Oxo carbon compound, pseudo-oxo-carbon compounds, and radialene compounds, and methods of these use

    公开(公告)号:JP5507057B2

    公开(公告)日:2014-05-28

    申请号:JP2008117345

    申请日:2008-04-28

    摘要: As organic doping agent for the doping of an organic semiconductive matrix material, as blocker layer, as charge injection layer or as organic semiconductor itself, an organic mesomeric compound, which is an oxocarbon, pseudooxocarbon or radialene compound, is used. As organic doping agent for the doping of an organic semiconductive matrix material, as blocker layer, as charge injection layer or as organic semiconductor itself, an organic mesomeric compound, which is an oxocarbon, pseudooxocarbon or radialene compound of formula (I), is used. n : 1-4; X 1-X 5C(CN) 2, (CF 3)C(CN), (NO 2)C(CN), C(halogen) 2, C(CF 3) 2, NCN, O, S, NR 1, groups of formulae (Ia)-(Iq), R 1-C(=X 4)-CH 2-C(=X 5)-R 2, R 1-C(=X 4)-CH 2-CN, Aryl-CH 2-Aryl, Aryl-CH 2-Y 1, Hetaryl-CH 2-Hetaryl, Hetaryl-CH 2-Y 1, R 1-C(=X 4)-CH 2-CF 3, ArO 2S-CH 2-CF 3, HetarylO 2S-CH 2-CF 3, HetarylO 2S-CH 2-CN, or ArO 2S-CH 2-CN; Y 1CN, NO 2, COR 1 or perhalogenated alkyl; aryl or Ar : optionally substituted aromatic hydrocarbon or biaryl, or optionally polycyclic; Hetaryl : optionally substituted aromatic heterocyclic compound or biheteroaryl, preferably electron-poor, optionally polynuclear or partially or completely hydrogenated or fluorinated;and R 1-R 8H, halo, CN, NO 2, COR 1, alkyl, alkoxy, aryl or heteroaryl. The aryl is partially or completely hydrogenated or fluorinated. Independent claims are included for the following: (1) new oxocarbon, pseudooxocarbon or radialene compounds of formula (I), their radical anionic salts, dianionic salts or charge transfer complexes with donors; (2) organic semiconductive material containing at least one organic matrix compound and one doping agent, where the doping agent is at least one oxocarbon, pseudooxocarbon or radialene compound; and (3) electronic component with an electronically functionally active area, where the electronically functionally active area is produced using at least one oxocarbon, pseudooxocarbon or radialene compounds. Provided that: (1) When n is 1, X 1 to X 5 is selected from C(CN) 2, (CF 3)C(CN), C(CF 3) 2, O or compounds of formula (Ia) to (Iq); Y 1 is selected from CN, COR 1, perhalogenated alkyl; and R 1 to R 8 are selected from hydrogen, halogen, CN, NO 2, COR 1, perhalogenated and/or partially halogenated alkyl, substituted and/or unsubstituted aryl or heteroaryl; (2) when n is 2, X 1 to X 5 is selected from C(CN) 2, (CF 3)C(CN), (NO 2)C(CN), C(CF 3) 2, NCN, O, S, NR 1 or compounds (Ia) to (Iq); Y 1 is selected from CN, NO 2, COR 1, or perhalogenated alkyl; and R 1 to R 8 are selected from hydrogen, halogen, CN, NO 2, COR 1, alkyl, alkoxy, preferably perhalogenated and/or partially halogenated alkyl, especially perfluorinated alkyl, substituted and/or unsubstituted aryl- or heteroaryl; (3) when n is 3, X 1 to X 5 is selected from C(CN) 2, (CF 3)C(CN), (NO 2)C(CN), C(halogen) 2, C(CF 3) 2, NCN, O, S, NR 1 or compounds (Ia) to (Iq); Y 1 is selected from CN, COR 1, perhalogenated alkyl, and R 1 to R 8 are selected from hydrogen, halogen, CN, NO 2, COR 1, alkyl, alkoxy, preferably perhalogenated and/or partially halogenated alkyl, especially perfluorinated alkyl, substituted and unsubstituted aryl- or heteroaryl; (4) when n is 4, X 1 to X 5 is selected from C(CN) 2, (CF 3)C(CN), (NO 2)C(CN), C(halogen) 2, C(CF 3) 2, NCN, O, S, NR 1 or compounds (Ia) to (Iq); Y 1 is selected from CN, COR 1, or perhalogenated alkyl and R 1 to R 8 are selected from hydrogen, halogen, CN, NO 2, COR 1, alkyl, alkoxy, preferably perhalogenated and/or partially halogenated alkyl, especially perfluorinated alkyl, optionally substituted aryl or heteroaryl; and (5) (I) excludes the following compounds: a) n is 1, X 1 to X 3 is (Ib) with X 4 is O; R 1 and R 3 is H and R 2 and R 4 is CH 3 or C 2H 5 or CH(CH 3) 2 or C(CH 3) 3; b) n is 1; X 1, X 2 is (Ib) with X 4 is O; X 3 is C(CN) 2 or X 3 is O; R 1 and R 3 is H and R 2 and R 4 is CH 3 or C 2H 5 or CH(CH 3) 2 or C(CH 3) 3; c) n is 1; X 1 and X 2 is C(CN) 2, C(CN)(COOR), C(COOR) 2, C(COR) 2, C(CN)(COR), C(COR)(COOR) with R is 1-6C-alkyl; X 3 is C(CN) 2, (C 6H 5)C(CN), (C 6H 5)C(COR), (C 6H 5SO 2)C(CN) with R is 1-6C-alkyl; d) n is 1; X 1 and X 2 is (Ij) with X 4 is O; R 1-8 is hydrogen; X 3 is O, C(CN) 2, (Ij) with X 4 is O and R 1-8 is hydrogen; e) n is 1; X 1 and X 2 is (Ie) and X 4 is O and R 1 to R 3 and R 6 is H and R 4,5 is C(CH 3) 3; X 3 is (Ie) with X 4 is O and R 1 to R 3 and R 6 is H and R 4 and R 5 is C(CH 3) 3; f) n is 1; X 1 to X 3 is NCN; g) n is 1; X 1 to X 3 is (Ic) with X 4 is C(CN) 2; h) n is 1; X 1 to X 3 is aryl-CH 2 or Hetaryl-CH 2-Hetaryl; i) n is 2; X 1 to X 3 is aryl-CH 2 or Hetaryl-CH 2-Hetaryl; j) n is 2; X 1 and X 3 is O or S; X 2 is C(CN) 2 or aryl-CH 2 with Ar is phenyl alkylphenyl, alkoxyphenyl or (Ir) with R 1 to R 8 is H or (Ib) with X 4 is O and R 1-4 is H, alkyl; k) n is 2; X 1 to X 3 is aryl-CH 2-aryl, Ar is Phenyl, Y 1 is CF 3; l) n is 2; X 1 to X 3 is (Ib) with X 4 is O; R 1 and R 3 is H and R 2 and R 4 is CH 3, C 2H 5, CH(CH 3) 2 or C(CH 3) 3; m) n is 3; X 1 to X 3 is O or C(CN) 2; n) n is 3; X 1 to X 3 is (Ir) or aryl-CH 2-Y 1; o) n is 4; X 1 to X 3 is (Ir) or aryl-CH 2-Y 1. 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    Method for making inclusion complex
    8.
    发明专利
    Method for making inclusion complex 审中-公开
    包含复合物的方法

