CN103201341A - 包含具有确定的硫酸根含量的聚噻吩的分散体 - Google Patents
包含具有确定的硫酸根含量的聚噻吩的分散体 Download PDFInfo
- Publication number
- CN103201341A CN103201341A CN2011800493234A CN201180049323A CN103201341A CN 103201341 A CN103201341 A CN 103201341A CN 2011800493234 A CN2011800493234 A CN 2011800493234A CN 201180049323 A CN201180049323 A CN 201180049323A CN 103201341 A CN103201341 A CN 103201341A
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- Prior art keywords
- composition
- polythiophene
- thiophene
- sulfate radical
- dispersion
- Prior art date
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- 229920000123 polythiophene Polymers 0.000 title claims abstract description 50
- 239000006185 dispersion Substances 0.000 title claims description 70
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 149
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 63
- 229930192474 thiophene Natural products 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 27
- 230000003647 oxidation Effects 0.000 claims abstract description 5
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 5
- -1 alkali metal salts Chemical class 0.000 claims description 62
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 32
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 29
- 229920000447 polyanionic polymer Polymers 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 239000002585 base Substances 0.000 claims description 20
- 229910052742 iron Inorganic materials 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 11
- 230000005540 biological transmission Effects 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 238000012360 testing method Methods 0.000 claims description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 4
- 235000011152 sodium sulphate Nutrition 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 238000010276 construction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 28
- 150000003839 salts Chemical class 0.000 description 17
- 150000002500 ions Chemical class 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 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 2
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 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 2
