Liquid crystal display device and method for manufacturing same

Abstract

The present invention relates to a liquid crystal display element including a pair of a substrate arranged opposite to each other, an electrode group disposed on one side or both sides of the pair of substrates facing each other, a plurality of active elements connected to the electrode group, a liquid crystal alignment film disposed on each facing side of the pair of substrates, and a liquid crystal layer interposed between the pair of substrates, wherein the liquid crystal alignment film is manufactured by irradiating linearly polarized light to a film obtained from polyamic acid or a derivative thereof having a photoisomerization structure in the main chain or a film being subject to heat-baking so as to provide alignment-controlling capability, and the liquid crystal layer is a liquid crystal composition having negative (−) dielectric anisotropy. By the present invention, a liquid crystal display element having improved image sticking characteristics and good alignment stability is provided.

1 . A liquid crystal display device, comprising
 a pair of substrates arranged opposite to each other,   an electrode group disposed on one side or both sides of the pair of substrates facing each other,   a plurality of active devices connected to the electrode group,   a liquid crystal alignment film disposed on each facing side of the pair of substrates, and   a liquid crystal layer interposed between the pair of substrates,   wherein the liquid crystal alignment film is manufactured by irradiating linearly polarized light to a film obtained from polyamic acid or a derivative thereof having a photoisomerization structure in the main chain or a film being subject to heat-baking so as to provide alignment-controlling capability, and   the liquid crystal layer comprises a liquid crystal composition having negative dielectric anisotropy and including at least one liquid crystal compound selected from the group of liquid crystal compounds of Formula (1-3), Formula (1-7), Formula (1-11), Formula (1-14), Formula (1-15), Formula (1-17), Formula (1-18), Formula (1-28), and Formula (1-32) as a first component:   
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons, where arbitrary hydrogen is replaced by fluorine; 
       
     
     
         2 . The liquid crystal display device of  claim 1 , wherein the liquid crystal composition having negative dielectric anisotropy comprises at least one selected from the group of liquid crystal compounds of Formula (1-7) and Formula (1-32) as a first component: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons where arbitrary hydrogen is replaced by fluorine. 
       
     
     
         3 . The liquid crystal display device of  claim 1 , wherein an electric field applied to a liquid crystal layer has a component parallel to the surface of the substrate. 
     
     
         4 . The liquid crystal display device of  claim 1 , wherein the polyamic acid or the derivative thereof having a photoisomerization structure is polyamic acid or a derivative thereof obtained by reacting at least one of a tetracarboxylic dianhydride or a diamine having a photoisomerization structure selected from the following Formulae (I) to (VII):
   [Formula 2]     R 2 —C≡C—R 3   (I)
     R 2 —C≡C—C≡C—R 3   (II)
     R 2 —C≡C—CH═CH—R 3   (III)
     R 2 —C≡C—R 4 —C≡C—R 3   (IV)
     R 2 —C≡C—R 1 —CH═CH—R 3   (V)
     R 2 —CH═CH—R 3   (VI)
     R 2 —N═N—R 3   (VII)
   wherein, in Formulae (I) to (VII), R 2  and R 3  are independently a monovalent organic group having —NH 2  or —CO—O—CO—, and R 4  is a divalent organic group including an aromatic ring.   
     
     
         5 . The liquid crystal display device of  claim 4 , wherein the tetracarboxylic dianhydride having the photoisomerization structure is at least one selected from the following Formula (PAN-1) and Formula (PAN-2): 
       
         
           
           
               
               
           
         
       
     
     
         6 . The liquid crystal display device of  claim 4 , wherein the diamine having the photoisomerization structure is at least one selected from the following Formula (PDI-1) to Formula (PDI-8): 
       
         
           
           
               
               
           
         
         wherein, in Formula (PDI-1) to Formula (PDI-8), as for a group of which a bonding position is not fixed to any one of carbon atoms constituting a ring, the bonding position is arbitrary, 
         in Formula (PDI-7), R 5  is independently —CH 3 , —OCH 3 , —CF 3 , or —COOCH 3 , and 
         b is an integer of 0 to 2. 
       
