A bipolar host containing carbazole/dibenzothiophene for efficient solution-processed blue and white phosphorescent OLEDs

Lin, Wei; Huang, Wei; Huang, Ming Hong; Fan, Chia Chan; Lin, Huey-Wen; Chen, Li Yin; Liu, Yen Wei; Lin, Jin Sheng; Chao, Teng‐Chih; Tseng, Mei-Rurng

doi:10.1039/c3tc31357c

Cited by 50 publications

(20 citation statements)

References 64 publications

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“…In recent years, dibenzofuran62 and dibenzothiophene63 have been explored as electron‐deficient or ‐withdrawing groups, as well as for the construction of bipolar host materials. The compounds CzDBF ( 26 ) and CzDBS ( 27 ) are typical examples.…”

Section: Solution‐processable Small‐molecular Host Materialsmentioning

confidence: 99%

“…An extremely high quantum efficiency of 23.9 % was obtained, which was better than any other data reported for solution‐processed blue phosphorescent organic light‐emitting diodes, and they owed this good data to the following three reasons: firstly, the low energy barrier for hole and electron injection favored the energy transfer process, in spite of electron trapping by the FIrPic dopant material; secondly, similar hole and electron current densities were observed for CzDBF, which enhanced the recombination efficiency of CzDBF devices; thirdly, the bipolar charge‐transport behavior of CzDBF balanced the hole and electron densities in the emitting layer, and broadened the recombination zone. In 2013, a novel small‐molecular host containing carbazole/dibenzothiophene (CzDBS, 27 ) was studied by the Lin group 63. Using this material, they fabricated the solution‐processed blue PhOLEDs with the architecture of ITO/PEDOT : PSS/CzDBS : FIrPic (10 wt%, 35 nm)/TmPyPB (60 nm)/CsF (1 nm)/Al.…”

Section: Solution‐processable Small‐molecular Host Materialsmentioning

confidence: 99%

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Reactivity of Tp^Me2‐Supported Yttrium Alkyl Complexes toward Aromatic N‐Heterocycles: Ring‐Opening or CC Bond Formation Directed by CH Activation

Zhang

Huang

et al. 2013

Chemistry A European J

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Unusual chemical transformations such as three-component combination and ring-opening of N-heterocycles or formation of a carbon-carbon double bond through multiple C-H activation were observed in the reactions of Tp(Me2) -supported yttrium alkyl complexes with aromatic N-heterocycles. The scorpionate-anchored yttrium dialkyl complex [Tp(Me2) Y(CH2 Ph)2 (THF)] reacted with 1-methylimidazole in 1:2 molar ratio to give a rare hexanuclear 24-membered rare-earth metallomacrocyclic compound [Tp(Me2) Y(μ-N,C-Im)(η(2) -N,C-Im)]6 (1; Im=1-methylimidazolyl) through two kinds of C-H activations at the C2- and C5-positions of the imidazole ring. However, [Tp(Me2) Y(CH2 Ph)2 (THF)] reacted with two equivalents of 1-methylbenzimidazole to afford a C-C coupling/ring-opening/C-C coupling product [Tp(Me2) Y{η(3) -(N,N,N)-N(CH3 )C6 H4 NHCHC(Ph)CN(CH3 )C6 H4 NH}] (2). Further investigations indicated that [Tp(Me2) Y(CH2 Ph)2 (THF)] reacted with benzothiazole in 1:1 or 1:2 molar ratio to produce a C-C coupling/ring-opening product {(Tp(Me2) )Y[μ-η(2) :η(1) -SC6 H4 N(CHCHPh)](THF)}2 (3). Moreover, the mixed Tp(Me2) /Cp yttrium monoalkyl complex [(Tp(Me2) )CpYCH2 Ph(THF)] reacted with two equivalents of 1-methylimidazole in THF at room temperature to afford a trinuclear yttrium complex [Tp(Me2) CpY(μ-N,C-Im)]3 (5), whereas when the above reaction was carried out at 55 °C for two days, two structurally characterized metal complexes [Tp(Me2) Y(Im-Tp(Me2) )] (7; Im-Tp(Me2) =1-methyl-imidazolyl-Tp(Me2) ) and [Cp3 Y(HIm)] (8; HIm=1-methylimidazole) were obtained in 26 and 17 % isolated yields, respectively, accompanied by some unidentified materials. The formation of 7 reveals an uncommon example of construction of a CC bond through multiple C-H activations.

