Synthesis and Characterization of Small molecular Organic  Semiconductors: Applications in Organic Electronics

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姓名

亞維明(Velusamy Arulmozhi) 查詢紙本館藏

畢業系所

化學學系

論文名稱

(Synthesis and Characterization of Small molecular Organic Semiconductors: Applications in Organic Electronics)

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至系統瀏覽論文 (2025-6-30以後開放)

摘要(中)

本論文主要可分為有機薄膜電晶體 (OFET)、染料敏化太陽能電池 (DSSC) 和鈣鈦
礦太陽能電池 (PSC) 的材料開發。
有機薄膜電晶體 (OFET) 的部分分為 N-type 及 P-type 材料，本研究成功以 TII
為核心，開發出四種不同碳鏈之醌型結構材料，包含 TIIQ-10、TIIQ-b8、TIIQ-b16 和
TIIQ-b17，其中 TIIQ-b16 在 N-type OFET 中表現出高達 2.54 cm2
V
-1
s
-1 的電子遷移
率，電流開關比為 105
~106，具有單極電子傳輸特性和強環境穩定性。同時成功以 DTTR 為
核心，外接不同共軛基團，開發另一系列材料 DFPT-DTTR 及 DFPbT-DTTR，其中 DFPTDTTR 在 P-type OFET 中表現出高達 0.48 cm2
V
-1
s
-1 的電洞遷移率。
鈣鈦礦太陽能電池 (PSC) 的部分，本研究利用 BCDT 作為核心，接上不同苯基烷
氧鏈，再分別於末端接上拉電子基團 IN、INCl 與 INBr，共開發出六種材料 INBCDT-8、
INBCDT-b8、INClBCDT-8、INClBCDT-b8、INBrBCDT-8、INBrBCDT-b8，其中以 INBrBCDT-b8 應
用於 PSC 中可獲得高達 22.20% 的 PCE 值，FF 值為 79%，JSC 值為 24.44 mA cm-2，VOC
值為 1.15 V ，還可有效地鈍化表面缺陷並增強元件界面處的電荷傳輸能力。同時成功合
成出以 maleimide 為核心的材料 MLIBP’-4D，其 PCE 值高達 21.20%。
目前已成功合成出應用於 OFET、DSSC 和 PSC 的共軛醌型化合物、有機染敏材料
和電洞傳輸材料，這些新材料經由 UV-Vis 及 DPV 測量其光學及電化學性質、DSC 及 TGA
測量其熱穩定性，且利用 X 射線衍射、原子力顯微鏡 (AFM) 和掠入射 X 射線衍射
(GIXRD) 了解分子結構、分子堆疊、薄膜形態、結晶度和元件效能之間的關係，多項材料
應用之光電元件正在優化中。

摘要(英)

A number of small molecular organic semiconductors have been designed and synthesized for
various organic electronics device applications such as organic field-effect transistors (OFETs),
dye-sensitized solar cells (DSSCs), and perovskite solar cells (PSCs). The optical, and
electrochemical properties of these newly synthesized materials were examined using differential
pulse voltammetry (DPV), and UV-Visible absorption spectroscopy. Thermal properties were
investigated by differential scanning calorimetry (DSC) and thermo-gravimetric analysis (TGA).
Thin-film microstructure and film morphology were examined by X-ray diffraction, atomic force
microscopy (AFM), and grazing incidence X-ray diffraction (GIXRD) to understand the
relationship between the molecular structure, film morphology/crystallinity, and device
performance. The molecular structures of organic semiconductors and their molecular packing
properties were determined by single-crystal X-ray diffraction. In this research, air-processed
TIIQ-b16 OFETs exhibit electron mobility up to 2.54 cm2 V
−1
s
−1 with a current ON/OFF ratio of
105–106
exhibiting unipolar electron transport characteristics and enhanced ambient stability.
DFPT-DTTR compound based OFETs exhibit efficient hole transport mobility up to 0.48 cm2 V
−1
s
−1
. Non-fullerene acceptor (INBrBCDT-b8) was used as an anti-solvent in PSCs yielding an
excellent PCE of up to 22.20% with FF of 79%, a JSC of 24.44 mA cm-2
, and a VOC of 1.15 V, also
effectively passivate surface defects and enhance charge transport at the device interface. Further,
maleimide-based HTM (MLIBP’-4D) with tetra-substituted triphenylamine donors exhibits highperformance PCE reaching up to 21.20 % in PSCs. Several conjugated quinoidal compounds,
organic dyes, and hole-transporting materials (HTMs) have been synthesized for OFETs, DSSCs,
and PSCs, respectively. Presently, device characterization and optimization of these newly
developed small molecules are in progress for future publications.

