CN108358905B - 一种化合物、发光材料及器件、显示装置 - Google Patents
一种化合物、发光材料及器件、显示装置 Download PDFInfo
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- CN108358905B CN108358905B CN201810265829.2A CN201810265829A CN108358905B CN 108358905 B CN108358905 B CN 108358905B CN 201810265829 A CN201810265829 A CN 201810265829A CN 108358905 B CN108358905 B CN 108358905B
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 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
- HITRWHKLCHWBNZ-UHFFFAOYSA-N triphenyl-[4-(9-phenylfluoren-9-yl)phenyl]silane Chemical compound C1=CC=CC=C1C1(C=2C=CC(=CC=2)[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 HITRWHKLCHWBNZ-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000001834 xanthenyl group Chemical group 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
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
Description
技术领域
本发明涉及有机电致发光材料技术领域,特别是涉及一种化合物、发光材料及器件、显示装置。
背景技术
根据发光机制,可用于OLED发光层的材料主要有以下四种:荧光材料、磷光材料、三线态-三线态湮灭(TTA)材料和热活化延迟荧光(TADF)材料。其中,荧光材料的理论最大内量子产率不超过25%,TTA材料的理论最大内量子产率不超过62.5%;磷光材料、TADF材料的理论最大内量子产率均可达100%。然而,磷光材料基本为Ir、Pt、Os、Re、Ru等重金属配合物,生产成本较高,不利于大规模生产;且在高电流密度下,磷光材料存在严重的效率滚降现象;此外,磷光器件的稳定性也并不好。
TADF材料主要为有机化合物,不需要稀有金属元素,生产成本低,并且可通过多种方法进行化学修饰。
发明内容
本发明提供了一种化合物、发光材料及器件、显示装置。
根据本发明的一方面,提供了一种化合物,具有式(I)所示的结构:
其中,D表示电子给体单元,A表示电子受体单元,L表示连接单元,L选自苯并环烷烃基团,并且所述每个D和每个A均与苯并环烷烃基团上的苯环直接相连,a、b各自独立地选自1、2或者3。
根据本发明的一个实施方式,所述苯并环烷烃基团选自苯并环戊烷基、苯并环己烷基、苯并环庚烷基、苯并二环戊烷基、苯并二环己烷基和苯并二环庚烷基中的任意一种。
根据本发明的一个实施方式,至少一个D单元和至少一个A单元与苯并环烷烃基团的苯环上的相邻-CH-相连。
根据本发明的一个实施方式,所述苯并环烷烃基团选自
中的任意一种,*表示与D单元或A单元连接的位置。
根据本发明的一个实施方式,D单元选自以下结构中的任意一种或一种以上:
其中,X1和X2各自独立地选自碳原子、氮原子、氧原子、硫原子或硅原子;
#表示与能够连接单元连接的位置;
m和n各自独立地选自0、1、2或3;
R1、R2、R3、R4各自独立地选自氢原子、碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为4-20的苯基、碳原子数为4-20的杂芳基、碳原子数为4-20的咔唑基、碳原子数为4-20的二苯胺基、碳原子数为4-20的吖啶基、碳原子数为4-20的吖嗪基中的任意一种或一种以上;
当X为氧原子和硫原子时,R3和R4不存在。
根据本发明的一个实施方式,D单元选自以下结构中的任意一种或一种以上:
其中,#表示与连接单元连接的位置,每个结构式中的R各自独立地表示碳原子数1-20的烷基、碳原子数1-20的烷氧基、碳原子数2-20的烯基、碳原子数2-20的炔基、碳原子数6-40的芳香基、碳原子数4-40的杂芳香基。
根据本发明的一个实施方式,D单元选自以下结构中的任意一种或一种以上:
其中,X选自碳原子、氮原子、氧原子、硫原子或硅原子;
#表示与连接单元连接的位置;
p、q、r、s各自独立地选自0、1、2或3;
R1、R2、R3、R4各自独立地选自氢原子、碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为4-20的苯基、碳原子数为4-20的杂芳基、碳原子数为4-20的咔唑基、碳原子数为4-20的二苯胺基、碳原子数为4-20的吖啶基、碳原子数为4-20的吖嗪基中的任意一种或一种以上;
当X为氧原子和硫原子时,R3和R4不存在。
根据本发明的一个实施方式,D单元选自以下结构中的任意一种或一种以上:
其中,#表示与连接单元连接的位置。
根据本发明的一个实施方式,D单元选自以下结构中的任意一种或一种以上:
#表示与连接单元连接的位置;
r、s各自独立地选自0、1、2或3;
R1、R2各自独立地选自氢原子、碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为4-20的苯基、碳原子数为4-20的杂芳基、碳原子数为4-20的咔唑基、碳原子数为4-20的二苯胺基、碳原子数为4-20的吖啶基、碳原子数为4-20的吖嗪基中的任意一种或一种以上。
根据本发明的一个实施方式,D单元选自以下结构中的任意一种或一种以上:
其中,#表示与连接单元连接的位置。
根据本发明的一个实施方式,D单元选自以下结构中的任意一种或一种以上:
其中,#表示能够与连接单元连接的位置。
根据本发明的一个实施方式,A单元选自含氮杂环类取代基、氰基类取代基、三芳基硼类取代基、苯甲酮类取代基、芳杂环甲酮类取代基和砜类取代基中的任意一种或一种以上。
根据本发明的一个实施方式,所述含氮杂环类取代基选自以下结构中的任意一种或一种以上:
其中,#表示能够与连接单元连接的位置;
R选自氢原子、碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为4-8的环烷基、碳原子数为4-20的芳基、碳原子数为4-20的杂芳基。
根据本发明的一个实施方式,所述氰基类取代基选自以下结构中的一种或一种以上:
其中,#表示能够与连接单元连接的位置。
根据本发明的一个实施方式,所述三芳基硼类取代基选自以下结构中的一种或一种以上:
其中,#表示能够与连接单元连接的位置。
