Highly Crystalline Low Band Gap Polymer Based on Thieno[3,4-c]pyrrole-4,6-dione for High-Performance Polymer Solar Cells with a >400 nm Thick Active Layer

ACS Applied Materials and Interfaces

Volumn 7, Issue 24, 2015, Pages 13666-13674

  Jung, Jae Woong ^a   Russell, Thomas P ^b   Jo, Won Ho ^a  

^a Seoul National University   (South Korea)

^b UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

polymer solar cell; thick active layer; thienylenevinylene

Indexed keywords

AROMATIC COMPOUNDS; COPOLYMERS; ENERGY GAP; PHOTOVOLTAIC EFFECTS; POLYMERS; SOLAR POWER GENERATION;

BIMOLECULAR RECOMBINATION; HIGH PERFORMANCE POLYMER SOLAR CELLS; HIGH POWER CONVERSION; PHOTOVOLTAIC PERFORMANCE; POLYMER SOLAR CELLS; THICK ACTIVE LAYERS; THIENYLENEVINYLENE; TRANSPORT CHARACTERISTICS;

SOLAR CELLS;

EID: 84932647182     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.5b03446     Document Type: Article

References (40)

1. Thompson, B. C.; Fréchet, J. M. J. Polymer-Fullerene Composite Solar Cells Angew. Chem., Int. Ed. 2008, 47, 58-77
2. Chochos, C. L.; Choulis, S. A. How the Structural Deviations on the Backbone of Conjugated Polymers Influence Their Optoelectronic Properties and Photovoltaic Performance Prog. Polym. Sci. 2011, 36, 1326-1414
3. Jung, J. W.; Jo, J. W.; Jo, W. H. Enhanced Performance and Air Stability of Polymer Solar Cells by Formation of a Self-Assembled Buffer Layer from Fullerene-End-Capped Poly(ethylene glycol) Adv. Mater. 2011, 23, 1782-1787
4. Small, C. E.; Chen, S.; Subbiah, J.; Amb, C. M.; Tsang, S.-W.; Lai, T.-H.; Reynolds, J. R.; So, F. High-Efficiency Inverted Dithienogermole-Thienopyrrolodione-Based Polymer Solar Cells Nat. Photonics 2012, 6, 115-120
5. You, J.; Dou, L.; Yoshimura, K.; Kato, T.; Ohya, K.; Moriarty, T.; Emery, K.; Chen, C.-C.; Gao, J.; Li, G.; Yang, Y. A Polymer Tandem Solar Cell with 10.6% Power Conversion Efficiency Nat. Commun. 2013, 4, 1446
6. Xu, T.; Yu, L. How To Design Low Bandgap Polymers for Highly Efficient Organic Solar Cells Mater. Today 2014, 17, 11-15
7. Boudreault, P.-L. T.; Najari, A.; Leclerc, M. Processable Low-Bandgap Polymers for Photovoltaic Applications Chem. Mater. 2011, 23, 456-469
8. Chen, H.-C.; Chen, Y.-H.; Liu, C.-C.; Chien, Y.-C.; Chou, S.-W.; Chou, P.-T. Prominent Short-Circuit Currents of Fluorinated Quinoxaline-Based Copolymer Solar Cells with a Power Conversion Efficiency of 8.0% Chem. Mater. 2012, 24, 4766-4772
9. Jung, J. W.; Jo, J. W.; Liu, F.; Russell, T. P.; Jo, W. H. A Low Band-Gap Polymer Based on Unsubstituted Benzo[1,2-b:4,5-b′]dithiophene for High Performance Organic Photovoltaics Chem. Commun. 2012, 48, 6933-6935
10. Jung, J. W.; Liu, F.; Russell, T. P.; Jo, W. H. Synthesis of Pyridine-Capped Diketopyrrolopyrrole and Its Use as a Building Block of Low Band-Gap Polymers for Efficient Polymer Solar Cells Chem. Commun. 2013, 49, 8495-8497
11. Chen, J.-D.; Cui, C.; Li, Y.-Q.; Zhou, L.; Ou, Q.-D.; Li, C.; Li, Y.; Tang, J.-X. Single-Junction Polymer Solar Cells Exceeding 10% Power Conversion Efficiency Adv. Mater. 2015, 27, 1035-1041
12. Liu, Y.; Zhao, J.; Li, Z.; Mu, C.; Ma, W.; Hu, H.; Jiang, K.; Lin, H.; Ade, H.; Yan, H. Aggregation and Morphology Control Enables Multiple Cases of High-Efficiency Polymer Solar Cells Nat. Commun. 2014, 5, 5293
