CN111662312B - 一种化合物、热激活延迟荧光材料及其应用 - Google Patents
一种化合物、热激活延迟荧光材料及其应用 Download PDFInfo
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- CN111662312B CN111662312B CN202010515099.4A CN202010515099A CN111662312B CN 111662312 B CN111662312 B CN 111662312B CN 202010515099 A CN202010515099 A CN 202010515099A CN 111662312 B CN111662312 B CN 111662312B
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- Electroluminescent Light Sources (AREA)
Abstract
本发明提供了一种化合物、热激活延迟荧光材料及其应用,尤其涉及一种化合物、热激活延迟荧光材料、显示面板以及电子设备,所述化合物具有式I的结构;热激活延迟荧光材料包括化合物中的任意一种或至少两种的组合;显示面板包括OLED器件,所述OLED器件包括阳极、阴极、以及位于阳极和阴极之间的至少一层有机层,所述有机层包括发光层,所述发光层包括热激活延迟荧光材料;电子设备包括显示面板;化合物的最低单重态S1与最低三重态T1态之间的能极差ΔEst=ES1‑ET1≤0.30eV,具备热激活延迟荧光材料发光机制,可以用于有机光电装置领域,降低驱动电压,提高发光效率和寿命,使包含其的电子设备具有更优异的性能。
Description
技术领域
本发明属于有机器件领域,涉及一种化合物、热激活延迟荧光材料及其应用,尤其涉及一种化合物、热激活延迟荧光材料、显示面板以及电子设备。
背景技术
近年来,基于有机材料的光电子器件已经变得越来越受欢迎。有机材料固有的柔性令其十分适合用于在柔性基板上制造,可根据需求设计、生产出美观而炫酷的光电子产品,获得相对于无机材料无以比拟的优势。此类有机光电子器件的示例包括有机发光二极管(OLED),有机场效应管,有机光伏打电池,有机传感器等。其中OLED发展尤其迅速,已经在信息显示领域取得商业上的成功。OLED可以提供高饱和度的红、绿、蓝三颜色,用其制成的全色显示装置无需额外的背光源,具有色彩炫丽,轻薄柔软等优点。
OLED器件核心为含有多种有机功能材料的薄膜结构。常见的功能化有机材料有:空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料,电子阻挡材料以及发光主体材料和发光客体(染料)等。通电时,电子和空穴被分别注入、传输到发光区域并在此复合,从而产生激子并发光。
人们已经开发出多种有机材料,结合各种奇特的器件结构,可以提升载流子迁移率、调控载流子平衡、突破电致发光效率、延缓器件衰减。出于量子力学的原因,常见的荧光发光体主要利用电子和空血结合时产生的单线态激子发光,现在仍然广泛地应用于各种OLED产品中。有些金属络合物如铱络合物,可以同时利用三线态激子和单线态激子进行发光,被称为磷光发光体,其能量转换效率可以比传统的荧光发光体提升高达四倍。热激发延迟荧光(TADF)技术通过促进三线态激子朝单线态激子的转变,在不采用金属配合物的情况下,仍然可以有效地利用三线态激子而实现较高的发光效率。热激发敏化荧光(TASF)技术则采用具TADF性质的材料,通过能量转移的方式来敏化发光体,同样可以实现较高的发光效率。但目前已发现的TADF材料较少,性能也有待提高,新型的可用于OLED器件的TADF材料亟待开发。
因此,更多种类、更高性能的TADF材料亟待开发,使包含其的器件具有更高的发光效率。
发明内容
为了开发更多种类、更高性能的TADF材料,以及更高的发光效率的器件,本发明的目的之一在于提供一种化合物,具有化学式I所示的结构:
式I中,R1和R2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、取代或未取代的C6-C30芳基氨基中的任意一种,且R1和R2均为供电子基;
式I中,R3和R4各自独立地选自取代或未取代的C3-C30吸电子氮杂芳基、取代或未取代的C6-C30含氰基芳基、取代或未取代的C3-C30含氰基杂芳基、取代或未取代的C6-C30含氟芳基、取代或未取代的C3-C30含氟杂芳基中的任意一种;
式I中,Ra、Rb和Rc各自独立地选自羰基、氰基、酰胺基、磷氧基、取代或未取代的C1-C20烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C2-C20烯基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种;
式I中,m、n和p各自独立地选自0-2的整数;
R1、R2、R3、R4、Ra、Rb和Rc中,所述取代的基团选自卤素、羰基、氰基、酰胺基、磷氧基、C1-C12的链状烷基、C3-C12的环烷基、C1-C6的烷氧基或硫代烷氧基、C2-C20烯基C6-C30芳基氨基、C3-C30杂芳基氨基、C6-C30的单环芳烃或稠环芳烃基团、C3-C30的单环杂芳烃或稠环杂芳烃基团中的任意一种。
本发明的目的之二在于提供一种热激活延迟荧光材料,所述热激活延迟荧光材料包括目的之一所述的化合物中的任意一种或至少两种的组合。
本发明的目的之三在于提供一种显示面板,所述显示面板包括OLED器件,所述OLED器件包括阳极、阴极、以及位于阳极和阴极之间的至少一层有机层,所述有机层包括发光层,所述发光层包括目的之二所述的热激活延迟荧光材料,且所述热激活延迟荧光材料用作主体材料、掺杂材料或共同掺杂材料中的任意一种。
本发明的目的之四在于提供一种电子设备,所述电子设备包括目的之三所述的显示面板。
相对于现有技术,本发明具有以下有益效果:
本发明提供的化合物基于分子结构的设计通过化学键形成D-A电荷转移作用,而且利用电子给体和电子受体的空间距离设计形成空间电荷转移作用,使HOMO和LUMO在分子内可以形成有效分离,降低△EST,使能级差ΔEST=ES1-ET1≤0.30eV,实现高效的反向系间窜跃的物理过程,使所述化合物具有典型的TADF特性;本发明提供的化合物可以在一个分子中存在两个D-A发光子单元,具有双重发射核的性质,有效提升了振子强度,提高发光效率;同时,所述化合物的双极性特性有利于传输电子和空穴。因此,本发明提供的化合物高度适于作为OLED器件发光层材料,拓宽发光层,提升OLED器件的发光效率和工作寿命。
附图说明
图1是本发明的一个具体实施方式中提供的OLED显示面板的示意图;
图2为本发明的一个具体实施方式中化合物M3的HOMO分布示意图;
