New deep-blue emitting materials based on fully substituted ethylene derivatives

Kim, Soo‐Kang; Park, Young‐Il; Kang, In‐Nam; Park, Jong‐Wook

doi:10.1039/b706606f

Cited by 106 publications

(34 citation statements)

References 30 publications

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“…The 4-(1,2,2-triphenylvinyl)phenylboronic acid pinacol ester 5 was prepared by a modication of a procedure reported previously. 45 The D-A-D types of molecules BT-2TPE, FBT-2TPE and 2FBT-2TPE were synthesized by Suzuki-Miyaura cross-coupling reaction using equimolar amounts of the corresponding comonomers, 10 mol% Pd(PPh 3 ) 4 and aqueous K 2 CO 3 to give BT-2TPE, FBT-2TPE and 2FBT-2TPE in a yield of 85%, 64% and 38%, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Hsu

Weng

2018

RSC Adv.

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Compounds consisting of unsubstituted, monofluoro and difluoro substituted benzothiadiazole bonded to two tetraphenylethenes were successfully prepared by palladium catalyzed Suzuki-Miyaura cross-coupling reaction of their corresponding co-monomers. All compounds exhibited aggregation-induced emission characteristics when the water fraction was higher than 60% in the THF/water mixtures. The emission maximum for the three compounds was blue-shifted when the water content reached 90% compared to that in THF solution. The intensity of emission maximum of difluorinated benzothiadiazole linked with two tetraphenylethenes was 2.5 times higher in 90% water compared to those in THF solution.Surprisingly, two liquid crystal phases with two distinct emission colors were observed only for the compound containing difluorinated benzothiadiazole bonded to two tetraphenylethene. All compounds showed remarkable solvatochromic properties in selected solvents with different polarities. The powder XRD results and mechanochromism of the compounds suggested that the solid state structures can change from one form to another by grinding, fuming or annealing processes.

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Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Hsu

Weng

2018

RSC Adv.

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“…These properties are consistent with the calculated non-coplanar conformation of POAn and the tert-butyl group's effect on its symmetry. [12,15] We also recorded atomic force microscopy (AFM) images to investigate the morphological stability POAn. As illustrated in Figure 2a, a thin film of POAn prepared through vapor deposition exhibited a uniform surface morphology having a root-mean-square (RMS) surface roughness of 0.350 nm.…”

Section: Thermal Propertiesmentioning

confidence: 99%

“…In general, anthracene-based molecules possess excellent photoluminescence (PL) and EL characteristics. [12][13][14][15][16][17][18] We suspected that appending two electron-deficient triphenylphosphine oxide (TPPO) groups at the 9-and 10-positions of 2-tert-butylanthracene would provide us with an electron-transporting blue-light-emitting material. [19][20][21][22][23] Theoretical calculations suggested that POAn would possess a noncoplanar conformation, which would effectively mitigate its close packing, thereby leading to the formation of stable amorphous films.…”

Section: Introductionmentioning

confidence: 99%

Multifunctional Deep‐Blue Emitter Comprising an Anthracene Core and Terminal Triphenylphosphine Oxide Groups

Chien

Chen

Hsu

et al. 2009

Adv Funct Materials

240

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A highly efficient blue‐light emitter, 2‐tert‐butyl‐9,10‐bis[4′‐(diphenyl‐phosphoryl)phenyl]anthracene (POAn) is synthesized, and comprises electron‐deficient triphenylphosphine oxide side groups appended to the 9‐ and 10‐positions of a 2‐tert‐butylanthracene core. This sophisticated anthracene compound possesses a non‐coplanar configuration that results in a decreased tendency to crystallize and weaker intermolecular interactions in the solid state, leading to its pronounced morphological stability and high quantum efficiency. In addition to serving as an electron‐transporting blue‐light‐emitting material, POAn also facilitates electron injection from the Al cathode to itself. Consequently, simple double‐layer devices incorporating POAn as the emitting, electron‐transporting, and ‐injecting material produce bright deep‐blue lights having Commission Internationale de L'Eclairage coordinates of (0.15,0.07). The peak electroluminescence performance was 4.3% (2.9 cd A−1). For a device lacking an electron‐transport layer or alkali fluoride, this device displays the best performance of any such the deep‐blue organic light‐emitting diodes reported to date.

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“…4 It is required for those red, green and blue emitters to show high EL efficiency, good thermal properties, long lifetime and pure color coordinates (1931 Commission Internationale de l'Eclairage (C.I.E. )), in order to be applied to large full-color displays.…”

Section: -3mentioning

confidence: 99%

“…Synthesis of 1-Borolane-3,5-diphenylbenzene [4]: Compound 3 (6.0 g, 38.7 mmol) was dissolved in 100 mL of anhydrous THF solution and stirred at −78°C, the 2.0 M nBuLi (12.4 mL) was added. Then isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4 mL) was added to the reaction mixture.…”

Section: (T 2h)mentioning

confidence: 99%

Effect of the Length of Side Group Substitution on Optical and Electroluminescene Properties

Shin¹,

Kang²,

Kim³

et al. 2014

Bulletin of the Korean Chemical Society

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Blue emitting materials, 9,10-bis-biphenyl-4-yl-anthracene (AC-P), 9,10-bis-[1,1';4',1'']terphenyl-4-yl-anthracene (AC-DP), and 9,10-bis[3' ',5''-deiphenyltriphenyl-4'-yl] A and (0.15, 0.12). A bulky and non-planar side group helps to prevent π-π* stacking interaction, which should lead to the formation of more reliable amorphous film. This is expected to have a positive effect on the high efficiency of the operating OLED device.

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New deep-blue emitting materials based on fully substituted ethylene derivatives

Cited by 106 publications

References 30 publications

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Multifunctional Deep‐Blue Emitter Comprising an Anthracene Core and Terminal Triphenylphosphine Oxide Groups

Effect of the Length of Side Group Substitution on Optical and Electroluminescene Properties

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