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Asymmetric Thermally Activated Delayed Fluorescence Materials Rendering High-performance OLEDs Through both Thermal Evaporation and Solution-processing

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Chemical Research in chinese Universities 2022年第6期38卷 1526-1531页

作者： GAO Shiyuan CHEN Xiaojie GE Xiangyu CHEN Zhu ZHAO Juan chi zhenguo State Key Laboratory of OEMT School of Materials Science and EngineeringSun Yat-sen UniversityGuangzhou510275P.R.China State Key Laboratory of OEMT School of ChemistrySun Yat-sen UniversityGuangzhou510275P.R.China

Exploring high-efficiency thermally activated delayed fluorescence(TADF)materials is of great importance regarding to organic light-emitting diode(OLED).Herein,we present a design strategy for developing asymmetric TADF materials based on a diphenyl sulfone-phenoxazine structure,resulting in efficient TADF emitters(CzPXZ and t-CzPXZ)with aggregation-induced emission properties,while t-CzPXZ is modified with tert-butyl *** two compounds exhibit high solid-state luminescence,efficient TADF,and significantly impressive device performances by both thermal evaporation and solution *** an instance,CzPXZ and t-CzPXZ enable the thermally-evaporated OLEDs with high external quantum efficiencies(EQEs)of over 20%.Meanwhile,t-CzPXZ allows the solution-processed device with a high EQE of 16.3%with low-efficiency roll-off,attributing to the enhanced molecular solubility and suppressed excitons quenching through tert-butyl modification on *** results reveal that the proposed asymmetric structure is a promising approach for developing high-efficiency TADF materials and OLEDs.

关键词： Thermally activated delayed fluorescence Asymmetric strategy Organic light-emitting diode Thermal evaporation Solution processing

Sulfonyldibenzene-based hole-transporting materials for efficient n-i-p perovskite solar cells

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Science china Chemistry 2021年第1期64卷 127-133页

作者： Tian Qin Fei Wu Yingxiao Mu Yubo Long Linna Zhu Juan Zhao zhenguo chi Chongqing Key Laboratory for Advanced Materials and Technologies of Clean Energy School of Materials&EnergySouthwest UniversityChongqing 400715China PCFM Lab GDHPPC LabGuangdong Engineering Technology Research Center for High-performance Organic and Polymer Photoelectric Functional FilmsState Key Laboratory of OEMTSchool of ChemistrySun Yat-sen UniversityGuangzhou 510275China School of Materials Science and Engineering Sun Yat-sen UniversityGuangzhou 510275China

Organic hole-transporting materials(HTMs)are an essential component in conventional perovskite solar cells(PSCs).In this work,two sulfonyldibenzene-based molecules,named CS-04 and CS-05,are synthesized and employed as HTMs in n-i-p *** comparison with CS-04,the carbazole-substituted methoxytriphenylamine(Cz MOTPA)group in CS-05 exhibits an increased degree of molecular distortion,thus endowing CS-05 with excellent solvent solubility and film-formation ***,CS-05 shows a high hole mobility,superior hole extraction and hole transporting *** a result,CS-05 yields impressive device performances with a high power conversion efficiency(PCE)of 20.15%,while that of CS-04 based device is 19.50%,which is comparable to that of the Spiro-OMe TAD based control device(19.59%).This finding illustrates the potential of sulfonyldibenzene-based molecules for the applications in PSCs,and also provides a novel avenue to improve the performances and stability of PSCs by tailoring the sulfonyldibenzene-based molecules.

关键词： sulfonyldibenzene hole-transporting material perovskite solar cell

Temperature-Induced Transformation from Large Compound Vesicles to Worm-like Aggregates by ABC Triblock Copolymer

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chinese Journal of Chemistry 2015年第12期33卷 1338-1346页

作者： Yupeng Wu Yangchun Tao Kuan Cai Siwei Liu Yi Zhang zhenguo chi Jiarui Xu Yen Wei PCFMLab and GD HPP School of Chemistry and Chemical Engineering Sun Yat-sen University Guangzhou Guangdong 510275 China Department of Chemistry Tsinghua University Beijing 10084 China