图3为本发明的一个具体实施方式中化合物M3的LUMO分布示意图;
图4是本发明的一个具体实施方式中提供的电子设备的示意图。
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化合物,具有化学式I所示的结构:
式I中,R1和R2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、取代或未取代的C6-C30芳基氨基中的任意一种,且R1和R2均为供电子基,其中供电子基是指能够提高苯环上电子云密度的基团;
式I中,R3和R4各自独立地选自取代或未取代的C3-C30氮杂芳基、取代或未取代的C6-C30含氰基芳基、取代或未取代的C3-C30含氰基杂芳基、取代或未取代的C6-C30含氟芳基、取代或未取代的C3-C30含氟杂芳基中的任意一种,且R1和R2均为吸电子基,其中吸电子基是指能够降低苯环上电子云密度的基团;
式I中,Ra、Rb和Rc各自独立地选自羰基、氰基、酰胺基、磷氧基、取代或未取代的C1-C20烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C2-C20烯基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种;
式I中,m、n和p各自独立地选自0-2的整数(例如0、1或2);
R1、R2、R3、R4、Ra、Rb和Rc中,所述取代的基团选自卤素、羰基、氰基、酰胺基、磷氧基、C1-C12的链状烷基、C3-C12的环烷基、C1-C6的烷氧基或硫代烷氧基、C2-C20烯基C6-C30芳基氨基、C3-C30杂芳基氨基、C6-C30的单环芳烃或稠环芳烃基团、C3-C30的单环杂芳烃或稠环杂芳烃基团中的任意一种。
式I中的采用R1、R2、R3、R4、Ra、Rb和Rc的方式来表示取代基,意义在于,R1、R2、R3、R4、Ra、Rb和Rc代表基团的选择范围,而并非代表一个具体的基团,当Ra、Rb或Rc的个数大于等于两个时,取代基可以相同也可以不同,示例性的,当母体基团上取代有两个Ra基团时,两个Ra基团可以是相同的,也可以是不同的。
C1-C20包括C1、C2、C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等。
C2-C20包括C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20等。
C3-C30包括C4、C6、C8、C10、C12、C14、C16、C18、C20、C22、C24、C26、C28等。
C6-C30包括C6、C8、C10、C12、C14、C16、C18、C20、C22、C24、C26、C28等。
C1-C6包括C2、C3、C4、C5等。
C1-C12包括C2、C3、C4、C5、C6、C7、C8、C9、C10、C11等。
C2-C12包括C3、C4、C5、C6、C7、C8、C9、C10、C11等。
C3-C12包括C4、C5、C6、C7、C8、C9、C10、C11等。
本发明提供的化合物以硼杂环结构为母体,并配合特定种类的吸电子基和供电子基,使R1-N-B-R3和R2-N-B-R4可以通过化学键形成D-A电荷转移作用,实现了HOMO和LUMO在分子内的有效分离,降低△EST,实现高效的反向系间窜跃的物理过程,使化合物具有典型的TADF特性。
本发明提供的具有式I结构的化合物中,同一个分子中存在两个D-A发光子单元,具有双重发射核的性质,可以有效地提升振子强度、提高发光效率,而且所述化合物具有双极性的特性,可以有效地传输电子和空穴,适于用作OLED器件发光层掺杂材料,提升OLED器件的发光效率和工作寿命。
本发明中化合物在制备过程中,避免过多官能团取代的引入,增加了分子电化学环境中的不稳定因素,影响器件的使用寿命,且分子量较大的化合物不易蒸镀,因此,在不影响化合物发光效率的前提下,尽量设计为结构简单的化合物。
在一个实施方式中,所述m、n和p各自独立地选自0或1。
在一个实施方式中,所述m和n均为1,p为0。
在本发明中,优选m和n均为1,p为0,可以避免过多官能团取代的引入,增加了分子电化学环境中的不稳定因素,影响器件的使用寿命,且分子量较大的化合物不易蒸镀,因此,在不影响化合物发光效率的前提下,尽量设计为结构简单的化合物。
在一个实施方式中,所述Ra、Rb和Rc各自独立地选自甲基、苯基、二联苯基、三联苯基、萘基、芴基或咔唑基中的任意一种。
在一个实施方式中,所述化合物具有式II所示的结构:
其中,R1、R2、R3和R4具有与上述相同的限定范围。
在本发明中,化合物选自式II所示的结构,能够提高分子的稳定性,通过空间位阻效应,扭曲分子结构,使分子HOMO、LUMO有效分离,降低△EST,实现高效的反向系间窜跃的物理过程,使化合物具有典型的TADF特性。
在一个实施方式中,所述化合物具有式III所示的结构:
其中,R1、R2、R3和R4具有与上述相同的限定范围。
在一个实施方式中,所述R1和R2各自独立地选自取代或未取代的如下基团中的任意一种:
其中,虚线表示基团的连接位点。
在一个实施方式中,R1和R2各自独立地选自如下基团中的任意一种:
在一个实施方式中,所述R1和R2相同。
在一个实施方式中,所述R3和R4各自独立地选自取代或未取代的噁二唑、取代或未取代的咪唑、取代或未取代的噁唑、取代或未取代的***、取代或未取代的喹啉、取代或未取代的三嗪、取代或未取代的邻菲啰林、取代或未取代的C6-C18含氰基芳基、取代或未取代的C3-C18含氰基杂芳基、取代或未取代的C6-C18含氟芳基、取代或未取代的C3-C18含氟杂芳基中的任意一种。
在一个实施方式中,所述R3和R4各自独立地选自如下基团中的任意一种:
其中,虚线表示基团的连接位点。
在一个实施方式中,所述R3和R4相同。
在一个实施方式中,所述化合物包括如下结构M1-M40中的任意一种:
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在一个实施方式中,所述化合物的最低单重态S1与最低三重态T1态之间的能极差ΔEst=ES1-ET1≤0.3eV,例如0.30eV、0.29eV、0.28eV、0.27eV、0.26eV、0.25eV、0.24eV、0.23eV、0.22eV、0.21eV、0.20eV、0.19eV、0.18eV、0.16eV、0.14eV、0.13eV、0.12eV、0.11eV、0.10eV、0.09eV、0.08eV、0.07eV、0.06eV、0.05eV、0.04eV、0.03eV、0.02eV、0.01eV等。
本发明的目的之二在于提供一种热激活延迟荧光材料,所述热激活延迟荧光材料包括目的之一所述的化合物中的任意一种或至少两种的组合。
