CN109956897B - 一种9，9’-联蒽衍生物的化合物、包含其的oled显示面板和电子设备 - Google Patents

一种9，9’-联蒽衍生物的化合物、包含其的oled显示面板和电子设备 Download PDF

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CN109956897B
CN109956897B CN201910333228.5A CN201910333228A CN109956897B CN 109956897 B CN109956897 B CN 109956897B CN 201910333228 A CN201910333228 A CN 201910333228A CN 109956897 B CN109956897 B CN 109956897B
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王湘成
陈文勇
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

本发明公开了一种9，9’‑联蒽衍生物的化合物、包含其的OLED显示面板和电子设备，化合物具有如下通式所示的化学结构：
Figure DDA0002038336580000011
x1、x2和x3各自独立地选自碳原子和/或氮原子，且其中至少一个为氮原子；R1、R2和R3各自独立地选自取代或未取代的环形成碳数为6～30的芳基、取代或未取代的环形成原子数为5～30的杂芳基、取代或未取代的碳数为1～30的烷基、取代或未取代的碳数为1～30的氟烷基、取代或未取代的环形成碳数为3～30的环烷基、取代或未取代的碳数为7～30的芳烷基、取代磷酰基、取代甲硅烷基、取代锗基、氰基、硝基或羧基。包含上述化合物的OLED显示面板和电子设备电荷传输能力强，电压低，高效率和寿命长。

