中文   |   English   |   Email Alert

有机共晶光电功能材料与器件

朱伟钢1,2, 甄永刚*1, 董焕丽1, 付红兵1, 胡文平1

化学进展 ›› 2014, Vol. 26 ›› Issue (08) :1292-1306

PDF (3070KB)
化学进展 ›› 2014, Vol. 26 ›› Issue (08) :1292-1306 DOI: 10.7536/PC140339
综述与评论
扫码查看或转发全文

有机共晶光电功能材料与器件

    朱伟钢1,2, 甄永刚*1, 董焕丽1, 付红兵1, 胡文平1
作者信息 +

Organic Cocrystal Optoelectronic Materials and Devices

  • Zhu Weigang1,2, Zhen Yonggang*1, Dong Huanli1, Fu Hongbing1, Hu Wenping1
Author information +
文章历史 +

摘要

在双组分或多组分有机共晶中,特殊的分子堆积方式和聚集态结构以及不同组分之间的协同和集合效应,使得有机共晶不仅保留了单一组分的固有属性,而且展现出更多新颖的宏观光电性质,在电导、铁电、双极性电荷传输、光响应、发光和给受体组分间电荷转移过程等方面具有重要的研究价值和应用前景,为有机单晶器件的高性能化和多功能化发展提供了新途径。因此,有机共晶的制备和性能研究逐渐成为近年来的热点。在本文中我们首先详细地介绍了有机共晶的分类情况,根据形成晶体的作用力分为电荷转移晶体、通过π-π相互作用形成的晶体和以分子间氢键、卤键相互作用为主的晶体;其次,以经典的7,7,8,8-四氰基对苯二醌二甲烷(TCNQ)、1,2,4,5-苯四甲腈(TCNB)和富勒烯(C60)三种典型的受体分子为例,列举了常见的有机给受体材料;再次,介绍了8种制备有机共晶的常用方法,讨论了有机共晶中分子排布方式对性能的影响;最后,介绍了有机共晶在光电器件中的应用。我们相信有机共晶的理论和应用研究会进一步丰富和推动有机晶体材料和光电子学领域的发展。

Abstract

Compared with one-component organic single crystals, organic cocrystals with unique packing structures and aggregate states show a variety of novel optoelectronic properties through multi-component synergistic and collective effects, paving the way to the development of high-performance or multifunctional optoelectronic devices, particularly in electrical conductors, ferroelectricity, ambipolar charge transporting, photoconductivity and luminescence. Moreover, the charge transfer pathway between donor (D) and acceptor (A) in organic cocrystal is also fundamentally interesting. Therefore, studies on organic cocrystals have gained much attentions in recent years. In this paper, firstly, we have classified organic cocrystals into three categories by the driving forces: charge transfer (CT), π-π interaction and halogen/hydrogen bond; secondly, we have introduced common organic donor materials, using 7,7,8,8-tetracyanoquinodimethane (TCNQ), 1,2,4,5-tetracyanobenzene (TCNB) and fullerene (C60) as the typical acceptors; Thirdly, we have listed eight popular methods used to prepare these organic cocrystals and discussed the relationship between molecule packing and performance of organic cocrystal; Finally, we have covered the applications of these novel cocrystals in organic optoelectronics. We believe that the study on the organic cocrystals is an effective way to achieve organic multi-functional single crystal materials and devices and to promote the development of organic solid state optoelectronics.

Contents
1 Introduction
2 Classification of organic cocrystals
2.1 Charge transfer complex crystals
2.2 Crystals formed by π-π interactions
2.3 Crystals formed by halogen and hydrogen bonds
2.4 Other crystals
3 Common donor/acceptor materials
3.1 TCNQ and its derivatives as acceptor
3.2 TCNB as acceptor
3.3 C60 as acceptor
4 Methods for preparation of crystals
4.1 Solution methods
4.2 Vapor phase method
4.3 Mechanochemical preparation
5 Relationship between molecular packing and function
6 Applications of organic cocrystals
6.1 Unipolar field effect transistors
6.2 Ambipolar field effect transistors
6.3 Photoresponse devices
6.4 Luminescent materials
6.5 Ambipolar field-effect and solid emitting crystals
6.6 Ferroelectric crystals
7 Conclusion and outlook

