JP5890424B2 - 明確な硫酸イオン含有量を持つポリチオフェンを含む分散液 - Google Patents
明確な硫酸イオン含有量を持つポリチオフェンを含む分散液 Download PDFInfo
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- JP5890424B2 JP5890424B2 JP2013533118A JP2013533118A JP5890424B2 JP 5890424 B2 JP5890424 B2 JP 5890424B2 JP 2013533118 A JP2013533118 A JP 2013533118A JP 2013533118 A JP2013533118 A JP 2013533118A JP 5890424 B2 JP5890424 B2 JP 5890424B2
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- polythiophene
- aliphatic
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- 239000006185 dispersion Substances 0.000 title claims description 59
- 229920000123 polythiophene Polymers 0.000 title claims description 45
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title claims description 40
- 239000000203 mixture Substances 0.000 claims description 136
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 45
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 44
- -1 aliphatic nitrile Chemical class 0.000 claims description 44
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 38
- 229940005642 polystyrene sulfonic acid Drugs 0.000 claims description 38
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 36
- 229920000447 polyanionic polymer Polymers 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 23
- 229930192474 thiophene Natural products 0.000 claims description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
- 150000002500 ions Chemical class 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000007800 oxidant agent Substances 0.000 claims description 14
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
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- 150000003839 salts Chemical class 0.000 claims description 6
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical group O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 4
- 235000011152 sodium sulphate Nutrition 0.000 claims description 4
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- 230000000996 additive effect Effects 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
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- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
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- 239000000758 substrate Substances 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 11
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 230000014509 gene expression Effects 0.000 description 7
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
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- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 229920002125 Sokalan® Polymers 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- 239000004713 Cyclic olefin copolymer Substances 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
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- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
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- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
