JP5303704B2 - セレン含有導電性ポリマー及び導電性ポリマーの製造方法 - Google Patents
セレン含有導電性ポリマー及び導電性ポリマーの製造方法 Download PDFInfo
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- JP5303704B2 JP5303704B2 JP2008179550A JP2008179550A JP5303704B2 JP 5303704 B2 JP5303704 B2 JP 5303704B2 JP 2008179550 A JP2008179550 A JP 2008179550A JP 2008179550 A JP2008179550 A JP 2008179550A JP 5303704 B2 JP5303704 B2 JP 5303704B2
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- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 19
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- HKGJYTRUDODVMH-UHFFFAOYSA-N selenopheno[2,3-b]selenophene Chemical compound C1=C[se]C2=C1C=C[se]2 HKGJYTRUDODVMH-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
第一層:
プラスチック又はガラス基板上のインジウムスズ酸化物層のような酸化物を含む電極、
第二層:
ドープ型導電性ポリマー及びポリアニオン(すなわちPEDOT/PSS)を含む水分散液から形成された導電性フィルム、
第三層及び/又は第四層:
p型半導体及びn型半導体の分離層又は混合物(ただしp型材料は下記繰り返し構造P1を有するモノマー、オリゴマー、コポリマー又はポリマー材料を含む。
第四層:
典型的にはカルシウム又はアルミニウムのような金属から作られた第二の電極。
第一層:
プラスチック又はガラス基板上のインジウムスズ酸化物層のような酸化物を含む電極、
第二層:
セレノロ[2,3‐c]チオフェン及びフッ素化スルホン酸ポリマーのドープ型重合単位を含む水分散液から形成された導電性フィルム、
第三層及び/又は第四層:
p型半導体及びn型半導体の分離層又は混合物(ただしp型材料は下記繰り返し構造P1を有するモノマー、オリゴマー、コポリマー又はポリマー材料を含む。
第四層:
典型的にはカルシウム又はアルミニウムのような金属から作られた第二の電極。
第一層:
プラスチック又はガラス基板上のインジウムスズ酸化物層のような酸化物を含む電極、
第二層:
セレノロ[2,3‐c]チオフェン及びフッ素化スルホン酸ポリマーのドープ型重合単位を含む水分散液から形成された導電性フィルム、
第三層及び/又は第四層:
p型半導体(p型材料はポリチオフェン及び/又はポリセレノフェンである)及びn型半導体(n型半導体はフラーレン及び/又は低分子及び/又はオリゴマー/ポリマーn型半導体である)の分離層又は混合物、
第四層:
典型的にはカルシウム又はアルミニウムのような金属から作られた第二の電極。
第一層:
例えばアルミニウム、ニオブ又はタンタルのような易酸化性金属箔、
第二層:
金属酸化物層、
第三層:
下記繰り返し構造P1を有する導電性モノマー、オリゴマー、コポリマー又はポリマー材料
第四層:
例えば、導電性の銀、銅又はカーボンブラックを充填した塗料などの電流の良導体である物質の薄層のような接触部。
例えば、P1及びM1で定義したRはα位を含有してよいので、分岐又は架橋が起こり得る。下記構造は、本発明の実施形態の分岐ポリマー材料を示す。
メタノール、エタノール及びi‐プロパノールのような脂肪族アルコール、
アセトン及びメチルエチルケトンのような脂肪族ケトン、
酢酸エチル及び酢酸ブチルのような脂肪族カルボン酸エステル、
トルエン及びキシレンのような芳香族炭化水素、
ヘキサン、ヘプタン及びシクロヘキサンのような脂肪族炭化水素、
ジクロロメタン及びジクロロエタンのような塩素化炭化水素、
アセトニトリルのような脂肪族ニトリル、
ジメチルスルホキシド及びスルホランのような脂肪族スルホキシド及びスルホン、
メチルアセトアミド及びジメチルホルムアミドのような脂肪族カルボキサミド、
ジエチルエーテル及びアニソールのような脂肪族及び芳香族脂肪族エーテル。
さらに、水又は水と上記有機溶媒の混合物を溶媒として使用することもできる。
ポリ(セレノロ[2,3‐c]チオフェン)の水中合成
50mgのセレノロ[2,3‐c]チオフェン及び830mgの18%ポリ(スチレンスルホン酸)の脱イオン水溶液10mLを25mLの一口フラスコに加えた。その混合物を600rpmで撹拌した。113.0mg(0.48mmol)の(NH4)2S2O8及び2mgのFe2(SO4)3を反応フラスコに加えた。酸化重合を1時間以上行なった。重合後、イオン交換カラム(Amberlite IR-120及びMP62)により水溶液を精製して濃い黒色のポリ(セレノロ[2,3‐c]チオフェン)/ポリ(スチレンスルホン酸)水分散液を得た。ポリ(セレノロ[2,3‐c]チオフェン)/ポリ(スチレンスルホン酸)の混合物を1,000rpmでガラス基板上にスピンコートすることにより透明フィルムを調製し、導電面を得た。
ポリ(セレノロ[2,3‐c]チオフェン)の水中合成
