Dimesitylboryl-functionalized fluorene derivatives: Promising luminophors with good electron-transporting ability for deep blue organic light-emitting diodes

Xu, Xiaofei; Ye, Shanghui; He, Bo; Chen, Bin; Xiang, Jiayun; Zhou, Jian; Lü, Ping; Zhao, Zujin; Qiu, Huayu

doi:10.1016/j.dyepig.2013.09.042

Cited by 21 publications

(11 citation statements)

References 43 publications

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“…The acceptor moieties were synthesized by reacting 1,4-dibromobenzenze ( 1 ) or 1,3,5-tribromobenzene ( 4 ) with dimesitylboron fluoride ( 2 ), yielding compounds 3 , 5 , and 6 (Scheme ) to afford N-ph-B, N 3 -ph-B, and N 3 -ph-B 2 .…”

Section: Resultsmentioning

confidence: 99%

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Charge Transfer Emission in Oligotriarylamine–Triarylborane Compounds

Bonn

Wenger

2015

J. Org. Chem.

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Donor-acceptor compounds exhibiting charge transfer emission are of interest in a variety of different contexts, for example, for nonlinear optical processes and for sensor applications. Recently investigated triarylamine-triarylborane compounds represent an important class of donor-acceptor systems, and we explored to what extent their charge-transfer properties can be further improved by using stronger amine donors and borane acceptors than prior studies. The oligotriarylamine employed here is a much stronger donor than previously used triarylamines containing single nitrogen centers. In order to increase the acceptor strength, the electron-accepting unit was equipped with two (instead of one) dimesitylboron substituents. In our comparative study, six donor-acceptor compounds were synthesized and investigated by cyclic voltammetry and optical spectroscopy. An increase of the donor strength through replacement of an ordinary triarylamine by an oligotriarylamine unit leads to the expected energetic stabilization of charge transfer (CT) excited states, but the emission solvatochromism is not more pronounced. The attempted increase of the acceptor strength by substitution of the acceptor moiety by two (instead of one) dimesitylboron groups leads to a drastic decrease of emission quantum yields. On the basis of these results, our purely experimental study provides fundamental guidelines for the design of new triarylamine-triarylborane donor-acceptor compounds with favorable charge-transfer emission properties.

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Section: Resultsmentioning

confidence: 99%

“…Compound 3 . 1,4-Dibromobenzene ( 1 ) (1.75 g, 7.42 mmol) was dissolved in dry Et 2 O (20 mL) under N 2 .…”

Section: Experimental Sectionmentioning

confidence: 99%

Charge Transfer Emission in Oligotriarylamine–Triarylborane Compounds

Bonn

Wenger

2015

J. Org. Chem.

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“…32) was reported to have a very high F F of 0.97 in THF and 0.54 in a thin lm. 152 The dimesitylboryl moiety (B(Mes) 2 ) is a strong electronacceptor; thus, it usually can enhance the F F 153,154 due to the non-planar arrangement of the bulky mesityl groups, which can diminish strong molecular aggregation in condensed phases to suppress the self-quenching effects. The undoped device with the conguration of ITO/NPB (40 nm)/SF31 (20 nm)/TPBI (40 nm)/LiF (0.5 nm)/Al (100 nm) can show a maximum EQE, CE, and PE of 4.3%, 3.3 cd A À1 , and 1.3 lm W À1 , respectively, with deep-blue emission CIE coordinates of (0.15, 0.09).…”

Section: Deep-blue Emitters Furnishing High-performance Oledsmentioning

confidence: 99%

Recent advances of the emitters for high performance deep-blue organic light-emitting diodes

2015

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“…The properties of the devices indicated that 47 as a multifunctional optoelectronic material can be utilized as a blue emitter and hole- and electron-transporting material. Xu et al reported 48 and 49 , possessing fluorene derivatives and Mes 2 B as deep blue emitting materials ( Figure 9 ) [ 78 ]. They showed deep blue emission peak at ~430 nm with excellent Φ F of up to 94% as thin film and low-lying LUMO energy levels, which indicated their excellent properties allowing them to be used as both emitter and electron transporting materials.…”

Section: Triarylborane-based Small Molecules/oligomersmentioning

confidence: 99%

Triarylborane-Based Materials for OLED Applications

2017

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Multidisciplinary research on organic fluorescent molecules has been attracting great interest owing to their potential applications in biomedical and material sciences. In recent years, electron deficient systems have been increasingly incorporated into fluorescent materials. Triarylboranes with the empty p orbital of their boron centres are electron deficient and can be used as strong electron acceptors in conjugated organic fluorescent materials. Moreover, their applications in optoelectronic devices, energy harvesting materials and anion sensing, due to their natural Lewis acidity and remarkable solid-state fluorescence properties, have also been investigated. Furthermore, fluorescent triarylborane-based materials have been commonly utilized as emitters and electron transporters in organic light emitting diode (OLED) applications. In this review, triarylborane-based small molecules and polymers will be surveyed, covering their structure-property relationships, intramolecular charge transfer properties and solid-state fluorescence quantum yields as functional emissive materials in OLEDs. Also, the importance of the boron atom in triarylborane compounds is emphasized to address the key issues of both fluorescent emitters and their host materials for the construction of high-performance OLEDs.

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Dimesitylboryl-functionalized fluorene derivatives: Promising luminophors with good electron-transporting ability for deep blue organic light-emitting diodes

Cited by 21 publications

References 43 publications

Charge Transfer Emission in Oligotriarylamine–Triarylborane Compounds

Charge Transfer Emission in Oligotriarylamine–Triarylborane Compounds

Recent advances of the emitters for high performance deep-blue organic light-emitting diodes

Triarylborane-Based Materials for OLED Applications

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