PUKYONG

Design, Synthesis and Photovoltaic Properties of Novel Conjugated Copolymers with Fluorinated Quinoxaline for OPVs

Metadata Downloads
Abstract
지하자원이 점점 고갈됨에 따라 세계 각국에서는 대체 에너지에 대해 관심을 가지고 있다. 그 중 태양 에너지를 이용한 태양전지 같은 경우에는 원자재 값이 들지 않는 장점 때문에 많은 연구가 진행되고 있다. 실리콘을 사용해서 만든 무기태양전지 같은 경우 에너지 변환 효율이 뛰어나지만 가격이 비싸다는 단점을 가지고 있는 반면 유기 태양 전지 같은 경우 저가격 대면적 생산이 가능하고, 유연성을 가질 수 있는 장점을 가지고 있어 가장 각광 받고 있는 분야이다. 최근 연구에 의하면 Bulkheterojunction(BHJ) 고분자 태양전지 같은 경우 10% 이상의 효율을 가지고 있다는 것이 보도되었다. 높은 효율을 내기 위해서는 고분자의 빛의 흡수량을 늘리는 것이 중요하고 이는 고분자가 좁은 밴드갭을 가지고 있어야 한다. 그리하여 본 연구에서는 좁은 밴드갭을 만들기 위해 Electron-acceptor로써 Quinoxaline 유도체를 사용 하였고 이에 치환기로 Fluorine을 0개, 1개 그리고 2개를 도입했다. 또한 Solubility를 높이기 위해 2개의 dodecyl기를 도입했다. 또한 분자 내 전하이동을 높이기 위해 Electron-donor로써 Thiophene 시리즈와 Fluorene과의 D-A Alternating 구조로 합성해 새로운 고분자를 만들었다. 이로 인해 고분자를 이용한 유기태양전지에서 Fluorine을 치환한 Quinoxaline과 Thiophene 그리고 Fluorene의 역할에 대해서 연구를 진행 하였다.
Author(s)
강영권
Issued Date
2016
Awarded Date
2016. 2
Type
Dissertation
Publisher
부경대학교 대학원
URI
https://repository.pknu.ac.kr:8443/handle/2021.oak/12805
http://pknu.dcollection.net/jsp/common/DcLoOrgPer.jsp?sItemId=000002229744
Affiliation
부경대학교 대학원
Department
대학원 공업화학과
Advisor
진영읍
Table Of Contents
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 5
I-3-1. Single layer Polymer Solar Cells 5
I-3-2. Bilayer Device 5
I-3-3. Bulk Heterojunction Polymer Solar Cells 6
I-4. Parameters of PSCs 9
I-4-1. Open-Circuit Voltage (Voc) 9
I-4-2. Short-Circuit Current Density (Jsc) 10
I-4-3. Fill Factor (FF) 11
I-4-4. Requirements for Materials in PSCs 13
I-5. Strategies to Synthesize Conjugated Polymers for High Performance 14
I-5-1. Donor-Acceptor (D-A) Alternating Structure 14
I-5-1-1. Selection of Donor Unit in Conjugated Polymer 17
I-5-1-2. Selection of Acceptor Unit in Conjugated Polymer 18
I-6. General Method for Synthesis of Conjugated Polymers 19
I-6-1. Stille Coupling Reactio 19
I-6-2. Suzuki Coupling Reaction 21
Chapter II. Experimental 23
II-1. Materials and Instruments 23
II-2. Synthesis of monomers 25
II-2-1. Synthesis of donor monomers 25
II-2-1-1. Synthesis of 2,7-dibromofluorene 25
II-2-1-2. Synthesis of 2,7-Dibromo-9,9'dioctyl-9H-fluorene 25
II-2-1-3. Synthesis of 2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)-bis[4,4, 5,5-tetramethyl-[1,3,2]dioxaborolane] 26
II-2-1-4. Synthesis of 2,5-bis(trimethylstannyl)thiophene 28
II-2-1-5. Synthesis of 5,5'-bis(trimethylstannyl)-2,2'-bithiophene 28
II-2-1-6. Synthesis of 2,5-Bis-trimethylstannyl-thieno[3,2-b]thiophene 29
II-2-1-7. Synthesis of Synthesis of 2,5-Dibromothiophene 30
II-2-1-8. Synthesis of tributyl(thiophen-2-yl)stannane 30
II-2-1-9. Synthesis of 2,2':5',2''-terthiophene 31
II-2-1-10. Synthesis of 2,5''-Bis(trimethylsilyl)-5,2',5',2''-terthiophene 31
II-2-2. Synthesis of acceptor monomers 34
II-2-2-1. Synthesis of 2,3-difluoro-1,4-bis-(trimethylsilyl)benzene 34
II-2-2-2. Synthesis of 1,4-dibromo2,3-difluoro-benzene 34
II-2-2-3. Synthesis of 1,4-dibromo-2,3-difiuoro-5,6-dinitro-benzene 35
II-2-2-4. Synthesis of 3,6-dibromo-4,5-difluorobenzene-1,2-diamine 35
II-2-2-5. Synthesis of hexacosane-13,14-dione 36
II-2-2-6. Synthesis of 5,8-dibromo-6,7-difluoro-2,3-didodecylquinoxaline 37
II-2-2-7. Synthesis of 2,5-dibromo-4-fluoro-nitrobenzene 39
II-2-2-8. Synthesis N-(2’,5’-dibromo-4’-fluorophenyl)-2,2,2-trifluoroacetamide 39
II-2-2-9. Synthesis of N-(2’,5’-dibromo-4’-fluoro-6’-nitrophenyl)-2,2,2-trifluoroacetamide 40
II-2-2-10. Synthesis of 2,5-dibromo-4-fluoro-6-nitroaniline 40
II-2-2-11. Synthesis of 2,5-dibromo-4-fluoro-5,6-benzenediamine 41
II-2-2-12. Synthesis of 5,8-dibromo-2,3-didodecyl-6-fluoroquinoxaline 41
II-2-2-13. Synthesis of benzo[c][1,2,5]thiadiazole 44
II-2-2-14. Synthesis of 4,7-Dibromo-2,1,3-benzothiadiazol 44
II-2-2-15. Synthesis of 3,6-dibromo-1,2-benzenediamine 45
II-2-2-16. Synthesis of Synthesis of 5,8-dibromo-2,3-didodecylquinoxaline 45
II-2-2-17. Synthesis of 2,3-didodecyl-6,7-difluoro-5,8-di(thiophen-2-yl)quinoxaline 47
II-2-2-18. Synthesis of 5,8-bis(5-bromothiophen-2-yl)-2,3-didodecyl-6,7-difluoroquinoxaline 47
II-2-2-19. Synthesis of 2,3-didodecyl-6-fluoro-5,8-di(thiophen-2-yl)quinoxaline 48
II-2-2-20. Synthesis of 5,8-bis(5-bromothiophen-2-yl)-2,3-didodecyl-6-fluoroquinoxaline 49
II-2-2-21. Synthesis of 2,3-didodecyl-5,8-di(thiophen-2-yl)quinoxaline 49
II-2-2-22. Synthesis of 5,8-bis(5-bromothiophen-2-yl)-2,3-didodecylquinoxaline 50
II-2-2-23. Synthesis of 3-hexylthiophene 52
II-2-2-24. Synthesis of 4-hexylthiophen-2-yl)trimethylstannane 52
II-2-2-25. Synthesis of 2,3-didodecyl-6,7-difluoro-5,8-bis(4-hexylthiophen-2-yl)quinoxaline 53
II-2-2-26. Synthesis of Synthesis of 5,8-bis(5-bromo-4-hexylthiophen-2-yl)-2,3-didodecyl-6,7-difluoroquinoxaline 54
II-2-2-27. Synthesis of 2,3-didodecyl-6-fluoro-5,8-bis(4-hexylthiophen-2-yl)quinoxaline 54
II-2-2-28. Synthesis of 5,8-bis(5-bromo-4-hexylthiophen-2-yl)-2,3-didodecyl-6-fluoroquinoxaline 55

