CN112574209B - 一种用于有机发光的化合物及其应用 - Google Patents
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Abstract
本发明涉及一种用于有机发光的化合物，所述化合物的结构如式(I)所示；其中，R1‑R4分别独立地选自氢、取代或未取代的芳基基团、取代或未取代的杂芳基基团、取代或未取代的烷基基团。本发明的一种用于有机发光的化合物可用作电子传输材料，其不仅具较高的稳定性，也具有高电荷转移能力和高玻璃化转变温度。
Description
技术领域
本发明涉及光电材料领域，尤其涉及一种用于有机发光的化合物及其应用。
背景技术
有机电致发光元件具有以空穴传输层和电子传输层夹持含有发光材料的发光层，进而在该夹层结构的两外侧安装阳极和阴极而形成的结构。有机电致发光元件是利用由注入发光层中的空穴及电子的再键合而产生的激子失活时放出光(荧光或磷光)的元件，被应用于显示器等。
为了使有机发光器件具有足够的优异特性，形成有机材料层的材料，例如空穴注入材料、空穴传输材料、发光材料、电子传输材料、电子注入材料等首先需要由稳定且有效的材料来支撑，然而，目前用于有机发光器件的有机材料层的稳定且有效的材料的开发仍然不足。因此，需要持续开发新材料，而且需要这些开发的材料还能应用于上述的其他有机电子器件。
发明内容
本发明的目的是针对现有技术中的不足，提供一种用于有机发光的化合物。
为实现上述目的，本发明采取的技术方案是：
本发明的第一方面是提供一种用于有机发光的化合物，所述化合物的结构如式(I)所示：
其中，R1-R4分别独立地选自氢、取代或未取代的芳基基团、取代或未取代的杂芳基基团、取代或未取代的烷基基团。
优选地，R1-R4分别独立地选自氢、取代或未取代的C6-C60的芳基基团、取代或未取代的C6-C60的杂芳基基团、取代或未取代的C1-C50的烷基基团。
优选地，所述未取代的C6-C60的芳基基团包括：苯基、萘基、蒽基、菲基、醌基、芴基、螺芴基。
优选地，所述未取代的C6-C60的杂芳基基团包括：呋喃基、噻吩基、吡咯基、咪唑基、恶唑基、噻唑基、苯并呋喃基、苯并咪唑基、喹啉基、异喹啉基。
优选地，所述未取代的C1-C50的烷基基团包括：甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、己基、环丙基、环丁基、环戊基、环己基。
优选地，R1和R3分别独立地选自苯基、萘基、甲基、乙基。
优选地，所述化合物的结构如下所示：
本发明的第二方面是提供一种电子传输材料，包括如上述的化合物。
本发明的第三方面是提供一种电子传输层，包括如上述的电子传输材料。
本发明的第四方面是提供一种OLED装置，包括如上述的电子传输层。
本发明采用以上技术方案，与现有技术相比，具有如下技术效果：
本发明的一种用于有机发光的化合物可用作电子传输材料，其不仅具较高的稳定性，也具有高电荷转移能力和高玻璃化转变温度。
具体实施方式
下面对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅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作出创造性劳动的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。
需要说明的是，在不冲突的情况下，本发明中的实施例及实施例中的特征可以相互组合。
下面结合具体实施例对本发明作进一步说明，但不作为本发明的限定。
实施例1
本实施例提供一种用于有机发光的化合物，其结构式如下所示：
其合成方法如下所示：
将99.95mmol化合物1和99.98mmol化合物2悬浮于200mL的1,4-二噁烷和20mL乙酸中。将所得混合物在回流下搅拌约6小时，并冷却至室温。用100mL水稀释混合物，之后过滤生成的固体，并用水和己烷洗涤得到化合物A。
