JP5324217B2 - 導電性ポリマー組成物 - Google Patents
導電性ポリマー組成物 Download PDFInfo
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- JP5324217B2 JP5324217B2 JP2008519493A JP2008519493A JP5324217B2 JP 5324217 B2 JP5324217 B2 JP 5324217B2 JP 2008519493 A JP2008519493 A JP 2008519493A JP 2008519493 A JP2008519493 A JP 2008519493A JP 5324217 B2 JP5324217 B2 JP 5324217B2
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- Prior art keywords
- fluorinated
- polymer
- acid
- layer
- wetted
- Prior art date
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- KMHNDBZHNQAYRY-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(1,2,2-trifluoroethenoxy)propoxy]ethanesulfonyl fluoride Chemical compound FC(F)=C(F)OC(F)(C(F)(F)F)C(F)(F)OC(F)(F)C(F)(F)S(F)(=O)=O KMHNDBZHNQAYRY-UHFFFAOYSA-N 0.000 claims description 3
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- 239000000243 solution Substances 0.000 description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
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- 239000002322 conducting polymer Substances 0.000 description 8
- ZAHSNWXGKUBLHM-UHFFFAOYSA-N hydroperoxy(hydroxy)silane Chemical compound OO[SiH2]O ZAHSNWXGKUBLHM-UHFFFAOYSA-N 0.000 description 8
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- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 7
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- 102100039298 Phosphatidylserine synthase 1 Human genes 0.000 description 4
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- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
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- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000003631 wet chemical etching Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Description
本出願は、2005年6月27日出願の米国仮特許出願第60/694279号に対する優先権を主張する。
陽極/緩衝層/EL材料/陰極
