Thermally evaporable 5,10-dihydroindeno[2,1-a]indenes form efficient interfacial layers in organic solar cells

Wei, Yi; Liu, Peijun; Lee, Ren-Hao; Chen, Chih‐Ping

doi:10.1039/c4ra11696h

Cited by 14 publications

(9 citation statements)

References 68 publications

(101 reference statements)

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“…P‐type organic small molecules have also been used to modify the anode in OSCs due to their good hole mobility and tunable energy level . Fichou and co‐workers reported a p‐type semiconductor 4,4′‐bis(diphenyl‐2,6‐thiapyrannylidene) (DITPY‐Ph 4 , Scheme ) for use as an AIM in P3HT:PC 61 BM devices .…”

Section: Small Molecule Anode Interlayermentioning

confidence: 99%

Small Molecule Interlayers in Organic Solar Cells

Zhang

Usman

2018

Advanced Energy Materials

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This review provides an up‐to‐date review about the small molecule interlayers (SMIs) in organic solar cells (OSCs). Compared to polymer interlayers, SMIs exhibit intrinsic advantages such as easy synthesis and purification, monodispersity, well‐defined chemical structure, and high batch‐to‐batch reproducibility. Recently, various SMIs have been reported with landmark efficiencies of over 10% in both conventional and inverted OSCs, exhibiting promising potential in commercial application. In this review, the authors summarize the progress of SMIs from a device fabrication point of view, paying particular attention to the material categories, molecular design, preparation process, and applicable device structure. In addition, the working mechanisms of different SMIs are also discussed, including the structure–property relationships and the corresponding impact on device performance. Finally, a brief outlook is provided that includes opportunities and challenges in this emerging area.

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Section: Small Molecule Anode Interlayermentioning

confidence: 99%

Small Molecule Interlayers in Organic Solar Cells

Zhang

Usman

2018

Advanced Energy Materials

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“…28 New solution-processable HTMs are still in demand and chemistry scientists have made great effort to explore new alternative materials. [29][30][31][32][33][34][35][36] Recently, we reported that PEDOT:SL as hole transporting material exhibited promising performance in polymer solar cells. 37 In order to study the effect of -OH and aggregation behaviour of lignosulfonate for the performance of PSCs, we choose LS and ALSs as starting materials in our previous manuscript 14 to study the effect in detail.…”

Section: Introductionmentioning

confidence: 99%

Effect of aggregation behavior and phenolic hydroxyl group content on the performance of lignosulfonate doped PEDOT as a hole extraction layer in polymer solar cells

et al. 2015

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†Electronic Supplementary Information (ESI) available: [the results including SEM images of various block-like self-assemblies from LS and ALS; DLS measurement of LS solution and ALS solution in H2O/EtOH (v/v, 1/3); Proposed schematic for the polymerization of EDOT in the presence of LS and ALS; UV absorption spectra of PEDOT:LS and PEDOT:ALS aqueous dispersion]. SeeUsing lignosulfonate (LS) and alkyl chain-coupled lignosulfonate-based polymer (ALS) as raw material, the aggregation behavior of LS and ALS was investigated, which all showed unique aggregation behavior to form block-like self-assembly for the first time. The aggregation behavior and mechanism of LS and ALS was investigated by SEM, TEM and DLS. The block-like aggregates prepared from ALS (micron size) were larger than that of LS (nano size). The unique aggregates were also further confirmed by XPS, meanwhile, SAXS was applied to explore the regular intrinsic characteristics of the blocklike aggregates. Inspired by the aggregation behavior of LS and ALS, the electron transfer properties of LS and ALS were also studied including electrochemical property and hole mobility measurement. The oxidation peaks at 1.2 V and 1.4 V were observed at the LS and ALS modified electrode, respectively. We studied hole transport property of LS and ALS with space-charge-limited current method (SCLC). The average hole mobilities of 2.95×10 -6 cm 2 V -1 s -1 and 3.18×10 -7 cm 2 V -1 s -1 were estimated for LS and ALS, respectively. The above results indicated that LS and ALS are potential water soluble polymeric p-type semiconductors, and the electron transfer property of LS is better than that of ALS. Based on the unique aggregation behavior and hole mobility above which will facilitate charge transport, water soluble PEDOT:LS and PEDOT:ALS were prepared and applied as hole extraction layer (HEL) in polymer solar cells. The PCE decreased with the decrease of phenolic hydroxyl group content (-OH), which suggested that -OH is important for the property of PCE. The application properties were consistent with the results of aggregation behavior and electron transfer properties. The power conversion efficiency (PCE) of 5.19% from PEDOT:LS-1:1 as HTL was achieved with device structure of ITO/HEL/PTB7:PC71BM/Al in our study. Our results showed the phenolic hydroxyl group content and conjugation structure of amorphous LS contribute its promising potential as dopant of semiconductors, such as PEDOT in organic electronics. Our result provides a novel perspective for the design of dopant for semiconductive polymer.All in one word, phenolic hydroxyl group of polymer will provide hole transport capability due to its oxidation during device orperation.

