Electroluminescent and photovoltaic properties of silole-based materials

Current Organic Chemistry

Volumn 16, Issue 11, 2012, Pages 1423-1446

  Fu, Huiying ^a   Cheng, Yuanrong ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Organic light emitting diodes; Organic photovoltaic devices; Silole

Indexed keywords

CARRIER MOBILITY; ELECTROLUMINESCENCE;

ELECTROLUMINESCENT PROPERTIES; LIGHTEMITTING DIODE; MATERIAL-BASED; OPTOELECTRONICS DEVICES; ORGANIC LIGHT-EMITTING; ORGANIC LIGHT-EMITTING DIODE; ORGANIC PHOTOVOLTAIC DEVICES; PHOTOVOLTAIC PROPERTY; SILOLE DERIVATIVES; SILOLES;

ORGANIC LIGHT EMITTING DIODES (OLED);

EID: 84861742445     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212800672637     Document Type: Review

References (134)

1. Murata, H.; Kafafi, Z.H.; Uchida, M. Efficient organic light-emitting diodes with undoped active layers based on silole derivatives. Appl. Phys. Lett., 2002, 80, 189-191.
2. Yu, G.; Yin, S.W.; Liu, Y.Q.; Chen, J.S.; Xu, X.J.; Sun, X.B.; Ma, D.G.; Zhan, X.W.; Peng, Q.; Shuai, Z.G.; Tang, B.Z.; Zhu, D.B.; Fang, W.H.; Luo, Y. Structures, electronic states, photoluminescence, and carrier transport properties of 1,1-disubstituted 2,3,4,5-tetraphenylsiloles. J. Am. Chem. Soc., 2005, 127, 6335-6346.
3. Sartin, M.M.; Boydston, A.J.; Pagenkopf, B.L.; Bard, A.J. Electrochemistry, spectroscopy, and electrogenerated chemiluminescence of silole-based chromophores. J. Am. Chem. Soc., 2006, 128, 10163-10170.
4. Jung, H.; Hwang, H.; Park, K.-M.; Kim, J.; Kim, D.-H.; Kang, Y. Palladiumcatalyzed cross-coupling reactions of dithienosilole with indium reagents: synthesis and characterization of dithienosilole derivatives and their applications to organic light-emitting diodes. Organometallics, 2010, 29, 2715-2723.
5. Chan, K.L.; McKiernan, M.J.; Towns, C.R.; Holmes, A.B. Poly(2,7-dibenzosilole): a blue light emitting polymer. J. Am. Chem. Soc., 2005, 127, 7662-7663.
6. Corey, J.Y. Chapter 1-Siloles: part 1: synthesis, characterization, and applications. Adv. Organomet. Chem., 2011, 59, 1-180.
7. Corey, J.Y. Chapter 2-Siloles: part 2: silaindenes (benzosiloles) and silafluorenes (dibenzosiloles): synthesis, characterization, and applications. Adv. Organomet. Chem., 2011, 59, 181-328.
8. Chen, J.W.; Cao, Y. Silole-containing polymers: chemistry and optoelectronic properties. Macromol. Rapid Commu., 2007, 28, 1714-1742.
9. Ohshida, J. Conjugated oligomers and polymers containing dithienosilole units. Macromol. Chem. Phys., 2009, 210, 1360-1370.
10. Wong, W.W.H.; Hooper, J.F.; Holmes, A.B. Silicon analogues of polyfluorene as materials for organic electronics. Aust. J. Chem., 2009, 62, 393-401.
11. Murata, H.; Malliaras, G.G.; Uchida, M.; Shen, Y.; Kafafi, Z.H. Nondispersive and air-stable electron transport in an amorphous organic semiconductor. Chem. Phys. Lett., 2001, 339, 161-166.
12. Chen, H.Y.; Lam, W.Y.; Luo, J.D.; Ho, Y.L.; Tang, B.Z.; Zhu, D.B.; Wong, M.; Kwok, H.S. Highly efficient organic lightemitting diodes with a silolebased compound. Appl. Phys. Lett., 2002, 81, 574-576.
13. Geramita, K.; McBee, J.; Shen, Y.L.; Radu, N.; Tilley, T.D. Synthesis and characterization of perfluoroaryl-substituted siloles and thiophenes: a series of electron-deficient blue light emitting materials. Chem. Mater., 2006, 18, 3261-3269.
14. Son, H.-J.; Han, W.-S.; Chun, J.-Y.; Lee, C.-J.; Han, J.-I.; Ko, J.; Kang, S.O. Spiro-silacycloalkyl tetraphenylsiloles with a tunable exocyclic ring: preparation, characterization, and device application of 1,1'-silacycloalkyl-2,3,4,5-tetraphenylsiloles. Organometallic, 2007, 26, 519-526.
15. Lu, G.; Usta, H.; Risko, C.; Wang, L.; Facchetti, A.; Ratner, M.A.; Marks, T.J. Synthesis, characterization, and transistor response of semiconducting silole polymers with substantial hole mobility and air stability. Experiment and theory. J. Am. Chem. Soc., 2008, 130, 7670-7685.
16. Tamao, K.; Yamagushi, S.; Ito, Y.; Matsuzaki, Y.; Yamabe, T.; Fukushima, M.; Mori, S. Silole-containing →-conjugated systems. 3.1 A series of silolethiophene cooligomers and copolymers: synthesis, properties, and electronic structures. Macromolecules, 1995, 28, 8668-8675.
