Synthesis and Properties of Low-Bandgap Copolymer Based on Fluorine Substituted Benzoimidazole for Polymer Solar Cells
- Abstract
- 에너지 소비가 급속하게 늘어남에 따라 지구온난화 등의 환경문제가 발생함으로 인해 대체에너지의 필요성이 대두되고 있으며 새로운 에너지원 개발은 필수불가결한 상황이다. 그 중 에너지 자원이 가장 많은 태양전지에 관한 연구가 진행되어 오고 있다. 기존의 실리콘 태양전지의 경우 비싼 제조원가로 인해 상대적으로 저렴한 유기태양전지의 연구가 집중되고 있는 가운데 최근 10% 이상의 에너지 전환효율을 가지면 상용화까지 가능하다고 알려져 있다. 최근 electron-donor와 electron-acceptor가 active layer에서 마구잡이로 blend 되어 있는 형태의 bulk-heterojunction 기법을 통해 에너지 전환효율이 8%이상을 띄는 물질들이 개발이 되어 오고 있다. 이렇게 에너지 전환효율을 높이기 위한 방법으로는 low-bandgap 물질의 합성, 디바이스 측면에서의 tandem 유기태양전지 등의 연구가 진행되고 있다. 본 연구에서는 electron-acceptor로 사용되고 있는 benzoimidazole에 fluorine을 도입한 새로운 low-bandgap 물질의 합성에 초점을 두었다. Fluorine이 가지는 electron-withdrawing 효과로 인해 conjugated polymer의 HOMO 에너지와 LUMO 에너지를 더 낮게하여 새로운 low-bandgap의 고분자를 합성하였고 이로 인해 고분자 물성의 향상과 이를 디바이스 적용시 높은 에너지 전환효율을 기대할 수 있다.
- Issued Date
- 2014
- Awarded Date
- 2014. 2
- Type
- Dissertation
- Publisher
- 부경대학교
- Affiliation
- 대학원
- Department
- 대학원 공업화학과
- Advisor
- 진영읍
- Table Of Contents
- Contents
Contents ………………………………….………….…………………………... I
List of Figures ………….………………….....………….………………...…... VI
List of Tables ……………….……………………….………………...……... VII
List of Schemes ……………………………………….……..………………..VII
Abstract …………………………………………………………………………IX
Chapter I. Introduction………………………………………………………..….1
I-1. The Background of Polymer solar cells (PSCs)………………….……..…... 1
I-2. Operating Principles of PSCs …….……………………………………...…. 4
I-3. Device structures of PSCs ….…….……………………………………...…...5
I-4. Parameters of PSCs ….………...……………………………………...….......7
I-5. Requirements for Materials in PSCs …………………………………...…….8
I-6. The Methods of Synthesis …………………………………………………..10
I-6-1. Stille Coupling Reaction ...…………………………………………… 10
I-6-2. Grignard Metathesis (GRIM) reactions Preparation of monomer….… 11
Chapter II. Results and Discussion ……………………….……………………. 13
II-1. Synthesis and Characterization..……………………………………….…. 13
II-1-1. Preparation of monomer...…………………………………………… 13
II-1-1-1. Preparation of 2,6-dibromo-4,8-bis((2-octyldodecyl)oxy)benzo[1,2
-b:4,5-b']dithiophene……………………………….………………………..13
II-1-1-2. Preparation of 4, 8-bis(octyloxy)benzo[1,2-b:4,5-b']dithiophene..16
II-1-1-3. Preparation of 4,7-dibromo-5,6-difluoro-2,2-dimethyl-2H-benzo[d]imidazole ………………………………………………………….17
II-1-1-4. Preparation of 5,8-dibromo-6,7-difluoro-2,3-dihexylquinoxaline…20
II-1-1-5. Preparation of 2,5-bis(trimethylstannyl)thiophene………………...21
II-1-2. Preparation of polymer……………………………………………….. 22
II-1-2-1. Preparation of poly[6,7-difluoro-2,3-dihexyl-5-methyl-8-(5- methylthiophen-2-yl)] ………………………………..……………..……….22
II-1-2-2. Preparation of poly[5,6-difluoro-2,2,4-trimethyl-7-(6-methyl-4,
8-bis(octyloxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)-2H-benzo[d]imidazole]
………...…………………………………….………………..……..……….23
II-1-2-3. Preparation of poly[5,6-difluoro-2,2,4-trimethyl-7-(6-methyl-4,8-bis((2-octyldodecyl)oxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)-2H benzo[d]imidazole] …………………………………………..……..……….24