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- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical class [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
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- 125000002228 disulfide group Chemical group 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
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- 238000003682 fluorination reaction Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
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- 238000009499 grossing Methods 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 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
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Description
I)チオフェン単量体および酸化剤を含む組成物Z1を準備する工程と、
II)この酸化剤を還元生成物へと還元し、チオフェン単量体を酸化することにより、このチオフェン単量体を酸化重合させ、ポリチオフェンおよび上記還元生成物を含む組成物Z2を形成する工程と、
III)工程II)で得られた組成物Z2から、この還元生成物を少なくとも部分的に除去して、組成物Z3を得る工程と
を含み、組成物Z3は、いずれの場合も組成物Z3の総重量に基づき、100ppm〜1,000ppmの範囲、好ましくは100ppm〜500ppmの範囲、特に好ましくは100ppm〜200ppmの範囲の硫酸イオン含有量を有する、製造方法によってなされる。
Aは、置換されていてもよいC1−C5−アルキレン残基を表し、
Rは、互いに独立に、H、直鎖状もしくは分枝状の、置換されていてもよいC1−C18−アルキル残基、置換されていてもよいC5−C12−シクロアルキル残基、置換されていてもよいC6−C14−アリール残基、置換されていてもよいC7−C18−アラルキル残基、置換されていてもよいC1−C4−ヒドロキシアルキル残基またはヒドロキシル残基を表し、
xは、0〜8の整数を表し、
複数の基RがAに結合されている場合、それらの基は、同じであってもよいしまたは異なってもよい)
である。一般式(I)は、x個の置換基Rがアルキレン残基Aに結合されていてもよいというように理解されるべきである。
i)2mPas〜1,000mPasの範囲、好ましくは10mPas〜500mPasの範囲、特に好ましくは60mPas〜250mPasの範囲の粘度;
ii)少なくとも600S/cm、好ましくは少なくとも500S/cm、特に好ましくは少なくとも400S/cmの、本願明細書に記載される試験方法による電気伝導率;
iii)いずれの場合も当該組成物の総重量に基づき0.05重量%〜50重量%の範囲、好ましくは0.1重量%〜10重量%の範囲、特に好ましくは1重量%〜5重量%の範囲のPEDOT/PSS含有量。
A)基板表面を持つ基板と、
B)この基板表面を少なくとも部分的に覆う層と、
を含み、この層は、本発明に係る組成物または本発明に係る方法によって得ることができる組成物に含まれる固形分から形成される、層構築物によってもなされる。
B1)当該層の内部透過率は、60%超、好ましくは70%超、特に好ましくは80%超である;
B2)当該層の粗度(Ra)は、50nm未満、好ましくは30nm未満、特に好ましくは20nm未満、とりわけ好ましくは10nm未満、またはさらには5nm未満である。
特段の記載がない限り、温度21℃、50%〜70%の範囲の大気湿度、大気圧の実験室中で試験を実施した。
分散液の硫酸イオン含有量は、イオンクロマトグラフィーによって決定した。この目的のために、イオン交換体を充填したカラムを、あとの電気伝導率測定とともに使用した。使用したイオンクロマトグラフはDionex 300であった。Dionex製の長さ50mmおよび内径4.0mmおよび粒径5μmのIonPac AG 11前処理カラムを使用した。Dionex製の、長さ250mmおよび内径4.0mmおよび粒径5μmのIonPac AS 11分離カラムを使用した。水を溶離液として使用した。流量は1.8mL/分であった。注入量は50μLであった。この構成における硫酸イオンについての保持時間はおよそ12.5分であった。Dionex ASRS−sサプレッサーを具えた電気伝導率検出器を用いて硫酸イオンを検出した。
当該分散液の鉄含有量は、誘導結合プラズマを用いる質量分析(ICP−MS)(Element 2;THERMO)を用いて決定した。較正は、2つの別個の較正溶液(低濃度標品および高濃度)を用いて実施し、そのために、ロジウム内部標準および多元素溶液(Merckより入手)を使用した。2gの本発明の試料を20mLに希釈し使用した。分析は、上記質量分析計の中分解能で実施した。同位体Fe(54)、Fe(56)およびRh(103)を検出し、この較正に基づいて、試料の鉄含有量を求めた。
洗浄したガラス基板をスピンコーターに置き、この基板上に10mLの本発明に係る組成物を広げた。次いで、残りの溶液を、プレートの回転により振り落とした。このあと、このようにコーティングした基板を、ホットプレートの上で、130℃で15分間乾燥した。次いで、層の厚さを測定する装置(Tencor、Alphastep 500)を用いて層の厚さを求めた。長さ2.5cmのAg電極を、シャドーマスクを介して10mmの距離で気相堆積することによって、電気伝導率を求めた。電位計(Keithly 614)を用いて求めた表面抵抗に層の厚さを掛け合わせ、比電気抵抗を得た。電気伝導率は、この比電気抵抗の逆数である。
粘度は、クリオスタットを取り付けたHaake RV 1レオメータを使用して求めた。ダブルギャップを持つDG43測定用シリンダーおよびDG43ローター(両方ともHaake製)を使用した。12gの水溶液をこの測定用シリンダーに秤量した。クリオスタットによって温度を20℃に制御した。所望の温度を確立するために、当該分散液を、まず50s−1のせん断速度で240秒間、調節した。次いでせん断速度を100s−1に高めた。このせん断速度を30秒間維持した。次いでさらに30秒間に、100s−1のせん断速度で30回の粘度測定(1測定/秒)を行った。次いで、これらの30個の測定値の平均値をその分散液の粘度として採用した。
