CN113277992A - 链状化合物和包含其的有机电致发光显示器件 - Google Patents

链状化合物和包含其的有机电致发光显示器件 Download PDF

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CN113277992A
CN113277992A CN202110569586.3A CN202110569586A CN113277992A CN 113277992 A CN113277992 A CN 113277992A CN 202110569586 A CN202110569586 A CN 202110569586A CN 113277992 A CN113277992 A CN 113277992A
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王湘成
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Abstract

本发明公开了链状化合物和包含其的有机电致发光显示器件，属于有机电致发光材料技术领域。该链状化合物的最大直线长度大于2.3nm，且在450nm光波长的折射率大于2.1，有机电致发光显示器件包括第一电极、有机发光层、第二电极以及与第二电极接触的覆盖层，光从覆盖层发出，且覆盖层材料采用上述链状化合物。与树枝状化合物相比，本发明的链状化合物作为覆盖层材料具有大的光提取优势，可以明显提高外量子效率，得到的有机电致发光显示器件发光效率高，驱动电压低和使用寿命长。

Description

链状化合物和包含其的有机电致发光显示器件
技术领域
本发明属于有机电致发光材料技术领域，具体地涉及链状化合物和包含其的有机电致发光显示器件。
背景技术
目前，有机电致发光显示器件(OLED)的发光效率是其应用中的重要参数，对面板亮度和功耗影响大。高的发光效率取决于发光内量子效率以及光从面板中透出效率，也称之为外量子效率，一般的显示面板发光材料发出的光经过发光材料各功能层、电极、基板后，只有20％能够从基板照出，剩下80％的光“陷获”在发光材料、电极以及基板中，最终以热或者其他能量方式损失掉，其中一部分光是因为各层之间的折射率差异较大，造成界面全反射而损失。当发出的光以一定角度从有机层到阴极时，由于膜层折射率的不同，有一部分光会发生全反射，这样就只有一部分光被利用，为了增加顶发射电致发光装置的出光率，有文献报道在半透阴极上增加一层高折射率的材料来提高光的提取率。OLED器件的覆盖层(Capping layer)材料主要由芳香胺构成，而且多以树枝状为主要构造。芳香胺具有优良的分子稳定性，但是折射率不高，正常情况下在450nm光波长下的折射率低于2.1。
发明内容
本发明的第一目的是提供一种链状化合物，其分子的最大直线长度大于2.3nm，且在450nm光波长的折射率大于2.1。
根据本发明的一些实施方式，所述链状化合物的最大直线长度大于2.5nm。
优选地，所述链状化合物的最大直线长度大于2.8nm。
根据本发明的一些实施方式，所述链状化合物在不同位置采用以下基团中的任意一种或一种以上：
Figure BDA0003082138410000021
其中，Ar独立地选自苯基或成环数为2至4的稠环芳基。
优选地，所述Ar选自以下基团中的任意一种或一种以上：
Figure BDA0003082138410000031
根据本发明的一些实施方式，所述链状化合物选自如下C01至C26任一所示结构的化合物：
Figure BDA0003082138410000032
Figure BDA0003082138410000041
本发明的链状化合物具有如下优势：链状化合物具有长链分子构造，最大直线长度大于2.3nm，在450nm光波长下的折射率大于2.1，具有高的折射率。
本发明的第二目的是提供一种有机电致发光显示器件，包括第一电极、有机发光层、第二电极以及与第二电极接触的覆盖层，且光从所述覆盖层发出，其中：所述链状化合物作为所述覆盖层材料。
本发明的有机电致发光显示器件具有如下优势：发光效率高，驱动电压低和使用寿命长。
与现有技术相比，本发明的链状化合物具有长链分子构造，最大直线长度大于2.3nm，在450nm光波长下的折射率大于2.1，折射率高，且光折射率随着链长的增加变大，主要原因在于：(1)分子增大过程，极性的增加量大于分子体积的增加量，从而导致折射率变大；(2)链状化合物具有相对较强的定向作用，即分子在蒸镀过程倾向于横向平行排列，这种排列方式对光的提取作用强；(3)链状化合物具有较强的吸电子基团或者供电子基团存在时折射率较高；(4)当链状化合物分子中的片段被限制旋转扭曲即刚性强时具有更高的折射率；与树枝状化合物相比，链状化合物用于OLED器件的覆盖层具有非常大的光提取优势，可以明显提高外量子效率。另外，本发明采用上述链状化合物作为覆盖层材料得到的有机电致发光显示器件发光效率高，驱动电压低和使用寿命长。
参考以下详细说明更易于理解本发明的上述以及其他特征、方面和优点。
附图说明
通过阅读参照以下附图对非限制性实施例所作的详细描述，本发明的其它特征、目的和优点将会变得更显著：
图1是实施例中有机电致发光显示器件的结构示意图。
具体实施方式
为使本发明实施例的目的、技术方案和优点更加清楚，下面将结合本发明实施例的附图，对本发明实施例的技术方案进行清楚、完整地描述。显然，所描述的实施例是本发明的一部分实施例，而不是全部的实施例。基于所描述的本发明的实施例，本领域普通技术人员在无需创造性劳动的前提下所获得的所有其它实施例，都属于本发明保护的范围。
以下合成实施例1-26分别描述了上述链状化合物C01、C02、C03、C04、C05、C06、C07、C08、C09、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20、C21、C22、C23、C24、C25和C26的合成，其中未注明制备方法的原料均为市售商品.
合成实施例1
