CN110283585A - 一种基于激基复合物体系的有机电致发光材料及其器件 - Google Patents
一种基于激基复合物体系的有机电致发光材料及其器件 Download PDFInfo
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Abstract
本发明提供一种基于激基复合物体系的有机电致发光材料及其器件,由电子给体2,6‑二咔唑‑1,5‑吡啶和电子受体2,5,8‑三(2,4‑二氟苯基)‑1,3,4,6,7,9,9b‑庚嗪组成。本发明通过选择庚嗪环衍生物2,5,8‑三(2,4‑二氟苯基)‑1,3,4,6,7,9,9b‑庚嗪作为电子受体,2,6‑二咔唑‑1,5‑吡啶作为电子给体,降低激基复合物体系的电荷转移特性,从而实现一种发光光谱窄、效率衰减慢的激基复合物体系有机发光器件。
Description
技术领域
本发明属于光电材料技术领域,尤其涉及一种发光光谱窄、效率减慢的基于激基复合物体系的有机发光材料及其器件。
背景技术
激基复合物有机发光材料体系通常具有很强的电荷转移特性,导致激基复合物体系有机发光器件存在发光光谱宽、效率衰减快等缺点,使其应用受限。因此,基于激基复合物体系开发一种发光光谱窄、效率衰减慢的有机发光器件具有较好的经济价值。
发明内容
本发明的目的在于解决上述现有技术存在的缺陷,提供一种发光光谱窄、效率衰减慢的基于激基复合物发光材料及其器件,利用了有机发光材料与器件现有技术的成熟性和激基复合物体系材料选择范围广的优点。
本发明采用如下技术方案:
一种基于激基复合物体系的有机电致发光材料,由电子给体2,6-二咔唑-1,5-吡啶(PYD2)和电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪(HAP-3DF)组成,2,6-二咔唑-1,5-吡啶结构式为:
2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的结构式为:
电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的制备方法,其步骤为:
步骤(1).2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪的合成,
将钾1,3,3a1,4,6,7,9–七氮杂菲2,5,8-三(堆积)、五氯化磷、三氯氧磷,按照物质的量之比为1:4:70加入到三口烧瓶中,加热至90-120℃,搅拌4-8小时,将溶液放置冷却至室温后,抽滤浓缩除去溶剂,加入30-100ml冰水,搅拌2-8分钟,快速抽滤,并用冰水冲洗,得到黄色固体,用滤纸包裹黄色固体并按压干燥,随后,将黄色固体放置于一个低压干燥器干燥12-36小时,得到产量2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪;
步骤(2).2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的合成
在0℃,将2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪、三氯化铝、1,3-二氟苯按照物质的量之比为1:5:30加入到三口烧瓶中,搅拌30-90分钟;
然后加热至60-100℃,搅拌6-10小时,将溶液放置冷却至室温后,加入冰水,搅拌30-90分钟;
随后,将溶液加热到60-100℃,搅拌30-90分钟;
将溶液自然冷却到室温后过滤,用水洗涤过滤后的固体,用甲苯溶解;
接着用柱层析法精制,得到2,5,8-三(2,4-二-二氟苯基)-1,3,4,6,7,9,9b-庚嗪
一种基于激基复合物体系的有机电致发光器件,包括阳极、有机层、阴极,有机层位于阳极与阴极之间,有机层包括发光层,所述发光层内由电子给体2,6-二咔唑-1,5-吡啶(PYD2)和电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪(HAP-3DF),2,6-二咔唑-1,5-吡啶结构式为:
2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的结构式为:
进一步的有机层还可包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层、电子注入层,使基于激基复合物体系构成的有机电致发光器件从上至下依次为阴极、电子注入层、电子传输层、空穴阻挡层、发光层、电子阻挡层、空穴传输层、空穴注入层、阳极。
本发明的有益效果:
激基复合物有机发光材料体系通常具有很强的电荷转移特性,导致激基复合物体系有机发光器件存在发光光谱宽、效率衰减快等缺点,使其应用受限。本发明通过选择庚嗪环衍生物HAP-3DF作为电子受体,PYD2作为电子给体,降低激基复合物体系的电荷转移特性,从而实现一种发光光谱窄、效率衰减慢的激基复合物体系有机发光器件。
附图说明
图1(a)、图1(b)为本发明的结构示意图;
图2为本发明的一种基于激基复合物体系的有机电致发光器件的结构示意图;
图3为2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪的合成示意图;
图4为2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的合成示意图。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚,下面本发明中的技术方案进行清楚、完整地描述,显然,所描述的实施例是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
如图1(a)、图1(b)、图2所示,一种基于激基复合物体系的有机电致发光材料,由电子给体2,6-二咔唑-1,5-吡啶(PYD2)和电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪(HAP-3DF)组成,2,6-二咔唑-1,5-吡啶结构式为:
