Facile Synthesis of Fluorine‐Substituted Benzothiadiazole‐Based Organic Semiconductors and Their Use in Solution‐Processed Small‐Molecule Organic Solar Cells

Cho, Nara; Song, Kihyung; Lee, Jae Kwan; Ko, Jaejung

doi:10.1002/chem.201201321

Cited by 65 publications

(54 citation statements)

References 38 publications

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“…Besides, molecules using oligothiophene as a highly extended π-conjugated bridge not only broaden the absorption region but also promote strong π-π stacking of conjugated backbones [40][41][42][43][44][45]. The chemical structures of compounds using oligothiophene as π-linkage are shown in Fig.…”

Section: Oligothiophene-linkagementioning

confidence: 99%

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

Yin

2016

Sci. China Mater.

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Much attention has been paid to the push-pullstructure organic small molecule (OSM) materials for photovoltaic (PV) application in the past decade, due to their facile reduction of energy band gap (Eg) and effective control of PV properties. π-bridge plays an important role in the push-pull-structure OSMs since an appropriate π-linkage is crucial for improving the PV performance of organic solar cells (OSCs). In this review, various π-bridge groups (thiophene, alkene, alkyne, arene and heterocycle) and the pertinent π-linkage effect will be systematically summarized. These results suggest that the in-depth study of the π-linkage effect is essential to deeply understanding the relationship between the molecular structure and property, thus improving PV performance.

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Section: Oligothiophene-linkagementioning

confidence: 99%

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

Yin

2016

Sci. China Mater.

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“…The other asymmetrical D-A or D-A-D types of chromophores such as cyano-substituted diphenylethene derivatives with AIE characteristics, vapochromic and mechanochromic properties have also been reported. [25][26][27] The compounds revealed a reversible conversion between the crystalline and amorphous forms by different processes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Hsu

Weng

2018

RSC Adv.

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Compounds consisting of unsubstituted, monofluoro and difluoro substituted benzothiadiazole bonded to two tetraphenylethenes were successfully prepared by palladium catalyzed Suzuki-Miyaura cross-coupling reaction of their corresponding co-monomers. All compounds exhibited aggregation-induced emission characteristics when the water fraction was higher than 60% in the THF/water mixtures. The emission maximum for the three compounds was blue-shifted when the water content reached 90% compared to that in THF solution. The intensity of emission maximum of difluorinated benzothiadiazole linked with two tetraphenylethenes was 2.5 times higher in 90% water compared to those in THF solution.Surprisingly, two liquid crystal phases with two distinct emission colors were observed only for the compound containing difluorinated benzothiadiazole bonded to two tetraphenylethene. All compounds showed remarkable solvatochromic properties in selected solvents with different polarities. The powder XRD results and mechanochromism of the compounds suggested that the solid state structures can change from one form to another by grinding, fuming or annealing processes.

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“…Cho et al [23] synthesized a fluorine-substituted benzothiadiazole-based small molecular donor 1, in which the electron-withdrawing unit mono-fluorinated benzothiadiazole core was linked with triphenylamine (TPA) groups through a -conjugated dithiophene bridge. The BHJ solar cells with this material as the donor and PC 71 BM as the acceptor exhibited a PCE of 2.95% and a high open-circuit voltage (V oc ) of 0.85 V.…”

Section: Donors With Triarylamine-based Electron-donating Unitmentioning

confidence: 99%

Recent progress of bulk heterojunction solar cells based on small-molecular donors

Huang

2013

Chin. Sci. Bull.

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Organic bulk heterojunction (BHJ) solar cells based on small molecular donors have received great attentions recently, because small molecules possess the merits of high purity, well-defined molecular structures, definite molecular weights and high charge carrier mobility. The highest power conversion efficiency (PCE) of BHJ solar cells based on small molecular donors and fullerene derivative acceptors has reached 7.38%. In this review, we will briefly summarize the development of small molecular donor based BHJ solar cells in the past two years. These results suggest that small molecular donors are promising candidates for high efficiency BHJ solar cells. Due to the environmental constraints and the predicatable exhaustion of fossil energy resources, it is one of the major challenges in the 21st century to find clean and renewable energy. Solar energy which has the potential to act as renewable and clean energy sources is believed one of the promising and long term alternatives to replace fossil energy in the future. Currently, solar cells based on silicon have been practically applied, however, the high cost hinders their wide applications. Comparing with the well-studied silicon solar cells, photovoltaic devices based on organic semiconductors have attracted great attentions recently because they can be fabricated on flexible substrate with large scale at low-cost [1,2]. In this review, we will mainly focus on the development of organic BHJ solar cells. Organic BHJ solar cells consist of electrodes (cathode and anode), donor and acceptor blended active layer and substrate. Based on the donor used into solar cells, they can be briefly divided into two classes, polymer donor solar cells and small molecular donor solar cells. Currently, the polymer donor solar cells have made great progress [3][4][5][6][7], and the highest power conversion efficiency (PCE) reported in literatures has been over 8% [8,9]. In spite of the high performance, there are disadvantages for polymer donors [10], for instance, the high molecular weight dispersity, the batch to batch reproducibility, and so on. On the other hand, small molecular donors do not have the drawbacks mentioned above. In contrast, they have high purity, well-defined molecular structures, definite molecular weights, as well as high charge carrier mobility [11]. As a result, small molecular donors have attracted more and more attentions for photovoltaic applications recently and the highest PCE of BHJ devices based on small molecular donors has reached 7.38% [12].Considering several reviews have summarized the application of small molecular donors in BHJ solar cells [13][14][15][16][17][18][19][20][21], in the present review, we will mainly focus on the development of small molecular donor BHJ solar cells in the past two years. The review will classify the donors based on their device fabrication technique. And the principle of organic solar cells which can be found in the previous reviews

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Facile Synthesis of Fluorine‐Substituted Benzothiadiazole‐Based Organic Semiconductors and Their Use in Solution‐Processed Small‐Molecule Organic Solar Cells

Cited by 65 publications

References 38 publications

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Recent progress of bulk heterojunction solar cells based on small-molecular donors

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