Review
  • Synthesis of Photoactive Layer Materials in Organic Photovoltaics: an Asymmetric Molecular Approach

  • Wooteak Jung, Sehwa Hong, Sung Mo Moon*, and Sung Yun Son*,†

  • Department of Chemical Engineering, Pohang University of Science and Technology, 77 Cheongam-Ro, Nam-Gu, Pohang, Gyeongbuk 37673, Korea
    *Department of Chemistry, Kwangwoon University, 20 Kwangwoon-Ro, Seoul 01897, Korea

  • 유기태양전지에서의 광활성층 물질 합성: 분자의 비대칭성적 접근

  • 정우택 · 홍세화 · 문성모* · 손성윤*,†

  • 포항공과대학교 화학공학과, *광운대학교 화학과

  • Reproduction, stored in a retrieval system, or transmitted in any form of any part of this publication is permitted only by written permission from the Polymer Society of Korea.

References
  • 1. Yuda, A. P.; Koraag, P. Y. E.; Iskandar, F.; Wasisto, H. S.; Sumboja, A. Advances of the Top-down Synthesis Approach for High-performance Silicon Anodes in Li-ion Batteries. J. Mater. Chem. A. 2021, 9, 18906.
  •  
  • 2. Meng, R.; Xufang, Q.; Yuetian, C.; Tianfu, W.; Yixin, Z. Potential Lead Toxicity and Leakage Issues on Lead Halide Perovskite Photovoltaics. J. Hazard. Mater. 2022, 426, 127848.
  •  
  • 3. Cheon, H. J.; An, T. K.; Kim, Y. H. Diketopyrrolopyrrole (DPP)-Based Polymers and Their Organic Field-Effect Transistor Applications: A Review, Macromol. Res. 2022,30, 71-84.
  •  
  • 4. Chau, H. D.; Kataria, M.; Kwon, N. Y. Improved Photovoltaic Performance of Ternary All-Polymer Solar Cells by Incorporating a New Y6-based Polymer Acceptor and PC61BM, Macromol. Res. 2022, 30, 587-596.
  •  
  • 5. Yousif, Q. A.; Agbolaghi, S. Retraction Note to: A Comparison Between Functions of Carbon Nanotube and Reduced Graphene Oxide and Respective Ameliorated Derivatives in Perovskite Solar Cells, Macromol. Res. 2022, 30, 686.
  •  
  • 6. Lee, M.; Hwang, E.; Kim, T.; Kwon, T.-H. Advancements in Non-fullerene Acceptors for Organic Solar Cells: Brief Review of Research Trends. Bull. Korean Chem. Soc. 2024, 45, 664-674.
  •  
  • 7. Gayathri, R. D.; Gokulnath, T.; Park, H. Y. Facile and Stable Fluorene Based Organic Hole Transporting Materials for Efficient Perovskite Solar Cells, Macromol. Res. 2022, 30, 745-750.
  •  
  • 8. (a) Jong, W. H.; Jung, J. G.; Ryu, D. H.; Lee, S. H.; Song, C. E.; Lim, B. G.; Jung, Y. G.; Park, J. M.; Hwang, D. H. Thienoquinolinone-based Acceptor-π-acceptor-type Building Block for Polymer Donors in Organic Solar Cells. Macromol. Res. 2023, 31, 25-31. (b) Lee, G. S.; Oh, J. G.; Suh, E. H. Naphthalene-Diimide-Based Small Molecule Containing a Thienothiophene Linker for n-Type Organic Field-Effect Transistors. Macromol. Res. 2022, 30, 470-476.
  •  
  • 9. Choi, H.; Ryu, S. U.; Lee, D. H.; Kim, H.; Song, S.; Kim, H. I.; Park, T. Advancements in Organic-Based Hybrid Tandem Solar Cells Considering Light Absorption and Spectral Matching of Organic Materials. ACS Energy Lett. 2024, 9, 3136-3168.
  •  
  • 10. Kim, H. U.; Kim, T.; Kim, C.; Kim, M.; Park, T. Recent Advances in Structural Design of Efficient Near-Infrared Light-Emitting Organic Small Molecules. Adv. Funct. Mater. 2022, 33, 2208082.