Graphical abstract

关键词

有机半导体 / 共晶 / 光电器件

Key words

organic semiconductors / cocrystals / optoelectronics

引用本文

引用格式 ▾
朱伟钢, 甄永刚, 董焕丽, 付红兵, 胡文平. 有机共晶光电功能材料与器件[J]. 化学进展, 2014, 26(08): 1292-1306 DOI:10.7536/PC140339
Zhu Weigang, Zhen Yonggang, Dong Huanli, Fu Hongbing, Hu Wenping. Organic Cocrystal Optoelectronic Materials and Devices[J]. Progress in Chemistry, 2014, 26(08): 1292-1306 DOI:10.7536/PC140339

登录浏览全文

4963

注册一个新账户 忘记密码

参考文献

[1] Wang C L, Dong H L, Hu W P, Liu Y Q, Zhu D B. Chem. Rev., 2011, 112: 2208.
[2] Hains A W, Liang Z Q, Woodhouse M A, Gregg B A. Chem. Rev., 2010, 110: 6689.
[3] Tang C W, VanSlyke S A. Appl. Phys. Lett., 1987, 51: 913.
[4] Takeya J, Yamagishi M, Tominari Y, Hirahara R, Nakazawa Y, Nishikawa T, Kawase T, Shimoda T, Ogawa S. Appl. Phys. Lett., 2007, 90: 102120.
[5] Stingelin-Stutzmann N, Smits E, Wondergem H, Tanase C, Blom P, Smith P, de Leeuw D. Nat. Mater., 2005, 4: 601.
[6] Li R J, Hu W P, Liu Y Q, Zhu D B. Acc. Chem. Res., 2010, 43: 529.
[7] Briseno A L, Mannsfeld S C B, Reese C, Hancock J M, Xiong Y J, Jenekhe S A, Bao Z N, Xia Y N. Nano Lett., 2007, 7: 2847.
[8] Jiang H, Zhao H P, Zhang K K, Chen X D, Kloc C, Hu W P. Adv. Mater., 2011, 23: 5075.
[9] Dadvand A, Moiseev A G, Sawabe K, Sun W H, Djukic B, Chung I, Takenobu T, Rosei F, Perepichka D F. Angew. Chem. Int. Ed., 2012, 51: 3837.
[10] Bisri S Z, Takenobu T, Yomogida Y, Shimotani H, Yamao T, Hotta S, Iwasa Y. Adv. Funct. Mater., 2009, 19: 1728.
[11] Bisri S Z, Sawabe K, Imakawa M, Maruyama K, Yamao T, Hotta S, Iwasa Y, Takenobu T. Sci. Rep., 2012, 2: 1.
[12] Zhao Y S, Fu H B, Peng A D, Ma Y, Liao Q, Yao J N. Acc. Chem. Res., 2009, 43: 409.
[13] Zheng J Y, Yan Y L, Wang X P, Zhao Y S, Huang J X, Yao J N. J. Am. Chem. Soc., 2012, 134: 2880.
[14] Xu Z Z, Liao Q, Shi Q, Zhang H L, Yao J N, Fu H B. Adv. Mater., 2012, 24: OP216.
[15] Jurchescu O D, Popinciuc M, van Wees B J, Palstra T T M. Adv. Mater., 2007, 19: 688.
[16] Kabe R, Nakanotani H, Sakanoue T, Yahiro M, Adachi C. Adv. Mater., 2009, 21: 4034.
[17] Nakanotani H, Saito M, Nakamura H, Adachi C. Appl. Phys. Lett., 2009, 95: 033308.
[18] Aakeroy C B, Salmon D J. CrystEngComm, 2005, 7: 439.
[19] Desiraju G R. CrystEngComm, 2003, 5: 466.
[20] Dunitz J D. CrystEngComm, 2003, 5: 506.
[21] Zhang J, Geng H, Virk T S, Zhao Y, Tan J H, Di C A, Xu W, Singh K, Hu W P, Shuai Z G, Liu Y Q, Zhu D B. Adv. Mater., 2012, 24: 2603.
