CN113735891B - 一种有机化合物及其应用 - Google Patents

一种有机化合物及其应用 Download PDF

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CN113735891B
CN113735891B CN202111038629.1A CN202111038629A CN113735891B CN 113735891 B CN113735891 B CN 113735891B CN 202111038629 A CN202111038629 A CN 202111038629A CN 113735891 B CN113735891 B CN 113735891B
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organic
organic compound
oled device
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CN113735891A (zh
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邓东阳
高威
代文朋
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Wuhan Tianma Microelectronics Co Ltd
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Wuhan Tianma Microelectronics Co Ltd
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Abstract

本发明提供一种有机化合物及其应用，所述有机化合物具有良好的热稳定性和成膜性，适宜的玻璃化温度Tg，利于在热真空蒸镀过程中形成稳定、均一的薄膜，同时减少相分离，保持器件的稳定性。具有较高的载流子传输速率以及平衡的载流子传输性能，以利于器件中空穴和电子传输的平衡，同时获得较宽的载流子复合区域，提高发光效率。适用于OLED器件的电子传输层和/或空穴阻挡层和/或发光层等，使得OLED器件具有较高的电流效率，较低的驱动电压以及较长的寿命。

Description

一种有机化合物及其应用
技术领域
本发明属于有机发光材料技术领域，涉及一种有机化合物及其应用。
背景技术
有机电致发光材料(OLED)作为新一代显示技术，具有超薄、自发光、视角宽、响应快、发光效率高、温度适应性好、生产工艺简单、驱动电压低、能耗低等优点，已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。
按发光机理可分为电致荧光和电致磷光两种，荧光是单重态激子的辐射衰减跃迁，磷光则是三重态激子辐射衰减到基态所发射的光。根据自旋量子统计理论，单重态激子和三重态激子的形成概率比例是1:3。荧光材料内量子效率不超过25％的限制，外量子效率普遍低于5％；电致磷光材料的内量子效率理论上达到100％，外量子效率可达20％。1998年，我国吉林大学的马於光教授和美国普林斯顿大学的Forrest教授分别报道了采用锇配合物和铂配合物作为染料掺杂入发光层，第一次成功得到并解释了磷光电致发光现象，并开创性的将所制备磷光材料应用于电致发光器件。
然而现在使用的蓝色电致发光材料存在寿命不够长，效率不够高的问题，其原因为材料的结构导致其性能不够好，限制了其应用于电致发光材料的效果，因此进一步开发性能优良的磷光主体材料是本领域的研究重点。
CN108117508A公开了一种螺芴环化合物，其结构为：其中，D1～D12独立地为氢、供电子基团或稠环基团，且不能同时为氢，所述供电子基团和稠环基团均独立地选自取代或未取代的C2～C30的芳基。本发明的以螺环为核的稠环芳烃衍生物，适合于在电发光显示器中作空穴传输材料，然而其器件的驱动电压仍然较高，电流效率较低。
