Synthesis and Characterization of Alternating D-A type Conjugated Polymer Containing Fluorinated Quinoxaline for Polymer Solar Cells
- Abstract
- 고분자 태양전지는 유연성을 가질 수 있고, 저가격 대면적의 용액공정을 할 수 있다는 장점을 가지고 있어 대체 에너지원으로 고려되어 많은 연구가 진행되고 있다. 최근 연구에서 단일층의 bulkheterojunction(BHJ) 고분자 태양전지의 효율은 8% 이상까지 보고되었다. 고 효율을 나타내는 태양전지에서 고분자는 빛의 흡수량을 늘리기 위해 좁은 밴드갭을 가져야 하며, 효과적인 전하분리를 위해 acceptor물질과 에너지레벨의 차이가 적당해야 하고, 분자 내 전하이동을 높이기 위해 donor-acceptor(D-A)구조의 고분자를 합성해야 한다.
본 연구에서는 액티브레이어에서 electron-acceptor로 가장 많이 사용되고 있는 BT와 유사한 구조를 가지는 quinoxaline에 치환기로 fluorine을 1개 또는 2개를 도입하였고 solubility를 증가시키기 위해 2개의 dodecyl기를 도입한 새로운 acceptor 단량체를 디자인하였고, 그를 포함하는 새로운 고분자를 합성하였다. 이를 통해 fluorine이 가지는 electron-withdrawing 효과가 태양전지에 나타나는 특성변화를 관찰하였다.
- Issued Date
- 2015
- Awarded Date
- 2015. 2
- Type
- Dissertation
- Publisher
- Pukyong National University
- Affiliation
- Department of Industrial chemistry, Pukyong National University
- Department
- 대학원 공업화학과
- Advisor
- Youngeup jin
- Table Of Contents
- Contents
Contents .………………………………………………………………………......…i
List of Figures .……………………………………….………………………….....vii
List of Tables ….………………………….………….………………………...........x
List of Schemes .……………………………………..……………………………...xi
Abstract ……………………………………………..……………………………...xii
Chapter I. Introduction ……………………………………………………….1
I-1. Background of Polymer Solar Cells (PSCs) ……………………..………1
I-2. Operating Principles of PSCs ………………………………………………..3
I-3. Device Structures of PSC …………………………………………………….....4
I-3-1. Bilayer Devices ………………………………………………………….4
I-3-2. Bulk Heterojunction Devices ………………...………………………….4
I-4. Parameters of PSCs ……………………………………………………………..7
I-4-1. Open-Circuit Voltage (Voc) …………………………………………………7
I-4-2. Short-Circuit Current Density (Jsc) …………………………………………8
I-4-3. Fill Factor (FF) …………………………………………………………......9
I-4-4. Requirements for Materials in PSCs ……………………………………….9
I-5. Strategies to Synthesize Conjugated Polymers for High Performance ………..10
I-5-1. Donor-Acceptor (D-A) Alternating Structure ……………………………..10
I-5-1-1. Selection of Donor Unit in Conjugated Polymer ……………………..13
I-5-1-2. Selection of Acceptor Unit in Conjugated Polymer …………………….13
I-5-2. Effects of Substitution Introduced in Conjugated Backbone ……………15
I-6. General Method for Synthesis of Conjugated Polymers ………………………16
Chapter II. Experimental …………………………………………………….......18
II-1. Materials and Instruments …………………………………………………….18
II-2. Synthesis of monomers ……………………………………………………20
II-2-1. Synthesis of donor monomers ……………………………………………20
II-2-1-1. Synthesis of 2,5-bis(trimethylstannyl)thiophene …………………20
II-2-1-2. Synthesis of thiophene-3-carbonyl chloride …………………..….20
II-2-1-3. Synthesis of N,N-diethylthiophene-3-carboxamide ………………21
II-2-1-4. Synthesis of benzo[1,2-b:4,5-b']dithiophene-4,8-dione .………….22
II-2-1-5. Synthesis of 4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene …….………….………………………………..…..…………………………...22
II-2-1-6. Synthesis of 2,6-bis(trimethyltin)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:3,4-b′]dithiophene ………………………………………………...23