17. Yamaguchi, S.; Goto, T.; Tamao, K. Silole-thiophene alternating copolymers with narrow band gaps. Angew. Chem. Int. Ed., 2000, 39, 1695-1697.
18. Boudreault, P.-L.T.; Michaud, A.; Leclerc, M. A new poly(2,7-dibenzosilole) derivative in polymer solar cells. Macromol. Rapid Commun., 2007, 28, 2176-2179.
19. Hou, J.H.; Chen, H.-Y.; Zhang, S.Q.; Li, G.; Yang, Y. Synthesis, and characterization, and photovoltaic properties of a low band gap polymer based on silole-containing polythiophenes and 2,1,3-benzothiadiazole. J. Am. Chem. Soc., 2008, 130, 16144-16145.
20. Chu, T.-Y.; Lu, J.P.; Beaupré, S.; Zhang, Y.G.; Pouliot, J.R.; Wakim, S.; Zhou, J.Y.; Leclerc, M.; Li, Z.; Ding, J.F.; Tao, Y. Bulk heterojunction solar cells using thieno[3,4-c]pyrrole-4,6-dione and dithieno[3,2-b:2',3'-d]silole copolymer with a power conversion efficiency of 7.3%. J. Am. Chem. Soc., 2011, 133, 4250-4253.
21. Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi, S. Silole derivatives as efficient electron transporting materials. J. Am. Chem. Soc., 1996, 118, 11974-11975.
22. Ohshita, J.; Nodono, M.; Kai, H.; Watanabe, T.; Kunai, A.; Komaguchi, K.; Shiotani, M.; Adachi, A.; Okita, K.; Harima, Y.; Yamashita, K.; Ishikawa, M. Synthesis and optical, electrochemical, and electron-transporting properties of silicon-bridged bithiophenes. Organometallics, 1999, 18, 1453-1459.
23. Luo, J.D.; Xie, Z.L.; Lam, J.W.Y.; Cheng, L.; Chen, H.Y.; Qiu, C.F.; Kwok, H.S.; Zhan, X.W.; Liu, Y.Q.; Zhu, D.B.; Tang, B.Z. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem. Commu., 2001, 1740-1741.
24. Chen, J.W.; Peng, H.; Law, C.C.W.; Dong, Y.P.; Lam, J.W.Y.; Williams, I.D.; Tang, B.Z. Hyperbranches poly(phenylenesilolene)s: synthesis, thermal stability, electronic conjugation, optical power limiting, and cooling enhanced light emission. Macromolecules, 2003, 36, 4319-4327.
25. Ren, Y.; Lam, J.W.Y.; Dong, Y.Q.; Tang, B.Z.; Wong, K.S. Enhanced emission efficiency and excited state lifetime due to restricted intramolecular motion in silole aggregates. J. Phys. Chem. B, 2005, 109, 1135-1140.
26. Chen, J.W.; Xu, B.; Yang, K.X.; Cao, Y.; Sung, H.H.Y.; Williams, I.D.; Tang, B.Z. Photoluminescence spectral reliance on aggregation order of 1,1-bis(2'-thienyl)-2,3,4,5-tetraphenylsilole. J. Phys. Chem. B, 2005, 109, 17086-17093.
27. Zhao, Z.J.; Wang, Z.M.; Lu, P.; Chan, C.Y.K.; Liu, D.D.; Lam, J.W.Y.; Sung, H.H.Y.; Williams, I.D.; Ma, Y.G.; Tang, B.Z. Structure modulation of solid-state emission of 2,5-bis(trialkylsilylethynyl)-3,4-diphenylsiloles. Angew. Chem., 2009, 121, 7744-7747.
28. Zhao, Z.J.; Chen, S.M.; Lam, J.W.Y.; Jim, C.K.W.; Chan, C.Y.K.; Wang, Z.M.; Lu, P.; Deng, C.M.; Kwok, H.S.; Ma, Y.G.; Tang, B.Z. Steric hindrance, electronic communication, and energy transfer in the photo-and electroluminescence process of aggregation-induced emission luminogens. J. Phys. Chem. C, 2010, 114, 7963-7972.
29. Chen, J.W.; Law, C.C.W.; Lam, J.W.Y.; Dong, Y.P.; Lo, S.M.F.; Williams, I.D.; Zhu, D.B.; Tang, B.Z. Synthesis, light emission, nanoaggregation, and restricted intramolecular rotation of 1,1-substituted 2,3,4,5-tetraphenylsiloles. Chem. Mater., 2003, 15, 1535-1546.
30. Liu, J.Z.; Lam, J.W.Y.; Tang, B.Z. Aggregation-induced emission of silole molecules and polymers: fundamental and applications. J. Inorg. Organomet. Polym. Mater., 2009, 19, 249-285.
31. Liu, J.Z.; Zhong, Y.C.; Lam, J.W.Y.; Lu, P.; Hong, Y.N.; Yu, Y.; Yue, Y.; Faisal, M.; Sung, H.H.Y.; Williams, I.D.; Wong, K.S.; Tang, B.Z. Hyperbranced conjugated polysiloles: synthesis, structure, aggregation-enhanced emission, multicolor fluorescent photopatterning, and superamplified detection of explosives. Macromolecules, 2010, 43, 4921-4936.