US9991450B2公开了一种螺芴环化合物，具有如下式所示结构：
其中R1至R8独立地选自氢原子、苯基、联苯基、三联苯基、萘基、菲基、三亚苯基、芴基、二苯并噻吩基、羰基、氨基或螺[环戊基]-三亚苯基-4,9'-芴]基团，作为发光层主体材料用于有机电致发光器件，但是其器件的驱动电压仍然较高，电流效率较低。
因此，在本领域，期望开发能够进一步提高器件效率和寿命，降低驱动电压的发光层材料或电子传输层材料或空穴阻挡层材料。
发明内容
针对现有技术的不足，本发明的目的在于提供一种有机化合物及其应用。
为达此目的，本发明采用以下技术方案：
本发明的目的之一在于提供一种有机化合物，所述所述有机化合物具有如下式I所示结构：
其中Z选自氢、取代或未取代的C6-C30的芳基、取代或未取代的C5-C30的杂芳基；X选自C或Si。
本发明中，所述C6～C30各自独立地可以为C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
所述C5～C30各自独立地可以为C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
本发明提供的有机化合物具有良好的热稳定性和成膜性，适宜的玻璃化温度Tg，利于在热真空蒸镀过程中形成稳定、均一的薄膜，同时减少相分离，保持器件的稳定性。具有较高的载流子传输速率以及平衡的载流子传输性能，以利于器件中空穴和电子传输的平衡，同时获得较宽的载流子复合区域，提高发光效率。
本发明的目的之二在于提供一种电致发光材料，所述电致发光材料包括如目的之一所述的有机化合物。
本发明的目的之三在于提供一种电子传输层材料，所述电子传输层材料包括如目的之一所述的有机化合物。
本发明的目的之四在于提供一种空穴阻挡层材料，所述空穴阻挡层材料包括如目的之一所述的有机化合物。
本发明的目的之五在于提供一种OLED器件，所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层，所述有机薄膜层的材料包括如目的之二所述的有机电致发光材料。
本发明的目的之六在于提供一种显示面板，所述显示面板包括如目的之五所述的OLED器件。
发明的目的之七在于提供一种电子设备，所述电子设备包括如目的之六所述的显示面板。
相对于现有技术，本发明具有以下有益效果：
本发明提供的有机化合物具有良好的热稳定性和成膜性，适宜的玻璃化温度Tg，利于在热真空蒸镀过程中形成稳定、均一的薄膜，同时减少相分离，保持器件的稳定性。具有较高的载流子传输速率以及平衡的载流子传输性能，以利于器件中空穴和电子传输的平衡，同时获得较宽的载流子复合区域，提高发光效率。适用于OLED器件的电子传输层和/或空穴阻挡层等，使得OLED器件具有较高的电流效率，较低的驱动电压以及较长的寿命。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了，所述实施例仅仅是帮助理解本发明，不应视为对本发明的具体限制。
本发明的目的之一在于提供一种有机化合物，所述所述有机化合物具有如下式I所示结构：
其中Z选自氢、取代或未取代的C6-C30的芳基、取代或未取代的C5-C30的杂芳基；X选自C或Si。
本发明中，所述C6～C30各自独立地可以为C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
所述C5～C30各自独立地可以为C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
本发明提供的有机化合物具有良好的热稳定性和成膜性，适宜的玻璃化温度Tg，利于在热真空蒸镀过程中形成稳定、均一的薄膜，同时减少相分离，保持器件的稳定性。具有较高的载流子传输速率以及平衡的载流子传输性能，以利于器件中空穴和电子传输的平衡，同时获得较宽的载流子复合区域，提高发光效率。
在一个实施方式中，所述Z选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的咔唑基、取代或未取代的喹啉基、取代或未取代的萘基、取代或未取代的吡啶基、取代或未取代的芘基、取代或未取代的菲基、取代或未取代的菲啰啉基。
