CN111574434B - 一种化合物及包含其的有机发光器件、显示面板和显示装置 - Google Patents
一种化合物及包含其的有机发光器件、显示面板和显示装置 Download PDFInfo
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- CN111574434B CN111574434B CN202010524204.0A CN202010524204A CN111574434B CN 111574434 B CN111574434 B CN 111574434B CN 202010524204 A CN202010524204 A CN 202010524204A CN 111574434 B CN111574434 B CN 111574434B
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- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
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Abstract
本发明提供了一种化合物及包含其的有机发光器件、显示面板和显示装置。所述化合物具有式I所示结构。所述有机发光器件包括阳极、阴极,以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括发光层、电子传输层和空穴阻挡层中的一种或至少两种的组合,且至少包括发光层;所述发光层、电子传输层和空穴阻挡层中的至少一层含有至少一种所述化合物。本发明提供的化合物具有较深的LUMO能级、较深的HOMO能级和较高的三线态能级,电子迁移率高,Tg高,热稳定性和化学稳定性好,不易结晶,可用于有机发光器件的发光层、电子传输层和/或空穴阻挡层中,降低器件开启电压,提高器件发光效率和寿命。
Description
技术领域
本发明属于有机光电材料技术领域,具体涉及一种化合物及包含其的有机发光器件、显示面板和显示装置。
背景技术
传统电致发光器件中使用的电子传输材料是Alq3,但Alq3的电子迁移率比较低(大约为l0-6cm2/Vs),使得器件的电子传输与空穴传输不均衡。随着电致发光器件产品化和实用化,人们希望得到传输效率更高、使用性能更好的电子传输材料。因此,设计开发稳定高效,能够同时具有高电子迁移率和高玻璃化转变温度的电子传输材料和/或电子注入材料,具有很重要的实际应用价值。
目前,市场上较多使用的电子传输材料,如红菲咯啉(batho-phenanthroline,BPhen)、浴铜灵(bathocuproine,BCP)和TmPyPB,大体上能符合有机电致发光面板的市场需求,但它们的玻璃化转变温度Tg较低,一般小于85℃,器件运行时,产生的焦耳热会导致分子的降解和分子结构的改变,使面板效率较低,热稳定性较差。同时,这种分子结构对称,长时间后很容易结晶。一旦电子传输材料结晶,分子间的电荷跃迀机制与正常运作的非晶态薄膜机制就会产生差异,导致电子传输的性能降低,使得整个器件的电子和空穴迀移率失衡,激子形成效率大大降低,并且激子形成会集中在电子传输层与发光层的界面处,导致器件效率和寿命严重下降。
由于当前有机发光器件的研究仍在发展阶段,良好的电子传输材料种类较少,因此,更多、更高性能的电子传输材料仍然有待于开发。
发明内容
针对现有技术存在的不足,本发明的目的在于提供一种化合物及包含其的有机发光器件、显示面板和显示装置。该化合物具有较深的LUMO能级、较深的HOMO能级和较高的三线态能级,电子迁移率高,Tg高,热稳定性和化学稳定性好,不易结晶,可用于有机发光器件的发光层、电子传输层和/或空穴阻挡层中,降低器件开启电压,提高器件发光效率和寿命。
为达此目的,本发明采用以下技术方案:
第一方面,本发明提供一种化合物,所述化合物具有如下式I所示结构:
其中,L1与L2各自独立地选自单键、取代或未取代的C6-C40芳基、取代或未取代的C3-C40杂芳基中的任意一种;
X1、X2、X3各自独立地为N原子或-CH,且至少一个为N原子;
Ar1、Ar2各自独立地选自取代或未取代的C6-C40芳基、取代或未取代的C3-C40杂芳基中的任意一种;
如上所述基团含有取代基时,所述取代基为甲基、乙基、异丙基、叔丁基、甲氧基、氰基、苯基、联苯基、三联苯基、萘基、蒽基、菲基、吡啶基、嘧啶基、三嗪基、咔唑基、二苯并呋喃基或二苯并噻吩基。
第二方面,本发明提供一种有机发光器件,包括阳极、阴极,以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括发光层、电子传输层和空穴阻挡层中的一种或至少两种的组合,且至少包括发光层;
所述发光层、电子传输层和空穴阻挡层中的至少一层含有至少一种第一方面所述的化合物。
第三方面,本发明提供一种显示面板,包括第二方面所述的有机发光器件。
第四方面,本发明提供一种显示装置,包括第三方面所述的显示面板。
与现有技术相比,本发明具有以下有益效果:
本发明提供的化合物具有较深的LUMO能级(<-1.70eV)、较深的HOMO能级(<-5.25eV)和较高的三线态能级(>2.30eV),电子迁移率高,Tg高,热稳定性和化学稳定性好,不易结晶,可用于有机发光器件的发光层、电子传输层和/或空穴阻挡层中,降低器件开启电压,提高器件发光效率和寿命。
附图说明
图1为本发明应用例提供的OLED器件的结构示意图;
图2为本发明应用例提供的一种有机发光显示装置的示意图;
