CN107325036A - 一种有机电致发光材料及其有机发光器件 - Google Patents

一种有机电致发光材料及其有机发光器件 Download PDF

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CN107325036A
CN107325036A CN201710568887.8A CN201710568887A CN107325036A CN 107325036 A CN107325036 A CN 107325036A CN 201710568887 A CN201710568887 A CN 201710568887A CN 107325036 A CN107325036 A CN 107325036A
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孙可
孙可一
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

本发明提供一种有机电致发光材料及其有机发光器件，属于有机光电材料技术领域。解决现有技术中有机光电材料发光效率低、驱动电压较高等发光性能差的技术问题。本发明所述的有机电致发光材料兼具有吸电子基团和推电子效应的基团，是一种新颖的双极性有机电致发光材料，可明显提高器件的发光效率。母核采用具有对称结构的共轭基团四苯基乙烯，具有较好的热稳定性，器件的使用寿命将会延长。实验结果表明，采用本发明的有机电致发光材料制备的有机发光器件，发光效率最高可达20.3cd/A，驱动电压最低为3.5V，是一种优异的OLED材料。

Description

一种有机电致发光材料及其有机发光器件
技术领域
本发明涉及有机光电材料技术领域，具体涉及一种有机电致发光材料及其有机发光器件。
背景技术
有机电致发光是指有机材料在电场作用下，受到电流和电场的激发而发光的现象。在过去三十年里，有机电致发光技术迅猛发展，其部分性能已经接近甚至超越了无机半导体材料，有望在大屏幕及超大屏幕显示领域挑战传统的CRT、LCD技术。
在OLED的研究中，有机材料的选择起着决定性的作用。OLED中用到的有机材料主要有空穴注入材料、空穴传输材料、发光材料、电子传输材料及电子注入材料等。一般地说，所有的空穴或电子传输型主体材料掺杂客发光体形成发光层，激子复合区域会选择性地偏上某一边，从而导致器件效率与光色的改变，甚为严重的可能会引起三重态之间的能量淬灭，导致高亮度下发光效率滚降严重。此外，器件的驱动电压较高，也不甚理想。
发明内容
有鉴于此，本发明的目的在于提供一种以四苯基乙烯为母核的有机电致发光材料及其有机发光器件，采用本发明所述一种有机电致发光材料制备的有机发光器件，具有更高的发光效率，及更低的驱动电压。
本发明首先提供了一种有机电致发光材料，其结构通式如I或II所示：
其中，M为含有氮原子的推电子杂环。
优选的，所述M选自如下结构中的任意一种：
其中，Ar选自取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳烷基、取代或未取代的C6-C50杂芳基中的任意一种；R1、R2独立的选自氢、取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳烷基、取代或未取代的C6-C50芳胺、取代或未取代的C3-C50杂芳基中的任意一种；
X选自氧、硫、SO2、CH2、C(CH3)2或CPh2。
优选的，所述的Ar选自取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基、取代或未取代的C6-C30杂芳基中的任意一种；R1、R2独立的选自氢、取代或未取代的C1-C10烷基、取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基、取代或未取代的C6-C30芳胺、取代或未取代的C3-C30杂芳基中的任意一种。
优选的，所述的一种有机电致发光材料，选自如下1-112结构中的任意一种：
本发明还提供一种有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层，至少一个有机化合物层包含至少一种本发明所述的有机电致发光材料。
优选的，所述有机化合物层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层。
本发明的有益效果：
本发明提供一种基于以四苯基乙烯为母核的有机电致发光材料及其有机发光器件。本发明所述的四苯基乙烯为母核的有机电致发光材料兼具有吸电子基团和推电子效应的基团，是一种新颖的双极性有机电致发光材料，可明显提高器件的发光效率。母核采用具有对称结构的共轭基团四苯基乙烯，具有较好的热稳定性，器件的使用寿命将会延长。实验结果表明，采用本发明的有机电致发光材料制备的有机发光器件，发光效率最高可达20.3cd/A，驱动电压最低为3.5V，是一种优异的OLED材料。
具体实施方式
下面将结合本发明实施例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。
本发明首先提供一种有机电致发光材料，结构通式如I或II所示：
其中，M为含有氮原子的推电子杂环。
本发明中，母核采用具有对称结构的共轭基团四苯基乙烯，具有较好的热稳定性，同时通过连接含有氮原子的推电子杂环M使得主体结构中兼具有吸电子基团和推电子效应的基团，得到一种新颖的双极性有机电致发光材料。所述M优选为含有N原子的五元或六元杂环，更优选为如下结构中的任意一种：
其中，Ar选自取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳烷基、取代或未取代的C6-C50杂芳基中的任意一种；R1、R2独立的选自氢、取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳烷基、取代或未取代的C6-C50芳胺、取代或未取代的C3-C50杂芳基中的任意一种；
X选自氧、硫、SO2、CH2、C(CH3)2或CPh2。
