CN105694859B - 有机电子发光材料 - Google Patents

有机电子发光材料 Download PDF

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CN105694859B
CN105694859B CN201610169071.3A CN201610169071A CN105694859B CN 105694859 B CN105694859 B CN 105694859B CN 201610169071 A CN201610169071 A CN 201610169071A CN 105694859 B CN105694859 B CN 105694859B
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CN105694859A (zh
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李哲
鲁锦鸿
戴雷
蔡丽菲
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Beijing Aglaia Technology Development Co Ltd
Guangdong Aglaia Optoelectronic Materials Co Ltd
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Beijing Aglaia Technology Development Co Ltd
Guangdong Aglaia Optoelectronic Materials Co Ltd
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Priority to TW105111987A priority Critical patent/TWI612030B/zh
Priority to JP2017563555A priority patent/JP2018521166A/ja
Priority to PCT/CN2016/080318 priority patent/WO2016197730A1/zh
Priority to US15/735,177 priority patent/US20180297950A1/en
Priority to KR1020177033228A priority patent/KR20180004735A/ko
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Abstract

本发明涉及有机电子发光材料，具有化学式(I)的结构，本发明的化学式(I)类型的化合物具有高稳定性的吸电子基团与供电子基团，它们之间具有稳定的化学键，且不存在较强的共轭。这些特点使式(I)类化合物具有较高的荧光量子效率和良好的电荷传输能力，且更接近国际标准的深蓝色，有利于实现更高色纯度的全彩显示器。

