Solution Processed Organic Double Light‐Emitting Layer Diode Based on Cross‐Linkable Small Molecular Systems

Liaptsis, Georgios; Hertel, Dirk; Meerholz, Klaus

doi:10.1002/ange.201303031

Cited by 15 publications

(11 citation statements)

References 54 publications

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“…Additionally, Meerholz and co-workers synthesized several Ir complexes by direct Pd-catalyzed C−N bond formation between metallacycle 288 and substituted diarylamine 289 (Scheme 60b). 207 A variety of cross-linkable green-emitting complexes (290) for the fabrication of OLED devices were successfully generated with this method. The properties of the final compounds were greatly improved by the addition of one, two, or three TPA groups bearing a cross-linkable oxetane fragment into the 2phenylpyridine ligands.…”

Section: Applications Of the Coupling Of Secondarymentioning

confidence: 99%

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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Pd-catalyzed cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption of these methods has been the continued development of reliable and versatile catalysts that function under operationally simple, user-friendly conditions. This review provides an overview of Pd-catalyzed N-arylation reactions found in both basic and applied chemical research from 2008 to the present. Selected examples of C–N cross-coupling reactions between nine classes of nitrogen-based coupling partners and (pseudo)aryl halides are described for the synthesis of heterocycles, medicinally relevant compounds, natural products, organic materials, and catalysts.

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Section: Applications Of the Coupling Of Secondarymentioning

confidence: 99%

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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“…Therefore, there are only a few reported examples of efficient OLEDs with a cross-linked emission layer. 16,17 The orthogonal-solvent strategy has arisen as a crucial alternative to enable the solution deposition of ETLs on top of a multilayer stack. 18−20 It is important to note that this approach does not require the application of high curing temperatures or photoinitiators as with cross-linking.…”

Section: ■ Introductionmentioning

confidence: 99%

Orthogonal Solution-Processable Electron Transport Layers Based on Phenylpyridine Side-Chain Polystyrenes

Lorente

Pingel

Miasojedovas

et al. 2017

ACS Appl. Mater. Interfaces

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This article reports the synthesis and characterization of a series of polystyrenes containing phenylpyridine moieties as side chains. Methanol solubility of these polymers is induced if the relative pyridine content of the overall aromatic units of the side chains is larger than 0.5. This allows for orthogonal processing of multilayered organic light emitting diode (OLED) stacks fabricated from solutions. The polymers show high thermal stability due to their glass-transition temperatures ranging from 136 up to 247 °C. High triplet energies of up to 2.8 eV are obtained by combination of the side-chain aromatic rings in the meta position. The use of the methanol soluble side-chain polymers as an electron transport layer (ETL) is demonstrated in an orthogonally processed three-layer green-emitting OLED stack. When depositing the ETL from methanol, redissolution of the underlying emission layer does not occur.

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“…To solve the issue of weak performance 19,20 and undesirable UV photodamage 21 units that have recently been improved, 22 the group of K. Meerholz et al has extensively studied oxetane-based materials used as insoluble hole-injection layers, 23,24 electroluminescent polymers layers, 25,26 and more recently phosphorescent layers. 27 This family of cross-linkable molecules, however, requests a two-step procedure: i, a first curing step at around 100 °C to achieve full cross-linking since the photopolymerized films remain still soluble after UV irradiation; ii, a second postcuring step at 180 °C after development to destroy the radical cations left after the photoinitiation and propagation steps. In the case of photo-cross-linkable phosphorescent complexes, it turns out that the use of a host matrix and large photodegradation were mentioned, conducting to reduced performances.…”

Section: Introductionmentioning

confidence: 99%

“…In the case of photo-cross-linkable phosphorescent complexes, it turns out that the use of a host matrix and large photodegradation were mentioned, conducting to reduced performances. 27 In contrast with oxetane units, the use of polymerizable acrylate moieties advantageously eliminates any postcuring step after photopolymerization. Whereas acrylate monomers are widely used in the industry for construction adhesives, only a few OLED architectures fabricated out of them have been published in the literature to the best of our knowledge.…”

Section: Introductionmentioning

confidence: 99%

All-Solution-Processed Organic Light-Emitting Diodes Based on Photostable Photo-cross-linkable Fluorescent Small Molecules

Derue

Olivier

Tondelier

et al. 2016

ACS Appl. Mater. Interfaces

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We demonstrate herein the fabrication of small molecule-based OLEDs where four organic layers from the hole- to the electron-transporting layers have successively been deposited by using an all-solution process. The key feature of the device relies on a novel photopolymerizable red-emitting material, made of small fluorophores substituted with two acrylate units, and displaying high-quality film-forming properties as well as high emission quantum yield as nondoped thin films. Insoluble emissive layers were obtained upon UV irradiation using low illumination doses, with no further need of postcuring. Very low photodegradation was noticed, giving rise to bright layers with a remarkable surface quality, characterized by a mean RMS roughness as low as 0.7 nm after development. Comparative experiments between solution-processed OLEDs and vacuum-processed OLEDs made of fluorophores with close architectures show external quantum efficiencies in the same range while displaying distinct behaviors in terms of current and power efficiencies. They validate the proof of concept of nondoped solution-processable emissive layers exclusively made of photopolymerized fluorophores, thereby reducing the amount of components and opening the way toward cost-effective fabrication of solution-processed OLED multilayer architectures.

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Solution Processed Organic Double Light‐Emitting Layer Diode Based on Cross‐Linkable Small Molecular Systems

Cited by 15 publications

References 54 publications

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Orthogonal Solution-Processable Electron Transport Layers Based on Phenylpyridine Side-Chain Polystyrenes

All-Solution-Processed Organic Light-Emitting Diodes Based on Photostable Photo-cross-linkable Fluorescent Small Molecules

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