CN115433118A - 一种含有酰亚胺结构的有机发光材料及其制备方法和应用 - Google Patents
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Abstract
本发明属于有机发光材料技术领域,公开了一种含有酰亚胺结构的有机发光材料及其制备方法和应用。所述有机发光材料具有如式(1)所示的结构。本发明的合成方法简单,价格低,容易纯化。所合成的有机发光材料具有明显的室温磷光特性,在撤去紫外灯后仍能够持续发光。且这一性质不止在晶体中呈现,在无定形状态下也可以获得。本发明可将获得的高校磷光材料用于有机电致发光器件中的发光层,或者电子传输层。除此之外,本发明的发光材料还可以用于检测,生物成像以及防伪等领域。
Description
技术领域
本发明属于有机发光材料技术领域,特别涉及一种含有酰亚胺结构的有机发光材料及其制备方法和应用。
背景技术
有机室温磷光材料在很多领域都具有重要应用,如显示,传感,防伪和生物成像等。对于有机发光材料,需要通过增加分子的系间窜越(inter-system crossing,ISC)来获得磷光。为了获得高效率的磷光,需要减少分子的伸缩振动和摇摆振动,减少非辐射跃迁的产生。目前常见的策略是将材料制备成结晶态,来减少分子的振动产生的非辐射跃迁。而另一种方法是将有机发光化合物分散在聚合物或者气凝胶中,这样得到非晶态的有机室温磷光材料。然而,目前很少有报道纯有机化合物的非晶态在室温下产生磷光的现象。在本发明中,我们发现了一种有机小分子,通过引入卤素原子,其无定形粉末在室温下产生稳定的磷光。
发明内容
为了克服现有技术的不足和缺点,本发明的首要目的在于提供一种含有酰亚胺结构的有机发光材料。
本发明的另一目的在于提供一种上述含有酰亚胺结构的有机发光材料的制备方法;该方法工艺简单,产率高,成本低,且易于纯化。
本发明的再一目的在于提供一种上述含有酰亚胺结构的有机发光材料的应用。
本发明的目的通过如下技术方案实现:
一种含有酰亚胺结构的有机发光材料,所述有机发光材料具有如式(1)或所示的结构:
其中,X表示卤素,包括F、Cl、Br、I。
上述的含有酰亚胺结构的有机发光材料的制备方法,包括以下操作步骤:将邻苯二甲酸酐与3,5-二卤代基苯胺在醋酸溶液中搅拌回流12h,停止反应后倒入水中析出固体,过滤后采用柱层析和重结晶的方法进行纯化,获得含有酰亚胺结构的有机发光材料。
上述的含有酰亚胺结构的有机发光材料作为发光层或者电子传输层在有机电致发光光器件中的应用。
上述的含有酰亚胺结构的有机发光材料在化学生物检测、生物成像、防伪领域中的应用。
本发明相对于现有技术具有如下的优点及效果:
(1)本发明的制备方法简单,价格低,容易纯化。
(2)本发明制备的有机发光材料具有明显的室温磷光特性,在撤去紫外灯后仍能够持续发光,且这一性质不止在晶体中呈现,在无定形状态下也可以获得。
(3)本发明可将获得的高校磷光材料用于有机电致发光器件中的发光层,或者电子传输层;除此之外,本发明的发光材料还可以用于检测,生物成像以及防伪等领域。
附图说明
图1是化合物PI-2Br的核磁共振氢谱图。
图2是化合物PI-2Cl的核磁共振氢谱图。
图3为化合物PI-2Br原始粉末和退火粉末的磷光光谱。
图4为化合物PI-2Br原始粉末和退火粉末的X射线粉末衍射图
具体实施方式
实施例1
化合物PI-2Br的合成
将邻苯二甲酸酐(2g,13.5mmol)加入250mL干燥的三颈瓶中,加入100mL乙酸溶解,通入氮气15分钟,而后加入3,5-二溴苯胺(4.07g,16.2mmol),升温至110℃;反应12小时后,停止反应,将混合液体倒入到冰水中,并充分搅拌析出固体,过滤,并使用水洗3次,将得到的滤渣使用柱层析进行纯化,得到产物4.53g,产率88%。所得化合物PI-2Br的核磁共振氢谱如图1所示:1H NMR(400MHz,DMSO)δ7.99(dt,J=6.9,3.5Hz,1H),7.97–7.95(m,1H),7.95–7.90(m,1H),7.78(d,J=1.7Hz,1H).
实施例2
化合物PI-2Cl的合成
将邻苯二甲酸酐(2g,13.5mmol)加入250mL干燥的三颈瓶中,加入100mL乙酸溶解,通入氮气15分钟,而后加入3,5-二氯苯胺(2.63g,16.2mmol),升温至110℃;反应12小时后,停止反应,将混合液体倒入到冰水中,并充分搅拌析出固体,过滤,并使用水洗3次,将得到的滤渣使用柱层析进行纯化,得到产物3.55g,产率90%。所得化合物PI-2Cl的核磁共振氢谱如图2所示:1H NMR(400MHz,DMSO)δ8.00(dt,J=7.1,3.5Hz,1H),7.97–7.87(m,1H),7.74(t,J=1.8Hz,1H),7.63(d,J=1.8Hz,1H).
本发明含有酰亚胺的新型有机发光化合物,在紫外灯下有较强的发光。而当熄灭紫外灯后,仍能够持续发光。且这种特性并不只在结晶状态中产生,对于无定形状态的化合物,仍具有撤去紫外灯后持续发光的特性。以化合物PI-2Br为例,如图3所示,化合物PI-2Br的原始粉末和退火后的粉末均表现出室温磷光的特性。采用X射线粉末衍射对他们的结晶状态进行测试,如图4所示,可以看到原始粉末为结晶状态,而退火后的粉末为无定形。可以发现,本发明所合成的化合物在无定形状态下仍具有室温磷光的特性。本发明所述材料可应用于有机电致发光器件的制备和生物成像等领域。
上述实施例为本发明较佳的实施方式,但本发明的实施方式并不受上述实施例的限制,其他的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化,均应为等效的置换方式,都包含在本发明的保护范围之内。
Claims (4)
2.根据权利要求1所述的含有酰亚胺结构的有机发光材料的制备方法,其特征在于包括以下操作步骤:将邻苯二甲酸酐与3,5-二卤代基苯胺在醋酸溶液中搅拌回流12h,停止反应后倒入水中析出固体,过滤后采用柱层析和重结晶的方法进行纯化,获得含有酰亚胺结构的有机发光材料。
3.根据权利要求1所述的含有酰亚胺结构的有机发光材料作为发光层或者电子传输层在有机电致发光光器件中的应用。
4.根据权利要求1所述的含有酰亚胺结构的有机发光材料在化学生物检测、生物成像、防伪领域中的应用。
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