Importance of Electron Transport Ability in Naphthalene Diimide-Based Polymer Acceptors for High-Performance, Additive-Free, All-Polymer Solar Cells

Chemistry of Materials

Volumn 27, Issue 15, 2015, Pages 5230-5237

  Choi, Joonhyeong ^a   Kim, Ki Hyun ^a   Yu, Hojeong ^b,c   Lee, Changyeon ^a   Kang, Hyunbum ^a   Song, Inho ^b   Kim, Youngwoong ^a   Oh, Joon Hak ^b   Kim, Bumjoon J ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Pohang University of Science and Technology (POSTECH)   (South Korea)

^c Ulsan National Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITIVES; ELECTRON MOBILITY; ELECTRON TRANSPORT PROPERTIES; ELECTRONS; FIELD EFFECT TRANSISTORS; HOLE MOBILITY; NAPHTHALENE; NONDESTRUCTIVE EXAMINATION; ORGANIC FIELD EFFECT TRANSISTORS; ORGANIC POLYMERS; SOLAR CELLS; SOLAR POWER GENERATION;

ALL-POLYMER SOLAR CELLS; ANISOTROPIC CHARGE TRANSPORT; ELECTRON TRANSPORT; HIGH POWER CONVERSION; INTERMOLECULAR INTERACTIONS; NAPHTHALENE DIIMIDE; PHOTOVOLTAIC PERFORMANCE; THREEDIMENSIONAL (3-D);

POLYMERS;

EID: 84939208993     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/acs.chemmater.5b01274     Document Type: Article

References (57)

