可溶性有機薄膜電晶體材料五環素與雙噻吩蒽分子衍生物之開發

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研究生：	莊哲維 Jhe-Wei Jhuang
論文名稱：	可溶性有機薄膜電晶體材料五環素與雙噻吩蒽分子衍生物之開發 Soluable Peantacene and Antradithiophene Derivatives for Organic Semiconductor
指導教授：	陳銘洲 Ming-Chou Chen
口試委員:
學位類別：	碩士 Master
系所名稱：	理學院 - 化學學系 Department of Chemistry
畢業學年度：	95
語文別：	中文
論文頁數：	138
中文關鍵詞：	雙噻吩蒽、五環素、有機薄膜電晶體
外文關鍵詞：	ADT, pentacene, OTFT, anthradithiophene
相關次數：	點閱：20 下載：0
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我們已經開發出6,13-Bis-phenylethynyl-pentacene (BPE-Pen)、5,11-Bis(phenylethyny)anthradithiophene (BPE-ADT)、6,13-Bis(4- Pentanoylphenylethynyl)pentacene (BPPE-Pen)、6,13-Bis(4- Pentanoyl phenylethynyl)antradithiophen (BBPE-ADT)、6,13-Bis(4-triethylsiliylphenylethynyl)pentacene (BTPE-Pen)、6,13-Bis(4-Pentanoylphenyl) pentacene (BPP-Pen)、6,13-Bis(4-Pentanoylphenyl)antradithiophene(BPP-ADT)、6,13-Bis(4-triethylsiliylphenyl)pentacene (BTE-Pen)八種有機半導體分子，目前已測量出BPE-Pen、BPE-ADT、BTE-Pen具有P型有機半導體材料之特性，其中BPE-ADT載子移動率可達1.42 x 10-2 cm2 V-1 s-1。藉由X光單晶繞射的解析，發覺BPE-ADT、BPE-Pen其外接苯環與其中心結構非共平面，其分子間堆疊與pentacene相同為魚骨狀構型，但載子移動率仍不如預期。
元件製作的部分，由西北大學Tobin J. Marks實驗室協助製作，以上所合成出的可溶性半導體將使用溶劑製程及真空蒸鍍的方法來製作元件。目前這些新材料的元件製備條件仍在嘗試階段，希望能找出最適合的製程條件，以利未來對此類分子的材料做更多的結構改良，以期提昇穩定度、溶解度和載子移動率並製作出元件效能更佳的有機薄膜電晶體。

Two new soluble organic semiconductor material systems were investigated. The first system is based on pentacene (Pen), five new organic semiconductor materials: 6,13-Bis(phenylethynyl)pentacene (BPE-Pen)、6,13-Bis(4-pentanoylphenylethynyl)pentacene (BPPE-Pen)、6,13-Bis(4-triethylsiliylphenylethynyl)pentacene (BTPE-Pen)、6,13-Bis(4-pentanoylphenyl)pentacene (BPP-Pen)、6,13-Bis(4-triethylsiliylphenyl)pentacene (BTE-Pen) were prepared. The second system is based on anthradithiophene (ADT), three new organic semiconductor materials: 5,11-Bis(phenylethynyl)anthradithiophene (BPE-ADT)、5,11-Bis(4-pentanoylphenylethynyl)antradithiophene (BBPE-ADT)、5,11-Bis(4-pentanoylphenyl)antradithiophene (BPP-ADT) were synthesized. BPE-Pen、BPE-ADT、BTE-Pen exhibited as P-type semiconductor。BPE-ADT shows the stability enhancement and with current mobility of 1.4x10-2 cm2/Vs, on/off ratio ~ 104 and threshold voltage -6.0V. The molecular structures of BPE-ADT and BPE-pen have been determined by single-crystal X-ray diffraction and reveal their herringbone packing and the phenyl group in both compounds are not coplanar to the central moiety, leading to a not very high mobility.
The device fabrications of all the eight materials are currently assisted by Tobin J. Marks group at Northwestern University, where the solution process and vacuum deposition will be examined. Hopefully, better mobility and easier fabrication will be obtained in the future.

