菲并咪唑类衍生物蓝光材料的研究进展
收稿日期: 2018-07-03
修回日期: 2018-09-20
网络出版日期: 2018-10-20
基金资助
广东省自然科学基金(No.2017A030310039)、国家自然科学基金(No.61671162)、广东省科技计划(No.2016A010103031)、广东省教育厅应用研究重大项目(No.2017KZDXM025)、广州市科技计划项目(No.201707010243)、广东省青年珠江学者(2016)资助项目.
Progress on Phenanthroimidazole Derivatives in Blue-Emitting Materials
Received date: 2018-07-03
Revised date: 2018-09-20
Online published: 2018-10-20
Supported by
Project supported by the Natural Science Foundation of Guangdong Province (No. 2017A030310039), the National Natural Science Foundation of China (No. 61671162), the Science and Technology Planning Project of Guangdong Province (No. 2016A010103031), the Key Project of Educational Commission of Guangdong Province (No. 2017KZDXM025), the Science and Technology Planning Project of Guangdong Province (No. 201707010243), and the Guangdong Youth Pearl River Scholar (2016).
即将出现的全球能源危机和低效的能源利用推动了节能设备在显示和照明领域中的应用.节能的有机发光二极管被认为是新一代智能显示器,成为未来节能照明光源最具竞争力的候选产品之一.而高效深蓝色材料的分子设计由于其固有的宽带隙,载流子电荷传输不平衡以及其在固态下的低效率,发展受到很大限制.菲并咪唑基团作为一种新型蓝光材料的构筑单元,具吸引力的双极特性和优异的荧光效率,引起了科研工作者的强烈兴趣.对于菲并咪唑基团深蓝光材料的分子设计及其光物理性能研究具有重要的意义.综述了近几年来含有菲并咪唑类基团蓝光材料的发展状况,对菲并咪唑基团衍生物电致发光器件的发光机理、设计思路与最新进展进行了综述,并对其在未来全彩显示和固态照明领域上的前景进行了展望.
邱志鹏 , 谭继华 , 蔡宁 , 王凯 , 籍少敏 , 霍延平 . 菲并咪唑类衍生物蓝光材料的研究进展[J]. 有机化学, 2019 , 39(3) : 679 -696 . DOI: 10.6023/cjoc201807007
The impending global energy crisis and inefficient energy utilization have driven the use of energy efficient devices for display and lighting applications. Energy-efficient organic light emitting diodes (OLEDs) are considered to be the next generation of smart displays, becoming one of the most competitive candidate for future energy-efficient lighting sources. The molecular design of high-efficiency deep blue materials are greatly limited due to their inherent wide bandgap, poor carrier charge balance and their low efficiency in the solid state. As a novel building block for blue-emitting materials, phenanthroimidazole (PI) group is attractive stems from their bipolar feature and excellent fluorescence efficiency, which has aroused strong interest of researchers. Molecular design and photophysical properties of phenanthroimidazole-based deep blue-emitting materials are of great significance. In this review, an overview of the recent studies on PI-based blue emitters for applications in organic light-emitting diodes (OLEDs) is presented. The luminescence mechanism, design and latest developments of the electroluminescent devices fabricated from phenanthroimidazole derivatives are described, and their prospects in the future of full-color display and solid-state lighting are forecasted.
[1] Tonzola, C. J.; Kulkarni, A. P.; Gifford, A. P.; Kaminsky, W.; Jenekhe, S. A. Adv. Funct. Mater. 2010, 17, 863.
[2] Forrest, S. R. Nature 2004, 428, 911.
[3] Mitschke, U.; Bäuerle, P. J. Chem. Mater. 2000, 10, 1471.
[4] Wei, B.; Liu, J. Z.; Zhang, Y.; Zhang, J. H.; Peng, H. N.; Fan, H. L.; He, Y. B.; Gao, X. C. Adv. Funct. Mater. 2010, 20, 2448.
[5] Chu, T. Y.; Song, O. K. Appl. Phys. Lett. 2007, 90, 151.