1. Kaltenbrunner, M.; White, M. S.; Glowacki, E. D.; Sekitani, T.; Someya, T.; Sariciftci, N. S.; Bauer, S. Ultrathin and lightweight organic solar cells with high flexibility Nat. Commun. 2012, 3, 770 10.1038/ncomms1772
2. Sondergaard, R.; Hosel, M.; Angmo, D.; Larsen-Olsen, T. T.; Krebs, F. C. Roll-to-roll fabrication of polymer solar cells Mater. Today 2012, 15, 36-49 10.1016/S1369-7021(12)70019-6
3. Nguyen, T. L.; Choi, H.; Ko, S. J.; Uddin, M. A.; Walker, B.; Yum, S.; Jeong, J. E.; Yun, M. H.; Shin, T. J.; Hwang, S.; Kim, J. Y.; Woo, H. Y. Semi-crystalline photovoltaic polymers with efficiency exceeding 9% in a similar to 300 nm thick conventional single-cell device Energy Environ. Sci. 2014, 7, 3040-3051 10.1039/C4EE01529K
4. Cabanetos, C.; El Labban, A.; Bartelt, J. A.; Douglas, J. D.; Mateker, W. R.; Frechet, J. M. J.; McGehee, M. D.; Beaujuge, P. M. Linear Side Chains in Benzo[1,2-b:4,5-b ']dithiophene-Thieno[3,4-c]pyrrole-4,6-dione Polymers Direct Self-Assembly and Solar Cell Performance J. Am. Chem. Soc. 2013, 135, 4656-4659 10.1021/ja400365b
5. Kang, T. E.; Kim, K. H.; Kim, B. J. Design of terpolymers as electron donors for highly efficient polymer solar cells J. Mater. Chem. A 2014, 2, 15252-15267 10.1039/C4TA02426E
6. He, Z. C.; Zhong, C. M.; Su, S. J.; Xu, M.; Wu, H. B.; Cao, Y. Enhanced power-conversion efficiency in polymer solar cells using an inverted device structure Nat. Photonics 2012, 6, 591-595 10.1038/nphoton.2012.190
7. Liao, S. H.; Jhuo, H. J.; Cheng, Y. S.; Chen, S. A. Fullerene Derivative-Doped Zinc Oxide Nanofilm as the Cathode of Inverted Polymer Solar Cells with Low-Bandgap Polymer (PTB7-Th) for High Performance Adv. Mater. 2013, 25, 4766-4771 10.1002/adma.201301476
8. Li, W.; Furlan, A.; Hendriks, K. H.; Wienk, M. M.; Janssen, R. A. J. Efficient Tandem and Triple-Junction Polymer Solar Cells J. Am. Chem. Soc. 2013, 135, 5529-5532 10.1021/ja401434x
9. Zhang, M.; Gu, Y.; Guo, X.; Liu, F.; Zhang, S.; Huo, L.; Russell, T. P.; Hou, J. Efficient Polymer Solar Cells Based on Benzothiadiazole and Alkylphenyl Substituted Benzodithiophene with a Power Conversion Efficiency over 8% Adv. Mater. 2013, 25, 4944-4949 10.1002/adma.201301494
10. Liang, Y.; Xu, Z.; Xia, J.; Tsai, S.-T.; Wu, Y.; Li, G.; Ray, C.; Yu, L. For the Bright Future-Bulk Heterojunction Polymer Solar Cells with Power Conversion Efficiency of 7.4% Adv. Mater. 2010, 22, E135-E138 10.1002/adma.200903528
11. Zhou, H.; Yang, L.; Stuart, A. C.; Price, S. C.; Liu, S.; You, W. Development of Fluorinated Benzothiadiazole as a Structural Unit for a Polymer Solar Cell of 7% Efficiency Angew. Chem. 2011, 123, 3051-3054 10.1002/ange.201005451
12. Liu, Y. H.; Zhao, J. B.; Li, Z. K.; Mu, C.; Ma, W.; Hu, H. W.; Jiang, K.; Lin, H. R.; Ade, H.; Yan, H. Aggregation and morphology control enables multiple cases of high-efficiency polymer solar cells Nat. Commun. 2014, 5, 5293 10.1038/ncomms6293
13. Lenes, M.; Wetzelaer, G.-J. A. H.; Kooistra, F. B.; Veenstra, S. C.; Hummelen, J. C.; Blom, P. W. M. Fullerene Bisadducts for Enhanced Open-Circuit Voltages and Efficiencies in Polymer Solar Cells Adv. Mater. 2008, 20, 2116-2119 10.1002/adma.200702438
14. Kim, K. H.; Kang, H.; Kim, H. J.; Kim, P. S.; Yoon, S. C.; Kim, B. J. Effects of Solubilizing Group Modification in Fullerene Bis-Adducts on Normal and Inverted Type Polymer Solar Cells Chem. Mater. 2012, 24, 2373-2381 10.1021/cm3010369
15. He, Y.; Chen, H.-Y.; Hou, J.; Li, Y. Indene-C60 Bisadduct: A New Acceptor for High-Performance Polymer Solar Cells J. Am. Chem. Soc. 2010, 132, 1377-1382 10.1021/ja908602j
