含咔唑、三苯胺和二苯甲酮的供體-受體交替和無規聚合物的合成、性質鑑定及有機場效電晶體之記憶體的應用

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研究生：	陳弈安 I-An Chen
論文名稱：	含咔唑、三苯胺和二苯甲酮的供體-受體交替和無規聚合物的合成、性質鑑定及有機場效電晶體之記憶體的應用 Synthesis, Characterization and OFET Memory Application of Donor-Acceptor Alternating and Random Polymers Containing Carbazoles, Triphenylamines and Benzophenones
指導教授：	游進陽 Chin-Yang Yu
口試委員:	施劭儒 Shao-Ju Shih 王丞浩 Chen-Hao Wang
學位類別：	碩士 Master
系所名稱：	工程學院 - 材料科學與工程系 Department of Materials Science and Engineering
論文出版年：	2023
畢業學年度：	111
語文別：	英文
論文頁數：	111
中文關鍵詞：	鈴木 -宮浦交叉偶聯反應、咔唑、三苯胺、二苯甲酮、交替聚合物、無規聚合物、有機場效應電晶體記憶體
外文關鍵詞：	alternating polymers, random polymers, carbazoles, triphenylamines, Suzuki-Miyaura cross-coupling polymerization, organic field-effect transistor memory
相關次數：	點閱：249 下載：0
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上一筆

在本研究中，我們通過
鈴木 -宮浦交叉偶聯聚合反應設計並合成了一系列含有咔
唑、三苯胺和二苯甲酮單元的電子供體與受體交替共聚物和無規聚合物。為了研
究不同電子供體在聚合物中的影響，我們研究了不同供體結構所造成的光學、電
化學和熱性質差異。由於 3,6-咔唑和二苯甲酮的共軛斷裂， 3,6-咔唑基聚合物與
2,7-咔唑基聚合物相比在吸收光譜中表現出完全不同的結果。另一方面，隨著
電子受體比例的增加，三苯胺基聚合物的最大吸收波長發生紅移，這應該與有效
分子內電荷轉移有關。隨著富含電子的氮原子參與共軛結構， 3,6-咔唑基和三苯
胺基聚合物表現出相對較高的最高占據分子軌域能級和紅移發射帶。由於結構中
含有豐富的芳香環，該聚合物表現出較高的熱穩定性。並且聚合物更進一步被
應用於有機場效應電晶體記憶體裝置，以討論高分子作為駐極體的性能。在基於
並五苯的 p型電晶體記憶體裝置中，所有交替聚合物都可以表現出很強的空穴捕
獲能力和光恢復性能。甚至在基於 N,N'-雙 (2-苯乙基 )-苝 -3,4:9,10-四羧基二酰亞
胺的 n 型電晶體記憶體裝置中 3,6-咔唑基和三苯胺基交替聚合物不僅表現出光
恢復行為，還表現出電子捕獲能力。

In this research, we designed and synthesized a series of donor-acceptor (D-A) alternating copolymers and random polymers containing carbazoles, triphenylamines and benzophenones via Suzuki-Miyaura cross-coupling polymerization. To investigate the effects of different electron donors in polymers, we examined the optical, electrochemical and thermal properties related to different donors in chemical structures. Due to the interruption of conjugation in 3,6-carbazoles and benzophenones, 3,6-carbazole-based polymers exhibited completely different results in absorption spectra compared to 2,7-carbazole-based polymers. On the other hand, triphenylamine-based polymers revealed red-shifted absorption wavelength as the increase of the ratio of electron acceptor possibly due to the effective interchain charge transfer between donor and acceptor moieties. Along with the involvement of electron-rich nitrogen atoms in the conjugation structure, 3,6-carbazole-based and triphenylamine-based polymers displayed relatively higher HOMO levels and red-shifted emission bands. The polymers showed high thermal stability owing to the abundant aromatic rings in the structures. In addition, the polymers were made into organic field-effect transistor (OFET) memory devices to discuss the performance of the polymers as an electret. In pentacene-based p-type transistor memories, strong hole trapping ability and photo-recovery property could be manifested in all alternating polymers. Furthermore, 3,6-carbazole-based and triphenylamine-based alternating polymers in N,N'-bis(2-phenylethyl)-perylene-3,4:9,10-tetracarboxylic diimide (BPE-PTCDI)-based n-type transistor memories demonstrated not only photo-recovery behavior but also electron trapping ability.

