CN114380865A - 一种含铋化合物、制备方法及应用 - Google Patents

一种含铋化合物、制备方法及应用 Download PDF

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CN114380865A
CN114380865A CN202011118628.3A CN202011118628A CN114380865A CN 114380865 A CN114380865 A CN 114380865A CN 202011118628 A CN202011118628 A CN 202011118628A CN 114380865 A CN114380865 A CN 114380865A
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bismuth
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孟鸿
陈小龙
缪景生
贺耀武
施明
蒋明杰
刘铭
贺超
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Peking University Shenzhen Graduate School
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Abstract

本发明涉及有机发光材料领域，具体涉及一种含铋化合物、制备方法及应用。该含铋化合物，在铋上引入不同的有机官能团，来改变材料的电子分布和分子堆积，调控材料的折射率和热稳定性，并且，不同官能团的引入可以改变材料溶解度，实现可溶液加工的有机光取出层材料。同时，基于铋类的有机化合物具有较强的荧光，不仅可以作为光取出层，也可以作为OLED器件的发光层，实现一种材料的多种功能化应用。

Description

一种含铋化合物、制备方法及应用
技术领域
本发明涉及有机发光材料领域，具体涉及一种含铋化合物、制备方法及应用。
背景技术
有机电致发光二极管(OLED)由于具有厚度小、重量轻、没有可视角度的问题、制造工艺简单、成本低、发光效率高、卷对卷加工等优点，在新型发光和显示领域有着广泛的应用，在智能手机、电视、照明，大屏显示等领域已取得成功的应用，受到了学术界和工业界的广泛重视和研究。
自从有机发光二极管(OLED)被发现以来，有机小分子发光材料和发光器件持续取得了进展，在发光效率和稳定性上面都有了很大的提高。根据OLED器件结构，我们可以将器件分为底发射和顶发射器件。对于底发射器件而言，在实际应用中，由于其光路要经过TFT阵列，出射光在经过TFT阵列会被散射、吸收，使得其器件出光率降低。对于顶发射OLED发光器件来说，由于受到波导效应等因素的影响，使得OLED器件所发出的光大部分在有机层内被层层反射，光在器件内部层层损失，并有部分转化成热量，影响有机层材料的稳定性，使得其效率滚降变得严重，寿命大幅度降低，在顶发射器件中，都只有20％左右的光能够导出器件被我们所用，降低的OLED的外发光效率，限制了其应用。因此，提高光取出效率也是当前需要解决的OLED研究重点。
目前来说，提高光取出效率的方法是在OLED器件电极表面镀上一层光取出层，增加光取出效率。通常选用一些高折射率的材料作为光取出层，减少光在器件内部损耗，提高发光效率。但是，目前常用的光取出层种类并不多，且大多都是一些金属氧化物，它们都需要通过蒸镀成膜，不利于大面积加工。因此，设计新型高折射率的光取出层材料至关重要。
发明内容
针对光取出层材料以上诸多不足，本发明提供一种含铋化合物、制备方法及应用。
本发明的技术方案通过如下方式实现：提供一种含铋化合物，分子式如下：
Figure BDA0002731221750000021
其中，R1、R2、R3为芳香基团，所述含铋化合物为半导体。
优选的，在本发明含铋化合物中，R1、R2、R3为相同或者不同的官能团。
优选的，在本发明含铋化合物中，R1、R2、R3为下列官能团中的任意一种：
Figure BDA0002731221750000022
Figure BDA0002731221750000031
Figure BDA0002731221750000041
另一方面，本发明还提供一种有机光取出层材料，使用前述含铋化合物作为单体聚合得到。
另一方面，本发明还提供一种含铋高分子化合物，为以Bi为主链的聚合物，通过将权利要求1-3中任意一项的含铋化合物作为单体聚合得到。
优选的，本发明含铋高分子化合物，为如下结构式中的一种：
Figure BDA0002731221750000051
另一方面，本发明还提供一种含铋高分子化合物的制备方法，制备原理如下：
Figure BDA0002731221750000052
其中，R1、R2、R3为芳香基团，使用的单体为含铋化合物，所述含铋化合物为半导体。
另一方面，本发明还提供一种含铋高分子化合物，将前述含铋化合物作为给体/受体单元，与其它的小分子给受体共聚形成D-A、D-A-D或A-D-A共聚物。
优选的，在本发明含铋高分子化合物中，所述其它的小分子给受体，为下列小分子单元中的任意一种：
Figure BDA0002731221750000061
优选的，本发明含铋高分子化合物，为如下结构式中的一种：
Figure BDA0002731221750000062
有益效果如下：
