CN114230559A - 一种有机电致发光的化合物及其应用 - Google Patents

一种有机电致发光的化合物及其应用 Download PDF

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CN114230559A
CN114230559A CN202111538531.2A CN202111538531A CN114230559A CN 114230559 A CN114230559 A CN 114230559A CN 202111538531 A CN202111538531 A CN 202111538531A CN 114230559 A CN114230559 A CN 114230559A
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李丹丹
张磊
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EverDisplay Optronics Shanghai Co Ltd
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Abstract

本发明涉及一种有机电致发光的化合物，所述化合物的结构如式(I)所示；其中，Ar1‑Ar2分别独立地选自取代或未取代的芳香族烃基；X1‑X3分别独立地选自N或CR；L1‑L2分别独立地选自直接键合、取代或未取代的脂肪族亚烃基或取代或未取代的芳香族亚烃基；Y选自NH、O或S。本发明的化合物具有高的电荷迁移率，因此可以有效地降低电压，提高光电效率，并且可提高OLED器件的寿命。

Description

一种有机电致发光的化合物及其应用
技术领域
本发明涉及有机电致发光技术领域，尤其涉及一种有机电致发光的化合物及其应用。
背景技术
有机发光器件(OLED)是自发射器件，与常规器件相比，其具有视角宽，对比度高、响应时间短、响应速度快，以及优异的亮度、节能省电、色彩显示等，因此具有广阔的应用前景。典型的有机发光器件包括阴极、阳极以及在阴极和阳极之间的有机发光层，从阳极提供的空穴可通过空穴传输区域朝着发射层移动，从阴极产生的电子通过电子传输区域朝着发射层移动，空穴和电子在发射层中复合以产生激子，这些激子从激发态跃迁到基态，由此产生光。
有机发光层的材料包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等，为了实现有机发光装置的优异性能，构成有机材料层的材料，应当是稳定的并且具有优良的效率，因此需要开发新的有机材料以不断提高有机发光器件的性能。
发明内容
本发明的目的是针对现有技术中的不足，提供一种有机电致发光的化合物及其应用。
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有机电致发光的化合物，所述化合物的结构如式(I)所示：
Figure BDA0003413635880000011
Figure BDA0003413635880000021
其中，Ar1-Ar2分别独立地选自取代或未取代的芳香族烃基；X1-X3分别独立地选自N或CR；L1-L2分别独立地选自直接键合、取代或未取代的脂肪族亚烃基或取代或未取代的芳香族亚烃基；Y选自NH、O或S。
优选地，Ar1-Ar2分别独立地选自取代或未取代的C6-C30的芳香族烃基。
优选地，Ar1-Ar2分别独立地选自苯基、萘基、蒽基、菲基、芴基、二苯并呋喃基、二苯并噻吩基、二甲基芴基或二苯基芴基。
优选地，X1-X3不全为CR。
优选地，L1-L2分别独立地选自直接键合、取代或未取代的C6-C30的脂肪族亚烃基或取代或未取代的C6-C30的芳香族亚烃基。
优选地，所述化合物选自：
Figure BDA0003413635880000022
Figure BDA0003413635880000031
Figure BDA0003413635880000041
Figure BDA0003413635880000051
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：
本发明的化合物具有高的电荷迁移率，因此可以有效地降低电压，提高光电效率，并且可提高OLED器件的寿命。
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1
本实施例提供一种有机电致发光的化合物及其制备方法，制备的步骤包括：
Figure BDA0003413635880000052
在氮气气氛下，将5g的化合物1-a、7g的化合物1-b、4g的无水磷酸钾粉末与200mL的无水1,4-二氧六环充分混合，回流加热到101℃下，向其中加入0.6g的催化剂Pd(PPh3)4，搅拌回流24h，使反应充分进行，利用薄层色谱检测反应基本完全；使混合物冷却至常温，再通过柱色谱层析，得到6.2g的化合物1-c。
Figure BDA0003413635880000061
将6g的化合物1-c、5g的联硼烷B2Pin2、3g的乙酸钾与200mL的无水1,4-二氧六环混合后充分搅拌，100℃下加热回流，加入0.4g的Pa2dba3，充分回流反应24h后，通过过滤、重结晶、柱色谱，得到6.6g的化合物1-d(产率70％)。
Figure BDA0003413635880000062
在氮气气氛下，将6g的化合物1-d、4.5g的化合物1-e、4.3g的无水磷酸钾粉末与200mL的无水1,4-二氧六环充分混合，向其中加入0.6g的催化剂Pd(PPh3)4，在101℃下回流加热24h，利用薄层色谱检测反应基本完全。通过重结晶，柱色谱层析，得到化合物1约5.6g(52％)。
表征数据如下：Tg(DSC)133℃，纯度99.9％，1H NMR(400MHz，DMSO)δ9.08(d，1H)，8.84(d，1H)，8.36(d，4H)，8.27(d，1H)，8.05(s，1H)，8.03(d，2H)，7.90(d，1H)，7.82(d，2H)，7.76(s，2H)，7.70(m，1H)，7.68(m，1H)，7.63(m，2H)，7.50(m，6H)。
实施例2
本实施例提供另一种有机电致发光的化合物及其制备方法，制备的步骤与实施例1类似：
Figure BDA0003413635880000071
得到化合物2约6.3g(产率59％)，表征数据如下：Tg(DSC)135℃，纯度99.9％，1HNMR(400MHz，DMSO)δ9.08(d，1H)，8.84(d，1H)，8.36(d，4H)，8.27(d，1H)，8.05(s，1H)，8.03(d，1H)，7.83(s，1H)，7.82(d，1H)，7.90(d，1H)，7.88(d，1H)，7.79(d，1H)，7.76(s，1H)，7.70(m，1H)，7.68(m，1H)，7.63(m，2H)，7.50(m，6H)。
实施例3
本实施例提供另一种有机电致发光的化合物及其制备方法，制备的步骤与实施例1类似：
Figure BDA0003413635880000072
Figure BDA0003413635880000081
得到化合物3约5.8g(产率49％)，表征数据如下：Tg(DSC)140℃，纯度99.9％，1HNMR(400MHz，DMSO)δ9.08(d，1H)，8.84(d，1H)，8.36(d，4H)，8.27(d，1H)，8.05(s，1H)，8.03(d，2H)，7.90(d，1H)，7.82(d，2H)，7.76(s，2H)，7.70(m，1H)，7.68(m，1H)，7.63(m，2H)，7.50(m，6H)，7.25(d，4H)。
实施例4
本实施例提供另一种有机电致发光的化合物及其制备方法，制备的步骤与实施例1类似：
Figure BDA0003413635880000082
得到化合物4约6.7g(产率55％)，表征数据如下：Tg(DSC)138℃，纯度99.9％，1HNMR(400MHz，DMSO)δ9.08(d，1H)，8.84(d，1H)，8.36(d，4H)，8.27(d，1H)，8.05(s，1H)，8.24(d，2H)，7.94(d，1H)，7.90(d，1H)，8.17(d，1H)，8.20(s，2H)，7.70(m，1H)，7.68(m，1H)，7.63(m，2H)，7.50(m，6H)。
应用实施例
本应用实施例提供一种有机电致发光器件，依次包括：阳极、空穴注入层、空穴传输层、发光层、电子传输层、阴极。
表1
Figure BDA0003413635880000091
Figure BDA0003413635880000092
检测实施例
本检测实施例提供如应用实施例所述有机电致发光器件的性能检测，结果如表2所示。
表2
Color LE(Cd/A) V(V) LT95(A.U.)
应用例1 green 70 5.0 150
应用例2 green 72 4.9 160
应用例3 green 71 4.8 155
应用例4 green 74 5.2 164
对比例 green 66 5.8 130
其中，器件性能(LE以及V)的数据是在1000nits亮度下测得的；寿命(LT95)的数据是在40mA/cm2的电流密度下计算得到的。
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 (9)

