JP2007529608A - 高分子酸コロイドおよび水混和性有機液体を含む水分散性ポリジオキシチオフェン - Google Patents
高分子酸コロイドおよび水混和性有機液体を含む水分散性ポリジオキシチオフェン Download PDFInfo
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- JP2007529608A JP2007529608A JP2007504028A JP2007504028A JP2007529608A JP 2007529608 A JP2007529608 A JP 2007529608A JP 2007504028 A JP2007504028 A JP 2007504028A JP 2007504028 A JP2007504028 A JP 2007504028A JP 2007529608 A JP2007529608 A JP 2007529608A
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- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical group [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000594 atomic force spectroscopy Methods 0.000 description 1
- HYGWNUKOUCZBND-UHFFFAOYSA-N azanide Chemical group [NH2-] HYGWNUKOUCZBND-UHFFFAOYSA-N 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical group O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
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- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
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- 238000001312 dry etching Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005672 electromagnetic field Effects 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
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- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 238000007756 gravure coating Methods 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
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- 150000002602 lanthanoids Chemical class 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000001755 magnetron sputter deposition Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002488 metal-organic chemical vapour deposition Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000885 poly(2-vinylpyridine) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920001798 poly[2-(acrylamido)-2-methyl-1-propanesulfonic acid] polymer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000003631 wet chemical etching Methods 0.000 description 1
Images
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Abstract
Description
アノード/バッファ層/EL材料/カソード
ポリジオキシチオフェンと、
コロイド形成性高分子酸と、
水混和性の有機液体と
を含み、
全ポリマーに対する有機液体の重量比が少なくとも0.1である、新規な水性分散液組成物。
(a)水と少なくとも1種のジオキシチオフェンモノマーとの水性混合物を提供する工程、
(b)高分子酸の水性分散液を提供する工程、
(c)ジオキシチオフェン混合物をコロイド形成性高分子酸の水性分散液と組み合わせる工程、
(d)工程(c)の組み合わせの前または後で、酸化剤および触媒を、任意の順序で、コロイド形成性高分子酸の水性分散液と組み合わせる工程、および
(e)少なくとも1種の水混和性の有機液体を加える工程であって、全ポリマーに対する有機液体の重量比が少なくとも約0.1である工程
を含む方法。
ポリジオキシチオフェンと、
コロイド形成性高分子酸と、
水混和性の有機液体と
を含み、
全ポリマーに対する有機液体の重量比が少なくとも0.1である、新規な水性分散液組成物。
(a)水と少なくとも1種のジオキシチオフェンモノマーとの水性混合物を提供する工程、
(b)高分子酸の水性分散液を提供する工程、
(c)ジオキシチオフェン混合物をコロイド形成性高分子酸の水性分散液と組み合わせる工程、
(d)工程(c)の組み合わせの前または後で、酸化剤および触媒を、任意の順序で、少なくとも1種の水混和性の有機液体の添加前にコロイド形成性高分子酸の水性分散液と組み合わせる工程、および
(e)少なくとも1種の水混和性の有機液体を加える工程であって、全ポリマーに対する有機液体の重量比が少なくとも約0.1である工程
