應用於有機電子元件之共軛分子的新合成方法

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研究生：	張書維 Chang, Shu-Wei
論文名稱：	應用於有機電子元件之共軛分子的新合成方法 New Synthesis Strategies for Conjugated Architectures and their Applications in Organic Electronics
指導教授：	堀江正樹 Horie, Masaki
口試委員:	蘇安仲劉振良游進陽陳信龍
學位類別：	博士 Doctor
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2015
畢業學年度：	103
語文別：	英文
論文頁數：	345
中文關鍵詞：	有機光伏打電池
外文關鍵詞：	PCPDTBT, OPV, direct arylation, crosslinking
相關次數：	點閱：54 下載：0
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Poly(cyclopentadithiophene-alt-benzothiadiazole) (PCPDTBT)為應用於有機光伏打電池(organic photovoltaic, OPV)第三代半導體高分子的第一個標竿材料，其特色在於主結構中具有交替式的與體及受體結構與縮合環之分子設計。本論文可分為兩大部分：探討及改善PCPDTBT，與合成以cyclopentadithiophene (CPDT)和 benzothiadiazole (BT)為基礎架構的新型高分子。
在第一個部分，我們發展了鈀金屬催化之直接芳基化聚合法來合成PCPDTBT。在添加K2CO3、Pd(OAc)2、pivalic acid (PivOH)、N-methylpyrrolidone (NMP)並加熱至攝氏80度反應20小時的最佳化條件下，可達成76%的高產率(Soxhlet純化之後)，並帶有71700之高平均分子量。最關鍵的是，以新聚合法所製作出來的PCPDTBT在OPV元件效率的表現上更勝於一般使用鈴木法所製備的PCPDTBT。直接芳基化法也被應用於其他低價帶共軛高分子的合成。未來此方法擁有大量合成高效能材料的潛力，其簡化了合成流程、更好的整體產率、綠色化學以及更低的生產成本。
我們也致力於提升PCPDTBT高分子的熱穩定性，利用添加熱膠聯官能基於CPDT分子之側鏈上。其OPV的生命週期較未經修飾的PCPDTBT得到了51%顯著的提升，此熱穩定的提升歸功於元件熱退火後所產生的高分子交聯體。此熱膠聯反應由紅外光譜儀(FT-IR)與溶解度測試所確認，而表面型態則由原子力顯微鏡(AFM)與 GISAXS進行鑑定。
另一方面，我們探討了與體-受體在交替式共軛高分子中的影響，藉由合成各式比例的CPDT與BT於重複單元中，是為-[(CPDT)x-(BT)y]n-。高分子群在薄膜狀態下擁有1.7至2.0電子伏特的光學能階差，其能階差由小至大依序為：x:y = 1:1、1:2、2:1、 2:2、3:3。最佳的OPV元件效率為2.45%，在不添加表面修飾劑下由x:y = 2:2的高分子與PC61BM作為主動層材料。OPV效率依序為：x:y = 2:2、2:1、1:1、3:3、 1:2，顯示了與體-受體之比例和長度對於OPV元件之影響。
在第二部分中，我們首先合成了CPDT-BT-CPDT之寡聚物以觀測其Ｘ光單晶繞射的結構。單晶的結構中證實了寡聚物並非完全地散亂無規則，而是以BT為中心做交叉式的堆疊，間距乃3.61 Å。其提供了對於了解高分子塊材結構極具參考價值的資料。雖然此寡聚物的OPV與有機場校電晶體(OFET)效率並不突出(移動率 = 5 × 10-3 cm2 V-1 s-1 與能源轉換效率 1.61%)，但其可以作為色素增感材料來增加PCPDTBT與P3HT之OPV元件光吸收能力，最適添加濃度下可提升總體效率約3~9%。
接下來，我們設計並合成出一系列以「CPDT-受體-CPDT」為核心結構的高分子群。結果顯示，隨著thiophene在主結構中的數量成長，高分子將呈現出階段式的藍位移光譜吸收與更好的π-π堆疊能力。在評估TPD與BT受體中，TPD系列之高分子群較BT之高分子群擁有約40 nm之藍位移吸收以及約0.2 V更深的HOMO能階。其中，同時含有TPD與BT受體的高分子在配合PC71BM與添加1,8-octanedithiol的條件下展現出最好的能源轉換效率3.0%。
最後，我們專注於利用開環置換聚合法合成全共軛之共嵌段高分子。受體性的dithienobenzothiadiazole-vinylene之環狀單體和與體性的cyclopentadithiophene-vinylene之環狀單體皆由McMurry反應製備而成。目標物第一段之製備始於受體性單體的開環反應，隨後在反應途中加入與體性單體使其成為第二段，從而完成了全共軛共嵌段聚合物之合成。此新型高分子展現出了多重光學與電化學的性質，使其能夠吸收300~700 nm寬廣的範圍。

