Scalable Synthesis of Fused Thiophene-Diketopyrrolopyrrole Semiconducting Polymers Processed from Nonchlorinated Solvents into High Performance Thin Film Transistors

Abstract

The synthesis and characterization of a fused thiophene-diketopyrrolopyrrole based semiconducting polymer PTDPPTFT4 is presented. A number of synthetic challenges have been overcome in the development of a practical scalable synthesis. Characterization by Gel Permeation Chromatography (GPC) over a range of temperatures has revealed the tendency of this polymer to aggregate even at elevated temperatures and confirmed that the molecular weight values obtained are for nonaggregated material. This polymer meets a number of important requirements for potential industrial applications, such as scalable synthesis, solubility in industrially suitable solvents, and material stability and processability into stable high performance thin film transistor devices. Computational modeling has been used to help explain the structure property relationships contributing to the high performance. Grazing incidence X-ray of the thin films showed out of plane lamellar packing and in plane π−π stacking, both good indicators of a preferentially oriented thin film, desirable for high charge carrier mobility. Hole mobilities in excess of 2 cm 2 /V•s, on/off ratio of >10 6 , and threshold voltage <2 V have been achieved.

Synthesis and characterization of solution-processable diketopyrrolopyrrole (DPP) and tetrathienothiophene (TTA)-based small molecules for organic thin film transistors and organic photovoltaic cells

“…As shown in Fig. 1, carrier hole mobilities of up to 2 cm 2 V À1 s À1 and 0.94 cm 2 V À1 s À1 have been reported for the polymers PTDPPTFT4 [37] and PDBT-c-TT [38], respectively. In particular, TTA-DPP-based polymer (PTTDPS) [39,40] achieved a high PCE of 4.5%.…”

Diketopyrrolopyrrole-based conjugated polymers containing alkyl and aryl side-chains for bulk heterojunction solar cells

“…3,6-Di(thiophen-2-yl)pyrrolo [3,4-c]pyrrole-1,4(2H,5H)-dione (DPP) [20], 9-(bromomethyl)nonadecane [21], and 2,5-bis(trimethylstannyl)thieno [3,2-b]thiophene [22] were synthesized according to the literatures. All other chemicals were purchased from commercial sources and solvents were purified by distillation prior to use.…”

Ambipolar copolymer of dithienocoronenedi-imide and benzo(bis)thiadiazole with balanced hole and electron mobility

“…Compared to traditional semiconductors such as silicon, organic semiconductors have a lot of advantages in flexible devices, abundant kinds and low cost. Recently, significant progress has been made in the performance of solutionprocessed organic field-effect transistors (OFET), organic light-emitting diodes (OLED) and organic solar cells (OSC) [3,[5][6][7][8][9][10][11][12][13][14]. To obtain good performance of organic optoelectronic devices, balanced charge carrier transport are of great importance [2,10,[15][16][17].…”