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Semi-crystalline photovoltaic polymers with siloxane-terminated hybrid side-chains

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Science China Chemistry 2017年第4期60卷 528-536页

作者： Yuxiang Li Seyeong Song Song Yi Park Jin young Kim han young woo Department of Cogno-Mechatronics Engineering Pusan National University Miryang 627-706 Republic of Korea Department of Energy and Chemical Engineering Ulsan National Institute of Science and Technology Ulsan 689-798 Republic of Korea Department of Chemistry Korea University Seoul 136-713 Republic of Korea

Three types of semi-cry stalline photovoltaic polymers were synthesized by incorporating a siloxane-terminated organic/inorganic hybrid side-chain and changing the number of fluorine substituents.A branch point away from a polymer main backbone in the siloxane-containing side-chains and the intra-and/or interchain noncovalent coulombic interactions enhance a chain planarity and facile interchain *** resulting polymers formed strongly agglomerated films with high roughness,suggesting strong intermolecular *** optical band gap of ca.1.7 eV was measured for all polymers with a pronounced shoulder peak due to tight π-π *** increasing the fluorine substituents,the frontier energy levels decreased and preferential face-on orientation was *** siloxane-terminated side-chains and fluorine substitution promoted the intermolecular packing,showing well resolved lamellar scatterings up to(300) for this series of polymers in the grazing incidence wide angle X-ray scattering *** PPsiDTBT,PPsiDTFBT and PPsiDT2 FBT devices showed a power conversion efficiency of 3.16%,4.40%and 5.65%,respectively,by blending with PC_(71)***-type bimolecular charge recombination was similar for three polymeric solar *** main loss in the photocurrent generation for PPsiDTBT:PC_(71)BM was interpreted to originate from the trap assisted charge recombination by measuring light-intensity dependent short-circuit current density(J_(SC)) and open-circuit voltage(V_(Oc)).Our results provide a new insight into the rational selection of solubilizing substituents for optimizing crystalline interchain packing with appropriate miscibility with PC71 BM for further optimizing polymer solar cells.

关键词： siloxane side-chain fluorine substitution semi-crystalline charge transport

High-efficiency organic solar cells enabled by an alcohol-washable solid additive

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Science China Chemistry 2021年第12期64卷 2161-2168页

作者： Yuanpeng Xie Hwa Sook Ryu Lili han Yunhao Cai Xiaopeng Duan Donghui Wei han young woo Yanming Sun School of Chemistry Beihang UniversityBeijing100191China Department of Chemistry College of ScienceKU-KIST Graduate School of Converging Science and TechnologyKorea UniversitySeoul136-713Korea College of Chemistry and Molecular Engineering Zhengzhou UniversityZhengzhou450001China

The solvent additive strategy has been widely utilized to boost the power conversion efficiency(PCE)of organic solar cells(OSCs).However,the residual solvent additive in the active layer tends to induce a gradual morphology degradation and further influences the long-term stability of ***,a solid additive,1,4-diiodobenzene(DIB),was introduced to fabricate efficient *** found that the treatment of DIB can lead to optimized morphology to form a bicontinuous network with intensified intermolecular packing in the donor and acceptor ***,DIB can be easily removed from the active layer via a simple alcohol washing process and no further post-thermal annealing is needed,which is desirable for large-scale manufacturing of *** a result,high efficiencies of 17.47%for PM6:Y6 and 18.13%(certified as 17.7%)for PM6:BTP-eC9 binary OSCs are achieved,which are among the highest efficiencies reported for binary OSCs thus ***,OSCs fabricated with DIB also exhibit superior stability compared with the as-cast and traditional solvent additive processed ***,DIB was successfully applied in different active layers,manifesting its general *** work provides a feasible approach to enhance both the efficiency and stability of OSCs.

关键词： organic solar cells solid additive alcohol washing process efficiency stability

Heteroatom substitution-induced asymmetric A–D–A type non-fullerene acceptor for efficient organic solar cells

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Journal of Energy Chemistry 2020年第1期29卷 144-150,I0006页

作者： Chao Lia Jiali Song Yunhao Cai Guangchao han Wenyu Zheng Yuanping Yi Hwa Sook Ryu han young woo Yanming Sun School of Chemistry Beihang UniversityBeijing 100191China Beijing National Laboratory for Molecular Science Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijing 100190China Department of Chemistry College of ScienceKorea UniversitySeoul 136-713Republic of Korea

Research on asymmetric A–D–A structured non-fullerene acceptors has lagged far behind the development of symmetric *** this contribution,by simply replacing one sulfur atom in indacenodithiophene unit with a selenium atom,an asymmetric building block Se PT and a corresponding asymmetric non-fullerene acceptor Se PT-IN have been *** Se PT-IN achieved a high efficiency of 10.20% in organic solar cells when blended with PBT1-C,much higher than that of symmetric TPT-IN counterpart(8.91%).Our results demonstrated an effective heteroatom substitution strategy to develop asymmetric A–D–A structured non-fullerene acceptors.

