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Highly efficient through-space charge transfer TADF molecule employed in TADF-and TADF-sensitized organic light-emitting diodes

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Science China Chemistry 2024年第4期67卷 1270-1276页

作者： Jiasen Zhang Deli Li Wei Li Yujie Wu Xilin Mu Chunyu Liu Kaibo Fang Ziyi Ge Zhejiang Provincial Engineering Research Center of Energy Optoelectronic Materials and Devices Ningbo Institute of Materials Technology and EngineeringChinese Academy of SciencesNingbo 315201China Center of Materials Science and Optoelectronics Engineering University of Chinese Academy of SciencesBeijing 100049China State Key Laboratory of Luminescent Materials and Devices and Institute of Polymer Optoelectronic Materials and Devices South China University of TechnologyGuangzhou 510640China

The inception and harnessing of excitons are paramount for the electroluminescence performance of organic light-emitting devices(OLEDs).Through-space charge transfer(TSCT)via intramolecular interaction has proved to be one of the most potent techniques employed to achieve 100% internal quantum efficiency.However,molecular strategies utilized to comprehensively enhance the electroluminescent performance of TSCT emitters regarding improving the photoluminescence quantum yield(PLQY)and elevating the light out-coupling efficiency remain arduous.To surmount this challenge,we deliberately designed and synthesized a proof-of-concept TSCT emitter called CzO-TRZ by incorporating an extra carbazole donor into spiroheterocyclic architecture.The introduction of rigid spiral fragments can immensely boost the horizontal orientation dipole ratio and establish an extra through-bond charge transfer(TBCT)radiative decay channel.As a result,a very high PLQY of 98.7%,fast kRISCof 2.2×10^(5)s^(-1)and high k_(r)^(s) of 2.2×10^(7)s^(-1),and an ultrahigh horizontal dipolar ratio of 90%were concurrently achieved for Cz O-TRZ blended films.Furthermore,corresponding thermally activated delayed fluorescence(TADF)-and TADF-sensitized fluorescence(TSF)-OLEDs based on CzO-TRZ demonstrated external quantum efficiencies(EQEs)of 33.4% and 30.3%,respectively,highlighting its versatile applications as both an emitter and sensitized host.

关键词： organic electronics organic light-emitting diodes polycyclic aromatic hydrocarbons multiple-resonance

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Thermoelectric Properties of an Indandione-Terminated Quinoidal Compound:Effect of the n-Type Dopants

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Chinese Journal of Chemistry 2024年第9期42卷 997-1003页

作者： Yingying Liu Cheng Wang Tianzuo Wang Fei Jiao Shaoqiang Dong Yunfeng Deng Yanhou Geng School of Materials Science and Engineering and Tianjin Key Laboratory of Molecular Optoelectronic Science Tianjin Universityand Collaborative Innovation Center of Chemical Science and Engineering(Tianjin)Tianjin 300072China Institute of Molecular Aggregation Science Tianjin UniversityTianjin 300072China Tianjin Key Laboratory of Molecular Optoelectronic Science Department of ChemistrySchoolof ScienceTianjin UniversityTianjin300072China Joint Schoolof NationalUniversity of Singapore and Tianjin University International Campus of Tianjin UniversityBinhai New City FuzhouFujian350207China

The investigation of n-type doping holds a significant interest for the application of thermoelectrics.Herein,the doping of an indandione-terminated compound Q-4F with a singlet open-shell ground state was studied using two n-dopants N-DMBI and LCV.Both of these two dopants can effectively dope Q-4F due to the large offset between the singly occupied molecular orbital(SOMO)of dopants and the lowest unoccupied molecular orbital(LUMO)of Q-4F.N-DMBI has a higher doping ability than LCV as demonstrated by the UV-vis-NIR and EPR measurements.However,in comparison to N-DMBI doped Q-4F,LCV doped system exhibits much higher electrical conductivity and power factor due to its unperturbed molecular packing and favorable morphology after doping.The optimal conductivity of LCV doped Q-4F is 7.16×10^(-2)±0.16 S·cm^(-1) and the highest power factor reaches 12.3±0.85μW·m–1·K^(-2).These results demonstrate that the modulation of n-dopants is a powerful strategy to balance the doping efficiency and microstructure toward a maximum thermoelectric performance.

关键词： n-Doping Indandione Quinoidal compounds organic thermoelectrics Electron transfer organic electronics Energy conversion

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organic electronics, a Promising King of Freedom to Change Future Life Style of Human Being

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Chinese Journal of Chemistry 2015年第8期33卷 803-805页

作者： Wei Huang[*] Linghai Xie[*] Key Laboratory for organic electronics & Information Displays (KLOEID) Institute of Advanced Materials (IAM) Nanjing University of Posts & Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210023 China

organic electronics is a fast-moving and inter- disciplinary research field beyond organic chemistry. In this area, two major research objects are organic semiconductors and their film devices. Device struc- tures are generally categorized into two types of archi- tecture; one is two-terminal devices such as diodes, and the other is three-terminal devices, such as transistors.