根据本发明的一个实施方式,所述苯甲酮类取代基、芳杂环甲酮类取代基选自以下结构中的一种或一种以上:
其中,#表示能够与连接单元连接的位置,每个结构式中的R各自独立地表示碳原子数1-20的烷基、碳原子数1-20的烷氧基、碳原子数2-20的烯基、碳原子数2-20的炔基、碳原子数6-40的芳香基、碳原子数4-40的杂芳香基。
根据本发明的一个实施方式,所述砜类取代基选自以下结构中的一种或一种以上:
其中,#表示能够与连接单元连接的位置。
根据本发明的一个实施方式,所述A单元选自以下结构中的一种或一种以上:
其中,#表示能够与连接单元连接的位置,每个结构式中的R各自独立地表示碳原子数1-20的烷基、碳原子数1-20的烷氧基、碳原子数2-20的烯基、碳原子数2-20的炔基、碳原子数6-40的芳香基、碳原子数4-40的杂芳香基。
根据本发明的一个实施方式,D单元为取代的,取代基选自碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为3-20的环烷基、碳原子数为6-30的芳香基和碳原子数为2-20的杂芳基中的任意一种或一种以上;
A单元为取代的,取代基选自碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为3-20的环烷基、碳原子数为6-30的芳香基、碳原子数为2-20的杂芳基、氟原子、三氟甲基、氰基、羰基、酯基、磺酰基和膦氧基中的任意一种或一种以上。
根据本发明的一个实施方式,所述化合物选自
根据本发明的另一方面,提供了如上所述化合物的制备方法,包括以下步骤:
将活化的苯并环烷烃基团与活化的D单元、活化的A单元分别反应,得到所述化合物。
根据本发明的又一方面,提供了一种发光材料,所述发光材料包含根据本发明的化合物。
根据本发明的一个实施方式,所述发光材料为热激活延迟荧光材料。
根据本发明的又一方面,提供了一种有机电致发光器件,包括:
基底;
设置于所述基底上的第一电极;
设置于第一电极上的有机功能层,所述有机功能层包括一层或多层有机膜层,且至少一层所述有机膜层为发光层;
设置于所述有机功能层上的第二电极;
所述发光层包含根据本发明的发光材料。
根据本发明的一个实施方式,所述发光材料作为所述发光层的主体材料或客体材料,或者所述发光材料单独构成所述发光层以制备非掺杂有机发光显示装置。
根据本发明的又一方面,提供了一种显示装置,包括根据本发明的有机电致发光器件。
根据本发明的显示装置例如可以是手机显示屏、电脑显示屏、液晶电视显示屏等。
根据本发明的化合物可作为热激活延迟荧光(TADF)材料,S1态与T1态之间的能隙值较小且T1态激子寿命较长时,在一定温度条件下,T1态激子可以逆向系间窜越(RISC)实现T1→S1的过程,再由S1态辐射衰减至基态S0。
根据本发明的化合物通过引入电子给体单元D和电子受体单元A以及大空间位阻的构建单元降低HOMO和LUMO的交叠程度,由于ΔEst与HOMO和LUMO的交叠程度呈正相关,因此根据本发明的化合物S1态与T1态之间的能级差ΔEst较小。
在有机电致发光器件中,热激活延迟荧光(TADF)材料作为掺杂体材料可在不引入贵金属或稀土金属的情况下实现S1态和T1态激子共同参与荧光发射,IQE理论值可达到100%,可媲美磷光OLED;TADF材料为纯有机材料,在合成成本上比磷光OLED具有更大的优势;TADF材料由纯有机化合物构成,具有更好的热稳定性、化学稳定性和器件工作稳定性;TADF材料为有机化合物,具有更多的化学修饰性,可根据需求合成相应的种类多样的目标分子。
在有机电致发光器件中,为了获得平衡的载流子传输性能,减缓效率滚降现象,需要主体材料具有良好的双极性传输特性。TADF材料由于具有良好的双极性传输特性,非常适合用作磷光材料或荧光材料的主体材料。
附图说明
图1为化合物P1的HOMO、LUMO能级分布图;其中,图1中的(a)为化合物P1的HOMO能级分布图,图1中的(b)为化合物P1的LUMO能级分布图。
图2为根据本发明的有机电致发光器件的结构示意图。
图3为手机显示屏的示意图。
其中,1-基底,2-第一电极2,3-有机功能层,4-第二电极,5-显示屏。
具体实施方式
具体实施方式仅为对本发明的说明,而不构成对本发明内容的限制,下面将结合具体的实施方式对本发明进行进一步说明和描述。
本发明提供了一种化合物、发光材料及器件、显示装置。
根据本发明的一方面,提供了一种化合物,具有式(I)所示的结构:
其中,D表示电子给体单元,A表示电子受体单元,L表示连接单元,L选自苯并环烷烃基团,并且所述每个D和每个A均与苯并环烷烃基团上的苯环直接相连,a、b各自独立地选自1、2或者3。
本发明采用苯单元,具有以下优势:
1)早期的电子供体基团D和电子受体基团A直接相连的分子结构,过大的HOMO和LUMO分离程度,妨碍了光的吸收和发射过程,具有较低的光致发光量子产率(PLQY);
2)通过苯环作为给电子基团D和受电子基团A的连接单元可以使分子的HOMO和LUMO在空间上的分离程度下降,实现较高的振子强度,进而实现高的PLQY;
3)苯基团在有机电子材料上有广泛的应用,并且具有优异的光学和电学性能;
4)苯的化学修饰方法广泛,开发成熟。
进一步地,本发明采用苯并环烷烃基团作为连接单元,具有以下优势:
1)保留了苯作为连接基团的优势,是能够实现好的光学和电学性能的前提;
2)苯并环烷烃上的环烷烃有较大的空间位阻,可以实现电子供体基团D和电子受体基团A形成有效的扭曲结构,有效地增大二面角,实现分子的HOMO和LUMO在空间上的有效分离;
3)环烷烃在分子中具有不同的构象异构体。
根据本发明的一个实施方式,所述苯并环烷烃基团选自苯并环戊烷基、苯并环己烷基、苯并环庚烷基、苯并二环戊烷基、苯并二环己烷基和苯并二环庚烷基中的任意一种。
根据本发明的一个实施方式,至少一个D单元和至少一个A单元与苯并环烷烃基团的苯环上的相邻-CH-相连。
当至少一个D单元和至少一个A单元与苯并环烷烃基团的苯环上的相邻-CH-相连时,具有以下优点:
首先,D单元和A单元之间通过苯并环烷烃的邻位连接,可以增大D单元和A单元之间的二面角,使D单元和A单元之间具有较大的空间位阻作用,从而获得较小的ΔEst;其次,邻位连接增加了分子内的空间限制作用,可以降低分子的正溶剂化变色效应,同时可以提高分子发光色纯度,实现较低的半峰宽。
根据本发明的一个实施方式,所述苯并环烷烃基团选自
中的任意一种,*表示与D单元或A单元连接的位置。
可以以苯环上的四个-CH中的任意两个或两个以上与D单元、A单元连接。
根据本发明的一个实施方式,D单元可选自咔唑类衍生物,具体可选自以下结构中的任意一种或一种以上:
其中,X1和X2各自独立地选自碳原子、氮原子、氧原子、硫原子或硅原子;
#表示与能够连接单元连接的位置;
m和n各自独立地选自0、1、2或3;
R1、R2、R3、R4各自独立地选自氢原子、碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为4-20的苯基、碳原子数为4-20的杂芳基、碳原子数为4-20的咔唑基、碳原子数为4-20的二苯胺基、碳原子数为4-20的吖啶基、碳原子数为4-20的吖嗪基中的任意一种或一种以上;