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- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
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- 125000006833 (C1-C5) alkylene group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及一种制备包含聚噻吩的组合物的方法,其包括如下方法步骤:I)提供包含噻吩类单体和氧化剂的组合物Z1;II)通过将所述氧化剂还原成还原产物并将所述噻吩类单体氧化而氧化聚合所述噻吩类单体,从而形成包含聚噻吩和所述还原产物的组合物Z2;III)从在方法步骤II)中获得的组合物Z2中至少部分移除所述还原产物以获得组合物Z3;其中组合物Z3的硫酸根含量为100-1,000ppm,基于组合物Z3的总重量。本发明还涉及一种可通过该方法作为组合物Z3获得的组合物、一种包含聚噻吩的组合物、一种层结构体、一种电子组件和组合物的用途。
Description
本发明涉及一种制备包含聚噻吩的组合物的方法、可通过所述方法获得的组合物、包含聚噻吩的组合物、层结构体、电子组件和组合物的用途。
由于与金属相比,聚合物具有就加工能力、重量和通过化学改性靶向调节性能的优点,导电聚合物的商业重要性日益提高。已知的π共轭聚合物实例为聚吡咯、聚噻吩、聚苯胺、聚乙炔、聚亚苯基和聚(对亚苯基-亚乙烯基)。由导电聚合物制成的层用于许多技术领域中,例如作为聚合物对电极用于电容器中或者用于在电子电路板中贯通接触。导电聚合物的制备通过由单体前体如取代的噻吩、吡咯和苯胺及其相应的任选低聚物衍生物氧化而化学或电化学地实现。特别地,化学氧化聚合被广泛使用,这是因为其在工业上可容易地在液体介质中和许多不同底物上实现。
工业上所用的特别重要的聚噻吩为聚(乙撑-3,4-二氧噻吩)(PEDOT或PEDT)例如公开于EP0339340A2中,其通过乙撑-3,4-二氧噻吩(EDOT或EDT)的化学聚合制备,且在其氧化形式下具有非常好的导电性。许多聚(亚烷基-3,4-二氧噻吩)衍生物、特别是聚(乙撑-3,4-二氧噻吩)衍生物、其单体组分、合成和用途的综述由L.Groenendaal,F.Jonas,D.Freitag,H.Pielartzik和J.R.Reynolds描述于Adv.Mater.12,(2000),第481-494页中。
工业上特别重要的是具有例如EP0440957A2所公开的聚阴离子如聚苯乙烯磺酸的PEDOT的分散体。由这些分散体可制备透明导电膜,所述导电膜具有许多用途,例如作为抗静电涂层或作为有机发光二极管(OLED)中的空穴注入层,如EP1227529A2所公开的那样。
EDOT的聚合在聚阴离子的水溶液中进行,并形成聚电解质配合物。包含聚阴离子作为抗衡离子以补偿电荷的阳离子聚噻吩通常也被本领域技术人员称为聚噻吩/聚阴离子配合物(PEDOT/PSS配合物)。由于以PEDOT作为聚阳离子且以PSS作为聚阴离子的聚电解质的性质,该配合物并非真溶液,而是分散体。聚合物或部分聚合物的溶解或分散程度取决于聚阳离子与聚阴离子的质量比、所述聚合物的电荷密度、周围的盐浓度以及周围的介质特性(V.Kabanov,Russian Chemical Reviews74,2005,3-20)。这些转变可为流体。出于该原因,在下文中对措辞“分散的”与“溶解的”不加以区分。类似地,对“分散性”与“溶解性”或者“分散剂”与“溶剂”不加以区分。相反,这些措辞在本文中等同使用。
现有技术中所述的导电聚合物分散体的缺点,特别是与现有技术所已知的PEDOT/PSS分散体有关的缺点在于,其在长期储存后倾向于“胶凝”。该分散体的胶凝尤其表现在当例如将所述分散体倾倒出容器中时,所述分散体不均匀流动,而是留下其中任何分散体难以保留的区域。所述材料的非均匀流动是常见的,其特征在于频繁的破裂。在出于涂覆目的将所述分散体所施加至其上的基材上,其也极其不均匀地铺展。然而,由于PEDOT/PSS分散体通常用于制备导电层且因此必须施加至基材表面,该胶凝也对均匀性且因此对所述PEDOT/PSS层的电性能具有决定性的影响。此外,现有技术所已知的PEDOT/PSS分散体的特征还在于用该分散体获得的层通常具有需要改进的导电性。
因此,本发明的目的是克服现有技术的与包含聚噻吩的组合物有关的缺点,特别是与PEDOT/PSS分散体有关的缺点,以及与由该组合物或由该分散体制备的层压体有关的缺点。
特别地,本发明的目的在于提供一种制备包含聚噻吩的组合物,优选PEDOT/PSS分散体的方法,其特征尤其在于即使在长储存时间后,也几乎不具有任何胶凝倾向或优选不具有胶凝倾向。
因此,此外,可用该方法获得的组合物或分散体的特征应在于,由所述组合物或分散体制备的层的特征在于具有特别高的电导率。
因此,本发明的目的还在于提供一种包含聚噻吩的组合物,优选PEDOT/PSS分散体,与现有技术所已知的组合物或分散体相比,其特征在于在由其制备的层中获得良好的加工性和高电导率的特别有利的组合。
本发明的另一目的在于母线的整流滤波(smoothing)。在OLED和OPV结构的情况下,由于将通常具有10-200nm厚度的其他层施加至所述聚噻吩层上,因此要求具有低表面粗糙度。如果具有高粗糙度,则会破坏该层结构。