[22] Zhang J, Tan J H, Ma Z Y, Xu W, Zhao G Y, Geng H, Di C A, Hu W P, Shuai Z G, Singh K, Zhu D B. J. Am. Chem. Soc., 2012, 135: 558.
[23] Ferraris J, Cowan D O, Walatka V, Perlstein J H. J. Am. Chem. Soc., 1973, 95: 948.
[24] Canevet D, Pérez E M, Martín N. Angew. Chem. Int. Ed., 2011, 50: 9248.
[25] Yan D, Delori A, Lloyd G O, Friš?i D?T, Day G M, Jones W, Lu J, Wei M, Evans D G, Duan X. Angew. Chem. Int. Ed., 2011, 50: 12483.
[26] Stojakovi D?J, Whitis A M, MacGillivray L R. Angew. Chem. Int. Ed., 2013, 52: 12127.
[27] Bosshard C, Pan F, Wong M S, Manetta S, Spreiter R, Cai C, Günter P, Gramlich V. Chem. Phys., 1999, 245: 377.
[28] Harris K D M, Stainton N M, Callan A M, Howie R A. J. Mater. Chem., 1993, 3: 947.
[29] Kumaresan S, Seethalakshmi P G, Kumaradhas P, Devipriya B. J. Mol. Struct., 2013, 1032: 169.
[30] Gagnière E, Mangin D, Puel F, Rivoire A, Monnier O, Garcia E, Klein J P. J. Cryst. Growth, 2009, 311: 2689.
[31] Lee S C, Ueda A, Kamo H, Takahashi K, Uruichi M, Yamamoto K, Yakushi K, Nakao A, Kumai R, Kobayashi K, Nakao H, Murakami Y, Mori H. Chem. Commun., 2012, 48: 8673.
[32] Boyineni A, Jayanty S, Pallepogu R. J. Cryst. Growth, 2013, 380: 241.
[33] Menard E, Podzorov V, Hur S H, Gaur A, Gershenson M E, Rogers J A. Adv. Mater., 2004, 16: 2097.
[34] Jiang H, Yang X J, Cui Z D, Liu Y C, Li H X, Hu W P. Appl. Phys. Lett., 2009, 94: 123308.
[35] Sakai M, Sakuma H, Ito Y, Saito A, Nakamura M, Kudo K. Phys. Rev. B, 2007, 76: 045111.
[36] Olmstead M M, Bettencourt-Dias A D, Lee H M, Pham D, Balch A L. Dalton Trans., 2003, 3227.
[37] Brook D J R, Koch T H. J. Mater. Chem., 1997, 7: 2381.
[38] Li J, Xiong Y, Wu Q H, Wang S T, Gao X K, Li H X. Eur. J. Org. Chem., 2012, 2012: 6136.
[39] Miller J S. Angew. Chem. Int. Ed., 2006, 45: 2508.
[40] Iwata S, Tanaka J, Nagakura S. J. Am. Chem. Soc., 1966, 88: 894.
[41] Reinheimer E, Zhao H H, Dunbar K. J. Chem. Crystallogr., 2010, 40: 514.
[42] Dillon R J, Bardeen C J. J. Phys. Chem. A, 2011, 115: 1627.
[43] Izuoka A, Tachikawa T, Sugawara T, Suzuki Y, Konno M, Saito Y, Shinohara H. J. Chem. Soc. Chem. Commun., 1992, 1472.
[44] Wakahara T, D’Angelo P, Miyazawa K, Nemoto Y, Ito O, Tanigaki N, Bradley D D C, Anthopoulos T D. J. Am. Chem. Soc., 2012, 134: 7204.
[45] Konarev D V, Lyubovskaya R N, Drichko N Y V, Yudanova E I, Shulga Y M, Litvinov A L, Semkin V N, Tarasov B P. J. Mater. Chem., 2000, 10: 803.
