Synthesis and Light-Emitting Properties of Bipolar Oligofluorenes Containing Triarylamine and 1,2,4-Triazole Moieties

Li, Zhong Hui; Wong, Man Shing; Fukutani, Hiroshi; Tao, Ye

doi:10.1021/ol0615477

Cited by 103 publications

(53 citation statements)

References 40 publications

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“…[16,17] By combining suitable electron-rich and -deficient moieties into a molecular structure the energy levels can be controlled, and the ability to transfer holes and electrons can also be introduced simultaneously. To improve the charge-transfer capability, a molecular structure that localizes the HOMOs and LUMOs at their respective hole-and electron-transporting moieties is desirable.…”

Section: Introductionmentioning

confidence: 99%

Spin‐Coated Highly Efficient Phosphorescent Organic Light‐Emitting Diodes Based on Bipolar Triphenylamine‐Benzimidazole Derivatives

Hayakawa

Ando

et al. 2008

Adv Funct Materials

257

130

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A new series of star‐shaped bipolar host molecules, tris(4′‐(1‐phenyl‐1H‐benzimidazol‐2‐yl)biphen‐yl‐4‐yl) amine (TIBN), tris(2′‐methyl‐4′‐(1‐phenyl‐1H‐benzimida zol‐2‐yl)biphenyl‐4‐yl)amine (Me‐TIBN), and tris(2,2′‐dimethyl‐4′‐(1‐phenyl‐1H‐benzimidazol‐2‐yl)biphenyl‐4‐yl)amine (DM‐TIBN), that contain hole‐transporting triphenylamine and electron‐transporting benzimidazole moieties are designed based on calculations using density functional theory and successfully prepared. The theoretical calculation of energy levels of TIBN derivatives affords helpful ideas to design molecules with a favorable localization of highest occupied/lowest unoccupied molecular orbital (HOMO/LUMO) levels and a predefined enhancement of the triplet energy gap. The TIBN derivatives are employed as hosts to fabricate phosphorescent organic light‐emitting diodes (OLEDs) by the two methods of spin‐coating and vacuum deposition. Notably, the spin‐coated Me‐TIBN and DM‐TIBN devices exhibit a much better performance than the vacuum‐deposited ones, in which the spin‐coated DM‐TIBN device (47 500 cd m−2, 27.3 cd A−1, 7.3 lm W−1) is outstanding with respect to other seminal work for solution‐processed OLEDs. More importantly, the new concept of localizing HOMO and LUMO levels for bipolar molecules is illustrated, and a facile strategy to tailor the energy levels by breaking the conjugation of hole‐ and electron‐transporting moieties is demonstrated.

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Section: Introductionmentioning

confidence: 99%

Spin‐Coated Highly Efficient Phosphorescent Organic Light‐Emitting Diodes Based on Bipolar Triphenylamine‐Benzimidazole Derivatives

Hayakawa

Ando

et al. 2008

Adv Funct Materials

257

130

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“…Oxadiazoles, including 1,2,4-oxadiazoles and 1,3,4-oxadiazoles which possess various bioactivities like antibacterial, antifungal and antitumor potencies [178], have relatively high reactivity due to the inductive effect of oxygen atom in the oxadiazole ring, and they have been investigated very well to transform into more stable heterocycles, especially 1,2,4-triazole derivatives [179][180][181][182][183][184][185][186][187]. In recent years, the prepared triazoles via rearrangement of oxadiazoles usually exhibited wide applications in medicinal chemistry especially as antitubercular [188] and antiproliferative agents [189], and also in supramolecular chemistry as progesterone receptors and ligands of coordination polymers [64,190,191].…”

Section: Transformations Of Five-membered Heterocyclic Compoundsmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

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“…[29][30][31][32][33][34][35] 1,2,4-triazole has other isomeric forms, namely, 1H-1,2,3-triazole and 2H-1,2,3-triazole as shown in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

Bipyridyl-substituted benzo[1,2,3]triazoles as a thermally stable electron transporting material for organic light-emitting devices

et al. 2011

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Synthesis and Light-Emitting Properties of Bipolar Oligofluorenes Containing Triarylamine and 1,2,4-Triazole Moieties

Cited by 103 publications

References 40 publications

Spin‐Coated Highly Efficient Phosphorescent Organic Light‐Emitting Diodes Based on Bipolar Triphenylamine‐Benzimidazole Derivatives

Spin‐Coated Highly Efficient Phosphorescent Organic Light‐Emitting Diodes Based on Bipolar Triphenylamine‐Benzimidazole Derivatives

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Bipyridyl-substituted benzo[1,2,3]triazoles as a thermally stable electron transporting material for organic light-emitting devices

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