CN114478490A - 一种有机化合物、电致发光材料及其应用 - Google Patents
一种有机化合物、电致发光材料及其应用 Download PDFInfo
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- CN114478490A CN114478490A CN202210142375.6A CN202210142375A CN114478490A CN 114478490 A CN114478490 A CN 114478490A CN 202210142375 A CN202210142375 A CN 202210142375A CN 114478490 A CN114478490 A CN 114478490A
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- substituted
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- heteroaryl
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- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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Abstract
本发明提供一种有机化合物、电致发光材料及其应用。本发明提供的有机化合物具有如下式I所示的结构。本发明通过将五元含氮杂环与含有杂原子的八元环共轭结构引入分子结构中,同时将氮原子中的孤对电子共轭到苯环上,可以使有机化合物的电荷传输更加平衡,有利于进一步提高化合物的稳定性,同时空穴传输效果明显加强;本发明提供的有机化合物作为发光层的主体材料,通过与合适的其他功能材料搭配制备有机发光器件,可有效地改善器件中载流子传输效率,器件可获得更高的效率和更长的寿命。
Description
技术领域
本发明属于有机电致发光材料技术领域,具体涉及一种有机化合物、电致发光材料及其应用。
背景技术
目前有机电致发光器件发光层通常由主体材料/掺杂剂的混合体系组成,这样有利于改进发光器件的色彩纯度,提高其发光效率以及器件稳定性。
通常来说,在主体材料/掺杂剂体系中,主体材料的选择至关重要,因为主体材料对发光器件的效率和寿命有重要的影响。性能优异的主体材料应具有合适的分子量、较高的玻璃化转变温度和热分解温度、高的电化学稳定性及与相邻功能层材料有良好的界面接触。对于红光主体材料,要求材料有良好的载流子传输能力,具有合适的三线态能级,确保在发光过程中能量可以有效地由主体材料转移到的客体材料,从而实现较高的器件效率。
目前报道的红光主体材料通常为分子中含有大共轭体系的芳香环,存在所制备器件的效率偏低和寿命偏低的问题。目前报道的器件存在效率偏低、稳定性欠佳的问题,原因是分子结构中较大的共轭体系所带来的三线态能级较低,不能有效地将激子能量由主体传递给客体,同时主体材料载流子传输的不平衡。
因此,如何提供一种发光主体材料,使其可以提供器件的效率和寿命,成为目前亟待解决的问题。
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、电致发光材料及其应用。本发明提供的有机化物,通过将五元含氮杂环与含有杂原子的八元环共轭结构引入分子结构中,同时将氮原子中的孤对电子共轭到苯环上,可以使材料的电荷传输更加平衡,有利于进一步提高材料的稳定性。本发明提供的有机化合物可作为发光层的主体材料,通过与合适的其他功能材料搭配制备有机发光器件,器件可获得更高的效率和更长的寿命。
为达到此发明目的,本发明采用以下技术方案:
第一方面,本发明提供一种有机化合物,所述有机化合物具有如下式I所示的结构:
其中,A、B、C、D各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基;
L选自单键、取代或未取代的C6-C30亚芳基、取代或未取代的C2-C30亚杂芳基、取代或未取代的C3-C30环烷基中的任意一种。
在本发明中,C6-C30各自独立地可以为C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20、C21、C22、C23、C24、C25、C26、C27、C28、C29、C30等。
在本发明中,C3-C30各自独立地可以为C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20、C21、C22、C23、C24、C25、C26、C27、C28、C29、C30等。