在一个实施方式中，所述Z选自苯基、联苯基、萘基、咔唑基、三嗪基、嘧啶基、吡嗪基、哒嗪基、苯并吡啶基、苯并吡唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、喹啉基、异喹啉基或喹喔啉基。
在一个实施方式中，所述基团含有取代基时，所述取代基各自独立地选自氘、氰基、卤素、未取代或卤代的C1～C10(例如C1、C2、C3、C4、C5、C6、C7、C8、C9或C10)直链或支链烷基、未取代或卤代的C1～C10(例如C1、C2、C3、C4、C5、C6、C7、C8、C9或C10)烷氧基、C6～C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基、C2～C20(例如C3、C4、C5、C6、C8、C10、C12、C14、C16或C18等)杂芳基或C6～C18(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基中的至少一种。
在一个实施方式中，所述Z选自
中的任意一种，其中波浪线代表基团的连接位点。
在一个实施方式中，所述有机化合物为如下化合物M1-M91中的任意一种：
本发明的目的之二在于提供一种电致发光材料，所述电致发光材料包括如目的之一所述的有机化合物。
本发明的目的之三在于提供一种电子传输层材料，所述电子传输层材料包括如目的之一所述的有机化合物。
本发明的目的之四在于提供一种空穴阻挡层材料，所述空穴阻挡层材料包括如目的之一所述的有机化合物。
本发明的目的之五在于提供一种OLED器件，所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层，所述有机薄膜层的材料包括如目的之二所述的有机电致发光材料。
在一个实施方式中，所述有机薄膜层包括发光层，所述发光层包括作为主体材料的如目的之二所述的有机电致发光材料。
在一个实施方式中，所述有机薄膜层包括电子传输层，所述电子传输层的材料包括如目的之二所述的有机电致发光材料。
在一个实施方式中，所述有机薄膜层包括空穴阻挡层，所述空穴阻挡层的材料包括如目的之二所述的有机电致发光材料。
在一个实施方式中，所述有机薄膜层包括发光层，所述发光层的材料包括如目的之二所述的有机电致发光材料。
在一个实施方式中，所述有机薄膜层还包括空穴注入层、空穴传输层、电子阻挡层或电子注入层中的任意一种或至少两种的组合。
本发明提供的OLED器件中，阳极材料可以为金属、金属氧化物或导电性聚合物；其中，所述金属包括铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金，所述金属氧化物包括氧化铟锡(ITO)、氧化铟锌(IZO)、氧化锌、氧化铟镓锌(IGZO)等，所述导电性聚合物包括聚苯胺、聚吡咯、聚(3-甲基噻吩)等。除以上有助于空穴注入的材料及其组合，还包括已知的适合做阳极的材料。
所述OLED器件中，阴极材料可以为金属或多层金属材料；其中，所述金属包括铝、镁、银、铟、锡、钛等及它们的合金，所述多层金属材料包括LiF/Al、LiO2/Al、BaF2/Al等。除以上有助于电子注入的材料及其组合，还包括已知的适合做阴极的材料。
所述OLED器件中，有机薄膜层包括至少一层发光层(EML)和设置于发光层两侧的空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、空穴阻挡层(HBL)、电子传输层(ETL)或电子注入层(EIL)中的任意一种或至少两种的组合。
所述OLED器件可以通过以下方法制备：在透明或不透明的光滑的基板上形成阳极，在阳极上形成有机薄层，在有机薄层上形成阴极。其中，形成有机薄层可采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
本发明的目的之六在于提供一种显示面板，所述显示面板包括如目的之五所述的OLED器件。
本发明的目的之七在于提供提供一种有机发光显示装置，包括如上文所述的显示面板。
