CN113929670A - 一种用于电子传输材料的有机电致发光化合物及其应用 - Google Patents

一种用于电子传输材料的有机电致发光化合物及其应用 Download PDF

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CN113929670A
CN113929670A CN202111316291.1A CN202111316291A CN113929670A CN 113929670 A CN113929670 A CN 113929670A CN 202111316291 A CN202111316291 A CN 202111316291A CN 113929670 A CN113929670 A CN 113929670A
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李晓龙
石鹏凯
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EverDisplay Optronics Shanghai Co Ltd
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Abstract

本发明涉及一种用于电子传输材料的有机电致发光化合物，所述有机电致发光化合物的结构如式(I)所示；其中，Ar1‑Ar3分别独立地选自取代或未取代的芳基或取代或未取代的杂芳基；X1选自CR1或N；X2选自O或S；L选自直接键合或亚苯基。本发明的有机电致发光化合物，具有较高的玻璃化转变温度和分子热稳定性，具有合适的HOMO和LUMO能级，应用至OLED器件制作中，可有效提高器件的发光效率和OLED器件的使用寿命。

Description

一种用于电子传输材料的有机电致发光化合物及其应用
技术领域
本发明涉及有机电致发光技术领域，尤其涉及一种用于电子传输材料的有机电致发光化合物及其应用。
背景技术
以20世纪50年底Bernanose的有机薄膜发光观测为起点，之后进行了针对由1965年利用蒽单晶蓝色电发光所发展出有机电致发光(EL)元件的研究，随之1987年由唐提出了分为空穴层和发光层这两个功能层层叠结构的有机电致发光元件。之后，为了制造高效率、高寿命的有机电致发光元件，发展出了在元件内导入各个特征有机层的形态，进而进行了用于此的专用物质的开发。
有关有机元件(EL)，从两电极注入的电荷在发光层重合而获得发光。为了获得高发光效率，空穴、电子的两电荷向发光层有效的输送、注入发光层的两电荷的平衡、生成的激子的紧闭等变得很重要。若提高从空穴传输层向发光层的空穴注入性，提高空穴传输层的电子阻挡性来防止电子从发光层向空穴传输层的泄露，则能提高在发光层的空穴与电子重合的概率，能够有效的生成激子。而且，在发光层内生成的激子不泄露到传输层，将该激子紧闭在发光层，由此能够获得高得发光效率。因此，空穴传输材料所起的作用是重要的，需要空穴注入性高、空穴迁移率大、电子阻挡性高且对电子的耐久性高的空穴传输材料。
为了改进有机元件EL的元件特性、提高元件制备的成品率，通过将空穴及电子的注入传输性、薄膜的稳定性及耐久性优异的材料组合，寻求空穴及电子能够高效率重合、发光效率高、驱动电压低且长寿命的元件。另外，对于不同结构的OLED器件搭配而言，所使用的光电功能材料具有较强的选择性，相同的材料在不同结构器件中的性能表现，也可能完全迥异。因此，针对当前OLED器件的产业应用要求，以及OLED器件的不同功能膜层，器件的光电特性需求，必须选择更适合，具有高性能的OLED功能材料或材料组合，才能实现器件的高效率、长寿命和低电压的综合特性。就当前OLED显示照明产业的实际需求而言，目前OLED材料的发展还远远落后于面板制造企业的要求，作为材料企业开发更高性能的有机功能材料显得尤为重要。
因此，本发明提供了一种长寿且高效的用于电子传输材料的有机电致发光化合物及其应用。
发明内容
本发明的目的是针对现有技术中的不足，提供一种用于电子传输材料的有机电致发光化合物及其应用。
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电子传输材料的有机电致发光化合物，所述有机电致发光化合物的结构如式(I)所示：
Figure BDA0003343751390000021
其中，Ar1-Ar3分别独立地选自取代或未取代的芳基或取代或未取代的杂芳基；X1选自CR1或N；X2选自O或S；L选自直接键合或亚苯基。
优选地，Ar1-Ar3分别独立地选自取代或未取代的C6-C60的芳基或取代或未取代的C6-C60的杂芳基。
优选地，Ar1-Ar3分别独立地选自苯基、萘基、蒽基、菲基、喹啉基、咔唑基、二苯并呋喃基、吩嗪基、吩喹嗪基。
优选地，R1选自H。
优选地，所述有机电致发光化合物选自：
Figure BDA0003343751390000031
本发明的第二方面是提供一种电子传输材料，包括：如上所述的有机电致发光化合物。
本发明的第三方面是提供一种电子传输层，包括：如上所述的电子传输材料。
本发明的第四方面是提供一种有机电致发光器件，包括：如上所述的电子传输层。
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：
本发明的有机电致发光化合物，具有较高的玻璃化转变温度和分子热稳定性，具有合适的HOMO和LUMO能级，应用至OLED器件制作中，可有效提高器件的发光效率和OLED器件的使用寿命。
具体实施方式
下面将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
本实施例提供一种如前所述有机电致发光化合物的制备方法，步骤包括：
Figure BDA0003343751390000041
在氮气气流下，将原料A、原料B加入甲苯/DME/H2O中，随后加入Pd(OAc)2、PPh3、NaCO3，搅拌混合，加热回流8小时。反应结束后，冷却至室温，利用二氯甲烷提取，然后加入MgSO4并过滤。从所得的有机层中将溶剂去除后，得到中间体1。
Figure BDA0003343751390000042
在氮气气流下，将中间体1、原料C加入甲苯/DME/H2O中，随后加入Pd(OAc)2、PPh3、NaCO3，搅拌混合，加热回流8小时。反应结束后，冷却至室温，利用二氯甲烷提取，然后加入MgSO4并过滤。从所得的有机层中将溶剂去除后，得到中间体2。
Figure BDA0003343751390000051
在氮气气流下，将中间体2、原料D加入甲苯/DME/H2O中，随后加入Pd(OAc)2、PPh3、NaCO3，搅拌混合，加热回流8小时。反应结束后，冷却至室温，利用二氯甲烷提取，然后加入MgSO4并过滤。从所得的有机层中将溶剂去除后，得到中间体3。
Figure BDA0003343751390000052
在氮气气流下，将中间体3、原料E加入甲苯/DME/H2O中，随后加入Pd(OAc)2、PPh3、NaCO3，搅拌混合，加热回流8小时。反应结束后，冷却至室温，利用二氯甲烷提取，然后加入MgSO4并过滤。从所得的有机层中将溶剂去除后，得到中间体4。
Figure BDA0003343751390000053
