CN113150251A - 一种红光聚合物电致发光材料及其制备方法 - Google Patents

一种红光聚合物电致发光材料及其制备方法 Download PDF

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CN113150251A
CN113150251A CN202110342179.9A CN202110342179A CN113150251A CN 113150251 A CN113150251 A CN 113150251A CN 202110342179 A CN202110342179 A CN 202110342179A CN 113150251 A CN113150251 A CN 113150251A
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樊嘉政
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Abstract

本发明属光电显示器件技术领域，具体涉及一种红光聚合物电致发光材料及其制备方法。本发明提供了一种红光聚合物电致发光材料，其化学式如式(I)所示。本发明还提供了一种红光聚合物电致发光材料的制备方法，包括式(V)所示化合物、式(VI)所示化合物、式(II)所示化合物通过Suzuki偶联反应制得式(I)所示聚合物。本发明提供了一种红光聚合物电致发光材料及其制备方法，解决了现有的红光材料发光效率低且色坐标不理想的技术问题。

Description

一种红光聚合物电致发光材料及其制备方法
技术领域
本发明属光电显示器件技术领域，具体涉及一种红光聚合物电致发光材料及其制备方法。
背景技术
有机电致发光(O/PLED)作为新一代平板显示技术应运而生，并逐渐走进人们的生活。与传统的阴极射线管相比，它具有重量轻、主动发光和视角大等优点，且节能、环保、高效照明、灵活显示和低加工成本等优良特性，这些优点使其适用于平板显示和白光照明。在基于红色、蓝色和绿色的发光材料中，仅有P-PPV及其衍生物等绿光高分子材料已经达到商业水平，而红光高分子材料的发光效率和色坐标有待改进，因此迫切需要开发高性能的红光聚合物材料成为了本领域技术人员亟待解决的技术问题。
发明内容
本发明提供了一种红光聚合物电致发光材料及其制备方法，解决了现有的红光材料发光效率低且色坐标不理想的技术问题。
本发明提供了一种红光聚合物电致发光材料，其化学式如式(I)所示：
Figure BDA0002999502130000011
其中，x＝0.1-1，n＝2-800。
本发明还提供了一种红光聚合物电致发光材料的制备方法，包括式(V)所示化合物、式(VI)所示化合物、式(II)所示化合物通过Suzuki偶联反应制得式(I)所示聚合物；
Figure BDA0002999502130000021
优选的，式(II)所示化合物通过以下步骤制得：
步骤1：将3,4-乙撑二氧噻吩和N-溴代丁二酰亚胺通过溴代反应制得式(IV)所示化合物；
Figure BDA0002999502130000022
步骤2：将式(IV)所示化合物和4-碘苯酚通过取代反应制得式(III)所示化合物；
Figure BDA0002999502130000031
步骤3：将4-(2,7-二溴咔唑-9-基)苯胺，式(III)所示化合物和1,10-菲咯啉通过取代反应制得式(II)所示化合物。
优选的，所述Suzuki偶联反应的温度为85℃。
本发明的有益效果如下：
本发明实施例4-7制得的聚合物的最佳电致发光性能数据，其电流效率为2.39cdA-1，其发光亮度为5236cd m-2，色坐标均为标准红光，位于(0.65,0.33)附近。
附图说明
图1为本发明实施例4-7制得的聚合物的热失重曲线；
图2为本发明实施例4-7制得的聚合物的甲苯溶液的紫外-可见(UV-vis)吸收光谱；
图3为本发明实施例4-7制得的聚合物的氯仿溶液的紫外-可见(UV-vis)吸收光谱；
图4为本发明实施例4-7制得的聚合物在薄膜状态下的紫外-可见(UV-vis)吸收光谱；
图5为本发明实施例4-7制得的聚合物的甲苯溶液的光致发光(PL)谱；
图6为本发明实施例4-7制得的聚合物在薄膜状态下的光致发光(PL)谱；
图7为本发明实施例4-7制得的聚合物的构型图。
具体实施方式
下面结合具体实施例对本发明做进一步详细说明，但实施例并不对本发明做任何形式的限定。除非特别说明，本发明采用的试剂、方法和设备为本技术领域常规试剂、方法和设备。
实施例1
在0-5℃下，向250ml的单口瓶内加入3,4-乙撑二氧噻吩(5mL,27.86mmol)，冰醋酸(50ml)及浓硫酸(50ml)，避光搅拌。然后分三次加(12.3g,180mmol)，N-溴代丁二酰亚胺(NBS)，再逐渐升至室温，反应过夜。用大量水稀释反应液，分离出固体，然后反复用NaHCO3水溶液和甲醇洗涤数次，晾干后用热氯苯溶剂纯化，制得式(IV)所示化合物(4.3g，产率70％)，其化学反应方程式为：
Figure BDA0002999502130000041
实施例2
将150mlDMF与式(IV)所示化合物(39.7g，180mmol)，4-碘苯酚(25.36g，115.27mmol)和碳酸钾(31.74g，229.65mmol)中。将反应混合物在氮气下加热至80℃回流过夜。然后将混合物冷却至室温，并加入200ml冷水。随后将混合物用500ml二氯甲烷萃取。合并有机相，并用500ml饱和盐水洗涤，用硫酸镁干燥并蒸发溶剂。将取得的粗产物通过柱色谱法(石油醚)纯化，得到式(III)所示化合物(46.6g，72％),其化学反应方程式为：
Figure BDA0002999502130000051
实施例3
在4-(2,7-二溴咔唑-9-基)苯胺(6.24g，15mmol)，式(III)所示化合物(10.08g，28mmol)，1,10-菲咯啉(0.09g，0.50mmol)，氯化铜(0.05g，0.51mmol)和氢氧化钾(4g，71.3mmol)中加入50ml甲苯，然后在氩气下回流反应48小时。然后将反应混合物冷却至室温并加入200ml水，再用200ml二氯甲烷萃取3次，合并有机相用水洗涤并且硫酸镁干燥，将溶剂蒸发，将粗产物以石油醚：三乙胺＝20:1为洗脱剂进行硅胶柱色谱纯化，得到式(II)所示化合物(11.6g，88％)，其化学反应方程式为：
