基于紫蒽酮衍生物的聚集态与光电性能研究
|
摘要
有机电子学的蓬勃发展使得具有共轭体系的有机材料在发光二极管、薄膜晶体管、太阳电池等方面的研究不断深入。对于有机太阳电池而言,要达到具有应用水平的光电转换效率,要求有机活性层不仅应具备窄带隙和合适的能级,还要求其电荷传输性能足够高。以上两点均要求分子不仅要具有连续的芳环体系以实现π电子在分子内的自由移动,还要有强烈的分子间相互作用以利于π电子在分子间的跳跃传输。据此,本硕士论文选择了兼具上述两种特征的紫蒽酮分子,首先通过分子修饰,合成了带有四种不同空间位阻支链的衍生物3、4、5和6,提高了其溶解性,使其具备应用于大规模器件的潜力。并通过热分析、紫外可见吸收光谱和循环伏安等手段比较了不同取代基对这四种有机小分子的光学性能以及能带结构等的影响,也表明了这四种材料均具备应用于太阳电池的窄带隙、合适能级和强分子间作用等特征。其次,通过不同浓度下核磁信号的变化规律以及DFT计算模拟,深入研究了紫蒽酮分子间π-π相互作用,并初步揭示了基于化合物3二聚体的构象及其因芳核π-π相互作用导致的强烈聚集行为。最后选择其中三种能带结构比较合适的烷氧基衍生物3、4和5作为光活性层材料制备本体异质结太阳电池,讨论了它们各自的能级结构、聚集态结构以及复合薄膜形貌对器件光伏性能的影响,其中基于分子5的太阳电池未经优化效率已达0.54%,主要归因于其复合薄膜均一度高、本体相电荷传输能力强等特征的共同作用。上述的研究结果为人们通过调控有机半导体材料的分子结构和聚集态结构来改善其光电性能提供了参考和借鉴。
The development of organic electronics advances the applications of organic semiconductors in the organic light-emitting diodes (OLEDs), organic field effect transistors (OFETs), and organic solar cells (OSCs). To obtain high-efficiency OSCs, not only the proper band structure with the narrow band gap, but also the excellent charge transport performance are required for the optical active layer. To meet these two demands, it is necessary that organic molecules should have large successiveπsystem as well as strong actions between molecules so that electrons can move easily within and between molecules. Accordingly, in this dissertation, four kinds of violanthrone derivatives with different substituents,3,4,5, and 6, were synthesized. Through thermal analysis, UV-Vis absorption and cyclic voltammetry, the effect of different substituents on optical properties and energy levels was investigated. It was found that four compounds can be potentially in applied in OSCs because of their narrow band gap, proper HOMO and LUMO levels, and strong intermolecular actions. Furthermore, by concentration-depend NMR spectroscopy and DFT calculations, the conformation of 3 dimer was disclosed:there exist stronger intermolecularπ-πactions. Finally, bulk heterojunction (BHJ) OSCs based on four violanthrone derivatives as active layer were fabricated to investigate the relationship between band structure, molecules aggregation, film morphology and performance of photovoltaic devices. Among 4 compounds, solar cells based on 5 achieved a conversion efficiency of 0.54% without optimization. This good performance depended on highly homogenous morphology of the active film and good charge transport properties in relative successive phase. The above results would provide us useful information and tools in the improvement of opto-electronic properties of organic semicondutors through the tuning of their molecular and aggregate structures.
The development of organic electronics advances the applications of organic semiconductors in the organic light-emitting diodes (OLEDs), organic field effect transistors (OFETs), and organic solar cells (OSCs). To obtain high-efficiency OSCs, not only the proper band structure with the narrow band gap, but also the excellent charge transport performance are required for the optical active layer. To meet these two demands, it is necessary that organic molecules should have large successiveπsystem as well as strong actions between molecules so that electrons can move easily within and between molecules. Accordingly, in this dissertation, four kinds of violanthrone derivatives with different substituents,3,4,5, and 6, were synthesized. Through thermal analysis, UV-Vis absorption and cyclic voltammetry, the effect of different substituents on optical properties and energy levels was investigated. It was found that four compounds can be potentially in applied in OSCs because of their narrow band gap, proper HOMO and LUMO levels, and strong intermolecular actions. Furthermore, by concentration-depend NMR spectroscopy and DFT calculations, the conformation of 3 dimer was disclosed:there exist stronger intermolecularπ-πactions. Finally, bulk heterojunction (BHJ) OSCs based on four violanthrone derivatives as active layer were fabricated to investigate the relationship between band structure, molecules aggregation, film morphology and performance of photovoltaic devices. Among 4 compounds, solar cells based on 5 achieved a conversion efficiency of 0.54% without optimization. This good performance depended on highly homogenous morphology of the active film and good charge transport properties in relative successive phase. The above results would provide us useful information and tools in the improvement of opto-electronic properties of organic semicondutors through the tuning of their molecular and aggregate structures.
引文
1. Eley, D. D. Nature 1948,162,819.
2. (a) Pope, M.; Kallmann, H.; Magnante, P. J. Chem. Phys.1963,38,2042. (b) Helfrich, W.; Schneider, W. G. Phys. Rev. Lett.1965,14,229.
3. Ferraris, J.; Cowan, D.O.; Walatka, V.; Perlstein, J. H. J. Am. Chem. Soc.1973, 95,948.
4. Chiang, C. K.; Shirakawa, H.; Frincher, C. R. J. Chem. Soc. Chem. Comm. 1977,39,1098.
5. Walatka, V. V.; Labes, M. M.; Perlstein, J. J. Phys. Rev. Lett.1973,31,1139.
6. (a) Berets, D. J.; Smith, D. S. Trans. Faraday Soc.1968,64,823. (b) Chiang, C. K.; Fincher, C. R.; Jr, Park, Y. W.; Heeger, A. J.; Shirakawa, H.; Louis, E. J.; Gau, S. C.; Alan; MacDiarmid, G. Phys. Rev. Lett.1977,39,1098.
7. Tang, C. W. Appl. Phys. Lett.1986,48,183.
8. (a) Koezuka, H. A.; Tsumara, T. A.; Synth. Met.1987,18,699. (b) Burroughes, J. H.; Jones, C. A.; Friend, R. H. Nature 1988,335,137. (c) Horowitz, D. F.; Peng, X. Z.; Xu, Z.; Garnier, F. Solid State Comm.1989,72,381.
9. Tang, C. W.; VanSlyke, S. A. Appl. Phys. Lett.1987,51,913. (b) Tang, C. W.; VanSlyke, S. A. J. Appl. Phys.1989,65,3610.
10. (a) Burroughes, J. H.; Bradley, D. C; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burn, P. L.; Holmes, A. B. Nature 1990,347,539. (b) Braun, D.; Heeger, A. J. Appl. Phys. Lett.1991,58,1982.
