
317 | R86 | R86 | R86 | R86 | R86 | R86 | -C6H12- |
318 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -C8H16- |
319 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -C8H16- |
320 | R86 | R86 | R86 | R86 | R86 | R86 | -C8H16- |
321 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -C9H18- |
322 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -C9H18- |
323 | R86 | R86 | R86 | R86 | R86 | R86 | -C9H18- |
324 | R86 | R86 | R86 | R86 | R86 | R86 | -CH(C8H17)CH2- |
325 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -C2H4(CF2)8C2H4- |
326 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -C2H4(CF2)8C2H4- |
327 | R86 | R86 | R86 | R86 | R86 | R86 | -C2H4(CF2)8C2H4- |
328 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -C≡C- |
329 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -C≡C- |
330 | R86 | R86 | R86 | R86 | R86 | R86 | -C≡C- |
331 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -1,4-(CH2)2-苯基-(CH2)2- |
332 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -1,4-(CH2)2-苯基-(CH2)2- |
333 | R86 | R86 | R86 | R86 | R86 | R86 | -1,4-(CH2)2-苯基-(CH2)2- |
334 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -1,3-(CH2)2-苯基-(CH2)2- |
335 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -1,3-(CH2)2-苯基-(CH2)2- |
336 | R86 | R86 | R86 | R86 | R86 | R86 | -1,3-(CH2)2-苯基-(CH2)2- |
337 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -1,4-(CH2)3-苯基-(CH2)3- |
338 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -1,4-(CH2)3-苯基-(CH2)3- |
339 | R86 | R86 | R86 | R86 | R86 | R86 | -1,4-(CH2)3-苯基-(CH2)3- |
340 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -1,3-(CH2)3-苯基-(CH2)3- |
341 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -1,3-(CH2)3-苯基-(CH2)3- |
342 | R86 | R86 | R86 | R86 | R86 | R86 | -1,3-(CH2)3-苯基-(CH2)3- |
343 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -1,4-苯基- |
344 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -1,4-苯基- |
345 | R86 | R86 | R86 | R86 | R86 | R86 | -1,4-苯基- |
346 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -1,3-苯基- |
347 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -1,3-苯基- |
348 | R86 | R86 | R86 | R86 | R86 | R86 | -1,3-苯基- |
28 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -O- |
349 | 甲基 | R86 | R86 | 甲基 | R86 | R86 | -O- |
350 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -O-Si(CH3)2-O- |
351 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -O-Si(CH3)(Ph)-O- |
352 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -O-Si(CH3)2-O-Si(CH3)2-O- |
353 | 甲基 | 甲基 | R86 | 甲基 | 甲基 | R86 | -O-Si(CH3)2-O-Si(CH3)2-O-Si(CH3)2-O- |
354 | 甲基 | -OSiMe3 | R86 | 甲基 | -OSiMe3 | R86 | -O- |
355 | 甲基 | 苯基 | R86 | 甲基 | 苯基 | R86 | -O- |
356 | 异丙基 | 异丙基 | R86 | 异丙基 | 异丙基 | R86 | -O- |
357 | 环戊基 | 环戊基 | R86 | 环戊基 | 环戊基 | R86 | -O- |
358 | 苯基 | 苯基 | R86 | 苯基 | 苯基 | R86 | -O- |
359 | 苯基 | R86 | R86 | 苯基 | R86 | R86 | -O- |
360 | R86 | R86 | R86 | R86 | R86 | R86 | -O- |
基体MaX | CIE | 300尼特下的电压,V |
Ma10 | 0.19/0.35 | 3.8 |
Claims (21)
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US25549909P | 2009-10-28 | 2009-10-28 | |
US61/255,499 | 2009-10-28 | ||
PCT/EP2010/066400 WO2011051404A1 (de) | 2009-10-28 | 2010-10-28 | Heteroleptische carben-komplexe und deren verwendung in der organischen elektronik |
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US (4) | US20120205645A1 (zh) |
EP (1) | EP2493906B1 (zh) |
JP (1) | JP5939984B2 (zh) |
KR (2) | KR101837095B1 (zh) |
CN (1) | CN102741265B (zh) |
WO (1) | WO2011051404A1 (zh) |
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CN108586539B (zh) * | 2018-04-13 | 2020-06-05 | 苏州科技大学 | 含二苯并噻吩环金属铱配合物及其作为有机电致发光器件发光层掺杂材料的应用 |
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US20200373503A1 (en) | 2020-11-26 |
US20240130221A1 (en) | 2024-04-18 |
US20220144869A1 (en) | 2022-05-12 |
JP5939984B2 (ja) | 2016-06-29 |
WO2011051404A1 (de) | 2011-05-05 |
KR20120096493A (ko) | 2012-08-30 |
EP2493906B1 (de) | 2015-10-21 |
KR101986469B1 (ko) | 2019-06-05 |
US20120205645A1 (en) | 2012-08-16 |
KR20180026583A (ko) | 2018-03-12 |
EP2493906A1 (de) | 2012-09-05 |
US11871654B2 (en) | 2024-01-09 |
CN102741265B (zh) | 2015-12-09 |
US11189806B2 (en) | 2021-11-30 |
JP2013509380A (ja) | 2013-03-14 |
KR101837095B1 (ko) | 2018-03-09 |
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