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Effect of the Selective Halogenation of Small Molecule Acceptors on the Blend Morphology and Voltage Loss of High-Performance Solar Cells

Journal Article · · Advanced Functional Materials
Herein, the impacts of the selective halogenation at two different positions of dicyanomethylene-3-indanone (IC) end groups and inner side chains of small molecular acceptors (SMAs) on the PD:SMA interfacial interactions, blend morphology, and resulting photovoltaic properties are described. In this study, four different SMAs (A1, A2, A3, and A4) with the same molecular backbone, but with different degrees of halogenation, are synthesized. The IC end groups on the backbones of the A1 and A3, and A2 and A4 SMAs are chlorinated and fluorinated, respectively; in addition, 6-phenoxyhexyl inner side chains of the A3 and A4 are chlorinated. The SMAs are paired with a chlorinated PBDT-Cl PD to construct organic solar cells (OSCs). The PBDT-Cl:A4-based OSC exhibits the highest power conversion efficiency of 17.2%, outperforming the PBDT-Cl:A1-(13.3%), PBDT-Cl:A2-(15.6%), and PBDT-Cl:A3-based OSC (16.5%). The Cl atoms on the side chains in the A3 and A4 SMAs enhance the molecular/energetic interactions at the PD:SMA interfaces and improve the blend morphology in terms of domain purity and spacing. These effects lead to the improved fill factors and reduced voltage loss of the PBDT-Cl:A3- and PBDT-Cl:A4-based OSCs. This study demonstrates the importance of appropriate halogenation of SMAs in optimizing the blend morphology, reducing voltage loss, and improving OSC performance.
Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)
Sponsoring Organization:
National Research Foundation of Korea (NRF); USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities (SUF)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1981345
Journal Information:
Advanced Functional Materials, Journal Name: Advanced Functional Materials Journal Issue: 25 Vol. 32; ISSN 1616-301X
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English

References (83)

Asymmetric Acceptors with Fluorine and Chlorine Substitution for Organic Solar Cells toward 16.83% Efficiency journal April 2020
Importance of Optimal Crystallinity and Hole Mobility of BDT‐Based Polymer Donor for Simultaneous Enhancements of V oc , J sc , and FF in Efficient Nonfullerene Organic Solar Cells journal September 2020
Importance of Terminal Group Pairing of Polymer Donor and Small‐Molecule Acceptor in Optimizing Blend Morphology and Voltage Loss of High‐Performance Solar Cells journal April 2021
Structure–Property Relationships of Precisely Chlorinated Thiophene‐Substituted Acceptors journal September 2021
Importance of High‐Electron Mobility in Polymer Acceptors for Efficient All‐Polymer Solar Cells: Combined Engineering of Backbone Building Unit and Regioregularity journal October 2021
Device Physics of PolymerFullerene Bulk Heterojunction Solar Cells journal June 2007
Single‐Junction Organic Photovoltaic Cells with Approaching 18% Efficiency journal March 2020
Single‐Junction Organic Photovoltaic Cell with 19% Efficiency journal August 2021
Regioregular Narrow‐Bandgap n‐Type Polymers with High Electron Mobility Enabling Highly Efficient All‐Polymer Solar Cells journal August 2021
17.6%‐Efficient Quasiplanar Heterojunction Organic Solar Cells from a Chlorinated 3D Network Acceptor journal July 2021
Bromination: An Alternative Strategy for Non‐Fullerene Small Molecule Acceptors journal February 2020
Chlorination: An Effective Strategy for High‐Performance Organic Solar Cells journal June 2020
Significance of Average Domain Purity and Mixed Domains on the Photovoltaic Performance of High-Efficiency Solution-Processed Small-Molecule BHJ Solar Cells journal July 2015
Controlling Molecular Orientation of Naphthalenediimide-Based Polymer Acceptors for High Performance All-Polymer Solar Cells journal June 2016
Design of Cyanovinylene-Containing Polymer Acceptors with Large Dipole Moment Change for Efficient Charge Generation in High-Performance All-Polymer Solar Cells journal September 2017
Effect of Ring-Fusion on Miscibility and Domain Purity: Key Factors Determining the Performance of PDI-Based Nonfullerene Organic Solar Cells journal July 2018