2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的结构式为:
一种基于激基复合物体系的有机电致发光器件,包括阳极、有机层、阴极,有机层位于阳极与阴极之间,有机层包括发光层,所述发光层内由电子给体2,6-二咔唑-1,5-吡啶(PYD2)和电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪(HAP-3DF)组成,2,6-二咔唑-1,5-吡啶结构式为:
2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的结构式为:
进一步的有机层还可包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层、电子注入层,使构成的有机电致发光器件从上至下依次为阴极、电子注入层、电子传输层、空穴阻挡层、发光层、电子阻挡层、空穴传输层、空穴注入层、阳极。
实施例1
电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的制备方法:
步骤1(1)2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪的合成,如图3所示。
将钾1,3,3a1,4,6,7,9–七氮杂菲2,5,8-三(堆积)(potassium 1,3,3a1,4,6,7,9-heptaazaphenalene-2,5,8-tris(olate))(10mmol)、五氯化磷(40mmol)加入到三口烧瓶中,然后加入700mmol的三氯氧磷,加热至110℃,搅拌6小时。将溶液放置冷却至室温后,抽滤浓缩除去溶剂,加入50ml冰水,搅拌5分钟,快速抽滤,并用冰水冲洗,得到黄色固体,用滤纸包裹黄色固体并按压干燥。随后,将黄色固体放置于一个低压干燥器干燥24小时,得到产量2.2g、产率80%的2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪。
步骤(2)2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的合成,如图4所示。
0℃下,将2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪(3.6mmol)、三氯化铝(18mmol)、1,3-二氟苯(108mmol)加入到三口烧瓶中,搅拌30分钟。然后加热至90℃,搅拌8小时。将溶液放置冷却至室温后,加入冰水,搅拌1小时。随后,将溶液加热到100℃,搅拌1小时。将溶液自然冷却到室温后过滤,用水洗涤过滤后的固体,用甲苯溶解。接着,使用柱层析法精制,得到产量0.46g、产率25%的2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪。
实施例2
电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的制备方法:步骤1(1)2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪的合成,如图3所示。
将钾1,3,3a1,4,6,7,9–七氮杂菲2,5,8-三(堆积)(potassium 1,3,3a1,4,6,7,9-heptaazaphenalene-2,5,8-tris(olate))(11.5mmol)、五氯化磷(46mmol)加入到三口烧瓶中,然后加入805mmol的三氯氧磷,加热至90℃,搅拌2-8小时。将溶液放置冷却至室温后,抽滤浓缩除去溶剂,加入30ml冰水,搅拌2-8分钟,快速抽滤,并用冰水冲洗,得到黄色固体,用滤纸包裹黄色固体并按压干燥。随后,将黄色固体放置于一个低压干燥器干燥12小时,得到产量2.5g、产率79%的2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪。步骤(2)2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的合成,如图3所示。
0℃下,将2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪(6mmol)、三氯化铝(30mmol)、1,3-二氟苯(180mmol)加入到1三口烧瓶中,搅拌30分钟。然后加热至60℃,搅拌6-8小时。将溶液放置冷却至室温后,加入冰水,搅拌30-90min。随后,将溶液加热到60℃,搅拌30-90小时。将溶液自然冷却到室温后过滤,用水洗涤过滤后的固体,用甲苯溶解。接着,使用柱层析法精制,得到产量0.8g、产率26%的2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪。
实施例3
电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的制备方法:步骤1(1)2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪的合成,如图3所示。
将钾1,3,3a1,4,6,7,9–七氮杂菲2,5,8-三(堆积)(potassium 1,3,3a1,4,6,7,9-heptaazaphenalene-2,5,8-tris(olate))(20mmol)、五氯化磷(80mmol)加入到三口烧瓶中,然后加入1400mmol的三氯氧磷,加热至120℃,搅拌2-8小时。将溶液放置冷却至室温后,抽滤浓缩除去溶剂,加入100ml冰水,搅拌2-8分钟,快速抽滤,并用冰水冲洗,得到黄色固体,用滤纸包裹黄色固体并按压干燥。随后,将黄色固体放置于一个低压干燥器干燥36小时,得到产量5.0g、产率90%的2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪。
步骤(2)2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的合成,如图4所示。