为了提高OLED顶发射器件中的外发光效率，基于目前的材料研究体系，我们以铋为核心，设计出基于铋类化合物的新型有机光取出层材料。在铋上引入不同的有机官能团，来改变材料的电子分布和分子堆积，调控材料的折射率和热稳定性，并且，不同官能团的引入可以改变材料溶解度，实现可溶液加工的有机光取出层材料。同时，基于铋类的有机化合物具有较强的荧光，不仅可以作为光取出层，也可以作为OLED器件的发光层，实现一种材料的多种功能化应用。
附图说明
图1为使用本发明含铋化合物制成的顶发射器件的结构示意图。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚，下面将结合本发明具体实施例及相应的附图对本发明技术方案进行清楚、完整地描述。显然，所描述的实施例仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
下面结合附图和实施例对本发明进一步详细的说明。
本发明的含铋化合物包括但不限于：
Figure BDA0002731221750000081
Figure BDA0002731221750000091
Figure BDA0002731221750000101
Figure BDA0002731221750000111
Figure BDA0002731221750000121
Figure BDA0002731221750000131
Figure BDA0002731221750000141
Figure BDA0002731221750000151
Figure BDA0002731221750000161
Figure BDA0002731221750000171
Figure BDA0002731221750000181
以上结构仅为部分代表，其他的含有同等思想的分子均在此专利保护范围之内，同时，在分子的芳香基上引入一些烷基链、烷氧基链、CN、F、Cl等基团也包括在此专利范围内。
实施例1(对称取代化合物的合成)：
Figure BDA0002731221750000182
惰性气体保护气氛下，将1.57g溴苯溶解到60ml无水THF中，加入两粒碘，2.16g新鲜镁屑，加热引发反应，并向其中缓慢加入7.85g溴苯，加热回流 2h，冷却，取6.3g BiCl3溶解在20mlTHF中加入到格式试剂中，搅拌反应过夜。加水淬灭反应，萃取，浓缩柱层析纯化，得到白色固体5.2g，产率59％。折射率为1.82。
对于非对称铋类化合物的合成，可以改变格式试剂的比例，来合成得到产物。
实施例2(非对称取代化合物的合成)：
Figure BDA0002731221750000191
惰性气体保护气氛下，将1.57g溴苯溶解到60ml无水THF中，加入两粒碘，2.16 g新鲜镁屑，加热引发反应，并向其中缓慢加入7.85g溴苯，加热回流2h，冷却，取9.45g BiCl3溶解在20mlTHF中加入到格式试剂中，搅拌反应过夜。加水淬灭反应，萃取，浓缩柱层析纯化，得到白色固体7.2g，产率60.3％。
惰性气体保护气氛下，将0.5g溴萘溶解到30ml无水THF中，加入两粒碘， 0.36g新鲜镁屑，加热引发反应，并向其中缓慢加入1.56g溴苯，加热回流2h，冷却，取3.98g二苯基氯化铋溶解在10mlTHF中加入到格式试剂中，搅拌反应过夜。加水淬灭反应，萃取，浓缩柱层析纯化，得到白色固体2.8g，产率57％。折射率1.88。
实施例3(稠环类化合物的合成)：
Figure BDA0002731221750000192
无水无氧氮气氛围下，取1.38g反应原料溶解于100ml四氢呋喃中，降温至 -78℃，向其中逐滴加入n-BuLi 24ml(2.5M)，滴加完毕后，反应体系升温加热回流3h，再次降温至-78℃，加入三溴化铋1.335g。升至室温，搅拌1h，降温至0℃，加入10.3g二异丙基乙氨，加热回流过夜。冷却，加水淬灭，氯仿萃取，浓缩，柱层析纯化，得到黄色固体0.52g，产率30.1％。折射率为1.91。
我们制备的含铋化合物进行了顶发射器件制备，其器件结构如下图1所示，器件性能见下表：
光取出层 CE(cd/A) EQE(％)
化合物11 110.5 28.2
化合物26 106.3 25.4
化合物32 127.4 34.3
化合物41 131.5 36.8
化合物48 118.4 31.4
化合物77 132.3 37.5
我们也考虑到将以上小分子作为侧链修饰引入到聚合物中，设计合成基于 Bi的高分子化合物，例如：
Figure BDA0002731221750000201
同时，我们也考虑将本发明含铋化合物作为单体进行聚合，得到以Bi为主链的聚合物，通过溶液法旋涂，得到我们所需的薄膜，其聚合结构示意如下，即我们可以得到线性聚合物和交联型聚合物：
Figure BDA0002731221750000202
基于本发明含铋化合物作为单体的部分聚合物结构例举如下：
Figure BDA0002731221750000211
此外，将本发明含铋化合物作为单体，作为给体/受体单元与其余的小分子给受体共聚形成D-A、D-A-D、A-D-A等共聚物，例如与以下小分子单元共聚，其中R为F、Cl、Br、CN、硝基、烷基链或者烷氧基链：
Figure BDA0002731221750000212
其可能结构式例举如下：
Figure BDA0002731221750000221
以上所列举的聚合物结构仅为部分代表，其他的含有同等思想的含Bi类聚合物分子均在此专利保护范围之内。
尽管上面已经示出和描述了本发明的实施例，可以理解的是，上述实施例是示例性的，不能理解为对本发明的限制，本领域的普通技术人员在本发明的范围内可以对上述实施例进行变化、修改、替换和变型。

