Metallocenyl Phthalocyanine Compounds and Use Thereof

Abstract

This invention relates to a novel metallocenyl phthalocyanine compound represented by the following general formula (I), in which at least one of the four benzene rings of phthalocyanine is connected with the organometallic complex group through a linker having one carbon atom. This invention also relates to the use of the phthalocyanine compounds in optical recording media. wherein all symbols are defined in the specification.

1 . A metallocenyl-phthalocyanine compound represented by formula (I):  
     
       
         
         
             
             
         
       
     
     wherein, 
 M 1  represents two hydrogen atoms, a divalent metal, a trivalent metal having one ligand, or a tetravalent metal having two ligands;  
 Y 1 , Y 2 , Y 3 , Y 4  each independently represents a group —O—R 1 , —S—R 1 , or —NR 1 R 2 ;  
 R 1  and R 2  each independently represents a hydrogen atom; a C 1 -C 10  straight-chain, branched, or cyclic alkyl; a C 2 -C 10  straight-chain, branched, or cyclic alkenyl; or a C 2 -C 10  straight, branched, or cyclic alkynyl;  
 Z represents the group of formula  
                     
 in which R 3  and R 4  each independently represents a hydrogen atom, a C 1 -C 4  alkyl, or a C 2 -C 4  alkenyl;  
 R 5  and R each independently represents a hydrogen atom, a halogen atom, a nitro group, a C 1 -C 4  alkyl, a C 1 -C 4  alkoxy, a C 1 -C 4  alkylamino, a di(C 1 -C 4 alkyl)amino, or a diarylphosphine group in which the aryl is unsubstituted or substituted;  
 M 2  is selected from an atom consisting of Fe(II), Co(II), and Ni(II);  
 wherein l, m, n, o each independently represents 0, 1 or 2, and l+m+n++o is between 1 and 8.  
 
   
   
       2 . The compound according to  claim 1 , wherein M 1  is two hydrogen atoms, or a atom selected from Cu(II), Pd(II), Zn(II), Co(II), or Ni(II).  
   
   
       3 . The compound according to  claim 1 , wherein M 1  is Cu(II) or Pd(II).  
   
   
       4 . The compound according to  claim 1 , wherein Y 1 , Y 2 , Y 3  and Y 4  each independently represents a group —O—R 1 .  
   
   
       5 . The compound according to  claim 1 , wherein all Y 1 , Y 2 , Y 3  and Y 4  are 2,4-dimethyl-3-pentyloxy.  
   
   
       6 . The compound according to  claim 1 , wherein both R 3  and R 4  are a hydrogen atom; R 5  and R 6  are independently hydrogen, C 1 -C 4  alkyl, or halogen; and M 2  is Fe(II).  
   
   
       7 . An optical recording medium, which comprises a substrate, a recording layer and a reflecting or partially reflecting layer, wherein the recording layer comprises the compound or mixtures according to any one of  claims 1  to  6 .  
   
   
       8 . A metallocenyl-phthalocyanine compound represented by formula (II):  
     
       
         
         
             
             
         
       
       wherein M 1  represents Cu(II) or Pd(II);  
       R 1  represents a hydrogen atom, a C 1 -C 10  straight-chain, branched, or cyclic alkyl; C 2 -C 10  straight-chain, branched, or a cyclic alkenyl; or a C 2 -C 10  straight-cha, branched, or cyclic alkynyl;  
       Z′ represents a group of formula  
       
         
           
           
               
               
           
         
       
       in which R 5  and R 6  each independently represents a hydrogen atom, a halogen atom, a nitro group, a C 1 -C 4  alkyl, a C 1 -C 4  alkoxy, a C 1 -C 4  alkylamino, a di(C 1 -C 4 alkyl)amino or a diarylphosphine group in which the aryl group is unsubstituted or substituted-M 2  is selected from an atom consisting of Fe(II), Co(II), and Ni(II);  
       wherein l′, m′, n′, o′ each independently represents 0, 1 or 2, and (l′+m′+n′+o′) is between 1 and 4.  
     
   
   
       9 . The compound according to  claim 8 , wherein R 1  is 2,4-dimethyl-3-pentyl.  
   
   
       10 . The compound according to  claim 8 , wherein R 5  and R 6  are independently hydrogen, C 1 -C 4  alkyl, halogen, and M 2  is Fe(II).  
   
   
       11 . An optical recording medium, which comprises a substrate, a recording layer and a reflecting or partially reflecting layer, wherein the recording layer comprises the compound or a mixture thereof according to any one of  claims 8  to  10 .  
   
   
       12 . A process for the preparation of the metallocenyl phthalocyanine compound according to  claim 8 , which comprise the reacting of a compound of formula (VIII) and a compound of formula (VI) via a Friedel-Crafts reaction in aprotic solvents and in the presence of an acidic catalyst at a temperature between 20 and 120° C.:  
     
       
         
         
             
             
         
       
     
     wherein, 
 M 1  represents Cu(I) or Pd(II);  
 R 1  represents a hydrogen atom; a C 1 -C 10  straight-chain, branched, or cyclic alkyl; a C 2 -C 10  straight-chain, branched, or cyclic alkenyl; or a C 2 -C 10  straight-chain, branched, or cyclic alkynyl;  
                     
 wherein L′ is a leaving group; R 5  and R 6  each independently represents a hydrogen atom, a halogen atom, a nitro group, a C 1 -C 4  alkyl, a C 1 -C 4  alkoxy, a C 1 -C 4  alkylamino, a di(C 1 -C 4 alkyl)amino, or a diarylphosphine group in which the aryl is unsubstituted or substituted; and  
 M 2  is selected from an atom consisting of Fe(II), Co(II), and Ni(II).