Synthesis and characterization of tris-(5-amino-8-hydroxyquinoline)aluminum complexes and their use as anode buffer layers in inverted organic solar cells

Manninen, Venla; Omar, Walaa A. E.; Heiskanen, Juha P.; Lemmetyinen, Helge; Hormi, Osmo

doi:10.1039/c2jm35292c

Cited by 24 publications

(22 citation statements)

References 34 publications

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“…PFDCTBT-C8 [81] Dark poly(fl uorenedicyclopentathiophene-altbenzothiadiazole) with octyl side chains a-PTPTBT [82] Dark Poly(thiophene-phenylene-thiophene -2,1,3-benzothia-diazole) [80][81][82][86][87][88][89][90][91][92][93][94][95] and under light (right). [ 73,78,[83][84][85] PCE represents the values at the point of stabilization of the aging curve ( E s value).…”

Section: Namementioning

confidence: 99%

Lifetime of Organic Photovoltaics: Status and Predictions

Gevorgyan

Madsen

Roth

et al. 2015

Advanced Energy Materials

137

124

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performance level, especially when considering large-scale mass-produced modules, is predicted to be signifi cantly lower. [ 8 ] Nevertheless, based on recent advances in the upscaling of OPV manufacture [9][10][11][12] it is reasonable to assume that the mass production of modules with an effi ciency of more than 5% is an achievable target today. Durability of OPV is however yet to be proven and demonstrated.Due to core architectural differences between OPV and inorganic technologies [ 13 ] the established testing standards of the latter are not applicable to the former. [ 1 ] Hence, for many years the stability testing of OPV has primarily been based on customized procedures that vary from one laboratory to another, generating incomparable data. [ 14 ] Moreover, due to the complexity of the OPV device architectures [ 15 ] and a multitude of aging mechanisms taking place at the same time [ 16 ] the aging curve of OPV often takes a complex shape, which is diffi cult to model, [ 14,17 ] thus making the identifi cation of a practical operational lifetime diffi cult or impossible. [ 18 ] As a result, even with a multitude of reported review articles discussing OPV stability [ 16,[19][20][21][22][23][24] at hand, it is still challenging to identify where the technology stands in terms of lifetime. To address this it is necessary to create a yardstick -a generic marker that allows accurate rating and comparison of the lifetime for OPV, and thus enabling the gauging of progress over time. An additional complication that has arisen due to the signifi cant improvements in OPV stability and durability in recent years is that the determination of OPV lifetimes has become an impractically long process, and establishing markers for both accelerated and real operational test conditions (if successful) would allow developing a prediction tool that could speed up the stability testing process and tackle this issue.The groundwork towards creating such a marker was laid in 2011 at the International Summit on OPV Stability (ISOS) where the ISOS testing guidelines were decided upon and described for OPV technologies. [ 18 ] These guidelines were primarily aimed at harmonizing testing procedures among different laboratories by offering a set of indoor and outdoor tests with controlled conditions. This has helped to reduce variations in the reported results, making the aging studies of different laboratories more comparable. [ 25 ] While the ISOS tests harmonized the test conditions, the questions of how to generically determine the lifetime from aging curves of diverse shapes, and how to build a technique for predicting the lifetime based on accelerated tests remained.The results of a meta-analysis conducted on organic photovoltaics (OPV) lifetime data reported in the literature is presented through the compilation of an extensive OPV lifetime database based on a large number of articles, followed by analysis of the large body of data. We fully reveal the progress of reported OPV lifetimes. Furthermore, a generic lifetime marker has...

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Section: Namementioning

confidence: 99%

Lifetime of Organic Photovoltaics: Status and Predictions

Gevorgyan

Madsen

Roth

et al. 2015

Advanced Energy Materials

137

124

View full text Add to dashboard Cite

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“…The Buchwald-Hartwig coupling was performed in the presence of Pd(OAc) 2 , JohnPhos and KOt-Bu in toluene leading to 16e in a yield of 40% (Scheme 1, Method A). 45 In order to improve the outcome, several substitution reactions were tried using 16d (Method B, C and D). 46,47 The best result was obtained reacting 16d with 6 equiv.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and fluorescent properties of boroisoquinolines, a new family of fluorophores

et al. 2018

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“…All solvents for the reactions were freshly distilled immediately prior to use. 8‐(Benzyloxy)‐5‐bromoquinoline, 8‐benzyloxy‐5‐(4,4,5,5‐tetramethyl‐[1,3,2]dioxaborolan‐2‐yl‐quinoline, N , N ‐bis(1‐butylpentyl)‐3,4,9,10‐perylene tetracarboxylic bisimides, 1‐bromo‐ N , N ‐bis(1‐butylpentyl)‐3,4,9,10‐perylene tetracarboxylic bisimides, 5,6‐difluoro‐4,7‐bis(thiophen‐2‐yl)‐2,1,3‐benzothiadiazole, compound 9, and compound 10 were synthesized according to previously reported procedures.…”

Section: Methodsmentioning

confidence: 99%

Achieving a High Fill Factor and Stability in Perylene Diimide–Based Polymer Solar Cells Using the Molecular Lock Effect between 4,4′‐Bipyridine and a Tri(8‐hydroxyquinoline)aluminum(III) Core

Zhang

Lee

et al. 2019

Adv Funct Materials

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Two novel perylene diimide (PDI)-based derivatives, Alq 3 -PDI and Alq 3 -PDI2, are synthesized by flanking a 3D tri(8-hydroxyquinoline)aluminum(III) (Alq 3 ) core with PDI and a helical PDI dimer (PDI2) to construct high-performance small molecular nonfullerene acceptors (SMAs). The 3D Alq 3 core significantly suppresses the molecular aggregation of the resulting SMAs, leading to a well-mixed blend with a PTTEA donor polymer and weak phase separation. Compared with Alq 3 -PDI, the extended π-conjugation of Alq 3 -PDI2 results in higher-order molecular packing, which improves the absorption and phase separation behavior. Thus, the Alq 3 -PDI2 devices have higher J sc and FF values and better device performance, which are further enhanced by a small amount of 4,4′-bipyridine (Bipy) as an additive. The coordination between Bipy and the Alq 3 core promotes molecular packing and phase separation, which lower charge recombination and enhanced charge collection in the resulting devices. Therefore, a largely improved J sc of 15.74 mA cm −2 and very high FF of 71.27% are obtained in the Alq 3 -PDI2 devices, resulting in a power conversion efficiency of 9.54%, which is the best value reported for PDI-based polymer solar cells. The coordination can also serve as a "molecular lock," which prevents molecular motion and thus improves device stability.

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Synthesis and characterization of tris-(5-amino-8-hydroxyquinoline)aluminum complexes and their use as anode buffer layers in inverted organic solar cells

Cited by 24 publications

References 34 publications

Lifetime of Organic Photovoltaics: Status and Predictions

Lifetime of Organic Photovoltaics: Status and Predictions

Synthesis and fluorescent properties of boroisoquinolines, a new family of fluorophores

Achieving a High Fill Factor and Stability in Perylene Diimide–Based Polymer Solar Cells Using the Molecular Lock Effect between 4,4′‐Bipyridine and a Tri(8‐hydroxyquinoline)aluminum(III) Core

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