Multifunctional derivatives of pyrimidine-5-carbonitrile and differently substituted carbazoles for doping-free sky-blue OLEDs and luminescent sensors of oxygen

Tsiko, Uliana; Bezvikonnyi, Oleksandr; Sych, Galyna; Keruckienė, Rasa; Volyniuk, Dmytro; Simokaitienė, Jūratė; Danyliv, Iryna; Danyliv, Yan; Bučinskas, Audrius; Tan, Xiaofeng

doi:10.1016/j.jare.2021.01.014

Cited by 15 publications

(9 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Grazulivicius and coworkers have also designed 5-cyanopyrimidine derivatives 2 bearing two carbazole fragments in position 4 and 6 (Chart 1). 53 These compounds all exhibit TADF properties with delayed fluorescence (Table 1), even if the photoluminescence quantum yields (PLQY) is significantly decreased when the carbazole fragments are substituted by methoxy groups (compounds 2c). These compounds are described as potential oxygen sensors.…”

Section: Carbazole Substituentsmentioning

confidence: 99%

Diazine-based thermally activated delayed fluorescence chromophores

et al. 2022

View full text Add to dashboard Cite

Section: Carbazole Substituentsmentioning

confidence: 99%

Diazine-based thermally activated delayed fluorescence chromophores

et al. 2022

View full text Add to dashboard Cite

“…More insights could be drawn by analyzing the fluorescence quantum yield (Φ F ) as well as radiative ( k r ) and non-radiative ( k nr ) fluorescence decay rates (see Table 2 ). The Φ PF was typical for carbazole–pyrimidine TADF compounds [ 31 , 43 – 44 ], in the range of 0.01–0.07 and decreased for compounds with stronger acceptor units (see Figure S28b in Supporting Information File 1 ). The radiative decay rate was in the range of 1.3–13.0 × 10 6 s −1 .…”

Section: Resultsmentioning

confidence: 99%

“…In case of TADF emitters, a pyrimidine ring is often connected with a donor unit through a phenylene group as a conjugate π-spacer (s) [ 25 – 28 ]. As the majority of research describes TADF compounds with D-s–A–s–D layout, reports on TADF properties of pyrimidine emitters where the pyrimidine moiety is directly bonded with a donor moiety are scarce [ 29 – 31 ], though several examples of such pyrimidine-based conjugates found utility as high triplet energy hosts [ 32 – 33 ]. Envisaging the potential of the pyrimidine–carbazole pair for achieving efficient deep-blue emission, we were interested to study the influence of substituents in position 2 of the pyrimidine ring on the TADF properties of pyrimidine–carbazole emitters.…”

Section: Introductionmentioning

confidence: 99%

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

Fiodorova¹,

Serevičius²,

Skaisgiris³

et al. 2022

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

The interest in organic materials exhibiting thermally activated delayed fluorescence (TADF) significantly increased in recent years owing to their potential application as emitters in highly efficient organic light emitting diodes (OLEDs). Simple modification of the molecular structure of TADF compounds through the selection of different electron-donating or accepting fragments opens great possibilities to tune the emission properties and rates. Here we present the synthesis of a series of novel pyrimidine–carbazole emitters and their photophysical characterization in view of effects of substituents in the pyrimidine ring on their TADF properties. We demonstrate that electron-withdrawing substituents directly connected to the pyrimidine unit have greater impact on the lowering of the energy gap between singlet and triplet states (ΔEST) for efficient TADF as compared to those attached through a phenylene bridge. A modification of the pyrimidine unit with CN, SCH3, and SO2CH3 functional groups at position 2 is shown to enhance the emission yield up to 0.5 with pronounced TADF activity.

show abstract

“…Pyrimidine-5-carbonitrile has electron withdrawal due to carbazole, tert-butylcarbazole and methoxy carbazole substituents. This feature led to high photoluminescence yields and synthesized by Uliana et al [4]. The donor-acceptor-donor properties of these synthesis components are intended for achieving both blue OLED and optical sensors.…”

Section: Introductionmentioning

confidence: 99%

“…The donor-acceptor-donor properties of these synthesis components are intended for achieving both blue OLED and optical sensors. [4].…”

Section: Introductionmentioning

confidence: 99%

Light-Emitting Properties of Pyrimidine-5-Carbonitrile Derivatives: a Theoretical Calculation

Karakoyun

Erkan

2022

International Journal of Innovative Engineering Applications

View full text Add to dashboard Cite

Conference paperIn this study, 4,6-Di (9H-carbazol-9-yl) pyrimidine-5-carbonitrile (C1), 4,6-bis (3,6-di-tert-butyl-9H-carbazol-9-yl) pyrimidine-5carbonitrile (C2), 4,6-bis (3,6-dimethoxy-9H-carbazol-9-yl) pyrimidine-5-carbonitrile (C3) compounds were optimized at the B3LYP/6-31G(d) level. Energy densities of frontier molecular orbitals were investigated with molecular properties. Vertical ionization potentials (IPv), adiabatic ionization potential (IPa) (in eV), vertical electron affinity (EAv), adiabatic electron affinity (EAa), the hole reorganization energy (h )and electron reorganization energy (e ) were calculated (in eV) for C1, C2 and C3 compounds. e values of the C1 and C3 compounds are 0.29 and 0.30 eV and the h value is 0.18 and 0.20 eV, respectively. It can be said that the C1 and C3 compounds are not suitable as an electron bearing layers (ETL) material since its e values are greater than 0.276 eV and that its h value is less than 0.290 eV, so they are a suitable material for the Hole bearing layers (HTL). The C2 compound is suitable for both ETL and HTL materials.

show abstract

Multifunctional derivatives of pyrimidine-5-carbonitrile and differently substituted carbazoles for doping-free sky-blue OLEDs and luminescent sensors of oxygen

Cited by 15 publications

References 56 publications

Diazine-based thermally activated delayed fluorescence chromophores

Diazine-based thermally activated delayed fluorescence chromophores

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

Light-Emitting Properties of Pyrimidine-5-Carbonitrile Derivatives: a Theoretical Calculation

Contact Info

Product

Resources

About