JP2009504860A - 固有導電性ポリマーを含む組成物 - Google Patents
固有導電性ポリマーを含む組成物 Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 229920001940 conductive polymer Polymers 0.000 title claims abstract description 40
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims abstract description 41
- 229910052738 indium Inorganic materials 0.000 claims abstract description 38
- 229920000767 polyaniline Polymers 0.000 claims abstract description 32
- 238000002347 injection Methods 0.000 claims abstract description 18
- 239000007924 injection Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- 229920000128 polypyrrole Polymers 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 229920000123 polythiophene Polymers 0.000 claims abstract description 8
- 239000000843 powder Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000002472 indium compounds Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000002471 indium Chemical class 0.000 claims description 6
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 6
- 229940005642 polystyrene sulfonic acid Drugs 0.000 claims description 6
- 229910000337 indium(III) sulfate Inorganic materials 0.000 claims description 3
- XGCKLPDYTQRDTR-UHFFFAOYSA-H indium(iii) sulfate Chemical compound [In+3].[In+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O XGCKLPDYTQRDTR-UHFFFAOYSA-H 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 5
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ODPYDILFQYARBK-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2SC2=C1 ODPYDILFQYARBK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 239000002322 conducting polymer Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- -1 iodine, peroxide Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920001197 polyacetylene Polymers 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 206010027146 Melanoderma Diseases 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HTMLHMOPVRAFNY-UHFFFAOYSA-L S(=O)(=O)([O-])[O-].[In+2] Chemical compound S(=O)(=O)([O-])[O-].[In+2] HTMLHMOPVRAFNY-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003545 alkoxy group Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001449 indium ion Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000015 polydiacetylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- 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]
- H10K50/17—Carrier injection layers
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Electroluminescent Light Sources (AREA)
- Conductive Materials (AREA)
Abstract
Description
初めに、ポリアニリン粉末を、EP329 768に記載の工程に従って調製した。脱イオン水4190g中ポリスチレンスルホン酸(PSSH)30%溶液とアニリン89mlの1010gを二重壁の反応装置に注入し、本溶剤を低温保持装置および冷媒によって1℃まで冷却することによって、PANI/PSSH(単量体とスルホン酸基の割合は、1:1.5)を生成した。脱イオン水420ml中280gのペルオキソ二硫酸アンモニウム(APS)の溶剤を、温度が5℃を上回らないように徐々に本溶剤に滴下した。得られた固体を、アセトンで沈殿させ、濾過し、アセトンで洗浄し、乾燥させた。
実施例1と類似の方法で、脱イオン水48.6ml中PSSH73.9g、アニリン7.44ml、および硫酸インジウム(II)16.3gを注入し、APS24gと反応させた。その後、実施例1と同様に仕上げた。