在本发明中,C2-C30各自独立地可以为C2、C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20、C21、C22、C23、C24、C25、C26、C27、C28、C29、C30等。
在本发明中,五元含氮杂环与八元环大共轭体系共环形成的结构通常具有较好的稳定性,同时空穴传输效果会明显加强,这与五元含氮杂环的电子结构分布有关,N原子孤对电子参与大共轭体系的构建,使得传输更匹配。通过引入八元环并含氮杂环到分子的共轭体系中,可提高材料分子的稳定性,同时以此作为发光层的主体材料进行制备有机发光器件,可有效地改善器件中载流子传输效率,进而提高发光器件的效率和寿命。
第二方面,本发明提供一种发光层,所述发光层包括如第一方面所述的有机化合物。
第三方面,本发明提供一种显示面板,所述显示面板包括第一电极和第二电极,所述第一电极和第二电极之间设置包括发光层的叠层,所述发光层包括如第二方面所述的发光层。
在本发明中,有机化合物分子结构中采用较大的八元环共轭芳香体系连接氮杂吸电子结构单元,可以显著提升器件效率,当与合适的p型材料搭配组合,可以使载流子传输平衡得到进一步的改善,从而解决有机发光器件的效率和寿命问题。
第四方面,本发明提供一种电子设备,所述电子设备包括如第三方面所述的显示面板。
相对于现有技术,本发明具有以下有益效果:
(1)本发明通过将五元含氮杂环与含有杂原子的八元环共轭结构引入分子结构中,同时将氮原子中的孤对电子共轭到苯环上,可以使有机化合物的电荷传输更加平衡,有利于进一步提高化合物的稳定性,同时空穴传输效果明显加强;
(2)本发明提供的有机化合物作为发光层的主体材料,通过与合适的其他功能材料搭配制备有机发光器件,可有效地改善器件中载流子传输效率,器件可获得更高的效率和更长的寿命。
附图说明
图1为本发明提供的OLED器件的结构示意图;
其中,110为玻璃基板、120为阳极、130为空穴注入层、140为空穴传输层A、150为空穴传输层B;160为发光层、170为电子传输层、180为阴极。
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。
第一方面,本发明提供一种有机化合物,所述有机化合物具有如下式I所示的结构:
其中,A、B、C、D各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基;
L选自单键、取代或未取代的C6-C30亚芳基、取代或未取代的C2-C30亚杂芳基、取代或未取代的C3-C30环烷基中的任意一种。
在本发明中,C6-C30各自独立地可以为C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20、C21、C22、C23、C24、C25、C26、C27、C28、C29、C30等。
在本发明中,C3-C30各自独立地可以为C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20、C21、C22、C23、C24、C25、C26、C27、C28、C29、C30等。
在本发明中,C2-C30各自独立地可以为C2、C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20、C21、C22、C23、C24、C25、C26、C27、C28、C29、C30等。
在本发明中,五元含氮杂环与八元环大共轭体系共环形成的结构通常具有较好的稳定性,同时空穴传输效果会明显加强,这与五元含氮杂环的电子结构分布有关,N原子孤对电子参与大共轭体系的构建,使得传输更匹配。通过引入八元环并含氮杂环到分子的共轭体系中,可提高材料分子的稳定性,同时以此作为发光层的主体材料进行制备有机发光器件,可有效地改善器件中载流子传输效率,进而提高发光器件的效率和寿命。
在本发明中,所述取代的芳基、取代的芳杂基、取代的亚芳基、取代的杂亚芳基、取代的环烷基中的取代基各自独立地选自氘、卤素、氰基、C1-C10(例如可以是C1、C2、C3、C4、C5、C6、C7、C8、C9、C10等)直链或支链烷基、C1-C10(例如可以是C1、C2、C3、C4、C5、C6、C7、C8、C9、C10等)烷氧基、C1-C10(例如可以是C1、C2、C3、C4、C5、C6、C7、C8、C9、C10等)烷硫基、C6-C20(例如可以是C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等)芳基、C2-C20(例如可以是C2、C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等)杂芳基或C6-C18(例如可以是C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18等)芳胺基中的任意一种。