20gの組成物を250mLのビーカーの中に入れた。次いでこの組成物を、45°の傾斜角度を有する滑らかなプラスチック表面に注ぎ込んだ。
a)ビーカーから注ぎ込んだときに、その組成物は、均等に流れず、この組成物が塊となってガラス壁に付着して残る領域および組成物がほとんど何も残っていない領域を残す。
b)その物質がプラスチック表面にわたって流れるとき、この物質は所々に塊となって残る。この流れは、均一でなく、何度も断裂する[図1]。
A)注ぎ出されたとき、均一な膜がビーカー壁に残り、この膜は、組成物の粘度に応じて薄いかまたは厚い。どの場合でも、膜は均一であり、不均等性をまったく示さない。
B)この物質がプラスチック表面にわたって流れるとき、均一な膜が生成する[図2]。
コーティングした基板の透過率は、2チャネル分光計(PerkinElmer製のLambda900)を用いて求めた。試料によって散乱した透過光のあらゆる部分をさらに検出するために、この装置に、球形光束計(Ulbricht Sphere)を取り付けられていた。測定対象の試料を球形光束計の入力開口部に固定した。
内部透過率は、Y/Y0×100%に対応する。
洗浄したガラス基板をスピンコーターに置き、この基板上に10mLの本発明に係る組成物を広げた。次いで、残りの溶液を、プレートの回転により振り落とした。このあと、このようにコーティングした基板を、ホットプレートの上で、130℃で15分間乾燥した。
記号Raによって表される平均粗度は、平均線からの −表面上での− 測定点の平均距離を与える。この平均線は、基準経路内の、(平均線に対する)プロファイルの偏差の合計が最小になるように、現実のプロファイルを横切る。
粒子の判定 − 顕微鏡による検査
検討対象の試料3滴を、ピペットを用いてスライドの上に置き、およそ1cm2の面積に広げた。次いで、このスライドを100℃の乾燥機の中で10分間乾燥した。冷却後、そのスライドを、顕微鏡(Zeiss Axioskop)のもとで、偏光フィルターを用いずに透過光を使用して、100×倍率で調べた。
上記混合物のために、以下の特性を持つPEDOT/PSS分散液(H.C.Starck Clevios GmbH、レーバークーゼン(Leverkusen)製のClevios P HC V4)を使用した:
粘度: 255mPas
固体物質含有量: 1.10%
硫酸イオン含有量: 7mg/kg
ナトリウム含有量: 138mg/kg
鉄含有量: 0.20mg/kg
電気伝導率: 426S/cm(5%ジメチルスルホキシドの添加後に測定した)。
上記の方法を用いた粒子濃度: なし
2000gの、固形分含量1.10%を有するPEDOT/PSS分散液(H.C.Starck Clevios GmbH製のClevios PH 500)を、限外濾過を用いて固形分含量2.20%に濃縮した。次いで、この分散液を、500mLのイオン交換体樹脂(Lewatit MP 62、Saltigo製)を充填したカラムの中に入れた。得られた分散液は、以下の特性を有していた:
粘度: 103mPas
固体物質含有量: 1.98%
硫酸イオン含有量: 1mg/kg
ナトリウム含有量: 5mg/kg
電気伝導率: 425S/cm(5% ジメチルスルホキシドの添加後に測定した)
鉄含有量 0.19mg/kg
上記の方法を用いた粒子濃度: なし
Claims (19)
- ポリチオフェンを含む組成物の製造方法であって、
I)チオフェン単量体および酸化剤を含む組成物Z1を準備する工程と、
II)前記酸化剤を還元生成物へと還元し、前記チオフェン単量体を酸化することにより、前記チオフェン単量体を酸化重合させ、ポリチオフェンおよび前記還元生成物を含む組成物Z2を形成する工程と、
III)工程II)で得られた前記組成物Z2から、前記還元生成物を少なくとも部分的に除去して、組成物Z3を得る工程と、
を含み、前記組成物Z3は、前記組成物Z3の総重量に基づき、100ppm〜1,000ppmの範囲の硫酸イオン含有量を有し、工程III)における前記還元生成物の少なくとも部分的な除去は、前記組成物Z2をイオン交換体で処理することによって行われる、製造方法。 - ポリチオフェンを含む前記組成物Z3は、前記組成物Z3に基づき100〜500ppmの範囲の硫酸イオン含有量を有する、請求項1に記載の製造方法。
- ポリチオフェンを含む前記組成物Z3は、前記組成物Z3に基づき100〜200ppmの範囲の硫酸イオン含有量を有する、請求項1に記載の製造方法。
- 前記組成物Z3の硫酸イオン含有量は、硫酸または硫酸の塩を組成物Z3に加えることにより調整される、請求項1から請求項3のいずれか1項に記載の製造方法。
- 前記チオフェン単量体は3,4−エチレンジオキシチオフェン(EDT)であり、前記ポリチオフェンはポリ(3,4−エチレンジオキシチオフェン)(PEDOT)である、請求項1から請求項4のいずれか1項に記載の製造方法。
- 工程I)で準備されるチオフェン単量体および酸化剤を含む前記組成物Z1は、ポリアニオンをも含む、請求項1から請求項5のいずれか1項に記載の製造方法。
- 前記ポリアニオンはポリスチレンスルホン酸(PSS)である、請求項6に記載の製造方法。
- 前記組成物Z3はPEDOT/PSS分散液である、請求項1から請求項7のいずれか1項に記載の製造方法。
- 前記硫酸の塩は、硫酸のアルカリ塩もしくはアンモニウム塩またはそれらの混合物である、請求項1から請求項8のいずれか1項に記載の製造方法。
- 前記硫酸のアルカリ塩は硫酸ナトリウムである、請求項9に記載の製造方法。
- ポリチオフェンを含む組成物であって、前記ポリチオフェンに加えて、前記組成物の総重量に基づき100ppm〜500ppmの範囲の硫酸イオンを含み、前記組成物の総重量に基づき200ppm未満の鉄を含み、また、前記組成物が、エーテル基を含む化合物、ラクトン基を含む化合物、アミド基またはラクタム基を含む化合物、スルホン、スルホキシド、糖または糖誘導体、フラン誘導体および二価アルコールまたは多価アルコールからなる群から選ばれる添加剤を含む、組成物。
- 前記組成物は、脂肪族アルコール、脂肪族ケトン、脂肪族カルボン酸エステル、芳香族炭化水素、脂肪族炭化水素、環状炭化水素、脂肪族ニトリル、脂肪族スルホキシド、脂肪族スルホン、脂肪族カルボン酸アミド、脂肪族エーテルおよび芳香族脂肪族エーテルからなる群から選ばれる溶媒をさらに含む、請求項11に記載の組成物。
- 前記組成物は、前記組成物の総重量に基づき20ppm未満の鉄を含む、請求項11から請求項12のいずれか1項に記載の組成物。
