2,5-Bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione-Based Donor-Acceptor Alternating Copolymer Bearing Benzothieno[3,2-b] benzothiophene as an Organic Semiconductor and Its Application to Thin Film Transistors

Abstract

dione) was successfully synthesized via Horner-Emmons condensation. The polymer showed a low bandgap energy (E g = 1.56 eV) in a film state. The polymer also exhibits good solubility in common organic solvents and good self-film-forming properties. The semiconducting properties of the polymer synthesized herein were evaluated in organic thin film transistors (OTFTs). The polymer exhibits charge carrier mobilities as high as 3.0 × 10 −3 cm 2 V −1 s −1 (I on/off = 10 5 ) after thermal annealing at 200 • C for 10 min, which is three times higher than that of thin film transistor made of the pristine film.

Synthesis, Molecular Packing, and Electrical Properties of New Regioisomeric n-type Semiconducting Molecules with Modification of Alkyl Substituents Position

“…For the synthesis of the core, the DPP moiety was substituted with 2-ethylhexyl or 2-hexyldecyl side chains to modulate the solution processability and intermolecular packing interaction. The alkylated DPP was converted into DPP-CHO in 70% yield via formylation with lithium diisopropylamide followed by quenching with N,N -dimethylformamide (DMF) . Two different electron-withdrawing end-groups (INCNO1 and INCNO2) were synthesized from 4- n -octylbenzoic acid.…”

“…The alkylated DPP was converted into DPP-CHO in 70% yield via formylation with lithium diisopropylamide followed by quenching with N,N-dimethylformamide (DMF). 35 Two different electron-withdrawing endgroups (INCNO1 and INCNO2) were synthesized from 4-noctylbenzoic acid. First, the carboxylic acid functional group in 4-n-octylbenzoic acid was transformed into acyl chloride by reacting with oxalyl chloride in the presence of a catalytic amount of DMF.…”

Organic n-Channel Transistors Based on [1]Benzothieno[3,2-b]benzothiophene–Rylene Diimide Donor–Acceptor Conjugated Polymers

“…However, only low-molecular-weight polymers were generated, and the polymers did not function in OFET devices due to the highly intertwisted structures within the polymer backbone. Alternating donor–acceptor-type copolymers containing diketopyrrolopyrrole and BTBT showed a poor μ h (0.003 cm 2 V –1 s –1 ) . Meanwhile, random copolymerization with the incorporation of only a small amount of BTBT within the polymer main chain has been shown to increase μ h significantly (up to 2.47 cm 2 V –1 s –1 ). , However, an alternating copolymer containing BTBT as a donor unit for high-performance n-type semiconductors is hitherto unknown.…”