本发明提供的化合物作为热激活延迟荧光材料时,ΔEst≤0.30eV,使得反向系间穿越更容易发生,寿命长的三线态激子很容易上转换成单线态激子,单线态激子以光的形式辐射衰减至基态S0,导致高的光致量子产率PLQY,可以有效降低滚降效应,使得器件具有良好的发光性能,可以作为有机光电装置中发光层的掺杂材料、共同掺杂材料或主体材料。
本发明的目的之三在于提供一种显示面板,所述显示面板包括OLED器件,所述OLED器件包括阳极、阴极、以及位于阳极和阴极之间的至少一层有机层,所述有机层包括发光层,所述发光层包括目的之二所述的热激活延迟荧光材料,且所述热激活延迟荧光材料用作主体材料、掺杂材料或共同掺杂材料中的任意一种。
在本发明中,发光层材料包括主体材料和客体材料,客体材料包括掺杂材料,当发光层的主体材料选用上述的化合物,客体材料选用磷光材料、荧光材料或热活化延迟荧光材料中的任意一种。
在本发明中,当发光层的客体材料选用上述的化合物,主体材料选用2,8-二(二苯基氧膦基)二苯并噻吩、4,4'-二(9-咔唑)联苯、3,3'-二(N-咔唑基)-1,1'-联苯、2,8-双(二苯基膦氧基)二苯并呋喃、双(4-(9H-咔唑基-9-基)苯基)二苯硅烷、9-(4-叔丁基苯基)-3,6-双(三苯基甲硅烷基)-9h-咔唑、二(2-二苯氧化膦基)二苯醚、1,3-双[3,5-二(吡啶-3-基)苯基]苯、4,6-双(3,5-二(3-吡啶)基苯基)-2-甲基嘧啶、9-(3-(9H-咔唑基-9-基)苯基)-9H-咔唑-3-氰基、9-苯基-9-[4-(三苯基硅烷基)苯基]-9H-芴、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯、二苯基[4-(三苯基硅烷基)苯基]氧膦、4,4',4”-三(咔唑-9-基)三苯胺、2,6-二咔唑-1,5-吡啶、聚乙烯基咔唑和聚芴中的任意一种或至少两种的组合。
优选地,所述有机层还包括空穴传输层、空穴注入层、电子阻挡层、空穴阻挡层、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。
在本发明提供的OLED显示面板中,第一电极(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。第一电极材料也可以选自金属氧化物如氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO)等第一电极材料还可以选自导电性聚合物例如聚苯胺、聚吡咯、聚(3-甲基噻吩)等。此外,第一电极材料还可以选自除以上列举的第一电极材料以外的有助于空穴注入的材料及其组合,其包括已知的适合做第一电极的材料。
在本发明提供的OLED显示面板中,第二电极(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。第二电极材料也可以选自多层金属材料例如LiF/Al、LiO2/Al、BaF2/Al等。除了以上列举的第二电极材料以外,第二电极材料还可以是有助于电子注入的材料及其组合,包括已知的适合做第二电极的材料。
OLED显示面板的基底可以是刚性基板,例如硼硅酸盐玻璃、浮法钠钙玻璃、高折射率玻璃、不锈钢等,也可以是柔性基板,例如聚酰亚胺(PI)塑料衬底、聚对苯二甲酸乙二酯(PET)塑料衬底、聚萘二甲酸乙二醇酯(PEN)塑料衬底、聚醚砜树脂衬底(PES)、聚碳酸酯塑料衬底(PC)、超薄柔性玻璃衬底、金属箔片衬底等。
在本发明提供的OLED显示面板中,空穴注入材料、空穴传输材料及电子阻挡材料均各自独立地选自N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺、4,4',4”-三(咔唑-9-基)三苯胺、1,3-二咔唑-9-基苯、4,4'-二(9-咔唑)联苯、3,3'-二(N-咔唑基)-1,1'-联苯、2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺、N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺、N,N'-二(萘-2-基)-N,N'-二(苯基)联苯-4,4'-二胺、聚(3,4-乙烯二氧噻吩)-聚苯乙烯磺酸、聚乙烯咔唑、9-苯基-3,9-联咔唑、三氧化钼中的任意1种或至少2种的组合。
在本发明提供的OLED显示面板中,空穴阻挡材料、电子传输材料、电子注入材料均各自独立地选自2,8-二(二苯基氧膦基)二苯并噻吩、TSPO1、TPBi、2,8-双(二苯基膦氧基)二苯并呋喃、二(2-二苯氧化膦基)二苯醚、氟化锂、4,6-双(3,5-二(3-吡啶)基苯基)-2-甲基嘧啶、4,7-二苯基-1,10-菲啰啉、1,3,5-三[(3-吡啶基)-3-苯基]苯、三[2,4,6-三甲基-3-(3-吡啶基)苯基]硼烷、1,3-双(3,5-二吡啶-3-基苯基)苯、1,3-双[3,5-二(吡啶-3-基)苯基]苯、2,4,6-三(联苯基-3-基)-1,3,5-三嗪、二苯基二[4-(吡啶-3-基)苯基]硅烷、碳酸铯、双(2-甲基-8-羟基喹啉-N1,O8)-(1,1'-联苯-4-羟基)铝、8-羟基喹啉-锂、三(8-羟基喹啉)铝中的任意1种或至少2种的组合。
在本发明实施例中,OLED显示面板的制作过程为:在透明或不透明的光滑的基板上形成阳极(第一电极),在阳极上形成有机薄层,在有机薄层上形成阴极(第二电极)。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。
本发明的目的之四在于提供一种电子设备,所述电子设备包括目的之三所述的显示面板。
在一个实施方式中,所述电子设备可以是手机、电脑、液晶电视、智能手表、智能汽车、VR或AR头盔等。
本发明提供的具有如式I所示结构的化合物示例性的通过如下合成路线制备得到:
其中,R1、R2、R3、R4、Ra、Rb、Rc、m、n和p具有与上述相同的限定范围。
本发明提供了若干个示例性的式1结构的化合物的制备方法。在随后的制备例中,对化合物的合成进行示例性的描述。
制备例1
化合物M3的合成:
(1)在250mL三口瓶中依次加入化合物A 5.60g(20mmol)、化合物B 7.95g(20mmol)、化合物C 8.94g(20mmol)、150mL除水除氧的甲苯、碳酸铯13.81g(30mmol)、四(三苯基膦)钯0.23g(0.2mmol),然后在氮气氛围下120℃反应24小时。冷却至室温,将反应液倒入200mL冰水中,二氯甲烷萃取三次,合并有机相,旋成硅胶,柱层析(二氯甲烷:正己烷,v:v=1:1)分离纯化,得到化合物D。
1H NMR(400MHz,Chloroform)δ9.36(s,1H),9.08(s,1H),7.69(s,2H),7.58(s,1H),7.43(s,2H),7.36–7.29(m,5H),7.25(d,J=11.6Hz,5H),7.08(s,2H),7.00(s,4H),2.13(s,6H).