在本发明中，OLED器件可以用在有机发光显示装置中，其中有机发光显示装置可以是手机显示屏、电脑显示屏、电视显示屏、智能手表显示屏、智能汽车显示面板、VR或AR头盔显示屏、各种智能设备的显示屏等。
本发明的目的之八在于提供一种电子设备，所述电子设备包括如目的之六所述的显示面板。
本发明中，具有如式I所示结构的有机化合物可以通过如下合成路线制备得到：
路线1，X＝C，
路线2，X＝Si，
以下示例性地列举几种本发明所述有机化合物的制备实施例：
制备实施例
1)中间体1的制备：在I L三口瓶中，加入反应物1(56.01g，0.20mol)，反应物2(44.9g，0.21mol)，碳酸钾(55.2g，0.40mol)，165.6g水，Pd(PPh3)4(1.156g，I.0mmol)，甲苯(400mL)，无水乙醇(100mL)，N2保护，升温至回流，保温反应8小时，停反应，降温至25℃，分液，收集有机相，水洗至中性，有机相减压脱去溶剂，采用纯甲苯柱层析纯化，甲苯、无水乙醇重结晶，得到中间体1(收率87.68％)。
2)中间体2的制备:在I L三口瓶中，加入中间体1(55.5g，0.15mol)，氢氧化钠(15.0g，0.375mol)，无水乙醇(400mL)，N2保护，升温至回流，保温反应3小时，降温至25℃，滴加10％稀盐酸溶液(0.375mol)搅拌0.5h，乙酸乙酯萃取，有机相过硅胶柱，减压脱除溶剂，得到粗品中间体2,甲苯、无水乙醇重结晶，得到精品中间体2，HPLC纯度99.42％，收率89.46％。
3)中间体3的制备:在500mL三口瓶中，加入中间体2(35.9g，0.10mol)，甲磺酸(240g)，N2保护，升温至70～75℃，保温反应6小时，降温至25℃，将反应液缓慢倒入250g碎冰中，搅拌，抽滤，50mL水淋洗，得到粗品中间体3,甲苯重结晶得到精品，HPLC纯度99.26％，收率79.37％。
4)中间体4的合成：在500mL三口烧瓶中，将中间体3溶于四氢呋喃(THF)中降温至-80℃，缓慢滴加丁基锂(1eq)，温度不超过-75℃，滴加完升至室温反应1h，将溶有反应物2的THF溶液加入反应瓶中，将混合液回流反应3h，TCL检测反应完毕后，降至室温。用二氯甲烷萃取后，合并有机相，旋除有机溶剂，用硅胶柱层(洗脱剂∶石油醚∶乙酸乙酯＝10∶1)分离得中间体4，收率为63.3％。化合物M28的合成：
氮气流下，将中间体4(14.9g，30mmol)和反应物3(9.7g，35mmol)溶解于四氢呋喃后，加入碳酸钾(70mmol)水溶液，加热搅拌。回流状态下，加入催化剂Pd(PPh3)4(0.6g，0.5mmol)，加热搅拌8小时。反应结束后，将温度降至室温后，去除碳酸钾溶液并过滤。将过滤的固体用乙醇洗涤，得到化合物M28(收率85％)
有机化合物M28的元素分析结果：分子式C52H29N3，理论值：C,89.76；H,4.20；N,6.04；测试值：C,89.76；H,4.20；N,6.04。
通过液相质谱联用分析得到其相对分子质量：理论值为695.24，测试值为695.25。
化合物M29的合成：
氮气流下，将中间体4(14.9g，30mmol)和反应物4(9.7g，35mmol)溶解于四氢呋喃后，加入碳酸钾(70mmol)水溶液，加热搅拌。回流状态下，加入催化剂Pd(PPh3)4(0.6g，0.5mmol)，加热搅拌8小时。反应结束后，将温度降至室温后，去除碳酸钾溶液并过滤。将过滤的固体用乙醇洗涤，得到化合物M29(收率82％)
有机化合物M29的元素分析结果：分子式C53H30N2，理论值：C,91.62；H,4.35；N,4.03；测试值：C,91.62；H,4.35；N,4.03。
通过液相质谱联用分析得到其相对分子质量：理论值为694.24，测试值为694.26。
化合物M30的合成
氮气流下，将中间体4(14.9g，30mmol)和反应物5(8.8g，35mmol)溶解于四氢呋喃后，加入碳酸钾(70mmol)水溶液，加热搅拌。回流状态下，加入催化剂Pd(PPh3)4(0.6g，0.5mmol)，加热搅拌8小时。反应结束后，将温度降至室温后，去除碳酸钾溶液并过滤。将过滤的固体用乙醇洗涤，得到化合物M30(收率81％)