当X为氧原子和硫原子时,R3和R4不存在。
更为优选的为以下结构:
其中,#表示与连接单元连接的位置,每个结构式中的R各自独立地表示碳原子数1-20的烷基、碳原子数1-20的烷氧基、碳原子数2-20的烯基、碳原子数2-20的炔基、碳原子数6-40的芳香基、碳原子数4-40的杂芳香基。
碳原子数1-20的烷基可以例如选自甲基、乙基、正丙基、异丙基、正丁基、仲丁基或叔丁基等饱和脂肪族烃基中的一种或几种。上述碳原子数1-20烷基可以具有取代基也可以不具有取代基。
碳原子数1-20的烷氧基可以例如选自甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基或叔丁氧基等饱和脂肪族烃氧基中的一种或几种。上述碳原子数1-20烷基可以具有取代基也可以不具有取代基。
碳原子数2-20的烯基可以例如选自乙烯基、丙烯基、正丁烯基、异烯基等基团中的一种或几种。上述碳原子数1-20的烯基可以具有取代基也可以不具有取代基。
碳原子数2-20的炔基可以例如选自乙炔基、丙炔基、正丁炔基等基团中的一种或几种。上述碳原子数1-20的炔基可以具有取代基也可以不具有取代基。
碳原子数6-40的芳基可以例如选自苯基、萘基、蒽基、菲基、二联苯基、9,10-苯并菲基、1,2-苯并菲基、9,9-芴基、苯三联苯基、苊烯基、苝基、芘基、茚基等芳香烃基中的一种或几种。上述碳原子数6-40的芳基可以具有取代基也可以不具有取代基。
碳原子数4-40的杂芳香基可以例如选自呋喃基、噻吩基、吡咯基、噁唑基、噻唑基、吡唑基、吡喃基、咪唑基、吡啶基、吡嗪基、嘧啶基、1,3,4-噁二唑基、1,2,4-三唑基、1,3,5-三嗪基、吲哚基、苯并咪唑基、二苯并呋喃基、二苯并噻吩基、咔唑基、喹啉基、喹喔啉基、邻菲罗啉基、吩嗪基、哒嗪基中的一种或一种以上。上述碳原子数4-40的杂芳香基可以具有取代基也可以不具有取代基。
当碳原子数1-20的烷基、碳原子数2-20的烯基、碳原子数6-40的芳香基、碳原子数4-40的杂芳香基具有取代基时,取代基可以例如选自烷基、烯基、芳基、杂芳基等。
对于本文中其他位置提到的碳原子数1-20的烷基、碳原子数2-20的烯基、碳原子数6-40的芳香基、碳原子数4-40的杂芳香基,也应作与以上相同的理解。
根据本发明的一个实施方式,D单元可选自吖啶类衍生物,具体可选自以下结构中的任意一种或一种以上:
其中,X选自碳原子、氮原子、氧原子、硫原子或硅原子;
#表示与连接单元连接的位置;
p、q、r、s各自独立地选自0、1、2或3;
R1、R2、R3、R4各自独立地选自氢原子、碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为4-20的苯基、碳原子数为4-20的杂芳基、碳原子数为4-20的咔唑基、碳原子数为4-20的二苯胺基、碳原子数为4-20的吖啶基、碳原子数为4-20的吖嗪基中的任意一种或一种以上;
当X为氧原子和硫原子时,R3和R4不存在。
更为优选的为以下结构:
其中,#表示与连接单元连接的位置。
根据本发明的一个实施方式,D单元可选自芳香胺类衍生物,具体选自以下结构中的任意一种或一种以上:
#表示与连接单元连接的位置;
r、s各自独立地选自0、1、2或3;
R1、R2各自独立地选自氢原子、碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为4-20的苯基、碳原子数为4-20的杂芳基、碳原子数为4-20的咔唑基、碳原子数为4-20的二苯胺基、碳原子数为4-20的吖啶基、碳原子数为4-20的吖嗪基中的任意一种或一种以上。
更为优选的为以下结构:
其中,#表示与连接单元连接的位置。
根据本发明的一个实施方式,D单元可选自不含氮原子的给电子基团,具体可选自呫吨基、芴基、螺二芴基、二苯醚基和环戊二烯并二吲哚基中的任意一种或一种以上:
其中,#表示能够与连接单元连接的位置。
本发明中,“#表示能够与连接单元连接的位置”是指当一个化学结构中存在两个或以上的#时,这些#中的任意一个都可以作为与连接单元连接的位置。对下文中的“#表示能够与连接单元连接的位置”也应作相同解释。
根据本发明的一个实施方式,A单元选自含氮杂环类取代基、氰基类取代基、三芳基硼类取代基、苯甲酮类取代基、芳杂环甲酮类取代基和砜类取代基中的任意一种或一种以上。
根据本发明的一个实施方式,所述含氮杂环类取代基选自1,3,5-三嗪类、1,3,4-噁二唑类和1,2,4-三唑类、嘧啶类或氮杂环并菲类,具体可选自1,3,5-三嗪基、1,2,4-三嗪基、1,3,4-噁二唑基、1,2,4-三唑基、嘧啶基、1,4-二氮杂苯并菲基、苯并咪唑基、苯并噁唑基、苯并噻唑基、吡唑基、噁二唑基、噻二唑基、苯并[1,2-d:4,5-d]二噻唑、苯并[1,2-d:4,5-d]二噁唑、苯并[1,2-d:5,4-d]二噁唑、苯并咪唑基、菲并[9,10-d]咪唑基、苯并咪唑[2,1-b]苯并噻唑基、1,2,3-三唑基、1,2,4-三唑基、吡嗪基、喹喔啉基、二苯并吩嗪基、二苯并[f,h]喹喔啉基、吡嗪并[2,3-f][1,10]邻菲罗啉基、吡嗪并[2,3-b]吡嗪基、二吡嗪并[2,3-b:2',3'-e]吡嗪基、二吡嗪并[2,3-f:2',3'-h]喹喔啉基、1,3,4,6,7,9,9b-七氮杂非那烯基、呋喃并[2,3-b:5,4-b']联吡啶基、5H-环戊二烯并[2,1-b:3,4-b']联吡啶基、1,3,5,2,4,6-环三膦腈基、双[1,2,5]噻二唑[3,4-f:3',4'-h]喹喔啉基、苯并噻二唑基中的任意一种或一种以上:
其中,#表示能够与连接单元连接的位置;
R选自氢原子、碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为4-8的环烷基、碳原子数为4-20的芳基、碳原子数为4-20的杂芳基。
根据本发明的一个实施方式,所述氰基类取代基可选自氰基苯类、氰基吡啶类、氰基嘧啶类或丙烯腈类,具体可选自氰基、氰基苯基、二氰基苯基、三氰基苯基、2-三氟甲基-氰基苯基、氰基吡啶基、二氰基吡啶基、二氰基吡嗪基、9H-芴基-2,7-二甲腈基、8-苯基-1-萘甲腈基、1,3-双(二氰基亚甲基)茚满基、氰基嘧啶基、二苯基丙烯腈基中的一种或一种以上:
其中,#表示能够与连接单元连接的位置。
根据本发明的一个实施方式,所述芳基硼类取代基选自以下结构中的一种或一种以上:
其中,#表示能够与连接单元连接的位置。
根据本发明的一个实施方式,所述苯甲酮类取代基、芳杂环甲酮类取代基可选自二苯甲酮基、联苯甲酰基、苯甲酰基二苯甲酮基、2,3,6,7-二苯并环庚三烯酮基、9-噻吨酮基、9-呫吨酮基、9,10-蒽二酮基、苯甲酰基吡啶基、10-硫-9-蒽酮基、10,10-二甲基蒽酮基9H-噻吨-9-酮-10,10-二氧基、茚并[1,2-b]芴-6,12-二酮基,苯甲酰吡啶基、二吡啶基甲酮基、1H-异吲哚-1,3(2H)-二酮基、5H-吡咯并[3,4-b]吡嗪-5,7(6H)-二酮基中的一种或一种以上:
其中,#表示能够与连接单元连接的位置,每个结构式中的R各自独立地表示碳原子数1-20的烷基、碳原子数2-20的烯基、碳原子数6-40的芳香基、碳原子数4-40的杂芳香基。
根据本发明的一个实施方式,所述砜类取代基可选自二苯基砜基、1,4-双(磺酰基苯基)苯基、1,3-双(磺酰基苯基)苯基、9,9-二甲基-9H-噻吨-10,10-二氧基、吩噁噻-10,10-二氧基、噻蒽-5,5,10,10-四氧基、二苯并噻吩砜基、苯甲砜基萘基中的一种或一种以上:
其中,#表示能够与连接单元连接的位置。
根据本发明的一个实施方式,所述A单元选自含硫杂环类衍生物,具体可选自二苯并噻吩基、噻蒽、10-苯基-10H-苯基膦-10-氧基、二苯基膦氧基、三氟甲基、三氟甲基苯基、萘酰亚胺、苝酰亚胺和三苯乙烯基中的任意一种或一种以上:
其中,#表示能够与连接单元连接的位置,每个结构式中的R各自独立地表示碳原子数1-20的烷基、碳原子数2-20的烯基、碳原子数6-40的芳香基、碳原子数4-40的杂芳香基。
根据本发明的一个实施方式,D单元为取代的,取代基选自碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为3-20的环烷基、碳原子数为6-30的芳香基和碳原子数为2-20的杂芳基中的任意一种或一种以上;
A单元为取代的,取代基选自碳原子数为1-20的烷基、碳原子数为1-20的烷氧基、碳原子数为3-20的环烷基、碳原子数为6-30的芳香基、碳原子数为2-20的杂芳基、氟原子、三氟甲基、氰基、羰基、酯基、磺酰基和膦氧基中的任意一种或一种以上。
根据本发明的一个实施方式,所述化合物选自化合物P1至P29。
根据本发明的另一方面,提供了如上所述化合物的制备方法,包括以下步骤:
将活化的苯并环烷烃基团与活化的D单元、A单元分别反应,得到所述化合物。
下面以化合物P1~P6,P19和P21的制备为例,对本发明化合物的制备方法进行说明。
化合物P1的合成
称取S1(30mmol)放入250mL两口烧瓶中,加入80mL乙腈溶解S1,逐滴滴入HCl的水溶液(体积比为15mL:50mL),反应混合溶液冷却至0℃,将上述混合溶液加入到NaNO2的水溶液(35mmol:50mL)中,在温度低于5℃的条件下反应30min。将上述反应混合溶液,加入到KI的水溶液中(44mmol:50mL),添加完毕后,将反应混合溶液在室温下搅拌过夜。反应结束后,将反应混合溶液加入到300mL水中,用二氯甲烷萃取,收集有机相,用无水Na2SO4干燥处理,减压蒸馏纯化得S2(24mmol,80%).
MALDI-TOF MS:m/z calcd for C10H10BrI:335.9;found:335.7.
将S2(10mmol)、S3(10.5mmol)、(二亚苄基丙酮)二钯(0)(0.05mmol)、叔丁醇钠(14mmol)、4,5-双二苯基膦-9,9-二甲基氧杂蒽(0.2mmol)投入50mL三口烧瓶中,一面搅拌,一面迅速反复3次脱气和氮气置换,通过注射器加入20mL甲苯。将该混合物在氮气气流下,加热回流3小时。反应后,在放置冷却至室温的反应溶液中添加水,利用二氯甲烷进行萃取,并利用饱和食盐水进行洗净。利用无水硫酸钠对有机层进行干燥后,将溶剂蒸馏去除,并使用柱层析法进行精制,获得中间体S4(8mmol、80%)。
MALDI-TOF MS:m/z calcd for C22H18BrNO:391.1;found:391.3.
在250ml三口烧瓶中,首先将S4(30mmol)、联硼酸频那醇酯(36mmol)、(1,1'-双(二苯基膦)二茂铁)二氯钯(Ⅱ)(0.3mmol)以及乙酸钾(75mmol)分别加入,一面搅拌,一面迅速反复3次脱气和氮气置换,通过注射器加入100mL四氢呋喃。在一定转速下搅拌,将所得的混合溶液反应物在反应温度80℃下加热回流5h;待反应结束后,冷却至室温并加入100ml水,用乙醚萃取,将所得有机相用无水硫酸钠干燥,将溶剂蒸馏去除,并使用柱层析法进行精制,得到中间体S5(25.5mmol,85%)。
MALDI-TOF MS:m/z calcd for C28H30BNO3:439.2;found:439.2.
在室温下,往50ml的单口烧瓶中加入20ml浓硫酸,然后加入6mL溴苯S6(57mmol),室温搅拌半小时,得白色浑浊液体,然后在半小时分批加入1.0g巯基水杨酸S7(6.5mmol)。室温搅拌24h,然后在100℃加热2-3h,冷却至室温后,小心倒入冰水中,抽滤,得到固体,然后加入20%的NaOH水溶液,搅拌2h,抽滤,水洗至中性,得黄色固体S8(5.2mmol,80%)。
1H NMR(400MHz,CDCl3,ppm):7.70-7.90(s,2H),7.40-7.60(m,4H),7.30(m,1H)。MALDI-TOF MS:m/z calcd for C13H7BrOS:289.9;found:290.0.
在室温下,往500mL的单口烧瓶中加入100mL冰醋酸和200mL二氯甲烷,加入原料中间体S8(20mmol),5倍当量30%的双氧水,55-60℃搅拌20-24h,冷却至室温后,二氯甲烷萃取,过柱得白色固体S9(17mmol,85%)。
MALDI-TOF MS:m/z calcd for C13H7BrO3S:321.9;found:321.8.
在氮气保护下,称取化合物S5(20mmol)、S9(20.1mmol)、[Pd2(dba)3]·CHCl3(0.4mmol)和HP(tBu)3·BF4(0.8mmol),加入到250mL的两口烧瓶中。向两口烧瓶内注入100mL甲苯(提前通N2 15min除氧气),然后再逐滴加入12mL浓度为1M的K2CO3水溶液(提前通N2 15min除氧气),室温搅拌过夜。反应结束后,加入100mL去离子水,再滴入几滴2M HCl.用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体P1(15.6mmol,78%)。
MALDI-TOF MS:m/z calcd for C35H25NO4S:555.2;found:555.1.
元素分析计算值:C,75.66;H,4.54;N,2.52;O,11.52;S,5.77;测试值:C,75.66;H,4.55;N,2.51;O,11.53;S,5.76。
化合物P2的合成
将S2(10mmol)、S10(10.5mmol)、(二亚苄基丙酮)二钯(0)(0.05mmol)、叔丁醇钠(14mmol)、4,5-双二苯基膦-9,9-二甲基氧杂蒽(0.2mmol)投入50mL三口烧瓶中,一面搅拌,一面迅速反复3次脱气和氮气置换,通过注射器加入20mL甲苯。将该混合物在氮气气流下,加热回流3小时。反应后,在放置冷却至室温的反应溶液中添加水,利用二氯甲烷进行萃取,并利用饱和食盐水进行洗净。利用无水硫酸钠对有机层进行干燥后,将溶剂蒸馏去除,并使用柱层析法进行精制,获得中间体S11(8.5mmol、85%)。
MALDI-TOF MS:m/z calcd for C25H24BrN:417.1;found:417.2.