Two triblock polymers, tetraaniline-block-poly（N-isopropyl acrylamide）-block-poly（hydroxyethyl acrylate）（TA-b-PNIPAM-b-PHEA） and TA-b-PHEA-b-PNIPAM, were synthesized with unambiguous structure by a two step method. The difference of these two diblock polymers is the connection order of carboxyl group to block, e.g., carboxyl group to PNIPAM block for PNIPAM-b-PHEA and to PHEA block for PHEA-b-PNIPAM. Secondly, block tetraaniline was linked to the diblock polymer through amidation to yield the corresponding triblock copolymer. Both of them have almost the identical chemical compositions. The only difference is the connection order of each block in the triblock polymers. When they were self-assembled at 45℃ in a suitable solution, both of their aggregates have spherical shape with slight defects on their surface with the average diameter of about 400 nm. However, when their aggregate dispersion was cooled down to 20 ℃, only TA-b-PHEA-b-PNIPAM＇s morphology changed, forming worm-like aggregates with the diameter of about 100-200 nm transformed from spherical ag- gregates. Both amphiphilic property and position of each block in this triblock copolymer are very essential for this morphology transformation. Since the worm-like aggregates presented here by our group have hollow structure in- side, its controlled release properties for doxorubicin were evaluated. Drug release experiment indicated that along with the temperature changes, the rearrangement of the intermediate layer structure caused morphology change in aggregate, thus accelerating the speed of drug release.

关键词： worm-like aggregates self-assembly block copolymers large compound vesicles drug release

Intrinsic persistent room temperature phosphorescence derived from 1H-benzo[f]indole itself as a guest

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chinese Chemical Letters 2023年第7期34卷 449-453页

作者： Danman Guo Yuyuan Wang Jinzheng Chen Yifeng Cao Yiling Miao Huahua Huang zhenguo chi Zhiyong Yang Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education Guangdong Engineering Technology Research Center for High-performance Organic and Polymer Photoelectric Functional FilmsSchool of ChemistrySun Yat-sen UniversityGuangzhou 510275China School of Materials Science and Engineering Sun Yat-sen UniversityGuangzhou 510275China Guangdong Provincial Key Laboratory of Optical Chemicals XinHuaYue GroupMaoming 525000China

The influence of 1H-benzo[f]indole(Bd) and its derivatives on room temperature phosphorescence(RTP)has raised great concern since they were found to significantly affect RTP of the extensively studied carbazole(Cz) derivatives. However, the role of Bd itself existing in Cz-based or other doping systems was still unclear. In order to clarify its intrinsic phosphorescent property, Bd was introduced as a guest into different organic matrixes including substituted Cz derivatives and polymers. The phosphorescence located in 560–620 nm was confirmed to be derived from Bd itself, which can be detected whatever Bd was doped in the crystal or amorphous state of Cz derivatives. The suitable energy gap between Cz derivatives and Bd is the key to achieve ultralong RTP of Bd. Additionally, when doped in polymers with plenty of hydrogen bonds, RTP of Bd with lifetime over 280 ms was easily obtained. Among them, Bd@PHEMA(poly(hydroxyethyl methacrylate) exhibited superior phosphorescence, with yellow afterglow lasting for over 2.5 s. Therefore, this work demonstrated that a new organic RTP phosphor, Bd, is discovered, and ultralong RTP of Bd can be achieved not only doped in Cz derivatives but also in polymers as the hosts.

关键词： Room temperature phosphorescence Host-guest 1H-benzo[f]indole Amorphous Hydrogen bonding

Achieving white-light emission in a single-component polymer with halogen-assisted interaction

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Science china Chemistry 2021年第3期64卷 467-477页

作者： Zhuxin Zhou Zhu Mao Zhan Yang Tingting Yang Longji Zhu Yubo Long zhenguo chi Siwei Liu Matthew P.Aldred Xudong Chen Jiarui Xu Yi Zhang Key Laboratory for Polymeric Composite&Functional Materials of Ministry of Education Key L aboratory for High-Performance Polymer Composites of Guangdong ProvinceGuangdong Engineering Technology Research Centre for High-performance Organic and Polymer Photoelectric Functional FilmsState Key Laboratory of Optoelectronic Materials and TechnologiesSchool of ChemistrySun Yat-sen UniversityGuangzhou 510275China Lomox Limited Bank HouseMarket SquareCongletonCheshire CW121ETUnited Kingdom Shenzhen Yanyi New Materials Co. Ltd.Shenzhen 518110China

White-light emitting(WLE) polymers have attracted continuous attention for their promising applications in solid-state lighting,flexible display and related fields. However, achieving dual-emission and pure white-light emission in a single-component polymer is still challenging. In this study, a brominated single-component polymer Br OD-TFB was designed and synthesized,which shows dual-emission and white light emission properties in solution and room-temperature phosphorescence(RTP) in thin films. The dual-emission properties can be tuned by concentration, solvent polarity, and excitation energy. Spectral analyses and theoretical calculations reveal that the origin of the high-energy emission band(HEB) is intramolecular charge transfer(ICT)along the polymer chain, whilst the low-energy emission band(LEB) originates from the excited-state related to the intra-chain and inter-chain C–Br···π interactions as demonstrated by the single-crystal structure of the model compound. Appropriate control of the formation and the destruction of the halogen-assisted interactions can initiate white-light emission in the singlecomponent polymer. More interestingly, by dispersing Br OD-TFB(0.1 wt%) in a non-emissive, colorless and transparent polymer, the characteristics of this white-light emission can be fully demonstrated while exhibiting unexpected RTP properties,with photoluminescence quantum efficiency(Φ_(PL)) of up to 23% and CIE coordinates of(0.32, 0.32).

