1,4‐Fullerene Derivatives: Tuning the Properties of the Electron Transporting Layer in Bulk‐Heterojunction Solar Cells

Varotto, Alessandro; Treat, Neil D.; Jo, Jang; Shuttle, Christopher G.; Batara, Nicolas A.; Brunetti, Fulvio G.; Seo, Jung Hwa; Chabinyc, Michael L.; Hawker, Craig J.; Heeger, Alan J.; Wudl, Fred

doi:10.1002/anie.201100029

Cited by 103 publications

(70 citation statements)

References 29 publications

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“…The LUMO levels of fullerene derivatives are one of the most important factors in evaluating their potential as electron acceptors in photovoltaic cells [31,44]. The electrochemical properties of ICBA, FICBA, MICBA, and BICBA were therefore estimated using cyclic voltammetry (CV).…”

Section: Resultsmentioning

confidence: 99%

“…in improved power conversion efficiencies (PCEs) of the PSCs compared to PCBM rarely has been reported due to the changes in other properties that are accompanied by the modifications, such as changes in the electrical properties, electro-chemical properties, and crystalline behavior [31,32,40,41]. Furthermore, the effects of chemical modification of fullerene derivatives have been rarely addressed in terms of the morphological interactions with conjugated polymers, although the changes of the solubility of the fullerene derivatives could significantly affect the interfacial interactions with polymers and the blend morphology.…”

Section: February 2015mentioning

confidence: 98%

“…The importance of the structural effects of the fullerene derivatives on the BHJ blend morphology can be amplified because they have much higher molecular mobility than polymers, resulting in the tendency to diffuse out of the polymer and thus, seriously affecting the BHJ blend morphology [24][25][26][27]. Initially, the solubilizing groups of the fullerenes were modified with the aim of tuning the LUMO levels, because the open-circuit voltage (V oc ) of the PSCs is proportional to the difference between the lowest unoccupied molecular orbital (LUMO) level of fullerene derivatives and the highest occupied molecular orbital (HOMO) level of the electron-donating polymers [28][29][30][31][32]. For example, several fullerene bis-adduct derivatives have been developed recently in order to effectively increase V oc and produce higher efficiencies in the PSCs [28,29,[33][34][35], because the fullerene bis-adducts have higher LUMO energy levels than fullerene mono-adducts.…”

Section: Introductionmentioning

confidence: 99%

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Molecular structure-device performance relationship in polymer solar cells based on indene-C60 bis-adduct derivatives

Cho

Kang

et al. 2014

Korean J. Chem. Eng.

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Interfacial tension between two materials is a key parameter in determining their miscibility and, thus, their morphological behavior in blend films. In bulk heterojunction (BHJ)-type polymer solar cells (PSCs), control of the interfacial tension between the electron donor and the electron acceptor is critically important in order to increase miscibility and achieve optimized BHJ morphology for producing efficient exciton dissociation and charge transport. Herein, we report the synthesis of a series of indene-C 60 bis-adducts (ICBA) derivatives by modifying their end-groups with fluorine (FICBA), methoxy (MICBA) and bromine (BICBA) functional units. We systematically studied the effects of their structural changes on the blend morphology with poly(3-hexylthiophene) (P3HT) and their performance in the PSCs. The end-group modification of ICBA derivatives induced a dramatic change in their interfacial tensions with P3HT (i.e., from 4.9 to 8.3 mN m −1 ), resulting in large variations in the power conversion efficiency (PCE) of the PSCs, ranging from 2.9 to 5.2%.

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Section: Resultsmentioning

confidence: 99%

Section: February 2015mentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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Molecular structure-device performance relationship in polymer solar cells based on indene-C60 bis-adduct derivatives

Cho

Kang

et al. 2014

Korean J. Chem. Eng.

