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 (II): 
     
       
         
         
             
             
         
       
     
     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; and 
 X represents an oxygen atom, a sulfur atom, —NH— or —NR 3 —, wherein 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. 
 
   
   
       2 . The hetero-polycyclic compound according to  claim 1 , wherein said alkyl group having 1 to 10 carbon atoms, as defined in R 1 , R 2  and R 3 , is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, various butyls, various pentyls, various hexyls, various octyls, various decyls, cyclopentyl, cyclohexyl, cyclooctyl, benzyl and phenethyl. 
   
   
       3 . The hetero-polycyclic compound according to  claim 1 , wherein said arylalkyl group having 7 to 30 carbon atoms, as defined in R 1  and R 2 , is selected from the group consisting of benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, 1-pyrrolylmethyl, 2-(1-pyrrolyl)ethyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, p-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. 
   
   
       4 . The hetero-polycyclic compound according to  claim 1 , wherein said aryl group having 6 to 20 carbon atoms, as defined in R 1 , R 2  and R 3 , is selected from the group consisting of phenyl, naphthyl, anthryl and pyrenyl. 
   
   
       5 . The hetero-polycyclic compound according to  claim 1 , wherein said heteroaryl group having 5 to 20 carbon atoms, as defined in R 1 , R 2  and R 3 , is selected from the group consisting of 1-aza-indolizine-2-yl, 1-aza-indolizine-3-yl, 1-aza-indolizine-5-yl, 1-aza-indolizine-6-yl, 1-aza-indolizine-7-yl, 1-aza-indolizine-8-yl, 2-aza-indolizine-1-yl, 2-aza-indolizine-3-yl, 2-aza-indolizine-5-yl, 2-aza-indolizine-6-yl, 2-aza-indolizine-7-yl, 2-aza-indolizine-8-yl, 6-aza-indolizine-1-yl, 6-aza-indolizine-2-yl, 6-aza-indolizine-3-yl, 6-aza-indolizine-5-yl, 6-aza-indolizine-7-yl, 6-aza-indolizine-8-yl, 7-aza-indolizine-1-yl, 7-aza-indolizine-2-yl, 7-aza-indolizine-3-yl, 7-aza-indolizine-5-yl, 7-aza-indolizine-6-yl, 7-aza-indolizine-7-yl, 7-aza-indolizine-8-yl, 8-aza-indolizine-1-yl, 8-aza-indolizine-2-yl, 8-aza-indolizine-3-yl, 8-aza-indolizine-5-yl, 8-aza-indolizine-6-yl, 8-aza-indolizine-7-yl, 1-indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizinyl, 8-indolizinyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl, 1,8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl, 1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl, 2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 10-phenothiazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-frazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl and 4-t-butyl-3-indolyl. 
   
   
       6 . The hetero-polycyclic compound according to  claim 1 , wherein said substituent of the alkyl group, arylalkyl group, aryl group and heteroaryl group, as defined in R 1 , R 2  and R 3 , is independently selected from the group consisting of an alkyl group, an alkoxyl group, a halogen atom, a cyano group, an alkoxycarbonyl group, a carboxyl group, an ester group, an amide group, a sulfoxyl group, a sulfonamide group, a nitro group, an aryl group and a heteroaryl group. 
   
   
       7 . The hetero-polycyclic compound according to  claim 1 , wherein R 1  and R 2  are each independently C 4 H 9 . 
   
   
       8 . The hetero-polycyclic compound according to  claim 1 , wherein X is an oxygen atom and R 1  and R 2  are each independently a butyl. 
   
   
       9 . A coloring matter comprising the hetero-polycyclic compound as described in  claim 1 . 
   
   
       10 . A pigment or a dye comprising the hetero-polycyclic compound as described in  claim 1 .