CN115010609A - 一种含有二苯基芴结构的胺基化合物及有机电致发光器件 - Google Patents
一种含有二苯基芴结构的胺基化合物及有机电致发光器件 Download PDFInfo
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Abstract
本发明公开了一种含有二苯基芴结构的胺基化合物及有机电致发光器件。本发明中的化合物均具有适当的分子量,该范围分子量的化合物具有更加合适的升华温度及蒸镀温度,可以有效避免由于升华及蒸镀温度过高从而导致材料裂解的量产性风险。该类化合物中9,9‑二苯基芴的苯环与二芳基胺的N相连接,显著增加了材料分子的空间位阻及空间旋转自由度,进而适当降低了材料分子的熔点,适当的熔点使得该类材料在蒸镀时处于熔融状态,有效避免材料在蒸镀时发生堵孔现象,进而有效提高器件制备的良率。
Description
技术领域
本发明涉及有机电致发光技术领域,具体涉及一种含有二苯基芴结构的胺基化合物及有机电致发光器件。
背景技术
通常,有机发光现象是指通过使用有机材料将电能转换成光能的现象。利用有机发光现象的有机发光器件具有诸如宽视角、优异的对比度、快速的响应时间,优异的亮度、驱动电压和响应速度的特性,并因此进行了许多研究。
有机发光器件通常具有包括阳极、阴极和介于阳极与阴极之间的有机材料层的结构。有机材料层通常具有包含不同材料的多层结构以提高有机发光器件的效率和稳定性,例如,有机材料层可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。在有机发光器件的结构中,如果在两个电极之间施加电压,则空穴从阳极注入有机材料层中,电子从阴极注入有机材料层中,并且当注入的空穴和电子彼此相遇时,形成激子,并且当激子再次落至基态时发光。
已有各种OLED制造方法。小分子OLED通常通过真空热蒸发来制造。聚合物OLED通过溶液法制造,例如旋涂,喷墨印刷和喷嘴印刷。如果材料可以溶解或分散在溶剂中,小分子OLED也可以通过溶液法制造。
OLED的发光颜色可以通过发光材料结构设计来实现。OLED可以包括一个发光层或多个发光层以实现期望的光谱。绿色,黄色和红色OLED,磷光材料已成功实现商业化。蓝色磷光器件仍然具有蓝色不饱和,器件寿命短和工作电压高等问题。商业全彩OLED显示器通常采用混合策略,使用蓝色荧光和磷光黄色,或红色和绿色。目前,磷光OLED的效率在高亮度情况下快速降低仍然是一个问题。此外,期望具有更饱和的发光光谱,更高的效率和更长的器件寿命。
发明内容
本发明的目的是针对上述技术问题,提供了一种含有二苯基芴结构的胺基化合物及有机电致发光器件。
本发明的目的可以通过以下措施达到:
一种含有二苯基芴结构的胺基化合物,其结构式如下式1所示:
其中,
R1为氘代或未氘代的C6-30芳香基;
R2为氘代或未氘代的苯基;
R3、R4、R5各自独立地为氢或者氘代或未氘代的苯基,且R3-R5不同时为苯基。
在一种优选方案中,`R1为氘代或未氘代下列基团:苯基、联苯基、三联苯基、蒽基或奈基。
在一种优选方案中,本发明化合物的结构式如下式2、式3或式4所示:
在一种优选方案中,R1为氘代或未氘代的联苯基。
在一种优选方案中,本发明的化合物为以下化合物中的任意一种:
本发明化合物的合成路线如下:
一种有机电致发光器件,包括第一电极、第二电极以及在第一电极和第二电极之间形成的有机层,有机层中含有上述化合物;特别是有机层包含空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层;空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层含有本发明的化合物;更特别的是第二空穴传输层中含有上述的化合物。
一种含有上述有机电致发光器件的电子显示设备。
一种含有上述有机电致发光器件的OLED照明设备。
本发明所述室温均为25±5℃。
本发明设计了一类全新的有机电致发光材料。该类材料具有以下特点:
本发明中的化合物均具有适当的分子量(均在750-850之间),该范围分子量的化合物具有更加合适的升华温度及蒸镀温度,可以有效避免由于升华及蒸镀温度过高从而导致材料裂解的量产性风险。
9,9-二苯基芴的苯环与二芳基胺的N相连接,显著增加了材料分子的空间位阻及空间旋转自由度,进而适当降低了材料分子的熔点,适当的熔点使得该类材料在蒸镀时处于熔融状态,有效避免材料在蒸镀时发生堵孔现象,进而有效提高器件制备的良率。并且蒸镀时处于熔融状态的材料具有更好的成膜性,有效改善了器件的寿命。同时,较高的旋转自由度增加材料分子的溶解性,从而有效降低材料的制备难度及加工成本。
