Synthesis and photovoltaic properties of π-conjugated polymers based on benzimidazole, arylene imide and benzooxadiazole for polymer solar cells
- Abstract
- 지난 10년 동안, 유기태양전지의 활성층으로 높은 전하 이동도를 가지는 regioregular poly(3-hexylthiophene) (rr-P3HT)가 많이 사용되었다. 그러나 rr-P3HT는 큰 band-gap을 가져 유기태양전지의 활성층으로 사용하기에 이상적인 물질이 아니다. 보다 많은 광자를 얻고, 에너지 준위를 조절하기 위한 시도 중의 하나는, main chain을 전자가 풍부한 unit (donor)과 전자가 부족한 unit (acceptor) 을 이용하여 conjugated 형태의 공중합체를 합성하는 것이다.
본 논문에서, 2-aryl benzimidazole (IMD), arylene imide (TI24T), 또는 2,1,3-benzooxadiazole (BO20) 유도체를 acceptor로 사용하여 작은 band-gap을 가지는 고분자를 합성하였다. POFTBT-IMD는 2-aryl benzimidazole 유도체를 포함하는 4,7-dithiophen-2-yl-benzo(2,1,3)thiadiazole (TBT)와 높은 용해도를 가지는 fluorene 유도체를 Suzuki coupling 중합법으로 중합하였다. 또한 arylene imide/2,1,3-benzooxadiazole 유도체와 thiophene/dithiophene을 Stille coupling 중합법을 이용하여, T-TI24T, 1T-BO20, 2T-BO20, 3T-BO20를 중합하였다. 합성된 고분자는 chloroform, chlorobenzene, dichlorobenzene, toluene과 같은 일반적인 유기용매에 대해 우수한 용해도를 가지며, UV-Vis spectrum과 순환 전압 전류법 (cyclic voltammetry, CV)으로 1.6-2.3 eV 정도의 광학적, 전기화학적 band-gap을 가지는 것을 확인하였다. 그리고 비교적 낮은 호모 (low highest occupied molecular orbital, HOMO) 에너지 준위와 태양전지에 적용하기 적합한 에너지 준위를 가지는 것을 확인하였다. 합성된 T-TI24T, 1T-BO20, 2T-BO20, 3T-BO20를 bulk hetero junction (BHJ) 구조의 태양전지의 활성층으로 적용하여 소자를 제작하였다.
- Issued Date
- 2013
- Awarded Date
- 2013. 2
- Type
- Dissertation
- Publisher
- 부경대학교
- Affiliation
- 부경대학교 대학원
- Department
- 대학원 고분자공학과
- Advisor
- 김주현
- Table Of Contents
- Contents
List of Figures
List of Tables
List of Schemes
Abstract
Chapter I. Introduction
I-1. Basic processes in organic solar cells (OSCs)
I-1-1. Absorption of photons
I-1-2. Exciton diffusion
I-1-3. Charge separation
I-1-4. Charge transport
I-1-5. Charge collection
I-2. Device Architecture
I-2-1. Single layer
I-2-2. Bilayer heterojunction
I-2-3. Bulk heterojunction (BHJ)
I-2-4. Diffuse bilayer heterojunction
I-3. Donor and acceptor materials for OSCs
I-3-1. Donor (p-type material)
I-3-2. Acceptor (n-type material)
I-4. Solar cell parameters
I-4-1. Open circuit voltage (Voc)
I-4-2. Short-circuit current (Jsc )
I-4-3. Fill factor (FF)
I-4-4. Incident photon to current efficiency (IPCE)
I-4-5. Power conversion efficiency (ηp)
I-5. Factors affect the efficiency of OSCs
I-5-1. Solvent, concentration and active layer thickness
I-5-2. Ratio between polymer and fullerene
I-5-3. Annealing temperature
I-5-4. Molecular weight
I-5-5. Processing additives
I-5-6. Other factors
I-6. Low Band gap Polymers
Chapter II. Synthesis and Characterization of -Conjugated Polymers Based on 2-Arylbenzimidazole and 4,7-Di-2-thienyl-2,1,3-benzothiadiazole
