有机电致发光技术在通讯、信息、显示和照明等领域显现出巨大的商业应用前景, 十几年来一直是光电信息领域的研究热点之一。相对于无机电致发光材料,有机电致发光材料具有许多优点。近年来,三苯基膦氧基团在合成高性能有机电致发光材料方面的研究吸引了大批研究者的关注。由于磷原子自身性质,可以形成5个共价键,所以膦氧基团极易和其他基团连接形成以其为核的衍生物。由于氧原子具有很强的电负性,这就使膦氧结构高度极化并具有强的吸电子性。吸电子的膦氧基团连接苯环形成的三苯基膦氧单元也具有较强的吸电子性,其对所形成的化合物的能级结构也会产生明显影响。本文从材料合成的角度综述了三苯基膦氧基团在合成高性能有机电致发光材料中的应用方面所取得的最新研究进展,重点介绍了三苯基膦氧基团在合成高性能磷光二极管主体材料、电子传输材料和单分子电致发光材料等方面的应用。最后讨论了三苯基膦氧基团在上述领域应用过程中所存在的问题和功能拓展方向,并对下一步需要研究的热点问题作了展望。
[1] Tang C W, VanSlyke S A. Appl. Phys. Lett., 1987, 51(12):913.
[2] Grimsdale A C, Chan K L, Martin R E, Jokisz P G, Holmes A B. Chem.Rev., 2009, 109(3):897.
[3] Adachi C, Baldo M A, Forrest S R, Thompson M E. Appl. Phys. Lett., 2000, 77(6):904.
[4] Baldo M A, Lamansky S, Burrows P E, Thompson M E, Forrest S R. Appl. Phys. Lett., 1999, 75(1):4.
[5] Lamansky S, Djurovich P, Murphy D, Abdel-Razzaq F, Lee H E, Adachi C, Burrows P E, Forrest S R, Thompson M E. J. Am. Chem. Soc., 2001, 123(18):4304.
[6] Sun Y R, Giebink N C, Kanno H, Ma B W, Thompson M E, Forrest S R. Nature, 2006, 440(7086):908.
[7] Reineke S, Lindner F, Schwartz G, Seidler N, Walzer K, Lussem B, Leo K. Nature, 2009, 459(7244):234.
[8] Baldo M A, Obrien D F, You Y, Shoustikov A, Sibley S, Thompson M E, Forrest S R. Nature, 1998, 395(6698):151.
[9] Su S J, Sasabe H, Takeda T, Kido J. Chem. Mater., 2008, 20(5):1691.
[10] Chaskar A, Chen H F, Wong K T. Adv. Mater., 2011, 23(34):3876.
[11] Tsai M H, Lin H W, Su H C, Ke T H, Wu C C, Tang F C, Liao Y L, Wong K T, Wu C I. Adv. Mater., 2006, 18(9):1216.
[12] Jiang H J. Asian. J. Org. Chem., 2014, 3(2):102.
[13] Ren X, Li J, Holmes R J, Djurovich P I, Forrest S R, Thompson M E. Chem. Mater., 2004, 16(23):4743.
[14] Holmes R J, Andrade B W D, Forrest S R, Ren X, Li J, Thompson M E. Appl. Phys. Lett., 2003, 83(18):3818.
[15] Tao Y, Wang Q, Ao L, Zhong C, Yang C, Qin J, Ma D. J Phys. Chem. C, 2009, 114(1):601.
[16] Rothmann M M, Haneder S, Como E D, Lennartz C, Schildknecht C, Strohriegl P. Chem. Mater., 2010, 22(7):2403.
[17] Son K, Yahiro M, Imai M T, Yoshizaki H, Adachi C. Chem Mater., 2008, 20(13):4439.
[18] Tao Y, Wang Q, Shang Y, Yang C, Ao L, Qin J, Ma D, Shuai Z. Chem. Commun., 2009, 1(1):77.
[19] Tao Y, Wang Q, Yang C, Wang Q, Zhang Z, Zou T, Qin J, Ma D. Angew. Chem. Int. Ed., 2008, 47(42):8104.
[20] Kim M K, Kwon J, Kwon T H, Hong J I. New. J. Chem., 2010, 34(7):1317.
[21] Jeon S O, Yook K S, Joo C W, Lee J Y. Adv. Funct. Mater., 2009, 19(22):3644.
[22] Sawada Y, Furumi S, Takai A, Takeuchi M, Noguchi K, Tanaka K. J. Am. Chem. Soc., 2012, 134(9):4080.