关键词： white-light emission single-component polymer halogen-assisted interaction functional polyimide mechanism

Multiple-resonance thermally activated delayed emitters through multiple peripheral modulation to enable efﬁcient blue OLEDs at high doping levels

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Aggregate 2024年第5期5卷 349-357页

作者： Yuyuan Wang Zhiwei Ma Junrong Pu Danman Guo Gaoyu Li Zhu Chen Shi-Jian Su Huangjun Deng Juan Zhao zhenguo chi PCFM Lab GD HPPC LabGuangdong Engineering Technology Research Center for High-Performance Organic and Polymer Photoelectric Functional FilmsState Key Laboratory of Optoelectronic Material and TechnologiesSchool of ChemistrySun Yat-sen UniversityGuangzhouChina State Key Laboratory of Luminescent Materials and Devices and Institute of Polymer Optoelectronic Materials and Devices South China University of TechnologyGuangzhouChina State Key Laboratory of Optoelectronic Material and Technologies School of Materials Science and EngineeringSun Yat-sen UniversityGuangzhouChina

Organic light-emitting diodes(OLEDs)based on multiple resonance-thermallyactivated delayedﬂuorescence(MR-TADF)have the advantages of high excitonutilization and excellent color ***,the large conjugated planarity of gen-eral MR-TADF emitters makes them easily aggregate in the form ofπ–πstacking,resulting in aggregation-caused quenching(ACQ)and the formation of excimers,which reduce exciton utilization efﬁciency and color *** address these issues,large shielding units can be incorporated to prevent interchromophore interactions,whereas the majority of reported molecules are limited to blue-green light *** work proposes a strategy of incorporating steric hindrance groups atdifferent sites of the B/N core to suppress interactions between chromophore,con-tributing to blue MR-TADF emitters with high photo-luminance quantum yields(PLQYs≥95%)and narrow full width at half maximum(FWHM),and importantly,great suppression of the ACQ ***,blue OLEDs achieve high externalquantum efﬁciencies up to 34.3%and high color purity with FWHM of about 27 nmand CIE around(0.12,0.15),even at a high doping concentration of 20 wt%.

关键词： blue emission color purity multiple-resonance organic light-emitting diodes thermally activated delayedﬂuorescence

Polymeric ultralong organic phosphorescence with excellent humidity and temperature resistance via hydrophobic effect

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Aggregate 2024年第2期5卷 222-228页

作者： Zhongyu Li Kexin Fu Huangjun Deng Kaixuan Nie Zhe Pan Zhu Mao Juan Zhao Gang Li Pengli Zhu zhenguo chi Rong Sun National Key Laboratory of Materials for Integrated Circuits Shenzhen Institute of Advanced Electronic MaterialsShenzhen Institute of Advanced TechnologyChinese Academy of SciencesShenzhenChina PCFM Lab GDHPPC LabGuangdong Engineering Technology Research Center for High-performance Organic and Polymer Photoelectric Functional FilmsState Key Laboratory of OEMTSchool of ChemistrySun Yat-sen UniversityGuangzhouChina State Key Laboratory of Optoelectronic Material and Technologies School of Materials Science and EngineeringSun Yat-sen UniversityGuangzhouChina

Polymeric ultralong organic phosphorescence(UOP)with persistent emission is of great importance in practical ***,achieving good water-resistance for long-term environmental stability is a formidable *** this contribution,through tailoring the alkyl-chain length of the hardeners and emitters,polymeric UOPs with varying crosslinking density and hydrophobic effect were ***,all the polymers show no obvious decrease in UOP emission after high temperature-humidity test(85◦C/85%relative humidity for 7 days).Detailed investigations demonstrate that the rigid covalent crosslinking networks suppress the quenching of triplet excitons while the hydrophobic microenvironment affords good water/moisture-resistance ***,the polymers with superior processability are successfully applied as optical coatings,prepreg,and afterglow *** this work,we provide a new strategy to promote the long-term stability of polymeric UOP materials in high-temperature-humidity conditions.

