A series of novel host materials based on the 10,11-dihydro-5H-dibenzo[b,f]azepine unit for highly efficient green and red organic light-emitting diodes

Sun, Bangjin; Tong, Kai‐Ning; Liu, Sheng-Nan; Fung, Man‐Keung; Fan, Jian

doi:10.1039/d0tc05457g

Cited by 4 publications

(4 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The absorption spectra of S -1 – S -9 become broader bands in cast film compared with their DCM solutions (Figure S3), which can be attributed to intermolecular interaction between chirality inducers . However, no absorption in the visible region was observed, indicating that these inducers S -1 – S -9 can act as an excellent energy donor for fabricating efficient green and red OLEDs …”

Section: Resultsmentioning

confidence: 99%

“…32 However, no absorption in the visible region was observed, indicating that these inducers S-1−S-9 can act as an excellent energy donor for fabricating efficient green and red OLEDs. 33 The photoluminescence (PL) emission of chirality inducers S-1−S-9 were located at the range from 361 to 518 nm in DCM solution (Figure S3). As compared with the PL solution emission, the cast film of S-1 exhibited bathochromic shift emission with a high-intensity peak at 381 nm and a shoulder peak at 449 nm.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Controllable Circularly Polarized Electroluminescence Performance Improved by the Dihedral Angle of Chiral-Bridged Binaphthyl-Type Dopant Inducers

Zhang

Quan

et al. 2021

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

Chirality of 1,1′-binaphthol (BINOL) is due to the restricted rotation between two naphthalene rings, and its skeletal structure of binaphthyl unit can be further modified by choosing functionalized substituents to afford the enlarged chiral induction effect. In this paper, we designed and synthesized nine chiral binaphthyl derivatives ( R/S-1–R/S-9) as circularly polarized electroluminescence (CP-EL) inducers by inserting various bridged alkyl chains into the hydroxyl groups of BINOL or introducing functionalized substituents with different steric hindrances on the 3,3′-position of 2,2′-methylenedioxy-1,1′-binaphthalene. Their molecular conformations and CPL behaviors of nine chiral inducers were significantly dependent on the length of the alkyl chain and the degree of substituent steric hindrance, which could further regulate their chiral induction effect on achiral fluorescent polymer F8BT from small to large in the doped films. Moreover, in virtue of the planar rigid conjugated molecular conformation of R/S-1, R/S-6, and R/S-9, the amplified CPL signals (|g PL|) were detected as high as 2.36 × 10–2, 2.06 × 10–2, and 1.26 × 10–2 from blends of F8BT and these chiral inducers. The circularly polarized organic light-emitting diode (CP-OLED) device on the blends of F8BT and chiral inducers ( R/S-6) with small dihedron angle and excellent carrier mobility showed a low turn-on voltage (V on < 4.5 V), high brightness (> 10509.6 cd/m2), and maximum |g EL| value of 1.86 × 10–2 (F8BT + 5% R/S-6). This work can develop and provide a valuable reference for CP-OLED device design through chiral dopant induction.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Controllable Circularly Polarized Electroluminescence Performance Improved by the Dihedral Angle of Chiral-Bridged Binaphthyl-Type Dopant Inducers

Zhang

Quan

et al. 2021

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

show abstract

“…The dibenzo[ b , f ]azepine ( 1a ) scaffold ( Figure 1 ) is featured in commercial pharmaceuticals [ 1 ] and other lead compounds [ 2 – 4 ], ligands [ 5 – 6 ] and in materials science with possible applications in organic light emitting diodes (OLEDs) [ 7 ] and dye-sensitized solar cells (DSSCs) [ 8 – 10 ].…”

Section: Introductionmentioning

confidence: 99%

“…4,4'-(5-(Pyridin-2-yl)-10,11-dihydro-5 H -dibenzo[ b,f ]azepine-2,8-diyl)bis( N,N -diphenylaniline) ( 9 ) exhibits properties suitable for the use in organic light emitting diodes [ 7 ] whereas dyes 10 – 12 were found suitable for the use in dye-sensitised solar cells ( Figure 4 ) [ 8 – 10 ].…”

Section: Introductionmentioning

confidence: 99%

Strategies in the synthesis of dibenzo[b,f]heteropines

Maier¹,

Bezuidenhoudt²,

Marais³

2023

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

The dibenzo[b,f]azepine skeleton is important in the pharmaceutical industry, not only in terms of existing commercial antidepressants, anxiolytics and anticonvulsants, but also in reengineering for other applications. More recently, the potential of the dibenzo[b,f]azepine moiety in organic light emitting diodes and dye-sensitized solar cell dyes has been recognised, while catalysts and molecular organic frameworks with dibenzo[b,f]azepine derived ligands have also been reported. This review provides a brief overview of the different synthetic strategies to dibenzo[b,f]azepines and other dibenzo[b,f]heteropines.

show abstract

Creating Efficient Red Thermally Activated Delayed Fluorescence Materials with Cyano‐Substituted 11,12‐Diphenyldipyrido[3,2‐a:2′,3′‐c]phenazine Acceptors

Bai,

Wang,

Zou

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

Red luminescent materials are essential components for full color display and white lightening based on organic light‐emitting diode (OLED) technology, but the extension of emission color towards red or deep red region generally leads to decreased photoluminescence and electroluminescence efficiencies. Herein, we wish to report two new luminescent molecules (2CNDPBPPr‐TPA and 4CNDPBPPr‐TPA) consisting of cyano‐substituted 11,12‐diphenyldipyrido[3,2‐a:2',3'‐c]phenazine acceptors and triphenylamine donors. As the increase of cyano substituents, the emission wavelength is greatly red‐shifted and the reverse intersystem crossing process is promoted, resulting in strong red delayed fluorescence. Meanwhile, due to the formation of intramolecular hydrogen bonds, the molecular structures become rigidified and planarized, which brings about large horizontal dipole ratios. As a result, 2CNDPBPPr‐TPA and 4CNDPBPPr‐TPA can perform as emitters efficiently in OLEDs, furnishing excellent external quantum efficiencies of 28.8% at 616 nm and 20.4% at 648 nm, which are significantly improved in comparison with that of the control molecule without cyano substituents. The findings in this work demonstrate that the introduction of cyano substituents to the acceptors of delayed fluorescence molecules could be a facile and effective approach to explore high‐efficiency red or deep red delayed fluorescence materials.

show abstract

A series of novel host materials based on the 10,11-dihydro-5H-dibenzo[b,f]azepine unit for highly efficient green and red organic light-emitting diodes

Abstract: Three novel host materials (D-PY, S-CZ and S-TPA) based on 10,11-dihydro-5H-dibenzo[b,f]azepine (AZ) motif were designed and synthesized. The donor groups, triphenylamine (TPA) and carbazole (CZ), were attached at the different...

Cited by 4 publications

References 55 publications

Controllable Circularly Polarized Electroluminescence Performance Improved by the Dihedral Angle of Chiral-Bridged Binaphthyl-Type Dopant Inducers

Controllable Circularly Polarized Electroluminescence Performance Improved by the Dihedral Angle of Chiral-Bridged Binaphthyl-Type Dopant Inducers

Strategies in the synthesis of dibenzo[b,f]heteropines

Creating Efficient Red Thermally Activated Delayed Fluorescence Materials with Cyano‐Substituted 11,12‐Diphenyldipyrido[3,2‐a:2′,3′‐c]phenazine Acceptors

Contact Info

Product

Resources

About