  •  
  • 11. Huarui, Z.; Guangliu, R.; Xinyue, C.; Yuqiang, L.; Zhe, Y.; Dawei, L.; Xueqing, M.; Wenlong, L.; Hao, L.; Rui, L.; Lei, C.; Wenkai, Z.; Siru, G.; Hongxiang, L.; Jifa, Y.; Yi, L.; Yahui, L.; Guanghao, L.; Zaifei, M.; Pei, C.; Zhishan, B. Mitigating Exciton Recombination Losses in Organic Solar Cells by Engineering Nonfullerene Molecular Crystallization Behavior. Adv. Energy Mater. 2023, 13, 2302063.
  •  
  • 12. Lim, E. P3HT-Based Polymer Solar Cells with Unfused Bithiophene–Rhodanine-based Nonfullerene Acceptors, Bull. Korean Chem. Soc. 2020, 41, 644-649.
  •  
  • 13. Lee, H.; Moon, B.; Son, S. Y.; Park, T.; Kang, B.; Cho, K. Charge Trapping in a Low-Crystalline High-Mobility Conjugated Polymer and Its Effects on the Operational Stability of Organic Field-Effect Transistors. ACS Appl. Mater. Interfaces. 2021, 13, 16722-16731.
  •  
  • 14. (a) Ryu, Y. H.; Choi, K.; Oh, D. H. Ionic Cross-Linkable Alendronate-Conjugated Biodegradable Polyurethane Films for Potential Guided Bone Regeneration. Macromol. Res. 2022,30, 99-106. (b) Oh, D. H.; Thi, P. L.; Park, K. D. A Comparative Study of Enzyme-Mediated Crosslinking of Catechol- and Phenol-Functionalized Tetronic Hydrogels. Macromol. Res. 2022, 30, 190-197.
  •  
  • 15. Nguyen, T. T. T.; Nguyen, H. T.; Trinh, H. T.; Effect of the Morphological Characteristic and Composition of Electrospun Polyvinylidene Fluoride/Graphene Oxide Membrane on Its Pb2+ Adsorption Capacity. Macromol. Res. 2022,30, 124-135.
  •  
  • 16. (a) Jeong, H.; Lee, D. Y.; Yang, D. H. Mechanical and Cell-Adhesive Properties of Gelatin/Polyvinyl Alcohol Hydrogels and Their Application in Wound Dressing. Macromol. Res. 2022, 30, 223-229. (b) Lee, S.; Jeon, I. S.; Jho, J. Y. Mechanical Properties of Polyetheretherketone Composites with Surface-Modified Hydroxyapatite Nanofibers and Carbon Fibers. Macromol. Res. 2022, 30, 261-270.
  •  
  • 17. Choi, J.; Jung, W.; Gonzalez-Carrero, S.; Durrant, J. R.; Cha, H.; Park, T. Understanding Charge Carrier Dynamics in Organic Photocatalysts for Hydrogen Evolution. Energy Environ. Sci. [Online early access]. DOI: 10.1039/D4EE01808G. Published Online: Jul 20, 2024. https://pubs.rsc.org/en/content/articlelanding/2024/ee/d4ee01808g (accessed Jul 20, 2024).
  •  
  • 18. Temurlu, S.; Abureesh, M. A. A.; Abourajab, A.; Karsili, P.; Dinleyici, M.; Altınışık, S.; Koyuncu, S.; Icil, H. Grafting of Perylene and Naphthalene Fluorophores Onto Chitosan for Improved Thermal, Optical and Electrical Properties. Macromol. Res. 2024, 32, 281-297.
  •  
  • 19. Do, Y.; Park, H.; Gokulnath, T. Significance of Siloxane Functionalized Side-Chain π-Conjugated Polymer Donor: Optimization of Active Layer Morphology Toward the Stable All-Polymer Solar Cells. Macromol. Res. 2022, 30, 183-189.
  •  