在本发明中,所述芳基选自苯基、联苯基、三联苯基、萘基、蒽基、菲基、9,9'-二甲基芴基、9,9'-二苯基芴基或螺二芴基中的任意一种。
在本发明中,所述杂芳基选自咔唑基、三嗪基、吡啶基、嘧啶基、咪唑基、噁唑基、噻唑基、吡喃基、噻唑基、苯并咪唑基、苯并噁唑基、苯并噻唑基、二苯并噻吩基、二苯并呋喃基、萘并咪唑基、萘并噁唑基、萘并噻唑基、菲并咪唑基、菲并噁唑基、菲并噻唑基、喹喔啉基、喹唑啉基、吲哚并咔唑基、吲哚并芴基、苯并噻吩并吡嗪基、苯并噻吩并嘧啶基、苯并呋喃并吡嗪基、苯并呋喃并嘧啶基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、吲哚并吡嗪基、吲哚并嘧啶基、茚并吡嗪基或茚并嘧啶基中的任意一种。
在本发明中,所述A、B、C各自独立地选自未取代或Ry1取代的苯基、未取代或Ry1取代的吡咯基、未取代或Ry1取代的呋喃基;未取代或Ry1取代的噻吩基;
所述Ry1选自C6-C20(例如可以是C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等)芳基或C2-C20(例如可以是C2、C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等)杂芳基中的任意一种。
在本发明中,所述L选自单键、亚苯基、亚联苯基、亚萘基或C3-C12(例如可以是C3、C4、C5、C6、C7、C8、C9、C10、C11、C12等)含氮亚杂芳基中的任意一种。
在本发明中,所述D选自未取代或Ry2取代的C3-C20(例如可以是C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等)杂芳基;
所述Ry2选自C6-C20(例如可以是C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等)芳基或C2-C20(例如可以是C2、C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等)杂芳基中的任意一种。
在本发明中,所述D选自以下结构中的任意一种:
其中,虚线表示基团的连接位置;
Rt1选自C6-C20芳基(例如可以是C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等)、C2-C20(例如可以是C2、C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等)杂芳基中的任意一种。
在本发明中,所述D选自以下结构中的任意一种:
其中,虚线表示基团的连接位点。
在本发明中,所述有机化合物包括如下M1-M40中的任意一种:
第二方面,本发明提供一种发光层,所述发光层包括如第一方面所述的有机化合物。
第三方面,本发明提供一种显示面板,所述显示面板包括第一电极和第二电极,所述第一电极和第二电极之间设置包括发光层的叠层,所述发光层包括如第二方面所述的发光层。
在本发明中,有机化合物分子结构中采用较大的八元环共轭芳香体系连接氮杂吸电子结构单元,可以显著提升器件效率,当与合适的p型材料搭配组合,可以使载流子传输平衡得到进一步的改善,从而解决有机发光器件的效率和寿命问题。
在本发明中,所述叠层还包括空穴注入层、空穴传输层、电子传输层和电子注入层中的任意一种或至少两种的组合。
第四方面,本发明提供一种电子设备,所述电子设备包括如第三方面所述的显示面板。
实施例1
本实施例提供一种有机化合物M1,结构式如下所示:
该有机化合物M1的制备方法包括以下步骤:
(1)化合物1-2的制备
在氮气气氛下,将原料1-1(20g,60mmol)、1,8-二溴萘(17.1g,60mmol)、四三苯基膦钯(0.5g)、碳酸钾(2.5g)和X-Phos(0.5g)依次加入到1000mL三口烧瓶中,然后将500mLTHF和50mL H2O加入烧瓶并抽真空,氮气置换三次,加热至90℃反应8h,旋转蒸发除去溶剂,用二氯甲烷和去离子水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂石油醚),得到17.9g化合物1-2,产率72.6%。
(2)化合物1-4的制备
在氮气气氛下,将化合物1-2(15g,36.4mmol)、1-3(11.9g,36.4mmol)、四三苯基膦钯(0.46g)、碳酸钾(2.5g)和X-Phos(0.46g)依次加入到1000mL三口烧瓶中,然后将500mLTHF和50mL H2O注入烧瓶并抽真空氮气置换三次,加热至90℃反应8h,结束反应后将反应混合液倒入500mL去离子水中并快速搅拌,期间不断有产物析出,布氏漏斗抽滤,将滤饼用二氯甲烷溶解并用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂V二氯甲烷:V石油醚=1:20),得到16.5g化合物1-4,产率85.2%。