を含む方法。
「アルコール」 −R3−OH
「アミドスルホネート」 −R3−C(O)N(R6)R4−SO3Z
「ベンジル」 −CH2−C6H5
「カルボキシレート」 −R3−C(O)O−Z
「エーテル」 −R3−O−R5
「エーテルカルボキシレート」 −R3−O−R4−C(O)O−Z
「エーテルスルホネート」 −R3−O−R4−SO3Z
「スルホネート」 −R3−SO3Z
「ウレタン」 −R3−O−C(O)−N(R6)2
(式中、「R」基はすべて、各出現で同一であるか異なっており、
R3は、一重結合またはアルキレン基であり、
R4は、アルキレン基であり、
R5は、アルキル基であり、
R6は、水素またはアルキル基であり、
Zは、H、アルカリ金属、アルカリ土類金属、N(R5)4またはR5である。)
上記の基はいずれも、さらに未置換であっても置換されていてもよく、どの基も、パーフルオロ基をはじめとして、1つまたは複数の水素で置換されたFを含むものであってもよい。
R1およびR2は各々独立に、水素、少なくとも1個の炭素原子を含むアルキルから選択されるか、
R1およびR2が一緒に、アリール、ヘテロアリール、アルキル、ヘテロアルキル、アルケニル、ヘテロアルケニル、アルコール、アミドスルホネート、ベンジル、カルボキシレート、エーテル、エーテルカルボキシレート、エーテルスルホネート、スルホネート、およびウレタンで任意に置換されていてもよい、少なくとも1個の炭素原子を有するアルキレン鎖を形成し、
nが少なくとも約4である。)
−(O−CF2CFRf)a−O−CF2CFR’fSO3X
(式中、RfおよびR’fは独立に、F、Clまたは1から10個の炭素原子を有する過フッ素化アルキル基から選択され、a=0、1または2であり、Xは、H、Li、Na、KまたはN(R1)(R2)(R3)(R4)であり、R1、R2、R3,およびR4は、同一であるか異なっており、および一実施形態では、H、CH3またはC2H5である。もうひとつの実施形態では、XはHである。上述したように、Xは多価であってもよい。
−O−CF2CF(CF3)−O−CF2CF2SO3X
(式中、Xは先に定義したとおりである。)このタイプのFSAポリマーは、米国特許公報(特許文献3)に開示されており、テトラフルオロエチレン(TFE)と過フッ素化ビニルエーテルCF2=CF−O−CF2CF(CF3)−O−CF2CF2SO2F、パーフルオロ(3,6−ジオキサ−4−メチル−7−オクテンスルホニルフルオリド)(PDMOF)を共重合させた後、スルホニルフルオリド基を加水分解してスルホン酸基に変換し、必要に応じてイオン交換してこれを所望のイオン形態に変換することで製造可能なものである。米国特許公報(特許文献4)および米国特許公報(特許文献5)に開示されているタイプのポリマーの一例は、側鎖−O−CF2CF2SO3X(式中、Xは先に定義したとおりである)を有する。このポリマーは、テトラフルオロエチレン(TFE)と過フッ素化ビニルエーテルCF2=CF−O−CF2CF2SO2F、パーフルオロ(3−オキサ−4−ペンテンスルホニルフルオリド)(POPF)とを共重合させた後、加水分解し、さらに必要に応じてイオン交換することで製造可能なものである。
本実施例は、pH4.1の水性分散液中で重量比(WR)を変えてPEDOT/ナフィオン(登録商標)にジエチレングリコールを加えることと、導電率への影響とについて説明するためのものである。
本実施例は、pH2.0の水性分散液中でWRを変えてジエチレングリコールをPEDT/ナフィオン(登録商標)に加えることと、これが導電率におよぼす影響とについて説明するためのものである。
本実施例は、pH7.0の水性分散液中でWRを変えてジエチレングリコールをPEDOT/ナフィオン(登録商標)に加えることと、これが導電率におよぼす影響とについて説明するためのものである。
本実施例は、2、5、10%(w/w)のN−メチル−2−ピロリジノン(NMP)が、pH約2の水性分散液を用いて得られるPEDOT/ナフィオン(登録商標)膜の導電率に対しておよぼす影響について説明するためのものである。
Claims (23)
- 水と、
ポリジオキシチオフェンと、
コロイド形成性高分子酸と、
水混和性の有機液体と
を含み、
全ポリマーに対する有機液体の重量比が少なくとも0.1であることを特徴とする水性分散液。 - 分散液が約1から8の範囲内のpHを有し、導電性ポリマー、金属粒子、グラファイト繊維、グラファイト粒子、カーボンナノチューブ、炭素ナノ粒子、金属ナノワイヤ、有機導電性インク、有機導電性ペースト、無機導電性インク、無機導電性ペースト、電荷輸送材料、半導電性無機酸化物ナノ粒子、絶縁性無機酸化物ナノ粒子、圧電性酸化物ナノ粒子、圧電性ポリマー、焦電性酸化物ナノ粒子、焦電性ポリマー、強誘電性酸化物ナノ粒子、強誘電性ポリマー、分散助剤、架橋剤、およびそれらの組み合わせから選択される少なくとも1種をさらに含むことを特徴とする請求項1に記載の水性分散液。
- 全ポリマーに対する有機液体の重量比が約0.3から5.0の範囲内であることを特徴とする請求項1に記載の水性分散液。
- 少なくとも1種の有機液体の沸点が100℃を超えることを特徴とする請求項1に記載の水性分散液。
- 有機液体が、N−メチルピロリドン、エチレングリコール、ジメチルアセトアミド、ジメチルホルムアミド、ジメチルスルホキシド、およびそれらの組み合わせから選択されることを特徴とする請求項1に記載の水性分散液。
- 有機液体がジエチレングリコールを含むことを特徴とする請求項1に記載の水性分散液。
- 有機液体がN−メチルピロリドンを含むことを特徴とする請求項1に記載の水性分散液。
- ポリジオキシチオフェンがポリ(3,4−エチレンジオキシチオフェン)を含むことを特徴とする請求項1に記載の水性分散液。
- コロイド形成性高分子酸がパーフルオロアルキレンスルホン酸を含むことを特徴とする請求項1に記載の水性分散液。
- (a)水と少なくとも1種のジオキシチオフェンモノマーとの水性混合物を提供する工程、
(b)少なくとも1種の高分子酸の水性分散液を提供する工程、
(c)ジオキシチオフェン混合物をコロイド形成性高分子酸の水性分散液と組み合わせる工程、
(d)工程(c)の組み合わせの前または後で、酸化剤および触媒を、任意の順序で、コロイド形成性高分子酸の水性分散液と組み合わせて、ポリジオキシチオフェンおよび高分子酸コロイドの水性分散液を形成する工程、および