  • 20. Haris, M.; Ullah, Z.; Lee, S.; Ryu, D. H.; Ryu, S. U.; Kang, B. J.; Jeon, N. J.; Kim, B. J.; Park, T.; Shin, W. S.; Song, C. E. Amplifying High-Performance Organic Solar Cells Through Differencing Interactions of Solid Additive with Donor/Acceptor Materials Processed from Non-Halogenated Solvent. Adv. Energy Mater. 2024, 14, 2401597.
  •  
  • 21. Kim, M.; Ryu, S. U.; Park, S. A.; Choi, K.; Kim, T.; Chung, D.; Park, T. Donor–Acceptor-Conjugated Polymer for High-Performance Organic Field-Effect Transistors: A Progress Report. Adv. Funct. Mater. 2020, 30, 1904545.
  •  
  • 22. Lim, E. Two A-D-A-type Non-Fullerene Small Molecule Acceptors Based on 1,3-Dimethylbarbituric Acid for OPVs. Bull. Korean Chem. Soc. 2017, 38, 285-288.
  •  
  • 23. Lee, S. W.; Jeong, M.; Whang, D. R.; Kim, J. H.; Chang, D. W. Effect of Fluorine Atom on Photovoltaic Properties of Triphenylamine-Substituted Quinoxaline-Based D-A Type Polymers. Macromol. Res. 2020, 28, 1297-1303.
  •  
  • 24. Abbas, Z.; Ryu, S. U.; Haris, M.; Song, C. E.; Lee, H. K.; Lee, S. K.; Shin, W. S.; Park, T.; Lee, J. C. Optimized Vertical Phase Separation via Systematic Y6 Inner Side-chain Modulation for Non-halogen Solvent Processed Inverted Organic Solar Cells. Nano Energy. 2022, 101, 107574.
  •  
  • 25. Kim, M.; Ryu, S. U.; Park, S. A.; Pu, Y. J.; Park, T. Designs and Understanding of Small Molecule-based Non-fullerene Acceptors for Realizing Commercially Viable Organic Photovoltaics. Chem Sci. 2021, 12, 14004-14023.
  •  
  • 26. Kim, I. B.; Kim, Y. J.; Kim, D.Y.; Jang, S. Y. A Thiophene Based Dopant-Free Hole-Transport Polymer for Efficient and Stable Perovskite Solar Cells. Macromol. Res 2022, 30, 391-396.
  •  
  • 27. (a) Amarasekara, A. S.; Leday, L. J.; Wang, D. Synthesis and Characterization of a New Cellulose Ether Derivative: Sodium Levulinate Cellulose. Macromol. Res. 2023, 31, 941-948. (b) Zhang, Q.; Chen, J.; Jin, B. A New Linear Heptafluoro Glycidyl Ether Binder: Synthesis, Characterization, and Mechanical Properties. Macromol. Res. 2023, 31, 699-709.
  •  
  • 28. Kim, T.; Shin, G.; Park, T.; Kim, M. Molecular Design Leveraging Non-Covalent Interactions for Efficient Light-Emitting Organic Small Molecules. Adv. Funct. Mater. [Online early access]. DOI: 10.1002/adfm.202412267. Published Online: Aug 30, 2024. https://onlinelibrary.wiley.com/doi/full/10.1002/adfm.202412267 (accessed Aug 30, 2024).
  •  
  • 29. Ha, J. W.; Jung, J. G.; Ryu, D. H.; Lee, S.; Song, C. E.; Lim, B.; Jung, Y. J.; Park, J. M.; Hwang, D. H. Thienoquinolinone-based Acceptor-π-acceptor-type Building Block for Polymer Donors in Organic Solar Cells. Macromol. Res. 2023, 31, 25-31.
  •  
  • 30. Park, S. A.; Kim, D. H.; Chung, D.; Kim, J.; Park, T.; Cho, S.; Kim, M. Asymmetric Polymer Additive for Morphological Regulation and Thermally Stable Organic Solar Cells. ACS Appl. 2023, 15, 27026-27033.
  •  
  • 31. Aryal, U. K.; Lee, J.; Kranthiraja, K.; Reddy, S. S.; Sree, V. G.; Park, T.; Song, M.; Jin, S. H. The Effect of Irregularity From Asymmetric Random π-conjugated Polymers on the Photovoltaic Performance of Fullerene-free Organic Solar Cells. Polym. Chem. 2019, 10, 4407-4412.
