Dimesitylboryl-functionalized tetraphenylethene derivatives: efficient solid-state luminescent materials with enhanced electron-transporting ability for nondoped OLEDs

Chen, Long; Lin, Gengwei; Peng, Huiren; Zhuang, Zeyan; Shen, Pingchuan; Ding, Siyang; Huang, Du Shu; Hu, Rongrong; Chen, Shuming; Huang, Fei; Qin, Anjun; Zhao, Zujin; Tang, Ben Zhong

doi:10.1039/c6tc01383j

Cited by 33 publications

(16 citation statements)

References 52 publications

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“…This value is much lower than the value of TPE (−1.22 eV), indicating that the introduction of the dimesitylborane group effectively reduces the LUMO energy level, which facilitates electron injection. Compared to devices with additional electron transport layers (TPBi), the use of a TPE‐DB OLED device as a light source for producing a [ITO/HATCN (20 nm)/NPB (40 nm)/TPE‐DB (60 nm)/LiF (1 nm)/Al (100 nm)] results in superior electroluminescence (EL) performance with high efficiency up to 13.5 cd/A and 4.6 % . The advantage of the dimesitylborane groups linking the TPE groups is that the electron transport of the material can be improved without reducing the emission efficiency, but the disadvantage is that the thermal stability of the material is reduced due to the poor thermal stability of dimesitylborane.…”

Section: Fluorescent Chromophores Containing Dimesitylboranes For Oledsmentioning

confidence: 99%

Design and Development of Highly Efficient Light‐Emitting Layers in OLEDs with Dimesitylboranes: An Updated Review

Huo

Wang

et al. 2019

The Chemical Record

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With excellent luminescent properties and transport properties, triarylborane compounds containing two mesitylenes (Mes) have gained much attention for their application in OLEDs as light‐emitting layers. This study serves as an updated review summarizing recent developments in the design of fluorescent chromophores and phosphorescent host materials for OLEDs comprising small molecular compounds of dimesitylborane (BMes2) as luminescent layers, with attention to the performance of different light‐emitting devices. Problems that need to be solved in the research and application of BMes2 in OLEDs are presented and the application prospects of such materials are suggested.

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Section: Fluorescent Chromophores Containing Dimesitylboranes For Oledsmentioning

confidence: 99%

Design and Development of Highly Efficient Light‐Emitting Layers in OLEDs with Dimesitylboranes: An Updated Review

Huo

Wang

et al. 2019

The Chemical Record

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“…Besides using DFT calculation, cyclic voltammetry (CV) measurements were also used to determine the HOMO and LUMO energy levels of the emitters. As shown in Figure 6, PN-BTZ-Cz and DP-BTZ-Cz exhibited a similar quasi-reversible oxidation process with onset potentials of 0.93 and 0.91 V. The energy levels of the HOMO and the LUMO were calculated from the onset oxidation potential ( E onset ) and the optical band gap E g using the following equations: HOMO = −(4.4 + E onset ) eV and LUMO = (HOMO + E g ) eV, where E g = 1240/λ onset and λ onset is the onset absorption wavelength, 20 and these were equal to −5.33 and −3.08 eV for PN-BTZ-Cz and −5.31 and −3.06 eV for DP-BTZ-Cz, respectively. The high HOMO energy of the molecules suggests that they possess good electron-transporting properties, and the narrow band gap of PN-BTZ-Cz and DN-BTZ-Cz, on the other hand, was consistent with their red emission.…”

Section: Resultsmentioning

confidence: 99%

In Situ Generation of Red-Emissive AIEgens from Commercial Sources for Nondoped OLEDs

Zhao

et al. 2018

ACS Omega

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Luminescent materials with red emission are promising materials for optoelectronic devices and biological sciences. However, their synthesis is often complicated. In this work, we developed a facile approach to generating red-emissive luminogens with aggregation-induced emission (AIE) characteristics from commercially available reactants. The new compounds, abbreviated PN-BTZ-Cz and DP-BTZ-Cz, were prepared by coupling 4,7-dibromobenzo[ c ][1,2,5]thiadiazole with (1-naphehyl)phenylamine or diphenylamine followed by the reaction of the monobromo-substituted compounds with carbazole. Although all of the reactants were non-AIE-active, PN-BTZ-Cz and DP-BTZ-Cz showed AIE characteristics. This suggested that the AIE chromophores were generated in situ through the reactions. PN-BTZ-Cz and DP-BTZ-Cz were soluble in common organic solvents and showed red emission with high fluorescence quantum yields of 42.2 and 38.3% in the film, respectively. They were thermally and morphologically stable, as revealed by their high decomposition temperature (up to 327 °C) and glass-transition temperature (up to 120 °C). Nondoped organic light-emitting diodes with a configuration of ITO/HATCN/TAPC/PN-BTZ-Cz or DP-BTZ-Cz/Bphen/Liq/Al were fabricated using these compounds as emitting layers, which emitted red electroluminescence at a low turn-on voltage (down to 2.8 V) with a maximum external quantum yield of up to 2.7% and a small efficiency roll-off.

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“…The introduction of electron‐transporting functional groups into the p‐conjugated system of the emitter is then a viable strategy to improve the charge balance. The incorporation into a TPE core of dimesitylboryl (DB) groups, which are inherently electron deficient, lowers the LUMO energy levels and thus enhances the electron affinities and electron‐transporting abilities . Devices fabricated by using TPE‐DB as both light‐emitting and electron‐transporting layers exhibit green emission (λ EL =521–525 nm) with turn‐on voltages between 3.9 and 4.9 V, luminance up to 38430 cd/m 2 and efficiencies of 13.5 cd/A and 4.6 %, which are much better than those from the device with 1,3,5‐tris‐(N‐phenylbenzimidazol‐2‐yl)benzene (TPBi) as the electron‐transporting layer, demonstrating that TPE‐DB is an efficient bifunctional material of light emitters and electron transporters for non‐doped OLEDs.…”

Section: Recent Aiegens Emitters For Non‐doped Oledsmentioning

confidence: 99%

Recent Developments in AIEgens for Non‐doped and TADF OLEDs

Rizzo

Cucinotta

2018

Israel Journal of Chemistry

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The design of innovative and more efficient Aggregation‐Induced Emission (AIE) chromophores has kept a very high scientific interest since the first report on 2001. Among the possible applications, the field of the organic electroluminescent diodes (OLEDs) is highly attractive. This review will focus on very recent development in the design of AIE molecules for OLEDs, with particular attention on the performance of different emitting devices. Another key point is the description of the new class of AIE luminogens showing Thermally Activated Delayed Fluorescence (TADF), which appears as possible solution to overcome the limitation of fluorescent dyes employed in electroluminescent devices.

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Dimesitylboryl-functionalized tetraphenylethene derivatives: efficient solid-state luminescent materials with enhanced electron-transporting ability for nondoped OLEDs

Abstract: Efficient n-type emitters are prepared from dimesitylboryl-functionalized tetraphenylethene derivatives.

Cited by 33 publications

References 52 publications

Design and Development of Highly Efficient Light‐Emitting Layers in OLEDs with Dimesitylboranes: An Updated Review

Design and Development of Highly Efficient Light‐Emitting Layers in OLEDs with Dimesitylboranes: An Updated Review

In Situ Generation of Red-Emissive AIEgens from Commercial Sources for Nondoped OLEDs

Recent Developments in AIEgens for Non‐doped and TADF OLEDs

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