50mgのセレノロ[2,3‐c]チオフェン及び5.55gの18%ポリ(スチレンスルホン酸)の脱イオン水溶液45mLを100mLの一口フラスコに加えた。その混合物を1200rpmで置換した。300mg(1.98mmol)のFe2(SO4)3を脱イオン水7mLに溶解させて反応フラスコに加えた。酸化重合を1時間以上行なった。重合後、イオン交換カラムにより水溶液を精製して、濃い黒色のポリ(1H‐チエノ[3,4‐d]イミダゾール‐2(3H)‐オン)/ポリ(スチレンスルホン酸)水分散液を得た。ポリ(セレノロ[2,3‐c]チオフェン)/ポリ(スチレンスルホン酸)の混合物を1,000rpmでガラス基板上にスピンコートすることにより透明フィルムを調製し、導電面を得た。
ポリ(セレノロ[2,3‐c]チオフェン)の水中合成
50mgのセレノロ[2,3‐c]チオフェン及び8.4gの12%NAFION(登録商標)過フッ素化イオン交換樹脂の脱イオン水分散液42mLを100mLの一口フラスコに加えた。その混合物を1200rpmで撹拌した。300mg(1.98mmol)のFe2(SO4)3を脱イオン水7mLに溶解させて反応フラスコに加えた。酸化重合を1時間以上行なった。重合後、イオン交換カラムにより水溶液を精製して、約2.0のpHを示している濃い黒色のポリ(セレノロ[2,3‐c]チオフェン)/NAFION(登録商標)水分散液を得た。ポリ(セレノロ[2,3‐c]チオフェン)/NAFION(登録商標)の混合物を1,000rpmでガラス基板上にスピンコートすることにより透明フィルムを調製し、導電面を得た。
ポリ(セレノロ[2,3‐c]チオフェン)の水中合成
50mgのセレノロ[2,3‐c]チオフェン及び8.4gの12%NAFION(登録商標)過フッ素化イオン交換樹脂の脱イオン水分散液42mLを100mLの一口フラスコに加えた。その混合物を1200rpmで撹拌した。113.0mg(0.48mmol)の(NH4)2S2O8及び2mgのFe2(SO4)3を反応フラスコに加えた。酸化重合を1時間以上行なった。重合後、イオン交換カラム(Amberlite IR-120及びMP62)によりその水溶液を精製して、濃い黒色のポリ(セレノロ[2,3‐c]チオフェン)/NAFION(登録商標)水分散液を得た。ポリ(セレノロ[2,3‐c]チオフェン)/NAFION(登録商標)の混合物を1,000rpmでガラス基板上にスピンコートすることにより透明フィルムを調製し、導電面を得た。
ポリ(セレノロ[2,3‐c]チオフェン)の溶媒(その場)合成
280mgのセレノロ[2,3‐c]チオフェンを無水n‐ブタノール15mLに溶解させた。2.25g(3.3mmol)のp‐トルエンスルホン酸鉄(III)六水和物を無水n‐ブタノール5mLに溶解させてモノマー溶液に加え、深紅色の溶液を得た。その混合物をガラス基板上にドロップキャストして乾燥させた。120℃以下の温度で、15分間以下でその乾燥フィルムを硬化させた。4点プローブ測定を行なったところ生成フィルムは導電性だった。形成したポリマーフィルムは、可視スペクトル帯を弱く均一に吸収するので、裸眼では灰色に見えた。
ポリ(セレノロ[2,3‐c]チオフェン)の電気化学合成及び特性
セレノロ[2,3‐c]チオフェンをヘキサフルオロリン酸テトラブチルアンモニウム/アセトニトリル溶液に溶解させて、モノマーを5mM及び電解質を100mMの濃度に調整し、白金ボタン(platinum button)作用電極(直径2mm)、白金フラッグ対極(1cm2)、及びAg/Ag+非水溶性参照電極(フェロセン溶液で較正することにより算出すると真空準位に対して4.82Vだった)を用いて三電極配置を採用して電気化学的に重合した。そのモノマーは5.6eVの時点で低い酸化電位を示した。繰り返し走査中の低レドックス電位では電流感度が一定間隔で増加することから、重合を確認した。
PLEDデバイス
洗剤、脱イオン水、メタノール、イソプロパノール、及びアセトンを用いて脱イオン水中で連続的に超音波処理することにより、10〜15Ω/□の表面抵抗率を持つ3パターンのITO基板を洗浄した(各々5〜10分間)。異なる洗浄溶剤でITO基板を乾燥させた(本実施例に使用した基板は図1の層1及び層2(層1はガラスであり、層2はITOである)に関する)。次に、SPI Prep II プラズマエッチャーの酸素プラズマを用いてITO基板を約10分間処理した。その後、Laurell型WS-400-N6PPスピナー上で、実施例3の分散液を用いてITO基板を1500rpmで1分間スピンコートした(この分散液は図1の層4に関するが、必要に応じて、性能を向上させるために、層4を堆積させる前に、図1の層3として示した1つ又は2つ以上の中間層材料を堆積させてよい)。次に、ITO基板を180℃で15分間アニールした。アニール後に、約80nm厚の(Sumitomo Chemical社製)LUMATION Green 1304の層をトルエン溶液からスピンコートした(LUMATION Green 1304は図1の層6に相当する。本実施例ではこの層を層4に直接堆積させたが、必要に応じて、1つ又は2つ以上の中間層を層4及び層6の間に堆積させて所望の性能を得てもよい)。次に、窒素保護下のホットプレート上で、そのサンプルを130℃で20分間ベーキングした。次に、アルゴン雰囲気下のグローブボックスの内部に置かれた真空乾燥チャンバーの中にサンプルを移した。約1.5Å(10−10m)/sの速度でマスクによって、5nm厚のBaの層を1×10−7Torr(1Torr≒133.322Pa)を下回る圧力で真空蒸着し、次に約3.0〜4.0Å/sの堆積速度で別の120nm厚のAgの層(この層は図1の層8に相当する)をBa層表面に真空蒸着した。次に、アルゴン雰囲気下のグローブボックス内で、このデバイスをガラス製蓋及び紫外線硬化性エポキシで密閉した。グローブボックスからデバイスを取り出し、次いで発電特性(I‐V曲線)及び輝度を測定した。このデバイスは5000cd/m2では12.5cd/Aの、2500cd/m2では12.6cd/Aの、及び1000cd/m2では12.3 cd/Aの電流輝度効率を示した。特性解析後、続いて5000cd/m2の初期輝度でのDC寿命試験に用いるCDT Eclipse PLED寿命試験器上にデバイスを置いた。デバイスの半減期とは、デバイスの輝度が初期値5000cd/m2の50%(すなわち2500cd/m2)に達するまでにかかる時間をいう。このデバイスの半減期は660時間であった。