对解决这些问题的贡献由一种制备包含聚噻吩的组合物的方法作出,所述方法包括如下方法步骤:
I)提供包含噻吩类单体和氧化剂的组合物Z1;
II)通过将所述氧化剂还原成还原产物并将所述噻吩类单体氧化而氧化聚合所述噻吩类单体,从而形成包含聚噻吩和所述还原产物的组合物Z2;
III)从在方法步骤II)中获得的组合物Z2中至少部分移除所述还原产物以获得组合物Z3;
其中组合物Z3的硫酸根含量为100-1,000ppm,优选为100-500ppm,特别优选为100-200ppm,在每种情况下基于组合物Z3的总重量。
令人惊讶地发现,如果在所述组合物或分散体中建立特定的硫酸根含量,其特征在于最小值为约100ppm且最大值为约1,000ppm,可显著提高包含聚噻吩的组合物,特别是PEDOT/PSS分散体的储存稳定性(就其“胶凝行为”而言)以及基于所述组合物或分散体获得的层的电导率。如果硫酸根的浓度低于100ppm,则不能通过添加硫酸根实现电导率的显著提高。如果硫酸根的浓度高于1000ppm,则观察到所述组合物或分散体的粘度显著提高,这最终导致胶凝并妨碍所述组合物或分散体的加工。
在本发明方法的方法步骤I)中,首先提供包含噻吩类单体和氧化剂的组合物Z1。
所用的噻吩类单体优选为式(I)化合物:
其中:
A表示任选取代的C1-C5亚烷基;
R彼此独立地表示H、直链或支化的任选取代的C1-C18烷基、任选取代的C5-C12环烷基、任选取代的C6-C14芳基、任选取代的C7-C18芳烷基、任选取代的C1-C4羟基烷基或羟基;
x表示0-8的整数,且
在多个基团R键接至A的情况下,所述基团可相同或不同。通式(I)应理解为取代基R可键接至亚烷基A上达x次。
特别优选其中A表示任选取代的C2-C3亚烷基且x表示0或1的通式(I)噻吩类单体。尤其优选作为噻吩类单体的为3,4-乙撑二氧噻吩,其在方法步骤II)中聚合以获得聚(3,4-乙撑二氧噻吩)。
根据本发明,C1-C5亚烷基A优选为亚甲基、亚乙基、亚正丙基、亚正丁基或亚正戊基。C1-C18烷基R优选表示直链或支化的C1-C18烷基,如甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、2,2-二甲基丙基、正己基、正庚基、正辛基、2-乙基己基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十六烷基或正十八烷基;C5-C12环烷基R表示例如环戊基、环己基、环庚基、环辛基、环壬基或环癸基;C6-C14芳基R表示例如苯基或萘基;且C7-C18芳烷基R表示例如苄基、邻甲苯基、间甲苯基、对甲苯基、2,3-二甲苯基、2,4-二甲苯基、2,5-二甲苯基、2,6-二甲苯基、3,4-二甲苯基、3,5-二甲苯基或基。上述列表用于示例性阐述本发明,且不应视为排他性的。
就本发明而言,基团A和/或基团R的其他可能的取代基为许多有机基团,例如烷基、环烷基、芳基、芳烷基、烷氧基、卤素、醚基、硫醚基、二硫醚基、亚砜基、砜基、磺酸酯基、氨基、醛基、酮基、羧酸酯基、羧酸基、碳酸酯基、羧酸盐基(carboxylate)、氰基、烷基硅烷基和烷氧基硅烷基以及羧酰胺基。
除所述噻吩类单体之外,方法步骤I)中所提供的配混物还包含氧化剂。作为氧化剂,可使用适于氧化聚合吡咯的氧化剂;所述氧化剂例如描述于J.Am.Chem.Soc.85,454(1963)中。优选地,出于实际原因,经济的且易于使用的氧化剂例如为铁III盐,如FeCl3、Fe(ClO4)3以及有机酸的铁III盐和具有有机基团的无机酸的铁III盐;以及H2O2、K2Cr2O7;过硫酸碱金属盐和铵盐;过硼酸碱金属盐;高锰酸钾和铜盐如四氟硼酸铜。所述过硫酸盐以及有机酸和具有有机基团的无机酸的铁III盐的应用在实践中具有很大的优势,因为其不具有腐蚀作用。具有有机基团的无机酸的铁III盐实例为硫酸的C1-C20链烷醇半酯的铁III盐,例如月桂基硫酸酯的Fe-III盐。有机酸的铁III盐实例为C1-C20烷基磺酸,如甲烷磺酸或十二烷磺酸的Fe-III盐;脂族C1-C20羧酸如2-乙基己基羧酸的Fe-III盐;脂族全氟羧酸如三氟乙酸和全氟辛酸的Fe-III盐;脂族二羧酸如草酸的Fe-III盐;和最重要的,任选被C1-C20烷基取代的芳族磺酸如苯磺酸、对甲苯磺酸和十二烷基苯磺酸的Fe-III盐。
理论上,对式I噻吩类单体的氧化聚合而言,每摩尔噻吩需要2.25当量的氧化剂(参见例如J.Polym.Sc.,Part A,Polymer Chemistry,第26卷,第1287页(1988))。然而,实际上,所述氧化剂通常以特定过量量,例如基于每摩尔噻吩过量0.1-2当量的量使用。
根据本发明方法的特别优选的实施方案,在方法步骤I)中提供的组合物还包含聚阴离子,其中聚阴离子优选应理解为包含至少2个,优选至少3个,特别优选至少4个,尤其优选至少10个相同的阴离子单体重复单元,然而其不必彼此之间连接的聚合物型阴离子。
聚阴离子例如可为聚合物羧酸的阴离子,例如聚丙烯酸、聚甲基丙烯酸或聚马来酸,或聚合磺酸如聚苯乙烯磺酸和聚乙烯基磺酸的阴离子。所述聚羧酸和聚磺酸也可为乙烯基羧酸和乙烯基磺酸与其他可聚合单体如丙烯酸酯和苯乙烯的共聚物。优选包含在方法步骤I)中所提供的分散体中且作为聚阴离子的为聚合物羧酸或磺酸的阴离子。
