CN109456256A - 化合物、显示面板以及显示装置 - Google Patents

化合物、显示面板以及显示装置 Download PDF

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CN109456256A
CN109456256A CN201811622667.XA CN201811622667A CN109456256A CN 109456256 A CN109456256 A CN 109456256A CN 201811622667 A CN201811622667 A CN 201811622667A CN 109456256 A CN109456256 A CN 109456256A
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aryl
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张磊
高威
牛晶华
李杨
卢艳
黄高军
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Wuhan Tianma Microelectronics Co Ltd
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Wuhan Tianma Microelectronics Co Ltd
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Priority to CN201811622667.XA priority Critical patent/CN109456256A/zh
Publication of CN109456256A publication Critical patent/CN109456256A/zh
Priority to US16/352,663 priority patent/US11411184B2/en
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Abstract

本发明属于OLED技术领域且提供了一种用作主体材料的化合物，具有式(I)的结构，其中a和b分别表示电子给体D和电子受体A的个数且分别选自1、2或3，c和d分别选自0、1或2；L1、L2和电子给体D各自独立地选自烷基、亚环烷基、杂环基、芳基、杂芳基、稠芳基或稠杂芳基电子受体A选自含氮杂环、含氰基、含磷氧基的取代基或三芳基硼类取代基。本发明化合物中的D‑(π)‑σ‑(π)‑A结构具有双极性，σ键可有效打断电子给体D与电子受体A之间的分子内电荷传输，使激发态限制为D或A的片段内的局域激发态，因而使化合物具有小的激发态偶极矩，当其用作发光层主体材料时，可有效降低蓝光材料的效率滚降，提升发光亮度和发光效率。

Description

化合物、显示面板以及显示装置
技术领域
本发明涉及有机电致发光材料技术领域，具体地涉及一种用作OLED发光主体材料的化合物以及包含该化合物的显示面板以及显示装置。
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，OLED发射的光可以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所发射的光，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％，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。
由于磷光重金属材料有较长的寿命(μs)，在高电流密度下，可能导致三线态-三线态湮灭和浓度淬灭，造成器件性能衰减，因此通常将重金属磷光材料掺杂到合适的主体材料中，形成一种主客体掺杂体系，使得能量传递最优化，发光效率和寿命最大化。在目前的研究现状中，重金属掺杂材料商业化已成熟，很难开发可替代的掺杂材料。因此，研发新的磷光主体材料成为了一个新的方向。
发明内容
有鉴于此，本发明提供一种具有D-(π)-σ-(π)-A结构的化合物，所述化合物具有式(I)所示的化学结构：
其中，D表示电子给体，A表示电子受体；其中，a和b分别表示电子给体D和电子受体A的个数且分别选自1、2或3，c和d分别表示L1和L2的个数且分别选自0、1或2；
L1和L2各自独立地选自单键、取代或未取代的C1-C20亚烷基、取代或未取代的C3-C20亚环烷基、取代或未取代的C3-C20亚杂环基、取代或未取代的C6-C40亚芳基、取代或未取代的C4-C40亚杂芳基、取代或未取代的C10-C60的亚稠芳基或取代或未取代的C10-C60的亚稠杂芳基中的至少一种；当c或d为2时，各个L1或L2之间可以相同或不同；
电子给体D选自取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C10-C60的亚稠芳基、取代或未取代的C10-C60的亚稠杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、C12-C40的吖啶基及其衍生物基团中的至少一种；当a为2或3时，各个电子给体D之间可以相同或不同；
电子受体A选自含氮杂环类取代基、含氰基类取代基、三芳基硼类取代基和含磷氧基类取代基中的至少一种；当b为2或3时，各个电子受体A之间可以相同或不同。
