Novel pyrene derivatives: Synthesis, properties and highly efficient non-doped deep-blue electroluminescent device

Wang, Zhiqiang; Xu, Chen; Wang, Weizhou; Dong, Xin‐Ming; Zhao, Bang‐Tun; Ji, Baoming

doi:10.1016/j.dyepig.2011.06.025

Cited by 35 publications

(13 citation statements)

References 20 publications

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“…[1][2][3] Salient features of pyrene are that its p-system does not require protection during functionalization, 4 its moderately long fluorescence lifetime, and excimer formation. 5 However, there are two major drawbacks of pyrenes when used in organic fluorescent materials, (i) the absorption and emission of the pyrene fluorophore lies in the near-ultraviolet (UV) region, whereas a good optoelectronic device emits in the visible region and (ii) excimer formation occurs in concentrated solutions or in the solid state, which decreases or quenches the fluorescence intensity, with a large red-shifted emission. [6][7][8] This common phenomenon is defined as aggregation-induced quenching (ACQ).…”

Section: Chemistry Of Pyrene and Its Derivativesmentioning

confidence: 99%

Pyrene-based aggregation-induced emission luminogens and their applications

Islam

Wang

et al. 2019

Mater. Chem. Front.

266

172

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Section: Chemistry Of Pyrene and Its Derivativesmentioning

confidence: 99%

Pyrene-based aggregation-induced emission luminogens and their applications

Islam

Wang

et al. 2019

Mater. Chem. Front.

266

172

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“…Investigation of the efficient organic light-emitting devices based on pyrene derivatives was also a stimulus to the synthesis of 1,6-disubstituted pyrenes, which contain various aryl groups 20 – 28 , such as presented in Scheme 12, Scheme 13, Scheme 14 and Scheme 15 [4,8,47,48,49,50]. All reactions used [Pd(PPh 3 ) 4 ] as a catalyst and are divided in reference to applied bases Na 2 CO 3 , NaOH, and K 2 CO 3 , and solvents PhMe/EtOH, 1,4-dioxane, and THF.…”

Section: Dibromopyrenesmentioning

confidence: 99%

Non-K Region Disubstituted Pyrenes (1,3-, 1,6- and 1,8-) by (Hetero)Aryl Groups—Review

Zych

2019

Molecules

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Disubstituted pyrenes at the non-K region by the same or different (hetero)aryl groups have proven to be an increasingly interesting area of research for scientists over the last decade due to their optical and photophysical properties. However, in this area, there is no systematization of the structures and synthesis methods nor their limitations. In this review, all approaches to the synthesis of these compounds, starting from the commercially available pyrene are described. Herein, the ways of obtaining of disubstituted intermediates based on bromination and acylation reaction are presented. This is crucial in the determination of the possibility of further functionalization by using coupling, cycloaddition, condensation, etc. reactions. Moreover, the application of disubstituted pyrenes in the synthesis of 1,3,6,8-tetrasubstituted was also reviewed. This review describes the directions of research on chemistry of disubstituted pyrenes.

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“…Up to now various conjugated systems, including pyrene, fluorene, anthracene, and phenanthroimidazole materials have been synthesized and used in OLED devices. Among the above‐mentioned materials, phenanthroimidazole is a deep‐blue emitting chromophore, has attracted remarkable attention because of the simple synthesis procedure, high fluorescence quantum yield, excellent thermal stability, and potential bipolar properties .…”

Section: Introductionmentioning

confidence: 99%

Near UV/Deep‐Blue Phenanthroimidazole‐Based Luminophores for Organic Light‐Emitting Diodes: Experimental and Theoretical Investigation

et al. 2019

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Two new deep blue phenanthroimidazole base luminophores 2-(4-(4-(4-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl) phenoxy)butoxy)phenyl)-1-phenyl-1H-phenanthro[9,10-d]imid -azole (DPIPOBn) and 2-(4-(4-(4-(1-(4-tert-butylphenyl)-1Hphenanthro[9,10-d]imidazol-2-yl) phenoxy)butoxy)phenyl)-1-(4tert-butylphenyl)-1H-phenanthro[9,10-d]imidazole (DPITBOBn) were designed and synthesized by linkage two phenanthroimidazole functional units via the highly flexible alkyl (butane) spacer with different N1 functional groups (benzene and tertbutylbenzene). The synthesized luminophores were structurally characterized by spectroscopic method ( 1 H, 13 C, and mass). The photophysical, electrochemical and electroluminescence properties of the luminophores were systematically studied. These luminophores emit intense blue PL emission in both solution and solid phase. The HOMO-LUMO energy level of the luminophores was calculated from Cyclic Voltammetry (CV) analysis and which agreed with the results from the densityfunctional-theory (DFT) calculation. The time-dependent DFT (TD-DFT) calculation was performed to know the excited states (singlet and triplet) of the luminophores. The solutionprocessed OLED was fabricated to test these materials as emissive materials and as emitters. All the doped devices exhibited near-UV emission with EL peaks centered around 380-395 nm with Commission International deL'Eclairage (CIE) coordinate of (0.16, 0.09 or 0.10). Among all the doped devices, DPITBOBn (3 wt%) based device displayed a power efficiency (PE) of 0.5 lm/W, a current efficiency (CE) of 1.2 cd/A and external quantum efficiency (EQE) of 1.9% at the brightness 100 cd/m 2 .[a] J. Tagare, Prof. S. Vaidyanathan

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Novel pyrene derivatives: Synthesis, properties and highly efficient non-doped deep-blue electroluminescent device

Cited by 35 publications

References 20 publications

Pyrene-based aggregation-induced emission luminogens and their applications

Pyrene-based aggregation-induced emission luminogens and their applications

Non-K Region Disubstituted Pyrenes (1,3-, 1,6- and 1,8-) by (Hetero)Aryl Groups—Review

Near UV/Deep‐Blue Phenanthroimidazole‐Based Luminophores for Organic Light‐Emitting Diodes: Experimental and Theoretical Investigation

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