0℃下,将2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪(18mmol)、三氯化铝(90mmol)、1,3-二氟苯(540mmol)加入到三口烧瓶中,搅拌90分钟。然后加热至100℃,搅拌6-8小时。将溶液放置冷却至室温后,加入冰水,搅拌30-90min。随后,将溶液加热到100℃,搅拌30-90min。将溶液自然冷却到室温后过滤,用水洗涤过滤后的固体,用甲苯溶解。接着,使用柱层析法精制,得到产量2.8g、产率31%的2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪。
实施例4
电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的制备方法:步骤1(1)2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪的合成,如图3所示
将钾1,3,3a1,4,6,7,9–七氮杂菲2,5,8-三(堆积)(potassium 1,3,3a1,4,6,7,9-heptaazaphenalene-2,5,8-tris(olate))(25mmol)、五氯化磷(100mmol)加入到三口烧瓶中,然后加入1750mmol的三氯氧磷,加热至120℃,搅拌4-6小时。将溶液放置冷却至室温后,抽滤浓缩除去溶剂,加入80ml冰水,搅拌4-8分钟,快速抽滤,并用冰水冲洗,得到黄色固体,用滤纸包裹黄色固体并按压干燥。随后,将黄色固体放置于一个低压干燥器干燥36小时,得到产量6.0g、产率87%的2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪。
步骤(2)2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的合成,如图4所示。
0℃下,将2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪(21mmol)、三氯化铝(105mmol)、1,3-二氟苯(630mmol)加入到三口烧瓶中,搅拌60分钟。然后加热至100℃,搅拌8-10小时。将溶液放置冷却至室温后,加入冰水,搅拌30-60min。随后,将溶液加热到100℃,搅拌60-90min。将溶液自然冷却到室温后过滤,用水洗涤过滤后的固体,用甲苯溶解。接着,使用柱层析法精制,得到产量3.5g、产率33%的2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪。
电子给体是普通的市场在售材料。
最后应说明的是:以上实施例仅用以说明本发明的技术方案,而非对其限制;尽管参照前述实施例对本发明进行了详细的说明,本领域的普通技术人员应当理解:其依然可以对前述各实施例所记载的技术方案进行修改,或者对其中部分技术特征进行等同替换;而这些修改或者替换,并不使相应技术方案的本质脱离本发明各实施例技术方案的精神和范围。
Claims (4)
1.一种基于激基复合物体系的有机电致发光材料,其特征在于,由电子给体2,6-二咔唑-1,5-吡啶和电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪组成,其中,2,6-二咔唑-1,5-吡啶结构式为:
2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的结构式为:
2.根据权利要求1所述的一种基于激基复合物体系的有机电致发光材料,其特征在于,电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的制备方法,其步骤为:
步骤(1).2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪的合成,
将钾1,3,3a1,4,6,7,9–七氮杂菲2,5,8-三(堆积)、五氯化磷、三氯氧磷,按照物质的量之比为1:4:70加入到三口烧瓶中,加热至90-120℃,搅拌4-8小时,将溶液放置冷却至室温后,抽滤浓缩除去溶剂,加入30-100ml冰水,搅拌2-8分钟,快速抽滤,并用冰水冲洗,得到黄色固体,用滤纸包裹黄色固体并按压干燥,随后,将黄色固体放置于一个低压干燥器中干燥12-36小时,得到产物2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪;
步骤(2).2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的合成
在0℃,将2,5,8-三氯-1,3,4,6,7,9,9b-庚嗪、三氯化铝、1,3-二氟苯按照物质的量之比为1:5:30加入到三口烧瓶中,搅拌30-90分钟;
然后加热至60-100℃,搅拌6-10小时,将溶液放置冷却至室温后,加入冰水,搅拌30-90分钟;
随后,将溶液加热到60-100℃,搅拌30-90分钟;
将溶液自然冷却到室温后过滤,用水洗涤过滤后的固体,用甲苯溶解;
接着用柱层析法精制,得到2,5,8-三(2,4-二-二氟苯基)-1,3,4,6,7,9,9b-庚嗪
3.一种基于激基复合物体系的有机电致发光器件,其特征在于,包括阳极、有机层、阴极,有机层位于阳极与阴极之间,有机层包括发光层,所述发光层内由电子给体2,6-二咔唑-1,5-吡啶和电子受体2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪,其中,2,6-二咔唑-1,5-吡啶结构式为:
2,5,8-三(2,4-二氟苯基)-1,3,4,6,7,9,9b-庚嗪的结构式为:
4.根据权利要求3所述的一种基于激基复合物体系的有机电致发光器件,其特征在于,有机层还包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层、电子注入层,使基于激基复合物体系的构成的有机电致发光器件从下至下依次为阴极、电子注入层、电子传输层、空穴阻挡层、发光层、电子阻挡层、空穴传输层、空穴注入层、阳极。
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