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From Perylene Dimide Polymers to Fused-Ring Electron Acceptors:A 15-Year Exploration Journey of Nonfullerene Acceptors

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Chinese Journal of Chemistry 2022年第13期40卷 1592-1607页

作者： Jiayu Wang xiaowei zhan Key Laboratory of Polymer Chemistry and Physics of Ministry of Education School of Materials Science and EngineeringPeking UniversityBeijing100871China

Fullerene derivatives are classic electron acceptor materials for organic solar cells (Oscs) but possess some intrinsic drawbacks such as weak visiblelightabsorption,limitedoptoelectronic property tunability,dificult purification and photochemical/morphological *** area bottleneck restricting further development of this field. Ourgroup pioneered the exploration of novel nonfulerene acceptors in China in 2006,andinitiated the research of two representative acceptor systems, rylene dimide polymer and fused-ring electron acceptor (FREA).FREA breaks the theoreticalefficiencylimit of fullerene-based OsCs (-13%) and promotes the whole field to an unprecedented prosperity with efficiency of 20%, heraldinga nonfullerene era for *** this review, we revisit 15-year nonfullerene exploration journey,summarize the design principles,molecular engineeringstrategies, physical mechanisms and device applications of these two nonfullerene acceptor systems, and propose some possible researchtopics in the nearfuture.

关键词： Energyconversion Semiconductors Electron-deficient compounds Rylene dimides Fused-ring electron acceptors

A new perspective for organic solar cells: triplet nonfullerene acceptors

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Science China Chemistry 2018年第6期61卷 637-638页

作者： xiaowei zhan Yongfang Li Department of Materials Science and Engineering College of Engineering Key Laboratory of Polymer Chemistry and Physics of Ministry of Education Peking University Institute of Chemistry Chinese Academy of Sciences

In the last decade,the rapid development of bulk heterojunction(BHJ)organic solar cells(OSCs)has been witnessed and the power conversion efficiencies(PCEs)have reached over 13%[1].Though fullerene derivatives have played dominant roles for BHJ OSCs,nonfullerene acceptors recently showed a promising potential in replacing fullerene derivatives since they possess readily tunable bandgaps,strong and broad absorption,and low cost production[2,3].

关键词：太阳能电池 fullerene 器官字节三位变换效率衍生物 PCE

Effects of Thieno[3,2-b]thiophene Number on Narrow-Bandgap Fused-Ring Electron Acceptors

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Chinese Journal of Polymer Science 2022年第8期40卷 914-920,I0008页

作者： Tengfei Li Guilong Cai Yuze Lin Xinhui Lu xiaowei zhan Key Laboratory of Polymer Chemistry and Physics of Ministry of Education School of Materials Science and EngineeringPeking UniversityBeijing100871China Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijing100190China Department of Physics The Chinese University of Hong KongHong Kong999077China

We synthesize and compare four near-infrared absorbing fused-ring electron acceptors named as nTTIC(n=2,3,4,and 5),based on different number of thieno[3,2-b]thiophene(TT)unit as the electron-donating *** increasing the TT unit,absorption spectrum of the TTIC series red shifts,and the highest occupied molecular orbital(HOMO)upshifts *** is worth noting that 4TTIC and 5TTIC exhibit absorption edges approaching 1100 nm,which is the photoresponse limit of solar cells based on crystal *** the TTIC series acceptors are blended with polymer donor PM6,the binary-blend organic solar cells based on 3TTIC show the best power conversion efficiency(PCE)of 13.1%.In contrast,2TTIC-based devices exhibit relatively lower PCE of 8.32%,mainly caused by the larger energy loss and blue-shifted *** to insufficient driving force of charge separation caused by very high HOMO,4TTIC and 5TTIC show poor PCEs lower than 3%.

关键词： Thieno[3,2-b]thiophene Near-infrared absorption Fused-ring electron acceptor Nonfullerene Organic solar cell

Effect of electron-withdrawing units on triphenylamine-based small molecules for solution-processed organic solar cells

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Science China Chemistry 2015年第2期58卷 331-338页

作者： Yifan Wang Huitao Bai Pei Cheng Mingyu zhang xiaowei zhan CAS Key Laboratory of Organic Solids Institute of Chemistry Chinese Academy of Sciences University of Chinese Academy of Sciences Department of Materials Science and Engineering College of Engineering Peking University

Organic small molecules （TPA-BT3T, TPA-PT3T, and TPA-DFBT3T） using triphenylamine as a donor unit, terthiophene as a bridge, and benzo-2,1,3-thiadiazole （BT）, [1,2,5]thiadiazolo[3,4-e]pyridine （PT） or 5,6-difluorobenzo[c][1,2,5]thiadiazole （DFBT） as an acceptor unit were designed and synthesized through Suzuki coupling reactions. These molecules exhibited good thermal stability with decomposition temperatures over 380℃ and broad absorption from 300 to 700 nm. Photovoltaic devices were fabricated with these small molecules as donors and PC71BM as an acceptor. The TPA-BT3T based devices exhibited a power conversion efficiency of 2.89%, higher than those of the TPA-PT3T- and TPA-DFBT3T-based devices （1.34% and 1.54% respectively）. The effects of electron-withdrawing units on absorption, energy level, charge transport, morphology, and photovoltaic properties also were investigated.