關鍵字(中)

★ 有機小分子
★ 有機半導體
★ 有機場效電晶體
★ 染料敏化電池
★ 鈣鈦礦電池

關鍵字(英)

★ organic small molecules
★ organic semiconductors
★ organic field-effect transistors
★ dye-sensitized solar cells
★ perovskite solar cells

論文目次

Table of Contents
摘要.................................................................................................................................................. i
Abstract.......................................................................................................................................... ii
Acknowledgements ......................................................................................................................iii
List of Figures............................................................................................................................... ix
List of Schemes............................................................................................................................ xv
List of Tables............................................................................................................................... xvi
Chapter Ⅰ ..................................................................................................................................... 1
Introduction................................................................................................................................... 1
1.1. Introduction.......................................................................................................................... 3
1.2. Applications of organic semiconductors.............................................................................. 8
1.2.1. Organic field-effect transistors (OFETs)....................................................................... 8
1.3. Perovskite solar cells (PSCs) ............................................................................................. 12
1.4. Dye-sensitized Solar Cells (DSSCs).................................................................................. 14
Chapter Ⅱ ................................................................................................................................... 17
n-type organic field-effect transistors (OFETs)........................................................................ 17
Thienoisoindigo (TII)-Based Quinoidal Small Molecules for High-Performance n-Type
OFETs ...................................................................................................................................... 19
2.1. Abstract .............................................................................................................................. 19
2.2. Introduction........................................................................................................................ 19
2.3. Results and Discussion ...................................................................................................... 24
2.3.1. Synthesis..................................................................................................................... 24
2.3.2. Physical Characterization............................................................................................ 26
2.3.3. Theoretical Calculations ............................................................................................. 30
2.3.4. Single Crystal Structure .............................................................................................. 31
2.3.5. Charge Transport Properties ....................................................................................... 35
2.3.6. Thin Film Morphology and Structural Analysis......................................................... 38
2.3.7. OFET stability............................................................................................................. 45
2.4. Experimental Section......................................................................................................... 47
2.4.1. General Procedures for Final Target Compounds (1-4):............................................. 47
2.4.2. Characterization:......................................................................................................... 48
2.4.3. Device Fabrication and Measurement: ....................................................................... 49
2.5. Conclusion ......................................................................................................................... 50
Difuran-dithioalkyl based Quinoidal Compounds for n-type OFETs................................ 51
2.6. Introduction........................................................................................................................ 51
2.7. Results and Discussion: ..................................................................................................... 53
2.7.1. Synthesis..................................................................................................................... 53
2.7.2. Physical Characterization............................................................................................ 54
2.7.3. Single Crystal Structure .............................................................................................. 57
2.8. Experimental Section......................................................................................................... 62
2.8.1. General Procedures for Final Target Compounds (1–3):............................................ 62
2.9. Conclusion ......................................................................................................................... 63
Diselenophene-dithioalkyl based Quinoidal Compounds for n-type OFETs .................... 64
2.10. Introduction...................................................................................................................... 64
2.11. Results and Discussion: ................................................................................................... 66
2.11.1. Synthesis ................................................................................................................... 66
2.11.2. Physical Characterization.......................................................................................... 67
2.12. Experimental Section....................................................................................................... 70
2.12.1. General Procedures for Final Target Compounds (1–3): .......................................... 70
2.13. Conclusion ....................................................................................................................... 71
Chapter Ⅲ ................................................................................................................................... 73
p-type organic field-effect transistors (OFETs)........................................................................ 73
Solution Processable Pentafluorophenyl End-capped Dithienothiophene (DTTR) Organic
Semiconductors for Efficient p-type Organic Field Effect Transistors.............................. 75
3.1. Abstract .............................................................................................................................. 75
3.2. Introduction........................................................................................................................ 75
3.3. Results and Discussion ...................................................................................................... 79