本发明的化合物具有D-(π)-σ-(π)-A结构，是一种双极性材料，可以替代现有传统的D-π-A骨架结构。传统的D-π-A双极性材料具有很强的分子内电荷传输，导致大的偶极矩μs，而本发明的化合物中的D-(π)-σ-(π)-A结构同样具有双极性，中间的σ键可以有效打断电子给体D与电子受体A之间这种传输，使得激发态限制为电子给体D或者电子受体A的片段内的局域激发态，因而使化合物具有小的激发态偶极矩，当其用于OLED器件的发光层的主体材料时，可以有效降低蓝光材料的效率滚降，提升发光亮度和发光效率。
本发明的化合物用作电致发光器件中的主体材料，具有较高的三线态能级ET和较大的分子密度，较高玻璃化温度和分子热稳定性，有效提高载流子的平衡迁移，扩宽激子复合区域，有效提高光的取出效率，使得器件的发光效率(EQE)和寿命有了很大提升，在电致发光器件技术领域中可以得到很好的应用。
附图说明
图1是本发明实施例提供的化合物的化学通式；
图2是本发明实施例提供的一种OLED器件的结构示意图；
图3是本发明实施例提供的一种显示装置的示意图。
具体实施方式
下面通过实施例和对比例进一步说明本发明，这些实施例只是用于说明本发明，本发明不限于以下实施例。凡是对本发明技术方案进行修改或者等同替换，而不脱离本发明技术方案的范围，均应涵盖在本发明的保护范围中。
本发明的一方面是提供一种化合物，所述化合物具有式(I)所示的化学结构：
其中，D表示电子给体，A表示电子受体；其中，a和b分别表示电子给体D和电子受体A的个数且分别选自1、2或3，c和d分别表示L1和L2的个数且分别选自0、1或2；
L1和L2各自独立地选自单键、取代或未取代的C1-C20亚烷基、取代或未取代的C3-C20亚环烷基、取代或未取代的C3-C20亚杂环基、取代或未取代的C6-C40亚芳基、取代或未取代的C4-C40亚杂芳基、取代或未取代的C10-C60的亚稠芳基或取代或未取代的C10-C60的亚稠杂芳基中的至少一种；
电子给体D选自取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C10-C60的亚稠芳基、取代或未取代的C10-C60的亚稠杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、C12-C40的吖啶基及其衍生物基团中的至少一种；
电子受体A选自含氮杂环类取代基、含氰基类取代基、三芳基硼类取代基和含磷氧基类取代基中的至少一种。
本发明的化合物中的D-(π)-σ-(π)-A结构同样具有双极性，中间的σ键可以有效打断电子给体D与电子受体A之间这种传输，使得激发态限制为电子给体D或者电子受体A的片段内的局域激发态，因而使化合物具有小的激发态偶极矩，当其用于OLED器件的发光层的主体材料时，可以有效降低蓝光材料的效率滚降，提升发光亮度和发光效率。
本发明的化合物用作电致发光器件中的主体材料，具有较高的三线态能级ET和较大的分子密度，较高玻璃化温度和分子热稳定性，有效提高载流子的平衡迁移，扩宽激子复合区域，有效提高光的取出效率，使得器件的发光效率(EQE)和寿命有了很大提升，在电致发光器件技术领域中可以得到很好的应用。
根据本发明所述化合物的一个实施方式，所述电子给体D选自以下基团中的至少一种：
其中，m、n和p各自独立地选自0、1、2或3；
U1、U2、U3各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种；
#表示连接位置。
根据本发明所述化合物的一个实施方式，所述电子给体D选自以下基团中的至少一种：
其中，R选自氢原子、取代或未取代的C1-C20烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C10-C30稠芳基、取代或未取代的C4-C40杂芳基。
根据本发明所述化合物的一个实施方式，所述电子给体D选自以下基团中的至少一种：
Z选自C原子、N原子、O原子、S原子或Si原子；
其中，m、n和q各自独立地选自0、1、2或3；U1、U2、U3和U4各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种；
当Z为氧原子或硫原子时，q为0；
#表示连接位置。
根据本发明所述化合物的一个实施方式，所述电子给体D选自以下基团中的至少一种：
根据本发明所述化合物的一个实施方式，所述电子给体D选自以下基团中的至少一种：
Z选自C原子、N原子、O原子、S原子或Si原子；X选自C原子、N原子、O原子或S原子；m、n、p和q各自独立地选自0、1、2或3；
U1、U2、U3、U4各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种；
当Z或X为氧原子或硫原子时，p或q为0；
#表示连接位置。
根据本发明所述化合物的一个实施方式，所述电子给体D选自以下基团中的至少一种：
其中，R1、R2、R3和R4分别独立地选自氢原子、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基。
根据本发明所述化合物的一个实施方式，所述电子受体A选自以下基团中的至少一种：
其中，#表示连接位置；
R选自氢原子、C1-C20烷基、C1-C20烷氧基、C4-C8环烷基、C6-C40芳基、C4-C40杂芳基。