关键词： organic solar cell small molecule triphenylamine electron-withdrawing unit

Perylene Diimide-Based Oligomers and Polymers for Organic Optoelectronics

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Accounts of Materials Research 2022年第3期3卷 309-318页

作者： Pei Cheng Xingang Zhao xiaowei zhan Key Laboratory of Polymer Chemistry and Physics of Ministry of Education School of Materials Science and EngineeringPeking UniversityBeijing 100871China College of Polymer Science and Engineering State Key Laboratory of Polymer Material and EngineeringSichuan UniversityChengdu 610065China Key Laboratory of Eco-functional Polymer Materials of Ministry of Education College of Chemistry and Chemical EngineeringNorthwest Normal UniversityLanzhou 730070China

CONSPECTUS:Perylene diimide(PDI)as a classical dye has some advantages,such as structural diversity,tunable optical and electronic properties,strong light absorption,high electron affinity,and good electron-transporting properties and *** PDI-based oligomers and polymers are good candidates for n-type semiconductors in organic electronics and photonic devices.A polymer solar cell(PSC)that converts sunlight into electricity is a promising renewable and clean energy technology and has some superiorities,such as simple preparation and being lightweight,low cost,semitransparent,and *** a long time,fullerene derivatives(e.g.,PCBM)have been the most important electron acceptors used in the active layer of ***,PCBM suffers from some disadvantages,for example,weak absorption,a large amount of energy loss,and unstable *** to PCBM,PDI-based materials present some advantages:intense visible-light absorption;lowest unoccupied molecular orbital(LUMO)energy levels can be modulated to achieve a suitable charge separation driving force and high open-circuit voltage(V_(OC));and the molecular configuration can be adjusted to achieve morphology ***,PDI-based oligomers and polymers are widely used as electron acceptors in the active layer of *** addition,PDI-based oligomers and polymers are widely used as n-type semiconductors in other electronic and photonic devices,such as organic field-effect transistors(OFETs),light-emitting diodes,lasers,optical switches,and photodetectors.

关键词： stability absorption separation

Fused thienobenzene-thienothiophene electron acceptors for organic solar cells

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Journal of Energy Chemistry 2019年第10期28卷 58-65页

作者： Ye Xu Haotian Jiang Tsz-Ki Lau Jingshuai Zhu Jiayu Wang Xinhui Lu xiaowei zhan Yuze Lin Department of Chemistry Capital Normal UniversityBeijing 100048China Department of Materials Science and Engineering Key Laboratory of Polymer Chemistry and Physics of Ministry of EducationCollege of EngineeringPeking UniversityBeijing 100871China Department of Physics The Chinese University of Hong KongNew TerritoriesHong KongChina

Small molecule ladder-type heteroarenes IHBT-2F is designed and synthesized with strong electrondonating and molecular packing properties, where the central unit, fused thienobenzene-thienothiphene (IHBT), is attached with the strong electron-deficient 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2FIC) as the end group. The counterpart IDBT-2F with indancenodibenzothiophene (IDBT) mainchain is sythesized for comparison, in which thieno[3,2-b]thiophene (TT) core of IHBT is replaced by benzene core. Relative to benzene-core IDBT-2F, TT-core IHBT-2F shows a much higher highest occupied molecular orbital energy level (IHBT-2F:-5.46 eV;IDBT-2F:-5.72 eV) and significantly redshifted absorption, due to the π-donor capability of the sulfur atom, the larger π-conjugation and stronger intermolecular π-π stacking. The as-cast organic solar cells (OSCs) based on blends of PTB7-Th donor and IHBT-2F acceptor without additional treatments exhibit power conversion efficiencies (PCEs) as high as 8.74%, which is much higher than that of PTB7-Th:IDBT-2F (6.73%).