32. Chan, K.L.; Watkins, S.E.; Mak, C.S.K.; McKiernan, M.J.; Towns, C.R.; Pascu, S.I.; Holmes, A.B. Poly(9,9-dialkyl-3,6-dibenzosilole)-a high energy gap host for phosphorescent light emitting devices. Chem. Commu., 2005, 5766-5768.
33. Wang, E.G.; Li, C.; Mo, Y.Q.; Zhang, Y.; Ma, G.; Shi, W.; Peng, J.B.; Yang, W.; Cao, Y. Poly(3,6-silafluorene-co-2,7-fluorene)-based high-efficiency and color-pure blue light-emitting polymers with extremely narrow band-width and high spectral stability. J. Mater. Chem., 2006, 16, 4133-4140.
34. Wang, J.; Zhang, C.Q.; Zhong, C.M.; Hu, S.J.; Chang, X.Y.; Mo, Y.Q.; Chen, X.W.; Wu, H.B. Highly efficient and stable deep blue light emitting poly(9,9-dialkoxyphenyl-2,7-silafluorene): synthesis and electroluminescent properties. Macromolecules, 2011, 44, 17-19.
35. Wang, E.G.; Li, C.; Zhang, W.L.; Peng, J.B.; Cao, Y. High-efficiency red and green light-emitting polymer based on a novel wide bandgap poly(2,7-silafluorene). J. Mater. Chem., 2008, 18, 797-801.
36. Wang, E.G.; Wang, L.; Lan, L.F.; Luo, C.; Zhuang, W.L.; Peng, J.B.; Cao, Y. High-performance polymer heterojunction solar cells of a polysilafluorene derivative. Appl. Phys. Lett., 2008, 92, 033307.
37. Jin, J.-K.; Choi, J.-K.; Kim, B.-J.; Kang, H.-B.; Yoon, S.-C.; You, H.; Jung, H.-J. Synthesis and photovoltaic performance of low-bandgap polymers on the basis of 9,9-dialkyl-3,6-dialkyloxysilafluorene. Macromolecules, 2011, 44, 502-511.
38. Usta, H.; Lu, G.; Facchetti, A.; Marks, T.J. Dithienosilole-and dibenzosilolethiophene copolymers as semiconductors for organic thin-film transistors. J. Am. Chem. Soc., 2006, 128, 9034-9035.
39. Ohshita, J.; Kai, H.; Takata, A.; Iida, T.; Kunai, A.; Ohta, N.; Komaguchi, K.; Shiotani, M.; Adachi, A.; Sakamaki, K.; Okita, K. Effects of conjugated substituents on the optical, electrochemical, and electron-transporting properties of dithienosiloles. Organometallics, 2001, 20, 4800-4805.
40. Liao, L.; Dai, L.M.; Smith, A.; Durstock, M.; Lu, J.P.; Ding, J.F.; Tao, Y. Photovoltaic-active dithienosilole-containing polymers. Macromolecules, 2007, 40, 9406-9412.
41. Huo, L.J.; Chen, H.-Y.; Hou, J.H.; Chen, T.L.; Yang, Y. Low band gap dithieno[3,2-b:2',3'-d] silole-containing polymers, synthesis, characterization and photovoltaic application. Chem. Commu., 2009, 5570-5572.
42. Beaujuge, P.M.; Pisula, W.; Tsao, H.N.; Ellinger, S.; Müllen, K.; Reynolds, J.R. Tailoring structure-property relationships in dithienosilolebenzothiadiazole donor-acceptor copolymers. J. Am. Chem. Soc., 2009, 131, 7514-7515.
43. Zhang, S.M.; Guo, Y.L.; Fan, H.J.; Liu, Y.; Chen, H.-Y.; Yang, G.W.; Zhan, X.W.; Liu, Y.Q.; Li, Y.F.; Yang, Y. Low bandgap-conjugated copolymers based on fused thiophenes and benzothiadiazole: synthesis and structureproperty relationship study. J. Polym. Sci. Part A: Polym. Chem., 2009, 47, 5498-5508.
44. Zhou, J.Y.; Wan, X.J.; Liu, Y.S.; Wang, F.; Long, G.K.; Li, C.X.; Chen, Y.S. Synthesis and photovoltaic properties of a poly(2,7-carbazole) derivative based on dithienosilole and benzothiadiazole. Macromol. Chem. Phys., 2011, 212, 1109-1114.
45. Hong, Y.R.; Wong, H.-K.; Moh, L.C.H.; Tan, H.-S.; Chen, Z.-K. Polymer solar cells based on copolymers of dithieno[3,2-b:2',3'-d]silole and thienopyrroledione. Chem. Commu., 2011, 47, 4920-4922.
46. Zhang, Y.; Zou, J.Y.; Yip. H.-L.; Sun, Y.; Davies, J.A.; Chen, K.-S.; Acton, O.; Jen, A.K.-Y. Conjugated polymers based on C, Si and N-bridged dithiophene and thienopyrroledione units: synthesis, field-effect transistors and bulk heterojunction polymer solar cell. J. Mater. Chem., 2011, 21, 3895-3902.
47. Huo, L.J.; Hou, J.H.; Chen, H.-Y.; Zhang, S.Q.; Jiang, Y.; Chen, T.L.; Yang, Y. Bandgap and molecular level control of the low-bandgap polymers based on 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione toward highly efficient polymer solar cells. Macromolecules, 2009, 42, 6564-6571.