根据本发明所述化合物的一个实施方式，所述电子受体A选自以下基团中的至少一种：
其中，#表示连接位置。
根据本发明所述化合物的一个实施方式，所述电子受体A选自以下基团中的至少一种：
其中，#表示连接位置。
根据本发明所述化合物的一个实施方式，所述电子受体A选自以下基团中的至少一种：
其中，#表示连接位置。
根据本发明所述化合物的一个实施方式，所述化合物选自下列化合物：
本发明还提供一种显示面板，所述显示面板包括有机发光器件，其中所述有机发光器件包括相对设置的阳极、阴极，以及位于阳极和阴极之间的发光层，其中发光层包括主体材料和客体材料，所述发光层的主体材料为本发明所述的化合物中的一种或多种。
根据本发明的显示面板，其中所述有机发光器件的主体材料的单重态能级S1高于所述客体材料的单重态能级S1,且主体材料的单重态能级S1与客体材料的单重态能级S1的差值小于0.8eV；所述主体材料的三重态能级T1高于所述客体材料的三重态能级T1，且主体材料的三重态能级T1与客体材料的三重态能级T1的差值小于0.4eV。
根据本发明的显示面板，当所述发光层的主体材料为红光发光材料时，所述红光发光材料的最低三重态能级T1为2.2eV；
当所述发光层的主体材料为绿光发光材料时，所述绿光发光主体材料的最低三重态能级T1为2.5eV；
当所述发光层的发光主体材料为蓝光发光材料时，所述蓝光发光主体材料的最低三重态能级T1为2.7eV。
根据本发明所述显示面板的一个实施方式，所述有机发光器件还包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层或电子注入层中的一层或多层。
根据本发明所述显示面板的一个实施方式，所述显示面板包括有机发光器件，其中所述有机发光器件包括相对设置的阳极、阴极，以及位于所述阴极背离所述阳极一侧的盖帽层，以及位于所述阳极与所述阴极之间的有机层，所述有机层包括电子传输层、空穴传输层和发光层，所述盖帽层与所述电子传输层、空穴传输层、发光层中的至少一者的材料为本发明所述的化合物。
在本发明所述的显示面板中，有机发光器件的阳极材料可以选自金属例如，铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金；金属氧化物例如，氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO)等；导电性聚合物例如，聚苯胺、聚吡咯、聚(3-甲基噻吩)等。除了以上有助于空穴注入材料及其组合之外，阳极材料还可包括其他已知的适合做阳极的材料。
在本发明所述的显示面板中，有机发光器件的阴极材料可以选自金属例如，铝、镁、银、铟、锡、钛等及它们的合金；多层金属材料例如，LiF/Al、LiO2/Al、BaF2/Al等。除以上有助于电子注入的材料及其组合之外，阴极材料还可包括其他已知的适合做阴极的材料。
在本发明的一个实施例中，所述的显示面板中的有机发光器件可以这样制作：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。有机薄层的形成可以采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。最后在阴极上制备一层有机光学覆盖层CPL(盖帽层)。光学覆盖层CPL的材料为本发明所述的化合物。光学覆盖层CPL可以通过蒸镀或溶液法加工制备。溶液加工法包括喷墨打印法、旋转涂布、刮刀涂布、丝网印刷、卷对卷印刷等方法。
下面提供几个示例性的化合物的合成示例。
实施例1
化合物H004的合成
在250mL圆底烧瓶中，将1,1-双(4-碘苯基)环己烷(15mmol)、碘化铜(15mmol)、叔丁醇钾(65mmol)、1,2-二氨基环己烷(12mmol)和二芳胺(25mmol)加入到干燥的1,4-二氧六环(400mL)中，在氮气氛围下回流48小时，得到的中间体冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到中间产物H004-1。
在250mL圆底烧瓶中，将中间产物H004-1(15mmol)和醋酸钾(40mmol)与干燥的1,4-二氧六环(60mL)、Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合，在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并采用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到中间产物H004-2。
在250mL圆底烧瓶中，H004-2(10mmol)、2-氯-4,6-二苯基-三嗪(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中，在氮气氛围下回流反应12h。将得到的混合物冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到最终产物H004。
化合物H004的元素分析结果(分子式C45H38N4)：理论值：C,85.14；H,6.03；N,8.83。测试值：C,85.14；H,6.02；N,8.84。通过液相质谱联用分析得ESI-MS(m/z)(M+)：理论值：634.31，测试值：634.51。
实施例2
化合物H022的合成