3.3.1. Synthesis..................................................................................................................... 79
3.3.2. Physical Characterization............................................................................................ 81
3.3.3. Theoretical Calculations ............................................................................................. 85
3.3.4. Charge Transport Properties ....................................................................................... 86
3.3.5. Thin Film Morphology and Structural Analysis......................................................... 88
3.4. Experimental Section......................................................................................................... 90
3.4.1. General Procedures for Final Target Compounds (1-2):............................................. 90
3.4.2. OFET devices fabrication and characterization:......................................................... 92
3.5. Conclusion ......................................................................................................................... 93
Chapter Ⅳ ................................................................................................................................... 95
Non-fullerene Acceptors (NFAs)................................................................................................ 95
Grain Boundary Passivation in Perovskite Solar Cells by Bicyclopentadithiophene
(BCDT)-based Organic Semiconductor for High Performance and Stability .................. 97
4.1. Abstract .............................................................................................................................. 97
4.2. Introduction........................................................................................................................ 97
4.2. Results and Discussion .................................................................................................... 102
4.2.1. Synthesis................................................................................................................... 102
4.2.2. Thermal, optical, and electrochemical properties..................................................... 104
4.2.3. The morphology and photo-physics of the perovskite films with and without
passivation, as well as the photovoltaic performance and stability of the corresponding cells
..............................................................................................................................................111
4.3. Experimental Section....................................................................................................... 126
4.3.1. Materials ................................................................................................................... 126
4.3.2. Synthesis of INXBCDT target compounds and its intermediates.............................. 127
4.4. Conclusion ....................................................................................................................... 136
Chapter Ⅴ ................................................................................................................................. 137
Dye-Sensitized Solar Cells (DSSCs) ........................................................................................ 137
Alkyl (R), thioalkyl (SR) substituted Terthiophene (tT) and Bithiophene imide (BTI)-based
Organic Sensitizers for Dye-Sensitized Solar cell Applications............................................ 139
5.1. Introduction...................................................................................................................... 139
5.2. Results and Discussion .................................................................................................... 141
5.2.1. Synthesis of dyes (1-4).............................................................................................. 141
5.2.2. Synthesis of dyes (5 and 6)....................................................................................... 142
5.2.3. Thermogravimetric analysis...................................................................................... 143
5.2.4. Optical properties...................................................................................................... 145
5.2.5. Electrochemical properties........................................................................................ 146
5.3. Experimental Section....................................................................................................... 148
5.3.1. General Procedures for Final Target Compounds (1-4):........................................... 148
5.3.2. General Procedures for Final Target Compounds (5-6):........................................... 150
5.4. Conclusion ....................................................................................................................... 152
Chapter Ⅵ ................................................................................................................................. 153
Hole-transporting materials (HTMs)...................................................................................... 153
Aryl functionalized-Maleimides with triphenylamine donors as Hole-Transporting Materials for Perovskite Solar Cells.................................................................................... 155
6.1. Introduction...................................................................................................................... 155
6.2. Results and Discussion .................................................................................................... 157
6.2.1. Synthesis................................................................................................................... 157
6.2.2. Thermogravimetric analysis...................................................................................... 158
6.2.3. Optical properties...................................................................................................... 159
6.2.4. Electrochemical properties........................................................................................ 161
6.3. Experimental Section....................................................................................................... 162
6.3.1. General Procedures for Final Target Compounds (1-4):........................................... 162
6.4. Conclusion ....................................................................................................................... 163
Chapter Ⅶ ................................................................................................................................. 165
Conclusion ................................................................................................................................. 165
7.1. Conclusion ....................................................................................................................... 167
References.................................................................................................................................. 169
Publications ............................................................................................................................... 195
Supporting Information ........................................................................................................... 197

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指導教授

陳銘洲(Ming-Chou Chen)

審核日期

2022-7-4

推文