Deep-blue electroluminescence from nondoped and doped organic light-emitting diodes (OLEDs) based on a new monoaza[6]helicene

Hua, Wanming; Li, Zhi; Duan, Lian; Dong, Guifang; Qiu, Yong; Zhang, Baojie; Cui, Deliang; Tao, Xutang; Cheng, Na; Liu, Yongjun

doi:10.1039/c4ra13486a

Cited by 81 publications

(56 citation statements)

References 53 publications

(67 reference statements)

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“…94 Most of the parameters of 4-based OLEDs are significantly higher when compared to devices fabricated from asymmetric extended carbazoles, but this observation is countered with deeper/purer blue emission seen for the latter. 39,41 A quite similar bright blue emission was observed for OLEDs based on trialkylsilylanthracene yet with much lower luminosity of 107 cd/m 2 at 10 V. 91 The sky-blue OLEDs designed from benzo[k]fluoranthene 90 are matching ours suggesting a great potential in application of the more extended fused polyaromatics. Yet a considerable amount of work is required before such materials will be competetive with the best oligomeric emitters.…”

Section: Optical and Photophysical Propertiesmentioning

confidence: 64%

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Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer

et al. 2016

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An in-depth analysis of the electro-optical and light emissive properties was carried out with a new fused heteroacene, the bis [(1,2)(5,6)] indoloanthracene. The compound was synthesized in a straightforward bidirectional manner from 1,4-dibromo-2,5-diodobenzene utilizing a reaction cascade of isomerisation and cyclisation sequences. Bis-[(1,2)(5,6)] indoloanthracene exhibits bright luminescence with high quantum yield in solution as well as in the solid state. By using this novel semiconductor as active layer, an efficient OLED has been fabricated for which its emission pattern resembles at least two emitters in a single emissive region originated from the same molecule. One has its origin from the single molecule and is similar to the luminescence spectra in solution, whereas the other functions through the formation of aggregates being similar with the emission pattern found with crystals of bis-[(1,2)(5,6)]indoloanthracene. As a result bright sky-blue OLEDs with very high luminance exceeding 10000 cd/m 2 were obtained. Such color pattern and performance has not previously been observed with low molecular weight, electron-rich fused polycyclic aromatic compounds and indicate a promising new class of materials for development.

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Section: Optical and Photophysical Propertiesmentioning

confidence: 64%

“…23,24,25,26,27,28 Reports on more π-extended polycyclic aromatic compounds bearing carbazole units are less frequent. 29 , 30, 31 Impressive examples of π-extended heteroacenes show that polycyclic aromatic and heteroaromatic compounds are good candidates for transistors 32,33,34,35,36,37,38 , OLED 39,40,41 and OPV 42,43 fabrications.…”

Section: Introductionmentioning

confidence: 99%

Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer

et al. 2016

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“…The solvent‐polarity independence of absorption and emission spectra indicates that its dipole moments remain unchanged on electronic transition. These favourable non‐polar properties of Cl‐CN‐DPQ would facilitate stability of blue light emitting materials and improvement in efficiency of the devices . Due to the difference in dipole moments of the donor–acceptor molecules in the ground and excited states and their stabilization by polar or non‐polar solvent molecules through various non‐covalent interactions like hydrogen bonding, salvation or dipole–dipole interactions, bipolar compounds generally exhibited solvatochromic behaviour …”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of high quantum yield and oscillator strength 6‐chloro‐2‐(4‐cynophenyl)‐4‐phenyl quinoline (cl‐CN‐DPQ) organic phosphor for solid‐state lighting

