CN112094287A - 一种空穴注入材料及oled器件 - Google Patents
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Abstract
本发明提供了一种空穴注入材料及OLED器件,具有硅杂环化合物和氰基、氟基、三氟甲基、或氰基、氟基、三氟甲基取代的烷基、烷氧基、芳基、杂芳基或芳氧基。本发明的技术方案具有良好的交叉超共轭特性,结合氰基、氟基等强吸电基团和硅基骨架,能够赋予分子较强的还原电位和良好的热稳定性,从而辅助空穴传输层高效地进行空穴注入。
Description
技术领域
本发明涉及OLED器件领域,具体地说,涉及一种空穴注入材料及具有其的OLED器件。
背景技术
有机发光二极管(Organic Light-Emitting Diode,OLED)又称为有机电激光显示、有机发光半导体。OLED显示技术具有自发光、广视角、几乎无穷高的对比度、较低耗电、极高反应速度等优点。
能级匹配对于有机电致发光器件至关重要,以经典的有机电致发光器件为例,其层叠结构包括:阴极、电子传输层、发光层、空穴传输层以及阳极。
一般使用ITO(Indium Tin Oxides,铟锡金属氧化物)作为阳极,但是它的功函数较高,与大部分空穴传输材料的能级相差达到0.4eV左右。因此,如果在阳极以及空穴传输层之间加入一层空穴注入层,一方面可以增加电荷的注入,另一方面还可以提高器件的整体效率以及寿命。
当然,将某些强氧化剂掺杂到空穴传输层中作为空穴注入层也是另一种提高有机电致发光器件的空穴注入效率的途径。不过该方法对于主体材料以及掺杂材料的能级有要求,一般而言,主体材料的HOMO(Highest Occupied Molecular Orbital,最高占据分子轨道)能级需要与客体材料的LUMO(Lowest Unoccupied Molecular Orbital,最低未占分子轨道)能级接近,这样一来,HOMO能级的电子就能更跳跃至掺杂剂的LUMO能级,从而使的空穴传输层形成自由空穴,实现器件电导率的提升。同时,掺杂还可以使界面能带发生弯曲,空穴就能够以穿隧的方式注入。对于掺杂剂的选择,路易酸型金属络合物、卤素、轴烯以及醌类都是比较常见的,但金属络合物以及卤素在器件加工时会存在不稳定等缺点。而轴烯类化合物在合成中步骤较多,成本较高。因此,该方法不能很好的提高有机电致发光器件的空穴注入效率。
因此,本发明提供了一种新型的空穴注入材料及具有其的OLED器件。
发明内容
针对现有技术中的问题,本发明的目的在于提供一种空穴注入材料及具有其的OLED器件,具有良好的交叉超共轭特性,结合氰基、氟基等强吸电基团和硅基骨架,能够赋予分子较强的还原电位和良好的热稳定性,从而辅助空穴传输层高效地进行空穴注入。
根据本发明的一个方面,提供了一种空穴注入材料,具有式I所示的结构的化合物:
优选的:所述式I所示的结构的化合物为:
优选的:所述式I所示的结构的化合物为:
优选的:所述式I所示的结构的化合物为:
优选的:所述式I所示的结构的化合物为:
优选的:所述式I所示的结构的化合物为:
优选的:所述式I所示的结构的化合物为:
根据本发明的另一个方面,还提供一种OLED器件,所述OLED器件中镀有包括根据上述任一项所述的空穴注入材料。
本发明的一种空穴注入材料及具有其的OLED器件,具有良好的交叉超共轭特性,结合氰基、氟基等强吸电基团,能够赋予分子较强的还原电位,从而辅助空穴传输层高效地进行空穴注入。同时,该类材料具有硅基骨架,具有良好的热稳定性,并且该结构赋予其良好的成膜性能。
具体实施方式
现在将参考实施例更全面地描述示例实施方式。然而,示例实施方式能够以多种形式实施,且不应被理解为限于在此阐述的实施方式。相反,提供这些实施方式使得本发明将全面和完整,并将示例实施方式的构思全面地传达给本领域的技术人员。
