Efficient Blue‐Light‐Emitting Electroluminescent Devices with a Robust Fluorophore: 7,8,10‐Triphenylfluoranthene

Chiechi, Ryan C.; Tseng, Ricky J.; Marchioni, Filippo; Yang, Yang; Wudl, Fred

doi:10.1002/adma.200501682

Cited by 129 publications

(71 citation statements)

References 15 publications

(10 reference statements)

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“…However, up to now, this has failed to produce an efficient, cheap and robust blue-light emitters. [2,33] Since the electronic and optical characteristics of the rigid F arise from its planar biphenyl moieties, the structurally related compound, indenofluorene (IF), with a planar, longer conjugated p-terphenyl moieties has been suggested as a promising building block. Indeed, its incorporation into polymer or oligomer backbones instead of F units has recently led to a strong enhancement of OLED properties.…”

Section: Introductionmentioning

confidence: 99%

Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Poriel¹,

Liang²,

Rault‐Berthelot³

et al. 2007

Chemistry A European J

131

229

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A series of new dispiro[fluorene-9',6,9'',12-indeno[1,2b]fluorenes] (DSF-IFs) has been synthesised. These new building blocks for blue-light-emitting devices and electroactive polymers combine indenofluorene (IF) and spirobifluorene (SBF) properties. We report here our synthetic investigations towards these new structures and their thermal, structural, photophysical and electrochemical properties. These properties have been compared to those of IF and SBF. We also report the anodic oxidation of DSF-IFs that leads to the formation of non-soluble transparent three-dimensional polymers. The structural and electrochemical behaviour of these polymers has been studied. The first application of these building blocks as new blue-light-emitting materials in organic light-emitting diodes (OLED) is also reported.

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Section: Introductionmentioning

confidence: 99%

Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Poriel¹,

Liang²,

Rault‐Berthelot³

et al. 2007

Chemistry A European J

131

229

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“…[1][2][3][4][5][6] Many green-and red-light-emitting organic materials have been developed for full-color displays but highly efficient and stable blue-light-emitting organic materials are still rare. [7][8][9][10] Due to the large band-gap of blue-light emitters, it is difficult to inject holes from the anode as well as electrons from the cathode in blue-light OLEDs. Promising candidates for blue-light-emitting materials include fluorene-based polymers and oligomers, due to their high photoluminescent quantum yield (PLQY), good thermal stability, and excellent solubility.…”

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confidence: 99%

Fluorene‐Based Oligomers for Highly Efficient and Stable Organic Blue‐Light‐Emitting Diodes

et al. 2009

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Organic light-emitting diodes (OLEDs) have great potential for applications such as flat panel displays and solid-state lighting. [1][2][3][4][5][6] Many green-and red-light-emitting organic materials have been developed for full-color displays but highly efficient and stable blue-light-emitting organic materials are still rare. [7][8][9][10] Due to the large band-gap of blue-light emitters, it is difficult to inject holes from the anode as well as electrons from the cathode in blue-light OLEDs. Promising candidates for blue-light-emitting materials include fluorene-based polymers and oligomers, due to their high photoluminescent quantum yield (PLQY), good thermal stability, and excellent solubility. [11][12][13] In this communication, we report a series of new blue-light-emitting materials consisting of oligofluorenyl blocks and electron-donating/electron-withdrawing groups, which facilitate the injection and transport of both holes and electrons. The device performance of undoped and doped devices indicates that they are very promising for OLEDs, with essential elements of high efficiency, good stability, and color purity for pure-blue emission.The target blue-light-emitting compounds were synthesized through three key steps (Scheme 1). First, 4-iodoaniline was coupled with carbazole through an Ullmann coupling reaction. In our first attempt, where N,N-dimethylacetamide (DMAc) was used as solvent, the reaction solution was heated at 160 8C for 24 h, and 76% yield of compound A was achieved. In our second attempt with diphenyl ether as solvent, the temperature was raised to 190 8C and the reaction yielded 92% of desired product. Compound A was then coupled with dibromo-oligofluorene (B1-B3), catalyzed by Pd(OAc) 2 , to afford compounds C1 to C3, which were eventually end-capped with cyanophenyl groups through a Suzuki coupling reaction. The three coupling reactions produced an overall yield of 55%, 37%, and 33% for D1, D2, and D3, respectively.The physical properties of the compounds are summarized in Table 1. All three compounds show high photoluminescent quantum yields, ranging from 59% to 64% in chloroform solution. With the number of fluorene units increasing from 1 to 3, the optical properties change remarkably. The optical bandgaps determined from the l 0-0 absorption-band edge are 2.78, 2.81, and 2.89 eV for D1, D2 and D3, respectively. The absorption maximum in the UV-vis spectrum of D3 in chloroform solution is blue-shifted by 9 nm, and the peak of photoluminescence (PL) spectrum of the thin film is largely blue-shifted by 33 nm compared with D1, as shown in Figure 1a. The OLED device performances also depend on the number of fluorene units, which will be described below.The preparation of the electroluminescent devices is briefly described as follows (see Experimental section): poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) and the light-emitting layer were spin-coated from solutions onto indium tin oxide (ITO) surfaces sequentially. 1,3,5-tris(phenyl-2-benzimidazolyl)benzene (TPBI...