13. Liao, S.-H.; Jhuo, H.-J; Yeh, P.-N.; Cheng, Y.-S.; Li, Y.-L.; Lee, Y.-H.; Sharma, S.; Chen, S.-A. Single Junction Inverted Polymer Solar Cell Reaching Power Conversion Efficiency 10.31% by Employing Dual-Doped Zinc Oxide Nano-film as Cathode Interlayer Sci. Rep. 2014, 4, 6813
14. Kaake, L. G.; Barbara, P. F.; Zhu, X.-Y. Intrinsic Charge Trapping in Organic and Polymeric Semiconductors: A Physical Chemistry Perspective J. Phys. Chem. Lett. 2010, 1, 628-635
15. Zhu, X.; Fang, J.; Lu, K.; Zhang, J.; Zhu, L.; Zhao, Y.; Shuai, Z.; Wei, Z. Naphtho[1,2- b:5, 6-b′]dithiophene Based Two-Dimensional Conjugated Polymers for High Efficient Thick-Film Inverted Polymer Solar Cells Chem. Mater. 2014, 26, 6947-6954
16. Zou, Y.; Najari, A.; Berrouard, P.; Beaupré, S.; Aich, B. R.; Tao, Y.; Leclerc, M. A Thieno[3,4-c]pyrrole-4,6-dione-Based Copolymer for Efficient Solar Cells J. Am. Chem. Soc. 2010, 132, 5330-5331
17. Chu, T.-Y.; Lu, J.; Beaupre, S.; Zhang, Y.; Pouliot, J.-R.; Wakim, S.; Zhou, J.; Leclerc, M.; Li, Z.; Ding, J.; Tao, Y. Bulk Heterojunction Solar Cells Using Thieno[3,4-c]pyrrole-4,6-dione and Dithieno[3,2-b:2′,3′-d]silole Copolymer with a Power Conversion Efficiency of 7.3% J. Am. Chem. Soc. 2011, 133, 4250-4253
18. Li, Z.; Tsang, S.-W.; Du, X.; Scoles, L.; Robertson, G.; Zhang, Y.; Toll, F.; Tao, Y.; Lu, J.; Ding, J. Alternating Copolymers of Cyclopenta[2,1-b;3,4-b′]dithiophene and Thieno[3,4-c]pyrrole-4,6-dione for High-Performance Polymer Solar Cells Adv. Funct. Mater. 2011, 21, 3331-3336
19. Jo, J.; Pron, A.; Berrouard, P.; Leong, W. L.; Yuen, J. D.; Moon, J. S.; Leclerc, M.; Heeger, A. J. A New Terthiophene-Thienopyrrolodione Copolymer-Based Bulk Heterojunction Solar Cell with High Open-Circuit Voltage Adv. Energy Mater. 2012, 2, 1397-1403
20. Yuan, J.; Zhai, Z.; Dong, H.; Li, J.; Jiang, Z.; Li, Y.; Ma, W. Efficient Polymer Solar Cells with a High Open Circuit Voltage of 1 V Adv. Funct. Mater. 2013, 23, 885-892
21. Warnan, J.; Cabanetos, C.; Labban, A. E.; Hansen, M. R.; Tassone, C.; Toney, M. F.; Beaujuge, P. M. Ordering Effects in Benzo[1,2- b:4,5-b′]difuran Thieno[3,4-c]pyrrole-4,6-dione Polymers with >7% Solar Cell Efficiency Adv. Mater. 2014, 26, 4357-4362
22. Kim, J.-H.; Park, J. B.; Xu, F.; Kim, D.; Kwak, J.; Grimsdale, A. C.; Hwang, D.-H. Effect of π-Conjugated Bridges of TPD-Based Medium Bandgap Conjugated Copolymers for Efficient Tandem Organic Photovoltaic Cells Energy Environ. Sci. 2014, 7, 4118-4131
23. Chen, H.; Cuo, Y.; Yu, G.; Zhao, Y.; Zhang, J.; Gao, D.; Liu, H.; Liu, Y. Highly π-Extended Copolymers with Diketopyrrolopyrrole Moieties for High-Performance Field-Effect Transistors Adv. Mater. 2012, 24, 4618-4622
24. Huang, H.; Chen, Z.; Ortiz, R. P.; Newman, C.; Usta, H.; Lou, S.; Youn, J.; Noh, Y.-Y.; Baeg, K.-J.; Chen, L. X.; Facchetti, A.; Marks, T. Combining Electron-Neutral Building Blocks with Intramolecular "Conformational Locks" Affords Stable, High-Mobility P- and N-Channel Polymer Semiconductors J. Am. Chem. Soc. 2012, 134, 10966-10973
25. Kim, J. Y.; Qin, Y.; Stevens, D. M.; Ugurlu, O.; Kalihari, V.; Hillmyer, M. A.; Frisbie, C. D. Low Band Gap Poly(thienylenevinylene)/Fullerene Bulk Heterojunction Photovoltaic Cells J. Phys. Chem. C 2009, 113, 10790-10797