R1は、独立に、各存在で同一または異なるよう選択されると共に、水素、アルキル、アルケニル、アルコキシ、アルカノイル、アルキルチオ(alkythio)、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、アクリル酸、リン酸、ホスホン酸、ハロゲン、ニトロ、シアノ、ヒドロキシル、エポキシ、シラン、シロキサン、アルコール、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、アミドスルホネート、エーテルスルホネート、エステルスルホネート、およびウレタンから選択され;または両方のR1基は一緒になって、任意選択的に1つまたは複数の二価の窒素、硫黄または酸素原子を含んでもよい3、4、5、6、または7員芳香族または脂環式環を完成させるアルキレンまたはアルケニレン鎖を形成してもよく、
およびnは少なくとも約4である。
「アルコール」−R3−OH
「アミド」−R3−C(O)N(R6)R6
「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または−R3−O−C(O)−Z
「エーテル」−R3−(O−R5)p−O−R5
「エーテルカルボキシレート」−R3−O−R4−C(O)O−Zまたは−R3−O−R4−O−C(O)−Z
「エーテルスルホネート」−R3−O−R4−SO3Z
「エステルスルホネート」−R3−O−C(O)R4−SO3Z
「スルホンイミド」−R3−SO2−NH−SO2−R5
「ウレタン」−R3−O−C(O)−N(R6)2
(式中、すべての「R」基は各存在で同一または異なると共に:
R3は、単一の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、
pは、0または1〜20の整数であり、
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)
R7は、各存在で同一または異なると共に、水素、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、エステルスルホネート、およびウレタンから選択され、ただし、少なくとも1つのR7は水素ではなく、
mは2または3であり、および
nは少なくとも約4である。
nは少なくとも約4であり;
R1は、独立に、各存在で同一または異なるよう選択されると共に、水素、アルキル、アルケニル、アルコキシ、アルカノイル、アルキルチオ(alkythio)、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、アクリル酸、リン酸、ホスホン酸、ハロゲン、ニトロ、シアノ、ヒドロキシル、エポキシ、シラン、シロキサン、アルコール、ベンジル、カルボキシレート、エーテル、アミドスルホネート、エーテルカルボキシレート、エーテルスルホネート、エステルスルホネート、およびウレタンから選択され;または両方のR1基は一緒になって、任意選択的に1つまたは複数の二価の窒素、硫黄または酸素原子を含んでもよい3、4、5、6、または7員芳香族または脂環式環を完成させるアルキレンまたはアルケニレン鎖を形成してもよく;および
R2は、独立に、各存在で同一または異なるよう選択されると共に、水素、アルキル、アルケニル、アリール、アルカノイル、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、エポキシ、シラン、シロキサン、アルコール、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、エステルスルホネート、およびウレタンから選択される。
nは少なくとも約4であり;
aは0〜4の整数であり;
bは1〜5の整数であり、ただし、a+b=5であり;および
R3は、独立に、各存在で同一または異なるよう選択されると共に、アルキル、アルケニル、アルコキシ、シクロアルキル、シクロアルケニル、アルカノイル、アルキルチオ(alkythio)、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、カルボン酸、ハロゲン、シアノ、または1つまたは複数のスルホン酸、カルボン酸、ハロ、ニトロ、シアノまたはエポキシ部分で置換されたアルキルから選択され;またはいずれか2つのR3基は一緒になって、任意選択的に1つまたは複数の二価の窒素、硫黄または酸素原子を含んでもよい3、4、5、6、または7員芳香族または脂環式環を完成させるアルキレンまたはアルケニレン鎖を形成してもよい。
QはSまたはNHであり;