特别优选作为聚阴离子的为聚苯乙烯磺酸(PSS)的阴离子。提供所述聚阴离子的聚酸的分子量(MW)优选为1,000-2,000,000,特别优选为2,000-500,000。分子量的测定通过凝胶渗透色谱法借助具有确定分子量的聚苯乙烯磺酸作为标定标样而进行。所述聚酸或其碱金属盐可商购获得,例如聚苯乙烯磺酸和聚丙烯酸,或者用已知方法制备(参见例如HoubenWeyl,Methoden der organischen Chemie[有机化学方法],第E20卷,Makromolekulare Stoffe[大分子物质],第2部分(1987),第1141页及随后各页)。
步骤I)中所提供的组合物中可包含所述聚阴离子和所述噻吩类单体,特别是以0.5:1-50:1,优选1:1-30:1,特别优选2:1-20:1的重量比。
根据本发明,除所述噻吩类单体、氧化剂和任选的聚阴离子之外,还优选步骤I)中所提供的组合物包含溶剂或分散剂或溶剂和/或分散剂的混合物,其中所述组分溶解或分散于其中。作为溶剂和/或分散剂例如提及下述物质:脂族醇,如甲醇、乙醇、异丙醇和正丁醇;脂族酮,如丙酮和甲基乙基酮;脂族羧酸酯,如乙酸乙酯和乙酸丁酯;芳族烃,如甲苯和二甲苯;脂族烃,如己烷、庚烷和环己烷;氯代烃,如二氯甲烷和二氯乙烷;脂族腈,如乙腈;脂族亚砜和砜,如二甲亚砜和环丁砜;脂族羧酰胺,如甲基乙酰胺、二甲基乙酰胺和二甲基甲酰胺;脂族和芳脂族醚,如乙醚和苯甲醚。此外,可使用水或水与上述有机溶剂的混合物作为溶剂或分散剂。优选的溶剂和分散剂为水或其他质子溶剂如醇,例如甲醇、乙醇、异丙醇和丁醇,以及水与所述醇的混合物,特别优选的溶剂或分散剂为水。
优选对方法步骤I)中所制备的组合物中所含的噻吩类单体和聚阴离子的量或浓度进行选择,以获得稳定的聚噻吩/聚阴离子分散体,其中所述分散体的固含量为0.05-50重量%,优选0.1-10重量%,特别优选1-5重量%。
在本发明方法的方法步骤II)中,通过将所述氧化剂还原成还原产物并将所述噻吩类单体氧化而氧化聚合所述噻吩类单体,从而形成优选包含阳离子聚噻吩和所述还原产物的组合物Z2,其中所述聚合优选在0-100°C的温度下进行。如果在方法步骤I)中所提供的组合物中存在聚阴离子,则在方法步骤II)中获得包含聚阴离子作为抗衡离子以补偿电荷的阳离子聚噻吩,如上所述,其通常也被本领域技术人员称为聚噻吩/聚阴离子配合物。根据本发明,特别优选的聚噻吩/聚阴离子配合物为PEDOT/PSS配合物。
就本发明而言,前缀“聚”应理解为意指所述聚合物或聚噻吩中包含超过一个相同或不同的重复单元。在方法步骤II)中形成的聚噻吩包含总共n个通式(I)的重复单元,其中n为2-2,000,优选2-100的整数。所述聚噻吩中的通式(I)重复单元可相同或不同,这取决于在方法步骤I)中所制备的组合物中是存在相同还是不同的噻吩类单体。
通过氧化聚合在方法步骤II)中形成的聚噻吩,特别是上述聚(3,4-乙撑二氧噻吩)可为电中性的或阳离子性的。在特别优选的实施方案中,其为阳离子性的,且措辞“阳离子性的”仅涉及位于聚噻吩主链上的电荷。取决于基团R上的取代基,所述聚噻吩可在结构单元中带有正电荷和负电荷,其中所述正电荷位于聚噻吩主链上且负电荷可任选位于被磺酸根或羧酸根取代的基团R上。聚噻吩主链上的正电荷可部分被可能存在于基团R上的阴离子基团补偿。总体来说,在这些情况下,所述聚噻吩可为阳离子性的、中性的或者甚至阴离子性的。然而,就本发明而言,由于聚噻吩主链上的正电荷是决定性的,将其全部视为阳离子聚噻吩。正电荷的数量优选至少为1且至多为n,其中n为聚噻吩中所有重复单元(相同或不同)的总数。
在本发明方法的方法步骤III)中,从在方法步骤II)中获得的组合物Z2中至少部分移除所述还原产物,从而获得组合物Z3。还原产物的移除优选通过用一种或多种离子交换剂处理组合物Z2而进行。借助所述方法,不仅使在方法步骤II)中获得的组合物脱除还原产物,而且通常脱除仍然存在的盐。可将所述离子交换剂例如搅入在方法步骤II)中获得的组合物Z2中,或者使在方法步骤II)中获得的组合物Z2通过一个或多个填充有离子交换剂的柱。特别优选用阴离子交换剂和阳离子交换剂二者处理在方法步骤II)中获得的组合物。合适的阳离子和阴离子交换剂的实例为可由Lanxess AG以商品名LEWATIT获得的离子交换剂。
根据本发明,特别优选组合物Z2或组合物Z3为包含PEDOT/PSS配合物的组合物。优选组合物Z2或组合物Z3为PEDOT/PSS分散体。其中硫酸根含量尚未设定为100-1,000ppm的组合物Z3的具体实例为可以以商品名获自H.C.Stark Clevios GmbH的分散体。
本发明方法的特征在于组合物Z3的硫酸根含量为100-1,000ppm,优选为100-500ppm,特别优选为100-200ppm,在每种情况下基于组合物Z3的总重量。在这种情况下,措辞“硫酸根”意指优选以溶解形式包含在所述组合物中的非化学键接的阴离子SO4 2-。措辞“硫酸根”还用于意指在低pH值下存在的硫酸根离子HSO4 -或H2SO4的质子化形式。
