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Diketopyrrolopyrrole 과 Silofulorene을 기본 골격으로 하는 낮은 밴드갭을 가지는 소재의 합성과 태양전지 적용

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Alternative Title
Synthesis of low band gap materials based on diketopyrrolopyrrole and Silofulorene and their application of solar cells
Abstract
Recently, there are many researches focus on finding another energy source since fossil fuel will be depleted. Organic solar cells (OSCs) are one of the candidates for alternative energy source by using solar energy. Herein we synthesize new small molecules and polymers based on diketopyrrolopyrrole (DPP) or Silafluorene (SiF) by using Suzuki coupling reaction. All of small molecules and polymers were soluble in common organic solvents such as chloroform, methylene chloride, ethyl acetate, toluene, chlorobenzene, dichlorobenzne and tetrahydrofurane. The band gap of small molecules and polymers were estimated UV-Vis spectroscopy and cyclic voltammogram between 1.44 ~ 2.10 eV. New small molecules and polymers were show broad absorption regions and had proper energy level to apply OSCs. The bulk hetero junction type organic photovoltaic cells were fabricated from polymer [ITO/PEDOT:PSS/Small molecules or Polymers:PCBM/Al]. In this thesis, we report the characterization of photovoltaic properties with new -conjugation material and application to OSCs.
Author(s)
박종현
Issued Date
2015
Awarded Date
2015. 2
Type
Dissertation
Publisher
부경대학교
URI
https://repository.pknu.ac.kr:8443/handle/2021.oak/11837
http://pknu.dcollection.net/jsp/common/DcLoOrgPer.jsp?sItemId=000001967456
Affiliation
부경대학교
Department
대학원 고분자공학과
Advisor
김주현
Table Of Contents
Contents ………………………………………………………………………. I
List of Figures ……………………………………………………………. XV
List of Tables ..………………………………………………………. XVIII
List of Schemes ……………………………………………………… XVIII
Abstract ………………………………………………………………… XIX



Chapter I. 서론 ……………………………………………………………… 1


I-1. 태양전지의 연구배경………………………………………………….. 1

I-2. 태양전지의 발전 ..........………………………………………………. 2
I-3. 유기태양전지의 구조 …………………………………………………. 7

I-4. 유기태양전지의 작동 메커니즘 …………………………………. 11
I-4-1. 태양빛의 흡수와 액시톤의 생성 ………………………………11
I-4-2. 액시톤 확산 및 분리 ………………..………………………….12
I-4-3. 전하의 이동과 수집 …………………………………………….13

I-5. 유기태양전지의 특성 …………………………………………………15
I-5-1. 단락전류 (Short Circuit Current: Jsc) ………………….....15
I-5-2. 개방전압 (Open Circuit Current: Voc) …………………….15
I-5-3. 충진지수 (Fill Factor: FF) ………………………………..…17



Chapter II. Diketopyrrolopyrrole을 기본 골격으로 한 낮은 band gap을 가지는 공액형 저분자 합성 및 특성 평가 …………………… 19


II-1. 서론 ……………………………………………………………………19

II-2. 실험 ……………………………………………………………………22
II-2-1. 시약 ………………..…………………………………………. 22
II-2-2. 전자받개 물질 합성 ……..…………………………………. 22
II-2-2-1. Toluene-4-sulfonic acid 2-butyl-octyl ester의 합성 (1) ………………………………………………… 22
II-2-2-2. Toluene-4-sulfonic acid 2-octyl-dodecyl ester의 합성 (2) ………………………………………………… 23
II-2-2-3. 3,6-Di-thiophen-2-yl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione (DPP)의 합성 (3) ………………………………………………………… 24
II-2-2-4. 2,5-Bis-(2-butyl-octyl)-3,6-di-thiophen-2-yl-2,5-dihydro-pyrrolo [3,4-c]pyrrole-1,4-dione 의 합성 (4) …………………………………….. 25
II-2-2-5. 2,5-Bis-(2-octyl-dodecyl)-3,6-di-thiophen-2-yl-2,5-dihydro-pyrrolo [3,4-c]pyrrole-1,4-dione 의 합성 (5) …………………………………….. 26
II-2-2-6. 3,6-Bis-(5-bromo-thiophen-2-yl)-2,5-bis-(2-butyl-octyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 의 합성 (6) ……………….. 27
II-2-2-7. 3,6-Bis-(5-bromo-thiophen-2-yl)-2,5-bis-(2-octyl-dodecyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 의 합성 (7) ………………. 28

II-2-3. 전자주개 물질 합성 …………………………………………. 30
II-2-3-1. 2-Anthracen-9-yl-4,4,5,5-tetramethyl-[1,3,2]
Dioxaborolane의 합성 (8) ………………………….. 30
II-2-3-2. 9-(4-Bromo-phenyl)-9H-carbazole의 합성 (9) …………………………………..………………………… 31
II-2-3-3. 9-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-9H-carbazole의 합성 (10) ………………………………… 32
II-2-3-4. 3-Bromo-perylene의 합성 (11) ………………... 33
II-2-3-5. 4,4,5,5-Tetramethyl-2-perylen-3-yl-[1,3,2]
dioxaborolane의 합성 (12)………………………... 33
II-2-3-6. Trimethyl-perylen-3-ylethynyl-silane의 합성 (13) ……………………………………………………… 34
II-2-3-7. 3-Ethynyl-perylene의 합성 (14) ………………. 35

