A benzoindole-cored building block for deep blue fluorescent materials: synthesis, photophysical properties, and applications in organic light-emitting diodes

Ye, Shanghui; Wu, Cong-Jin; Gu, Pengfei; Tai, Xue–Cheng; Zhang, Senyu; Jing, Tongtong; Wang, Shi; Yang, Xiaodi; Li, Yonghua; Huang, Wei

doi:10.1039/d0tc04221h

Cited by 6 publications

(2 citation statements)

References 71 publications

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“…Benzo[ g ]indole scaffold is used in the synthesis of fluorescent organic molecules that have wide biomedical and technical applications [ 26 , 27 ]. Our interest in the photophysics of the synthesized benzo[ g ]pyrroloimidazoindoles 6 is instigated by the presence of intense long-wavelength ( λ abs (max)~410 nm, ε ≈ 40,000 M −1 cm −1 ) electronic absorption bands with maxima in the violet region and blue photoluminescence, which could make them attractive materials in optoelectronics for blue organic light-emitting diodes (OLEDs).…”

Section: Resultsmentioning

confidence: 99%

Contributing to Biochemistry and Optoelectronics: Pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and Cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles via [3+2] Annulation of Acylethynylcycloalka[b]pyrroles with Δ1-Pyrrolines

Опарина

Kolyvanov

Ushakov

et al. 2023

IJMS

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Available pyrrolylalkynones with tetrahydroindolyl, cycloalkanopyrrolyl, and dihydrobenzo[g]indolyl moieties, acylethynylcycloalka[b]pyrroles, are readily annulated with Δ1-pyrrolines (MeCN/THF, 70 °C, 8 h) to afford a series of novel pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles functionalized with an acylethenyl group in up to an 81% yield. This original synthetic approach contributes to the arsenal of chemical methods promoting drug discovery. Photophysical studies show that some of the synthesized compounds, e.g., benzo[g]pyrroloimidazoindoles, are prospective candidates for TADF emitters of OLED.

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Section: Resultsmentioning

confidence: 99%

Contributing to Biochemistry and Optoelectronics: Pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and Cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles via [3+2] Annulation of Acylethynylcycloalka[b]pyrroles with Δ1-Pyrrolines

Опарина

Kolyvanov

Ushakov

et al. 2023

IJMS

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“…Metal halide perovskites are regarded as the most promising forefront emissive materials for ultrahigh-definition displays owing to their excellent optoelectronic properties of high photoluminescence quantum yield (PLQY), widely tunable band gap, narrow full-width at half-maximum (FWHM), wide color gamut (140%), and low-cost solution processability. − The cutting-edge external quantum efficiencies (EQEs) have exceeded 20% for near-infrared, red, and green perovskite light-emitting diodes (PeLEDs) so far. − Nevertheless, the state-of-the-art blue PeLEDs demonstrate an inferior device performance in terms of brightness, EQE, and operational stability. − Remarkably, the sky-blue PeLEDs with an emission wavelength of 475–495 nm have obtained peak EQEs in the range of 10%–13.8%, demonstrating the latest advancement of blue PeLEDs. − Meanwhile, the display industry urgently needs the saturated blue emission with the wavelength of 467 nm according to the Rec. 2020 standards. , Previous research has found that blue PeLED’s luminous efficiency enormously depends on the emission wavelength as summarized in Table S1, and the best blue PeLED emitting at 467 nm could only reach an EQE of 5.5% by using mixed bromide/chloride perovskites .…”

Section: Introductionmentioning

confidence: 99%

Basic Amino Acids Modulated Neutral-pH PEDOT:PSS for Stable Blue Perovskite Light-Emitting Diodes

Liu

Dong

et al. 2022

ACS Appl. Mater. Interfaces

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State-of-the-art external quantum efficiencies (EQEs) have exceeded 20% for near-infrared, red, and green perovskite light-emitting diodes (PeLEDs) so far. Nevertheless, the cutting-edge blue counterparts demonstrate an inferior device performance, which impedes the commercialization and industrialization of PeLEDs in ultrahigh-definition displays. As the most popular hole transport layer, poly(3,4-ethylenedioxythiophene):polystyrenesulfonate (PEDOT:PSS) bears the acidic and hygroscopic drawbacks, which deteriorates the device efficiency and long-term stability of blue PeLEDs. In this work, the basic amino acids with zwitterionic characteristics are proposed to modulate the pH of PEDOT:PSS, which are arginine, lysine, and histidine. It is found that they play a triple function to the blue perovskite films: modulating the acidity of PEDOT:PSS, controlling the crystalline process, and passivating the defects at the PEDOT:PSS/perovskite interface. As a result, the utilization of neutral PEDOT:PSS leads to a significant enhancement in stability and photoluminescence quantum yield. Eventually, the pure-blue PeLEDs achieve a record EQE of 5.6% with the emission peak at 467 nm. This research proves that the interfacial engineering of hole transport layers is a reliable strategy to enhance the device efficiency and operation stability of blue PeLEDs.

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Tunable Intramolecular Charge Transfer Effect on Diphenylpyrazine‐Based Linear Derivatives and Their Expected Performance in Blue Emitters

Luo

et al. 2021

Advanced Optical Materials

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High efficiency deep‐blue emitters are one of the basic requests for an outstanding full‐color organic light emitting diode (OLED) display. Herein, a linear D‐A‐D diphenylpyrazine structure is designed for maximizing the π‐conjugation effect, whilst two deep‐blue (DPP‐DPhC and DPP‐D3C) and one blue (DPP‐DTPA) fluorophores are synthesized by incorporating the N‐phenylcarbazole and triphenylamine donor units, respectively. As a result, they emit bright deep‐blue to blue fluorescence with the luminescence quantum yields of 0.312–0.888 in solid state. Fortunately, all the non‐doped and doped OLED devices show deep‐blue (N‐phenylcarbazole disubstituted compounds, DPP‐DPhC and DPP‐D3C) and blue (triphenylamine derivative, DPP‐DTPA) electroluminescence (EL) performance with the maximum external quantum efficiencies (EQEs) of >4%. Comprehensively considering other parameters, the deep‐blue non‐doped OLED device based on DPP‐DPhC exhibits the best EL performance with the maximum EQE of 5.73% with the Commission International de L'Eclairage (CIEx,y) coordinate of (0.151, 0.078) among them. These results demonstrate the feasibility of this strategy and provide a simple method to achieve high efficiency deep‐blue emitters.

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A benzoindole-cored building block for deep blue fluorescent materials: synthesis, photophysical properties, and applications in organic light-emitting diodes

Abstract: Deep blue fluorescent materials are crucial in the commercialization of organic light-emitting diodes (OLEDs) for full-color displays or solid-state lighting sources. In this work, a series of aromatic ring compounds...

Cited by 6 publications

References 71 publications

Contributing to Biochemistry and Optoelectronics: Pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and Cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles via [3+2] Annulation of Acylethynylcycloalka[b]pyrroles with Δ1-Pyrrolines

Contributing to Biochemistry and Optoelectronics: Pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and Cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles via [3+2] Annulation of Acylethynylcycloalka[b]pyrroles with Δ1-Pyrrolines

Basic Amino Acids Modulated Neutral-pH PEDOT:PSS for Stable Blue Perovskite Light-Emitting Diodes

Tunable Intramolecular Charge Transfer Effect on Diphenylpyrazine‐Based Linear Derivatives and Their Expected Performance in Blue Emitters

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