CN114685419A - 含螺环结构的有机化合物及有机电致发光器件 - Google Patents
含螺环结构的有机化合物及有机电致发光器件 Download PDFInfo
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- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000011364 vaporized material Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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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Abstract
本发明提供了一种式I所示的含螺环结构的有机化合物。本发明还提供了所述有机化合物在电致发光器件中的应用。所述含螺环结构的有机化合物相较于现有技术的有机化合物具有较低折射率,应用于有机电致发光器件时,可以有效的增加光取出率,能够提高器件的发光效率。
Description
技术领域
本发明涉及一种含螺环结构的有机化合物及有机电致发光器件。
背景技术
有机电致发光现象是1963年Pope等人最早发现的,直到1987年柯达公司的邓青云博士等人报道了基于荧光效率高、电子传输性好的8-羟基喹啉铝和空穴传输性良好的芳香二胺两种有机半导体材料,通过真空热蒸镀制备了器件为三明治型的有机电致发光器件。在驱动电压小于10V的电压下,前述有机电致发光器件的外量子效率达到了1%,使得有机电致发光材料及器件具有了实用性的可能,从此引起了众多科学家和产业界对有机电致发光材料及器件的研究。
近年来,有机电致发光技术作为新一代的显示技术逐渐进入人们的视野,广泛的应用前景和技术上的突飞猛进使得有机电致发光技术成为显示领域和科学研究产品开发最热门的研究之一。
目前,有机电致发光器件或屏体仍然存在驱动电压高、电流效率低的缺陷,为了改善这些缺陷,一方面器件结构需要进一步优化,另一方面也需要改进各功能层光材料的性能,其中,电子阻挡层材料影响着器件的效率,因此,开发新型的电子阻挡材料具有十分重要的意义。
发明内容
本发明的目的是为了克服现有技术中有机电致发光器件存在的驱动电压高、发光效率低的问题。
为了实现上述目的,本发明的第一方面提供一种新的含螺环结构的有机化合物,其结构如式I所示,
其中,X选自氧或硫;
L选自单键、含取代基或不含取代基的C6-C30亚芳基和含取代基或不含取代基的C6-C30亚杂芳基;
R1选自含取代基或不含取代基的C6-C40芳基和含取代基或不含取代基的C6-C40杂芳基;
R2选自含取代基或不含取代基的C9-C40稠环芳基、含取代基或不含取代基的C5-C40稠环杂芳基和-NR21R22,其中R21和R22相同或不同,各自独立选自含取代基或不含取代基的C6-C40芳基、含取代基或不含取代基的C3-C40杂芳基、含取代基或不含取代基的C9-C40稠环芳基和含取代基或不含取代基的C5-C40稠环杂芳基。
根据本发明的一些实施方式,所述取代基选自卤素、氰基、C1-C10烷基和C1-C10烷氧基。
根据本发明的一些实施方式,所述卤素选自氟、氯、溴和碘。
根据本发明的一些实施方式,所述C1-C10烷基选自甲基、乙基、正丙基、异丙基、正丁基、叔丁基、异丁基、正戊基、异戊基、正己基和正庚基。
根据本发明的一些实施方式,所述C1-C10烷氧基选自甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、异丁氧基、正戊氧基、异戊氧基、正己氧基和正庚氧基。
根据本发明的一些实施方式,所述有机化合物的结构如式II或式III所示,
其中,X选自氧或硫;
L选自单键、含取代基或不含取代基的C6-C30亚芳基和含取代基或不含取代基的C6-C30亚杂芳基,R1选自含取代基或不含取代基的C6-C40芳基和含取代基或不含取代基的C6-C40杂芳基;
R21和R22相同或不同,各自独立选自含取代基或不含取代基的C6-C40芳基、含取代基或不含取代基的C3-C40杂芳基、含取代基或不含取代基的C9-C40稠环芳基和含取代基或不含取代基的C5-C40稠环杂芳基;
R23选自含取代基或不含取代基的C9-C40稠环芳基和含取代基或不含取代基的C5-C40稠环杂芳基。
根据本发明的一些实施方式,L选自单键、含取代基或不含取代基的C6-C20亚芳基和含取代基或不含取代基的C6-C20亚杂芳基。
根据本发明的一些实施方式,L选自单键、亚苯基、亚联苯基或亚萘基。
根据本发明的一些实施方式,L选自如下所示的亚芳基:
根据本发明的一些实施方式,所述有机化合物的结构如式IIA、式IIB、式IIIA或式IIIB所示
其中,X选自氧或硫;
R1选自含取代基或不含取代基的C6-C40芳基和含取代基或不含取代基的C6-C40杂芳基;
R21和R22相同或不同,各自独立选自含取代基或不含取代基的C6-C40芳基、含取代基或不含取代基的C3-C40杂芳基、含取代基或不含取代基的C9-C40稠环芳基和含取代基或不含取代基的C5-C40稠环杂芳基;
R23选自含取代基或不含取代基的C9-C40稠环芳基和含取代基或不含取代基的C5-C40稠环杂芳基。
根据本发明的一些实施方式,所述有机化合物的结构如式IIB-1、式IIB-2、式IIIB-1或式IIIB-2所示
其中,X选自氧或硫;
R1选自含取代基或不含取代基的C6-C40芳基和含取代基或不含取代基的C6-C40杂芳基;
R21和R22相同或不同,各自独立选自含取代基或不含取代基的C6-C40芳基、含取代基或不含取代基的C3-C40杂芳基、含取代基或不含取代基的C9-C40稠环芳基和含取代基或不含取代基的C5-C40稠环杂芳基;
R23选自含取代基或不含取代基的C9-C40稠环芳基和含取代基或不含取代基的C5-C40稠环杂芳基。
根据本发明的一些实施方式,R1选自含取代基或不含取代基的C6-C30芳基和含取代基或不含取代基的C6-C30杂芳基。
根据本发明的一些实施方式,R1选自含取代基或不含取代基的C6-C20芳基。
根据本发明的一些实施方式,R1选自含取代基或不含取代基的苯基、联苯基、萘基。
根据本发明的一些实施方式,R1选自以下基团:
