CN111574692A - 一种具有高荧光量子效率的红光聚合物及其制备方法 - Google Patents

一种具有高荧光量子效率的红光聚合物及其制备方法 Download PDF

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CN111574692A
CN111574692A CN202010544311.XA CN202010544311A CN111574692A CN 111574692 A CN111574692 A CN 111574692A CN 202010544311 A CN202010544311 A CN 202010544311A CN 111574692 A CN111574692 A CN 111574692A
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李建辉
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Abstract

本发明属有机发光显示领域，特别涉及一种具有高荧光量子效率的红光聚合物及其制备方法。本发明提供了一种具有高荧光量子效率的红光聚合物，具有式(I)所示结构。本发明还提供了一种具有高荧光量子效率的红光聚合物的制备方法，包括如下步骤：步骤1：氮气保护下，将(4,7‑二(5‑溴‑2‑噻吩基)‑5,6‑二辛氧基苯并噻二唑)和2,7‑二溴‑2'，3'，6'，7'‑四辛基‑螺硅双芴进行Suzuki偶联反应得到中间聚合物；步骤2：在中间聚合物中加入2,7‑二(4,4,5,5‑四甲基‑1,3,2‑二氧杂硼烷)‑9,9‑二辛基芴和苯硼酸封端得到式(I)所示聚合物。本发明解决了现有的红光聚合物红色发光纯度不高且荧光量子效率较低的技术问题。

Description

一种具有高荧光量子效率的红光聚合物及其制备方法
技术领域
本发明属有机发光显示领域，特别涉及一种具有高荧光量子效率的红光聚合物及其制备方法。
背景技术
1990年，英国剑桥大学J.H.Burroughes等首次推出了PPV聚合物发光二极管，开创了溶液法加工制备器件的先河，预见了其用作柔性显示的可能性。聚合物发光二极管的成功研制，确定了该项技术的可行性，让人们看到了该项技术用作平板显示或大面积柔性显示屏幕的希望。众所周知，在较低的电压驱动下，电致发光材料发出高效率的、高亮度的三基色光对于全色显色是非常必要的。然而，红光发光聚合物在亮度、效率等方面相对蓝光和绿光来说稍逊一筹。通常，红光聚合物是通过将卟啉和含吡喃的化合物与铕和铱配合物等掺杂在如Alq3宽带隙主体材料中。但是，当掺杂浓度较高时，这些掺杂红光发光材料很容易聚集在固体薄膜上，导致发光器件的荧光量子效率较低；而当掺杂浓度较低时，能量转移不能完全从主体材料到红色发光材料中，这通常会造成器件红色发光纯度不高。
因此，现有的掺杂红光聚合物红色发光纯度不高且荧光量子效率较低成为了本领域技术人员亟待解决的技术问题。
发明内容
本发明的目的在于提供一种具有高荧光量子效率的红光聚合物。
本发明的另一目在于是提供上述具有高荧光量子效率的红光聚合物的制备方法。
本发明上述目的通过以下技术方案实现：
本发明提供了一种具有高荧光量子效率的红光聚合物，具有式(I)所示结构：
Figure BDA0002540002810000021
其中，x＝0.5，n＝500-1000。
本发明还提供了一种具有高荧光量子效率的红光聚合物的制备方法，包括如下步骤：
步骤1：氮气保护下，将(4,7-二(5-溴-2-噻吩基)-5,6-二辛氧基苯并噻二唑)和2,7-二溴-2'，3'，6'，7'-四辛基-螺硅双芴进行Suzuki偶联反应得到中间聚合物；
步骤2：在中间聚合物中加入2,7-二(4,4,5,5-四甲基-1,3,2-二氧杂硼烷)-9,9-二辛基芴和苯硼酸封端得到式(I)所示聚合物。
优选的，步骤1中所述Suzuki偶联反应的时间为8-48h。
优选的，步骤1中所述Suzuki偶联反应的时间为32h。
优选的，步骤2中所述封端反应的时间为6h。
优选的，步骤2中所述封端反应的温度为90℃。
优选的，步骤2中所述2,7-二(4,4,5,5-四甲基-1,3,2-二氧杂硼烷)-9,9-二辛基芴的物质的量为2mmol。
与现有技术相比，本发明具有如下优点和有益效果：
本发明实施例制备的聚合物的甲苯溶液的光致发光光谱，在620nm左右有明显红光发射峰，表明本发明制备了发光纯度较高的红光。且聚合物的薄膜荧光光谱始终表现出单峰发射，说明分子内能量转移较为完全，分子间的聚集效应并没有随聚合度增加而不断增强。本发明制备的具有高荧光量子效率的红光聚合物具有良好的荧光量子效率，最高荧光量子效率达99.01％。
附图说明
图1为本发明实施例制备的具有高荧光量子效率的红光聚合物在薄膜状态下的光致发光光谱。
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
步骤1：氮气保护下，向50ml两口瓶中加入(4,7-二(5-溴-2-噻吩基)-5,6-二辛氧基苯并噻二唑)(357.3mg，0.5mmol)，2,7-二溴-2'，3'，6'，7'-四辛基-螺硅双芴(477mg，0.5mmol)，2,7-二(4,4,5,5-四甲基-1,3,2-二氧杂硼烷)-9,9-二辛基芴(1285.2mg，2mmol),2mg醋酸钯，5mg三环己基膦，2ml四乙基羟胺和30ml甲苯，利用双排管抽排氮气8次，避光条件下100℃下加热搅拌48小时得到中间聚合物；
步骤2：反应完毕将10mg苯硼酸溶于甲苯后然后加入到中间聚合物的反应体系中，再加入5ml溴苯在90℃下进行封端，6小时后反应完毕，将反应液冷却后滴加至200ml甲醇中沉析，过滤，干燥后滤渣在索氏提取器中先后用甲醇，丙酮，正己烷各抽提12小时得到固体。
步骤3：将固体重新溶解在甲苯中，以二氯甲烷为淋洗剂采用200-300目的硅胶柱层层析，浓缩后将聚合物溶于甲苯溶液并再次沉析在200ml甲醇中，过滤后在真空中干燥，得到橙色絮状固体聚合物P1(576.03mg，产率80％)，其中，化学反应方程式为：
Figure BDA0002540002810000041
实施例2
本实施例与实施例1的区别为：步骤1中的反应时间为40h,，最终得到橙色絮状固聚合物P2(538.21mg，产率81％)。
实施例3
本实施例与实施例1的区别为：步骤1中的反应时间为32h,，最终得到橙色絮状固聚合物P3(496mg，产率85％)。
实施例4
本实施例与实施例1的区别为：步骤1中的反应时间为24h,，最终得到橙色絮状固聚合物P4(432mg，产率82％)。
实施例5
本实施例与实施例1的区别为：步骤1中的反应时间为16h,，最终得到橙色絮状固聚合物P5(390mg，产率81％)。
实施例6
本实施例与实施例1的区别为：步骤1中的反应时间为8h,，最终得到橙色絮状固聚合物P6(306mg，产率80％)。
图1为本发明实施例1-6制备的红光聚合物的薄膜光致发光光谱，由图1可知，本发明实施例制得的聚合物发射峰均在620nm左右，均为纯度较高的红光发射，说明引入且随着聚合度降低，聚合物的光谱始终表现出单峰发射，说明分子内能量转移较为完全，分子间的聚集效应并没有随聚合度增加而不断增强，本发明通过在芴单元中引入噻吩和螺芴，使制得的聚合物具有较大的共轭平面，分子内的D-A相互作用较强，荧光性较好，由此可推测本发明实施例1-6制备的具有高荧光量子效率的红光聚合物具有较好的荧光量子效率。
其中，将芘并咪唑衍生物的固体溶于乙酸乙酯溶液中，通过荧光仪测试聚合物P1-P6的荧光量子效率，其结果如表1所示
表1实施例1-6制备的红光聚合物的荧光量子效率
聚合物 P1 P2 P3 P4 P5 P6
Q<sub>PL</sub>(％) 98.14 98.23 99.01 98.76 98.56 98.21
由表1可知，且聚合物P1-P6具有良好的荧光量子效率，且在乙酸乙酯中最高可获得99.01％的荧光量子效率。
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 (7)