9,9-二甲基芴的3号位置使用苯环保护起来,增加了材料分子的扭矩,进而提高了材料的三线态能级,避免了能量由发光层向传输层的反向传递,进而提高了器件的发光效率。
附图说明
图1是本发明有机电致发光器件的结构示意图;
图中标号分别代表:1-阳极、2-空穴注入层、3-第一空穴传输层、4-第二空穴传输层、5-发光层、6-空穴阻挡层、7-电子传输层、8-电子注入层、9-阴极。
图2是本发明实施例1中所制备的化合物10的HPLC图。
图3是本发明实施例1中所制备的化合物10的DSC图谱,由图3可知,化合物10的Tg值为157.00℃。
图4是本发明实施例1中所制备的化合物10的TGA图谱,由图4可知,热失重温度Td值为447.93℃。
图5是本发明应用例1和对照例1中有机电致发光器件的寿命图;由图5可知,本发明应用例1和对照例1所制备的有机电致发光器件的T97%寿命分别为723h和432h。
图6是本发明实施例4中所制备的化合物7的核磁图谱。
具体实施方式
以下进一步说明和描述了各个方面的实施例。应当理解,本文的描述并非旨在将权利要求书限制于所描述的特定方面。相反,旨在覆盖可包括在由所附权利要求书限定的本公开的精神和范围内的替代、修改和等同物。
如本文所用,在“取代的”或“未取代的”中,术语“取代的”是指该基团中的至少一个氢与氘、烃基、烃衍生物基、卤素或氰基(-CN)重新配位。术语“未取代的”是指该基团中的至少一个氢不与氘、烃基、烃衍生物基、卤素或氰基(-CN)重新配位。烃基或烃衍生物基团的实例可包括C1至C30烷基、C2至C30烯基、C2至C30炔基、C6至C30芳基、C5至C30杂芳基、C1至C30烷氨基、C6至C30芳氨基、C6至C30杂芳氨基、C6至C30芳基杂芳氨基等,但不限于此。
本发明中的氘,是指氢的一种稳定形态同位素,也被称为重氢,其元素符号为D。
本发明中的芳香基,是指6至30个碳原子的全碳单环或稠合多环基团,具有完全共轭的π电子系统。芳基的非限制性实施例有苯基、萘基、蒽基、联苯基、邻三联苯基、间三联苯基、对三联苯基、苯并菲基、三苯基[1,12-bcd]呋喃基、菲基等。
实施例中未注明具体条件者,按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者,均为可以通过市售购买获得的常规产品。
实施例1:
化合物10的合成方法如下:
氮气保护下,在三口烧瓶中,将1-a(40g,0.14mol,1.02eq)和1-b(32g,0.133mol,1eq)溶于300mL甲苯中,加入Pd2(dba)3(2.6g,2.8mmol,2%eq),三叔丁基膦(8.5mL,4.1mmol,3%eq),叔丁醇钠(20g,0.205mol,1.5eq),110℃下回流反应,HPLC监测反应进度。
HPLC监测显示中间体1-b反应完全,停止反应,降室温,加水300mL,分液,有机相过硅胶和无水硫酸镁,有机相减压浓缩,加入乙醇热煮过夜,降温抽滤,少量乙醇冲洗,得1-c重20g,纯度99.5%,收率70.2%。
氮气保护下,在三口烧瓶中,将1-c(40g,91.5mmol,1eq)和1-d(34.5g,86.9mmol,0.95eq)溶于300mL甲苯中,加入Pd2(dba)3(1.7g,1.74mmol,2%eq),三叔丁基膦(5.3mL,2.6mmol,3%eq),叔丁醇钠(12.6g,0.13mol,1.5eq),110℃下回流反应,HPLC监测反应进度。
HPLC监测显示中间体1-c反应完全,停止反应,降室温,加水300mL,抽滤,滤饼用200mL乙醇冲洗,10倍体积甲苯溶解,过硅胶(200-300目,用量100g),加活性炭(50g),降温析晶,再用10倍体积甲苯重结晶三次得化合物10(27.5g,纯度99.97%,收率42.3%)。ESI-MS(m/z)(M+):理论值753.97,实测值753.35;元素分析结果(分子式C58H43N):理论值C,92.39;H,5.75;N,1.86;实测值C,92.37;H,5.76;N,1.87。
以类似方式获得如下产物化合物:
表1
上文所制备的化合物的合成鉴别结果如下表2所示:
表2
材料性质测试:
测试本发明化合物1、3、7、10、13、14、23、26、37、47、49、51、52、55、61、63、67、73、74、75、79、83的热失重温度Td和玻璃化转变温度Tg,测试结果如下表3所示。
