CN110845709B - 三臂和六臂三聚茚聚合物及其在电致变色领域中的应用 - Google Patents
三臂和六臂三聚茚聚合物及其在电致变色领域中的应用 Download PDFInfo
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Abstract
本发明涉及三臂和六臂三聚茚聚合物及其在电致变色领域的应用。所述的三臂和六臂三聚茚聚合物其结构式如下,其中Ar1和Ar2为可进行电化学聚合的芳香基团,当Ar2为H时为三臂三聚茚聚合物,当Ar1和Ar2同为可进行电化学聚合的芳香基团为六臂三聚茚聚合物;所述R为H、C1~50烷基直链或支化链、酮基、丙二腈;所述n和m为1~10000的自然数。该聚合物具有多孔形貌,电化学和动力学稳定性高,制备出的器件具有高的电致变色性能。
Description
技术领域
本发明涉及有机光电领域,具体涉及三臂和六臂三聚茚聚合物的设计合成及其在电致变色中的应用。
背景技术
电致变色材料是指通过改变施加在材料上的外加电压可以调控其掺杂程度,使材料的能带结构发生变化,从而引起其光学吸收性能的变化,在视觉上则表现为材料薄膜颜色的变化。随着掺杂(氧化)程度的增加,电致变色材料可以在价带和导带之间形成具有更低带隙的极化子和双极化子能级,这些新能级的形成改变了价电子跃迁过程中所需的能量,在光谱电化学上则表现为吸收峰的变化。这类材料在低能耗显示器件、电子纸、变色皮肤、信息存储显示等多个领域展现出商业化前景,可用于多种可穿戴电子设备的更新与功能集成化。
电致变色材料性能的评价是面临最重要的问题,科研工作者将电致变色性能用如下参数和指标进行评定:
(1)光学对比度:(Electrochromic contrast,ΔT)在单一波长下电致变色材料的氧化态(Oxidated)和中性态(Neutral)之间的光学透射率(Tox和Tneut。)之差,它是衡量材料类电致变色性能的重要参数之一。此波长是根据材料的吸收光谱确定的(同一材料也可能出现多个波长),也就是材料在氧化态或中性态的最大吸收峰所对应的波长。材料的吸收光谱是指材料在不同波长下对应的吸光度或透过率曲线,通过吸收光谱吸光度的大小来衡量材料的颜色变化,除此之外,光谱电化学实验还可以根据所施加的不同电压来反应材料中单极化子或双极化子的生成。
(2)着色效率:(Coloration efficiency,CE)是指电致变色材料在特定的波长下,单位面积下导电聚合物膜注入一定电量时吸光度的变化与发生的透过率转化的电荷密度之间的比值。一般情况下,同一种聚合物薄膜在氧化或还原过程中,着色效率的值是固定不变的,与薄膜的厚度也是无关的。着色效率计算公式为:
其中,△OD为光学密度变化值,指聚合物薄膜在特定的波长λ max下,氧化态和还原态透过率的比值;Q d是电荷密度,指单位面积上注入的电荷量。
(3)响应时间:(Switching time)电致变色材料或器件完成一个氧化(着色态)或还原(褪色态)转化过程所需要的时间,氧化(着色)过程对应为着色响应时间,还原(褪色)过程对应为褪色响应时间。响应时间一般采用透过率变化95%所需的时间来计算,影响转化时间的因素主要有:电解池的组成(溶剂的酸碱性、支持电解质的离子传导能力)、氧化还原过程施加的电压和离子在电致变色材料中的扩散难易程度等。
(4)开路光学记忆效应:(Open circuit memory)是指电致变色材料在没有施加外在电压的情况下聚合物保持氧化态或还原态颜色的能力,在操作上是将聚合物在施加一定时间外压的情况下测试光学透过率,然后断开外压测试光学透过率,这种变化就是该材料或者器件的记忆度。相关的应用表现在发光二极管(LEDs)可以在断电情况下保持所显示的内容。值得指出的是对在溶液中显色的电致变色材料或器件而言,由于存在离子扩散或交换作用,电致变色材料或器件所显示的颜色会很快退去,而全固态电致变色器件具有较好的记忆效应。
