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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 謝國煌 | |
| dc.contributor.author | Yan-Nian Chen | en |
| dc.contributor.author | 陳彥年 | zh_TW |
| dc.date.accessioned | 2021-06-15T04:52:11Z | - |
| dc.date.available | 2012-09-23 | |
| dc.date.copyright | 2010-08-04 | |
| dc.date.issued | 2010 | |
| dc.date.submitted | 2010-07-30 | |
| dc.identifier.citation | 1. A. E. Becquerel, Compt. Rend. Acad. Sci. 9 (1839) 145.
2. C. W. Tang, Appl. Phys. Lett. 48 (1986) 183. 3. M. Hiramoto, H Fujiwara, M. Yokoyama, J. Appl. Phys. 72 (1992) 3781. 4. (A) N. S. Sariciftci, L. Smilowitz, A. J. Heeger, F. Wudl, Science 258 (1992) 258. (B) L. Smilowitz, N. S. Sariciftci, R. Wu, C. Gettinger, A. J. Heeger, F. Wudl, Phys. Rev. B 47 (1993) 13835. 5. J. J. M. Halls, C. A. Walsh, N. C. Greenham, E. A. Marseglia, R. H. Friend, S. C. Moratti, A. B. Holmes, Nature 376 (1995) 498. 6. M. Granström, K Petritsch, A. C. Arias, A.Lux, M. R. Anderson, R. H. Friend, Nature 395 (1998) 257. 7. (A) W. L. Ma, C. Y. Yang, X. Gong, K. Lee, A. J. Heeger, Adv. Funct. Mater. 15 (2005) 1617. (B) Y. Y. Kim, S. Cook, S. M. Tuladhar, S. A. Choulis, J. Nelson, J. R. Durrant, D. D. C. Bradley, M. Giles, I. Mcculloch, C.-S. Ha, M. Ree, Nat. Mater. 5 (2006) 197. (C) J. Y. Kim, K. Lee, N. E. Coates, D. Moses, T.-Q. Nguyen, M. Dante, A. J. Heeger, Science 317 (2007) 222. (D) G. Li, V. Shrotriya, J. S. Huang, Y. Yao, T. Moriarty, K. Emery, Y. Yang, Nat. Mater. 4 (2005) 864. (E) J. Peet, J. Y. Kim, N. E. Coates, W. L. Ma, D. Moses, A. J. Heeger, G. C. Bazan, Nat. Mater. 6 (2007) 497. (F) W.-Y. Wong, X.-Z. Wang, Z. He, A. B. Djurišić, C.-T. Yip, K.-Y. Cheung, H. Wang, C. S. K. Mak, W.-K. Chan, Nat. Mater. 1 (2007) 6521. 8. (A) J. G. Xue, B. P. Rand, S. Uchida, S. R. Forrest, Adv. Mater. 17 (2005) 66. (B) M. Y. Chan, S. L. Lai, M. K. Fung, C. S. Lee, S. T. Lee, Appl. Phys. Lett. 90 (2007) 023504 . (C) J. G. Xue, S. Uchida, B. P. Rand, S. R. Forrest, Appl. Phys. Lett. 85 (2004) 5757. 9. A. Moliton, J. M. Nunzi, Polym. Int. 55 (2006) 583. 10. B. C. Thompson, J. M. J. Fréchet, Angew.Chem. Int. Ed. 47 (2008) 58. 11. M. C. Scharber, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, A. J. Heeger, C. J. Brabec, Adv.Mater.18 (2006) 789. 12. S. Gunes, H. Neugebauer, N. S. Sariciftci, Chem. Rev. 107 (2007) 1324. 13. H. Hoppe, N. S. Sariciftci, J. Mater. Res. 19 (2004) 1924. 