Patent DE-102008039562-A1 (DE)
Title: New anthra(2,1,9-def;6,5,10-d'e'f')diisoquinoline-1,3,8,10-tetraone compounds useful e.g. as pigments for glue- or water- colors, lacquers and tracers in biochemistry, and in organic light emitting diode and photovoltaic devices
Inventor: LANGHALS HEINZ
IPC: C09D7/12
Filed: 2008-08-25
Abstract: Anthra[2,1,9-def;6,5,10-d'e'f']diisoquinoline-1,3,8,10-tetraone compounds (VII), are new. Anthra[2,1,9-def;6,5,10-d'e'f']diisoquinoline-1,3,8,10-tetraone compounds of formula (VII), are new. R 1>-R 8>H or 37C-alkyl residue, where 1-10 CH 2-units are optionally substituted by carbonyl groups, O, S, Se, Te, cis or trans-CH=CH-groups, where one CH unit is optionally substituted by N, C?=C, 1,2-, 1,3 - or 1,4-substituted phenyl residues, 2,3, 2,4, 2,5, 2,6, 3,4 - or 3,5-disubstituted pyridine residues, 2,3, 2,4, 2,5 or 3,4-disubstituted thiophene residues, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 2,3, 2,6 or 2,7-disubstituted naphthalene residues, where one or two CH groups are optionally substituted by N, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 1,9, 1,10, 2,3, 2,6, 2,7, 2,9, 2,10- or 9,10-disubstituted anthracene residues, where one or two CH groups are optionally substituted by N, up to 12 H atoms of CH 2-groups are optionally substituted on the same carbon atoms by halogens, CN or up to 18C-alkyl, where 1-6 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, where one CH-unit is optionally substituted by N, C?=C, 1,2, 1,3 or 1,4-substituted phenyl residues, 2,3, 2,4, 2,5, 2,6, 3,4- or 3,5-disubstituted pyridine residues, 2,3, 2,4, 2,5- or 3,4-disubstituted thiophene residues, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 2,3, 2,6- or 2,7-disubstituted naphthalene residues, where 1-2C are optionally substituted by N, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 1,9, 1,10, 2,3, 2,6, 2,7, 2,9, 2,10- or 9,10-disubstituted anthracene residues, where 1-2C are optionally substituted by N, up to 12 H of the CH 2of the alkyl residues are optionally substituted on the same carbon atoms by halo, CN or up to 18C-alkyl, where 1-6 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, where one CH-unit is optionally substituted by N, C?=C groups, 1,2, 1,3- or 1,4-substituted phenyl residues, 2,3, 2,4, 2,5, 2,6, 3,4- or 3,5-disubstituted pyridine residues, 2,3, 2,4, 2,5- or 3,4-disubstituted thiophene residues, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8-2,3, 2,6- or 2,7-disubstituted naphthalene residues; and X : at least or at most 37C-alkyl residue, where 1-10 CH 2-units are optionally substituted by carbonyl groups, O, S, Se, Te, cis or trans-CH=CH-groups, where one CH unit is optionally substituted by N, C?=C, 1,2-, 1,3 - or 1,4-substituted phenyl residues, 2,3, 2,4, 2,5, 2,6, 3,4 - or 3,5-disubstituted pyridine residues, 2,3, 2,4, 2,5 or 3,4-disubstituted thiophene residues, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 2,3, 2,6 or 2,7-disubstituted naphthalene residues, where one or two CH groups are optionally substituted by N, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 1,9, 1,10, 2,3, 2,6, 2,7, 2,9, 2,10- or 9,10-disubstituted anthracene residues, where one or two CH groups are optionally substituted by N, up to 12 H atoms of CH 2-groups are optionally substituted on the same carbon atoms by halo, CN or up to 18C-alkyl, where 1-6 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, where one CH-unit is optionally substituted by N, C?=C, 1,2, 1,3 or 1,4-substituted phenyl residues, 2,3, 2,4, 2,5, 2,6, 3,4- or 3,5-disubstituted pyridine residues, 2,3, 2,4, 2,5- or 3,4-disubstituted thiophene residues, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 2,3, 2,6- or 2,7-disubstituted naphthalene residues, where 1-2C are optionally substituted by N, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 1,9, 1,10, 2,3, 2,6, 2,7, 2,9, 2,10- or 9,10-disubstituted anthracene residues, where 1-2C are optionally substituted by N, up to 12 H of the CH 2of the alkyl residues are optionally substituted on the same carbon atoms by halo, CN or up to 18C-alkyl, where 1-6 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, where one CH-unit is optionally substituted by N, C?=C groups, 1,2, 1,3- or 1,4-substituted phenyl residues, 2,3, 2,4, 2,5, 2,6, 3,4- or 3,5-disubstituted pyridine residues, 2,3, 2,4, 2,5- or 3,4-disubstituted thiophene residues, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8-2,3, 2,6- or 2,7-disubstituted naphthalene residues in which one or two carbon atoms are optionally substituted by N, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted anthracene residue in which one or two carbon atoms are optionally substituted by N. Provided that: instead of the substituents, the free valences of the methyne groups and/or the quaternary carbon-atoms are linked in pairs, to form a ring, e.g. cyclohexane ring, and the R 1>-R 9>residues further contain F, Cl, Br or I. Independent claims are included for: (1) a perylenetetracarboxylic acid bisimide compound of formula (V); and (2) the preparation of (VII). [Image] [Image].