R8、R9、R10、およびR11は、独立に、各存在で同一または異なるよう選択されると共に、水素、アルキル、アルケニル、アルコキシ、アルカノイル、アルキルチオ(alkythio)、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、アクリル酸、リン酸、ホスホン酸、ハロゲン、ニトロ、シアノ、ヒドロキシル、エポキシ、シラン、シロキサン、アルコール、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、アミドスルホネート、エーテルスルホネート、エステルスルホネートおよびウレタンから選択され;および
R8およびR9、R9およびR10、ならびにR10およびR11の少なくとも1つは一緒になって、任意選択的に1つまたは複数の二価の窒素、硫黄または酸素原子を含んでもよい5または6員芳香族環を完成させるアルケニレン鎖を形成する。
QはSまたはNHであり;および
Tは、各存在で同一または異なると共に、S、NR6、O、SiR6 2、Se、およびPR6から選択され;
R6は水素またはアルキルである。
QはSまたはNR6であり;
Tは、S、NR6、O、SiR6 2、Se、およびPR6から選択され;
Zは、アルケニレン、アリーレン、およびヘテロアリーレンから選択され;
R6は水素またはアルキルであり;
R12は、各存在で同一または異なると共に、水素、アルキル、アルケニル、アルコキシ、アルカノイル、アルキルチオ(alkythio)、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、アクリル酸、リン酸、ホスホン酸、ハロゲン、ニトロ、ニトリル、シアノ、ヒドロキシル、エポキシ、シラン、シロキサン、アルコール、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、アミドスルホネート、エーテルスルホネート、およびウレタンから選択され;または両方のR12基は一緒になって、任意選択的に1つまたは複数の二価の窒素、硫黄または酸素原子を含んでもよい3、4、5、6、または7員芳香族または脂環式環を完成させるアルキレンまたはアルケニレン鎖を形成してもよい。
qは1〜5の整数であり、
R13はOHまたはNHR14であり、および
R14は、アルキル、フルオロアルキル、スルホニルアルキル、またはスルホニルフルオロアルキルである。
Wは、(CF2)q、O(CF2)q、S(CF2)q、(CF2)qO(CF2)r、およびSO2(CF2)qから選択され、
qおよびrは、独立に1〜5の整数であり、
R13はOHまたはNHR14であり、および
R14は、アルキル、フルオロアルキル、スルホニルアルキル、またはスルホニルフルオロアルキルである。
Rfは、フッ素化アルキレン、フッ素化ヘテロアルキレン、フッ素化アリーレン、またはフッ素化ヘテロアリーレンから選択され;
Rgは、フッ素化アルキレン、フッ素化ヘテロアルキレン、フッ素化アリーレン、フッ素化ヘテロアリーレン、アリーレン、またはヘテロアリーレンから選択され;および
nは少なくとも4である。
Rgは、フッ素化アルキレン、フッ素化ヘテロアルキレン、フッ素化アリーレン、フッ素化ヘテロアリーレン、アリーレン、またはヘテロアリーレンから選択され;
R15は、フッ素化アルキレン基またはフッ素化ヘテロアルキレン基であり;
R16は、フッ素化アルキルまたはフッ素化アリール基であり;および
pは、0または1〜4の整数である。
R16は、フッ素化アルキルまたはフッ素化アリール基であり;
a、b、c、d、およびeは、それぞれ独立に0または1〜4の整数であり;および
nは少なくとも4である。
R17〜R20は、独立にH、ハロゲン、1〜10個の炭素原子のアルキルまたはアルコキシ、Y、C(Rf’)(Rf’)OR21、R4YまたはOR4Yであり;
Yは、COE2、SO2E2、またはスルホンイミドであり;
R21は水素または酸解離性保護基であり;
Rf’は、各存在で同一または異なると共に、1〜10個の炭素原子のフルオロアルキル基であり、または共に(CF2)e(ここでeは2〜10である)であり;
R4はアルキレン基であり;
E2は、OH、ハロゲン、またはOR7であり;および
R5はアルキル基であり;
ただし、R17〜R20の少なくとも1つがY、R4YまたはOR4Yである。
この実施例は、新たな導電性ポリマー組成物の調製において用いられる有機溶剤でぬらすことができるスルホン酸ポリマーの調製を例示する。ポリマーは、1,1−ジフルオロエチレン(「VF2」)および2−(1,1−ジフルオロ−2−(トリフルオロメチル)アリルオキシ)−1,1,2,2−テトラフルオロエタンスルホニルフッ化物(「PSEBVE」)のコポリマーであり、これをスルホン酸形態に転化した。得られたポリマーは、「VF2−PSSEBVE」として称される。