根据本发明的一些实施方式,R21和R22相同或不同,各自独立选自含取代基或不含取代基的C6-C30芳基,含取代基或不含取代基的C3-C30杂芳基、含取代基或不含取代基的C9-C30稠环芳基、含取代基或不含取代基的C5-C30稠环杂芳基。
根据本发明的一些实施方式,R21和R22相同或不同,各自独立选自含取代基或不含取代基的C6-C20芳基,含取代基或不含取代基的C3-C20杂芳基、含取代基或不含取代基的C9-C20稠环芳基、含取代基或不含取代基的C5-C20稠环杂芳基。
根据本发明的一些实施方式,R21和R22相同或不同,R21选自含取代基或不含取代基的C6-C20芳基,R22选自含取代基或不含取代基的C6-C20芳基、含取代基或不含取代基的C9-C20稠环芳基和含取代基或不含取代基的C5-C20稠环杂芳基。
根据本发明的一些实施方式,R21和R22相同或不同,各自独立选自含取代基或不含取代基的苯基、含取代基或不含取代基的联苯基、含取代基或不含取代基的萘基、含取代基或不含取代基的苯基萘基、含取代基或不含取代基的二苯并呋喃基、含取代基或不含取代基的二苯并噻吩基、含取代基或不含取代基的咔唑基、含取代基或不含取代基的苯基咔唑基、含取代基或不含取代基的二苯基咔唑基、含取代基或不含取代基的萘基咔唑基和含取代基或不含取代基的芴基。
根据本发明的一些实施方式,R21选自含取代基或不含取代基的C6-C15芳基,R22选自含取代基或不含取代基的C6-C15芳基,例如,R21选自含取代基或不含取代基的苯基和含取代基或不含取代基的联苯基,R22选自含取代基或不含取代基的苯基和含取代基或不含取代基的联苯基。
根据本发明的一些实施方式,R21选自含取代基或不含取代基的C6-C15芳基,R22选自含取代基或不含取代基的C9-C20稠环芳基,例如,R21选自含取代基或不含取代基的苯基和含取代基或不含取代基的联苯基,R22选自含取代基或不含取代基的萘基、含取代基或不含取代基的苯基萘基和含取代基或不含取代基的芴基。
根据本发明的一些实施方式,R21选自含取代基或不含取代基的C6-C15芳基,R22选自含取代基或不含取代基的C5-C20稠环杂芳基,例如,R21选自含取代基或不含取代基的苯基和含取代基或不含取代基的联苯基,R22选自含取代基或不含取代基的二苯并呋喃基、含取代基或不含取代基的二苯并噻吩基、含取代基或不含取代基的咔唑基、含取代基或不含取代基的苯基咔唑基、含取代基或不含取代基的二苯基咔唑基和含取代基或不含取代基的萘基咔唑基。
根据本发明的一些实施方式,R21选自含取代基或不含取代基的C9-C20稠环芳基,R22选自含取代基或不含取代基的C9-C20稠环芳基,例如,R21选自含取代基或不含取代基的萘基、含取代基或不含取代基的苯基萘基和含取代基或不含取代基的芴基,R22选自含取代基或不含取代基的萘基、含取代基或不含取代基的苯基萘基和含取代基或不含取代基的芴基。
根据本发明的一些实施方式,R21选自含取代基或不含取代基的C5-C20稠环杂芳基,R22选自含取代基或不含取代基的C5-C20稠环杂芳基,例如,R21选自含取代基或不含取代基的二苯并呋喃基、含取代基或不含取代基的二苯并噻吩基、含取代基或不含取代基的咔唑基、含取代基或不含取代基的苯基咔唑基、含取代基或不含取代基的二苯基咔唑基和含取代基或不含取代基的萘基咔唑基,R22选自含取代基或不含取代基的二苯并呋喃基、含取代基或不含取代基的二苯并噻吩基、含取代基或不含取代基的咔唑基、含取代基或不含取代基的苯基咔唑基、含取代基或不含取代基的二苯基咔唑基和含取代基或不含取代基的萘基咔唑基。
根据本发明的一些实施方式,R21和R22相同或不同,各自独立选自以下基团:
根据本发明的一些实施方式,R23选自含取代基或不含取代基的C9-C20稠环芳基、含取代基或不含取代基的C5-C20稠环杂芳基。
根据本发明的一些实施方式,R23选自含取代基或不含取代基的咔唑基、含取代基或不含取代基的苯基咔唑基、含取代基或不含取代基的二苯基咔唑基和含取代基或不含取代基的萘基咔唑基。
根据本发明的一些实施方式,R23选自以下基团:
本发明中,各基团上的星号*表示基团与其他部分的连接点。
本发明的有机化合物的具体例子包括但不限于以下化合物:
本发明的有机化合物结构中所涉及的元素,如果包含同位素,其同位素也在本发明的保护范围以内。
将本发明所述含有螺环结构的有机化合物用于有机电致发光器件中,具有以下优势:
1、本发明的母核为螺环结构,具有较高的三线态能级,可有效的阻挡激子扩散,应用于有机电致发光器件中能够有效的提高发光效率。
2、本发明母核的1位被芳基取代,一方面可以调节化合物的堆积方式,使其具有合适的载流子迁移率,应用于有机电致发光器件时能够降低驱动电压,同时本发明的化合物在增加位阻时,不会显著改变本发明化合物的LUMO能级,能够有效的阻挡电子,防止漏电,进一步地能够提高器件的发光效率;另一方面,本发明的化合物因为同时具有螺环结构和在1位取代的芳基,从而使化合物的堆积较为松散,因此本发明的化合物具有较低折射率,应用于有机电致发光器件时,可以有效的增加光取出率,能够提高器件的发光效率。
本发明的第二方面提供前述含有螺环结构的有机化合物在电子器件尤其是有机电致发光器件中的应用。
根据本发明的一些实施方式,所述有机化合物用于空穴传输层、电子阻挡层和发光层中的至少一层。
根据本发明的一些实施方式,所述有机化合物用于电子阻挡层中。
本发明的第三方面提供了一种有机电致发光器件,所述有机电致发光器件包括依次层叠设置的设置的阳极、空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和阴极。
根据本发明的一些实施方式,所述化合物存在于该有机电致发光器件的空穴传输层、电子阻挡层和发光层的至少一层中。
根据本发明的一些实施方式,所述有机化合物存在于该有机电致发光器件的电子阻挡层中。
根据本发明的一些实施方式,形成所述阳极的阳极材料,通常优选具有大功函数的材料,从而能够降低空穴注入势垒,例如能够在本发明中使用的阳极材料选自以下材料的一种或多种,金属,如钒、铬、铜和金,或其他合金:金属氧化物,如:氧化锌、氧化铟、氧化铟锡、氧化铟锌和二氧化锡,金属和氧化物的组合,如:氧化锌:铝,但不限于此。