关键词： aqueous environment hydrophobic effect long-term stability polymeric phosphorescence room temperature phosphorescence

Remarkable mechanochromism and force-induced thermally activated delayed fluorescence enhancement from white-light-emitting organic luminogens with aggregation-induced emission

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chinese Chemical Letters 2022年第10期33卷 4536-4540页

作者： Yitao Zheng Lingqi Zuo Letian Zhang Zihao Huang Shufeng Li Zhan Yang Zhu Mao Suilian Luo Cong Liu Fengqiang Sun Guang Shi zhenguo chi Bingjia Xu Key Laboratory of Theoretical Chemistry of Environment Ministry of Education/School of ChemistrySouth China Normal UniversityGuangzhou 510006China State Key Laboratory of Optoelectronic Materials and Technologies(Sun Yat-sen University) Guangzhou 510275China School of Chemistry Sun Yat-sen UniversityGuangzhou 510275China Shenzhen Institute of Advanced Electronic Materials Shenzhen Institutes of Advanced TechnologyChinese Academy of SciencesShenzhen 518055China

The development of organic materials with white-light emission and thermally activated delayed fluorescence(TADF)properties in the solid state remain a ***,a series of white-light-emitting organic luminogens have been developed and are found to show aggregation-induced delayed fluorescence(AIDF)*** AIDF emitters present dual-emission consisted of prompt fluorescence and TADF in the crystalline *** white-light emissions can be easily tuned by altering the chemical structure and connecting position of the heterocyclic aromatic *** the stimuli of mechanical force and solvent vapor,the compounds exhibit remarkable and reversible mechanochromism,in which their emission colors are switchable between white and *** grinding,they also display linearly tunable luminescence colors,as well as force-induced TADF enhancement,which may be associated with the more compact molecular packing and the restriction of intramolecular *** results from time-resolved emission scanning and theoretical calculation suggest that the dual-emission of the AIDF luminogens likely results from the twisted intramolecular charge transfer transitions of the molecules,and the reversible mechanochromism properties probably stem from the interconversion of the quasi-axial and the quasi-equatorial conformations.

关键词： White-light emission Thermally activated delayed fluorescence Aggregation-induced delayed fluorescence mechanochromism Force-induced emission enhancement

Hybridized Local and Charge-Transfer Excited-State Fluorophores through the Regulation of the Donor-Acceptor Torsional Angle for Highly Efficient Organic Light-Emitting Diodes

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CCS Chemistry 2022年第4期4卷 1284-1294页

作者： Xiaojie Chen Dongyu Ma Tiantian Liu Zhu Chen Zhan Yang Juan Zhao Zhiyong Yang Yi Zhang zhenguo chi PCFM Lab GD HPPC LabGuangdong Engineering Technology Research Centre for High-Performance Organic and Polymer Photoelectric Functional FilmsState Key Laboratory of Optoelectronic Materials and TechnologiesSchool of ChemistrySun Yat-sen UniversityGuangzhou 510275 State Key Laboratory of Optoelectronic Materials and Technologies School of Materials Science and EngineeringSun Yat-sen UniversityGuangzhou 510275

Hybridized local and charge-transfer(HLCT)excitedstate fluorophores,which enable full exciton utilization through a reverse intersystem crossing fromhigh-lying triplet states to singlet state,have attracted increasing attention toward organic light-emitting diodes(OLEDs)***,we report three D-π-A-π-D-type isomers o-2CzBT,m-2CzBT,and p-2CzBT by adjusting the donor(D)units from ortho-,meta-,to para-substituted positions with the acceptor(A)core unit,*** HLCT properties of the three compounds are evidently confirmed by theoretical calculations,solvatochromic behaviors,and transient decay lifetimes *** the substituted position changes from the ortho-,meta-,and para-positions,the reduced steric hindrance brings about decreased torsional angle between D and A moieties,resulting in increased oscillator ***,the parasubstituted p-2CzBT is endowed with a more locally excited component that accounts for faster radiative decay,leading to a higher fluorescent efficiency than that of o-2CzBT and *** expected,p-2CzBT enables its nondoped and doped OLEDs with higher external quantum efficiencies(EQEs)of 12.3% and 15.0%,respectively,which are among the state-ofthe-art efficiencies of HLCT-based ***,o-2CzBT and m-2CzBT are also utilized as host materials for high-performance OLEDs,thus extending the application of HLCT materials.

关键词： hybridized local and charge-transfer torsional angle oscillator strength high efficiency OLED