Description

一种9，9’-联蒽衍生物的化合物、包含其的OLED显示面板和电 子设备
技术领域
本发明属于电子显示技术领域，具体涉及一种9，9’-联蒽衍生物的化合物、包含其的OLED显示面板和电子设备。
背景技术
现有的OLEDs由基板、阳极、阴极以及夹在两电极中间的有机层组成，其中有机层至少包含空穴传输层、发光层和电子传输层，空穴由阳极发出经过空穴传输层进入发光层，电子由阴极发出经过电子传输层进入发光层，电子和空穴在发光层中进行复合释放能量发光。因此电子和空穴到达发光层的量决定了有机电致发光器件的电压、效率和寿命。常规的电子传输材料电子迁移率比空穴传输材料的空穴迁移率慢很多，使得器件电荷不平衡，导致电压高、效率低和寿命差。传统OLED器件中电子阻挡层的厚度通常为3-8nm，其电子迁移率较差，影响其电子传输能力和器件整体使用寿命。
发明内容
为了克服上述现有技术的缺陷，本发明的目的在于提供一种9，9’-联蒽衍生物的化合物、包含其的OLED显示面板和电子设备，采用具有如通式(Ⅰ)所示化学结构的9，9’-联蒽衍生物的化合物作为电子阻挡层，可以大大提高电子阻挡层的厚度，可达30nm，改善OLED显示面板及其电子设备的电子迁移率，增强电子传输能力，降低电压，提升效率，延长器件整体使用寿命。
为实现上述发明目的，本发明采用如下技术方案：
本发明的9，9’-联蒽衍生物的化合物，所述化合物具有如通式(Ⅰ)所示的化学结构；其中：
Figure BDA0002038336560000011
x1、x2和x3各自独立地选自碳原子和/或氮原子，且其中至少一个为氮原子；
R1、R2和R3各自独立地选自取代或未取代的环形成碳数为6～30的芳基、取代或未取代的环形成原子数为5～30的杂芳基、取代或未取代的碳数为1～30的烷基、取代或未取代的碳数为1～30的氟烷基、取代或未取代的环形成碳数为3～30的环烷基、取代或未取代的碳数为7～30的芳烷基、取代磷酰基、取代甲硅烷基、取代锗基、氰基、硝基或羧基。
进一步，所述化合物选自如下式所示化学结构之一的化合物：
Figure BDA0002038336560000021
Figure BDA0002038336560000031
Figure BDA0002038336560000041
Figure BDA0002038336560000051
Figure BDA0002038336560000061
Figure BDA0002038336560000071
Figure BDA0002038336560000081
Figure BDA0002038336560000091
Figure BDA0002038336560000101
Figure BDA0002038336560000111
Figure BDA0002038336560000121
Figure BDA0002038336560000131
Figure BDA0002038336560000141
Figure BDA0002038336560000151
Figure BDA0002038336560000161
Figure BDA0002038336560000171
Figure BDA0002038336560000181
本发明的OLED显示面板，包括所述9，9’-联蒽衍生物的化合物。
进一步，所述OLED显示面板包括顶发光结构或底发光结构，顶发光为光从远离TFT基板方向发光，底发光为穿透TFT基板发光，底发光和顶发光的区别在于顶发光在阴极上覆盖有覆盖层(CPL)。底发光的结构为阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/阴极。在某些优选实施方案中，所述有机电致发光元件的结构依次阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/空穴阻挡层/电子传输层/阴极。顶发光的结构为阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/阴极/覆盖层。在某些优选实施方案中，所述有机电致发光元件的结构依次阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/空穴阻挡层/电子传输层/阴极/覆盖层。
所述空穴阻挡层(HBL)包括所述的9，9’-联蒽衍生物的化合物。
进一步，所述空穴阻挡层(HBL)的厚度为3-30nm。
更进一步，所述空穴阻挡层(HBL)的厚度为10-30nm。
进一步，所述发光层(EML)的发光颜色选自红光、绿光、蓝光、黄光或白光中的一种或两种以上组合。
进一步，所述电子传输层(ETL)采用质量比为95％：5％～99％：1％之间的有机化合物和N型有机化合物的混合材料，或者质量比为50％：50％～99％：1％的有机化合物与金属化合物的混合材料，或者质量比为85％：15％～95％：5％的有机化合物与金属的混合材料。
本发明的电子设备，包括上述OLED显示面板。
与现有技术相比，本发明的有益效果在于：
传统OLED器件中电子阻挡层的其电子迁移率较差，厚度通常为3-8nm，影响电子传输能力和使用寿命。当电子传输层采用含有金属或者金属化合物时，金属离子会透过薄薄的空穴阻挡层，进入发光层，导致发光淬灭。本发明采用具有如通式(Ⅰ)所示化学结构的9，9’-联蒽衍生物的化合物作为电子阻挡层，可以大大提高电子阻挡层的厚度，可达30nm，改善OLED显示面板及其电子设备的电子迁移率，增强电子传输能力，降低电压，提升效率，延长使用寿命。
附图说明
图1为实施例中OLED显示面板底发光器件的结构示意图。
图2是实施例中OLED显示面板顶发光器件的结构示意图。
具体实施方式
下面结合附图和具体实例详细说明本发明的技术方案。
合成实施例：
本化合物的合成通过suziki反应即可获得，合成通式如下：
Figure BDA0002038336560000191
举例化合物1的合成：
Figure BDA0002038336560000192
在干净250mL的三口烧瓶中，加入固体原料20克(39.1mmol)原料1-1，以及10.8克(39.1mmol)1-2，溶解于溶剂THF。在氮气保护下，加入4.5克(3.91mmol)催化剂Pd(PPh3)4，反应液置于100°的油浴中加热回流24小时，过程采用TLC监测。硅藻土过滤，滤液用乙酸乙酯、水分液。旋干有机相，采用柱层析分离，获得15.5克中间体1-3，收率60％。
在干净250mL的三口烧瓶中，加入10克(15.0mmol)中间体1-3，以及5.4克(15.0mmol)1-4，溶解于溶剂THF。在氮气保护下，加入1.5克(1.5mmol)催化剂Pd(PPh3)4，反应液置于100°的油浴中加热回流24小时，过程采用TLC监测。硅藻土过滤，滤液用乙酸乙酯、水分液。旋干有机相，采用柱层析分离，获得9.5克化合物1，收率70)。
实施例1
制备有机电致发光元件，包括玻璃基板1、厚度为
Figure BDA0002038336560000193
的ITO电极2、厚度为
Figure BDA0002038336560000194
的第一空穴传输层3、厚度为
Figure BDA0002038336560000195
的第二空穴传输层4、厚度为
Figure BDA0002038336560000196
的电子阻挡层mCP(9,9'-(1,3-苯基)二-9H-咔唑)5、厚度为
Figure BDA0002038336560000197
的发光层6、厚度为
Figure BDA0002038336560000198
的空穴阻挡层HBL7、厚度为
Figure BDA0002038336560000201
的第一电子传输层8和厚度为
Figure BDA0002038336560000202
的银电极9；其中：
第一空穴传输层3为P型结构
Figure BDA0002038336560000203
的掺杂材料，主体材料为
Figure BDA0002038336560000204
P型材料和主体材料的质量比为1:50；第二空穴传输层4为NPB材料；发光层6为BH
Figure BDA0002038336560000205
:BD
Figure BDA0002038336560000206
材料，其中BH:BD质量比为19:1；空穴阻挡层HBL7为本发明的化合物1
Figure BDA0002038336560000207
第一电子传输层8为有机电致发光材料，包括
Figure BDA0002038336560000208
和金属Yb，其中ETM：Yb的质量比为5.5:1。
实施例2
空穴阻挡层HBL采用本发明的化合物11
Figure BDA0002038336560000209
替代。
实施例3
空穴阻挡层HBL采用本发明的化合物16
Figure BDA0002038336560000211
替代。
实施例4
空穴阻挡层HBL采用本发明的化合物21
Figure BDA0002038336560000212
替代。
实施例5
空穴阻挡层HBL采用本发明的化合物36
Figure BDA0002038336560000213
替代。
对比例1
空穴阻挡层HBL采用
Figure BDA0002038336560000214
替代。
对比例2
空穴阻挡层HBL采用
Figure BDA0002038336560000215
替代。
在10mA/cm2下测试上述实施例和对比例中元器件的发光性能，如表1所示。
表1
电压(V@10mA/cm<sup>2</sup>) 光效率(Cd/A@10mA/cm<sup>2</sup>)
实施例1 3.6V 8.2
实施例2 3.5V 8.0
实施例3 3.5V 8.1
实施例4 3.4V 8.3
实施例5 3.5V 7.9
对比例1 3.6V 7.8
对比例2 3.9V 6.5
制备有机电致发光元件，包括玻璃基板1、厚度为
Figure BDA0002038336560000221
的ITO电极2、厚度为
Figure BDA0002038336560000222
的第一空穴传输层3、厚度为
Figure BDA0002038336560000229
的第二空穴传输层4、厚度为
Figure BDA0002038336560000223
的电子阻挡层mCP(9,9'-(1,3-苯基)二-9H-咔唑)5、厚度为
Figure BDA0002038336560000224
的发光层6、厚度为
Figure BDA0002038336560000225
的空穴阻挡层HBL7、厚度为
Figure BDA0002038336560000226
的第一电子传输层8和厚度为
Figure BDA0002038336560000227
的银电极9，具体如表2所示。
表2
Figure BDA0002038336560000228

