Polymerizable compound, mixture, polymerizable liquid crystal composition, polymer, optical film, optically anisotropic product, polarizing plate, flat panel display device, organic electroluminescence display device, and anti-reflection film

Abstract

Disclosed is a mixture containing polymerizable compounds having Formulas (III) and (IV) wherein Ar 1 and Ar 2 are divalent aromatic hydrocarbon or heteroaromatic ring group having D1 or D2 as a substituent; D 1 and D 2 are C1-C20 organic group having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon ring and heteroaromatic ring; A 11 -A 22 and B 11 -B 22 are alicyclic or aromatic group which may have a substituent, Y 11 -Y 22 and L 11 -L 22 are single bond, —O—, —CO—, —C0—O—, —O—CO—, —NR 21 —CO—, —CO—NR 22 —, —O—CO—O—, —NR 23 —CO—O—, —O—CO—NR 24 — or —NR 25 —CO—NR 26 — where R 21 -R 26 are hydrogen or C1-C6 alkyl group; R 4 -R 9 are hydrogen, methyl group or chlorine; one of f and k is integer of 1 to 3 with the other being integer of 0 to 3; g, j, m and q are integer of 1 to 20; and h, i, n and p are 0 or 1.

1 - 7 . (canceled) 
     
     
         8 . A polymerizable compound having the following Formula (III): 
       
         
           
           
               
               
           
         
         where Ar 1  represents divalent aromatic hydrocarbon ring group having D 1  as a substituent, or divalent heteroaromatic ring group having D 1  as a substituent, 
         D 1  represents C1-C20 organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and a heteroaromatic ring, 
         Z 11  and Z 12  represent each independently —CO—O—, —O—CO—, —NR 31 —CO— or —CO—NR 32 —, where R 31  and R 32  represent each independently hydrogen or C1-C6 alkyl group, 
         A 11 , A 12 , B 11  and B 12  represent each independently alicyclic group which may have a substituent, or aromatic group which may have a substituent, 
         Y 11 , Y 12 , L 11  and L 12  represent each independently single bond, —O—, —CO—, —CO—O—, —O—CO—, —NR 21 —CO—, —CO—NR 22 —, —O—CO—O—, —NR 23 —CO—O—, —O—CO—NR 24 — or —NR 25 —CO—NR 26 —, where R 21  to R 26  represent each independently hydrogen or C1-C6 alkyl group, 
         R 4  to R 7  represent each independently hydrogen, methyl group or chlorine, 
         one of f and k is an integer of 1 to 3 with the other being an integer of 0 to 3, 
         g and j represent each independently an integer of 1 to 20, and 
         h and i are each independently 0 or 1. 
       
     
     
         9 . The polymerizable compound of  claim 8 , wherein Ar 1 -D 1  is a divalent group having the following Formula (V): 
       
         
           
           
               
               
           
         
         where Ax represents C2-C20 organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and a heteroaromatic ring, and 
         Ra represents hydrogen or C1-C20 organic group which may have a substituent. 
       
     
     
         10 . The polymerizable compound of  claim 9 , wherein Ax is a group having the following Formula (VI): 
       
         
           
           
               
               
           
         
         where RX represents hydrogen, halogen, C1-C6 alkyl group, cyano group, nitro group, C1-C6 fluoroalkyl group, C1-C6 alkoxy group, or —C(═O)—O—R b , where R b  represents C1-C20 alkyl group which may have a substituent, C2-C20 alkenyl group which may have a substituent, C3-C12 cycloalkyl group which may have a substituent, or C5-C12 aromatic hydrocarbon ring group which may have a substituent, each Rx may be the same or different, and at least one CRx constituting the ring may be replaced by nitrogen. 
       
     
     
         11 . The polymerizable compound of  claim 9 , wherein Ra is C1-C20 alkyl group which may have a substituent, C2-C20 alkenyl group which may have a substituent, C2-20 alkynyl group which may have a substituent, or C6-C18 aromatic group which may have a substituent. 
     