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Section: Solution‐processable Small‐molecular Host Materialsmentioning

confidence: 99%

Section: Solution‐processable Small‐molecular Host Materialsmentioning

confidence: 99%

Reactivity of Tp^Me2‐Supported Yttrium Alkyl Complexes toward Aromatic N‐Heterocycles: Ring‐Opening or CC Bond Formation Directed by CH Activation

Zhang

Huang

et al. 2013

Chemistry A European J

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“…31 Carbazole derivatives are established as hosts for PhOLEDs due to carbazole's high triplet energy and favorable hole-transporting properties. [32][33][34][35] The small-molecule mCP [1,3-bis(9-carbazolyl)benzene] which has a triplet energy of 2.9 eV is widely used in this context. [36][37][38][39][40][41] However, mCP tends to crystallize as a consequence of its rather low T g (glass transition temperature, 60 °C).…”

Section: Introductionmentioning

confidence: 99%

Solution-Processed Blue/Deep Blue and White Phosphorescent Organic Light-Emitting Diodes (PhOLEDs) Hosted by a Polysiloxane Derivative with Pendant mCP (1,3-bis(9-carbazolyl)benzene)

Sun¹,

Zhou

Liu³

et al. 2015

ACS Appl. Mater. Interfaces

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Shouke (2015) 'Solution-processed blue/deep blue and white phosphorescent organic light emitting diodes (PhOLEDs) hosted by a polysiloxane derivative with pendant mCP (1, 3-bis(9-carbazolyl)benzene).', ACS applied materials interfaces., 7 (51). pp. 27989-27998. Further information on publisher's website:http://dx.doi.org/10.1021/am507592sPublisher's copyright statement:This document is the Accepted Manuscript version of a Published Work that appeared in nal form in ACS Applied Materials and Interfaces, copyright c 2015 American Chemical Society after peer review and technical editing by the publisher. To access the nal edited and published work see http://dx.doi.org/10.1021/am507592s. Additional information:Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-pro t purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details.

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“…No carbazole derivative is absolutely electron-rich or deficient, which is strongly determined by the types of units and specific intermolecular linkage model because of "inductive" and "resonance" effects of different units, [63][64][65] and multifunctional hosts, which can be ambipolar, hole-blocking, or electron-transporting hosts, seem to be more power- ful for simplifying device structure and improving device performance. [66] As for organic electroluminescence, blue light is still lagging behind red and green lights in efficiency and stability.…”

Section: Discussionmentioning

confidence: 99%

Hosts for High‐Performance Phosphorescent Organic Light‐Emitting Diodes Based on Carbazole Derivatives

Jiang

2014

Asian J Org Chem

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Organic electroluminescent (EL) materials have many advantages when compared with their inorganic counterparts and, therefore, they have a wide range of potential applications in communication, information display, illumination, and so on. Phosphorescent organic lightemitting diodes (PHOLEDs) that contain late transition-metal complexes as emitters are particularly attractive due to their ability to harvest singlet and triplet excitons, which makes it possible to achieve an internal quantum efficiency of 100 %. To suppress concentration quenching, a phosphorescent emitter is usually dispersed in a suitable host to obtain a high photoluminescent quantum yield. Developing a host with a suitable triplet energy level, charge-transporting ability, and thermal and film stability is thus the key to improving the performance of PHOLEDs. Carbazole-based chromophores are widely used in the synthesis of highly efficient hosts for PHOLEDs. However, these compounds are not universal or unique segments for constructing high performance hosts. Herein, up-to-date methods for chemical modifications to obtain hosts for high-performance PHOLEDs based on carbazole derivatives are presented in detail. These methods include heterocycle replacement and extension of the conjugated structure of the carbazole skeleton. Finally, some issues to be addressed and hotspots to be further investigated are also discussed.

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A bipolar host containing carbazole/dibenzothiophene for efficient solution-processed blue and white phosphorescent OLEDs

Cited by 50 publications

References 64 publications

Reactivity of Tp^Me2‐Supported Yttrium Alkyl Complexes toward Aromatic N‐Heterocycles: Ring‐Opening or CC Bond Formation Directed by CH Activation

Reactivity of Tp^Me2‐Supported Yttrium Alkyl Complexes toward Aromatic N‐Heterocycles: Ring‐Opening or CC Bond Formation Directed by CH Activation

Solution-Processed Blue/Deep Blue and White Phosphorescent Organic Light-Emitting Diodes (PhOLEDs) Hosted by a Polysiloxane Derivative with Pendant mCP (1,3-bis(9-carbazolyl)benzene)

Hosts for High‐Performance Phosphorescent Organic Light‐Emitting Diodes Based on Carbazole Derivatives

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A bipolar host containing carbazole/dibenzothiophene for efficient solution-processed blue and white phosphorescent OLEDs

Cited by 50 publications

References 64 publications

Reactivity of TpMe2‐Supported Yttrium Alkyl Complexes toward Aromatic N‐Heterocycles: Ring‐Opening or CC Bond Formation Directed by CH Activation

Reactivity of TpMe2‐Supported Yttrium Alkyl Complexes toward Aromatic N‐Heterocycles: Ring‐Opening or CC Bond Formation Directed by CH Activation

Solution-Processed Blue/Deep Blue and White Phosphorescent Organic Light-Emitting Diodes (PhOLEDs) Hosted by a Polysiloxane Derivative with Pendant mCP (1,3-bis(9-carbazolyl)benzene)

Hosts for High‐Performance Phosphorescent Organic Light‐Emitting Diodes Based on Carbazole Derivatives

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Reactivity of Tp^Me2‐Supported Yttrium Alkyl Complexes toward Aromatic N‐Heterocycles: Ring‐Opening or CC Bond Formation Directed by CH Activation

Reactivity of Tp^Me2‐Supported Yttrium Alkyl Complexes toward Aromatic N‐Heterocycles: Ring‐Opening or CC Bond Formation Directed by CH Activation