CN110016018B - 化合物、显示面板以及显示装置 - Google Patents
化合物、显示面板以及显示装置 Download PDFInfo
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- CN110016018B CN110016018B CN201910380644.0A CN201910380644A CN110016018B CN 110016018 B CN110016018 B CN 110016018B CN 201910380644 A CN201910380644 A CN 201910380644A CN 110016018 B CN110016018 B CN 110016018B
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—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
- 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
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
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Abstract
本发明提供一种具有D‑π‑A型化学结构的化合物,所述化合物具有化学式I所示结构;D1和D2表示给电子基团;m、n、p和q独立地选自0、1或2;X和Y独立地选自S原子、N原子、O原子、Si原子、C原子中的一种;D1和D2各自独立地选自取代或未取代的C12‑C40的咔唑基及其衍生物基团、取代或未取代的C12‑C40的二苯胺基及其衍生物基团、取代或未取代的C18‑C60的三苯胺基及其衍生物基团、C12‑C40的吖啶基及其衍生物基团中的至少一种;A1和A2表示受电子基团,且A1和A2选自含氮杂环类取代基、含氰基类取代基、芳基硼类取代基、含羰基类取代基、含氟类取代基、砜类取代基和含磷氧基类取代基中的至少一种。本发明通过在芳杂环母核上连接给电子基团和受电子基团,形成D‑π‑A型结构。
Description
技术领域
本发明涉及有机电致发光材料技术领域,具体地涉及一种化合物以及包括该化合物的显示面板以及显示装置。
背景技术
随着电子显示技术的发展,有机发光器件(OLED)广泛应用于各种显示设备中,对OLED的发光材料的研究和应用也日益增多。
根据发光机制,用于OLED发光层的材料主要包括以下四种:
(1)荧光材料;(2)磷光材料;(3)三线态-三线态湮灭(TTA)材料;(4)热活化延迟荧光(TADF)材料。
对于荧光材料,根据自旋统计,激子中单线态和三线态激子的比例是1:3,所以荧光材料最大内量子产率不超过25%。依据朗伯发光模式,光取出效率为20%左右,因此基于荧光材料的OLED的外量子效应(EQE)不超过5%。
对于磷光材料,磷光材料由于重原子效应,可以通过自旋偶合作用,加强分子内部系间窜越,可以直接利用75%的三线态激子,从而实现在室温下S1和T1共同参与的发射,理论最大内量子产率可达100%。依据朗伯发光模式,光取出效率为20%左右,因此基于磷光材料的OLED的外量子效应可以达到20%。但是,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。在高电流密度下,磷光材料存在严重的效率滚降现象,同时磷光器件的稳定性并不好。
对于三线态-三线态湮灭(TTA)材料,两个相邻的三线态激子,复合生成一个更高能级的单线激发态分子和一个基态分子,但是两个三线态激子产生一个单线态激子,所以理论最大内量子产率只能达到62.5%。为了防止产生较大的效率滚降现象,在这个过程中三线态激子的浓度需要调控。
对于热活化延迟荧光(TADF)材料,当单线激发态和三线激发态的能级差较小时,分子内部发生反向系间窜越(RISC),T1态激子通过吸收环境热上转换到S1态,可以同时利用75%的三线态激子和25%的单线态激子,理论最大内量子产率可达100%。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。TADF材料可以通过多种方法进行化学修饰。但目前已发现的TADF材料较少,因此亟待开发新型的可用于OLED的TADF材料。
发明内容
鉴于此,本发明提供一种具有热活化延迟荧光(TADF)性质的化合物,所述化合物具有化学式Ⅰ所示的结构:
其中,D1和D2表示给电子基团;m、n、p和q独立地选自0、1或2;X和Y独立地选自S原子、N原子、O原子、Si原子、C原子中的一种;
给电子基团D1和D2各自独立地选自取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、取代或未取代的C18-C60的三苯胺基及其衍生物基团、C12-C40的吖啶基及其衍生物基团中的至少一种;
A1和A2表示受电子基团,且A1和A2选自含氮杂环类取代基、含氰基类取代基、芳基硼类取代基、砜类取代基和含磷氧基类取代基中的至少一种。
本发明通过在苯杂环上连接给电子基团和受电子基团,形成D-π-A型共轭连接分子结构。特别地,形成的D-π-A型分子结构,尤其是含有硫原子的非共轭连接,可以得到更高的三线态能级,更宽的光学带隙,可以与掺杂体材料形成高效的能量转移,抵制三线态激子的非辐射跃迁过程,从而提高发光效率。此外,受电子基团A的引入可以使整个化合物分子具有双极性,有利于电子和空穴两种载流子的传输。
本发明还提供了一种显示面板和一种显示装置。
附图说明
图1是本发明实施例提供的化合物的化学通式;
图2是本发明实施例提供的一种OLED的结构示意图;
图3是本发明实施例提供的一种显示装置的示意图。
具体实施方式
下面通过实施例和对比例进一步说明本发明,这些实施例只是用于说明本发明,本发明不限于以下实施例。
本发明的一方面提供一种化合物,所述化合物具有化学式Ⅰ所示的结构:
其中,D1和D2表示给电子基团;m、n、p和q独立地选自1或2;X和Y独立地选自S原子、N原子、O原子、Si原子、C原子中的一种;
给电子基团D1和D2各自独立地选自取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、取代或未取代的C18-C60的三苯胺基及其衍生物基团、C12-C40的吖啶基及其衍生物基团中的至少一种;
A1和A2表示受电子基团,且A1和A2选自含氮杂环类取代基、含氰基类取代基、芳基硼类取代基、砜类取代基和含磷氧基类取代基中的至少一种。
根据本发明所述化合物的一个实施方式,m、n、p和q独立地选自1或2。
根据本发明所述化合物的一个实施方式,X和Y中的一者为S原子。
根据本发明所述化合物的一个实施方式,X和Y均为S原子。当X和Y均为S原子时,噻吩单元作为连接基团具有以下优点:
1.基于噻吩单元的化学修饰方法已经非常成熟,能够通过多种方法有效地对噻吩单元的不同位点进行功能化修饰,在很大的范围内调控材料的物理化学性能;
2.噻吩类材料具有优异的化学性能和物理性能;
3.噻吩基材料具有良好的稳定性,具有独特的电学、光学、氧化还原和自组装性能,使之成为有机电子学材料的重要候选者;
4.噻吩环上的硫原子具有良好的可极化性和高的富电子性,使噻吩类有机材料具有良好的电荷传输性能和给电子性能。
在本发明的D-A型分子结构优选采用邻位连接具有以下优点:
1.D-A型分子结构有利于实现HOMO和LUMO的有效分离;
2.D单元和A单元之间通过噻吩环的邻位连接,会提升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;
3.增加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。
根据本发明所述化合物的一个实施方式,所述给电子基团D1和D2选自以下咔唑类基团中的任意一种或一种以上:
其中,Y、Y1和Y2各自独立地选自碳原子、氮原子、氧原子、硫原子或硅原子;
x和y各自独立地选自0、1、2或3;
#表示与式(I)连接的位置;
R1、R2、R3、R4各自独立地选自氢原子、C1-C20烷基、C1-C20烷氧基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、取代或未取代的C3-C40的吖嗪基及其衍生物基团;
当Y为氧原子或硫原子时,R3不存在;当Y1为氧原子或硫原子时,R3不存在;当Y2为氧原子或硫原子时,R4不存在。
根据本发明所述化合物的一个实施方式,所述给电子基团D1和D2选自以下咔唑类基团中的任意一种或一种以上:
其中,#表示与式(I)连接的位置,R表示C1-C20烷基、C1-C20烷氧基、C2-C20烯基、C2-C20炔基、C6-C40芳香基、C4-C40杂芳香基。
根据本发明所述化合物的一个实施方式,所述给电子基团D1和D2选自以下基团中的任意一种或一种以上:
其中,Y、Y1、Y2各自独立地选自碳原子、氮原子、氧原子、硫原子或硅原子;
#表示与式(I)连接的位置;
r、s各自独立地选自0、1、2或3;p、q各自独立地选自0、1;
