J. Semicond. > 2020, Volume 41 > Issue 12 > Article Number: 122201

Small molecule donors with different conjugated π linking bridges: Synthesis and photovoltaic properties

Xiyue Dong 1, 2, , Dingqin Hu 1, , Pengyu Chen 3, , Xuexin Dai 4, , Chao Hu 1, , Zeyun Xiao 1, , and Shirong Lu 1, ,

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  • Corresponding author: Zeyun Xiao, xiao.z@cigit.ac.cn; Shirong Lu, Email: lushirong@cigit.ac.cn
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    Abstract: Three small molecule (SM) donors, namely B-T-CN, B-TT-CN and B-DTT-CN, with different π conjugated bridges were synthesized in this research. Interestingly, with the conjugated fused rings of the π linking bridge increasing, the SM HOMO levels exhibit a decline tendency with –5.27 eV for B-T-CN, –5.31 eV for B-TT-CN and –5.40 eV for B-DTT-CN. After blending the SM donors with the fullerene acceptor PC71BM, the all SM organic solar cells (OSCs) achieved high Vocs of 0.90 to 0.96 V. However, the phase separation morphology and molecule stacking are also unexpectedly changed together with the enhancement of conjugated degree of π bridges, resulting in a lower power conversion efficiency (PCE) for the B-DTT-CN:PC71BM device. Our results demonstrate and provide a useful way to enhance OSC Voc and the morphology needs to be further optimized.

    Key words: organic solar cellsmall molecule donormolecule energy levelsmorphology



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    Yang L Y, Zhang S Q, He C, et al. Modulating molecular orientation enables efficient non-fullerene small-molecule organic solar cells. Chem Mater, 2018, 30, 30

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    [1]

    Lu L Y, Zheng T Y, Wu Q H, et al. Recent advances in bulk heterojunction polymer solar cells. Chem Rev, 2015, 115, 12666

    [2]

    Zhao F W, Dai S X, Wu Y, et al. Single-junction binary-blend nonfullerene polymer solar cells with 12.1% efficiency. Adv Mater, 2017, 29, 1700144

    [3]

    Lin Y Z, Zhan X W. Oligomer molecules for efficient organic photovoltaics. Acc Chem Res, 2016, 49, 175

    [4]

    Hou J, Inganäs O, Friend R H, et al. Organic solar cells based on non-fullerene acceptors. Nat Mater, 2018, 17, 119

    [5]

    Liu Q S, Jiang Y F, Jin K, et al. 18% efficiency organic solar cells. Sci Bull, 2020, 65, 272

    [6]

    Cui Y, Yao H F, Zhang J Q, et al. Single-junction organic photovoltaic cells with approaching 18% efficiency. Adv Mater, 2020, 32, 1908205

    [7]

    Chen Y S, Wan X J, Long G K. High performance photovoltaic applications using solution-processed small molecules. Acc Chem Res, 2013, 46, 2645

    [8]

    Collins S D, Ran N A, Heiber M C, et al. Small is powerful: Recent progress in solution-processed small molecule solar cells. Adv Energy Mater, 2017, 7, 1602242

    [9]

    Huo Y, Zhang H L, Zhan X W. Nonfullerene all-small-molecule organic solar cells. ACS Energy Lett, 2019, 4, 1241

    [10]

    Zhou Z C, Xu S J, Song J N, et al. High-efficiency small-molecule ternary solar cells with a hierarchical morphology enabled by synergizing fullerene and non-fullerene acceptors. Nat Energy, 2018, 3, 952

    [11]

    Yuan J, Zhang Y Q, Zhou L Y, et al. Single-junction organic solar cell with over 15% efficiency using fused-ring acceptor with electron-deficient core. Joule, 2019, 3, 1140

    [12]

    Dong X Y, Yang K, Tang H, et al. Improving molecular planarity by changing alky chain position enables 12.3% efficiency all-small-molecule organic solar cells with enhanced carrier lifetime and reduced recombination. Sol RRL, 2020, 4, 1900326

    [13]

    Yue Q H, Wu H, Zhou Z C, et al. 13.7% efficiency small-molecule solar cells enabled by a combination of material and morphology optimization. Adv Mater, 2019, 31, 1904283

    [14]

    Ge J F, Xie L C, Peng R X, et al. 13.34% efficiency non-fullerene all-small-molecule organic solar cells enabled by modulating the crystallinity of donors via a fluorination strategy. Angew Chem Int Ed, 2020, 59, 2808

    [15]

    Gao J, Ge J F, Peng R X, et al. Over 14% efficiency nonfullerene all-small-molecule organic solar cells enabled by improving the ordering of molecular donors via side-chain engineering. J Mater Chem A, 2020, 8, 7405

    [16]

    Chen H Y, Hu D Q, Yang Q G, et al. All-small-molecule organic solar cells with an ordered liquid crystalline donor. Joule, 2019, 3, 3034

    [17]

    Liu Y S, Wan X J, Wang F, et al. High-performance solar cells using a solution-processed small molecule containing benzodithiophene unit. Adv Mater, 2011, 23, 5387

    [18]

    Kan B, Zhang Q, Li M M, et al. Solution-processed organic solar cells based on dialkylthiol-substituted benzodithiophene unit with efficiency near 10%. J Am Chem Soc, 2014, 136, 15529

    [19]