就此而言,优选通过将硫酸或硫酸的盐添加至组合物Z3中而调节组合物Z3中的硫酸根含量。优选地,在如上所述优选通过用一种或多种离子交换剂处理组合物Z2而至少部分移除所述还原产物之后,向以此方式获得的组合物中添加合适量的硫酸或合适量的硫酸盐或合适量的硫酸与硫酸盐的混合物。所用的硫酸盐可为本领域技术人员所已知的任意硫酸盐,其中特别优选使用水溶性硫酸盐。合适硫酸盐的实例例如为硫酸的碱金属盐,如硫酸钠或硫酸钾;硫酸的铵盐,如硫酸铵或硫酸氢铵;硫酸的碱土金属盐,如硫酸镁或硫酸钙;或三价阳离子的硫酸盐,如硫酸铝或明矾。
对解决上述问题的贡献也由一种可通过上述方法作为组合物Z3获得的组合物作出,其优选具有100-1,000ppm,优选100-500ppm,特别优选100-200ppm的硫酸根含量,在每种情况下基于组合物Z3的总重量。
对解决上述问题的贡献也由一种包含聚噻吩的组合物作出,其中所述组合物除所述聚噻吩之外,还包含100-1,000ppm的硫酸根,优选100-500ppm的硫酸根,特别优选100-200ppm的硫酸根,在每种情况下基于所述组合物的总重量。在这种情况下,措辞“硫酸根”也意指优选以溶解形式包含于所述组合物中的非化学键接的阴离子SO4 2-。措辞“硫酸根”还用于意指在低pH值下存在的硫酸根离子HSO4 -或H2SO4的质子化形式。
根据本发明组合物的优选实施方案,组合物Z3的铁浓度小于200ppm,优选小于50ppm,尤其优选小于10ppm,在每种情况下基于所述组合物的总重量。
根据本发明的优选实施方案,通过下文方法测定的分散体中的基于交联聚苯乙烯衍生物的颗粒状离子交换剂的颗粒浓度为小于20,优选小于10,特别优选小于5。在使用基于交联聚苯乙烯衍生物的其他离子交换剂下,这也可同样适用。粒度通常为0.1-4mm的所述颗粒状离子交换剂也可包含5-100μm的更小的颗粒级分,特别是所述离子交换剂经受机械载荷时。
在另一优选实施方案中,铁浓度和离子交换剂含量二者均处于前两段中所述的限度之内。
根据本发明组合物的优选实施方案,所述聚噻吩为聚(3,4-乙撑二氧噻吩)。
根据本发明,还优选所述组合物除所述聚噻吩之外,优选除聚(3,4-乙撑二氧噻吩)之外,还包含聚阴离子,其中作为聚阴离子,优选上文就本发明方法的优选聚阴离子所给出的化合物。就此而言,特别优选的聚阴离子为聚苯乙烯磺酸(PSS)的阴离子。就此而言,还优选本发明的组合物包含PEDOT/PSS配合物。如上文就本发明方法所述的那样,这类组合物可通过使3,4-乙撑二氧噻吩在聚苯乙烯磺酸的存在下氧化聚合而获得。就此而言,特别优选本发明的组合物为PEDOT/PSS分散体。
根据本发明组合物的特定实施方案,所述组合物具有至少一种下述性能,但优选具有全部性能:
i)粘度为2-1,000mPas,优选为10-500mPas,特别优选为60-250mPas;
ii)根据本文所述的测试方法测得的电导率为至少600S/cm,优选至少500S/cm,特别优选至少400S/cm;
iii)PEDOT/PSS含量为0.05-50重量%,优选为0.1-10重量%,特别优选为1-5重量%,在每种情况下基于所述组合物的总重量。
根据本发明,特别优选具有性能i)和ii)的组合物。
对解决上述问题的贡献还由一种层结构体作出,其包括:
A)具有基材表面的基材,和
B)至少部分覆盖所述基材表面的层,
其中所述层由本发明组合物或可通过本发明方法获得的组合物中所含的固体形成。
本发明上下文中所优选的基材为塑料膜,特别优选为透明塑料膜,其厚度通常为5-5,000μm,优选为10-2,500μm,特别优选为100-1,000μm。这类塑料膜可例如基于聚合物,如聚碳酸酯、聚酯如PET和PEN(聚对苯二甲酸乙二醇酯或聚萘二甲酸乙二醇酯)、共聚碳酸酯、聚砜、聚醚砜(PES)、聚酰亚胺、聚酰胺、聚乙烯、聚丙烯或环状聚烯烃或环状烯烃共聚物(COC)、聚氯乙烯、聚苯乙烯、氢化苯乙烯聚合物或氢化苯乙烯共聚物。
在用本发明组合物涂覆之前,可对所述基材表面进行预处理,例如电晕处理、火焰处理、氟化或等离子处理,以提高所述表面的极性且因此提高润湿性和化学亲和力。
在将本发明的组合物或可通过本发明方法获得的组合物施加至所述基材表面上以形成层之前,可向所述组合物中添加能提高导电性的其他添加剂,例如含醚基的化合物,例如四氢呋喃;含内酯基的化合物,如丁内酯、戊内酯;含酰胺基或内酰胺基的化合物,如己内酰胺、N-甲基己内酰胺、N,N-二甲基乙酰胺、N-甲基乙酰胺、N,N-二甲基甲酰胺(DMF)、N-甲基甲酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮(NMP)、N-辛基吡咯烷酮、吡咯烷酮;砜和亚砜,如环丁砜(四亚甲基砜)、二甲亚砜(DMSO);糖或糖衍生物,如蔗糖、葡萄糖、果糖、乳糖;糖醇,如山梨糖醇、甘露糖醇;呋喃衍生物,如2-呋喃甲酸、3-呋喃甲酸;和/或二元醇或多元醇,如乙二醇、甘油、二甘醇或三甘醇。特别优选使用四氢呋喃、N-甲基甲酰胺、N-甲基吡咯烷酮、乙二醇、二甲亚砜或山梨糖醇作为导电性提高添加剂。
也可向所述组合物中添加一种或多种可溶于有机溶剂或水中的有机粘合剂,例如聚乙酸乙烯酯、聚碳酸酯、聚乙烯醇缩丁醛、聚丙烯酸酯、聚丙烯酰胺、聚甲基丙烯酸酯、聚甲基丙烯酰胺、聚苯乙烯、聚丙烯腈、聚氯乙烯、聚乙烯基吡咯烷酮、聚丁二烯、聚异戊二烯、聚醚、聚酯、聚氨酯、聚酰胺、聚酰亚胺、聚砜、聚硅氧烷、环氧树脂、苯乙烯/丙烯酸酯共聚物、乙酸乙烯酯/丙烯酸酯共聚物和乙烯/乙酸乙烯酯共聚物、聚乙烯醇或纤维素。当使用时,所述聚合物粘合剂的比例通常为0.1-90重量%,优选为0.5-30重量%,特别优选为0.5-10重量%,基于所述涂料组合物的总重量。
