CN110628413A - 一种新型紫精电致变色材料的制备及其应用 - Google Patents
一种新型紫精电致变色材料的制备及其应用 Download PDFInfo
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Abstract
本发明涉及一种新型紫精电致变色材料的制备及其应用。该制备方法以4,4’‑联吡啶为原料,与卤代烷烃进行Menschutkin反应,合成单取代4,4’‑联吡啶盐;然后通过在单取代4,4’‑联吡啶盐中,引入芳香性的的基团,能够增加分子的共轭结构,进而增加分子的稳定性,提高分子链的耐辐射和耐温性能。此外,随着分子链的增长和芳香性基团的引入,改善了紫精化合物核心基团4,4’‑联吡啶上的缺电子状态,选择合适的取代基,调节分子轨道能级和电荷迁移能力可以获得不同的颜色,为实现多色显示提供了可能。本发明得到的紫精类电致变色材料,其透过率差值更高,变色更快,变色电压较低,使用寿命较长,使用其制备得到的电致变色器件具有突出的变色性能和成本优势。
Description
技术领域
本发明属于光电材料的技术领域,具体涉及一种新型紫精电致变色材料的制备及其应用。
背景技术
电致变色是指在外加电场作用下,材料的光学性能(透射率或反射率)在可见光范围内产生稳定的可逆变化的现象。在外观上表现为颜色及透明度的可逆变化,具有电致变色能力的材料被称为电致变色材料,使用电致变色材料制造的器件称为电致变色器件。电致变色器件的性能与其中的电致变色材料的性能关系密切,选择合适的电致变色材料,使得到的电致变色器件具有颜色变化丰富、颜色变化范围大和低驱动电压等优点。电致变色器件在智能窗、防眩目后视镜以及显示器等领域具有广阔的应用前景。
根据组成的不同,电致变色材料可分为无机电致变色材料和有基电致变色材料。紫精又名紫罗精,是目前研究最为广泛的电致变色化合物之一。紫精类化合物的基本化学结构是由联吡啶的大共轭π-π键骨架和杂原子组成,紫精类化合物具有颜色种类丰富、变色对比度高、变色响应时间短、制备成本低、使用寿命长等优点,但关于制备紫罗精基电致变色凝胶电解质,实现多色电致变色显示的研究较少。
目前所报道的紫精化合物主要是在联吡啶的氮原子上引入饱和烷烃类取代基,由于饱和烷烃基团不与联二吡啶基团产生共轭作用,因此,这些烷烃类取代基团对所构建的紫精化合物的电化学性质影响非常有限,不利于对紫精化合物的电子接收能力以及其变色范围进行调控。例如,在紫精分子上连接甲基、乙基等基团得到的甲基紫精、乙基紫精等,其颜色变化可以从无色变为蓝色,除此之外,单庚基取代的紫精化合物化合物可以显现出与传统烷基取代紫精通常表现的蓝色不同的品红色。因此,芳香性基团的引入,改善了紫精化合物核心基团4,4’-联吡啶上的缺电子状态,调节分子轨道能级和电荷迁移能力可以获得不同的颜色,为实现多色显示提供了可能。
发明内容
本发明是为了克服现有技术合成过程复杂,变色电压高,透过率差值小,颜色种类单一,溶液型电致变色器件电解液泄漏的不足而提供一种新型紫精电致变色材料,该紫精电致变化合物引入芳香性基团,改善了紫精化合物核心基团4,4’-联吡啶上的缺电子状态,降低其电致变色电压,透过率差值更高,变色更快,使用寿命较长,使用其制备得到的电致变色器件具有突出的变色性能和成本优势。
本发明是通过如下技术实现:
本发明提供一种新型紫精电致变色材料,所述电致变色成分的结构是
中的一种或几种组成的混合物,其中,所述结构中的R为碳原子数是1~12的碳链;Z为碳原子数是1~12的碳链;X-为I-、Cl-、Br-、ClO4 -、BF4、PF6-、TFSI-中的一种,或其组合。
所述一种新型紫精电致变色材料制备方法的合成路线分别如下:
其中,所述结构中的R为碳原子数是1~12的碳链;Z为碳原子数是1~12的碳链;X-为I-、Cl-、Br-、ClO4 -、BF4、PF6-、TFSI-中的一种,或其组合。
所述一种新型紫精电致变色材料可应用于锂离子电池、超级电容器、电致变色器件领域。
所述一种新型紫精电致变色材料的制备方法,其步骤如下:
(1)将4,4’-联吡啶溶于乙腈中,向其中缓慢滴入一卤代烷的乙腈溶液,并将溶液在50℃下反应72h,过滤并用无水乙醚洗涤,经真空干燥,得到单取代4,4’-联吡啶盐;
(2)将步骤(1)制得的固体产物溶于N,N-二甲基甲酰胺(DMF),通过单取代4,4’-联吡啶盐的芳香族亲核胺化,将溶液在60℃下反应72h,过滤并用无水乙醚洗涤,经真空干燥,得到可聚合非对称型紫精。
(3)将步骤(2)制得的固体产物溶于去离子水中,并加入KPF6的水溶液,常温下搅拌反应24h,将产物抽滤,并用去离子水洗涤,经真空干燥,得到目标产物式(1)。
(4)将步骤(1)制得的固体产物溶于N,N-二甲基甲酰胺(DMF),向其中缓慢滴入1,6-二溴己烷的DMF溶液,并将溶液在60℃下反应72h,过滤并用无水乙醚洗涤,经真空干燥,得到交联型紫精。
(5)将步骤(4)制得的固体产物溶于去离子水中,并加入KPF6的水溶液,常温下搅拌反应24h,将产物抽滤,并用去离子水洗涤,经真空干燥,得到目标产物式(2)。
(6)将步骤(2)制得的固体产物溶于N,N-二甲基甲酰胺(DMF),向其中缓慢滴入偶氮二异丁腈(AIBN)的DMF溶液,并将溶液在70℃下反应10h,减压蒸去溶剂,过滤并用无水乙醚洗涤,经真空干燥,得到侧链紫精聚合物。
(7)将步骤(6)制得的固体产物溶于去离子水中,并加入KPF6的水溶液,常温下搅拌反应24h,将产物抽滤,并用去离子水洗涤,经真空干燥,得到目标产物式(3)。
(8)将步骤(3)、(5)或(7)中制得的固体产物、二茂铁和聚离子液体,以质量比1~50:1~50:100~1000,加入到一定量的碳酸丙烯酯中,搅拌溶解后,得到电致变色凝胶态电解质。
(9)将步骤(8)中制得的电致变色凝胶态电解质均匀刮涂在覆盖有ITO的玻璃上,有效区域为双面胶围成的长方形,另一块同样大小的涂有ITO一面的玻璃覆盖住载有电解质的玻璃,压实保证没有任何气泡,得到电致变色器件。
本发明通过核磁共振(NMR)、红外光谱(IR)表征该类新型紫精电致变色材料结构,并采用光谱电化学法研究了器件的电致变色性能。
本发明的有益效果:
本发明通过在传统紫精类化合物中引入芳香性基团,得到了一种新的紫精类电致变色化合物,其变色范围更宽、透过率差值更高,变色更快,变色电压较低,使用寿命较长,使用其制备得到的电致变色器件具有突出的变色性能和成本优势。此外,本发明中电致变色活性物质包含在凝胶电解质中,解决了溶液型电致变色器件电解液泄漏的问题,而且,在电致变色器件中加入聚离子液体,体系不需要添加其它支持电解质,组成简单,变色程度深,器件稳定性好。
附图说明
图1为本发明实施例得到的电致变色化合物红外谱图。
图2为本发明实施例得到的电致变色化合物核磁共振谱图。
图3为含有本发明实施例1得到的电致变色化合物(1)的电致变色器件在两端电压分别为1.3V和0V下的颜色变化情况。
图4为含有本发明实施例1得到的电致变色化合物(1)的电致变色器件的循环伏安图。
图5为含有本发明实施例1得到的电致变色化合物(1)的电致变色器件的透过率-时间曲线图。
具体实施方式
为更好地说明本发明,下面结合实施例对本发明涉及的新型紫精类电致变色材料的制备及其在电致变色器件中的应用做进一步的说明,但本发明的实施方式不限如此。
实施例1
本实施例提供一种紫精电致变色材料式(1),它的制备方法包括以下步骤:
(1)将1.825g 4,4-联吡啶溶于10ml ACN中,向其中缓慢滴入2g经10ml ACN稀释的1-溴庚烷溶液,50℃下搅拌反应72h,过滤并用无水乙醚洗涤,50℃真空干燥24h,得到溴化1-庚基-4,4’-联吡啶盐(MHVBr),产率为47%。