R1、R2、R3、R4各自独立地选自氢原子、C1-C20烷基、C1-C20烷氧基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、取代或未取代的C13-C40的吖啶基及其衍生物基团、取代或未取代的C3-C40的吖嗪基及其衍生物基团;
当Y为氧原子或硫原子时,p=0或q=0;当Y为氮原子时,p、q各自独立地选自0或1;当Y为碳原子或硅原子时,p、q各自独立地选自0、1。
根据本发明所述化合物的一个实施方式,所述给电子基团D1和D2选自以下吖啶类基团中的任意一种或一种以上:
其中,#表示与式(I)连接的位置。
根据本发明所述化合物的一个实施方式,所述给电子基团D1和D2选自以下二苯胺类基团中的任意一种或一种以上:
#表示与式(I)连接的位置;
u、v各自独立地选自0、1、2或3;
R1、R2各自独立地选自氢原子、C1-C20烷基、C1-C20烷氧基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、取代或未取代的C3-C40的吖嗪基及其衍生物基团。
根据本发明所述化合物的一个实施方式,所述给电子基团D1和D2选自以下二苯胺类基团中的任意一种或一种以上:
其中,#表示与式(I)连接的位置。
根据本发明所述化合物的一个实施方式,所述给电子基团D1和D2还可以选自以下基团中的任意一种或一种以上:
其中,#表示与式(I)连接的位置。
根据本发明所述化合物的一个实施方式,所述受电子基团A1和A2选自以下含氮杂环类基团中的至少一种:
其中,#表示与式(I)连接的位置;
R选自氢原子、C1-C20烷基、C1-C20烷氧基、C4-C8环烷基、C6-C40芳基、C4-C40杂芳基中的一种。
根据本发明所述化合物的一个实施方式,所述受电子基团A1和A2选自以下含氰基类基团中的至少一种:
其中,#表示与式(I)连接的位置。
根据本发明所述化合物的一个实施方式,所述含硼类受电子基团A1和A2选自以下基团中的至少一种:
其中,R15-R23各自独立地选自氢原子、烷基、烷氧基、芳基或芳杂基;X选自地硼原子、氧原子、硫原子、氮原子,当X为氧原子或硫原子时,R13不存在;
#表示与式(I)连接的位置。
根据本发明所述化合物的一个实施方式,所述芳基硼类取代基选自以下基团中的任意一种或一种以上:
#表示与式(I)连接的位置。
根据本发明所述化合物的一个实施方式,所述受电子基团A1和A2选自以下含砜类基团中的至少一种:
根据本发明所述化合物的一个实施方式,所述受电子基团A选自以下含膦氧基基团中的至少一种:
X选自O、S、BR11、C(R11)2、Si(R11)2和NR11中的任意一种;
R0、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11均各自独立地选自氢原子、取代或未取代的C1~C20烷基、取代或未取代的C3~C20环烷基、取代或未取代的C1~C20烷氧基、取代或未取代的C3~C20杂环基、取代或未取代的C6~C40芳基、取代或未取代的C2~C40杂芳基中的任意一种;
#表示与式(I)连接的位置。
根据本发明所述化合物的一个实施方式,所述受电子基团A选自以下含羰基类基团中的至少一种:
其中,#表示能够与式(I)连接的位置,R表示C1-C20烷基、C1-C20烷氧基、C2-C20烯基、C2-C20炔基、C4-C8环烷基、C6-C40芳香基、C4-C40杂芳基。
根据本发明所述化合物的一个实施方式,所述受电子基团A1和A2选自氟原子和三氟甲基的含氟类取代基中的至少一种。
根据本发明所述化合物的一个实施方式,D1与D2相同,且A1和A2相同。
根据本发明所述化合物的一个实施方式,m=n=p=q=1。
根据本发明所述化合物的一个实施方式,所述化合物选自下列化合物中的一种:
根据本发明所述化合物的一个实施方式,所述化合物的最低单重态能级S1与最低三重态能级T1之间的能级差ΔEst=ES1-ET1≦0.30eV。
根据本发明的化合物可以用作OLED发光层的主体材料。
本发明提供了几个示例性化合物P7、P23、P29、P31、P32的制备方法,如下示例性实施例1至实施例5所述。
实施例1
化合物P7的合成
将S1(5.0mmol)、9,9一二甲基-9,10一二氢吖啶S2(10.4mmol)、(二亚苄基丙酮)二钯(0)(0.2mmol)、叔丁醇钠(14.0mmol)、4,5-双二苯基膦-9,9-二甲基氧杂蒽(0.2mmol)投入250mL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50mL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P7(3.4mmol、68%)。
