Naphthalene diimide-based random terpolymer for efficient all-polymer solar cells with high open circuit voltage

Zhang, Tao; Lu, Mingyu; Wang, Wen; Lv, Wei; Cui, Jianyu; Feng, Wenhuai; Ling, Qidan

doi:10.1016/j.dyepig.2017.07.007

Cited by 19 publications

(16 citation statements)

References 55 publications

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“…The n-type semiconducting random copolymers P(NDI2OD-Se-Th x) (x = 0, 0.5, 0.7, 0.8, 0.9, 1. 46 The detailed synthetic schemes and conditions are described in the Supporting Information, and molecular structures confirmed by nuclear magnetic resonance (NMR) spectra are presented in Figures S1 and S2. The actual compositions of NDI, Se-Th, and SeTh units in P(NDI2OD-Se-Th x) P A 's well matched with feed ratios in the copolymerization.…”

Section: Resultsmentioning

confidence: 99%

Naphthalene Diimide-Based Terpolymers with Controlled Crystalline Properties for Producing High Electron Mobility and Optimal Blend Morphology in All-Polymer Solar Cells

et al. 2020

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We report a series of new n-type random copolymers (P(NDI2OD-Se-Th x), where x = 0, 0.5, 0.7, 0.8, 0.9, 1.0) consisting of naphthalene diimide (NDI), selenophene-2,2′-thiophene (Se-Th), and seleno[3,2-b]thiophene (SeTh) to demonstrate their use in producing efficient all-polymer solar cells (all-PSCs) and organic field-effect transistors (OFETs). To investigate the effect of polymer crystallinity on the performance of all-PSCs and OFETs, we tuned the composition of the Se-Th and SeTh moieties in the P(NDI2OD-Se-Th x) polymers, resulting in enhanced crystalline properties with a higher Se-Th ratio. Thus, the OFET electron mobility was increased with a higher Se-Th ratio, exhibiting the highest value of 1.38 × 10–1 cm2 V–1 s–1 with P(NDI2OD-Se-Th 1.0). However, the performance of all-PSCs based on PBDB-T:P(NDI2OD-Se-Th x) showed a nonlinear trend relative to the Se-Th ratio and the performance was optimized with P(NDI2OD-Se-Th 0.8) exhibiting the highest power conversion efficiency of 8.30%. This is attributed to the stronger crystallization-driven phase separation in all-polymer blends for higher Se-Th ratio. At the optimal crystallinity of P(NDI2OD-Se-Th 0.8) in all-PSCs, the degree of phase separation, domain purity, and electron mobility were optimized, resulting in enhanced charge generation and transport. Our works describe the structure–property–performance relationships to design effective n-type polymers in terms of crystalline and electrical properties suitable for both efficient OFETs and all-PSCs.

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Section: Resultsmentioning

confidence: 99%

Naphthalene Diimide-Based Terpolymers with Controlled Crystalline Properties for Producing High Electron Mobility and Optimal Blend Morphology in All-Polymer Solar Cells

et al. 2020

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“…Owing to their enlarged lattice distortion and decreased backbone planarity, the lamellar spacing and π–π stacking distance of the resulting terpolymers was slightly increased, resulting in a better compatibility between the donor and acceptor polymers. Among them, 56 c showed an increased miscibility with donor polymer D11 while providing the most balanced μ h,SCLC and μ e,SCLC , thus, the highest PCE of 5.4 % was demonstrated for 56 c with a high V oc of 1.05 V. The ultra‐high V oc originated from the well‐matched energy levels between 56 c and D11 , resulting in a large offset between the 56 c LUMO and D11 HOMO . Very recently, Li and co‐workers reported another series of dye‐incorporated NDI‐based terpolymers 57 as the acceptor polymers for all‐PSCs.…”

Section: Ndi‐based Polymer Semiconductorsmentioning

confidence: 99%

“…Among them, 56 c showed an increased miscibility with donor polymer D11 while providing the most balanced m h,SCLC and m e,SCLC ,t hus, the highest PCE of 5.4 %w as demonstrated for 56 c with ah igh V oc of 1.05 V. The ultra-high V oc originated from the well-matched energy levels between 56 c and D11, resultingi nalarge offset between the 56 c LUMO and D11 HOMO. [71] Very recently, Li and co-workers reported another series of dye-incorporated NDI-based terpolymers 57 as the acceptor polymers for all-PSCs. By introducingarhodamine derivatived ye into the side chain, the absorption coefficient of the resulting terpolymers was greatly increased,l eading to a more efficient photon capturing and thus an increased J sc .…”

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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“…[1,6,7] NDIs are considered to be one of the most promising units for n-type polymer acceptors. [8,9] The imide functionalization of NDIs has little effect on the molecularlevel electronic and optical properties, whereas the presence of one or more substituents at the 2-, 3-, 6-, and 7-positions of core-substituted NDIs can significantly affect these properties. Thus, although interest in core-substituted naphthalene diimides (cNDIs) has increased in recent years, [8][9][10] studies of the properties of cNDIs are still limited by synthetic difficulties.…”

Section: Introductionmentioning

confidence: 99%

“…The bromination of 1,4,5,8-naphthalenetetracarboxylic dianhydride can be realized in several ways, [8,[22][23][24][25] but we used 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) in H 2 SO 4 . [8] We have developed a method for the isolation of 2,6-BrNDI through crystallization from chloroform with the addition of silica, which allows time-consuming chromatographic methods to be bypassed (Figure 1a, Step III).…”

Section: Introductionmentioning

confidence: 99%

Naphthalene Diimides Prepared by a Straightforward Method and Their Characterization for Organic Electronics

et al. 2018

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A new approach for the synthesis of acetylene‐substituted naphthalene diimides in polar solvents with PdCl2, Et3N, and electrolytic copper powder was developed. This simplified approach allows for high‐throughput synthesis, and the reaction products can be readily separated. DFT studies revealed that the electronic structures of these compounds are mainly determined by the central naphthalene diimide unit and the acetylene groups. The obtained thermally stable and soluble compounds undergo reversible reduction with electron affinities of 4.18 to 4.28 eV. They emit green light with photoluminescence quantum yields of ca. 6 % in chloroform and in the range 3–12 % as thin films. The compounds were applied as emitting layers for both nondoped and doped single‐layer organic light‐emitting diodes (OLEDs) fabricated by solution processing. Under an applied external voltage, they exhibit orange or red electroluminescence.

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Naphthalene diimide-based random terpolymer for efficient all-polymer solar cells with high open circuit voltage

Cited by 19 publications

References 55 publications

Naphthalene Diimide-Based Terpolymers with Controlled Crystalline Properties for Producing High Electron Mobility and Optimal Blend Morphology in All-Polymer Solar Cells

Naphthalene Diimide-Based Terpolymers with Controlled Crystalline Properties for Producing High Electron Mobility and Optimal Blend Morphology in All-Polymer Solar Cells

Imide‐Functionalized Polymer Semiconductors

Naphthalene Diimides Prepared by a Straightforward Method and Their Characterization for Organic Electronics

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