48. Ding, J.F.; Song, N.H.; Li, Z. Synthesis, characterization and photovoltaic applications of a low band gap polymer based on s-tetrazine and dithienosilole. Chem. Commu., 2010, 46, 8668-8670.
49. Zhang, M.J.; Fan, H.J.; Guo, X.; He, Y.H.; Zhang, Z.G.; Min, J.; Zhang, J.; Zhao, G.J.; Zhan, X.W.; Li, Y.F. Synthesis and photovoltaic properties of bithiazole-based donor-acceptor copolymers. Macromolecules, 2010, 43, 5706-5712.
50. Zhang, M.J.; Guo, X.; Li, Y.F. Synthesis and characterization of a copolymer based on thiazolothiazole and dithienosilole for polymer solar cells. Adv. Energy Mater., 2011, 1, 557-560.
51. Xiao, H.B.; Shen, H.; Lin, Y.G.; Su, J.H.; Tian, H. Spirosilafluorene linked bistriphenylamine: synthesis and application in hole transporting and twophoton fluorescent imaging. Dyes Pigm., 2007, 73, 224-229.
52. Yamaguchi, S.; Xu, C.H.; Tamao, K. Bis-silicon-bridged stilbene homologues synthesized by new intramolecular reductive double cyclization. J. Am. Chem. Soc., 2003, 125, 13662-13663.
53. Xu, C.H.; Yamada, H.; Wakamiya, A.; Yamaguchi, S.; Tamao, K. Ladder bis-silicon-bridged stilbenes as a new building unit for fluorescent-conjugated polymers. Macromolecules, 2004, 37, 8978-8983.
54. Shimizu, M.; Mochida, K.; Hiyama, T. Highly efficient blue fluorescence from 3,2-silylene-bridged 2-phenylindole in the solid state. J. Phys. Chem. C, 2011, 115, 11265-11274.
55. Li, L.C.; Xiang, J.F.; Xu, C.H. Synthesis of novel ladder bis-silicon-bridged p-terphenyls. Org. Lett., 2007, 9, 4877-4879.
56. Ashraf, R.S.; Chen, Z.Y.; Leem, D.S.; Bronstein, H.; Zhang, W.M.; Schroeder, B.; Geerts, Y.; Smith, J.; Watkins, S.; Anthopoulos, T.D.; Sirringhaus, H.; De Mello, J.C.; Heeney, M.; McCulloch, I. Silaindacenodithiophene semiconducting polymers for efficienct solar cells and high-mobility ambipolar transistors. Chem. Mater., 2011, 23, 768-770.
57. Khabashesku, V.N.; Balaji, V.; Boganov, S.E.; Nefedov, O.M.; Michl, J. Matrix isolation of silacyclopentadienes: UV-visible and IR spectra and photochemical interconversion. J. Am. Chem. Soc. 1994, 116, 320-329.
58. Chen, J.W.; Xie, Z.L.; Lam, J.W.Y.; Law, C.C.W.; Tang, B.Z. Silolecontaining polyacetylenes. Synthesis, thermal stability, light emission, nanodimensional aggregation, and restricted intramolecular rotation. Macromolecules, 2003, 36, 1108-1117.
59. Hong, Y.N.; Lam, J.W.Y.; Tang, B.Z. Aggregation-induced emission: phenomenon, mechanism and applications. Chem. Commu., 2009, 4332-4353.
60. Li, Z.; Dong, Y.Q.; Mi, B.X.; Tang, Y.H.; Häussler, M.; Tong, H.; Dong, Y.P.; Lam, J.W.Y.; Ren, Y.; Sung, H.H.Y.; Wong, K.S.; Gao, P.; Williams, I.D.; Kwok, H.S.; Tang, B.Z. Structural control of the photoluminescence of silole regioisomers and their utility as sensitive regiodiscriminating chemosensors and efficient electroluminescent materials. J. Phys. Chem. B, 2005, 109, 10061-10066.
61. Mi, B.X.; Dong, Y.Q.; Li, Z.; Lam, J.W.Y.; Häußler, M.; Sung, H.H.Y.; Kwok, H.S.; Dong, Y.P.; Williams, I.D.; Liu, Y.Q.; Luo, Y.; Shuai, Z.G.; Zhu, D.B.; Tang, B.Z. Making silole photovoltaically active by attaching carbazolyl donor groups to the silolyl acceptor core. Chem. Commu., 2005, 3583-3585.
62. Li, Z.; Dong, Y.Q.; Lam, J.W.Y.; Sun, J.X.; Qin, A.J.; Häußler, M.; Dong, Y.P.; Sung, H.H.Y.; Williams, I.D.; Hwok, H.S.; Tang, B.Z. Functionalized siloles: versatile synthesis, aggregation-induced emission, and sensory and device applications. Adv. Funct. Mater., 2009, 19, 905-917.
63. Habrard, F.; Ouisse, T.; Stéphen, O.; Aubouy, L.; Gerbier, Ph.; Hirsch, L.; Huby, N.; Van der Lee, A. Organic light-emitting diodes and organic lightemitting electrochemical cells based on silole-fluorene derivatives. Synth. Met., 2006, 156, 1262-1270.
64. Aubouy, L.; Huby, N.; Hirsch, L.; Van der Lee, A.; Gerbier, P. Molecular engineering to improve the charge carrier balance in single-layer silole-based OLEDs. New J. Chem., 2009, 33, 1290-1300.
