Novel Polycyclic Fused Amide Derivatives: Properties and Applications for Sky-blue Electroluminescent Devices

Yang, Guangsai; Liu, Deng-Hui; Jiang, Simin; Yang, Zhihai; Chen, Zijian; Qiu, Weidong; Gan, Yiyang; Liu, Kun-Kun; Li, De-Li; Su, Shi‐Jian

doi:10.3390/molecules27165181

Cited by 2 publications

(1 citation statement)

References 34 publications

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“…The development of organic fluorophores is an important theme for the advancement of functional materials research. Fused aromatic rings are widely utilized to produce fluorescent materials because of their planar and large π-conjugated structures [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. Recently, the fluorophores with longer fluorescence peaks are utilized in the biological probes because the fluorophores with shorter fluorescence peaks are affected by organs.…”

Section: Introductionmentioning

confidence: 99%

Bathochromic Shift of Fluorescence Peak in Dipyrrolo[1,2-a:2′,1′-c]quinoxaline by Introducing Each of Electron-Donating and Electron-Withdrawing Substituent

2023

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Development of organic fluorophore is an important theme. Especially, the fluorophores with longer fluorescence peaks are useful to biological probes. One of the methods to change the fluorescence peak is the introduction of substituents. However, opposing characteristics of the substituents lead to different changes in the fluorescence peaks. Furthermore, the introduction of the substituent also affects their electric properties. Thus, if the materials were developed with the substituent effect on the optical and electric properties separately, it will be useful to design the functional materials related to both optical and electric properties. Herein, we investigated the substituent effect of dipyrrolo[1,2-a:2′,1′-c]quinoxalines on fluorescence properties. We synthesized the compounds bearing electron-donating or electron-withdrawing substituents at the benzene ring on dipyrrolo[1,2-a:2′,1′-c]quinoxaline, which would have more direct influence on the optical properties. By introducing each substituent at the 6 position of dipyrrolo[1,2-a:2′,1′-c]quinoxaline, the bathochromic shift was observed in the fluorescence spectra. In the case of fluorine substituent, the change of the fluorescence peak reached was about 19 nm. Using a TDDFT calculation, we explained the reason for such a substituent effect that large on the increment of LUMO energy or decrement of HOMO energy occurred by introducing electron-withdrawing or electron-donating substituents at the 6 position, respectively. The substituent effect on the change of orbital energies is typical although the different characteristics of substituents resulted in the similar tendency about the change of fluorescence peak. Furthermore, with the introduction of phenyl substituents at the 3 and 10 positions, we achieved 40–50 nm longer fluorescence peaks compared with that of the original dipyrrolo[1,2-a:2′,1′-c]quinoxaline.

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Section: Introductionmentioning

confidence: 99%

Bathochromic Shift of Fluorescence Peak in Dipyrrolo[1,2-a:2′,1′-c]quinoxaline by Introducing Each of Electron-Donating and Electron-Withdrawing Substituent

2023

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Triplet–Triplet Annihilation Enhanced Deep‐Blue Organic Light‐Emitting Diodes by Naphtho[1,2‐d]imidazole‐Isomer Derivatives with Spin–Orbit Coupling

Yang,

Liu,

et al. 2023

Advanced Optical Materials

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The utilization of triplet excitons is of great importance for organic light‐emitting diodes (OLEDs). Triplet–triplet annihilation (TTA) is one of the effective tactics to achieve high efficiency deep‐blue organic electroluminescence emitters by converting two triplet excitons into one singlet exciton. Whereas, in addition to the 25% electrogenerated singlet excitons, the proportion of radiative singlet excitons (RSE) produced by the TTA process is usually only 15%; thus the total radiative excitons are 40%. In this study, ≈35% of RSE is achieved by the TTA process (total 60%) with two deep‐blue emitters based on the isomeric naphthoimidazole (NI) unit and anthracene bridge. As a result, non‐doped OLEDs based on the two NI derivatives as emitting layers achieve maximum external quantum efficiencies of 10.9% and 11.2% with an identical deep‐blue emission peak of 452 nm, which are the best TTA OLEDs with a Commission Internationale de l'Eclairage chromaticity Y coordinate below 0.15. Theoretical and experimental results demonstrate that the TTA process can be improved owing to the efficient spin–orbit interactions, even though the energy levels of the triplet pairs are higher than the calculated second triplet excited states.

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Novel Polycyclic Fused Amide Derivatives: Properties and Applications for Sky-blue Electroluminescent Devices

Cited by 2 publications

References 34 publications

Bathochromic Shift of Fluorescence Peak in Dipyrrolo[1,2-a:2′,1′-c]quinoxaline by Introducing Each of Electron-Donating and Electron-Withdrawing Substituent

Bathochromic Shift of Fluorescence Peak in Dipyrrolo[1,2-a:2′,1′-c]quinoxaline by Introducing Each of Electron-Donating and Electron-Withdrawing Substituent

Triplet–Triplet Annihilation Enhanced Deep‐Blue Organic Light‐Emitting Diodes by Naphtho[1,2‐d]imidazole‐Isomer Derivatives with Spin–Orbit Coupling

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