本合成实施例中链状化合物C01的合成路线如下：
Figure BDA0003082138410000061
在三口烧瓶中，加入固体原料1-1(15g，62.7mmol)、1-2(11g，29mmol)、醋酸钯(0.15g，1％)和碳酸铯(30g，94mmol)，加入溶剂甲苯120mL、乙醇10mL和纯净水10mL，抽真空，氮气保护以及置换3次，反应置于外温为100°的油浴锅中，反应4小时。冷却后，硅藻土过滤，滤液在旋转蒸发仪上旋干，得到灰色固体粗品，用二氯甲烷/乙醇＝1：4(v/v)室温打浆过夜，过滤固体，用四氢呋喃/乙醇＝1：4(共计100mL)室温打浆过夜，过滤固体，得到类白色固体粗品，用50mL甲苯加热重结晶，过滤，得到白色固体链状化合物C01(15g，收率74.6％)。
合成实施例2
本合成实施例中链状化合物C02的合成路线如下：
Figure BDA0003082138410000062
在三口烧瓶中，加入固体原料2-1(15g，62.7mmol)、2-2(7.6g，29mmol)、醋酸钯(0.15g，1％)和碳酸铯(30g，94mmol)，加入溶剂甲苯120mL、乙醇10mL和纯净水10mL，抽真空，氮气保护以及置换3次，反应置于外温为100°的油浴锅中，反应4小时，冷却后，硅藻土过滤，滤液在旋转蒸发仪上旋干，得到灰色固体粗品，用二氯甲烷/乙醇＝1：4(v/v)室温打浆过夜，过滤固体，用甲苯/乙醇＝1：1(共计100mL)室温打浆过夜，过滤固体，得到类白色固体粗品，用50mL甲苯加热重结晶，过滤，得到白色固体链状化合物C02(14g，收率71％)。
合成实施例3
本合成实施例中链状化合物C03的合成路线如下：
Figure BDA0003082138410000063
在三口烧瓶中，加入固体原料3-1(15g，62.7mmol)、3-2(9g，29mmol)、醋酸钯(0.15g，1％)和碳酸铯(30g，94mmol)，加入溶剂甲苯120mL、乙醇10mL和纯净水10mL，抽真空，氮气保护以及置换3次，反应置于外温为100°的油浴锅中，反应3小时，冷却后，硅藻土过滤，滤液在旋转蒸发仪上旋干，得到灰色固体粗品，用二氯甲烷/乙醇＝1：4(v/v)室温打浆过夜，过滤固体，用四氢呋喃/乙醇＝1：3(共计100mL)室温打浆过夜，过滤固体，得到类白色固体粗品，用50mL甲苯加热重结晶，过滤，得到白色固体链状化合物C03(16g，收率75.8％)。
合成实施例4
本合成实施例中链状化合物C04的合成路线如下：
Figure BDA0003082138410000071
在三口烧瓶中，加入固体原料4-1(15g，32.6mmol)、4-2(15.6g，32.6mmol)、醋酸钯(0.15g，1％)和碳酸铯(15.6g，48.9mmol)，加入溶剂甲苯100mL、乙醇10mL和纯净水10mL，抽真空，氮气保护以及置换3次，反应置于外温为100°的油浴锅中，反应6小时，冷却后，硅藻土过滤，滤液在旋转蒸发仪上旋干，得到灰色固体粗品，用四氢呋喃/乙醇＝1：3(v/v)室温打浆过夜，过滤固体，用四氢呋喃/乙醇＝1：3(共计100mL)室温打浆过夜，过滤固体，得到类白色固体粗品，用50mL甲苯加热重结晶，过滤，得到白色固体链状化合物C04(21g，收率75％)。
其他链状化合物C05、C06、C07、C08、C09、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20、C21、C22、C23、C24、C25和C26的合成方法和原料摩尔比参照合成实施例1至4的步骤进行，测试得到的26种链状化合物、对比化合物1
Figure BDA0003082138410000072
和对比化合物2
Figure BDA0003082138410000073
分别在450nm、550nm和610nm光波长下的折射率，结果如表1所示。
表1
Figure BDA0003082138410000081
以下器件实施例1至10中有机电致发光显示器件采用如图1所示的单色器件结构，链状化合物用于覆盖层在红光、绿光、蓝光、等各种光色。
器件实施例1
按照如图1所示的结构制作蓝光有机电致发光显示器件，制备工艺为：在玻璃材质的基底101上，形成透明阳极ITO膜层，膜厚150nm，得到第一电极102作为阳极，之后蒸镀
Figure BDA0003082138410000091
与化合物
Figure BDA0003082138410000092
的混合材料作为空穴注入层103，混合比例为3:97(质量比)，之后蒸镀100nm厚度的化合物
Figure BDA0003082138410000093
得到第一层空穴传输层104，然后蒸镀20nm厚度化合物
Figure BDA0003082138410000094
得到第二层空穴传输层105，然后以95:5的蒸镀速率蒸镀
Figure BDA0003082138410000095
30nm，制作蓝光发光单元106，然后蒸镀10nm
Figure BDA0003082138410000096
形成电子阻挡层107，然后
Figure BDA0003082138410000097
Figure BDA0003082138410000098
混合比例为4:6(质量比)形成厚度30nm的电子传输层108，之后形成厚度15nm的镁银(质量比1：9)，作为第二电极109，然后上面蒸镀60nm的本发明的链状化合物C01作为覆盖层材料，形成110层。
器件实施例2至10中分别采用链状化合物C02、C03、C04、C05、C06、C07、C11、C14、C18替代器件实施例1中使用的链状化合物C01制作蓝光有机电致发光显示器件，对比例1和对比例2分别以
Figure BDA0003082138410000101
替代器件实施例1中使用的链状化合物C01制作蓝光有机电致发光显示器件，所得有机电致发光显示器件进行电压、效率和使用寿命的性能测试，具体如表2所示。
表2
Figure BDA0003082138410000102

