Synthesis and side-chain engineering of phenylnaphthalenediimide (PNDI)-based n-type polymers for efficient all-polymer solar cells

Cho, Han‐Hee; Kim, Taesu; Kim, Kimyung; Lee, Changyeon; Kim, Felix Sunjoo; Kim, Bumjoon J.

doi:10.1039/c6ta10978k

Cited by 30 publications

(16 citation statements)

References 70 publications

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“…As stated in earlier section and previous reports, conjugated polymers with shorter and linear alkyl side chains possess more pronounced, densely packed molecular ordering in thin films, and may perform better in devices. However, conjugated polymers with one shorter alkyl side chain usually suffer from poor solubility in common organic solvents.…”

Section: Resultssupporting

confidence: 69%

Pronounced Dependence of All‐Polymer Solar Cells Photovoltaic Performance on the Alkyl Substituent Patterns in Large Bandgap Polymer Donors

et al. 2020

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For all-polymer solar cells which are composed of polymer donors and polymer acceptors, the effect of alkyl side chains on photovoltaic performance is a matter of some debate, and this effect remains difficult to forecast. In this concise contribution, we demonstrate that three alkyls namely branched alkyl 2butyloctyl (2BO), long linear alkyl n-dodecyl (C12), and doubleshort linear alkyl n-hexyls (DC6) incorporated into the side chains of large bandgap polymer donor PBDT-TTz can induce considerable, of significance, and different electronic, optical, and morphological parameters. Systematic studies shed light on the critical role of the double-short linear alkyl n-hexyls (DC6) in (i) producing large ionization potential value, (ii) increasing propensity of the polymer to order along the π-stacking direction, (iii) generating polymer crystallites with more preferential "face-on" orientation, consequently, (iv) improvement of carriers transportation, (v) suppression of charge recombination, (vi) reduction of energy loss in allpolymer devices. In parallel, we unearth that the PBDT-TTz with double-short linear alkyl n-hexyls (DC6) represents the highest efficiency of 8.3 %, whereas, the other two PBDT-TTz analogues (2BO, C12) yield efficiencies of less than 3 % in optimized allpolymer solar cells. Though branched or long linear alkyl side chains (2BO, C12) have been applied to provide the solution processability of conjugated polymers, motifs bearing multiple short linear alkyl substituents (DC6) are proved critical to the development of high performing polymers.[a] J. . Measured (a) J SC , and (b) V OC of all-polymer BHJ solar cells made with polymer donors DC6, C12, 2BO, and polymer acceptor N2200, plotted vs. P light (symbols) on a logarithmic scale, together with the linear fits to the data (solid lines). ChemPhysChemArticles

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Section: Resultssupporting

confidence: 69%

Pronounced Dependence of All‐Polymer Solar Cells Photovoltaic Performance on the Alkyl Substituent Patterns in Large Bandgap Polymer Donors

et al. 2020

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“…One of the major challenges in the development of organic electronics is increasing the charge-carrier mobility [1,2,3,4]. Since charge transport in the constituent materials of organic electronics is an essential property, this phenomenon has been widely studied by using organic field-effect transistors as a platform of investigation [19,20]. Charge transport in organic semiconductor films is known to depend strongly on the crystalline structure, molecular orientation, and morphology of the films [21,22].…”

Section: Introductionmentioning

confidence: 99%

Synergistic Effects of Processing Additives and Thermal Annealing on Nanomorphology and Hole Mobility of Poly(3-hexylthiophene) Thin Films

Park

Kim

2019

Polymers

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Control of the nanoscale molecular ordering and charge-carrier mobility of poly(3-hexylthiophene-2,5-diyl) (P3HT) was achieved by the combined use of processing additives and thermal annealing. Evaluation of four processing additives (1,8-octanedithiol (ODT), diphenyl ether (DPE), 1-chloronaphthalene (CN), and 1,8-diiodooctane (DIO), which are commonly used for the fabrication of organic solar cells, revealed that the nanoscale molecular ordering and, therefore, the charge-carrier mobility, are largely affected by the additives, as demonstrated by spectral absorption, X-ray diffraction, and atomic force microscopy. Thermal annealing selectively influenced the morphological changes, depending on the solubility of P3HT in the additive at high temperature. In the case of CN, in which P3HT can be dissolved at moderate temperature, significant molecular ordering was observed even without thermal annealing. For DIO, in which P3HT is only soluble at elevated temperature, the mobility reached 1.14 × 10−1 cm2 V−1 s−1 only after annealing. ODT and DPE were not effective as processing additives in a single-component P3HT. This study provides insight for designing the processing conditions to control the morphology and charge-transport properties of polymers.

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“…It was observed that introducing bulky phenyl rings showed minimal effects on the polymer π‐conjugation length. Among the series, 47 b with 2‐butyloctyl chain displayed a well‐organized packing structure and favorable domain size when mixed with D1 polymer, leading to the highest PCE of 4.25 % . Chen et al.…”

Section: Ndi‐based Polymer Semiconductorsmentioning

confidence: 99%

“…Amongt he series, 47 b with 2-butyloctyl chain displayed aw ell-organized packings tructure and favorable domain size when mixed with D1 polymer,l eadingt ot he highest PCE of 4.25 %. [58] Chen et al also reported two NDI polymers 48 a and 48 b with at hiophene moiety on the alkyl side chains, whichl ed to ab roadened absorption and suppressed aggregation of the materials, thus yielding aP CE of 4.75 %. Alkoxy chain containingN DI molecules were first reported by Sullivane tal.…”

Section: Introductionmentioning

confidence: 99%

Imide‐Functionalized Polymer Semiconductors

Sun

Wang

et al. 2018

Chemistry A European J

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Imide‐functionalized π‐conjugated polymer semiconductors have received a great deal of interest owing to their unique physicochemical properties and optoelectronic characteristics, including excellent solubility, highly planar backbones, widely tunable band gaps and energy levels of frontier molecular orbitals, and good film morphology. The organic electronics community has witnessed rapid expansion of the materials library and remarkable improvement in device performance recently. This review summarizes the development of imide‐functionalized polymer semiconductors as well as their device performance in organic thin‐film transistors and polymer solar cells, mainly achieved in the past three years. The materials mainly cover naphthalene diimide, perylene diimide, and bithiophene imide, and other imide‐based polymer semiconductors are also discussed. The perspective offers our insights for developing new imide‐functionalized building blocks and polymer semiconductors with optimized optoelectronic properties. We hope that this review will generate more research interest in the community to realize further improved device performance by developing new imide‐functionalized polymer semiconductors.

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Synthesis and side-chain engineering of phenylnaphthalenediimide (PNDI)-based n-type polymers for efficient all-polymer solar cells

Abstract: We designed and synthesized a series of n-type conjugated polymers by introducing phenylnaphthalenediimide (PNDI) as a novel n-type building block, and investigated the effect of side-chain engineering in the polymer acceptor on the performance of all-polymer solar cells (all-PSCs).

Cited by 30 publications

References 70 publications

Pronounced Dependence of All‐Polymer Solar Cells Photovoltaic Performance on the Alkyl Substituent Patterns in Large Bandgap Polymer Donors

Pronounced Dependence of All‐Polymer Solar Cells Photovoltaic Performance on the Alkyl Substituent Patterns in Large Bandgap Polymer Donors

Synergistic Effects of Processing Additives and Thermal Annealing on Nanomorphology and Hole Mobility of Poly(3-hexylthiophene) Thin Films

Imide‐Functionalized Polymer Semiconductors

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