(3)化合物1-5的制备
在氮气气氛下,将化合物1-4(15g)、双三环己基膦二氯化钯(0.6g)和碳酸铯(22g)依次加入到500mL三口烧瓶中,然后将200mL干燥的二甲基乙酰胺和10mL特戊酸注入烧瓶并抽真空氮气置换三次,加热至170℃回流反应4h,结束反应后将反应混合液倒入500mL去离子水中并快速搅拌,期间不断有产物析出,布氏漏斗抽滤,将滤饼用二氯甲烷溶解并用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂二氯甲烷:石油醚=1:20),得到7.4g化合物1-5,产率70.3%。
(4)化合物1-6的制备
在氮气气氛下,将化合物1-5(7g)和三乙基膦(6g)依次加入到500mL三口烧瓶中,然后将200mL干燥的二甲基甲酰胺注入烧瓶并抽真空,氮气置换三次,加热至160℃回流反应5h,结束反应后将反应混合液倒入500mL去离子水中并快速搅拌,期间不断有产物析出,布氏漏斗抽滤,将滤饼用二氯甲烷溶解并用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂二氯甲烷:石油醚=1:20),得到6.5g化合物1-6,产率90.3%。
(5)化合物M1的制备
在氮气气氛下,将化合物1-6(6g)、原料1-7(6.2g)、三氟醋酸钯(0.35g)和碳酸铯(12g)依次加入到500mL三口烧瓶中,然后将200mL干燥的甲苯注入烧瓶并抽真空,氮气置换三次,加热至110℃回流反应12h,结束反应后将反应混合液倒入500mL去离子水中并快速搅拌,期间不断有产物析出,布氏漏斗抽滤,将滤饼用二氯甲烷溶解并用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂V二氯甲烷:V石油醚=1:20),得到6.1g化合物M1(固体粉末),产率59.6%。
MS[M+H]+calcd for C47H29N4:649.78,found:649.23.
实施例2
本实施例提供一种有机化合物M2,结构式如下所示:
该有机化合物M2的制备方法包括以下步骤:
(1)化合物2-3的制备
在氮气气氛下,将原料2-1(20g)、原料2-2(16.9g)、四三苯基膦钯(0.5g)、碳酸钾(2.5g)和X-Phos(0.5g)依次加入到1000mL三口烧瓶中,然后将500mL THF和50mL H2O注入烧瓶并抽真空,氮气置换三次,加热至90℃反应8h,旋转蒸发除去溶剂用二氯甲烷和去离子水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂石油醚),得到18.6g化合物2-3,产率70.3%。
(2)化合物2-4的制备
在氮气气氛下,将化合物2-3(15g)、双三环己基膦二氯化钯(0.6g)和碳酸铯(22g)依次加入到500mL三口烧瓶中,然后将200mL干燥的二甲基乙酰胺和10mL特戊酸注入烧瓶并抽真空,氮气置换三次,加热至170℃回流反应4h,结束反应后将反应混合液倒入500mL去离子水中并快速搅拌,期间不断有产物析出,布氏漏斗抽滤,将滤饼用二氯甲烷溶解并用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂V二氯甲烷:V石油醚=1:20),得到8.6g化合物2-4,产率67.8%。
(3)化合物2-5的制备
在氮气气氛下,将化合物2-4(8g)和三乙基膦(6g)依次加入到500mL三口烧瓶中,然后将200mL干燥的二甲基甲酰胺注入烧瓶并抽真空,氮气置换三次,加热至160℃回流反应5h,结束反应后将反应混合液倒入500mL去离子水中并快速搅拌,期间不断有产物析出,布氏漏斗抽滤,将滤饼用二氯甲烷溶解并用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂V二氯甲烷:V石油醚=1:20),得到6.8g化合物2-5,产率92.5%。
(4)化合物M2的制备
在氮气气氛下,将化合物2-5(6g)、原料2-6(5.7g)、三氟醋酸钯(0.35g)和碳酸铯(12g)依次加入到500mL三口烧瓶中,然后将200mL干燥的甲苯注入烧瓶并抽真空,氮气置换三次,加热至110℃回流反应12h,结束反应后将反应混合液倒入500mL去离子水中,并快速搅拌,期间不断有产物析出,布氏漏斗抽滤,将滤饼用二氯甲烷溶解并用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂V二氯甲烷:V石油醚=1:20),得到6.5g化合物M2(固体粉末),产率61.6%。
MS[M+H]+calcd for C51H32N5:714.85,found:714.26.