[6] Huang, H.; Wang, Y.; Wang, B.; Zhuang, S.; Pan, B.; Yang, X.; Wang, L.; Yang, C. J. Mater. Chem. C 2013, 1, 5899.
[7] Chien, C. H.; Chen, C. K.; Hsu, F. M.; Shu, C. F.; Chou, P. T.; Lai, C. H. Adv. Funct. Mater. 2010, 19, 560.
[8] Goushi, K.; Kou, Y.; Sato, K.; Adachi, C. Nat. Photonics 2012, 6, 253.
[9] Lin, M. S.; Chi, L. C.; Chang, H. W.; Huang, Y. H.; Tien, K. C.; Chen, C. C.; Chang, C. H.; Wu, C. C.; Chaskar, A.; Chou, S. H. J. Chem. Mater. 2011, 22, 870.
[10] Chou, H. H.; Cheng, C. H. Adv. Mater. 2010, 22, 2468.
[11] Yook, K. S.; Lee, J. Y. Adv. Mater. 2012, 24, 3169.
[12] Lee, S. J.; Park, J. S.; Yoon, K. J.; Kim, Y. I.; Jin, S. H.; Kang, S. K.; Gal, Y. S.; Kang, S.; Lee, J. Y.; Kang, J. W. Adv. Funct. Mater. 2010, 18, 3922.
[13] Zhao, G.; Liu, Y.; Zhiming, W.; Shen, F.; He, L.; Sun, G.; Liang, Y.; Ying, L.; Ping, L.; Ma, Y. Chemistry. 2013, 19, 2602.
[14] Shih, P. I.; Chuang, C. Y.; Chien, C. H.; Diau, E. W. G.; Shu, C. F. Adv. Funct. Mater. 2010, 17, 3141.
[15] Kim, R.; Lee, S.; Kim, K. H.; Lee, Y. J.; Kwon, S. K.; Kim, J. J.; Kim, Y. H. Chem. Commun. 2013, 49, 4664.
[16] Zheng, C. J.; Zhao, W. M.; Wang, Z. Q.; Huang, D.; Ye, J.; Ou, X. M.; Zhang, X. H.; Lee, C. S.; Lee, S. T. J. Chem. Mater. 2010, 20, 1560.
[17] Moorthy, J. N.; Natarajan, P.; Venkatakrishnan, P.; Huang, D. F.; Chow, T. J. Org. Lett. 2007, 9, 5215.
[18] Tao, S. L.; Peng, Z. K.; Zhang, X. H.; Wang, P. F.; Lee, C. S.; Lee, S. T. Adv. Funct. Mater. 2010, 15, 1716.
[19] Tong, Q. X.; Lai, S. L.; Chan, M. Y.; Zhou, Y. C.; Kwong, H. L.; Lee, C. S.; Lee, S. T. Chem. Mater. 2008, 20, 6310.
[20] Lin, S. L.; Chan, L. H.; Lee, R. H.; Yen, M. Y.; Kuo, W. J.; Chen, C. T.; Jeng, R. J. Adv. Mater. 2008, 20, 3947.
[21] Zhang, Q.; Li, J.; Shizu, K.; Huang, S.; Hirata, S.; Miyazaki, H.; Adachi, C. J. Am. Chem. Soc. 2012, 134, 14706.
[22] Hirata, S.; Sakai, Y.; Masui, K.; Tanaka, H.; Lee, S. Y.; Nomura, H.; Nakamura, N.; Yasumatsu, M.; Nakanotani, H.; Zhang, Q. Nat. Mater. 2015, 14, 330.
[23] Zhang, Y.; Lai, S. L.; Tong, Q. X.; Lo, M. F.; Ng, T. W.; Chan, M. Y.; Wen, Z. C.; He, J.; Jeff, K. S.; Tang, X. L. Chem. Mater. 2012, 24, 61.
[24] Li, W.; Liu, D.; Shen, F.; Ma, D.; Wang, Z.; Feng, T.; Xu, Y.; Yang, B.; Ma, Y. Adv. Funct. Mater. 2012, 22, 2797.
