Synthesis and Photovoltaic Properties of Novel Thiophene-bridged Quinoxaline-containing D-π-A Type Copolymers
- Abstract
- 최근 환경오염과 에너지 수급문제를 대체하기 위한 친환경적 신 재생 에너지 개발의 필요성이 대두되고 있다. 여러 신 재생 에너지 중에서 태양발전은 무기계 실리콘 재료에 거의 전적으로 의지해오고 있는데, 이러한 실리콘 태양전지는 제조 비용이 높아 원료수급에 대한 경제적인 어려움이 많다. 따라서 저가 소자에 대한 필요성이 대두되고 있는 태양전지 분야에서 장기적으로 경제성이 있는 유기계 재료를 적용함으로써 이러한 문제점을 해결해 줄 수 있다. 유기재료는 무기계 재료에 비해 상대적으로 손쉬운 가공성과 저렴성, 다양성을 갖추고 있을 뿐만 아니라 roll-to-roll 방법이 가능한 flexible 소자의 제작이 가능하므로 전자 소자의 공정을 단순화 하여 제작 단가를 현저하게 낮출 수 있다.
본 연구에서는 태양전지의 구성부분인 active layer에 적용되는 conjugated polymer을 합성하고 연구하였다. 가장 많이 사용되고 있는 Benzothiadiazole (BT)와 유사한 구조를 가지는 quinoxaline (Qx)에 전자를 당기는 치환체로 fluorine을 도입하여 electron-withdrawing 효과에 의한 특성변화를 연구하였고 solubility를 향상시키기 위해 hexyl 또는 dodecyl기를 Qx에 적용시켰다. 이렇게 설계한 퀴녹살린 acceptor와 서로 다른 doner와의 D-A alternating polymerization을 통해 각 도너에 따라 다르게 나타나는 polymer의 태양전지적 특성을 알아 보고자 하였다.
- Issued Date
- 2016
- Awarded Date
- 2016. 2
- Type
- Dissertation
- Keyword
- Polymer Solar Cell
- Publisher
- 부경대학교 대학원
- Affiliation
- 부경대학교 대학원
- Department
- 대학원 공업화학과
- Advisor
- 진영읍
- Table Of Contents
- Chapter I. Introduction ……………………………………………………….1
I-1. The Background of Polymer Solar Cells (PSCs) ……………………..………1
I-2. Operating Principles of PSCs ………………………………………………..3
I-2-1. Absorption of Light and Exciton Generation………………………………4
I-2-2. Exciton Diffusion ………………………………………………………….4
I-2-3. Exciton Dissociation ……………………………………………………….4
I-2-4. Charge Transport ………………………………………………………….5
I-3. Power Conversion Efficiency (PCE) ………………………………………….5
I-4. Strategies to Synthesize Conjugated Polymers for High Performanc ………7
I-4-1. Low-Bandgap Polymer Design…………………………………………….7
I-4-2. Donor-Acceptor (D-A) Alternating Structure………………………………8
I-4-2-1. Selection of Donor Unit in Conjugated Polymer …………………….10
I-4-2-2. Selection of Acceptor Unit in Conjugated Polymer …………………11
I-4-3. Bulk Heterojunction Devices ……………………………………………13
I-5. General Method for Synthesis of Conjugated Polymers ………………………14
I-5-1. Synthesis of Polymers with Suzuki Coupling Reaction …………………14
I-5-2. Synthesis of Polymers with Stille Coupling Reaction ……………………15
Chapter II. Experimental ………………………………………………………16
II-1. Materials and Instruments ……………………………………………………16
II-2. Synthesis of Monomers ……………………………………………………18
II-2-1. Synthesis of Donor Monomers …………………………………………18
II-2-1-1. Synthesis of 4,4'-dibromo-2-nitrobiphenyl …………………………18
II-2-1-2. Synthesis of 2,7-dibromocarbazole …………………………………19
II-2-1-3. Synthesis of octylmagnesium bromide ……………………………19
II-2-1-4. Synthesis of heptadecan-9-ol ………………………………………20
II-2-1-5. Synthesis of 9-heptadecane p-toluenesulfonate ……………………20
II-2-1-6. Synthesis of 2,7-dibromo-9-(heptadec-9-yl)carbazole ……………21
II-2-1-7. Synthesis of 2,7-bis(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolan-2’-
yl)-N-9”-heptadecanylcarbazole ……………………………………22
II-2-2. Synthesis of Acceptor Monomers ………………………………………24
II-2-2-1. Synthesis of benzo[c][1,2,5]thiadiazole ……………………………24
II-2-2-2. Synthesis of 4,7-dibromo-2,1,3-benzothiadiazole .…………….….…24
II-2-2-3. Synthesis of 3,6-dibromo-1,2-benzenediamine ……………………25
II-2-2-4. Synthesis of hexacosane-13,14-dione ………………………………26
II-2-2-5. Synthesis of 5,8-dibromo-2,3-didodecylquinoxaline ………………..26
II-2-2-6. Synthesis of 2,5-dibromo-4-fluoro-nitrobenzene ……………………28
II-2-2-7. Synthesis of N-(2’,5’-dibromo-4’-fluorophenyl)-2,2,2-
trifluoroacetamide …………………………………………………28
II-2-2-8. Synthesis of N-(2’,5’-dibromo-4’-fluoro-6’-nitrophenyl)-2,2,2-
trifluoroacetamide …………………………………………………29
II-2-2-9. Synthesis of 2,5-dibromo-4-fluoro-6-nitroaniline …………………29