中文摘要.........................................................................................................I
英文摘要........................................................................................................II
謝誌...............................................................................................................III
目錄................................................................................................................V
Equation........................................................................................................IX
Figure..............................................................................................................X
Scheme.......................................................................................................XIII
Table...........................................................................................................XIV
附錄目錄.....................................................................................................XV
第一章、 緒論
1- 1 前言...............................................................................................2
1- 2 有機薄膜電晶體導論...................................................................5
1- 3 有機薄膜電晶體之元件結構.......................................................9
1- 4 有機薄膜電晶體其操作原理.....................................................10
1- 5 有機薄膜電晶體導電機制與分子堆疊.....................................12
1-5-1有機半導體分子間電子傳遞.................................................12
1-5-2有機半導體分子間堆疊對於載子移動率之影響.................14
1- 6有機薄膜電晶體半導體材料......................................................17
1- 7 有機薄膜的製備方式
1-7-1氣相沈積.................................................................................19
1-7-2 液相製程.................................................................................21
1- 8 載子移動率之計算.....................................................................25
1- 9 研究目的與動機.........................................................................28
第二章、實驗部份
2-1 實驗藥品
2-1-1 實驗所用之化學藥品..........................................................34
2-1-2 實驗所用之溶劑除水部分................................................. 36
2-2 實驗儀器
2-2-1核磁共振光譜儀...................................................................36
2-2-2高解析質譜儀.......................................................................37
2-2-3紫外光/可見光吸收光譜儀..................................................37
2-2-4式差熱掃描卡計...................................................................38
2-2-5熱重分析儀...........................................................................38
2-2-6電化學裝置...........................................................................39
2-3 合成步驟
2-3-1  1-Phenyl-1,3-butadiene(3)的合成..........................................39
2-3-2  2-Butyl-2-(4-ethynyl-phenyl)-[1,3]dioxolane
(7)的合成.....................................................................................42
2-3-3  1-Ethyny-4-triethylsilylbenzene(11)的合成...........................46
2-3-4  6,13-Bis(phenylethynyl)pentacene
(BPE-Pen ; 13) 之合成.................................................................48
2-3-5  5,11-Bis(phenylethyny)anthradithiophene
(BPE-ADT，15)之合成...............................................................51
2-3-6  5,11-Bis(triethylsilylethynyl)anthradithiophene
(TES-ADT，16)之合成...............................................................54
2-3-7  6,13-Bis(4-pentanoylphenylethynyl)pentacene
(BPPE-Pen，19)之合成...............................................................56
2-3-8  5,11-Bis(4-pentanoylphenylethynyl)antradithiophen
(BBPE-ADT，21)的合成.............................................................59
2-3-9  6,13-Bis(4-triethylsiliylphenylethynyl)pentacene
(BTPE-Pen，22)的合成...............................................................61
2-3-10 6,13-Bis(4-pentanoylphenyl)pentacene
(BPP-Pen，23)的合成..................................................................63
2-3-11 5,11-Bis(4-Pentanoylphenyl)antradithiophene
(BPP-ADT，24) 的合成...............................................................64
2-3-12 6,13-Bis(4-triethylsiliylphenyl)pentacene
(BTE-Pen，25)的合成.................................................................66
2-4  OTFT元件製作..........................................................................68
第三章、結果與討論
3-1  有機半導體分子於合成上之探討
3-1-1  1-Phenyl-1,3-butadiene(3)合成上之探討.............................71
3-1-2  BPPE-PEN(19)的合成探討...................................................72
3-2  有機半導體分子其穩定性之探討
3-2-1  Penatcene衍生物於含光與氧環境下其分子穩定性
之探討.............................................................................................73
3-2-2  ADT衍生物於含光與氧之環境其分子穩定性探討...........79
3-2-3  有機半導體分子熱穩定性的探討.......................................84
3-3  有機半導體分子堆疊性與其載子移動率之探討
3-3-1  有機半導體堆疊性...............................................................90
3-3-2  有機半導體載子移動率的測量............................................94
第四章、結論 ...................................................................................103
參考文獻 ...........................................................................................105
附錄....................................................................................................109

                                

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