謝誌.............................................................................................................................. IV
Abstract ......................................................................................................................... V
中文摘要...................................................................................................................... VI
Table of Content ........................................................................................................ VII
Chapter 1. Introduction and Aims .................................................................................. 1
1 Conjugated polymer ............................................................................................. 1
2 Band gap and charge transport in conjugated polymer ........................................ 2
3 Introduction of carbazoles, triphenylamines and benzophenones ........................ 4
3.1 Introduction of carbazoles ............................................................................. 4
3.2 Introduction of triphenylamines (TPA) ......................................................... 5
3.3 Introduction of benzophenones ..................................................................... 6
4 Copolymer ............................................................................................................ 7
5 Organic semiconductor ........................................................................................ 8
5.1 Organic field-effect transistor (OFET) .......................................................... 9
5.2 OFET photomemory .................................................................................... 13
6 Aim of Project .................................................................................................... 16
Chapter 2. Result and Discussion ................................................................................ 17
1 Synthesis and characterization of monomers ..................................................... 17
1.1 Synthesis of monomers ................................................................................ 17
1.2 Characterization of monomers ..................................................................... 20
2 Synthesis and characterization of target polymers ............................................. 31
2.1 Synthesis of target polymers ........................................................................ 31
2.2 Characterization of target polymers ............................................................ 35
3 Properties of polymers ....................................................................................... 43
3.1 Optical properties of polymers .................................................................... 43
VIII
3.2 Electrochemical properties of polymers ...................................................... 51
3.3 Thermal properties of polymers .................................................................. 55
3.4 Morphology of polymers ............................................................................. 59
4 The properties of OFET memories of polymers ................................................ 61
4.1 P-type OFET memories of polymers ........................................................... 62
4.2 N-type OFET memories of polymers .......................................................... 65
Chapter 3. Conclusion .................................................................................................. 68
Chapter 4. Experimental Section ................................................................................. 70
1 General procedures ............................................................................................. 70
2 Synthesis of monomers ...................................................................................... 71
2.1 Synthesis of 4,4’-dibromo-2-nitrophenyl (1) ............................................... 71
2.2 Synthesis of 2,7-dibromo-9H-carbazole (2) ................................................ 71
2.3 Synthesis of 2,7-dobromo-9-octyl-9H-carbazole (M1) ............................... 72
2.4 Synthesis of 9-octyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (M2) ............................................................................................... 73
2.5 Synthesis of 3,6-dibromo-9H-carbazole (3) ................................................ 73
2.6 Synthesis of 3,6-dibromo-9-octyl-9H-carbazole (M3) ................................ 74
2.7 Synthesis of 9-octyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (M4) ............................................................................................... 75
2.8 Synthesis of 4-octyl-N,N-diphenylaniline (4) .............................................. 75
2.9 Synthesis of 4-bromo-N-(4-bromophenyl)-N-(4-octylphenyl)aniline (M5) 76
2.10 Synthesis of 4-octyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline (M6) ......................................................................................... 77
2.11 Synthesis of bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanone (M7) ................................................................................... 78
3 Synthesis of polymers ........................................................................................ 78
3.1 Synthesis of alternating copolymer (mczbp-50) .......................................... 78
3.2 Synthesis of random copolymer (mczbp-25) ............................................... 79
3.3 Synthesis of random copolymer (mczbp-15) ............................................... 80
3.4 Synthesis of random copolymer (mczbp-5) ................................................. 80
IX
3.5 Synthesis of homopolymer (homo-mcz) ..................................................... 81
3.6 Synthesis of alternating copolymer (pczbp-50) ........................................... 81
3.7 Synthesis of random copolymer (pczbp-25) ................................................ 82
3.8 Synthesis of random copolymer (pczbp-15) ................................................ 82
3.9 Synthesis of random copolymer (pczbp-5) .................................................. 83
3.10 Synthesis of homopolymer (homo-pcz) .................................................... 83
3.11 Synthesis of alternating copolymer (tpabp-50) ......................................... 84
3.12 Synthesis of random copolymer (tpabp-25) .............................................. 84
3.13 Synthesis of random copolymer (tpabp-15) .............................................. 85
3.14 Synthesis of random copolymer (tpabp-5) ................................................ 86
3.15 Synthesis of homopolymer (homo-tpa) ..................................................... 86
References .................................................................................................................... 88
Appendix ......................................................................................................................... i
                                

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全文公開日期 2028/08/02 (校內網路)
全文公開日期本全文未授權公開 (校外網路)
全文公開日期 2028/08/02 (國家圖書館：臺灣博碩士論文系統)

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