II-2-2-10. Synthesis of 2,5-dibromo-4-fluoro-5,6-benzenediamine …………30
II-2-2-11. Synthesis of 5,8-dibromo-2,3-didodecyl-6-fluoroquinoxaline …….30
II-2-2-12. Synthesis of 2,3-difluoro-1,4-bis-(trimethylsilyl)benzene …………32
II-2-2-13. Synthesis of 1,4-dibromo2,3-difluoro-benzene …………………….32
II-2-2-14. Synthesis of 1,4-dibromo-2,3-difiuoro-5,6-dinitro-benzene ………33
II-2-2-15. Synthesis of 3,6-dibromo-4,5-difluorobenzene-1,2-diamine ……….33
II-2-2-16. Synthesis of 5,8-dibromo-6,7-difluoro-2,3-didodecylquinoxaline …34
II-2-2-17. Synthesis of Tetradecane-7,8-dione ……………………………….34
II-2-2-18. Synthesis of 5,8-Dibromo-6,7-difluoro-2,3-dihexylquinoxaline …35
II-2-2-19. Synthesis of 2,3-didodecyl-5,8-di(thiophen-2-yl)quinoxaline …….37
II-2-2-20. Synthesis of 5,8-bis(5-bromothiophen-2-yl)-2,3-didodecylquinoxaline
………………………………………………………………………37
II-2-2-21. Synthesis of 2,3-didodecyl-6-fluoro-5,8-di(thiophen-2-yl)quinoxaline
………………………………………………………………………38
II-2-2-22. Synthesis of 5,8-bis(5-bromothiophen-2-yl)-2,3-didodecyl-6-
fluoroquinoxaline …………………………………………………39
II-2-2-23. Synthesis of 2,3-didodecyl-6,7-difluoro-5,8-di(thiophen-2-
yl)quinoxaline ……………………………………………………39
II-2-2-24. Synthesis of 5,8-bis(5-bromothiophen-2-yl)-2,3-didodecyl-6,7-
difluoroquinoxaline ………………………………………………40
II-2-2-25. Synthesis of 6,7-difluoro-2,3-dihexyl-5,8-di(thiophen-2-yl)
quinoxaline ………………………………………………………41
II-2-2-26. Synthesis of 5,8-bis(5-bromothiophen-2-yl)-6,7-difluoro-2,3-
dihexylquinoxaline ………………………………………………42
II-2-2-27. Synthesis of tributyl(thiophen-2-yl)stannane ………………………42
II-3. Synthesis of Polymers ………………………………………………………44
II-3-1. Synthesis of Poly[2-(5-(2,3-didodecyl-8-(5-phenylthiophen-2-yl)
quinoxalin-5-yl)thiophen-2-yl)-9-(heptadecan-9-yl)-7-phenyl-9H-
carbazole] (YJ-35) ………………………………………………………44
II-3-2. Synthesis of Poly[2-(5-(2,3-didodecyl-7-fluoro-8-(thiophen-2-yl)
quinoxalin-5-yl)thiophen-2-yl)-9-(heptadecan-9-yl)-9H-
carbazole] (YJ-36) ………………………………………………………46
II-3-3. Synthesis of poly[2-(5-(2,3-didodecyl-6,7-difluoro-8-(thiophen-2-yl)
quinoxalin-5-yl)thiophen-2-yl)-9-(heptadecan-9-yl)-9H-
carbazole] (YJ-37) ………………………………………………………48
II-3-4. Synthesis of poly[5-(5-(4,8-bis((2-butyloctyl)oxy)benzo[1,2-b:4,5-b']
dithiophen-2-yl)thiophen-2-yl)-6,7-difluoro-2,3-dihexyl-8-(thiophen-2-yl)
quinoxaline] (YJ-38) ……………………………………………………50
II-3-5. Synthesis of poly[5-(5-(4,8-bis((2-butyloctyl)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-39) …………………………………………………52
II-3-6. Synthesis of poly[2,3-didodecyl-6,7-difluoro-5-(4,4,9,9-tetrakis(4-hexylphenyl)-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophen-2-yl)
quinoxaline] (YJ-49) ……………………………………………………54
II-3-7. Synthesis of poly[2,3-didodecyl-6,7-difluoro-5-(5-(4,4,9,9-tetrakis(4-hexylphenyl)-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophen-2-yl)
thiophen-2-yl)-8-(thiophen-2-yl)quinoxaline] (YJ-50) …………………56
Chapter III. Results and Discussion …………………………………………….58
III-1. Physical Properties …………………………………………………………58
III-2. Optical Properties ……………………………………………………………60
III-3. Electrochemical Properties …………………………………………………67
III-4. Photovoltaic Properties ……………………………………………………...69
Chapter IV. Conclusions …………………………………………………………75
References ………………………………………………………………………76
- Degree
- Master
- Files in This Item:
-
-
Download
Synthesis and Photovoltaic Properties of Novel Thiophene-bridged Quinoxaline-containing D-π-A Type C.pdf
기타 데이터 / 1.3 MB / Adobe PDF
-
Items in Repository are protected by copyright, with all rights reserved, unless otherwise indicated.