Fluorescent diketopyrrolopyrrole analogues

• Main Authors: SMITH DAVID MACDONALD, MORTON COLIN, IQBAL ABUL
• Format: Patent
• Language: English
• Published: 09.05.2006
• Subjects: ADHESIVES; BASIC ELECTRIC ELEMENTS; CHEMICAL PAINT OR INK REMOVERS; CHEMISTRY; COATING COMPOSITIONS, e.g. PAINTS, VARNISHES ORLACQUERS; COMPOSITIONS BASED THEREON; CORRECTING FLUIDS; DYES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR; ELECTRICITY; FILLING PASTES; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; INKS; INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIRCHEMICAL OR PHYSICAL PROPERTIES; LAKES; MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FORELSEWHERE; MEASURING; MEDICAL OR VETERINARY SCIENCE; METALLURGY; MISCELLANEOUS APPLICATIONS OF MATERIALS; MISCELLANEOUS COMPOSITIONS; MORDANTS; NATURAL RESINS; OPTICAL ELEMENTS, SYSTEMS, OR APPARATUS; OPTICS; ORGANIC CHEMISTRY; ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES; ORGANIC MACROMOLECULAR COMPOUNDS; PAINTS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; PHYSICS; POLISHES; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SEMICONDUCTOR DEVICES; SPECIFIC USE OF COSMETICS OR SIMILAR TOILETPREPARATIONS; TESTING; THEIR PREPARATION OR CHEMICAL WORKING-UP; USE OF INORGANIC OR NON-MACROMOLECULAR ORGANIC SUBSTANCES ASCOMPOUNDING INGREDIENTS; USE OF MATERIALS THEREFOR; WOODSTAINS

The present invention relates to fluorescent diketopyrrolopyrrole analogues of the general formula (I), wherein A1 and A2 are C1-C18alkyl, C2-C18alkenyl, C2-C18alkynyl, C5-C8cycloalkyl, C5-C8cycloalkenyl, aryl or heteroaryl, A3 and A4 are independently of each other C1-C18alkyl, Ar3, -CR30R31-(CH2)m-Ar3, or Y-R32, wherein R30 and R31 independently of each other stand for hydrogen or C1-C4alkyl, or phenyl which can be substituted up to three times with C1-C3alkyl, Ar3 stands for aryl, in particular phenyl or 1- or 2-naphthyl, C5-C8cycloalkyl, in particular cyclohexyl, or heteroaryl, which can be substituted one to three times with C1-C8alkyl, C1-C8alkoxy, halogen or phenyl, which can be substituted with C1-C8alkyl or C1-C8alkoxy one to three times, and m stands for 0, 1, 2, 3 or 4, Y is C(O)- or SO2- and R32 is C1-C18alkyl, Ar3, or aralkyl and A3 can additionally be hydrogen, C1-C8alkyloxycarbonyl, such as tertbutoxycarbonyl, or aralkyloxycarbonyl, such as benzyloxycarbonyl, a process for their preparation and their use for the preparation of inks, colourants, pigmented plastics for coatings, non-impact printing material, colour filters, cosmetics, polymeric ink particles, toners, dye lasers and electroluminescent devices, or as fluorescent markers for immunoassays and fluorescent tracers for leak detection of fluids. The diketopyrrolopyrrole analogues of the general formula I show a high solid state fluorescence