Soluble and Stable N‐Heteropentacenes with High Field‐Effect Mobility

Abstract

An exploratory study on a group of silylethynylated N‐heteropentacenes as soluble and stable organic semiconductors is presented. An interesting finding is that a silylethynylated N‐heteropentacene can function as a p‐type, n‐type, or ambipolar organic semiconductor depending on the structure of its π‐backbone. The tetraazapentacene derivative is one of the best performing n‐type organic semiconductors with an electron mobility of up to 3.3 cm2 V−1 s−1.

Electron Mobility Exceeding 10 cm2 V−1 s−1 and Band‐Like Charge Transport in Solution‐Processed n‐Channel Organic Thin‐Film Transistors

“…The n-type organic semiconductor studied here is 6,13-bis((triisopropylsilyl)ethynyl)-5,7,12,14-tetraazapentacene (TIPS-TAP) [15] as shown in Figure 1a. TIPS-TAP exhibited a field effect mobility of 2.57 ± 0.89 cm 2 V −1 s −1 in solutionprocessed OTFTs, where the high-k dielectric layer of AlO x / TiO y was modified with a SAM of 12-cyclohexyldodecyl-phosphonic acid (CDPA, as shown in Figure 1b) to achieve high molecular ordering and good wettability by common organic solvents simultaneously.…”

Trends in molecular design strategies for ambient stable n-channel organic field effect transistors

“…To improve the electron mobility, TIPS groups were introduced at the 6 and 13 positions of tetraazapentacene derivatives in analogy with high performance p-channel 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS pentacene). The positions of the N-atoms were varied from terminal (6b) to centre (6c) by Liang et al 262,263 This strongly influences the LUMO energy levels and charge carrier mobilities in 6b and 6c. The LUMO of 6b lies at À3.68 eV whereas it lowers to À4.01 eV in 6c.…”

Application of double-hybrid density functionals to charge transfer in N-substituted pentacenequinones

“…To further disentangle the role played by pyrazine rings, we have also calculated values for 6,13-pentacenequinone, indeed a major impurity in pentacene, to find the opposite behavior since h ·+ < e ·− , as found for pentacene too. It thus seems that the introduction of pyrazine rings confirms at a molecular scale the successful strategy followed before to have n-conducting molecules, 9 or even ambipolar behavior, 43 exhibiting π -stacking motifs.…”