13C NMR(100MHz,Chloroform)δ146.93(s),140.83(s),140.21(s),134.42(s),129.38–128.87(m),127.54(s),127.38–127.04(m),125.65(s),124.67(s),122.99(s),122.20(s),121.16(s),119.25(s),95.28(s),13.27(s).
(2)在250ml三口瓶中,加入底物D17.51g(20mmol)、THF(80mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 20mL(50mmol),滴加完全后搅拌30min。再缓慢滴加TMS-Cl 4.35g(40mmol),升温至0℃反应4h。结束后加入冰水淬灭。加入DCM(80mL*2)萃取。收集有机相旋蒸,使用Tol/EtOH析晶得到固体。在200mL闷罐中依次加入固体16.97g(20mmol)、无水甲苯溶液(70mL)和三溴化硼3.04mL(40mmol)。120℃搅拌12h。反应结束后H2O(100mL)淬灭。用DCM(100mL*3)萃取反应液,收集有机相,干燥过滤,旋蒸去除溶剂。使用DCM/EtOH析晶得到固体E。
1H NMR(400MHz,Chloroform)δ9.36(s,1H),9.08(s,1H),δ7.69(s,2H),7.60(d,J=16.0Hz,3H),7.50(s,2H),7.32(s,2H),7.24(s,4H),7.08(s,4H),7.00(s,2H),6.55(s,1H),6.50(s,1H),2.13(s,6H).
13C NMR(100MHz,Chloroform)δ146.93(s),142.85(s),140.54(s),134.71(s),129.48(s),129.27(s),128.58–128.29(m),126.84(s),125.89(s),124.67(s),122.99(s),122.24(s),119.94(s),119.32(s),113.19(s),14.23(s).
(3)将化合物E14.74g(20mmol)加入之反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再缓慢滴加化合物F10.56g(40mmol)的甲苯溶液至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。以柱层析方法(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M3。
1H NMR(400MHz,Chloroform)δ8.25(s,4H),7.69(s,2H),7.60(d,J=16.0Hz,4H),7.50(s,2H),7.32(s,2H),7.24(s,4H),7.08(s,4H),7.00(s,2H),6.65(s,1H),6.52(s,1H),2.13(s,6H).
13C NMR(100MHz,Chloroform)δ172.45(s),169.25(s),166.72(s),153.94(s),146.93(s),142.85(s),140.54(s),134.71(s),134.34(s),130.26(s),129.48(s),129.27(s),128.46(d,J=3.7Hz),127.46(s),126.84(s),124.70(d,J=5.7Hz),122.99(s),122.24(s),114.39(s),112.01(s),14.23(s).
制备例2
化合物M1的合成
(1)在250mL三口瓶中依次加入化合物A 8.94g(20mmol)、化合物B 3.98g(10mmol)、150mL除水除氧的甲苯、碳酸铯13.81g(30mmol)、四(三苯基膦)钯0.23g(0.2mmol),然后在氮气氛围下120℃反应24小时。冷却至室温,将反应液倒入200mL冰水中,二氯甲烷萃取三次,合并有机相,旋成硅胶,柱层析(二氯甲烷:正己烷,v:v=1:1)分离纯化,得到化合物D。
1H NMR(400MHz,Chloroform)δ7.50–7.44(m,6H),7.32–7.24(m,8H),7.22–7.17(m,6H),7.14–7.07(m,10H),6.67(s,2H),2.29(s,6H).
13C NMR(100MHz,Chloroform)δ146.34,144.20,137.71,134.55,134.13,133.53,130.17,129.22,127.64,126.89,125.87,123.63,122.29,96.94,14.03.
(2)在250ml三口瓶中,加入底物D10.43g(10mmol)、THF(80mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 20mL(50mmol),滴加完全后搅拌30min。再缓慢滴加TMS-Cl 4.35g(40mmol),升温至0℃反应4h。结束后加入冰水淬灭。加入DCM(80mL*2)萃取。收集有机相旋蒸,使用Tol/EtOH析晶得到固体。在200mL闷罐中依次加入固体20.32g(20mmol)、无水甲苯溶液(70mL)和三溴化硼3.04mL(40mmol)。120℃搅拌12h。反应结束后H2O(100mL)淬灭。用DCM(100mL*3)萃取反应液,收集有机相,干燥过滤,旋蒸去除溶剂。使用DCM/EtOH析晶得到固体E。
1H NMR(400MHz,Chloroform)δ7.51–7.43(m,6H),7.31–7.25(m,8H),7.23–7.14(m,6H),7.14–7.07(m,12H),2.24(d,J=0.7Hz,6H).
13C NMR(100MHz,Chloroform)δ146.34,144.61,138.34,137.75,132.52,129.22,127.64,126.89,123.66,123.46,123.27,122.16,119.93,15.51,-7.68.
(3)将化合物E18.08g(20mmol)加入之反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再缓慢滴加化合物F 9.52g(40mmol)的甲苯溶液至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。以柱层析方法(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M1。
1H NMR(400MHz,Chloroform)δ9.71(s,3H),8.31(s,3H),7.44–7.35(m,6H),7.31–7.24(m,10H),7.20–7.15(m,3H),7.13–7.05(m,15H),2.23(d,J=0.7Hz,6H).
