New hydroxyperylene-bisimide-, aliphatic ether and aliphatic N-substituted perylene-lactamimide dyes, useful e.g. as intercalating or fluorescent dyes, pigments, tracers or starting materials for organic superconductor or in data storage

摘要

New perylene dyes are hydroxy-perylene-3,4:9,10-tetracarbimides (I), in which the hydroxyl group and/or one or both nitrogen atoms may have a 1-37C alkyl substituent, where 1-10 methylene units may be replaced by carbonyl, oxygen, sulfur, selenium, tellurium, cis- or trans-dimethine, azadimethine, acetylene, divalent phenyl, pyridine or thiophene group or by a naphthylene or anthracene group, and where 1 or 2 methine groups may be replaced by nitrogen, and numerous other substituents. New perylene dyes are hydroxy-perylene-3,4:9,10-tetracarbimides (I) of formula (11): R1-R3H, 1-37C linear alkyl, in which 1-10 CH2 units may be replaced by X; X : carbonyl, O, S, Se, Te, or cis- or trans-CH=CH in which 1 CH unit may be replaced by N, Ctriple boundC, 1,2-, 1,3- or a 1,4-substituted phenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-di-substituted pyridine, 2,3-, 2,4-, 2,5- or 3,4-di-substituted thiophene group or a 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-di-substituted naphthylene 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-di-substituted anthracene group in which 1 or 2 CH2 groups may be replaced by N, where 1-12 H atoms of the CH2 groups, including those on the same C atom, may be replaced by halogen, F, Cl, Br, I, CN, or 1-18 C linear alkyl in which 1-6 CH2 groups may be replaced by C and, in turn, 1-6 CH2 units of the alkyl groups may be replaced by C; or free valencies of the methine groups or quaternary C atoms may be linked in pairs to form rings, e.g. cyclohexane rings Independent claims are also included for the following (1) new N,N'-bis(2-alkyl-3-hydroxypropyl)-perylene-3,4:9,10-tetracarbimide dyes of formula (12); (2) new N,N'-bis(2-alkyl-3-hydroxypropyl)-1-hydroxy-perylene-3,4:9,10-tetracarbimide dyes of formula (13); (3) new N,N'-bis(2-alkyl-3-hydroxypropyl)-pyrrolo[3,4-bc]perylo[9,10-b'c']pyridine dyes of formula (14); (4) new N,N'-bis(2-alkyl-3-hydroxypropyl)-1-hydroxy-pyrrolo[3,4-bc]perylo[9,10-b'c']pyridine dyes of formula (15); (5) new N-2-alkyl-3-hydroxypropyl-pyrrolo[3,4-bc]perylo[9,10-b'c']pyridine dyes (16); (6) process using dipolar aprotic solvent with addition of alcohol as reaction medium. R4as for R1-R3. [Image] [Image] [Image] [Image].