14. J. Peet, M. L. Senatore, A. J. Heeger, G. C. Bazan, Adv. Mater. 21(2009) 1521. 15. Jayakannan, M., P.A. Van Hal, and R.A.J. Janssen, J. Polymer Sci. Chem. 40 (2002) 251. 16. Winder, C. and N.S. Sariciftci, J. Mater. Chem. 14 (2004) 1077). 17. Yu, G., et al., Science 270 (1995) 1789. 18. Iraqi, A.; Wataru, I. Chem. Mater. 16 (2004) 442. 19. Blouin, N.; Michaud, A.; Gendron, D.; Wakim, S.; Blair, E.; Neagu-Plesu, R.; Bellete ˆte, M.; Durocher, G.; Tao, Y.; Leclerc, M. J. Am. Chem. Soc. 130 (2008) 732. 20. Leclerc, N.; Michaud, A.; Sirois, K.; Morin, J. F.; Leclerc, M. Adv. Funct. Mater. 16 (2006) 1694. 21. Hou, J.; Tan, Z.; Yan, Y.; He, Y.; Yang, C.; Li, Y. J. Am. Chem. Soc. 128 (2006) 4911. 22. Chang, Y.-T.; Hsu, S.-L.; Chen, G.-Y.; Su, M.-H.; Singh, T. A.; Diau, E. W.-G.; Wei, K.-H. AdV. Funct. Mater. 18 (2006) 2356. 23. (A) 蔣尚德, 含苯並噻二唑及卡唑小分子衍生物之合成及其應用在有機太陽能電池之研究,國立台灣大學, 台北 (2009). (B)吳韋霖, 含苯並噻二唑側鏈之卡唑高分子衍生物之合成及其光電特性, 國立台灣大學, (2009). 24. Sergio M. Bonesi and Rosa Erra-Balsells. J. Heterocyclic Chem. 38 (2001) 77. 25. 林佳華, 咔唑之共軛高分子的合成及其應用於發光二極體之研究,國立台灣大學, (2007). 26. C. J. Brabec, Sol. Energy Mater. Sol. Cells 83 (2004) 273. 27. C. J. Brabec, A. Cravino, D. Meissner, N. S. Sariciftci, M. T. Rispens, L. Sanchez, J. C. Hummelen, T. Fromherz, Thin Solid Films 368 (2002) 403. 28. (A) J. Gao, F. Hide, H. Wang, Synth. Met. 84 (1997) 979. (B) J. Liu, Y. Shi, Y. Yang, Adv. Funct. Mater. 11 (2001) 420. 29. (A) H. Frohne, S.E. Shaheen, C. J. Brabec, D. C. Müller, N. S. Sariciftci, K. Meerholz, Chem Phys Chem. 9 (2002) 795. (B) V. D. Mihailetchi, P. W. M. Blom, J. C. Hummelen, M. T. Rispens, J. Appl. Phys. 94 (2003) 6849. 30. (A) C. J. Brabec, S. E. Shaheen, C. Winder, N. S. Sariciftci, P. Denk, Appl. Phys. Lett. 80 (2002) 1288. (B) F. L. Zhang, M. Johansson, M. R. Anderson, J. C. Hummelen, O. Inganäs, Synth. Met. 137 (2003) 1401. 31. M. C. Scharber, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, A. J. Heeger, C. J. Brabec, Adv. Mater. 18 (2006) 789. 32. C. D. Dimitrakopoulos, D. J. Mascaro, IBM J. Res. Dev. 45 (2001) 11. 33. E. Buhleier, W. Wehner, F. Vögtle, Synthesis 1978 (1978) 155. 34. N. Kopidakis, W. J. Mitchell, J. v. d. Lagemaat, D. S. Ginley, G. Rumbles, S. E. Shaheen, Appl. Phys. Lett. 89 (2006) 103524. 35. C.-Q. Ma, M. Fonrodona, M. C. Schikora, M. M. Wienk, R. A. J. Janssen, P. Baüerle, Adv. Funct. Mater. 18 (2008) 3323. 36. X. Sun, Y. Zhou, W. Wu, Y. Liu, W. Tian, G. Yu, W. Qiu, S. Chen, D. Zhu, J. Phys. Chem. B 110 (2006) 7702. 