有機メソメリー化合物の使用、有機半導体物質、及び、電子素子

Japanese Patent JP5465940

B2

Use of an organic mesomer compound (I) as an organic dopant for doping an organic semi conducting matrix material to the variation of the electric characteristics, where (I) is a quinone or its derivative and (I) under smaller or same evaporation conditions, exhibits a evaporability than tetrafluorotetracyanochinondimethane (F4TCNQ), where the molecular doping ratio of dopant to matrix molecule is 1:5-1:1000. Use of an organic mesomer compound (I) as an organic dopant for doping an organic semi conducting matrix material to the variation of the electric characteristics, where (I) is a quinone or its derivative and (I) under smaller or same evaporation conditions, exhibits a evaporability than tetrafluorotetracyanochinondimethane (F4TCNQ), where the molecular doping ratio of dopant to matrix molecule and/or monomer units of a polymer matrix molecule is 1:5-1:1000. Independent claims are also included for: (1) an organic semi conducting material comprising an organic matrix molecule and an organic dopant (I); (2) preparation of organic semi conducting material (comprising an organic matrix molecule and an organic dopant (I)), comprising evaporating the dopant from its precursor compound that releases the dopant during heating and/or irradiating; (3) electronic building element with an organic semi conducting material, which is endowed with an organic dopant for the change of the electronic characteristics of the semi conducting matrix material, where the doping takes place using at least one or more of (I); and (4) a dopant and doping of an organic semi conducting matrix material, where the dopant is a group of organic mesomer quinone or its derivative compounds of formula (1-9), and the dopant on same evaporation conditions, exhibits a smaller evaporability than (F4TCQ). In formula (1): R 1-R 4Cl, CN or (hetero)aryl (optionally substituted with CN, NO 2, CF 3, perfluoroalkyl, SO 3R and/or halo); and A, B1 : NC-CH 2-CN, NC-CF 3or N-Ctriple boundN. In formula (2):R 1-R 8= Cl, F, CN, perfluoroalkyl or (hetero)aryl (optionally substituted with CN, NO 2, NO, perfluoroalkyl, SO 3R and/or halo). In formula (3): R 1-R 6Cl, F, CN, NO 2, NO, perfluoroalkyl or (hetero)aryl (optionally substituted with CN, NO 2, perfluoroalkyl, SO 3R and/or halo); and A, B1 : NC-CH 2-CN, NC-CF 3or N-Ctriple boundN. In formula (4): R 1-R 8Cl, F, prefluoroalkyl, CN, NO 2, NO or (hetero)aryl (optionally substituted with CN, NO 2, perfluoroalkyl, SO 3R and/or halo); and A, B1 : NC-CH 2-CN, NC-CF 3or N-Ctriple boundN. In formulae (5-7):R 1-R 6= Cl, F, CN, NO 2, NO, perfluoroalkyl or (hetero)aryl (optionally substituted with CN, NO 2, perfluoroalkyl, SO 3R and/or halo). In formula (8):R 1-R 12= Cl, F, CN, NO 2, NO, perfluoroalkyl or (hetero)aryl (optionally substituted with CN, NO 2, perfluoroalkyl, SO 3R and/or halo; where R 1, R 3, R 9und R 12is H and R 2, R 4, R 8, R 10or R 11is Cl, F, CN, NO 2, NO, perfluoroalkyl or (hetero)aryl (optionally substituted with CN, NO 2, perfluoroalkyl, SO 3R and/or halo). In formula (9): R 1-R 12Cl, F, CN, NO 2, NO, perfluoroalkyl or (hetero)aryl (optionally substituted with CN, NO 2, perfluoroalkyl, SO 3R and/or halo. [Image] [Image] [Image] [Image].

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Olaf, Cure
Horst, hartmann
Olaf, Tsaika
Martin, Pfeiffer
Yousheng, Zen

JP2009165062A

April 09, 2014

July 13, 2009

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Nova Red Actien Gezel Shaft

H01L51/30; H01L51/50; A61K31/53; C07C251/22; C07D339/08; C07F5/04; C09K11/06; H01L21/04; H01L21/24; H01L29/786; H01L29/861; H01L29/868; H01L31/00; H01L35/24; H01L51/00; H01L51/05; H01L51/40; H01L51/42; H01L51/54; H05B33/14

JP8250016A
JP2003264085A
JP4230997A

WO2003016599A1

日本化学会 編,化学総説No.42,1983,伝導性低次元物質の化学,日本,学会出版センター,1983年11月10日,p.59-65
J. Diekmann et al.,"Substituted Quinodimethans. VII. Substituent and Structural Effects in Cyano-Substituted Quinodimethans",Journal of Organic Chemistry,米国,American Chemical Society,1963年10月,Vol. 28,p.2719-2724

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