关键词： organic chemistry organic electronics organic semiconductors

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Recent advances of dithienobenzodithiophene-based organic semiconductors for organic electronics

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Science China Chemistry 2021年第3期64卷 358-384页

作者： Bing Zheng Lijun Huo School of Chemistry Beihang UniversityBeijing 100191China

In recent years, fused aromatic dithienobenzodithiophene(DTBDT)-based functional semiconductors have been potential candidates for organic electronics. Due to the favorable features of excellent planarity, strong crystallinity, high mobility, and so on, DTBDT-based semiconductors have demonstrated remarkable performance in organic electronic devices, such as organic feld-effect transistor(OFET), organic photovoltaic(OPV), organic photodetectors(OPDs). Driven by this success, recent developments in the area of DTBDT-based semiconductors for applications in electronic devices are reviewed, focusing on OFET, OPV, perovskite solar cells(PSCs), and other organic electronic devices with a discussion of the relationship between molecular structure and device performance. Finally, the remaining challenges, and the key research direction in the near future are proposed, which provide a useful guidance for the design of DTBDT-based materials.

关键词： dithienobenzodithiophene organic semiconductor extended conjugation crystallinity high mobility organic electronics

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n-Type Semiconductive Polymers Based on Pyrene-1,5,6,10-Tetracarboxyl Diimide

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高分子科学:英文版 2023年第10期41卷 1584-1590页

作者： Xu-Dong Bai Zi-Di Yu Yao Li Tian-Yu Zhang Di Zhang Jie-Yu Wang Jian Pei Da-Hui Zhao Beijing National Laboratory for Molecular Sciences Centre of Soft Matter Science and Engineering and Key Lab of Polymer Chemistry&Physics of Ministry of EducationCollege of ChemistryPeking UniversityBeijing100871China

Donor-acceptor(D-A)conjugated polymers comprising electron-deficient aromatic dicarboximide units represent an important type of organic semiconductors,especially for electron transporting properties.Pyrene-1,5,6,10-tetracarboxyl diimide(PyDI),a new PAH dicarboximide molecule recently reported by us,provides a fine balance between the electron-stabilizing ability andπ-stacking tendency,as compared to the naphthalenediimide(NDI)and perylenediimide(PDI)analogues.In this study,using thienylene-vinylene-thienylene(TVT)and biselenophene(BS)as the electron donating comonomer,along with PyDI as the acceptor moiety,we develop two new D-A type conjugated polymers,which exhibit impressive electron-transporting performance.Specifically,in the solution-processed OFET devices,electron mobility of 0.18 and 0.20 cm^(2)·V^(−1)·s^(−1) are achieved with these polymers,respectively.Such findings further prove the optimal potential of PyDI for application as an electron-acceptor building block in the development of polymeric n-type semiconductors among all various high-performance functional D-A polymers.

关键词： Pyrenedimide Conjugated polymers Donor-acceptor organic electronics

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Enzymatic synthesis of indigo derivatives by tuning P450 BM3 peroxygenases

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Synthetic and Systems Biotechnology 2023年第3期8卷 452-461页

作者： Li Ma Tianjian Sun Yunjie Liu Yue Zhao Xiaohui Liu Yuxuan Li Xinwei Chen Lin Cao Qianqian Kang Jiawei Guo Lei Du Wei Wang Shengying Li State Key Laboratory of Microbial Technology Shandong UniversityQingdao266237China School of Materials Science and Engineering Ocean University of ChinQingdao266100China Laboratory for Marine Biology and Biotechnology Qingdao National Laboratory for Marine Science and TechnologyQingdao266237China

Indigoids,a class of bis-indoles,have long been applied in dyeing,food,and pharmaceutical industries.Recently,interest in these‘old’molecules has been renewed in the field of organic semiconductors as functional building blocks for organic electronics due to their excellent chemical and physical properties.However,these indigo derivatives are difficult to access through chemical synthesis.In this study,we engineer cytochrome P450 BM3 from an NADPH-dependent monooxygenase to peroxygenases through directed evolution.A select number of P450 BM3 variants are used for the selective oxidation of indole derivatives to form different indigoid pigments with a spectrum of colors.Among the prepared indigoid organic photocatalysts,a majority of indigoids demonstrate a reduced band gap than indigo due to the increased light capture and improved charge separation,making them promising candidates for the development of new organic electronic devices.Thus,we present a useful enzymatic approach with broad substrate scope and cost-effectiveness by using low-cost H2O2 as a cofactor for the preparation of diversified indigoids,offering versatility in designing and manufacturing new dyestuff and electronic/sensor components.