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“…Four dopant materials (1,2,5,6) had the diphenylaminofluorene-7-yl-vinylfluorene core unit end-capped with triphenylsilylphenyl, trimethylsilylphenyl, trimethylsilyl, and triphenylsilyl groups. Five dopant materials (7,8,9,10,11) had end-capping groups such as 4-triphenylsilylphenyl, 4-triphenylsilylnaphthyl, 4-triphenylsilylfluorenyl, 3-triphenylsilylfluorenyl, and 3,5-bis-triphenylsilylfluorenyl groups on the diphenylaminofluorene-7-yl-vinylphenyl core unit. Compound 12 had two diphenylaminofluorene-7-yl-vinylphenyl groups on the tetraphenylsilane unit.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, most researches were focused on the development of blueemitting materials as the design of blue materials with high efficiency, color purity, and long operation time was difficult due to the wide energy bandgap of blue materials. [5][6][7][8][9][10][11] It is well known that a dopant/host emitter system can significantly improve the device performances such as electroluminescence (EL) efficiency, emissive color, and operational lifetime. [1] Energy transfer from the host to the dopant was the main mechanism for the light emission in the host/dopant system and dopant emission was mainly observed.…”

Section: Introductionmentioning

confidence: 99%

Molecular Engineering of Blue Fluorescent Molecules Based on Silicon End‐Capped Diphenylaminofluorene Derivatives for Efficient Organic Light‐Emitting Materials

Lee

Kang

Lee

et al. 2010

Adv Funct Materials

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Blue fluorescent materials based on silicone end‐capped 2‐diphenylaminofluorene derivatives are synthesized and characterized. These materials are doped into a 2‐methyl‐9,10‐di‐[2‐naphthyl]anthracene host as blue dopant materials in the emitting layer of organic light‐emitting diode devices bearing a structure of ITO/DNTPD (60 nm)/NPB (30 nm)/emitting layer (30 nm)/Alq3 (20 nm)/LiF (1.0 nm)/Al (200 nm). All devices exhibit highly efficient blue electroluminescence with high external quantum efficiencies (3.47%–7.34% at 20 mA cm−2). The best luminous efficiency of 11.2 cd A−1 and highest quantum efficiency of 7.34% at 20 mA cm−2 are obtained in a device with CIE coordinates (0.15, 0.25). A deep‐blue OLED with CIE coordinates (0.15, 0.14) exhibits a luminous efficiency of 3.70 cd A−1 and quantum efficiency of 3.47% at 20 mA cm−2.

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Efficient Blue‐Light‐Emitting Electroluminescent Devices with a Robust Fluorophore: 7,8,10‐Triphenylfluoranthene

Cited by 129 publications

References 15 publications

Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Fluorene‐Based Oligomers for Highly Efficient and Stable Organic Blue‐Light‐Emitting Diodes

Molecular Engineering of Blue Fluorescent Molecules Based on Silicon End‐Capped Diphenylaminofluorene Derivatives for Efficient Organic Light‐Emitting Materials

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