Indacene and azaindacene compounds and higher homologues and the use thereof

An electronic component, comprising at least one compound of the formula (I):

• or their radical anions, radical anionic salts, radical cations, radical cationic salts, dianions, dianionic salts, dications, dicationic salts or their charge transfer complexes with donors or acceptors,
• in which
• n is 1,
• A is C—R1, B is nitrogen or C—R2, C is nitrogen or C—R3, D is nitrogen or C—R4, E is nitrogen or C—R5 and F is nitrogen or C—R6,
• each G1n is nitrogen or C—R1n,
• each H1n is nitrogen or C—R2n,
• wherein R1 is selected from halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R2 is selected from hydrogen, halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R3 is selected from halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R4 is selected from halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R5 is selected from hydrogen, halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R6 is selected from halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R11 and R21 are independently selected from hydrogen,
• halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein each C6-C14-aryl and heteroaryl is unsubstituted or substituted with either one or more than one electron acceptor group, which is selected from cyano, nitro, fluoro, perfluoro (C1-C5-alkyl), OCF3, SF5, SO2CF3, chloro, bromo and C6-C14-aryl, which is unsubstituted or substituted by 1, 2, 3, or 4 electron acceptor group, which is selected from cyano, nitro, halogen, perfluoro (C1-C5-alkyl), OCF3, SF5, SO2CF3, or with either one or more than one electron donor group, which are selected from C1-C30-alkyl, C3-C10-cycloalkyl, C1-C15-alkoxy, C6-C14-aryloxy, di(C6-C14-aryl)amino, di(C1-C15-alkyl)amino and di(C3-C10-cycloalkyl)amino,
• wherein heterocycloalkyl is unsubstituted or substituted with 1, 2, 3, 4 or 5 radicals RG which is selected from halogen, cyano, OCF3, SF5, SO2CF3, ═O, or two adjacent RG together with the carbon atoms, which they are attached to form a C6-C10 aryl, which is unsubstituted or substituted with 1, 2, 3 or 4 identical or different halogen, and wherein the heterocycloalkyl is connected with the remaining molecule via a heteroatom,
• wherein RX and RY independently from each other selected from hydrogen, C1-C15-alkyl, C1-C10-alkyl and C6-C14-aryl, wherein alky is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from cyano and halogen, and cycloalyl and aryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from cyano, halogen, C1-C4 alkyl and C1-C4 haloalkyl,
• wherein R7 is selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C6-C14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals CN, halogen, C1-C4-alkyl or C1-C4-haloalkyl,
• wherein RA is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• wherein RB is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• wherein RC is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• wherein RD is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• wherein RE is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• wherein RF is selected from C1-C10-alkyl, phenyl, tolyl, Anisyl, Mesityl,
• or RE and RF bound to the same or to different nitrogen atoms form a C3-C10 heterocycloalkyl,
• with the proviso that
• are excluded.

A compound of the formula (I),

• or their radical anions, radical anionic salts, radical cations, radical cationic salts, dianions, dianionic salts, dications, dicationic salts or their charge transfer complexes with donors or acceptors,
• in which
• n is 1,
• A is C—R1, B is nitrogen or C—R2, C is nitrogen or C—R3, D is nitrogen or C—R4, E is nitrogen or C—R5 and F is nitrogen or C—R6,
• each G1n is nitrogen or C—R1n,
• each H1n is nitrogen or C—R2n,
• wherein 0, 1, 2, 3 or 4 non-adjacent groups A, B, C, D, E or F are a nitrogen atom,
• wherein R1 is selected from halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R2 is selected from hydrogen, halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R3 is selected from halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R4 is selected from halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R5 is selected from hydrogen, halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R6 is selected from halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein R11 and R21 are independently selected from hydrogen,
• halogen, cyano, perfluoro (C1-C5-alkyl), NRXRY, C1-C15-alkoxy, C3-C10-cycloalkyloxy, C6-C14-aryloxy, C1-C15-alkyl, C3-C10-cycloalkyl, C3-C10-heterocycloalkyl comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing group as ring members selected from N, NR7, O, S, SO and SO2, C6-C14-aryl and heteroaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2, 3 or 4 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR7, O, S, SO and SO2, N═P(RARBRC), N═C(RD)NRERF), N—C(NRERF)NRERF,
• wherein each C6-C14-aryl and heteroaryl is unsubstituted or substituted with either one or more than one electron acceptor group, which is selected from cyano, nitro, fluoro, perfluoro (C1-C5-alkyl), OCF3, SF5, SO2CF3, chloro, bromo and C6-C14-aryl, which is substituted by 1, 2, 3, or 4 electron acceptor group, which is selected from cyano, nitro, halogen, perfluoro (C1-C5-alkyl), OCF3, SF5, SO2CF3, or with either one or more than one electron donor group, which are selected from C1-C30-alkyl, C3-C10-cycloalkyl, C1-C15-alkoxy, C6-C14-aryloxy, di(C6-C14-aryl)amino, di(C1-C15-alkyl)amino and di(C3-C10-cycloalkyl)amino,
• wherein heterocycloalkyl is unsubstituted or substituted with 1, 2, 3, 4 or 5 radicals RG which is selected from halogen, cyano, OCF3, SF5, SO2CF3, ═O, or two adjacent RG together with the carbon atoms, which they are attached to form a C6-C10 aryl, which is unsubstituted or substituted with 1, 2, 3 or 4 identical or different halogen, and wherein the heterocycloalkyl is connected with the remaining molecule via a heteroatom.
• wherein RX and RY independently from each other selected from hydrogen, C1-C15-alkyl, C1-C10-alkyl and C6-C14-aryl, wherein alky is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from cyano and halogen, and cycloalyl and aryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from cyano, halogen, C1-C4 alkyl and C1-C4 haloalkyl,
• wherein R7 is selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C6-C14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals CN, halogen, C1-C4-alkyl or C1-C4-haloalkyl,
• wherein RA is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• wherein RB is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• wherein RC is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• wherein RD is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• wherein RE is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• wherein RF is selected from C1-C10-alkyl, phenyl, tolyl, anisyl, mesityl,
• or RE and RF bound to the same or to different nitrogen atoms form a C3-C10 heterocycloalkyl,
• with the proviso that
• are excluded.