Polymerisable diketopyrrolopyrroles, use of such compounds in colour filters and polymers prepared from these compounds

Abstract

The present invention relates to the use of polymerisable diketopyrrolopyrroles in colour filters, which can themselves be used for example in electro-optical systems such as TV screens, liquid crystal displays, charge coupled devices, plasma displays or electroluminescent displays and the like. In contrast to conventional pigments the polymerisable diketopyrrolopyrroles do not tend to aggregate and, hence, show very good dispersibility. Color filters prepared by using the polymerisable diketopyrrolopyrroles have high transparence and pure hue. In addition, they facilitate adjustment of color points and enable a large choice of shades.

1 . A colour filter comprising a transparent substrate and a layer comprising from 1 to 75% by weight, based on the overall weight of the layer, of a diketopyrrolopyrrole of the general formula (I) dispersed in a high molecular mass organic material:  
       
         
           
           
               
               
           
         
       
       wherein A and B independently of one another are a group of the formula  
       
         
           
           
               
               
           
         
         R 3  and R 4  independently of one another are hydrogen, halogen, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, —NR 16 R 17 , —CONHR 18 , —COOR 19 , —SO 2 NH—R 20 , C 1 -C 18 alkoxycarbonyl, C 1 -C 18 alkylaminocarbonyl, —CN, —NO 2 , trifluoromethyl, C 5 -C 7 cycloalkyl, —C═N—(C 1 -C 18 alkyl),  
         
           
             
             
                 
                 
             
           
         
         imidazolyl, pyrazolyl, triazolyl, piperazinyl, pyrrolyl, oxazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, morpholinyl, piperidinyl or pyrrolidinyl,  
         G is —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, —CH═N—, —N═N—, —O—, —S—, —SO—, —SO 2 —, —CONH— or —NR 9 —,  
         R 5  and R 6  independently of one another are hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 18 alkoxy or —CN,  
         R 7  and R 8  independently of one another are hydrogen, halogen or C 1 -C 6 alkyl and R 9  is hydrogen or C 1 -C 6 alkyl,  
         R 1  and R 2  are independently of each other C 1 -C 18 alkyl, C 1 -C 18 alkyl, which is interrupted one or more times by O or S, C 6 -C 12 aryl, C 7 -C 12 aralkyl, or a group of the formula —C(O)OR 10 , wherein R 10  is C 1 -C 18 alkyl, C 5 -C 10 cycloalkyl, C 6 -C 12 aryl, or C 7 -C 12 aralkyl, or  
         a group of the formula  
           —X 2 —X 3   (II), wherein  
         X 2  is an alkylene, arylene, aralkylene or cycloalkylene spacer containing optionally one or more groups —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or —COO— as linking bridge,  
         X 3  is OH, NH 2 , —C(R 11 )═CH 2 , —OC(O)—C(R 12 )═CH 2 , —C(O)—C(R 12 )═CH 2 , C 5 -C 7 cycloalkenyl,  
         
           
             
             
                 
                 
             
           
         
           —OC(O)—N—X 4 —N—C(O)—O—X 5 —O—C(O)—C(R 12 )═CH 2 ; wherein  
         R 11  is hydrogen, or C 1 -C 4 alkyl, or halogen,  
         R 12  is hydrogen, C 1 -C 4 alkyl, or halogen,  
         R 13  is hydrogen, C 1 -C 4 alkyl, or C 6 -C 12 aryl,  
         R 14  and R 15  are independently of each other hydrogen, C 1 -C 8 alkyl, or C 6 -C 12 aryl,  
         R 16 , R 17 , R 18  and R 20  are independently of each other hydrogen, C 1 -C 18 alkyl, C 6 -C 12 aryl, or C 7 -C 12 aralkyl,  
         R 19  is C 1 -C 18 alkyl, C 6 -C 12 aryl, or C 7 -C 12 aryl, and  
         X 4  and X 5  are independently of each other an alkylene, arylene, aralkylene or cycloalkylene spacer,  
         R 3 , R 4 , R 5 , R 6 , R 7 , and R 8  can also be a group of formula  
           —X 1 —X 2 —X 3   (III), wherein  
         X 1  is —O—, —S—, —NH—, —CONH—, —COO—, —SO 2 —NH—, or —SO 2 —O—, and  
         X 2  and X 3  are as defined above,  
         with the proviso that at least one, preferably two, of the groups of the formula (II) and/or (III) is present per molecule.  
       