この実施例は、新たな導電性ポリマー組成物の調製において用いられる有機溶剤でぬらすことができるスルホン酸ポリマーの調製を例示する。ポリマーは、エチレン(「E」)および2−(2−(1,2,2−トリフルオロビニルオキシ)−1,1,2,3,3,3−ヘキサフルオロプロポキシ)−1,1,2,2−テトラフルオロエタンスルホニルフッ化物(「PSEPVE」)のコポリマーであり、これをスルホン酸形態に転化した。得られたポリマーは、「E−PSEPVE酸」として称される。
この実施例は、市販されている導電性ポリマーと有機溶剤でぬらすことができるフッ素化酸ポリマーとをブレンドすることによる導電性ポリマー組成物の調製を例示する。導電性ポリマーはPEDT/PSSであった。有機溶剤でぬらすことができるフッ素化酸ポリマーは、実施例2からのE−PSEPVE酸であった。
この実施例は、ベイトロン(Baytron)−P(登録商標)AI4083(Lot番号HCD04P012、固体:1.5%、pH約1.7;PEDT/PSSの間のw/w比1:6)と、実施例1において形成した2.5%(w/w)VF2/PSEBVEスルホン酸の水溶液とをブレンドすることにより形成した新たな導電性ポリマー組成物を例示している。
この実施例は、ベイトロン(Baytron)−P(登録商標)の素子性能を例示する。
この実施例は、ベイトロン(Baytron)−Pと、ナフィオン(Nafion)(登録商標)ぬらすことができないパーフルオロ−高分子スルホン酸とのブレンド製のフィルムの高接触角を例示する。ベイトロン(Baytron)−P/ナフィオン(Nafion)(登録商標)ブレンドは、1モルPEDT対ナフィオン(Nafion)(登録商標)の0.2酸均等物の比を有する。
この実施例は、ベイトロン(Baytron)−Pと、ナフィオン(Nafion)(登録商標)、ぬらすことができないパーフルオロ−高分子スルホン酸とのブレンドの高接触角を例示している。ベイトロン(Baytron)−P/ナフィオン(Nafion)(登録商標)ブレンドは、1モルPEDT対ナフィオン(Nafion)(登録商標)の0.8酸均等物の比を有している。
この実施例は、高%E−PSEPVEスルホン酸と、ベイトロン(Baytron)−P(登録商標)AI4083とのブレンドを例示すると共に、および素子性能へのpHの影響を例示する。
この実施例は、高%VF2/PSEBVEスルホン酸とベイトロン(Baytron)−P(登録商標)AI4083とのブレンドを例示すると共に、素子性能へのpHの影響を例示する。
本発明は以下の実施の態様を含むものである。
1.少なくとも1種の有機溶剤でぬらすことができるフッ素化酸ポリマーと混合状態にある少なくとも1種のドープ導電性ポリマーを含むことを特徴とするポリマー組成物。
2.導電性ポリマーが、ポリチオフェン、ポリピロール、ポリアニリン、高分子縮合多環式ヘテロ芳香族、これらのコポリマー、およびこれらの組み合わせから選択されることを特徴とする前記1.に記載の組成物。
3.ポリチオフェンが式I
R 1 は、独立に、各存在で同一または異なるよう選択されると共に、水素、アルキル、アルケニル、アルコキシ、アルカノイル、アルキルチオ、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、アクリル酸、リン酸、ホスホン酸、ハロゲン、ニトロ、シアノ、ヒドロキシル、エポキシ、シラン、シロキサン、アルコール、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、アミドスルホネート、エーテルスルホネート、エステルスルホネート、およびウレタンから選択され;または両方のR 1 基は一緒になって、任意選択的に1つまたは複数の二価の窒素、硫黄または酸素原子を含んでもよい3、4、5、6または7員芳香族または脂環式環を完成させるアルキレンまたはアルケニレン鎖を形成してもよく、および
nは少なくとも約4である)
を有することを特徴とする前記2.に記載の組成物。
4.ポリチオフェンが式I(a)
R 7 は、各存在で同一または異なると共に、水素、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、エステルスルホネート、およびウレタンから選択され、ただし、少なくとも1つのR 7 は水素ではなく、
mは2または3であり、および
nは少なくとも約4である)
を有することを特徴とする前記2.に記載の組成物。
5.ポリピロールが式II
nは少なくとも約4であり;
