CN101421862B - 作为有机半导体的醌型体系 - Google Patents
作为有机半导体的醌型体系 Download PDFInfo
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- CN101421862B CN101421862B CN200780013179.2A CN200780013179A CN101421862B CN 101421862 B CN101421862 B CN 101421862B CN 200780013179 A CN200780013179 A CN 200780013179A CN 101421862 B CN101421862 B CN 101421862B
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- Prior art keywords
- unsubstituted
- alkyl
- replaces
- compound
- phenyl
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- 239000004065 semiconductor Substances 0.000 title claims description 71
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 32
- 125000003118 aryl group Chemical group 0.000 claims abstract description 29
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 25
- 230000005669 field effect Effects 0.000 claims abstract description 22
- 239000010409 thin film Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 tetralyl Chemical group 0.000 claims description 104
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000001624 naphthyl group Chemical group 0.000 claims description 32
- 150000001721 carbon Chemical group 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- ZVGCGHVMJAECEG-UHFFFAOYSA-N Chinol Natural products COC1=C(O)C(C)=C(C)C(O)=C1OC ZVGCGHVMJAECEG-UHFFFAOYSA-N 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 230000008021 deposition Effects 0.000 claims description 22
- 239000002243 precursor Substances 0.000 claims description 21
- 125000001544 thienyl group Chemical group 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 20
- 239000010408 film Substances 0.000 claims description 19
- 125000005561 phenanthryl group Chemical group 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 17
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 17
- 125000002541 furyl group Chemical group 0.000 claims description 17
- 125000001725 pyrenyl group Chemical group 0.000 claims description 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 17
- 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 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 150000008065 acid anhydrides Chemical class 0.000 claims description 9
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 9
- 150000003949 imides Chemical group 0.000 claims description 9
- 150000002596 lactones Chemical class 0.000 claims description 9
- 229920003026 Acene Polymers 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000009434 installation Methods 0.000 claims 4
- 125000001118 alkylidene group Chemical group 0.000 claims 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 230000003252 repetitive effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 41
- 239000000047 product Substances 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
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- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
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- 238000010438 heat treatment Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 8
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
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- 238000010992 reflux Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 6
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- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
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- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 5
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
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- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
- H10K10/474—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising a multilayered structure
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
- H10K10/474—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising a multilayered structure
- H10K10/476—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising a multilayered structure comprising at least one organic layer and at least one inorganic layer
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- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- Spectroscopy & Molecular Physics (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
T[℃] | μ[cm2/Vs] | VON[V] | Vt[V] | loff[A] | lon/loff |
030457590 | 8.5×10-38.7×10-36.4×10-32.2×10-39.5×10-4 | -0.6+1.8+2.3-0.2+0.9 | -4.5-1.4-3.2-1.7-0.9 | 1×10-115×10-105×10-111×10-111×10-11 | 5×1045×1031×1041×1045×103 |
样品 | μ[cm2/Vs] | VON[V] | Vt[V] | loff[A] | lon/loff |
具有OTS无OTS(参考样品) | 1.0×10-22.0×10-5 | -0.5-12.6 | -4~-12 | <5×10-121×10-12 | 1×1065×102 |
Claims (21)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06112585 | 2006-04-13 | ||
EP06112585.2 | 2006-04-13 | ||
PCT/EP2007/053314 WO2007118799A1 (en) | 2006-04-13 | 2007-04-04 | Quinoid systems as organic semiconductors |
Publications (2)
Publication Number | Publication Date |
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CN101421862A CN101421862A (zh) | 2009-04-29 |
CN101421862B true CN101421862B (zh) | 2013-01-02 |
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CN200780013179.2A Active CN101421862B (zh) | 2006-04-13 | 2007-04-04 | 作为有机半导体的醌型体系 |
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US (1) | US8471019B2 (zh) |
EP (1) | EP2005497B1 (zh) |
JP (1) | JP5275218B2 (zh) |
CN (1) | CN101421862B (zh) |
TW (1) | TWI451609B (zh) |
WO (1) | WO2007118799A1 (zh) |
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US7781076B2 (en) | 2007-06-26 | 2010-08-24 | Eastman Kodak Company | Heteropyrene-based semiconductor materials for electronic devices and methods of making the same |
KR101810352B1 (ko) | 2008-07-18 | 2017-12-19 | 유디씨 아일랜드 리미티드 | 전자 용품을 위한 아자피렌 |
DE102008061843B4 (de) * | 2008-12-15 | 2018-01-18 | Novaled Gmbh | Heterocyclische Verbindungen und deren Verwendung in elektronischen und optoelektronischen Bauelementen |
US8283659B2 (en) * | 2010-12-23 | 2012-10-09 | Xerox Corporation | Tetrahydrotetraazapentacenes in thin-film transistors |
EP2873300B1 (en) * | 2012-07-13 | 2019-05-01 | Merck Patent GmbH | Organic electronic device comprising an organic semiconductor formulation |
JP6184234B2 (ja) * | 2013-08-02 | 2017-08-23 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料 |
WO2016072455A1 (ja) * | 2014-11-07 | 2016-05-12 | 富士フイルム株式会社 | 有機半導体素子及び化合物 |
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US5028643A (en) * | 1989-06-27 | 1991-07-02 | Ciba-Geigy Corporation | Tetrabenzodiazadiketoperylene pigment |
JP2000231987A (ja) * | 1999-02-10 | 2000-08-22 | Fujitsu Ltd | 有機エレクトロルミネッセンス素子及びそれを使用した表示装置 |
JP4171170B2 (ja) * | 2000-10-17 | 2008-10-22 | 富士フイルム株式会社 | 有機エレクトロルミネッセンス素子及びそれを使用した表示装置 |
DE10109333C1 (de) * | 2001-02-27 | 2002-11-21 | Siemens Ag | Hochkondensierte Borkomplexverbindungen, Herstellungsverfahren und Verwendung dazu |
JP2005250435A (ja) * | 2004-02-04 | 2005-09-15 | Mitsubishi Chemicals Corp | 近赤外線吸収フィルター |
WO2006120143A1 (en) * | 2005-05-13 | 2006-11-16 | Ciba Specialty Chemicals Holding Inc. | Azaperylenes as organic semiconductors |
-
2007
- 2007-04-04 JP JP2009504695A patent/JP5275218B2/ja active Active
- 2007-04-04 US US12/226,182 patent/US8471019B2/en active Active
- 2007-04-04 WO PCT/EP2007/053314 patent/WO2007118799A1/en active Application Filing
- 2007-04-04 CN CN200780013179.2A patent/CN101421862B/zh active Active
- 2007-04-04 EP EP07727784.6A patent/EP2005497B1/en active Active
- 2007-04-11 TW TW096112639A patent/TWI451609B/zh active
Also Published As
Publication number | Publication date |
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EP2005497B1 (en) | 2014-10-08 |
TWI451609B (zh) | 2014-09-01 |
WO2007118799A1 (en) | 2007-10-25 |
TW200810165A (en) | 2008-02-16 |
CN101421862A (zh) | 2009-04-29 |
EP2005497A1 (en) | 2008-12-24 |
JP2009533852A (ja) | 2009-09-17 |
JP5275218B2 (ja) | 2013-08-28 |
US8471019B2 (en) | 2013-06-25 |
US20090261321A1 (en) | 2009-10-22 |
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