実施例1と類似の方法で、脱イオン水48.6ml中PSSH73.9g、アニリン7.44ml、およびインジウム顆粒944mgを注入し、APS24gと反応させた。さらに仕上げを行う前に、非反応インジウム顆粒残留物を分離した。残留固体を洗浄し、乾燥させると、残渣685mgが残った。
実施例1と同様の方法で、脱イオン水48.6ml中PSSH73.9g、アニリン7.44mlを注入し、APS24gと反応させた。反応が完了すると、インジウム顆粒985mgを反応混合物に添加し、本混合物を22時間撹拌した。さらに仕上げを行う前に、非反応インジウム顆粒残留物を分離した。残留固体を洗浄し、乾燥させると、残渣610mgが残った。
初めに、正確な計測分量を判断することができるように、粉末(実施例1乃至4による)の残留湿度を測定した。その後、粉末16g(実施例1、2、3または4から)を脱イオン水500mlに添加し、Ultraturraxを用いて速度10,000rpmで1.5時間分散させた。
実施例1から得られた粉末の散剤を、実施例5に従って調製した。本散剤は、重量比1:1の硫酸インジウムを含むポリスチレンスルホン酸(PSSH)の30%水溶液を30重量部使用して生成された。
実施例1から得られた粉末の散剤(120g)を、実施例5に従って調製した。インジウム顆粒650mgを、本散剤に添加し、その散剤を72時間撹拌した。その後、黒色帯域フィルタで濾過した。フィルタに残留したインジウムを、脱イオン水で洗浄し、乾燥させた。インジウム563mgが残った。従って、本散剤には、散剤1グラム当たりインジウム0.72mgが含まれた。
実施例1から得られた粉末の散剤(100g)を、実施例5に従って調製した。水中(Liquion Solution LQ‐1115、110EW)で15%のペルフルオロスルホン酸co‐テトラフルオロエチレン溶液20gを、本散剤に添加し、その散剤を20分間撹拌した。その後、得られた散剤を、実施例7のようにさらに処理した。
本発明に相当する組成物をポリピロールで調製するために、実施例1乃至5および6乃至8を同様に再処理し、(PPy)を、PANIの代わりに固有導電性ポリピロールとして使用した。
相当する組成物をPEDOTで調製するために、実施例6乃至8と同様に仕上げを行い、市販製品Baytron P AI4083の形態のPEDOTを、PANIの代わりに固有導電性重合体として使用した。
Claims (23)
- 少なくとも1つの固有導電性重合体およびインジウムを含む組成物。
- ポリアニリン、ポリチオフェン、ポリピロール、またはそれらの誘導体を固有導電性重合体として含む、請求項1に記載の組成物。
- ポリ(3,4‐エチレンジオキシ‐2,5‐チオフェン)、ポリアニリン、またはポリチエノチオフェンを固有導電性重合体として含む、請求項2に記載の組成物。
- 前記固有導電性重合体をドープ形態で含む、請求項1乃至3のいずれかに記載の組成物。
- 前記固有導電性重合体が、ポリスチレンスルホン酸またはポリフルオロスルホン酸co‐テトラフルオロエチレンでドープされている、請求項4に記載の組成物。
- インジウムを元素形態またはイオン形態で含む、請求項1乃至5のいずれかに記載の組成物。
- インジウム塩、特にインジウムポリスチレンスルホン酸または硫酸インジウムとしてインジウムを含む、請求項6に記載の組成物。
- 混合物、特に溶剤または散剤として存在する、請求項1乃至7のいずれかに記載の組成物。
- 固有導電性重合体およびインジウムの化合物である、請求項1乃至8のいずれかに記載の組成物。
- ポリアニリンおよびインジウムの化合物である、請求項9に記載の組成物。
- 固有導電性重合体が、散剤または溶剤の存在下でインジウムと接触させられる、請求項1乃至10のいずれかに記載の組成物を調製するための工程。
- 固有導電性重合体は、特にドープ形態で、インジウム塩と接触させられる、請求項11に記載の工程。
- 固有導電性重合体は、特にドープ形態で、元素インジウムと接触させられる、請求項11に記載の工程。
- 前記固有導電性重合体は、インジウム化合物または元素インジウムの存在下で調製される、請求項11に記載の工程。
- 前記組成物が分散される、請求項10乃至14のいずれかに記載の工程。
- 請求項11乃至15のいずれかに記載の工程によって得ることが可能な組成物。
- 請求項1乃至10または16のいずれかに記載の組成物を含む、電子装置。
- 発光ダイオードである、請求項17に記載の装置。
- 前記組成物は、前記発光ダイオードの電極間の層に存在する、請求項18に記載の装置。
- 前記組成物は、正孔注入層に存在し、特に該層を形成する、請求項19に記載の装置。
- 請求項1乃至10または16のいずれかに記載の組成物が使用される、電子装置を製造するための工程。
- 電子装置の製造のための、請求項1乃至10または16のいずれかに記載の組成物の使用。
- 前記組成物が、発光ダイオードの電極間の層、特に正孔注入層として使用される、請求項22に記載の使用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005039608A DE102005039608A1 (de) | 2005-08-19 | 2005-08-19 | Zusammensetzung mit intrinsisch leitfähigem Polymer |
PCT/EP2006/008165 WO2007020100A1 (de) | 2005-08-19 | 2006-08-18 | Zusammensetzung mit intrinsisch leitfähigem polymer enthaltend iridium |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2011185115A Division JP5566973B2 (ja) | 2005-08-19 | 2011-08-26 | 固有導電性重合体を含む組成物 |
Publications (2)
Publication Number | Publication Date |
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JP2009504860A true JP2009504860A (ja) | 2009-02-05 |
JP2009504860A5 JP2009504860A5 (ja) | 2011-10-13 |
