Polycyclic fused ring type .pi.-conjugated organic...

C - Chemistry – Metallurgy – 07 – F

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C07F 7/08 (2006.01) C09K 11/06 (2006.01) H05B 33/14 (2006.01) H05B 33/22 (2006.01)

Patent

CA 2544427

A polycyclic fused ring type n-conjugated organic material (VIIa, VIIb, VIIc, VIId) is obtained in the following manner. 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) HMe2SiC1). 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 NH4C1). In this way, the polycyclic fused ring type ri-conjugated organic material is obtained. The polycyclic fused ring type n-conjugated organic material, an intermediate therefor, a method for producing the polycyclic fused ring type n-conjugated organic material, and a method for producing the intermediate make it possible to provide a polycyclic fused ring type n-conjugated organic material having excellent light-emitting and charge-transporting properties.

L'invention concerne des matériaux organiques conjugués .PI. polycycliques à anneaux condensés (VIIa à VIId). Lesdits matériaux sont obtenus, tel que le montre le schéma suivant (1), à l'aide d'un procédé consistant à soumettre le matériau (I) de départ à une dimétallation avec une base organométallique, et à piéger le composé organométallique obtenu avec un réactif d'organosilicium (i: 1) n-BuLi ou t-BuLi; 2) HMe¿2?SiCl) afin d'obtenir l'intermédiaire (II), à mettre ensuite en réaction l'intermédiaire avec un agent de réduction métallique pour provoquer une réaction de cyclisation de réduction intramoléculaire afin d'obtenir un intermédiaire de dianion, puis à piéger l'intermédiaire de dianon à l'aide d'un agent électrophile (ii: 1) LiNaph, THF, rt, 5 min; 2) électrophile ou NH¿4?Cl). Les matériaux organiques conjugués .PI. polycycliques à anneaux condensés possèdent d'excellentes propriétés luminescentes et de transport de charge. [Formule chimique 1] Schéma 1

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