II-1-2-4. Preparation of poly[5,6-difluoro-2,2-dimethyl-4-(5-(6-methyl-4,8-bis((2-octyldodecyl)oxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)thiophen-2-yl)-7-(5-methylthiophen-2-yl)-2H-benzo[d]imidazole]…………...………………26
II-2. Characterization of the Polymers…………………………………………28
II-3. Optical Properties of the Polymer…………………………………………32
II-4. Electrochemical Properties of the Polymer………….……………………. 36
II-5. Photovoltaic Properties of the Polymer……………………………………38
Chapter III. Conclusions………………………………………………………41
Chapter IV. Experimental………………………………………………………. 42
IV-1. Synthesis of donor monomer………………………………………….. 44
IV-1-1. Synthesis of thiophene-3-carbonyl chloride ………………………… 44
IV-1-2. Synthesis of N,N-diethylthiophene-3-carboxamide ………………… 44
IV-1-3. Synthesis of 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophen-4,8-dione….. 45
IV-1-4. Synthesis of 2-octyl-1-dodecyliodide ….………………………….… 46
IV-1-5. Synthesis of 4,8-Bis(2-octyldodecyloxy)benzo[1,2-b:3,4-b]dithiophene ….…………………………………………………………………………..… 46
IV-1-6. Synthesis of 2,6-dibromo-4,8-di(2-octyldodecylloxy)benzo[1,2-b;3,4-b]dithiophene ….……………………………………………………..……… 47
IV-1-7. Synthesis of 2,6-Bis(trimethyltin)-4,8-bis(2-octyldodecyloxy)benzo[1,2-b:3,4-b′]dithiophene… …………...……………..48
IV-1-8. Synthesis of 4,8-Bis(2-octyloxy)benzo[1,2-b:3,4-b]dithiophene …… 49
IV-1-9. Synthesis of 4,8-Bis(octyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane)…………………………………………………... 50
IV-1-10. Synthesis of 2,5-bis(trimethylstannyl)thiophene….…………….… 51
IV-2. Synthesis of acceptor monomer………………..……………………...…52
IV-2-1. Synthesis of 2,3-Difluoro-1,4-bis-(trimethylsilyl)benzene …..…52
IV-2-2. Synthesis of 1,4-dibromo2,3-Difluoro-benzene….……………..52
IV-2-3. Synthesis of 1,4-dibromo-2,3-difiuoro-5,6-dinitro-benzene..…...53
IV-2-4. Synthesis of 3,6-dibromo-4,5-difluorobenzene-1,2-diamine....…53
IV-2-5. Synthesis of 4,7-dibromo-5,6-difluoro-2,2-dimethyl-2H-benzo[d]imidazole ………………………………………………………….....54
IV-2-6. Synthesis of Tetradecane-7,8-dione…..……………………………... 55
IV-2-7. Synthesis of 5,8-Dibromo-6,7-difluoro-2,3-dihexylquinoxaline ……. 56
IV-3. Synthesis of polymer………………………………...………………….....57
IV-3-1. Synthesis of Preparation of poly[6,7-difluoro-2,3-dihexyl-5-methyl-8-(5-methylthiophen-2-yl)quinoxaline…………………………………...……..57
IV-3-2. Synthesis of Preparation of poly[5,6-difluoro-2,2,4-trimethyl-7-(6-methyl-4,8-bis(octyloxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)-2H-benzo[d]imidazole]…………………………………………………………....57
IV-3-3. Synthesis of Preparation of poly[5,6-difluoro-2,2,4-trimethyl-7-(6-methyl-4,8-bis((2-octyldodecyl)oxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)-2H-benzo[d]imidazole]…………………………………………………………....58
IV-3-4. Synthesis of Preparation of [5,6-difluoro-2,2-dimethyl-4-(5-(6-methyl-4,8-bis((2-octyldodecyl)oxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)thiophen-2-yl)-7-(5-methylthiophen-2-yl)-2H-benzo[d]imidazole] ……..….…………..59
References ……………………………………………………….……………...61
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