Substituted Rylene Derivatives

A rylene derivative of the general formula Ia

• in which the variables are each defined as follows:
• B are joined together with formation of a six-membered ring to give a radical of the formula (a), (b) or (c)
• are both hydrogen or a —COOM radical, or one of the two radicals is an A radical or Hal and the other radical is hydrogen;
• B′, independently of B, are joined together with formation of a six-membered ring to give a radical of the formula (a), (b) or (c), or are both hydrogen or a —COOM radical;
• A is a radical of the formula
• where the A radicals may be the same or different when n>1;
• Y is a (thio)phenoxy radical of the formula
• where the Y radicals may be the same or different when y>1;
• X is —O— or —S—;
• R are identical or different radicals:
• (i) C1-C30-alkyl which has no more than one tertiary carbon atom in the 1-position and whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —C≡C—, —CR2═CR2— and/or —CO— moieties and which may be mono- or polysubstituted by C1-C12-alkoxy, hydroxy and/or halogen;
• (ii) C3-C8-cycloalkyl which has no more than one tertiary carbon atom in the 1-position and whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —CR2═CR2— and/or —CO— moieties and which may be mono- or polysubstituted by C1-C18-alkyl, C1-C12-alkoxy and/or C1-C6-alkylthio;
• (iii) aryl or hetaryl, to each of which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by C1-C18-alkyl, C1-C12-alkoxy, —C≡CR2, —CR2═CR22, hydroxy, halogen, —NR3R4, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR3 and/or —SO3R3;
• (iv) a —U-aryl radical which may be mono- or polysubstituted by the above radicals specified as substituents for the aryl radicals (iii), where U is an —O—, —S—, —NR2—, —CO—, —SO— or —SO2— moiety;
• (v) C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxy, mercapto, halogen, cyano, nitro, —NR3R4, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR3 or —SO3R3;
• R′ are identical or different radicals:
• hydrogen;
• one of the radicals specified for R (i), (ii), (iii), (iv) and (v), where the alkyl radicals (i) and the cycloalkyl radicals (ii) may have a tertiary carbon atom in the 1-position;
• P is a 5- to 9-membered ring which is bonded via a nitrogen atom and whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —CO— and/or —SO2— moieties, to each of which may be fused one or two unsaturated or saturated 4- to 8-membered rings whose carbon chain may likewise be interrupted by these moieties and/or —N═, where the entire ring system may be mono- or polysubstituted by:
• hydroxy, nitro, —NR3R4, —COOR3, —CONR3R4 and/or —NR2COR3;
• C1-C30-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —CO— and/or —SO2— moieties and which may be mono- or polysubstituted by cyano, hydroxy, nitro, C1-C6-alkoxy, —COOR3, —CONR3R4, aryl which may be substituted by C1-C18-alkyl or C1-C6-alkoxy, and/or a 5- to 7-membered heterocyclic radical which is bonded via a nitrogen atom and may comprise further heteroatoms and be aromatic;
• C5-C8-cycloalkyl whose carbon skeleton may be interrupted by one or more —O—, —S— and/or —NR2— moieties and/or which may be mono- or polysubstituted by C1-C6-alkyl;
• aryl or hetaryl, each of which may be mono- or polysubstituted by C1-C18-alkyl, C1-C6-alkoxy, cyano, nitro, halogen, —CONR3R4, —NR3COR4, —SO3R3, —SO2NR3R4 and/or aryl- or hetarylazo, each of which may be mono- or polysubstituted by C1-C10-alkyl, C1-C6-alkoxy and/or cyano,
• where the P radicals may be the same or different when p>1;
• Hal is fluorine, chlorine, bromine or iodine,
• E is 1,2-phenylene, 1,8- or 2,3-naphthylene or 2,3- or 3,4-pyridylene, each of which may be substituted by C1-C12-alkyl, C1-C6-alkoxy, hydroxy, nitro and/or halogen,
• where the E radicals may be the same or different when they occur more than once in formula Ia;
• M is hydrogen, alkali metal cation, NH4+ or NR34+;
• R1 is hydrogen;
• C1-C30-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—N═CR2—, —C≡C—, —CR2CR2—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by the radicals specified for R (ii), (iii), (iv) and/or (v);
• C3-C8-cycloalkyl to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties,
• where the entire ring system may be mono- or polysubstituted by the radicals specified for R (i), (ii), (iii), (iv) and/or (v);
• aryl or hetaryl, to each of which may be fused further saturated or unsaturated, 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR+2-, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by the radicals specified for R (i), (ii), (iii), (iv), (v) and/or aryl- and/or hetarylazo, each of which may be mono- or polysubstituted by C1-C10-alkyl, C1-C6-alkoxy and/or cyano,
• where the R1 radicals may be the same or different when they occur more than once in the formula Ia;
• R2 is hydrogen or C1-C18-alkyl;
• R3, R4 are each independently hydrogen;
• C1-C18-alkyl which may be mono- or polysubstituted by C1-C6-alkoxy, hydroxy, halogen and/or cyano;
• aryl or hetaryl, each of which may be mono- or polysubstituted by C1-C6-alkyl and/or the above radicals specified as substituents for alkyl;
• m is 0, 1 or 2;
• n is from 1 to 8;
• p is from 0 to 6 where n+p≦8;
• y is from 0 to 7 where n+p+y≦8;
• z is from 0 to 8 where n+p+y+z≦10.