实施例3
本实施例提供一种有机化合物M3,结构式如下所示:
(1)化合物3-3的制备
在氮气气氛下,将原料3-1(20g)、3-2(14.4g)、四三苯基膦钯(0.5g)、碳酸钾(2.5g)和X-Phos(0.5g)依次加入到1000mL三口烧瓶中,然后将500mL THF和50mL H2O注入烧瓶并抽真空,氮气置换三次,加热至90℃反应8h,旋转蒸发除去溶剂,并用二氯甲烷和去离子水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂石油醚),得到20.1g化合物3-3,产率78.8%。
(2)化合物3-4的制备
在氮气气氛下,将化合物3-3(18g)、双三环己基膦二氯化钯(0.6g)和碳酸铯(22g)依次加入到500mL三口烧瓶中,然后将200mL干燥的二甲基乙酰胺和10mL特戊酸注入烧瓶并抽真空,氮气置换三次,加热至170℃回流反应4h,结束反应后将反应混合液倒入500mL去离子水中并快速搅拌,期间不断有产物析出,抽滤后再次用二氯甲烷将产物溶解,用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂V二氯甲烷:V石油醚=1:20),得到10.4g化合物3-4,产率67.2%。
(3)化合物3-5的制备
在氮气气氛下,将化合物3-4(10g)和三乙基膦(6g)依次加入到500mL三口烧瓶中,然后将200mL干燥的二甲基甲酰胺注入烧瓶并抽真空,氮气置换三次,加热至160℃回流反应5h,结束反应后将反应混合液倒入500mL去离子水中并快速搅拌,期间不断有产物析出,抽滤后再次用二氯甲烷将产物溶解,并用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂V二氯甲烷:V石油醚=1:20),得到8.7g化合物3-5,产率92.6%。
(4)化合物M3的制备
在氮气气氛下,将化合物3-5(8g)、原料3-6(6.5g)、三氟醋酸钯(0.35g)和碳酸铯(12g)依次加入到500mL三口烧瓶中,然后将200mL干燥的甲苯注入烧瓶并抽真空,氮气置换三次,加热至110℃回流反应12h,结束反应后将反应混合液倒入500mL去离子水中并快速搅拌,期间不断有产物析出,抽滤后再次用二氯甲烷将产物溶解,用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂V二氯甲烷:V石油醚=1:20),得到8.5g化合物M3(固体粉末),产率64.3%。
MS[M+H]+calcd for C55H36N5:782.93,found:782.28.
