Japan Science and Technology Agency

Chisso Corporation

Shin-etsu Chemical Co., Ltd.

Nagoya University

Sumitomo Chemical Company, Limited

Kansai Technology Licensing Organization Co., Ltd.

Shigehiro Yamaguchi

Kohei Tamao

Manabu Uchida

Kenji Furukawa

Takenori Izumizawa

Caihong Xu

Chenguang Wang

Chizu Sekine

Hiroshi Yabu

Takaharu Nakano

Makoto Kitano

Satoshi Kobayashi

Yoshihiko Ito

Toshihiro Koike

Yuta Saito

Shohei Saito

Shunpei Nobusue

Kouhei Tamao

Aiko Naka

Aiko Fukazawa

Yoshiki Nakagawa

Masayasu Taki

Eriko Yamaguchi

Toshihiro Okamoto

A phosphole compound represented by the formula (wherein Arand Arare the same or different, and represent an optionally substituted aromatic hydrocarbon ring or an optionally substituted heteroaromatic ring; Arrepresents a divalent &#x3c0;-conjugated unit; Rrepresents an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group; Rand Rare the same or different, and represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group; and Z represents a reactive group) can provide a fluorescent dye capable of maintaining a high fluorescence quantum yield irrespective of solvent polarity, and providing an improved fluorescence quantum yield and light resistance even in environments containing large amounts of water.

Phosphole compound

Provided is a mechanochromic resin by which a stress applied to a material can be visualized in real time, and a mechanochromic luminescent material that is used in the synthesis of the mechanochromic resin. Stress can be visualized in real time by means of a mechanochromic luminescent material represented by formula (1) or formula (2) and a mechanochromic resin obtained by crosslinking the mechanochromic luminescent material. [Chemical formula 1] (In the formula, Yand Yeach denote a substituent group that inhibits aggregation of the mechanochromic luminescent material represented by formula (1), and Yand Ymay be same as or different from each other. Zand Zeach denote a polymerizable group, and may be same as or different from each other.) [Chemical formula 2] (In the formula, Yand Yeach denote a substituent group that inhibits aggregation of the mechanochromic luminescent material represented by formula (2), and Yand Ymay be same as or different from each other. Zand Zeach denote a polymerizable group, and may be same as or different from each other). 

Mechanochromic luminescent material, mechanochromic resin obtained by crosslinking mechanochromic luminescent material, method for producing mechanochromic luminescent material, and method for producing mechanochromic

The following formula is an example of a phosphole compound of the present invention. The phosphole compound of the present invention has the characteristic of maintaining a high fluorescence quantum yield in a wide range of solvents from low-polarity solvents to high-polarity solvents, as well as the characteristic in which the fluorescence wavelength shifts to the longer wavelength side as the polarity of the solvent increases. Because of these characteristics, the phosphole compound of the present invention is expected to be used, for example, for quantitatively determining the polarity in the environment therearound by using the absorption wavelength and fluorescence wavelength thereof, or used as a new fluorescent probe dye or a highly efficient luminescent material in organic electronic devices. 

Phosphole compound and fluorescent dye containing the same

A diacetylene derivative was used as a starting material, and was subjected to dilithiation using an organolithium reagent. The resulting product was allowed to react with an excessive amount of chalcogen. Accordingly, an intramolecular cyclization reaction proceeded simultaneously with formation of skeletons of three rings. As a result, a chalcogen-containing fused polycyclic organic material was found to be obtained which has the three rings and a dichalcogenid bond. Further, by subjecting the resulting compound to a dechalcogenation reaction, a heteroacene was found to be obtained in a satisfactory yield. These synthetic techniques have made it possible to synthesize a series of highly planar chalcogen-containing &#x3c0;-electron system materials. Therefore, it is possible to provide (i) a chalcogen-containing fused polycyclic organic material capable of exhibiting excellent charge-transporting properties and (ii) a method for producing the material.

Chalcogen-containing fused polycyclic organic material and method for producing same

A polycyclic fused ring type &#x3c0;-conjugated organic material (VIIa, VIIb, VIIc, VIId) is obtained in the following manner. That is, as shown in Scheme 1 below, a starting material (I) is dimetalated with an organometallic base. The starting material (I) thus dimetalated is trapped with an organosilicon reagent (i: (1) n-BuLi or t-BuLi; (2) HMeSiCl). As a result, an intermediate is obtained. Thereafter, the intermediate is allowed to react with a metal reductant. This causes an intramolecular reductive cyclization reaction to proceed. As a result, a dianion intermediate is produced. The dianion intermediate is trapped with an electrophile (ii: (1) LiNaph, THF, rt, 5 min; (2) electrophile or NHCl) In this way, the polycyclic fused ring type &#x3c0;-conjugated organic material is obtained. The polycyclic fused ring type &#x3c0;-conjugated organic material, an intermediate therefor, a method for producing the polycyclic fused ring type &#x3c0;-conjugated organic material, and a method for producing the intermediate make it possible to provide a polycyclic fused ring type &#x3c0;-conjugated organic material having excellent light-emitting and charge-transporting properties.