优选的，所述的Ar选自取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基、取代或未取代的C6-C30杂芳基中的任意一种；R1、R2独立的选自氢、取代或未取代的C1-C10烷基、取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基、取代或未取代的C6-C30芳胺、取代或未取代的C3-C30杂芳基中的任意一种。
优选的，所述的有机电致发光材料，选自如下1-112结构中的任意一种：
本发明所述有机电致发光材料可通过如下反应路线制备得到：
其中，M为含有氮原子的推电子杂环。
优选的，M选自如下结构中的任意一种：
其中，Ar选自取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳烷基、取代或未取代的C6-C50杂芳基中的任意一种；R1、R2独立的选自氢、取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳烷基、取代或未取代的C6-C50芳胺、取代或未取代的C3-C50杂芳基中的任意一种；
X选自氧、硫、SO2、CH2、C(CH3)2或CPh2。
优选的，所述的Ar选自取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基、取代或未取代的C6-C30杂芳基中的任意一种；R1、R2独立的选自氢、取代或未取代的C1-C10烷基、取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基、取代或未取代的C6-C30芳胺、取代或未取代的C3-C30杂芳基中的任意一种。
本发明对上述各类反应的反应条件没有特殊要求，以本领域技术人员熟知的此类反应的常规条件即可。本发明对上述各类反应中所采用的原料的来源没有特别的限制，可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。
本发明还提供一种有机发光器件，所述有机发光器件为本领域技术人员所熟知的有机发光器件即可。本发明所述有机发光器件包括第一电极、第二电极和置于两电极之间的一个或多个有机化合物层，至少一个有机化合物层包含至少一种本发明所述的有机电致发光材料。所述有机化合物层优选包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层与电子注入层中的至少一层，优选所述的发光层中含有本发明所述的有机电致发光材料。
实施例1：化合物1的制备
Step1，取100mmol的双(4-溴苯)甲酮，加入120mmol的三甲基硅基乙炔，1000mmol三乙胺，1mmol PdCl2(PPh3)，2mmol CuI，脱气后的四氢呋喃，氩气置换三次，回流温度下反应10h，粗产品经由柱层析，得到产品86mmol化合物1-1。
Step2，将86mmol芴溶解在无水THF中，降温到-78摄氏度，缓慢滴加2.5当量正丁基锂，反应2h，加入2当量的1-1的THF溶液。在缓慢升温至室温反应3h。反应完成后，加入大量水，有白色产品析出，过滤，滤饼经由柱层析得到71mmol产品1-2。
Step3，将71mmol 1-2溶解在甲苯中，加入2当量的对甲基苯磺酸，回流反应2h。反应后将溶剂旋干，得到粗品经由柱层析，得到62mmol产品1-3。
Step4，将1-3 62mmol溶解在四氢呋喃中，加入1当量的丁基氟化铵，回流反应2h。反应后将溶剂旋干，得到粗品经由柱层析，得到55mmol产品1-4。
Step5，取1-4 55mmol，加入1当量的咔唑，165mmol叔丁醇钾，0.6mmol Pd2(dba)3，甲苯，氩气置换三次，加入1.2mmol三叔丁基膦，再次氩气置换三次，回流温度下反应10h，粗产品经由柱层析，得到产品44mmol化合物1。
实施例2：化合物2的制备
Step1～Step4同实施例1中Step1～Step4。
Step5，取1-4 55mmol，加入1当量的硼酸，165mmol碳酸钠，0.6mmol四三苯基磷钯，甲苯，乙醇，水的混合溶剂，氩气置换三次，回流温度下反应10h，粗产品经由柱层析，得到产品47mmol化合物2。
实施例3：化合物3的合成
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例4：化合物4的合成
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例5：化合物5的合成
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例6：化合物6的合成
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例7：化合物7的合成
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例8：化合物8的合成
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例9：化合物11的合成
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例10：化合物12的合成
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例11：化合物25的合成
Step0，取100mmol 2-溴代咔唑，加入1当量的吡啶硼酸，300mmol碳酸钠，1mmol四三苯基磷钯，甲苯，乙醇，水的混合溶剂，氩气置换三次，回流温度下反应10h，粗产品经由柱层析，得到产品86mmol化合物25-0。
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例12：化合物29的合成
Step0，取100mmol溴代-10H-吩噻嗪，加入1当量的1,3,5-三嗪，300mmol叔丁醇钾，1mmol Pd2(dba)3，甲苯，氩气置换三次，加入2mmol三叔丁基膦，再次氩气置换三次，回流温度下反应10h，粗产品经由柱层析，得到产品44mmol化合物29-0。