II-2-2. Synthesis of acceptor monomers ................................................................25
II-2-2-1. Synthesis of 2,3-difluoro-1,4-bis-(trimethylsilyl)benzene ..................25
II-2-2-2. Synthesis of 1,4-dibromo2,3-difluoro-benzene ...................................25
II-2-2-3. Synthesis of 1,4-dibromo-2,3-difiuoro-5,6-dinitro-benzene ………...26
II-2-2-4. Synthesis of 3,6-dibromo-4,5-difluorobenzene-1,2-diamine ………...26
II-2-2-5. Synthesis of hexacosane-13,14-dione ………………………………..27
II-2-2-6. Synthesis of 5,8-dibromo-6,7-difluoro-2,3-didodecylquinoxaline …..28
II-2-2-7. Synthesis of 2,5-dibromo-4-fluoro-nitrobenzene …………………....30
II-2-2-8. Synthesis of Synthesis of N-(2’,5’-dibromo-4’-fluorophenyl)-2,2,2-trifluoroacetamide ..............................................................................30
II-2-2-9. Synthesis of N-(2’,5’-dibromo-4’-fluoro-6’-nitrophenyl)-2,2,2-trifluoroacetamide …………………………………………………..31
II-2-2-10. Synthesis of 2,5-dibromo-4-fluoro-6-nitroaniline ………………….31
II-2-2-11. Synthesis of 2,5-dibromo-4-fluoro-5,6-benzenediamine …………...32
II-2-2-12. Synthesis of 5,8-dibromo-2,3-didodecyl-6-fluoroquinoxaline ..........32
II-2-2-13. Synthesis of tributyl(thiophen-2-yl)stannane ………………………35
II-2-2-14. Synthesis of 2,3-didodecyl-6,7-difluoro-5,8-di(thiophen-2-yl)quinoxaline ……………………………………………………….35
II-2-2-15. Synthesis of 5,8-bis(5-bromothiophen-2-yl)-2,3-didodecyl-6,7-difluoroquinoxaline …………………………………………………36
II-2-2-16. Synthesis of 2,3-didodecyl-6-fluoro-5,8-di(thiophen-2-yl)quinoxaline ……………………………………………………………………….36
II-2-2-17. Synthesis of 5,8-bis(5-bromothiophen-2-yl)-2,3-didodecyl-6-fluoroquinoxaline …………………………………………………...37
II-3. Synthesis of polymers ………………………………………………………...39
II-3-1. Synthesis of poly[2,3-didodecyl-6,7-difluoro-5-(thiophen-2-yl)quinoxaline] (YJ-20) …………………………………………………………………...39
II-3-2. Synthesis of poly[2,3-didodecyl-7-fluoro-5-(thiophen-2-yl)quinoxaline] (YJ-21) …………………………………………………………………...41
II-3-3. Synthesis of poly[5-(4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)-2,3-didodecyl-6,7-difluoroquinoxaline] (YJ-22) …...43
II-3-4. Synthesis of poly[5-(4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)-2,3-didodecyl-7-fluoroquinoxaline] (YJ-23) ……….45
II-3-5. Synthesis of poly[5-(5-(4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)thiophen-2-yl)-2,3-didodecyl-6,7-difluoro-8-(thiophen-2-yl)quinoxaline] (YJ-24) ………………………………………………..47
II-3-6. Synthesis of poly[8-(5-(4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)thiophen-2-yl)-2,3-didodecyl-6-fluoro-5-(thiophen-2-yl)quinoxaline] (YJ-25) ………………………………………………….49
Chapter III. Results and Discussion …………………………………………….51
III-1. Polymerization results ……………………………………………………….51
III-2. Optical Properties of Polymers ………………………………………………53
III-3. Electrochemical Properties of Polymers ……………………………………59
III-4. Photovoltaic Properties of Polymers ………………………………………...61
III-5. Film morphology analysis …………………………………………………...67
Chapter IV. Conclusions …………………………………………………………70
References ………………………………………………………………………….72
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