Electroluminescence and contact formation of 1-(pyridin-2-yl)-3-(quinolin-2-yl)imidazo[1,5-a]quinoline thin films

Albrecht, G.; Geis, Christian; Herr, Jasmin; Ruhl, Julia; Göttlich, Richard; Schlettwein, Derck

doi:10.1016/j.orgel.2018.11.032

Cited by 20 publications

(24 citation statements)

References 34 publications

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“…Since imidazo [1,5-a]pyridines are a well-established class of fluorophores, we investigated the effect of the quaternization reaction on the photophysical features [2,3,20,21,49]. The UV-Vis absorption spectrum of 1 in DCM displayed an intense high-energy band at 323 nm, together with a shoulder located at 380 nm.…”

Section: Notes About the Photophysical Propertiesmentioning

confidence: 99%

“…Despite the large interest in these compounds, depicted by numerous works on the quaternization onto the imidazo [1,5-a]pyridine moiety in mono-or dimeric forms, a systematic study about the quaternization reaction onto pyridylimidazo [1,5-a]pyridine derivatives and their optical properties is still lacking. This is of utter importance as both pyridylimidazo [1,5-a]pyridine derivatives and their salts are gaining considerable interest for optoelectronic applications such as solution-processed light-emitting devices (OLEDs [20,21] and LECs [22,23]). In the latter field, two issues are particularly bothersome: the first is the lack of high-energy stable emitters, while the second one is the lack of sustainable ionic emitters [24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

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Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts

et al. 2021

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In the last few years, imidazo[1,5-a]pyridine scaffolds and derivatives have attracted growing attention due to their unique chemical structure and optical behaviors. In this work, a series of pyridylimidazo[1,5-a]pyridine derivatives and their corresponding pyridinium salts were synthesized and their optical properties investigated to evaluate the effect of the quaternization on the optical features both in solution and polymeric matrix. A critical analysis based on the spectroscopic data, chemical structures along with density functional theory calculation is reported to address the best strategies to prevent aggregation and optimize the photophysical properties. The obtained results describe the relationship between chemical structure and optical behaviors, highlighting the role of pendant pyridine. Finally, the presence of a positive charge is fundamental to avoid any possible aggregation process in polymeric films.

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Section: Notes About the Photophysical Propertiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts

et al. 2021

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“…As a first step to show the applicability of the studied class of molecules in electro-optical devices, a prototype OLED structure was prepared with IQ5, which shows the highest molecular photoluminescence quantum yield ( Table 2). Suitable contact materials, able to inject charge carriers, fitting to the frontier orbital energies and a layer architecture already developed for IQ3 [18] have been used, and a model device ITO/PEDOT:PSS/IQ5/ BCP/Al has been prepared by spin coating (PEDOT:PSS) and PVD (all other layers) on a commercial indium tin oxide (ITO) substrate. The results of this test OLED with IQ5 as an active emitting layer are shown in Figure 10.…”

Section: Structure and Electronic Coupling In Crystals And Thin Solidmentioning

confidence: 99%

“…This was also seen before for IQ3 in the same contacting scheme. [18] The diode produces blue/greenish-white electroluminescence at stable electrical performance and reasonable current density (the inset in Figure 10). Its emission color according to the CIE 1931 XYZ color space with a 2 observer is found at x ¼ 0.27, y ¼ 0.36, and z ¼ 0.37.…”

Section: Structure and Electronic Coupling In Crystals And Thin Solidmentioning

confidence: 99%

“…Also, IQs have exhibited suitable material properties for application in OLEDs . Using 1‐(pyridin‐2‐yl)‐3‐(quinolin‐2‐yl)imidazo[1,5‐ a ]quinoline in a layer architecture with typical contact materials, blue OLEDs were prepared recently . The substitution with different functional groups up to now has mainly been studied on the IP core .…”

Section: Introductionmentioning

confidence: 99%

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Optimization of the Substitution Pattern of 1,3‐Disubstituted Imidazo[1,5‐a]Pyridines and ‐Quinolines for Electro‐Optical Applications

Albrecht

Rössiger

Herr

et al. 2020

Physica Status Solidi (b)

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A series of recently synthesized 1,3‐disubstituted imidazo[1,5‐a]pyridines (IPs) and ‐quinolines (IQs) targeting at increased efficiency of luminescence is investigated. The properties of molecules in solution as well as their change in the solid state are reported and assessed regarding possible application in organic electronics. The influence of increased ring size by substitution, e.g., exchanging phenyl to naphthalenyl, as well as pyridyl to quinolinyl moieties, and by means of a larger IQ fluorophore is discussed. A higher oscillator strength and quantum yield can be achieved. Frontier orbital energies are estimated based on cyclic voltammetry and density functional theory (DFT) calculations. Single crystals of molecules are grown. A red‐shift in the photoluminescence spectra found for crystals of IQs compared with those in solution is proposed to be caused by intermolecular coupling based on the parallel stacking of the enlarged fluorophore units. Thin films deposited by physical vapor deposition exhibit similar effects, showing promise as active layers in organic light‐emitting diodes (OLEDs). An amorphous morphology is inferred for these films from both spectral broadening in photoluminescence and atomic force microscopy. An OLED test structure is prepared, using the most efficient IQ lumophore and demonstrating the feasibility of obtaining electroluminescence from such thin films.

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Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Volpi

2022

Asian J Org Chem

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In the last few years, imidazo[1,5‐a]pyridine derivatives have attracted growing attention due to their remarkable emissive behaviours, structural modification and biological properties. Previously published works emphasize the possible technological applications of this luminescent scaffold and demonstrate the stringent relationship between chemical substituents and optical properties. The main goal of this work is to provide a complete list of the reported achievements concerning these promising heterocyclization reactions obtained starting from a huge variety of reagents, catalysts, oxidants, dehydrating agents involved in various reaction conditions. Particular attention is focused on the final possible substitutions, conjugations and structural modifications of the reported synthetic approaches, a powerful aspect to design innovative and employable new luminescent imidazo[1,5‐a]pyridine products.

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Electroluminescence and contact formation of 1-(pyridin-2-yl)-3-(quinolin-2-yl)imidazo[1,5-a]quinoline thin films

Cited by 20 publications

References 34 publications

Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts

Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts

Optimization of the Substitution Pattern of 1,3‐Disubstituted Imidazo[1,5‐a]Pyridines and ‐Quinolines for Electro‐Optical Applications

Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

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