Crosslinkable hole-transporting polymers by palladium-catalyzed C—N-coupling reaction

Braig, Thomas; Müller, David C.; Groß, Markus; Meerholz, Klaus; Nuyken, Oskar

doi:10.1002/1521-3927(20000601)21:9<583::aid-marc583>3.0.co;2-o

Cited by 36 publications

(7 citation statements)

References 7 publications

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“…The commercially available photoinitiator [4‐[(2‐hydroxytetradecyl)oxy]phenyl] phenyl‐iodonium hexafluoroantimonate, which can undergo photolysis at 210–254 nm was added to initiate the crosslinking process. During ultraviolet (UV) illumination, this photoinitiator decomposes via a multiple‐step mechanism to generate protons, which open the oxetane ring and start the polymerization reaction …”

Section: Resultsmentioning

confidence: 99%

“…A common method used to overcome this obstacle is to render the applied polymer layer by crosslinking before the subsequent coating step. The crosslinking process for obtaining phosphorescent polymer light‐emitting diodes (Ph‐PLED) can be carried out via a variety of strategies such as thermal, light, or chemical treatment . Polymeric hole‐transport materials and host materials can be designed and synthesized in this manner to facilitate efficient singlet and triplet energy transfer in the solid state.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, an additional hole‐transport layer (HTL) or HIL can be combined with a conventional HIL material to form an optimal cascade energy profile to achieve efficient hole injection and charge confinement. For the fabrication of multilayered devices solely by solution processing, either photo‐ or thermally crosslinked hole‐transporting materials are frequently used …”

Section: Introductionmentioning

confidence: 99%

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Novel 9,9′-(1,3-phenylene)bis-9H-carbazole-containing copolymers as hole-transporting and host materials for blue phosphorescent polymer light-emitting diodes

Yoon

Shin

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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Novel photo‐crosslinkable hole‐transport and host materials incorporated into multilayer blue phosphorescent polymer light‐emitting diodes (Ph‐PLEDs) were demonstrated in this study. The oxetane‐containing copolymers, which function as hole‐transport layers (HTL), could be cured by UV irradiation in the presence of a cationic photoinitiator. The composition of the two monomers was varied to yield three different hole‐transporting copolymers, [Poly(9,9′‐(5‐(((4‐(7‐(4‐(((3‐methyloxetan‐3‐yl)methoxy)methyl)phenyl)octan‐3‐yl)benzyl)oxy)methyl)−1,3‐phenylene)bis(9H‐carbazole)) (P(mCP‐Ox)‐I, ‐II, and ‐III)]. In addition, monomer 1 was copolymerized with styrene to produce copolymer P(mCP‐Ph) as a host material for bis[2‐(4,6‐difluorophenyl)pyridinato‐C2,N](picolinato)iridium(III) (FIrpic), a blue‐emitting dopant. All mCP‐based copolymers displayed high glass transition temperatures (Tg) of up to 130–140 °C and triplet energies of up to 3.00 eV. The blue Ph‐PLEDs exhibited a maximum external quantum efficiency of 2.55%, in addition to a luminous efficiency of 8.75 cd A−1 when using the device configuration of indium tin oxide/poly(3,4‐ethylenedioxythiophene):poly(styrene sulfonate)/P(mCP‐OX)‐III/P(mCP‐Ph):FIrpic(15 wt %)/3,3′‐[5′‐[3‐(3‐pyridinyl)phenyl][1,1′:3′,1′′‐terphenyl]‐3,3′′‐diyl]bispyridine/LiF/Al. The device bearing P(mCP‐Ox)‐III HTL, containing the highest composition of mCP unit, exhibited better performance than the other devices, which is attributed to induction of more balanced charge carriers and carrier recombination in the emissive layer. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 707–718

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Novel 9,9′-(1,3-phenylene)bis-9H-carbazole-containing copolymers as hole-transporting and host materials for blue phosphorescent polymer light-emitting diodes

Yoon

Shin

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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“…It controls the efficiency of hole injection and transport from the anode into a light EML. The interfacial contact between indium tin oxide (ITO)/hole injection layer (HIL) or HIL/HTL particularly limits charge injection and transport 13–16. In green phosphorescent polymer LEDs, large bandgap host materials, such as poly( N ‐vinylcarbazole) (PVK) or polyfluorene, with a triplet energy higher than that of the phosphorescent Ir(III) complex could be used because of the high highest occupied molecular orbital (HOMO) energy level of these large bandgap polymers,17 the efficiency of the hole injection from the ITO to the EML may be suppressed if only a poly(3,4‐ethylenedioxythiophene)/(polystyrenesulfonate) (PEDOT:PSS) layer is used in the device.…”

