Thermally Activated n‐Doping of Organic Semiconductors Achieved by N‐Heterocyclic Carbene Based Dopant

Ding, Yifan; Yang, Chi‐Yuan; Huang, Chun‐Xi; Lü, Yang; Yao, Ze‐Fan; Pan, Chen-Kai; Wang, Jieyu; Pei, Jian

doi:10.1002/anie.202011537

Cited by 23 publications

(27 citation statements)

References 45 publications

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“…Such species are strong σ-electron donors (Lewis bases) and nucleophiles. The formation of a such a NHC, from the thermal activation of a stable precursor, 1,3-dimethylimidazolium-2-carboxylate (DMImC), has been recently reported for sequential doping of n-type OSCs sequential processing . The carbene was suggested to chemically react with the OSC to form a radical anion, as indicated by absorption and EPR measurements.…”

Section: Molecular Doping Of Organic Semiconductorsmentioning

confidence: 98%

“…The formation of a such a NHC, from the thermal activation of a stable precursor, 1,3-dimethylimidazolium-2-carboxylate (DMImC), has been recently reported for sequential doping of n-type OSCs sequential processing. 267 The carbene was suggested to chemically react with the OSC to form a radical anion, as indicated by absorption and EPR measurements. Unlike the free carbene, the carbene precursor exhibited excellent air stability, and the doping species could be formed in situ with high doping efficiency, resulting in a substantial improvement in the OSC film conductivity.…”

Section: Dopant Materialsmentioning

confidence: 99%

“…4ethylbenzenesulfonic acid (EBSA) capped with an o-nitrobenzyl capping moiety (EBSAc) can be solution coprocessed with P3HT, PBTTT, and p(g 4 2T-T), followed by thermal activation at 140 °C, which releases 2-nitrosobenzaldehyde and frees the EBSA acid dopant, leading to p-doping of the bulk sample (Figure 21). 267,425 We anticipate that latent n-dopants such as a recently reported N-heterocyclic carbene-based dopant, which is thermally activated at 160 °C, 425 may ease bulk processing of n-type conductors. Bulk materials can be prepared through coprocessing if suitable counterions are selected that impart melt-and/or solution processability.…”

Section: Doping Of Bulk Materialsmentioning

confidence: 99%

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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: 98%

Section: Dopant Materialsmentioning

confidence: 99%

Section: Doping Of Bulk Materialsmentioning

confidence: 99%

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Doping Approaches for Organic Semiconductors

et al. 2021

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“…We developed an adduct of carbon dioxide and NHC, 1,3-dimethylimidazolium-2-carboxylate (DMImC), which can generate free NHC molecules in situ via thermal activation . DMImC exhibited good air-stability at room temperature.…”

Section: Solution-processable N-dopants For Efficient N-dopingmentioning

confidence: 99%

“…46,47 We developed an adduct of carbon dioxide and NHC, 1,3dimethylimidazolium-2-carboxylate (DMImC), which can generate free NHC molecules in situ via thermal activation. 48 DMImC exhibited good air-stability at room temperature. Thermal gravity analysis (TGA) proved that the decarboxylation temperature of DMImC is about 159 °C.…”

Section: N-heterocyclic Carbene Derivativesmentioning

confidence: 99%

Achieving Efficient n-Doping of Conjugated Polymers by Molecular Dopants

2021

Self Cite

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Metrics & MoreArticle Recommendations CONSPECTUS: Molecular doping is one of the most central propositions in the field of organic electronics. Unlike classical inorganic semiconductors doped by atomic substitution, organic conjugated materials react with molecular dopants, and then intermolecular charge transfer is involved within. Therefore, the complex noncovalent interactions between two components often cause the molecular dopant to destroy the orderly stacking of the host organic materials and reduce the original properties of the material, such as carrier mobility, which here we call the "doping dilemma." Recently, many studies focus on improving p-doping efficiency and electrical conductivity of doped conjugated polymers; however, the development of n-type molecular doping currently lags far behind that of its p-counterpart. It is well-known that both efficient p-and n-type molecular doping are indispensable in various organic electronic devices, including light-emitting diodes, photovoltaics, field-effect transistors, and thermoelectrics. It is thus an urgent requirement to achieve efficient n-doping in conjugated polymers.In this Account, we give a brief overview of our efforts to improve the n-doping efficiency in conjugated polymers with several strategies from the aspects of the polymer/dopant molecular design and the exploration of the ntype molecular doping mechanism and charge transport mechanism in n-doped organic materials. For the conjugated polymer engineering, we first demonstrate that increasing the electron affinity of the host polymer through halogen substitution can boost the n-doping efficiency. Still, the rigid coplanar backbones of conjugated polymers play a crucial role in the polaron delocalization and final electrical performance. In addition, we emphasize the importance of morphology control in the doped polymers to address the "doping dilemma." For n-dopants designing, we summarize some basic guidelines from molecular sizes and shapes, the interaction between dopants (or dopant cations) and polymers, and the effects of dopants on morphology to design high-efficacy n-type molecular dopants. We propose that the polymers and the dopants need to be treated as a whole system; while enhancing the ionization efficiency, more attention should be paid to the carrierization (free-carrier generation) efficiency of these binary systems.In the end, we adopt the n-type polymer thermoelectric material as an example to discuss the grand challenges encountered in practical applications of n-doped conjugated polymers. The air stability and micrometer-thick thermo-leg processing of n-doped polymers are highlighted for thermoelectric applications. It is our hope that this Account showcases a blueprint for rational approaches and a deep understanding toward the design and development of efficient n-doping in conjugated polymers, bringing ndoped organic materials into the next era.

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Molecular Doping Efficiency in Organic Semiconductors: Fundamental Principle and Promotion Strategy

Yan

2021

Adv Funct Materials

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Molecular doping, a fascinating technique to modulate the electrical property of organic solids by importing additional charges, has been one of the focal points of active research over the last three decades. Due to the potential applications in clean energy and artificial intelligence, molecular doping is experiencing a second golden stage by virtue of its compatibility with solution‐processed organic functional devices. The central challenge at present promoting the doping efficiency. This perspective starts with revisiting the basic concepts in doping process and discusses the recent progress in efficiency improvements. Based on the journey of molecular doping, it is concluded that molecular doping can be as efficient as atomic doping is in inorganic semiconductors; future directions to achieve this goal are shared.

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Thermally Activated n‐Doping of Organic Semiconductors Achieved by N‐Heterocyclic Carbene Based Dopant

Cited by 23 publications

References 45 publications

Doping Approaches for Organic Semiconductors

Doping Approaches for Organic Semiconductors

Achieving Efficient n-Doping of Conjugated Polymers by Molecular Dopants

Molecular Doping Efficiency in Organic Semiconductors: Fundamental Principle and Promotion Strategy

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