Fluorescent diketopyrrolopyrroles
AssigneeBASF SE Ludwigshafen
InventorsHiroshi Yamamoto, Hidetaka Oka, Mathias Düggeli
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Abstract
The present invention relates to fluorescent diketopyrrolopyrroles of the formula (I), or (III), a process for their preparation and their use for the preparation of inks, colorants, pigmented plastics for coatings, non-impact-printing material, color filters, cosmetics, polymeric ink particles, toners, as fluorescent tracers, in color changing media, in solid dye lasers, EL lasers and electroluminescent devices. A luminescent device comprising a compound, or composition according to the present invention is high in the efficiency of electrical energy utilization and high in luminance.
Claims4
A fluorescent diketopyrrolopyrrole of the formula
- wherein R1 and R2 may be the same or different and are selected from a C1-C25alkyl group, an allyl group, which can be substituted one to three times with C1-C3alkyl, a cycloalkyl group, which can optionally be substituted one to three times with C1-C8alkyl and/or C1-C8alkoxy, a cycloalkyl group, which is condensed one or two times by phenyl which can be substituted one to three times with C1-C4-alkyl, halogen, nitro, or cyano, an alkenyl group, a cycloalkenyl group, an alkynyl group, a heterocyclic group, haloalkyl, haloalkenyl, haloalkynyl, a heterocyclic group, a ketone or aldehyde group, an ester group, a carbamoyl group, a silyl group, a siloxanyl group, aryl, heteroaryl, or —CR3R4—(CH2)m-A3 wherein R3 and R4 independently from each other stand for hydrogen or C1-C4alkyl, or phenyl which can be substituted one to three times with C1-C3alkyl, A3 stands for aryl, or heteroaryl, which can be substituted one to three times with C1-C8alkyl and/or C1-C8alkoxy, and m stands for 0, 1, 2, 3 or 4,
- A1 stands for
- wherein R25′ is a C6-C12aryl group, which may be substituted by one, or more C1-C8alkyl, or C1-C8alkoxy groups, R300 is C1-C8alkyl, a C6-C24aromatic, or C2-C17heteroaromatic group, which may be substituted by one, or more C1-C8alkyl, or C1-C8alkoxy groups,
- R21, R22, R23, R25 and R26 are independently of each other hydrogen, C1-C8alkyl, a hydroxyl group, a mercapto group, C1-C8alkoxy, C1-C8alkylthio, halogen, halo-C1-C8alkyl, a cyano group, an aldehyde group, a ketone group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group,
- R27 and R28 are independently of each other
- wherein R29, R30 and R31 are independently of each other hydrogen, C1-C8alkyl, C1-C8alkoxy or a group —NR32R33, wherein R32 and R33 are independently of each other
- wherein R34 is hydrogen, C1-C8alkyl or C1-C8alkoxy, or
- R27 and R28 together with the nitrogen atom to which they are bonded form a five or six membered heterocyclic ring, which can be condensed by one or two optionally substituted phenyl groups, R29′ and R30′ independently from each other stands for hydrogen, C1-C8-alkyl or C1-C8-alkoxy, and A2 stands for A1 with the proviso that A2 and A1 have different meanings within the same molecule;
- A2 stands for
- wherein R122 to R123 may be the same or different and are selected from hydrogen, C1-C25group, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, a mercapto group, alkoxy, alkylthio, an aryl ether group, an aryl thioether group, aryl, a heterocyclic group, halogen, haloalkyl, haloalkenyl, haloalkynyl, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, a group NR27R28, wherein R27 and R28 are as defined above, a nitro group, a silyl group, a siloxanyl group, a substituted or unsubstituted vinyl group, or at least two adjacent substituents R115 to R121 form an aromatic, heteroaromatic or aliphatic fused ring system,
- R124 and R125 may be the same or different and are selected from C1-C18alkyl;
- or R124 and R125 together form a five-, six- or seven-membered ring, which can optionally be substituted by C1-C8alkyl, or which can optionally be condensed one or two times by phenyl which can be substituted one to three times with C1-C8-alkyl, C1-C8-alkoxy, halogen and cyano;
- or
- A2 stands for a heteroaromatic group
- wherein R131 to R152 may be the same or different and are selected from hydrogen, C1-C25alkyl group, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, a mercapto group, alkoxy, alkylthio, an aryl ether group, an aryl thioether group, aryl, a heterocyclic group, halogen, haloalkyl, haloalkenyl, haloalkynyl, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, a group NR27R28, wherein R27 and R28 are as defined above, a nitro group, a silyl group, a siloxanyl group, a substituted or unsubstituted vinyl group.
Dependencies are inferred from the claim text.