[23] Baba K, Tobisu M, Chatani N. Angew. Chem. Int. Ed., 2013, 52(45):11892.
[24] Wang K, Wang S P, Wei J B, Chen S Y, Liu D, Liu Y, Wang Y. J. Mater. Chem. C, 2014, 2(33):6817.
[25] Zhang Q W, Fang D, Jiang H J, Zhang X W, Zhang H M. Org. Electron., 2015, 27:173.
[26] Liu X K, Zheng C J, Lo M F, Xiao J, Lee C S, Fung M K, Zhang X H. Chem. Commun., 2014, 50(16):2027.
[27] Thiery S, Tondelier D, Geffroy B, Jacques E, Robin M, Mtivier R, Jeannin O, Berthelot J R, Poriel C. Org. Lett., 2015, 17(19):4682.
[28] Han C M, Zhu L P, Li J, Zhao F C, Zhang Z, Xu H, Deng Z P, Ma D G, Yan P F. Adv. Mater., 2014, 26(41):7070.
[29] Burrows P E, Padmaperuma A B, Sapochak L S, Djurovich P, Thompson M E. Appl. Phys. Lett., 2006, 88(18):183503.
[30] Jeon S O, Lee J Y. J. Mater. Chem., 2012, 22(10):4233.
[31] Kim D, Salman S, Coropceanu V, Salomon E, Padmaperuma A B, Sapochak L S, Kahn A, Bredas J L. Chem. Mater., 2010, 22(1):247.
[32] Sapochak L S, Padmaperuma A B, Cai X, Male J L, Burrows P E. J. Phys. Chem. C, 2008, 112(21):7989.
[33] Cai X, Padmaperuma A B, Sapochak L S, Vecchi P A, Burrows P E. Appl. Phys. Lett., 2008, 92(8):083308.
[34] Jeon S O, Yook K S, Joo C W, Lee J Y. Adv. Mater., 2010, 22(16):1872.
[35] Son H S, Seo C W, Lee J Y. J. Mater. Chem., 2011, 21(15):5638.
[36] Ding J, Wang Q, Zhao L, Ma D, Wang L, Jing X, Wang F. J. Mater. Chem., 2010, 20(37):8126.
[37] Chou H H, Cheng C H. Adv. Mater., 2010, 22(22):2468.
[38] Holmes R J, Forrest S R, Tung Y J, Kwong R C, Brown J J, Garon S, Thompson M E. Appl. Phys. Lett., 2003, 82(15):2422.
[39] Jeon S O, Jang S E, Son H S, Lee J Y. Adv. Mater., 2011, 23(12):1436.
[40] Wu M F, Yeh S J, Chen C T, Murayama H, Tsuboi T, Li W, Chao I, Liu S, Wang J K. Adv. Funct. Mater., 2007, 17(12):1887.
[41] Yook K S, Lee J Y. Org. Electron., 2011, 12(10):1711.
[42] Jeon S O, Lee J Y. Tetrahedron, 2010, 66(36):7295.
[43] Han C M, Zhu L P, Zhao F C, Zhang Z, Wang J Z, Deng Z P, Xu H, Li J, Ma D G, Yan P F. Chem. Commun., 2014, 50(20):2670.
[44] Cui L S, Liu Y, Li Q, Jiang Z Q, Liao L S. Org. Electron., 2014, 15(7):1368.
[45] Liu H, Cheng G, Hu D H, Shen F Z, Lv Y, Sun G N, Yang B, Lu P, Ma Y G. Adv. Funct. Mater., 2012, 22(13):2830.
[46] Liu H, Bai Q, Yao L, Hu D H, Tang X Y, Shen F Z, Zhang H H, Gao Y, Lu P, Yang B. Adv. Funct. Mater., 2014, 24(37):5881.
[47] 毛炳雪(Mao B X), 张大鹏(Zhang D P),华晓阳(Hua X Y),姜鸿基(Jiang H J),陈润锋(Chen R F),邓先宇(Deng X Y).化学进展(Progress in Chemistry), 2010, 22(12):2353.
[48] Padmaperuma A B, Sapochak L S, Burrows P E. Chem. Mater., 2006, 18(9):2389.
[49] Son H S, Lee J Y. Org. Electron., 2011, 12(6):1025.
[50] Jang S E, Joo C W, Lee J Y. Thin Solid Films, 2010, 519(2):906.
[51] Jeon S O, Yook K S, Joo C W, Son H S, Lee J Y. Thin Solid Films, 2010, 518(14):3716.
[52] Jang S E, Jang C W, Jeon S O, Yook K S, Lee J Y. Org. Electron., 2010, 11(6):1059.