MALDI-TOFMS:m/z计算值:C42H28N6S2:680.2;测量值:680.5。
元素分析计算值:C,74.09;H,4.15;N,12.34;S,9.42;测试值:C,74.13;H,4.17;N,12.31;S,9.39。
实施例2
化合物P23的合成
在氮气保护下,称取化合物S3(7.5mmol)、S4(15.5mmol),[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N215min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2mL2MHCl。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S5(5.6mmol,75%)。
MALDI-TOFMS:m/z计算值:C40H20Br2N8S2:834.0;测量值:834.2。
将S5(2.0mmol)、9,9一二甲基-9,10一二氢吖啶S2(4.2mmol)、(二亚苄基丙酮)二钯(0)(0.25mmol)、叔丁醇钠(7.5mmol)、四氟硼酸三叔丁基膦(0.5mmol)投入500mL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150mL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P23(1.26mmol、63%)。
MALDI-TOFMS:m/z计算值:C64H36N10S2:1008.3;测量值:1008.4
元素分析计算值:C,76.17;H,3.60;N,13.88;S,6.35;测试值:C,76.21;H,3.62;N,13.85;S,6.32。
实施例3
化合物P29的合成
将S7(2.7mmol)、9,9一二甲基-9,10一二氢吖啶S2(5.7mmol)、(二亚苄基丙酮)二钯(0)(0.35mmol)、叔丁醇钠(10.0mmol)、四氟硼酸三叔丁基膦(0.7mmol)投入500mL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200mL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P23(1.60mmol、59%)。
MALDI-TOFMS:m/z计算值:C38H30Br2N2S2:736.0;测量值:736.2
在250ml三口烧瓶中,首先将S9(7.5mmol)、联硼酸频那醇酯(8.5mmol)、(1,1’-双(二苯基膦)二茂铁)二氯钯(Ⅱ)(0.1mmol)以及乙酸钾(20mmol)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25mL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25ml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S10(6.2mmol,83%)。
MALDI-TOFMS:m/z计算值:C19H19BO5S:370.1;测量值:370.5
在氮气保护下,称取化合物S8(1.5mmol)、S10(3.2mmol),[Pd2(dba)3]·CHCl3(0.1mmol)和HP(tBu)3·BF4(0.2mmol),加入到100mL的两口烧瓶中。向两口烧瓶内注入30mL甲苯(提前通N215min除氧气),然后再逐滴加入2.5mL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20mL去离子水,再滴入几滴2MHCl。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P29(1.1mmol,71%)。
MALDI-TOFMS:m/z计算值:C64H44N2O6S4:1064.2;测量值:1064.4元素分析计算值:C,72.16;H,4.16;N,2.63;O,9.01;S,12.04;测试值:C,72.20;H,4.18;N,2.61;O,8.99;S,12.02。
实施例4
化合物P31的合成