II-1. Introduction
II-2. Experimental Section
II-2-1. Materials and Synthesis
II-2-1-1. 3,6-Dibromo-benzene-1,2-diamine (1)
II-2-1-2. 4,7-Dibromo-2-(4-tert-butyl-phenyl)-1H-benzoimidazole (2)
II-2-1-3. 4,7-Dibromo-2-(4-tert-butyl-phenyl)-1-ethyl-1H-benzoimidazole (3)
II-2-1-4. 2-(4-tert-butyl-phenyl)-1-ethyl-4,7-di-thiophen-2-yl-1H-benzoimidazole (4)
II-2-1-5. 4,7-Bis-(5-bromo-thiophen-2-yl)-2-(4-tert-butyl-phenyl)-1-ethyl-1H-benzoimidazole (5)
II-2-1-6. Synthesis of Polymers POFTBT-IMD
II-2-2. Measurement
II-3. Results and Discussion
II-3-1. Thermal Properties
II-3-2. Optical Properties
II-3-3. Electrochemical Properties
II-4. Conclusions
Chapter III. Synthesis and Characterization of π-Conjugated Polymer Based on Arylene Imide for Organic Solar Cells
III-1. Introduction
III-2. Experimental Section
III-2-1. Materials and Synthesis
III-2-1-1. 1,2-Bis-decyloxy-benzene (1)
III-2-1-2. 1,2-Diiodo-4,5-bis-decyloxy-benzene (2)
III-2-1-3. 1,2-Dicyano-4,5-bis-decyloxy-benzene (3)
III-2-1-4. 4,5-Bis-decyloxy-phthalic acid (4)
III-2-1-5. 2-Butyl-5,6-bis-decyloxy-isoindole-1,3-dione (5)
III-2-1-6. 4,7-Dibromo-2-butyl-5,6-bis-decyloxy-isoindole-1,3-dione (6)
III-2-1-7. 2-Butyl-5,6-bis-decyloxy-4,7-di-thiophen-2-yl-isoindole-1,3-dione (7)
III-2-1-8. 4,7-Bis-(5-bromo-thiophen-2-yl)-2-butyl-5,6-bis-decyloxy-isoindole-1,3-dione (8)
III-2-1-9. Synthesis of Polymer T-TI24T
III-2-2. Fabrication of Device
III-2-3. Measurement
III-3. Results and Discussion
III-3-1. Thermal Properties
III-3-2. Optical Properties
III-3-3. Electrochemical Properties
III-3-4. Photovoltaic Properties
III-4. Conclusion
Chapter IV. Synthesis, Characterization and photovoltaic properties of π-Conjugated Polymers Based on Thiophene and 2,1,3-Benzooxadiazole Derivatives for Organic Solar Cells
IV-1. Introduction
IV-2. Experimental Section
IV-2-1. Materials and Synthesis
IV-2-1-1. 1,2-Dinitro-4,5-bis-decyloxy benzene (3)
IV-2-1-2. 5,6-Bis(decyloxy)benzo[c][1,2,5]oxadiazole (4)
IV-2-1-3. 4,7-Dibromo-5,6-bis(decyloxy)benzo[c][ 1,2,5]oxadiazole (5)
IV-2-1-4. 5,6-Bis(decyloxy)-4,7-di(thien-2-yl)benzo[c][1,2,5]oxadiazole (6)
IV-2-1-5.4,7-Bis(5-bromothien-2-yl)-5,6-bis(decyloxy)benzo[c][1,2,5] oxadiazole (7)
IV-2-1-6. Synthesis of polymers (1T-BO20, 2T-BO20 and 3T-BO20)
IV-2-2. Fabrication of Device
IV-2-3. Measurement
IV-3. Results and Discussion
IV-3-1. Thermal Properties
IV-3-2. Optical Properties
IV-3-3. Electrochemical Properties
IV-3-4. Photovoltaic Properties
IV-4. Conclusions
References
Acknowledgment
- Degree
- Master
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