11. (a) Yang, Y; Chang, S. C; Bharathan, J.; Liu, J. J. Mater. Sci. Mater. Electron. 2000,11,89. (b) Hoth, C. N.; Schilinsky, P.; Choulis, S. A.; Brabec, C. J. Nano. Lett.2008,8,2806.
12. Schilinsky, P.; Waldauf, C; Brabec, C. J. Adv. Funct. Mater.2006,16,1669.
13. Shaheen, S. E.; Radspinner, R.; Peyghambarian, N.; Jabbour, G. E. Appl. Phys. Lett.2001,79,2996.
14. (a) Su, S. J.; Gonmori, E.; Sasabe, H.; Kido, J. Adv. Mater.2009,21,361. (b) Su, S. J.; Chiba, T.; Takeda, T.; Kido, J. Adv. Mater.2008,20,1. (c) Huang, F.; Shih, P. I.; Shu, C. F.; Chi, Y A.; Jen, K. Y Adv. Mater.2009,21,361.
15. (a) Wang, E.; Wang, L.; Lan, L.; Luo, C; Zhuang, W.; Peng, J.; Cao, Y. Appl. Phys. Lett.2008,92,033307. (b) Irwin, M. D.; Buchholz, D. B.; Hains, A. W.; Chang, R. P. H.; Marks, T. J. Proc. Natl. Acad. Sci. USA,2008,105,2783. (c) Hou, J.; Chen, H. Y; Zhang, S.; Li, G; Yang, Y J. Am. Chem. Soc.2008,130, 16144. (d) Peet, J.; Kim, J. Y; Coates, N. E.; Ma, W. L.; Moses, D.; Heeger, A. J.; Bazan, G. C. Nat. Mater.2007,6,497.
16. (a) Yan, H.; Chen, Z.; Zheng, Y; Newman, C; Quinn, J. R.; Dotz, F.; Kastler, M.; Facchetti, A. Nature 2009,457,679. (b) Tang, M.; Reichardt, A.; Miyaki, N.; Stoltenberg, R. M.; Bao, Z. J. Am. Chem. Soc.2008,130,6064. (c) Klauk, H.; Zschieschang, U.; Pflaum. J.; Halik, M. Nature 2007,445,745. (d) Tsao, H. N.; Cho, D.; Andreasen, J. W.; Rouhanipour, A.; Breiby, D. W.; Pisula, W.; Mullen, K. Adv. Mater.2009,21,209.
17. Scott, J. C.; Bozano, L. D. Adv. Mater.2007,19,1452.
18. Liang, Y. Y.; Xu, Z.; Xia, J. B.; Tsai, S. T.; Wu, Y.; Li, G; Ray, C; Yu, L. P.; Angew. Chem. Int. Ed.2010,22,1.
19. Sze, S. M. Semiconductor Devices:Physics and Technology Wiley, New York, 1985,6,216,507.
20. Moore, G. E. IEEE IEDM Tech. Dig.1975,11.
21. Subramanian, V. IEEE Trans. Comp. Pack. Tech.2005,28,742.
22. (a) Torsi, L.; Dodabalapur, A. Anal. Chem. A-Pages,2005,77,380. (b) Katz, H. E. J. Appl. Phys.2002,91,1572.
23. Muccini, M. Nat. Mater.2006,5,605.
24. (a) Kitamura, M. Jpn. J. Appl. Phys.2003,42,2483. (b) Huitema, H. E. A. Adv. Mater.2002,14,1201.
25. (a) Wang, Z. Adv. Mater.2003,15,1009. (b) Halik, M. Adv. Mater.2002,14, 1717. (c) Sirringhaus, H. Science 2000,290,2123.
26. (a) Yamaguchi, S. Pure Appl. Chem.2006,78,721. (b) Kunugi, Y. Chem. Mater. 2003,15,6. (c) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater.2002,14, 99.
27. Carswell, D. J. Nature 1954,173,736.
28. (a) Rang, Z. Appl. Phys. Lett.2001,79,2731. (b) Klauk, H. IEEE Trans. Electron Dev.1999,46,1258. (c) Horowitz, G. Synth. Met.1991,41,1127.
29. (a) Sundar, V. Science 2004,303,1644. (b) Hulea, I. N. Appl. Phys. Lett.2006, 88,113512. (c) Stingelin-Stutzmann, N. Nat. Mater.2005,4,601. (d) Briseno, A. L. Adv. Mater.2006,18,2320.
30. Wurthner, F.; Schmidt, R. ChemPhysChem 2006,7,793.
31. Lin, Y. Y. IEEE Trans. Electron Dev. Lett.1997,18,606.
32. Klauk, H. J. Appl. Phys.2002,92,5259.
33. Laudise, R. A. J. Cryst. Growth 1998,187,449.
34. (a) Minakata, T. J. Appl. Phys.1992,72,4178. (b) Minakata, T. J. Appl. Phys. 1993,74,1079.
35. Kagan, C. R. Appl. Phys. Lett.2005,86,193505.
36. (a) Huang, C. J. Appl. Phys.2006,100,114512. (b) Lee, C. A. Appl. Phys. Lett. 2006,88,252102. (c) Kobayashi, S. Nat. Mater.2004,3,317.
37. (a) Hamadani, B. H. Nano Lett.2006,6,1303. (b) Tsukagoshi, K. Appl. Phys. Lett.2006, 89,113507. (c) Salleo, A. Appl. Phys. Lett.2002,81,4383. (d) Facchetti, A. Adv. Mater.2005,17,1705.
38. Fritz, S. E. J. Phys. Chem. B 2005,109,10574.
39. Pratontep, M. Synth. Met.2004,745,387.
40. Locklin, J. Macromol. Sci. Polym. Rev.2006,46,79.
41. Lee, H. S.Adv. Funct. Mater.2006,16,1859.
42. Horowitz, G. Synth. Met.1992,51,419.
43. Garnier, F. J. Am. Chem. Soc.1993,115,8716.
44. Hajlaoui, M. E. Synth. Met.2002,129,215.
45. Akimichi, H.Appl. Phys. Lett.1991,58,1500.
46. (a) Katz, H. E. Nature 2000,404,478. (b) Gamier, F. Chem. Mater.1998,10, 3334.
47. Facchetti, A. J. Am. Chem. Soc.2004,126,13480.
48. Barbarella, G. J. Am. Chem. Soc.1999,121,8920.
49. Murphy, A. R. J. Am. Chem. Soc.2004,126,1596.
50. Laquindanum, J. G. Adv. Mater.1997,9,36.
51. Li, X. C. J. Am. Chem. Soc.1998,120,2206.
52. Ichikawa, M. Adv. Mater.2002,14,1272.
53. Ponomarenko, S. A. Chem. Mater.2006,18,579.
54. Meng, H. J. Am. Chem. Soc.2001,123,9214.
55. Laquindanum, J. G. J. Am. Chem. Soc.1998,120,664.
56. Barbe, D. F. J. Phys. Chem. Solids 1970,31,2679.
57. (a) Madru, R. Chem. Phys. Lett.1988,145,343. (b) Bao, Z. Appl. Phys. Lett. 1996,69,3066.
