CN113278135A - 一种绿光聚合物电致发光材料及其制备方法 - Google Patents

一种绿光聚合物电致发光材料及其制备方法 Download PDF

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CN113278135A
CN113278135A CN202110343559.4A CN202110343559A CN113278135A CN 113278135 A CN113278135 A CN 113278135A CN 202110343559 A CN202110343559 A CN 202110343559A CN 113278135 A CN113278135 A CN 113278135A
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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，具体涉及一种绿光聚合物电致发光材料及其制备方法。本发明提供了一种绿光聚合物电致发光材料，其化学式如式(I)所示。本发明提供了一种绿光聚合物电致发光材料的制备方法，包括将聚合单体2,7‑二溴‑9,9‑二辛基‑9H‑芴、2,2'‑(9,9‑二辛基‑9H‑芴‑2,7‑二基)双(4,4,5,5‑四甲基‑1,3,2‑二氧杂硼烷)、式(II)所示化合物和4，7‑二溴‑苯并噻二唑通过Suzuki偶联反应制得式(I)所示聚合物；本发明提供了一种绿光聚合物电致发光材料及其制备方法，解决了现有的绿光材料发光效率低且色谱纯度不理想的技术问题。

Description

一种绿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，具体涉及一种绿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、绿色和绿色的发光材料中，仅 有P-PPV及其衍生物等高分子材料已经达到商业水平，而现有的绿光高分子材 料的发光效率和色谱纯度仍有待改进，因此迫切需要开发高性能的绿光聚合物 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
本发明提供了一种绿光聚合物电致发光材料及其制备方法，解决了现有的 绿光材料发光效率低且色谱纯度不理想的技术问题。
本发明提供了一种绿光聚合物电致发光材料，其化学式如式(I)所示：
Figure BDA0003000025620000011
其中，R为芳基、三苯胺基、碳原子数1～20的直链或支链烷基，或碳原子 数1～20的烷氧基，x＝0.03-0.08，y＝0.02，n＝200-500。
本发明提供了一种绿光聚合物电致发光材料的制备方法，包括将聚合单体 2,7-二溴-9,9-二辛基-9H-芴、2,2'-(9,9-二辛基-9H-芴-2,7-二基)双 (4,4,5,5-四甲基-1,3,2-二氧杂硼烷)、式(II)所示化合物和4，7-二溴- 苯并噻二唑通过Suzuki偶联反应制得式(I)所示聚合物；
Figure BDA0003000025620000021
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 BDA0003000025620000022
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 BDA0003000025620000023
Figure BDA0003000025620000031
步骤3：将4-(2,7-二溴咔唑-9-基)苯胺(6.24g，15mmol)，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90℃。
优选的，所述Suzuki偶联反应的时间为24h。
本发明的有益效果如下：
本发明实施例4-7制得的聚合物的电致发光性能数据中，启动电压为3.8V， 其最佳电流效率为9.8cd A-1，其发光亮度为18870cd m-2，色坐标均为标准绿光。
附图说明
图1为本发明实施例4-7制得的聚合物在薄膜状态下的紫外-可见吸收光 谱；
图2为本发明实施例4-7制得的聚合物在薄膜状态下的PL发射光谱。
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
在0-5℃下，向250ml的单口瓶内加入3,4-乙撑二氧噻吩(5mL,27.86 mmol)，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 BDA0003000025620000041
实施例2
将150mlDMF与式(IV)所示化合物(39.7g，180mmol)，4-碘苯酚(25.36 g，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 BDA0003000025620000042
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 BDA0003000025620000051
实施例4
