CN107759508A - 一种吡啶衍生物及其用途和有机电致发光器件 - Google Patents

一种吡啶衍生物及其用途和有机电致发光器件 Download PDF

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CN107759508A
CN107759508A CN201711064627.3A CN201711064627A CN107759508A CN 107759508 A CN107759508 A CN 107759508A CN 201711064627 A CN201711064627 A CN 201711064627A CN 107759508 A CN107759508 A CN 107759508A
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

本发明提供了一种吡啶衍生物，其具有如下结构式：该吡啶衍生物具有较好的热稳定性，高发光效率，高发光纯度，可以应用于有机电致发光器件、有机太阳能电池、有机薄膜晶体管或有机光感受器领域。本发明还提供了一种有机电致发光器件，该器件包含阳极、阴极和有机层，有机层包含发光层、空穴注入层、空穴传输层、空穴阻挡层、电子注入层、电子传输层中的至少一层，有机层中至少有一层含有如结构式I的化合物，采用吡啶衍生物制作的有机电致发光器件具有电致发光效率良好和色纯度优异以及寿命长的优点。

Description

一种吡啶衍生物及其用途和有机电致发光器件
技术领域
本发明涉及有机电致发光材料领域，具体涉及一种吡啶衍生物及其用途，还涉及一种有机电致发光器件。
背景技术
有机电致发光器件(OLEDs)为在两个金属电极之间通过旋涂或者真空蒸镀沉积一层有机材料制备而成的器件，一个经典的三层有机电致发光器件包含空穴传输层，发光层和电子传输层。由阳极产生的空穴经空穴传输层跟由阴极产生的电子经电子传输层结合在发光层形成激子，而后发光。有机电致发光器件可以根据需要通过改变发光层的材料来调节发射各种需要的光。
有机电致发光器件作为一种新型的显示技术，具有自发光、宽视角、低能耗、效率高、薄、色彩丰富、响应速度快、适用温度范围广、低驱动电压、可制作柔性可弯曲与透明的显示面板以及环境友好等独特优点，可以应用在平板显示器和新一代照明上，也可以作为LCD的背光源。
自从20世纪80年代底发明以来，有机电致发光器件已经在产业上有所应用，比如作为相机和手机等屏幕，但是目前的OLED器件由于效率低，使用寿命短等因素制约其更广泛的应用，特别是大屏幕显示器。而制约其中的一个重要因素就是有机电致发光器件中的有机电致发光材料的性能。另外由于OLED器件在施加电压运行的时候，会产生焦耳热，使得有机材料容易发生结晶，影响了器件的寿命和效率，因此，也需要开发稳定高效的有机电致发光材料。
在OLED材料中，由于大多有机电致发光材料传输空穴的速度要比传输电子的速度快，容易造成发光层的电子和空穴数量不平衡，这样器件的效率就比较低。三(8-羟基喹啉)铝(Alq3)自发明以来，已经被广泛地研究，但是作为电子传输材料它的电子迁移率还是很低，并且自身会降解的内在特性，在以之为电子传输层的器件中，会出现电压下降的情况，同时，由于较低的电子迁移率，使得大量的空穴进入到Alq3层中，过量的空穴以非发光的形式辐射能量，并且在作为电子传输材料时，由于它发绿光的特性，在应用上受到了限制。因此，发展稳定并且具有较大电子迁移率的电子传输材料，对有机电致发光器件的广泛使用具有重大的价值。
发明内容
本发明首先提供一种吡啶衍生物，其为具有如下结构式I的化合物：
其中，Ar选自取代或者未取代的C6-C30的芳基、取代或者未取代的C3-C30的杂芳基；
Py1和Py2中至少有一个基团为吡啶基。
可选的，Ar独立地选自苯基、萘基、三并苯基、蒽基、菲基、芘基、苝基、荧蒽基、(9,9-二烷基)芴基、(9,9-二取代或者未取代的芳基)芴基、9,9-螺芴基、取代或者未取代的C12-C30的二苯并噻吩基、取代或者未取代的C12-C30的二苯并呋喃基、吡啶基、嘧啶基、哒嗪基、三嗪基、咪唑基、噁唑基、氮杂二苯并呋喃基、氮杂二苯并噻吩基、咪唑基，以上芳基和杂芳基还可以进一步为C1-C12的烷基取代。
可选的，吡啶衍生物为下列结构式1-30的化合物：
本发明的吡啶衍生物可以应用在有机电致发光器件、有机太阳能电池、有机薄膜晶体管或有机光感受器领域。
本发明还提供了一种有机电致发光器件，包括阳极、阴极和有机层，有机层包含发光层、空穴注入层、空穴传输层、空穴阻挡层、电子注入层或电子传输层中的至少一层；
可选的，有机层为发光层和电子传输层；
或者有机层为发光层、空穴注入层、空穴传输层和电子传输层；
或者有机层为发光层、空穴注入层、空穴传输层、电子传输层和电子注入层；
或者有机层为发光层、空穴注入层、空穴传输层、电子传输层、电子注入层和阻挡层；
或者有机层为发光层、空穴传输层、电子传输层、电子注入层和阻挡层；
或者有机层为发光层、空穴传输层、电子注入层和阻挡层。
有机层中至少一层包含有所述的吡啶衍生物；
所述吡啶衍生物所在的有机层为电子传输层或电子注入层中的至少一层。
电子传输层或者电子注入层中的化合物为结构式1-30的化合物，或者与其他化合物混合使用。
所述电子传输层或者电子注入层中的化合物为结构式1-30的化合物中的一种或者为至少两种化合物的混合物。
本发明的有机电致发光器件有机层的总厚度为1-1000nm，优选50-500nm。
本发明的有机电致发光器件在使用本发明具有结构式I的化合物时，可以使用搭配其他材料，如空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阻挡层等，而获得蓝光、绿光、黄光、红光或者白光。