     
         12 . A mixture comprising:
 the polymerizable compound of  claim 8 ; and   a polymerizable compound having the following Formula (IV):   
       
         
           
           
               
               
           
         
         where Ar 2  represents divalent aromatic hydrocarbon ring group having D 2  as a substituent, or divalent heteroaromatic ring group having D 2  as a substituent, 
         D 2  represents C1-C20 organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and a heteroaromatic ring, 
         Z 21  and Z 22  represent each independently —CO—O—, —O—CO—, —NR 31 —CO— or —CO—NR 32 —, where R 31  and R 32  represent each independently hydrogen or C1-C6 alkyl group, 
         A 21 , A 22 , B 21  and B 22  represent each independently alicyclic group which may have a substituent, or aromatic group which may have a substituent, 
         Y 21 , Y 22 , L 21  and L 22  represent each independently single bond, —O—, —CO—, —CO—O—, —O—CO—, —NR 21 —CO—, —CO—NR 22 —, —O—CO—O—, —NR 23 —CO—O—, —O—CO—NR 24 — or —NR 25   13  CO—NR 26 —, where R 21  to R 26  represent each independently hydrogen or C1-C6 alkyl group, 
         R 8  and R 9  represent each independently hydrogen, methyl group or chlorine, 
         m and q represent each independently an integer of 1 to 20, and 
         n and p are each independently 0 or 1. 
       
     
     
         13 . The mixture of  claim 12 , wherein Ar 1 -D 1  is a divalent group having the following Formula (V): 
       
         
           
           
               
               
           
         
         where Ax represents C2-C20 organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and a heteroaromatic ring, and 
         Ra represents hydrogen or C1-C20 organic group which may have a substituent, and wherein 
         Ar 2 -D 2  is a divalent group having the following Formula (VII): 
       
       
         
           
           
               
               
           
         
         where Ay represents C2-C20 organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and a heteroaromatic ring, and 
         Rc represents hydrogen or C1-C20 organic group which may have a substituent. 
       
     
     
         14 . The mixture of  claim 13 , wherein Ax and Ay are each independently a group having the following Formula (VI): 
       
         
           
           
               
               
           
         
         where R x  represents hydrogen, halogen, C1-C6 alkyl group, cyano group, nitro group, C1-C6 fluoroalkyl group, C1-C6 alkoxy group, or —C(═O)—O—R b , where R b  represents C1-C20 alkyl group which may have a substituent, C2-C20 alkenyl group which may have a substituent, C3-C12 cycloalkyl group which may have a substituent, or C5-C12 aromatic hydrocarbon ring group which may have a substituent, each R x  may be the same or different, and at least one C—R x  constituting the ring may be replaced by nitrogen. 
       
     
     
         15 . The mixture of  claim 13 , wherein Ra is C1-C20 alkyl group which may have a substituent, C2-C20 alkenyl group which may have a substituent, C2-20 alkynyl group which may have a substituent, or C6-C18 aromatic group which may have a substituent, and
 Rc is C1-C20 alkyl group which may have a substituent, C2-C20 alkenyl group which may have a substituent, C2-20 alkynyl group which may have a substituent, or C6-C18 aromatic group which may have a substituent.   
     
     
         16 . The mixture of  claim 12 , wherein a mass ratio of the polymerizable compound having Formula (III) to the polymerizable compound having Formula (IV) (polymerizable compound having Formula (III): polymerizable compound having Formula (IV)) is 1:1,000 to 20:100. 
     
     
         17 . A polymerizable liquid crystal composition comprising:
 the mixture of  claim 12 ; and   a polymerization initiator.   
     
     
         18 . A polymer obtainable by polymerization of the mixture of  claim 12 . 
     
     
         19 . A polymer obtainable by polymerization of the polymerizable liquid crystal composition of  claim 17 . 
     
     
         20 . An optical film comprising the polymer of  claim 18  as a constituent material. 
     
     
         21 . An optically anisotropic product comprising a layer which comprises the polymer of  claim 18  as a constituent material. 
     
     
         22 . A polarizing plate comprising:
 the optically anisotropic product of  claim 21 ; and   a polarizing film.   
     
     
         23 . A flat panel display device comprising:
 the polarizing plate of  claim 22 ; and   a liquid crystal panel.   
     
     
         24 . An organic electroluminescence display device comprising:
 the polarizing plate of  claim 22 ; and   an organic electroluminescence panel.   
     
     
         25 . An anti-reflection film comprising the polarizing plate of  claim 22 .