Improved performance of solution processed OLEDs using <i>N</i>-annulated perylene diimide emitters with bulky side-chains

Dayneko, Sergey V.; Cieplechowicz, Edward; Bhojgude, Sachin Suresh; Humbeck, Jeffrey F. Van; Pahlevani, Majid; Welch, Gregory C.

doi:10.1039/d0ma00827c

Cited by 26 publications

(15 citation statements)

References 38 publications

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“…1) and perylene diimide (PDI, Fig. 1) are the keystones of many reference n-type semiconducting materials 5,6 used in various optoelectronic applications such as organic field effect transistors (OFETs), 7,8 fluorescent sensors, 9,10 electro-photographic devices, 11 laser dyes, [12][13][14] organic photovoltaics (OPV) [15][16][17][18] or organic light-emitting diodes (OLEDs), [19][20][21] CO 2 reduction, 22 and H 2 production. 23 The related benzothioxanthene imide (BTI, Fig.…”

Section: Introductionmentioning

confidence: 99%

Thiochromenocarbazole imide: a new organic dye with first utility in large area flexible electroluminescent devices

Castán

Amruth

Josse

et al. 2022

Mater. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Thiochromenocarbazole imide: a new organic dye with first utility in large area flexible electroluminescent devices

Castán

Amruth

Josse

et al. 2022

Mater. Chem. Front.

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“…A class of synthetically versatile organic compounds, known as π-conjugated materials, have been extensively used for a number of applications including charge transport/extraction, − light emission, − and even small-molecule catalysis. − Among the numerous π-conjugated material designs, the arrangement of electron-deficient (acceptor) and electron-rich (donor) organic units in an acceptor–donor–acceptor (A–D–A) motif has been popularized owing to the fact that the optical band gap, electron affinity, and/or redox stability can be easily tuned . Generally speaking, improved semiconducting properties are observed in A–D–A systems with an extended π-orbital overlap; this can be achieved by materials that exhibit either a highly planar ring-fused organic backbone or by those that promote conformational locking interactions between heteroatom-containing functional groups in the organic backbone. − ,, While nearly an infinite number of specialized organic building blocks may be pieced together to make these A–D–A π-conjugated materials, it is important that a reliable, selective, efficient, and atom-economical synthetic protocol be developed for these materials to ever be produced on the industrial scale. , With these criteria in mind, the use of direct (hetero)arylation (DHA) to develop these π-conjugated materials has been leveraged as a highly effective cross-coupling method.…”

Section: Introductionmentioning

confidence: 99%

Systematic Investigation of Core and Endcap Selection on the Development of Functional π-Conjugated Materials

et al. 2022

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We investigate the optoelectronic properties of four new πconjugated materials, which feature either a 3,4-ethylenedioxythiophene (EDOT) or an EDOT-flanked benzothiadiazole aryl core with two N-annulated perylene diimide (NPDI) or theobromine endcaps. Endcap selection was an important factor for the preferred molecular geometry, where the use of NPDI endcaps induced a dragonfly-type conformation and the use of theobromine endcaps promoted a corkscrew-like conformation. Electrochemically, the choice of aryl πconjugated core was found to have a strong influence on the molecule's highest occupied molecular orbital (HOMO) energy level, while the choice of endcap had a more profound effect on the lowest unoccupied molecular orbital (LUMO) energy level. Although the optical absorption profiles were generally dominated by endcap contributions, using the larger EDOT-flanked benzothiadiazole aryl core was found to decrease the optical energy band gap. Proof-of-concept organic photovoltaic (OPV) devices, using a PM6:Y6 bulk heterojunction (BHJ) photoactive layer, were fabricated using the four new π-conjugated materials as the cathode interlayer (CIL). The molecules featuring the EDOT aryl core (A and B) enabled OPV device power conversion efficiencies (PCEs) by around 12%, comparable to control devices using PDINN as the CIL, while those featuring the EDOT-flanked benzothiadiazole aryl core (C and D) obtained PCEs of 10.5%. The observed differences in OPV device performance were attributed to superior solubility and subsequent CIL film formation in the case of A and B, compared to C and D, which, in turn, led to improved contact between the Ag top electrode and the BHJ photoactive layer.