注:热失重温度Td是在氮气气氛中失重5%的温度,在TGAN-1000热重分析仪上进行测定,测定时氮气流量为10mL/min,Tg(玻璃化转变温度)由示差扫描量热法(DSC,新科DSC N-650)测定,升温速率10℃/min。
表3:
由上述数据可知,本发明所合成的化合物的热稳定性优良,说明符合本发明结构通式的化合物都具有优良的热稳定性,可以满足有机电致发光材料使用的要求。
器件性能测试:
应用例1:
采用ITO作为反射层阳极基板材料,并依次用水、丙酮、N2等离子对其进行表面处理;
在ITO阳极基板上方,沉积10nm掺杂有质量比为2%NDP-9的HT-1,形成空穴注入层(HIL);
在空穴注入层(HIL)上方蒸镀100nm的HT-1形成第一空穴传输层(HTL);
在第一空穴传输层(HTL)上方真空蒸镀本发明设计的化合物10,形成厚度为30nm的第二空穴传输层(GPL);
将化合物G1与G2按照5:5的质量比例作为绿光主体材料进行共同蒸镀,GD-1作为掺杂材料(GD-1用量为G1与G2总质量的8%)蒸镀在第二空穴传输层(GPL)上形成厚度为30nm的发光层;
将HB-1蒸镀到发光层上得到厚度为20nm的空穴阻挡层(HBL);
将ET-1与LiQ按照5:5的质量比例进行共同蒸镀到空穴阻挡层(HBL)上得到厚度为30nm的电子传输层(ETL);
将镁(Mg)和银(Ag)以9:1的质量比例混合蒸镀到电子传输层(ETL)上方,形成厚度为50nm的电子注入层(EIL);
此后将银(Ag)蒸镀到电子注入层上方,形成厚度为100nm的阴极,在上述阴极封口层上沉积50nm厚度的DNTPD,此外,在阴极表面以UV硬化胶合剂和含有除湿剂的封装薄膜(seal cap)进行密封,以保护有机电致发光器件不被大气中的氧气或水分所影响至此制备获得有机电致发光器件。
应用例2-22
分别以本发明实施例2-22中的化合物1、3、7、13、14、23、26、37、47、49、51、52、55、61、63、67、73、74、75、79、83作为第二空穴传输材料,其他部分与应用例1一致,据此制作出应用例2-22的有机电致发光器件。
对照例1-4:
与应用例1的区别在于,分别用KR1020220008668A中的化合物A、化合物B以及WO2022080715A1中的A1、A3分别代替本申请中的化合物10作为第二空穴传输材料,其余与应用例1相同。
上述应用例制造的有机电致发光器件及对照例制造的有机电致发光器件的特性是在电流密度为10mA/cm2的条件下测定的,结果如表4所示。
表4:
由如上表4可知,本发明化合物应用于有机电致发光器件中,在相同电流密度下,发光效率得到了较大幅度的提升,器件的启动电压有所下降,器件的功耗相对降低,器件的寿命相应提高。
分别将对照例1-4、应用例1-8所制备的有机电致发光器件进行发光寿命测试,得到发光寿命T97%数据(发光亮度降低至初始亮度97%的时间),测试设备为TEO发光器件寿命测试系统。结果如表5所示:
表5:
由上表5可知,将本发明化合物应用于有机电致发光器件中,在相同电流密度下,使用寿命得到较大程度提升,具有广阔的应用前景。
Claims (10)
2.如权利要求1所述的化合物,其特征在于,R1为氘代或未氘代下列基团:苯基、联苯基、三联苯基、蒽基或奈基。
4.如权利要求1所述的化合物,其特征在于,R1为氘代或未氘代的联苯基。
6.一种有机电致发光器件,其特征在于,包括第一电极、第二电极以及在所述第一电极和所述第二电极之间形成的有机层,所述有机层中含有如权利要求1-4中任一项所述的化合物。
7.如权利要求5所述的有机电致发光器件,其特征在于,所述有机层包含空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层;所述空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层含有权利要求1-4中任一项所述的化合物。
8.如权利要求6所述的有机电致发光器件,其特征在于,所述第二空穴传输层中含有如权利要求1-3中任一项所述的化合物。
9.一种电子显示设备,其特征在于,含有如权利要求5所述的有机电致发光器件。
10.一种OLED照明设备,其特征在于,含有如权利要求5所述的有机电致发光器件。
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