1.一种具有高荧光量子效率的红光聚合物，其特征在于，具有式(I)所示结构：
Figure FDA0002540002800000011
其中，x＝0.5，n＝500-1000。
2.一种具有高荧光量子效率的红光聚合物的制备方法，其特征在于，包括如下步骤：
步骤1：氮气保护下，将(4,7-二(5-溴-2-噻吩基)-5,6-二辛氧基苯并噻二唑)和2,7-二溴-2'，3'，6'，7'-四辛基-螺硅双芴进行Suzuki偶联反应得到中间聚合物；
步骤2：在中间聚合物中加入2,7-二(4,4,5,5-四甲基-1,3,2-二氧杂硼烷)-9,9-二辛基芴和苯硼酸封端得到式(I)所示聚合物。
3.根据权利要求2所述的具有高荧光量子效率的红光聚合物的制备方法，其特征在于，步骤1中所述Suzuki偶联反应的时间为8-48h。
4.根据权利要求2所述的具有高荧光量子效率的红光聚合物的制备方法，其特征在于，步骤1中所述Suzuki偶联反应的时间为32h。
5.根据权利要求2所述的具有高荧光量子效率的红光聚合物的制备方法，其特征在于，步骤2中所述封端反应的时间为6h。
6.根据权利要求2所述的具有高荧光量子效率的红光聚合物的制备方法，其特征在于，步骤2中所述封端反应的温度为90℃。
7.根据权利要求2所述的具有高荧光量子效率的红光聚合物的制备方法，其特征在于，步骤2中所述2,7-二(4,4,5,5-四甲基-1,3,2-二氧杂硼烷)-9,9-二辛基芴的物质的量为2mmol。
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