根据本发明的一些实施方式,形成所述空穴注入层的材料,作为空穴注入材料优选的化合物要具有传输空穴的能力,因此,所述空穴注入层的材料具有注入阳极中的空穴效应,对发光层或发光材料具有优异的空穴注入效应,防止发光层中产生的激子移动至电子注入层或电子注入材料,此外,具有优异的薄膜形成能力。空穴注入材料的HOMO优选在阳极材料的功函数与周围有机材料层的HOMO之间。
根据本发明的一些实施方式,形成所述空穴传输层的材料为能够接收来自阳极或空穴注入层的空穴、使空穴移动至发光层并对空穴具有高迁移率的材料。
根据本发明的一些实施方式,所述空穴注入材料和空穴传输材料包括芳香族胺衍生物(例如NPB、SqMA1)、六氮杂苯并菲衍生物(例如HACTN)、吲哚并咔唑衍生物、导电聚合物(例如PEDOT/PSS),酞菁或卟啉衍生物、二苯并茚并芴胺、螺二芴胺中的至少一种,但不限于此。
根据本发明的一些实施方式,所述空穴注入层和空穴传输层例如可采用如下通式的芳香族胺衍生物形成:
上述通式中的R1至R9的基团各自独立地选自单键、氢、氘、烷基、苯、二联苯、三联苯、萘、蒽、菲、苯并菲、芘、芴、二甲基芴、螺二芴、咔唑、噻吩、苯并噻吩、二苯并噻吩、呋喃、苯并呋喃、二苯并呋喃、吲哚、吲哚咔唑、茚并咔唑、吡啶、嘧啶、咪唑、噻唑、喹啉、异喹啉、喹喔啉、喹唑啉、卟啉、咔啉、吡嗪、哒嗪或三嗪。
根据本发明的一些实施方式,电子阻挡层的形成材料不受特别限制,一般情况下,能够具备如下第1或/和第2个条件的化合物均可考虑采用:
第1:具备较高的LUMO能级(绝对值较小),其目的就是减少离开发光层的电子数目,从而提高电子和空穴在发光层的复合几率。
第2:具备较大的三线态能量,其目的就是减少离开发光层的激子数量,从而提高激子转换发光的效率。
根据本发明的一些实施方式,当所述器件的发光层中含有本发明前述第一方面中所述的化合物时,形成所述电子阻挡层的材料包括但不限于芳香族胺衍生物(例如NPB)、螺二芴胺(例如SpMA2),其中部分电子阻挡材料和空穴注入材料和空穴传输材料的结构类似。
根据本发明的一些实施方式,当所述器件的电子阻挡层中含有本发明前述第一方面中所述的化合物时,发光层的发光材料是能够通过接收分别来自空穴传输层和电子传输层的空穴和电子并使空穴和电子结合而发出可见光区域内的光的材料,并且优选对荧光或磷光有良好的量子效率的材料。
根据本发明的一些实施方式,发光层可以包含主体材料和客体材料。
根据本发明的一些实施方式,所述的主体材料可以包括蒽类衍生物、咔唑类衍生物、芴类衍生物、芳胺类衍生物、有机硅类衍生物、咔唑-三嗪类衍生物、磷氧基类衍生物,但不限于此。
在本发明的一些优选实施方式中,所述蒽类衍生物具有如下所示的通式:
所述磷氧基类衍生物具有如下所示的通式:
在上述蒽类衍生物和磷氧基类衍生物的通式中,R11、R12、R13、R14、R15和R16各自独立地选自单键、氢、氘、烷基、苯、二联苯、三联苯、四联苯、萘、苯基萘、蒽、菲、苯并菲、芘、芴、咔唑、噻吩、苯并噻吩、二苯并噻吩、呋喃、苯并呋喃、二苯并呋喃、吲哚、吲哚咔唑、茚并咔唑、吡啶、嘧啶、咪唑、噻唑、喹啉、异喹啉、喹喔啉、喹唑啉、卟啉、咔啉、吡嗪、哒嗪或三嗪,以及它们的取代物表示的基团。
根据本发明的一些实施方式,客体材料优选为经由磷光、荧光、TADF(热激活延迟荧光)、MLCT(金属到配体电荷转移)、HLCT(具有杂化CT态)和三线态-三线态消灭方法中的至少一种方法产生发射的化合物。
根据本发明的一些实施方式,发光层中的客体材料中可以包括苝的衍生物、蒽的衍生物、芴类衍生物、二苯乙烯基芳类衍生物、芳胺类衍生物、有机硅类衍生物、有机硼类衍生物、咔唑-三嗪类衍生物、吖啶类衍生物、含有酮类衍生物、砜基类衍生物、氰基衍生物和氧杂蒽类衍生物,但不限于此。
在本发明的一些优选实施方式中,所述砜基类衍生物具有如下所示的通式:
所述酮类衍生物具有如下所示的通式:
在上述砜基类衍生物和酮类衍生物的通式中,R20、R21、R22和R23各自独立地选自单键、氢、氘、烷基、苯、二联苯、三联苯、四联苯、萘、苯基萘、蒽、菲、苯并菲、芘、芴、咔唑、噻吩、苯并噻吩、二苯并噻吩、呋喃、苯并呋喃、二苯并呋喃、吲哚、吲哚咔唑、茚并咔唑、吡啶、嘧啶、咪唑、噻唑、喹啉、异喹啉、喹喔啉、喹唑啉、卟啉、咔啉、吡嗪、哒嗪或三嗪,以及它们的取代物表示的基团。
根据本发明的一些实施方式,空穴阻挡层的材料优选为具备如下第1和/或第2个条件的化合物:
第1:具备较高的HOMO能级(绝对值较大),其目的就是减少离开发光层的空穴数目,从而提高电子和空穴在发光层的复合几率。
第2:具备较大的三线态能量,其目的就是减少离开发光层的激子数量,从而提高激子转换发光的效率。
根据本发明的一些实施方式,形成所述空穴阻挡层的材料可以包括含有菲啰啉衍生物(例如Bphen,BCP),苯并菲衍生物,苯并咪唑衍生物,但不限于此。
根据本发明的一些实施方式,电子注入层是注入来自电极的电子的层,并且电子注入材料优选为这样的化合物:其具有传输电子的能力,具有注入来自阴极的电子的效应,具有将电子注入发光层或发光材料的优异效应,防止发光层中产生的激子移动至空穴注入层,此外还具有优异的薄膜形成能力。电子注入层材料例如包括LiF、CsF、Cs2CO3、LiQ,但不限于此。
根据本发明的一些实施方式,形成所述阴极材料通常优选具有小功函数的材料,可以使电子顺利注入有机材料层,能够在本公开内容中使用的阴极材料可以选自以下材料的一种或多种,Al、Mg和Ag中的一种或多种。
根据本发明的一些实施方式,本发明的有机电致发光器件优选借助于真空蒸镀的方法涂布一个层或者多个层。在真空蒸镀***中,真空度需达到10-3Pa以下,优选小于10- 4Pa以下,开始真空蒸镀本发明提供化合物的有机薄膜。如果低于该真空度,在沉积薄膜时,由于腔体内气体分子的散射,使有机分子沉积到基底上的速率不均匀,易形成不规则排列,导致缺陷或针孔。同时也降低了薄膜的沉积速率,浪费材料,导致腔体污染,并把腔体内气体分子作为杂质引入薄膜。
根据本发明的一些实施方式,对于薄膜生长过程,则需在抽真空前,即需要把高纯待蒸发的材料放置在束源中,并且样品要先用掩膜挡住,待材料蒸发速率合适后再换对应的掩膜板露出需要沉积薄膜的部分,材料被加热蒸发出来以后,有机材料或金属原子将具有一定初速度,会脱离材料表面向外飞散,如果飞散过程中碰上气体分子,这些被蒸发出来的分子有可能被散射,相反则一部分从材料表面做匀速直线运动到样品表面,并沉积下来,形成一层薄膜,薄膜厚度分布与束源和样品的相对位置及发散角有关。在薄膜沉积过程中,优选控制薄膜厚度均匀和蒸发速率恒定。