13C NMR(100MHz,Chloroform)δ161.08,156.89,146.34,145.99,144.25,141.92,138.02,133.53,130.99,129.98,129.43,127.84,126.89,125.11,124.05,123.27,122.11,119.27,52.33,15.28.
制备例3
化合物M2的合成
(1)在250mL三口瓶中依次加入化合物A 9.22g(20mmol)、化合物B 3.98g(10mmol)、150mL除水除氧的甲苯、碳酸铯13.81g(30mmol)、四(三苯基膦)钯0.23g(0.2mmol),然后在氮气氛围下120℃反应24小时。冷却至室温,将反应液倒入200mL冰水中,二氯甲烷萃取三次,合并有机相,旋成硅胶,柱层析(二氯甲烷:正己烷,v:v=1:1)分离纯化,得到化合物D。
1H NMR(400MHz,Chloroform)δ7.52–7.46(m,4H),7.34–7.28(m,4H),7.15(dd,J=7.3,1.8Hz,6H),7.11(td,J=7.2,1.5Hz,6H),7.07(td,J=7.3,1.8Hz,2H),6.78(dd,J=7.4,1.6Hz,4H),6.67(s,2H),2.29(s,6H).
13C NMR(100MHz,Chloroform)δ146.45,139.72,137.77,134.55,134.13,133.40,133.34,130.17,126.28,126.22,125.77,123.92,122.95,120.19,116.50,96.94,14.03.
(2)在250ml三口瓶中,加入底物D10.71g(10mmol)、THF(80mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 20mL(50mmol),滴加完全后搅拌30min。再缓慢滴加TMS-Cl 4.35g(40mmol),升温至0℃反应4h。结束后加入冰水淬灭。加入DCM(80mL*2)萃取。收集有机相旋蒸,使用Tol/EtOH析晶得到固体。在200mL闷罐中依次加入固体20.87g(20mmol)、无水甲苯溶液(70mL)和三溴化硼3.04mL(40mmol)。120℃搅拌12h。反应结束后H2O(100mL)淬灭。用DCM(100mL*3)萃取反应液,收集有机相,干燥过滤,旋蒸去除溶剂。使用DCM/EtOH析晶得到固体E。
1H NMR(400MHz,Chloroform)δ7.51–7.44(m,6H),7.38–7.32(m,4H),7.21(s,2H),7.18–7.04(m,12H),6.78(dd,J=7.3,1.7Hz,4H),2.24(d,J=0.7Hz,6H).
13C NMR(100MHz,Chloroform)δ146.45,139.72,138.34,137.30,133.40,132.22,126.28,126.22,123.66,123.51,123.46,122.68,120.17,119.76,116.41,15.51,-7.68.
(3)将化合物E18.64g(20mmol)加入之反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再缓慢滴加化合物F 9.56g(40mmol)的甲苯溶液至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。以柱层析方法(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M2。
1H NMR(400MHz,Chloroform)δ8.35(d,J=14.8Hz,6H),7.50–7.44(m,4H),7.39–7.32(m,6H),7.18–7.03(m,14H),6.78(dd,J=7.4,1.6Hz,4H),2.22(d,J=0.7Hz,6H).
13C NMR(100MHz,Chloroform)δ171.33,168.23,165.31,159.25,157.16,145.20,141.92,139.84,138.04,133.44,130.99,129.98,126.42,126.41,125.11,124.06,124.05,122.68,120.19,119.27,115.80,52.33,15.28.
制备例4
化合物M4的合成
(1)在250mL三口瓶中依次加入化合物A 3.71g(10mmol)、化合物B 3.98g(10mmol)、化合物C 4.87g(10mmol)、150mL除水除氧的甲苯、碳酸铯13.81g(30mmol)、四(三苯基膦)钯0.23g(0.2mmol),然后在氮气氛围下120℃反应24小时。冷却至室温,将反应液倒入200mL冰水中,二氯甲烷萃取三次,合并有机相,旋成硅胶,柱层析(二氯甲烷:正己烷,v:v=1:1)分离纯化,得到化合物D。
1H NMR(400MHz,Chloroform)δ7.99(dd,J=7.3,1.6Hz,1H),7.57–7.44(m,6H),7.41–7.31(m,2H),7.25–7.17(m,4H),7.17(dd,J=7.5,1.5Hz,2H),7.09–6.99(m,6H),6.72–6.66(m,2H),2.31–2.27(m,6H),1.56(s,6H).
13C NMR(100MHz,Chloroform)δ156.30,154.65,142.47,140.25,139.22,138.36,136.73,134.45,134.36,134.17,134.08,133.42,133.33,130.26,130.17,129.44,128.69,127.21,125.96,125.87,125.08,124.43,123.99,123.92,123.64,122.90,121.79,117.85,117.80,111.70,111.27,97.02,96.94,37.50,27.89,14.09,14.03.
(2)在250ml三口瓶中,加入底物D10.05g(10mmol)、THF(80mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 20mL(50mmol),滴加完全后搅拌30min。再缓慢滴加TMS-Cl 4.35g(40mmol),升温至0℃反应4h。结束后加入冰水淬灭。加入DCM(80mL*2)萃取。收集有机相旋蒸,使用Tol/EtOH析晶得到固体。在200mL闷罐中依次加入固体19.84g(20mmol)、无水甲苯溶液(70mL)和三溴化硼3.04mL(40mmol)。120℃搅拌12h。反应结束后H2O(100mL)淬灭。用DCM(100mL*3)萃取反应液,收集有机相,干燥过滤,旋蒸去除溶剂。使用DCM/EtOH析晶得到固体E。
1H NMR(400MHz,Chloroform)δ8.03–7.98(m,1H),7.69–7.65(m,1H),7.57–7.44(m,7H),7.41–7.32(m,2H),7.30(dd,J=7.5,1.5Hz,1H),7.26–7.17(m,5H),7.17(dd,J=7.4,1.6Hz,2H),7.09–7.02(m,4H),2.27–2.23(m,6H),1.56(s,6H).