当下对电致变色材料和器件的要求主要是光学对比度高、着色效率高、响应时间短、记忆效应好、色彩变化明显、稳定性好等,美国佐治亚理工学院Reynolds教授、土耳其Toppare教授、中科大徐春叶教授、北京大学孟鸿教授、电子科技大学贾春阳教授、江西科技师范大学徐景坤教授等在电致变色领域做出了重要贡献。对高性能电致变色材料与器件的追求一直是科研工作者的重要使命,但是在性能指标中最最容易被科研工作者忽略或者不能解决的问题正是电致变色稳定性即寿命问题。
发明内容
为了克服稳定性差的缺点,本发明的目的在于提供一种稳定性高的电致变色聚合物。其核心技术为合成三臂和六臂三聚茚聚合前驱体,然后在电化学作用下聚合成网状稳定的聚合物,最终能制备得到高效稳定的电致变色器件。
本发明的目的通过下述方案实现:
三臂和六臂三聚茚聚合物,其特征在于,具有如下结构:
其中,所述R为H、C1~50烷基直链或支化链、酮基、丙二腈;所述n和m为1~10000的自然数;Ar1和Ar2为可进行电化学聚合的芳香基团,Ar2可为H(三臂三聚茚聚合物),也可与Ar1同为噻吩、呋喃、硒吩、吡咯、噻唑、苯、芴、咔唑、硅芴、苯并二噻吩、苯并二硒吩、苯并二呋喃、联噻吩、并噻吩、并呋喃、噻吩并环戊二烯、噻吩并吡咯、噻吩并噻咯、3,4-乙烯二氧噻吩、3,4-丙烯二氧噻吩、3,4-乙烯二氧硒吩、3,4-乙烯二硫噻吩及以上所有结构的衍生物的一种以上(六臂三聚茚聚合物)。
所述三臂和六臂三聚茚聚合物,其特征在于,其中共轭单元Ar1和Ar2具有如下结构的一种或多种偶联结构:
所述聚合物材料的制备方法,其特征在于,具体为如下步骤:三聚茚经锂氢交换反应、溴化反应、偶联反应得到所述聚合物的聚合前驱体,聚合前驱体经电化学聚合的方法获得本发明所述的新型三聚茚电致变色聚合物。
所述的三臂和六臂三聚茚聚合物在电致变色领域得到应用。
本发明与现有技术相比具有以下优点:
(1)本发明设计合成了一种新型三臂和六臂三聚茚聚合物。
本发明实现了具有优异稳定性和高性能的电致变色器件。
附图说明
图1为具体实施的新型三臂(Tr-3T)和六臂(Tr-6T)三聚茚电致变色聚合物的合成路线图。
图2为电致变色器件结构示意图。
图3为光谱电化学图。
图4为动力学稳定性图。
图5为受保护的结构图。
具体实施方式
下面通过具体实施例对本发明作进一步的说明,其目的在于帮助更好的理解本发明的内容,具体包括聚合物的合成和器件制备方法,但这些具体实施方案不以任何方式限制本发明的保护范围。
本发明的实践可采用本领域技术内的聚合物化学的常规技术。在以下实施例中,努力确保所用数字(包括量、温度、反应时间等)的准确性,但应考虑一些实验误差和偏差。在以下实施例中所用的温度以°C表示,压力为大气压或接近大气压。所用溶剂为分析纯或色谱纯购买,并且所有的反应在氮气氛围中进行。除非另外指出,否则所有试剂都要商业获得的。
具体实施方法
实施例1
三臂三聚茚聚合前驱体(结构4,Tr-3T)的制备
化学反应流程如下所示,具体反应步骤和反应条件如下:
(1)
原料或中间反应物:盐酸、冰醋酸、正丁基锂、1-溴正己烷、三氯化铁、液溴为安耐吉科技有限公司、北京百灵威科技有限公司、苏州纳凯科技有限公司等公司购买所得。
(2) 单体1的制备
1-茚酮(20.0 g,151 mmol)溶解在冰醋酸(120 mL)和浓盐酸(60 mL)的混合溶液中,在剧烈搅拌下加热到120摄氏度回流24小时。反应结束后将反应液直接倒入1 L冰水中,加入碳酸钠固体来中和酸,大约一个小时后黄色沉淀析出。将黄色沉淀先后进行水洗、丙酮洗和二氯甲烷洗获得白色固体(11 g,75%)。
(3) 单体2的制备