关键词： Organic solar cell Fused ring electron acceptor Thienobenzene Non-fullerene

Comparison of conventional and inverted structures in fullerene-free organic solar cells

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Journal of Energy Chemistry 2015年第6期24卷 744-749页

作者： Yifan Wang Huitao Bai xiaowei zhan Beijing National Laboratory for Molecular Sciences Institute of ChemistryChinese Academy of Sciences University of Chinese Academy of Sciences Department of Materials Science and Engineering College of EngineeringKey Laboratory of Polymer Chemistry and Physics of Ministry of EducationPeking University

A n-type small molecule DC-IDT2E with 4,4,9,9-tetrakis（4-hexylphenyl）-indaceno[1,2-b：5,6-bt]dithiophene as a central building block, furan as rr-bridges, and 1,1 -dicyanomethylene-3-indanone as end acceptor groups, was synthesized and used as an electron acceptor in solution-processed organic solar cells （OSCs）. DC-IDT2F exhibited good thermal stability, broad and strong absorption in 500-850 rim, a narrow bandgap of 1.54 eV, LUMO of-3.88 eV, HOMO of-5.44 eV and an electron mobility of 6.5 × 10-4 cm2/（V.s）. DC-IDT2F-based OSCs with conventional and inverted structures exhibited power conversion efficiencies of 2.26 and 3.08% respec- tively. The effect of vertical phase separation and morphology of the active layer on the device performance in the two structures was studied.

关键词： Organic solar cells Non-fullerene acceptors Fullerene free Vertical phase separation Inverted structure

The impact of fluorination on both donor polymer and non-fullerene acceptor:The more fluorine,the merrier

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Nano Research 2019年第9期12卷 2400-2405页

作者： Nicole Bauer Qianqian zhang Jeromy James Rech Shuixing Dai Zhengxing Peng Harald Ade Jiayu Wang xiaowei zhan Wei You Department of Chemistry University of North Carolina at Chapel HillNorth Carolina 27599USA Department of Materials Science and Engineering College of EngineeringKey Laboratory of Polymer Chemistry and Physics of Ministry EducationPeking UniversityBeijing 100871China Department of Physics and ORaCEL North Carolina State UniversityRaleighNorth Carolina 27695USA

Fluorination of the donor polymer or non-fullerene acceptor (NFA) in an organic photovoltaic device is an effective method to improve device *** there have been many studies on donor polymer fluorination,blends containing both a fluorinated donor and fluorinated NFA have rarely been *** this study,we use two donor polymers (4'-FT-HTAZ and 4'-FT-FTAZ) and two NFAs (ITIC-Th and ITIC-Th1) with different amounts of fluorine (from 2F to 6F) to investigate how the degree of fluorination in a blend impacts device *** find that fluorinating the NFA leads to a higher short-circuit current density (Jsc) and fill factor (FF),however,the open-circuit voltage (Voc) is decreased due to a depressed lowest unoccupied molecular orbital (LUMO) *** additional fluorine to the donor polymer does not have a large effect on the Jsc or FF,but it does lead to an improved *** fluorinating the NFA and having more fluorine on the donor polymer,we obtain both a high Jsc and Voc simultaneously,leading to a power conversion efficiency over 10% in the case of 4'-FT-FTAZ:ITIC-Th1,which has the most amount of fluorine (6F).

关键词： organic solar cells non-fullerene acceptors fluorination bulk heterojunction

Ultrafast and broadband photodetectors based on a perovskite/organic bulk heterojunction for large-dynamic-range imaging

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Light(Science & Applications) 2020年第1期9卷 1723-1730页

作者： Chenglong Li Hailu Wang Fang Wang Tengfei Li Mengjian Xu Hao Wang Zhen Wang xiaowei zhan Weida Hu Liang Shen State Key Laboratory of Integrated Optoelectronics College of Electronic Science and EngineeringJilin University2699 Qianjin StreetChangchun 130012China State Key Laboratory of Infrared Physics Shanghai Institute of Technical PhysicsChinese Academy of Sciences500 Yutian RoadShanghai 200083China University of Chinese Academy of Sciences Beijing 100049China Department of Materials Science and Engineering College of EngineeringKey Laboratory of Polymer Chemistry and Physics of Ministry of EducationPeking UniversityBeijing 100871China

Organic-inorganic hybrid perovskite(OIHP)photodetectors that simultaneously achieve an ultrafast response and high sensitivity in the near-infrared(NIR)region are prerequisites for expanding current monitoring,imaging,and optical communication ***,we demonstrate photodetectors constructed by OIHP and an organic bulk heterojunction(BHJ)consisting of a low-bandgap nonfullerene and polymer,which achieve broadband response spectra up to 1μm with a highest external quantum efficiency of approximately 54%at 850 nm,an ultrafast response speed of 5.6 ns and a linear dynamic range(LDR)of 191 *** sensitivity,ultrafast speed and a large LDR are preeminent prerequisites for the practical application of ***,due to the high-dynamicrange imaging capacity,high-quality visible-NIR actual imaging is achieved by employing the OIHP *** believe that state-of-the-art OIHP photodetectors can accelerate the translation of solution-processed photodetector applications from the laboratory to the imaging market.

关键词： heterojunction dynamic photodetector