65. Lee, J.H.; Yuan, Y.-Y.; Kang, Y.J.; Jia, W.-L.; Lu, Z.-H.; Wang, S.N. 2,5-Functionalized spiro-bisiloles as highly efficient yellow-light emitters in electroluminescent devices. Adv. Funct. Mater., 2006, 16, 681-696.
66. Zhan, X.W.; Haldi, A.; Yu, J.S.; Kondo, T.; Domercq, B.; Cho, J.Y.; Barlow, S.; Kippelen, B.; Marder, S.R. Synthesis, electron mobility, and electroluminescence of a polynorbornene-supported silole. Polymer, 2009, 50, 397-403.
67. Wang, F.; Luo, J.; Chen, J.W.; Huang, F.; Cao, Y. Conjugated random and alternating 2,3,4,5-tetraphenylsilole-containing polyfluorenes: synthesis, characterization, strong solution photoluminescence, and light-emitting diodes. Polymer, 2005, 46, 8422-8429.
68. Liu, Z.T.; Wang, L.; Chen, J.W.; Wang, F.; Ouyang X.Y.; Cao, Y. Synthesis and optoelectronic properties of silole-containing polyfluorenes with binary structures. J. Polym. Sci. Part A: Polym. Chem., 2007, 45, 756-767.
69. Liu, Z.T.; Zou, J.H.; Chen, J.W.; Huang, L.; Peng, J.B.; Cao, Y. Largely enhanced LED efficiency of carbazole-fluorene-silole copolymers by using TPBI hole blocking layer. Polymer, 2008, 49, 1604-1610.
70. Palilis, L.C.; Murata, H.; Uchida, M.; Kafafi, Z.H. High efficiency molecular organic light-emitting diodes based on silole derivatives and their exciplexes. Org. Electron., 2003, 4, 113-121.
71. Palilis, L.C.; Mäkinen, A.J.; Uchida, M.; Kafari, Z.H. Highly efficient molecular organic light-emitting diodes based on exciplex emission. Appl. Phys. Lett., 2003, 7, 2209-2211.
72. Chen, H.Y.; Chen, J.W.; Qiu, C.F.; Tang, B.Z.; Wong, M.; Kwok, H.S. Blue organic light-emitting diode based on 1,2,3,4,5-pentaphenyl-1-(8-phenyl-1,7-octadiynyl)silole. IEEE J. Sel. Top Quant. 2004, 10, 10-15.
73. Lee, J.; Liu, Q.H.; Motala, M.; Dane, J.; Gao, J.; Kang, Y.; Wang, S. Photoluminescence, electroluminescence, and complex formation of novel N-7-azaindolyl-and 2,2'-dipyridylamino-functionalized siloles. Chem. Mater., 2004, 16, 1869-1877.
74. Aubouy, L.; Gerbier, P.; Huby, N.; Wantz, G.; Vignau, L.; Hirsch, L.; Janot, J.M. Synthesis of new dipyridylphenylaminosiloles for highly emissive organic electroluminescent devices. New J. Chem., 2004, 28, 1086-1090.
75. Zhan, X.W.; Haldi, A.; Risko, C.; Chan, C.K.; Zhan, W.; Timofeeva, T.V.; Korlyukov, A.; Antipin, M.Y.; Montgomery, S.; Thompson, E.; An, Z.S.; Momercq, B.; Barlow, S.; Kahn, A.; Kippelen, B.; Brédas, J.L.; Marder, S.R. Fluorenyl-substituted silole molecules: geometric, electronic, optical, and device properties. J. Mater. Chem., 2008, 18, 3157-3166.
76. Aubouy, L.; Gerbier, P.; Guérin, C.; Huby, N.; Hirsch, L.; Vignau, L. Study of the influence of the molecular organization on single-layer OLEDs' performance. Synth. Met., 2007, 157, 91-97.
77. Lee, J.; Liu, Q.D.; Bai, D.R.; Kang, Y.; Tao, Y.; Wang, S.N. 2,3,4,5-Tetrafunctionalized siloles: synthesis, structures, luminescence, and electroluminescence. Organomettallics, 2004, 23, 6205-6213.
78. Wang, Y.; Hou, L.T.; Yang, K.X.; Chen, J, W.; Wang, F.; Cao, Y. Conjugated silole and carbazole copolymers: synthesis, characterization, singlelayer light-emitting diode, and field effect carrier mobility. Macromol. Chem. Phys., 2005, 206, 2190-2198.
79. Wang, F.; Wang, L.; Chen, J.W.; Cao, Y. Simple silole-containing polyfluorene for white electroluminescence with simultaneous blue, green, and red emission. Macromol. Rapid Commu., 2007, 28, 2012-2018.
80. Uchida, M.; Izumizawa, T.; Nakano, T.; Yamaguchi, S.; Tamao, K.; Furukawa, K. Structural optimization of 2,5-diarylsiloles as excellent electrontransporting materials for organic electroluminescent devices. Chem. Mater., 2001, 13, 2680-2683.
81. Son, H.-J.; Han, W.-S.; Wee, K.R.; Lee, S.-H.; Hwang, A.-R.; Kwon, S.; Cho, D.W.; Suh, I.-H.; Kang, S.O. Intermolecular peripheral 2,5-bipyridyl interactions by cyclization of 1,1'-silanylene unit of 2,3,4,5-aryl substituted siloles: enhanced thermal stability, high charge carrier mobility, and their application to electron transporting layers for OLEDs. J. Mater. Chem., 2009, 19, 8964-8973.