在250mL圆底烧瓶中，将1,1-双(4-碘苯基)环己烷(15mmol)、碘化铜(15mmol)、叔丁醇钾(65mmol)、1,2-二氨基环己烷(12mmol)和9-咔唑(25mmol)加入到干燥的1,4-二氧六环(400mL)中，在氮气氛围下回流48小时，得到的中间体冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并采用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到中间产物H013-1。
在250mL圆底烧瓶中，将中间产物H013-1(15mmol)和醋酸钾(40mmol)与干燥的1,4-二氧六环(60mL)、Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合，在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到中间产物H013-2。
在250mL圆底烧瓶中，H013-2(10mmol)、2-氯-4-(二苯基膦酰基)-二苯并噻吩(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中，在氮气氛围下回流反应12h。将得到的混合物冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并采用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到最终产物H013。
化合物H013的元素分析结果(分子式C54H42NOPS)：理论值：C,82.73；H,5.40；N,1.79；O,2.04；P,3.95；S,4.09。测试值：C,82.73；H,5.41；N,1.78；O,2.04；P,3.95；S,4.09。通过液相质谱联用分析得ESI-MS(m/z)(M+)：理论值：783.27，测试值：783.86。
实施例3
化合物H048的合成
在250mL圆底烧瓶中，将1,1-双(4-碘苯基)环己烷(15mmol)、碘化铜(15mmol)、叔丁醇钾(65mmol)、1,2-二氨基环己烷(12mmol)和9,9-二甲基吖啶(25mmol)加入到干燥的1,4-二氧六环(400mL)中，在氮气氛围下回流48小时，得到的中间体冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并采用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到中间产物H048-1。
在250mL圆底烧瓶中，将中间产物H048-1(15mmol)和醋酸钾(40mmol)与干燥的1,4-二氧六环(60mL)、Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合，在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并采用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到中间产物H048-2。
在250mL圆底烧瓶中，H048-2(10mmol)、4-溴-2,6-二苯基吡啶-3,5-二羰腈(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中，在氮气氛围下回流反应12h。将得到的混合物冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并采用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到最终产物H048。
化合物H048的元素分析结果(分子式C52H42N4)：理论值：C,86.39；H,5.86；N,7.75。测试值：C,86.39；H,5.87；N,7.74。通过液相质谱联用分析得ESI-MS(m/z)(M+)：理论值：722.34，测试值：722.67。
实施例4
化合物H077的合成
在250mL圆底烧瓶中，将1,1-双(4-碘苯基)环己烷(15mmol)、碘化铜(15mmol)、叔丁醇钾(65mmol)、1,2-二氨基环己烷(12mmol)和9,9-二苯基-9,10-二氢吖啶(25mmol)加入到干燥的1,4-二氧六环(400mL)中，在氮气氛围下回流48小时，得到的中间体冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并采用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到中间产物H077-1。
在250mL圆底烧瓶中，将中间产物H077-1(15mmol)和醋酸钾(40mmol)与干燥的1,4-二氧六环(60mL)、Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合，在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并采用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到中间产物H077-2。