Ghate

Dahule

Kalyani³

et al. 2017

Luminescence

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A novel blue luminescent 6-chloro-2-(4-cynophenyl) substituted diphenyl quinoline (Cl-CN DPQ) organic phosphor has been synthesized by the acid-catalyzed Friedlander reaction and then characterized to confirm structural, optical and thermal properties. Structural properties of Cl-CN-DPQ were analyzed by Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR) spectroscopy, X-ray diffraction technique (XRD) and scanning electron microscopy (SEM) and energy dispersive analysis of X-ray (EDAX) spectroscopy. FTIR spectra confirmed the presence of different functional groups and bond stretching. H-NMR and C-NMR confirmed the formation of an organic Cl-CN-DPQ compound. X-ray diffraction study provided its crystalline nature. The surface morphology of Cl-CN-DPQ was analyzed by SEM, while EDAX spectroscopy revealed the elemental analysis. Differential thermal analysis (TGA/DTA) disclosed its thermal stability up to 250°C. The optical properties of Cl-CN-DPQ were investigated by UV-vis absorption and photoluminescence (PL) measurements. Cl-CN-DPQ exhibits intense blue emission at 434 nm in a solid-state crystalline powder with CIE co-ordinates (0.157, 0.027), when excited at 373 nm. Cl-CN-DPQ shows remarkable Stokes shift in the range 14800-5100 cm , which is the characteristic feature of intense light emission. A narrow full width at half-maximum (FWHM) value of PL spectra in the range 42-48 nm was observed. Oscillator strength, energy band gap, quantum yield, and fluorescence energy yield were also examined using UV-vis absorption and photoluminescence spectra. These results prove its applications towards developing organic luminescence devices and displays, organic phosphor-based solar cells and displays, organic lasers, chemical sensors and many more.

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“…[1][2][3][4][5][6][7] These molecules are great importance in fundamental theoretical researches as well as device applications such as field-effect transistors, 3,[8][9][10][11][12][13][14] solar cells, [15][16][17][18][19][20] lightemitting diodes. [21][22][23][24] PAH derivatives have various structural isomers based on the differences in positions of condensed benzene rings. For example, pentacene (acene) and picene (phenacene) consisting of five fused benzene rings are planar structural isomers.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Control of Photophysical Process and Circularly Polarized Luminescence of [5]Carbohelicene Derivatives Substituted by Maleimide Units

et al. 2016

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A series of [5]carbohelicene derivatives substituted by electron-withdrawing maleimide and electron-donating methoxy such as maleimide-substituted [5]carbohelicene (HeliIm), and methoxy-substituted HeliIm (MeO-HeliIm) were newly designed and synthesized to examine the electrochemical properties, excited-state dynamic and circularly polarized luminescence (CPL). First, electrochemical measurements and DFT calculations of [5]carbohelicene derivatives were performed by comparing with the structural isomers: picene derivatives. Introduction of an electron-withdrawing maleimide group onto a [5]carbohelicene core contributes to the stabilized LUMO state in HeliIm as compared to that of [5]carbohelicene (Heli), whereas the energy level of HOMO state in MeO-HeliIm increases by introducing electron-donating methoxy (MeO) groups onto a HeliIm skeleton. The HOMO-LUMO gap of MeO-HeliIm is smaller than those of HeliIm and Heli, which is similar to the steady-state spectroscopic measurements. The absolute fluorescence quantum yield (Φ FL ) of HeliIm (0.37) largely increased as compared to [5]carbohelicene, Heli (0.04), whereas Φ FL of MeO-HeliIm (0.22) was slightly smaller than that of HeliIm. Theses photophysical processes including intersystem crossing are successfully explained by the kinetic discussions. Since [5]carbohelicene derivatives show the chirality, measurements of circular dichroism (CD) and circularly polarized luminescence (CPL) were successfully performed. In particular, HeliIm and MeO-HeliIm have provide excellent circularly polarized luminescence (CPL) and the values of the anisotropy factor g lum were estimated to be 2.4 × 10 −3 and 2.3 × 10 −3 , relatively. This is the first observation of CPL in [5]carbohelicene derivatives.

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Deep-blue electroluminescence from nondoped and doped organic light-emitting diodes (OLEDs) based on a new monoaza[6]helicene

Abstract: Electroluminescent properties of a new monoaza[6]helicene as deep-blue light emitters in nondoped and doped OLEDs were investigated.

Cited by 81 publications

References 53 publications

Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer

Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer

Synthesis and characterization of high quantum yield and oscillator strength 6‐chloro‐2‐(4‐cynophenyl)‐4‐phenyl quinoline (cl‐CN‐DPQ) organic phosphor for solid‐state lighting

Synthetic Control of Photophysical Process and Circularly Polarized Luminescence of [5]Carbohelicene Derivatives Substituted by Maleimide Units

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