82. Wang, F.; Luo, J.; Yang, K.X.; Chen, J.W.; Huang, F.; Cao, Y. Conjugated fluorene and silole copolymers: synthesis, characterization, electronic transition, light emission, photovoltaic cell, and field effect hole mobility. Macromolecules, 2005, 38, 2253-2260.
83. Chen, J.W.; Cao, Y. Development of novel conjugated donor polymers for high-efficiency bulk-heterojunction photovoltaic devices. Acc. Chem. Res., 2009, 42, 1709-1718.
84. Mo, Y.Q.; Tian, R.Y.; Shi, W.; Cao, Y. Ultraviolet-emitting conjugated polymer poly(9,9'-alkyl-3,6-silafluorene) with a wide band gap of 4.0 eV. Chem. Commu., 2005, 4925-4926.
85. Chen, R.-F.; Fan, Q.-L.; Liu, S.-J.; Zhu, R.; Pu, K.-Y.; Huang, W. Fluorene and silafluorene conjugated copolymer: a new blue light-emitting polymer. Synth. Met., 2006, 156, 1161-1167.
86. Wang, E.G.; Li, C.; Peng, J.B.; Cao, Y. High-efficiency blue emitting polymers based on 3,6-silafluorene and 2,7-silafluorene. J. Polym. Sci. Part A: Polym. Chem., 2007, 45, 4941-4949.
87. Mo, Y.-Q.; Deng, X.-Y.; Jiang, X.; Cui, Q.-H. Blue electroluminescence from 3,6-silafluorene-based copolymers. J. Polym. Sci. Part A: Polym. Chem., 2009, 47, 3286-3295.
88. Keyworth, C.W.; Chan, K.L.; Labram, J.G.; Anthopoulos, T.D.; Watkins, S.E.; Mckiernan, M.; White, A.J.P.; Holmes, A.B.; Williams, C.K. The tuning of the energy levels of dibenzosilole copolymers and applications in organic electronics. J. Mater. Chem., 2011, 21, 11800-11814.
89. Zhang, X.J.; Jiang, C.Y.; Mo, Y.Q.; Xu, Y.H.; Shi, H.H.; Cao, Y. Highefficiency blue light-emitting electrophosphorescent device with conjugated polymers as the host. Appl. Phys. Lett., 2006, 88, 051116.
90. List, E.J.W.; Guentner, R.; Scanducci de Freitas, P.; Scherf, U. The effect of keto defect sites on the emission properties of polyfluorene-type materials. Adv. Mater., 2002, 14, 374-378.
91. Lupton, J.M.; Craig, M.R.; Meijer, E.W. On-chain defect emission in electroluminescent polyfluorenes. Appl. Phys. Lett., 2002, 80, 4489-4491.
92. Sims, M.; Bradley, D.D.C.; Ariu, M.; Koeberg, M.; Asimakis, A.; Grell, M.; Lidzey, D.G. Understanding the origin of the 535 nm emission band in oxidized poly(9,9-dioctylfluorene): the essential role of the inter-chain/intersegment interactions. Adv. Funct. Mater., 2004, 14, 765-781.
93. Cai, W.Z.; Wang, M.; Zhang, J.; Wang, E.G.; Yang, T.B.; He, C.; Moon, J.S.; Wu, H.B.; Gong, X.; Cao, Y. Solvent effect leading to high performance of bulk heterojunction polymer solar cells by novel polysilafluorene derivatives. J. Phys. Chem. C, 2011, 115, 2314-2319.
94. Koster, L.J.A.; Mihailetchi, V.D.; Blom, P.W. Ultimate efficiency of polymer/fullerene bulk heterojunction solar cells. Appl. Phys. Lett., 2006, 88, 093511.
95. Scharber, M.C.; Mühlbacher, D.; Koppe, M.; Denk, P.; Waldauf, C.; Heeger, A.J.; Brabec, C.J. Design rules for donors in bulk-heterojunction solar cellstowards 10 % energy conversion efficiency. Adv. Mater., 2005, 18, 789-794.
96. Osaka, I.; Zhang, R.; Sauvé, G.; Smilgies, D.-M.; Kowalewski, T.; McCullough, R.D. High-lamellar ordering and amorphous-like-network in short-chain thiazolothiazole-thiophene copolymers lead to high mobilities. J. Am. Chem. Soc., 2009, 131, 2521-2529.
97. Lee, S.K.; Kang, I.N.; Lee, J.C.; Shin, W.S.; So, W.W.; Moon, S.J. Synthesis and characterization of thiazolothiazole-based polymers and their applications in polymer solar cells. J. Polym. Sci. Part A: Polym. Chem., 2011, 49, 3129-3137.
98. Duan, C.H.; Cai, W.Z.; Huang, F.; Zhang, J.; Wang, M.; Yang, T.B.; Zhong, C.M.; Gong, X.; Cao, Y. Novel silafluorene-based conjugated polymers with pendant acceptor groups for high performance solar cells. Macromolecules, 2010, 43, 5262-5268.
99. Zhou, E.J.; Cong, J.Z.; Wei, Q.S.; Tajima, K.; Yang, C.H.; Hashimoto, K. All-polymer solar cells from perylene diimide based copolymers: materials design and phase separation control. Angew. Chem., 2011, 123, 2851-2855.