(2)将步骤(1)中制得的固体产物1.675g溶于10ml DMF中,向其中缓慢滴入1.53g经5ml DMF稀释的对氯甲基苯乙烯溶液,于60℃下搅拌反应72h,过滤并用无水乙醚洗涤,50度真空干燥24h,得到氯化溴化1-庚基-1-[4’-(乙烯基)苄基]-4,4’-联吡啶盐(HBVBrCl),产率为60%。
(3)将0.5g步骤(2)中制得的氯化溴化1-庚基-1-[4-(乙烯基)苄基]-4,4’-联吡啶盐溶于10ml去离子水中,逐滴滴加0.507g KPF6水溶液(5ml),有沉淀析出,室温下搅拌反应24h,过滤,并用去离子水洗涤,50℃真空干燥24h,得到1-庚基-1-[4’-(乙烯基)苄基]紫精双六氟磷酸盐(HBV(PF6)2),产率为58%(电致变色化合物的红外谱图、核磁共振谱图分别如图1、图2所示)。。
(4)将步骤(3)中制得的固体产物、二茂铁和聚离子液体,以质量比5:1:200,加入到2.4ml的碳酸丙烯酯中,搅拌溶解后,得到电致变色凝胶态电解质。
(5)将步骤(4)中制得的电致变色凝胶态电解质均匀刮涂在覆盖有ITO的玻璃上,有效区域为双面胶围成的长方形,另一块同样大小的涂有ITO一面的玻璃覆盖住载有电解质的玻璃,压实保证没有任何气泡,得到电致变色器件。
通过紫外可见吸收光谱测试(UV-vis),循环伏安测试(CV),该紫精类电致变色器件在1.3V左右呈现蓝色状态,断电即可恢复无色状态(电致变色器件在两端电压分别为1.3V和0V下的颜色变化情况、CV曲线和透过率随时间变化分别如图3、图4、图5所示)。
实施例2
本实施例提供一种紫精电致变色材料式(2),它的制备方法包括以下步骤:
(1)将1.825g 4,4-联吡啶溶于10ml ACN中,向其中缓慢滴入2g经10ml ACN稀释的1-溴庚烷溶液,于50度下搅拌反应72h,过滤并用无水乙醚洗涤,50度真空干燥24h,得到溴化1-庚基-4,4’-联吡啶盐,产率为47%。
(2)将步骤(1)制得的固体产物0.9g溶于10ml DMF中,向其中缓慢滴入0.33g经5mlDMF稀释的1,6-二溴己烷溶液,于60℃下搅拌反应72h,过滤并用无水乙醚洗涤,50℃干燥24h,得到四溴化1-庚基-1-[1-己基-1-庚基-4,4’-联吡啶]-4,4’-联吡啶盐,产率为36%。
(3)将0.3g步骤(2)制得的四溴化1-庚基-1-[1-己基-1-庚基-4,4’-联吡啶]-4,4’-联吡啶盐溶于5ml去离子水中,逐滴滴加0.364g KPF6水溶液(5ml),有沉淀析出,室温下搅拌反应24h,将产物抽滤,并用去离子水洗涤,50℃真空干燥24h,得到1-庚基-1-[1-己基-1-庚基-4,4’-联吡啶]基紫精四六氟磷酸盐,产率为34%。
(4)将步骤(3)中制得的固体产物、二茂铁和聚离子液体,以质量比5:1:200,加入到2.4ml的碳酸丙烯酯中,搅拌溶解后,得到电致变色凝胶态电解质。
(5)将步骤(4)中制得的电致变色凝胶态电解质均匀刮涂在覆盖有ITO的玻璃上,有效区域为双面胶围成的长方形,另一块同样大小的涂有ITO一面的玻璃覆盖住载有电解质的玻璃,压实保证没有任何气泡,得到电致变色器件。
通过紫外可见吸收光谱测试(UV-vis),循环伏安测试(CV),该紫精类电致变色器件在1.3V左右呈现蓝色状态,断电即可恢复无色状态。
实施例3
本实施例提供一种紫精电致变色材料式(3),它的制备方法包括以下步骤:
(1)将1.825g 4,4-联吡啶溶于10ml ACN中,向其中缓慢滴入2g经10ml ACN稀释的1-溴庚烷溶液,50℃下搅拌反应72h,过滤并用无水乙醚洗涤,50℃真空干燥24h,得到溴化1-庚基-4,4’-联吡啶盐(MHVBr),产率为47%。