Claims (8)

1.9,9’-联蒽衍生物的化合物，其特征在于，所述化合物选自如下所示化学结构之一：
Figure DEST_PATH_IMAGE002
。
2.OLED显示面板，其特征在于，包括权利要求1所述9,9’-联蒽衍生物的化合物。
3.根据权利要求2所述的OLED显示面板，其特征在于，包括顶发光结构或底发光结构，所述底发光结构依次包括基板、阳极、空穴注入层、空穴传输层Ⅰ、空穴传输层Ⅱ、发光层、空穴阻挡层、电子传输层和阴极，所述顶发光结构依次包括基板、阳极、空穴注入层、空穴传输层Ⅰ、空穴传输层Ⅱ、发光层、空穴阻挡层、电子传输层、阴极和覆盖层；
上述结构中所述空穴阻挡层均包括权利要求1所述9,9’-联蒽衍生物的化合物。
4.根据权利要求3所述的OLED显示面板，其特征在于，所述空穴阻挡层的厚度为3-30nm。
5.根据权利要求4所述的OLED显示面板，其特征在于，所述空穴阻挡层的厚度为10-30nm。
6.根据权利要求3所述的OLED显示面板，其特征在于，所述发光层的发光颜色选自红光、绿光、蓝光、黄光或白光中的一种或两种以上组合。
7.根据权利要求3所述的OLED显示面板，其特征在于，所述电子传输层采用质量比为95：5-99：1的有机化合物和N型有机化合物的混合材料、或质量比为50：50-99：1的有机化合物与金属化合物的混合材料、或质量比为85：15-95：5的有机化合物与金属的混合材料。
8.一种电子设备，其特征在于，包括权利要求2-7任一项所述的OLED显示面板。
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