关键词： Asymmetric non-fullerene acceptors Heteroatom substitution Organic solar cells Power conversion efficiency

Germinant ZnO nanorods as a charge-selective layer in organic solar cells

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Journal of Materials Science & Technology 2020年第20期52卷 89-94页

作者： Kunsik An Jaehoon Kim Mohammad Afsar Uddin Seunghyun Rhee Hyeok Kim Kyung-Tae Kang han young woo Changhee Lee Department of Electrical and Computer Engineering Seoul National UniversitySeoul 08826Republic of Korea Micro/Nano Process Group Korea Institute of Industrial Technology(KITECH)Sangnok-guAnsan-si 15588Republic of Korea Department of Chemistry College of ScienceKorea UniversitySeoul 02841Republic of Korea Department of Electrical Engineering Engineering Research Institute(ERI)Gyeongsang National UniversityJinju 52828Republic of Korea

A facile method was introduced and demonstrated to synthesize zinc oxide(ZnO) nanorods(NRs) as an electron transporting layer(ETL) for organic solar cells(OSCs).Hydrothermal synthesis of the NRs showed a constant growth rate of 5.5 nm min-1 from germination to sub-micrometer *** properties were characterized using scanning electron microscopy(SEM),transmission electron microscopy(TEM),absorption spectrophotometry and so *** on these measurements,the germinant growth mechanism and its corresponding orientation characteristics were *** an ETL of the OSCs,ZnO NRs enhance the charge extraction from the active layer due to their increased interfacial surface area,but there is an optimal length because of the shunt path formation and UV absorption of long ZnO *** a re sult,the OSC with the ZnO NRs as ETL shows power conversion efficiency(PCE) up to 6.2%.The J-V characteristics and incident photon-to-current conversion efficiency(IPCE) measurement also reveal that the efficiency enhancement is an assembly of individual results from optical,physical and electrical characteristic of the ZnO NRs.

关键词： ZnO nanorods Solar cells Self-assembly Oriented growth mechanism Hydrothermal synthesis

Optimization of solvent swelling for efficient organic solar cells via sequential deposition

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Materials Reports(Energy) 2021年第4期1卷 77-83页

作者： Qiaogan Liao Bangbang Li Huiliang Sun Chang woo Koh Xianhe Zhang Bin Liu han young woo Xugang Guo Department of Materials Science and Engineering Southern University of Science and TechnologyShenzhen 518055GuangdongPR China Guangdong Provincial Key Laboratory of Functional Oxide Materials and Devices Southern University of Science and Technology(SUSTech)Shenzhen 518055GuangdongPR China School of Materials Science and Engineering Harbin Institute of TechnologyHarbin 150001PR China Research Institute for Natural Sciences Department of ChemistryKorea UniversitySeoul 136-713South Korea

Compared to bulk heterojunction(BHJ)organic solar cells(OSCs)prepared by the blend casting in“one step process”,sequential deposition(SD)processed OSCs can realize an ideal profile of vertical component distribution due to the swelling of polymer ***,we did trials on several kinds of second solvents for swelling the polymer layer,and investigated the packing structure and morphology of the swollen films and the performance of the resulting *** found that an optimized morphology can be achieved by solvent swelling while using orthodichlorobenzene(o-DCB)as the second layer processing-solvent,with polymer donor PffBT-3 as bottom layer,PC71BM as top layer and bicontinuous networks in the *** solvent swelling process also makes the SD method exempt from thermal annealing *** device based on SD yields a power conversion effi-ciency(PCE)up to 8.7%without any post-treatment,outperforming those from the devices based on SD using other solvents and that(7.06%)from BHJ device,*** also extended the use of this approach to allpolymer blend system,and successfully improved the efficiency from 4.72%(chloroform)to 9.35%(o-DCB),which is among the highest PCEs in all-polymer-based OSCs fabricated with SD *** results demonstrate that the swelling of the polymer by the second layer solvent is a necessity for SD,paving the way towards additivefree high-performance OSCs.