R 1 は、独立に、各存在で同一または異なるよう選択されると共に、水素、アルキル、アルケニル、アルコキシ、アルカノイル、アルキルチオ、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、アクリル酸、リン酸、ホスホン酸、ハロゲン、ニトロ、シアノ、ヒドロキシル、エポキシ、シラン、シロキサン、アルコール、ベンジル、カルボキシレート、エーテル、アミドスルホネート、エーテルカルボキシレート、エーテルスルホネート、エステルスルホネート、およびウレタンから選択され;または両方のR 1 基は一緒になって、任意選択的に1つまたは複数の二価の窒素、硫黄または酸素原子を含んでもよい3、4、5、6または7員芳香族または脂環式環を完成させるアルキレンまたはアルケニレン鎖を形成してもよく;および
R 2 は、独立に、各存在で同一または異なるよう選択されると共に、水素、アルキル、アルケニル、アリール、アルカノイル、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、エポキシ、シラン、シロキサン、アルコール、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、エステルスルホネート、およびウレタンから選択される)
を有することを特徴とする前記2.に記載の組成物。
6.ポリアニリンが、式III、式IV、およびこれらの組み合わせ
nは少なくとも約4であり;
pは0〜4の整数であり;
mは1〜5の整数であり、ただし、p+m=5であり;および
R 3 は、独立に、各存在で同一または異なるよう選択されると共に、アルキル、アルケニル、アルコキシ、シクロアルキル、シクロアルケニル、アルカノイル、アルキルチオ、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、カルボン酸、ハロゲン、シアノ、または1つまたは複数のスルホン酸、カルボン酸、ハロ、ニトロ、シアノまたはエポキシ部分で置換されたアルキルから選択され;またはいずれか2つのR 3 基は一緒になって、任意選択的に1つまたは複数の二価の窒素、硫黄または酸素原子を含んでもよい3、4、5、6または7員芳香族または脂環式環を完成させるアルキレンまたはアルケニレン鎖を形成してもよい)
から選択される式を有することを特徴とする前記2.に記載の組成物。
7.高分子縮合多環式ヘテロ芳香族が式V
QはSまたはNHであり;
R 8 、R 9 、R 10 、およびR 11 は、独立に、各存在で同一または異なるよう選択されると共に、水素、アルキル、アルケニル、アルコキシ、アルカノイル、アルキルチオ、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、アクリル酸、リン酸、ホスホン酸、ハロゲン、ニトロ、シアノ、ヒドロキシル、エポキシ、シラン、シロキサン、アルコール、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、アミドスルホネート、エーテルスルホネート、エステルスルホネート、およびウレタンから選択され;および
R 8 およびR 9 、R 9 およびR 10 、ならびにR 10 およびR 11 の少なくとも1つは一緒になって、任意選択的に1つまたは複数の二価の窒素、硫黄または酸素原子を含んでもよい5または6員芳香族環を完成させるアルケニレン鎖を形成する)
を有するモノマーから誘導されることを特徴とする前記2.に記載の組成物。
8.導電性ポリマーが式VI
QはSまたはNR 6 であり;
Tは、S、NR 6 、O、SiR 6 2 、Se、およびPR 6 から選択され;
Zは、アルケニレン、アリーレン、およびヘテロアリーレンから選択され;
R 6 は水素またはアルキルであり;
R 12 は、各存在で同一または異なると共に、水素、アルキル、アルケニル、アルコキシ、アルカノイル、アルキルチオ、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、アクリル酸、リン酸、ホスホン酸、ハロゲン、ニトロ、ニトリル、シアノ、ヒドロキシル、エポキシ、シラン、シロキサン、アルコール、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、アミドスルホネート、エーテルスルホネート、エステルスルホネート、およびウレタンから選択される)
を有する前駆体モノマーから誘導されることを特徴とする前記2.に記載の組成物。
