Aldol Condensation‐Polymerized <i>n</i>‐Doped Conjugated Polyelectrolytes for High‐Performance Nonfullerene Polymer Solar Cells

Tian, Liangliang; Jing, Jianhua; Tang, Haoran; Liang, Yuanying; Hu, Zhicheng; Rafiq, Muhammad; Huang, Fei; Cao, Yong

doi:10.1002/solr.202000523

Cited by 15 publications

(8 citation statements)

References 78 publications

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“…As mentioned above, many of these materials are based on the NDI and PDI conjugate cores, often reaching excellent PCE and outperforming conventional materials (refs , , , − , and − ). Additional self-doping materials have been synthesized and tested for this purpose, for example: benzodifurandione-centered oligo( p -phenylenevinylene) (BDOPV)-fluorene polymers, DPP-TP based polymers, azaphenalene diradicaloids, and 3,3′-(5′-(3-(pyridin-3-yl)phenyl)-[1,1′:3′,1″-terphenyl]-3,3″-diyl)dipyridine (TmPyPB) salts for OLED applications …”

Section: Molecular Doping Of Organic Semiconductorsmentioning

confidence: 99%

Doping Approaches for Organic Semiconductors

et al. 2021

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Electronic doping in organic materials has remained an elusive concept for several decades. It drew considerable attention in the early days in the quest for organic materials with high electrical conductivity, paving the way for the pioneering work on pristine organic semiconductors (OSCs) and their eventual use in a plethora of applications. Despite this early trend, however, recent strides in the field of organic electronics have been made hand in hand with the development and use of dopants to the point that are now ubiquitous. Here, we give an overview of all important advances in the area of doping of organic semiconductors and their applications. We first review the relevant literature with particular focus on the physical processes involved, discussing established mechanisms but also newly proposed theories. We then continue with a comprehensive summary of the most widely studied dopants to date, placing particular emphasis on the chemical strategies toward the synthesis of molecules with improved functionality. The processing routes toward doped organic films and the important doping−processing−nanostructure relationships, are also discussed. We conclude the review by highlighting how doping can enhance the operating characteristics of various organic devices.

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Section: Molecular Doping Of Organic Semiconductorsmentioning

confidence: 99%

Doping Approaches for Organic Semiconductors

et al. 2021

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“…The self‐doping effect should be ascribed to the charge transfer from the electron‐donating Lewis basicity (bromide ion) to the electron withdrawing conjugated backbone. [ 22,46 ] Whereas for PIIDNDI‐Br , only the normal broaden and red‐shifted peaks were observed, suggesting doping activity probably not occurs in the thin film. The optical bandgaps ( E opt g) were estimated as 1.42 and 1.30 eV from the onsets of the film absorption of PIIDNDI‐Br and PDPPNDI‐Br , respectively (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…The dependence of device performances based on the PM6:Y6 active layer on ETLs thicknesses were investigated by changing the solution concentration of the CPEs during spin‐coating. Differ from PFN‐Br , [ 22,30,50 ] whose photovoltaic performances decline rapidly as the film thickness increase, the devices based on PIIDNDI‐Br and PDPPNDI‐Br displayed good tolerance to thicker films. It seems PDPPNDI‐Br possesses excellent thickness tolerance with a high PCE of 15% maintained at a thickness of 45 nm and a PCE of 11% at an even thicker ETL layer of 100 nm for its corresponding devices, and the photovoltaic parameters are summarized in Table S2 (Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…[22,24] These materials are composed of a conjugated backbone and pendent polar groups such as quaternary ammonium, sulfonic, anionic carboxyl, etc. [22,25,26] The conjugated backbone of CPEs plays a crucial role in the electric characteristics, charge transport, and performance of the device. However, CPEs with p-type conjugated backbones generally exhibit poor charge mobility and conductivity.…”

Section: Introductionmentioning

confidence: 99%

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Doped/Undoped A1‐A2 Typed Copolymers as ETLs for Highly Efficient Organic Solar Cells