     
     
         2 . A colour filter according to  claim 1 , wherein the diketopyrrolopyrrole is a pigment having the general formula  
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  are independently of each other a group of the formula  
         —X 2 —X 3   (II), wherein  X 2  is an alkylene, arylene, aralkylene or cycloalkylene spacer containing optionally a group —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or —COO— as linking bridge,    X 3  is —OH, —NH 2 , —C(R 11 )═CH 2 , —OC(O)—C(R 12 )═CH 2 , —C(O)—C(R 12 )═CH 2 , or      —OC(O)—N—X 4 —N—C(O)—O—X 5 —O—C(O)—C(R 12 )═CH 2 ; wherein    R 11  is hydrogen, or methyl,    R 12  is hydrogen, or methyl,    R 14  and R 15  are independently of each other hydrogen, C 1 -C 8 alkyl, or C 6 -C 12 aryl, and X 4  and X 5  are as defined in  claim 1 ,    R 3  and R 4  independently of one another are hydrogen, halogen, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, —NR 16 R 17 , —CONHR 18 , —COOR 19 , —SO 2 NH—R 20 , C 1 -C 18 alkoxycarbonyl, C 1 -C 18 alkylaminocarbonyl, —CN, —NO 2 , trifluoromethyl, C 5 -C 7 cycloalkyl, wherein R 16 , R 17 , R 18 , R 19  and R 20  are as defined in  claim 1 .    
     
     
         3 . A colour filter according to  claim 1 , wherein the diketopyrrolopyrrole is a pigment having the general formula  
       
         
           
           
               
               
           
         
       
       in which R 21  and R 22  are independently of one another hydrogen, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is interrupted one or more times by O or S, C 7 -C 12 aralkyl or a group of the formula  
       
         
           
           
               
               
           
         
       
       in which R 5  is C 1 -C 18 alkyl, 
 R 23  and R 24  independently of one another are a group of formula  
   —X 1 —X 2 —X 3 , wherein  
 X 1  is —O—, —S—, —NH—, —CONH—, —COO—, —SO 2 —NH—, or —SO 2 —O—,  
 X 2  is an alkylene, arylene, aralkylene or cycloalkylene spacer containing optionally one or more groups —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or —COO— as linking bridge,  
 X 3  is —OH, —NH 2 , —C(R 11 )═CH 2 , —OC(O)—C(R 12 )═CH 2 , —C(O)—C(R 12 )═CH 2 , or  
   —OC(O)—N—X 4 —N—C(O)—O—X 5 —O—C(O)—C(R 12 )═CH 2 ; wherein  
 R 11  is hydrogen, or methyl,  
 R 12  is hydrogen, or methyl,  
 R 14  and R 15  are independently of each other hydrogen, C 1 -C 8 alkyl, or C 6 -C 12 aryl, and X 4  and X 5  are as defined in  claim 1 .  
 
     
     
         4 . A diketopyrrolopyrrole of the general formula  
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  are independently of each other a group of the formula  
         —X 2 —X 3   (II), wherein  X 2  is an alkylene, arylene, aralkylene or cycloalkylene spacer containing optionally one or more groups —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or —COO— as linking bridge,    X 3  is OH, NH 2 , —C(R 11 )═CH 2 , —OC(O)—C(R 12 )═CH 2 , —C(O)—C(R 12 )═CH 2 , or      —OC(O)—N—X 4 —N—C(O)—O—X 5 —O—C(O)—C(R 12 )═CH 2 ; wherein    R 11  is hydrogen, or methyl,    R 12  is hydrogen, or methyl,    R 14  and R 15  are independently of each other hydrogen, C 1 -C 8 alkyl, or C 6 -C 12 aryl, and X 4  and X 5  are as defined in  claim 1 ,    R 3  and R 4  independently of one another are C 1 -C 18 alkyl, C 1 -C 18 alkylmercapto, C 1 -C 18 alkoxy, —NR 16 R 17 , —CONHR 18 , COOR 19 , —SO 2 NH—R 20 , C 1 -C 18 alkoxycarbonyl, C 1 -C 18 alkylaminocarbonyl, wherein R 16 , R 17 , R 18 , R 19  and R 20  are C 1 -C 18 alkyl.    
     
     
         5 . A diketopyrrolopyrrole according to  claim 4 , wherein R 1  and R 2  are independently of each other a radical of the formula  
         —X 2 —X 3 , wherein  X 2  is C 1 -C 18 alkylene and    X 3  is —NH 2 , —OH, —CH═CH 2 , —C(CH 3 )═CH 2 , —CO—CH═CH 2 , —CO—C(CH 3 )═CH 2 , —CO—CH═CH 2  or —CO—C(CH 3 )═CH 2 .    
     
