Comparative study of soluble naphthalene diimide derivatives bearing long alkyl chains as n-type organic thin-film transistor materials

Abstract

Abstract:In this study, several naphthalene tetracarboxylic acid diimide (NTCDI) 2 derivatives substituted at the N and N' positions with long normal alkyl chains of different lengths were evaluated as soluble n-type organic thin-film transistor (TFT) materials. NTCDI derivatives with diundecyl (NTCDI-C11), didodecyl (NTCDI-C12), and ditridecyl (NTCDI-C13) exhibited acceptable solubility in chloroform, and their TFTs showed typical n-type TFT performance with relatively high field effect electron mobility (~0.2 cm 2 /Vs) after annealing at a workable temperature of 150 °C. Although NTCDI with dioctyl (NTCDI-C8) showed good solubility in chloroform, the TFT performance of this material was highly inferior to that of NTCDI-C11, NTCDI-C12, or NTCDI-C13. We could not anneal NTCDI-C8 thin films at workable temperatures in vacuo because of sublimation of the material from the substrates. In contrast, NTCDI with dipentadecyl (NTCDI-C15) and dioctadecyl (NTCDI-C18) exhibited both poor solubility for chloroform and poor TFT performance. In short, these compounds are not suitable as soluble n-type organic TFT materials.

Nonfullerene Electron Transporting Material Based on Naphthalene Diimide Small Molecule for Highly Stable Perovskite Solar Cells with Efficiency Exceeding 20%

“…In previously reported NDI derivatives, introducing N ‐substituted flexible alkyl groups resulted in high solubility in common organic solvents. However, the derivatives showed various mesophasic phase transitions at relatively low temperatures (in some cases, about 100 °C) due to high conformational freedom and flexibility of alkyl groups . Electronic devices, including PSCs, may exhibit decreased long‐term temporal stability due to low‐temperature mesophasic phase transitions in the ETM.…”

Illumination and dipole layer effects on the density of state distribution in n-type organic thin film phototransistors based on naphthalene bis-benzimidazole: Experiment and modeling

“…3 can be simplified as: (4) where the final expression of the threshold voltage under illumination, V th,ill , is [35], illumination, which presumably reflects the increase in the deep-level trapped charge density at the gate insulator/organic semiconductor interface [36][37][38]. The deep-level trapped charge density can be determined according to the following equation [26,39]: (6) where C i is the insulator capacitance per unit area and q is the electronic charge. The obtained values of were given in Table 1.…”

“…Organic semiconductors (OSCs) are of great interest as active materials for many technology devices due to many fundamental advantages, including lightweight, low-cost processing, large area capability, structural flexibility and low-temperature process [1][2][3]. The efforts in the research and development of OSCs lead to developing industrial electronic and optoelectronic organic devices such as organic light-emitting diodes (LEDs), organic photovoltaic cells (OPVs), organic thin film transistors (OTFTs), organic memories and organic sensors [4][5][6][7][8][9][10].…”

Studies of photosensitivity and photo-induced negative differential resistance (NDR) of TIPS-pentacene-poly(3-hexyl)thiophene blend organic thin film transistor

“…Organic semiconductors have gained considerable attention due to their potential applications in organic light-emitting diodes (OLEDs) [1][2][3][4], organic photovoltaics (OPVs) [5][6][7][8] and organic thin film transistors (OTFTs) [9,10]. In fabrication of the organic thin film transistors (OTFTs), conjugated polymers, oligomers, or small molecules are generally used as organic active layer.…”

“…Moreover, soluble organic semiconductors enable simple processing techniques, such as spin coating and drop-casting [11], and printing processes which are ideally suited to the realization of low-cost, flexible [17]. Among solution processed OSCs, thiophene and pentacene derivatives exhibit good TFT performance [10]. Sheraw et al [18] reported that with a simple modification of 6,13-pentacenequinone, 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS-pentacene) can be synthesized.…”