9.導電性ポリマーが、ポリ(3,4−エチレンジオキシチオフェン)、非置換ポリピロール、非置換ポリアニリン、ポリ(チエノ(2,3−b)チオフェン)、ポリ(チエノ(3,2−b)チオフェン)、およびポリ(チエノ(3,4−b)チオフェン)から選択されることを特徴とする前記1.に記載の組成物。
10.ドープ導電性ポリマーが、非フッ素化高分子酸ドーパントを含むことを特徴とする前記1.に記載の組成物。
11.ドープ導電性ポリマーが、高分子スルホン酸を含むことを特徴とする前記1.に記載の組成物。
12.有機溶剤でぬらすことができるフッ素化酸ポリマーが、カルボン酸基、スルホン酸基、スルホンイミド基、リン酸基、ホスホン酸基、およびこれらの組み合わせから選択される酸性基を含むことを特徴とする前記1.に記載の組成物。
13.有機溶剤でぬらすことができるフッ素化酸ポリマーが、ポリオレフィン、ポリアクリレート、ポリメタクリレート、ポリイミド、ポリアミド、ポリアラミド、ポリアクリルアミド、およびこれらのコポリマーから選択される主鎖を含むことを特徴とする前記1.に記載の組成物。
14.有機物でぬらすことができるフッ素化酸ポリマーが、アルキル基、アルコキシ基、アミド基、エーテル基、およびこれらの組み合わせから選択されるフッ素化側鎖を含むことを特徴とする前記1.に記載の組成物。
15.有機溶剤でぬらすことができるフッ素化酸ポリマーが、フッ素化エーテルスルホネート基およびフッ素化エーテルスルホンイミド基から選択されるフッ素化オレフィン主鎖および側基を含むことを特徴とする前記1.に記載の組成物。
16.有機溶剤でぬらすことができるフッ素化酸ポリマーが、
1,1−ジフルオロエチレンおよび2−(2,2−ジフルオロ−2−(トリフルオロメチル)アリルオキシ)−1,1,2,2−テトラフルオロエタンスルホン酸のコポリマー;エチレンおよび2−(2−(1,2,2−トリフルオロビニルオキシ)−1,1,2,3,3,3−ヘキサフルオロプロポキシ)−1,1,2,2−テトラフルオロエタンスルホン酸のコポリマー;およびこれらの組み合わせから選択されることを特徴とする前記1.に記載の組成物。
17.有機溶剤でぬらすことができるフッ素化酸ポリマーが、フッ素化および部分スルホン化アリーレンエーテルスルホンを含むことを特徴とする前記1.に記載の組成物。
18.有機溶剤でぬらすことができるフッ素化酸ポリマーが式VIIおよび式VIII
qは1〜5の整数であり、
R 13 はOHまたはNHR 14 であり、および
R 14 は、アルキル、フルオロアルキル、スルホニルアルキル、またはスルホニルフルオロアルキルである);
および式VIII
Wは、(CF 2 ) q 、O(CF 2 ) q 、S(CF 2 ) q 、(CF 2 ) q O(CF 2 ) r から選択され、
qおよびrは、独立に1〜5の整数であり、
R 13 はOHまたはNHR 14 であり、および
R 14 は、アルキル、フルオロアルキル、スルホニルアルキル、またはスルホニルフルオロアルキルである)
から選択される式を有する少なくとも1種のモノマーから誘導されることを特徴とする前記1.に記載の組成物。
19.有機溶剤でぬらすことができるフッ素化酸ポリマーが式IX
R f は、フッ素化アルキレン、フッ素化ヘテロアルキレン、フッ素化アリーレン、およびフッ素化ヘテロアリーレンから選択され;および
nは少なくとも20である)
を有することを特徴とする前記1.に記載の組成物。
20.有機物でぬらすことができるフッ素化酸ポリマーが式X
R 15 は、フッ素化アルキレン基またはフッ素化ヘテロアルキレン基であり;
R 16 は、フッ素化アルキルまたはフッ素化アリール基であり;および
pは、0または1〜4の整数である)
を有する側鎖を含むフッ素化ポリマー主鎖を含むことを特徴とする前記1.に記載の組成物。
21.有機溶剤でぬらすことができるフッ素化酸ポリマーが式XI
R 16 は、フッ素化アルキルまたはフッ素化アリール基であり;
a、b、c、dおよびeは、それぞれ独立に0または1〜3の整数であり;および
nは少なくとも4である)
を有することを特徴とする前記1.に記載の組成物。
22.有機溶剤でぬらすことができるフッ素化酸ポリマーが、接触角40°以下でフェニルヘキサンによってぬらすことができるフィルムを形成することを特徴とする前記1.に記載の組成物。
23.フッ素化酸ポリマーが、接触角35°以下でフェニルヘキサンによってぬらすことができるフィルムを形成することを特徴とする前記9.に記載の組成物。
24.少なくとも1種の有機溶剤でぬらすことができるフッ素化酸ポリマーとブレンドされた少なくとも1種の導電性ポリマーを含むポリマー組成物の水性分散体であって、前記組成物が1.5〜4のpHを有することを特徴とする水性分散体。