     
         6 . A diketopyrrolopyrrole according to  claim 4 , wherein R 3  and R 4  are independently of each other C 1 -C 18 alkylmercapto, C 1 -C 18 alkoxy, or —NR 16 R 17 , wherein one of the groups R 16  and R 17  is hydrogen and the other is C 1 -C 18 alkyl or both groups R 16  and R 17  are independently of each other C 1 -C 18 alkyl.  
     
     
         7 . A diketopyrrolopyrrole of the general formula  
       
         
           
           
               
               
           
         
       
       in which R 21  and R 22  are independently of one another hydrogen, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is interrupted one or more times by O or S, C 7 -C 12 aralkyl or a group of the formula  
       
         
           
           
               
               
           
         
       
       in which R 5  is C 1 -C 18 alkyl, 
 R 23  and R 24  independently of one another are a group of formula  
   —X 1 —X 2 —X 3 , wherein  
 X 1  is —O—, —S—, —NH—, —CONH—, —COO—, —SO 2 —NH—, or —SO 2 —O—,  
 X 2  is an alkylene, arylene, aralkylene or cycloalkylene spacer containing optionally one or more groups —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or —COO— as linking bridge,  
 X 3  is —OH, —NH 2 , —C(R 11 )═CH 2 , —OC(O)—C(R 12 )═CH 2 , —C(O)—C(R 12 )═CH 2 , or  
   —OC(O)—N—X 4 —N—C(O)—O—X 5 —O—C(O)—C(R 12 )═CH 2 ; wherein  
 R 11  is hydrogen, or methyl,  
 R 12  is hydrogen, or methyl,  
 R 14  and R 15  are independently of each other hydrogen, C 1 -C 8 alkyl, or C 6 -C 12 aryl, C 1 -C 4 alkyl, or C 6 -C 12 aryl, and  
 X 4  and X 5  are independently of each other an an alkylene, arylene, aralkylene or cycloalkylene spacer.  
 
     
     
         8 . A diketopyrrolopyrrole according to  claim 7 , wherein R 23  and R 24  independently of one another are a group of formula  
         —X 1 —X 2 —X 3 , wherein  X 1  is —S—, —SO 2 NH— or —NH—,    X 2  is a C 1 -C 18 alkylene group, and    X 3  is —OH, —NH 2 , —CH═CH 2 , —C(CH 3 )═CH 2 , —CO—CH═CH 2 , —CO—C(CH 3 )═CH 2 , —CO—CH═CH 2 , or —CO—C(CH 3 )═CH 2 .    
     
     
         9 . A diketopyrrolopyrrole according to  claim 7 , wherein R 21  and R 22  independently of one another are hydrogen, or C 1 -C 18 alkyl.  
     
     
         10 . A polymer, obtainable by polyreacting a mixture consisting of 
 (A) from 0.5 to 20, preferably from 1 to 10% by weight, based on the sum of the components (A) and (B), of a diketopyrrolopyrrole IV or V, and    (B) from 99.5 to 80, preferably from 99 to 90% by weight, based on the sum of the components (A) and (B), of a monomer which is copolymerisable with the diketopyrrolopyrroles IV and V, the sums of (A) and (B) making up 100% by weight.    
     
     
         11 . A colour filter according to  claim 1  comprising a transparent substrate and a layer comprising from 5 to 50% by weight, based on the overall weight of the layer, of a diketopyrrolopyrrole of the general formula (I) dispersed in a high molecular mass organic material.  
     
     
         12 . A colour filter according to  claim 1  comprising a transparent substrate and a layer comprising from 25 to 40% by weight, based on the overall weight of the layer, of a diketopyrrolopyrrole of the general formula (I) dispersed in a high molecular mass organic material.  
     
     
         13 . A diketopyrrolopyrrole according to  claim 5 , wherein R 3  and R 4  are independently of each other C 1 -C 18 alkylmercapto, C 1 -C 18 alkoxy, or —NR 16 R 17 , wherein one of the groups R 16  and R 17  is hydrogen and the other is C 1 -C 18 alkyl or both groups R 16  and R 17  are independently of each other C 1 -C 18 alkyl.  
     
     
         14 . A diketopyrrolopyrrole according to  claim 8 , wherein R 21  and R 22  independently of one another are hydrogen, or C 1 -C 18 alkyl.