在250ml三口烧瓶中,首先将S11(30mmol)、联硼酸频那醇酯(36mmol)、(1,1,-双(二苯基膦)二茂铁)二氯钯(Ⅱ)(0.3mmol)以及乙酸钾(75mmol)分别加入,一面搅拌,一面迅速反复3次脱气和氮气置换,通过注射器加入100mL四氢呋喃。在一定转速下搅拌,将所得的混合溶液反应物在反应温度80℃下加热回流5h;待反应结束后,冷却至室温并加入100ml水,用乙醚萃取,将所得有机相用无水硫酸钠干燥,将溶剂蒸馏去除,并使用柱层析法进行精制,得到中间体S12(25.5mmol,85%)。
MALDI-TOF MS:m/z calcd for C31H36BNO2:465.3;found:465.3.
在氮气保护下,称取化合物S12(20mmol),S9(20.2mmol),[Pd2(dba)3]·CHCl3(0.5mmol)和HP(tBu)3·BF4(1mmol),加入到250mL的两口烧瓶中。向两口烧瓶内注入100mL甲苯(提前通N2 15min除氧气),然后再逐滴加入12mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入100mL去离子水,再滴入几滴2M HCl.用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体P2(17.6mmol,88%)。
MALDI-TOF MS:m/z calcd for C38H31NO3S:581.2;found:581.3.
元素分析计算值:C,78.46;H,5.37;N,2.41;O,8.25;S,5.51;测试值:C,78.46;H,5.38;N,2.40;O,8.26;S,5.50。
化合物P3的合成
在250ml三口烧瓶中,首先将S13(30mmol)、联硼酸频那醇酯(36mmol)、(1,1,-双(二苯基膦)二茂铁)二氯钯(Ⅱ)(0.3mmol)以及乙酸钾(75mmol)分别加入,一面搅拌,一面迅速反复3次脱气和氮气置换,通过注射器加入100mL四氢呋喃。在一定转速下搅拌,将所得的混合溶液反应物在反应温度80℃下加热回流5h;待反应结束后,冷却至室温并加入100ml水,用乙醚萃取,将所得有机相用无水硫酸钠干燥,将溶剂蒸馏去除,并使用柱层析法进行精制,得到中间体S14(24mmol,80%)。
MALDI-TOF MS:m/z calcd for C15H20BFO2:262.2;found:262.1.
在氮气保护下,称取化合物S14(15mmol),S9(15.2mmol),[Pd2(dba)3]·CHCl3(0.3mmol)和HP(tBu)3·BF4(0.6mmol),加入到250mL的两口烧瓶中。向两口烧瓶内注入100mL甲苯(提前通N2 15min除氧气),然后再逐滴加入12mL浓度为1M的K2CO3水溶液(提前通N2 15min除氧气),室温搅拌过夜。反应结束后,加入100mL去离子水,再滴入几滴2M HCl.用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体S15(13.2mmol,88%)。
MALDI-TOF MS:m/z calcd for C22H15FO3S:378.1;found:378.2.
在氮气保护下,称取化合物S16(25mmol)加入到250mL的两口烧瓶中,加入50mL干燥的无水四氢呋喃溶解S16。取NaH(储存在60%的油中,30mmol)用正己烷反复冲洗三次,加入到两口烧瓶中,搅拌30min。然后向两口烧瓶中添加S15,室温下反应,搅拌过夜。用甲醇和水淬灭反应,用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后通过升华纯化得到固体P3(19.5mmol,78%)。
MALDI-TOF MS:m/z calcd for C42H39NO3S:637.3;found:637.4.
元素分析计算值:C,79.09;H,6.16;N,2.20;O,7.53;S,5.03;测试值:C,79.09;H,6.17;N,2.19;O,7.54;S,5.02。
化合物P4的合成
在氮气保护下,称取化合物S5(15mmol),S17(15mmol),[Pd2(dba)3]·CHCl3(0.3mmol)和HP(tBu)3·BF4(0.6mmol),加入到100mL的两口烧瓶中。向两口烧瓶内注入30mL甲苯(提前通N2 15min除氧气),然后再逐滴加入3.6mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入50mL去离子水,再滴入几滴2M HCl.用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体P4(13.2mmol,88%)。
MALDI-TOF MS:m/z calcd for C30H23N3O:441.2;found:441.2;
元素分析计算值:C,81.61;H,5.25;N,9.52;O,3.62;测试值:C,81.61;H,5.26;N,9.51;O,3.62。
化合物P5的合成
在氮气保护的条件下,称取S18(30mmol),加入60mL的醋酸,在搅拌的条件下,逐滴滴加液溴(36mmol),将所得的混合溶液在80℃下搅拌5h。用NaHSO3水溶液淬灭多余的溴单质,用二氯甲烷萃取(100mL×3),收集有机相,用无水Na2SO4干燥处理.过滤,用旋转蒸发仪减压蒸馏除去溶剂,得到粗产物。粗产物通过硅胶柱色谱梯度淋洗纯化,最后使用正己烷重结晶纯化得到固体粉末S19(25.2mmol,84%)。
MALDI-TOF MS:m/z calcd for C12H7BrS2:293.9;found:293.8.
在室温下,往50mL的单口烧瓶中加入40mL冰醋酸和20mL二氯甲烷,加入原料中间体S19(4mmol),5倍当量30%的双氧水,55-60℃搅拌20-24h,冷却至室温后,二氯甲烷萃取,过柱得白色固体S20(3.4mmol,85%)。
MALDI-TOF MS:m/z calcd for C12H7BrO4S2:357.9;found:358.0.
称取S21(30mmol)放入250mL两口烧瓶中,加入80mL乙腈溶解S1,逐滴滴入HCl的水溶液(体积比为15mL:50mL),反应混合溶液冷却至0℃,将上述混合溶液加入到NaNO2的水溶液(35mmol:50mL)中,在温度低于5℃的条件下反应30min。将上述反应混合溶液,加入到KI的水溶液中(44mmol:50mL),添加完毕后,将反应混合溶液在室温下搅拌过夜。反应结束后,将反应混合溶液加入到300mL水中,用二氯甲烷萃取,收集有机相,用无水Na2SO4干燥处理,减压蒸馏纯化得S22(24mmol,80%).
MALDI-TOF MS:m/z calcd for C22H17Br2O4S2:693.8;found:693.7.
将S22(10mmol)、S3(10.5mmol)、(二亚苄基丙酮)二钯(0)(0.05mmol)、叔丁醇钠(14mmol)、4,5-双二苯基膦-9,9-二甲基氧杂蒽(0.2mmol)投入50mL三口烧瓶中,一面搅拌,一面迅速反复3次脱气和氮气置换,通过注射器加入20mL甲苯。将该混合物在氮气气流下,加热回流3小时。反应后,在放置冷却至室温的反应溶液中添加水,利用二氯甲烷进行萃取,并利用饱和食盐水进行洗净。利用无水硫酸钠对有机层进行干燥后,将溶剂蒸馏去除,并使用柱层析法进行精制,获得中间体S23(8.2mmol、82%)。
MALDI-TOF MS:m/z calcd for C22H18BrNO:391.1;found:391.0.