58. Bao, Z. Adv. Mater.1997,9,42.
59. Someya, T. Proc. Nat. Acad. Sci USA,2005,102,12321.
60. Tang, Q. Adv. Mater.2006,18,65.
61. Pron, A.; Rannou, P. Prog. Polym. Sci.2002,27,135.
62. McCullough, R. D. Adv. Mater.1998,10,93.
63. Assadi, Appl.Phys.Lett.1988,53,195.
64. Tsumura, A. Synth. Met.1991,41,1181.
65. Paloheimo, J. Synth. Met.1991,41,563.
66. Katz, H. E. Acc. Chem. Res.2001,34,359.
67. Paloheimo, J. Appl. Phys. Lett.1990,56,1157.
68. Tanese, M. C, Chem. Mater.2006,18,778.
69. Bredas, J. L. J. Chem. Phys.1985,82,3808.
70. (a) Chen, T. A. J. Am. Chem. Soc.1995,117,233. (b) Sirringhaus, H. Nature 1999,401,685. (c) Bao, Z. Appl. Phys. Lett.1996,69,4108. (d) Sirringhaus, H. Science 1998,280,1741.
71. (a) Kline, R. J. Macromolecules 2005,38,3312. (b) Zen, A. Macromolecules 2006,39,2162.
72. Chang, J. F. Chem. Mater.2004,16, 4772.
73. (a) Majewski, L. A. Appl. Phys. Lett.2006,88,222108. (b) Surin, M. J. Appl. Phys.2006,100,033712.
74. Jia, H. J. Vac. Sci. Tech. A 2006,24,1228.
75. Kim, D. H. J. Phys. Chem. B 2006,110,15763.
76. Hoshino, S. J. Appl. Phys.2004,95,5088.
77. Bao, Z. Chem. Mater.1997,9,1299.
78. Ong, B. S. J. Am. Chem. Soc.2004,126,3378.
79. McCulloch, I. Nat. Mater.2006,5,328.
80. Lim, E. J. Polym. Sci. Part A:Polym. Chem.2006,44,4709.
81. Kim, Y. Macromolecules 2006,39,4081.
82. Usta, H. J. Am. Chem. Soc.2006,128,9034.
83. Chua. L. L. Adv. Mater.2004.16.1609.
84. (a) Li, Y. Macromolecules 2006,39,6521. (b) Drolet, N. Adv. Funct. Mater. 2005,15,1671.
85. Majewski, L. A. Adv. Funct Mater.2005,15,1017.
86. Veres, J. Chem. Mater.2004,16,4543.
87. Newman, C. R. Chem. Mater.2004,16,4436.
88. Chua, L. L. Nature 2005,434,194.
89. Yoon, M. H. J. Am. Chem. Soc.2006,128,12851.
90. Facchetti, A. Angew. Chem. Int. Ed.2000,39,4547.
91. (a) Facchetti, A. Adv. Mater.2003,15,33. (b) Facchetti, A. J. Am. Chem. Soc. 2004,126,13859.
92. Facchetti, A. Angew. Chem. Int. Ed.2003,42,3900.
93. Yoon, M. H. J. Am. Chem. Soc.2006,128,5792.
94. Yoon, M. H. J. Am. Chem. Soc.2005,127,1348.
95. Letizia, J. A. J. Am. Chem. Soc.2005,127,13476.
96. Facchetti, A. Chem. Mater.2004,16,4715.
97. Ando, S. J. Am. Chem. Soc.2005,127,14996.
98. Naraso J. Am. Chem. Soc.2006,128,9598.
99. (a) Ostrick, J. R. J. Appl. Phys.1997,81,6804. (b) Uchida, T. Bull. Chem. Soc. Jpn.1961,34,1015.
100.Rademacher, A. Chem. Ber.1982,115,2927.
101.Katz, H. E. J. Am. Chem. Soc.2000,122,7787.
102.Laquindanum, J. G. J. Am. Chem. Soc.1996,118,11331.
103.Katz, H. E. Nature 2000,404,478.
104.Malenfant, P. R. L. Appl. Phys. Lett.2002,80,2517.
105.Chesterfield, R. J. J. Appl. Phys.2004,95,6396.
106.Tatemichi, S. Appl. Phys. Lett.2006,89,112108/1.
107 Jones, B. Angew. Chem. Int. Ed.2004,43,6363.
108.Yoo, B. IEEE Electron Dev. Lett.2006,27,737.
109.Sakamoto, Y. J. Am. Chem. Soc.2004,126,8138.
110.Schlettwein, D. Chem. Mater.1994,6,3.
111.Bao, Z. J. Am. Chem. Soc.1998,120,207.
112.Kastner, J. Solid State Sciences Kuzmany, H. (eds.), Springer, New York,1993.
113.Haddon, R. C. Appl. Phys. Lett.1995,67,121.
114.Stefan, C. B.; Mannsfeld, A. S.; Liu, S. H.; Roberts, M. E.; McCulloch, I.; Heeney, M.; Bao, Z. N. Adv. Mater.2008,20,4044.
115.Kelley, T. W. in Organic Electronics. Materials, Manufacturing and Applications (Ed:H. Klauk,) Wiley-VCH, Weinheim 2006,33.
116.Yu, G.; Hummelen, J. C; Wudl, F.; Heeger, A. J. Science 1995,270,1789.
117.Kippelen, B.; Bredas, J. L. Energy Environ. Sci.2009,2,251.
118.Blom, P. W. M; Mihailetchi, V. D.; Koster, L. A. J.; Markov, D. E. Adv. Mater. 2007,79,1551.
119.Yu, G.; Hummelen, J. C; Wudl, F.; Heeger, A. J. Science 1995,270,1789.
120.Halls, J. J. M.; Pichler, K.; Friend, R. H.; Moratti, S. C; Holmes, A. B. Appl. Phys. Lett.1996,68,3120.
121.(a) Hwang, I. W.; Moses, D.; Heeger, A. J. J. Phys. Chem. C 2008,112,4350. (b) De, S.; Pascher, T.; Maiti, M.; Jespersen, K. G.; Kesti, T.; Zhang, F. L.; Inganas, O.;Yartsez, A.; Sundstrom, V. J. Am. Chem. Soc.2007,129,8466. (c) Mihailetchi, V. D.; Koster, L. J. A.; Hummelen, J. C; Blom, P. W. M. Phys. Rev. Lett.2004,93,216601.
122.Mihailetchi, V. D.; Blom, P. W. M.; Hummelen, J. C; Rispens, M. T. J. Appl. Phys.2003,94,6849.