Claims (10)

1.一种含铋化合物，其特征在于，分子式如下：
Figure FDA0002731221740000011
其中，R1、R2、R3为芳香基团，所述含铋化合物为半导体。
2.根据权利要求1所述的含铋化合物，其特征在于，R1、R2、R3为相同或者不同的官能团。
3.根据权利要求1所述的含铋化合物，其特征在于，R1、R2、R3为下列官能团中的任意一种：
Figure FDA0002731221740000012
Figure FDA0002731221740000021
Figure FDA0002731221740000031
4.一种有机光取出层材料，特征在于，使用权利要求1-3中任意一项的含铋化合物作为单体聚合得到。
5.一种含铋高分子化合物，其特征在于，为以Bi为主链的聚合物，通过将权利要求1-3中任意一项的含铋化合物作为单体聚合得到。
6.根据权利要求5所述的含铋高分子化合物，其特征在于，为如下结构式中的一种：
Figure FDA0002731221740000041
7.一种含铋高分子化合物的制备方法，其特征在于，制备原理如下：
Figure FDA0002731221740000042
其中，R1、R2、R3为芳香基团，使用的单体为含铋化合物，所述含铋化合物为半导体。
8.一种含铋高分子化合物，其特征在于，将权利要求1-3中任意一项的含铋化合物作为给体/受体单元，与其它的小分子给受体共聚形成D-A、D-A-D或A-D-A共聚物。
9.根据权利要求8所述的含铋高分子化合物，其特征在于，所述其它的小分子给受体，为下列小分子单元中的任意一种：
Figure FDA0002731221740000051
10.根据权利要求8所述的含铋高分子化合物，其特征在于，为如下结构式中的一种：
Figure FDA0002731221740000052
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