37. A. B. Tamayo, B. Walker, T.-Q. Nguyen, J. Phys. Chem. C 112 (2008) 11545. 38. M. L. Sun, L. Wang, X. H. Zhu, B. Du, R. S. Liu, W. Yang, Y. Cao, Sol. Energy Mater. Sol. Cells 91 (2007) 1681. 39. M. L. Sun, L. Wang, B. Du, Y. Xiong, R. S. Liu, Y. Cao, Synth. Met. 158 (2008) 125. 40. M. L. Sun, L. Wang, Y. Cao, Synth. Met. 159 (2009) 556. 41. L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, E. Moons, R. H. Friend, J. D. Mackenzie, Science 293 (2001) 1119. 42. K Hubner, Chemie in unserer Zeit 40 (2006) 274. 43. 辜政脩，聚氨酯共聚高分子於電激發光元件之電洞傳輸層應用，國立台灣大學，台北(2008)。 44. S.-L. Lin, L.-H. Chan, R.-H. Lee, M.-Y. Yen, W.-J. Kuo, C.-T. Chen, R.-J. Jeng, Adv. Mater. 20 (2008) 3947. 45. J. Cremer, P. Baüerle, Eur. J. Org. Chem. (2005) 3715. 46. J. Cremer, P. Baüerle, J. Mater. Chem. 16 (2006) 874. 47. Mei, J.; Ogawa, K.; Kim, Y.-G.; Heston, N. C.; Arenas, D. J.;Nasrollahi, Z.; McCarley, T. D.; Tanner, D. B.; Reynolds, J. R.;Schanze, K. S. ACS Appl. Mater. Interfaces (2009) 150. 48. Dante, M., Garcia, A., Nguyen, T.-Q. J. Phys. Chem. C. 113 (2009) 1596. 49. Woo, C. H., Thompson, B. C., Kim, B. J., Toney, M. F., Fre ´chet, J. M. J. J. Am. Chem. Soc. 130 (2008) 16324. 50. Okamoto, T., Jiang, Y.,Qu, F., Mayer, A. C., Parmer, J. E.; McGehee M. D., Bao, Z. Macromolecules 41 (2008) 6977. 51. Vinich Promarak, Auradee Pankvuang Somsak Ruchirawat, Tetrahedron Letters 48 (2007) 1151. 52. Jianguo Mei, Nathan C. Heston, Svetlana V. Vasilyeva, and John R. Reynolds, Macromolecules 42 (2009) 1482. 53. Kuang-Chieh Li, Jen-Hsien Huang, Ying-Chan Hsu, Kung-Hwa Wei, Macromolecules 42 (2009) 3681. 54. Lijun Huo, Teresa L. Chen, Yi Zhou, Jianhui Hou, Hsiang-Yu Chen, Yang Yang, a Yongfang Li, Macromolecules 42 (2009) 4377. 55. Wei Yue, Yun Zhao, Hongkun Tian, De Song, Zhiyuan Xie, Donghang Yan,Yanhou Geng, Fosong Wang, Macromolecules 42 (2009) 6510 56. Laure Biniek, Christos L. Chochos, Nicolas Leclerc, Georges Hadziioannou, Joannis K. Kallitsis, Rony Bechara, Thomas Heiser, J. Mater. Chem. 19 (2009) 4946. 57. J. A. Mikroyannidis, A. N. Kabanakis, Anil Kumar, S. S. Sharma, Y. K. Vijay and G. D. Sharma Langmuir 26 (2010) 12909. 58. Seon Kyoung Son, Yoon Suc Choi, Woo Hyung Lee, J. Polymer Sci. Chem. 48 (2010) 635. 59. Jing Zhang, Yi Yang, Chang He, Youjun He, Guangjin Zhao, Yongfang Li, Macromolecules 42 (2009) 7619. 60. Zheng-Ming Tang, Ting Lei, Jin-Liang Wang, Yuguo Ma, Jian Pei, J. Org. Chem. 75 (2010) 3644. 