123.(a) Bredas, J. L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev.2004,104, 4971. (b) Scharber, M. C; Muhlbacher, D.; Koppe, M.; Denk, P.; Waldauf, C. Heeger, A. J.;Brabec, C. J. Adv. Mater.2006,18,789.
124.(a) Kim, J. Y.; Lee, K.; Coates, N. E.; Moses, D.; Nguyen, T. Q.; Dante, M.; Heeger, A. J. Science 2007,317,222. (b) Dennler, G.; Scharber. M. C; Ameri, T. Denk, P.; Forberich, K.; Waldauf, C.;Brabec, C. J. Adv. Mater.2008,20,579.
125.Kline, R. J.; McGehee, M. D. Polym. Rev.2006,46,27.
126.(a) Ma, W. L.; Yang, C. Y.; Gong, X.; Lee, K.; Heeger, A. J. Adv. Funct Mater. 2005,15,1617. (b) Padinger, F.; Rittberger, R. S.; Sariciftci, N. S. Adv. Funct. Mater.2003,13,85.
127.(a) Li, G.; Shrotriya, V.; Huang, J. S.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y. Nat. Mater.2005,4,864. (b) Pivrikas, A.; Stadler, P.; Neugebauer, H.; Sariciftci, N. S. Org. Electron.2008,9,775. (c) Moule, A. J.; Meerholz, K. Adv. Mater. 2008,20,240.
128.Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Chem. Rev.2007,107,1324.
129.(a) Yao, Y.; Hou, J. H.; Xu, Z.; Li, G.; Yang, Y. Adv. Funct. Mater.2008,18, 1783. (b) Campoy-Quiles, M.; Ferenczi, T.; Angostinelli, T.; Etchegoin, P. G.; Kim, Y.; Anthopoulos, T. D.; Stavrinou, P. N.; Bradley, D. D. C; Nelson J. Nat. Mater.2008,7,158.
130.Coropceanu, V.; Cornil, J.; da Silva, D. A.; Olivier, Y.; Silbey, R.; Bredas, J. L. Chem. Rev.2007,107,926.
131.(a) Cho, S. N.; Yuen, J.; Kim, J. Y.; Lee, K.; Heeger, A. J. Appl. Phys. Lett.2006, 89,153505. (b) Cho, S.; Lee, J. K.; Moon, J. S.; Yuen, J.; Lee, K.; Heeger, A. J. Org. Electron.2008,9,1107.
132.Clarke, T. M.; Ballantyne, A. M.; Nelson, J.; Bradley, D. D. C; Durrant, J. R. Adv. Funct. Mater.2008,18,4029.
133.Jiang, X. M.; Osterbacka, R.; Korovyanko, O.; An, C. P.; Horovitz, B.; Janssen,R. A. J.; Vardeny, Z. V. Adv. Funct. Mater.2002,12,587.
134.Arkhipov, V. I.; Heremans, P.; Bassler, H. Appl. Phys.Lett.2003,82,4605.
135.Malenfant, P. R. L.; Dimitrakopoulos, C. D.; Gelorme, J. D.; Kosbar, L. L. Graham, T. O.; Curioni, A.; Andreoni, W. Appl. Phys. Lett.2002,80,2517.
136.(a) Graser, F.; Hadicke, E. Liebigs Ann. Chem.1980,1994. (b) Klebe, G.; Graser, F.; Hadicke, E.; Berndt, J. Acta Crystallogr.1989, B45,69.
137.Stepanenko, V.; Stocker, M.; Muller, P.; Buchner, M.; Wurthner, F. J. Mater. Chem.2009,19,6816.
138.(a) Chen, H. Z.; Shi, M. M; Mo, X.; Wang, M.; Bao, Z. Chem. Mater.2007,19, 816. (b) Chen, H. Z.; Shi, M. M.; Aernouts, T.; Wang, M.; Borghs, G.; Heremans, P. Sol. Energy Mater. Sol. Cells 2005,87,521. (c) Shi, M. M.; Chen, H. Z.; Shi, Y. W.; Sun, J. Z.; Wang, M. J. Phys. Chem. B 2004,108,5901. (d) Shi, M. M.; Chen, H. Z.; Sun, J. Z.; Ye, J.; Wang, M. Chem. Commun.,2003,14,1710.
139.Chen, J.; Shi, M. M.; Hu, X. L.; Wang, M.; Chen, H. Z. Polymer 2010,51,2897. (b) Deng, D.; Shi, M. M.; Chen, F.; Chen, L.; Jiang, X. X.; Chen, H. Z. Solar Energy 2010,84,771.
140.Inokuchi, H. Bull. Chem. Soc. Jpn.1955,28,570.
141.Akamatu, H.; Inokuchi, H. J. Chem. Phys.1950,18,810.
142.Vivo, P.; Vuorinen, T.; Chukharev, V.; Tolkki, A.; Kaunisto, K.; Ihalainen, P.; Peltonen, J.; Lemmetyinen, H. J. Phys. Chem. C2010,114,8559.
1. 赵俊国.染料工业,1999,1,23.
2. 朱为宏,范多,紫蒽酮类似物及其用途,CN 101270064A,2008.
1.刘立维,萘酞菁类化合物光电转换性质的研究,浙江大学硕士论文,2008.
2.吴世康,汪鹏飞,有机电子学概论,化学工业出版社,北京,2010.
3. Scharber, M. C.; Muhlbacher, D.; Koppe, M; Denk, P.; Waldauf, C.; Heeger, A. J.; Brabec, C. J. Adv. Mater.2006,18,789.
4.刘楠,硅／有机半导体复合光电材料与器件的研究,浙江大学博士论文,2008.
5. Thompson, B. C.; Frechet, J. M. J. Angew. Chem. Int. Ed.2008,47,58.
1. Frisch,M.J.T.,G.W,.；Schlegel,H.B.；Scusera，G. E.；Robb,M.A.；Cheeseman, J.R.；Montgomery,J.A.Jr.；Vreven,T.；Kudin,K.N.；Burant,J.C.；Millarn,J. M.；Iyengar,S.S.；Tomai,J.；Barone,V；Mennucci,B.；Cossi,M.；Scalmani,G； Rega,N.；Petersson,G. A.；Nakatsuji,H.；Hada,M.；Ehara,M.；Toyota,K.； Fukuda,R.；Hasegawa,J.；Shida,M.；Nakajima，T.；Honda,Y.；Kitao,O.；Nakai, H.；Klene,M.；Li,X.；Knox,J.E.；Hratchian,H.P.；Cross,J.B.；Adamo,C.； Jaramillo,J.；Gomperts,R.；Stratmann,R.E.；Yazyev,O.；Austin,A.J.；Cammi, R.；omelli,C.；Ochterski,J.W:；Ayala,P.Y；Morokuma,K.G；Voth,A.；alvador, P.；Dannenberg,J.J.；Zakrzewski,V.G；Dapprich,S.；Daniels,A.D.；Strain,M. C.；Farkas,O.；Malick,D.K.；Rabuk,A.D.；Raghavachari,K.；Foresman,J.B.； Oniz,J.V；Cui,Q.；Baboul,A.G；Clifford,S.；Cioslowski,J.；Stefanov，B.B.； Liu,G；Liashenko,A.；Piskorz,P.；Komaromi,I.；Martin,R.L.；Fox,D.J.；Keith, T.；A1-Laham,M.A.；Peng,C.Y；Nanayakkara,A.；Challacombe,M.；Gill,P.M. W.；Johnson,B.；Chen,W.；Wong,M.W.；Gonzalez,C.；Pople,J.A.Gaussian 03, Gaussian,Inc.Pittsburgh,PA,2003.
