N-phenyl[60]fulleropyrrolidines: alternative acceptor materials to PC<sub>61</sub>BM for high performance organic photovoltaic cells

Karakawa, Makoto; Nagai, Takabumi; Adachi, Kenji; Ie, Yutaka; Aso, Yoshio

doi:10.1039/c4ta04857a

Cited by 28 publications

(35 citation statements)

References 71 publications

(24 reference statements)

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“…However, and as far as we know, this is the only study in the literature in which devices with standard architecture ITO/PEDOT:PSS/BHJ/Al and based on N-alkyl-fulleropyrrolidine acceptors achieved efficiencies comparable to reference PC 61 BM-based devices. In 2015 Liang et al [54] also reported that N-phenyl-fulleropyrrolidines produced higher-performing devices than N-alkyl-fulleropyrrolidines, in accordance with the work of Karakawa et al [83].…”

Section: Resultssupporting

confidence: 62%

“…Based on this rationale, lowering the electron density on the N-atom of pyrrolidine, i.e., lowering its basicity, can be effective at improving the device performance. This study by Karakawa et al also referred us to some other previous studies reporting similar results but, according to these authors, not adequately explained [54,83,84]. In 2014, the same authors [83] had tested N-alkyland N-phenyl-fulleropyrrolidines in P3HT based OPV devices with the standard architecture ITO/PEDOT:PSS/BHJ/Al.…”

Section: Resultsmentioning

confidence: 84%

“…This study by Karakawa et al also referred us to some other previous studies reporting similar results but, according to these authors, not adequately explained [54,83,84]. In 2014, the same authors [83] had tested N-alkyland N-phenyl-fulleropyrrolidines in P3HT based OPV devices with the standard architecture ITO/PEDOT:PSS/BHJ/Al. OPV cells based on the N-alkyl-fulleropyrrolidines (more basic) exhibited low performances, while the performances obtained using the N-phenyl-fulleropyrrolidines (less basic) were comparable to or even higher than that of the corresponding PC 61 BM-based devices.…”

Section: Resultsmentioning

confidence: 84%

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PffBT4T-2OD Based Solar Cells with Aryl-Substituted N-Methyl-Fulleropyrrolidine Acceptors

et al. 2019

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Novel C60 and C70 N-methyl-fulleropyrrolidine derivatives, containing both electron withdrawing and electron donating substituent groups, were synthesized by the well-known Prato reaction. The corresponding highest occupied molecular orbital (HOMO)/lowest unoccupied molecular orbital (LUMO) energy levels were determined by cyclic voltammetry, from the onset oxidation and reduction potentials, respectively. Some of the novel fullerenes have higher LUMO levels than the standards PC61BM and PC71BM. When tested in PffBT4T-2OD based polymer solar cells, with the standard architecture ITO/PEDOT:PSS/Active-Layer/Ca/Al, these fullerenes do not bring about any efficiency improvements compared to the standard PC71BM system, however they show how the electronic nature of the different substituents strongly affects the efficiency of the corresponding organic photovoltaic (OPV) devices. The functionalization of C70 yields a mixture of regioisomers and density functional theory (DFT) calculations show that these have systematically different electronic properties. This electronic inhomogeneity is likely responsible for the lower performance observed in devices containing C70 derivatives. These results help to understand how new fullerene acceptors can affect the performance of OPV devices.

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Section: Resultssupporting

confidence: 62%

Section: Resultsmentioning

confidence: 84%

Section: Resultsmentioning

confidence: 84%

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PffBT4T-2OD Based Solar Cells with Aryl-Substituted N-Methyl-Fulleropyrrolidine Acceptors

et al. 2019

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“…7 and Table 4, the use of ZnO:PFN composite CBL caused a increase of FF from 64% to 71%, and consequently lead to an improvement of PCE from 6.30% to 7.17%. It is worth noting that an average PCE as 6.6% and the highest PCE as 7.17% for PTB7:PC 61 BM device with ZnO:PFN composite layer is among the highest reported efficiencies for PTB7 based low-bad gap polymer solar cells using C 60 derivative as the electron acceptor [36]. This value is also close to that of PTB7:PC 71 BM device [15,18].…”

Section: The Use Of Zno:pfn Composite Film In Low Band-gap Polymer Sosupporting

confidence: 70%

Zinc oxide: Conjugated polymer nanocomposite as cathode buffer layer for solution processed inverted organic solar cells

Luo

Bao

et al. 2015

Solar Energy Materials and Solar Cells

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“…Indeed, a large part of the OPV research reported so far, from the study of elementary processes and limiting factors to the optimization of material design and thin-film morphology, has been based on the use of PC 61 BM or PC 71 BM as n-type material. 3 As such, although several high-performance nonfullerene n-type materials have been reported recently, [4][5][6][7][8] fullerenes are still attractive scaffolds in constructing new n-type molecules for OPVs, [9][10][11] if one considers their favorable characteristics and the rich accumulated knowledge.…”

mentioning

confidence: 99%

Fullerene-Based n-Type Materials That Can Be Processed by a Photoprecursor Approach for Photovoltaic Applications

Kawajiri

Kawanoue

Yamato

et al. 2017

ECS J. Solid State Sci. Technol.

