Fluorene-based Polymer and Oligomer Electrolytes for Polymer Solar Cells
- Abstract
- A series fluorene-based conjugated polymer, poly[6,6'-(2-(thiophen-2-yl)-9H-fluorene-9,9-diyl)bis(N,N,N-trimethylhexan-1-aminium) bromide] (PFT Salt), poly[6,6'-(2-phenyl-9H-fluorene-9,9-diyl)bis(N,N,N-trimethylhexan-1-aminium) bromide] (PFB Salt), poly[9,9-bis(6-(3,5-bis(bromomethyl)phenoxy) hexyl)-2,7-dibromo-9H-fluorene-thiophene] (P[IsoPh-OH-T]), poly[1,1',1'',1'''-(((2-(thiophen-2-yl)-9H-fluorene-9,9-diyl)bis(hexane-6,1-diyl))bis (benzene-5,3,1-triyl)) tetrakis (N,N,N-trimethylmethanaminium) bromide] (P[IsoPh-Br-T] Salt), and oligomer, 6,6',6'',6'''-(phenyl-2,5-diylbis(9H-fluorene-9,9,2-triyl))tetrakis(N,N,N-trimethyl-hexan-1-aminium) bromide (FBF Salt), 6,6',6'',6'''-(thiophene-2,5-diylbis(9H-fluorene-9,9,2-triyl))tetrakis(N,N,N-trimethylhexan-1-aminium) bromide (FTF Salt), 6,6'-(2,7-diphenyl-9H-fluorene-9,9-diyl) bis(N,N,N-trimethylhexan-1-aminium) bromide (BFB Salt), 6,6'-(2,7-di(thiophen-2-yl)-9H-fluorene-9,9-diyl) bis(N,N,N-trimethylhexan-1-aminium) bromide (TFT Salt), 6,6'-(2,7-bis(2,4-difluorophenyl)-9H-fluorene-9,9-diyl)bis(N,N,N-trimethylhexan-1-aminium) bromide (Bf-F-Bf Salt) has been synthesized and utilized as cathode interfacial layer in inverted polymer solar cell. Cathode interfacial layer (CIL) or usually known as electron transfer layer (ETL) is interpretative to improving the power conversion efficiency (PCE) and long-term stability of an organic photovoltaic cell that utilizes a high work function cathode. The KPM result that the polymers: PFt salt, PFB salt, P-IsoPh-Br-T salt, P-IsoPh-OH-T, and the oligomers, demonstrates a strong impact on the interfacial interaction to the electrode by reducing the work function of ITO. To investigate the effect of CIL on the photovoltaic properties, inverted type PSCs with a device configuration of ITO/ZnO/CIL/PTB7-PC71BM/MoO3/Ag were fabricated. Maximum power conversion efficiency (PCE) of the PSCs based on polyfluorene is showed up to 7.91% from the device based PFB salt and for the oligomer is showed up to 8.26% from the device based BfFBf salt. Nevertheless all the result indicate that fluorene-based conjugated electrolytes are excellent CIL materials for polymer solar cells.
- Issued Date
- 2017
- Awarded Date
- 2017. 8
- Type
- Dissertation
- Publisher
- 부경대학교
- Affiliation
- 부경대학교 대학원
- Department
- 대학원 고분자공학과
- Advisor
- Prof. Joo Hyun Kim
- Table Of Contents
- I. Introduction 1
I-1. Introduction to organic solar cells 1
I-2. The operating principle of an organic solar cell 2
I-2-1 Absorption of light and exciton generation 4
I-2-2. Exciton diffusion 4
I-2-3. Exciton dissociation 5
I-2-4. Charge transport and charge collection 6
I-3. Interfacial layer 7
I-3-1. Anode interface layer/ HTL 8
I-3-1-1. Poly (3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT:PSS) 9
I-3-1-2. Metal Oxide (MOx) 10
I-3-2. Cathode interface layer/ ETL 11
I-3-2-1. Zinc Oxide (ZnO) 12
I-3-2-2. Water/alcohol soluble conjugated polymers (WSCPs) 13
I-3-2-3. Fluorene derivatives 14
II. Polyfluorene-based electrolytes as interfacial layer of inverted polymer solar cells 17
II-1. Introduction 17
II-2. Experimental 18
II-2-1. Material and Synthesis 18
II-2-1-1. Materials 18
II-2-1-2. Synthesis 19
II-2-1-2-1. General procedure of Suzuki coupling polymerization reaction 19
II-2-1-2-2. General procedure of Stille coupling polymerization reaction 19
II-2-1-2-3. Synthesis of 2,7-dibromo-9,9-bis-(6-bromo-hexyl)-9H-fluorene (2) 20
II-2-1-2-4. Synthesis of poly[2-[9,9-Bis-(6-bromo-hexyl)-9H-fluoren-2-yl]-thiophene] (PFT) 21
II-2-1-2-5. Synthesis of poly[2-[9,9-bis-(6-bromo-hexyl)-9H-fluoren-2-yl]-benzene] (PFB) 22
II-2-1-2-6. Synthesis of poly[6,6'-(2-(thiophen-2-yl)-9H-fluorene-9,9-diyl)bis(N,N,N trimethylhexan-1-aminium) bromide] (PFT Salt) 23