在250ml三口烧瓶中,首先将S13(30mmol)、联硼酸频那醇酯(36mmol)、(1,1,-双(二苯基膦)二茂铁)二氯钯(Ⅱ)(0.3mmol)以及乙酸钾(75mmol)分别加入,一面搅拌,一面迅速反复3次脱气和氮气置换,通过注射器加入100mL四氢呋喃。在一定转速下搅拌,将所得的混合溶液反应物在反应温度80℃下加热回流5h;待反应结束后,冷却至室温并加入100ml水,用乙醚萃取,将所得有机相用无水硫酸钠干燥,将溶剂蒸馏去除,并使用柱层析法进行精制,得到中间体S14(24mmol,80%)。
MALDI-TOF MS:m/z calcd for C28H30BNO3:439.2;found:439.2.
在氮气保护下,称取化合物S24(25mmol),S20(25.2mmol),[Pd2(dba)3]·CHCl3(0.5mmol)和HP(tBu)3·BF4(1mmol),加入到250mL的两口烧瓶中。向两口烧瓶内注入100mL甲苯(提前通N2 15min除氧气),然后再逐滴加入12mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入100mL去离子水,再滴入几滴2M HCl.用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体P5(18.8mmol,75%)。
MALDI-TOF MS:m/z calcd for C34H25NO5S2:591.1;found:591.2.
元素分析计算值:C,69.02;H,4.26;N,2.37;O,13.52;S,10.84;测试值:C,69.02;H,4.27;N,2.36;O,13.53;S,10.83。
化合物P6的合成
在250ml三口烧瓶中,首先将S25(30mmol)、联硼酸频那醇酯(36mmol)、(1,1,-双(二苯基膦)二茂铁)二氯钯(Ⅱ)(0.3mmol)以及乙酸钾(75mmol)分别加入,一面搅拌,一面迅速反复3次脱气和氮气置换,通过注射器加入100mL四氢呋喃。在一定转速下搅拌,将所得的混合溶液反应物在反应温度80℃下加热回流5h;待反应结束后,冷却至室温并加入100ml水,用乙醚萃取,将所得有机相用无水硫酸钠干燥,将溶剂蒸馏去除,并使用柱层析法进行精制,得到中间体S26(27mmol,90%)。
MALDI-TOF MS:m/z calcd for C15H20BFO2:262.2;found:262.1.
在氮气保护下,称取化合物S26(20mmol),S20(mmol),[Pd2(dba)3]·CHCl3(0.5mmol)和HP(tBu)3·BF4(1mmol),加入到250mL的两口烧瓶中。向两口烧瓶内注入100mL甲苯(提前通N2 15min除氧气),然后再逐滴加入12mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入50mL去离子水,再滴入几滴2M HCl.用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体S27(17mmol,85%)。
MALDI-TOF MS:m/z calcd for C21H15FO4S2:414.0;found:414.1.
在氮气保护下,称取化合物S16(25.2mmol)加入到250mL的两口烧瓶中,加入50mL干燥的无水四氢呋喃溶解S16。取NaH(储存在60%的油中,30mmol)用正己烷反复冲洗三次,加入到两口烧瓶中,搅拌30min。然后向两口烧瓶中添加S27(25mmol),室温下反应,搅拌过夜。用甲醇和水淬灭反应,用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后通过升华纯化得到固体P6(18.8mmol,75%)。
MALDI-TOF MS:m/z calcd for C41H39NO4S2:673.2;found:673.2.
元素分析计算值:C,73.07;H,5.83;N,2.08;O,9.50;S,9.52;测试值:C,73.07;H,5.84;N,2.07;O,9.51;S,9.51。
化合物P19的合成
在氮气保护下,称取化合物S28(20mmol),S29(20.2mmol),[Pd2(dba)3]·CHCl3(0.5mmol)和HP(tBu)3·BF4(1mmol),加入到250mL的两口烧瓶中。向两口烧瓶内注入100mL甲苯(提前通N2 15min除氧气),然后再逐滴加入12mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入100mL去离子水,再滴入几滴2M HCl.用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体S30(16mmol,80%)。
MALDI-TOF MS:m/z calcd for C13H11F2N3:247.1;found:247.1.
在氮气保护下,称取化合物S31(21mmol)加入到250mL的两口烧瓶中,加入50mL干燥的无水四氢呋喃溶解S31。取NaH(储存在60%的油中,30mmol)用正己烷反复冲洗三次,加入到两口烧瓶中,搅拌30min。然后向两口烧瓶中添加S30(10mmol),室温下反应,搅拌过夜。用甲醇和水淬灭反应,用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后通过升华纯化得到固体P19(7.8mmol,78%)。
MALDI-TOF MS:m/z calcd for C43H41N7:655.3;found:655.3.
元素分析计算值:C,78.75;H,6.30;N,14.95;测试值:C,78.75;H,6.31;N,14.94。
化合物P21的合成
在250ml三口烧瓶中,首先将S31(30mmol)、联硼酸频那醇酯(36mmol)、(1,1,-双(二苯基膦)二茂铁)二氯钯(Ⅱ)(0.3mmol)以及乙酸钾(75mmol)分别加入,一面搅拌,一面迅速反复3次脱气和氮气置换,通过注射器加入100mL四氢呋喃。在一定转速下搅拌,将所得的混合溶液反应物在反应温度80℃下加热回流5h;待反应结束后,冷却至室温并加入100ml水,用乙醚萃取,将所得有机相用无水硫酸钠干燥,将溶剂蒸馏去除,并使用柱层析法进行精制,得到中间体S32(24mmol,80%)。
MALDI-TOF MS:m/z calcd for C20H28BFO2:330.2;found:330.2.
在氮气保护下,称取化合物S32(20mmol),S33(20mmol),[Pd2(dba)3]·CHCl3(0.5mmol)和HP(tBu)3·BF4(1mmol),加入到250mL的两口烧瓶中。向两口烧瓶内注入100mL甲苯(提前通N2 15min除氧气),然后再逐滴加入12mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入50mL去离子水,再滴入几滴2M HCl.用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体S34(16mmol,80%)。
MALDI-TOF MS:m/z calcd for C20H18FN7:375.2;found:375.3.
在氮气保护下,称取化合物S10(25.2mmol)加入到250mL的两口烧瓶中,加入50mL干燥的无水四氢呋喃溶解S10。取NaH(储存在60%的油中,30mmol)用正己烷反复冲洗三次,加入到两口烧瓶中,搅拌30min。然后向两口烧瓶中添加S34(25mmol),室温下反应,搅拌过夜。用甲醇和水淬灭反应,用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后通过升华纯化得到固体P21(19.5mmol,78%)。
MALDI-TOF MS:m/z calcd for C35H32N8:564.3;found:564.4.