Polycyclic fused ring type &#x3c0;-conjugated organic material, intermediate therefor, process for producing polycyclic fused ring type &#x3c0;-conjugated organic material, and process for producing intermediate of polycyclic fused ring type &#x3c0;-conjugated organic material

The invention provides condensed polycyclic &#x3c0;-conjugated organic materials and manufacturing methods for the materials. A metal reducing agent is reacted with a straight-chain, triple bond-containing hydrocarbon (aryl acetylene compound, phenyl acetylene compound), the hydrocarbon being a benzene ring with an organic silicon as a substituent, so as to allow an intramolecular reductive cyclization reaction to proceed between the silicon and the triple-bond carbon. The reaction produces condensed polycyclic &#x3c0;-conjugated organic materials of the invention. The invention provides light-emitting materials applicable for organic electroluminescent devices, condensed polycyclic &#x3c0;-conjugated organic materials applicable for charge transport materials, their intermediate products, and a manufacture method for condensed polycyclic &#x3c0;-conjugated organic materials.

Condensed polycyclic &#x3c0;-conjugated organic material, intermediate product therefor, and method of manufacturing condensed polycyclic &#x3c0;-conjugated organic material

A polymer characterized by comprising repeating units represented by the following formula (1) and having a number-average molecular weight, in terms of polystyrene, of 10to 10. (In the formula, Rrepresents hydrogen, alkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, arylalkoxy, arylalkylthio, arylalkenyl, arylalkynyl, amino, substituted amino, silyl, substituted silyl, silyloxy, substituted silyloxy, monovalent heterocyclic group, or halogeno; and rings D and E each represents an optionally substituted aromatic ring.)

Polymer and polymeric luminescent element comprising the same

Organic electroluminescent device

An electroluminescence element (EL) obtained by using a silacyclopentadiene derivation expressed by the general formula (I) and the derivative are provided. ##STR1## (wherein X and Y are independently hydrocarbon radicals with from 1 to 6 atoms and R.sub.1 to R.sub.4 are hydrogen, halogens, alkyl radicals with from 1 to 6 carbon atoms, or a condensed (un)substituted ring if being adjacent).

Silacyclopentadiene derivatives and an organic electroluminescent

The present invention provides a silacyclopentadiene derivative represented by the following Formula (1): ##STR1## wherein X.sub.1 and Y.sub.1 represent independently a halogen atom, an amino group, a hydroxyl group, or an amino group or a hydroxyl group each having a substituent; R.sub.1 to R.sub.4 represent independently a hydrogen atom, a halogen atom, an alkyl group, an amino group, a silyl group, an aryl group, a cyano group, or the respective groups describe above each having a substituent; out of the groups represented by R.sub.1 to R.sub.4, those adjacent may be combined with each other to form rings; when R.sub.1 and R.sub.4 are phenyl groups or when combined are R.sub.1 with R.sub.2 and R.sub.3 with R.sub.4 respectively to form benzene rings, X.sub.1 and Y.sub.1 are not a chlorine atom or a hydroxyl group; and when R.sub.1 and R.sub.4 are methyl groups, X.sub.1 and Y.sub.1 are not bromine atoms.

Silacyclopentadiene derivative

An electroluminescence element (EL) obtained by using a silacyclopentadiene. derivation expressed by the general formula (I) and the derivative are provided. ##STR1## (wherein X and Y are independently hydrocarbon radicals with from 1 to 6 atoms and R.sub.1 to R.sub.4 are hydrogen, halogens, alkyl radicals with from 1 to 6 carbon atoms, or a condensed (un)substituted ring if being adjacent).

2,5-Reactive substituent group-containing siloles of the following general formula are provided ##STR1## wherein R.sup.1 to R.sup.4 may be the same or different and independently represent a monovalent hydrocarbon group having from 1 to 12 carbon atoms or a hydrogen atom, and R.sup.5 and R.sup.6 may be the same or different and independently represent a group selected from monovalent hydrocarbon-substituted sulfur, selenium, silicon, germanium, tin and phosphorus, or a halogen atom. Polycondensates of the siloles and processes for preparing the siloles and polycondensates are described.

2,5-reactive substituent group-containing siloles, silole

A thiophene-silole copolymer represented by the formula below and its method of manufacture are disclosed; ##STR1## wherein, R is a monofunctional hydrocarbon group having 1 to 20 carbon atoms or hydrogen, A and B are alkyl groups, aromatic groups, alkenyl groups, or represent an aliphatic group forming a ring wherein A is bonded to B, m and p are integers no less than 1, n is a natural number which can be 0, X is a hydrogen or halogen atom, and Y is a hydrogen atom, halogen atom or thiophene.

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Nagoya, Japan

Shigehiro Yamaguchi