26. Speros, J. C.; Paulsen, B. D.; White, S. P.; Wu, Y.; Jackson, E. A.; Slowinski, B. S.; Frisbie, C. D.; Hillmyer, M. A. An ADMET Route to Low-Band-Gap Poly(3-hexadecylthienylene vinylene): A Systematic Study of Molecular Weight on Photovoltaic Performance Macromolecules 2012, 45, 2190-2199
27. -1 Chem. Mater. 2011, 23, 4663-4665
28. Cheon, Y. R.; Kim, Y. J.; Ha, J.-J.; Kim, M.-J.; Park, C. E.; Kim, Y.-H. TPD-Based Copolymers with Strong Interchain Aggregation and High Hole Mobility for Efficient Bulk Heterojunction Solar Cells Macromolecules 2014, 47, 8570-8577
29. Jung, E. H.; Jo, W. H. π-Extended Low Bandgap Polymer Based on Isoindigo and Thienylvinylene for High Performance Polymer Solar Cells Energy Environ. Sci. 2014, 7, 650-654
30. Jung, J. W.; Liu, F.; Russell, T. P.; Jo, W. H. A High Mobility Conjugated Polymer Based on Dithienothiophene and Diketopyrrolopyrrole for Organic Photovoltaics Energy Environ. Sci. 2012, 5, 6857-6861
31. Jung, J. W.; Liu, F.; Russell, T. P.; Jo, W. H. Semi-crystalline Random Conjugated Copolymers with Panchromatic Absorption for Highly Efficient Polymer Solar Cells Energy Environ. Sci. 2013, 6, 3301-3307
32. Wu, J.-L.; Chen, F.-C.; Hsiao, Y.-S.; Chien, F.-C.; Chen, P.; Kuo, C.-H.; Huang, M. H.; Hsu, C.-S. Surface Plasmonic Effects of Metallic Nanoparticles on the Performance of Polymer Bulk Heterojunction Solar Cells ACS Nano 2011, 5, 959-967
33. Stuart, A. C.; Tumbleston, J. R.; Zhou, H. X.; Li, W. T.; Liu, S. B.; Ade, H.; You, W. Fluorine Substituents Reduce Charge Recombination and Drive Structure and Morphology Development in Polymer Solar Cells J. Am. Chem. Soc. 2013, 135, 1806-1815
34. Cowan, S. R.; Wang, J.; Yi, J.; Lee, Y. J.; Olson, D. C.; Hsu, J. W. P. Intensity and Wavelength Dependence of Bimolecular Recombination in P3HT: PCBM Solar Cells: A White-Light Biased External Quantum Efficiency Study J. Appl. Phys. 2013, 113, 154504
35. Liu, F.; Gu, Y.; Wang, C.; Zhao, W.; Chen, D.; Briseno, A. L.; Russell, T. P. Efficient Polymer Solar Cells Based on a Low Bandgap Semi-crystalline DPP Polymer-PCBM Blends Adv. Mater. 2012, 24, 3947-3951
36. Lim, B.; Baeg, K.-J.; Jeong, H.-G.; Jo, J.; Kim, H.; Park, J.-W; Noh, Y.-Y.; Vak, D.; Park, J. H.; Park, J.-W.; Kim, D.-Y. A New Poly(thienylenevinylene) Derivative with High Mobility and Oxidative Stability for Organic Thin-Film Transistors and Solar Cells Adv. Mater. 2009, 21, 2808-2814
37. Wang, D. H.; Pron, A.; Leclerc, M.; Heeger, A. J. Additive-Free Bulk-Heterojuction Solar Cells with Enhanced Power Conversion Efficiency, Comprising a Newly Designed Selenophene-Thienopyrrolodione Copolymer Adv. Funct. Mater. 2013, 23, 1297-1304
38. Jung, J. W.; Jo, J. W.; Chueh, C.-C.; Liu, F.; Jo, W. H.; Russell, T. P.; Jen, A. K.-Y. Fluoro-Substituted n-Type Conjugated Polymers for Additive-Free All-Polymer Bulk Heterojunction Solar Cells with High Power Conversion Efficiency of 6.71% Adv. Mater. 2015, 27, 3310-3317
39. Jung, J. W.; Liu, F.; Russell, T. P.; Jo, W. H. Anthracene-Based Medium Bandgap Conjugated Polymers for High Performance Polymer Solar Cells Exceeding 8% PCE without Additive and Annealing Process Adv. Energy Mater. 2015, 5, 1500065
40. Jung, J. W.; Jo, W. H. Low Band-Gap Copolymer Composed of Thienyl Substituted Anthracene and Diketopyrrolopyrrole Compatible with Multiple Electron Acceptors for High Efficiency Polymer Solar Cells Polym. Chem. 2015, 6, 4013-4019