其中,1为基板,2为阳极,3为空穴注入层,4为第一空穴传输层,5为第二空穴传输层,6为发光层,7为空穴阻挡层,8为电子传输层,9为阴极,10为手机显示屏。
具体实施方式
下面结合附图并通过具体实施例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。
第一方面,本发明提供一种化合物,所述化合物具有如下式I所示结构:
其中,L1与L2各自独立地选自单键、取代或未取代的C6-C40(例如可以是C6、C8、C10、C12、C15、C18、C21、C24、C28、C30、C34、C36或C40等)芳基、取代或未取代的C3-C40(例如可以是C3、C4、C5、C6、C8、C10、C12、C15、C18、C21、C24、C28、C30、C34、C36或C40等)杂芳基中的任意一种;
A1与A2各自独立地选自取代或未取代的C6-C40(例如可以是C6、C8、C10、C12、C15、C18、C21、C24、C28、C30、C34、C36或C40等)芳基、取代或未取代的C3-C40(例如可以是C3、C4、C5、C6、C8、C10、C12、C15、C18、C21、C24、C28、C30、C34、C36或C40等)杂芳基中的任意一种,且A1与A2至少一个选自基团中的任意一种,#代表基团的连接位置;
X1、X2、X3各自独立地为N原子或-CH,且至少一个为N原子;
Ar1、Ar2各自独立地选自取代或未取代的C6-C40(例如可以是C6、C8、C10、C12、C15、C18、C21、C24、C28、C30、C34、C36或C40等)芳基、取代或未取代的C3-C40(例如可以是C3、C4、C5、C6、C8、C10、C12、C15、C18、C21、C24、C28、C30、C34、C36或C40等)杂芳基中的任意一种;
如上所述基团含有取代基时,所述取代基为甲基、乙基、异丙基、叔丁基、甲氧基、氰基、苯基、联苯基、三联苯基、萘基、蒽基、菲基、吡啶基、嘧啶基、三嗪基、咔唑基、二苯并呋喃基或二苯并噻吩基。
本发明提供的化合物以连接氮杂环为核心结构,其分子中有大的共轭结构,具有较高的电子迁移率,有助于提高激子的产生速率;具有较深的LUMO能级,电子注入势垒小,利于电子的注入;具有较深的HOMO能级,有利于阻挡空穴;具有较高的三线态能级,可有效阻挡激子,将激子限制在发光层中;其Tg(玻璃化转变温度)高,热稳定性和化学稳定性好,有助于减少使用其的有机发光器件在工作时产生的焦耳热对器件寿命和效率的影响;不易结晶,有利于减少光散射和结晶诱导产生的降解或器件效率衰减。本发明提供的化合物可用于有机发光器件的发光层、电子传输层和/或空穴阻挡层中,降低有机发光器件的开启电压,提高发光效率和寿命。
需要说明的是,本发明提供的化合物的LUMO能级和HOMO能级为负值,本发明中HOMO能级或LUMO能级“高”或“浅”,均是指其数值大,绝对值小;HOMO能级或LUMO能级“低”或“深”,均是指其数值小,绝对值大。
在本发明一实施方式中,所述化合物具有如下式II所示结构:
在本发明一实施方式中,所述L1与L2各自独立地选自单键、亚苯基、亚联苯基、亚萘基、亚蒽基、亚呋喃基、亚噻吩基、亚吡啶基、亚嘧啶基、亚三嗪基和亚芴基中的任意一种。
在本发明一实施方式中,所述Ar1、Ar2各自独立地选自苯基、联苯基、三联苯基、萘基、蒽基、菲基、吡啶基、嘧啶基、三嗪基、二苯并呋喃基、二苯并噻吩基、咔唑基、芴基和螺芴基中的任意一种。
在本发明一实施方式中,所述化合物具有如下式III或式IV所示结构:
其中,L1与L2各自独立地选自单键、亚苯基、亚联苯基、亚萘基、亚蒽基、亚呋喃基、亚噻吩基、亚吡啶基、亚嘧啶基、亚三嗪基和亚芴基中的任意一种;
Ar1与Ar2各自独立地选自苯基、联苯基、三联苯基、萘基、蒽基、菲基、吡啶基、嘧啶基、三嗪基、二苯并呋喃基、二苯并噻吩基、咔唑基、芴基和螺芴基中的任意一种。
在本发明一实施方式中,所述化合物具有式IV所示结构;
其中,L1与L2各自独立地为单键、亚苯基或亚萘基;
Ar1与Ar2各自独立地选自苯基、联苯基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基和芴基中的任意一种。
在本发明一实施方式中,所述化合物选自如下化合物H1~H81中的任意一种:
第二方面,本发明提供一种有机发光器件(OLED器件),包括阳极、阴极,以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括发光层、电子传输层和空穴阻挡层中的一种或至少两种的组合,且至少包括发光层;
所述发光层、电子传输层和空穴阻挡层中的至少一层含有至少一种第一方面所述的化合物。
在本发明一实施方式中,所述有机薄膜层还包括空穴注入层、空穴传输层、电子阻挡层和电子注入层中的一种或至少两种的组合。
在本发明一实施方式中,所述发光层包括主体材料和发光材料,所述发光层的主体材料包括第一方面所述的化合物中的一种或至少两种的组合。
在本发明一实施方式中,所述电子传输层的材料选自第一方面所述的化合物中的一种或至少两种的组合;
或者所述电子传输层包括主体材料和客体材料,所述电子传输层的主体材料选自第一方面所述的化合物中的一种或至少两种的组合。
在本发明一实施方式中,所述空穴阻挡层的材料选自第一方面所述的化合物中的一种或至少两种的组合,且所述发光层的发光材料的最低三线态能级低于所述化合物的最低三线态能级。
第三方面,本发明提供一种显示面板,包括第二方面所述的有机发光器件。
第四方面,本发明提供一种显示装置,包括第三方面所述的显示面板。