61. Jung-HsunTsai, Wen-YaLee, Wen-ChangChen, Chao-YingYu, Gue-WuuHwang, Ching Ting, Chem. Mater. 22 (2010) 3290. 62. Pierre M. Beaujuge, Jegadesan Subbiah, Kaushik Roy Choudhury, Stefan Ellinger, Tracy D. McCarley, Franky So and John R. Reynolds, Chem. Mater. 22 (2010) 2093. 63. Chunhui Duan, Wanzhu Cai, Fei Huang, Jie Zhang, Ming Wang, Tingbin Yang, Chengmei Zhong, Xiong Gong and Yong Cao, Macromolecules 43 (2010) 5262. 64. N. M. Kronenberg, M. Deppisch, F. Würthner, H. W. A. Lademann, K. Deinga, K. Meerholz, Chem. Commun. (2008) 6489. 65. T. Rousseau, A. Cravino, T. Bura, G. Ulrich, R. Ziessel, J. Roncali, Chem. Commun. (2009) 1673. | |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/46043 | - |
| dc.description.abstract | 本研究運用烏曼偶合(Ullmann coupling)及鈴木偶合(Suzuki coupling)合成出以卡唑(carbazole)為主體，並由卡唑9號位置引入噻吩(thiophene)及苯並噻二唑(benzothiadiazole)的施體-受體(donor-acceptor)分子結構O1及O2，並在合成過程中得到卡唑對稱分子CBC、CTC及C2TC。進而以Yamamoto反應聚合成卡唑為主鏈，噻吩及苯並噻二唑為側鏈之聚合物P1。聚合物以凝膠滲透層析儀(GPC)測試，分析結果P1之重量平均分子量(Mw)為4333 g/mol，PDI為1.28。在熱性質上，各組化合物皆展現了良好的熱穩定性，熱裂解溫度(Td 5%)都在350℃以上。在光學性質方面，證實了在分子結構內引入噻吩確實能達到使吸收光譜紅移的效果，其中O2薄膜的最大吸收波長紅移至493 nm、吸收起始波長為604 nm，光學能隙為2.05 eV，O1和P1的能隙則分別為2.20 eV及2.18 eV。電化學分析顯示，隨著噻吩的增加，最高填滿分子軌域(highest occupied molecular orbital, HOMO)有向上提升的趨勢，不過各組材料大多落在-5.4 eV的位置，而結構內酯基的引入有助於最低未填分子軌域能階(lowest unoccupied molecular orbital, LUMO)的下降，這點在此材料的能階設計上有正面的影響。此外，三組卡唑對稱分子的HOMO及LUMO能階介於ITO (4.80 eV)和Alq3 (5.80 eV)之間，有機會作為發光二極體之電洞傳遞層材料。體異質接面太陽能電池元件的初步測試以O1和O2為主。O1與PCBM以1: 2的重量比例混摻，在以氯仿作為溶劑、900 rpm旋轉塗佈的條件下，得到最佳效率值為0.056%，其中開路電壓為0.53 V、短路電流0.32 mA/cm2、填充因子為0.33；
而O2以相同溶劑和旋轉塗佈轉速下，與PCBM 1:4重量比混摻，效率值為0.045%，其中開路電壓為0.44 V、短路電流0.38 mA/cm2、填充因子為0.27。 | zh_TW |
| dc.description.abstract | In this study, two carbazole derivatives (O1 and O2) with thiophene and benzothiadiazole-containing donor-acceptor structure were synthesized via Ullmann coupling and Suzuki coupling reactions. During the synthesizing process, three extra N-carbazole endcapped derivatives (CBC, CTC, and C2TC) were obtained. We also tried polymerizing the carbazole derivative monomers with thiophene and benzothiadiazole-containing side chain via Yamamoto coupling reaction, and Homopolymer P1 were synthesized with weight-average molecular weight of 4333 g/ mol, PDI 1.28. All derivatives were found with good thermal stability, and 5% thermal degradation temperature over 350 oC. The optical properties indicated that the absoption and emission maxma were