物理化学学报 >> 2016, Vol. 32 >> Issue (6): 1534-1542.doi: 10.3866/PKU.WHXB201603232

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一步法合成螺双芴及螺氧杂蒽衍生物及其在有机发光二极管中的应用：性能增强及相关的光学现象关

关玉巧1,#,宋娟1,#,孙威1,章琴1,汤超2,李雪3,冯晓苗1,钱妍1,陶友田2,陈淑芬1,*(),汪联辉1,黄维2,*()   

  1. 1 南京邮电大学信息材料与纳米技术研究院,先进生物与化学制造协同创新中心,有机电子与信息显示国家重点实验室培育基地,南京210023
    2 南京工业大学,先进生物与化学制造协同创新中心,柔性电子重点实验室,南京211816
    3 南京工程学院机械工程学院,南京211167
  • 收稿日期:2016-01-05 发布日期:2016-06-03
  • 通讯作者: 陈淑芬,黄维 E-mail:iamsfchen@njupt.edu.cn;wei-huang@njtech.edu.cn
  • 基金资助:
    国家重点基础研究发展规划项目(9732015CB932202, 2012CB933301);国家自然科学基金(61274065, 51173081, 61136003, BZ2010043, 51372119, 51172110, 21304047, 21373114, 21003076);教育部创新团队(IRT1148);教育部人文社会科学基金(13YJCZH091);江苏省自然科学基金(BK20141424);江苏高校优势学科建设工程资助项目(YX030001);江苏省普通高校研究生实践创新项目(SJLX15_0390);南京邮电大学攀登项目(NY214085);吉林大学开放课题(IOSKL2015KF32)

One-Step Synthesis of Spirobi[fluorene] and Spiro[fluorene-9,9′-xanthene] Derivatives and Their Applications in Organic Light-Emitting Devices: Performance Enhancement and Related Optical Phenomena

Yu-Qiao GUAN1,#,Juan SONG1,#,Wei SUN1,Qin ZHANG1,Chao TANG2,Xue LI3,Xiao-Miao FENG1,Yan QIAN1,You-Tian TAO2,Shu-Fen CHEN1,*(),Lian-Hui WANG1,Wei HUANG2,*()   

  1. 1 Key Laboratory for Organic Electronics and Information Displays and Institute of Advanced Materials, and Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing University of Posts and Telecommunications, Nanjing 210023, P. R. China
    2 Key Laboratory of Flexible Electronics and Institute of Advanced Materials, National Synergistic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, P. R. China
    3 Mechanical Engineering Institute, Nanjing Institute of Technology, Nanjing 211167, P. R. China
  • Received:2016-01-05 Published:2016-06-03
  • Contact: Shu-Fen CHEN,Wei HUANG E-mail:iamsfchen@njupt.edu.cn;wei-huang@njtech.edu.cn
  • Supported by:
    The project was supported by the National Key Basic Research Program of China(9732015CB932202, 2012CB933301);National Natural Science Foundation of China(61274065, 51173081, 61136003, BZ2010043, 51372119, 51172110, 21304047, 21373114, 21003076);Innovation Team of the Ministry of Education of China(IRT1148);Ministry of Education Humanities and Social Science Research Projects, China(13YJCZH091);Natural Science Foundation of Jiangsu Province, China(BK20141424);Priority Academic Program Development of Jiangsu Provincial Higher Education Institutions, China(YX030001);Ordinary University Graduate Student Practical Innovation Projects of Jiangsu Province, China(SJLX15_0390);Pandeng Project of Nanjing University of Posts and Telecommunications, China(NY214085);Open Foundation from Jilin University, China(IOSKL2015KF32)

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摘要：

以芴为原料，以钯为催化剂一步合成了2-(9-苯基芴基)-9,9′螺二芴(PF-SBF)。以PF-SBF作为有机发光二极管的发光及主体材料(FIrpic为磷光客体)时，观察到了不同于PF-SBF及FIrpic发光的红光带。这分别源于PF-SBF分子间的聚集和发光层/传输层诱导的激基复合物。通过选择合适的空穴和电子传输层，有效抑制了激基复合物的发光。同时，PF-SBF和TAPC双主体的结构不仅实现了纯FIrpic和Ir(ppy)3蓝光和绿光，还大幅提升了器件性能。蓝光、绿光器件的最大电流效率和最大亮度分达到16.7、50.5 cd·A-1和7857 cd·m-2(11 V)、23390 cd·m-2(8 V)。另外，除了PF-SBF，利用相似的合成方法，我们也合成了2-(9-苯基芴基)-9,9′螺芴氧杂蒽(PF-SFX)，其较大的三线态能级(2.8 eV)较PF-SBF更适合做蓝光主体。以TAPC和PFSFX为双主体的器件最大电流效率提升到了22.6 cd·A-1。所有实验结果均表明，PF-SBF和PF-SFX是构建高效绿光/蓝光磷光主体材料的有效结构单元。

关键词: 钯催化, 一步法, 激基复合物, 双主体, 蓝光有机发光二极管

Abstract:

Employing fluorene as substrate, we synthesized a new spirobifluorene derivative, 2′-(9-phenylfluoren- 9-yl)-9,9′-spirobi[fluorene] (PF-SBF), through a one-step palladium-catalyzed cross-coupling reaction. Utilizing PF-SBF as an emitter and as a host of the blue phosphor bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2- carboxypyri-dyl))iridium(III) (FIrpic) in organic light-emitting devices (OLEDs), we observed a red light band different from the intrinsic blue emission of PF-SBF and FIrpic. This was attributed to the intermolecular aggregation of PF-SBF and to exciplexes generated at the interfaces of the emitting layer and the electron transport layer. The exciplex emission was then restrained through a suitable selection of hole and electron transport layer. Employing PF-SBF with di-[4-(N,N-ditolyl-amino)-phenyl]cyclohexane (TAPC) as a cohost, we obtained high-performance blue and green emissions from FIrpic and tris(2-phenylpyridine)iridium(III) (Ir(ppy)3). The maximum current efficiencies and luminances of the blue and green OLEDs were as high as 16.7 and 50.5 cd·A-1 and 7857 (at 11 V) and 23390 cd·m-2 (at 8 V), respectively. As an alternative to PF-SBF, we also synthesized a new xanthene derivative, 2-(9-phenyl-fluoren-9-yl)spiro[fluorene-9,9′-xanthene] (PF-SFX), with a large triplet energy level of 2.8 eV. Using PF-SFX similarly as a host of FIrpic, the current efficiency and luminance were significantly improved to 22.6 cd·A-1 and 6421 cd·m-2 (at 10 V). These results demonstrate the potential of PF-SBF and PF-SFX as new building blocks for high-efficiency green/blue phosphorescent host materials.

Key words: Palladium catalysis, One-step method, Exciplex, Cohost, Blue organic light-emitting diode