Yang

Shen

Chen

et al. 2023

Adv Funct Materials

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The electron transport layer (ETL) is a critical component in achieving high device performance and stability in organic solar cells. Conjugated polyelectrolytes (CPEs) have become an attractive alternative due to film‐forming properties and ease of preparation. However, p‐type CPEs generally exhibit poor charge mobility and conductivity, incorporation of electron‐withdrawing units forming alternated D‐A conjugated backbone can make up for these deficiencies. Herein, the ratio of electron withdrawing moieties are further increased and two poly(A1‐alt‐A2) typed PIIDNDI‐Br and PDPPNDI‐Br based on the combination of naphthalene diimide (NDI) with isoindigo (IID) or diketopyrrolopyrrole (DPP) via direct arylation polycondensation are synthesized. These CPEs possess excellent alcohol solubility, a suitable lowest unocuppied molecular orbital energy level, and work function tunability. Surprisingly, the incorporation of IID and DPP units generate distinct self‐doping behaviors, which are confirmed by UV–vis absorption and ESR spectra. However, no matter doped or undoped, both CPEs present better charge‐transporting properties and conductivity when utilized as ETLs. The PIIDNDI‐Br and PDPPNDI‐Br display good universal compatibility with the blend of PM6:Y6 and PM6:L8‐BO, and PCEs of 18.32% and 18.36% are obtained, respectively, which also present excellent storage stability. In short, the combination of two different acceptors demonstrates an efficient strategy to design highly efficient ETLs for high performance photovoltaic devices.

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“…The charge transfer from the Lewis base (bromide ion) that donates electrons to the conjugated backbone that withdraws electrons causes the selfdoping effect. 50,52 Huang et al found that the doping effect of nitrogen atoms on dimethylamine was significantly lower than that of bromide ions, which is attributed to the fact that the electron cloud density of bromide anions was higher than that of nitrogen atoms. 18 Therefore, we assume that the ethylmodified benzene ring in HPDIN-B02 promotes the doping of anions into the PDI-conjugated backbone.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Hyperbranched Perylene Diimide Polymers as Electron Transport Layers for Efficient Organic Solar Cells

Xia,

Chen,

Fang

et al. 2023

Macromolecules

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The electron transport layer (ETL) plays a crucial role in achieving high performance and stability of organic solar cells (OSCs). ETL materials suffering from low conductivity can impede charge collection and transport. Hyperbranched polymers display advantages of excellent film-forming property and facile preparation, which, however, often show low conductivity. In this work, we designed two hyperbranched polymers, HPDIN-B01 and HPDIN-B02, integrating the PDIN segments using two tribromomethylbenzene cores through a green and environmentally-friendly quaternization polymerization reaction. Both hyperbranched polymers possess outstanding alcohol solubility and suitable energy levels. Notably, HPDIN-B02 bearing three ethyl units on the benzene core exhibits a strong self-doping behavior as confirmed by electron spin resonance measurements, which is favorable for charge extraction and transport. As a result, when using HPDIN-B02 as ETL, PM6:L8-BO-based OSCs delivered a high power conversion efficiency (PCE) of 18.62%, and the performance is more insensitive to the thickness of the HPDIN-B02 film compared to that using HPDIN-B01. More importantly, HPDIN-B02-based devices also display remarkable durability under various conditions such as when stored in a glovebox, under thermal treatment, or under light illumination. This study demonstrates the great potential of the perylene diimide-based hyperbranched polymer as an efficient ETL for high-performing and stable OSCs.

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Aldol Condensation‐Polymerized n‐Doped Conjugated Polyelectrolytes for High‐Performance Nonfullerene Polymer Solar Cells

Cited by 15 publications

References 78 publications

Doping Approaches for Organic Semiconductors

Doping Approaches for Organic Semiconductors

Doped/Undoped A1‐A2 Typed Copolymers as ETLs for Highly Efficient Organic Solar Cells

Hyperbranched Perylene Diimide Polymers as Electron Transport Layers for Efficient Organic Solar Cells

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