Figure BDA0002999502130000052
实施例4
将聚合单体式(V)所示化合物(0.34g，0.9mmol)、式(VI)所示化合物(0.47g，1mmol)、式(II)所示化合物(0.089g，0.1mmol)以及催化剂Pd(PPh3)4(8mg)、相转移催化剂四丁基溴化铵(120mg)放入150ml单口烧瓶中，利用双排管抽排氮气8次，然后加入脱气后的甲苯(10mL)和碳酸钾水溶液(8mL，2M)，升温至85℃并且剧烈搅拌，在氮气氛围下反应三天后将10mg苯硼酸溶于甲苯后然后加入到反应体系中，六个小时后加入溴苯。封端处理过夜后，将反应粗产物进行多次水洗、二氯甲烷萃取，将收集的油层进行硫酸镁干燥后，然后浓缩至2毫升左右，最后将其逐滴加入到处于剧烈搅拌中的甲醇溶液中。过滤然后将滤渣分别用甲醇、丙酮、正己烷和二氯甲烷进行索氏抽提处理，然后进行真空干燥，得到聚合物P1(3.65g，产率76％)
Figure BDA0002999502130000061
实施例5
本实施例与实施例4的区别为：式(V)所示化合物(0.26g，0.7mmol)式(II)所示化合物(0.267g，0.3mmol)，最终制得聚合物P2(4.25g，产率75％),其化学式为：
Figure BDA0002999502130000062
实施例6
本实施例与实施例4的区别为：式(V)所示化合物(0.185g，0.5mmol)式(II)所示化合物(0.445g，0.5mmol)，最终制得聚合物P3(5.89g，产率75％),其化学式为：
Figure BDA0002999502130000071
实施例7
本实施例与实施例4的区别为：式(V)所示化合物(0.111g，0.3mmol)式(II)所示化合物(0.623g，0.7mmol)，最终制得聚合物P4(6.91g，产率74％),其化学式为：
Figure BDA0002999502130000072
实施例8
制备电致发光器件：首先用ITO清洗剂、去离子水、丙酮和异丙醇在超声波下清洗ITO玻璃，然后用氮气吹扫，放入120℃的恒温烘箱中干燥，在紫外-臭氧清洗机中处理纯ITO片等离子体10分钟，然后在纯ITO片上涂覆PEDOT:PSS水分散液。转速为3000r/min，2分钟后放入120℃温度调节器，干燥30分钟，除去残留溶剂，然后形成厚度为30nm的薄膜。随后，本发明实施例4-7中合成的发光聚合物的无水氯仿溶液(12mg/ml)在薄膜厚度为95nm的PEDOT:PSS改性的氧化铟锡表面涂层上形成发光层；并在活性面积为0.09cm2、沉积压力为110-4Pa的真空镀膜机上依次蒸发20nmCa和100nmAl的阴极层，以制造具有ITO/PEDOT:PSS/Polymer/Ca/Al结构的器件。薄膜厚度通过Tencor Alfa Step-500台阶仪进行测定，金属电极真空沉积速率及其厚度通过厚度/速度仪(STM-100)测定。器件的包封通过环氧树脂和薄层玻璃在紫外光中固化封装，封装后即可在空气中测定器件的电致发光光谱，色坐标以及外量子效率。
图1为本发明实施例制得的聚合物P1-P4的热失重曲线，本发明实施例4-7制得的聚合物采用德国耐驰公司型号为NETZSCH STA409PC的热失重分析仪，加热速率为10℃/min，加热温度范围为25-800℃，测试样品为10mg，整个测试在氮气氛围下进行，从图1中可以发现，聚合物的热分解温度均超过了365℃，体现出良好的热稳定性能。
图2-图4为本发明实施例制得的聚合物的甲苯溶液、氯仿溶液和薄膜的紫外-可见(UV-vis)吸收光谱，其中溶液的紫外吸收光谱采用型号为SHIMADZU UV-3600，UV-Vis-NIR的紫外吸收分光光度计测定，温度为25℃，扫描范围为250nm-780nm，每个样品的浓度均为1.33×10-6M，图2-4可知，吸收光谱在375nm处均有明显吸收，可归因于分子主链骨架π-π*的跃迁吸收，从图2和图3中可知，吸收光谱几乎没有红移和宽化，说明基态情况下溶剂极性对分子的吸收光谱没有显著影响。由图4可知，由于聚合物分子主链空间的扭曲构型抑制了分子间的聚集，吸收光谱产生微小的蓝移。
图5-图6分别为本发明实施例4-7制得的聚合物的甲苯溶液与薄膜的光致发光(PL)谱图，由图可知，聚合物无论在溶液中还是薄膜状态下，其荧光光谱均实现了完全的红光发射，在图6中，随式(II)所示化合物含量增加，光谱有略微红移，分子间聚集作用增强，导致光谱红移。
本发明实施例采用Gaussian 09E.01对本发明实施例7制得的聚合物进行了B3LYP-D3/6-311G(d,p)级别的密度泛函(DFT)计算，其构型如图7所示，其中，聚合物P4的HOMO在式(II)所示化合物上均有分布，而它的LUMO仍然主要分布在硫氧芴中，表明聚合物内可以形成有效的分子内π-π相互作用。
基于本发明实施例制得的聚合物P1-P4的电致发光二极管的性能数据如表1所示(聚合物器件的电致发光光谱是在电压为12V的条件下测定)
表1本发明实施例4-7制得聚合物的电致发光性能
实施例 V<sub>on</sub> L(cd/m<sup>2</sup>) LE(cd/A) CIE(x，y)
实施例4 6.1 1025 0.36 (0.65,0.35)
实施例5 5.2 2365 0.97 (0.63,0.37)
实施例6 4.3 2875 1.26 (0.62,0.37)
实施例7 3.7 5236 2.39 (0.62,0.37)
由表1可知，本发明实施例4-7制得的聚合物的最佳电致发光性能数据，其电流效率为2.39cd A-1，其发光亮度为5236cd m-2，色坐标均为标准红光。位于(0.65,0.33)附近。
上述实施例为本发明较佳的实施方式，但本发明的实施方式并不受上述实施例的限制，其他的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化，均应为等效的置换方式，都包含在本发明的保护范围之内。