本发明实施例中示例性地提供下述化合物及其制备方法,并应用其示例性地制备有机发光器件。本领域技术人员应该明了,这仅仅是帮助理解本发明,不应视为对本发明的具体限制。
制备例1
化合物H2的制备,具体步骤如下:
在250mL圆底烧瓶中,将6-碘-12-溴-(12mmol)、苯基硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H2-1。
中间产物H2-1的表征结果:
元素分析结果:C24H15Br,理论值:C,75.21;H,3.94;Br,20.85;测试值:C,75.21;H,3.95;Br,20.84。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为382.04,测试值为382.28。
在250mL圆底烧瓶中,将中间产物H2-1(12mmol)、(4-氯萘基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H2-2。
中间产物H2-2的表征结果:
元素分析结果:C34H21Cl,理论值C,87.82;H,4.55;Cl,7.62;测试值:C,87.82;H,4.54;Cl,7.63。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为464.13;测试值:464.98。
在250mL圆底烧瓶中,将中间产物H2-2(12mmol)、(2,6-二苯基-2-吡啶基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H2。
化合物H2的表征结果:
元素分析结果:C51H33N,理论值:C,92.84;H,5.04;N,2.12;测试值:C,92.84;H,5.05;N,2.11。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为659.26,测试值为659.81。
制备例2
化合物H8的制备,具体步骤如下:
在250mL圆底烧瓶中,将6-碘-12-溴-(12mmol)、苯基硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H8-1。
中间产物H8-1的表征结果:
元素分析结果:C24H15Br,理论值:C,75.21;H,3.94;Br,20.85;测试值:C,75.21;H,3.95;Br,20.84。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:382.04;测试值为:383.28。
在250mL圆底烧瓶中,将中间产物H8-1(12mmol)、(4-氯萘基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H8-2。
中间产物H8-2的表征结果:
元素分析结果:C34H21Cl,理论值:C,87.82;H,4.55;Cl,7.62;测试值:C,87.82;H,4.54;Cl,7.63。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:464.13;测试值为:464.98。
在250mL圆底烧瓶中,将中间产物H8-2(12mmol)、2-硼酸-4,6-二苯基-三嗪(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H8。
化合物H8的表征结果:
元素分析结果:C49H31N3,理论值:C,88.93;H,4.72;N,6.35;测试值:C,88.95;H,4.74;N,6.31。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为661.25,测试值为661.79。
制备例3
化合物H15的制备,具体步骤如下:
在250mL圆底烧瓶中,将6-碘-12-溴-(12mmol)、(4-二苯并呋喃)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H15-1。
中间产物H15-1的表征结果:
元素分析结果:C30H17BrO,理论值:C,76.12;H,3.62;Br,16.88;O,3.38;测试值:C,76.12;H,3.64;Br,16.87;O,3.37。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:472.05;测试值为:473.36。
在250mL圆底烧瓶中,将中间产物H15-1(12mmol)、(4-氯萘基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H15-2。
中间产物H15-2的表征结果:
元素分析结果:C40H23ClO,理论值:C,86.55;H,4.18;Cl,6.39;O,2.88;测试值:C,86.55;H,4.17;Cl,6.40;O,2.88。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:554.14;测试值为:555.06。
在250mL圆底烧瓶中,将中间产物H15-2(12mmol)、2-硼酸-4,6-二苯基-三嗪(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H15。
化合物H15的表征结果:
元素分析结果:C55H33N3O,理论值:C,87.86;H,4.42;N,5.59;O,2.13;测试值:C,87.88;H,4.45;N,5.57;O,2.10。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为751.26,测试值为751.87。
制备例4
化合物H31的制备,具体步骤如下:
在250mL圆底烧瓶中,将6-碘-12-溴-(12mmol)、吡啶基硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H31-1。
中间产物H31-1的表征结果:
元素分析结果:C23H14BrN,理论值:C,71.89;H,3.67;Br,20.79;N,3.65;测试值:C,71.89;H,3.69;Br,20.78;N,3.66。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:383.03;测试值为:384.27。
在250mL圆底烧瓶中,将中间产物H31-1(12mmol)、(4-氯萘基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H31-2。
中间产物H31-2的表征结果:
元素分析结果:C33H20ClN,理论值:C,85.06;H,4.33;Cl,7.61;N,3.01;测试值:C,85.06;H,4.31;Cl,7.61;N,3.03。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:465.13;测试值为:465.97。
在250mL圆底烧瓶中,将中间产物H31-2(12mmol)、2-硼酸-4,6-二苯基-三嗪(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H31。
化合物H31的表征结果:
元素分析结果:C48H30N4,理论值:C,86.98;H,4.56;N,8.45;测试值:C,86.98;H,4.58;N,8.43。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为662.25,测试值为662.78。
制备例5
化合物H33的制备,具体步骤如下:
在250mL圆底烧瓶中,将6-碘-12-溴-(12mmol)、苯基硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H33-1。
中间产物H33-1的表征结果:
元素分析结果:C24H15Br,理论值:C,75.21;H,3.94;Br,20.85;测试值:C,75.21;H,3.95;Br,20.84。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:382.04;测试值为:383.28。
在250mL圆底烧瓶中,将中间产物H33-1(12mmol)、(4-氯萘基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H33-2。
中间产物H33-2的表征结果:
元素分析结果:C34H21Cl,理论值:C,87.82;H,4.55;Cl,7.62;测试值:C,87.82;H,4.54;Cl,7.63。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:464.13;测试值为:464.98。
在250mL圆底烧瓶中,将中间产物H33-2(12mmol)、2-硼酸-4-(1-二苯并呋喃)-6-苯基-三嗪(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H33。
化合物H33的表征结果:
元素分析结果:C55H33N3O,理论值:C,87.86;H,4.42;N,5.59;O,2.13;测试值:C,87.81;H,4.45;N,5.58;O,2.16。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为751.26,测试值为751.87。
制备例6
化合物H34的制备,具体步骤如下:
在250mL圆底烧瓶中,将6-碘-12-溴-(12mmol)、9-苯基咔唑基硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H34-1。
中间产物H34-1的表征结果:
元素分析结果:C36H22BrN,理论值:C,78.83;H,4.04;Br,14.57;N,2.55;测试值:C,78.83;H,4.01;Br,14.58;N,2.57。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:547.09;测试值为:548.47。
在250mL圆底烧瓶中,将中间产物H34-1(12mmol)、(4-氯萘基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H34-2。
中间产物H34-2的表征结果:
元素分析结果:C46H28ClN,理论值:C,87.67;H,4.48;Cl,5.63;N,2.22;测试值:C,87.67;H,4.45;Cl,5.65;N,2.23。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:629.19;测试值为:630.17。
在250mL圆底烧瓶中,将中间产物H34-2(12mmol)、2-硼酸-4,6-二苯基-三嗪(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H34。
