Efficient blue organic light-emitting diode using anthracene-derived emitters based on polycyclic aromatic hydrocarbons

Bin, Jong-Kwan; Hong, Jong‐In

doi:10.1016/j.orgel.2011.02.011

Cited by 39 publications

(25 citation statements)

References 34 publications

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“…These precursors could be readily converted into the final products 1-3 from the Suzuki-Miyaura coupling with (3-CF 3 -phenyl) boronic acid in moderate yields (44-48%). The formation of compounds 1-3 was confirmed by 1 H, 13 C NMR, 19 F NMR spectroscopy (Figures S1-S6, Supplementary Materials), and elemental analysis (EA). The 1 H and 13 C NMR spectra of all DAA derivatives were in good agreement with the predicted structures.…”

Section: Synthesis and Characterizationmentioning

confidence: 90%

“…The 19 F NMR signals of 1-3 detected around δ-62 ppm also indicated the presence of the CF 3 -phenyl unit. Moreover, the chemical shifts of the resonances associated with the proton and carbon atoms in these molecules were in the expected range.…”

Section: Synthesis and Characterizationmentioning

confidence: 90%

“…As a notable candidate for effective blue-emitting materials, anthracene derivatives have attracted much attention in OLEDs because of their excellent optical and electroluminescent properties [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28]. However, these organic fluorescent π-conjugated compounds pose small problems, such as poor thermal stability and device failure caused by intermolecular π-stacking features.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Electroluminescence Properties of 3-(Trifluoromethyl)phenyl-Substituted 9,10-Diarylanthracene Derivatives for Blue Organic Light-Emitting Diodes

Kwak

Lee

et al. 2017

Applied Sciences

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Diaryl-substituted anthracene derivatives containing 3-(trifluoromethyl)phenyl) groups, 9,10-diphenyl-2-(3-(trifluoromethyl)phenyl)anthracene (1), 9,10-di([1,1 -biphenyl]-4-yl)-2-(3-(trifluoromethyl)phenyl)anthracene (2), and 9,10-di(naphthalen-2-yl)-2-(3-(trifluoromethyl)phenyl) anthracene (3) were synthesized and characterized. The compounds 1-3 possessed high thermal stability and proper frontier-energy levels, which make them suitable as host materials for blue organic light-emitting diodes. The electroluminescent (EL) emission maximum of the three N,N-diphenylamino phenyl vinyl biphenyl (DPAVBi)-doped (8 wt %) devices for compounds 1-3 was exhibited at 488 nm (for 1) and 512 nm (for 2 and 3). Among them, the 1-based device displayed the highest device performances in terms of brightness (L max = 2153.5 cd·m −2 ), current efficiency (2.1 cd·A −1 ), and external quantum efficiency (0.8%), compared to the 2-and 3-based devices.

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Section: Synthesis and Characterizationmentioning

confidence: 90%

Section: Synthesis and Characterizationmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Electroluminescence Properties of 3-(Trifluoromethyl)phenyl-Substituted 9,10-Diarylanthracene Derivatives for Blue Organic Light-Emitting Diodes

Kwak

Lee

et al. 2017

Applied Sciences

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“…Several blue-emitting OLED materials with high brightness and good stability such as distyrylarylene 6 and anthracene derivatives [7][8][9][10][11][12][13][14][15][16][17] have been developed. In spite of their excellent electronic and optical properties, these organic π-conjugated materials have some problems about device failure and thermal stability.…”

mentioning

confidence: 99%

2-Triphenylsilyl-9,10-di-1-naphthalenylanthracene and its Application for Blue Organic Light Emitting Diodes