在氮气气流下，将中间体4、原料F加入甲苯/DME/H2O中，随后加入Pd(OAc)2、PPh3、NaCO3，搅拌混合，加热回流8小时。反应结束后，冷却至室温，利用二氯甲烷提取，然后加入MgSO4并过滤。从所得的有机层中将溶剂去除后，得到中间体5。
Figure BDA0003343751390000054
氮气氛围下，称取中间体5并溶解于甲苯/DME/H2O中，随后加入原料G及Pd(Pddf)Cl2、XPhos、KOAc，搅拌混合，再加入1,4-二噁烷，将上述反应物的混合溶液于反应温度70-90℃下，加热回流8小时。反应结束后，冷却加水、混合物用二氯甲烷萃取，萃取液用无水硫酸钠干燥，过滤并在减压下浓缩，所得残余物过硅胶柱纯化，得到中间体A1。
或
Figure BDA0003343751390000061
在氮气气流下，将中间体5、原料H加入甲苯/DME/H2O中，随后加入Pd(OAc)2、PPh3、NaCO3，搅拌混合，加热回流8小时。反应结束后，冷却至室温，利用二氯甲烷提取，然后加入MgSO4并过滤。从所得的有机层中将溶剂去除后，得到中间体6。
Figure BDA0003343751390000062
氮气氛围下，称取中间体6并溶解于甲苯/DME/H2O中，随后加入原料E及Pd(Pddf)Cl2、XPhos、KOAc，搅拌混合，再加入1,4-二噁烷，将上述反应物的混合溶液于反应温度70-90℃下，加热回流8小时。反应结束后，冷却加水、混合物用二氯甲烷萃取，萃取液用无水硫酸钠干燥，过滤并在减压下浓缩，所得残余物过硅胶柱纯化，得到中间体A2。
Figure BDA0003343751390000063
Figure BDA0003343751390000071
在氮气气流下，将中间体A1/中间体A2、原料X加入甲苯/DME/H2O中，随后加入Pd(OAc)2、PPh3、NaCO3，搅拌混合，加热回流8小时。反应结束后，冷却至室温，利用二氯甲烷提取，然后加入MgSO4并过滤。从所得的有机层中将溶剂去除后，得到化合物。
表1
Figure BDA0003343751390000072
Figure BDA0003343751390000081
以化合物1为例：
Figure BDA0003343751390000082
Figure BDA0003343751390000091
HPLC纯度为99％，收率为77.6％。元素分析结构(分子式C40H27N4O)：理论值C，82.88；H，4.69；N，9.67；O，2.76；测试值：C，82.25；H，4.5；N，9.36；O，2.66。ESI-MS(m/z)(M+)：理论值为579.68，实测值为579.32。
同样地，化合物2：HPLC纯度为99.1％，收率为77％。元素分析结构(分子式C40H27N4S)：理论值C，80.65；H，4.59；N，9.4；S，5.38；测试值：C，80.45；H，4.29；N，9.34；S，5.48。ESI-MS(m/z)(M+)：理论值为575.2.，实测值为575.32。
化合物4：HPLC纯度为99％，收率为77.1％。元素分析结构(分子式C40H27N4S)：理论值C，82.8；H，4.75；N，7.07；S，5.38；测试值：C，82.81；H，4.79；N，7.06；S，5.48。ESI-MS(m/z)(M+)：理论值为594.2.，实测值为594.22。
化合物6：HPLC纯度为99.2％，收率为77.1％。元素分析结构(分子式C45H33N4O)：理论值C，83.7；H，5.15；N，8.68；O，2.48；测试值：C，83.65；H，5.25；N，8.58；O，2.46。ESI-MS(m/z)(M+)：理论值为645.27，实测值为645.3。
化合物9：HPLC纯度为98.8％，收率为77.3％。元素分析结构(分子式C45H36N5O)：理论值C，81.55；H，5.47；N，10.57；O，2.41；测试值：C，81.52；H，5.44；N，10.51；O，2.45。ESI-MS(m/z)(M+)：理论值为662.3，实测值为662.97。
化合物10：HPLC纯度为98.9％，收率为77.3％。元素分析结构(分子式C49H35N4O)：理论值C，84.55；H，5.07；N，8.05；O，2.31；测试值：C，84.52；H，5.01；N，8.0；O，2.38。ESI-MS(m/z)(M+)：理论值为695.3，实测值为695.28。
化合物14：HPLC纯度为99.1％，收率为76.8％。元素分析结构(分子式C59H41N4O)：理论值C，86.21；H，5.07；N，6.82；O，1.95；测试值：C，86.25；H，5.06；N，6.84；O，1.98。ESI-MS(m/z)(M+)：理论值为821.33，实测值为821.4。
化合物22：HPLC纯度为99.1％，收率为76.9％。元素分析结构(分子式C55H35N4O2)：理论值C，84.27；H，4.5；N，7.15；O，4.08；测试值：C，84.25；H，4.51；N，7.18；O，4.1。ESI-MS(m/z)(M+)：理论值为783.28，实测值为783.3。
应用实施例
本应用实施例提供一种有机电致发光器件的制备方法，步骤包括：
清洗透明基板层上的ITO(氧化铟锡)阳极层，依次采用去离子水、丙酮、乙醇超声清洗15分钟，并在等离子体清洗器中处理2分钟；
在ITO阳极层上，通过真空蒸镀方式蒸镀空穴注入材料HAT-CN，厚度为10nm，这层作为空穴注入层；
在空穴注入层上，通过真空蒸镀方式蒸镀空穴传输材料NPB，厚度为80nm，该层为空穴传输层或电子阻挡层；
在空穴传输层/电子阻挡层上，通过真空蒸镀方式蒸镀发光层，主体材料为GH，掺杂材料为Ir(ppy)3，且GH与Ir(ppy)3的质量比为50:10，厚度为30nm；
在发光层上，通过真空蒸镀方式蒸镀电子传输材料化合物1-26/Alq3/T1/T2，厚度为40nm，该层为空穴阻挡层/电子传输层；
在空穴阻挡层/电子传输层上，通过真空蒸镀方式蒸镀电子注入材料LiF，厚度为1nm，该层为电子注入层；
在电子注入层上，通过真空蒸镀方式蒸镀阴极材料Mg:Ag/Ag，Mg:Ag的掺杂比例为9:1，厚度为15nm，Ag的厚度为3nm，该层为阴极层。
Figure BDA0003343751390000111
检测实施例
本检测实施例提供一种如前所述有机电致发光器件的性能测试
表2
Figure BDA0003343751390000112
Figure BDA0003343751390000121
其中，驱动电压在电流密度为10mA/cm2时测得的，器件性能在1000nits亮度下测得的，寿命在恒定电流密度40mA/cm2条件下计算得到的。
由上表可知，本发明的有机电致发光化合物高度适用于OLED器件中，所制备得到的有机电致发光器件具有很好的性能。与同比例的元件相比，光取出得到明显提升，相同电流密度下，器件亮度和器件效率都得到了提升，由于亮度及效率得到提升，OLED器件在定亮度下的功耗相对降低，使用寿命也得到提高。
综上所述，本发明的有机电致发光化合物，具有较高的玻璃化转变温度和分子热稳定性，具有合适的HOMO和LUMO能级，应用至OLED器件制作中，可有效提高器件的发光效率和OLED器件的使用寿命。
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 (8)