16. Zhou, E.; Cong, J. Z.; Hashimoto, K.; Tajima, K. Control of Miscibility and Aggregation Via the Material Design and Coating Process for High-Performance Polymer Blend Solar Cells Adv. Mater. 2013, 25, 6991-6996 10.1002/adma.201303170
17. Jung, I. H.; Lo, W. Y.; Jang, J.; Chen, W.; Zhao, D. L.; Landry, E. S.; Lu, L. Y.; Talapin, D. V.; Yu, L. P. Synthesis and Search for Design Principles of New Electron Accepting Polymers for All-Polymer Solar Cells Chem. Mater. 2014, 26, 3450-3459 10.1021/cm500832h
18. Facchetti, A. Polymer donor-polymer acceptor (all-polymer) solar cells Mater. Today 2013, 16, 123-132 10.1016/j.mattod.2013.04.005
19. Mu, C.; Liu, P.; Ma, W.; Jiang, K.; Zhao, J. B.; Zhang, K.; Chen, Z. H.; Wei, Z. H.; Yi, Y.; Wang, J. N.; Yang, S. H.; Huang, F.; Facchetti, A.; Ade, H.; Yan, H. High-Efficiency All-Polymer Solar Cells Based on a Pair of Crystalline Low-Bandgap Polymers Adv. Mater. 2014, 26, 7224-7230 10.1002/adma.201402473
20. Mori, D.; Benten, H.; Okada, I.; Ohkita, H.; Ito, S. Highly efficient charge-carrier generation and collection in polymer/polymer blend solar cells with a power conversion efficiency of 5.7% Energy Environ. Sci. 2014, 7, 2939-2943 10.1039/C4EE01326C
21. Kang, H.; Uddin, M. A.; Lee, C.; Kim, K.-H.; Nguyen, T. L.; Lee, W.; Li, Y.; Wang, C.; Woo, H. Y.; Kim, B. J. Determining the Role of Polymer Molecular Weight for High-Performance All-Polymer Solar Cells: Its Effect on Polymer Aggregation and Phase Separation J. Am. Chem. Soc. 2015, 137, 2359-2365 10.1021/ja5123182
22. Lee, C.; Kang, H.; Lee, W.; Kim, T.; Kim, K.-H.; Woo, H. Y.; Wang, C.; Kim, B. J. High-Performance All-Polymer Solar Cells Via Side-Chain Engineering of the Polymer Acceptor: The Importance of the Polymer Packing Structure and the Nanoscale Blend Morphology Adv. Mater. 2015, 27, 2466-2471 10.1002/adma.201405226
23. Zhou, Y.; Kurosawa, T.; Ma, W.; Guo, Y. K.; Fang, L.; Vandewal, K.; Diao, Y.; Wang, C. G.; Yan, Q. F.; Reinspach, J.; Mei, J. G.; Appleton, A. L.; Koleilat, G. I.; Gao, Y. L.; Mannsfeld, S. C. B.; Salleo, A.; Ade, H.; Zhao, D. H.; Bao, Z. N. High Performance All-Polymer Solar Cell via Polymer Side-Chain Engineering Adv. Mater. 2014, 26, 3767-3772 10.1002/adma.201306242
24. Deshmukh, K. D.; Qin, T.; Gallaher, J. K.; Liu, A. C. Y.; Gann, E.; O'Donnell, K.; Thomsen, L.; Hodgkiss, J. M.; Watkins, S. E.; McNeill, C. R. Performance, morphology and photophysics of high open-circuit voltage, low band gap all-polymer solar cells Energy Environ. Sci. 2015, 8, 332-342 10.1039/C4EE03059A
25. 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 10.1002/adma.201501214
26. Hwang, Y.-J.; Earmme, T.; Courtright, B. A. E.; Eberle, F. N.; Jenekhe, S. A. n-Type Semiconducting Naphthalene Diimide-Perylene Diimide Copolymers: Controlling Crystallinity, Blend Morphology, and Compatibility Toward High-Performance All-Polymer Solar Cells J. Am. Chem. Soc. 2015, 137, 4424-4434 10.1021/ja513260w
27. Mori, D.; Benten, H.; Okada, I.; Ohkita, H.; Ito, S. Low-Bandgap Donor/Acceptor Polymer Blend Solar Cells with Efficiency Exceeding 4% Adv. Energy Mater. 2014, 4, 1301006 10.1002/aenm.201301006
28. Huang, H.; Zhou, N.; Ortiz, R. P.; Chen, Z.; Loser, S.; Zhang, S.; Guo, X.; Casado, J.; López Navarrete, J. T.; Yu, X.; Facchetti, A.; Marks, T. J. Alkoxy-Functionalized Thienyl-Vinylene Polymers for Field-Effect Transistors and All-Polymer Solar Cells Adv. Funct. Mater. 2014, 24, 2782-2793 10.1002/adfm.201303219
29. Earmme, T.; Hwang, Y. J.; Murari, N. M.; Subramaniyan, S.; Jenekhe, S. A. All-Polymer Solar Cells with 3.3% Efficiency Based on Naphthalene Diimide-Selenophene Copolymer Acceptor J. Am. Chem. Soc. 2013, 135, 14960-14963 10.1021/ja4085429