为了调节pH值,可例如向所述涂料组合物中添加酸或碱。优选这类添加剂不妨碍所述分散体成膜,例如为碱2-(二甲氨基)乙醇、2,2'-亚氨基二乙醇或2,2',2''-次氮基三乙醇。
然后可使用已知方法如旋涂、浸涂、倾注、滴流、注射、喷涂、刮刀涂覆、涂漆或印刷如喷墨印刷、丝网印刷、凹版印刷、胶版印刷或移印将所述涂料组合物以0.5-250μm的湿膜厚度,优选2-50μm的湿膜厚度施加至基材上,随后在20-200°C的温度下干燥。
优选至少部分覆盖所述基材表面的层在本发明的层压体中具有0.01-50μm,特别优选0.1-25μm,尤其优选1-10μm的层厚。
就本发明的层结构体而言,进一步优选层B)显示出如下性质:
B1)所述层的内透射率大于60%,优选大于70%,特别优选大于80%;
B2)所述层的粗糙度(Ra)小于50nm,优选小于30nm,特别优选小于20nm,尤其优选小于10nm或者甚至小于5nm。
在一些情况下,获得最高为99.5%的内透射率。在一些情况下,还获得至少0.3nm的表面粗糙度。
对解决上述问题的贡献还由一种电子组件作出,其包含本发明的层压体。优选的电子组件尤其为有机发光二极管、有机太阳能电池或电容器,其中特别优选用于电容器中,尤其是在具有作为电介质的氧化铝的电容器中用作固体电解质。
对解决上述问题的贡献还由本发明组合物或可通过本发明方法获得的组合物在制备电子组件,尤其是有机发光二极管、有机太阳能电池或电容器中的导电层中的用途作出。
现在将参照测试方法和非限制性的实施例更详细地阐述本发明。
测试方法
除非另有说明,否则所述测试在实验室中于21°C的温度、50-70%的大气湿度和大气压下进行。
硫酸根含量的测定
分散体的硫酸根含量借助离子色谱法测定。为此,使用具有离子交换剂的柱,随后进行电导率测定。所用的离子交换色谱仪为Dionex300。使用长度为50mm、内径为4.0mm且粒径为5μm的获自Dionex的IonPac AG11预处理柱。使用长度为250mm、内径为4.0mm且粒径为5μm的获自Dionex的IonPac AS11分离柱。使用水作为洗脱液。流速为1.8ml/分钟。注入体积为50μl。硫酸根在该装置中的保留时间大约为12.5分钟。借助具有DionexASRS-s抑制器的电导率检测仪检测硫酸根离子。
为了进行标定,使用95%硫酸(超纯)。将200mg硫酸化物以0.1mg的精度称量至1,000ml的量筒中,然后用水填充至标定刻度。对>5mg/kg浓度的分析精度为3%,基于测量值。在值处于1-5mg/kg的范围之内时,最大为10%,基于测量值。
离子含量的测定
借助电感耦合等离子体质谱仪(ICP-MS)(Element2;THERMO)测定分散体的离子含量。用两种独立的标定溶液(低和高标准)进行标定,对其使用Rhodium内标和多元素溶液(获自Merck)。将2g本发明试样稀释至20ml并使用。在所述质谱仪的中等分辨率下进行分析。检测同位素Fe(54)、Fe(56)和Rh(103),且基于所述标定测定铁含量。
电导率的测定
将经清洁的基材置于旋涂机上,并在该基材上分布10ml的本发明组合物。然后,通过旋转该板旋走剩余的溶液。随后,将由此涂覆的基材在130°C下于热板上干燥15分钟。然后借助层厚测定仪(Tencor,Alphastep500)测定层厚。通过如下方式测定电导率:将2.5cm长的Ag电极在10mm距离下经由掩膜气相沉积。将使用静电计(Keithly614)测得的表面电阻乘以层厚以获得比电阻率。电导率是比电阻率的倒数。
粘度的测定
使用连接有低温恒温器的Haake RV1粘度计测定粘度。使用具有双间隙的DG43量筒和DG43转子(二者均获自Haake)。将12g水溶液称量至量筒中。通过所述低温恒温器将温度调节至20°C。为了建立所需的温度,首先将分散体在50s-1的剪切速率下调混240秒。随后将剪切速率升至100s-1。保持该剪切速率30秒。然后再在100s-1的剪切速率下进行30次粘度测量达30秒(1次测量/秒)。然后,取这30个测量值的平均值作为所述分散体的粘度。胶凝行为的测定
将20g组合物置于250ml烧杯中。然后将所述组合物倾倒于倾斜角为45°的光滑塑料表面上。
在胶凝组合物的情况下,产生如下效果:
a)当倾倒出烧杯时,所述组合物不均匀流出,而是在玻璃壁上留下其中组合物粘合成团的区域和其中几乎没有残留任何组合物的区域;
b)当所述材料在塑料表面上流动时,材料在原地保持团状。流动不均匀,而是反复间断。[图1]
在均一组合物的情况下,产生如下效果:
(A)当倾倒出时,在烧杯壁上留下或厚或薄(取决于所述组合物的粘度)的均匀膜。在每种情况下,所述膜是均一的,不显示出任何不均匀性。
(B)当所述材料在塑料表面上流动时,形成均匀膜。[图2]
基于这些标准,可将组合物分成胶凝的或者均匀的。透射率的测定
用2通道分光光度计(获自PerkinElmer的Lambda900)测定涂覆基材的透射率。此外,为了检测被所述试样散射的任何比例的透射光,所述仪器装备有光度计球(Ulbricht球)。将待测试的试样固定在所述光度计球的输入口中。
