CN114805181A - 一种热激活延迟荧光离子型有机-无机纳米复合插层材料 - Google Patents
一种热激活延迟荧光离子型有机-无机纳米复合插层材料 Download PDFInfo
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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Abstract
本发明设计了一种有机热激活延迟荧光(TADF)离子型插层材料。这类材料含有TADF分子,使得其具有TADF特性。无机层状化合物层状结构具有特定的空间结构,可以为特殊离子的引入提供空间需求,能有效避免TADF分子的聚集淬灭,抑制诸如三线态‑极化子淬灭(TPQ)和三线态‑三线态湮灭(TTA)的不利影响。TADF材料可以同时利用单重态激子和三重态激子发光,当单重态和三重态的能级差(ΔEST)较小时,三重态激子可以被热激活成单重态激子,最终以辐射跃迁的方式实现延迟荧光。本发明通过将离子型TADF分子插层到层状纳米板中,利用层状纳米板有效的隔离作用,抑制了TADF分子的分子间相互作用,降低了TADF分子的猝灭,提高了TADF分子电致发光的内部量子效率,最终获得热激活延迟荧光离子型有机‑无机纳米复合插层材料。
Description
技术领域
本发明属于化合物技术领域,具体涉及一种热激活延迟荧光离子型有机-无机纳米复合插层材料。
背景技术
无机层状化合物结构规则,可以在其层板间嵌入离子或分子即插层形成纳米复合材料。层状材料同一层板内原子通过强化学键彼此连接,形成特定的结构单元,结构单元之间通过共角或者共边相互堆砌形成稳定的刚性骨架和开放的孔道结构,构成无机层状化合物的每一个层板都可看成是一个巨大的平面分子,而层状化合物就是由这些平面大分子相互叠加而成,因此层状化合物表现出高度的各向异性。层板间则填充着可以移动的离子或者是中性分子,以使整个化合物电位平衡。无机层状化合物的这种特殊的结构使它具有以下两个特点:(1)层板间离子的可交换性,并且发生离子交换的同时不会使层板的主体结构发生改变;(2)插层后产物的稳定性变得更高,并且产物能够兼具主体材料与客体材料两个方面的性质。已被研究的层状材料有很多,石墨是其中的典型,除石墨外,还有许多其他的层状材料,如层状硅酸盐(天然的层状硅酸盐、人工合成层状沸石类等)、层状过渡金属硫化物(VS2、MoS2、MgPS3等)、层状金属氧化物(Al2O3、WO3、V2O5等)、过渡金属氧化物(TMO)、层状双金属氢氧化物 (LDHs)、层状过渡金属含氧酸盐(如K2Ti4O9、KTiNbO5等)和其他化合物,例如金属多卤化物、磷酸盐等。
基于小分子热激活延迟荧光(TADF)材料的蓝、绿、红以及白色OLED器件的最大外量子效率(External quantum efficiency,EQE)打破了传统荧光材料5%的理论极限,同时还可以与贵金属配合物磷光器件相媲美,被认为是继荧光材料和磷光材料之后的第三代OLED材料。 TADF材料具有高的激子利用效率特性,在单重态和三重态具有较小能极差时,通常反向系间窜越(RISC)实现三重态到单重态的能量转换。TADF的设计原则是要求具有较小的ΔEST(< 0.3eV),从而确保热活化RISC过程有效地进行。较小的ΔEST可以通过空间上分离的最高分子占据轨道(Highest occupied molecular orbital,HOMO)和最低分子未占据轨道(Lowest unoccupied molecular orbital,LUMO)来实现。一般来说,HOMO的分布主要是由分子结构中的给体单元(Donor,D)决定,LUMO的分布主要取决于分子结构中的受体单元(Acceptor,A),在构建TADF材料时,选择合适的D和A单元是实现高RISC速率的关键。然而,TADF材料作为发光材料,其另外一个重要的性能就是高的光致发光量子效率(Photoluminescence quantum yields,PLQY)。根据Franck-Condon理论,HOMO和LUMO在空间上一定的重叠是获得高PLQY TADF材料的必要条件,这一要求与小的ΔEST相矛盾。因此,对于TADF材料,获取优异TADF性质的关键在于有效地调节分子中HOMO/LUMO的分布。一般认为有明显的TADF现象的体系ΔEST需小于0.3eV,基于D-A结构设计的TADF分子是目前此类材料的理想构型,其HOMO和LUMO分布在电子给体D和受体A基团上。常用于构筑TADF材料的给体结构主要集中在具有较强的给电子能力、高的三线态能级、较好的稳定性以及制备工艺简单等特点的芳胺单元,如咔唑、吖啶、二苯胺及它们的衍生物;受体主要是具有较强吸电子能力及结构易于修饰特点的三嗪、二苯砜、二苯甲酮以及氧化硫芴等。
发明内容