Quantifying and Understanding Voltage Losses Due to Nonradiative Recombination in Bulk Heterojunction Organic Solar Cells with Low Energetic Offsets journal June 2019
Altering the Positions of Chlorine and Bromine Substitution on the End Group Enables High‐Performance Acceptor and Efficient Organic Solar Cells journal October 2020
Organic Solar Cells—The Path to Commercial Success journal November 2020
Efficient, Thermally Stable, and Mechanically Robust All‐Polymer Solar Cells Consisting of the Same Benzodithiophene Unit‐Based Polymer Acceptor and Donor with High Molecular Compatibility journal December 2020
Enabling High Efficiency of Hydrocarbon‐Solvent Processed Organic Solar Cells through Balanced Charge Generation and Non‐Radiative Loss journal October 2021
Systematically Controlling Acceptor Fluorination Optimizes Hierarchical Morphology, Vertical Phase Separation, and Efficiency in Non‐Fullerene Organic Solar Cells journal November 2021
Synergistic Engineering of Side Chains and Backbone Regioregularity of Polymer Acceptors for High‐Performance All‐Polymer Solar Cells with 15.1% Efficiency journal November 2021
Highly Flexible and Efficient All-Polymer Solar Cells with High-Viscosity Processing Polymer Additive toward Potential of Stretchable Devices journal September 2018
Detailed balance and reciprocity in solar cells journal December 2008
Role of Energy Offset in Nonradiative Voltage Loss in Organic Solar Cells journal June 2020
15.4% Efficiency all-polymer solar cells journal January 2021
Non-fullerene acceptor pre-aggregates enable high efficiency pseudo-bulk heterojunction organic solar cells journal November 2021
The impact of fluorination on both donor polymer and non-fullerene acceptor: The more fluorine, the merrier journal March 2019
Reducing Voltage Losses in the A-DA′D-A Acceptor-Based Organic Solar Cells journal September 2020
Understanding Energy Loss in Organic Solar Cells: Toward a New Efficiency Regime journal January 2018
A Chlorinated π-Conjugated Polymer Donor for Efficient Organic Solar Cells journal August 2018
Single-Junction Organic Solar Cell with over 15% Efficiency Using Fused-Ring Acceptor with Electron-Deficient Core journal April 2019
Trifluoromethylation Enables a 3D Interpenetrated Low-Band-Gap Acceptor for Efficient Organic Solar Cells journal March 2020
Prediction of non-radiative voltage losses in organic solar cells using machine learning journal November 2021
Importance of 2D Conjugated Side Chains of Benzodithiophene-Based Polymers in Controlling Polymer Packing, Interfacial Ordering, and Composition Variations of All-Polymer Solar Cells journal October 2017
Selenophene-Incorporated Quaterchalcogenophene-Based Donor–Acceptor Copolymers To Achieve Efficient Solar Cells with J sc Exceeding 20 mA/cm 2 journal November 2017
Organoboron Polymer for 10% Efficiency All-Polymer Solar Cells journal January 2020
Recent Advances, Design Guidelines, and Prospects of All-Polymer Solar Cells journal June 2019
Trifluoromethyl Group-Modified Non-Fullerene Acceptor toward Improved Power Conversion Efficiency over 13% in Polymer Solar Cells journal February 2020
New Phase for Organic Solar Cell Research: Emergence of Y-Series Electron Acceptors and Their Perspectives journal April 2020
Intrinsically Stretchable Organic Solar Cells with Efficiencies of over 11% journal June 2021
New Random Copolymer Acceptors Enable Additive-Free Processing of 10.1% Efficient All-Polymer Solar Cells with Near-Unity Internal Quantum Efficiency journal April 2019
Eco-Friendly Polymer Solar Cells: Advances in Green-Solvent Processing and Material Design journal October 2020
Donor–Acceptor Alternating Copolymer Compatibilizers for Thermally Stable, Mechanically Robust, and High-Performance Organic Solar Cells journal November 2021
Small-Molecule Thiophene-C 60 Dyads As Compatibilizers in Inverted Polymer Solar Cells journal October 2010
Effects of Solubilizing Group Modification in Fullerene Bis-Adducts on Normal and Inverted Type Polymer Solar Cells journal June 2012
Quantitative Determination of Organic Semiconductor Microstructure from the Molecular to Device Scale journal June 2012
