CN111635506A - 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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CN111635506A
CN111635506A CN202010544906.5A CN202010544906A CN111635506A CN 111635506 A CN111635506 A CN 111635506A CN 202010544906 A CN202010544906 A CN 202010544906A CN 111635506 A CN111635506 A CN 111635506A
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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，包括将式(II)所示化合物，2,7‑二溴‑2'，3'，6'，7'‑四辛基‑螺硅双芴和2,7‑二(4,4,5,5‑四甲基‑1,3,2‑二氧杂硼烷)‑9,9‑二辛基芴通过Suzuki偶联反应制得式(I)所示聚合物。本发明解决了现有的红光聚合物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 BDA0002540325500000021
其中，n＝10-800。
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，包括将式(II)所示化合物，2,7-二溴-2'，3'，6'，7'-四辛基-螺硅双芴和2,7-二(4,4,5,5-四甲基-1,3,2-二氧杂硼烷)-9,9-二辛基芴通过Suzuki偶联反应制得式(I)所示聚合物。
优选的，所述Suzuki偶联反应的时间为24-46h。
优选的，所述Suzuki偶联反应的时间为42h。
优选的，所述Suzuki偶联反应的温度为90℃。
与现有技术相比，本发明具有如下优点和有益效果：
本发明实施例制得的聚合物在甲苯溶液的PL光谱中，随着聚合度的增加，聚合物链内能量转移程度提高，表明本发明实施例制得的聚合物能够得到较高的荧光量子产率。本发明制得的聚合物P1-P5具有良好的荧光量子效率，且在乙酸乙酯中最高可获得97.76％的荧光量子效率。
附图说明
图1为本发明实施例制得的聚合物在非极性溶剂甲苯的光致发光光谱；
图2为本发明实施例制得的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
将2-氨基苯甲醛(4.8g，40mmol)和50mL丙酮加入250mL圆底烧瓶内，冰浴下搅拌30min后，向体系中滴加6％氢氧化钠溶液(120mL)，待滴加完毕，撤去冰浴，常温搅拌12h；后将体系转移至1000mL烧杯内，加入适量冰水，8％稀盐酸溶液调节体系pH至5.5，析出大量黄色固体，抽滤，用乙醇/水＝2:1重结晶，得式(III)所示化合物(5.15，产率80％)，其化学反应方程式为：
Figure BDA0002540325500000031
实施例2
向500mL烧瓶中加入4,7-二溴-2，1，3-苯并噻二唑(2.95g，10mmol)，碳酸钾(4g，30mmol)和80mL乙腈。在氩气下搅拌溶解后加入式(III)所示化合物(4.8g.30mmol)，于85℃下搅拌回流，TLC检测反应进程；反应结束后，滤掉碳酸钾，减压除去溶剂，将获得的粗产物以石油/乙酸乙酯＝10/1为洗脱剂进行硅胶色谱纯化。然后将产物在乙醇中重结晶，得到式(IV)所示化合物(6.54g，产率72％。)，其化学反应方程式为：
Figure BDA0002540325500000041
实施例3
向250ml的单口反应瓶内加入式(IV)所示化合物(4.54g，10mmol)，再加入三氯甲烷溶剂直至原料完全溶解(100ml)，将NBS粉末(7.12g，40mmol)溶解在30ml的三氯甲烷溶液中，逐滴滴加到反应瓶内，避光反应24小时。用DCM萃取三次，水洗一次，收集有机相，旋干DCM，再用THF重结晶纯化，得到式(II)所示化合物(11.3g，产率为92％)，其化学反应方程式为：
Figure BDA0002540325500000042
实施例4
氮气保护下，向50ml两口瓶中加入式(II)所示化合物(0.52g，0.5mmol)，2,7-二溴-2'，3'，6'，7'-四辛基-螺硅双芴(0.48g，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(0.64g，1mmol),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90℃下加热搅拌28小时得到中间聚合物；反应完毕将10mg苯硼酸溶于甲苯后然后加入到反应体系中，再加入5ml溴苯进行封端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。将固体重新溶解在甲苯中，以氯苯为淋洗剂采用200-300目的硅胶柱层层析，得到聚合物P1(0.89g，产率80％)，其中，化学反应方程式为：
Figure BDA0002540325500000051
实施例5
本实施例与实施例4的区别为：实施例4的反应时间为28h，本实施例的反应时间为34h，最终得到聚合物P2(1.21g，产率81％)。
实施例6
本实施例与实施例1的区别为：实施例4的反应时间为28h，本实施例的反应时间为38h，最终得到橙色絮状固聚合物P3(1.68，产率85％)。
实施例7
本实施例与实施例1的区别为：实施例4的反应时间为28h，本实施例的反应时间为42h，最终得到橙色絮状固聚合物P4(2.58g，产率82％)。
实施例8
本实施例与实施例1的区别为：实施例4的反应时间为28h，本实施例的反应时间为46h，最终得到橙色絮状固聚合物P5(3.25mg，产率81％)。
图1是本发明实施例制得的聚合物在非极性溶剂甲苯的光致发光光谱。在甲苯溶液中，当聚合度较低时，聚合物在430nm附近有明显的发射峰，这主要是噻唑的本征发射，当聚合度逐渐升高时发射峰也逐渐红移；由于五元环的噻唑单元与相邻的螺芴单元存在一定扭转角，共轭长度缩短导致光谱蓝移现象。同时分子链内给受体间电荷转移作用(ICT效应)增强，430nm处的发射峰逐渐减弱，510nm左右的发射峰逐渐增强并成为主峰。随着聚合度的增加，聚合物链内能量转移程度提高，表明本发明实施例制得的聚合物能够得到较高的荧光量子产率。
图2为本发明实施例制得的聚合物在薄膜状态下的光致发光光谱，在薄膜状态下，分子间聚集使分子链间作用增强，当聚合度较低时，聚合物的PL发射峰在516nm左右，主体噻唑单元的能量转移完全转移到附近的螺芴单元中。光谱仍表现出先红移后蓝移，与甲苯溶液中类似。
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-P5的荧光量子效率，其结果如表1所示
表1实施例4-8制备的红光聚合物的荧光量子效率
Figure BDA0002540325500000061
Figure BDA0002540325500000071
由表1可知，且聚合物P1-P5具有良好的荧光量子效率，且在乙酸乙酯中最高可获得97.76％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 (5)

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 FDA0002540325490000011
其中，n＝10-800。
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，包括将式(II)所示化合物，2,7-二溴-2'，3'，6'，7'-四辛基-螺硅双芴和2,7-二(4,4,5,5-四甲基-1,3,2-二氧杂硼烷)-9,9-二辛基芴通过Suzuki偶联反应制得式(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，所述Suzuki偶联反应的时间为24-46h。
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，所述Suzuki偶联反应的时间为42h。
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，所述Suzuki偶联反应的温度为90℃。
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