随后,测量无涂层基材的透射率。所用基材为厚度2mm且切成50mm×50mm正方形的玻璃板。为了涂覆所述基材,将该基材置于旋涂机上,并在该基材上分布10ml的本发明组合物。然后通过旋转该板将剩余的溶液旋走。随后,将由此涂覆的基材在130°C下于热板上干燥15分钟。
随后,测量具有涂层的基材的透射率。然后使基材上的涂层在光度计球的前面朝向该球。
记录可见光区域,即320-780nm内的透射光谱,步长为5nm。由所述光谱,基于10°观察者和光类型D65,根据DIN5033计算所述试样的标准色值Y(亮度)。内透射率由具有涂层的基材的亮度(Y)与不具有涂层的那些(Y0)的比值如下计算:
内透射率=Y/Y0*100%
粗糙度的测定
将清洁的玻璃基材置于旋涂机上,并将10ml的本发明组合物分布于该基材上。然后通过旋转该板而旋走剩余的溶液。随后,将由此涂覆的基材在130°C下于热板上干燥15分钟。
表面粗糙度借助机械外形仪(获自KLA-Tencor的Tencor Alpha Step500)测定。为此,使传感针运动通过400μm的距离,且该仪器记录作为水平偏差函数的垂直偏差。根据其定义计算平均粗糙度(Ra)(参见下文和http://de.wikipedia.org/wiki/Rauheit)。使所述传感针的接触重量保持很小,以至于所述针不导致表面发生改变。这可通过在同一位置重复记录抽样的外形而检测。
平均粗糙度的定义(Ra)
平均粗糙度(以符号Ra表示)给出了表面上的测量点与平均线的平均距离。该平均线与实际外形在参照路径中相交,从而使得总外形偏差(相对于平均线)为最小。
因此,平均Ra对应于与平均线的偏差的算术平均值。在两个维度中,其如下计算:
且平均值如下计算:
方法
粒子测定—显微镜观察
借助移液管将3滴待研究的试样置于载玻片上并分布在约1cm2的面积上。然后,将所述载玻片在干燥箱中于100°C下干燥10分钟。在冷却后,在显微镜(Zeiss Axioskop)下以100倍的放大倍数使用透射光检查该载玻片,其中不使用偏振滤光片。
使用照相机(Olympus Altra20)记录图像,检查总共5个任意选择的200μm×200μm区域,对这5张照片中的离子交换剂的粒子数进行计数,并选择具有最高粒子计数的照片以测定粒子浓度。
实施例
实施例基于获自H.C.Starck Clevios GmbH的市售PEDOT/PSS分散体。由于所述分散体可在市场上公开且自由获得,此处不给出制备该PEDOT/PSS分散体的合成说明。然而,该分散体的制备细节可参见例如EP0440957A2。
实施例1:
对于所述混合物,使用具有如下性质的PEDOT/PSS分散体(Clevios PHC V4,获自H.C.Starck Clevios GmbH,Leverkusen):
粘度: 255mPas
固体物质含量: 1.10%
硫酸根含量: 7mg/kg
钠含量: 138mg/kg
铁含量: 0.20mg/kg
电导率: 426S/cm(在添加5%二甲亚砜后测定)
用上述方法测定的粒子浓度:无
将不同量的硫酸添加至200g的分散体试样中。硫酸的摩尔质量为98g/mol。其包含96g硫酸根/摩尔。在下文实施例中考虑该硫酸根的质量。硫酸根的量适于1和2中,以mg/kg计。在0、4、11和18天后测定所述分散体的粘度,并检查所述试样在该时间后是否胶凝。粘度数据汇总于表1中。
表1:在实施例1中制备的PEDOT:PSS分散体在添加硫酸根且随后储存之后的粘度
还在制备后测定所述试样的电导率。为此,将5g二甲亚砜添加至95g上述PEDOT/PSS分散体与硫酸的混合物中,并测定这些试样的电导率。结果示于下表2中。
表2:获自实施例1的具有不同硫酸根浓度的PEDOT/PSS分散体的电导率
使用涂覆有包含200mg/kg硫酸根的分散体的实施例的玻璃基材测定粗糙度和透射率。所述试样的粗糙度为3.53nm。所述试样的层厚为142nm,所述试样的内透射率为88.6%。
实施例2:
借助超滤将2000g固含量为1.10%的PEDOT/PSS分散体(Clevios PH500,获自H.C.Starck Clevios GmbH)浓缩至固含量为2.20%。然后将所述分散体置于填充有500ml离子交换树脂的柱(Lewatit MP62,获自Saltigo)中,所得分散体具有如下性质:
粘度: 103mPas
固体物质含量: 1.98%
硫酸根含量: 1mg/kg
钠含量: 5mg/kg
电导率: 425S/cm(在添加5%二甲亚砜之后测定)
铁含量: 0.19mg/kg
用上述方法测定的粒子浓度:无
向该分散体中添加硫酸钠。将不同量的硫酸钠添加至200g根据实施例1的程序制备的分散体试样中。硫酸根的量示于表3和4中,以mg/kg计。在0、4、11和18天之后测定所述分散体的粘度,并检查所述试样在该段时间后是否胶凝。
表3:在实施例2中制备的PEDOT:PSS分散体在添加硫酸根且随后储存之后的粘度
还在制备后测定所述试样的电导率。为此,将5g二甲亚砜添加至95g上述PEDOT/PSS分散体与硫酸的混合物中,并测定这些试样的电导率。结果示于下表4中。
表4:获自实施例2的具有不同硫酸根浓度的PEDOT/PSS分散体的电导率
