Carbazole derivatives containing one or two tetra-/triphenylethenyl units as efficient hole-transporting OLED emitters

Nasiri, Sohrab; Cekaviciute, Monika; Simokaitienė, Jūratė; Petrauskaite, Aina; Volyniuk, Dmytro; Andrulevičienė, Viktorija; Bezvikonnyi, Oleksandr; Gražulevičius, Juozas V.

doi:10.1016/j.dyepig.2019.04.045

Cited by 16 publications

(5 citation statements)

References 48 publications

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“…In 2019, Grazulevicius et al [ 48 ] synthesized a carbazole‐based non‐D–A ( 58–62 ) system that showed a significant blue or green emission depending on the substitution. Molecules 58 – 60 were substituted with one arylethenyl moiety and showed emission maxima of 480, 458, and 479 nm, respectively, whereas 61 and 62 were substituted with TPE/TriPE moiety and showed emission maxima of 500 and 517 nm, respectively.…”

Section: Molecules With Non‐d–a Structuresmentioning

confidence: 99%

Approaches for Fabricating Tri‐ and Tetraphenylethene‐Based Blue Organic Light‐Emitting Diodes Using Donor–Acceptor and Non‐Donor–Acceptor Molecular Architectures

Harshini

Devibala

Angela

et al. 2022

Physica Rapid Research Ltrs

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Organic light‐emitting diodes (OLEDs) have exceeded expectations in terms of portability and affordability; still there is potential for advancement in terms of efficiency and color changeability. Research on flexible displays and OLED light emission is hampered by the low solid‐state efficiency and bandgap discrepancies of blue light emitters. However, aggregation‐induced emission (AIE) presents an opportunity to create efficient blue emitters. By suppressing the π‐π stacking interactions, triphenylethene (TriPE) and tetraphenylethene (TPE) molecule‐based AIE luminogens exhibit outstanding solid‐state emission and increased device efficiency. Additionally, the presence of TriPE and TPE donor units in the architecture of non‐donor–acceptor (non‐D–A)‐ and donor–acceptor (D–A)‐based architectures has increased chemical and thermal stability with high efficiency. This article emphasizes multiple device architectures and different light emissions (blue, red, and green) set forth by potential electron donating/accepting molecules possessing intriguing efficiency in the device fabrication. It also presents the substitution effect on TriPE and TPE donor units and the applicability of non‐D–A and D–A systems in OLEDs.

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Section: Molecules With Non‐d–a Structuresmentioning

confidence: 99%

Approaches for Fabricating Tri‐ and Tetraphenylethene‐Based Blue Organic Light‐Emitting Diodes Using Donor–Acceptor and Non‐Donor–Acceptor Molecular Architectures

Harshini

Devibala

Angela

et al. 2022

Physica Rapid Research Ltrs

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“…In recent years, the phenanthroimidazole (PI)-based derivatives have emerged as potential organic emitters because of their favorable properties such as easier synthesis, high photoluminescence quantum efficiency, appropriate π-conjugation length, rigid geometry with high thermal stability, and inherent bipolar characteristics. , On the other hand, carbazole, a popular hole-transporting material with high triplet energy, offers an immense opportunity for functionalization at various positions by a simple modification of widely available synthetic methodologies. − Hence, it has been routinely used in constructing fluorescent and phosphorescent organic light-emitting diodes, − thermally activated delayed fluorescence, − and hybridized local and charge transfer (HLCT) emitters. − Therefore, promising bipolar fluorescent emitters are expected from carbazole–phenanthroimidazole-conjugated fluorophores. , In the literature, there are some reports available where carbazole–PI-based systems have shown promising results toward the development of blue emitters. For example, Lu and co-workers synthesized new carbazole–phenanthroimidazole derivatives with different spacer units like phenylvinyl or phenylvinylcarbazolylvinyl and used them for saturated blue emission with CIE x , y of (0.16, 0.17), showing good electroluminescence properties .…”

Section: Introductionmentioning

confidence: 99%

Effect of Cyano on the Functional Properties of Phenanthroimidazole-Substituted Carbazole Derivatives

Sharma

Thomas

Kesavan

et al. 2021

ACS Appl. Electron. Mater.

