<i>ortho‐, meta‐</i>, and <i>para</i>‐Dihydroindenofluorene Derivatives as Host Materials for Phosphorescent OLEDs

A series of non‐fullerene acceptors based on perylene monoimides coupled in the peri position through phenylene linkers were synthesized via Suzuki‐coupling reactions. Various substitution patterns were investigated using density functional theory (DFT) calculations in combination with experimental data to elucidate the geometry and their optical and electrochemical properties. Further investigations of the bulk properties with grazing incidence wide angle X‐ray scattering (GIWAXS) gave insight into the stacking behavior of the acceptor thin films. Electrochemical and morphological properties correlate with the photovoltaic performance of devices with the polymeric donor PBDB‐T and a maximum efficiency of 3.17 % was reached. The study gives detailed information about structure–property relationships of perylene‐linker‐perylene compounds.

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“…The same trend has been observed for p,m,o triphenyls. [49] Therefore, the trimeric compound 7 d has the lowest thermal stability (163 °C).…”

Section: Thermal Properties and Solubilitymentioning

confidence: 99%

Phenylene‐Bridged Perylene Monoimides as Acceptors for Organic Solar Cells: A Study on the Structure–Property Relationship

Schweda

Reinfelds

Hofinger

et al. 2022

Chemistry A European J

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“…The exponential development of organic electronic leads to an always growing demand of new, highly efficient organic semiconductors (OSCs) adapted to their use in specific devices 1 including organic light-emitting diodes (OLED) based on fluorescent emitting materials, [2][3][4][5][6][7][8] or based on phosphorescent materials, [9][10][11][12][13][14][15][16][17][18][19] organic field-effect transistor (OFET) [20][21][22][23][24] or organic photovoltaic (OPV). 1,25 Historically, in the field of OFETs, the design of p-type materials (hole-transporting) such as pentacene, 26 oligothiophene 27 or bridged oligoarylene [28][29] 33 (see 1-4 structures in Chart 1).…”

Section: Introductionmentioning

confidence: 99%

“…Among the molecular features that allow the modulation of OSC properties, regioisomerism can have remarkable consequences on the properties of the molecules. 6,21,[37][38] A simple structural modification can indeed drastically influence the oxidation potentials, 3,6,11,[39][40][41] the fluorescence properties, [3][4][5] the intermolecular π-π stacking, [42][43] which determines the magnitude of the charge-transfer integral and thus the charge transport in OSC devices. An interesting example of such architecture modification inducing strong changes both in the film morphology and OFETs performances has been reported for 2D π-expanded quinoidal terthiophenes.…”

Section: Introductionmentioning

confidence: 99%

Electron-Deficient Dihydroindaceno-Dithiophene Regioisomers for n-Type Organic Field-Effect Transistors

Peltier

Heinrich

Donnio

et al. 2017

ACS Appl. Mater. Interfaces

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In this work, we wish to report the first member of a new family of organic semi-conductors constructed on a meta dihydroindacenodithiophene core, that is 2,2'-(2,8-dihexyl-4,6-dihydro-s-indaceno [1,2-b:7,6-b']dithiophene-4,6-diylidene)dimalononitrile (called meta-IDT(=C(CN) 2 ) 2 ). The properties of this molecule have been studied in detail through a structure properties relationship study with its regioisomer, that is 2,2'-(2,7-dihexyl-4,9-dihydro-s-indaceno [1,2-b:5,6-b']dithiophene-4,9-diylidene)dimalononitrile (para-IDT(=C(CN) 2 ) 2 ) (see isomers structures in blue in Chart 2). The influence of the bridge functionalization has also been investigated by comparison with their diketone analogues meta-IDT(=O) 2 and para-IDT(=O) 2 . This study sheds light on the impact of regioisomerism on the electronic properties at the molecular level (electrochemistry, absorption spectroscopy, molecular modelling) and also on the supramolecular arrangement (SWAXS), and finally on the OFET performances and stabilities. The significant effect of self-assembled monolayers of 4-(dimethylamino) benzenethiol (DABT) grafted on the gold drain and source electrodes or of the use of flexible substrate (polyethylene naphtalate: PEN) instead of glass on the OFET performances and stabilities are also reported. In the light of these results (maximum mobility reaching 7.1×10 -2 cm² V -1 cm -1 , high Id on /Id off of 2.3×10 7 and

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“…To guarantee a high E T , wide energy gap materials are usually designed ,. However, due to the deep HOMO and high LUMO levels of wide band gap materials, simultaneously injecting holes and electrons into the host is difficult and requires multilayer devices, leading to high costs and a high turn‐on voltage ( V on ).…”

Section: Introductionmentioning

confidence: 99%

Modulation of the Physicochemical Properties of Donor–Spiro–Acceptor Derivatives through Donor Unit Planarisation: Phenylacridine versus Indoloacridine—New Hosts for Green and Blue Phosphorescent Organic Light‐Emitting Diodes (PhOLEDs)

Thiery

Tondelier

Geffroy

et al. 2016

Chemistry A European J

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This work reports a detailed structure-property relationship study of a series of efficient host materials based on the donor-spiro-acceptor (D-spiro-A) design for green and sky-blue phosphorescent organic light-emitting diodes (PhOLEDs). The electronic and physical effects of the indoloacridine (IA) fragment connected through a spiro bridge to different acceptor units, namely, fluorene, dioxothioxanthene or diazafluorene moiety, have been investigated in depth. The resulting host materials have been easily synthesised through short, efficient, low-cost, and highly adaptable synthetic routes by using common intermediates. The dyes possess a very high triplet energy (ET ) and tuneable HOMO/LUMO levels, depending on the strength of the donor/acceptor combination. The peculiar electrochemical and optical properties of the IA moiety have been investigated though a fine comparison with their phenylacridine counterparts to study the influence of planarisation. Finally, these molecules have been incorporated as hosts in green and sky-blue PhOLEDs. For the derivative SIA-TXO2 as a host, external quantum efficiencies as high as 23 and 14 % have been obtained for green and sky-blue PhOLEDs, respectively.

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ortho‐, meta‐, and para‐Dihydroindenofluorene Derivatives as Host Materials for Phosphorescent OLEDs

Cited by 25 publications

References 30 publications

Phenylene‐Bridged Perylene Monoimides as Acceptors for Organic Solar Cells: A Study on the Structure–Property Relationship

Phenylene‐Bridged Perylene Monoimides as Acceptors for Organic Solar Cells: A Study on the Structure–Property Relationship

Electron-Deficient Dihydroindaceno-Dithiophene Regioisomers for n-Type Organic Field-Effect Transistors

Modulation of the Physicochemical Properties of Donor–Spiro–Acceptor Derivatives through Donor Unit Planarisation: Phenylacridine versus Indoloacridine—New Hosts for Green and Blue Phosphorescent Organic Light‐Emitting Diodes (PhOLEDs)

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