[46] Douthwaite R E, Green M L H, Heyes S J, Rosseinsky M J, Turner J F C. J. Chem. Soc. Chem. Commun., 1994, 1367.
[47] Ito Y, Virkar A A, Mannsfeld S, Oh J H, Toney M, Locklin J, Bao Z N. J. Am. Chem. Soc., 2009, 131: 9396.
[48] Wakahara T, Sathish M, Miyazawa K, Hu C P, Tateyama Y, Nemoto Y, Sasaki T, Ito O. J. Am. Chem. Soc., 2009, 131: 9940.
[49] Lei Y L, Jin Y, Zhou D Y, Gu W, Shi X B, Liao L S, Lee S T. Adv. Mater., 2012, 24: 5345.
[50] Liu C, Minari T, Lu X, Kumatani A, Takimiya K, Tsukagoshi K. Adv. Mater., 2011, 23: 523.
[51] Park S K, Varghese S, Kim J H, Yoon S J, Kwon O K, An B K, Gierschner J, Park S Y. J. Am. Chem. Soc., 2013, 135: 4757.
[52] Tremblay N J, Gorodetsky A A, Cox M P, Schiros T, Kim B, Steiner R, Bullard Z, Sattler A, So W Y, Itoh Y, Toney M F, Ogasawara H, Ramirez A P, Kymissis I, Steigerwald M L, Nuckolls C. Chem Phys Chem, 2010, 11: 799.
[53] Black H T, Perepichka D F. Angew. Chem. Int. Ed., 2014, 53: 2138.
[54] Braga D, Maini L, Grepioni F. Chem. Soc. Rev., 2013, 42: 7638.
[55] Friš?i D?T, Jones W. Cryst. Growth Des., 2009, 9: 1621.
[56] Bechgaard K, Kistenmacher T J, Bloch A N, Cowan D O. Acta Crystallogr. B, 1977, 33: 417.
[57] Pope M. Electronic Processes in Organic Crystals and Polymers. 2nd ed. Oxford: Oxford University Press, 1999.
[58] Rao K V, Jayaramulu K, Maji T K, George S J. Angew. Chem. Int. Ed., 2010, 49: 4218.
[59] Sagade A A, Rao K V, Mogera U, George S J, Datta A, Kulkarni G U. Adv. Mater., 2013, 25: 559.
[60] Sato S, Nikawa H, Seki S, Wang L, Luo G F, Lu J, Haranaka M, Tsuchiya T, Nagase S, Akasaka T. Angew. Chem. Int. Ed., 2012, 51: 1589.
[61] Kobayashi H, Nakayama J. Bull. Chem. Soc. Jpn., 1981, 54: 2408.
[62] Zhu L Y, Yi Y P, Li Y, Kim E G, Coropceanu V, Brédas J L. J. Am. Chem. Soc., 2012, 134: 2340.
[63] Wu H D, Wang F X, Xiao Y, Pan G B. J. Mater. Chem. C, 2013, 1: 2286.
[64] Wei L, Yao J N, Fu H B. ACS Nano, 2013, 7: 7573.
[65] Yu W, Wang X Y, Li J, Li Z T, Yan Y K, Wang W, Pei J. Chem. Commun., 2013, 49: 54.
[66] Wu H D, Wang F X, Xiao Y, Pan G B. J. Mater. Chem. C, 2014, 2: 2328.
[67] Lei Y L, Liao L S, Lee S T. J. Am. Chem. Soc., 2013, 135: 3744.
[68] Horiuchi S, Ishii F, Kumai R, Okimoto Y, Tachibana H, Nagaosa N, Tokura Y. Nat. Mater., 2005, 4: 163.
[69] Horiuchi S, Hasegawa T, Tokura Y. J. Phys. Soc. Jpn., 2006, 75: 051016.

PDF (3070KB)

6409

访问

0

被引

详细

导航
相关文章

/

〈 〉