对比例1
本对比例提供一种有机化合物N1,结构式如下所示:
(1)化合物4-3的制备
氮气保护下,将化合物4-1(20.2g,50mmol)、化合物4-2(17.2g,100mmol)、四(三苯基磷)钯(3.5g,3mmol)、四丁基溴化铵(8.1g,25mmol)和氢氧化钠(4g,100mmol)依次加入到500mL的三口瓶中,再将200mL甲苯和50mL去离子水加入,抽真空,氮气置换三次后,加热110℃搅拌反应24h;结束反应,将反应液旋转蒸发掉大部分溶剂,用二氯甲烷溶解水洗三次,合并有机相经硅胶柱层析分离纯化(淋洗剂石油醚),得到18.7g化合物4-3,产率75%。
(2)化合物4-4的制备
将化合物4-3(14.9g,30mmol)和100mL N,N-二甲基甲酰胺加入250mL单口瓶中,冰浴下滴加30mmol NBS的N,N-二甲基甲酰胺溶液,避光搅拌反应12h,结束反应,将反应液倒入到300mL水中,抽滤,滤渣重结晶,得到17.3g化合物4-4,产率90%。
(3)化合物N1的合成
在氮气保护下,将化合物4-4(34.4g,20mmol)、化合物4-5(11.5g,20mmol)、四(三苯基磷)钯(0.7g,0.6mmol)、四丁基溴化铵(3.2g,10mmol)和氢氧化钠(1.6g,40mmol)依次加入到500mL三口烧瓶中,然后将200mL甲苯和50mL去离子水注入烧瓶并抽真空,氮气置换三次,加热至110℃回流反应12h,结束反应后旋转蒸发除去溶剂,然后用二氯甲烷将产物溶解,用饱和食盐水萃取三次,合并有机相经硅胶柱层析分离纯化(淋洗剂V二氯甲烷:V石油醚=1:10),得到18.7g对比化合物N1(固体粉末),产率85%。
MS[M+H]+calcd for C48H34N:624.81,found:624.26.
应用例1
本应用例提供一种OLED器件ITO/HI/HI-1/HT-2/EML/ET:Liq/Al,如图1所示,有机发光器件包括玻璃基板110、阳极120、空穴注入层130、空穴传输层A 140、空穴传输层B150、发光层160、电子传输层170和阴极180;
OLED器件的制备步骤如下:
(1)将玻璃基板110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30min,然后在臭氧下暴露约10min来进行清洁;将所得的具有ITO阳极120的玻璃基板安装到真空沉积设备上;
(2)在ITO阳极120上真空蒸镀化合物HI,厚度30nm,作为空穴注入层130;
(3)在空穴注入层130上真空蒸镀化合物HT-1,厚度60nm,作为空穴传输层A 140;
(4)在空穴传输层A 140上真空蒸镀化合物HT-2,厚度10nm,作为空穴传输层B150;
(5)在空穴传输层B 150上真空蒸镀重量比为100:3的化合物M1(实施例1提供)和红光客体材料RD,厚度40nm,作为发光层160;
(6)在发光层160上真空蒸镀重量比为50:50的化合物ET和Liq,厚度30nm,作为电子传输层170;
(6)在电子传输层170上真空蒸镀铝电极,厚度100nm,作为阴极180。
上述的化合物HI、HT-1、HT-2、红光客体材料RD、ET和Liq的结构如下所示:
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(5)中的有机化合物M1替换为同等质量的实施例2提供的有机化合物M2;其它制备步骤均相同。
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,将步骤(5)中的有机化合物M1替换为同等质量的实施例3提供的有机化合物M3;其它制备步骤均相同。
对比应用例1
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(5)中的有机化合物M1替换为同等质量的对比例1提供的化合物N1;其它制备步骤均相同。
测试例1
化合物的模拟计算
模拟计算方法: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HOMC和LUMO的分布情况和能级,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最低单线态能级ES1和最低三线态能级ET1,结果如表1和表2所示:
表1
表2
有机化合物 | E<sub>S1</sub>(eV) | E<sub>T1</sub>(eV) |
M1 | 2.67 | 2.19 |
M2 | 2.25 | 2.20 |
M3 | 2.37 | 2.18 |
N1 | 3.04 | 2.37 |
由表1和表2数据可知,与化合物N1相比,本发明提供的有机化合物通过引入五元含氮杂环与八元环共轭体系,使得有机化合物具有合适的HOMO/LUMO能级,有利于相邻层化合物的能级匹配,也能覆盖客体的能级。
测试例2
OLED器件的性能评价
测试方法:
寿命测试方法,初始在1000nits对应的恒定电流密度下,器件的发光亮度下降到其初始亮度95%时的器件连续工作时间。
电流效率测试方法:采用I-V-L测试设备,测得亮度为1000nits下对应的电流密度,计算得到电流效率。
测试结果如表3所示。
表3
通过与对比应用例1的对比可知,本发明(应用例1-3)提供的OLED器件具有更高的效率和更长的寿命。本发明通过将五元含氮杂环与含有杂原子的八元环共轭结构引入分子结构中,同时将氮原子中的孤对电子共轭到苯环上,可以使有机化合物的电荷传输更加平衡,有利于进一步提高化合物的稳定性;这是因为五元含氮杂环与八元环大共轭体系共环形成的结构通常具有较好的稳定性,同时空穴传输效果会明显加强,这与五元含氮杂环的电子结构分布有关,N原子孤对电子参与大共轭体系的构建,使得传输更匹配。
本发明提供的有机化合物作为发光层的主体材料,通过与合适的其他功能材料搭配制备有机发光器件,可有效地改善器件中载流子传输效率,器件可获得更高的效率和更长的寿命。
申请人声明,本发明通过上述实施例来说明本发明的工艺方法,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 (14)
2.根据权利要求1所述的有机化合物,其特征在于,所述取代的芳基、取代的芳杂基、取代的亚芳基、取代的杂亚芳基、取代的环烷基中的取代基各自独立地选自氘、卤素、氰基、C1-C10直链或支链烷基、C1-C10烷氧基、C1-C10烷硫基、C6-C20芳基、C2-C20杂芳基或C6-C18芳胺基中的任意一种。
3.根据权利要求1或2所述的有机化合物,其特征在于,所述芳基选自苯基、联苯基、三联苯基、萘基、蒽基、菲基、9,9'-二甲基芴基、9,9'-二苯基芴基或螺二芴基中的任意一种。
4.根据权利要求1或2所述的有机化合物,所述杂芳基选自咔唑基、三嗪基、吡啶基、嘧啶基、咪唑基、噁唑基、噻唑基、吡喃基、噻唑基、苯并咪唑基、苯并噁唑基、苯并噻唑基、二苯并噻吩基、二苯并呋喃基、萘并咪唑基、萘并噁唑基、萘并噻唑基、菲并咪唑基、菲并噁唑基、菲并噻唑基、喹喔啉基、喹唑啉基、吲哚并咔唑基、吲哚并芴基、苯并噻吩并吡嗪基、苯并噻吩并嘧啶基、苯并呋喃并吡嗪基、苯并呋喃并嘧啶基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、吲哚并吡嗪基、吲哚并嘧啶基、茚并吡嗪基或茚并嘧啶基中的任意一种。
5.根据权利要求1或2所述的有机化合物,其特征在于,所述A、B、C各自独立地选自未取代或Ry1取代的苯基、未取代或Ry1取代的吡咯基、未取代或Ry1取代的呋喃基;未取代或Ry1取代的噻吩基;
所述Ry1选自C6-C20芳基或C2-C20杂芳基中的任意一种。
6.根据权利要求1或2所述的有机化合物,其特征在于,所述L选自单键、亚苯基、亚联苯基、亚萘基或C3-C12含氮亚杂芳基中的任意一种。
7.根据权利要求1或2所述的有机化合物,其特征在于,所述D选自未取代或Ry2取代的C3-C20杂芳基;
所述Ry2选自C6-C20芳基或C2-C20杂芳基中的任意一种。
11.一种发光层,其特征在于,所述发光层包括如权利要求1-10任一项所述的有机化合物。
12.一种显示面板,其特征在于,所述显示面板包括第一电极和第二电极,所述第一电极和第二电极之间设置包括发光层的叠层,所述发光层包括如权利要求10所述的发光层。
13.根据权利要求11所述的显示面板,其特征在于,所述叠层还包括空穴注入层、空穴传输层、电子传输层和电子注入层中的任意一种或至少两种的组合。
14.一种电子设备,其特征在于,所述电子设备包括如权利要求11或12所述的显示面板。
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