Functional organic click-materials: application in phosphorescent organic light emitting diodes

Kautny, Paul; Zhao, Chenyang; Kader, Thomas; Stöger, Berthold; Horkel, Ernst; Chen, Jiangshan; Ma, Dongge; Fröhlich, Johannes; Lumpi, Daniel

doi:10.1039/c6ra28212a

Cited by 10 publications

(5 citation statements)

References 62 publications

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“…[5b] These modifications allow to tune the emission color of such chromophores over a wide range,[5b] which is of practical importance for applications in the field of organic light‐emitting diodes (OLEDs). Related 1,2,3‐triazole based materials were successfully applied as host materials for phosphorescent OLEDs . Furthermore, simple silyl capped fragmentation products feature layered crystallization behavior, a feature that has been reported for other silyl acetylene substituted materials and is of particular importance for the use of organic material in applications, which require high charge carrier mobilities e.g.…”

Section: Introductionmentioning

confidence: 86%

“…While our previous investigation focused on simple fragmentation products of methyl‐substituted thiophene, symmetric double‐sided ring‐opened structures may give rise to diverse applications (e.g. as monomers for polymerization, symmetric chromophores). Moreover, the nature of a π‐conjugated spacer has a decisive impact on the intrinsic properties of the target molecules.…”

Section: Introductionmentioning

confidence: 99%

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Spacer‐Extended Bis‐Ene‐Yne Compounds: Scope, Limitations, and Properties

et al. 2018

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The paper outlines a synthetic approach towards novel spacer‐extended bis‐ene‐yne structures via a tandem thiophene ring‐opening reaction to selectively obtain the Z,Z‐isomers. Various unsaturated spacer moieties are matter of interest in these investigations owing to potential applications in organic electronics. As a result, the successful application of the tandem ring‐opening process on a representative set of spacer‐extended substrates is demonstrated and the limitations regarding substrate and product scope are revealed in terms of ring‐opening ability and stability. Additionally, a general oxidation protocol for ene‐yne compounds capable of accessing double‐sided sulfone species is developed. The comparison of the photophysical and electronic properties before and after oxidation reveals significant effects of the chemical modification on the intrinsic characteristics of the materials and thus a wide variability of the developed molecular building blocks.

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Section: Introductionmentioning

confidence: 86%

Section: Introductionmentioning

confidence: 99%

Spacer‐Extended Bis‐Ene‐Yne Compounds: Scope, Limitations, and Properties

et al. 2018

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“…Absorption maxima in contrast are represented by the triphenylamine centred p-p* transitions at 294.5 and 293.5 nm, a feature that has been previously observed. 39 Notably, the absorption onset of ZMSM-15TPA is shifted to higher energy (354 nm) compared to ZMSM-14TPA (366 nm) indicative of a decreased degree of conjugation due to the highly twisted conformation of ZMSM-15TPA.…”

Section: Photophysical Characterizationmentioning

confidence: 98%

“…37 Furthermore, the incorporation of 1,2,3-triazoles as linkers proved to be advantageous in the design of bipolar materials with high nonlinear activity 38 and tailored photophysical properties. 38,39 The application of thio-ene-yne compounds as starting materials for the synthesis of Click-derived functional materials allows for easy and versatile modification of molecular properties due to various chemical transformations of this particular structural scaffold. The possibility to selectively isomerize the double bond from Z to the thermodynamically more favourable E configuration 37 alters the spatial arrangement of the functional groups, whereas sulphur oxidation converts the electron donating substituent to a strongly electron withdrawing sulfone.…”

Section: Introductionmentioning

confidence: 99%

Charge-transfer states in triazole linked donor–acceptor materials: strong effects of chemical modification and solvation

Kautny

Glöcklhofer

Kader

et al. 2017

Phys. Chem. Chem. Phys.

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A series of 1,2,3-triazole linked donor-acceptor chromophores are prepared by Click Chemistry from ene-yne starting materials. The effects of three distinct chemical variations are investigated: enhancing the acceptor strength through oxidation of the sulphur atom, alteration of the double bond configuration, and variation of the triazole substitution pattern. A detailed photophysical characterization shows that these alterations have a negligible effect on the absorption while dramatically altering the emission wavelengths. In addition, strong solvatochromism is found leading to significant red shifts in the case of polar solvents. The experimental findings are rationalized and related to the electronic structure properties of the chromophores by time-dependent density functional theory as well as the ab initio algebraic diagrammatic construction method for the polarization propagator in connection with a new formalism allowing to model the influence of solvation onto long-lived excited states and their emission energies. These calculations highlight the varying degree of intramolecular charge transfer character present for the different molecules and show that the amount of charge transfer is strongly modulated by the conducted chemical modifications, by the solvation of the chromophores, and by the structural relaxation in the excited state. It is, furthermore, shown that enhanced charge separation, as induced by chemical modification or solvation, reduces the singlet-triplet gaps and that two of the investigated molecules possess sufficiently low gaps to be considered as candidates for thermally activated delayed fluorescence.

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“…Although triazoles have shown that they can be used as conjugative π-spacers in intramolecular electron transfer processes [26], to the best of our knowledge 1,2,4-triazoles has only been used as electron acceptor units in organic light emitting diodes [27][28][29][30]. Since several π-spacer units that contains electron-deficient moieties have been reported, some which have produced efficiencies of 8.70% [5], it was worthwhile to assess electron-deficient 1,2,4-triazole as a π-spacer unit.…”

Section: Introductionmentioning

confidence: 99%

A theoretical investigation of decorated novel triazoles as DSSCs in PV devices

2021

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Some novel metal-free 1,2,4-triazole compounds A1-A8, based on the 3,5-bis(2-hydroxyphenyl)-1,2,4triazole derivatives were examined for Photovoltaic properties using density functional theory (DFT) and time dependent density functional theory (TD-DFT) calculations for the use of dye sensitized solar cells (DSSCs). Through deductive logic, the fluorescence emission (Φf) and charge collection (ηc) efficiencies of these compounds as dyes were obtained and used to determine each dye's incident conversion efficiency (IPCE). Furthermore, these parameters were also employed to assess the dye's potential for photovoltaic technology. However, this technique is more suitable to predict the suitability of the dye for photovoltaic applications, and cannot measure the efficiency of DSSCs

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Functional organic click-materials: application in phosphorescent organic light emitting diodes

Abstract: 1,2,3-Triazole has been applied as a novel linker in donor–acceptor materials to control intramolecular charge transfer phenomena.

Cited by 10 publications

References 62 publications

Spacer‐Extended Bis‐Ene‐Yne Compounds: Scope, Limitations, and Properties

Spacer‐Extended Bis‐Ene‐Yne Compounds: Scope, Limitations, and Properties

Charge-transfer states in triazole linked donor–acceptor materials: strong effects of chemical modification and solvation

A theoretical investigation of decorated novel triazoles as DSSCs in PV devices

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