Pyrrolo[3,4-c]pyrrole-1,3-dione-based large band gap polymers containing benzodithiophene derivatives for highly efficient simple structured polymer solar cells

Tamilavan, Vellaiappillai; Roh, Kyung Hwan; Agneeswari, Rajalingam; Lee, Dal Yong; Cho, Shinuk; Jin, Youngeup; Park, Sung Heum; Hyun, Myung Ho

doi:10.1002/pola.27424

Cited by 10 publications

(12 citation statements)

References 54 publications

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“…The polymer PBDPD, poly [4,8- [3,4-c]pyrrole-1,3(2H,5H)-dione), was synthesized according to the literature. 49 The detailed synthesis procedure and characterization of PBDPD are summarized in the Supporting Information. The optical, electrochemical, crystallinity, optimized structure, and photovoltaic properties of PBDPD are summarized below for a better understanding, although some properties have already been reported elsewhere.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The optical, electrochemical, crystallinity, optimized structure, and photovoltaic properties of PBDPD are summarized below for a better understanding, although some properties have already been reported elsewhere. 49,57 As seen in Figure 3a, the absorption band covers the region from 300 to 600 nm with an optical band-gap (E g ) of 2.04 eV for PBDPD, and the determined HOMO and lowest unoccupied molecular orbital (LUMO) levels are approximately −5.44 eV and −3.40, respectively. 49 The absorption spectrum and energy levels of PC 70 BM are also shown in Figure 3a for better understanding.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…49,57 As seen in Figure 3a, the absorption band covers the region from 300 to 600 nm with an optical band-gap (E g ) of 2.04 eV for PBDPD, and the determined HOMO and lowest unoccupied molecular orbital (LUMO) levels are approximately −5.44 eV and −3.40, respectively. 49 The absorption spectrum and energy levels of PC 70 BM are also shown in Figure 3a for better understanding.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…For example, polymer PBDPD incorporating 4,8-bis(5-(2ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene (BDTT) and 2,5-dioctyl-4,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,3(2H,5H)-dione (PD) units gave a maximum PCE of ∼7% with a V oc of 0.90 V, a J sc of 11.38 mA/cm 2 , and an FF of 0.72. 49 The good PCE along with the high V oc and FF obtained for PBDPD urges us to use it as an electron donor along with NFAs. The chemical structure of PBDPD is shown in Figure 1.…”

Section: ■ Introductionmentioning

confidence: 99%

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Pyrrolopyrrole-1,3-dione-Based Wide Band-Gap Polymeric Donors Exemplify High Voltage and Diminutive Energy Loss for Efficient Binary and Tandem Nonfullerene Organic Solar Cells with Efficiency Exceeding 15.7%

Tamilavan

Lee

Jang

et al. 2022

ACS Appl. Energy Mater.

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Here, the potential of pyrrolo[3,4-c]pyrrole-1,3(2H,5H)-dione-based polymers, namely, poly[4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene-alt-2,5-dioctyl-4,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,3(2H,5H)-dione) (PBDPD), is tested as an electron donor in nonfullerene electron acceptor-based organic solar cells (NFA OSCs). Polymer PBDPD shows an intense absorption between 300 and 600 nm with a deeper highest occupied molecular orbital of −5.44 eV. Noticeably, PBDPD displays good complementary absorption and well-matched energy levels with various NFAs. The binary NFA OSCs are fabricated by using PBDPD without any additive or postannealing treatment, providing a maximum power conversion efficiency (PCE) of 11.24% with an impressive open-circuit voltage (V oc) of 1.004 V and a low energy loss (E loss) of 0.496 eV. These results suggest that PBDPD could be a useful candidate for tandem NFA OSCs. Therefore, the tandem NFA OSCs are fabricated using PBDPD with the aim of further maximizing the V oc of the NFA OSCs. The respective tandem NFA OSCs provide an impressive PCE of 15.71% with a greatly improved V oc of 1.73 V. This study suggests that the PD-based polymers are efficient candidates for NFA OSCs, and it opens a new platform for researchers planning to develop efficient wide band-gap polymers for NFA OSCs.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Pyrrolopyrrole-1,3-dione-Based Wide Band-Gap Polymeric Donors Exemplify High Voltage and Diminutive Energy Loss for Efficient Binary and Tandem Nonfullerene Organic Solar Cells with Efficiency Exceeding 15.7%

Tamilavan

Lee

Jang

et al. 2022

ACS Appl. Energy Mater.

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“…55 The incorporation of DPP or TPD acceptor units into P27a affords terpolymers P27b-P27c and P27d, respectively. 56,57 The optical bandgap is reduced from 2.11 eV for P27a to 1.43 and 1.39 eV for P27b and P27c, respectively, by increasing the DPP contents in the conjugated backbones.…”