Systematic Merging of Nonfullerene Acceptor π-Extension and Tetrafluorination Strategies Affords Polymer Solar Cells with >16% Efficiency journal April 2021
A Wide-Bandgap Donor Polymer for Highly Efficient Non-fullerene Organic Solar Cells with a Small Voltage Loss journal April 2017
Drastic Control of Texture in a High Performance n-Type Polymeric Semiconductor and Implications for Charge Transport journal July 2011
High-Performance All-Polymer Solar Cells Based on Face-On Stacked Polymer Blends with Low Interfacial Tension journal September 2014
High-efficiency polymer solar cells with small photon energy loss journal December 2015
Ultrathin and lightweight organic solar cells with high flexibility journal January 2012
Flexible, highly efficient all-polymer solar cells journal October 2015
Fast charge separation in a non-fullerene organic solar cell with a small driving force journal June 2016
Reducing the efficiency–stability–cost gap of organic photovoltaics with highly efficient and stable small molecule acceptor ternary solar cells journal November 2016
Impact of interfacial molecular orientation on radiative recombination and charge generation efficiency journal July 2017
Enabling low voltage losses and high photocurrent in fullerene-free organic photovoltaics journal February 2019
Over 16% efficiency organic photovoltaic cells enabled by a chlorinated acceptor with increased open-circuit voltages journal June 2019
Cathode engineering with perylene-diimide interlayer enabling over 17% efficiency single-junction organic solar cells journal June 2020
Material insights and challenges for non-fullerene organic solar cells based on small molecular acceptors journal July 2018
A unified description of non-radiative voltage losses in organic solar cells journal June 2021
Next-generation organic photovoltaics based on non-fullerene acceptors journal February 2018
High-efficiency organic solar cells with low non-radiative recombination loss and low energetic disorder journal January 2020
Critical review of the molecular design progress in non-fullerene electron acceptors towards commercially viable organic solar cells journal January 2019
A top-down strategy identifying molecular phase stabilizers to overcome microstructure instabilities in organic solar cells journal January 2019
A chlorinated nonacyclic carbazole-based acceptor affords over 15% efficiency in organic solar cells journal January 2020
Over 14% efficiency all-polymer solar cells enabled by a low bandgap polymer acceptor with low energy loss and efficient charge separation journal January 2020
Recent progress in reducing voltage loss in organic photovoltaic cells journal January 2021
Flexible-spacer incorporated polymer donors enable superior blend miscibility for high-performance and mechanically-robust polymer solar cells journal January 2021
Progress and prospects of the morphology of non-fullerene acceptor based high-efficiency organic solar cells journal January 2021
Achieving highly efficient all-polymer solar cells by green-solvent-processing under ambient atmosphere journal January 2021
Non-fullerene acceptors with direct and indirect hexa-fluorination afford >17% efficiency in polymer solar cells journal January 2022
Green solvent-processed, high-performance organic solar cells achieved by outer side-chain selection of selenophene-incorporated Y-series acceptors journal January 2021
Recent Advances of Chlorination in Organic Solar Cells journal June 2021
Detailed Balance Limit of Efficiency of p‐n Junction Solar Cells journal March 1961
Polar and Nonpolar Interactions in Adhesion journal January 1973
Control over π-π stacking of heteroheptacene-based nonfullerene acceptors for 16% efficiency polymer solar cells journal August 2020
Organic photovoltaic cell with 17% efficiency and superior processability journal December 2019
Trap-limited hole mobility in semiconducting poly(3-hexylthiophene) journal December 2004
Recombination in polymer-fullerene bulk heterojunction solar cells journal December 2010
Scherrer grain-size analysis adapted to grazing-incidence scattering with area detectors journal October 2009

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