DPP-based small molecule, non-fullerene acceptors for “channel II” charge generation in OPVs and their improved performance in ternary cells

Kim, Y.; Song, Chang Eun; Ko, Eunji; Kim, D.; Moon, Sang Jin; Lim, Eunhee

doi:10.1039/c4ra12184h

Cited by 32 publications

(17 citation statements)

References 66 publications

(63 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All reagents purchased commercially were used without further purification, except for toluene and tetrahydrofuran (THF) used as solvents, which were dried over sodium/benzophenone. 1,3‐Di(2′‐bromothien‐5′‐yl)‐5‐(2‐ethylhexyl)thieno[3,4‐ c ]pyrrole‐4,6‐dione ( 1 ) and 3,6‐bis‐(5‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxabrolan‐2‐yl)thiophen‐2‐yl))‐ N , N ′‐bis((2‐ethylhexy)‐1,4‐dioxopyrrolo[3,4‐ c ]pyrrole ( 2 ) were prepared according to procedures in the literature.…”

Section: Methodsmentioning

confidence: 99%

TPD‐ and DPP‐based Small Molecule Donors Containing Pyridine End Groups for Organic Photovoltaic Cells

Kim

Song

Lee

et al. 2016

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

We synthesized two new thieno [3,4-c]pyrrole-4,6-dione (TPD)-and diketopyrrolopyrrole (DPP)-based small molecules having pyridine end groups, TPDTPy and DPPTPy, using the Stille and Suzuki coupling reactions, respectively. The optical, electrochemical, and photovoltaic properties of these small molecules depended on the introduced electron-accepting units of TPD and DPP. DPPTPy exhibited a relatively low-energy bandgap (E g ) of 1.82 eV compared to TPDTPy (2.22 eV) because of the stronger electron-withdrawing ability of DPP compared to TPD. Organic photovoltaic cells with the inverted ITO/ZnO/small molecule:(6,6)-phenyl-C 71 -butyric acid methyl ester/MoO 3 /Ag structure were fabricated. The DPPTPy-based device showed a relatively high power conversion efficiency of 0.62% compared to TPDTPy (0.16%), mainly because of the red-shifted UV absorption, lower E g , and the higher short-circuit current of DPPTPy.

show abstract

Section: Methodsmentioning

confidence: 99%

TPD‐ and DPP‐based Small Molecule Donors Containing Pyridine End Groups for Organic Photovoltaic Cells

Kim

Song

Lee

et al. 2016

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

show abstract

“…Lin et al synthesized three diketopyrrolopyrrole(DPP)‐thiophene‐based oligomers, p ‐, m ‐, and o ‐DPP‐PhCNs, which, when paired with a P3HT donor, showed different photovoltaic performance owing to their distinct physical properties. To acquire the synergistic effect from high LUMO energy level of o ‐DPP‐PhCN and strong light absorption of p ‐DPP‐PhCN, both two acceptors were combined in a ternary system with P3HT.…”

Section: Different Types Of Ternary Systems Based On Non‐fullerene Acmentioning

confidence: 99%

Advances in Non‐Fullerene Acceptor Based Ternary Organic Solar Cells

2017

View full text Add to dashboard Cite

Ternary blend organic solar cells integrating multiple donor or acceptor materials in one photoactive layer have emerged as a promising strategy to simultaneously improve all device parameters compared with traditional binary solar cells. Recently, a large number of high‐performance non‐fullerene acceptor materials have been developed. Their preeminent advantages, such as strong light absorption ability and the tunability of optoelectronic properties, make them a compelling choice for fabricating ternary organic solar cells. Thus far, the state‐of‐the‐art efficiency of ternary blend system containing non‐fullerene acceptor has reached over 12%, and shows great potential in further improving the photovoltaic performance of the organic solar cells. In this review, we first describe the possible operation mechanisms in ternary systems and then primarily summarize the major achievements in different types of ternary systems based on non‐fullerene acceptors over the past few years. In the end, we conclude with the summary and prospects of non‐fullerene acceptor based organic ternary solar cells.

show abstract

“…In order to combine them with low bandgap donors, acceptors should be designed to have low‐lying LUMO energy levels with sufficient LUMO offset between donor and acceptor. The conventional way to induce low energy level is to utilize electron‐withdrawing groups such as cyano groups on the molecular backbone. For example, by replacing the thio group of rhodanine (RH) with a dicyanomethylene group of 2‐(1,1‐dicyanomethylene)rhodanine (CNRH), a small molecule donor based on oligothiophene showed relatively lower‐lying molecular orbital energy levels, narrower bandgap, and stronger electron‐withdrawing property …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of a 2‐(1,1‐Dicyanomethylene) rhodanine‐based Nonfullerene Acceptor for OPVs

Koh

Lim

2018

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

We synthesized an A–π–D–π–A‐type nonfullerene small molecule acceptor (Flu‐CNRH) based on fluorene and 2‐(1,1‐dicyanomethylene)rhodanine (CNRH) by a Knoevenagel condensation of the diformyl compound (Flu‐T‐CHO) and CNRH for the use as acceptors in organic photovoltaic cells (OPVs). Introduction of CNRH end groups effectively lowered the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels of the acceptor compared to those of the corresponding rhodanine‐based acceptor (Flu‐RH). The HOMO and LUMO levels of Flu‐CNRH are −5.71 and −3.60 eV, respectively. For comparison, Flu‐RH has HOMO and LUMO energy levels of −5.58 and −3.53 eV, respectively. This lowered LUMO energy level enables Flu‐CNRH to be combined with low bandgap polymer donors PTB7 and PTB7‐Th by providing proper LUMO offsets between donor and acceptor. OPV cells were fabricated with the device configuration of ITO/PEDOT:PSS/active layer/LiF/Al. The best power conversion efficiency of 1.47% was obtained in the P3HT:Flu‐CNRH devices at a D:A ratio of 1:1.5 and with annealing at 140°C. Moreover, Flu‐CNRH showed compatibility with low bandgap polymer donor PTB7 (1.22%) with external quantum efficiency response at a longer wavelength region up to 750 nm, while Flu‐RH had no photovoltaic behavior with PTB7 and PTB7‐Th.

show abstract

DPP-based small molecule, non-fullerene acceptors for “channel II” charge generation in OPVs and their improved performance in ternary cells

Abstract: Three diketopyrrolopyrrole-thiophene-based small molecules were synthesized substituting electron-withdrawing cyanide group in different positions and introduced as acceptors in organic photovoltaic cells.

Cited by 32 publications

References 66 publications

TPD‐ and DPP‐based Small Molecule Donors Containing Pyridine End Groups for Organic Photovoltaic Cells

TPD‐ and DPP‐based Small Molecule Donors Containing Pyridine End Groups for Organic Photovoltaic Cells

Advances in Non‐Fullerene Acceptor Based Ternary Organic Solar Cells

Synthesis and Characterization of a 2‐(1,1‐Dicyanomethylene) rhodanine‐based Nonfullerene Acceptor for OPVs

Contact Info

Product

Resources

About