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Stable Radical TEMPO Terminated Perylene Bisimide(PBI) Based Small Molecule as cathode interlayer for Efficient Organic Solar Cells

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Chemical Research in Chinese Universities 2023年第2期39卷 213-218页

作者： ZHANG Ziwei XIA Dongdong XIE Qian ZHAO Chaowei FANG Jie WU Yonggang LI Weiwei College of Chemistry and Environmental Science Hebei UniversityBaoding071002P.R.China Institute of Applied Chemistry Jiangxi Academy of SciencesNanchang330096P.R.China Beijing Advanced Innovation Center for Soft Matter Science and Engineering and State Key Laboratory of Organic-Inorganic Composites Beijing University of Chemical TechnologyBeijing100029P.R.China

By combining stable radical tetramethylpiperidine nitrogen oxide(TEMPO)as end groups and perylene bisimide(PBI)as the core,a small molecular cathode interlayer(CIL)(PBI-TEMPO)was synthesized.Detailed physical-chemical characterizations indicate that PBI-TEMPO can form smooth film,owns low unoccupied molecular orbital(LUMO)level of−3.67 eV and can reduce the work function of silver electrode.When using PBI-TEMPO as CIL in non-fullerene organic solar cells(OSCs),the PM6:BTP-4Cl based OSCs delivered high power conversion efficiencies(PCEs)up to 17.37%,higher than those using commercial PDINO CIL with PCEs of 16.95%.Further device characterizations indicate that PBI-TEMPO can facilitate more efficient exciton dissociation and reduce charge recombination,resulting in enhanced current density and fill factor.Moreover,PBI-TEMPO displays higher thermal stability than PDINO in solution.When PBI-TEMPO and PDINO solution were heated at 150℃ for 2 h and then were used as CIL in solar cells,PBI-TEMPO-based OSCs provided a PCE of 15%,while PDINO-based OSCs only showed a PCE of 10%.These results demonstrate that incorporating TEMPO into conjugated materials is a useful strategy to create new organic semiconductors for application in OSCs.

关键词： Tetramethylpiperidine nitrogen oxide(TEMPO) Perylene bisimide cathode interlayer Organic solar cell Power conversion efficiency

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Interface Engineering of Inverted Perovskite Solar Cells Using a Self-doped Perylene Diimide Ionene Terpolymer as a Thickness-Independent cathode interlayer

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Chinese Journal of Chemistry 2023年第23期41卷 3326-3332页

作者： Daizhe Wang Tengling Ye Dongqing He Xiaochen Sun Yong Zhang Department of Applied Chemistry School of Chemistry and Chemical EngineeringHarbin Institute of TechnologyHarbinHeilongjiang150001 China School of Materials Science and Engineering Harbin Institute of TechnologyHarbinHeilongjiang150001 China State Key Laboratory of Luminescent Materials and Devices South China University of TechnologyGuangzhouGuangdong510640 China Institute of Advanced Technology Heilongjiang Academy of SciencesHarbinHeilongjiang150020 China

Inverted perovskite solar cells(PerSCs)are a highly promising candidate in the photovoltaic field due to their low-temperature fabrication process,negligible hysteresis,and easy integration with Si-based solar cells.A cathode interlayer(CIL)is necessary in the development of inverted devices to reduce the trap density and energy barrier between the electron transport layer(ETL)and the electrode.However,most CILs are highly thickness-sensitive due to low conductivity and poor film-forming.In this study,we report on a self-doping perylene imide-based ionene polymer(PNPDIN)used as CIL material to modify electrode in inverted PerSCs.PNPDIN exhibits high conductivity and a good solubility in polar solvent,which results in an improved power conversion efficiency(PCE)from 10.05%(device without a CIL)to 16.97%.When the blend of PNPDIN and Bphen was used as a mixed CIL,the PCE of PerSCs can be further increased to 21.28%owing to the excellent morphology and matched energy level.More importantly,the PCE of the device is highly tolerant to the thickness of the mixed CIL,which benefited from the high conductivity of PNPDIN.This development is expected to provide an excellent mixed CIL material for roll-to-roll processing efficient and stable inverted PerSCs.