    公开(公告)号:JP2012025781A

    公开(公告)日:2012-02-09

    申请号:JP2011238594

    申请日:2011-10-31

    摘要: PROBLEM TO BE SOLVED: To provide a batch method for making cyclopropene complex in which a vessel is not sealed while the method is performed.SOLUTION: There is provided a batch method of making cyclopropene complex involving mixture comprising (i) one or more molecular encapsulating agents and (ii) a solvent, wherein the ratio of the amount of the (i) to the amount of the (ii) is higher than the solubility of the molecular encapsulating agent in the solvent. There is also provided continuous methods for making cyclopropene complex in which the ratio of the rate of addition of the molecular encapsulating agent to the rate of addition of the solvent is higher than the solubility of the molecular encapsulating agent in the solvent.

    摘要翻译: 待解决的问题:提供在执行该方法时容器不被密封的环丙烯络合物的分批方法。 提供了一种制备涉及混合物的环丙烯络合物的分批方法,其包括(i)一种或多种分子包封剂和(ii)溶剂,其中(i)的量与 (ii)高于分子包封剂在溶剂中的溶解度。 还提供连续的制备环丙烯络合物的方法,其中分子包封剂的加入速率与溶剂加入速率的比例高于分子包封剂在溶剂中的溶解度。 版权所有(C)2012,JPO&INPIT