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“…+ intermediate (Scheme 1); 20 2) reaction of C 60 with arylhydrazine and sodium nitrite producing 1,4-C 60 Ar(OH), 21 which react with arenes in the presence of p-toluenesulfonic acid giving 1,4-C 60 Ar 2 (Scheme 2); 22 3) hydroarylation reaction of C 60 in the presence of trichloroaluminum and a small amount of water giving C 60 Ar 2 H 2 , 23 which is deprotonated by base, followed by oxidation of the resulting fullerene anions by copper(I) salt to produce 1,4-C 60 Ar 2 (Scheme 3); 24 4) rhodiumcatalyzed addition reaction of arylboronic acids to C 60 producing monoadducts C 60 ArH, 25 which undergo palladium-catalyzed cross-coupling reaction with aryl halide to obtain 1,4-C 60 Ar 2 (Scheme 4). 26 Although diarylfullerene is a stable compound, its performance as an electron-acceptor in organic thin-film solar cells is limited.…”

Section: ç Improvement Of Open-circuit Voltage By Installation Of Elementioning

confidence: 99%

Design Concept for High-LUMO-level Fullerene Electron-acceptors for Organic Solar Cells

Matsuo

2012

Chemistry Letters

113

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This review article describes design concept, synthesis, and features of fullerene derivatives having high lowest unoccupied molecular orbital (LUMO) levels to achieve high open-circuit voltage in organic thin-film photovoltaic devices. Installation of organic electron-donating groups onto fullerene and decrease of the size of the fullerene ³-electron-conjugated system raise the LUMO levels, affording high-performance organic solar cells. Addition of the methano group as the smallest carbon addend to fullerene to obtain 56³-electron fullerene derivatives is likely a promising strategy for this purpose. Ç IntroductionOrganic thin-film solar cells are lightweight and flexible, and thus are expected to allow for low-cost production through a printing process. 1 The active layer that converts light into electricity contains organic semiconductors, whose development is the key to improving power conversion efficiency. Accordingly, organic chemistry has a major role to play. Up to now, the development of organic thin-film solar cells has been led by material scientists and device engineers, but there is increasing demand for collaboration with synthetic chemists who can design and synthesize organic semiconductor molecules.Although the power conversion efficiency of organic thinfilm solar cells was about 1% before 2000, a sharp increase in conversion efficiency was seen after 2000, owing to the discovery of the combination of poly(3-hexylthiophene) (P3HT; an organic electron-donor) and phenyl-C 61 -butyric acid methyl ester (PCBM; an organic electron-acceptor).2 When heated and exposed to solvent vapor, P3HT undergoes self-assembly and forms ³-stacked structures, improving its electrical properties and light absorption characteristics. Furthermore, PCBM is a fullerene derivative that is soluble in organic solvents, and its solubility allows for blend solutions containing P3HT to be prepared over a range of concentrations. Furthermore, thin films prepared through the use of a P3HT/PCBM blend solution have made it possible to develop composite films with a bulk heterojunction structure, in which an electron-donor and an electron-acceptor are suitably mixed.3 In comparison with conventional pn heterojunction devices, bulk heterojunction devices have a greater interface area between the donor and acceptor and charge separation is more efficient. In this way, around 2005, power conversion efficiency reached 45%. 4 In the last few years, the power conversion efficiency of organic thin-film solar cells has increased further to about 10%. 5This vast improvement was largely due to the development of new materials, for example, new electron-donors such as low band gap polymers, 6 which are capable of absorbing longwavelength light. These materials are alternating copolymers with electron-rich and electron-deficient parts, and for this reason they have high-lying HOMO and low-lying LUMO levels. Intermolecular charge transfer from electron-rich parts to electron-deficient parts makes such materials capable of absorbing...

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“…Fig. 7 Structures of bisPCBM [169], C-PCBSD [171], and some of the 1, 4-addends (PF8, ANP, PEHOB, PCVM, and PTHOB/PTPOB) [172] The stacking of fullerene derivatives in BHJs influences both the carrier transport and the stability of the OSCs [173]. However, functional groups which facilitate the solution of fullerenes may disorder the stacking of fullerene derivatives, resulting in low short-circuit current density (J SC ) and low fill factor (FF).…”

Section: Fullerene Derivatives As Electron Acceptors In Polymer-basedmentioning

confidence: 99%

Carbon nanomaterials for photovoltaic process

Zhang

Qin

et al. 2015

Nano Energy

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1,4‐Fullerene Derivatives: Tuning the Properties of the Electron Transporting Layer in Bulk‐Heterojunction Solar Cells

Cited by 103 publications

References 29 publications

Molecular structure-device performance relationship in polymer solar cells based on indene-C60 bis-adduct derivatives

Molecular structure-device performance relationship in polymer solar cells based on indene-C60 bis-adduct derivatives

Design Concept for High-LUMO-level Fullerene Electron-acceptors for Organic Solar Cells

Carbon nanomaterials for photovoltaic process

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