II-2-4. D-A-D 구조를 가지는 공액형 저분자 합성 …………… 37
II-2-4-1. 3,6-Bis-(5-anthracen-9-yl-thiophen-2-yl)-2,5-bis-(2-butyl-octyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione의 합성 (ANTDPP12) ………………………………………….. 37
II-2-4-2. 2,5-Bis-(2-butyl-octyl)-3,6-bis-[5-(4-carbazol-9-yl-phenyl)-thiophen-2-yl]-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 의 합성 (PCTDPP12)…………………………………….. 38
II-2-4-3. 3,6-Bis-[5-(4-carbazol-9-yl-phenyl)-thiophen-2-yl]-2,5-bis-(2-octyl-tetradecyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 의 합성 (PCTDPP20) ……………………………….. 39
II-2-4-4. 2,5-Bis-(2-butyl-octyl)-3,6-bis-(5-perylen-3-yl-thiophen-2-yl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 의 합성 (PERDPP12) ………………………………………….. 40
II-2-4-5. 2,5-Bis-(2-octyl-tetradecyl)-3,6-bis-(5-perylen-3-yl-thiophen-2-yl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 의 합성 (PERDPP20) ……………………………………………41
II-2-4-6. 2,5-Bis-(2-octyl-dodecyl)-3,6-bis-(5-perylen-3-ylethynyl-thiophen-2-yl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 의 합성 (TPERDPP20) …………………………………...41

II-3. 측정 및 소자 제작 …………………………………………………. 44
II-3-1. 측정 ……………………………………………………………. 44
II-3-1-1. 구조 분석 ………………………………………………. 44
II-3-1-2. 광학적 전기적 특성 분석 ……………………………. 44
II-3-1-3. 광전변환특성 분석 ……………………………………. 45
II-3-2. 소자 제작 …………………………………………………….. 45

II-4. 결과 및 토론…………………………………………………………. 46

II-5. 결론 ………………………………………………………………….. 65



Chapter III. Silafluorene (SiF)과 다양한 전자받개 단량체를 이용한 낮은 band gap을 가지는 공액형 고분자 합성 및 특성 평가 ……… 67


III-1. 서론 …………………………………………………………………. 67

III-2. 실험 …………………………………………………………………. 70
III-2-1. 시약 ………………………………………………………..... 70
III-2-2. 전자받개 단량체 합성 …………………………………… 71
III-2-2-1. 1,2-Bis-decyloxy-benzene의 합성 (1) …… 71
III-2-2-2. 1,2-Bis-decyloxy-4,5-dinitro-benzene의 합성 (2) ………………………………………………………. 72
III-2-2-3. 5,6-Bis-decyloxy-benzo[1,2,5]thiadiazole 의 합성 (3) ……………………………………………….. 73
III-2-2-4. 4,7-Dibromo-5,6-bis-decyloxy-benzo[1,2,5]thiadiazole 의 합성 (4) ………………74
III-2-2-5. 5,6-Bis-decyloxy-4,7-di-thiophen-2-yl-benzo[1,2,5]thiadiazole 의 합성 (5) ………………75
III-2-2-6. 4,7-Bis-(5-bromo-thiophen-2-yl)-5,6-bis-decyloxy-benzo[1,2,5]thiadiazole 의 합성 (6)…76
III-2-2-7. 3,6-Di-thiophen-2-yl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) 의 합성 (7) ..……………………………………………………….77
III-2-2-8. 2,5-Dioctyl-3,6-di-thiophen-2-yl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 의 합성 (8) ………………………………………………….78
III-2-2-9. 3,6-Bis-(5-bromo-thiophen-2-yl)-2,5-dioctyl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 의 합성 (9) ……………………………….79

III-2-3. 전자주개 단량체 합성 ……………………………………….81
III-2-3-1. 4,4'-Dibromo-2,2'-dinitro-biphenyl 의 합성 (10)……………………………………………………. 81
III-2-3-2. 4,4'-Dibromo-biphenyl-2,2'-diamine 의 합성 (11)……………………………………………………. 82
III-2-3-3. 4,4'-Dibromo-biphenyl-2,2'-diamine 의 합성 (12)…………………………………………………….. 82
III-2-3-4. 4,4'-Dibromo-2,2'-diiodo-biphenyl 의 합성 (13) ……………………………………………………………. 83
III-2-3-5. 2,7-Dibromo-9,9-dioctyl-9H-dibenzosilole 의 합성(14)…………………………………………………. 84
III-2-3-6. 4,4,5,5-Tetramethyl-9,9-dioctyl-2,7 –silafluorene-[1,3,2] dioxaborolane 의 합성 (15)…………………………………………….………… 84

III-2-4. 고분자 중합 …………………………………………………. 87

III-2-4-1. Poly[3-[5-(7-Methyl-9,9-dioctyl-9H-dibenzosilol-2-yl)-thiophen-2-yl]-6-(5-methyl-thiophen-2-yl)-2,5-dioctyl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione]의 중합 (PSiFDPP8) ………………………………………87

III-2-4-2. Poly[5,6-Bis-decyloxy-4-[5-(7-methyl-9,9-dioctyl-9H-dibenzosilol-2-yl)-thiophen-2-yl]-7-(5-methyl-thiophen-2-yl)-benzo[1,2,5]thiadiazole]의 중합 (PSiFDTBTal)
…...…………………………………………………………88

III-3. 측정 및 소자 제작 ………………………………………………... 90
III-3-1. 측정 ……….………………………………………………….. 90
III-3-1-1. 구조 분석 ………………………………………………. 90
III-3-1-2. 광학적 전기적 특성 분석 …………………………… 90
III-3-1-3. 광전변환특성 분석 …………………………………… 90
II-3-2. 소자 제작 ………………………………………..………… 91

III-4. 결과 및 토론 ………………………………………………………..92

III-5. 결론 …………………………………………………………………103

References …………………………………………………………………104
Degree
Master
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