在装有温度计的50ml三口烧瓶里装入磁力搅拌子，将聚合单体2,7-二溴 -9,9-二辛基-9H-芴(0.17g，0.45mmol)、2,2'-(9,9-二辛基-9H-芴-2,7-二基) 双(4,4,5,5-四甲基-1,3,2-二氧杂硼烷)(0.32g，0.5mmol)、式(II)所示 化合物(26.7mg，0.03mmol)和4，7-二溴-苯并噻二唑(5mg，0.02mmol)依次 加入三口烧瓶中，再加入0.0045g(0.02mmol)的Pd(OAc)2、0.022g(0.06mmol) 的P(Cy)3、8ml质量分数为25％的TEAOH和5ml的甲苯，搅拌均匀。抽真空 通氮气，恒温90℃反应24h。最后加入苯硼酸(0.061g,0.5mmol)反应4h，继 续加入0.0785g(0.5mmol)的溴苯反应6h。反应完毕将三口烧瓶里的反应液用 无水甲醇进行沉淀，过滤收集固体产物并烘干，然后将粗产物用硅胶柱层析提 纯，得到聚合物P1，产率为65％。
Figure BDA0003000025620000061
实施例5
本实施例与实施例4的区别为：2,7-二溴-9,9-二辛基-9H-芴的含量为 (0.167g，0.44mmol)，式(II)所示化合物的含量为(35.6mg，0.04mmol)， 最终制得聚合物P2，产率64％,其化学式为：
Figure BDA0003000025620000062
实施例6
本实施例与实施例4的区别为：2,7-二溴-9,9-二辛基-9H-芴的含量为 (0.159g，0.42mmol)，式(II)所示化合物的含量为(53.4mg，0.06mmol)， 最终制得聚合物P4，产率62％,其化学式为：
Figure BDA0003000025620000071
实施例7
本实施例与实施例4的区别为：2,7-二溴-9,9-二辛基-9H-芴的含量为 (0.151g，0.4mmol)，式(II)所示化合物的含量为(71.2mg，0.08mmol)， 最终制得聚合物P6，产率62％，其化学式为：
Figure BDA0003000025620000072
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4-8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110-4 Pa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。
综上，图1为本发明实施例4-7制得的聚合物在薄膜状态下的紫外-可见吸 收光谱，由图可知，在330和350nm处观察到两个额外的吸收带，其中，330nm 处的吸收带可归因于式(II)所示化合物中的支链，350nm处的吸收带可归因于 主链中的π-π*跃迁。
图2为本发明实施例4-7制得的聚合物在薄膜状态下的PL发射光谱，由图 2可知，本发明实施例制得的聚合物的发射波长位于520-540nm左右，表现出绿 光发射。
将实施例4-7和对比例1在电流密度为10mA/cm2的条件下进行性能测试， 其结果如表1所示。
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 4.6 820 5.6 (0.31,0.59)
实施例5 4.4 2689 6.8 (0.27,0.65)
实施例6 4.7 1247 5.9 (0.28,0.64)
实施例7 4.6 14370 6.2 (0.27,0.63)
由表1可知，本发明实施例4-7制得的聚合物的电致发光性能数据中，最 佳启动电压为4.4V，其最佳电流效率为9.8cd A-1，其发光亮度为18870cd m-2， 色坐标均为标准绿光。
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)

1.一种绿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 FDA0003000025610000011
其中，R为芳基、三苯胺基、碳原子数1～20的直链或支链烷基，或碳原子数1～20的烷氧基，x＝0.03-0.08，y＝0.02，n＝200-500。
2.一种绿光聚合物电致发光材料的制备方法，其特征在于，包括将聚合单体2,7-二溴-9,9-二辛基-9H-芴、2,2'-(9,9-二辛基-9H-芴-2,7-二基)双(4,4,5,5-四甲基-1,3,2-二氧杂硼烷)、式(II)所示化合物和4，7-二溴-苯并噻二唑通过Suzuki偶联反应制得式(I)所示聚合物；
Figure FDA0003000025610000012
3.根据权利要求2所述的绿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 FDA0003000025610000021
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 FDA0003000025610000022
步骤3：将4-(2,7-二溴咔唑-9-基)苯胺(6.24g，15mmol)，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。
4.根据权利要求2所述的绿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90℃。
5.根据权利要求2所述的绿光聚合物电致发光材料的制备方法，其特征在于，所述Suzuki偶联反应的时间为24h。
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Citations (3)

* 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

Patent Citations (3)

* 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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