Section: Introductionmentioning

confidence: 99%

Cascade hole transport in efficient green phosphorescent light‐emitting devices achieved by layer‐by‐layer solution deposition using photocrosslinkable‐conjugated polymers containing oxetane side‐chain moieties

Shin

Cho

et al. 2011

J. Polym. Sci. A Polym. Chem.

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A hole‐injection/transport bilayer structure on an indium tin oxide (ITO) layer was fabricated using two photocrosslinkable polymers with different molecular energy levels. Two photoreactive polymers were synthesized using 2,7‐(or 3,6‐)‐dibromo‐9‐(6‐((3‐methyloxetan‐3‐yl)methoxy)hexyl)‐9H‐carbazole) and 2,4‐dimethyl‐N,N‐bis(4‐ (4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)aniline via a Suzuki coupling reaction. When the oxetane groups were photopolymerized in the presence of a cationic photoinitiator, the photocured film showed good solvent resistance and compatibility with a poly(N‐vinylcarbazole) (PVK)‐based emitting layer. Without the use of a conventional hole injection layer (HIL) of poly(3,4‐ethylenedioxythiophene)/(polystyrenesulfonate) (PEDOT:PSS), the resulting green light‐emitting device bearing PVK: 5‐4‐tert‐butylphenyl‐1,3,4‐oxadiazole (PBD):Ir(Cz‐ppy)3 exhibited a maximum external quantum efficiency of 9.69%; this corresponds to a luminous efficiency of 29.57 cd/A for the device K‐4 configuration ITO/POx‐I/POx‐II/PVK:PBD:Ir(Cz‐ppy)3/triazole/Alq3/LiF/Al. These values are much higher than those of PLEDs using conventional PEDOT:PSS as a single HIL. The significant improvement in device efficiency is the result of suppression of the hole injection/transport properties through double‐layered photocrosslinked‐conjugated polymers. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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“…These photopolymers have a wide variety of applications in the fields of macroand microlithography, 1,2 liquid crystals, 3,4 tissue engineering, 5 -7 biosensors, 8 UV-curing adhesives, 9 hole transporting materials in organic light emitting diodes 10 and optical anisotropy.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and properties of photoresponsive polymers comprising photocrosslinkable pendant chalcone moieties

Tamilvanan

Pandurangan

Reddy

et al. 2006

Polymer International

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New methacrylate monomers, namely 4-methacryloyloxyphenyl-4 -fluorostyryl ketone and 4-methacryloyloxyphenyl-4 -ethylstyryl ketone comprising a free radical polymerizable group and a photocrosslinkable group, were synthesized by reacting the respective hydroxychalcones with methacryloyl chloride in the presence of triethylamine. The monomers were polymerized in the presence of ethyl methyl ketone (EMK) at 70• C using benzoyl peroxide as the initiator. The chemical structures were characterized using various spectroscopic techniques: ultraviolet, Fourier transform infrared, 1 H NMR and 13 C NMR. The thermal stability of the polymers was studied using thermogravimetric analysis in nitrogen atmosphere. Differential scanning calorimetry was used to determine the glass transition temperature of the homopolymers. Photocrosslinking of the synthesized homopolymers was investigated in solution. The two homopolymers were crosslinked within 10-15 min. After crosslinking, the homopolymers were insoluble in the same solvent.

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Crosslinkable hole-transporting polymers by palladium-catalyzed C—N-coupling reaction

Cited by 36 publications

References 7 publications

Novel 9,9′-(1,3-phenylene)bis-9H-carbazole-containing copolymers as hole-transporting and host materials for blue phosphorescent polymer light-emitting diodes

Novel 9,9′-(1,3-phenylene)bis-9H-carbazole-containing copolymers as hole-transporting and host materials for blue phosphorescent polymer light-emitting diodes

Cascade hole transport in efficient green phosphorescent light‐emitting devices achieved by layer‐by‐layer solution deposition using photocrosslinkable‐conjugated polymers containing oxetane side‐chain moieties

Synthesis, characterization and properties of photoresponsive polymers comprising photocrosslinkable pendant chalcone moieties

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