  •  
  • 32. Jia, B.; Wang, J.; Wu, Y.; Zhang, M.; Jiang, Y.; Tang, Z.; Russell, T. P.; Zhan, X. Enhancing the Performance of a Fused-Ring Electron Acceptor by Unidirectional Extension, J. Am. Chem. Soc. 2019, 141, 19023-19031.
  •  
  • 33. Lee, J. Y.; Han, J. G.; Lee, S. H.; Kim, D. H.; Lee, Y. S. Synthesis and Characterization of an Isoindigo–Naphthalene Polymer along with a Small Molecule of Naphthalene–Isoindigo–Naphthalene. Bull. Korean Chem. Soc. 2015, 36, 2974-2977.
  •  
  • 34. Lin, Y.; Wang, J.; Zhang, Z. G.; Bai, H.; Li, Y.; Zhu, D.; Zhan, X. An Electron Acceptor Challenging Fullerenes for Efficient Polymer Solar Cells. Adv. Mater. 2015, 27, 1170-1174.
  •  
  • 35. Park, J.; Chetan, L.; Kim, H.; Jee, J. S.; Gal, Y. S.; Jin, S. H. New Pyrazine-based π-conjugated Polymer for Dopant-free Perovskite Solar Cell. Macromol. Res. 2024, 32, 505-513.
  •  
  • 36. Seo, J. Y.; Kang, S. H.; Lee, M. R.; Synthesis of Thermo-Controlled Cyclic Olefin Polymers via Ring Opening Metathesis Polymerization: Effect of Copolymerization with Flexible Modifier. Macromol. Res. 2022, 30, 205-211.
  •  
  • 37. Hu, H.; Ge, J.; Chen, Z.; Song, W.; Xie, L.; Ge, Z. The Asymmetric Strategy of Small-Molecule Materials for Organic Solar Cells. Adv. Energy Mater. 2024, 14, 2304242.
  •  
  • 38. Hoang, M. H.; Park, G. E.; Phan, D. L.; Ngo, T. T.; Nguyen, T. V.; Park, C. G.; Cho, M. J.; Choi, D. H. Synthesis of Conjugated Wide-Bandgap Copolymers Bearing Ladder-Type Donating Units and Their Application to Non-Fullerene Polymer Solar Cells. Macromol. Res. 2018, 26, 844-850.
  •  
  • 39. Gao, W.; Zhang, M.; Liu, T.; Ming, R.; An, Q.; Wu, K.; Xie, D.; Luo, Z.; Zhong, C.; Liu, F. Asymmetrical Ladder-Type Donor-Induced Polar Small Molecule Acceptor to Promote Fill Factors Approaching 77% for High-Performance Nonfullerene Polymer Solar Cells. Adv. Mater. 2018, 30, 1800052.
  •  
  • 40. Jeong, M.; Chen, S.; Lee, S. M.; Wang, Z.; Yang, Y.; Zhang, Z. G.; Zhang, C.; Xiao, M.; Li, Y.; Yang, C. Feasible D1–A–D2–A Random Copolymers for Simultaneous High-Performance Fullerene and Nonfullerene Solar Cells. Adv. Energy Mater. 2017, 8, 1702166.
  •  
  • 41. Chen, S.; Cho, H. J.; Lee, J.; Yang, Y.; Zhang, Z. G.; Li, Y.; Yang, C. Modulating the Molecular Packing and Nanophase Blending via a Random Terpolymerization Strategy toward 11 Efficiency Nonfullerene Polymer Solar Cells. Adv. Energy Mater. 2017, 7, 1701125.
  •  
  • 42. Kim, S. W.; Choi, J.; Bui, T. T. T.; Lee, C.; Cho, C.; Na, K.; Jung, J.; Song, C. E.; Ma, B.; Lee, J. Y.; Shin, W. S.; Kim, B. J. Rationally Designed Donor–Acceptor Random Copolymers with Optimized Complementary Light Absorption for Highly Efficient All-Polymer Solar Cells. Adv. Funct. Mater. 2017, 27, 1703070.
  •  
  • 43. (a) Namikoshi, T.; Watanabe, Y.; Kaneda, A.; Ishikawa, K.; Watanabe, S.; Murata , M. Controlled Cationic Polymerization of Sulfide-Containing Vinyl Ethers. Macromol. Res. 2022, 30, 16-25. (b) Gunasekara, D. S. W.; Niu, X.; Lqbal, W; He, Y.; Liu, H. Pyrrole Coating with In Situ Polymerization for Piezoresistive Sensor Development - A Review. Macromol. Res. 2022, 30, 153-162.