red-shifted with increasing number of thiophene unit. The optical band gap of O1, O2 and P1 are 2.20 eV, 2.05 eV, 2.18 eV respectively. We also observed that the HOMO of these derivatives increased with increasing number of thiophene unit. The energy level of the three N-carbazole endcapped derivatives were found suitable for application of hole transporting layer of OLED. The preliminary bulk heterojunction solar cell device were fabricated with compound O1 and O2. The power conversion efficiency of the device based on O1: PCBM = 1 : 2 and O2: PCBM = 1 : 4 are 0.056% and 0.045% under AM 1.5G solar simulator. | en |
| dc.description.provenance | Made available in DSpace on 2021-06-15T04:52:11Z (GMT). No. of bitstreams: 1 ntu-99-R97524057-1.pdf: 2716650 bytes, checksum: c25c81bc20724435817b6a7493a56ff1 (MD5) Previous issue date: 2010 | en |
| dc.description.tableofcontents | 摘要 I
Abstract II 目錄 III 表目錄 VI 圖目錄 VII 第一章 緒論 1 1-1前言 1 1-2太陽能電池的種類 1 第二章 文獻回顧 3 2-1有機太陽能電池發展簡介 3 2-2 有機太陽能電池元件種類 4 2-3有機太陽能電池之工作原理 5 2-4有機太陽能電池之特性分析 6 2-4-1 開路電壓 7 2-4-2 短路電流 7 2-4-3 填充因子 7 2-4-4 能量轉換效率 8 2-5有機太陽能電池之分子設計 9 2-6有機太陽能電池材料回顧 10 2-6-1卡唑為主體之材料 11 2-6-2具共軛側鏈之噻吩材料 12 2-7 研究目的與材料合成方向 13 第三章 實驗部分 15 3-1 實驗藥品 15 3-2 實驗溶劑及材料 18 3-3 實驗儀器 19 3-4實驗架構 20 3-5 各化合物之合成步驟 21 3-6 性質分析 39 3-6-1 液態超導氫核磁共振儀測試 39 3-6-2 熱重損失分析儀測試 39 3-6-3 微差掃描熱卡計測試 39 3-6-4 循環伏安儀測試 39 3-6-5 紫外光-可見光分光光譜儀測試 40 3-6-6 太陽能電池元件測試 40 第四章 結果與討論 41 4-1合成步驟與討論 41 4-1-1 小分子化合物之合成 41 4-1-2 單體之合成與聚合反應 45 4-2 合成結果分析 47 4-3熱性質分析 49 4-3-1熱重分析儀測試 49 4-3-2 微差掃描熱卡計分析 50 4-4 光學性質分析 54 4-4-1紫外光-可見光分光光譜儀 54 4-4-2螢光光譜儀 59 4-5電化學性質分析 59 4-6 太陽能電池元件測試 65 第五章 結論 68 參考文獻 69 附錄：化合物之1H-NMR圖譜 75 | |
| dc.language.iso | zh-TW | |
| dc.title | 含卡唑及噻吩衍生物之合成及其在有機太陽能電池應用之光電特性 | zh_TW |
| dc.title | Synthesis and Characterizations of Carbazole and Thiophene-Containing Derivatives for Organic Solar Cell Applications | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 98-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 王怡仁,韓錦鈴,郭昭輝,黃智楷 | |
| dc.subject.keyword | 卡唑,噻,吩,苯並噻,二唑,施體-受體,體異質接面有機太陽能電池, | zh_TW |
| dc.subject.keyword | carbazole,thiophene,benzothiadiazole,donor-accepto,bulk heterojunction solar cell, | en |
| dc.relation.page | 93 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2010-08-02 | |
| dc.contributor.author-college | 工學院 | zh_TW |
| dc.contributor.author-dept | 化學工程學研究所 | zh_TW |
| 顯示於系所單位： | 化學工程學系 | |
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