US 7,501,076 B2
Fluorescent diketopyrrolopyrroles
Hiroshi Yamamoto, Nishinomiya (Japan); and Norihisa Dan, Yawata (Japan)
Assigned to Ciba Specialty Chemicals Corporation, Tarrytown, N.Y. (US)
Appl. No. 10/551,976
PCT Filed Apr. 01, 2004, PCT No. PCT/EP2004/050403
§ 371(c)(1), (2), (4) Date Jul. 13, 2006,
PCT Pub. No. WO2004/090046, PCT Pub. Date Oct. 21, 2004.
Claims priority of application No. 03100972 (EP), filed on Apr. 10, 2003.
Prior Publication US 2007/0010672 A1, Jan. 11, 2007
Int. Cl. C09K 11/06 (2006.01); B32B 9/00 (2006.01); C07D 401/14 (2006.01)
U.S. Cl. 252—301.16  [252/301.26; 428/690; 428/917; 546/256; 546/276.7] 12 Claims
 
1. A fluorescent diketopyrrolopyrrole of formula I

OG Complex Work Unit Drawing
wherein
R1 and R2 may be the same or different and are a C1-C25alkyl group, which can be substituted by fluorine, chlorine or bromine, an allyl group, which can be substituted one to three times with C1-C4alkyl, C5-C12-cycloalkyl which can be substituted one to three times with C1-C8alkyl and/or C1-C8alkoxy, C5-C12cycloalkyl 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 haloalkyl group, a haloalkenyl group, a haloalkynyl group, an aldehyde group, an ester group, a carbamoyl group, a ketone group, a silyl group, a siloxanyl group, A3 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-C4alkyl,
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 and A2 are independently of each other a group

OG Complex Work Unit Drawing
wherein
R5 is a group NR8R9,
wherein R8 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a heterocyclic group, an aralkyl group,
R9 is an aryl group or a heteroaryl group,
or R8 and R9 together with the nitrogen atom to which they are bonded form a five or six membered heterocyclic ring condensed by one or two optionally substituted phenyl groups,
wherein
R6 and R7 may be the same or different and are a hydrogen atom, a C1-C25alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group, a heterocyclic group, a halogen atom, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, a cyano group, an aldehyde group, a carboxyl group, an ester group, a carbamoyl group, a nitro group, a silyl group, a siloxanyl group, a substituted or unsubstituted vinyl group, a group NR8R9, wherein R8 and R9 independently of each other stand for a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a heterocyclic group, an aralkyl group, or R8 and R9 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.