Claims (20)
- 下記式の繰り返し単位
- 半導性コロイドを形成するのに十分な酸強度のポリマー酸でドープされており、かつ下記式の繰り返し単位
溶媒又は水
を含む組成物。 - 組成物が水分散液である請求項5に記載の組成物。
- 組成物が溶液である請求項5に記載の組成物。
- 組成物が有機溶媒及び水を含む請求項5に記載の組成物。
- ポリマー酸がポリ(スチレンスルホン酸)である請求項5に記載の組成物。
- ポリマー酸がフッ素化スルホン酸ポリマーである請求項5に記載の組成物。
- 化合物が下記繰り返し単位
- 組成物が、微粒子状の銅、銀、ニッケル、アルミニウム、カーボンブラック、タルク、雲母、珪灰石、シリカ、クレー、TiO2、染料、顔料、及びこれらの組み合わせからなる群から選択される添加剤を含む請求項5に記載の組成物。
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US11/777,386 US7981323B2 (en) | 2007-07-13 | 2007-07-13 | Selenium containing electrically conductive copolymers |
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JP (1) | JP5303704B2 (ja) |
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Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101563389B (zh) * | 2006-12-22 | 2013-07-17 | 默克专利股份有限公司 | 包含稠合硒吩的聚合物 |
US7981323B2 (en) | 2007-07-13 | 2011-07-19 | Konarka Technologies, Inc. | Selenium containing electrically conductive copolymers |
US8148548B2 (en) * | 2007-07-13 | 2012-04-03 | Konarka Technologies, Inc. | Heterocyclic fused selenophene monomers |
US7982055B2 (en) | 2007-07-13 | 2011-07-19 | Konarka Technologies, Inc. | Heterocyclic fused selenophene monomers |
US20090140219A1 (en) * | 2007-07-13 | 2009-06-04 | Air Products And Chemicals, Inc. | Selenium Containing Electrically Conductive Polymers and Method of Making Electrically Conductive Polymers |
WO2009034571A2 (en) * | 2007-09-10 | 2009-03-19 | Yeda Research And Development Co. Ltd. | Selenophenes and selenophene-based polymers, their preparation and uses thereof |
US8268195B2 (en) * | 2008-09-29 | 2012-09-18 | Air Products And Chemicals, Inc. | Electrically conductive films formed from dispersions comprising polythiophenes and ether containing polymers |
US20100270055A1 (en) * | 2009-04-27 | 2010-10-28 | Air Products And Chemicals, Inc. | Electrically Conductive Films Formed From Dispersions Comprising Conductive Polymers and Polyurethanes |
US8470205B2 (en) | 2009-06-05 | 2013-06-25 | Air Products And Chemicals, Inc. | Electrically conductive films formed from dispersions comprising conductive polymers and hyperbranched polymers |
CN101922668B (zh) * | 2009-06-17 | 2012-12-05 | 上海宏源照明电器有限公司 | 照明装置 |
