Haptacyclic Carbazole-Based Ladder-Type Nonfullerene Acceptor with Side-Chain Optimization for Efficient Organic Photovoltaics

Yu Tang Hsiao, Chia Hua Li, Shao Ling Chang, Soowon Heo, Keisuke Tajima, Yen-Ju Cheng*, Chain-Shu Hsu

*Corresponding author for this work

Research output: Contribution to journalArticle

28 Scopus citations

Abstract

In this research, a haptacyclic carbazole-based dithienocyclopentacarbazole (DTCC) ladder-type structure was formylated to couple with two 1,1-dicyanomethylene-3-indanone (IC) moieties, forming a new nonfullerene acceptor DTCCIC-C17 using a bulky branched 1-octylnonayl side chain at the nitrogen of the embedded carbazole and four 4-octylphenyl groups at the sp 3 -carbon bridges. The rigid and coplanar main-chain backbone of the DTCC core provides a broad light-absorbing window and a higher-lying LUMO energy level, whereas the bulky flanked side chains reduce intermolecular interactions, making DTCCIC-C17 amorphous with excellent solution processability. The DTCCIC-C17 as an acceptor is combined with a medium band gap polymer poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1,2-b:4,5-b′]dithiophene))-alt-(5,5-(1′,3′-di-2-thienyl-5′,7′-bis(2-ethylhexyl)benzo[1′,2′-c:4′,5′-c′]dithiophene-4,8-dione))] (PBDB-T) as the donor in the active layer to obtain suitable highest occupied molecular orbital/lowest unoccupied molecular orbital energy alignments and complimentary absorption. The devices with an inverted configuration (ITO/ZnO/active layer/MoO 3 /Ag) without using an aqueous poly(3,4-ethylenedioxythiophene) polystyrene sulfonate layer were fabricated for better device stability. When the diiodooctane-treated PBDB-T:DTCCIC-C17 active layer was thermally annealed at 50 °C for 10 min, the device achieved the highest efficiency of 9.48% with a high V oc of 0.98 V, a J sc of 14.27 mA cm -2 , and an FF of 0.68.

Original languageEnglish
Pages (from-to)42035-42042
Number of pages8
JournalACS Applied Materials and Interfaces
Volume9
Issue number48
DOIs
StatePublished - 6 Dec 2017

Keywords

  • bulk heterojunction
  • carbazole
  • ladder-type
  • nonfullerene
  • organic photovoltaics

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