元素分析计算值:C,74.44;H,5.71;N,19.84;测试值:C,74.44;H,5.72;N,19.83。
根据本发明的又一方面,提供了一种发光材料,所述发光材料包含根据本发明的化合物。
根据本发明的一个实施方式,所述发光材料为热激活延迟荧光材料。
根据本发明的又一方面,提供了一种有机电致发光器件,包括:
基底;
设置于所述基底上的第一电极;
设置于第一电极上的有机功能层,所述有机功能层包括一层或多层有机膜层,且至少一层所述有机膜层为发光层;
设置于所述有机功能层上的第二电极;
所述发光层包含根据本发明的发光材料。
根据本发明的一个实施方式,所述发光材料作为所述发光层的主体材料或客体材料,或者所述发光材料单独构成所述发光层以制备非掺杂有机发光显示装置。
根据本发明的一个实施方式,所述发光材料作为所述发光层的掺杂体材料。当所述发光材料作为发光层的掺杂体材料时,所述主体材料优先选自2,8-二(二苯基氧膦基)二苯并噻吩(PPT)、4,4'-二(9-咔唑)联苯(CBP)、2,8-双(二苯基膦氧基)二苯并呋喃(PPF)、双(4-(9H-咔唑基-9-基)苯基)二苯硅烷(SiCz)、二(2-二苯氧化膦基)二苯醚(DPEPO)、1,3-双[3,5-二(吡啶-3-基)苯基]苯(BMPYPHB)、4,6-双(3,5-二(3-吡啶)基苯基)-2-甲基嘧啶(B3PYMPM)、9-(3-(9H-咔唑基-9-基)苯基)-9H-咔唑-3-氰基(mCPCN)、9-苯基-9-[4-(三苯基硅烷基)苯基]-9H-芴(TPSi-F)、聚乙烯基咔唑(PVK)、聚芴(PFO)等材料中的一种或一种以上,但不仅仅局限于以上几种主体材料。
本发明的发光材料也可作为发光层的主体材料。当所述发光材料作为发光层的主体材料时,所述掺杂体材料选自BczVBi、香豆素-6、DCJTB等荧光材料,也可选自磷光发光材料,也可选自TADF掺杂体发光材料,但不局限于以上几种材料。
根据本发明的有机功能层还包括空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、空穴阻挡层(HBL)、电子传输层(ETL)、电子注入层(EIL)。
所述空穴注入材料、空穴传输材料及电子阻挡材料可选自N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(α-NPD)、4,4',4”-三(咔唑-9-基)三苯胺(TCTA)、1,3-二咔唑-9-基苯(mCP)、4,4'-二(9-咔唑)联苯(CBP)、3,3'-二(N-咔唑基)-1,1'-联苯(mCBP)、2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲(HATCN)、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺(TAPC)、N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(α-NPB)、N,N'-二(萘-2-基)-N,N'-二(苯基)联苯-4,4'-二胺(NPB)、聚(3,4-乙烯二氧噻吩)-聚苯乙烯磺酸(PEDOT:PSS)、聚乙烯咔唑(PVK)、9-苯基-3,9-联咔唑(CCP)、三氧化钼(MoO3)等材料,但不局限于以上几种材料。
所述空穴阻挡材料、电子传输材料、电子注入材料可选自2,8-二(二苯基氧膦基)二苯并噻吩(PPT)、TSPO1、TPBi、2,8-双(二苯基膦氧基)二苯并呋喃(PPF)、二(2-二苯氧化膦基)二苯醚(DPEPO)、氟化锂(LiF)、4,6-双(3,5-二(3-吡啶)基苯基)-2-甲基嘧啶(B3PYMPM)、4,7-二苯基-1,10-菲啰啉(Bphen)、1,3,5-三[(3-吡啶基)-3-苯基]苯(TmPyBP)、三[2,4,6-三甲基-3-(3-吡啶基)苯基]硼烷(3TPYMB)、1,3-双(3,5-二吡啶-3-基苯基)苯(B3PYPB)、1,3-双[3,5-二(吡啶-3-基)苯基]苯(BMPYPHB)、2,4,6-三(联苯基-3-基)-1,3,5-三嗪(T2T)、二苯基二[4-(吡啶-3-基)苯基]硅烷(DPPS)、碳酸铯(Cs2O3)、双(2-甲基-8-羟基喹啉-N1,O8)-(1,1'-联苯-4-羟基)铝(BAlq)、8-羟基喹啉-锂(Liq)、三(8-羟基喹啉)铝(Alq3)等材料,但不局限于以上几种材料。
根据本发明的阳极材料可以是金属,例如铜、金、银、铁、铬、镍、锰、钯、铂等;可以是金属氧化物,例如金属氧化物-氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO)等;可以是合金;可以是导电性聚合物,例如聚苯胺、聚吡咯、聚(3-甲基噻吩)等。除了上述这些有助于空穴注入的材料及其组合外,还可以是其他已知的适合做阳极的材料。
根据本发明的阴极材料可以是金属,例如铝、镁、银、铟、锡、钛等;可以是合金,如Mg/Ag;可以是金属与无机化合物的复合材料,例如多层金属材料-LiF/Al、LiO2/Al、BaF2/Al等;除了上述有助于电子注入的材料及其组合外,还可以是其他已知的适合做阴极的材料。
根据本发明的基底可以是刚性基板(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)。
根据本发明的有机电致发光器件的结构如图2所示,其中,基底1为玻璃或其他适合材质(如塑料);第一电极2为ITO或IGZO等透明电极;有机功能层3包括一层或多层有机膜层;第二电极4为金属阴极。其中,第一电极2和第二电极4可互换,即第一电极2为金属阴极,第二电极4为ITO或IGZO等透明电极。
根据本发明的有机电致发光器件可以采用真空蒸镀法制备得到。
有机电致发光器件的蒸镀制备过程
将具有膜厚为100nm的ITO薄膜的阳极基板用蒸馏水、丙酮、异内醇超声清洗并放入烘箱干燥,通过UV处理表面30分钟,然后移至真空蒸镀腔中。在真窄度为2×10-6Pa下开始蒸镀各层薄膜,蒸镀5nm厚的HATCN形成空穴注入层,蒸镀40nm厚的N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(α-NPD),然后蒸镀10nm厚的4,4',4”-三(咔唑-9-基)三苯胺(TCTA)形成空穴传输层(HTL)。在空穴传输层上,用本发明的目标化合物作为发光层的掺杂材料,3,3'-二(N-咔唑基)-1,1'-联苯(mCBP)作为发光层的主体材料,同时蒸镀该掺杂材料和主体材料,形成30nm厚的发光层。然后在发光层上蒸镀二苯基[4-(三苯基硅烷基)苯基]氧膦(TSPO1)形成5nm厚的空穴阻挡层(HBL)。在空穴阻挡层上蒸镀:4,7-二苯基-1,10-菲啰啉(Bphen)以形成30nm的电子传输层(ETL)。在电子传输层上依次蒸镀2.5nm厚的LIF和100nm厚的Al作为电子注入层(EIL)和阴极,从而制成有机光电装置。
