New 3 pi-2Spiro Ladder-Type Phenylene Materials: Synthesis, Physicochemical Properties and Applications in OLEDs

Nicolas Cocherel; Cyril Poriel; Joelle Rault-Berthelot; Frederic Barriere; Nathalie Audebrand; Alexandra M. Z. Slawin; Laurence Vignau

doi:10.1002/chem.200801428

New 3 pi-2Spiro Ladder-Type Phenylene Materials: Synthesis, Physicochemical Properties and Applications in OLEDs

Nicolas Cocherel, Cyril Poriel, Joelle Rault-Berthelot, Frederic Barriere, Nathalie Audebrand, Alexandra M. Z. Slawin, Laurence Vignau

Research output: Contribution to journal › Article › peer-review

Abstract

New routes to ladder-type phenylene materials I and 2 are described. The oligomers I and 2, which possess a "3 pi-2spiro" architecture, have been synthesized by using extended diketone derivatives 3 and 10 as key intermediates. The physicochemical properties of the new blue-light emitter 2 were studied in detail and compared with those of the less-extended 1. Owing to the recent development Of fluorenone derivatives and their corresponding more conjugated analogues as potential electron-transport materials in organic light-emilting diodes (OLEDs) and as n-type materials for photovoltaic applications, we also report herein the thermal, optical and electrochemical behavior of the key intermediates, diketones 3 and 10. Finally, the application of dispiro 2 as a new light-emitting material in OLEDs is reported.

Original language	English
Pages (from-to)	11328-11342
Number of pages	15
Journal	Chemistry - A European Journal
Volume	14
Issue number	36
DOIs	https://doi.org/10.1002/chem.200801428
Publication status	Published - 2008

Keywords

ladder pentaphenylenes
luminescence
organic light-emitting diodes
semiconductors
spiro compounds
LIGHT-EMITTING-DIODES
SPIRO-TYPE MOLECULES
OPTICAL-PROPERTIES
BUILDING-BLOCKS
PHOTOPHYSICAL PROPERTIES
CONJUGATED OLIGOMERS
COMMON INTERMEDIATE
TRANSPORT MATERIALS
BLUE EMISSION
POLYMERS

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/chem.200801428

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@article{b50f35ede4cc47d7a97ede041e947f04,

title = "New 3 pi-2Spiro Ladder-Type Phenylene Materials: Synthesis, Physicochemical Properties and Applications in OLEDs",

abstract = "New routes to ladder-type phenylene materials I and 2 are described. The oligomers I and 2, which possess a {"}3 pi-2spiro{"} architecture, have been synthesized by using extended diketone derivatives 3 and 10 as key intermediates. The physicochemical properties of the new blue-light emitter 2 were studied in detail and compared with those of the less-extended 1. Owing to the recent development Of fluorenone derivatives and their corresponding more conjugated analogues as potential electron-transport materials in organic light-emilting diodes (OLEDs) and as n-type materials for photovoltaic applications, we also report herein the thermal, optical and electrochemical behavior of the key intermediates, diketones 3 and 10. Finally, the application of dispiro 2 as a new light-emitting material in OLEDs is reported.",

keywords = "ladder pentaphenylenes, luminescence, organic light-emitting diodes, semiconductors, spiro compounds, LIGHT-EMITTING-DIODES, SPIRO-TYPE MOLECULES, OPTICAL-PROPERTIES, BUILDING-BLOCKS, PHOTOPHYSICAL PROPERTIES, CONJUGATED OLIGOMERS, COMMON INTERMEDIATE, TRANSPORT MATERIALS, BLUE EMISSION, POLYMERS",

author = "Nicolas Cocherel and Cyril Poriel and Joelle Rault-Berthelot and Frederic Barriere and Nathalie Audebrand and Slawin, {Alexandra M. Z.} and Laurence Vignau",

year = "2008",

doi = "10.1002/chem.200801428",

language = "English",

volume = "14",

pages = "11328--11342",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley & Sons, Ltd",

number = "36",

}

TY - JOUR

T1 - New 3 pi-2Spiro Ladder-Type Phenylene Materials: Synthesis, Physicochemical Properties and Applications in OLEDs

AU - Cocherel, Nicolas

AU - Poriel, Cyril

AU - Rault-Berthelot, Joelle

AU - Barriere, Frederic

AU - Audebrand, Nathalie

AU - Slawin, Alexandra M. Z.

AU - Vignau, Laurence

PY - 2008

Y1 - 2008

N2 - New routes to ladder-type phenylene materials I and 2 are described. The oligomers I and 2, which possess a "3 pi-2spiro" architecture, have been synthesized by using extended diketone derivatives 3 and 10 as key intermediates. The physicochemical properties of the new blue-light emitter 2 were studied in detail and compared with those of the less-extended 1. Owing to the recent development Of fluorenone derivatives and their corresponding more conjugated analogues as potential electron-transport materials in organic light-emilting diodes (OLEDs) and as n-type materials for photovoltaic applications, we also report herein the thermal, optical and electrochemical behavior of the key intermediates, diketones 3 and 10. Finally, the application of dispiro 2 as a new light-emitting material in OLEDs is reported.

AB - New routes to ladder-type phenylene materials I and 2 are described. The oligomers I and 2, which possess a "3 pi-2spiro" architecture, have been synthesized by using extended diketone derivatives 3 and 10 as key intermediates. The physicochemical properties of the new blue-light emitter 2 were studied in detail and compared with those of the less-extended 1. Owing to the recent development Of fluorenone derivatives and their corresponding more conjugated analogues as potential electron-transport materials in organic light-emilting diodes (OLEDs) and as n-type materials for photovoltaic applications, we also report herein the thermal, optical and electrochemical behavior of the key intermediates, diketones 3 and 10. Finally, the application of dispiro 2 as a new light-emitting material in OLEDs is reported.

KW - ladder pentaphenylenes

KW - luminescence

KW - organic light-emitting diodes

KW - semiconductors

KW - spiro compounds

KW - LIGHT-EMITTING-DIODES

KW - SPIRO-TYPE MOLECULES

KW - OPTICAL-PROPERTIES

KW - BUILDING-BLOCKS

KW - PHOTOPHYSICAL PROPERTIES

KW - CONJUGATED OLIGOMERS

KW - COMMON INTERMEDIATE

KW - TRANSPORT MATERIALS

KW - BLUE EMISSION

KW - POLYMERS

U2 - 10.1002/chem.200801428

DO - 10.1002/chem.200801428

M3 - Article

SN - 0947-6539

VL - 14

SP - 11328

EP - 11342

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 36

ER -

New 3 pi-2Spiro Ladder-Type Phenylene Materials: Synthesis, Physicochemical Properties and Applications in OLEDs

Abstract

Keywords

UN SDGs

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