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例13：化合物33的合成
将实施例1中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例1。
实施例14：化合物42的合成
将实施例2中的M换成如上述所述的结构M，其余步骤同实施例2。
实施例15：化合物57的合成
Step1，将86mmol芴溶解在无水THF中，降温到-78摄氏度，缓慢滴加2.5当量正丁基锂，反应2h，加入2当量的二溴苯甲基酮的THF溶液。在缓慢升温至室温反应3h。反应完成后，加入大量水，有白色产品析出，过滤，滤饼经由柱层析得到71mmol产品57-1。
Step2，将71mmol57-1溶解在甲苯中，加入2当量的对甲基苯磺酸，回流反应2h。反应后将溶剂旋干，得到粗品经由柱层析，得到57-2产品62mmol。
Step3，取57-2 62mmol，加入0.5当量的1,2,4-三氮唑，180mmol叔丁醇钾，0.6mmolPd2(dba)3，甲苯，氩气置换三次，加入1.2mmol三叔丁基膦，再次氩气置换三次，回流温度下反应10h，粗产品经由柱层析，得到产品44mmol化合物57-3。
Step4，取44mmol化合物57-3，加入1当量的咔唑，150mmol叔丁醇钾，0.5mmol Pd2(dba)3，甲苯，氩气置换三次，加入1.0mmol三叔丁基膦，再次氩气置换三次，回流温度下反应10h，粗产品经由柱层析，得到产品28mmol化合物57。
实施例16：化合物58的合成
Step1～Step3同实施例57中的Step1～Step3。
Step4，取44mmol化合物57-3，加入1当量的9-苯基咔唑硼酸，135mmol碳酸钠，0.5mmol四三苯基磷钯，甲苯，乙醇，水的混合溶剂，氩气置换三次，回流温度下反应10h，粗产品经由柱层析，得到产品37mmol化合物58。
实施例17：化合物59的合成
将实施例57中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例57。实施例18：化合物60的合成
将实施例57中的M＝咔唑换成如上述所述的结构M，其余步骤同实施例57。
本发明实施例制备得到的有机电致发光材料的FD-MS值见表1所示。
表1本发明实施例制备的化合物FD-MS值
对比应用实施例1：
取ITO透明玻璃为阳极，超声清洗后干燥至于真空腔中，抽真空至5×10-5Pa，在上述阳极基板上真空蒸镀NPB作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀厚度为70nm。在空穴传输层上真空蒸镀TAPC/FIrpic作为发光层，掺杂浓度为10wt％，蒸镀速率为0.005nm/s，蒸镀厚度为30nm。在发光层上真空蒸镀Alq3作为电子传输层，蒸镀速率为0.01nm/s，蒸镀厚度为50nm。在电子传输层上真空蒸镀Al层作为阴极，厚度为200nm。
应用实例1：
取ITO透明玻璃为阳极，超声清洗后干燥至于真空腔中，抽真空至5×10-5Pa，在上述阳极基板上真空蒸镀NPB作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀厚度为70nm。在空穴传输层上真空蒸镀化合物1/FIrpic作为发光层，掺杂浓度为10wt％，蒸镀速率为0.005nm/s，蒸镀厚度为30nm。在发光层上真空蒸镀Alq3作为电子传输层，蒸镀速率为0.01nm/s，蒸镀厚度为50nm。在电子传输层上真空蒸镀Al层作为阴极，厚度为200nm。
应用实例2：
将应用实施例1中的化合物1换成化合物2。测量该器件的发光性能，结果见表2。
应用实例3：
将应用实施例1中的化合物1换成化合物3。测量该器件的发光性能，结果见表2。
应用实例4：
将应用实施例1中的化合物1换成化合物4。测量该器件的发光性能，结果见表2。
应用实例5：
将应用实施例1中的化合物1换成化合物5。测量该器件的发光性能，结果见表2。
应用实例6：
将应用实施例1中的化合物1换成化合物6。测量该器件的发光性能，结果见表2。
应用实例7：
将应用实施例1中的化合物1换成化合物7。测量该器件的发光性能，结果见表2。
应用实例8：
将应用实施例1中的化合物1换成化合物8。测量该器件的发光性能，结果见表2。
应用实例9：
将应用实施例1中的化合物1换成化合物11。测量该器件的发光性能，结果见表2。
应用实例10：
将应用实施例1中的化合物1换成化合物12。测量该器件的发光性能，结果见表2。
应用实例11：
将应用实施例1中的化合物1换成化合物29。测量该器件的发光性能，结果见表2。
应用实例12：
将应用实施例1中的化合物1换成化合物33。测量该器件的发光性能，结果见表2。
应用实例13：
将应用实施例1中的化合物1换成化合物42。测量该器件的发光性能，结果见表2。
应用实例14：
将应用实施例1中的化合物1换成化合物57。测量该器件的发光性能，结果见表2。
应用实例15：
将应用实施例1中的化合物1换成化合物58。测量该器件的发光性能，结果见表2。
应用实例16：
将应用实施例1中的化合物1换成化合物59。测量该器件的发光性能，结果见表2。
应用实例17：
将应用实施例1中的化合物1换成化合物60。测量该器件的发光性能，结果见表2。
测量实施例1：对比样品以及样品的发光性能
对比样品以及样品是采用Keithley SMU235，PR650评价发光效率和驱动电压，结果列于表2中：
表2本发明实施例制备的发光器件的发光特性
以上可以看出，本发明的一种以四苯基乙烯为母核的有机发光材料在电致发光器件中进行应用，发光效率最高可达20.3cd/A，驱动电压最低为3.5V，较大的提高了器件的发光效率，是性能良好的有机发光材料。
虽然本发明用示范性实施方案进行了特别的描述，但应该理解在不偏离权利要求所限定的本发明的精神与范围的情况下，本领域普通技术人员可对其进行各种形式和细节上的改变。