    Zhou J Y, Wan X J, Liu Y S, et al. Small molecules based on benzo[1, 2-b: 4, 5-b’]dithiophene unit for high-performance solution-processed organic solar cells. J Am Chem Soc, 2012, 134, 16345

    [20]

    Ni W, Li M M, Wan X J, et al. A high-performance photovoltaic small molecule developed by modifying the chemical structure and optimizing the morphology of the active layer. RSC Adv, 2014, 4, 31977

    [21]

    Shen S L, Jiang P, He C, et al. Solution-processable organic molecule photovoltaic materials with bithienyl-benzodithiophene central unit and indenedione end groups. Chem Mater, 2013, 25, 2274

    [22]

    Sun K, Xiao Z, Lu S, et al. A molecular nematic liquid crystalline material for high-performance organic photovoltaics. Nat Commun, 2015, 6, 6013

    [23]

    Qiu B, Xue L, Yang Y, et al. All-small-molecule nonfullerene organic solar cells with high fill factor and high efficiency over 10%. Chem Mater, 2017, 29, 7543

    [24]

    Bin H J, Yao J, Yang Y K, et al. High-efficiency all-small-molecule organic solar cells based on an organic molecule donor with alkylsilyl-thienyl conjugated side chains. Adv Mater, 2018, 30, 1706361

    [25]

    Wang Y, Liu B, Koh C W, et al. Facile synthesis of polycyclic aromatic hydrocarbon (PAH)-based acceptors with fine-tuned optoelectronic properties: Toward efficient additive-free nonfullerene organic solar cells. Adv Energy Mater, 2019, 9, 1803976

    [26]

    Wan J H, Xu X P, Zhang G J, et al. Highly efficient halogen-free solvent processed small-molecule organic solar cells enabled by material design and device engineering. Energy Environ Sci, 2017, 10, 1739

    [27]

    Deng D, Zhang Y J, Zhang J Q, et al. Fluorination-enabled optimal morphology leads to over 11% efficiency for inverted small-molecule organic solar cells. Nat Commun, 2016, 7, 13740

    [28]

    Duan T N, Babics M, Seitkhan A, et al. F-Substituted oligothiophenes serve as nonfullerene acceptors in polymer solar cells with open-circuit voltages >1 V. J Mater Chem A, 2018, 6, 9368

    [29]

    Liu D X, Kan B, Ke X, et al. Extended conjugation length of nonfullerene acceptors with improved planarity via noncovalent interactions for high-performance organic solar cells. Adv Energy Mater, 2018, 8, 1801618

    [30]

    Xie Q, Liao X F, Chen L, et al. Random copolymerization realized high efficient polymer solar cells with a record fill factor near 80%. Nano Energy, 2019, 61, 228

    [31]

    Proctor C M, Kuik M, Nguyen T Q. Charge carrier recombination in organic solar cells. Prog Polym Sci, 2013, 38, 1941

    [32]

    Cowan S R, Roy A, Heeger A J. Recombination in polymer-fullerene bulk heterojunction solar cells. Phys Rev B, 2010, 82, 245207

    [33]

    Kirchartz T, Deledalle F, Tuladhar P S, et al. On the differences between dark and light ideality factor in polymer: Fullerene solar cells. J Phys Chem Lett, 2013, 4, 2371

    [34]

    Wheeler S, Deledalle F, Tokmoldin N, et al. Influence of surface recombination on charge-carrier kinetics in organic bulk heterojunction solar cells with nickel oxide interlayers. Phys Rev Appl, 2015, 4, 024020

    [35]

    Liang R Z, Babics M, Savikhin V, et al. Carrier transport and recombination in efficient “all-small-molecule” solar cells with the nonfullerene acceptor IDTBR. Adv Energy Mater, 2018, 8, 1800264

    [36]

    Zhao F W, Wang C R, Zhan X W. Morphology control in organic solar cells. Adv Energy Mater, 2018, 8, 1703147

    [37]

    Duan T N, Gao J, Xu T L, et al. Simple organic donors based on halogenated oligothiophenes for all small molecule solar cells with efficiency over 11%. J Mater Chem A, 2020, 8

    [38]

    Yang L Y, Zhang S Q, He C, et al. Modulating molecular orientation enables efficient non-fullerene small-molecule organic solar cells. Chem Mater, 2018, 30, 30

    [39]

    Vohra V, Kawashima K, Kakara T, et al. Efficient inverted polymer solar cells employing favourable molecular orientation. Nat Photonics, 2015, 9, 403

    [40]

    Jung J, Lee W, Lee C, et al. Controlling molecular orientation of naphthalenediimide-based polymer acceptors for high performance all-polymer solar cells. Adv Energy Mater, 2016, 6, 1600504

    [41]

    Chen S S, Cho H J, Lee J, et al. 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

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    X Y Dong, D Q Hu, P Y Chen, X X Dai, C Hu, Z Y Xiao, S R Lu, Small molecule donors with different conjugated π linking bridges: Synthesis and photovoltaic properties[J]. J. Semicond., 2020, 41(12): 122201. doi: 10.1088/1674-4926/41/12/122201.

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    History

    Manuscript received: 27 April 2020 Manuscript revised: 14 May 2020 Online: Accepted Manuscript: 06 August 2020 Uncorrected proof: 15 September 2020 Published: 08 December 2020

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