Claims (4)

1.一种红光聚合物电致发光材料，其特征在于，其化学式如式(I)所示：
Figure FDA0002999502120000011
其中，x＝0.1-1，n＝2-800。
2.一种红光聚合物电致发光材料的制备方法，其特征在于，包括式(V)所示化合物、式(VI)所示化合物、式(II)所示化合物通过Suzuki偶联反应制得式(I)所示聚合物；
Figure FDA0002999502120000012
3.根据权利要求2所述的红光聚合物电致发光材料的制备方法，其特征在于，式(II)所示化合物通过以下步骤制得：
步骤1：将3,4-乙撑二氧噻吩和N-溴代丁二酰亚胺通过溴代反应制得式(IV)所示化合物；
Figure FDA0002999502120000021
步骤2：将式(IV)所示化合物和4-碘苯酚通过取代反应制得式(III)所示化合物；
Figure FDA0002999502120000022
步骤3：将4-(2,7-二溴咔唑-9-基)苯胺，式(IV)所示化合物和1,10-菲咯啉通过取代反应制得式(II)所示化合物。
4.根据权利要求2所述的红光聚合物电致发光材料的制备方法，其特征在于，所述Suzuki偶联反应的温度为85℃。
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Publication number Priority date Publication date Assignee Title
CN1419574A (zh) * 2000-01-05 2003-05-21 剑桥显示技术有限公司 聚合物,及其制备和应用
CN1702066A (zh) * 2005-06-22 2005-11-30 中国科学院长春应用化学研究所 以9－苯基咔唑为核的空穴传输材料及其制备方法
CN102399359A (zh) * 2011-11-25 2012-04-04 华南理工大学 含磷酸酯基的三苯胺共轭聚合物及其应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1419574A (zh) * 2000-01-05 2003-05-21 剑桥显示技术有限公司 聚合物,及其制备和应用
CN1702066A (zh) * 2005-06-22 2005-11-30 中国科学院长春应用化学研究所 以9－苯基咔唑为核的空穴传输材料及其制备方法
CN102399359A (zh) * 2011-11-25 2012-04-04 华南理工大学 含磷酸酯基的三苯胺共轭聚合物及其应用

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