[53] Yu D, Zhao Y, Xu H, Han C, Ma D, Deng Z, Gao S, Yan P. Chem.-Eur. J., 2011, 17(9):2592.
[54] Hsu F M, Chien C H, Shu C F, Lai C H, Hsieh C C, Wang K W, Chou P T. Adv. Funct. Mater., 2009, 19(17):2834.
[55] Wu J, Wu S X, Wu Y, Kan Y H, Geng Y, Su Z M. Phys. Chem. Chem. Phys., 2013, 15(7):2351.
[56] Ding L, Dong S C, Jiang Z Q, Chen H, Liao L S. Adv. Funct. Mater., 2015, 25(4):645.
[57] Yu D H, Zhao F C, Han C M, Xu H, Li J, Zhang Z, Deng Z P, Ma D G, Yan P F. Adv. Mater., 2012, 24(4):509.
[58] Zhang Z, Zhang Z S, Chen R F, Jia J L, Han C M, Zheng C, Xu H, Yu D H, Zhao Y, Yan P F, Liu S Y, Huang W. Chem.-Eur. J., 2013, 19(29):9549.
[59] Ding D X, Zhang Z, Wei Y, Yan P F, Xu H. J. Mater. Chem. C, 2015, 3(43):11385.
[60] Han C M, Zhao F C, Zhang Z, Zhu L P, Xu H, Li J, Ma D G, Yan P F. Chem. Mater., 2013, 25(24):4966.
[61] Gong S L, Chang Y L, Wu K L, White R, Lu Z H, Song D T, Yang C L. Chem. Mater., 2014, 26(3):1463.
[62] Zhuang J Y, Li W F, Su W M, Zhou M, Cui Z. New. J. Chem., 2014, 38(2):650.
[63] Lee C W, Lee J Y. Adv. Mater., 2013, 25(38):5450.
[64] Lee J H, Cheng S H, Yoo S J, Shin H, Chang J H, Wu C, Wong K T, Kim J J. Adv. Funct. Mater., 2015, 25(3):361.
[65] Sun M Z, Zhu L P, Kan W J, Wei Y, Ma D G, Fan X F, Huang W, Xu H. J. Mater. Chem. C, 2015, 3(36):9469.
[66] Han C M, Zhang Z S, Xu H, Yue S Z, Li J, Yan P R, Deng Z P, Zhao Y, Yan P F, Liu S Y. J. Am. Chem. Soc., 2012, 34(46):19179.
[67] Huang H, Yang X, Wang Y X, Pan B, Wang L, Chen J S, Ma D G, Yang C L. Org. Electron., 2013, 14(10):2573.
[68] Zhuang J Y, Su W M, Wu W C, Li W F, Shen Q, Zhou M. Tetrahedron, 2013, 69(43):9038.
[69] Fan C C, Duan C B, Wei Y, Ding D X, Xu H, Huang W. Chem. Mater., 2015, 27(14):5131.
[70] Wang B, Lv X L, Pan B, Tan J H, Jin J J, Wang L. J. Mater. Chem. C, 2015, 3(42):11192.
[71] Jia J, Zhu L, Wei Y, Wu Z, Xu H, Ding D, Chen R, Ma D, Huang W. J. Mater. Chem. C, 2015, 3(19):4890.
[72] Shao S Y, Ding J Q, Wang L X. Jing X B. Wang F S. J. Am. Chem. Soc., 2012, 134(37):15189.
[73] Shao S Y, Ding J Q, Wang L X, Jing X B, Wang F S. J. Am. Chem. Soc., 2012, 134(50):20290.
[74] Liu C, Li Y H, Li Y F, Yang C L, Wu H B, Qin J G, Cao Y. Chem. Mater., 2013, 25(16):3320.
[75] Mallesham G, Swetha C, Niveditha S, Mohanty M E, Babu N J, Kumar A, Bhanuprakash K, Rao V J. J. Mater. Chem. C, 2015, 3(6):1208.
[76] Joly D, Bouit P A, Hissler M. J. Mater. Chem. C, 2016, 4(17):3686.
[77] Uoyama H, Goushi K, Shizu K, Nomura H, Adachi C. Nature, 2012, 492:234.
[78] Shao S Y, Ding J Q, Ye T L, Xie Z Y, Wang L X, Jing X B, Wang F S. Adv. Mater., 2011, 23(31):3570.
[79] Duan C B, Li J, Han C M, Ding D X, Yang H, Wei Y, Xu H. Chem. Mater., 2016, 28(16):5667.