II-2-1-2-7. Synthesis of poly[6,6'-(2-phenyl-9H-fluorene-9,9-diyl)bis(N,N,N-trimethylhexan-1-aminium) bromide] (PFB Salt) 24
II-2-2. Fabrication of PSCs 26
II-2-3. Measurement 27
II-3. Result and discussion 29
II-3-1. XPS elemental analysis 29
II-3-2. Optical and electrochemical properties 30
II-3-3. Interfacial properties 37
II-3-4. Photovoltaic properties 38
II-4. Conclusion 42
III. Alcohol-soluble conjugated polymer as interfacial layer of inverted polymer solar cells 43
III-1. Introduction 43
III-2. Experimental 44
III-2-1. Material and synthesis 44
III-2-1-1. Materials 44
III-2-1-2. Synthesis 44
III-2-1-2-1. General Procedure of Stille coupling polymerization reaction 44
III-2-1-2-2. Synthesis of 2,7-dibromo-9,9-bis-(6-bromo-hexyl)-9H-fluorene (1) 44
III-2-1-2-3. Synthesis of tetramethyl 5,5'-(((2,7-dibromo-9H-fluorene-9,9-diyl)bis(hexane-6,1-diyl))bis(oxy))diisophthalate (2) 46
III-2-1-2-4. Synthesis of ((((2,7-dibromo-9H-fluorene-9,9-diyl)bis(hexane-6,1-diyl))bis(oxy))bis(benzene-5,3,1-triyl))tetramethanol (3) 47
III-2-1-2-5. Synthesis of 9,9-bis(6-(3,5-bis(bromomethyl)phenoxy)hexyl)-2,7-dibromo-9H-fluorene (4) 48
III-2-1-2-6. Synthesis of poly((((2,7-dibromo-9H-fluorene-9,9-diyl)bis(hexane-6,1-diyl))bis(oxy))bis(benzene-5,3,1-triyl))tetramethanol-thiophene (P[IsoPh-OH-T]) 51
III-2-1-2-7. Synthesis of poly[9,9-bis(6-(3,5-bis(bromomethyl)phenoxy) hexyl)-2,7-dibromo-9H-fluorene-thiophene] (P[IsoPh-Br-T]) 52
III-2-1-2-8. Synthesis of poly[1,1',1'',1'''-(((2-(thiophen-2-yl)-9H-fluorene-9,9-diyl)bis(hexane-6,1-diyl))bis(benzene-5,3,1-triyl))tetrakis(N,N,N-trimethylmethanaminium) bromide] (P[IsoPh-Br-T] Salt) 53
III-2-2. Fabrication of PSCs 55
III-2-3. Measurement 56
III-3. Result and Discussion 58
III-3-1. XPS elemental analysis 58
III-3-2. Optical and electrochemical properties 59
III-3-3. Interfacial Properties 65
III-3-4. Photovoltaic properties 67
III-4. Conclusion 71
IV. Conjugated oligo-electrolytes as cathode interfacial layer for IPSCs 72
IV-1. Introduction 72
IV-2. Experimental 72
IV-2-1. Material and synthesis 72
IV-2-1-1. Materials 72
IV-2-1-2. Synthesis 73
IV-2-1-2-1. General procedure of Suzuki coupling reaction 73
IV-2-1-2-2. General procedure of stille coupling reaction 73
IV-2-1-2-3. Synthesis of 2-bromo-9,9-bis-(6-bromo-hexyl)-9H-fluorene (2) 74
IV-2-1-2-4. Synthesis of 4,4,5,5,4',4',5',5'-Octamethyl-[2,2']bi[[1,3,2]dioxa-borolanyl]-Benzene (4) 75
IV-2-1-2-5. Synthesis of 2,5-bis-[9,9-bis-(6-bromo-hexyl)-9H-fluoren-2-yl]-Benzene (FBF) 76
IV-2-1-2-6. Synthesis of 2,5-bis-[9,9-bis-(6-bromo-hexyl)-9H-fluoren-2-yl]-thiophene (FTF) 77
IV-2-1-2-7. Synthesis of 6,6',6'',6'''-(phenyl-2,5-diylbis(9H-fluorene-9,9,2-triyl))tetrakis(N,N,N-trimethylhexan-1-aminium) bromide (FBF Salt) 78
IV-2-1-2-8. Synthesis of 6,6',6'',6'''-(thiophene-2,5-diylbis(9H-fluorene-9,9,2-triyl))tetrakis(N,N,N-trimethylhexan-1-aminium) bromide (FTF Salt) 79
IV-2-1-2-9. Synthesis of 2,2'-(9,9-bis(6-bromohexyl)-9H-fluorene-2,7-diyl) dithiophene (TFT) 81
IV-2-1-2-10. Synthesis of 9,9-bis (6-bromohexyl)- 2,7-diphenyl-9H-fluorene (BFB) 82
IV-2-1-2-11. Synthesis of 9,9-bis(6-bromohexyl)-2,7-bis(2,4-difluoro-phenyl)- 9H-fluorene (BfFBf) 83
IV-2-1-2-12. Synthesis of 6,6'-(2,7-di(thiophen-2-yl)-9H-fluorene-9,9-diyl) bis(N,N,N-trimethylhexan-1-aminium) bromide (TFT Salt) 85
IV-2-1-2-13. Synthesis of 6,6'-(2,7-diphenyl-9H-fluorene-9,9-diyl) bis(N,N,N-trimethylhexan-1-aminium) bromide (BFB Salt) 85
IV-2-1-2-14. Synthesis of 6,6'-(2,7-bis(2,4-difluorophenyl)-9H-fluorene-9,9-diyl)bis(N,N,N-trimethylhexan-1-aminium) bromide (BfFBf Salt) 86
IV-2-2. Fabrication of PSCs 89
IV-2-3. Measurement 90
IV-3. Result and Discussion 92
IV-3-1. XPS elemental analysis 92
IV-3-2. Optical and electrochemical properties 94
IV-3-3. Interfacial properties 101
IV-3-4. Photovoltaic properties 103
IV-4. Conclusion 108
References 109
Acknowledgement 116
- Degree
- Master
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