关键词： Cytochrome P450 enzymes P450 BM3 peroxygenase Indigoids Dyestuff organic electronics

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Customizable 2D Covalent organic Frameworks for Optoelec-tronic Applications

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Chinese Journal of Chemistry 2023年第10期41卷 1260-1285页

作者： Mingchao Shao Yunqi Liu Yunlong Guo Beijing National Laboratory for Molecular Sciences Institute of ChemistryChinese Academy of SciencesBeijing 100190China University of Chinese Academy of Sciences Beijing 100049China

2D covalent organic framework(2D-COF),a modular three-dimensional material,is easily influenced by the component module.The assembly of different functionalized modules gives 2D-COF unique performance.The modular structure not only allows for customi-zation but also allows for variety,which gives 2D-COF a wide range of functions.Hence,many building blocks with catalytic,ligand,semiconductor,luminescent,and redox centers are integrated into the COF scaffold.The connection and assembly of such modules determine the nature of the final block material.The intra-layer connections of the modules form a monolayer mesh chemical structure,and the subsequent stacking of the monolayer mesh structure produces the final crystalline porous material-2D-COF.This review describes in detail the potential of COF materials as optoelectronic materials and our understanding of optoelectronic processes,starting from monolayer reticulation chemistry to final 3D stacked structures,thus establishing a new paradigm for the ra-tional design of well-defined novel 2D-COF optoelectronic materials and devices.

关键词： 2D covalent organic frameworks Optoelectronic π-Conjugation Stacking Doping Charge transfer organic electronics Donor-acceptor systems

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High-performance and multifunctional organic field-effect transistors

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中国化学快报:英文版 2023年第9期34卷 100-118页

作者： Yujie Zhao Wei Wang Zihan He Boyu Peng Chong-An Di Hanying Li MOE Key Laboratory of Macromolecular Synthesis and Functionalization International Research Center for X PolymersDepartment of Polymer Science and EngineeringZhejiang UniversityHangzhou 310027China Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijing 100190China School of Chemical Sciences University of Chinese Academy of SciencesBeijing 100049China

organic field-effect transistors(OFETs)refer to field-effect transistors that use organic semiconductors as channel materials.Owing to the advantages of organic materials such as solution processability and intrinsic flexibility,OFETs are expected to be applicable in emergent technologies including wearable electronics and sensors,flexible displays,internet-of-things,neuromorphic computing,etc.Improving the electrical performance and developing multifunctionalities of OFETs are two major and closely relevant aspects for OFETs-related research.The former one aims for investigating the device physics and expanding the horizons of OFETs,while the later one is critical for leading OFETs into practical and emergent applications.The development in each of the two aspects would undoubtfully promote the other and bring more confidence for future development of OFETs.Hence,this review is divided into two parts that respectively summarize the recent progress in high-performance OFETs and multifunctional OFETs.

关键词： organic filed-effect transistors organic semiconductors High-performance Multifunctionality organic electronics

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1,2,5,6-Naphthalene Diimides:A Class of Promising Building Blocks for organic Semiconductors

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Chinese Journal of Chemistry 2023年第10期41卷 1226-1234页

作者： Zheng Zhao Congwu Ge Xueqian Zhao Jintao Huang Xike Gao Key Laboratory of Synthetic and Self-Assembly Chemistry for organic Functional Molecules Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China

organic semiconductors have drawn extensive atten-tion due to their optoelectronic properties and wide applications in organic optoelectronics.In comparison with the popular 1,4,5,8-naphthalene diimides(1,4,5,8-NDIs),the angular-shaped 1,2,5,6-NDIs have exhibited tunable photophysical properties,self-as-sembly behaviors and charge transporting properties.Due to these unique features,1,2,5,6-NDIs show great potential for construction of high performance n-func-tional materials.In this review,we highlight the recent advances and future prospects of 1,2,5,6-NDI-basedπ-systems in the field of organic optoelectronics,in-cluding molecular design,synthesis,structure-prop-erty relationships as well as the applications in high performance organic field-effect transistors,organic photovoltaics,perovskite solar cells,and so on.

关键词： organic semiconductors Electron acceptors Design and synthesis 1,2,5,6-NDI Structural isomerism Polymer acceptors organic electronics

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organic single-crystal light-emitting transistors with external quantum efficiency over 20%

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聚集体(英文) 2023年第4期4卷 122-127页

作者： Jian Deng Zejian Zhang Pengpeng Sang Shujun Yin Shitong Zhang Yuan Li Bing Yang Cheng Gu Yuguang Ma State Key Laboratory of Luminescent Materials and Devices Institute of Polymer Optoelectronic Materials and DevicesSouth China University of TechnologyGuangzhouP.R.China School of Information Science and Engineering Shandong UniversityQingdaoP.R.China State Key Laboratory of Supramolecular Structure and Materials Institute of Theoretical ChemistryCollege of ChemistryJilin UniversityChangchunP.R.China Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates South China University of TechnologyGuangzhouP.R.China

organic light-emitting transistors(OLETs)have attracted increasing attention because of their potential applications in next-generation displays and high-energy operating devices.However,the simultaneous achievement of high luminescent efficiency and carrier mobility in organic semiconductors remains challenging because the localized excitons are advantageous for light emission,whereas the delocalized carriers are beneficial for efficient charge migration.Herein,we report an organic single crystal of a cyano-substituted styrene derivative with balanced mobility yielding a record-high external quantum efficiency of 20.5%in OLETs.Temperature-dependent I–V curves and electronic structure analyses based on firstprinciples calculations were performed to disclose the underlying mechanism as a band transport,which provides an efficient way to achieve high quantum efficiency in OLETs.

关键词： organic electronics organic light-emitting transistors single crystals styrene

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