Hetero-polycyclic compounds, and coloring matters, pigments, dyes, color-changing material compositions, and color-changing films, made by using the compounds

Abstract

Provided are novel hetero-polycyclic compounds having a specific structure, color-changing material compositions comprising (A) a fluorescent coloring matter comprising at least one of the hetero-polycyclic compounds described above and (B) a binder material, color-changing films comprising the above hetero-polycyclic compounds, coloring matters comprising the above hetero-polycyclic compounds, and pigments or dyes comprising the hetero-polycyclic compounds described above, and provided are color-changing material compositions which are not deteriorated in a color-changing performance even after used for long time and which are prevented from being unusable due to deposition of coloring matters during storage and color-changing films produced by using the same, and novel hetero-polycyclic compounds, coloring matters and pigments or dyes which actualize them.

1 . A hetero-polycyclic compound represented by the following Formula (III): 
     
       
         
         
             
             
         
       
       wherein R 1  and R 2  each represent independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent, and they may be combined with each other to form a cyclic structure or may form a cyclic structure together with a benzene ring to which a nitrogen atom is bonded; 
       Y represents an oxygen atom, a sulfur atom or —NR 4 — (R 4  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); and 
       Ar represents an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent. 
     
   
   
       2 . A hetero-polycyclic compound represented by the following Formula (IV): 
     
       
         
         
             
             
         
       
       wherein R 1  and R 2  each represent independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent, and they may be combined with each other to form a cyclic structure or may form a cyclic structure together with a benzene ring to which a nitrogen atom is bonded; 
       Y represents an oxygen atom, a sulfur atom or —NR 4 — (R 4  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); and 
       Ar represents an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent. 
     
   
   
       3 . A hetero-polycyclic compound represented by the following Formula (V): 
     
       
         
         
             
             
         
       
       wherein R 1  and R 2  each represent independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent, and they may be combined with each other to form a cyclic structure or may form a cyclic structure together with a benzene ring to which a nitrogen atom is bonded; 
       X represents an oxygen atom, a sulfur atom, —NH— or —NR 3 — (R 3  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); 
       Y represents an oxygen atom, a sulfur atom, —NH— or —NR 4 — (R 4  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); and 
       Ar represents an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent. 
     
   
   
       4 . A hetero-polycyclic compound represented by the following Formula (VI): 
     
       
         
         
             
             
         
       
       wherein R 1  and R 2  each represent independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent, and they may be combined with each other to form a cyclic structure or may form a cyclic structure together with a benzene ring to which a nitrogen atom is bonded; 
       X represents an oxygen atom, a sulfur atom, —NH— or —NR 3 — (R 3  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); 
       Y represents an oxygen atom, a sulfur atom, —NH— or —NR 4 — (R 4  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); and 
       Ar represents an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent. 
     
   
   
       5 . A hetero-polycyclic compound represented by the following Formula (VII): 
     
       
         
         
             
             
         
       
       wherein R 1  and R 2  each represent independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent, and they may be combined with each other to form a cyclic structure or may form a cyclic structure together with a benzene ring to which a nitrogen atom is bonded; 
       X represents an oxygen atom, a sulfur atom, —NH— or —NR 3 — (R 3  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); 
       Y represents an oxygen atom, a sulfur atom, —NH— or —HR 4 — (R 4  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); and 
       Ar represents an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent. 
     
   
   
       6 . A hetero-polycyclic compound represented by the following Formula (VIII): 
     
       
         
         
             
             
         
       
       wherein R 1  and R 2  each represent independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent, and they may be combined with each other to form a cyclic structure or may form a cyclic structure together with a benzene ring to which a nitrogen atom is bonded; 
       X represents an oxygen atom, a sulfur atom, —NH— or —NR 3 — (R 3  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); 
       Y represents an oxygen atom, a sulfur atom, —NH— or —NR 4 — (R 4  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); and 
       Ar represents an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent. 
     
   
   
       7 . A color-changing material composition comprising (A) a fluorescent coloring matter comprising at least one of hetero-polycyclic compounds represented by the following Formulas (III) to (VIII) and (B) a binder material: 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       wherein R 1  and R 2  each represent independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent, and they may be combined with each other to form a cyclic structure or may form a cyclic structure together with a benzene ring to which a nitrogen atom is bonded; 
       X represents an oxygen atom, a sulfur atom, —NH— or —NR 3 — (R 3  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent); 
       Y represents an oxygen atom, a sulfur atom, —NH— or —NR 4 — (R 4  represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent), provided that Y represents an oxygen atom, a sulfur atom or —NR 4 — in Formulas (III) and (IV); and 
       Ar represents an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 5 to 20 carbon atoms which may have a substituent. 
     
   
   
       8 . The color-changing material composition as described in  claim 7 , wherein (B) the binder material described above is an optically reactive resin. 
   
   
       9 . The color-changing material composition as described in  claim 7 , wherein (B) the binder material described above is a thermosetting resin. 
   
   
       10 . The color-changing material composition as described in  claim 7 , wherein (B) the binder material described above is a thermoplastic resin. 
   
   
       11 . The color-changing material composition as described in  claim 7 , wherein (B) the binder material described above comprises (C) a methacrylic acid ester-methacrylic acid copolymer and (D) a monomer and/or oligomer having a photopolymerizable, ethylenically unsaturated group. 
   
   
       12 . The color-changing material composition as described in  claim 11 , wherein (B) the binder material described above comprises 10 to 200 parts by weight of (D) the monomer and/or oligomer having a photopolymerizable, ethylenically unsaturated group per 100 parts by weight of (C) the methacrylic acid ester-methacrylic acid copolymer. 
   
   
       13 . The color-changing material composition as described in  claim 7 , further comprising (E) a compound having an epoxy group. 
   
   
       14 . The color-changing material composition as described in  claim 13 , comprising 0.5 to 15% by weight of (E) the compound having an epoxy group based on the whole amount of the solid matters of the color-changing material composition described above. 
   
   
       15 . The color-changing material composition as described in  claim 7 , comprising 0.1 to 10% by weight of (A) the component described above based on the whole amount of the solid matters of the color-changing material composition described above. 
   
   
       16 . The color-changing material composition as described in  claim 7 , further comprising a fluorescent coloring matter comprising at least one selected from Rhodamine base fluorescent coloring matters. 
   
   
       17 . A coloring matter comprising the hetero-polycyclic compound as described in  claim 1 . 
   
   
       18 . A pigment or a dye comprising the hetero-polycyclic compound as described in  claim 1 .