关键词： Perylene diimide Perovskite solar cells Interface engineering cathode interlayer Thickness-independent

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Surfactant-Encapsulated Polyoxometalate Complex as a cathode interlayer for Nonfullerene Polymer Solar Cells

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CCS Chemistry 2022年第3期4卷 975-986页

作者： Jing Qiu Yue Zhang Yan Liu Huiru Liu Dongdong Xia Fan Yang Chaowei Zhao Weiwei Li Lixin Wu Fenghong Li State Key Laboratory of Supramolecular Structure and Materials Jilin UniversityChangchun 130012 Institute of Applied Chemistry Jiangxi Academy of SciencesNanchang 330096 Beijing National Laboratory for Molecular Sciences Institute of ChemistryChinese Academy of SciencesBeijing 100190 College of Chemistry Chemical Engineering and Materials ScienceCollaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of ShandongKey Laboratory of Molecular and Nano ProbesMinistry of EducationShandong Normal UniversityJinan 250014 State Key Laboratory of Organic-Inorganic Composites Beijing University of Chemical TechnologyBeijing 100029

An alcohol-soluble,environmentally friendly,and low-cost surfactant-encapsulated polyoxometalate complex[(C8H17)4N]4[SiW_(12)O40](TOASiW_(12))as a cathode interlayer(CIL)has exhibited excellent universality for various active layers and cathodes in nonfullerene polymer solar cells(NF-PSCs).In particular,incorporating TOASiW_(12) as the CIL enhanced power conversion efficiencies(PCEs)of the PM6:Y6-based NF-PSCs with Al or Ag cathode to 16.14%and 15.89%,respectively,and the PCEs of PM6:BTP-BO4Cl-based NF-PSCs with Al or Ag cathode to 17.04%and 17.00%,respectively.More importantly,the performances of the devices with TOASiW_(12) were insensitive to the TOASiW_(12) thickness from 3 to 33 nm.Furthermore,the NF-PSCs with TOASiW_(12) exhibited better device stability.Combined characterization of the photocurrent density versus effective voltage,capacitance versus voltage and electron mobility demonstrated that TOASiW_(12) as the CIL effectively promoted exciton dissociation,charge-carrier extraction,built-in potential,charge-carrier density,and electron mobility in the NF-PSCs.These findings suggest that TOASiW_(12) is a promising,competitive CIL for NF-PSCs fabricated by roll-to-roll processing.

关键词： surfactant-encapsulated polyoxometalate complex nonfullerene polymer solar cells cathode interlayer device stability thickness-insensitive low-cost

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Edge-functionalized graphene quantum dots as a thickness-insensitive cathode interlayer for polymer solar cells

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Nano Research 2018年第8期11卷 4293-4301页

作者： Han Xu Lu Zhang Zicheng Ding Junli Hu Jun Liu Yichun Liu Key Laboratory of UV-Emitting Materials and Technology (Northeast Normal University) Ministry of Education Changchun 130024China State Key Laboratory of Polymer Physics and Chemistry Changchun Institute of Applied Chemistry Chinese Academy of SciencesChangchun 130022 China Han Xu and Lu Zhang contributed equally to this work.

A thickness-insensitive cathode interlayer （CIL） is necessary for large-area polymer solar cells （PSCs）, in which thickness variation is unavoidable. These C1L materials are typically based on n-type conjugated polymer/molecule backbones, which show strong light absorption in the visible/near-infrared （NIR） region. This interferes with the sunlight absorption by the active layer and deteriorates device efficiency. In this study, we developed graphene quantum dots functionalized with ammonium iodide （GQD-NI） at the edge as a thickness-insensitive CIL with high optical transparency. The peripheral ammonium iodide groups of GQD-NI formed the desired interfacial dipole with the cathode to decrease the work function. The graphene basal planes of GQD-NI with a lateral size of ca. 3 nm demonstrated a good conductivity of 3.56 ×10-6 S.cm-1 and high transparency in the visible/NIR region （λmax abs = 228 nm）. Moreover, GQD-NI was readily soluble in polar organic solvents, e.g., methanol, which enabled multilayer device fabrication with orthogonal solvent processing. As a result, the PSC device with GQD-NI as the CIL exhibited a power conversion efficiency （PCE） of 7.49%, which was much higher than that of the device without the CIL （PCE = 5.38%） or with calcium as the CIL （PCE = 6.72%）. Moreover, the PSC device performance of GQD-NI was insensitive to the GQD-NI layer thickness in the range of 2-22 nm. These results indicate that GQD-NI is a very promising material for application as a CIL in large-area printed PSCs.