Poly(cyclopentadithiophene-alt-benzothiadiazole) (PCPDTBT) was the first breakthrough on the third generation semiconducting polymer in organic photovoltaic (OPV) applications, featuring alternating donor-acceptor moieties and design of fused ring in the polymer main chain. This thesis involves two parts: the studies and improvements of PCPDTBT; the synthesis of new polymers and oligomers based on cyclopentadithiophene (CPDT) and benzothiadiazole (BT) units.
In the first part, we developed Pd-catalyzed direct arylation polymerization for the synthesis of PCPDTBT, being produced in 76% yield after Soxhlet with high number-average molecular weight (Mn) of 71700 in the presence of K2CO3, Pd(OAc)2, and pivalic acid (PivOH) in N-methylpyrrolidone (NMP) at 80 °C for 20 hours. Most importantly, OPV device of the best PCPDTBT shows improved power conversion efficiency (PCE) over the one by Suzuki coupling. The optimized reaction condition was also applied to other monomers to obtain various low-bandgap conjugated copolymers. This synthetic route allows scale-up synthesis of high performing polymers with fewer synthetic steps, higher yield, greener chemistry, and at a lower cost.
Then we worked on enhancing the stability of PCPDTBT OPV devices by synthesizing thermally crosslinkable group on the side chains on CPDT. The lifetime of the OPV was 51% enhanced over an OPV using standard PCPDTBT. This higher stability is accounted for the crosslinkable structure of the polymer after annealing. The crosslinking reaction was confirmed by solubility tests, Fourier transform infrared spectroscopy, and morphological analysis conducted by atomic force microscopy and simultaneous synchrotron grazing-incidence small-/wide-angle X-ray scattering.
We also studied on the effect of donor-acceptor ratio by synthesizing various and lengths of CPDT to BT repeating units, -[(CPDT)x-(BT)y]n-. The polymers showed optical band gap between 1.7 and 2.0 eV in film. Polymer with ratios of CPDT:BT (x:y = 1:1) units showed lowest energy bandgap, followed by x:y = 1:2, 2:1, 2:2 and 3:3. OPV devices of these polymers with PC61BM as the electron acceptor in the absence of any additives show the best PCE of 2.45% using the polymer with ratios of CPDT:BT (x:y = 2:2) units, followed by the ratios of x:y = 2:1, 1:1, 3:3 and 1:2, indicating relevance of ratios and length of donor and acceptor units in OPV performance.
In the second part, we started with the investigation of the X-ray single crystal structure of CPDT-BT-CPDT oligomer, which confirms that they are not entirely disordered, but are actually stacking directly across each other at the central BT units with an intermolecular distance of 3.61 Å, providing valuable insight into the polymer bulk structure. While showing moderate mobility of 5 × 10-3 cm2 V-1 s-1 and a PCE of 1.61%, one potential use for the oligomer could be as a sensitizer in a ternary blend with P3HT–PC61BM or PCPDTBT–PC61BM OPVs; the PCE can be relatively increased by 3–9% depending on concentration, primarily as a result of increased short circuit current density.
Then a series of polymers containing “CPDT-Acceptor-CPDT” structure has been designed and synthesized. We show that the increasing amount of thiophene in the polymer backbone can affect stepwise blue shift of the UV-vis absorption and better π-π stacking ability. When comparing with BT and TPD acceptor, polymers containing TPD unit showed about 40 nm blue shift of the UV absorption and 0.2 V deeper HOMO levels according to cyclic voltammetry measurement. Among them, polymer containing both TPD and BT shows best PCE of 3.0% with PC71BM in the presence of 1,8-octanedithiol.
Finally, we targeted on synthesis of fully conjugated block copolymer (BCP) by ring-opening metathesis polymerization (ROMP). Novel conjugated cyclophanes comprising electron donating cyclopentadithiophene-vinylene and accepting dithienobenzothiadiazole-vinylene have been synthesized by McMurry coupling. ROMP of the acceptor monomer and the subsequent addition of the donor monomer allows the preparation of a fully conjugated BCP. The BCP exhibits multiple optical and electrochemical functions, giving wide range of light absorption from 300 to 700 nm.