根据本发明的一些实施方式,本发明的有机电致发光器件优选通过有机气相沉积方法或者借助于载气升华来涂布一个层或者多个层。在有机气相淀积中,有机小分子材料置于一个外部单独的、热可控的容器单元中,通过惰性载运气体(如氮气)来携带和输运从加热容器单元中蒸发的材料,气流速率、压力和温度为该工艺的控制参数。在热壁OVDP反应室中,材料从高于基板几厘米上方的喷头喷出,淀积在冷却的基板上。淀积速率主要由载运气体流速控制。
根据本发明的一些实施方式,本发明的有机电致发光器件优选通过光引发热成像或热转印,来形成一层或者多层结构。
根据本发明的一些实施方式,本发明的有机电致发光器件优选将本发明的有机化合物配制成溶液,通过旋涂或借助于任何印刷方式,例如丝网印刷、柔性版印刷、喷墨印刷、平版印刷,更优选的是喷墨印刷,来形成一个层或者多个层结构。但是,用这种方法来制作多个层时,容易出现层与层之间的破坏,即当制作完成一个层时,再用溶液制作另外一个层时,溶液中的溶剂会破坏掉已经形成的层,这不利于器件制作。本发明提供的有机化合物能够通过结构修饰取代,让本发明的有机化合物在加热或者紫外曝光的情况下发生交联作用,从而保持完整的层而不会被破坏。本发明的有机化合物另外可从溶液中施加,并且通过后续的在聚合物网络中的交联或者固定在相应的层中。
在本发明的一些优选实施方式中,通过从溶液中施加一个或者多个层和通过升华方法施加一个或者多个层来制造本发明的有机电致发光器件。
根据本发明的一些实施方式,本发明的制备有机电致发光器件的优选的溶剂选自甲苯、苯甲醚、邻二甲苯、间二甲苯、对二甲苯、苯甲酸甲酯、均三甲苯、萘满、邻二甲氧基苯、THF、甲基-THF、THP、氯苯、苯氧基甲苯,特别是3-苯氧基甲苯、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯烷酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、苯并噻唑、苯甲酸丁酯、异丙醇、异丙苯、环己醇、环己酮、环己基苯、十氢萘、十二烷基苯、苯甲酸甲酯、NMP、对甲基异并基苯、苯***、1,4-二异丙基苯、二苄醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二丁基醚、二乙二醇单丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-异丙基萘、戊苯、己苯、庚苯、辛苯、1,1-双(3,4-二甲基苯基)乙烷、2-庚醇、3-庚醇,或这些溶剂的混合物。
在本发明的一些优选实施方式中,在制备本发明的有机电致发光器件时,将本发明的有机化合物和其它化合物先充分混合,然后再通过上述施加方式,来形成一个层或者多个层。更加优选的是,在真空蒸镀***中,在小于10-3Pa、优选小于10-4Pa的初始压力下,通过气相沉积施加各化合物,来形成一个层或者多个层。
具体实施方式
本发明对制备式所示通式结构的化合物的制备方法没有特别的限制,本领域技术人员能够根据本发明提供的有机化合物的结构式结合制备例的制备方法确定合适的合成方法。
进一步地,本发明的制备例中示例性地给出了一些有机化合物的制备方法,本领域技术人员可以根据这些示例性的制备例的制备方法得到本发明提供的有机化合物。本发明在此不再详述制备本发明的各种化合物的具体制备方法,本领域技术人员不应理解为对本发明的限制。
实施例中未注明具体条件者,按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者,均为可以通过市购获得的常规产品。
在没有特别说明的情况下,下文所述的室温均表示25±1℃。
中间体M-1的合成
中间体M-1的合成:在1L三口瓶,氮气保护下加入2-溴苯酚(17.2g,0.1mol)溶于180ml二甲苯溶剂中,依次加入邻氯碘苯(11.9g,0.05mol),氯化亚铜(0.3g,0.03mol),水合1,10-菲啰啉(3.96g,0.02mol),氢氧化钾(16.83g,0.3mol),升温搅拌,升温至130℃时,向其中滴加邻氯碘苯(11.9g,0.05mol)和20ml的二甲苯混合液,滴加完毕后保持回流反应,20h后检测原料反应完毕,滴加15ml浓盐酸,滴加完毕后搅拌1h,过滤,向滤液中加入1L水,静置分液,水洗有机相两次,加入无水硫酸钠,干燥2h,过滤干燥剂,旋干有机溶剂。将残余物通过硅胶柱色谱分离,得到白色固体(收率:68%)。
质谱:C12H8BrClO,理论值:281.94,实测值:281.9。元素分析:理论值:C:50.83%,H:2.84%,实测值:C:50.85%,H:2.81%。
中间体M-2的合成
中间体M-2的合成:在1L三口瓶,加入2-溴硫代苯酚(18.8g,0.1mol)溶于200ml二甲苯溶剂中,依次加入邻氯碘苯(11.9g,0.05mol),氯化亚铜(0.3g,0.03mol),水合1,10-菲啰啉(3.96g,0.02mol),氢氧化钾(16.83g,0.3mol),升温搅拌,升温至130℃时,向其中滴加邻氯碘苯(11.9g,0.05mol)和20ml的二甲苯混合液,滴加完毕后保持回流反应,22h后检测原料反应完毕,滴加15ml浓盐酸,滴加完毕后搅拌1h,过滤,向滤液中加入1L水,静置分液,水洗有机相两次,加入无水硫酸钠,干燥2h,过滤干燥剂,旋干有机溶剂。将残余物通过硅胶柱色谱分离,得到白色固体(收率:685%)。
质谱:C12H8BrClS,理论值:297.92,实测值:297.9。元素分析:理论值:C:48.10%,H:2.69%,实测值:C:48.12%,H:2.67%。
中间体M-3的合成
中间体M-3的合成:在1L的三口瓶中,氮气保护下,加入1-溴-9-芴酮(25.8g,0.1mol),苯硼酸(12.2g,0.1mol),甲苯(135ml)、乙醇(90ml)和水(45ml)的混合溶液,开始搅拌,再次加入碳酸钾(34.5g,0.25mol),四(三苯基膦)钯(1.16g,1mmol),升温至回流6h,检测原料反应完毕,向反应液中加入300ml去离子水,搅拌10分钟,取有机相用甲苯洗涤三次,合并有机相,无水硫酸镁干燥。过滤干燥剂,旋干有机溶剂,残余物通过硅胶色谱柱分离,得到黄色固体(收率:69%)。
质谱:C19H12O,理论值:256.09,实测值:256.1。元素分析:理论值:C:89.04%,H:4.72%,实测值:C:84.01%,H:4.76%。