化合物H34的表征结果:
元素分析结果:C61H38N4,理论值:C,88.59;H,4.63;N,6.77;测试值:C,88.59;H,4.65;N,6.75。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为826.31,测试值为826.98。
制备例7
化合物H36的制备,具体步骤如下:
在250mL圆底烧瓶中,将6-碘-12-溴-(12mmol)、苯基硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H36-1。
中间产物H36-1的表征结果:
元素分析结果:C24H15Br,理论值:C,75.21;H,3.94;Br,20.85;测试值:C,75.21;H,3.95;Br,20.84。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:382.04;测试值为:383.28。
在250mL圆底烧瓶中,将中间产物H36-1(12mmol)、(6-氯吡啶基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H36-2。
中间产物H36-2的表征结果:
元素分析结果:C29H18ClN,理论值:C,83.75;H,4.36;Cl,8.52;N,3.37;测试值:C,83.75;H,4.38;Cl,8.51;N,3.36。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:415.11;测试值为:415.91。
在250mL圆底烧瓶中,将中间产物H36-2(12mmol)、2-硼酸-4,6-二苯基-三嗪(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H36。
化合物H36的表征结果:
元素分析结果:C44H28N4,理论值:C,86.25;H,4.61;N,9.14;测试值:C,86.25;H,4.62;N,9.13。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为612.23,测试值为612.72。
制备例8
化合物H37的制备,具体步骤如下:
在250mL圆底烧瓶中,将6,12-二溴-(12mmol)、2-硼酸-4,6-二苯基-三嗪(25mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H37。
化合物H37的表征结果:
元素分析结果:C48H30N6,理论值:C,83.46;H,4.38;N,12.17;测试值:C,83.42;H,4.39;N,12.20。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为690.25,测试值为690.79。
制备例9
在250mL圆底烧瓶中,将6-碘-12-溴-(12mmol)、2-硼酸-4,6-二吡啶基-吡啶(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H41-1。
中间产物H41-1的表征结果:
元素分析结果:C33H20BrN3,理论值:C,73.61;H,3.74;Br,14.84;N,7.80;测试值:C,73.61;H,3.75;Br,14.84;N,7.79。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:537.08;测试值为:538.44。
在250mL圆底烧瓶中,将中间产物H41-1(12mmol)、(4-氯萘基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H41-2。
中间产物H41-2的表征结果:
元素分析结果:C43H26ClN3,理论值:C,83.28;H,4.23;Cl,5.72;N,6.78;测试值:C,83.28;H,4.24;Cl,5.72;N,6.77。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:619.18;测试值为:620.14。
在250mL圆底烧瓶中,将中间产物H41-2(12mmol)、2-硼酸-4,6-二苯基-三嗪(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H41。
化合物H41的表征结果:
元素分析结果:C58H36N6,理论值:C,85.27;H,4.44;N,10.29;测试值:C,85.22;H,4.46;N,10.32。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为816.30,测试值为816.95。
制备例10
化合物H43的制备,具体步骤如下:
在250mL圆底烧瓶中,将6-碘-12-溴-(12mmol)、联苯基硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H43-1。
中间产物H43-1的表征结果:
元素分析结果:C30H19Br,理论值:C,78.44;H,4.17;Br,17.39;测试值:C,78.43;H,4.19;Br,17.38。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:458.07;测试值为:459.38。
