An object of the present invention is to provide an organic semiconductor composition, which makes it possible to obtain an organic semiconductor film having high mobility and being excellent in film uniformity and heat resistance, and a method for manufacturing an organic semiconductor element.

The organic semiconductor composition of the present invention contains an organic semiconductor as Component A and an organic solvent, which is represented by Formula B-1 and has a melting point of equal to or lower than 25° C. and a boiling point of equal to or higher than 150° C. and equal to or lower than 280° C., as Component B, in which an ionization potential of Component A is equal to or higher than 5.1 eV. In the formula, X represents O, S, S═O, O═S═O, or NR, Y.sub.1 to Y.sub.4 each independently represent NR.sub.1 or CR.sub.10R.sub.11, R, R.sub.1, R.sub.10, and R.sub.11 each independently represent a hydrogen atom or a substituent, and n represents 1 or 2.

##STR00001##

Disclosed herein is a novel method for preparing cyclophanes, comprising forming a disulfide cyclophane by contacting a linker moiety which includes two or more thiol groups, with a metal salt and an oxidant. The disulfide cyclophane is then desulfurized to form a thiacyclophane comprising thioether bridges. This thiacyclophane optionally may be further desulfurized to form an unsaturated hydrocarbon cyclophane, which can then be reduced to form a saturated hydrocarbon cyclophane. The various cyclophanes can be synthesized in a ring form, such as a dimer, trimer or tetramer etc., or they can be synthesized in a tetrahedral or larger structure. Also disclosed are novel cyclophanes formed by the disclosed method.

Disclosed herein is a novel method for preparing cyclophanes, comprising forming a disulfide cyclophane by contacting a linker moiety which includes two or more thiol groups, with a metal salt and an oxidant. The disulfide cyclophane is then desulfurized to form a thiacyclophane comprising thioether bridges. This thiacyclophane optionally may be further desulfurized to form an unsaturated hydrocarbon cyclophane, which can then be reduced to form a saturated hydrocarbon cyclophane. The various cyclophanes can be synthesized in a ring form, such as a dimer, trimer or tetramer etc., or they can be synthesized in a tetrahedral or larger structure. Also disclosed are novel cyclophanes formed by the disclosed method.

A method of synthesizing a fused heteroaromatic compound includes obtaining a first intermediate from a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, obtaining a second intermediate including a ring having a chalcogen element from the first intermediate, and obtaining a fused heteroaromatic compound by a cyclization reaction of the second intermediate.

A method of synthesizing a fused heteroaromatic compound includes obtaining a first intermediate from a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, obtaining a second intermediate including a ring having a chalcogen element from the first intermediate, and obtaining a fused heteroaromatic compound by a cyclization reaction of the second intermediate.

The present invention provides compounds of formula (1) wherein o is 1, 2 or 3, p is 0, 1 or 2, n is 0, 1 or 2, m is 0, 1 or 2, and A is a mono- or polycyclic ring system, which may contain at least one heteroatom, and an electronic device comprising the compounds as semiconducting material. ##STR00001##

The present invention provides compounds of formula (1) wherein o is 1, 2 or 3, p is 0, 1 or 2, n is 0, 1 or 2, m is 0, 1 or 2, and A is a mono- or polycyclic ring system, which may contain at least one heteroatom, and an electronic device comprising the compounds as semiconducting material. ##STR00001##

An object is to provide an organic semiconductor element having excellent carrier mobility and heat resistance of a semiconductor active layer, an organic semiconductor composition for obtaining this element, an organic semiconductor film, and a method of manufacturing an organic semiconductor element in which the composition is used, and another object is to provide a compound and an oligomer or a polymer that are suitably used in the organic semiconductor element, the organic semiconductor composition, the organic semiconductor film, and the method of manufacturing an organic semiconductor element.

The organic semiconductor element of the present invention includes a compound represented by Formula 1 below in a semiconductor active layer. In Formula 1, X represents a chalcogen atom, p and q each independently represent an integer of 0 to 2, and R.sup.1 and R.sup.2 each independently represent a halogen atom or a group represented by Formula W below.

##STR00001##

An object is to provide an organic semiconductor element having excellent carrier mobility and heat resistance of a semiconductor active layer, an organic semiconductor composition for obtaining this element, an organic semiconductor film, and a method of manufacturing an organic semiconductor element in which the composition is used, and another object is to provide a compound and an oligomer or a polymer that are suitably used in the organic semiconductor element, the organic semiconductor composition, the organic semiconductor film, and the method of manufacturing an organic semiconductor element.

The organic semiconductor element of the present invention includes a compound represented by Formula 1 below in a semiconductor active layer. In Formula 1, X represents a chalcogen atom, p and q each independently represent an integer of 0 to 2, and R.sup.1 and R.sup.2 each independently represent a halogen atom or a group represented by Formula W below.

##STR00001##

A fused polycyclic heteroaromatic compound represented by Chemical Formula 1, and an organic thin film, an organic thin film transistor, and an electronic device including the fused polycyclic heteroaromatic compound are provided. The fused polycyclic heteroaromatic compound may have a conjugation structure but reinforce planarity among adjacent rings and have further dense packing and thus much increase charge mobility.