化合物A的产率为78％。表征数据：熔点(DSC)267℃，纯度99.9％；1H NMR(400MHz，CDCl3)δ(ppm)：7.70(s，2H)，7.48-7.32(m，8H)，7.30-7.22(m，12H)。
实施例2
本实施例提供一种用于有机发光的化合物，其结构式如下所示：
其合成方法与实施例1类似，仅需将原料进行相应的替换即可。
化合物B的产率为81％。表征数据：熔点(DSC)281℃，纯度99.9％；1H NMR(400MHz，CDCl3)δ(ppm)：8.68-8.64(m，2H)，7.70-7.60(m，8H)，7.48-7.32(m，4H)，7.30-7.22(m，9H)。
实施例3
本实施例提供一种用于有机发光的化合物，其结构式如下所示：
其合成方法与实施例1类似，仅需将原料进行相应的替换即可。
化合物C的产率为76％。表征数据：熔点(DSC)262℃，纯度99.9％；1H NMR(400MHz，CDCl3)δ(ppm)：7.70(s，2H)，7.48-7.32(m，8H)，7.30-7.22(m，7H)，3.72-3.79(m，2H)，1.50-1.54(m，3H)。
实施例4
本实施例提供一种用于有机发光的化合物，其结构式如下所示：
其合成方法与实施例1类似，仅需将原料进行相应的替换即可。
化合物D的产率为74％。表征数据：熔点(DSC)296℃，纯度99.9％；1H NMR(400MHz，CDCl3)δ(ppm)：7.93-7.90(m，4H)，7.70(s，2H)，7.48-7.39(m，8H)，7.32-7.22(m，16H)。
应用例
提供一种OLED器件，制备方法：在已有反射层的基板上形成ITO阳极，并依次蒸镀阳极、空穴注入层、空穴传输层、电子阻挡层、发光层、电子传输层、电子注入层、阴极及覆盖层。
各层的组成材料如下：
空穴注入层：主体材料NPD，客体材料F4-TCNQ，客体材料的摩尔百分含量为3％；空穴注入层的厚度为10nm；
空穴传输层：NPD，厚度为125nm；
电子阻挡层：TCTA，厚度为10nm；
发光层：主体材料ADN，客体材料t-Bu-Perylene，客体材料的摩尔百分含量为6％；厚度为30nm；
电子传输层：主体材料BPhen，客体材料Liq，主体材料和客体材料，厚度以及其摩尔百分含量如表1所示；
阴极：Mg/Ag，比例为9:1，厚度15nm；
覆盖层：覆盖层材料DNTPD，厚度为680nm。
表1
上述材料中简称所对应的结构式如下：
器件性能测试：
将应用例和对比例提供的OLED器件进行发光效率的测试，测试项目包括效率、驱动电压和寿命(LT95，亮度衰减到95％的时间)。
其中，器件光电性能数据在电流密度15mA/cm2条件下测得，寿命(LT95)数据在电流密度30mA/cm2条件下计算得到。
性能测试结果如下表所示：
表2
| 项目 | 效率(Cd/A) | 电压(V) | 寿命LT95(h) |
| 应用例1 | 6.7 | 3.7 | 129 |
| 应用例2 | 5.9 | 3.6 | 147 |
| 应用例3 | 6.4 | 3.6 | 136 |
| 应用例4 | 5.6 | 3.6 | 126 |
| 对比例1 | 4.8 | 4.0 | 108 |
由表中的性能数据可知，本发明材料高度适合用作OLED器件中的电子传输材料，并且具有较好的电子传输性能。与对比例的BPhen材料相比，本发明的材料具有更高的效率(不低于5.6Cd/A)，更低的电压(不高于3.7V)，更长的寿命(不低于126h)。
以上所述仅为本发明较佳的实施例，并非因此限制本发明的实施方式及保护范围，对于本领域技术人员而言，应当能够意识到凡运用本发明说明书内容所作出的等同替换和显而易见的变化所得到的方案，均应当包含在本发明的保护范围内。
Claims (1)
1.一种用于有机发光的化合物在电子传输材料或电子传输层中的应用，其特征在于，所述化合物的结构如下所示：
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