在250mL圆底烧瓶中,将中间产物H43-1(12mmol)、(4-氯萘基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H43-2。
中间产物H43-2的表征结果:
元素分析结果:C40H25Cl,理论值:C,88.79;H,4.66;Cl,6.55;测试值:C,88.79;H,4.67;Cl,6.54。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:540.16;测试值为:541.08。
在250mL圆底烧瓶中,将中间产物H43-2(12mmol)、2-硼酸-4,6-二联苯基-三嗪(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H43。
化合物H43的表征结果:
元素分析结果:C67H43N3,理论值:C,90.41;H,4.87;N,4.72;测试值:C,90.37;H,4.88;N,4.75。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为889.35,测试值为890.08。
制备例11
化合物H71的制备,具体步骤如下:
在250mL圆底烧瓶中,将6-碘-12-溴-(12mmol)、(1-二苯并呋喃)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H71-1。
中间产物H71-1的表征结果:
元素分析结果:C30H17BrO,理论值:C,76.12;H,3.62;Br,16.88;O,3.38;测试值:C,76.12;H,3.60;Br,16.89;O,3.39。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:472.05;测试值为:473.36。
在250mL圆底烧瓶中,将中间产物H71-1(12mmol)、(4-氯萘基)硼酸(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H71-2。
中间产物H71-2的表征结果:
元素分析结果:C40H23ClO,理论值:C,86.55;H,4.18;Cl,6.39;O,2.88;测试值:C,86.55;H,4.16;Cl,6.40;O,2.89。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为:554.14;测试值为:555.06。
在250mL圆底烧瓶中,将中间产物H71-2(12mmol)、2-硼酸-4,6-二吡啶基-嘧啶(12mmol)和Na2CO3(80mmol)分别加入到甲苯/EtOH(无水乙醇)/H2O(75/25/50,mL)混合溶剂中,形成混合溶液,然后将Pd(PPh3)4(0.48mmol)加入到上述混合溶液中,在氮气气氛下进行回流反应20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,同时用二氯甲烷萃取,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H71。
化合物H71的表征结果:
元素分析结果:C54H32N4O,理论值:C,86.15;H,4.28;N,7.44;O,2.13;测试值:C,86.15;H,4.30;N,7.43;O,2.12。
通过液相色谱-质谱联用分析得到ESI-MS(m/z)(M+):理论值为752.26,测试值为752.86。
化合物能级的模拟计算:
运用密度泛函理论(DFT),针对本发明实施例提供的有机化合物,以及对比化合物1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,同时基于含时密度泛函理论(TDDFT)模拟计算了化合物分子的最低三线态能级ET1,结果如下表1所示。
表1
表1中,Eg=LUMO-HOMO。
从表1可以看出,本发明的化合物H2、H8、H15、H33、H37、H41、H43相比于对比化合物1具有更深的LUMO能级(<-1.70eV),这有利于本发明的化合物与相邻层材料匹配,LUMO能级越深,从阴极产生的电子越容易注入和传输,利于降低器件启亮阈值和工作电压,降低器件功耗;具有较深的HOMO能级(<-5.25eV),有利于阻挡空穴;具有较高的最低三线态能级(>2.30eV),有利于阻挡激子,将激子限制在发光层中,提高器件发光效率。
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,其结构如图1所示,包括依次层叠的基板1、阳极2、空穴注入层3、第一空穴传输层4、第二空穴传输层5、发光层6、空穴阻挡层7、电子传输层8和阴极9,图1中的箭头代表器件的出光方向。
上述OLED器件的具体制备步骤如下:
1)将带有氧化铟锡(ITO)阳极(厚度为15nm)的玻璃基板切成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,将清洗后的玻璃基板安装到真空沉积设备上;
2)在ITO阳极2上,通过真空蒸镀方式共同蒸镀空穴注入层材料化合物b和P-掺杂材料化合物a,掺杂比例为3%(质量比);厚度为5nm,这层作为空穴注入层3;
3)在空穴注入层3上真空蒸镀空穴传输材料化合物b,厚度为100nm,作为第一空穴传输层4;
4)在第一空穴传输层4上真空蒸镀空穴传输材料化合物d,厚度为5nm,作为第二空穴传输层5;
5)在第二空穴传输层5上真空共同蒸镀发光主体材料化合物e和掺杂材料化合物f,掺杂比例为3%(质量比),厚度为30nm,作为发光层6;