所述有机电致发光器件也可以采用溶液加工法制备得到。
制备非掺杂器件的具体步骤包括:将ITO玻璃依次使用丙酮、碱性洗液、超纯水、异丙醇各超声清洗两次,每次15分钟,然后用臭氧清洗机处理15分钟。向玻璃基底上旋转涂布40nm厚的PEDOT:PSS溶液,放置于真空烘箱120℃下45分钟烘干,在PEDOT:PSS上分别制备TAPC层和mCP层作为空穴传输层和电子阻挡层,然后涂布根据本发明的化合物的甲苯溶液(浓度为12mg/mL)作为发光层,厚度为40nm。将基片转移到真空腔室进行热蒸发镀膜,制备电子传输层(TmPyPb,50nm)、电子注入层(LiF,0.5-1nm)和阴极(Al,100nm),形成完整的器件。
制备掺杂器件的步骤还包括:分别配制主体发光材料和客体发光材料的邻二氯苯溶液(浓度为12mg/mL),用移液枪移取50uL(5%)的客体材料溶液加入到主体材料溶液中,磁力搅拌均匀后涂布发光层。其他均与制备非掺杂器件的具体步骤相同。
优选地,所述溶液加工法为喷墨打印法。
根据本发明的又一方面,提供了一种显示装置,包括根据本发明的有机电致发光器件。
根据本发明的显示装置例如可以是手机显示屏、电脑显示屏、液晶电视显示屏等,本实施例对比不作特殊限定。图3为手机显示屏的示意图,其中,5表示显示屏。
由此可见,根据本发明的化合物、发光材料、有机电致发光器件和显示装置的可选因素较多,根据本发明的权利要求可以组合出不同的实施例。本发明的实施例仅作为对本发明的具体描述,并不作为对本发明的限制。
下面将结合含有本发明的化合物的有机电致发光器件作为实施例对本发明进行进一步描述。
实施例1~8
图1示出了化合物P1的轨道排布情况,其中,图1中的(a)为化合物P1的HOMO能级分布图,图1中的(b)为化合物P1的LUMO能级分布图。从图1中可以明显看出,化合物P1的HOMO和LUMO分别排布在不同的单元上,实现了完全的分离,这有助于减小系间能差ΔEST,从而提高反向系间窜越能力。
运用密度泛函理论(DFT),针对化合物P1-P6、P19、P21,利用Gaussian 09程序包在B3LYP/6-31G(d)计算水平下,优化并计算得到了分子前线轨道的分布情况;同时基于含时密度泛函理论(TDDFT),模拟计算了分子的最低单线态能级S1和最低三线态能级T1。
实施例1~8的相关数据如表1所示。由表1可以看出,所有化合物的ΔEST均小于0.3ev,实现了较小的单线态和三线态能级差;同时,所有化合物的荧光寿命都在微秒量级,具有明显的延迟荧光效应。(表1中,S1表示单线态能级,T1表示三线态能级,ΔEST表示单线态和三线态能级差,Eg表示HOMO-LUMO能级差,τ表示荧光寿命。)
表1八个化合物的模拟计算结果
将化合物P1-P6、P19、P21作为发光材料,采用真空蒸镀法,设计了非掺杂器件N1至N8,结构为:ITO(100nm)/α-NPD(40nm)/TCTA(10nm)/P(40nm)/TmPyPb(50nm)/LiF(0.5nm)/Al(100nm),结果如表2所示。
表2真空蒸镀法制备的非掺杂器件的性能结果(P1-P6、P19、P21作为发光体)
由表2可以看出,同采用经典蓝光发光材料BCzVBi作为荧光掺杂剂的对比器件相比,N9-N16(掺杂)器件的EQE(max)均明显高于对比器件,这主要得益于本发明化合物自身的TADF特性,可以利用传统荧光分子(如BCzVBi)跃迁禁阻的三线态激子来发光,从而提高了器件效率。
将化合物P1-P6、P19、P21作为荧光掺杂剂,CBP作为主体材料,采用真空蒸镀法,设计了掺杂器件N9至N16,结构为:ITO(100nm)/α-NPD(40nm)/TCTA(10nm)/CBP:P(40nm)/TmPyPb(50nm)/LiF(0.5nm)/Al(100nm)。并且,作为对比例,将BCzVBi作为荧光掺杂剂,CBP作为主体材料,设计了掺杂器件C1,结构为ITO(100nm)/α-NPD(40nm)/TCTA(10nm)/CBP:BCzVBi(40nm,5%)/TmPyPb(50nm)/LiF(0.5nm)/Al(100nm)。结果如表3所示。
表3真空蒸镀法制备的掺杂器件的性能结果(P1-P6、P19、P21作为荧光掺杂剂)
将化合物P6为主体材料,荧光材料或磷光材料作为掺杂体,设计了掺杂器件N17至N18,结构为:ITO(100nm)/α-NPD(40nm)/TCTA(10nm)/P:掺杂体(荧光材料或磷光材料)(40nm)/TmPyPb(50nm)/LiF(0.5nm)/Al(100nm)。其中荧光材料选自红荧烯,磷光材料选自Ir(ppy)3。结果如表4所示。
表4真空蒸镀法制备掺杂器件性能
由表4可以看出,以本专利发明的化合物为主体材料,红荧烯和Ir(ppy)3为掺杂体材料的掺杂器件分别取得了6.8%和18.6%的最大外量子效率,说明本发明专利中的化合物可以作为荧光材料和磷光材料的主体材料。
同时发明人还采用溶液法加工法制作了相应的掺杂器件N19、非掺杂器件N20。
掺杂器件结构为:ITO(100nm)/PEDOT:PSS(40nm)/PVK:P3(40nm)/TmPyPb(50nm)/LiF(0.5nm)/Al(100nm)。
非掺杂器件,结构为:ITO(100nm)/PEDOT:PSS(40nm)/P3(40nm)/TmPyPb(50nm)/LiF(0.5nm)/Al(100nm);结果如表5所示。
表5溶液法制备的器件的性能结果
由表5可以看出,溶液法制备的以本发明设计的化合物为发光材料的非掺杂和掺杂器件分别取得了6.5%和12.3%的最大外量子效率。
显然,本领域的技术人员可以对本发明进行各种改动和变型而不脱离本发明的精神和范围。这样,倘若本发明的这些修改和变型属于本发明权利要求及其等同技术的范围之内,则本发明也意图包含这些改动和变型在内。
Claims (7)
3.一种发光材料,其特征在于,所述发光材料包含如权利要求1或2所述的化合物。
4.根据权利要求3所述的发光材料,其特征在于,所述发光材料为热激活延迟荧光材料。
5.一种有机电致发光器件,其特征在于,包括:
基底;
设置于所述基底上的第一电极;
设置于第一电极上的有机功能层,所述有机功能层包括一层或多层有机膜层,且至少一层所述有机膜层为发光层;
设置于所述有机功能层上的第二电极;
所述发光层包含权利要求3或4所述的发光材料。
6.根据权利要求5所述的有机电致发光器件,其特征在于,所述发光材料作为所述发光层的主体材料或客体材料,或者所述发光材料单独构成所述发光层以制备非掺杂有机发光显示装置。
7.一种显示装置,其特征在于,包括如权利要求5或6所述的有机电致发光器件。
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