30. Schubert, M.; Collins, B. A.; Mangold, H.; Howard, I. A.; Schindler, W.; Vandewal, K.; Roland, S.; Behrends, J.; Kraffert, F.; Steyrleuthner, R.; Chen, Z. H.; Fostiropoulos, K.; Bittl, R.; Salleo, A.; Facchetti, A.; Laquai, F.; Ade, H. W.; Neher, D. Correlated Donor/Acceptor Crystal Orientation Controls Photocurrent Generation in All-Polymer Solar Cells Adv. Funct. Mater. 2014, 24, 4068-4081 10.1002/adfm.201304216
31. Zhou, N.; Lin, H.; Lou, S. J.; Yu, X.; Guo, P.; Manley, E. F.; Loser, S.; Hartnett, P.; Huang, H.; Wasielewski, M. R.; Chen, L. X.; Chang, R. P. H.; Facchetti, A.; Marks, T. J. Morphology-Performance Relationships in High-Efficiency All-Polymer Solar Cells Adv. Energy Mater. 2014, 4, 1300785 10.1002/aenm.201300785
32. Kang, H.; Kim, K. H.; Choi, J.; Lee, C.; Kim, B. J. High-Performance All-Polymer Solar Cells Based on Face-On Stacked Polymer Blends with Low Interfacial Tension ACS Macro Lett. 2014, 3, 1009-1014 10.1021/mz500415a
33. Sommer, M. Conjugated polymers based on naphthalene diimide for organic electronics J. Mater. Chem. C 2014, 2, 3088-3098 10.1039/C3TC31755B
34. Steyrleuthner, R.; Schubert, M.; Jaiser, F.; Blakesley, J. C.; Chen, Z.; Facchetti, A.; Neher, D. Bulk Electron Transport and Charge Injection in a High Mobility n-Type Semiconducting Polymer Adv. Mater. 2010, 22, 2799-2803 10.1002/adma.201000232
35. Vasimalla, S.; Senanayak, S. P.; Sharma, M.; Narayan, K. S.; Iyer, P. K. Improved Performance of Solution-Processed n-Type Organic Field-Effect Transistors by Regulating the Intermolecular Interactions and Crystalline Domains on Macroscopic Scale Chem. Mater. 2014, 26, 4030-4037 10.1021/cm501780p
36. Kim, Y.; Hong, J.; Oh, J. H.; Yang, C. Naphthalene Diimide Incorporated Thiophene-Free Copolymers with Acene and Heteroacene Units: Comparison of Geometric Features and Electron-Donating Strength of Co-units Chem. Mater. 2013, 25, 3251-3259 10.1021/cm401829x
37. Wurthner, F.; Stolte, M. Naphthalene and perylene diimides for organic transistors Chem. Commun. 2011, 47, 5109-5115 10.1039/c1cc10321k
38. Yan, H.; Chen, Z. H.; Zheng, Y.; Newman, C.; Quinn, J. R.; Dotz, F.; Kastler, M.; Facchetti, A. A high-mobility electron-transporting polymer for printed transistors Nature 2009, 457, 679-686 10.1038/nature07727
39. Kim, R.; Amegadze, P. S. K.; Kang, I.; Yun, H. J.; Noh, Y. Y.; Kwon, S. K.; Kim, Y. H. High-Mobility Air-Stable Naphthalene Diimide-Based Copolymer Containing Extended pi-Conjugation for n-Channel Organic Field Effect Transistors Adv. Funct. Mater. 2013, 23, 5719-5727 10.1002/adfm.201301197
40. Chen, H. J.; Guo, Y. L.; Yu, G.; Zhao, Y.; Zhang, J.; Gao, D.; Liu, H. T.; Liu, Y. Q. Highly p-Extended Copolymers with Diketopyrrolopyrrole Moieties for High-Performance Field-Effect Transistors Adv. Mater. 2012, 24, 4618-4622 10.1002/adma.201201318
41. Yun, H. J.; Choi, H. H.; Kwon, S. K.; Kim, Y. H.; Cho, K. Conformation-Insensitive Ambipolar Charge Transport in a Diketopyrrolopyrrole-Based Co-polymer Containing Acetylene Linkages Chem. Mater. 2014, 26, 3928-3937 10.1021/cm5014703
42. Chen, H. J.; Guo, Y. L.; Mao, Z. P.; Yu, G.; Huang, J. Y.; Zhao, Y.; Liu, Y. Q. Naphthalenediimide-Based Copolymers Incorporating Vinyl-Linkages for High-Performance Ambipolar Field-Effect Transistors and Complementary-Like Inverters under Air Chem. Mater. 2013, 25, 3589-3596 10.1021/cm401130n