使用涂覆有包含200mg/kg硫酸根的分散体的实施例的玻璃基材测定粗糙度和透射率。所述试样的粗糙度为1.39nm。所述试样的层厚为66nm,所述试样的内透射率为95.2%。
实施例1和2的结果显示,如果确保所述PEDOT/PSS分散体中的硫酸根含量为100-1,000ppm,则可获得高电导率和有利的储存稳定性的特别有利的性能组合。如果硫酸根含量低于100ppm,则尽管可获得有利的储存稳定性,但电导率较低。如果硫酸根含量高于1,000ppm,则电导率高,但仅在付出较差的储存稳定性的代价下才能获得。
Claims (25)
1.一种制备包含聚噻吩的组合物的方法,其包括如下方法步骤:
I)提供包含噻吩类单体和氧化剂的组合物Z1;
II)通过将所述氧化剂还原成还原产物并将所述噻吩类单体氧化而氧化聚合所述噻吩类单体,从而形成包含聚噻吩和所述还原产物的组合物Z2;
III)从在方法步骤II)中获得的组合物Z2中至少部分移除所述还原产物以获得组合物Z3;
其中组合物Z3的硫酸根含量为100-1,000ppm,基于组合物Z3的总重量。
2.根据权利要求1的方法,其中所述包含聚噻吩的组合物Z3的硫酸根含量为100-500ppm,基于组合物Z3。
3.根据权利要求1的方法,其中所述包含聚噻吩的组合物Z3的硫酸根含量为100-200ppm,基于组合物Z3。
4.根据前述权利要求中任一项的方法,其中通过向组合物Z3中添加硫酸或硫酸盐而调节组合物Z3的硫酸根含量。
5.根据前述权利要求中任一项的方法,其中所述噻吩类单体为3,4-乙撑二氧噻吩(EDT)且所述聚噻吩为聚(3,4-乙撑二氧噻吩)(PEDOT)。
6.根据前述权利要求中任一项的方法,其中在方法步骤I)中提供的包含噻吩类单体和氧化剂的组合物Z1还包含聚阴离子。
7.根据权利要求6的方法,其中所述聚阴离子为聚苯乙烯磺酸(PSS)。
8.根据前述权利要求中任一项的方法,其中组合物Z3为PEDOT/PSS分散体。
9.根据前述权利要求中任一项的方法,其中所述硫酸盐为硫酸的碱金属盐或铵盐或其混合物。
10.根据权利要求9的方法,其中所述硫酸的碱金属盐为硫酸钠。
11.根据前述权利要求中任一项的方法,其中在方法步骤III)中至少部分移除所述还原产物通过用离子交换剂处理组合物Z2而进行。
12.一种可根据前述权利要求中任一项的方法作为组合物Z3获得的组合物。
13.一种包含聚噻吩的组合物,其中所述组合物除所述聚噻吩之外,还包含100-1,000ppm的硫酸根,基于所述组合物的总重量。
14.根据权利要求13的组合物,其中所述组合物除所述聚噻吩之外,还包含100-500ppm的硫酸根,基于所述组合物的总重量。
15.根据权利要求13的组合物,其中所述组合物除所述聚噻吩之外,还包含100-200ppm的硫酸根,基于所述组合物的总重量。
16.根据权利要求13-15中任一项的组合物,其中所述组合物包含小于20ppm的铁,基于所述组合物的总重量。
17.根据权利要求13-16中任一项的组合物,其中所述聚噻吩为聚(3,4-乙撑二氧噻吩)。
18.根据权利要求13-17中任一项的组合物,其中所述组合物除所述聚噻吩之外,还包含聚阴离子。
19.根据权利要求19的组合物,其中所述聚阴离子为聚苯乙烯磺酸。
20.根据权利要求13-19中任一项的组合物,其中所述组合物为PEDOT/PSS配合物。
21.根据权利要求20的组合物,其中所述组合物具有至少一种下述性质:
i)粘度为60-250mPas;
ii)根据本文所述的测试方法测得的电导率为至少400S/cm;
iii)PEDOT/PSS含量为1-5重量%,基于所述组合物的总重量。
22.一种层结构体,其包括:
A)具有基材表面的基材,和
B)至少部分覆盖所述基材表面的层,
其中所述层由根据权利要求12-22中任一项的组合物中所含的固体形成。
23.根据权利要求22的层结构体,其中层B)具有如下性质:
B1)所述层的内透射率大于80%;
B2)所述层的粗糙度(Ra)小于20nm。
24.一种电子组件,其包括根据权利要求22或23的层结构体。
25.根据权利要求12-21中任一项的组合物在制备电子组件中的导电层中的用途。
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DE102010048031A DE102010048031A1 (de) | 2010-10-12 | 2010-10-12 | Polythiophene beinhaltende Dispersionen mit definiertem Sulfat-Gehalt |
DE102010048031.2 | 2010-10-12 | ||
US201161471861P | 2011-04-05 | 2011-04-05 | |
US61/471,861 | 2011-04-05 | ||
PCT/EP2011/005021 WO2012048824A1 (en) | 2010-10-12 | 2011-10-07 | Dispersions comprising polythiophenes with a defined sulfate content |
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