25.pHが2〜3であることを特徴とする前記24.に記載の分散体。
26.少なくとも1種の有機溶剤でぬらすことができるフッ素化酸ポリマーとブレンドされた少なくとも1種のドープ導電性ポリマーを含むポリマー組成物を含む少なくとも1つの緩衝層を含むことを特徴とする電子素子。
27.導電性ポリマーが、ポリチオフェン、ポリピロール、ポリアニリン、高分子縮合多環式ヘテロ芳香族、これらのコポリマー、およびこれらの組み合わせから選択されることを特徴とする前記26.に記載の素子。
28.導電性ポリマーが、ポリ(3,4−エチレンジオキシチオフェン)、非置換ポリピロール、非置換ポリアニリン、ポリ(チエノ(2,3−b)チオフェン)、ポリ(チエノ(3,2−b)チオフェン)、およびポリ(チエノ(3,4−b)チオフェン)から選択されることを特徴とする前記26.に記載の素子。
29.有機溶剤でぬらすことができるフッ素化酸ポリマーが、カルボン酸基、スルホン酸基、スルホンイミド基、リン酸基、ホスホン酸基、およびこれらの組み合わせから選択される酸性基を含むことを特徴とする前記26に記載の素子。
30.有機溶剤でぬらすことができるフッ素化スルホン酸ポリマーが、ポリオレフィン、ポリアクリレート、ポリメタクリレート、ポリイミド、ポリアミド、ポリアラミド、ポリアクリルアミド、およびこれらのコポリマーから選択される主鎖を含むことを特徴とする前記26.記載の素子。
31.有機溶剤でぬらすことができるフッ素化スルホン酸ポリマーが、フッ素化オレフィン主鎖および側鎖フッ素化エーテルスルホネート基を含むことを特徴とする前記26.に記載の素子。
32.有機溶剤でぬらすことができるフッ素化スルホン酸ポリマーが、
1,1−ジフルオロエチレンおよび2−(2,2−ジフルオロ−2−(トリフルオロメチル)アリルオキシ)−1,1,2,2−テトラフルオロエタンスルホン酸のコポリマー;エチレンおよび2−(2−(1,2,2−トリフルオロビニルオキシ)−1,1,2,3,3,3−ヘキサフルオロプロポキシ)−1,1,2,2−テトラフルオロエタンスルホン酸のコポリマー;およびこれらの組み合わせから選択されることを特徴とする前記26.に記載の素子。
33.有機溶剤でぬらすことができるフッ素化酸ポリマーが、フッ素化および部分スルホン化アリーレンエーテルスルホンを含むことを特徴とする前記26.に記載の素子。
Claims (3)
- 少なくとも1種のフッ素化酸ポリマーとブレンドされた少なくとも1種のドープ導電性ポリマーを含むポリマー組成物の水性分散体であって、前記組成物が1.5〜4のpHを有し、
前記フッ素化酸ポリマーは、2−(1,1−ジフルオロ−2−トリフルオロメチル)アリルオキシ−1,1,2,2−テトラフルオロエタンスルホニルフッ化物と1,1−ジフルオロエチレンとの共重合体、または2−(2−(1,2,2−トリフルオロビニルオキシ)−1,1,2,3,3,3−ヘキサフルオロプロポキシ)−1,1,2,2−テトラフルオロエタンスルホニルフッ化物とエチレンとの共重合体であり、
そのフィルムがフェニルヘキサンによって40°未満の接触角でぬらすことができることを特徴とする水性分散体。 - 陰極、緩衝層、電子活性層、および陽極層を含む電子素子であって、
前記緩衝層は少なくとも1種のフッ素化酸ポリマーとブレンドされた少なくとも1種のドープ導電性ポリマーを含み、
前記フッ素化酸ポリマーは、2−(1,1−ジフルオロ−2−トリフルオロメチル)アリルオキシ−1,1,2,2−テトラフルオロエタンスルホニルフッ化物と1,1−ジフルオロエチレンとの共重合体、または2−(2−(1,2,2−トリフルオロビニルオキシ)−1,1,2,3,3,3−ヘキサフルオロプロポキシ)−1,1,2,2−テトラフルオロエタンスルホニルフッ化物とエチレンとの共重合体であり、
そのフィルムがフェニルヘキサンによって40°未満の接触角でぬらすことができることを特徴とする電子素子。 - 前記請求項1に記載の水性分散体から堆積された少なくとも1つの緩衝層を含む電子素子。
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WO2007002683A2 (en) | 2007-01-04 |
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EP1899993B1 (en) | 2012-06-27 |
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