[25] Zhang, Y.; Lai, S. L.; Tong, Q. X.; Chan, M. Y.; Ng, T. W.; Wen, Z. C.; Zhang, G. Q.; Lee, S. T.; Kwong, H. L.; Lee, C. S. J. Chem. Mater. 2011, 21, 8206.
[26] Huang, H.; Wang, Y.; Zhuang, S.; Yang, X.; Wang, L.; Yang, C. J. Phys. Chem. C 2012, 116, 19458.
[27] Yuan, Y.; Chen, J. X.; Lu, F.; Tong, Q. X.; Yang, Q. D.; Mo, H. W.; Ng, T. W.; Wong, F. L.; Guo, Z. Q.; Ye, J. Chem. Mater. 2013, 25, 4957.
[28] Chen, W. C.; Yuan, Y.; Wu, G. F.; Wei, H. X.; Tang, L.; Tong, Q. X.; Wong, F. L.; Lee, C. S. Adv. Opt. Mater. 2014, 2, 626.
[29] Yuan, Y.; Li, D.; Zhang, X.; Zhao, X.; Liu, Y.; Zhang, J.; Wang, Y. New J. Chem. 2011, 35, 1534.
[30] Richaud, A.; Barba-Behrens, N.; Méndez, F. Org. Lett. 2011, 13, 972.
[31] Duan, L.; Qiao, J.; Sun, Y.; Qiu, Y. Adv. Mater. 2011, 23, 1137.
[32] Wang, Z.; Lu, P.; Chen, S.; Gao, Z.; Shen, F.; Zhang, W.; Xu, Y.; Kwok, H. S.; Ma, Y. J. Chem. Mater. 2011, 21, 5451.
[33] Wang, Z.; Feng, Y.; Zhang, S.; Gao, Y.; Gao, Z.; Chen, Y.; Zhang, X.; Lu, P.; Yang, B.; Chen, P. Phys. Chem. Chem. Phys. 2014, 16, 20772.
[34] Liang, X.; Wang, Z.; Wang, L.; Hanif, M.; Hu, D.; Su, S.; Xie, Z.; Gao, Y.; Yang, B.; Ma, Y. Chin. J. Chem. 2017, 35.
[35] Chen, W. C.; Tong, Q. X.; Lee, C. S. Sci. Adv. Mater. 2015, 7, 2193.
[36] Jiang, J.; Hu, D.; Hanif, M.; Li, X.; Su, S.; Xie, Z.; Liu, L.; Zhang, S.; Yang, B.; Ma, Y. Adv. Opt. Mater. 2016, 4, 2109.
[37] Gong, S.; Chen, Y.; Luo, J.; Yang, C.; Zhong, C.; Qin, J.; Ma, D. Adv. Funct. Mater. 2011, 21, 1168.
[38] Eakins, G. L.; Alford, J. S.; Tiegs, B. J.; Breyfogle, B. E.; Stearman, C. J. J. Phys. Org. Chem. 2011, 24, 1119.
[39] Tan, Y.; Zhao, Z.; Shang, L.; Liu, Y.; Wei, C.; Li, J.; Wei, H.; Liu, Z.; Bian, Z.; Huang, C. J. Mater. Chem. C 2017, 5, 11901.
[40] Li, W.; Pan, Y.; Xiao, R.; Peng, Q.; Zhang, S.; Ma, D.; Li, F.; Shen, F.; Wang, Y.; Yang, B. Adv. Funct. Mater. 2014, 24, 1609.
[41] Wang, Q.; Ma, D. Chem. Soc. Rev. 2010, 39, 2387.
[42] Zhang, S.; Li, W.; Yao, L.; Pan, Y.; Shen, F.; Xiao, R.; Yang, B.; Ma, Y. Chem. Commun. 2013, 49, 11302.
[43] Zhang, S.; Yao, L.; Peng, Q.; Li, W.; Pan, Y.; Xiao, R.; Gao, Y.; Gu, C.; Wang, Z.; Lu, P.; Li, F.; Su, S.; Yang, B.; Ma, Y. Adv. Funct. Mater. 2015, 25, 1755.