Contents
Chapter 1 
Conjugated polymers for application of organic electronics
Introduction    14
1.1 Organic photovoltaic (OPV)    16
1.2 Organic field effect transistor (OFET)    20
1.3 Conjugated polymers    24
References    27
Chapter 2
Synthesis and device characteristics of cyclopentadithiophene-benzothiadiazole oligomers
Introduction    30
2.1 Organic electronics of small molecules     30
Results and Discussion    33
2.2 Preparation of oligomers    33
2.3 Crystallographic structures    37
2.4 Morphological characteristics    40
X-ray diffraction    40
Atomic force microscopy    45
2.5 Optical, electrochemical, and thermal properties    46
2.6 Device characterization    49
OFET devices    49
OPV devices    50
Conclusion    52
References    53
Chapter 3
Palladium-catalyzed direct arylation polymerization for synthesis of low-bandgap conjugated polymers
Introduction    55
3.1 Direct arylation    55
3.2 Polycondenzation of conjugated polymers    58
Results and Discussion    61
3.3 Synthesis and optimization of PCPDTBT    61
3.4 Characterization of PCPDTBT    68
1H NMR spectroscopies    68
MALDI-TOF mass spectroscopy    69
UV-vis spectroscopy    70
3.5 Synthesis of other low bandgap conjugated polymers    71
3.6 OPV characteristics    73
Conclusion    75
References    76
Chapter 4
Synthesis of CPDT based low bandgap conjugated polymers: facile control of optical and electronic properties and their photovoltaic characteristics
Introduction    77
Results and Discussion    80
4.1 Preparation of materials    80
Monomer synthesis    80
Polymer synthesis    95
4.2 Optical properties    103
4.3 Electrochemical properties    106
4.4 OPV characteristics    108
Conclusion    110
References    111
Chapter 5
Cyclopentadithiophene-benzothiadiazole copolymers with various lengths of repeating unit; synthesis, optical and electrochemical properties and photovoltaic characteristics
Introduction    112
Results and Discussion    114
5.1 Preparation of materials    114
Synthesis of monomers    114
Synthesis of polymers    125
5.2 Optical properties    130
5.3 Electrochemical properties    133
5.4 Device characteristics    137
SCLC device  characteristics    137
OPV device characteristics    138
Conclusion    140
References    141
Chapter 6
Organic photovoltaics based on a cross linkable PCPDTBT analogue; synthesis, morphological studies, solar cell performance and enhanced lifetime
Introduction    142
Results and Discussion    144
6.1 Preparation of materials and characterization    144
Monomer synthesis    144
Synthesis of polymers    148
1H NMR spectroscopies    150
6.2. FTIR and optical absorption spectra    152
Evidence of crosslinking and the effect of Heck coupling    152
Dependence of insolubility upon ratio of crosslinkable group    154
6.3 Electrical and optical analysis    155
Charge transport properties    155
OPV characteristics    157
6.4 Morphological characterization    161
Atomic force microscopy (AFM)    161
X-ray diffraction (XRD)    162
Grazing incidence small angle X-ray scattering (GISAXS)    163
Conclusion    165
References    166
Chapter 7
A donor-acceptor conjugated BCP of poly(arylenevinylene)s by ring-opening metathesis polymerization
Introduction    167
7.1 Conjugated block copolymers    167
7.2 Ring-opening metathesis polymerization (ROMP)    169
Results and discussion    171
7.3 Synthesis and characterization    171
Monomers    171
Homopolymers    181
Block copolymers    185
7.4 Optical properties    188
7.5 Electrochemical properties    190
Conclusion    192
References    193
Chapter 8
Supporting information
Experimental section for chapter 2    195
8.1 General methods    195
8.2 Synthesis of oligomers     196
8.3 1H and 13C and DEPT and 1H-1H NOESY NMR and ESI mass spectra    200
8.4 OFET devices    208
8.5 OPV devices    209
8.6 X-ray single crystallographic data    214
8.7 Other data    214
Experimental section for chapter 3    218
8.8 General methods    218
8.9 Synthesis of PCPDTBTs    219
8.10 Synthesis of related small molecules    222
8.11 Reactants, yield and characterization of other polymers    226
8.12 1H and 13C NMR spectra    227
8.13 Other data    235
Experimental section for chapter 4    238
8.14 General methods    238
8.15 Synthesis of monomers    239
8.16 Synthesis of polymers    242
Experimental section for chapter 5    254
8.17 General methods     254
8.18 Synthesis of monomers    255
8.19 Synthesis of polymers    258
Experimental section for chapter 6    262
8.20 General procedures    262
8.21 Synthesis of materials    263
8.22 GISAXS measurement    275
8.23 Fabrication of Space-Charge Limited Current (SCLC) devices     275
8.24 Fabrication of OPVs     276
8.25 Other data    278
Experimental section for chapter 7    280
8.26 General methods    280
8.27 Synthesis of materials    281
Synthesis of monomers    281
Synthesis of polymers    294
8.28 1H and 13C and 1H-13C HSQC NMR and ESIMS spectra    297
CPDT-based compounds    297
TBT-based compounds    315
Polymers    329
8.29 GPC traces    333
8.30 Crystallographic data    334

                                

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