在氮气保护下,称取化合物S8(2.5mmol),S11(5.2mmol),[Pd2(dba)3]·CHCl3(0.2mmol)和HP(tBu)3·BF4(0.4mmol),加入到250mL的两口烧瓶中。向两口烧瓶内注入80mL甲苯(提前通N215min除氧气),然后再逐滴加入2mL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20mL去离子水,再滴入几滴2MHCl.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P31(1.8mmol,73%)。
MALDI-TOFMS:m/z计算值:C54H36F6N4S2:918.2;测量值:918.5
元素分析计算值:C,70.57;H,3.95;F,12.40;N,6.10;S,6.98;测试值:C,70.60;H,3.98;F,12.38;N,6.08;S,6.96。
实施例5
化合物P32的合成
将S7(2.7mmol)、9,9一二甲基-9,10一二氢吖啶S6(5.7mmol)、(二亚苄基丙酮)二钯(0)(0.35mmol)、叔丁醇钠(10.0mmol)、四氟硼酸三叔丁基膦(0.7mmol)投入500mL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200mL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S12(1.60mmol、59%)。
MALDI-TOFMS:m/z计算值:C32H20Br2N2S2:653.9;测量值:654.0
称取Mg条(100mmol)投入250mL三口烧瓶中,一面搅拌,一面迅速反复3次脱气和氮气置换,加入S23(100mmol)和干燥的四氢呋喃(50mL),加热引发反应,在回流的状态下反应2h,将反应混合物冷却至0℃,在0℃下逐滴加入三氟化硼乙醚溶液(45mmol),再次回流反应2h,获得S24在THF中的悬浊液,减压蒸馏去除溶剂,柱色谱纯化,用正己烷为淋洗剂,去除溶剂得到S24(78mmol,78%).
MALDI-TOFMS:m/z计算值:C18H22BF:268.2;测量值:268.1
称取S22(2.5mmol)投入100mL两口烧瓶中,一面搅拌,一面迅速反复3次脱气和氮气置换,加入40mL干燥乙醚溶解S22,在-78℃逐滴加入n-BuLi溶液(2.7mmol),持续搅拌15min,缓慢升温至室温搅拌1h,再次降温至-78℃,逐滴滴加S24的乙醚溶液(5.1mmolin25mL),搅拌30min,缓慢升温至室温过夜,减压蒸馏去除挥发性溶剂,用甲醇清洗粗产物(5×10mL),最后使用柱层析法进行精制,获得化合物P32(1.8mmol,72%)。MALDI-TOFMS:m/z计算值:C68H62B2N2S2:992.4;测量值:992.3
元素分析计算值:C,82.25;H,6.29;B,2.18;N,2.82;S,6.46;测试值:C,82.28;H,6.32;B,2.16;N,2.80;S,6.44。
化合物性能测试
(1)化合物模拟计算
运用密度泛函理论(DFT),利用Gaussian09程序包在B3LYP/6-31G(d)计算水平下,优化并计算得到本发明的化合物P7、P23、P29、P30、P31、P32、P33和P34的分子前线轨道的分布情况;同时基于含时密度泛函理论(TD-DFT),模拟计算了P7、P23、P29、P30、P31、P32、P33和P34各化合物分子的单线态能级S1和三线态能级T1,结果如表1所示,其中△EST=S1-T1,Eg=HOMO-LUMO,Eg的数值取绝对值。
表1化合物的参数表征
由表1可以看出,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,适于作为热活化延迟荧光材料。(表1中,S1表示单线态能级,T1表示三线态能级,△EST表示单线态和三线态能级差,Eg表示HOMO-LUMO能级差。)
本发明还提供一种显示面板,所述显示面板包括相对设置的阳极、阴极以及位于所述阳极和所述阴极之间的发光层,其中,所述发光层的发光材料包括所述的化合物中的一种或一种以上。
根据本发明的显示面板的一个实施方式,所述发光层的发光材料包括主体材料和客体材料,所述主体材料为本发明以上所述的化合物中的一种或一种以上。
根据本发明的显示面板的一个实施方式,所述发光层的发光材料包括主体材料和客体材料,所述客体材料为本发明以上所述的化合物中的一种或一种以上。
根据本发明的显示面板的一个实施方式,当所述发光层的发光材料为红光发光材料时,所述红光发光材料的单重态能级为1.61-1.99eV;
当所述发光层的发光材料为绿光发光材料时,所述绿光发光材料的单重态能级为2.15-2.52eV;