13C NMR(100MHz,Chloroform)δ156.30,154.58,142.47,139.22,139.02,138.42,138.34,137.30,136.59,132.60,132.52,129.44,128.69,126.56,124.73,124.17,124.09,124.05,123.99,123.64,123.54,123.46,123.09,122.71,122.17,119.84,119.76,117.71,117.53,111.70,110.97,37.50,27.89,16.04,15.97,-7.59,-7.68.
(3)将化合物E17.34g(20mmol)加入之反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再缓慢滴加化合物F 9.56g(40mmol)的甲苯溶液至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。以柱层析方法(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M4。
1H NMR(400MHz,Chloroform)δ8.89(s,3H),8.23–8.16(m,3H),8.10(s,1H),7.99(dd,J=7.3,1.6Hz,1H),7.74(d,J=7.5Hz,2H),7.69–7.65(m,1H),7.54(dd,J=7.5,1.6Hz,2H),7.48(td,J=7.5,1.4Hz,2H),7.44–7.39(m,2H),7.42–7.34(m,3H),7.37–7.29(m,1H),7.26–7.18(m,4H),7.17(dd,J=7.6,1.6Hz,2H),7.10–7.01(m,4H),2.22(dd,J=3.1,0.7Hz,6H),1.56(s,6H).
13C NMR(100MHz,Chloroform)δ161.08,160.99,156.05,154.23,148.97,148.92,148.88,144.24,143.50,143.42,141.33,141.25,139.86,139.72,139.21,139.18,139.13,139.09,138.54,138.05,137.99,136.68,133.00,132.93,132.45,131.89,131.80,131.73,129.44,128.48,128.00,127.94,126.01,125.52,125.47,125.38,124.93,124.33,124.24,124.13,124.09,123.60,123.42,122.75,122.51,120.07,119.99,119.44,118.28,116.70,116.64,116.58,111.75,111.13,109.44,109.36,37.50,27.89,15.35,15.28,6.01,5.91.
制备例5
化合物M21的合成
(1)在250mL三口瓶中依次加入化合物A 9.22g(20mmol)、化合物B 3.98g(10mmol)、150mL除水除氧的甲苯、碳酸铯13.81g(30mmol)、四(三苯基膦)钯0.23g(0.2mmol),然后在氮气氛围下120℃反应24小时。冷却至室温,将反应液倒入200mL冰水中,二氯甲烷萃取三次,合并有机相,旋成硅胶,柱层析(二氯甲烷:正己烷,v:v=1:1)分离纯化,得到化合物D。
1H NMR(400MHz,Chloroform)δ7.47–7.41(m,4H),7.32–7.24(m,8H),7.19–7.14(m,4H),7.17–7.07(m,14H),2.39(s,6H),2.26(s,6H).
13C NMR(100MHz,Chloroform)δ146.34,143.99,140.82,137.16,135.48,133.61,131.41,130.31,129.22,127.84,126.89,123.30,122.08,100.28,12.54,11.75.
(2)在250ml三口瓶中,加入底物D10.71g(10mmol)、THF(80mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 20mL(50mmol),滴加完全后搅拌30min。再缓慢滴加TMS-Cl 4.35g(40mmol),升温至0℃反应4h。结束后加入冰水淬灭。加入DCM(80mL*2)萃取。收集有机相旋蒸,使用Tol/EtOH析晶得到固体。在200mL闷罐中依次加入固体20.87g(20mmol)、无水甲苯溶液(70mL)和三溴化硼3.04mL(40mmol)。120℃搅拌12h。反应结束后H2O(100mL)淬灭。用DCM(100mL*3)萃取反应液,收集有机相,干燥过滤,旋蒸去除溶剂。使用DCM/EtOH析晶得到固体E。
1H NMR(400MHz,Chloroform)δ7.49–7.43(m,4H),7.31–7.21(m,8H),7.19–7.14(m,4H),7.17–7.06(m,14H),2.41(s,6H),2.22(s,6H).
13C NMR(100MHz,Chloroform)δ146.34,144.44,139.53,137.03,133.33,132.38,129.82,129.22,127.64,126.89,124.61,122.03,120.47,13.45,12.57.
(3)将化合物E18.65g(20mmol)加入之反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再缓慢滴加化合物F 9.52g(40mmol)的甲苯溶液至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。以柱层析方法(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M21。
1H NMR(400MHz,Chloroform)δ9.71(s,4H),8.31(s,4H),7.42–7.37(m,4H),7.31–7.24(m,8H),7.19–7.13(m,4H),7.13–7.08(m,8H),7.09(dd,J=3.5,1.9Hz,6H),2.41(s,6H),2.22(s,6H).
13C NMR(100MHz,Chloroform)δ161.08,156.89,148.33,146.34,146.25,144.45,140.55,138.01,137.63,133.53,129.89,129.49,129.43,128.89,127.81,126.89,124.34,121.98,119.69,32.05,13.45,12.57.
制备例6
化合物M22的合成
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(1)在250mL三口瓶中依次加入化合物A 9.22g(20mmol)、化合物B 3.98g(10mmol)、150mL除水除氧的甲苯、碳酸铯13.81g(30mmol)、四(三苯基膦)钯0.23g(0.2mmol),然后在氮气氛围下120℃反应24小时。冷却至室温,将反应液倒入200mL冰水中,二氯甲烷萃取三次,合并有机相,旋成硅胶,柱层析(二氯甲烷:正己烷,v:v=1:1)分离纯化,得到化合物D。
1H NMR(400MHz,Chloroform)δ7.48–7.43(m,4H),7.35–7.29(m,4H),7.15(dd,J=7.3,1.8Hz,8H),7.11(td,J=7.2,1.5Hz,4H),7.07(td,J=7.3,1.8Hz,4H),6.78(dd,J=7.4,1.6Hz,4H),5.78(s,2H),2.33(s,6H).
13C NMR(100MHz,Chloroform)δ146.45,139.73,137.88,136.15,136.00,133.40,129.08,128.85,126.28,126.22,123.66,122.79,120.23,120.19,116.50,95.90,13.82.