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“…[1][2][3][4][5] In general, conventional fluorophores such as perylene, xanthene, cyanine, coumarin, and BODIPY skeletons have been modified by introducing various substituents or fusing aromatic ring to function as the desired sensors, probes or emitters for precision applications. [6][7][8][9][10] On the other hand, the development of new type of fluorophores can create new applications, as well as leading to dramatic improvement in fluorescence sensing and imaging and device performances. Thus, for this purpose, we have developed benzofuro [2,3-c]carbazoloquinone BfCzQ-1 as a useful intermediate which allows us to create various kinds of fluorophores (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-<i>c</i>]carbazoloquinol Fluorescent Dyes

et al. 2021

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Benzofuro [2,3-c]carbazoloquinol derivatives, a new type of fluorescent dyes, were derived from the corresponding quinone, and their optical and electrochemical properties were investigated by photoabsorption and fluorescence spectroscopy, cyclic voltammetry (CV) and density functional theory (DFT) calculation. The quinol derivatives in 1,4-dioxane showed the photoabsorption band at around 435 nm (molar extinction coefficient (εmax) = ca. 6000-8000 M -1 cm -1 ) and the fluorescence band at around 520 nm (fluorescence quantum yield (Φfl) = 0.24-0.28). The CV demonstrated that the quinol derivatives exhibit an irreversible oxidation wave at around 0.28 V versus Fc/Fc + . The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels of the quinol derivatives which were calculated using DFT at the B3LYP/6-31G(d,p) level are in good agreement with the experimental results. Key word: Benzofuro[2,3-c]carbazoloquinol; Photoabsorption; Fluorescence; Redox 2.1. General 1 H NMR spectra were recorded on a JNM-LA-400 (400 MHz) FT NMR spectrometer with tetramethylsilane (TMS) as an internal standard. IR spectra were recorded on a Perkin Elmer Spectrum One FT-IR spectrometer by ATR method. Cyclic voltammograms were recorded in acetonitrile/Et4NClO4 (0.1 M) solution with a three-electrode system consisting of Ag/Ag + as reference electrode, Pt plate as working electrode, and Pt wire as counter electrode, by using a Hokuto Denko HAB-151 potentiostat equipped with a functional generator. Column chromatography was performed on silica gel (KANTO CHEMICAL, 60N, spherical, neutral). Photoabsorption spectra were observed with a Shimadzu UV-3150 spectrophotometer, and fluorescence spectra were measured with a Hitachi F-4500 spectrophotometer. The fluorescence quantum yields (Φfl) were determined by a Hamamatsu C9920-01 equipped with CCD by using a calibrated integrating sphere system (λ ex = 325 nm). SynthesisGeneral synthetic procedure for YK-1 and YK-2: To a THF solution of BfCzQ-1 under an Ar atmosphere was added ethereal solution of organolithium (2.5 equivalent BuLi or PhLi) at -108 °C over 15 min. After stirring for 15 min at room temperature, the reaction was quenched with saturated NH4Cl solution. The solvent was evaporated, and the residue was extracted with CH2Cl2. The organic extract was washed with water. The CH2Cl2 extract was evaporated, and the residue was chromatographed on silica gel (CH2Cl2 : AcOEt = 3 : 1 as eluent) to give YK-1 or YK-2 with recovery

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Improved performance of solution processed OLEDs using N-annulated perylene diimide emitters with bulky side-chains

Abstract: We report the design and synthesis of three N-annulated perylene diimide (PDI) compounds containing sterically bulky alkyl-substituted benzyl moieties (PDI-X, where X = 1, 2, 3) and explore their use as light emitting materials in solution processed OLED devices.

Cited by 26 publications

References 38 publications

Thiochromenocarbazole imide: a new organic dye with first utility in large area flexible electroluminescent devices

Thiochromenocarbazole imide: a new organic dye with first utility in large area flexible electroluminescent devices

Systematic Investigation of Core and Endcap Selection on the Development of Functional π-Conjugated Materials

Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-<i>c</i>]carbazoloquinol Fluorescent Dyes

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