关键词： graphene quantum dots ammonium edge-functionalization cathode interlayer polymer solar cells

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Block copolymers as efficient cathode interlayer materials for organic solar cells

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Frontiers of Chemical Science and Engineering 2021年第3期15卷 571-578页

作者： Dingqin Hu Jiehao Fu Shanshan Chen Jun Li Qianguang Yang Jie Gao Hua Tang Zhipeng Kan Tainan Duan Shirong Lu Kuan Sun Zeyun Xiao Chongqing Institute of Green and Intelligent Technology Chongqing SchoolUniversity of Chinese Academy of Sciences(UCAS Chongqing)Chinese Academy of SciencesChongqing 400714China MOE Key Laboratory of Low-Grade Energy Utilization Technologies and Systems School of Energy&Power EngineeringChongqing UniversityChongqing 400044China Library&Information Center Anhui University of Finance and EconomicsBengbu 233030China

Emerging needs for the large-scale industrialization of organic solar cells require high performance cathode interlayers to facilitate the charge extraction from organic semiconductors.In addition to improving the efficiency,stability and processability issues are major challenges.Herein,we design block copolymers with well controlled chemical composition and molecular weight for cathode interlayer applications.The block copolymer coated cathodes display high optical transmittance and low work function.Conductivity studies reveal that the block copolymer thin film has abundant conductive channels and excellent longitudinal electron conductivity due to the interpenetrating networks formed by the polymer blocks.Applications of the cathode interlayers in organic solar cells provide higher power conversion efficiency and better stability compared to the most widelyapplied ZnO counterparts.Furthermore,no post-treatment is needed which enables excellent processability of the block copolymer based cathode interlayer.

关键词： organic solar cell block copolymer cathode interlayer

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Printable SnO2 cathode interlayer with up to 500 nm thickness-tolerance for high-performance and large-area organic solar cells

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Science China Chemistry 2020年第7期63卷 957-965页

作者： Yiming Bai Chunyan Zhao Shuai Zhang Shaoqing Zhang Runnan Yu Jianhui Hou Zhan’ao Tan Yongfang Li State Key Laboratory of Alternate Electrical Power System with Renewable Energy Sources North China Electric Power UniversityBeijing 102206China Beijing Advanced Innovation Center for Soft Matter Science and Engineering Beijing University of Chemical TechnologyBeijing 100029China Institute of Chemistry Chinese Academy of SciencesBeijing 100190China

The printable electrode interlayer with excellent thickness tolerance is crucial for mass production of organic solar cells(OSCs)by solution-based print techniques. Herein, high-quality printable SnO2 films are simply fabricated by spin-coating or bladecoating the chemical precipitated SnO2 colloid precursor with post thermal annealing treatment. The SnO2 films possess outstanding optical and electrical properties, especially extreme thickness-insensitivity. The interfacial electron trap density of SnO2 cathode interlayers(CILs) are very low and show negligible increase as the thicknesses increase from 10 to 160 nm,resulting in slight change of the power conversion efficiencies(PCEs) of the PM6:Y6 based OSCs from 16.10% to 13.07%. For blade-coated SnO2 CIL, the PCE remains high up to 12.08% even the thickness of SnO2 CIL is high up to 530 nm. More strikingly, the large-area OSCs of 100 mm2 with printed SnO2 CILs obtain a high efficiency of 12.74%. To the best of our knowledge, this work presents the first example for the high-performance and large-area OSCs with the thickness-insensitive SnO2 CIL.

关键词： organic solar cells printable Sn02 cathode interlayer thickness-insensitivity large-area

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Revival of Insulating Polyethylenimine by Creatively Carbonizing with Perylene into Highly Crystallized Carbon Dots as the cathode interlayer for High-Performance Organic Solar Cells

Revival of Insulating Polyethylenimine by Creatively Carboni...

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第九届新型太阳能材料科学与技术学术研讨会

作者： Yiman Dong Yizhao Qing Rui Shi Gangfeng Su Huanyu Ma Qi Dang Zhanao Tan Beijing Advanced Innovation Center for Soft Matter Science and Engineering State Key Laboratory of Organic-Inorganic Composites Beijing University of Chemical Technology

The development of new electron transporting layer(ETL) materials to improve the charge carrier extraction and collection ability between cathode and the active layer has been demonstrated to be an effective approach to enhance the photovoltaic performance of organic solar cells(OSCs). Herein, water-soluble carbon dots(CDs) as ETL material have been creatively synthesized by a vigorous chemical reaction between polyethylenimine(PEI) and 3,4,9,10-perylenetetracarboxylic dianhydride(PTCDA) via a simple one-step hydrothermal method. Taking full advantage of the high electron transfer property of PTCDA and the work function(WF) reduction ability of PEI, CD gained high electron mobility due to its large π-conjugated area and reduced the WF of indium tin oxide(ITO) by 0.75 e V. As for the photovoltaic performance of devices, inverted OSCs based on CDs have achieved a high power conversion efficiency(PCE) of 17.35%, exhibiting no burn-in effect with no reduction in PCE after more than 4000 h of storage. The successful application of CDs in OPV has developed a new avenue for designing efficient ETL materials that benefits the photovoltaic performance of OSCs.