有机化合物M30的元素分析结果：分子式C51H28N2，理论值：C,91.59；H,4.22；N,4.19；测试值：C,91.59；H,4.22；N,4.19。
通过液相质谱联用分析得到其相对分子质量：理论值为668.23，测试值为668.25。
化合物M31的合成
氮气流下，将中间体4(14.9g，30mmol)和反应物6(13.2g，35mmol)溶解于四氢呋喃后，加入碳酸钾(70mmol)水溶液，加热搅拌。回流状态下，加入催化剂Pd(PPh3)4(0.6g，0.5mmol)，加热搅拌8小时。反应结束后，将温度降至室温后，去除碳酸钾溶液并过滤。将过滤的固体用乙醇洗涤，得到化合物M31(收率79％)
有机化合物M31的元素分析结果：分子式C61H34N2，理论值：C,92.16；H,4.31；N,3.52；测试值：C,92.16；H,4.31；N,3.52。
通过液相质谱联用分析得到其相对分子质量：理论值为794.27，测试值为794.27。
化合物M32的合成
氮气流下，将中间体4(14.9g，30mmol)和反应物7(13.2g，35mmol)溶解于四氢呋喃后，加入碳酸钾(70mmol)水溶液，加热搅拌。回流状态下，加入催化剂Pd(PPh3)4(0.6g，0.5mmol)，加热搅拌8小时。反应结束后，将温度降至室温后，去除碳酸钾溶液并过滤。将过滤的固体用乙醇洗涤，得到化合物M32(收率81％)
有机化合物M32的元素分析结果：分子式C60H33N3，理论值：C,90.54；H,4.18；N,5.28；测试值：C,90.54；H,4.18；N,5.28。
通过液相质谱联用分析得到其相对分子质量：理论值为795.27，测试值为795.27。
化合物M33的合成
氮气流下，将中间体4(14.9g，30mmol)和反应物8(7.0g，35mmol)溶解于四氢呋喃后，加入碳酸钾(70mmol)水溶液，加热搅拌。回流状态下，加入催化剂Pd(PPh3)4(0.6g，0.5mmol)，加热搅拌8小时。反应结束后，将温度降至室温后，去除碳酸钾溶液并过滤。将过滤的固体用乙醇洗涤，得到化合物M33(收率86％)
有机化合物M33的元素分析结果：分子式C48H27N，理论值：C,93.33；H,4.41；N,2.27；测试值：C,93.33；H,4.41；N,2.27。
通过液相质谱联用分析得到其相对分子质量：理论值为617.21，测试值为617.23。
化合物M34的合成
氮气流下，将中间体4(14.9g，30mmol)和反应物9(9.6g，35mmol)溶解于四氢呋喃后，加入碳酸钾(70mmol)水溶液，加热搅拌。回流状态下，加入催化剂Pd(PPh3)4(0.6g，0.5mmol)，加热搅拌8小时。反应结束后，将温度降至室温后，去除碳酸钾溶液并过滤。将过滤的固体用乙醇洗涤，得到化合物M34(收率82％)
有机化合物M34的元素分析结果：分子式C53H28N2，理论值：C,91.88；H,4.07；N,4.04；测试值：C,91.88；H,4.07；N,4.04。
通过液相质谱联用分析得到其相对分子质量：理论值为692.23，测试值为692.25。
化合物M36的合成
氮气流下，将中间体4(14.9g，30mmol)和反应物10(6.0g，35mmol)溶解于四氢呋喃后，加入碳酸钾(70mmol)水溶液，加热搅拌。回流状态下，加入催化剂Pd(PPh3)4(0.6g，0.5mmol)，加热搅拌8小时。反应结束后，将温度降至室温后，去除碳酸钾溶液并过滤。将过滤的固体用乙醇洗涤，得到化合物M36(收率84％)
有机化合物M36的元素分析结果：分子式C45H22N2，理论值：C,91.50；H,3.75；N,4.74；测试值：C,C,91.50；H,3.75；N,4.74。
通过液相质谱联用分析得到其相对分子质量：理论值为590.18，测试值为590.20。
化合物M55的合成