中间体M-4的合成
中间体M-4的合成:合成方法同中间体M-3的合成方法相同,得到黄色固体(收率:66%)。
质谱:C25H16O,理论值:332.12,实测值:332.1。元素分析:理论值:C:90.33%,H:4.85%,实测值:C:90.36%,H:4.82%。
中间体M-5的合成
中间体M-5的合成:合成方法同中间体M-3的合成方法相同,得到黄色固体(收率:70%)。
质谱:C25H16O,理论值:332.12,实测值:332.1。元素分析:理论值:C:90.33%,H:4.85%,实测值:C:90.32%,H:4.83%。
中间体M-6的合成
中间体M-6的合成:在500ml三口瓶中,将中间体M-1(2.82g,0.01mol)加入无水THF(35ml),氮气保护,降温至-78℃,滴加2.5mol/L的正丁基锂4.5ml,-78℃保温0.5小时,升温至室温,保持1小时,再降温至-78℃加入中间体M-3,升温至室温,1h后加水淬灭过滤,滤液用氯仿萃取三遍,无水硫酸钠干燥后过滤干燥剂,得到粗品,将粗品溶于1,2-二氯乙烷(50ml),降温至0℃,逐滴加入0.1mol的三氟甲烷磺酸,滴加完毕后,加热回流2小时,冷却至室温,加NaHCO3水溶液调节溶液至中性,无水硫酸钠干燥后过滤,将滤液减压旋干,通过柱层析得到白色固体(收率:55%)。
质谱:C31H19ClO,理论值:442.11,实测值:442.1。元素分析:理论值:C:84.06%,H:4.32%,实测值:C:84.03%,H:4.36%。
中间体M-7的合成
中间体M-7的合成:合成方法同中间体M-6的合成方法相同,得到白色固体(收率:51%)。
质谱:C37H23ClO,理论值:518.14,实测值:518.2。元素分析:理论值:C:85.62%,H:4.47%,实测值:C:85.67%,H:4.43%。
中间体M-8的合成
中间体M-8的合成:合成方法同中间体M-6的合成方法相同,得到白色固体(收率:48%)。
质谱:C37H23ClO,理论值:518.14,实测值:518.1。元素分析:理论值:C:85.62%,H:4.47%,实测值:C:85.65%,H:4.44%。
中间体M-9的合成
中间体M-9的合成:合成方法同中间体M-6的合成方法相同,得到白色固体(收率:57%)。
质谱:C31H19ClS,理论值:458.09,实测值:458.1。元素分析:理论值:C:81.12%,H:4.17%,实测值:C:81.16%,H:4.18%。
中间体M-10的合成
中间体M-10的合成:合成方法同中间体M-6的合成方法相同,得到白色固体(收率:55%)。
质谱:C37H23ClS,理论值:534.12,实测值:534.1。元素分析:理论值:C:83.05%,H:4.33%,实测值:C:83.10%,H:4.35%。
制备例1:化合物1的合成
化合物1的合成:在1L三口瓶中,通入氮气保护,依次将中间体M-6(13.26g,0.03mol),二苯胺(5.07g,0.03mol),叔丁醇钠(7.21g,0.075mol),三(二亚苄基丙酮)二钯(0.22g,0.3mmol),三叔丁基膦(0.06g,0.3mmol)和甲苯溶剂(200ml),通氮气下搅拌,升温至回流3h,HPLC检测原料反应完毕,将反应液降温至室温,向其中加入稀盐酸调节为中性,加入200ml的去离子水,进行搅拌,分液,取有机相用甲苯溶剂洗涤三次,用无水硫酸镁进行干燥,有机相用旋转蒸发除去溶剂,残余物通过硅胶柱色谱分离得到白色固体(收率:76%)。
质谱:C43H29NO,理论值:575.22,实测值:575.2。1H-NMR(400MHz,CDCl3)(ppm)δ=6.83~6.92(2H,m),6.94~7.11(9H,m),7.15~7.19(2H,m),7.20~7.22(2H,m),7.23~7.25(2H,m),7.27~7.32(2H,m),7.34~7.41(3H,m),7.42~7.47(2H,m),7.49~7.57(1H,m),7.62~7.70(2H,m),7.88~7.92(1H,m),7.98~8.02(1H,m)。
制备例2:化合物17的合成
化合物17的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:75%)。
质谱:C52H37NO,理论值:691.29,实测值:691.3。1H-NMR(400MHz,CDCl3)(ppm)δ=1.68~1.70(6H,s),6.83~6.94(2H,m),6.96~7.10(5H,m),7.15~7.19(2H,m),7.20~7.22(2H,m),7.23~7.25(2H,m),7.27~7.32(2H,m),7.34~7.41(4H,m),7.42~7.50(3H,m),7.52~7.58(2H,m),7.64~7.70(2H,m),7.84~7.92(4H,m),7.98~8.02(1H,m)。
制备例3:化合物24的合成
化合物24的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:78%)。
质谱:C55H37NO,理论值:727.29,实测值:727.3。1H-NMR(400MHz,CDCl3)(ppm)δ=6.83~6.92(2H,m),6.94~7.04(3H,m),7.05~7.07(1H,m),7.08~7.10(1H,m),7.15~7.24(4H,m),7.27~7.32(2H,m),7.34~7.44(5H,m),7.45~7.54(6H,m),7.56~7.63(3H,m),7.66~7.78(6H,m),7.88~7.95(2H,m),7.98~8.02(1H,m),8.08~8.13(1H,m)。
制备例4:化合物29的合成
化合物29的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:77%)。
质谱:C55H37NO,理论值:727.29,实测值:727.3。1H-NMR(400MHz,CDCl3)(ppm)δ=6.83~7.01(3H,m),7.02~7.06(1H,m),7.15~7.25(3H,m),7.27~7.32(1H,m),7.34~7.41(8H,m),7.41~7.45(3H,m),7.46~7.50(4H,m),7.51~7.54(4H,m),7.56~7.58(2H,m),7.59~7.63(1H,m),7.66~7.70(1H,m),7.42~7.78(4H,m),7.88~7.92(1H,d),7.98~8.02(1H,d)。