Description

有机电子发光材料
技术领域
本发明涉及新型的有机光电材料，通过真空蒸镀、印刷、打印等方式形成薄膜，可应用于电致发光器件、薄膜晶体管、太阳能电池和光电传感器、氧气浓度探测器，属于有机光电材料领域。
背景技术
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、厚度薄、色彩丰富、响应速度快、可制作柔性与透明的发光器件等优点，因此有机电致发光器件技术可以应用在新型平板显示器、面光源照明及可穿戴设备等应用领域，也可以作为LCD的背光源。
经过多年的发展，有机电致发光器件技术(OLED)已经达到市场化水平。但目前广泛使用的高效率磷光材料需要用到铱、铂等稀有贵重金属而成本高昂，是OLED成本高居不下的重要因素之一。为了降低OLED材料的成本，开发可以充分利用电激发器件中三线态能级的低成本、高稳定性材料，例如具有热激发延迟荧光的化合物，是有希望解决高性能OLED材料高成本问题的方法之一。
发明内容
本发明的目的在于提供一种新型有机电致发光材料，并将其应用于有机光电器件，该材料具有较低的单线态与三线态之间的能级差，可作为有机电致发光器件中发光层的主体材料或客体材料，也可作为电子传输材料或空穴传输材料。使用该材料可获得更接近国际标准的深蓝色的电致发光器件，有利于实现更高色纯度的全彩显示器。
本发明所述的新型光电材料，具有化学式(I)的结构：
其中，Ar为未取代或者至少有一个R4取代的苯环、萘环、蒽环，n＝0-3；
D为含有氮原子的供电子基团，为以下基团中的一个：
当D为-N(R2)2时，n不为零；
R1，R3，R4各自独立地选自氢H，氘D，氟F，氯Cl，溴Br，碘I，羟基OH，氰基CN，氨基NH2，硝基NO2，具有1至20个碳原子的成环或不成环的烷基，具有1至20个碳原子的成环或不成环的烷氧基，具有1至20个碳原子的成环或不成环的烷硫基，C6-C40的含一个或者多个取代基R5取代或者未取代的芳基，C6-C40的含一个或者多个取代基R5取代或者未取代的芳烃基，C5-C40的含一个或者多个取代基R5取代或者未取代的含有一个或者多个杂原子的杂芳基；R2-R4基团中的两个或多个基团可以互相连接成环；
R2独立选自C6-C40的含一个或者多个取代基R5取代或者未取代的芳基，C6-C40的含一个或者多个取代基R5取代或者未取代的芳烃基，C5-C40的含一个或者多个取代基R5取代或者未取代的含有一个或者多个杂原子的杂芳基；
R5选自氟F，氯Cl，溴Br，碘I，羟基OH，氰基CN，氨基NH2，硝基NO2，具有1至20个碳原子的成环或不成环的烷基；
所述杂原子为B，O，S，Se，N，P。
优选地，R1，R3，R4各自独立地选自氢H，氟F，氯Cl，溴Br，碘I，羟基OH，氰基CN，氨基NH2，硝基NO2，具有1至4个碳原子的烷基，具有1至4个碳原子的烷氧基，具有1至4个碳原子的烷硫基，C6-C25的含一个或者多个取代基R5取代或者未取代的芳基，C6-C25的含一个或者多个取代基R5取代或者未取代的芳烃基，C5-C25的含一个或者多个取代基R5取代或者未取代的含有一个或者多个杂原子的杂原子芳基；R2独立选自C6-C25的含一个或者多个取代基R5取代或者未取代的芳基，C6-C25的含一个或者多个取代基R5取代或者未取代的芳烃基，C5-C25的含一个或者多个取代基R5取代或者未取代的含有一个或者多个杂原子的杂芳基；R1-R4基团中的两个或多个基团可以互相连接成环；
R5选自氢H，氟F，氯Cl，溴Br，碘I，羟基OH，氰基CN，氨基NH2，硝基NO2，具有1至4个碳原子的烷基；所述杂原子为O，S，N，
Ar为未取代或有一个R4取代的苯环、萘环、蒽环。
更优选地，R1，R3,R4各自独立地选自氢H，氟F，氯Cl，溴Br，具有1至4个碳原子的烷基，C6-C25的含一个或者多个取代基R5取代或者未取代的芳基，C6-C25的含一个或者多个取代基R5取代或者未取代的芳烃基，C5-C25的含一个或者多个取代基R5取代或者未取代的含有一个或者多个杂原子的杂原子芳基；R2独立选自C6-C25的含一个或者多个取代基R5取代或者未取代的芳基，C5-C25的含一个或者多个取代基R5取代或者未取代的含有一个或者多个杂原子的杂芳基；R1-R4基团中的两个或多个基团可以互相连接成环；
R5选自氢H，氟F，氯Cl，溴Br，具有1至4个碳原子的烷基；
所述杂原子为O，S，N。
进一步优选：
R1选自具有1至4个碳原子的烷基，含一个或者多个取代基R5取代或者未取代的苯基、萘基、蒽基；
R2独立为含一个或者多个取代基R5取代或者未取代的苯基、萘基或蒽基；
R3选自氢H，氟F，氯Cl，溴Br，碘I，具有1至4个碳原子的烷基，含一个或者多个取代基R5取代或者未取代的苯基、萘基或蒽基；
R4选自氢H，氟F，氯Cl，溴Br，碘I，具有1至4个碳原子的烷基，苯基，萘基；