中间体C的制备：将50mmol反应物A溶于750mL THF，将50mmol反应物B溶于250mLTHF中，将反应物B的溶液逐滴添加至反应物A的溶液中，并且将得到的混合物在室温下搅拌16小时。在真空下除去溶剂后，将残余物溶于250mL二氯甲烷中，再用200mL蒸馏水洗涤三次，用硫酸镁干燥，将有机相蒸发，残余物用二噁烷重结晶5次，得到中间体C。
氮气流下，将中间体C(15.4g，30mmol)和反应物4(6.0g，35mmol)溶解于四氢呋喃后，加入碳酸钾(70mmol)水溶液，加热搅拌。回流状态下，加入催化剂Pd(PPh3)4(0.6g，0.5mmol)，加热搅拌8小时。反应结束后，将温度降至室温后，去除碳酸钾溶液并过滤。将过滤的固体用乙醇洗涤，得到化合物M55(收率81％)
有机化合物M55的元素分析结果：分子式C52H30N2Si，理论值：C,87.86；H,4.25；N,3.94；Si,3.95；测试值：C,87.86；H,4.25；N,3.94；Si,3.95。
通过液相质谱联用分析得到其相对分子质量：理论值为710.22，测试值为710.24。
化合物的模拟计算：
运用密度泛函理论(DFT)，针对本发明提供的有机化合物，通过Guassian 09程序包(Guassian Inc.)在B3LYP/6-31G(d)计算水平下，优化并计算得到了分子前线轨道HOMO和LUMO的分布情况和能级，根据HOMO和LUMO能级得到带隙Eg，同时基于含时密度泛函理论(TD-DFT)模拟计算了化合物分子的单线态能级ES，结果如表1所示。
表1有机化合物高斯模拟计算结果
根据表1的计算结果可知，本发明提供的有机化合物，HOMO和LUMO之间的重叠程度较低，HOMO能级与LUMO能级更深，单线态能级ES比较高，可以很好地与现有量产运用的相邻层材料的能级相匹配，有效地传输电子，将空穴和激子限制在发光区，利于扩宽发光区域，提升器件发光效率和寿命。比较适合作为OLED材料。
以下列举几种本发明所述有机化合物应用于OLED器件中的应用例：
应用例1
本应用例提供一种OLED器件，所述OLED器件依次包括：基板、ITO阳极10nm、空穴注入层10nm、第一空穴传输层40nm、第二空穴传输层10nm、发光层20nm、电子传输层30nm、电子注入层2nm、阴极(铝电极)100nm。
OLED器件的制备步骤如下：
(1)将玻璃基板切成50mm×50mm×0.7mm的大小，分别在丙酮、异丙醇和去离子水中超声处理30min，然后在臭氧中清洁10min；将所得的具有ITO阳极的玻璃基板安装到真空沉积设备上；
(2)在真空度为2×10-6Pa下，在ITO阳极层上真空蒸镀上空穴注入层材料HAT-CN，厚度为10nm；
(3)在空穴注入层上蒸镀NPB和TAPC分别作为第一空穴传输层和第二空穴传输层，厚度分别为40nm和10nm；
(4)在空穴传输层上真空共蒸镀一层发光层，其中，以化合物CPB作为发光层的主体材料，化合物FIrpic作为发光层的掺杂材料，掺杂比例为5％，厚度为20nm；
(5)在发光层上真空蒸镀本发明提供的有机化合物M28作为电子传输层，厚度为30nm；
(6)在电子传输层上真空蒸镀LiF作为电子注入层，厚度为2nm；
(7)在电子注入层上真空蒸镀铝电极作为阴极，厚度为100nm。
应用例2
本应用例与应用例1的区别仅在于，将步骤(5)中的有机化合物M28用等量的有机化合物M29替换，其他制备步骤均相同。
应用例3
本应用例与应用例1的区别仅在于，将步骤(5)中的有机化合物M28用等量的有机化合物M30替换，其他制备步骤均相同。
应用例4
本应用例与应用例1的区别仅在于，将步骤(5)中的有机化合物M28用等量的有机化合物M31替换，其他制备步骤均相同。
应用例5
本应用例与应用例1的区别仅在于，将步骤(5)中的有机化合物M28用等量的有机化合物M32替换，其他制备步骤均相同。
应用例6
本应用例与应用例1的区别仅在于，将步骤(5)中的有机化合物M28用等量的有机化合物M33替换，其他制备步骤均相同。
应用例7
本应用例与应用例1的区别仅在于，将步骤(5)中的有机化合物M28用等量的有机化合物M34替换，其他制备步骤均相同。