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The active layer of organic photovoltaic cells (OPVs) is typically a blend of p-and n-type semiconductors, and the arrangement of these materials largely affects the device performance. We have recently proposed a unique deposition technique in which α-diketone-type photoprecursors are solution-deposited and then subjected to in-situ photoreaction to form acene-based semiconductors, as an effective means for controlling the morphology and vertical composition profile in organic molecular blends. However, the applicability of this "photoprecursor approach" has been limited to p-type materials so far, restricting the flexibility in designing photovoltaic layers. Herein, we report α-diketone-type photoprecursors of two fullerene-anthracene conjugates which have been designed to serve as n-type material in OPVs. The new α-diketones, named N601DK and N602DK, are successfully applied to the photoprecursor approach, affording smooth thin films of the corresponding photoreaction products N601 and N602. The n-type materials thus produced are evaluated in bulk-heterojunction (BHJ) OPVs and found to show good photovoltaic response. Especially, N601 performs as well as PC 61 BM, a fullerene-based benchmark n-type material. These results will serve as a basis for further improvement of OPVs through optimization of the molecular arrangement in solution-processed photovoltaic layers. have been considered as the standard n-type materials in solutionprocessed organic photovoltaic layers. The strength of these compounds lies in the well-balanced electronic and electric properties of fullerene cages and the high processability derived from the flexible addend. Indeed, a large part of the OPV research reported so far, from the study of elementary processes and limiting factors to the optimization of material design and thin-film morphology, has been based on the use of PC 61 BM or PC 71 BM as n-type material. 3As such, although several high-performance nonfullerene n-type materials have been reported recently, 4-8 fullerenes are still attractive scaffolds in constructing new n-type molecules for OPVs, 9-11 if one considers their favorable characteristics and the rich accumulated knowledge.Meanwhile, we are applying a "photoprecursor approach" to the preparation of organic photovoltaic layers, in which semiconducting thin films are prepared by solution deposition of precursors followed by in-situ photoreaction to generate corresponding target compounds. Specifically, our process employs α-diketone-type photoprecursors that can be quantitatively converted to acene compounds with extrusion of carbon monoxide upon visible-light irradiation ( Figure 1a). 12 We have shown that this method is effective in preparing wellperforming photovoltaic layers comprising highly crystalline, scarcely soluble p-type molecular semiconductors which are otherwise hard to process by solution-based techniques. [13][14][15] The photoprecursor approach is also useful for the preparation of multilayer thin films by solution processes, provided that the solub...

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N-phenyl[60]fulleropyrrolidines: alternative acceptor materials to PC₆₁BM for high performance organic photovoltaic cells

Abstract: Novel [60]fulleropyrrolidine derivatives were synthesized and evaluated based on device performance. TheN-phenyfulleropyrrolidines showed better photovoltaic performance than theN-alkyl derivatives and showed high PCE up to 7.3% on combination with PTB7.

Cited by 28 publications

References 71 publications

PffBT4T-2OD Based Solar Cells with Aryl-Substituted N-Methyl-Fulleropyrrolidine Acceptors

PffBT4T-2OD Based Solar Cells with Aryl-Substituted N-Methyl-Fulleropyrrolidine Acceptors

Zinc oxide: Conjugated polymer nanocomposite as cathode buffer layer for solution processed inverted organic solar cells

Fullerene-Based n-Type Materials That Can Be Processed by a Photoprecursor Approach for Photovoltaic Applications

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N-phenyl[60]fulleropyrrolidines: alternative acceptor materials to PC61BM for high performance organic photovoltaic cells

Abstract: Novel [60]fulleropyrrolidine derivatives were synthesized and evaluated based on device performance. TheN-phenyfulleropyrrolidines showed better photovoltaic performance than theN-alkyl derivatives and showed high PCE up to 7.3% on combination with PTB7.

Cited by 28 publications

References 71 publications

PffBT4T-2OD Based Solar Cells with Aryl-Substituted N-Methyl-Fulleropyrrolidine Acceptors

PffBT4T-2OD Based Solar Cells with Aryl-Substituted N-Methyl-Fulleropyrrolidine Acceptors

Zinc oxide: Conjugated polymer nanocomposite as cathode buffer layer for solution processed inverted organic solar cells

Fullerene-Based n-Type Materials That Can Be Processed by a Photoprecursor Approach for Photovoltaic Applications

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N-phenyl[60]fulleropyrrolidines: alternative acceptor materials to PC₆₁BM for high performance organic photovoltaic cells