在250mL圆底烧瓶中，H077-2(10mmol)、1-溴-3,5-双(2,6-二苯基嘧啶)苯(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中，在氮气氛围下回流反应12h。将得到的混合物冷却到室温，加入水中，然后通过硅藻土垫过滤，滤液用二氯甲烷萃取，然后用水洗涤，并采用无水硫酸镁干燥，过滤和蒸发后，用硅胶柱层析纯化粗产物得到最终产物H077。
化合物H077的元素分析结果(分子式C81H61N5)：理论值：C,88.09；H,5.57；N,6.34。测试值：C,88.09；H,5.58；N,6.33。通过液相质谱联用分析得ESI-MS(m/z)(M+)：理论值：1103.49，测试值：1103.84。
表1化合物的能级值
化合物 HOMO(eV) LUMO(eV) Eg(ev) E<sub>T</sub>(ev)
H004 -5.423 -2.327 3.096 2.9147
H022 -5.459 -2.291 3.168 2.9983
H048 -5.416 -2.315 3.101 2.9208
H077 -5.503 -2.372 3.131 2.9314
由上表1可以看出，作为主体材料，化合物H004、H022、H048和H077显示出合适的HOMO与LUMO能级以及很高的三线态能量ET(>2.9ev)，适合应用于红光(ET至少>2.2ev)，绿光(ET至少>2.5ev)，蓝光(ET至少>2.7ev)的主体材料，可以有效地实现主体材料和客体材料之间的能量传递而不存在电荷回传的风险。
实施例5
本实施例提供了一种有机发光器件。如图2所示，有机发光器件包括：玻璃基板1、ITO阳极2、第一空穴传输层3、第二空穴传输层4、发光层5、第一电子传输层6、第二电子传输层7、阴极8(镁银电极，镁银质量比为9:1)和盖帽层(CPL)9，其中ITO阳极2的厚度是15nm，第一空穴传输层3的厚度是10nm、第二空穴传输层4的厚度是95nm、发光层5的厚度是30nm、第一电子传输层6的厚度是35nm、第二电子传输层7的厚度是5nm、镁银电极8的厚度是15nm和盖帽层(CPL)9的厚度是100nm。
本发明的有机发光器件的制备步骤如下：
1)将玻璃基板1切成50mm×50mm×0.7mm的大小，分别在异丙醇和去离子水中超声处理30分钟，然后暴露在臭氧下约10分钟来进行清洁；将所得的具有ITO阳极2的玻璃基板1安装到真空沉积设备上；
2)在ITO阳极2上，通过真空蒸镀方式蒸镀空穴注入层材料HAT-CN，厚度为10nm，该层作为第一空穴传输层3；
3)在第一空穴传输层3上真空蒸镀第二空穴传输层2材料为TAPC，厚度为110nm，作为第二空穴传输层4；
4)空穴传输层4上共沉积发光层5，其中，化合物H004作为主体材料，Ir(ppy)3作为掺杂材料，化合物H004与Ir(ppy)3的质量比为19:1，厚度为30nm；
5)在发光层5上真空蒸镀第一电子传输层6，第一电子传输层6的材料为BPen，厚度为30nm；
6)在第一电子传输层6上真空蒸镀第二电子传输层7，第二电子传输层7的材料为Alq3，厚度为5nm；
7)在第二电子传输层7上真空蒸镀镁银电极，其中，质量比Mg:Ag为9:1，厚度为15nm，作为阴极8；
8)在阴极8上真空蒸镀高折射率的空穴型材料CBP，厚度为100nm，作为阴极覆盖层(盖帽层或CPL)9使用。
本实施例涉及的化合物及其结构如下所示。
实施例6
器件制作过程同实施例5，不同之处在于主体材料为H022，其他各层材料均相同。
实施例7
器件制作过程同实施例5，不同之处在于主体材料为H048，其他各层材料均相同。
实施例8
器件制作过程同实施例5，不同之处在于主体材料为H077，其他各层材料均相同。
器件对比例1
对比器件制作过程同实施例5，不同之处在于主体材料为CzTRZ，其他各层材料均相同。
表2器件发光性能测试结果
由上表2可以看出，采用本发明的化合物作为主体材料的发光器件具有更低的驱动电压，相对于对比器件1下降约8.5％，因此可以有效降低器件的功耗。与对比器件1相比，采用本发明的化合物作为主体材料的发光器件具有更高的发光效率，比对比器件1约提升10％-25％左右，可以有效地提升器件的发光亮度；采用本发明的化合物的作为发光主体材料的器件具有更长的寿命，提升约18％以上。
本发明的又一方面还提供一种显示装置，其包括如上文所述的有机发光显示面板。
在本发明中，有机发光器件可以是OLED，其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、液晶电视显示屏、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。图3是根据本发明实施例提供的一种显示装置的示意图。在图3中，11表示手机显示屏。
本申请虽然以较佳实施例公开如上，但并不是用来限定权利要求，任何本领域技术人员在不脱离本申请构思的前提下，都可以做出若干可能的变动和修改，因此本申请的保护范围应当以本申请权利要求所界定的范围为准。

Claims (18)

1.一种化合物，所述化合物具有式(I)所示的化学结构：
其中，D表示电子给体，A表示电子受体；其中，a和b分别表示电子给体D和电子受体A的个数且分别选自1、2或3，c和d分别表示L1和L2的个数且分别选自0、1或2；
L1和L2各自独立地选自单键、取代或未取代的C1-C20亚烷基、取代或未取代的C3-C20亚环烷基、取代或未取代的C3-C20亚杂环基、取代或未取代的C6-C40亚芳基、取代或未取代的C4-C40亚杂芳基、取代或未取代的C10-C60的亚稠芳基或取代或未取代的C10-C60的亚稠杂芳基中的至少一种；