当所述发光层的发光材料为蓝光发光材料时,所述蓝光发光材料的单重态能级为2.52-2.73eV。
根据本发明的显示面板的一个实施方式,所述主体材料的单重态能级高于所述客体材料的单重态能级,且主体材料的单重态能级与客体材料的单重态能级之差小于1.0eV。
根据本发明的显示面板的一个实施方式,所述发光层的发光材料包括主体材料和客体材料,主体材料选自所述的化合物中的一种或一种以上,客体材料选自荧光材料、热活化延迟荧光材料或磷光发光材料;所述主体材料的HOMO能级与所述客体材料的HOMO能级之差小于0.6eV,或所述主体材料的LUMO能级与所述客体材料的LUMO能级之差小于0.6eV。
根据本发明的显示面板的一个实施方式,所述发光层的发光材料包括主体材料和客体材料,主体材料选自所述的化合物中的一种或一种以上,客体材料选自荧光材料或热活化延迟荧光材料,所述客体材料的单重态能级小于所述主体材料的单重态能级,且主体材料的单重态能级与客体材料的单重态能级之差小于1.0eV。
根据本发明的显示面板的一个实施方式,所述发光层的发光材料包括主体材料和客体材料,主体材料选自所述的化合物中的一种或一种以上,客体材料选自磷光材料,所述客体材料的三重态能级小于所述主体材料的三重态能级,且主体材料的三重态能级与客体材料的三重态能级之差小于1.0eV。
在本发明提供的显示面板中,有机发光器件的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。阳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;阳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,阳极材料还可以选自除以列举的阳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阳极的材料。
在本发明提供的显示面板中,有机发光器件的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。阴极材料也可以选自多层金属材料例如LiF/Al、LiO2/Al、BaF2/Al等。除了以上列举的阴极材料以外,阴极材料还可以是有助于电子注入的材料及其组合,包括已知的适合做阴极的材料。
有机发光器件可以按照本领域公知的方法进行制作,在此不再详述。在本发明中,有机发光器件可以这样制作:在透明或不透明的光滑的基板上形成阳极,在阳极上形成有机薄层,在有机薄层上形成阴极。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。
在本发明所述显示面板的一个实施方式中,有机发光器件(OLED)的结构如图2所示。其中,1为玻璃或其他适合材质(如塑料)做成的基底(substrate);2为ITO或IGZO等透明阳极;3为有机膜层(包括发光层);4为金属阴极,共同构成一个完整的OLED器件。
下面提供了示例性的器件实施例,用于说明本发明的化合物在有机发光显示面板中的实际应用。
器件实施例1
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。在真空度为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(NPB),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P7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,从而制成有机发光显示装置。
所述有机电致发光器件也可以采用溶液加工法制备得到。
器件实施例2
与器件实施例1的区别在于,将化合物P7替换为化合物P23,其它制备步骤均与实施例1中相应步骤相同。
器件实施例3
与器件实施例1的区别在于,将化合物P7替换为化合物P29,其它制备步骤均与实施例1中相应步骤相同。
器件实施例4
与器件实施例1的区别在于,将化合物P7替换为化合物P30,其它制备步骤均与实施例1中相应步骤相同。
器件实施例5
与器件实施例1的区别在于,将化合物P7替换为化合物P31,其它制备步骤均与实施例1中相应步骤相同。
器件实施例6
与器件实施例1的区别在于,将化合物P7替换为化合物P32,其它制备步骤均与实施例1中相应步骤相同。
器件实施例7
与器件实施例1的区别在于,将化合物P7替换为化合物P33,其它制备步骤均与实施例1中相应步骤相同。
器件实施例8
与器件实施例1的区别在于,将化合物P7替换为化合物P34,其它制备步骤均与实施例1中相应步骤相同。
器件对比例1