JP5410251B2 (ja) * | 2009-11-26 | 2014-02-05 | Necトーキン株式会社 | 導電性高分子懸濁液およびその製造方法、導電性高分子材料、電解コンデンサ、ならびに固体電解コンデンサおよびその製造方法 |
US11732527B2 (en) | 2009-12-22 | 2023-08-22 | View, Inc. | Wirelessly powered and powering electrochromic windows |
US11630366B2 (en) | 2009-12-22 | 2023-04-18 | View, Inc. | Window antennas for emitting radio frequency signals |
TWI397189B (zh) * | 2009-12-24 | 2013-05-21 | Au Optronics Corp | 製作太陽能薄膜電池之方法及其結構 |
US8338698B2 (en) | 2010-08-27 | 2012-12-25 | Primestar Solar, Inc. | Anisotropic conductive layer as a back contact in thin film photovoltaic devices |
US8187912B2 (en) | 2010-08-27 | 2012-05-29 | Primestar Solar, Inc. | Methods of forming an anisotropic conductive layer as a back contact in thin film photovoltaic devices |
GB201016222D0 (en) * | 2010-09-27 | 2010-11-10 | Natural Enviromental Res Council | Aerosol detection |
EP2697283A4 (en) * | 2011-04-15 | 2015-12-16 | Univ Chicago | SEMICONDUCTOR POLYMERS |
WO2013116643A1 (en) | 2012-02-03 | 2013-08-08 | The University Of Chicago | Semiconducting polymers |
TWI523038B (zh) * | 2012-05-04 | 2016-02-21 | Elite Optoelectronic Co Ltd | A flexible transparent display structure and method for forming a light emitting diode |
US9790330B2 (en) * | 2012-10-28 | 2017-10-17 | Polym Technology Corporation | Method for forming conjugated heteroaromatic homopolymer and copolymer, and products thereof |
US9627147B2 (en) * | 2012-10-28 | 2017-04-18 | Polym Technology Corporation | Composition and method for forming electroactive coating comprising conjugated heteroaromatic polymer, capacitor and antistatic object comprising the electroactive coating, and solid electrolytic capacitor and method for fabricating the same |
US9882109B2 (en) * | 2012-11-06 | 2018-01-30 | Empire Technology Development Llc | Bi-polar organic semiconductors for thermoelectric power generation |
JP5556917B2 (ja) * | 2013-02-12 | 2014-07-23 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
KR20180108917A (ko) * | 2013-10-31 | 2018-10-04 | 카티바, 인크. | 잉크젯 인쇄를 위한 폴리티오펜-포함 잉크 조성물 |
US10020089B2 (en) * | 2014-09-05 | 2018-07-10 | Shin-Etsu Chemical Co., Ltd. | Conductive polymer composite and substrate |
CN112615135A (zh) | 2014-11-25 | 2021-04-06 | 唯景公司 | 窗天线 |
US11114742B2 (en) | 2014-11-25 | 2021-09-07 | View, Inc. | Window antennas |
US20220019117A1 (en) * | 2014-11-25 | 2022-01-20 | View, Inc. | Electromagnetic-shielding electrochromic windows |
JP6499535B2 (ja) * | 2015-07-09 | 2019-04-10 | 信越化学工業株式会社 | 被覆品、及びパターン形成方法 |