在本发明的实施例中,提供了一种空穴注入材料及具有其的OLED器件,具有式I所示的结构的化合物:
本发明的实施例具有良好的交叉超共轭特性,结合氰基、氟基等强吸电基团和硅基骨架,能够赋予分子较强的还原电位和良好的热稳定性,从而辅助空穴传输层高效地进行空穴注入。
在本发明的实施例中,为硅杂环化合物,优选其中含Si的数量为1-2个,优选为三元环化合物、四元环化合物、五元环化合物或六元环化合物,并优选可为单杂环化合物或稠杂环化合物。硅基骨架,能够赋予分子良好的热稳定性,从而辅助空穴传输层高效地进行空穴注入。
并优选式I所示的结构的化合物为:
在本发明的实施例中,优选硅杂环化合物上的R选自氰基或氰基取代的烷基、烷氧基、芳基、杂芳基或芳氧基;或者,氟基或氟基取代的烷基、烷氧基、芳基、杂芳基或芳氧基;或者,三氟甲基或三氟甲基取代的烷基、烷氧基、芳基、杂芳基或芳氧基。氰基、氟基等强吸电基团能够赋予分子较强的还原电位,从而辅助空穴传输层高效地进行空穴注入。
并优选式I所示的结构的化合物为:
下面具体实施例描述本发明:
实施例1
制备方程式为:
步骤为:
向反应瓶中加入叔丁醇钾(336.63mg,3mmol),a-1(490.26mg,1mmol)以及10mLTHF(四氢呋喃),在室温下搅拌6小时之后生成a-2,该生成物不提纯直接进入下一步反应。
加入羰基二氰化物(240.00mg,3mmol)搅拌1小时,紧接着加入氟化钾(174.30mg,3mmol)以及四丁基氟化锂(784.38mg,3mmol)继续搅拌1小时。反应溶液浓缩并过柱得到a-3。
最终产物经测得,MS:244.0;
13C-NMR:(3H,82),(4H,117.2),(2H,118),(2H,165)
实施例2
制备方程式为:
步骤为:
向反应瓶中加入中间体b-1(221.91mg,1mmol)、中间体b-2(516.06mg,2mmol)、碳酸钠(211.98mg,2mmol)、四(三苯基膦)钯(11.55mg,1%mmol)和甲苯(10ml),在氮气保护下加热回流24小时,冷却,除去甲苯,加入二氯甲烷,水洗、干燥,粗产品过柱,再用二氯甲烷和乙醇重结晶纯化得到化合物b-3。
最终产物经测得,MS:578.0;
1H-NMR:(4H,7.73),(2H,7.74)
实施例3
制备方程式为:
步骤为:
向反应瓶中加入中间体c-1(295.86mg,1mmol)、中间体c-2(1032.12mg,4mmol)、碳酸钠(211.98mg,2mmol)、四(三苯基膦)钯(11.55mg,1%mmol)和甲苯(10ml),在氮气保护下加热回流24小时,冷却,除去甲苯,加入二氯甲烷,水洗、干燥,粗产品过柱,再用二氯甲烷和乙醇重结晶纯化得到化合物c-3。
最终产物经测得,MS:1008.0;
1H-NMR:(4H,5.20),(8H,7.73),(4H,7.74)
实施例4
制备方程式为:
步骤为:
向反应瓶中加入中间体d-1(247.86mg,1mmol)、中间体d-2(1032.12mg,4mmol)、碳酸钠(211.98mg,2mmol)、四(三苯基膦)钯(11.55mg,1%mmol)和甲苯(10ml),在氮气保护下加热回流24小时,冷却,除去甲苯,加入二氯甲烷,水洗、干燥,粗产品过柱,再用二氯甲烷和乙醇重结晶纯化得到化合物d-3。
最终产物经测得,MS:960;
1H-NMR:(4H,5.30),(8H,7.73),(4H,7.74)
对照试验
实施例5-8
将透明阳极电极ITO基板在异丙醇中超声清洗10min,并暴露在紫外光下30min,随后用等离子体处理10min。随后将处理后的ITO基板放入蒸镀设备。