100. Tamao, K.; Ohno, S.; Yamaguchi, S. Silole-pyrrole co-oligomers: their synthesis, structure and UV-VIS absorption spectra. Chem. Commu. 1996, 1873-1874.
101. Kim, D.-H., Ohshita, J.; Lee, K.-H.; Kunugi, Y.; Kunai, A. Synthesis of-conjugated oligomers containing dithienosilole units. Organomettallics, 2006, 25, 1511-1516.
102. Lee, T.; Jung, I.; Song, K.H.; Lee, H.; Choi, J.; Lee, K.; Lee, B.J.; Pak, J.; Lee, C.; Kang, S.O.; Ko, J. Synthesis and luminescence of silicon-bridged bithiophene-and triarylamine-containing molecules. Organometallics, 2004, 23, 5280-5285.
103. Son, H.-J.; Han, W.-S.; Chun, J.-Y.; Kwon, S.-N.; Ko, J.; Kang, S.O. Enhanced charge-carrier mobility derived from cyclization of a silanylene unit on dithienosiloles: syntheses, photophysical properties, and device fabrication of dithieno-spiro-siloles. Organometallics, 2008, 27, 2464-2473.
104. Ohshita, J.; Kurushima, Y.; Lee, K.-H.; Kunai, A.; Ooyama, Y.; Harima, Y. Synthesis of bis(diarylphosphino)dithienosilole derivatives as novel photoand electroluminescence materials. Organometallics, 2007, 26, 6591-6595.
105. Lee, I.-S.; Kim, S.-J.; Kwak, Y.-W.; Choi, M.-C.; Park, J.-W.; Ha, C.-S. Synthesis of 2,6-diaryl-4,4-diphenyldithienosiloles and their luminescent properties. J. Ind. Eng. Chem., 2008, 14, 344-349.
106. Liu, M.S.; Luo, J.D.; Jen, A.K.-Y. Efficient green-light-emitting diodes from silole-containing copolymers. Chem. Mater., 2003, 15, 3496-3500.
107. Liao, L.; Cirpan, A.; Chu, Q.H.; Karasz, F.E.; Pang, Y. Synthesis and optical properties of light-emitting-conjugated polymers containing biphenyl and dithienosilole. J. Polym. Sci. Part A: Polym. Chem., 2007, 45, 2048-2058.
108. Ohshita, J.; Hamamoto, D.; Kimura, K.; Kunai, A. Anodic polymerization of dithienosilole and electroluminescent properties of the resulting polymer. J. Organomet. Chem., 2005, 690, 3027-3032.
109. Ohshita, J.; Kimura, K.; Lee, K.-H.; Kunai, A.; Kwak, Y.-W.; Son, E.-C.; Kunugi, Y. Synthesis of silicon-bridged polythiophene derivatives and their applications to EL device materials. J. Polym. Sci. Part A: Polym. Chem., 2007, 45, 4588-4596.
110. Ohshita, J.; Kai, H.; Sumida, T.; Kunai, A.; Adachi, A.; Sakamaki, K.; Okita, K. Synthesis of novel bithiophene derivatives with an organosilanylene bridge, and their applications to electron-transporting materials in EL devices. J. Organomet. Chem., 2002, 642, 137-142.
111. Ohshita, J.; Nodono, M.; Takata, A.; Kai, H.; Adachi, A.; Sakamaki, K.; Okita, K.; Kunai, A. Synthesis and properties of alternating polymers containing 2,6-diaryldithienosilole and organosilicon units. Macromol. Chem. Phys., 2000, 201, 851-857.
112. Ohshita, J.; Sumida, T.; Kunai, A.; Adachi, A.; Sakamaki, K.; Okita, K. Synthesis of polymers composed of alternating diphenylenedithienosilole and diethynylenesilylene units and their applications to hole transport in double-layer EL devices. Macromolecules, 2000, 33, 8890-8893.
113. Lee, K.H.; Ohshita, J.; Kimura, K.; Kunugi, Y.; Kunai, A. Synthesis of oligomers having a pendant dithienosilole unit and their applications to EL device materials. J. Organomet. Chem., 2005, 690, 333-337.
114. Lee, K.-H.; Ohshita, J.; Kunai, A. Synthesis and properties of bis(methylthio)dithienosilole and its oxides. Organometallics, 2004, 23, 5481-5487.
115. Chen, C.-H.; Hsieh, C.-H.; Dubosc, M.; Cheng, Y.-J.; Hsu, C.-S. Synthesis and characterization of bridged bithiophene-based conjugated polymers for photovoltaic applications: acceptor strength and ternary blends. Macromolecules, 2010, 43, 697-708.
116. Zhu, Z.G.; Waller, D.; Gaudiana, R.; Morana, M.; Mühlbacher, D.; Scharber, M.; Brabec, C. Panchromatic conjugated polymers containing alternating donor/acceptor units for photovoltaic applications. Macromolecules, 2007, 40, 1981-1986.
117. Scharber, M.C.; Koppe, M.; Gao, J.; Cordella, F.; Loi, M.A.; Denk, P.; Morana, M.; Egelhaaf, H.-J.; Forberich, K.; Dennler, G.; Gaudiana, R.; Waller, D.; Zhu, Z.G.; Shi, X.B.; Brabec, C.J. Influence of the bridged atom on the performance of a low-bandgap bulk heterojuction solar cell. Adv. Mater., 2010, 22, 367-370.