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A series of carbazole-based structural isomers appended with phenanthroimidazole and/or cyano chromophores are designed and synthesized. The structure−property relationship of bifunctionalized dyes is studied and compared with that of monofunctionalized dyes. The position of the chromophoric connectivity to the core carbazole is found to determine the physiochemical and electroluminescence properties of the isomeric dyes. The dyes with phenanthroimidazole incorporated at the C2 position of the carbazole offer a higher π-conjugation as compared to the dye with the C2 cyano-functionalized derivative. The incorporation of a phenylene spacer between the carbazole and phenanthroimidazole led to a red shift in emission, which is attributable to the reorganization of dye in the excited state. The C2 and C7 substituted bipolar dye offers more red-shifted emission because of the increased charge transfer component, which is further confirmed by its polar excited state in solvatochromism studies. The bifunctionalized dyes displayed high thermal/ morphological stability with a thermal decomposition and glass transition temperature greater than 411 and 119 °C, respectively. Moreover, electrochemical measurements of the dyes reveal that the addition of a cyano substitution on the carbazole facilitates the stabilization of the LUMO. The materials are employed as dopant emitters in solution-processed multilayer organic light-emitting diode (OLED) devices and display deep-blue electroluminescence with Commission International L'Eclairage (CIE) coordinates of (0.16, 0.06) and external quantum efficiency of 5.7%, indicating the potential application for efficient blue OLEDs.

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“…Compounds based on carbazole [17][18][19] or triphenylamine [20,21] moieties substituted by tetraphenylethene and/or triphenylethene units were previously reported to show AIE or AIEE effects. Due to the specific linkage topology, some of them displayed blue/sky-blue fluorescence [22,23]. In addition to carbazole and triphenylamine, nitrogen-containing heteroaromatic acridan derivatives are also well established in OLED technology, some of them as blue emitters.…”

Section: Introductionmentioning

confidence: 99%

Towards Blue AIE/AIEE: Synthesis and Applications in OLEDs of Tetra-/Triphenylethenyl Substituted 9,9-Dimethylacridine Derivatives

et al. 2020

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Aiming to design blue fluorescent emitters with high photoluminescence quantum yields in solid-state, nitrogen-containing heteroaromatic 9,9-dimethylacridine was refined by tetraphenylethene and triphenylethene. Six tetra-/triphenylethene-substituted 9,9-dimethylacridines were synthesized by the Buchwald-Hartwig method with relatively high yields. Showing effects of substitution patterns, all emitters demonstrated high fluorescence quantum yields of 26–53% in non-doped films and 52–88% in doped films due to the aggregation induced/enhanced emission (AIE/AIEE) phenomena. In solid-state, the emitters emitted blue (451–481 nm) without doping and deep-blue (438–445 nm) with doping while greenish-yellow emission was detected for two compounds with additionally attached cyano-groups. The ionization potentials of the derivatives were found to be in the relatively wide range of 5.43–5.81 eV since cyano-groups were used in their design. Possible applications of the emitters were demonstrated in non-doped and doped organic light-emitting diodes with up to 2.3 % external quantum efficiencies for simple fluorescent devices. In the best case, deep-blue electroluminescence with chromaticity coordinates of (0.16, 0.10) was close to blue color standard (0.14, 0.08) of the National Television System Committee.

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Carbazole derivatives containing one or two tetra-/triphenylethenyl units as efficient hole-transporting OLED emitters

Cited by 16 publications

References 48 publications

Approaches for Fabricating Tri‐ and Tetraphenylethene‐Based Blue Organic Light‐Emitting Diodes Using Donor–Acceptor and Non‐Donor–Acceptor Molecular Architectures

Approaches for Fabricating Tri‐ and Tetraphenylethene‐Based Blue Organic Light‐Emitting Diodes Using Donor–Acceptor and Non‐Donor–Acceptor Molecular Architectures

Effect of Cyano on the Functional Properties of Phenanthroimidazole-Substituted Carbazole Derivatives

Towards Blue AIE/AIEE: Synthesis and Applications in OLEDs of Tetra-/Triphenylethenyl Substituted 9,9-Dimethylacridine Derivatives

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