[44] Liu, B.; Yuan, Y.; He, D.; Huang, D. Y.; Luo, C. Y.; Zhu, Z. L.; Lu, F.; Tong, Q. X.; Lee, C. S. Chemistry 2016, 22, 12130.
[45] Chen, W. C.; Yuan, Y.; Ni, S. F.; Tong, Q. X.; Wong, F. L.; Lee, C. S. Chem. Sci. 2017, 8, 3599.
[46] Liu, B.; Yu, Z. W.; He, D.; Zhu, Z. L.; Zheng, J.; Yu, Y. D.; Xie, W. F.; Tong, Q. X.; Lee, C.-S. J. Mater. Chem. C 2017, 5, 5402.
[47] Wang, Z. Y.; Liu, B.; Zhao, J. W.; Ruan, G. L.; Tao, S. L.; Tong, Q. X. Org. Electron. 2018, 52, 89.
[48] Chen, W. C.; Yuan, Y.; Zhu, Z. L.; Jiang, Z. Q.; Liao, L. S.; Lee, C. S. Adv. Opt. Mater. 2018, 6, 1700855.
[49] Zhu, Z. L.; Ni, S. F.; Chen, W.; Chen, M.; Zhu, J.; Yuan, Y.; Tong, Q. X.; Wong, F. L.; Lee, C. J. Mater. Chem. C 2018, 6, 3584.
[50] Zhao, J.; Liu, B.; Wang, Z.; Tong, Q. X.; Du, X.; Zheng, C. J.; Lin, H.; Tao, S. L.; Zhang, X. H. ACS Appl. Mater. Interfaces 2018, 10, 9629.
[51] Sinha, S.; Rothe, C.; Güntner, R.; Scherf, U.; Monkman, A. P. Phys. Rev. Lett. 2003, 90, 127402.
[52] Chiang, C. J.; Kimyonok, A.; Etherington, M. K.; Griffiths, G. C.; Jankus, V.; Turksoy, F.; Monkman, A. P. Adv. Funct. Mater. 2013, 23, 739.
[53] Kido, J.; Iizumi, Y. Appl. Phys. Lett. 1998, 73, 2721.
[54] Kondakov, D. Y.; Pawlik, T. D.; Hatwar, T. K.; Spindler, J. P. J. Appl. Phys. 2009, 106, 30.
[55] Chen, Y. H.; Lin, C. C.; Huang, M. J.; Hung, K.; Wu, Y. C.; Lin, W. C.; Chencheng, R. W.; Lin, H. W.; Cheng, C. H. Chem. Sci. 2016, 7, 4044..
[56] Chou, P. Y.; Chou, H. H.; Chen, Y. H.; Su, T. H.; Liao, C. Y.; Lin, H. W.; Lin, W. C.; Yen, H. Y.; Chen, I. C.; Cheng, C. H. Chem. Commun. 2014, 50, 6869.
[57] Zhang, D.; Zhang, D.; Duan, L. ACS Appl. Mater. Interfaces 2016, 8, 23197.
[58] Kim, B.; Park, Y.; Lee, J.; Yokoyama, D.; Lee, J. H.; Kido, J.; Park, J. J. Mater. Chem C 2012, 1, 432
[59] Shan, T.; Gao, Z.; Tang, X.; He, X.; Gao, Y.; Li, J.; Sun, X.; Liu, Y.; Liu, H.; Yang, B.; Lu, P.; Ma, Y. Dyes Pigm. 2017, 142, 189.
[60] Tang, X.; Bai, Q.; Shan, T.; Li, J.; Gao, Y.; Liu, F.; Liu, H.; Peng, Q.; Yang, B.; Li, F.;Lu, P. Adv. Funct. Mater. 2018, 28, 11.
[61] Baldo, M. A.; O'Brien, D. F.; Thompson, M. E.; Forrest, S. R. Phys. Rev. B 1999, 60, 14422.