制备例5:化合物42的合成
化合物42的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:73%)。
质谱:C58H41NO,理论值:767.32,实测值:767.3。1H-NMR(400MHz,CDCl3)(ppm)δ=1.68~1.70(6H,s),6.83~6.95(2H,m),6.96~7.06(2H,m),7.15~7.20(2H,m),7.20~7.25(2H,m),7.27~7.29(1H,m),7.30~7.32(1H,m),7.34~7.41(7H,m),7.42~7.50(5H,m),7.52~7.59(5H,m),7.66~7.70(1H,m),7.72~7.77(2H,m),7.82~7.89(3H,m),7.91~7.92(1H,m),7.98~8.02(1H,m)。
制备例6:化合物51的合成
中间体51-1的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:66%)。
化合物51的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:72%)。
质谱:C61H39NOS,理论值:833.28,实测值:833.3。1H-NMR(400MHz,CDCl3)(ppm)δ=6.83~6.94(2H,m),6.96~7.06(3H,m),7.14~7.22(2H,m),7.23~7.25(4H,m),7.27~7.32(2H,m),7.33~7.47(7H,m),7.48~7.54(5H,m),7.55~7.61(4H,m),7.66~7.70(1H,m),7.72~7.77(4H,m),7.84~7.92(2H,m),7.98~8.02(1H,m),8.31~8.35(1H,m),8.43~8.47(1H,m)。
制备例7:化合物55的合成
中间体55-1的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:68%)。
化合物55的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:72%)。
质谱:C59H39NO,理论值:777.30,实测值:777.3。1H-NMR(400MHz,CDCl3)(ppm)δ=6.81~6.98(3H,m),6.99~7.04(1H,m),7.12~7.22(5H,m),7.24~7.26(1H,m),7.27~7.38(9H,m),7.39~7.47(5H,m),7.49~7.56(4H,m),7.63~7.71(3H,m),7.72~7.76(3H,m),7.83~7.89(2H,m),7.95~7.99(1H,m),8.43~8.50(1H,m),8.89~8.94(1H,d)。
制备例8:化合物59的合成
化合物59的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:75%)。
质谱:C55H35NO2,理论值:741.27,实测值:741.3。1H-NMR(400MHz,CDCl3)(ppm)δ=6.82~6.93(2H,m),6.95~7.05(2H,m),7.13~7.16(1H,m),7.16~7.23(5H,m),7.26~7.31(2H,m),7.32~7.40(5H,m),7.40~7.49(7H,m),7.51~7.57(3H,m),7.62~7.69(2H,m),7.72~7.76(2H,m),7.87~7.91(1H,m),7.95~8.01(2H,m),8.20~8.21(1H,d)。
制备例9:化合物77的合成
化合物77的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:70%)。
质谱:C61H45NO,理论值:807.35,实测值:807.4。1H-NMR(400MHz,CDCl3)(ppm)δ=1.68~1.70(12H,s)6.83~6.95(2H,m),6.96~7.06(2H,m),7.15~7.25(4H,m),7.27~7.29(1H,m),7.31~7.35(4H,m),7.36~7.41(4H,m),7.42~7.49(3H,m),7.50~7.56(3H,m),7.59~7.63(2H,m),7.66~7.70(1H,m),7.80~7.85(2H,m),7.87~7.92(4H,m),7.98~8.02(1H,m)。
制备例10:化合物85的合成
化合物85的合成:在500ml的三口瓶中,氮气保护下,依次加入中间体M-6(22.1g,0.05mol),9H-咔唑(8.35g,0.05mol),活化铜粉(6.4g,0.1mol),18-冠-6(2.64g,0.01mol),碳酸钾(17.25g,0.125mol)和邻二氯苯(250ml),加热搅拌,升温至回流60h,将反应液降温至室温,补加200ml甲苯,过滤,减压旋干滤液,用石油醚/乙酸乙酯为洗脱剂柱层析,得到淡黄色固体(收率:72%)。
质谱:C43H27NO,理论值:573.21,实测值:573.2。1H-NMR(400MHz,CDCl3)(ppm)δ=6.96~7.03(1H,m),7.03~7.25(9H,m),7.27~7.32(1H,m),7.34~7.48(7H,m),7.49~7.61(3H,m),7.66~7.70(1H,m),7.88~7.92(1H,m),7.98~8.02(1H,m),8.15~8.21(2H,m),8.53~8.57(1H,m)。
制备例11:化合物98的合成
化合物98的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:78%)。
质谱:C49H33NS,理论值:667.23,实测值:667.2。1H-NMR(400MHz,CDCl3)(ppm)δ=6.68~6.72(1H,m),6.86~6.94(2H,m),6.96~7.10(5H,m),7.20~7.25(2H,m),7.27~7.41(8H,m),7.42~7.50(5H,m),7.51~7.58(3H,m),7.66~7.77(4H,m),7.88~8.02(3H,m)。