与器件实施例1的区别在于,将化合物P7替换为化合物DBP,其它制备步骤均与实施例1中相应步骤相同。
器件对比例2
与器件实施例1的区别在于,将化合物P7替换为化合物BCzVBi,其它制备步骤均与实施例1中相应步骤相同。
表2器件性能表征
由表2可知,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,P31和P34(掺杂)器件的EQE(max)均明显高于对比器件,这主要得益于P31和P34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。同采用经典红光发光材料DBP作为荧光掺杂剂的对比器件相比,P7和P23(掺杂)器件的EQE(max)均明显高于对比器件,这主要得益于P7和P23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。
本发明还提供了一种显示装置,其包括如上文所述的有机发光显示面板。在本发明中,有机发光器件可以是OLED,其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、液晶电视显示屏、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3是根据本发明实施例提供的一种显示装置的示意图。在图3中,10表示手机显示面板,20表示显示装置。
本申请虽然以较佳实施例公开如上,但并不是用来限定权利要求,任何本领域技术人员在不脱离本申请构思的前提下,都可以做出若干可能的变动和修改,因此本申请的保护范围应当以本申请权利要求所界定的范围为准。
Claims (14)
2.根据权利要求1所述的化合物,其特征在于,D1与D2相同,且A1和A2相同。
3.根据权利要求1所述的化合物,其特征在于,m=n=p=q=1。
5.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能级S1与最低三重态能级T1之间的能级差ΔEst=ES1-ET1≦0.30eV。
6.一种显示面板,其特征在于,包括相对设置的阳极、阴极以及位于所述阳极和所述阴极之间的发光层,其中,所述发光层的发光材料包括权利要求1至5中任一项所述的化合物中的一种或一种以上。
7.根据权利要求6所述的显示面板,其特征在于,所述发光层的发光材料包括主体材料和客体材料,所述主体材料为权利要求1至5中任一项所述的化合物中的一种或一种以上。
8.根据权利要求6所述的显示面板,其特征在于,所述发光层的发光材料包括主体材料和客体材料,所述客体材料为权利要求1至5中任一项所述的化合物中的一种或一种以上。
9.根据权利要求6所述的显示面板,其特征在于,当所述发光层的发光材料为红光发光材料时,所述红光发光材料的单重态能级为1.61-1.99eV;
当所述发光层的发光材料为绿光发光材料时,所述绿光发光材料的单重态能级为2.15-2.52eV;
当所述发光层的发光材料为蓝光发光材料时,所述蓝光发光材料的单重态能级为2.52-2.73eV。
10.根据权利要求7所述的显示面板,其特征在于,所述主体材料的单重态能级高于所述客体材料的单重态能级,且主体材料的单重态能级与客体材料的单重态能级之差小于1.0eV。
11.根据权利要求6所述的显示面板,其特征在于,所述发光层的发光材料包括主体材料和客体材料,主体材料选自权利要求1至5中任一项所述的化合物中的一种或一种以上,客体材料选自荧光材料、热活化延迟荧光材料或磷光发光材料;所述主体材料的HOMO能级与所述客体材料的HOMO能级之差小于0.6eV,或所述主体材料的LUMO能级与所述客体材料的LUMO能级之差小于0.6eV。
12.根据权利要求6所述的显示面板,其特征在于,所述发光层的发光材料包括主体材料和客体材料,主体材料选自权利要求1至5中任一项所述的化合物中的一种或一种以上,客体材料选自荧光材料或热活化延迟荧光材料,所述客体材料的单重态能级小于所述主体材料的单重态能级,且主体材料的单重态能级与客体材料的单重态能级之差小于1.0eV。
13.根据权利要求6所述的显示面板,其特征在于,所述发光层的发光材料包括主体材料和客体材料,主体材料选自权利要求1至5中任一项所述的化合物中的一种或一种以上,客体材料选自磷光材料,所述客体材料的三重态能级小于所述主体材料的三重态能级,且主体材料的三重态能级与客体材料的三重态能级之差小于1.0eV。
14.一种显示装置,包括权利要求6至13任一项所述的显示面板。
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