     
     
         7 . The liquid crystal display device of  claim 6 , wherein the diamine having the photoisomerization structure is at least one selected from the following Formula (PDI-6-1) and Formula (PDI-7-1): 
       
         
           
           
               
               
           
         
       
     
     
         8 . The liquid crystal display device of  claim 4 , which comprises at least one of the group of a tetracarboxylic dianhydride represented by the following Formula (AN-I) to Formula (AN-VII), as a tetracarboxylic dianhydride in addition to the tetracarboxylic dianhydride having the photoisomerization structure: 
       
         
           
           
               
               
           
         
         wherein, in Formula (AN-I), Formula (AN-IV), and Formula (AN-V), X is independently a single bond or —CH 2 —; 
         in Formula (AN-II), G is a single bond, alkylene having 1 to 20 carbons, —CO—, —O—, —S—, —SO 2 —, —C(CH 3 ) 2 —, or —C(CF 3 ) 2 —; and 
         in Formula (AN-II) to Formula (AN-IV), Y is independently one selected from the group of the following trivalent groups: 
       
       
         
           
           
               
               
           
         
         wherein arbitrary hydrogen of the groups is optionally replaced by methyl, ethyl, or phenyl; 
         in Formula (AN-Ill) to Formula (AN-V), ring A is a monocyclic hydrocarbon group having 3 to 10 carbons or a condensed polycyclic hydrocarbon group having 6 to 10 carbons, wherein arbitrary hydrogen of the groups is optionally replaced by methyl, ethyl, or phenyl, a bond bound to the ring is bound to arbitrary carbon constituting the ring, or two bonds is optionally bound to the same carbon; 
         in Formula (AN-VI), X 10  is alkylene having 2 to 6 carbons; 
         Me is methyl; 
         Ph is phenyl; 
         in Formula (AN-VII), G 10  is independently —O—, —COO—, or —OCO—; and 
         r is independently 0 or 1. 
       
     
     
         9 . The liquid crystal display device of  claim 8 , wherein the tetracarboxylic dianhydride in addition to the tetracarboxylic dianhydride having the photoisomerization structure comprises at least one selected from the group of the following Formula (AN-1-1), Formula (AN-1-13), Formula (AN-2-1), Formula (AN-3-1), Formula (AN-3-2), Formula (AN-4-5), Formula (AN-4-17), Formula (AN-4-21), Formula (AN-4-28), Formula (AN-4-29), Formula (AN-7-2), Formula (AN-10), and Formula (AN-11-3): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein, in Formula (AN-4-17), m is an integer of 1 to 12. 
       
     
     
         10 . The liquid crystal display device of  claim 4 , which comprises at least one selected from the group of the following Formula (DI-1) to Formula (DI-15), as a diamine in addition to the diamine having the photoisomerization structure selected from Formula (I) to Formula (VII): 
       
         
           
           
               
               
           
         
         wherein, in Formula (DI-1), m is an integer of 1 to 12; 
         in Formula (DI-3) and Formula (DI-5) to Formula (DI-7), G 21  is independently a single bond, —NH—, —O—, —S—, —S—S—, —SO 2 —, —CO—, —CONH—, —CONCH 3 —, —NHCO—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —(CH 2 ) m —, —O—(CH 2 ) m —O—, —N(CH 3 )—(CH 2 ) k —N(CH 3 )—, or —S—(CH 2 ) m —S—, m′ is independently an integer of 1 to 12, and k is an integer of 1 to 5; 
         in Formula (DI-6) and Formula (DI-7), G 22  is independently a single bond, —O—, —S—, —CO—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, or alkylene having 1 to 10 carbons; 
         arbitrary —H of a cyclohexane ring and a benzene ring of Formula (DI-2) to Formula (DI-7) is optionally replaced by —F, —CH 3 , —OH, —CF 3 , —CO 2 H, —CO 2 H, —CONH 2 , or benzyl, or that in Formula (DI-4) is optionally replaced by the following Formula (DI-4-a) to Formula (DI-4-c): 
       
       
         
           
           
               
               
           
         
         wherein, in Formula (DI-4-a) and Formula (DI-4-b), R 20  is independently —H or —CH 3 ; 
         in Formula (DI-2)-Formula (DI-7), as for a group of which a bonding position is not fixed to any one of carbon atoms constituting a ring, the bonding position is arbitrary; and 
         a bonding position of NH 2  bound to the cyclohexane ring or benzene ring is arbitrary except a bonding position of G 21  or G 22 , 
       
       
         
           
           
               
               