关键词： Organic solar cells Bulk heterojunction Sequential deposition Solvent swelling Vertical phase separation Second solvent

A High Dielectric N-Type Small Molecular Acceptor Containing Oligoethyleneglycol Side-Chains for Organic Solar Cellst

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Chinese Journal of Chemistry 2018年第3期36卷 199-205页

作者： Bomee Jang Changyeon Lee young woong Lee Donguk Kim Mohammad Afsar Uddin Felix Sunjoo Kim Bumjoon J. Kim han young woo Department of Chemistry Korea University Seoul 02841 Republic of Korea Department of Chemical and Biornolecular Engineering Korea Advanced Institute of Science and Technology (KAIST) Daejeon 34141 Republic of Korea School of Chemical Engineering and Materials Science Chung-Ang UniversitySeoul 06974 Republic of Korea

We report a new small molecular acceptor, ITIC-OEG, which is based on indacenodithieno[3,2-b]thiophene and 1,1-（dicyanomethylene）-3- indanone including oligoethyleneglycol （OEG） side-chains. ITIC-OEG was found to have higher dielectric constant （ε1=5.6} than that of a reference molecule of ITIC with normal alkyl substituents （ε1=3.9）. The dielectric constant of medium influences significantly the exciton binding energy and the resulting charge separation and recombination. The optical, electrochemical and morphological properties of ITIC-OEG and its photovoltaic characteristics were investigated by blending with a semi-crystalline donor polymer, PPDT2FBT, with comparison to those of ITIC. ITIC-OEG shows more red-shifted absorption and stronger crystalline packing than ITIC. However, the lower photovoltaic performance （with 1.58% power conversion efficiency, PCE） was measured for PPDT2FBT-ITIC-OEG, compared to PPDT2FBT：ITIC （5..52% PCE）. The incompatibility between PPDT2FBT and ITIC-OEG （due to high hydrophilic nature of OEG chains） resulted in poor intermixing with large domain separation over 300 nm, showing inefficient charge separation and significant charge recombination. Therefore, to investigate the effect of dielectric constant of the materials on the charge separation and recombination, the blend morphology of the PPDT2FBT：ITIC-OEG should be optimized first by improving their miscibility and phase separation.

关键词： N-type small molecule dielectric constant morphology organic solar cells

Organic solar cells based on chlorine functionalized benzo[1,2-b:4,5-b′]difuran-benzo[1,2-c:4,5-c′]dithiophene-4,8-dione copolymer with efficiency exceeding 13%

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Science China Chemistry 2020年第4期63卷 483-489页

作者： Linglong Ye Xueshan Li Yunhao Cai Hwa Sook Ryu Guangkai Lu Donghui Wei Xiaobo Sun han young woo Songting Tan Yanming Sun School of Chemistry Beihang UniversityBeijing 100191China Department of Chemistry College of ScienceKorea UniversityAnam-ro 145Seongbuk-guSeoul 136-713Republic of Korea The College of Chemistry and Molecular Engineering Zhengzhou UniversityZhengzhou 450001China Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education College of ChemistryXiangtan UniversityXiangtan 411105China

Benzo[1,2-b:4,5-b′]dithiophene(BDT) has been widely used to construct donor-acceptor(D-A) copolymers in organic solar cells(OSCs). However, benzo[1,2-b:4,5-b′]difuran(BDF), an analogue of BDT, has received less attention than BDT. The photovoltaic performance of BDF copolymers has lagged behind that of BDT copolymers. Here, we designed and synthesized two BDF copolymers, PBF1-C and PBF1-C-2Cl. PBF1-C-2Cl, which is composed of BDF and benzo[1,2-c:4,5-c′]dithiophene-4,8-dione connected by a chlorinated thiophene π-bridge, displays a low-lying highest occupied molecular orbital energy level,which helps in yielding a high open-circuit voltage(Voc) in OSCs. As a result, when blended with Y6, PBF1-C-2Cl-based devices showed a high Voc of 0.83 V and a power conversion efficiency(PCE) of 13.10%. To the best of our knowledge, the PCE of 13.10% is among the highest efficiency values for OSCs based on BDF copolymers.

关键词： organic solar cells benzo[1,2-b,5-b′]difuran benzo[1,2-c,5-c′]dithiophene-4,8-dione chlorinated thiophene π-bridge

Over 18.2% efficiency of layer–by–layer all–polymer solar cells enabled by homoleptic iridium(Ⅲ)carbene complex as solid additive

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Science Bulletin 2024年第18期69卷 2862-2869页