R5选自氢H，具有1至4个碳原子的烷基。
特别优选：
R1选自具有1至4个碳原子的烷基；
R2独立为苯基、萘基或蒽基；
R3选自氢H，具有1至4个碳原子的烷基，苯基，萘基；
R4选自氢H，具有1至4个碳原子的烷基，苯基，萘基。
下面列出优选的化合物进一步阐明本发明。它们不应被视为以任何方式限制本发明。
再优选：
本发明的具有化学式(I)类型的化合物具有高稳定性的吸电子基团与供电子基团，它们之间具有稳定的化学键，且不存在较强的共轭。这些特点使式(I)类化合物具有较高的荧光量子效率和良好的电荷传输能力，实验表明，更接近国际标准的深蓝色，有潜力应用于有机电致发光器件领域。
本发明的具有结构式(I)的化合物具有刚性分子结构和较少的非辐射退激发途径，其不对称的donor-acceptor结构具有小的单线态-三线态能隙，从而获得高的发光效率；同时，本发明的具有能传输电子或空穴的基团。以上特点使得本发明的化合物可以用于有机电致发光器件、有机薄膜晶体管、有机太阳能电池和有机光电传感器等领域。
附图说明
图1为本发明的器件结构图，10代表玻璃基板，20代表阳极ITO，30代表为空穴传输层，40代表电子/激子阻挡层，50代表为发光层，60代表为激子阻挡层，70代表为电子传输层，80代表为电子注入层，90代表为阴极。
图2为化合物1的1H-NMR图。
具体实施方式
下面结合实施例对本发明做进一步的详细说明。但不应被视为以任何方式限制本发明。
实施例1：化合物1的合成
向反应容器中依次加入2g(0.018mol)二甲氨基甲酰氯，20ml四氢呋喃溶剂，对装置进行除氧、通入氮气保护，冷却降温至反应液温度至-75～-65℃，缓慢滴加10ml 1.6Mn-BuLi/THF溶液，控制反应液温度在-75～-65℃，滴加完毕后，继续保持此温度反应0.5-1h。后将6g化合物1-1滴加进去，控制反应液温度在-75～-65℃，滴加完毕后，继续保持此温度反应0.5-1h，后反应液移至室温自然升温反应4-6h，停止反应。加入乙酸乙酯/去离子水萃取，水层再用乙酸乙酯萃取，合并有机层，无水硫酸镁干燥，抽滤，滤液浓缩得到灰白色固体。将得到的固体进行柱层析，得到白色固体粉末3g。
实施例2：下面是本发明化合物的应用实例。
器件结构如图1。器件制备方式：
首先，将透明导电ITO玻璃(带有阳极20的玻璃基板10)依次经洗涤剂溶液、去离子水、丙酮超声清洗，异丙醇蒸汽清洗，再用氧气等离子处理5分钟。
然后，在ITO上蒸镀35nm厚的NPB作为空穴传输层30。
然后，蒸镀5nm厚的mCP作为电子/激子阻挡层40。
然后，蒸镀20nm厚的发光层50，以mCP作为主体材料，本发明的化合物1作为掺杂材料，掺杂浓度为3％。
然后，蒸镀10nm厚的mCP作为激子阻挡层60。
然后，蒸镀30nm厚的TPBi作为电子传输层70。
最后，蒸镀1nm厚的LiF作为电子注入层80和100nm Al作为阴极90。
本发明所制备的有机电致发光器件发射近紫外光，发射波长在416nm,色坐标为(0.17,0.09)。
比较例
比较例采用文献Angew.Chem.Int.Ed.2014,53，6402–6406中报道的化合物Cz2BP代替化合物1，器件结构与文献中一致，且与实施例6中的器件结构基本相同，除了主体材料及激子阻挡材料采用DPEPO。比较例制备的有机电致发光器件发射波长在446nm,色坐标为(0.16,0.14)。
因此，本发明的材料相比较已报道材料，具有更加接近于国家电视标准委员会(National Television Standards Committee，NTSC)关于深蓝光的标准(0.14,0.08)的色坐标。

Claims (5)

1.有机电子发光材料，具有化学式(I)的结构：
D为含有氮原子的供电子基团，为以下基团：
其中R1选自具有1至4个碳原子的烷基，
R3选自氢H，氟F，氯Cl，溴Br，碘I，具有1至4个碳原子的烷基，含一个或者多个取代基R5取代或者未取代的苯基、萘基或蒽基；
R4选自氢H，氟F，氯Cl，溴Br，碘I，具有1至4个碳原子的烷基，苯基，萘基；
R5选自氢H，具有1至4个碳原子的烷基；
Ar为未取代或有一个R4取代的苯环，n＝1。
2.根据权利要求1所述的有机电子发光材料，其中R1选自具有1至4个碳原子的烷基；
R3选自氢H，具有1至4个碳原子的烷基，苯基，萘基；
R4选自氢H，具有1至4个碳原子的烷基，苯基，萘基。
3.根据权利要求2所述的有机电子发光材料，为下列化合物中的一个：
4.根据权利要求3所述的有机电子发光材料，为下列化合物：
5.权利要求1-4任一有机电子发光材料在有机电致发光器件、有机太阳能电池和有机光电传感器上的应用。
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