[62] Tan, J. H.; Huo, Y. P.; Cai, N.; Ji, S, M.; Li, Z. Z.; Zhang, L. Chin. J. Org. Chem. 2017, 37, 2457(in Chinese). (谭继华, 霍延平, 蔡宁, 籍少敏, 李宗植, 张力, 有机化学, 2017, 37, 2457.)
[63] Endo, A.; Mai, O.; Takahashi, A.; Yokoyama, D.; Kato, Y.; Adachi, C. Adv. Mater. 2010, 21, 4802.
[64] Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Nature 2012, 492, 234.
[65] Hirata, S.; Sakai, Y.; Masui, K.; Tanaka, H.; Lee, S. Y.; Nomura, H.; Nakamura, N.; Mao, Y.; Nakanotani, H.; Zhang, Q. Nat. Mater. 2015, 14, 330.
[66] Huang, Z.; Xiang, S.; Zhang, Q.; Lv, X.; Ye, S.; Guo, R.; Wang, L. J. Mater. Chem. C 2018, 6, 2379.
[67] Pei, Q.; Yang, Y.; Yu, G.; Zhang, C.; Heeger, A. J. J. Am. Chem. Soc. 1996, 118, 3922.
[68] Matyba, P.; Yamaguchi, H.; Chhowalla, M.; Robinson, N. D.; Edman, L. ACS Nano. 2011, 5, 574.
[69] Pertegás, A.; Tordera, D.; Serrano-Pérez, J. J.; Ortí, E.; Bolink, H. J. J. Am. Chem. Soc. 2013, 135, 18008.
[70] Subeesh, M. S.; Shanmugasundaram, K.; Sunesh, C. D.; Won, Y. S.; Choe, Y. J. Mater. Chem. C 2015, 3, 4683.
[71] Subeesh, M. S.; Shanmugasundaram, K.; Sunesh, C. D.; Chitumalla, R. K.; Jang, J.; Choe, Y. J. Phys. Chem. C 2016, 120, 12207.
[72] Subeesh, M. S.; Shanmugasundaram, K.; Sunesh, C. D.; Nguyen, T. P.; Choe, Y. J. Phys. Chem. C 2015, 119, 23676.
[73] Subeesh, M. S.; Nguyen, T. P.; Choe, Y. J. Phys. Chem. C 2017, 121, 14811.
[74] Zhao, G. S.; Shi, C. X.; Guo, Z. Q.; Zhu, W. H.; Zhu, S. Q. Chin. J. Org. Chem. 2012, 32, 1620(in Chinese). (赵国生, 史川兴, 郭志前, 朱为宏, 朱世琴, 有机化学, 2012, 32, 1620.)
[75] Li, Z. Z.; Huo, Y. P.; Yang, X. H.; Ji, S. M. Chin. J. Org. Chem. 2016, 36, 2317(in Chinese). (李宗植, 霍延平, 阳香华, 籍少敏, 有机化学, 2016, 36, 2317.)
[76] Cai, Y.; Du, L.; Samedov, K.; Gu, X.; Fei, Q. I.; Sung, H. H.; Patrick, B. O.; Yan, Z.; Jiang, X.; Zhang, H. Chem. Sci. 2018, 9, 4662.
[77] Qiu, S. H.; Xu, S. J.; Zhou, G. F.; Shui, L. L.; Zhu, X. Z. Chin. J. Org. Chem. 2015, 35, 1746(in Chinese). (邱淑海, 许胜杰, 周国富, 水玲玲, 朱晓张, 有机化学, 2015, 35, 1746.)
[78] Song, M.; Chen, Z.; Yu, G. B.; Yin, J.; Liu, S. H. Chin. J. Org. Chem. 2015, 35, 681(in Chinese). (宋敏, 陈钊, 余广鳌, 尹军, 刘盛华, 有机化学, 2015, 35, 681.)
[79] Jadhav, T.; Choi, J. M.; Shinde, J.; Lee, J. Y.; Misra, R. J. Mater. Chem. C 2017, 5, 6014.
[80] Ekbote, A.; Han, S. H.; Jadhav, T.; Mobin, S. M.; Lee, J. Y.; Misra, R. J. Mater. Chem. C 2018, 6, 2077.