US9752045B2 (en) * | 2015-08-25 | 2017-09-05 | Shin-Etsu Chemical Co., Ltd. | Conductive polymer composite and substrate |
JP6474358B2 (ja) | 2015-08-25 | 2019-02-27 | 信越化学工業株式会社 | 導電性ポリマー複合体及び基板 |
CN107799324B (zh) * | 2016-09-06 | 2019-07-16 | 江西科技师范大学 | 应用于超级电容器的聚硒吩衍生物薄膜电极及其制备方法 |
KR20180051748A (ko) * | 2016-11-08 | 2018-05-17 | 삼성디스플레이 주식회사 | 헤테로환 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20220114526A (ko) * | 2019-09-06 | 2022-08-17 | 마이클 존 아놀드 | 유기 중합체 조성물 |
CN114496571A (zh) * | 2020-10-26 | 2022-05-13 | 钰邦科技股份有限公司 | 生产电解电容器的方法 |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8505285D0 (en) | 1985-03-01 | 1985-04-03 | Beecham Group Plc | Compounds |
EP0440957B1 (de) | 1990-02-08 | 1996-03-27 | Bayer Ag | Neue Polythiophen-Dispersionen, ihre Herstellung und ihre Verwendung |
JPH08245636A (ja) * | 1995-03-06 | 1996-09-24 | Fuji Electric Co Ltd | セレノロセレノフェンオリゴマおよびその製造方法 |
US6585914B2 (en) | 2000-07-24 | 2003-07-01 | Northwestern University | N-type thiophene semiconductors |
TWI287130B (en) * | 2001-01-16 | 2007-09-21 | Au Optronics Corp | Backlight module and a frame for fixing a light guide plate |
US6709808B2 (en) | 2001-05-14 | 2004-03-23 | Eastman Kodak Company | Imaging materials comprising electrically conductive polymer particle layers |
KR20030010508A (ko) | 2001-07-25 | 2003-02-05 | 메르크 파텐트 게엠베하 | 모노-, 올리고- 및 폴리-4-플루오로티오펜 및 전하 이동물질로서의 이들의 용도 |
DE60235679D1 (de) | 2001-08-17 | 2010-04-29 | Merck Patent Gmbh | Konjugierte Copolymere aus Dithienothiophen und Vinylen oder Acetylen |
ATE473251T1 (de) | 2001-09-29 | 2010-07-15 | Merck Patent Gmbh | Mono-, oligo- und polymere aus benzo(b)thiophen und 2,2'-bisbenzothiophen und ihre verwendung als ladungstransportmaterial |
SG124249A1 (en) | 2001-12-07 | 2006-08-30 | Sumitomo Chemical Co | New polymer and polymer light-emitting device using the same |
US7572879B2 (en) | 2002-07-11 | 2009-08-11 | Air Products And Chemicals, Inc. | Fluorinated alkyl substituted-thieno[3,4-b]thiophene monomers and polymers therefrom |
US7118692B2 (en) | 2004-10-04 | 2006-10-10 | Air Products And Chemicals, Inc. | Substituted thienothiophene monomers and conducting polymers |
US7071289B2 (en) | 2002-07-11 | 2006-07-04 | The University Of Connecticut | Polymers comprising thieno [3,4-b]thiophene and methods of making and using the same |
US7125479B2 (en) | 2002-07-11 | 2006-10-24 | The University Of Connecticut | Polymeric compositions comprising thieno[3,4-b]thiophene, method of making, and use thereof |