2. (a)Lin,Y.Y.；Gundlach,D.J.；Nelson,S.F.IEEE Electron Device Lett.1997, 18,606.(b)Pyo,K.S.；Song,C.K.Thin Solid Films.2005,485,230.(c)Wang,R. W.；Wunder,S.L.,Phys.Chem.B 2001,,105,173.
3. (a)Kim,P.；Zhang,X.H.；Domercq,B.；Jones,S.C.；Hotchkiss,P.J.；Marder,S. R.；Kippelen,B.；Perry,J.W.App,.Phys.Lett.2008,93,013302.(b)Huanglg,T. S.；Su,Y.K.；Wang,P.C.Appl.Phys.Lett.2007,9,,092116.(c)Pyo,S.；Son, H.；Choi,K.Y.；Yi,M.H.；Hong,S.K.App,.Phys.Lett.2005,86,133508.(d) Lee, J.; Kim, J. H.; Im, S. J. Appl. Phys.2004,95,3733. (e) Park, S. Y.; Park, M.; Lee, H. H. Appl. Phys. Lett.2004,55,2283.
1. Meng,L.Y；Shang,Y；Li,Q.K.；Li,Y F.；Zhan,X.W.；Shuai,Z.G；Kimber,R. G E.；Walker,A.B.J.Phys.Chem.B2010,114,36.
2. 徐浩,基于对吡咯施主-受主共轭聚合物有机电子器件研究,浙江大学硕士论文,2010.
3. (a)Gebeyehu,D.；Pf.eiffer,M.；Maenning,B.；Drechsel,J.；Werner,A.；Leo,K. Thin Solid Film 2004,29,451.(b) Yohannes,T.；Zhang,F.；Svensson,M.； Hummelen,J.C.；Andersson,M.R.；Inganas,O.；Thin Solid Flim 2004,449,152.
2. (a) Pope, M.; Kallmann, H.; Magnante, P. J. Chem. Phys.1963,38,2042. (b) Helfrich, W.; Schneider, W. G. Phys. Rev. Lett.1965,14,229.
3. Ferraris, J.; Cowan, D.O.; Walatka, V.; Perlstein, J. H. J. Am. Chem. Soc.1973, 95,948.
4. Chiang, C. K.; Shirakawa, H.; Frincher, C. R. J. Chem. Soc. Chem. Comm. 1977,39,1098.
5. Walatka, V. V.; Labes, M. M.; Perlstein, J. J. Phys. Rev. Lett.1973,31,1139.
6. (a) Berets, D. J.; Smith, D. S. Trans. Faraday Soc.1968,64,823. (b) Chiang, C. K.; Fincher, C. R.; Jr, Park, Y. W.; Heeger, A. J.; Shirakawa, H.; Louis, E. J.; Gau, S. C.; Alan; MacDiarmid, G. Phys. Rev. Lett.1977,39,1098.
7. Tang, C. W. Appl. Phys. Lett.1986,48,183.
8. (a) Koezuka, H. A.; Tsumara, T. A.; Synth. Met.1987,18,699. (b) Burroughes, J. H.; Jones, C. A.; Friend, R. H. Nature 1988,335,137. (c) Horowitz, D. F.; Peng, X. Z.; Xu, Z.; Garnier, F. Solid State Comm.1989,72,381.
9. Tang, C. W.; VanSlyke, S. A. Appl. Phys. Lett.1987,51,913. (b) Tang, C. W.; VanSlyke, S. A. J. Appl. Phys.1989,65,3610.
10. (a) Burroughes, J. H.; Bradley, D. C; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burn, P. L.; Holmes, A. B. Nature 1990,347,539. (b) Braun, D.; Heeger, A. J. Appl. Phys. Lett.1991,58,1982.
11. (a) Yang, Y; Chang, S. C; Bharathan, J.; Liu, J. J. Mater. Sci. Mater. Electron. 2000,11,89. (b) Hoth, C. N.; Schilinsky, P.; Choulis, S. A.; Brabec, C. J. Nano. Lett.2008,8,2806.
12. Schilinsky, P.; Waldauf, C; Brabec, C. J. Adv. Funct. Mater.2006,16,1669.
13. Shaheen, S. E.; Radspinner, R.; Peyghambarian, N.; Jabbour, G. E. Appl. Phys. Lett.2001,79,2996.
14. (a) Su, S. J.; Gonmori, E.; Sasabe, H.; Kido, J. Adv. Mater.2009,21,361. (b) Su, S. J.; Chiba, T.; Takeda, T.; Kido, J. Adv. Mater.2008,20,1. (c) Huang, F.; Shih, P. I.; Shu, C. F.; Chi, Y A.; Jen, K. Y Adv. Mater.2009,21,361.
15. (a) Wang, E.; Wang, L.; Lan, L.; Luo, C; Zhuang, W.; Peng, J.; Cao, Y. Appl. Phys. Lett.2008,92,033307. (b) Irwin, M. D.; Buchholz, D. B.; Hains, A. W.; Chang, R. P. H.; Marks, T. J. Proc. Natl. Acad. Sci. USA,2008,105,2783. (c) Hou, J.; Chen, H. Y; Zhang, S.; Li, G; Yang, Y J. Am. Chem. Soc.2008,130, 16144. (d) Peet, J.; Kim, J. Y; Coates, N. E.; Ma, W. L.; Moses, D.; Heeger, A. J.; Bazan, G. C. Nat. Mater.2007,6,497.
16. (a) Yan, H.; Chen, Z.; Zheng, Y; Newman, C; Quinn, J. R.; Dotz, F.; Kastler, M.; Facchetti, A. Nature 2009,457,679. (b) Tang, M.; Reichardt, A.; Miyaki, N.; Stoltenberg, R. M.; Bao, Z. J. Am. Chem. Soc.2008,130,6064. (c) Klauk, H.; Zschieschang, U.; Pflaum. J.; Halik, M. Nature 2007,445,745. (d) Tsao, H. N.; Cho, D.; Andreasen, J. W.; Rouhanipour, A.; Breiby, D. W.; Pisula, W.; Mullen, K. Adv. Mater.2009,21,209.