1.一种有机电致发光的化合物，其特征在于，所述化合物的结构如式(I)所示：
Figure FDA0003413635870000011
其中，Ar1-Ar2分别独立地选自取代或未取代的芳香族烃基；X1-X3分别独立地选自N或CR；L1-L2分别独立地选自直接键合、取代或未取代的脂肪族亚烃基或取代或未取代的芳香族亚烃基；Y选自NH、O或S。
2.根据权利要求1所述的化合物，其特征在于，Ar1-Ar2分别独立地选自取代或未取代的C6-C30的芳香族烃基。
3.根据权利要求2所述的化合物，其特征在于，Ar1-Ar2分别独立地选自苯基、萘基、蒽基、菲基、芴基、二苯并呋喃基、二苯并噻吩基、二甲基芴基或二苯基芴基。
4.根据权利要求1所述的化合物，其特征在于，X1-X3不全为CR。
5.根据权利要求1所述的化合物，其特征在于，L1-L2分别独立地选自直接键合、取代或未取代的C6-C30的脂肪族亚烃基或取代或未取代的C6-C30的芳香族亚烃基。
6.根据权利要求1所述的化合物，其特征在于，所述化合物选自：
Figure FDA0003413635870000021
Figure FDA0003413635870000031
Figure FDA0003413635870000041
7.一种电子传输材料，其特征在于，包括：如权利要求1-6任一项所述的化合物。
8.一种电子传输层，其特征在于，包括：如权利要求7所述的电子传输材料。
9.一种有机电致发光器件，其特征在于，包括：如权利要求8所述的电子传输层。
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CN111315740A (zh) * 2017-09-15 2020-06-19 喜星素材株式会社 杂环化合物与包含其的有机发光装置
CN112028883A (zh) * 2020-09-02 2020-12-04 南京高光半导体材料有限公司 一种化合物及有机电致发光器件
CN112094261A (zh) * 2020-09-02 2020-12-18 南京高光半导体材料有限公司 一种化合物、组合物及有机电致发光器件

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CN112028883A (zh) * 2020-09-02 2020-12-04 南京高光半导体材料有限公司 一种化合物及有机电致发光器件
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