Vinyl-group-containing fluorene compound

Abstract

A novel vinyl-group-containing fluorene compound and a method for producing the same, a polymerizable monomer and cross-linking agent including the compound, a leaving-group-containing fluorene compound, a monovinyl-group-containing fluorene compound, and methods for producing the same. The vinyl-group-containing fluorene compound is represented by formula (1) in which W 1 and W 2 represent a group represented by formula (2), a group represented by formula (4), a hydroxyl group, or a (meth)acryloyloxy group, R 3a and R 3b represent a cyano group, a halogen atom, or a monovalent hydrocarbon, and n1 and n2 are integers of 0-4. In formulas (2) and (4), (Z) is an aromatic hydrocarbon ring, X is a single bond or a group represented by —S—, R 1 is a single bond or a C1-4 alkylene group, R 2 is a substituent such as a monovalent hydrocarbon, and m is an integer of 0 or more).

1 . A (meth)acryloyloxy group-containing fluorene-based compound represented by the following general formula (19): 
       
         
           
           
               
               
           
         
       
       wherein W 13  and W 14  each independently represent a group represented by the following general formula (12), a hydroxyl group, or a (meth)acryloyloxy group, provided that at least one of W 13  and W 14  represents a group represented by the following general formula (12); R 3a  and R 3b  each independently represent a cyano group, a halogen atom, or a monovalent hydrocarbon group; and n1 and n2 each independently represent an integer of 0 to 4, 
       
         
           
           
               
               
           
         
         wherein a ring Z represents a fused polycyclic aromatic hydrocarbon ring; X represents a single bond or —S—; R 1  represents a single bond; R 2  represents substituent group A or B, 
         wherein substituent group A represents a monovalent hydrocarbon group, a hydroxyl group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR 4c , a group represented by —N(R 4d ) 2 , a (meth)acryloyloxy group, or a sulfo group; and substituent group B represents a group formed by substituting at least a part of hydrogen atoms bonded to carbon atoms of the substituents contained in substituent group C below with a monovalent hydrocarbon group, a hydroxyl group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR 4c , a group represented by —N(R 4d ) 2 , a (meth)acryloyloxy group, a mesyloxy group, or a sulfo group,
 wherein substituent group C represents a monovalent hydrocarbon group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a group represented by —NHR 4 c or a group represented by —N(R 4d ) 2 ; 
 R 4a  to R 4d  each independently represent a monovalent hydrocarbon group; and 
 m is an integer of 0 or more. 
 
       
     
     
         2 . The (meth)acryloyloxy group-containing fluorene-based compound according to  claim 1 , wherein the ring Z is a naphthalene ring. 
     
     
         3 . A process for producing a (meth)acryloyloxy group-containing fluorene-based compound according to  claim 1 , the process comprising obtaining the (meth)acryloyloxy group-containing fluorene-based compound from a hydroxyl group-containing fluorene-based compound represented by the following general formula (3): 
       
         
           
           
               
               
           
         
       
       wherein W 3  and W 4  each independently represent a group represented by the following general formula (4) or a hydroxyl group, provided that W 3  and W 4  do not simultaneously represent a hydroxyl group; R 3a  and R 3b  each independently represent a cyano group, a halogen atom, or a monovalent hydrocarbon group; and n1 and n2 each independently represent an integer of 0 to 4, 
       
         
           
           
               
               
           
         
       
       wherein a ring Z represents a fused polycyclic aromatic hydrocarbon ring; X represents a single bond or —S—; R 1  represents a single bond; R 2  represents substituent group A or B, wherein substituent group A represents a monovalent hydrocarbon group, a hydroxyl group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR 4c , a group represented by —N(R 4d ) 2 , a (meth)acryloyloxy group, or a sulfo group; and
 substituent group B represents a group formed by substituting at least a part of hydrogen atoms bonded to carbon atoms of the substituents contained in substituent group C below with a monovalent hydrocarbon group, a hydroxyl group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR 4c , a group represented by —N(R 4d ) 2 , a (meth)acryloyloxy group, a mesyloxy group, or a sulfo group;
 wherein substituent group C represents a monovalent hydrocarbon group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a group represented by —NHR 4c  or a group represented by —N(R 4d ) 2 ; and 
 
 R 4a  to R 4d  each independently represent a monovalent hydrocarbon group; and m is an integer of 0 or more. 
 
     
     
         4 . The process for producing a vinyl-group-containing fluorene-based compound according to  claim 3  wherein the ring Z is a naphthalene ring.