17. Scott, J. C.; Bozano, L. D. Adv. Mater.2007,19,1452.
18. Liang, Y. Y.; Xu, Z.; Xia, J. B.; Tsai, S. T.; Wu, Y.; Li, G; Ray, C; Yu, L. P.; Angew. Chem. Int. Ed.2010,22,1.
19. Sze, S. M. Semiconductor Devices:Physics and Technology Wiley, New York, 1985,6,216,507.
20. Moore, G. E. IEEE IEDM Tech. Dig.1975,11.
21. Subramanian, V. IEEE Trans. Comp. Pack. Tech.2005,28,742.
22. (a) Torsi, L.; Dodabalapur, A. Anal. Chem. A-Pages,2005,77,380. (b) Katz, H. E. J. Appl. Phys.2002,91,1572.
23. Muccini, M. Nat. Mater.2006,5,605.
24. (a) Kitamura, M. Jpn. J. Appl. Phys.2003,42,2483. (b) Huitema, H. E. A. Adv. Mater.2002,14,1201.
25. (a) Wang, Z. Adv. Mater.2003,15,1009. (b) Halik, M. Adv. Mater.2002,14, 1717. (c) Sirringhaus, H. Science 2000,290,2123.
26. (a) Yamaguchi, S. Pure Appl. Chem.2006,78,721. (b) Kunugi, Y. Chem. Mater. 2003,15,6. (c) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater.2002,14, 99.
27. Carswell, D. J. Nature 1954,173,736.
28. (a) Rang, Z. Appl. Phys. Lett.2001,79,2731. (b) Klauk, H. IEEE Trans. Electron Dev.1999,46,1258. (c) Horowitz, G. Synth. Met.1991,41,1127.
29. (a) Sundar, V. Science 2004,303,1644. (b) Hulea, I. N. Appl. Phys. Lett.2006, 88,113512. (c) Stingelin-Stutzmann, N. Nat. Mater.2005,4,601. (d) Briseno, A. L. Adv. Mater.2006,18,2320.
30. Wurthner, F.; Schmidt, R. ChemPhysChem 2006,7,793.
31. Lin, Y. Y. IEEE Trans. Electron Dev. Lett.1997,18,606.
32. Klauk, H. J. Appl. Phys.2002,92,5259.
33. Laudise, R. A. J. Cryst. Growth 1998,187,449.
34. (a) Minakata, T. J. Appl. Phys.1992,72,4178. (b) Minakata, T. J. Appl. Phys. 1993,74,1079.
35. Kagan, C. R. Appl. Phys. Lett.2005,86,193505.
36. (a) Huang, C. J. Appl. Phys.2006,100,114512. (b) Lee, C. A. Appl. Phys. Lett. 2006,88,252102. (c) Kobayashi, S. Nat. Mater.2004,3,317.
37. (a) Hamadani, B. H. Nano Lett.2006,6,1303. (b) Tsukagoshi, K. Appl. Phys. Lett.2006, 89,113507. (c) Salleo, A. Appl. Phys. Lett.2002,81,4383. (d) Facchetti, A. Adv. Mater.2005,17,1705.
38. Fritz, S. E. J. Phys. Chem. B 2005,109,10574.
39. Pratontep, M. Synth. Met.2004,745,387.
40. Locklin, J. Macromol. Sci. Polym. Rev.2006,46,79.
41. Lee, H. S.Adv. Funct. Mater.2006,16,1859.
42. Horowitz, G. Synth. Met.1992,51,419.
43. Garnier, F. J. Am. Chem. Soc.1993,115,8716.
44. Hajlaoui, M. E. Synth. Met.2002,129,215.
45. Akimichi, H.Appl. Phys. Lett.1991,58,1500.
46. (a) Katz, H. E. Nature 2000,404,478. (b) Gamier, F. Chem. Mater.1998,10, 3334.
47. Facchetti, A. J. Am. Chem. Soc.2004,126,13480.
48. Barbarella, G. J. Am. Chem. Soc.1999,121,8920.
49. Murphy, A. R. J. Am. Chem. Soc.2004,126,1596.
50. Laquindanum, J. G. Adv. Mater.1997,9,36.
51. Li, X. C. J. Am. Chem. Soc.1998,120,2206.
52. Ichikawa, M. Adv. Mater.2002,14,1272.
53. Ponomarenko, S. A. Chem. Mater.2006,18,579.
54. Meng, H. J. Am. Chem. Soc.2001,123,9214.
55. Laquindanum, J. G. J. Am. Chem. Soc.1998,120,664.
56. Barbe, D. F. J. Phys. Chem. Solids 1970,31,2679.
57. (a) Madru, R. Chem. Phys. Lett.1988,145,343. (b) Bao, Z. Appl. Phys. Lett. 1996,69,3066.
58. Bao, Z. Adv. Mater.1997,9,42.
59. Someya, T. Proc. Nat. Acad. Sci USA,2005,102,12321.
60. Tang, Q. Adv. Mater.2006,18,65.
61. Pron, A.; Rannou, P. Prog. Polym. Sci.2002,27,135.
62. McCullough, R. D. Adv. Mater.1998,10,93.
63. Assadi, Appl.Phys.Lett.1988,53,195.
64. Tsumura, A. Synth. Met.1991,41,1181.
65. Paloheimo, J. Synth. Met.1991,41,563.
66. Katz, H. E. Acc. Chem. Res.2001,34,359.
67. Paloheimo, J. Appl. Phys. Lett.1990,56,1157.
68. Tanese, M. C, Chem. Mater.2006,18,778.
69. Bredas, J. L. J. Chem. Phys.1985,82,3808.
70. (a) Chen, T. A. J. Am. Chem. Soc.1995,117,233. (b) Sirringhaus, H. Nature 1999,401,685. (c) Bao, Z. Appl. Phys. Lett.1996,69,4108. (d) Sirringhaus, H. Science 1998,280,1741.
71. (a) Kline, R. J. Macromolecules 2005,38,3312. (b) Zen, A. Macromolecules 2006,39,2162.
72. Chang, J. F. Chem. Mater.2004,16, 4772.
73. (a) Majewski, L. A. Appl. Phys. Lett.2006,88,222108. (b) Surin, M. J. Appl. Phys.2006,100,033712.
74. Jia, H. J. Vac. Sci. Tech. A 2006,24,1228.
75. Kim, D. H. J. Phys. Chem. B 2006,110,15763.
76. Hoshino, S. J. Appl. Phys.2004,95,5088.
77. Bao, Z. Chem. Mater.1997,9,1299.
78. Ong, B. S. J. Am. Chem. Soc.2004,126,3378.
79. McCulloch, I. Nat. Mater.2006,5,328.
80. Lim, E. J. Polym. Sci. Part A:Polym. Chem.2006,44,4709.
81. Kim, Y. Macromolecules 2006,39,4081.
82. Usta, H. J. Am. Chem. Soc.2006,128,9034.
83. Chua. L. L. Adv. Mater.2004.16.1609.
84. (a) Li, Y. Macromolecules 2006,39,6521. (b) Drolet, N. Adv. Funct. Mater. 2005,15,1671.