Claims (6)

1.一种有机电致发光材料，其结构通式如式I或II所示：
其中，M为含有氮原子的推电子杂环。
2.根据权利要求1所述的一种有机电致发光材料，其特征在于，M选自如下结构中的任意一种：
其中，Ar选自取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳烷基、取代或未取代的C6-C50杂芳基中的任意一种；R1、R2独立的选自氢、取代或未取代的C1-C30烷基、取代或未取代的C6-C50芳基、取代或未取代的C6-C50芳烷基、取代或未取代的C6-C50芳胺、取代或未取代的C3-C50杂芳基中的任意一种；
X选自氧、硫、SO2、CH2、C(CH3)2或CPh2。
3.根据权利要求2所述的一种有机电致发光材料，其特征在于，所述的Ar选自取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基、取代或未取代的C6-C30杂芳基中的任意一种；R1、R2独立的选自氢、取代或未取代的C1-C10烷基、取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基、取代或未取代的C6-C30芳胺、取代或未取代的C3-C30杂芳基中的任意一种。
4.根据权利要求2所述的一种有机电致发光材料，其特征在于，选自如下结构中的任意一种：
5.一种有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层，其特征在于，至少一个有机化合物层包含至少一种如权利要求1～4任意一项中所述的一种有机电致发光材料。
6.根据权利要求5所述的一种有机发光器件，其特征在于，所述有机化合物层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层。
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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN107057684A (zh) * 2017-04-19 2017-08-18 长春海谱润斯科技有限公司 一种基于双极磷光衍生物的有机发光材料及其有机发光器件
CN111233753A (zh) * 2020-02-16 2020-06-05 常州大学 一种aie金属有机凝胶的制备方法
US20210313518A1 (en) * 2018-11-23 2021-10-07 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107057684A (zh) * 2017-04-19 2017-08-18 长春海谱润斯科技有限公司 一种基于双极磷光衍生物的有机发光材料及其有机发光器件
US20210313518A1 (en) * 2018-11-23 2021-10-07 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same
US11980090B2 (en) * 2018-11-23 2024-05-07 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
CN111233753A (zh) * 2020-02-16 2020-06-05 常州大学 一种aie金属有机凝胶的制备方法

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