Section: D2a-type Conjugated D-a Terpolymersmentioning

confidence: 99%

Conjugated D–A terpolymers for organic field-effect transistors and solar cells

Luo

Liu

Zhang

2017

Polym J

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The incorporation of additional electron donors or acceptors into the backbones of conjugated polymers with alternating donors and acceptors results in various conjugated D-A terpolymers. The presence of additional electron donors or acceptors in the conjugated backbones can modulate the electronic absorptions and highest occupied molecular orbital/lowest unoccupied molecular orbital levels, as well as interchain interactions and thin-film morphology. Because of these structural features, conjugated D-A terpolymers have been intensively investigated in recent years for applications in field-effect transistors and photovoltaic cells. In this review, we introduce the recent developments of conjugated D-A terpolymers with various combinations of electron donors and acceptors, and discuss the future perspectives for conjugated terpolymers. In recent decades, conjugated polymers have demonstrated promising applications in flexible, large-area and low-cost electronic devices, such as organic field-effect transistors (OFETs) 1-3 and solar cells (OSCs). [4][5][6][7] This is attributed to the conjugated electronic and polymeric structures of these polymers, resulting in semiconducting properties with good solution processability, mechanical property and thermal stability. 8,9 Among the conjugated polymers, conjugated alternating polymers consisting of both electron donors (D) and electron acceptors (A), referred to as conjugated D-A polymers, [10][11][12][13][14][15][16][17] have been extensively investigated in recent years. The studies indicate that electronic absorptions, highest occupied molecular orbital/lowest unoccupied molecular orbital (HOMO/LUMO) energies (and bandgaps), interchain interactions and thin-film morphologies of conjugated D-A polymers can be effectively tuned 10-17 by properly varying the electron donors and acceptors as well as the linkers. Consequently, the semiconducting performance of conjugated D-A polymers can be tuned in this way. In fact, polymeric p-type, n-type and even ambipolar semiconductors with high charge mobilities have been developed on the basis of conjugated D-A polymers. 18-21 Moreover, conjugated D-A polymers have been successfully utilized as either electron donors or acceptors for OSCs with high power conversion efficiencies (PCEs). [22][23][24][25] Apart from conjugated polymers with alternating electron donor and acceptor moieties, conjugated D-A terpolymers, which contain either one kind of acceptor/two types of electron donors (2D1A) or one kind of donor/two types of electron acceptors (1D2A) in the backbones as illustrated in Scheme 1, have received increased attention. It is expected that an additional dimension is generated for tuning the electronic structures of conjugated polymers and thus their absorptions and HOMO/LUMO levels as well as interchain packing 8,26 with such conjugated D-A terpolymers. Moreover, the combination of existing electron donors and acceptors can yield a huge number of terpolymers, which can be prepared in the same manner as conventional D-A ...

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Visible to Near‐Infrared‐Absorbing Polymers Containing Bithiazole and 2,3‐Didodecyl‐6,7‐Difluoroquinoxaline Derivatives for Polymer Solar Cells

Agneeswari

Kong

Lee

et al. 2019

Bulletin Korean Chem Soc

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Electron donor and electron acceptor materials for solution‐processable polymer solar cells (PSCs) should ideally exhibit a narrow band gap (Eg) and high solubility for improved performance. Herein, we synthesized two new near‐infrared‐absorbing alternating polymers, namely P(BTz‐FQ) and P(BTz‐DTFQ), via Stille polymerization of 4‐butoxy‐5‐(4‐butoxy‐2‐(trimethylstannyl)thiazol‐5‐yl)‐2‐(trimethylstannyl)thiazole and 5,8‐dibromo‐2,3‐didodecyl‐6,7‐difluoroquinoxaline or 5,8‐bis(5‐bromothiophen‐2‐yl)‐2,3‐didodecyl‐6,7‐difluoroquinoxaline. The absorption spectra of P(BTz‐FQ) and P(BTz‐DTFQ) ranged from 300 to 900 nm with two distinct absorption maxima at 718 and 800 nm and 665 and 718 nm, respectively. Both polymers exhibited an identical Eg of 1.41 eV, which is the lowest value reported for quinoxaline‐based polymers to date. Their highest occupied (−5.04 and −5.09 eV) and lowest unoccupied (−3.63 and −3.68 eV) molecular orbital levels were suitable for their use as electron donors along with the fullerene derivative, [6,6]‐phenyl C71 butyric acid methyl ester, as the electron acceptor in PSCs. The maximum power conversion efficiencies obtained for the PSCs utilizing P(BTz‐FQ) and P(BTz‐DTFQ) were 0.51% and 0.71%, respectively. These findings demonstrate that thiazole and fluoroquinoxaline derivatives are promising materials for PSCs and other optoelectronic devices.

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Pyrrolo[3,4-c]pyrrole-1,3-dione-based large band gap polymers containing benzodithiophene derivatives for highly efficient simple structured polymer solar cells

Cited by 10 publications

References 54 publications

Pyrrolopyrrole-1,3-dione-Based Wide Band-Gap Polymeric Donors Exemplify High Voltage and Diminutive Energy Loss for Efficient Binary and Tandem Nonfullerene Organic Solar Cells with Efficiency Exceeding 15.7%

Pyrrolopyrrole-1,3-dione-Based Wide Band-Gap Polymeric Donors Exemplify High Voltage and Diminutive Energy Loss for Efficient Binary and Tandem Nonfullerene Organic Solar Cells with Efficiency Exceeding 15.7%

Conjugated D–A terpolymers for organic field-effect transistors and solar cells

Visible to Near‐Infrared‐Absorbing Polymers Containing Bithiazole and 2,3‐Didodecyl‐6,7‐Difluoroquinoxaline Derivatives for Polymer Solar Cells

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