1.一种用于电子传输材料的有机电致发光化合物，其特征在于，所述有机电致发光化合物的结构如式(I)所示：
Figure FDA0003343751380000011
其中，Ar1-Ar3分别独立地选自取代或未取代的芳基或取代或未取代的杂芳基；X1选自CR1或N；X2选自O或S；L选自直接键合或亚苯基。
2.根据权利要求1所述的有机电致发光化合物，其特征在于，Ar1-Ar3分别独立地选自取代或未取代的C6-C60的芳基或取代或未取代的C6-C60的杂芳基。
3.根据权利要求2所述的有机电致发光化合物，其特征在于，Ar1-Ar3分别独立地选自苯基、萘基、蒽基、菲基、喹啉基、咔唑基、二苯并呋喃基、吩嗪基、吩喹嗪基。
4.根据权利要求1所述的有机电致发光化合物，其特征在于，R1选自H。
5.根据权利要求1所述的有机电致发光化合物，其特征在于，所述有机电致发光化合物选自：
Figure FDA0003343751380000021
6.一种电子传输材料，其特征在于，包括：如权利要求1-5任一项所述的有机电致发光化合物。
7.一种电子传输层，其特征在于，包括：如权利要求6所述的电子传输材料。
8.一种有机电致发光器件，其特征在于，包括：如权利要求7所述的电子传输层。
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