Sumitomo Chemical Company, Limited

Osaka University

Daikin Industries, Ltd.

Ishihara Sangyo Kaisha, Ltd.

Yutaka Ie

Yoshio Aso

Masato Ueda

Kenji Adachi

Takabumi Nagai

Yoshikazu Umemoto

Makoto Karakawa

Takuji Seo

Taichi Moriyama

Masashi Ueta

Masashi Nitani

Makoto Okabe

Shreyam Chatterjee

Syun Kudo

Provided are a compound having an excellent semiconductor property and a method for producing the compound, an intermediate of the compound and a method for producing the intermediate, and an organic semiconductor material and an organic semiconductor device each obtained with use of the organic semiconductor material. A compound represented by general formula (2):

Compound, production method therefor, and organic semiconductor material obtained using said compound

An object of the present invention is to provide a novel fullerene derivative usable in n-type semiconductor materials for organic thin-film solar cells and the like. The object is achieved by a fullerene derivative represented by formula (1) wherein Rrepresents aryl optionally substituted with at least one substituent, Rrepresents an organic group, Rrepresents an organic group, with the proviso that at least one of Rand Ris alkyl optionally substituted with at least one substituent or alkyl ether optionally substituted with at least one substituent, Rrepresents hydrogen or an organic group, and a ring A represents a fullerene ring.

Fullerene derivative and n-type semiconductor material

In order to provide a naphthobischalcogenadiazole derivative that can be used as an intermediate for producing a naphthobischalcogenadiazole compound into which a fluorine atom has been introduced, the naphthobischalcogenadiazole derivative in accordance with an aspect of the present invention is represented by a formula (I): 

Naphthobischalcogenadiazole derivative and production method therefor

The present invention is a material having excellent performance as an n-type semiconductor material, in particular for organic thin-film solar cells. The present invention provides an n-type semiconductor consisting of a fullerene derivative having a purity of 99% or more, the fullerene derivative being represented by formula (1): 

Fullerene derivative and N-type semiconductor material

Nitrogen-containing fused ring compound having at least one structural unit selected from the group consisting of a structural unit represented by the formula (1-1) and a structural unit represented by the formula (1-2).

Nitrogen-containing fused ring compound, nitrogen-containing fused ring polymer, organic thin film, and organic thin film element

It is an object of the present invention to provide a nitrogen-containing condensed ring compound, which can be used as an organic n-type semiconductor having an excellent electron transport property and which is also excellent in terms of solubility in an organic solvent. The nitrogen-containing condensed ring compound of the present invention has a structural unit represented by the following formula (1-1) or formula (1-2):  wherein Arrepresents an aromatic ring; one of Yand Yrepresents a single bond, and the other represents &#x2014;C(R)(R)&#x2014; or &#x2014;C(&#x2550;X)&#x2014;; one of Yand Yrepresents a single bond, and) the other represents &#x2014;C(R)(R)&#x2014; or &#x2014;C(&#x2550;X)&#x2014;, and one of Yto Yrepresents &#x2014;C(R)(R)&#x2014; or &#x2014;C(R)(R)&#x2014;; at least one of Wand Wrepresents &#x2014;N&#x2550;; and Zand Zeach represent any one of the groups represented by the formula (i) to the formula (ix).

Nitrogen-containing condensed ring compound, nitrogen-containing condensed ring polymer, organic thin film, and organic thin film element

According to the first invention group there are provided conjugated compounds having two or more groups represented by the following formula (I) or the following formula (II): wherein one of Ar and Ar' represents a C6 or greater divalent aromatic hydrocarbon group and the other represents a C4 or greater divalent heterocyclic group, wherein the groups each may have a substituent, with the proviso that the groups as a whole contain no fluorine atoms, Rand Reach independently represent a hydrogen atom, a halogen atom or a monovalent group, and Ar&#x2033; represents a trivalent aromatic hydrocarbon or trivalent heterocyclic group; when the conjugated compound has two or more groups represented by formula (I), the portion excluding these groups contain no fluorine atoms. According to the second group of the present invention there are provided nitrogen-containing fused-ring compounds represented by the following formula (&#x3b1;-I): in formula (&#x3b1;-I), Rand Reach independently represent a hydrogen atom, a halogen atom or an optionally substituted monovalent group, and Zand Zeach independently represent any one of the groups represented by the following formulas (&#x3b1;-i)-(&#x3b1;-ix); wherein R, R, Rand Reach independently represent a hydrogen atom, a halogen atom or a monovalent group, and Rand Rmay bond together to form a ring, the left side and the right side of the group represented by formula (&#x3b1;-viii) may be interchanged.

Conjugated compound, nitrogenated condensed-ring compound, nitrogenated condensed-ring polymer, organic thin film, and organic thin film element

A condensation compound of a fluorinated cyclopentane ring and an aromatic ring, which is useful, for example, for electronic materials, and a process for producing the same are provided. For instance, according to Scheme 1 below, a compound (68) containing a condensed structure formed of a hexafluorocyclopentane ring and an aromatic ring is synthesized. The aromatic ring is not limited to a thiophene ring but can be any ring and any substituent can be used. Thus a compound containing a condensed ring structure formed of a hexafluorocyclopentane ring and an aromatic ring, particularly, for instance, a thiophene ring, which was impossible to produce conventionally, can be produced easily with high yield. The compound of the present invention is particularly suitable to be applied to, for example, electronic materials or semiconductors. When it is polymerized and thereby the &#x3c0;-electronic conjugation is extended, it also is expected to be applied to, for example, n-type organic semiconductors and molecular wires that are indispensable for developing molecular electronics elements. 

Condensation compound between fluorinated cyclopentane ring and aromatic ring, and process for producing the same

Fluorinated compounds of the invention are represented by the following general formula (I): 

Fluorine-containing compound and method for producing same, fluorine-containing polymer, organic thin film, and organic thin film device

A polymer having a repeating unit represented by the following general formula (I) and a ferrocene-based reduction potential of &#x2212;1.5 to &#x2212;0.5 V as measured by a cyclic voltammetry method 

Polymer having unit obtained by condensation of difluorocyclopentanedione ring and aromatic ring, organic thin film using the same, and organic thin film device

A polymer comprising a repeating unit represented by the following general formula (I). (In the formula, Arrepresents a divalent aromatic hydrocarbon or divalent heterocyclic group, X, Y, Xand Yeach independently represent a fluorine atom or alkylthio group, and Xand Yand Xand Ymay together form a carbonyl or thiocarbonyl group with their bonding carbon atom.) 

Polymer comprising unit comprising fluorocyclopentane ring fused with aromatic ring and organic thin film and organic thin film element both comprising the same

Growing community of inventors

Osaka, Japan

Yutaka Ie