Patent EP-1988587-A1 (EP)
Inventor: HARTMANN HORST PROF DR
IPC: C07C255/51
Filed: 2007-04-30
Abstract: 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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