(e)水混和性の有機液体を加える工程であって、全ポリマーに対する有機液体の重量比が少なくとも約0.1である工程
を含むことを特徴とする水性分散液の製造方法。 - 少なくとも1種の共酸が重合に含まれることを特徴とする請求項10に記載の方法。
- ポリジオキシチオフェンおよびコロイド形成性高分子酸の水性分散液を少なくとも1種のイオン交換樹脂と接触させる工程をさらに含むことを特徴とする請求項11に記載の方法。
- ポリジオキシチオフェンおよびコロイド形成性高分子酸の水性分散液をカチオン交換樹脂と接触させ、その後、アニオン系交換樹脂と接触させることを特徴とする請求項12に記載の方法。
- 少なくとも1種の導電率添加剤を加える工程をさらに含むことを特徴とする請求項12に記載の方法。
- 水と、
ポリジオキシチオフェンと、
コロイド形成性高分子酸と、
水混和性の有機液体と
を含み、
全ポリマーに対する有機液体の重量比が少なくとも約0.1である組成物から形成される層を少なくとも含むことを特徴とする有機電子デバイス。 - 組成物のpHが約1から8の範囲内であることを特徴とする請求項15に記載のデバイス。
- 全ポリマーに対する有機液体の重量比が、約0.3から5.0の範囲内であることを特徴とする請求項15に記載のデバイス。
- 有機液体の沸点が100℃を超えることを特徴とする請求項1に記載の水性分散液。
- 有機液体が、N−メチルピロリドン、エチレングリコール、ジエチレングリコール、ジメチルアセトアミド、ジメチルホルムアミド、ジメチルスルホキシド、およびそれらの組み合わせから選択されることを特徴とする請求項1に記載の水性分散液。
- 組成物がパーフルオロアルキレンスルホン酸を含むことを特徴とする請求項1に記載のデバイス。
- 組成物を含む少なくとも1層が、少なくとも約40℃の温度まで加熱されたバッファ層であることを特徴とする請求項15に記載のデバイス。
- 組成物が、ポリマー、染料、塗布助剤、カーボンナノチューブ、金属粒子、グラファイト繊維、グラファイト粒子、炭素粒子、炭素ナノ粒子、金属ナノワイヤ、有機導電性インク、有機導電性ペースト、無機導電性インク、無機導電性ペースト、電荷輸送材料、架橋剤、およびそれらの組み合わせから選択される少なくとも1種をさらに含むことを特徴とする請求項15に記載のデバイス。
- デバイスが、発光ダイオード、発光ダイオードディスプレイ、ダイオードレーザー、光導電素子、光センサ、フォトレジスタ、光スイッチ、フォトトランジスタ、フォトチューブ、IR検出器、光起電力デバイス、太陽電池、トランジスタ、ダイオード、メモリ記憶装置デバイス、エレクトロクロミックディスプレイ、電磁遮蔽デバイス、およびバイオセンサから選択されることを特徴とする請求項15に記載のデバイス。
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PCT/US2005/008565 WO2005090434A1 (en) | 2004-03-17 | 2005-03-16 | Water dispersible polydioxythiophenes with polymeric acid colloids and a water-miscible organic liquid |
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US7990684B2 (en) | 2008-04-21 | 2011-08-02 | Tayca Corporation | Dispersion liquid of a conductive composition, a conductive composition, and a solid electrolytic capacitor |
JPWO2009131012A1 (ja) * | 2008-04-21 | 2011-08-18 | テイカ株式会社 | 導電性組成物の分散液、導電性組成物および固体電解コンデンサ |
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JP2013539806A (ja) * | 2010-10-12 | 2013-10-28 | ヘレウス プレシャス メタルズ ゲーエムベーハー ウント コンパニー カーゲー | 明確なチオフェン単量体含有量を持つポリチオフェンを含む分散液 |
US9053839B2 (en) | 2010-10-12 | 2015-06-09 | Heraeus Precious Metals Gmbh & Co. Kg | Dispersions comprising polythiophenes with a defined content of thiophene monomer |
JP2016503557A (ja) * | 2012-10-26 | 2016-02-04 | ヘレウス プレシャス メタルズ ゲーエムベーハー ウント コンパニー カーゲー | Oledにおける高電気伝導率及び高効率の透明な層、及びそれらの製造プロセス |
Also Published As
Publication number | Publication date |
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TW200604257A (en) | 2006-02-01 |
TWI370150B (en) | 2012-08-11 |
EP1725601B1 (en) | 2012-02-01 |
KR101189857B1 (ko) | 2012-10-10 |
US20050208328A1 (en) | 2005-09-22 |
CN1976969B (zh) | 2011-10-05 |
CN1976969A (zh) | 2007-06-06 |
KR20070012411A (ko) | 2007-01-25 |
WO2005090434A1 (en) | 2005-09-29 |
EP1725601A1 (en) | 2006-11-29 |
US7338620B2 (en) | 2008-03-04 |
EP2305731A1 (en) | 2011-04-06 |
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