(2)将步骤(1)中制得的固体产物1.675g溶于10ml DMF中,向其中缓慢滴入1.53g经5ml DMF稀释的对氯甲基苯乙烯溶液,于60℃下搅拌反应72h,过滤并用无水乙醚洗涤,50度真空干燥24h,得到氯化溴化1-庚基-1-[4’-(乙烯基)苄基]-4,4’-联吡啶盐(HBVBrCl),产率为60%。
(3)将1g步骤(2)制得的氯化溴化1-庚基-1-[4-(乙烯基)苄基]-4,4’-联吡啶盐溶于5ml DMF中,缓慢滴入0.02g用5ml DMF稀释的偶氮二异丁睛,于70℃下恒温搅拌反应10h,减压蒸去溶剂,过滤并用无水乙醚洗涤,50℃真空干燥24h,得到聚氯化溴化1-庚基-1-[4-(乙烯基)苄基]-4,4’-联吡啶盐,产率为74%。
(4)将0.5g步骤(3)制得的固体产物溶于10ml去离子水中,逐滴滴加0.76g KPF6水溶液(7ml),有黄色沉淀析出,室温下搅拌反应24h,过滤,并用去离子水洗涤,50℃真空干燥24h,得到聚(1-庚基-1-[4-(乙烯基)苄基]紫精双六氟磷酸盐),产率为42%。
(5)将步骤(4)中制得的固体产物、二茂铁和聚离子液体,以质量比5:1:200,加入到2.4ml的碳酸丙烯酯中,搅拌溶解后,得到电致变色凝胶态电解质。
(6)将步骤(5)中制得的电致变色凝胶态电解质均匀刮涂在覆盖有ITO的玻璃上,有效区域为双面胶围成的长方形,另一块同样大小的涂有ITO一面的玻璃覆盖住载有电解质的玻璃,压实保证没有任何气泡,得到电致变色器件。
通过紫外可见吸收光谱测试(UV-vis),循环伏安测试(CV),该紫精类电致变色器件在1.3V左右呈现蓝色状态,断电即可恢复无色状态。
对照例1
CN 104610132A中的实施例1得到的紫精化合物。
本实施例提供一种紫精类化合物、其制备方法与实施例1中的基本一致,不同的是:采用了长碳链的烷基基团作为取代基团。最终制得的电致变色材料变色范围窄,颜色种类单一,光学对比度低,循环寿命较差。
以上对本发明的具体实施例进行了详细描述,但其只是作为范例,本发明并不限制于以上描述具体实施例。对于本领域技术人员而言,任何对本发明进行的等同修改和替代也都在本发明的范畴之中。因此,在不脱离本发明的精神和范围下所作的任何等同替换和修改,都包含在本发明的保护范围之内。
Claims (7)
1.一种新型紫精电致变色材料,其特征在于,所述电致变色成分的结构是
中的一种或几种组成的混合物,其中,所述结构中的R为碳原子数是1~12的碳链;Z为碳原子数是1~12的碳链;X-为I-、Cl-、Br-、ClO4 -、BF4、PF6-、TFSI-中的一种,或其组合。
2.根据权利要求1所述的一种新型紫精电致变色材料,其特征在于,所述电致变色成分还包括电子介质和聚离子液体。
3.根据权利要求2所述的一种新型紫精电致变色材料,其特征在于,所述电子介质包括二茂铁。
4.根据权利要求2所述的一种新型紫精电致变色材料,其特征在于,所述聚离子液体通过将离子液体和引发剂溶于乙醇中进行聚合得到。
5.根据权利要求4所述的一种新型紫精电致变色材料,其特征在于,所述离子液体包括1-丁基-3-乙烯基咪唑溴盐、1-丁基-3-乙烯基咪唑六氟磷酸盐、1-丁基-3-乙烯基咪唑双三氟甲基磺酰亚胺盐和1-丁基-3-乙烯基咪唑四氟硼酸盐。
6.根据权利要求4所述的一种新型紫精电致变色材料,其特征在于,所述引发剂包括偶氮二异丁腈和偶氮二异庚腈。
7.根据权利要求1所述的一种新型紫精电致变色材料,其特征在于所述结构的合成路线分别如下:
其中,所述结构中的R为碳原子数是1~12的碳链;Z为碳原子数是1~12的碳链;X-为I-、Cl-、Br-、ClO4 -、BF4、PF6-、TFSI-中的一种,或其组合。
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