Claims (8)

1.一种链状化合物，其特征在于，其分子的最大直线长度大于2.3nm，且在450nm光波长的折射率大于2.1。
2.根据权利要求1所述的链状化合物，其特征在于，所述链状化合物的最大直线长度大于2.5nm。
3.根据权利要求1所述的链状化合物，其特征在于，所述链状化合物的最大直线长度大于2.8nm。
4.根据权利要求1至3任一项所述的链状化合物，其特征在于，所述链状化合物在不同位置采用以下基团中的任意一种或一种以上：
Figure FDA0003082138400000011
Figure FDA0003082138400000021
其中，Ar独立地选自苯基或成环数为2至4的稠环芳基。
5.根据权利要求4所述的链状化合物，其特征在于，Ar选自以下基团中的任意一种或一种以上：
Figure FDA0003082138400000022
6.根据权利要求1至5所述的链状化合物，其特征在于，所述链状化合物选自如下C01至C26任一所示结构：
Figure FDA0003082138400000031
Figure FDA0003082138400000041
7.一种有机电致发光显示器件，其特征在于，包括权利要求1至6任一项所述的链状化合物。
8.根据权利要求7所述的有机电致发光显示器件，其特征在于，包括第一电极、有机发光层、第二电极以及与第二电极接触的覆盖层，光从所述覆盖层发出；
所述链状化合物作为所述覆盖层的材料。
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