本发明有机电致发光器件的有机电子传输材料要求具有很好的电子传输性能，能够有效地把电子从阴极传输到发光层中，具有很大的电子迁移率。除本发明的具有结构式I化合物外，还可以选择或者搭配如下化合物，但是不限于此，氧杂恶唑、噻唑类化合物、三氮唑类化合物、三氮嗪类化合物、三氮杂苯类化合物、喔啉类化合物、二氮蒽类化合物、含硅杂环类化合物、喹啉类化合物、菲啰啉类化合物、金属螯合物(如Alq3，8-羟基喹啉锂)、氟取代苯类化合物及苯并咪唑类化合物。
本发明有机电致发光器件的电子注入层，可以有效的把电子从阴极注入到有机层中，除本发明的具有结构式I化合物外，主要选自碱金属或者碱金属的化合物，或选自碱土金属或者碱土金属的化合物或者碱金属络合物，可以选择如下化合物，但是不限于此，碱金属、碱土金属、稀土金属、碱金属的氧化物或者卤化物、碱土金属的氧化物或者卤化物、稀土金属的氧化物或者卤化物、碱金属或者碱土金属的有机络合物；优选为锂、氟化锂、氧化锂、氮化锂、8-羟基喹啉锂、铯、碳酸铯、8-羟基喹啉铯、钙、氟化钙、氧化钙、镁、氟化镁、碳酸镁、氧化镁，这些化合物可以单独使用也可以混合物使用，也可以跟其他有机电致发光材料配合使用。
本发明的有机电致发光器件中有机层的每一层，可以通过真空蒸镀法、分子束蒸镀法、溶于溶剂的浸涂法、旋涂法、棒涂法或者喷墨打印等方式制备。对于金属电机可以使用蒸镀法或者溅射法进行制备。
器件实验表明，本发明如结构式I所述的吡啶衍生物具有较好热稳定性，高发光效率，高发光纯度。采用该吡啶衍生物制作的有机电致发光器件具有电致发光效率良好和色纯度优异以及寿命长的优点。
附图说明
图1为化合物25的核磁共振谱图；
图2为本发明实施例的有机电致发光器件结构示意图，
其中，110代表为玻璃基板，120代表为阳极，130代表为空穴传输层，140代表为发光层，150代表为电子传输层，160代表为电子注入层，170代表为阴极。
具体实施方式
为了更详细叙述本发明，特举以下例子，但是不限于此。
实施例1
化合物7的合成路线
中间体7-1的合成方法
在烧瓶中，加入2-碘-4,4’-二溴联苯(2.5g，5.8mmol)，3,5-二苯基苯硼酸(1.6g，5.8mmol)，碳酸钾(1.6g，11.6mmol)，四氢呋喃(20mL)和水(10mL)，四三苯基膦钯(0.2g)，在氮气保护下加热回流10小时，冷却，用二氯甲烷萃取，干燥，浓缩，粗产物经柱层析纯化得到产物2g，产率为63％。
化合物7的合成方法
在烧瓶中，加入中间体7-1(2g，3.7mmol)，3-吡啶硼酸频哪醇酯(2.2g，11mmol)，碳酸钾(1g，7.4mmol)，四氢呋喃(20mL)和水(10mL)，四三苯基膦钯(0.2g)，在氮气保护下加热回流24小时，冷却，用二氯甲烷萃取，干燥，浓缩，粗产物经柱层析纯化得到产物1.1g，产率为58％。
实施例2
化合物8的合成路线
中间体8-1的合成方法
合成方法跟中间体7-1的合成一样，所用硼酸为2-三并苯硼酸，产率为70％。化合物8的合成方法
合成方法跟化合物7的合成一样，所用原料为中间体8-1，产率为62％。
实施例3
化合物13的合成路线
中间体13-1的合成方法
合成方法跟中间体7-1的一样，所用原料为9,9-螺二芴-2硼酸，产率为65％。
化合物13的合成方法
合成方法跟化合物7的一样，所用原料为中间体13-1，产率为64％。
实施例4
化合物21的合成路线
中间体21-1的合成方法
合成方法跟中间体7-1的合成一样，所用原料为B-[4-(1-苯基-1H-苯并咪唑-2-基)苯基]-硼酸，产率为52％。
化合物21的合成方法
合成方法跟化合物7的合成一样，所用原料为中间体21-1，产率为49％。
实施例5
化合物25的合成路线
中间体25-1的合成方法
合成方法跟中间体7-1的合成一样，所用硼酸酯为2-(3-苯硼酸频哪醇酯)-4,6-二苯基三嗪，产率为49％。
化合物25的合成方法
合成方法跟化合物7的合成一样，所用原料为中间体25-1，产率为40％，其核磁共振谱图如图1所示。
实施例6-10
有机电致发光器件的制备
使用本发明的化合物制备OLED
首先，将透明导电ITO玻璃基板110(上面带有阳极120)(中国南玻集团股份有限公司)依次经：去离子水，乙醇，丙酮和去离子水洗净，再用氧等离子处理30秒。
然后，蒸镀NPB，形成60nm厚的空穴传输层130。
然后，在空穴传输层上蒸镀37.5nm厚的Alq3掺杂1％C545T作为发光层140。
然后，在发光层上蒸镀37.5nm厚本发明化合物作为电子传输层150。
最后，蒸镀1nm LiF为电子注入层160和100nm Al作为器件阴极170。
所制备的器件(结构示意图见图2)用Photo Research PR650光谱仪测得的在20mA/cm2的电流密度下的效率如表1。
比较例1
除了电子传输层用Alq3代替本发明化合物外，其他的跟实施例6-10一样。
所制备的器件(结构示意图见图2)用Photo Research PR650光谱仪测得的在20mA/cm2的电流密度下的效率如表1。
表1
实施例 化合物 功率效率(lm/W) 颜色
6 7 6.3 绿光
7 8 6.4 绿光
8 13 6.3 绿光
9 21 6.6 绿光
10 25 6.8 绿光
比较例1 Alq3 5.0 绿光
在相同的条件下，应用本发明的吡啶衍生物制备的有机电致发光器件的效率高于比较例，如上所述，本发明的化合物具有高的稳定性，本发明制备的有机电致发光器件具有高的效率和光纯度。
器件中所述化合物的结构式如下：
以上详细描述了本发明的较佳具体实施例。应当理解，本领域的普通技术人员无需创造性劳动就可以根据本发明的构思作出诸多修改和变化。因此，凡本技术领域中技术人员依本发明的构思在现有技术的基础上通过逻辑分析、推理或者有限的实验可以得到的技术方案，皆应在由权利要求书所确定的保护范围内。