电子给体D选自取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C10-C60的亚稠芳基、取代或未取代的C10-C60的亚稠杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、C12-C40的吖啶基及其衍生物基团中的至少一种；
电子受体A选自含氮杂环类取代基、含氰基类取代基、三芳基硼类取代基和含磷氧基类取代基中的至少一种。
2.根据权利要求1所述的化合物，其特征在于，所述电子给体D选自以下基团中的至少一种：
其中，m、n和p各自独立地选自0、1、2或3；
U1、U2、U3各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种；
#表示连接位置。
3.根据权利要求2所述的化合物，其特征在于，所述电子给体D选自以下基团中的至少一种：
其中，R选自氢原子、取代或未取代的C1-C20烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C10-C30稠芳基、取代或未取代的C4-C40杂芳基。
4.根据权利要求1所述的化合物，其特征在于，所述电子给体D选自以下基团中的至少一种：
Z选自C原子、N原子、O原子、S原子或Si原子；
其中，m、n和q各自独立地选自0、1、2或3；U1、U2、U3和U4各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种；
当Z为氧原子或硫原子时，q为0；
#表示连接位置。
5.根据权利要求4所述的化合物，其特征在于，所述电子给体D选自以下基团中的至少一种：
6.根据权利要求1所述的化合物，其特征在于，所述电子给体D选自以下基团中的至少一种：
Z选自C原子、N原子、O原子、S原子或Si原子；X选自C原子、N原子、O原子或S原子；m、n、p和q各自独立地选自0、1、2或3；
U1、U2、U3、U4各自独立地选自氢原子、取代或未取代的C1-C30烷基、取代或未取代的亚甲硅烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠芳基中的至少一种；
当Z或X为氧原子或硫原子时，p或q为0；
#表示连接位置。
7.根据权利要求6所述的化合物，其特征在于，所述电子给体D选自以下基团中的至少一种：
其中，R1、R2、R3和R4分别独立地选自氢原子、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基。
8.根据权利要求1所述的化合物，其特征在于，所述电子受体A选自以下基团中的至少一种：
其中，#表示连接位置；
R选自氢原子、C1-C20烷基、C1-C20烷氧基、C4-C8环烷基、C6-C40芳基、C4-C40杂芳基。
9.根据权利要求1所述的化合物，其特征在于，所述电子受体A选自以下基团中的至少一种：
其中，#表示连接位置。
10.根据权利要求1所述的化合物，其特征在于，所述电子受体A选自以下基团中的至少一种：
其中，#表示连接位置。
11.根据权利要求1所述的化合物，其特征在于，所述电子受体A选自以下基团中的至少一种：
其中，#表示连接位置。
12.根据权利要求1所述的化合物，其特征在于，所述化合物选自下列化合物：
13.一种显示面板，包括有机发光器件，其中所述有机发光器件包括相对设置的阳极、阴极，以及位于阳极和阴极之间的发光层，其中发光层包括主体材料和客体材料，其特征在于，所述发光层的主体材料为权利要求1至12任一项所述的化合物中的一种或多种。
14.根据权利要求13所述的显示面板，其特征在于，所述主体材料的单重态能级S1高于所述客体材料的单重态能级S1，且主体材料的单重态能级S1与客体材料的单重态能级S1的差值小于0.8eV；所述主体材料的三重态能级T1高于所述客体材料的三重态能级T1，且主体材料的三重态能级T1与客体材料的三重态能级T1的差值小于0.4eV。
15.根据权利要求13所述的显示面板，其特征在于，当所述发光层的主体材料为红光发光材料时，所述红光发光材料的最低三重态能级T1为2.2eV；
当所述发光层的主体材料为绿光发光材料时，所述绿光发光主体材料的最低三重态能级T1为2.5eV；
当所述发光层的发光主体材料为蓝光发光材料时，所述蓝光发光主体材料的最低三重态能级T1为2.7eV。
16.根据权利要求13至15任一项所述的显示面板，其特征在于，所述有机发光器件还包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层或电子注入层中的一层或多层。
17.一种显示面板，包括有机发光器件，其中所述有机发光器件包括相对设置的阳极、阴极，以及位于所述阴极背离所述阳极一侧的盖帽层，以及位于所述阳极与所述阴极之间的有机层，所述有机层包括电子传输层、空穴传输层和发光层，所述盖帽层与所述电子传输层、空穴传输层、发光层中的至少一者的材料为权利要求1至12任一项所述的化合物。
18.一种显示装置，包括权利要求13至17任一项所述的显示面板。
CN201811622667.XA 2018-12-28 2018-12-28 化合物、显示面板以及显示装置 Pending CN109456256A (zh)

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