(2)在250ml三口瓶中,加入底物D10.71g(10mmol)、THF(80mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 20mL(50mmol),滴加完全后搅拌30min。再缓慢滴加TMS-Cl 4.35g(40mmol),升温至0℃反应4h。结束后加入冰水淬灭。加入DCM(80mL*2)萃取。收集有机相旋蒸,使用Tol/EtOH析晶得到固体。在200mL闷罐中依次加入固体20.87g(20mmol)、无水甲苯溶液(70mL)和三溴化硼3.04mL(40mmol)。120℃搅拌12h。反应结束后H2O(100mL)淬灭。用DCM(100mL*3)萃取反应液,收集有机相,干燥过滤,旋蒸去除溶剂。使用DCM/EtOH析晶得到固体E。
1H NMR(400MHz,Chloroform)δ7.50–7.44(m,4H),7.40–7.34(m,4H),7.33(s,2H),7.18–7.04(m,12H),6.78(dd,J=7.3,1.7Hz,4H),5.96(s,2H),2.31(s,6H).
13C NMR(100MHz,Chloroform)δ146.45,139.76,137.36,133.40,131.72,131.17,130.67,130.50,126.28,126.22,122.82,122.61,120.34,120.17,116.41,114.31,14.06.
(3)将化合物E18.65g(20mmol)加入之反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再缓慢滴加化合物F 9.52g(40mmol)的甲苯溶液至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。以柱层析方法(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M22。
1H NMR(400MHz,Chloroform)δ8.41(s,2H),8.33(s,4H),7.50–7.43(m,6H),7.40–7.34(m,4H),7.18–7.03(m,14H),6.78(dd,J=7.4,1.6Hz,4H),2.31(s,6H).
13C NMR(100MHz,Chloroform)δ176.77,168.39,165.31,159.25,157.37,145.20,139.88,138.73,136.22,133.44,132.97,128.16,127.17,126.42,126.41,122.78,122.61,120.19,120.16,117.56,115.80,78.65,14.06.
制备例7
化合物M30的合成
(1)在250mL三口瓶中依次加入化合物A 4.47g(10mmol)、化合物B 3.98g(10mmol)、化合物C 4.77g(10mmol)、150mL除水除氧的甲苯、碳酸铯13.81g(30mmol)、四(三苯基膦)钯0.23g(0.2mmol),然后在氮气氛围下120℃反应24小时。冷却至室温,将反应液倒入200mL冰水中,二氯甲烷萃取三次,合并有机相,旋成硅胶,柱层析(二氯甲烷:正己烷,v:v=1:1)分离纯化,得到化合物D。
1H NMR(400MHz,Chloroform)δ7.48–7.43(m,4H),7.35–7.29(m,4H),7.15(dd,J=7.3,1.8Hz,8H),7.11(td,J=7.2,1.5Hz,4H),7.07(td,J=7.3,1.8Hz,4H),6.78(dd,J=7.4,1.6Hz,4H),5.78(s,2H),2.33(s,6H).
13C NMR(100MHz,Chloroform)δ146.45,139.73,137.88,136.15,136.00,133.40,129.08,128.85,126.28,126.22,123.66,122.79,120.23,120.19,116.50,95.90,13.82.
(2)在250ml三口瓶中,加入底物D10.73g(10mmol)、THF(80mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 20mL(50mmol),滴加完全后搅拌30min。再缓慢滴加TMS-Cl 4.35g(40mmol),升温至0℃反应4h。结束后加入冰水淬灭。加入DCM(80mL*2)萃取。收集有机相旋蒸,使用Tol/EtOH析晶得到固体。在200mL闷罐中依次加入固体20.88g(20mmol)、无水甲苯溶液(70mL)和三溴化硼3.04mL(40mmol)。120℃搅拌12h。反应结束后H2O(100mL)淬灭。用DCM(100mL*3)萃取反应液,收集有机相,干燥过滤,旋蒸去除溶剂。使用DCM/EtOH析晶得到固体E。
1H NMR(400MHz,Chloroform)δ7.50–7.44(m,4H),7.40–7.34(m,4H),7.33(s,2H),7.18–7.04(m,12H),6.78(dd,J=7.3,1.7Hz,4H),5.96(s,2H),2.31(s,6H).
13C NMR(100MHz,Chloroform)δ146.45,139.76,137.36,133.40,131.72,131.17,130.67,130.50,126.28,126.22,122.82,122.61,120.34,120.17,116.41,114.31,14.06.
(3)将化合物E18.68g(20mmol)加入之反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再缓慢滴加化合物F 4.78g(20mmol)和化合物E 3.51g(20mmol)的甲苯溶液至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。以柱层析方法(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M30。
1H NMR(400MHz,Chloroform)δ8.35(d,J=15.6Hz,3H),8.10(s,1H),7.66–7.59(m,2H),7.51–7.44(m,4H),7.39–7.31(m,4H),7.31–6.98(m,16H),6.78(dd,J=7.4,1.6Hz,2H),6.42(d,J=7.5Hz,1H),2.22(d,J=0.7Hz,6H).
13C NMR(100MHz,Chloroform)δ171.02,168.23,164.53,159.25,157.16,146.03,144.50,143.22,142.47,141.92,139.84,139.83,138.62,138.04,134.09,134.02,133.46,130.99,129.38,128.08,127.17,126.97,126.42,126.41,126.01,125.31,124.05,123.99,123.67,123.34,122.68,122.55,120.19,119.35,119.27,119.16,118.21,116.94,115.80,115.19,115.03,52.33,50.76,15.28.
