A new thermally crosslinkable hole injection material for OLEDs

Hung, Wen‐Yi; Lin, Chi-Yen; Cheng, Tsang-Lung; Yang, Shanglin; Chaskar, Atul; Fan, Gang-Lun; Wong, Ken‐Tsung; Chao, Teng‐Chih; Tseng, Mei-Rurng

doi:10.1016/j.orgel.2012.06.023

Cited by 33 publications

(17 citation statements)

References 21 publications

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“…Compared with an orthogonal solvent system, a crosslinking system can yield various HTMs such as small molecules, star-shaped macromolecules, and main-/side-chain polymers. To date, many types of crosslinkable HTMs have been proposed. − ,− Among various reactive moieties, vinyl units were often employed to design thermally crosslinkable small molecules and polymers. − Tseng and colleagues demonstrated a thermally crosslinkable hole-injection small molecule (VB-DATA) based on 4,4′,4″-tris[(3-methylphenyl)phenylamino]triphenylamine having three peripheral styryl (vinylbenzene) moieties. The crosslinked VB-DATA thin films could be prepared by spin-casting followed by thermal treatment at 190 °C and were applied to green-emitting OLEDs .…”

Section: Introductionmentioning

confidence: 99%

“…To date, many types of crosslinkable HTMs have been proposed. − ,− Among various reactive moieties, vinyl units were often employed to design thermally crosslinkable small molecules and polymers. − Tseng and colleagues demonstrated a thermally crosslinkable hole-injection small molecule (VB-DATA) based on 4,4′,4″-tris[(3-methylphenyl)phenylamino]triphenylamine having three peripheral styryl (vinylbenzene) moieties. The crosslinked VB-DATA thin films could be prepared by spin-casting followed by thermal treatment at 190 °C and were applied to green-emitting OLEDs . Very recently, Cha’s group reported a thermally crosslinkable hole-transporting poly(indenofluorene- co -triphenylamine) copolymer (X-IFTPA) containing a vinyl-functionalized triphenylamine moiety.…”

Section: Introductionmentioning

confidence: 99%

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Hole-Transporting Side-Chain Polymer Bearing a Thermally Crosslinkable Bicyclo[4.2.0]octa-1,3,5-trien-3-yl Group for High-Performing Thermally Activated Delayed Fluorescence OLED

Jeong

Godumala

Yoon

et al. 2019

ACS Appl. Mater. Interfaces

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A new side-chain polymer (X-TPACz) bearing hole-transporting pendant groups accompanying a thermally crosslinkable entity was synthesized using N-([1,1′-biphenyl]-4-yl)-N-(4-(9-(4-vinylbenzyl)-9H-carbazol-3-yl)phenyl)bicyclo[4.2.0]octa-1(6),2,4-trien-3-amine (6) via addition polymerization. The X-TPACz could be spontaneously crosslinked without using any further reagents and showed a good film-forming property upon low-temperature thermal treatment. The thermal curing temperature for the X-TPACz film was optimized to be 180 °C based on a differential scanning calorimetry thermogram. Moreover, the thermal degradation temperature of X-TPACz measured to be over 467 °C using thermogravimetric analysis demonstrated that it shows excellent thermal stability. In particular, X-TPACz exhibits the highest occupied molecular orbital (HOMO) energy level to be −5.26 eV, which is beneficial for facile hole injection and transportation. Consequently, the thermally activated delayed fluorescence organic light-emitting diodes fabricated using X-TPACz as the hole-transporting material showed state-of-the-art performances with a low turn-on voltage (V on) of only 2.7 V and a high external quantum efficiency (EQE) of 19.18% with a high current efficiency (CE) of 66.88 cd/A and a high power efficiency (PE) of 60.03 lm/W, which are highly superior to those of the familiar poly(9-vinylcarbazole) (PVK)-based devices (V on = 3.9 V, EQE of 17.42%, with CE of 58.33 cd/A and PE of 33.32 lm/W). The extremely low turn-on voltage and high EQE were found to be due to the higher-lying highest occupied molecular orbital energy level (E HOMO = −5.23 eV) and better hole-transporting property of X-TPACz than those of PVK.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hole-Transporting Side-Chain Polymer Bearing a Thermally Crosslinkable Bicyclo[4.2.0]octa-1,3,5-trien-3-yl Group for High-Performing Thermally Activated Delayed Fluorescence OLED

Jeong

Godumala

Yoon

et al. 2019

ACS Appl. Mater. Interfaces

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“…To avoid mixing the upper and lower layers like this, most of the research groups are utilizing cross-linkable materials [7][8][9][10] . However, most of the cross-linkable hole transport layers (XHTLs) showed significantly low mobility than HTLs fabricated by vacuum deposition technology [11,12] .…”

Section: Introductionmentioning

confidence: 99%

P‐183: Improved Device Stability for Solution‐Processed Green Phosphorescent OLEDs via Interface Mixing Effect

Park

Ahn

Jung

et al. 2018

Symp Digest of Tech Papers

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“…The use of a number of crosslinking techniques was reported over the years of research on OLEDs. Those techniques usually involve UV or thermal crosslinking reaction and these approaches were proved as useful tools for application on charge injecting, transporting, blocking and emitting layers of OLEDs [9][10][11]. Both polymers and monomer precursors were used for obtaining the crosslinked polymer films [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Fluorescent thiol-epoxy thermosets obtained from diglycidylether of bisphenol A and carbazole based diepoxy monomer

Korychenska

Guzmán

Serra

et al. 2017

Reactive and Functional Polymers

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A new epoxy resin containing carbazole moieties was synthesized and added in several proportions to diglycidylether of bisphenol A (DGEBA) and trimethylolpropane tris(3-mercaptopropionate) (TTMP) formulations that were thermally cured by thiol-epoxy click reaction. The curing was catalyzed by a latent amine precursor, which after triggering at high temperature liberates the amine that enables the formation of thiolate groups. The curing process of the different formulations was monitored by calorimetric analysis, which allowed to observe that the increase of the proportion of the synthesized epoxy resin with carbazole groups in the formulation decreased the curing rate. However, all these formulations cured quickly after triggering, which make them adequate for the formation of layers in multilayer devices.\ud \ud Thermal characteristics of the obtained thermosets were determined by calorimetric, thermomechanical and thermogravimetric analysis. The obtained thermosets have good thermal stability. Their glass transition temperature increased when the proportion of the carbazole containing resin was increased in the formulation. The photophysical properties of the thermoset films were studied and it was proved that they exhibit fluorescence in the range of 352 to 369 °C.Postprint (author's final draft

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A new thermally crosslinkable hole injection material for OLEDs

Cited by 33 publications

References 21 publications

Hole-Transporting Side-Chain Polymer Bearing a Thermally Crosslinkable Bicyclo[4.2.0]octa-1,3,5-trien-3-yl Group for High-Performing Thermally Activated Delayed Fluorescence OLED

Hole-Transporting Side-Chain Polymer Bearing a Thermally Crosslinkable Bicyclo[4.2.0]octa-1,3,5-trien-3-yl Group for High-Performing Thermally Activated Delayed Fluorescence OLED

P‐183: Improved Device Stability for Solution‐Processed Green Phosphorescent OLEDs via Interface Mixing Effect

Fluorescent thiol-epoxy thermosets obtained from diglycidylether of bisphenol A and carbazole based diepoxy monomer

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