将化合物1(10 g, 29 mmol)置于500 mL两颈烧瓶中,抽换气三次,在氩气保护下注入THF(200 mL),将反应瓶置于–78 °C条件下,剧烈搅拌。在–78 °C条件下将n-BuLi(115.2 mL,2.5 M)逐滴加入到上述溶液中,并进行低温反应2h。反应结束后,1-溴正己烷(48.2 g)漫漫加入到上述反应液中,然后将反应液漫漫升温到室温,在室温下搅拌过夜。反应结束后将反应液倒入到1 L饱和的NH4Cl水溶液中以淬灭多余的n-BuLi。水相用乙酸乙酯进行萃取,萃取的有机相用无水硫酸镁干燥。旋干溶剂,粗产物拌粉进行柱层析提纯,洗脱剂为正己烷,获得白色固体(22 g,95%)。此步产物直接用于下一步反应。
(4) 单体3的制备
化合物2(2.4 g,2.8 mmol)、无水FeCl3(5 mg)和氯仿(15 mL)混合并进行常温搅拌活化,活化后10分钟之后转移到0 °C冰浴,将稀释在5 mL氯仿中的液溴(0.5 mL,10mmol)逐滴滴加到上述反应液中,反应过夜。反应结束后,Na2SO3水溶液(50 mL)加入到上述反应液中以出去多余的液溴。反应液用二氯甲烷进行萃取,将获得的有机相用无水MgSO4干燥,旋干溶剂,粗产物拌粉进行柱层析提纯,洗脱剂为正己烷,重结晶后获得白色固体(2.65g,89%)。
实施例2
三臂三聚茚聚合前驱体电化学聚合成三聚茚聚合物(PTr-3T)
化学反应流程如下所示,具体反应步骤和反应条件如下:
(1) 电化学聚合支持电解质六氟化磷四丁基胺为百灵威公司购买所得。
(2) 在氮气保护下,将三臂三聚茚聚合前驱体溶解于二氯甲烷中,浓度为1 M,循环伏安法电化学聚合成三聚茚聚合物。
实施例3
以实施例2所得聚合物材料为例应用在电致变色中
(1) 光谱电化学
将实施例2制备的沉积在ITO导电玻璃上的聚合物薄膜,放在三电极电解池中,电解池中有溶有六氟化磷四丁基胺的乙腈溶液;其中工作电极为附有聚合物薄膜的ITO导电玻璃,对电极为铂片,参比电极为Ag/AgCl电极。利用恒电位方法,通过电化学工作站调节施加在工作电极上的电压,同时用紫外可见光谱仪记录聚合物在不同电压下吸收光谱的变化趋势,即得到了聚合物的光谱电化学图谱。如图3所示。
图3中425 nm下是聚合物本身的特征峰,随着电压的升高,在780 nm处出现新的峰,这主要是由于产生极化子所造成的。
实施例4
(1) 聚合物膜的动力学稳定性研究
利用紫外可见分光光度计来测定方波电位下,聚合物膜在特定波长下,氧化态和还原态的透过率,从而计算出光学对比度,影响时间等。紫外可见分光光度计记录的为时间-透过率曲线,电化学工作站记录的为时间-电流曲线,根据这两条曲线还可计算出着色效率。
图4是PTr-3T在780nm处的动力学稳定性研究图谱,方波电位间隔为10s。
PTr-3T的透过率值约为21%,但是在扫描1000s后,其透过率依然保持95%以上,展示出比较好的动力学稳定性,提高器件的寿命,降低器件成本。
本发明的上述实施例仅仅是为清楚地说明本发明所作的举例,而并非是对本发明的实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等,均应包含在本发明权利要求的保护范围之内。
Claims (3)
1.三臂三聚茚聚合物,其特征在于,具有如下结构:
;
其中,所述三臂三聚茚聚合物经电化学聚合而成;
所述n为10000的自然数;
三臂三聚茚聚合前驱体的制备化学反应流程如下所示:
。
2.权利要求1所述聚合物的制备方法,其特征在于,具体为如下步骤:三聚茚经锂氢交换反应、溴化反应、偶联反应得到聚合物的聚合前驱体,聚合前驱体经电化学聚合的方法获得三聚茚电致变色聚合物。
3.权利要求1所述的三臂三聚茚聚合物在电致变色领域的应用。
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