[81] Xie, Z.; Chen, C.; Xu, S.; Li, J.; Zhang, Y.; Liu, S.; Xu, J.; Chi, Z. Angew. Chem., Int. Ed. 2015, 127, 7181.
[82] Xu, S.; Liu, T.; Mu, Y.; Wang, Y. F.; Chi, Z.; Lo, C. C.; Liu, S.; Zhang, Y.; Lien, A.; Xu, J. Angew. Chem., Int. Ed. 2015, 54, 874.
[83] Li, G.; Zhao, J.; Zhang, D.; Shi, Z.; Zhu, Z.; Song, H. Q.; Zhu, J.; Tao, S. L.; Lu, F.; Tong, Q. X. J. Mater. Chem. C 2016, 4, 8787.
[84] Fleetham, T.; Li, G.; Wen, L.; Li, J. Adv. Mater. 2014, 26, 7116.
[85] Zhang, C.; Ji, K.; Wang, X.; Wu, H.; Liu, C. Chem. Commun. 2015, 51, 8173.
[86] Dou, C.; Han, L.; Zhao, S.; Zhang, H.; Wang, Y. J. Phys. Chem. Lett. 2011, 2, 666.
[87] Karabunarliev, S.; Baumgarten, M.; Tyutyulkov, N.; Muellen, K. J. Phy. Chem. 1994, 98, 11892.
[88] Romain, M.; Tondelier, D.; Vanel, J. C.; Geffroy, B.; Jeannin, O.; Raultberthelot, J.; Métivier, R.; Poriel, C. Angew. Chem. Int. Ed. 2013, 125, 14397.
[89] Romain, M.; Thiery, S.; Shirinskaya, A.; Declairieux, C.; Tondelier, D.; Geffroy, B.; Jeannin, O.; Rault-Berthelot, J.; Métivier, R.; Poriel, C. Angew. Chem. Int. Ed. 2015, 54, 1176.
[90] Jing, H.; Ning, S.; Dong, Y.; Tang, R.; Ping, L.; Ping, C.; Li, Q.; Ma, D.; Qin, J.; Zhen, L. Adv. Funct. Mater. 2013, 23, 2329.
[91] Zhu, Z. L.; Chen, W. C.; Zhang, L. D.; Liu, X. L.; Tong, Q. X.; Wong, F. L.; Lu, F.; Lee, C. S. J. Mater. Chem. C 2016, 26, 6249
[92] Du, X.; Li, G.; Zhao, J.; Tao, S.; Zheng, C.; Lin, H.; Tong, Q.; Zhang, X. Adv. Opt. Mater. 2017, 5, 23.
[93] He, D.; Yuan, Y.; Liu, B.; Huang, D. Y.; Luo, C. Y.; Lu, F.; Tong, Q. X.; Lee, C. S. Dyes Pigm. 2017, 136, 347.
[94] Chen, W. C.; Yuan, Y.; Xiong, Y.; Rogach, A. L.; Tong, Q. X.; Lee, C. S. ACS Appl Mater Interfaces. 2017, 9, 26268.
[95] Zhang, F.; Li, W.; Wei, D.; Wei, X.; Li, Z.; Zhang, S.; Li, S.; Wei, B.; Cao, G.; Zhai, B. RSC Adv. 2016, 6, 60264.
[96] Wang, Z.; Feng, Y.; Li, H.; Gao, Z.; Zhang, X.; Lu, P.; Chen, P.; Ma, Y.; Liu, S. Phys. Chem. Chem. Phys. 2014, 16, 10837.
[97] Wang, Z.; Li, X.; Xue, K.; Li, H.; Zhang, X.; Liu, Y.; Yu, Z. Q.; Lu, P.; Chen, P. J. Mater. Chem. C 2016, 4, 1886.
[98] Huo, Y. P.; Tan, J. H.; Zhou, P. Q.; Chen, G. W.; Su, S. J.; Cai, X. Y.; CN 108148001, 2018.
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