Hole-Transporting Spirothioxanthene Derivatives as Donor Materials for Efficient Small-Molecule-Based Organic Photovoltaic Devices

Chan, Chin‐Yiu; Wong, Yi Chun; Chan, Mei‐Yee; Cheung, Sin Hang; So, Shu Kong; Yam, Vww

doi:10.1021/cm5033699

Cited by 44 publications

(63 citation statements)

References 40 publications

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“…However, there are very limited examples of a single class of N^C‐chelate boron compounds that show tunable emission colors covering the entire visible spectrum. With our interests and previous works on various functionalized boron(III) compounds and spiro derivatives,, it was anticipated that the combination of the rigid nature of the N^C boron chelate and a bulky spiro structure can yield stable boron compounds with interesting photophysical properties. Herein, we report the design, synthesis, electrochemical, photophysical and electroluminescence properties of a new class of spiro‐containing N^C‐chelated four‐coordinate boron(III) compounds which exhibit very strong luminescence in both solution and solid‐state thin films.…”

Section: Introductionmentioning

confidence: 99%

Air‐Stable Spirofluorene‐Containing Ladder‐Type Bis(alkynyl)borane Compounds with Readily Tunable Full Color Emission Properties

Wong

et al. 2016

Chemistry A European J

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A series of air-stable spiro-fused ladder-type boron(III) compounds has been designed, synthesized, and the electrochemistry and photophysical behavior have been characterized. By simply varying the substituents on the pyridine ring and extending the π-conjugation of the spiro framework, the emission color of these compounds can be easily fine-tuned spanning the visible spectrum from blue to red. All compounds exhibit a broad and structureless emission band across the entire visible region, assigned as an intramolecular charge-transfer transition originating from the thiophene of the spiro framework to the pyridine-borane moieties. In addition, these compounds demonstrate high photoluminescence quantum yields of up to 0.81 in dichloromethane solution and 0.86 in doped thin films. Some of the compounds have also been employed as emissive materials, in which solution-processed organic light-emitting devices (OLEDs) with tunable emission colors spanning the visible spectrum from blue, green to red have been realized, demonstrating the potential applications of these boron compounds in OLEDs.

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Section: Introductionmentioning

confidence: 99%

Air‐Stable Spirofluorene‐Containing Ladder‐Type Bis(alkynyl)borane Compounds with Readily Tunable Full Color Emission Properties

Wong

et al. 2016

Chemistry A European J

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“…In recent years, sulfone was introduced as an electron-accepting building block in luminescent materials for organic light-emitting diodes (OLEDs) [27][28][29][30][31][32][33][34][35] . The structure of diphenyl sulfone has also been applied [36][37][38][39][40][41] .…”

Section: Formation Of Intramolecular Dimer Radical Ions Of Diphenyl Smentioning

confidence: 99%

Formation of intramolecular dimer radical ions of diphenyl sulfones

Okamoto

Kawai

Kozawa

2020

Sci Rep

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Dimer radical ions of aromatic molecules in which excess charge is localized in a pair of rings have been extensively investigated. While dimer radical cations of aromatics have been previously produced in the condensed phase, the number of molecules that form dimer anions is very limited. In this study, we report the formation of intramolecular dimer radical ions (cations and anions) of diphenyl sulfone derivatives (DPs) by electron beam pulse radiolysis in the liquid phase at room temperature. The density functional theory (DFT) calculations also showed the formation of the dimer radical ions. The torsion barrier of the phenyl ring of DPs was also calculated. It was found that the dimer radical ions show the larger barrier than the neutral state. Finally, stability of the dimer radical anion is dependent on not only the inductive effect of the sulfonyl group but the conjugation involving the d-orbital of the S atom and the phenyl rings.

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“…Different from fluorene, the 9H‐thioxanthene 10,10‐dioxide unit is nonplanar, and the dihedral angle between the least‐squares planes through the benzene rings is about 130° . The spiro[fluorene‐9,9′‐thioxanthene‐ S,S ‐dioxide] isomers of 2,7‐diyl spiro[fluorene‐9,9′‐thioxanthene‐ S,S ‐dioxide] (FSO) and 2′,7′‐diyl spiro[fluorene‐9,9′‐thioxanthene‐ S,S ‐dioxide] (SOF) based small molecule materials exhibited a high hole mobility in OPV and a high current efficiency in OLED, respectively …”

Section: Introductionmentioning

confidence: 99%

Deep‐blue light‐emitting polyfluorenes containing spiro[fluorene‐9,9′‐thioxanthene‐S,S‐dioxide] isomers

Peng

Zhang

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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Blue light‐emitting polyfluorenes, PPF‐FSOs and PPF‐SOFs were synthesized via introducing spiro[fluorene‐9,9′‐thioxanthene‐S,S‐dioxide] isomers (2,7‐diyl and 2′,7′‐diyl) (FSO/SOF) into the poly[9,9‐bis(4‐(2‐ethylhexyloxy) phenyl)fluorene‐2,7‐diyl] (PPF) backbone, respectively. With the increasing contents of FSO and SOF moieties, the absorption and PL spectra of PPF‐FSOs show slight red shift, while that of PPF‐SOFs exhibit blue shift, respectively. The HOMO and LUMO levels reduce gradually with increasing SOF unit in PPF‐SOFs. The polymers emit blue light peaked around 430–445 nm and show an excellent spectral stability with the variation in current densities. The distinctly narrowing EL spectra were observed with the incorporation of isomers in the polymers. The full width at half maximum reduced by 15 nm for PPF‐SOFs, resulting in a blue shift with the CIE coordinates from (0.16, 0.11) to (0.16, 0.08). With a device configuration of ITO/PEDOT:PSS/EML/CsF/Al, a maximum luminance efficiency (LEmax) of 2.00 cd A−1, a maximum external quantum efficiency (EQEmax) of 3.76% with the CIE coordinates of (0.16, 0.08) for PPF‐SOF15 and a LEmax of 1.68 cd A−1, a EQEmax of 2.38% with CIE (0.16, 0.12) for PPF‐FSO10 were obtained, respectively. The result reveals that spiro[fluorene‐9,9′‐thioxanthene‐S,S‐dioxide] isomers are promising blocks for deep‐blue light‐emitting polymers. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2332–2341

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Hole-Transporting Spirothioxanthene Derivatives as Donor Materials for Efficient Small-Molecule-Based Organic Photovoltaic Devices

Cited by 44 publications

References 40 publications

Air‐Stable Spirofluorene‐Containing Ladder‐Type Bis(alkynyl)borane Compounds with Readily Tunable Full Color Emission Properties

Air‐Stable Spirofluorene‐Containing Ladder‐Type Bis(alkynyl)borane Compounds with Readily Tunable Full Color Emission Properties

Formation of intramolecular dimer radical ions of diphenyl sulfones

Deep‐blue light‐emitting polyfluorenes containing spiro[fluorene‐9,9′‐thioxanthene‐S,S‐dioxide] isomers

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