应用例8
本应用例与应用例1的区别仅在于，将步骤(5)中的有机化合物M28用等量的有机化合物M36替换，其他制备步骤均相同。
应用例9
本应用例与应用例1的区别仅在于，将步骤(5)中的有机化合物M28用等量的有机化合物M55替换，其他制备步骤均相同。
对比例1
本对比例与应用例1的区别仅在于，将步骤(5)中的有机化合物M28用等量的对比化合物M0替换，其他制备步骤均相同。
OLED器件的性能评价：
用Keithley 2365A数字纳伏表测试OLED器件在不同电压下的电流，然后用电流除以发光面积得到OLED器件在不同电压下的电流密度；用Konicaminolta CS-2000分光辐射亮度计测试OLED器件在不同电压下的亮度和辐射能流密度；根据OLED器件在不同电压下的电流密度和亮度，得到在相同电流密度下(10mA/cm2)的启亮电压和电流效率(CE，Cd/A)，Von为亮度1Cd/m2下的启亮电压；通过测量OLED器件的亮度达到初始亮度的95％时的时间而获得寿命LT95(在50mA/cm2测试条件下)；具体数据如表2所示。
表2应用例与对比例的器件性能测试结果
由表2可知，本发明提供的OLED显示面板具有较低的驱动电压、以及较高的发光效率和使用寿命，其中驱动电压小于3.45V，发光效率在48.5Cd/A以上，使用寿命大于140h。其中，相比于对比例1，电压降低5％左右，效率提升7％左右，寿命提升10％左右。显示面板的以上性能均具有比较明显的提升，这主要得益于本发明的材料具有较深的HOMO值，可以有效地阻挡空穴越过发光层，将空穴限制在发光层内，提升空穴与电子的复合几率；且具有利于电子注入的LUMO能级，电子迁移率也较高，从而降低驱动电压，提高器件效率。
申请人声明，本发明通过上述实施例来说明本发明的有机化合物及其应用，但本发明并不局限于上述工艺步骤，即不意味着本发明必须依赖上述工艺步骤才能实施。所属技术领域的技术人员应该明了，对本发明的任何改进，对本发明所选用原料的等效替换及辅助成分的添加、具体方式的选择等，均落在本发明的保护范围和公开范围之内。

Claims (13)

1.一种有机化合物，其特征在于，所述有机化合物具有如下式I所示结构：
其中Z选自
中的任意一种，其中波浪线代表基团的连接位点；
X选自C或Si。
2.根据权利要求1所述的有机化合物，其特征在于，所述有机化合物为如下化合物M1-M91中的任意一种：
3.一种有机电致发光材料，其特征在于，所述有机电致发光材料包括如权利要求1或2所述的有机化合物。
4.一种电子传输层材料，其特征在于，所述电子传输层材料包括如权利要求1或2所述的有机化合物。
5.一种空穴阻挡层材料，其特征在于，所述空穴阻挡层材料包括如权利要求1或2所述的有机化合物。
6.一种OLED器件，其特征在于，所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层，所述有机薄膜层的材料包括如权利要求3所述的有机电致发光材料。
7.根据权利要求6所述的OLED器件，其特征在于，所述有机薄膜层包括发光层，所述发光层包括作为主体材料的如权利要求3所述的有机电致发光材料。
8.根据权利要求6所述的OLED器件，其特征在于，所述有机薄膜层包括电子传输层，所述电子传输层的材料包括如权利要求3所述的有机电致发光材料。
9.根据权利要求6所述的OLED器件，其特征在于，所述有机薄膜层包括空穴阻挡层，所述空穴阻挡层的材料包括如权利要求3所述的有机电致发光材料。
10.根据权利要求6所述的OLED器件，其特征在于，所述有机薄膜层包括发光层，所述发光层的材料包括如权利要求3所述的有机电致发光材料。
11.一种显示面板，其特征在于，所述显示面板包括如权利要求6～10任一项所述的OLED器件。
12.一种有机发光显示装置，其特征在于，包括如权利要求11所述的显示面板。
13.一种电子设备，其特征在于，所述电子设备包括如权利要求11所述的显示面板。
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