JP4582286B2 (ja) | 2003-07-18 | 2010-11-17 | 日産化学工業株式会社 | スルホオキシアルキニルチオフェン化合物及びその製造法 |
US7060846B2 (en) | 2004-10-04 | 2006-06-13 | Air Products And Chemicals, Inc. | Pentafluorosulfanyl-substituted thienothiophene monomers and conducting polymers |
US7569158B2 (en) | 2004-10-13 | 2009-08-04 | Air Products And Chemicals, Inc. | Aqueous dispersions of polythienothiophenes with fluorinated ion exchange polymers as dopants |
JP2008546898A (ja) * | 2005-06-27 | 2008-12-25 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 導電性ポリマー組成物 |
WO2007002740A2 (en) * | 2005-06-28 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Buffer compositions |
EP1754736B1 (en) | 2005-08-16 | 2011-05-11 | Merck Patent GmbH | Process for the polymerisation of thiophene or selenophene derivatives |
US20070085061A1 (en) * | 2005-10-14 | 2007-04-19 | Elder Delwin L | Conductivity enhancement of conductive polymers by solvent exposure |
US20070170401A1 (en) * | 2005-12-28 | 2007-07-26 | Che-Hsiung Hsu | Cationic compositions of electrically conducting polymers doped with fully-fluorinated acid polymers |
US20070278458A1 (en) * | 2006-04-13 | 2007-12-06 | Martello Mark T | Electrically conductive polymer compositions |
US20070278453A1 (en) * | 2006-06-02 | 2007-12-06 | Steffen Zahn | Electrically conductive polymers and method of making electrically conductive polymers |
KR101387894B1 (ko) * | 2006-06-30 | 2014-04-25 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전도성 중합체 및 부분적으로 플루오르화된 산 중합체의 안정화된 조성물 |
JP5121355B2 (ja) * | 2006-08-25 | 2013-01-16 | 住友化学株式会社 | 有機薄膜の製造方法 |
CN101563389B (zh) * | 2006-12-22 | 2013-07-17 | 默克专利股份有限公司 | 包含稠合硒吩的聚合物 |
US20080191172A1 (en) * | 2006-12-29 | 2008-08-14 | Che-Hsiung Hsu | High work-function and high conductivity compositions of electrically conducting polymers |
US7982055B2 (en) * | 2007-07-13 | 2011-07-19 | Konarka Technologies, Inc. | Heterocyclic fused selenophene monomers |
US20090140219A1 (en) | 2007-07-13 | 2009-06-04 | Air Products And Chemicals, Inc. | Selenium Containing Electrically Conductive Polymers and Method of Making Electrically Conductive Polymers |
US7981323B2 (en) | 2007-07-13 | 2011-07-19 | Konarka Technologies, Inc. | Selenium containing electrically conductive copolymers |
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TW200906897A (en) | 2009-02-16 |
US20090014693A1 (en) | 2009-01-15 |
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