作者： hang Zhou Yingjie Sun Miao Zhang Yuheng Ni Fenghua Zhang Sang young Jeong Tianhuan Huang Xiong Li han young woo Jian Zhang Wai-Yeung Wong Xiaoling Ma Fujun Zhang Key Laboratory of Luminescence and Optical Information(Ministry of Education) Beijing Jiaotong UniversityBeijing 100044China Department of Applied Biology and Chemical Technology and Research Institute for Smart Energy The Hong Kong Polytechnic UniversityHong Kong 999077China Department of Physics Beijing Technology and Business UniversityBeijing 100048China Organic Optoelectronic Materials Laboratory Department of ChemistryCollege of ScienceKorea UniversitySeoul 02841Republic of Korea School of Materials Science and Engineering Engineering Research Center of Electronic Information Materials and DevicesMinistry of EducationGuangxi Key Laboratory of Information MaterialsGuilin University of Electronic TechnologyGuilin 541004China Tangshan Research Institute of Beijing Jiaotong University Tangshan 063000China

The vertical phase distribution of active layers plays a vital role in balancing exciton dissociation and cha rge transport for achieving efficient polymer solar cells(PSCs).The layer-by-layer(LbL)PSCs are commonly prepared by using sequential spin-coating method from donor and acceptor solutions with distinct solvents and solvent *** enhanced exciton dissociation is expected in the LbL PSCs with efficient charge transport in the relatively neat donor or acceptor *** this work,a series of LbL all-polymer solar cells(APSCs)were fabricated with PM6 as donor and PY-DT as acceptor,and triplet material m-Ir(CPmPB)_(3)is deliberately incorporated into PY-DT layer to prolong exciton lifetimes of active *** power conversion efficiency(PCE)of LbL APSCs is improved to 18.24%from 17.32%by incorporating 0.3 wt%m-Ir(CPMPB)_(3)in PY-DT layer,benefiting from the simultaneously enhanced short-circuit current density(Isc)of 25.17 mA cm^(-2)and fill factor(FF)of 74.70%.The enhancement of PCE is attributed to the efficient energy transfer of m-Ir(CPmPB)_(3)to PM6 and PY-DT,resulting in the prolonged exciton lifetime in the active layer and the increased exciton diffusion *** efficient energy transfer from m-Ir(CPmPB)_(3)to PM6 and PY-DT layer can be confirmed by the increased photoluminescence(PL)intensity and the prolonged PL lifetime of PM6 and PY-DT in PM6+m-Ir(CPmPB)_(3)and PY-DT+m-Ir(CPmPB)_(3)*** study indicates that the triplet material as solid additive has great potential in fabricating efficient LbL APSCs by prolonging exciton lifetimes in active layers.

关键词： Layer-by-layer All-polymer solar cells Additive strategy Triplet material Energy transfer

Regioisomeric Polymer Semiconductors Based on Cyano-Functionalized Dialkoxybithiophenes:Structure-Property Relationship and Photovoltaic Performance

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Transactions of Tianjin University 2022年第5期28卷 385-397页

作者： Qingqing Bai Jun Huang han Guo Suxiang Ma Jie Yang Bin Liu Kun Yang Huiliang Sun han young woo Li Niu Xugang Guo Center for Advanced Analytical Science School of Chemistry and Chemical EngineeringGuangzhou UniversityGuangzhou 510006China Department of Materials Science and Engineering Southern University of Science and TechnologyShenzhen 518055China State Key Laboratory of Luminescent Materials and Devices South China University of TechnologyGuangdong 510640China Department of Chemistry Korea UniversitySeoul 136-713South Korea

Cyano substitution is vital to the molecular design of polymer semiconductors toward highly efficient organic solar ***,how regioselectivity impacts relevant optoelectronic properties in cyano-substituted bithiophene systems remain poorly *** regioisomeric cyano-functionalized dialkoxybithiophenes BT_(HH),BT_(HT),and BT_(TT) with headto-head,head-to-tail,and tail-to-tail linkage,respectively,were synthesized and characterized in this *** resulting polymer semiconductors(PBDTBTs)based on these building blocks were prepared *** regiochemistry and property relationships of PBDTBTs were investigated in *** BTHH moiety has a higher torsional barrier than the analogs BT_(HT) and BT_(TT),and the regiochemistry of dialkoxybithiophenes leads to fine modulation in the optoelectronic properties of these polymers,such as optical absorption,band gap,and energy levels of frontier molecular *** field-effect transistors based on PBDTBT_(HH) had higher hole mobility(4.4×10^(-3) cm^(2)/(V·s))than those(ca.10^(-4) cm^(2)/(V·s))of the other two polymer *** different short-circuit current densities and fill factors were obtained in polymer solar cells using PBDTBTs as the electron *** difference was probed in greater detail by performing space-charge-limited current mobility,thin-film morphology,and transient photocurrent/photovoltage *** findings highlight that the BTHH unit is a promising building block for the construction of polymer donors for highperformance organic photovoltaic cells.

关键词： Cyano substitution Regioselectivity Organic photovoltaic cells Polymer semiconductors Mobility