Substituted phthalocyanine

Abstract

Compound of formula wherein M is a divalent metal, oxo metal, halogenometal or hydroxymetal, or 2 hydrogen atoms, A is a radical which may be unsubstituted or substituted by phenoxy, naphthyloxy, phenylthio or by naphthylthio, X is a hetero atom selected from the group consisting of N, O and S, m being the number 0 when X is O or S and the number 1 when X is N, Y is any desired substituent that is inert towards alkylating reagents, Z is hydrogen, Z′ or COOB, Z′ is C 2 -C 12 alkylene-N(COOB) 2 , C 2 -C 12 alkylene-NHCOOB, C 2 -C 12 alkylene-OCOOB or C 2 -C 12 alkylene-SCOOB, x is a number from 1 to 4, and y is a number from 0 to 15, wherein the sum of x and y is a maximum of 16 and, optionally, a plurality of radicals X, Y, Z and/or Z′ may be identical or different, and B is an alkyl-, alkenyl-, alkynyl-, aralkyl- or polyglycol- or polyamine-substituted alkylene group. The compound according to the invention is used as a colourant and a pigment precursor, especially in light-sensitive compositions for colour filters.

1 . A compound of formula  
       
         
           
           
               
               
           
         
       
       wherein 
 M is a divalent metal, oxo metal, halogenometal or hydroxymetal, or 2 hydrogen atoms,  
 A is a radical  
                     
 which may be unsubstituted or substituted by phenoxy, naphthyloxy, phenylthio or by naphthylthio,  
 X is a hetero atom selected from the group consisting of N, O and S, m being the number 0 when X is O or S and the number 1 when X is N,  
 Y is any desired substituent that is inert towards alkylating reagents,  
 Z is hydrogen, Z′ or COOB,  
 Z′ is C 2 -C 12 alkylene-N(COOB) 2 , C 2 -C 12 alkylene-NHCOOB, C 2 -C 12 alkylene-OCOOB or C 2 -C 12 alkylene-SCOOB,  
 x is a number from 1 to 4, and y is a number from 0 to 15,  
 wherein the sum of x and y is a maximum of 16 and, optionally, a plurality of radicals X, Y, Z and/or Z′ may be identical or different, and  
 B is a group of the formula  
                     
 wherein  
 R 1  is hydrogen or C 1 -C 6 alkyl,  
 R 2  and R 3  are each independently of the other C 1 -C 6 alkyl,  
 R 4  and R 8  are each independently of the other C 1 -C 6 alkyl, C 1 -C 6 alkyl interrupted by O, S or by NR 12 , phenyl or biphenyl unsubstituted or substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen, cyano or by nitro,  
 R 5 , R 6  and R 7  are each independently of the others hydrogen or C 1 -C 6 alkyl,  
 R 9  is hydrogen, C 1 -C 6 alkyl or a group of the formula  
                     
 R 10  and R 11  are each independently of the other hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen, cyano, nitro, N(R 12 ) 2 , or phenyl unsubstituted or substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl or by C 1 -C 6 alkoxy,  
 R 12  and R 13  are each C 1 -C 6 alkyl, R 14  is hydrogen or C 1 -C 6 alkyl and R 15  is C 1 -C 6 alkyl, or phenyl unsubstituted or substituted by C 1 -C 6 alkyl,  
 E is p,q-C 2 -C 6 alkylene unsubstituted or mono- or poly-substituted by C 1 -C 6 alkoxy, C 1 -C 6 -alkythio or by C 2 -C 12 dialkylamino, wherein p and q are different position numbers,  
 X′ is a hetero atom selected from the group consisting of N, O and S, m′ being the number 0 when X′ is O or S and the number 1 when X′ is N, and  
 L 1  and L 2  are each independently of the other C 1 -C 6 alkyl or [-p′,q′-C 2 -C 6 alkylene)Z″-] n —C 1 -C 6 alkyl unsubstituted or mono- or poly-substituted by C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 2 -C 12 dialkylamino, C 6 -C 12 aryloxy, C 6 -C 12 arylthio, C 7 -C 18 arylalkylamino or by C 12 -C 24 -diarylamino, wherein n is a number from 1 to 1000 and p′ and q′ are different position numbers, each Z″ independently of the other(s) is a hetero atom O, S or C 1 -C 12 alkyl-substituted N, and the C 2 -C 6 alkylene radicals in the repeating units [—C 2 -C 6 alkylene-Z″—] may be identical or different,  
 and L 1  and L 2  may be saturated or unsaturated from one to ten times, may be uninterrupted or interrupted at any positions by from 1 to 10 groups selected from the group consisting of —(C═O)— and —C 6 H 4 —, and may carry no further substituents or from 1 to 10 further substituents selected from the group consisting of halogen, cyano and nitro.  
 
     
     
         2 . A compound according to  claim 1  of formula  
       
         
           
           
               
               
           
         
       
     
     
         3 . A compound according to  claim 1 , wherein M is Cu, Pd, Pb, Co, Ni, Zn, Mn or V(═O).  
     
     
         4 . A compound according to  claim 1 , wherein X is N or O and Z′ is C 2 -C 12 alkylene-NHCOOB or C 2 -C 12 alkylene-OCOOB.  
     
     
         5 . A compound according to  claim 1 , wherein X is N, Z is COOB and Z′ is C 2 -C 12 alkylene-OCOOB.  
     
     
         6 . A compound according to  claim 1 , wherein Z′ is C 2 -C 6 alkylene-N(COOB) 2 , C 2 -C 6 alkylene-NHCOOB, C 2 -C 6 alkylene-OCOOB or C 2 -C 6 alkylene-SCOOB.  
     
     
         7 . A compound according to  claim 1 , wherein B is  
       
         
           
           
               
               
           
         
       
     
     
         8 . A high molecular weight organic material comprising in the mass thereof a colourant of formula (I) according to  claim 1  wherein Z′ is C 2 -C 12 alkylene-OH, C 2 -C 12 alkylene-SH or C 2 -C 12 alkylene-NH 2 , produced in situ by thermal degradation of a compound of formula (I) according to  claim 1 .  
     
     
         9 . A heat-, photo- or chemo-sensitive recording material, an ink for ink-jet printing, a toner for an electrophotographic recording process, a coloured ribbon for thermal transfer printing, or a light-sensitive negative or positive resist composition that comprises a compound of formula (I).  
     
     
         10 . A method of producing structured colour images or colour filters, which method comprises the pattern-wise irradiation, development and heat treatment of a positive or negative resist comprising a colourant of formula (I) according to  claim 1 , wherein the heat treatment may take place at the time of the irradiation or development or later and the thermal conversion yields a colourant of formula (I) according to  claim 1  wherein Z′ is C 2 -C 12 alkylene-OH, C 2 -C 12 alkylene-SH or C 2 -C 12 alkylene-NH 2 .