43. Schubert, M.; Dolfen, D.; Frisch, J.; Roland, S.; Steyrleuthner, R.; Stiller, B.; Chen, Z. H.; Scherf, U.; Koch, N.; Facchetti, A.; Neher, D. Influence of Aggregation on the Performance of All-Polymer Solar Cells Containing Low-Bandgap Naphthalenediimide Copolymers Adv. Energy Mater. 2012, 2, 369-380 10.1002/aenm.201100601
44. Yan, H. P.; Collins, B. A.; Gann, E.; Wang, C.; Ade, H.; McNeill, C. R. Correlating the Efficiency and Nanomorphology of Polymer Blend Solar Cells Utilizing Resonant Soft X-ray Scattering ACS Nano 2012, 6, 677-688 10.1021/nn204150f
45. Collins, B. A.; Li, Z.; Tumbleston, J. R.; Gann, E.; McNeill, C. R.; Ade, H. Absolute Measurement of Domain Composition and Nanoscale Size Distribution Explains Performance in PTB7:PC71BM Solar Cells Adv. Energy Mater. 2013, 3, 65-74 10.1002/aenm.201200377
46. Swaraj, S.; Wang, C.; Yan, H. P.; Watts, B.; Jan, L. N.; McNeill, C. R.; Ade, H. Nanomorphology of Bulk Heterojunction Photovoltaic Thin Films Probed with Resonant Soft X-ray Scattering Nano Lett. 2010, 10, 2863-2869 10.1021/nl1009266
47. Sun, K.; Xiao, Z. Y.; Lu, S. R.; Zajaczkowski, W.; Pisula, W.; Hanssen, E.; White, J. M.; Williamson, R. M.; Subbiah, J.; Ouyang, J. Y.; Holmes, A. B.; Wong, W. W. H.; Jones, D. J. A molecular nematic liquid crystalline material for high-performance organic photovoltaics Nat. Commun. 2015, 6, 6013 10.1038/ncomms7013
48. Mei, J. G.; Kim, D. H.; Ayzner, A. L.; Toney, M. F.; Bao, Z. A. Siloxane-Terminated Solubilizing Side Chains: Bringing Conjugated Polymer Backbones Closer and Boosting Hole Mobilities in Thin-Film Transistors J. Am. Chem. Soc. 2011, 133, 20130-20133 10.1021/ja209328m
49. Lee, J.; Han, A. R.; Yu, H.; Shin, T. J.; Yang, C.; Oh, J. H. Boosting the Ambipolar Performance of Solution-Processable Polymer Semiconductors via Hybrid Side-Chain Engineering J. Am. Chem. Soc. 2013, 135, 9540-9547 10.1021/ja403949g
50. Rivnay, J.; Steyrleuthner, R.; Jimison, L. H.; Casadei, A.; Chen, Z.; Toney, M. F.; Facchetti, A.; Neher, D.; Salleo, A. Drastic Control of Texture in a High Performance n-Type Polymeric Semiconductor and Implications for Charge Transport Macromolecules 2011, 44, 5246-5255 10.1021/ma200864s
51. Lee, J.; Han, A. R.; Kim, J.; Kim, Y.; Oh, J. H.; Yang, C. Solution-Processable Ambipolar Diketopyrrolopyrrole-Selenophene Polymer with Unprecedentedly High Hole and Electron Mobilities J. Am. Chem. Soc. 2012, 134, 20713-20721 10.1021/ja308927g
52. Steyrleuthner, R.; Di Pietro, R.; Collins, B. A.; Polzer, F.; Himmelberger, S.; Schubert, M.; Chen, Z. H.; Zhang, S. M.; Salleo, A.; Ade, H.; Facchetti, A.; Neher, D. The Role of Regioregularity, Crystallinity, and Chain Orientation on Electron Transport in a High-Mobility n-Type Copolymer J. Am. Chem. Soc. 2014, 136, 4245-4256 10.1021/ja4118736
53. Piliego, C.; Holcombe, T. W.; Douglas, J. D.; Woo, C. H.; Beaujuge, P. M.; Frechet, J. M. J. Synthetic Control of Structural Order in N-Alkylthieno[3,4-c]pyrrole-4,6-dione-Based Polymers for Efficient Solar Cells J. Am. Chem. Soc. 2010, 132, 7595-7597 10.1021/ja103275u
54. Qi, B. Y.; Wang, J. Z. Fill factor in organic solar cells Phys. Chem. Chem. Phys. 2013, 15, 8972-8982 10.1039/c3cp51383a
55. 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 10.1002/adfm.201202541
56. Chang, W.-H.; Meng, L.; Dou, L.; You, J.; Chen, C.-C.; Yang, Y.; Young, E. P.; Li, G.; Yang, Y. A Selenophene Containing Benzodithiophene-alt-thienothiophene Polymer for Additive-Free High Performance Solar Cell Macromolecules 2015, 48, 562-568 10.1021/ma502132t
57. Salim, T.; Wong, L. H.; Brauer, B.; Kukreja, R.; Foo, Y. L.; Bao, Z. N.; Lam, Y. M. Solvent additives and their effects on blend morphologies of bulk heterojunctions J. Mater. Chem. 2011, 21, 242-250 10.1039/C0JM01976C