首先混合蒸镀一层50nm的NPB以及本发明实施例1-4中制备的空穴注入材料(实施例1-4中制备的空穴注入材料和NPB的摩尔比为1:33.3),接着在该混合膜层上蒸镀膜厚为30nm的NPB,然后混合蒸镀CBP以及5%的Ir(ppy)3 膜厚为30nm,随后蒸镀30nm的Alq3(8-羟基喹啉铝),然后再蒸镀2nm LiF,最后蒸镀150nm的金属Al,形成金属阴极,制作本发明的实施例5-8的有机发光元件。
基于本发明的实施例1-4制备的实施例5-8的有机发光元件的结构为:
ITO/NPB:实施例1-4的空穴注入材料/NPB/CBP:Ir(ppy)3/Alq3/LiF/Al。
对比例1
与实施例5-8的区别在于:在实施例5-8混合蒸镀一层50nm的NPB以及实施例1-4的空穴注入材料时不进行空穴注入材料的混合蒸镀,而只蒸镀NPB,其余相同。
对比例1制备的有机发光元件的结构为:
ITO/NPB/CBP:Ir(ppy)3/Alq3/LiF/Al。
性能测试
将本发明实施例5-8和对比例1进行如下性能测试:
(1)驱动电压:测试方法为测定电流密度10mA/cm2下的驱动电压;
(2)寿命:测试方法为在25℃下初始亮度1000nit和DC恒定电流驱动下的发光的半衰寿命。
测试结果如表1所示:
表1:驱动电压和半衰期说明对比
样品 | 驱动电压 | 半衰期寿命(小时) |
实施例5 | 3.8V | 7500 |
实施例6 | 3.9V | 7600 |
实施例7 | 4.1V | 7450 |
实施例8 | 4.1V | 7200 |
对比例1 | 4.6V | 6000 |
从表1结果可以看出,相较于对比例1,本发明实施例5-8的由于掺杂了实施例1-4制备的空穴注入材料而形成空穴注入层,因此,驱动电压更低(大概低0.5V以上)。这是因为本发明实施例1-4制备的空穴注入材料接有强吸电子基团,配合交叉共轭的π键,使得空穴能够在更大区域内出现,形成自由空穴,获得较高的空穴提取率。
同时,本发明实施例1-4制备的空穴注入材料基于稳定的Si-C键,提高了空穴注入材料的热稳定性,延长了器件的使用寿命。
综上,本发明的一种空穴注入材料及具有其的OLED器件,具有良好的交叉超共轭特性,结合氰基、氟基等强吸电基团,能够赋予分子较强的还原电位,从而辅助空穴传输层高效地进行空穴注入。同时,发明的一种空穴注入材料材料及具有其的OLED器件具有硅基骨架,具有良好的热稳定性,赋予了其良好的成膜性能。
以上内容是结合具体的优选实施方式对本发明所作的进一步详细说明,不能认定本发明的具体实施只局限于这些说明。对于本发明所属技术领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干简单推演或替换,都应当视为属于本发明的保护范围。
Claims (10)
10.一种OLED器件,其特征在于:所述OLED器件中镀有根据权利要求1-9任一项所述的空穴注入材料。
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CN111825600A (zh) * | 2019-04-22 | 2020-10-27 | 上海和辉光电有限公司 | 一种含有c60稠环的有机光电材料及其制备方法和应用 |
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CN111825600A (zh) * | 2019-04-22 | 2020-10-27 | 上海和辉光电有限公司 | 一种含有c60稠环的有机光电材料及其制备方法和应用 |
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