Determination of Solubility Parameters for Organic Semiconductor Formulations

Machui, Florian; Abbott, Steven; Waller, David; Koppe, Markus; Brabec, Christoph J.

doi:10.1002/macp.201100284

Cited by 109 publications

(107 citation statements)

References 24 publications

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“…Moreover, a solvation index like the Hansen solubility parameters cannot account for solidstate effects, such as how polymer-fi lm crystallinity infl uences swelling. [ 83 ] Instead, we can quantify the solvent-polymer fi lm interaction by calculating Flory-Huggins interaction parameters ( χ ) from the results of our swelling experiments (see SI for Flory-Huggins calculation details). [ 51,70,71,74,84 ] Figure 3 a shows the calculated values of χ for the solventpolymer fi lm pairs explored in Figure 2 ; stronger solvent-polymer fi lm interactions give lower values for χ .…”

Section: (4 Of 11)mentioning

confidence: 99%

Sequential Processing for Organic Photovoltaics: Design Rules for Morphology Control by Tailored Semi‐Orthogonal Solvent Blends

Aguirre

Hawks

Ferreira

et al. 2015

Advanced Energy Materials

166

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Design rules are presented for significantly expanding sequential processing (SqP) into previously inaccessible polymer:fullerene systems by tailoring binary solvent blends for fullerene deposition. Starting with a base solvent that has high fullerene solubility, 2‐chlorophenol (2‐CP), ellipsometry‐based swelling experiments are used to investigate different co‐solvents for the fullerene‐casting solution. By tuning the Flory‐Huggins χ parameter of the 2‐CP/co‐solvent blend, it is possible to optimally swell the polymer of interest for fullerene interdiffusion without dissolution of the polymer underlayer. In this way solar cell power conversion efficiencies are obtained for the PTB7 (poly[(4,8‐bis[(2‐ethylhexyl)oxy]benzo[1,2‐b:4,5‐b′]dithiophene‐2,6‐diyl)(3‐fluoro‐2‐[(2‐ethylhexyl)carbonyl]thieno[3,4‐b]thiophenediyl)]) and PC61BM (phenyl‐C61‐butyric acid methyl ester) materials combination that match those of blend‐cast films. Both semicrystalline (e.g., P3HT (poly(3‐hexylthiophene‐2,5‐diyl)) and entirely amorphous (e.g., PSDTTT (poly[(4,8‐di(2‐butyloxy)benzo[1,2‐b:4,5‐b′]dithiophene‐2,6‐diyl)‐alt‐(2,5‐bis(4,4′‐bis(2‐octyl)dithieno[3,2‐b:2′3′‐d]silole‐2,6‐diyl)thiazolo[5,4‐d]thiazole)]) conjugated polymers can be processed into highly efficient photovoltaic devices using the solvent‐blend SqP design rules. Grazing‐incidence wide‐angle x‐ray diffraction experiments confirm that proper choice of the fullerene casting co‐solvent yields well‐ordered interdispersed bulk heterojunction (BHJ) morphologies without the need for subsequent thermal annealing or the use of trace solvent additives (e.g., diiodooctane). The results open SqP to polymer/fullerene systems that are currently incompatible with traditional methods of device fabrication, and make BHJ morphology control a more tractable problem.

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Section: (4 Of 11)mentioning

confidence: 99%

Sequential Processing for Organic Photovoltaics: Design Rules for Morphology Control by Tailored Semi‐Orthogonal Solvent Blends

Aguirre

Hawks

Ferreira

et al. 2015

Advanced Energy Materials

166

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“…These endeavors have fostered a renewed interest in solubility parameters and their application to polymeric materials. However, current methods for estimating the solubility parameters of conjugated polymers and organic semiconductor moieties, for example, fullerene and fullerene derivatives, suffer from theoretical and computational deficiencies that have led to many questions and investigations that seek improvement in the solubility parameter theory of these compounds …”

Section: Introductionmentioning

confidence: 99%

Impact of Varying Binary Solvent Gradients on the Solubility Parameters of Poly(3‐hexylthiophene)