6)在发光层6上真空蒸镀化合物g,厚度为30nm,作为空穴阻挡层7;
7)在空穴阻挡层7上真空共同蒸镀化合物H2和N-掺杂材料化合物h,掺杂质量比例为1:1;厚度为5nm,作为电子传输层8;
8)在电子传输层8上真空蒸镀镁银电极,其中,Mg:Ag质量比为1:9,厚度为10nm,作为阴极9。
上述OLED器件制备过程中使用的化合物如下:
应用例2
本应用例提供一种OLED器件,与应用例1的区别仅在于,将步骤7)中的化合物H2替换为化合物H8,其他制备步骤均相同。
应用例3
本应用例提供一种OLED器件,与应用例1的区别仅在于,将化合物H2替换为化合物H15,其他制备步骤均相同。
应用例4
本应用例提供一种OLED器件,与应用例1的区别仅在于,将化合物H2替换为化合物H31,其他制备步骤均相同。
应用例5
本应用例提供一种OLED器件,与应用例1的区别仅在于,将化合物H2替换为化合物H33,其他制备步骤均相同。
应用例6
本应用例提供一种OLED器件,与应用例1的区别仅在于,将化合物H2替换为化合物H34,其他制备步骤均相同。
应用例7
本应用例提供一种OLED器件,与应用例1的区别仅在于,将化合物H2替换为化合物H36,其他制备步骤均相同。
应用例8
本应用例提供一种OLED器件,与应用例1的区别仅在于,将化合物H2替换为H37,其他制备步骤均相同。
应用例9
本应用例提供一种OLED器件,与应用例1的区别仅在于,将化合物H2替换为H41,其他制备步骤均相同。
应用例10
本应用例提供一种OLED器件,与应用例1的区别仅在于,将化合物H2替换为H43,其他制备步骤均相同。
应用例11
本应用例提供一种OLED器件,与应用例1的区别仅在于,将化合物H2替换为化合物H71,其他制备步骤均相同。
对比例1
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)的工作电压和电流效率(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);E/CIEy是指蓝光中的Blue Index,也是衡量蓝光发光效率的参数,E指电流效率,CIEy指根据器件发光半峰宽波长带入CIE1930软件中得到的纵坐标色点。测试数据如表2所示。
表2
OLED器件 | 电子传输层材料 | V<sub>on</sub>(V) | E/CIEy | 寿命LT95(h) |
应用例1 | 化合物H2 | 3.87 | 150.1 | 67 |
应用例2 | 化合物H8 | 3.85 | 152.2 | 66 |
应用例3 | 化合物H15 | 3.84 | 151.8 | 68 |
应用例4 | 化合物H31 | 3.81 | 152.0 | 64 |
应用例5 | 化合物H33 | 3.83 | 150.9 | 67 |
应用例6 | 化合物H34 | 3.84 | 152.7 | 65 |
应用例7 | 化合物H36 | 3.85 | 151.3 | 66 |
应用例8 | 化合物H37 | 3.83 | 152.4 | 68 |
应用例9 | 化合物H41 | 3.85 | 151.5 | 65 |
应用例10 | 化合物H43 | 3.82 | 153.0 | 66 |
应用例11 | 化合物H71 | 3.84 | 152.9 | 67 |
对比例1 | 对比化合物1 | 3.98 | 141.8 | 60 |
从表2可以看出,应用例1至应用例7相比于对比例1,具有更低的工作电压、更高的B.I.发光效率、更长的器件寿命;以上参数分别提升3.8%、7.2%、10%左右。这主要是因为本发明化合物具有更深的LUMO能级,与相邻层材料LUMO能级之间带隙差更小,有利于电子的有效注入和传输;同时,器件寿命的提升,也基于本发明化合物具有较深的LUMO能级,且能与N-掺杂剂更好地络合。
本发明的又一应用例提供了一种显示面板,包括如上文所述的OLED器件。
本发明的又一应用例提供了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。图2是本发明应用例提供的一种有机发光显示装置的示意图;其中,10为手机显示屏。
申请人声明,以上所述仅为本发明的具体实施方式,但本发明的保护范围并不局限于此,所属技术领域的技术人员应该明了,任何属于本技术领域的技术人员在本发明揭露的技术范围内,可轻易想到的变化或替换,均落在本发明的保护范围和公开范围之内。
Claims (5)
2.一种有机发光器件,其特征在于,所述有机发光器件包括阳极、阴极,以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括发光层、电子传输层和空穴阻挡层中的一种或至少两种的组合,且至少包括发光层;
所述电子传输层的材料选自如权利要求1所述的化合物中的一种或至少两种的组合;
或者所述电子传输层包括主体材料和客体材料,所述电子传输层的主体材料选自如权利要求1所述的化合物中的一种或至少两种的组合。
3.根据权利要求2所述的有机发光器件,其特征在于,所述空穴阻挡层的材料选自如权利要求1所述的化合物中的一种或至少两种的组合,且所述发光层的发光材料的最低三线态能级低于所述化合物的最低三线态能级。
4.一种显示面板,其特征在于,包括权利要求2或3所述的有机发光器件。
5.一种显示装置,其特征在于,包括权利要求4所述的显示面板。
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