85. Majewski, L. A. Adv. Funct Mater.2005,15,1017.
86. Veres, J. Chem. Mater.2004,16,4543.
87. Newman, C. R. Chem. Mater.2004,16,4436.
88. Chua, L. L. Nature 2005,434,194.
89. Yoon, M. H. J. Am. Chem. Soc.2006,128,12851.
90. Facchetti, A. Angew. Chem. Int. Ed.2000,39,4547.
91. (a) Facchetti, A. Adv. Mater.2003,15,33. (b) Facchetti, A. J. Am. Chem. Soc. 2004,126,13859.
92. Facchetti, A. Angew. Chem. Int. Ed.2003,42,3900.
93. Yoon, M. H. J. Am. Chem. Soc.2006,128,5792.
94. Yoon, M. H. J. Am. Chem. Soc.2005,127,1348.
95. Letizia, J. A. J. Am. Chem. Soc.2005,127,13476.
96. Facchetti, A. Chem. Mater.2004,16,4715.
97. Ando, S. J. Am. Chem. Soc.2005,127,14996.
98. Naraso J. Am. Chem. Soc.2006,128,9598.
99. (a) Ostrick, J. R. J. Appl. Phys.1997,81,6804. (b) Uchida, T. Bull. Chem. Soc. Jpn.1961,34,1015.
100.Rademacher, A. Chem. Ber.1982,115,2927.
101.Katz, H. E. J. Am. Chem. Soc.2000,122,7787.
102.Laquindanum, J. G. J. Am. Chem. Soc.1996,118,11331.
103.Katz, H. E. Nature 2000,404,478.
104.Malenfant, P. R. L. Appl. Phys. Lett.2002,80,2517.
105.Chesterfield, R. J. J. Appl. Phys.2004,95,6396.
106.Tatemichi, S. Appl. Phys. Lett.2006,89,112108/1.
107 Jones, B. Angew. Chem. Int. Ed.2004,43,6363.
108.Yoo, B. IEEE Electron Dev. Lett.2006,27,737.
109.Sakamoto, Y. J. Am. Chem. Soc.2004,126,8138.
110.Schlettwein, D. Chem. Mater.1994,6,3.
111.Bao, Z. J. Am. Chem. Soc.1998,120,207.
112.Kastner, J. Solid State Sciences Kuzmany, H. (eds.), Springer, New York,1993.
113.Haddon, R. C. Appl. Phys. Lett.1995,67,121.
114.Stefan, C. B.; Mannsfeld, A. S.; Liu, S. H.; Roberts, M. E.; McCulloch, I.; Heeney, M.; Bao, Z. N. Adv. Mater.2008,20,4044.
115.Kelley, T. W. in Organic Electronics. Materials, Manufacturing and Applications (Ed:H. Klauk,) Wiley-VCH, Weinheim 2006,33.
116.Yu, G.; Hummelen, J. C; Wudl, F.; Heeger, A. J. Science 1995,270,1789.
117.Kippelen, B.; Bredas, J. L. Energy Environ. Sci.2009,2,251.
118.Blom, P. W. M; Mihailetchi, V. D.; Koster, L. A. J.; Markov, D. E. Adv. Mater. 2007,79,1551.
119.Yu, G.; Hummelen, J. C; Wudl, F.; Heeger, A. J. Science 1995,270,1789.
120.Halls, J. J. M.; Pichler, K.; Friend, R. H.; Moratti, S. C; Holmes, A. B. Appl. Phys. Lett.1996,68,3120.
121.(a) Hwang, I. W.; Moses, D.; Heeger, A. J. J. Phys. Chem. C 2008,112,4350. (b) De, S.; Pascher, T.; Maiti, M.; Jespersen, K. G.; Kesti, T.; Zhang, F. L.; Inganas, O.;Yartsez, A.; Sundstrom, V. J. Am. Chem. Soc.2007,129,8466. (c) Mihailetchi, V. D.; Koster, L. J. A.; Hummelen, J. C; Blom, P. W. M. Phys. Rev. Lett.2004,93,216601.
122.Mihailetchi, V. D.; Blom, P. W. M.; Hummelen, J. C; Rispens, M. T. J. Appl. Phys.2003,94,6849.
123.(a) Bredas, J. L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev.2004,104, 4971. (b) Scharber, M. C; Muhlbacher, D.; Koppe, M.; Denk, P.; Waldauf, C. Heeger, A. J.;Brabec, C. J. Adv. Mater.2006,18,789.
124.(a) Kim, J. Y.; Lee, K.; Coates, N. E.; Moses, D.; Nguyen, T. Q.; Dante, M.; Heeger, A. J. Science 2007,317,222. (b) Dennler, G.; Scharber. M. C; Ameri, T. Denk, P.; Forberich, K.; Waldauf, C.;Brabec, C. J. Adv. Mater.2008,20,579.
125.Kline, R. J.; McGehee, M. D. Polym. Rev.2006,46,27.
126.(a) Ma, W. L.; Yang, C. Y.; Gong, X.; Lee, K.; Heeger, A. J. Adv. Funct Mater. 2005,15,1617. (b) Padinger, F.; Rittberger, R. S.; Sariciftci, N. S. Adv. Funct. Mater.2003,13,85.
127.(a) Li, G.; Shrotriya, V.; Huang, J. S.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y. Nat. Mater.2005,4,864. (b) Pivrikas, A.; Stadler, P.; Neugebauer, H.; Sariciftci, N. S. Org. Electron.2008,9,775. (c) Moule, A. J.; Meerholz, K. Adv. Mater. 2008,20,240.
128.Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Chem. Rev.2007,107,1324.
129.(a) Yao, Y.; Hou, J. H.; Xu, Z.; Li, G.; Yang, Y. Adv. Funct. Mater.2008,18, 1783. (b) Campoy-Quiles, M.; Ferenczi, T.; Angostinelli, T.; Etchegoin, P. G.; Kim, Y.; Anthopoulos, T. D.; Stavrinou, P. N.; Bradley, D. D. C; Nelson J. Nat. Mater.2008,7,158.
130.Coropceanu, V.; Cornil, J.; da Silva, D. A.; Olivier, Y.; Silbey, R.; Bredas, J. L. Chem. Rev.2007,107,926.
131.(a) Cho, S. N.; Yuen, J.; Kim, J. Y.; Lee, K.; Heeger, A. J. Appl. Phys. Lett.2006, 89,153505. (b) Cho, S.; Lee, J. K.; Moon, J. S.; Yuen, J.; Lee, K.; Heeger, A. J. Org. Electron.2008,9,1107.
132.Clarke, T. M.; Ballantyne, A. M.; Nelson, J.; Bradley, D. D. C; Durrant, J. R. Adv. Funct. Mater.2008,18,4029.