Choi¹,

Kim²,

An³

et al. 2013

Bulletin of the Korean Chemical Society

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The red, green, and blue emitters with relatively equal stability, efficiency, and color purity are needed to achieve full-color displays for organic light emitting diode (OLED). 1,2Compared with red and green emitters, 3,4 further improvement of blue-emitting OLED materials is still required. 5Generally, it is very difficult to develop new blue-emitting materials with excellent electroluminescence property because of their intrinsic wide band gap. Several blue-emitting OLED materials with high brightness and good stability such as distyrylarylene 6 and anthracene derivatives 7-17 have been developed. In spite of their excellent electronic and optical properties, these organic π-conjugated materials have some problems about device failure and thermal stability. Recently, new silicon-cored anthracene derivatives were reported in the literature to overcome such problems and to improve thermal properties.18 In this regard, we designed a new blue-emitting anthracene derivative having siliconsubstituent such as 2-triphenylsilyl-9,10-di-1-naphthalenylanthracene (1) to combine two concepts from anthracene derivative with excellent electronic/optical properties and silicon-cored system with improved thermal stability. The introduction of the bulky triphenylsilyl group in 2 position of anthracene and naphthalenyl groups in 9, 10 positions of anthracene may prevent the aggregation of planar anthracenes as well as increase the chemical stability, the thermal stability, and solubility, which results in a bright blue EL emission.Scheme 1 illustrates the synthetic route for compound 1 via reaction of 2-bromo-9,10-di-1-naphthalenylanthracene, which is prepared according to a published procedure, 19 with n-BuLi followed by chlorotriphenylsilane. Compound 1 was obtained as air-stable colorless powder in the yield of 39%. The formation of 1 has been confirmed by 1 H and 13 C{ 1 H} NMR spectroscopy and high-resolution mass spectrometry. The thermal property of 1 was investigated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) under a nitrogen atmosphere. TGA curve showed that 1 exhibits excellent thermal stability with its 5% weight loss temperature (ΔT 5% ) at 351 o C, which is stable enough to endure the high temperature for the vacuum vapor deposition. Also, the morphological stability of 1 was monitored by DSC, which was performed from 0 to 450 o C at a heating rate of 10 o C/min and a glass transition temperature (T g ) and melting temperature (T m ) occurred at 254 o C and 332 o C, respectively. The results of the second scan were recorded to eliminate differences from the sample history. Despite relatively low molecular weight of 1, its excellent thermal stability might be originated from both the steric protection of triphenylsilyl group and non-planarity of its molecular structure.As shown in Figure 1, the optical properties of 1 were investigated by means of UV-Vis absorption and photoluminescence (PL) spectroscopy. 1 in dilute toluene solution exhibits the characteristic π-π* transition p...

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“…PSCs using MEH-PPV as the donor show a bigger V oc and limited J sc compared to PSCs with P3HT as the donor material [13,14]. A series of interfacial layers, LiF, MoO 3 and ZnO, were applied to improve device performances [15][16][17][18][19]. In this study, we used ultrathin LiF interfacial layer to improve OLED performance and Bphen interfacial layer to enhance PSC performance.…”

mentioning

confidence: 99%

Luminescent and photovoltaic properties of poly(9,9-dioctylfluorene-co-bithiophene) in organic electronic devices

Zhu

Bian

et al. 2012

Chin. Sci. Bull.

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We studied the luminescent and photovoltaic properties of poly(9,9-dioctylfluorene-co-bithiophene) (F8T2) based on ITO/ PEDOT : PSS/F8T2/Bphen/LiF(0 or 1 nm)/Al and ITO/PEDOT : PSS/F8T2 : PCBM/Bphen/Al. A stable and bright yellow emission was obtained from polymer F8T2, and the electroluminescence power reached 45 W at a 15 V driving voltage. Polymer F8T2 shows a broad absorption band from 400 to 500 nm, and has a shorter absorption edge at about 560 nm compared to that of the typical electron donor P3HT (650 nm). The photoluminescence quenching of F8T2 occurs with only a small fraction of blended PCBM due to the effective exciton dissociation at the interface between F8T2 and PCBM. Polymer solar cells (PSCs) using F8T2 : PCBM as the active layer show a low power conversion efficiency ( The electron donor band gap and energy level alignment between donor and acceptor strongly influence the absorption, exciton dissociation and charge transfer, finally determining the PCE of PSCs [3][4][5]. Fullerene and its derivatives are considered to be the best electron acceptors so far, which is attributed to its ultrafast photo-induced charge transfer, high electron mobility, and better phase separation in the blend films [6,7]. The lowest unoccupied molecular orbit (LUMO) of typical donor material P3HT is about 0.5 eV higher than that of PCBM, which favors electron transfer from P3HT to PCBM. However, the relatively high-lying highest occupied molecular orbit (HOMO) limits the maximum open-circuit voltage (V oc ) and causes oxidation instability of the cells at ambient conditions [4]. To further improve the photovoltaic propriety of PSCs, effort should be

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Efficient blue organic light-emitting diode using anthracene-derived emitters based on polycyclic aromatic hydrocarbons

Cited by 39 publications

References 34 publications

Synthesis and Electroluminescence Properties of 3-(Trifluoromethyl)phenyl-Substituted 9,10-Diarylanthracene Derivatives for Blue Organic Light-Emitting Diodes

Synthesis and Electroluminescence Properties of 3-(Trifluoromethyl)phenyl-Substituted 9,10-Diarylanthracene Derivatives for Blue Organic Light-Emitting Diodes

2-Triphenylsilyl-9,10-di-1-naphthalenylanthracene and its Application for Blue Organic Light Emitting Diodes

Luminescent and photovoltaic properties of poly(9,9-dioctylfluorene-co-bithiophene) in organic electronic devices

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