Claims (9)

1.一种吡啶衍生物，其特征在于，其为具有如下结构式I的化合物：
其中，Ar选自取代或者未取代的C6-C30的芳基、取代或者未取代的C3-C30的杂芳基；
Py1和Py2中至少有一个基团为吡啶基。
2.如权利要求1所述的吡啶衍生物，其特征在于，Ar独立地选自苯基、萘基、三并苯基、蒽基、菲基、芘基、苝基、荧蒽基、(9,9-二烷基)芴基、(9,9-二取代或者未取代的芳基)芴基、9,9-螺芴基、取代或者未取代的C12-C30的二苯并噻吩基、取代或者未取代的C12-C30的二苯并呋喃基、吡啶基、嘧啶基、哒嗪基、三嗪基、咪唑基、噁唑基、氮杂二苯并呋喃基、氮杂二苯并噻吩基，或者以上芳基和杂芳基进一步被C1-C12的烷基取代。
3.如权利要求1所述的吡啶衍生物，其特征在于，为下列结构式1-30的化合物：
4.如权利要求1所述的吡啶衍生物在有机电致发光器件中的应用。
5.有机电致发光器件，包括阳极、阴极和有机层，有机层包含发光层、空穴注入层、空穴传输层、空穴阻挡层、电子注入层或电子传输层中的至少一层，其特征在于，有机层中至少一层包含有如权利要求1所述的吡啶衍生物。
6.如权利要求5所述的有机电致发光器件，其特征在于，所述吡啶衍生物所在的有机层为电子传输层或电子注入层中的至少一层。
7.如权利要求6所述的有机电致发光器件，其特征在于，所述电子传输层或者电子注入层中的化合物为权利要求3中所述的结构式1-30的化合物，或者与其他化合物混合使用。
8.如权利要求6所述的有机电致发光器件，其特征在于，所述电子传输层或者电子注入层中的化合物为结构式1-30的化合物中的一种或者为至少两种化合物的混合物。
9.如权利要求5所述的有机电致发光器件，其特征在于，所述有机层的总厚度为1-1000nm。
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