133.Jiang, X. M.; Osterbacka, R.; Korovyanko, O.; An, C. P.; Horovitz, B.; Janssen,R. A. J.; Vardeny, Z. V. Adv. Funct. Mater.2002,12,587.
134.Arkhipov, V. I.; Heremans, P.; Bassler, H. Appl. Phys.Lett.2003,82,4605.
135.Malenfant, P. R. L.; Dimitrakopoulos, C. D.; Gelorme, J. D.; Kosbar, L. L. Graham, T. O.; Curioni, A.; Andreoni, W. Appl. Phys. Lett.2002,80,2517.
136.(a) Graser, F.; Hadicke, E. Liebigs Ann. Chem.1980,1994. (b) Klebe, G.; Graser, F.; Hadicke, E.; Berndt, J. Acta Crystallogr.1989, B45,69.
137.Stepanenko, V.; Stocker, M.; Muller, P.; Buchner, M.; Wurthner, F. J. Mater. Chem.2009,19,6816.
138.(a) Chen, H. Z.; Shi, M. M; Mo, X.; Wang, M.; Bao, Z. Chem. Mater.2007,19, 816. (b) Chen, H. Z.; Shi, M. M.; Aernouts, T.; Wang, M.; Borghs, G.; Heremans, P. Sol. Energy Mater. Sol. Cells 2005,87,521. (c) Shi, M. M.; Chen, H. Z.; Shi, Y. W.; Sun, J. Z.; Wang, M. J. Phys. Chem. B 2004,108,5901. (d) Shi, M. M.; Chen, H. Z.; Sun, J. Z.; Ye, J.; Wang, M. Chem. Commun.,2003,14,1710.
139.Chen, J.; Shi, M. M.; Hu, X. L.; Wang, M.; Chen, H. Z. Polymer 2010,51,2897. (b) Deng, D.; Shi, M. M.; Chen, F.; Chen, L.; Jiang, X. X.; Chen, H. Z. Solar Energy 2010,84,771.
140.Inokuchi, H. Bull. Chem. Soc. Jpn.1955,28,570.
141.Akamatu, H.; Inokuchi, H. J. Chem. Phys.1950,18,810.
142.Vivo, P.; Vuorinen, T.; Chukharev, V.; Tolkki, A.; Kaunisto, K.; Ihalainen, P.; Peltonen, J.; Lemmetyinen, H. J. Phys. Chem. C2010,114,8559.
1. 赵俊国.染料工业,1999,1,23.
2. 朱为宏,范多,紫蒽酮类似物及其用途,CN 101270064A,2008.
1.刘立维,萘酞菁类化合物光电转换性质的研究,浙江大学硕士论文,2008.
2.吴世康,汪鹏飞,有机电子学概论,化学工业出版社,北京,2010.
3. Scharber, M. C.; Muhlbacher, D.; Koppe, M; Denk, P.; Waldauf, C.; Heeger, A. J.; Brabec, C. J. Adv. Mater.2006,18,789.
4.刘楠,硅／有机半导体复合光电材料与器件的研究,浙江大学博士论文,2008.
5. Thompson, B. C.; Frechet, J. M. J. Angew. Chem. Int. Ed.2008,47,58.
1. Frisch,M.J.T.,G.W,.；Schlegel,H.B.；Scusera，G. E.；Robb,M.A.；Cheeseman, J.R.；Montgomery,J.A.Jr.；Vreven,T.；Kudin,K.N.；Burant,J.C.；Millarn,J. M.；Iyengar,S.S.；Tomai,J.；Barone,V；Mennucci,B.；Cossi,M.；Scalmani,G； Rega,N.；Petersson,G. A.；Nakatsuji,H.；Hada,M.；Ehara,M.；Toyota,K.； Fukuda,R.；Hasegawa,J.；Shida,M.；Nakajima，T.；Honda,Y.；Kitao,O.；Nakai, H.；Klene,M.；Li,X.；Knox,J.E.；Hratchian,H.P.；Cross,J.B.；Adamo,C.； Jaramillo,J.；Gomperts,R.；Stratmann,R.E.；Yazyev,O.；Austin,A.J.；Cammi, R.；omelli,C.；Ochterski,J.W:；Ayala,P.Y；Morokuma,K.G；Voth,A.；alvador, P.；Dannenberg,J.J.；Zakrzewski,V.G；Dapprich,S.；Daniels,A.D.；Strain,M. C.；Farkas,O.；Malick,D.K.；Rabuk,A.D.；Raghavachari,K.；Foresman,J.B.； Oniz,J.V；Cui,Q.；Baboul,A.G；Clifford,S.；Cioslowski,J.；Stefanov，B.B.； Liu,G；Liashenko,A.；Piskorz,P.；Komaromi,I.；Martin,R.L.；Fox,D.J.；Keith, T.；A1-Laham,M.A.；Peng,C.Y；Nanayakkara,A.；Challacombe,M.；Gill,P.M. W.；Johnson,B.；Chen,W.；Wong,M.W.；Gonzalez,C.；Pople,J.A.Gaussian 03, Gaussian,Inc.Pittsburgh,PA,2003.
2. (a)Lin,Y.Y.；Gundlach,D.J.；Nelson,S.F.IEEE Electron Device Lett.1997, 18,606.(b)Pyo,K.S.；Song,C.K.Thin Solid Films.2005,485,230.(c)Wang,R. W.；Wunder,S.L.,Phys.Chem.B 2001,,105,173.
3. (a)Kim,P.；Zhang,X.H.；Domercq,B.；Jones,S.C.；Hotchkiss,P.J.；Marder,S. R.；Kippelen,B.；Perry,J.W.App,.Phys.Lett.2008,93,013302.(b)Huanglg,T. S.；Su,Y.K.；Wang,P.C.Appl.Phys.Lett.2007,9,,092116.(c)Pyo,S.；Son, H.；Choi,K.Y.；Yi,M.H.；Hong,S.K.App,.Phys.Lett.2005,86,133508.(d) Lee, J.; Kim, J. H.; Im, S. J. Appl. Phys.2004,95,3733. (e) Park, S. Y.; Park, M.; Lee, H. H. Appl. Phys. Lett.2004,55,2283.
1. Meng,L.Y；Shang,Y；Li,Q.K.；Li,Y F.；Zhan,X.W.；Shuai,Z.G；Kimber,R. G E.；Walker,A.B.J.Phys.Chem.B2010,114,36.
2. 徐浩,基于对吡咯施主-受主共轭聚合物有机电子器件研究,浙江大学硕士论文,2010.
3. (a)Gebeyehu,D.；Pf.eiffer,M.；Maenning,B.；Drechsel,J.；Werner,A.；Leo,K. Thin Solid Film 2004,29,451.(b) Yohannes,T.；Zhang,F.；Svensson,M.； Hummelen,J.C.；Andersson,M.R.；Inganas,O.；Thin Solid Flim 2004,449,152.