制备例12:化合物104的合成
化合物104的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:75%)。
质谱:C49H31NOS,理论值:681.21,实测值:681.2。1H-NMR(400MHz,CDCl3)(ppm)δ=6.68~6.72(1H,m),6.85~6.94(2H,m),6.96~7.04(3H,m),7.05~7.10(2H,m),7.20~7.25(2H,m),7.26~7.41(8H,m),7.42~7.50(4H,m),7.52~7.57(2H,m),7.66~7.71(2H,m),7.80~7.84(1H,m),7.88~7.92(1H,m),7.96~8.02(2H,m),8.21~8.23(1H,d)。
制备例13:化合物113的合成
化合物113的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:77%)。
质谱:C55H37NS,理论值:743.26,实测值:743.2。1H-NMR(400MHz,CDCl3)(ppm)δ=6.68~6.72(1H,m),6.85~6.97(2H,m),7.01~7.06(2H,m),7.20~7.28(1H,m),7.29~7.41(10H,m),7.42~7.50(7H,m),7.52~7.54(3H,m),7.56~7.58(2H,m),7.66~7.71(2H,m),7.72~7.79(5H,m),7.88~7.92(1H,d),7.98~8.02(1H,d)。
制备例14:化合物124的合成
化合物124的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:71%)。
质谱:C64H45NS,理论值:859.33,实测值:859.3。1H-NMR(400MHz,CDCl3)(ppm)δ=1.68~1.71(6H,s),6.68~6.72(1H,m),6.85~6.99(2H,m),7.01~7.06(2H,m),7.20~7.27(7H,m),7.29~7.47(10H,m),7.48~7.50(2H,m),7.52~7.57(4H,m),7.66~7.71(2H,m),7.72~7.78(4H,m),7.83~7.85(1H,m),7.88~7.89(2H,m),7.91~7.92(1H,m),7.98~8.02(1H,m)。
制备例15:化合物131的合成
化合物131的合成:合成方法同化合物1的合成方法相同,得到白色固体(收率:72%)。
质谱:C58H41NS,理论值:783.30,实测值:783.3。1H-NMR(400MHz,CDCl3)(ppm)δ=1.68~1.70(6H,s),6.68~6.72(1H,m),6.85~6.99(2H,m),7.01~7.06(2H,m),7.15~7.22(2H,m),7.23~7.28(3H,m),7.30~7.41(8H,m),7.42~7.47(3H,m),7.48~7.58(5H,m),7.66~7.77(5H,m),7.84~7.89(2H,m),7.91~7.92(1H,m),7.98~8.02(1H,m)。
制备例16:化合物150的合成
化合物150的合成:合成方法同化合物161的合成方法相同,得到白色固体(收率:85%)。
质谱:C49H31NS,理论值:665.22,实测值:665.2。1H-NMR(400MHz,CDCl3)(ppm)δ=6.98~7.08(2H,m),7.09~7.17(3H,m),7.19~7.28(2H,m),7.31~7.41(4H,m),7.42~7.54(9H,m),7.56~7.64(4H,m),7.65~7.71(2H,m),7.73~7.78(1H,m),7.88~7.92(1H,m),7.98~8.02(1H,m),8.13~8.15(1H,d),8.53~8.57(1H,d)。
制备例17:化合物161的合成
化合物161的合成:在1L三口瓶中,氮气保护下,加入中间体M-6(22.1g,0.05mol),B-[4-[双(联苯-4-基)氨基]苯基]硼酸(22.06g,0.05mol),甲苯(250ml),二环己基(2’,4’,6’-三异丙基-(1,1’-联苯基)-2-基)膦酸(1.19g,2.5mmol),三(二亚苄基丙酮)二钯(0.36g,0.5mmol),含有磷酸二氢钾(17g,0.125mol)的水溶液80ml,开始搅拌并加热至90℃过夜反应,28h后将反应降至40℃,在降至0℃保持3h,过滤得到粗品,将粗品水洗(250ml),然后用甲醇洗(250ml),得到的固体用甲苯为洗脱剂,残余物用硅胶柱色谱分离得到淡黄色固体化合物(收率:80%)。
质谱:C61H41NO,理论值:803.32,实测值:803.3。1H-NMR(400MHz,CDCl3)(ppm)δ=6.96~7.03(1H,m),7.15~7.30(5H,m),7.31~7.32(1H,m),7.34~7.41(10H,m),7.42~7.50(7H,m),7.51~7.58(8H,m),7.66~7.70(1H,m),7.72~7.79(5H,m),7.83~7.92(2H,m),7.98~8.02(1H,m)。
器件实施例1
将涂布了ITO透明导电层的玻璃板进行超声处理,在去离子水中冲洗,在丙酮∶乙醇混合溶剂(体积比1∶1)中超声除油,在洁净环境下烘烤至完全除去水分,用紫外光和臭氧清洗,并用低能阳离子束轰击表面;
将上述带有阳极的玻璃基片置于真空腔内,抽真空至1×10-4Pa,在上述阳极层膜上真空蒸镀HAT-CN作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀总膜厚为5nm;接着蒸镀空穴传输层NPB,蒸镀速率为0.1nm/s,厚度为60nm;空穴传输层上真空蒸镀化合物1作为电子阻挡层,蒸镀速率为0.1nm/s,厚度为10nm;
在空穴传输层之上真空蒸镀器件的发光层,发光层包括主体材料和客体材料,利用多源共蒸的方法,调节主体材料ADN蒸镀速率为0.1nm/s,客体材料BD蒸镀速率为主体材料的蒸镀速率的6%比例设定,蒸镀总膜厚为30nm;
