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Polycyclic fused ring type π-conjugated organic material, intermediate therefor, process for producing polycyclic fused ring type π-conjugated organic material, and process for producing intermediate of polycyclic fused ring type π-conjugated organic material

外国特許コード F110005486
整理番号 K05604WO
掲載日 2011年9月6日
出願国 アメリカ合衆国
出願番号 57835204
公報番号 20090143605
公報番号 7973190
出願日 平成16年11月5日(2004.11.5)
公報発行日 平成21年6月4日(2009.6.4)
公報発行日 平成23年7月5日(2011.7.5)
国際出願番号 JP2004016433
国際公開番号 WO2005044826
国際出願日 平成16年11月5日(2004.11.5)
国際公開日 平成17年5月19日(2005.5.19)
優先権データ
  • 特願2003-378923 (2003.11.7) JP
  • 特願2004-224771 (2004.7.30) JP
  • 2004WO-JP16433 (2004.11.5) WO
発明の名称 (英語) Polycyclic fused ring type π-conjugated organic material, intermediate therefor, process for producing polycyclic fused ring type π-conjugated organic material, and process for producing intermediate of polycyclic fused ring type π-conjugated organic material
発明の概要(英語) (US7973190)
A polycyclic fused ring type &pgr;-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) HMe2SiCl).
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 NH4Cl) In this way, the polycyclic fused ring type &pgr;-conjugated organic material is obtained.
The polycyclic fused ring type &pgr;-conjugated organic material, an intermediate therefor, a method for producing the polycyclic fused ring type &pgr;-conjugated organic material, and a method for producing the intermediate make it possible to provide a polycyclic fused ring type &pgr;-conjugated organic material having excellent light-emitting and charge-transporting properties.
特許請求の範囲(英語) [claim1]
1. A polycyclic fused ring type pi -conjugated organic material having a structure represented by following formula (3):
where Ar3 is an aryl group, a substituted aryl group, a bivalent oligoarylene group, a bivalent substituted oligoarylene group, a monovalent heterocyclic group, a monovalent substituted heterocyclic group, a monovalent oligoheterocyclic group, or a monovalent substituted oligoheterocyclic group; R1 and R2 are independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an allyl group, an amio group, a substituted amino group, a silyl group, a substituted silyl group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, an alkylsulfonyloxy group, a monovalent heterocyclic group, or a halogen atom; R3 is a hydrogen group, an alkyl group, an alkylthio group, an aryl group, an arylthio group, an arylalkyl group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an allyl group, a hydroxyalkyl group, a hydroxymethyl group, a substituted hydroxymethyl group, a silyl group, a substituted silyl group, a stannyl group, a substituted stannyl group, magnesium halide, zinc halide, boronic acid, boronic ester, a boryl group, a monovalent heterocyclic group, or a halogen atom; R5 is a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an allyl group, an amio group, a substituted amino group, a silyl group, a substituted silyl group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, an alkylsulfonyloxy group, a substituted boryl group, a monovalent heterocyclic group, or a halogen atom; and o is an integer of 2.
[claim2]
2. A polycyclic fused ring type pi -conjugated organic material having a structure represented by following formula (4):
where R1 and R2 are independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an allyl group, an amio group, a substituted amino group, a silyl group, a substituted silyl group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, an alkylsulfonyloxy group, a monovalent heterocyclic group, or a halogen atom; R3 is a hydrogen group, an alkyl group, an alkylthio group, an aryl group, an arylthio group, an arylalkyl group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an allyl group, a hydroxyalkyl group, a hydroxymethyl group, a substituted hydroxymethyl group, a silyl group, a substituted silyl group, a stannyl group, a substituted stannyl group, magnesium halide, zinc halide, boronic acid, boronic ester, a boryl group, a monovalent heterocyclic group, or a halogen atom; R4 and R5 are independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an allyl group, an amio group, a substituted amino group, a silyl group, a substituted silyl group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, an alkylsulfonyloxy group, a substituted boryl group, a monovalent heterocyclic group, or a halogen atom; n is an integer of 0 to 5; and o is an integer of 2.
[claim3]
3. A polycyclic fused ring type pi -conjugated organic material having a structure represented by following formula (17):
where R1 and R2 are independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an allyl group, an amio group, a substituted amino group, a silyl group, a substituted silyl group, a silyloxy group, a substituted silyloxy group, an arylsulfonyloxy group, an alkylsulfonyloxy group, a monovalent heterocyclic group, or a halogen atom; R6 and R7 are either (i) independently a hydrogen atom, an alkyl group, an aryl group, a substituted aryl group, a monovalent heterocyclic group, a monovalent substituted heterocyclic group, an alkoxy group, an aryloxy group, an arylalkyl group, an arylalkoxy group, an arylalkenyl group, an arylalkynyl group, or an allyl group, or (ii) mutually a bivalent biaryl group; and R8 and R9 are either (a) independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a substituted aryl group, an arylalkyl group, an arylalkenyl group, an arylalkynyl group, an allyl group, a silyl group, a substituted silyl group, an acyl group, or a monovalent heterocyclic group, or (b) mutually a bivalent biaryl group.
  • 発明者/出願人(英語)
  • YAMAGUCHI SHIGEHIRO
  • XU CAIHONG
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
米国特許分類/主・副
  • C07F007/08C4B
  • C09K011/06
  • H05B033/14
  • M09K211/10D4N
参考情報 (研究プロジェクト等) PRESTO Synthesis and Control AREA
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