118. Chen, H.-Y.; Hou, J.H.; Hayden, A.E.; Yang, H.; Houk, K.N.; Yang, Y. Silicon atom substitution enhances interchain packing in a thiophene-based polymer system. Adv. Mater., 2010, 22, 371-375.
119. Morana, M.; Azimi, H.; Dennler, G.; Egelhaaf, H.-J.; Scharber, M.; Forberich, K.; Hauch, J.; Gaudiana, R.; Waller, D.; Zhu, Z.G.; Hingerl, K.; Van Bavel, S.S.; Loos, J.; Brabec, C.J. Nanomorphology and charge generation in bulk heterojunctions based on low-bandgap dithiophene polymers with different bridging atoms. Adv. Funct. Mater., 2010, 20, 1180-1188.
120. Coffin, R.C.; Peet, J.; Rogers, J.; Bazan, G.C. Streamlined microwaveassisted preparation of narrow-bandgap conjugated polymers for highperformance bulk heterojunction solar cells. Nat. Chem., 2009, 1, 657-661.
121. Tong, M.H.; Cho, S.; Rogers, J.T.; Schmidt, K.; Hsu, B.B.Y.; Moses, D.; Coffin, R.C.; Kramer, E.J.; Bazan, G.C.; Heeger, A.J. Higher molecualr weight leads to improved photoresponsivity, charge transport and interfacial ordering in a narrow bandgap semiconducting polymer. Adv. Funct. Mater., 2010, 20, 3959-3965.
122. Hoven, C.V.; Dang, X.D.; Coffin, R.C.; Peet, J.; Nguyen, T.Q.; Bazan, G.C. Improved performance of polymer bulk heterojunction solar cells through the reduction of phase separation via solvent additives. Adv. Mater., 2010, 22, E63-E66.
123. Caputo, B.J.A.; Welch, G.C.; Kamkar, D.A.; Henson, Z.B.; Nguyen, T.-Q.; Bazan, G.C. A dithienosilole-benzooxadiazole donor-acceptor copolymer for utility in organic solar cells. Small, 2011, 7, 1422-1426.
124. Amb, C.M.; Chen, S.; Graham, K.R.; Subbiah, J.; Small, C.E.; So. F.; Reynolds, J.R. Dithienogermole as a fused electron donor in bulk heterojunction solar cells. J. Am. Chem. Soc., 2011, 133, 10062-10065.
125. Yuan, M.-C.; Chou, Y.-J.; Chen, C.-M.; Hsu, C.-L.; Wei, K.-H. A crystalline low-bandgap polymer comprising dithienosilole and thieno[3,4-c] pyrrole-4,6-dione units for bulk heterojunction solar cells. Polymer, 2011, 52, 2792-2798.
126. Huang, J.-H.; Teng, C.-M.; Hsiao, Y.-S.; Yen, F.-W.; Chen, P. L.; Chang, F.-C.; Chu, C.-W. Nanoscale correlation between exciton dissociation and carrier transport in silole-containing cyclopentadithiophene-based bulk heterojunction films. J. Phys. Chem. C, 2011, 115, 2398-2405.
127. Padhy, H.; Sahu, D.; Patra, D.; Pola, M.K.; Huang, J.-H.; Chu, C.-W.; Wei, K.-H.; Lin, H.-C. Synthesis and applications of cyano-vinylene-based polymers containing cyclopentadithiophene and dithienosilole units for photovoltaic cells. J. Polym. Sci. Part A: Polym. Chem., 2011, 49, 3417-3425.
128. Lin, H.-W.; Lin, L.-Y.; Chen, Y.-H.; Chen, C.-W.; Lin, Y.-T.; Chiu, S.-W.; Wong, K.-T. A new donor-acceptor molecule with uniaxial anisotropy for efficient vacuum-deposited organic solar cells. Chem. Commu., 2011, 47, 7872-7874.
129. Lee, S.H.; Jang, B.-B.; Kafafi, Z.H. Highly fluorescent solid-state asymmetric spirosilabifluorene derivatives. J. Am. Chem. Soc., 2005, 127, 9071-9078.
130. Xiao, H.B.; Leng, B.; Tian, H. Hole transport triphenylaminespirosilabifluorene alternating copolymer: synthesis and optical, electrochemical and electroluminescent properties. Polymer, 2005, 46, 5707-5713.
131. Xu, C.H.; Wakamiya, A.; Yamaguchi, S. Ladder oligo(pphenylenevinylene) s with silicon and carbon bridges. J. Am. Chem. Soc., 2005, 127, 1638-1639.
132. Mouri, K.; Wakamiya, A.; Yamada, H.; Kajiwara, T.; Yamaguchi, S. Ladder distyrylbenzenes with silicon and chalcogen bridges: synthesis, structures, and properties. Org. Lett., 2007, 9, 93-96.
133. Li, L.C.; Xu, C.H.; Li, S.H. New types of fluorescent polymers with bissilicon-bridged p-terphenyl as a building unit. Macromol. Chem. Phys., 2007, 210, 1097-1103.
134. Wang, J.-Y.; Hau, S.K.; Yip, H.-L.; Davies, J.A.; Chen, K.-S.; Zhang, Y.; Sun, Y.; Jen, A.K.-Y. Benzobis(silolothiophene)-based low bandgap polymers for efficient polymer solar cells. Chem. Mater., 2011, 23, 765-767.