A rylene derivative of the general formula Ib

• in which the variables are each defined as follows:
• D are identical or different radicals:
• hydrogen, an A radical or a Y radical, where at least one of the D radicals is an A radical,
• A is a radical of the formula
• Y is a (thio)phenoxy radical of the formula
• X is —O— or —S—;
• R are identical or different radicals:
• (i) C1-C30-alkyl which does not have a tertiary carbon atom in the 1-position and whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —C≡C—, —CR2═CR2— and/or —CO— moieties and which may be mono- or polysubstituted by C1-C12-alkoxy, hydroxy and/or halogen;
• (ii) C3-C8-cycloalkyl which does not have a tertiary carbon atom in the 1-position and whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —CR2═CR2— and/or —CO— moieties and which may be mono- or polysubstituted by C1-C18-alkyl, C1-C12-alkoxy and/or C1-C6-alkylthio;
• (iii) aryl or hetaryl, to each of which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO— —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by C1-C18-alkyl, C1-C12-alkoxy, —C≡CR2, —CR2═CR22, hydroxy, halogen, —NR3R4, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR3 and/or —SO3R3;
• (iv) a —U-aryl radical which may be mono- or polysubstituted by the above radicals specified as substituents for the aryl radicals (iii), where U is an —O—, —S—, —NR2—, —CO—, —SO— or —SO2— moiety;
• (v) C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxy, mercapto, halogen, cyano, nitro, —NR3R4, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR3 or —SO3R3;
• R′ are identical or different radicals:
• hydrogen;
• one of the radicals specified for R (i), (ii), (iii), (iv) and (v), where the alkyl radicals (i) and the cycloalkyl radicals (ii) may have a tertiary carbon atom in the 1-position;
• R1 is hydrogen;
• C1-C30-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —C≡C—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by the radicals specified for R (ii), (ii), (iv) and/or (v);
• C3-C8-cycloalkyl to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by the radicals specified for R (i), (ii), (iii), (iv) and/or (v);
• aryl or hetaryl, to each of which may be fused further saturated or unsaturated, 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by the radicals specified for R (i), (ii), (iii), (iv), (v) and/or aryl- and/or hetarylazo, each of which may be mono- or polysubstituted by C1-C10-alkyl, C1-C6-alkoxy and/or cyano,
• where the R1 radicals may be the same or different when they occur more than once in the formula Ib;
• R2 is hydrogen or C1-C18-alkyl;
• R3, R4 are each independently hydrogen;
• C1-C18-alkyl which may be mono- or polysubstituted by C1-C6-alkoxy, hydroxy, halogen and/or cyano;
• aryl or hetaryl, each of which may be mono- or polysubstituted by C1-C6-alkyl and/or the above radicals specified as substituents for alkyl;
• m is 1 or 2.