Sharp

Taylor

Andrews

et al. 2018

Macro Chemistry & Physics

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Current methods for estimating the solubility parameters (SPs) of a solute, particularly conjugated polymers and organic semiconductor moieties, suffer from theoretical and computational deficiencies that have led to many questions and investigations that seek improvement in solubility parameter theory. This investigation focuses on the variation of SPs of a protype conjugated polymer, poly(3‐hexylthiophene), using (1) different set of solvents and binary solvent mixtures having a broad range of chemical characteristics, and (2) multiple computational methodologies, for example, functional solubility parameter and Hansen solubility parameter approaches. The results reveal that the choice of solvents and the fitting methodology impact the empirical SPs when using the binary gradient method. The validity of the observed SPs and the relative contributions of the dispersion, polar, and hydrogen‐bonding interactions are further rationalized using linear solvation energy relationship modeling of the solubility data.

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“…One interesting tool is the Hansen solubility parameters (HSP) analysis, which has been demonstrated to provide relevant insights into different key aspects in OPVs such as the morphology of the bulk heterojunction layer, [ 17 ] fi nding suitable additives, [ 18 ] or new formulations that may enable to replace halogenated solvents. [ 4,[6][7][8] We have recently shown for a polymer:fullerene system that alternative green solvents can be identifi ed by determining in the fi rst place the solubility parameters for the materials under investigation and, in a second step, comparing the solubility parameters for the donor and acceptor materials with tabulated data for different solvents. [ 4 ] It would be particularly interesting to generalize our fi ndings to other materials systems in order to advance a simple general rationale for the identifi cation of green solvents and, in particular, those compatible with small molecule based OPV.…”

Section: Determination Of Hsp Of N(ph-2t-dcn-et) 3 and Pc 70 Bm Usimentioning

confidence: 99%

Solubility Based Identification of Green Solvents for Small Molecule Organic Solar Cells

Burgués‐Ceballos

Machui

Min

et al. 2013

Adv Funct Materials

Self Cite

138

116

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Replacing halogenated solvents in the processing of organic solar cells by green solvents is a required step before the commercialization of this technology. With this purpose, some attempts have been made, although a general method is yet to be developed. Here, the potential of the Hansen solubility parameters (HSP) analysis for the design of green ink formulations for solution‐processed active layer in bulk heterojunction photovoltaic devices based on small molecules is demonstrated. The motivation of moving towards organic small molecules stems from their lower molecular weight and more definite structure which makes them more likely to be dissolved in a wider variety of organic solvents. In the first step, the HSP of selected active materials are determined, namely, the star‐shaped D‐π‐A tris{4‐[5′′‐(1,1‐dicyanobut‐1‐en‐2‐yl)‐2,2′‐bithiophen‐5‐yl]phenyl}amine N(Ph‐2T‐DCN‐Et)3 small molecule and fullerene derivative [6,6]‐phenyl‐C71‐butyric acid methyl ester (PC70BM). Secondly, computer simulations based on HSP allow the prediction of suitable green solvents for this specific material system. The most promising green solvents, according to the simulations, are then used to fabricate solar cell devices using pristine solvents and two solvents mixtures. These devices show power conversion efficiencies around 3.6%, which are comparable to those obtained with halogenated solvents. This good performance is a result of the sufficient solubility achieved after a successful prediction of good (green) solvents.

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Determination of Solubility Parameters for Organic Semiconductor Formulations

Cited by 109 publications

References 24 publications

Sequential Processing for Organic Photovoltaics: Design Rules for Morphology Control by Tailored Semi‐Orthogonal Solvent Blends

Sequential Processing for Organic Photovoltaics: Design Rules for Morphology Control by Tailored Semi‐Orthogonal Solvent Blends

Impact of Varying Binary Solvent Gradients on the Solubility Parameters of Poly(3‐hexylthiophene)

Solubility Based Identification of Green Solvents for Small Molecule Organic Solar Cells

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