本发明的目的为了得到一种热激活延迟荧光离子型有机-无机纳米复合插层材料,这类材料含有TADF分子,使得其具有TADF特性。无机层状化合物层状结构具有特定的空间结构,可以为特殊离子的引入提供空间需求,能有效避免TADF分子的聚集淬灭,抑制诸如三线态- 极化子淬灭(TPQ)和三线态-三线态湮灭(TTA)的不利影响。
为了实现上述目的,本发明采用的技术方案如下:
一种热激活延迟荧光离子型有机-无机纳米复合插层材料,其特征在于:具体合成通式如下:通式(1)
或
通式(2)
进一步的,通式(1)中所述的●结构采用如下其中一种:
进一步的,通式(1)中的▲的结构采用如下其中一种:
进一步的,通式(1)和通式(2)中的i为阴离子,其结构如下:
优选地,上述的热激活延迟荧光材料为具有如下结构的化合物:
C1
C2
C3
C4
C5
C6
上述技术方案可以得到以下有益效果:
小分子TADF发光材料相比磷光材料无铱、铂、锇等稀有金属元素,无金属污染。另外, TADF发光材料在热激活作用下可以同时利用单重态激子和三重态激子进行辐射跃迁。因而,这种TADF器件可以实现理论上100%的激子利用率和IQE,其器件效率甚至可以与磷光 OLED相媲美。此外,TADF发光材料采用的是纯有机材料,这极大地降低了成本,有利其实现商业化发展。但是小分子TADF器件在高电流密度下存在高浓度的三线态激子,效率滚降严重并且小分子TADF发光材料易结晶,导致溶解性差。因此,它们大多是通过高温真空热蒸发沉积而成,成本相对较高而且只能生产小尺寸OLED器件。无机层状化合物的结构特点,给TADF材料提供了载体,可以用作层间客体分子排列取向的模板,使得TADF材料可以被固定在这种刚性结构中,有效地减少了TADF分子的聚集淬灭。另外,无机材料的引入大大改善了发光材料的溶解性,使得这种插层材料具有很好的溶液加工性、热稳定性和阻燃性,使其可以作为光致发光材料应用于有机电致发光器件的研究中。
附图说明
图1所示无机层状化合物。
具体实施方式
下面结合实施例对本发明做进一步的说明:
实施例1
合成C1:
在回流条件下,将4,4-二氟二苯砜(5g,19.7mmol),3-溴-9H-咔唑(9.8g,40 mmol)和NaH(0.5g,19.7mmol)在100mL除水四氢呋喃溶液中反应24h合成该化合物。然后将溶液冷却至室温,猝灭NaH,二氯甲烷萃取,无水硫酸钠干燥后旋干,粗产品用石油醚/乙酸乙酯柱层析,旋干得到1。将1(2g,3.4mmol),4-甲酯基苯硼酸(1.15g,7mmol),四(三苯基膦)钯(0.12g,0.1mmol)和Na2CO3(2.2g,20.4 mmol)在THF和H2O各为50mL和5mL中反应24h合成该化合物。然后将溶液冷却至室温,旋干后用二氯甲烷和水萃取,取二氯甲烷层旋干,粗产品用石油醚/乙酸乙酯柱层析,旋干得到C1。
实施例2
合成C2:
在回流条件下,将2,7-二氟9H-噻吨-9-一10,10-二氧化物(5g,17.8mmol),3- 溴-9H-咔唑(8.76g,35.6mmol)和NaH(0.4g,17.8mmol)在80mL除水四氢呋喃溶液中反应24h合成该化合物。然后将溶液冷却至室温,猝灭NaH,二氯甲烷萃取,无水硫酸钠干燥后旋干,粗产品用石油醚/乙酸乙酯柱层析,旋干得到2。将2(2g,3.3 mmol),4-甲酯基苯硼酸(1.1g,6.6mmol),四(三苯基膦)钯(0.12g,0.1mmol)和 Na2CO3(2.2g,20.4mmol)在THF和H2O各为50mL和5mL中反应24h合成该化合物。然后将溶液冷却至室温,旋干后用二氯甲烷和水萃取,取二氯甲烷层旋干,粗产品用石油醚/乙酸乙酯柱层析,旋干得到C2。
实施例3
合成Cx(x=1,2)/水滑石纳米复合插层材料:
在搅拌下,60℃的氮气气氛中,将硝酸镁和硝酸铝溶液(0.24mol dm-3 Mg2+-0.12mol dm-3Al3+,pH约3)滴加到1mol dm-3NaOH溶液(pH约14)中。溶液 pH值降低,在pH值为10时,对含有形成的白色沉淀的溶液部分进行取样,离心分离白色沉淀,用水洗涤后得到HT-NO3。
将Cx嵌入水滑石中,由于Cx无法直接插入HT-NO3中,因此使用了客体客体交换法。首先,将HT-NO3和甲酰胺(50%)在室温下搅拌2周得到前驱体。然后将前驱体与5mM的Cx溶液混合,搅拌2周,得到Cx/水滑石。所得产物用去离子水洗涤并在9000r/min下离心5分钟,最后在真空烘箱中干燥36小时即得到Cx/水滑石热激活延迟荧光纳米复合材料。
以上所述均为本发明的优选实施方式,对于本技术领域的普通技术人员,在不脱离本发明的原理前提下,对本发明的各种等价形式的修改均属于本申请所附权利要求的保护范围。
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