II-3. Synthesis of polymers 57
II-3-1. Synthesis of poly[2,3-didodecyl-6,7-difluoro-5-(3-hexyl-[2,2'-bithiophen]-5-yl)-8-(4-hexylthiophen-2-yl)quinoxaline] (YJ-26) 57
II-3-2. Synthesis of poly[2,3-didodecyl-6-fluoro-8-(3-hexyl-[2,2'-bithiophen]-5-yl)-5-(4-hexylthiophen-2-yl)quinoxaline] (YJ-27) 57
II-3-3. Synthesis of poly[2,7-dibromo-9,9-dioctyl-9H-fluorene-co-5,8-Dibromo-6,7-difluoro-2.3-didodecylquinoxaline] (YJ-28 to YJ- 31) 59
II-3-4. Synthesis of poly[5-(5-(9,9-dioctyl-9H-fluoren-2-yl)thiophen-2-yl)-2,3-didodecyl-6,7-difluoro-8-(thiophen-2-yl)quinoxaline] (YJ-32) 60
II-3-5. Synthesis of poly[5-([2,2':5',2''-terthiophen]-5-yl)-2,3-didodecyl-7-fluoroquinoxaline] (YJ-40 to YJ-42) 62
II-3-6. Synthesis of poly[5-([2,2':5',2''-terthiophen]-5-yl)-2,3-didodecyl-6,7-difluoroquinoxaline] and poly[5-([2,2':5',2''-terthiophen]-5-yl)-2,3-didodecylquinoxaline] (YJ-33 to YJ-34) 62
II-3-7. Synthesis of poly[5-([2,2'-bithiophen]-5-yl)-2,3-didodecyl-6,7-difluoroquinoxaline] (YJ-43) 65
II-3-8. Synthesis of poly[5-([2,2'-bithiophen]-5-yl)-2,3-didodecyl-7-fluoroquinoxaline] (YJ-44) 65
II-3-9. Synthesis of poly[2,3-didodecyl-6,7-difluoro-5-(thieno[3,2-b]thiophen-2-yl)quinoxaline] (YJ-45) 67
II-3-10. Synthesis of poly[2,3-didodecyl-7-fluoro-5-(thieno[3,2-b]thiophen-2-yl)quinoxaline] (YJ-46) 67
II-3-11. Synthesis of poly[2,3-didodecyl-6,7-difluoro-5-(5-(thieno[3,2-b]thiophen-2-yl)thiophen-2-yl)-8-(thiophen-2-yl)quinoxaline] (YJ-47) 69
II-3-12. Synthesis of poly[2,3-didodecyl-6-fluoro-8-(5-(thieno[3,2-b]thiophen-2-yl)thiophen-2-yl)-5-(thiophen-2-yl)quinoxaline] (YJ-48) 69
Chapter III. Results and Discussion 71
III-1. Polymerization results 71
III-2. Optical Properties of Polymers 77
III-3. Electrochemical Properties of Polymers 84
III-4. Photovoltaic Properties of Polymers 90
Chapter IV. Conclusions 96
References 98
Degree
Master
Appears in Collections:
대학원 > 공업화학과
Authorize & License
  • Authorize공개
Files in This Item:

Items in Repository are protected by copyright, with all rights reserved, unless otherwise indicated.