           
         
         wherein, in Formula (DI-8), R 21  and R 22  are independently alkyl having 1 to 3 carbons or phenyl; 
         G 23  is independently C1-C6 alkylene, phenylene, or alkyl-substituted phenylene; 
         n is an integer of 1-10; 
         in Formula (DI-9), R 23  is independently alkyl having 1 to 5 carbons, alkoxy having 1 to 5 carbons, or —Cl; 
         p is independently an integer of 1 to 3; 
         q is an integer of 0 to 4; 
         in Formula (DI-10), R 24  is —H, alkyl having 1 to 4 carbons, phenyl, or benzyl; 
         in Formula (DI-11), G 24  is —CH 2 — or —NH—; 
         in Formula (DI-12), G 25  is a single bond, alkylene having 2 to 6 carbons, or 1,4-phenylene; 
         r is 0 or 1; 
         in Formula (DI-12), as for a group of which a bonding position is not fixed to any one of carbon atoms constituting a ring, the bonding position is arbitrary; and 
         in Formula (DI-9), Formula (DI-11), and Formula (DI-12), a bonding position of NH 2  bound to the benzene ring is arbitrary, 
       
       
         
           
           
               
               
           
         
         wherein, in Formula (DI-13), G 31  is a single bond, alkylene having 1 to 20 carbons, —CO—, —O—, —S—, —SO 2 —, —C(CH 3 ) 2 —, or —C(CF 3 ) 2 —; 
         in Formula (DI-14), ring B is optionally a cyclohexane ring, a benzene ring, or a naphthalene ring, where arbitrary hydrogen of the rings is optionally replaced by methyl, ethyl, or phenyl; 
         in Formula (DI-15), rings C are each independently a cyclohexane ring or a benzene ring, where arbitrary hydrogen of the rings is optionally replaced by methyl, ethyl, or phenyl; and 
         Y is a single bond, alkylene having 1 to 20 carbons, —CO—, —O—, —S—, —SO 2 —, —C(CH 3 ) 2 —, or —C(CF 3 ) 2 —. 
       
     
     
         11 . The liquid crystal display device of  claim 10 , wherein the diamine in addition to the diamine having the photoisomerization structure selected from Formula (I) to Formula (VII) comprises at least one selected from the group of the following Formula (DI-1-3), Formula (DI-1-4), Formula (DI-4-1), Formula (DI-5-1), Formula (DI-5-5), Formula (DI-5-9), Formula (DI-5-12), Formula (DI-5-21), Formula (DI-5-28), Formula (DI-5-30), Formula (DI-5-31), Formula (DI-7-3), Formula (DI-9-1), Formula (DI-13-1), Formula (DI-13-2), Formula (DI-14-1), or Formula (DI-14-2): 
       
         
           
           
               
               
           
         
         wherein in Formula (DI-5-1), Formula (DI-5-12), Formula (DI-7-3), and Formula (DI-13-2), m is an integer of 1 to 12; 
         in Formula (DI-5-30), k is an integer of 1 to 5; and 
         in Formula (DI-7-3), n is 1 or 2. 
       
     
     
         12 . The liquid crystal display device of  claim 1 , wherein the liquid crystal alignment film is formed by a liquid crystal alignment agent including the polyamic acid or the derivative thereof having a photoisomerization structure in the main chain, and other polymers. 
     
     
         13 . The liquid crystal display device of  claim 1 , wherein the liquid crystal alignment film is formed of a liquid crystal alignment agent further comprising at least one selected from the group of compounds of an alkenyl-substituted nadimide compound, a compound having a radical-polymerizable unsaturated double bond, an oxazine compound, an oxazoline compound, and an epoxy compound. 
     
     
         14 . The liquid crystal display device of  claim 1 , which is manufactured by applying a liquid crystal alignment agent on a substrate, heat-drying the substrate applied with the liquid crystal alignment agent, and irradiating linearly polarized light to provide alignment capability. 
     
     
         15 . The liquid crystal display device of  claim 1 , which is manufactured by applying a liquid crystal alignment agent on a substrate, heat-drying the substrate applied with the liquid crystal alignment agent, irradiating linearly polarized light to provide alignment capability, and then heat-baking the resultant film. 
     
     
         16 . The liquid crystal display device of  claim 1 , which is manufactured by applying a liquid crystal alignment agent on a substrate, heat-drying the substrate applied with the liquid crystal alignment agent, heat-baking the dried film, and irradiating linearly polarized light to provide alignment capability.