关键词： carbon dot cathode interlayer electron transporting layer interface engineering inverted organic solar cell

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Ionic liquids with variable cations as cathode interlayer for conventional polymer solar cells

Ionic liquids with variable cations as cathode interlayer fo...

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第四届新型太阳能电池学术研讨会

作者： Wei Yu Xin Guo Can Li State Key Laboratory of Catalysis Dalian National Laboratory for Clean Energy Dalian Institute of Chemical Physics Chinese Academy of Sciences

Interfacial layer materials have been demonstrated to be crucial for high-efficiency polymer solar cells(PSCs).In this work, we use ionic liquid(IL) as cathode interfacial layer(CIL) for highly efficient conventional PSCs(c-PSCs) and investigate functions of ILs with different cations and substituents.Employing IL as the CIL, PBDTTT-C:PCBM-based c-PSC affords a power conversion efficiency(PCE) of 7.29%, much higher than that without the CIL(2.78%) and that with Ca/Al electrode(6.18%).When the photoactive layer is a PTB7-Th:PCBM blend, a higher PCE of 8.67% can be obtained.The ILs reduce the energy barrier due to the existence of interfacial dipole in c-PSCs, leading to increased electron and hole mobilities, reduced series resistance and enhanced contact at the cathode interface.Meanwhile, alkyl chain-substituted ILs offer higher fill factor and PCE than aromatic groups-substituted analogue, which is mainly contributed to more balanced electron and hole mobilities.This work suggests that the ILs are qualified candidates as the CIL for c-PSCs and that one should take the substitution effect into account when choosing a CIL from a large library of materials.

关键词： Conventional polymer solar cells Ionic liquids cathode interlayer Mobility

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Printable SnO2 cathode interlayer with up to 500 nm thickness-tolerance for high-performance and large-area organic solar cells

Printable SnO2 cathode interlayer with up to 500 nm thicknes...

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第七届新型太阳能电池材料科学与技术学术研讨会

作者： Shuai Zhang Yiming Bai Yiman Dong Wenbo Huo Yuting Liu Ruyue Wang Zhan'ao Tan Beijing Advanced Innovation Center for Soft Matter Science and Engineering Beijing University of Chemical Technology State Key Laboratory of Alternate Electrical Power System with Renewable Energy Sources North China Electric Power University

The printable electrode interlayer with excellent thickness tolerance is crucial for mass production of organic solar cells(OSCs) by solution-based print techniques.Herein,high-quality printable SnO films are simply fabricated by spin-coating or blade-coating the chemical precipitated SnO colloid precursor with post thermal annealing treatment.The interfacial electron trap density of SnO cathode interlayers(CILs) are very low and show negligible increase as the thicknesses increase from 10 to 160 nm,resulting in slight change of the power conversion efficiencies(PCEs) of the PM6:Y6 based OSCs from 16.10% to 13.07%.For blade-coated SnO CIL,the PCE remains high up to 12.08% even the thickness of SnO CIL is high up to 530 nm.More strikingly,the large-area OSCs of 100 mm with printed SnO CILs obtain a high efficiency of 12.74%.

关键词： organic solar cells printable SnO2 cathode interlayer thickness-insensitivity large-area

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Perylene-diimide derived organic photovoltaic materials

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Science China Chemistry 2022年第3期65卷 462-485页

作者： Ming Zhang Yang Bai Chenkai Sun Lingwei Xue Haiqiao Wang Zhi-Guo Zhang State Key Laboratory of Organic/Inorganic Composites Beijing Advanced Innovation Center for Soft Matter Science and EngineeringBeijing University of Chemical TechnologyBeijing 100029China College of Chemistry and Green Catalysis CenterZhengzhou UniversityZhengzhou 450001China School of Chemical and Environmental Engineering Pingdingshan UniversityPingdingshan 467000China Beijing Engineering Research Center for the Synthesis and Applications of Waterborne Polymers Beijing University of Chemical TechnologyBeijing 100029China

In organic solar cells(OSCs), the material design on photovoltaic layers and interlayers has significantly contributed to the rapid progress of the device performance. Perylene-diimides(PDIs), owing to their distinct advantages of high electron affinity, high electron mobility and facial chemical modification, are being widely studied in OSCs, especially designed as photovoltaic acceptors and cathode interlayers. In this review, recent progress on those PDI derived photovoltaic materials is systematically summarized. Due to the different working mechanism in devices, the design strategies on modification of the parent PDI units towards their application as acceptors and cathode interlayers are explained. After disclosing the fundamental structure-property relationships, we disclose some common features in the design of those tailor-made PDI-based photovoltaic materials, and we also highlight the challenges and opportunities in improving their device performance in the future.

关键词： organic solar cells perylene-diimides photovoltaic acceptor cathode interlayer

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