- 前記ポリチオフェンはポリ(3,4−エチレンジオキシチオフェン)である、請求項11から請求項13のいずれか1項に記載の組成物。
- 前記ポリチオフェンに加えて、前記組成物はポリアニオンを含む、請求項11から請求項14のいずれか1項に記載の組成物。
- 前記ポリアニオンはポリスチレンスルホン酸である、請求項15に記載の組成物。
- 前記組成物はPEDOT/PSS錯体である、請求項11から請求項16のいずれか1項に記載の組成物。
- 前記組成物は、以下の特性:
i)60mPas〜250mPasの範囲の粘度、
ii)少なくとも400S/cmの電気伝導率、
iii)前記組成物の総重量に基づき1重量%〜5重量%の範囲のPEDOT/PSS 含有量、
のうちの少なくとも1つを有する、請求項17に記載の組成物。 - 電子部品における導電層を製造するための、請求項11から請求項18のいずれか1項に記載の組成物の使用。
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DE3843412A1 (de) | 1988-04-22 | 1990-06-28 | Bayer Ag | Neue polythiophene, verfahren zu ihrer herstellung und ihre verwendung |
EP0440957B1 (de) | 1990-02-08 | 1996-03-27 | Bayer Ag | Neue Polythiophen-Dispersionen, ihre Herstellung und ihre Verwendung |
EP0593111B1 (en) * | 1992-10-14 | 1998-06-17 | Agfa-Gevaert N.V. | Antistatic coating composition |
DE19841803A1 (de) * | 1998-09-12 | 2000-03-16 | Bayer Ag | Hilfsschichten für elektrolumineszierende Anordnungen |
DE10103416A1 (de) | 2001-01-26 | 2002-08-01 | Bayer Ag | Elektrolumineszierende Anordnungen |
KR20030024690A (ko) * | 2001-04-17 | 2003-03-26 | 코닌클리케 필립스 일렉트로닉스 엔.브이. | 저 황산염 및 고 금속 이온 함량을 갖는 전도성 투명중합체 층을 포함하는 led |
US6811897B2 (en) * | 2002-03-29 | 2004-11-02 | Kabushiki Kaisha Toshiba | Ink for forming a hole injection layer of organic EL display devices and manufacturing method thereof, organic EL display devices, and manufacturing method of the same |
JP4281442B2 (ja) * | 2003-05-29 | 2009-06-17 | セイコーエプソン株式会社 | 正孔輸送材料 |
DE102004006583A1 (de) * | 2004-02-10 | 2005-09-01 | H.C. Starck Gmbh | Polythiophenformulierungen zur Verbesserung von organischen Leuchtdioden |
US7438832B2 (en) * | 2005-03-29 | 2008-10-21 | Eastman Kodak Company | Ionic liquid and electronically conductive polymer mixtures |
WO2007006833A2 (es) * | 2005-07-13 | 2007-01-18 | Fundacion Cidetec | Sensores de presión distribuidos de gran superficie basados en politiofenos |
JP2009221417A (ja) * | 2008-03-18 | 2009-10-01 | Fujifilm Corp | 導電性ポリマー及びその精製方法 |
DE102009036282A1 (de) * | 2009-08-06 | 2011-02-10 | H.C. Starck Clevios Gmbh | Neue Polymerbeschichtungen enthaltend leitfähige Polymere |
JPWO2011065213A1 (ja) * | 2009-11-27 | 2013-04-11 | コニカミノルタホールディングス株式会社 | 分散液、透明電極、および有機エレクトロルミネッセンス素子 |
DE102010048032A1 (de) * | 2010-10-12 | 2012-04-12 | Heraeus Clevios Gmbh | Polythiophene beinhaltende Dispersionen mit definiertem Gehalt an Thiophen-Monomer |
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- 2011-10-07 KR KR1020137012171A patent/KR101783508B1/ko active IP Right Grant
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US20140145118A1 (en) | 2014-05-29 |
TW201217426A (en) | 2012-05-01 |
CN103201341A (zh) | 2013-07-10 |
KR101783508B1 (ko) | 2017-09-29 |
JP2013540865A (ja) | 2013-11-07 |
WO2012048824A1 (en) | 2012-04-19 |
DE102010048031A1 (de) | 2012-04-12 |
EP2627711A1 (en) | 2013-08-21 |
TWI598373B (zh) | 2017-09-11 |
KR20130101084A (ko) | 2013-09-12 |
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