在发光层之上真空蒸镀器件的空穴阻挡层TPBi,蒸镀速率为0.1nm/s,厚度为5nm;然后蒸镀电子传输层,利用多源共蒸的方法,调节ET-1和ET-2的蒸镀速率均为0.1nm/s,蒸镀总膜厚为30nm;
在电子传输层(ETL)上真空蒸镀厚度为1nm的LiF作为电子注入层,厚度为150nm的Al层作为器件的阴极。
器件实施例2-17
采用与器件实施例1相似的方法制备器件实施例2-17的有机发光器件,所不同的是,将器件实施例1中的化合物1替换成表1中的相应化合物。
涉及的分子结构如下:
器件对比例1
采用与器件实施例1相似的方法制备器件对比例1的有机电致发光器件,所不同的是,将器件实施例1中的化合物1分别替换成Ref-1。
质谱:C19H33NO,理论值:651.26,实测值:651.3。1H-NMR(400MHz,CDCl3)(ppm)δ=6.84~6.89(1H,m),6.91~6.97(1H,m),6.99~7.06(2H,m),7.18~7.19(1H,m),7.21~7.22(1H,m),7.23~7.25(1H,m),7.26~7.29(1H,m),7.30~7.32(1H,m),7.34~7.36(3H,m),7.37~7.42(4H,m),7.42~7.44(1H,m),7.45~7.47(1H,m),7.48~7.50(2H,m),7.51~7.54(3H,m),7.56~7.58(2H,m),7.66~7.68(1H,m),7.69~7.71(1H,m),7.72~7.74(2H,m),7.75~7.78(2H,m),7.88~7.89(1H,m),7.91~7.92(1H,m)。
测试例1
在亮度1000cd/m2下,测定器件实施例1-17和器件对比例1中制备得到的有机电致发光器件的驱动电压和电流效率,结果见表1。
表1
从表1所示的实验结果可以看出,由本发明的化合物作为有机电致发光器件的电子阻挡层材料时,与现有技术相比,具有更低的驱动电压及更高的发光效率。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于此。在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,包括各个技术特征以任何其它的合适方式进行组合,这些简单变型和组合同样应当视为本发明所公开的内容,均属于本发明的保护范围。
Claims (10)
2.根据权利要求1所述的有机化合物,其特征在于,所述取代基选自卤素、氰基、C1-C10烷基和C1-C10烷氧基,优选所述卤素选自氟、氯、溴和碘,所述C1-C10烷基选自甲基、乙基、正丙基、异丙基、正丁基、叔丁基、异丁基、正戊基、异戊基、正己基和正庚基;所述C1-C10烷氧基选自甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、异丁氧基、正戊氧基、异戊氧基、正己氧基和正庚氧基。
3.根据权利要求1或2所述的有机化合物,其特征在于,结构如式II或式III所示,
其中,X选自氧或硫;
L选自单键、含取代基或不含取代基的C6-C30亚芳基和含取代基或不含取代基的C6-C30亚杂芳基;
R1选自含取代基或不含取代基的C6-C40芳基和含取代基或不含取代基的C6-C40杂芳基;
R21和R22相同或不同,各自独立选自含取代基或不含取代基的C6-C40芳基、含取代基或不含取代基的C3-C40杂芳基、含取代基或不含取代基的C9-C40稠环芳基和含取代基或不含取代基的C5-C40稠环杂芳基;
R23选自含取代基或不含取代基的C9-C40稠环芳基和含取代基或不含取代基的C5-C40稠环杂芳基。
4.根据权利要求1-3中任一项所述的有机化合物,其特征在于,L选自单键、含取代基或不含取代基的C6-C20亚芳基和含取代基或不含取代基的C6-C20亚杂芳基,优选选自单键、亚苯基、亚联苯基或亚萘基。
7.根据权利要求1-6中任一项所述的有机化合物,其特征在于,R1选自含取代基或不含取代基的C6-C30芳基和含取代基或不含取代基的C6-C30杂芳基;优选选自含取代基或不含取代基的C6-C20芳基,更优选选自含取代基或不含取代基的苯基、联苯基、萘基;例如R1选自以下基团:
R21和R22相同或不同,各自独立选自含取代基或不含取代基的C6-C30芳基、含取代基或不含取代基的C3-C30杂芳基、含取代基或不含取代基的C9-C30稠环芳基和含取代基或不含取代基的C5-C30稠环杂芳基;
优选选自含取代基或不含取代基的C6-C20芳基、含取代基或不含取代基的C3-C20杂芳基、含取代基或不含取代基的C9-C20稠环芳基和含取代基或不含取代基的C5-C20稠环杂芳基;
更优选选自含取代基或不含取代基的苯基、含取代基或不含取代基的联苯基、含取代基或不含取代基的萘基、含取代基或不含取代基的苯基萘基、含取代基或不含取代基的二苯并呋喃基、含取代基或不含取代基的二苯并噻吩基、含取代基或不含取代基的咔唑基、含取代基或不含取代基的苯基咔唑基、含取代基或不含取代基的二苯基咔唑基、含取代基或不含取代基的萘基咔唑基和含取代基或不含取代基的芴基;例如R21和R22相同或不同,各自独立选自以下基团:
R23选自含取代基或不含取代基的C9-C30稠环芳基和含取代基或不含取代基的C5-C30稠环杂芳基;优选选自含取代基或不含取代基的C9-C20稠环芳基、含取代基或不含取代基的C5-C20稠环杂芳基;更优选选自含取代基或不含取代基的咔唑基、含取代基或不含取代基的苯基咔唑基、含取代基或不含取代基的二苯基咔唑基和含取代基或不含取代基的萘基咔唑基;例如R23选自以下基团:
9.根据权利要求1-8中任意一项所述的有机化合物在电子器件尤其是有机电致发光器件中的应用,优选地,所述有机化合物用于空穴传输层、电子阻挡层和发光层中的至少一层,尤其是用于电子阻挡层中。
10.一种有机电致发光器件,所述有机电致发光器件包括依次层叠设置的阳极、空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和阴极,其中所述空穴传输层、电子阻挡层和发光层的至少一层中包括根据权利要求1-8中任意一项所述的有机化合物,优选所述电子阻挡层中包括根据权利要求1-8中任意一项所述的有机化合物。
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