  •  
  • 44. Salma, S. A.; Kim, J. H. Effect of the Side Chain Functionality of the Conjugated Polyelectrolytes as a Cathode Interlayer Material on the Photovoltaic Performances. Macromol. Res. 2022, 30, 146-151.
  •  
  • 45. Kim, J.; Park, J.; Song, D.; Jee, J.; Gokulnath, T.; Han, S. C.; Jin, S. H.; Lee, J. W. BDT-based Donor Polymer for Organic Solar Cells to Achieve High Efficiency over 15% for Ternary Organic Solar Cells. Macromol. Res. 2023, 31, 489-497.
  •  
  • 46. Rasanani, A. H.; Kaffashi, B.; Ahmadi, S. Assessment of Surface, Structural, and Viscoelastic Properties of Immiscible Polylactic Acid/Polyvinylidene Fluoride Blends. Macromol. Res. 2022, 30, 285-294.
  •  
  • 47. Jeong, Y. G.; Park, S. Y.; Kim, J. S. Relationship Between the Chemical Structure, Morphology, and Water Absorption of Styrene-co-itaconate Ionomers. Macromol. Res. 2023, 31, 245-255.
  •  
  • 48. Ghalia, M. A.; Inuwa, I.; Hassan, A. RETRACTED ARTICLE: Viscoelastic Behavior and Mechanical Properties of Polypropylene/Nano-Calcium Carbonate Nanocomposites Modified by a Coupling Agent. Macromol. Res. 2022, 30, 842-852.
  •  
  • 49. Raj, M. R.; Kim, H. I.; Lee, G. Y.; Kim, G. W.; Park, T. Morphological Study of Polymer/fullerene Interfaces via benzene–PCBM Interaction. Org. Electron. 2015, 26, 230-238.
  •  
  • 50. Kim, M.; Choi, Y.; Hwan Lee, D.; Min, J.; Pu, Y. J.; Park, T. Roles and Impacts of Ancillary Materials for Multi-Component Blend Organic Photovoltaics towards High Efficiency and Stability. ChemSusChem. 2021, 14, 3475-3487.
  •  
  • 51. Wang, G.; Melkonyan, F. S.; Facchetti, A.; Marks, T. J. All-Polymer Solar Cells: Recent Progress, Challenges, and Prospects. Angew. Chem. Int. Ed. Engl. 2019, 58, 4129-4142.
  •  
  • 52. Zhou, N.; Dudnik, A. S.; Li, T. I.; Manley, E. F.; Aldrich, T. J.; Guo, P.; Liao, H. C.; Chen, Z.; Chen, L. X.; Chang, R. P. All-Polymer Solar Cell Performance Optimized via Systematic Molecular Weight Tuning of Both Donor and Acceptor Polymers. J. Am. Chem. Soc. 2016, 138, 1240-1251.
  •  
  • 53. Wang, G.; Eastham, N. D.; Aldrich, T. J.; Ma, B.; Manley, E. F.; Chen, Z.; Chen, L. X.; de la Cruz, M. O.; Chang, R. P. H.; Melkonyan, F. S. Photoactive Blend Morphology Engineering through Systematically Tuning Aggregation in All-Polymer Solar Cells. Adv. Energy Mater. 2018, 8, 1702173.
  •  
  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 0379-153X(Print)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2023 Impact Factor : 0.4
  • Indexed in SCIE

This Article

  • 2024; 48(6): 594-602

    Published online Nov 25, 2024

  • 10.7317/pk.2024.48.6.594
  • Received on Sep 6, 2024
  • Revised on Oct 16, 2024
  • Accepted on Oct 18, 2024

Correspondence to

  • Sung Yun Son

  • *Department of Chemistry, Kwangwoon University, 20 Kwangwoon-Ro, Seoul 01897, Korea

  • E-mail: syson@kw.ac.kr