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“…For example, the reaction of the multisubstituted diene 3 a led to the formation of the tetraphenyl‐substituted 5,10‐dihydroindeno[2,1‐ a ]indene (DII) 4 a in 88 % yield at 80 °C, and was synthesized previously by multistep methods in low yields 18. 19 Similarly, the reaction of the multisubstituted diene 3 b , having electron‐donating p ‐tolyl groups, reacted at room temperature to give the corresponding product 4 b in 99 % yield.…”

Section: Methodsmentioning

confidence: 99%

Thermal Kinetic Parameters of Lead Azide and Lead Styphnate with Antistatic Additives

Liu

Jiang

Tong

et al. 2015

Propellants Explo Pyrotec

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1IntroductionIn the field of energetic materials, lead azide (LA)a nd lead styphnate (LS) are widely used as primary explosives. They both have goodm echanical and electrostatic sensitivities and are frequently adopted on pyrotechnics and ammunitions. However,a sh ighly insulatingm aterials, LA and LS have high staticp roperties. Especially LS easily accumulates static charge, even detonation with an energy sparka sl ow as 0.2-0.3mJ [ 1,2] has beeno bserved. According to statistics, about 10-20 %o ft he explosives blasting accidentsa re caused by electrostatic discharge [3].A tp resent, ag rowing number of studies are directed to improve their antistatic properties [4][5][6].S pear [7] added conductive compounds such as graphite to LS, which significantly reducedthe electrostatic spark sensitivity.Z hou [8] added lauryl dimethylamine betaine (BS-12) to LS and LA, whicha lso reducedt he electrostatic sensitivity.M eanwhile, Li [9] investigated the electrostatic sensitivity of LS to which graphenen anoplatelets (GNP) were added.In their work, merely the electrostatic sensitivity was investigated;t hey did not further study the influence of the antistatica dditives on the reactionk inetics of the primary explosive. Studies on the thermal kinetic parameters of the antistaticp rimary explosivec an determine not only the compatibility of primary explosive but also the thermal decomposition process of primary explosive,a nd allow to determine whether the antistatic additives affectt he explosive property.In this paper,t he thermal decompositionp rocesses of LA and LS, which are added to antistatic additives, are presented by real-time, on-line, continuous, and direct dynamic vacuum stability test (DVST) [10][11][12].T he curves of pressure changingo ver time are obtained, and then thermal kinetic parameters are calculated,t he influence of antistatica dditives on primary explosive is analyzed. 2R esults and Discussion Thermal Decomposition Mechanism of Antistatic Primary Explosive by DVSTThis paper chooses the best of the foura ntistatic modified explosive LA/poval (PVA), LA/dextrin (DEX), LS/carboxymethyl cellulose (CMC), LS/dextrin( DEX) to compare with LA and LS without antistatic additives takingD VST experiments. Four samples (LA/DEX, LA/PVA, LS/CMC,L S/DEX) are filled into four tubes under room temperature, the initial pressure is less than 0.1 kPa. Te mperature is raised to 80, 90, 100, 110, and 120 8C, respectively,a fterwardsv acuum stabilityt est is carried on under ac onstant temperature for 48 h. DVST records the pressure of gas generated by thermal decompositionc hanging over time,t he curve (p-t)o f the standard pressure (p)c hangingw ith the heating time (t)i so btaineda fter standardizationp rogram processing by subtracting the initial pressure value. Ta king LA/DEX as an example (see Figure 1), the curve (p-t)o ft he standard pressure (p)i sg radually raised changing over time and the curves( p-t)o ft he other samples are similar to LA/DEX. The compatibility of antistatic additives with explosive is tes...

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Thermally evaporable 5,10-dihydroindeno[2,1-a]indenes form efficient interfacial layers in organic solar cells

Abstract: Several bis(diarylamino)dihydroindenoindene derivatives were synthesized for use as hole transporting materials (HTMs) in OPVs. An optimized device having the structure ITO/HTM/P3HT:PCBM/Ca/Al operated with a fill factor of 67.8%.

Cited by 14 publications

References 68 publications

Small Molecule Interlayers in Organic Solar Cells

Small Molecule Interlayers in Organic Solar Cells

Effect of aggregation behavior and phenolic hydroxyl group content on the performance of lignosulfonate doped PEDOT as a hole extraction layer in polymer solar cells

Thermal Kinetic Parameters of Lead Azide and Lead Styphnate with Antistatic Additives

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