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Application Number | Title | Priority Date | Filing Date |
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JP2008526450A Withdrawn JP2009504860A (ja) | 2005-08-19 | 2006-08-18 | 固有導電性ポリマーを含む組成物 |
JP2011185115A Expired - Fee Related JP5566973B2 (ja) | 2005-08-19 | 2011-08-26 | 固有導電性重合体を含む組成物 |
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US (1) | US7989533B2 (ja) |
EP (1) | EP1917666B1 (ja) |
JP (2) | JP2009504860A (ja) |
KR (1) | KR20080040005A (ja) |
CN (1) | CN101243523A (ja) |
AT (1) | ATE545937T1 (ja) |
CA (1) | CA2618563A1 (ja) |
DE (1) | DE102005039608A1 (ja) |
WO (1) | WO2007020100A1 (ja) |
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DE102004003784B4 (de) * | 2004-01-23 | 2011-01-13 | Ormecon Gmbh | Dispersion intrinsisch leitfähigen Polyanilins und deren Verwendung |
DE102004030388A1 (de) * | 2004-06-23 | 2006-01-26 | Ormecon Gmbh | Artikel mit einer Beschichtung von elektrisch leitfähigem Polymer und Verfahren zu deren Herstellung |
DE102005010162B4 (de) * | 2005-03-02 | 2007-06-14 | Ormecon Gmbh | Leitfähige Polymere aus Teilchen mit anisotroper Morphologie |
ATE546032T1 (de) * | 2006-09-13 | 2012-03-15 | Enthone | Artikel mit beschichtung aus elektrisch leitendem polymer und edel-/halbedelmetal sowie herstellungsverfahren dafür |
US9053083B2 (en) | 2011-11-04 | 2015-06-09 | Microsoft Technology Licensing, Llc | Interaction between web gadgets and spreadsheets |
WO2014048543A1 (de) | 2012-09-25 | 2014-04-03 | Merck Patent Gmbh | Formulierungen enthaltend leitfähige polymere sowie deren verwendung in organischen, elektronischen vorrichtungen |
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2006
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- 2006-08-18 JP JP2008526450A patent/JP2009504860A/ja not_active Withdrawn
- 2006-08-18 CA CA002618563A patent/CA2618563A1/en not_active Abandoned
- 2006-08-18 US US12/063,642 patent/US7989533B2/en not_active Expired - Fee Related
- 2006-08-18 KR KR1020087006602A patent/KR20080040005A/ko not_active Application Discontinuation
- 2006-08-18 CN CNA2006800297914A patent/CN101243523A/zh active Pending
- 2006-08-18 WO PCT/EP2006/008165 patent/WO2007020100A1/de active Application Filing
- 2006-08-18 AT AT06776958T patent/ATE545937T1/de active
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Also Published As
Publication number | Publication date |
---|---|
CA2618563A1 (en) | 2007-02-22 |
CN101243523A (zh) | 2008-08-13 |
WO2007020100A1 (de) | 2007-02-22 |
JP5566973B2 (ja) | 2014-08-06 |
KR20080040005A (ko) | 2008-05-07 |
DE102005039608A1 (de) | 2007-03-01 |
US20100140592A1 (en) | 2010-06-10 |
JP2011241405A (ja) | 2011-12-01 |
EP1917666B1 (de) | 2012-02-15 |
ATE545937T1 (de) | 2012-03-15 |
US7989533B2 (en) | 2011-08-02 |
EP1917666A1 (de) | 2008-05-07 |
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