实施例1
本应用例提供一种OLED器件,如图1所示,所述OLED器件依次包括:基板1、ITO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、第一电子传输层7、第二电子传输层8、电子注入层9、阴极10(铝电极)和盖帽层(CBP)11,其中ITO阳极的厚度为15nm、空穴注入层的厚度为10nm、空穴传输层的厚度为110nm、发光层的厚度为30nm、第一电子传输层的厚度为30nm、第二电子传输层的厚度为5nm、阴极的厚度为15nm(镁银电极,镁银质量比为1:9)、盖帽层的厚度为100nm,其中图中箭头表示出光方向。
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,分别在异丙醇和去离子水中超声处理30min,然后暴露在臭氧下清洁10min,得到基板;将所得的具有厚度为15nm的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化合物HAT-CN,厚度为10nm,作为空穴注入层;
(3)在空穴注入层上真空蒸镀化合物TAPC作为空穴传输层,厚度为110nm;
(4)在空穴传输层上共沉积发光层,其中,用本发明实施例1提供的有机化合物M1作为发光层的掺杂材料,化合物mCBP作为发光层的主体材料,M1与mCBP的质量比为1:9,厚度为30nm;
(5)在发光层上真空蒸镀化合物TPBi作为第一电子传输层,厚度为30nm;
(6)在第一电子传输层上真空蒸镀化合物Alq3作为第二电子传输层,厚度为5nm;
(7)在第二电子传输层上真空蒸镀镁银电极作为阴极,厚度为15nm;
(8)在阴极上真空蒸镀CBP作为阴极覆盖层(盖帽层),厚度为100nm。
所述OLED器件中用到的化合物结构如下:
实施例2-7
与实施例1的区别仅在于,将实施例1中的M1替换为M2、M3、M4、M21、M22以及M30,得到实施例2-7。
对比例1
与实施例1的区别仅在于,将实施例1中的M1替换为DCJTB。
性能测试:
(1)化合物的模拟计算
有机材料的单线态和三线态的能级差可以通过Guassian 09软件(Guassian Inc.完成,能级差ΔEst具体的模拟方法参照J.Chem.Theory Comput.,2013,DOI:10.1021/ct400415r,分子结构优化和激发均可用TD-DFT方法“B3LYP”和基组“6-31g(d)”完成,Tg采用差示扫描量热法测量,本案针对制备例1-7制备的化合物以及对比例选用的化合物DCJTB,结果如表1所示。
表1
从表1中的数据可得,本发明提供的制备例制备得到的所有化合物的△EST均小于0.3eV,实现了较小的单线态和三线态能级差,利于反向系间穿越。
通过高斯模拟计算本发明提供的化合物的HOMO和LUMO能级,其中,本发明提供的化合物M3的HOMO和LUMO分布示意图分别如图2和图3所示。从图2和图3可以看出,M3的HOMO和LUMO在空间上有较好的分离,有助于降低△EST。
(2)OLED器件的性能评价
采用Spectroscan PR 705光谱仪和Keithley 236电流电压源测量***检测器件的效率、电压,电压和效率均是在电流密度为10mA/cm2测得的,LT95的寿命测试如下:使用亮度计在10000cd/m2亮度下,保持恒定的电流,测量有机电致发光器件的亮度降为9500cd/m2的时间,单位为小时结果如表2所示。
表2
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3.85V,电流效率大于27.5Cd/A,使用寿命大于89h。相对于对比例1,这主要得益于本发明所述化合物自身所具有的TADF特性,具有较低的△EST(<0.3eV),单线态和三线态之间存在高效的反向系间窜跃的光物理过程,可以利用传统荧光分子跃迁禁阻的三线态激子来发光,从而提高了器件效率,进而在一定程度上提升了器件的工作寿命。
本发明实施例的又一方面提供了一种电子设备,包括上文所述的有机光电装置,其中电子设备可以为触摸显示屏、手机、平板计算机、笔记本电脑、电纸书、电视机、VR或AR头盔或智能手表等任何具有显示功能的电子设备。图4为本发明实施例提供的一种电子设备的示意图。其中,100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 (15)
1.一种化合物,其特征在于,所述化合物具有式I所示的结构:
式I中,R1和R2各自独立地选自如下基团中的任意一种:
式I中,R3和R4各自独立地选自取代或未取代的噁二唑基、取代或未取代的咪唑基、取代或未取代的噁唑基、取代或未取代的***基、取代或未取代的喹啉基、取代或未取代的三嗪基中的任意一种;
式I中,Ra、Rb和Rc各自独立地选自氰基、取代或未取代的C1-C10烷基、取代或未取代的C6-C20芳基、取代或未取代的C3-C20杂芳基中的任意一种;
式I中,m、n和p各自独立地选自0-2的整数;
R3、R4、Ra、Rb和Rc中,所述取代的基团选自卤素、氰基、C1-C12的链状烷基、C6-C20的单环芳烃或稠环芳烃基团、C3-C20的单环杂芳烃或稠环杂芳烃基团中的任意一种。
2.根据权利要求1所述的化合物,其特征在于,所述m、n和p各自独立地选自0或1。
3.根据权利要求1所述的化合物,其特征在于,所述m和n均为1,p为0。
4.根据权利要求1所述的化合物,其特征在于,所述Ra、Rb和Rc各自独立地选自甲基、苯基、二联苯基、三联苯基、萘基、芴基或咔唑基中的任意一种。
5.根据权利要求1所述的化合物,其特征在于,所述化合物具有式II所示的结构:
其中,R1、R2、R3和R4具有与权利要求1相同的限定范围。
6.根据权利要求5所述的化合物,其特征在于,所述化合物具有式III所示的结构:
其中,R1、R2、R3和R4具有与权利要求5相同的限定范围。
7.根据权利要求1所述的化合物,其特征在于,所述R1和R2相同。
8.根据权利要求1所述的化合物,其特征在于,所述R3和R4各自独立地选自如下基团中的任意一种:
其中,虚线表示基团的连接位点。
9.根据权利要求1所述的化合物,其特征在于,所述R3和R4相同。
10.根据权利要求1所述的化合物,其特征在于,所述化合物为如下结构中的任意一种:
11.根据权利要求1所述的化合物,其特征在于,所述化合物的最低单重态S1与最低三重态T1态之间的能极差ΔEst=ES1-ET1≤0.3eV。
12.一种热激活延迟荧光材料,其特征在于,所述热激活延迟荧光材料包括权利要求1-11任一项所述的化合物中的任意一种或至少两种的组合。
13.一种显示面板,其特征在于,所述显示面板包括OLED器件,所述OLED器件包括阳极、阴极、以及位于阳极和阴极之间的至少一层有机层,所述有机层包括发光层,所述发光层包括权利要求12所述的热激活延迟荧光材料,且所述热激活延迟荧光材料用作主体材料、掺杂材料或共同掺杂材料中的任意一种。
14.根据权利要求13所述的显示面板,其特征在于,所述有机层还包括空穴传输层、空穴注入层、电子阻挡层、空穴阻挡层、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。
15.一种电子设备,其特征在于,所述电子设备包括权利要求13或14所述的显示面板。
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