Organic Compound, Optical Film and Method of Production thereof

Abstract

An organic compound has the general structural formula I. In the formula I, Core is a conjugated organic unit capable of forming a rod-like macromolecule, n is a number of the conjugated organic units in the rod-like macromolecule, G k is a set of ionogenic side-groups, and k is a number of the side-groups in the set G k . The set of the ionogenic side-groups provide solubility of the organic compound or its salts and give rigidity to the rod-like macromolecule. The number n provides molecule anisotropy that promotes self-assembling of macromolecules in a solution of the organic compound or its salts, forming lyotropic liquid crystal. The solution is capable of forming a solid optical retardation layer of positive A-type substantially transparent to electromagnetic radiation in the visible spectral range. An optical film based on an organic compound of the general formula I and a method of making same are also disclosed.

1 . An organic compound of the general structural formula I: 
       
         
           
           
               
               
           
         
         where Core is a conjugated organic unit capable of forming a rod-like macromolecule, 
         n is a number of the conjugated organic units in the rod-like macromolecule,
 G k  is a set of ionogenic side-groups, and 
 k is a number of the side-groups in the set G k ; 
 
         wherein the set of the ionogenic side-groups provides solubility of the organic compound or its salts and gives rigidity to the rod-like macromolecule; 
         the number n provides a molecule anisotropy that promotes self-assembling of macromolecules in a solution of the organic compound or its salts, forming lyotropic liquid crystal; and 
         wherein the solution is capable of forming a solid optical retardation layer of positive A-type substantially transparent to electromagnetic radiation in the visible spectral range. 
       
     
     
         2 . An organic compound according to  claim 1 , wherein the number k is equal to 0, 1, 2, 3, 4, 5, 6, 7, or 8 and the number n belongs to the range from 10 to 100000. 
     
     
         3 . An organic compound according to  claim 1 , wherein under the increased shear rate the viscosity of the solution decreases down to a value in the range from 10 to 200 mPa·s. 
     
     
         4 . An organic compound according to  claim 1 , wherein the rod-like macromolecule is a polymeric main rigid-chain, and wherein the conjugated organic units are the same. 
     
     
         5 . An organic compound according to  claim 1 , wherein the rod-like macromolecule is a copolymeric main rigid-chain, and wherein at least one conjugated organic unit is different from others. 
     
     
         6 . An organic compound according to  claim 1 , wherein the number k is more than 1, and the ionogenic side-groups are the same. 
     
     
         7 . An organic compound according to  claim 1 , wherein the number k is more than 1, and at least one said side-group is different from others. 
     
     
         8 . An organic compound according to  claim 1 , wherein at least one conjugated organic unit (Core) of the rod-like macromolecule has the general structural formula III: 
       
         
           
           
               
               
           
         
         wherein Core 1  and Core 2  are conjugated organic components, Z is selected from the list comprising —O— and —NR—, where R is a substituent selected from the list comprising hydrogen, linear and branched (C 1 -C 4 )alkyls, phenyl and substituted phenyl, wherein substituents on the phenyl include linear and branched (C 1 -C 4 )alkyls 
       
     
     
         9 . An organic compound according to  claim 8 , wherein Core1 and Core2, comprising ionogenic groups G, are same or different and independently selected from the structures having general formula 1 to 2: 
       
         
           
           
               
               
           
         
         wherein the ionogenic side-groups G are selected from the list comprising —COOH, —SO 3 H, and —H 2 PO 3 , k is equal to 0, 1 or 2, p is equal to 1, 2 or 3. 
       
     
     
         10 . An organic compound according to  claim 1 , which is selected from structures 3-7: 
       
         
           
           
               
               
           
         
       
     
     
         11 . An organic compound according to  claim 1 , further comprising additional side-groups independently selected from the list comprising linear and branched (C 1 -C 20 )alkyl, (C 2 -C 20 )alkenyl, and (C 2 -C 20 )alkinyl. 
     
     
         12 . An organic compound according to  claim 11 , wherein at least one of the additional side-groups is connected with the Core via a bridging group A. 
     
     
         13 . An organic compound according to  claim 12 , wherein the bridging group A is selected from the list comprising —C(O)—, —C(O)O—, —C(O)—NH—, —(SO 2 )NH—, —O—, —CH 2 O—, —NH—, >N—, and any combination thereof. 
     
     
         14 . An organic compound according to  claim 1 , wherein the salt of the organic compound is selected from the list comprising alkali-metal salts and ammonium salt. 
     
     
         15 . An optical film comprising:
 a substrate having front and rear surfaces, and   at least one solid optical retardation layer on the front surface of the substrate,   wherein the solid optical retardation layer comprises at least one organic compound of the general structural formula II   
       
         
           
           
               
               
           
         
         where Core is a conjugated organic unit capable of forming a rod-like macromolecule, 
         n is a number of the conjugated organic units in the rod-like macromolecule, 
         G k  is a set of ionogenic side-groups, 
         k is a number of the side-groups in the set G k , 
         X is a counterion selected from a list comprising H + , NH (3-m) R m   +  (where R is alkyl, m is 1, 2 or 3) Na + , K + , Li + , Cs + , Ba 2+ , Ca 2+ , Mg 2+ , Sr 2+ , Pb 2+ , Zn 2+ , La 3+ , Ce 3+ , Y 3+ , Yb 3+ , Gd 3+ , Zr 4+  and any combination thereof, 
         t is the number of counterions; wherein the side-groups and the number m provide solubility of the organic compound and give rigidity to the rod-like macromolecule, 
         number n provides molecule anisotropy that promotes self-assembling of macromolecules in solution of the organic compound or its salts, forming lyotropic liquid crystal; 
         wherein the solid optical retardation layer is an uniaxial positive A-type layer and is substantially transparent to electromagnetic radiation in the visible spectral range. 
       
     
     
         16 . An optical film according to  claim 15 , wherein the number k is equal to 0, 1, 2, 3, 4, 5, 6, 7, or 8 and the number n belongs to the range from 10 to 100000. 
     
     
         17 . An optical film according to  claim 15 , wherein under the increased shear rate the viscosity of the solution decreases down to a value in the range from 10 to 200 mPa·s. 
     
     
         18 . An optical film according to  claim 15 , wherein the rod-like macromolecule is a polymeric main rigid-chain, and wherein the conjugated organic units are the same. 
     
     
         19 . An optical film according to  claim 15 , wherein the rod-like macromolecule is a copolymeric main rigid-chain, and wherein at least one conjugated organic unit is different from others. 
     
     
         20 . An optical film according to  claim 15 , wherein the number k is more than 1, and the ionogenic side-groups are the same. 
     
     
         21 . An optical film according to  claim 15 , wherein the number k is more than 1, and at least one said side-group is different from others. 
     
     
         22 . An optical film according to  claim 15 , wherein at least one conjugated organic unit (Core) of the rod-like macromolecule has the general structural formula III: 
       
         
           
           
               
               
           
         
         wherein Core 1  and Core 2  are conjugated organic components, Z is selected from the list comprising —O— and —NR—, where R is a substituent selected from the list comprising hydrogen, linear and branched (C 1 -C 4 )alkyls, phenyl and substituted phenyl, wherein substituents on the phenyl include linear and branched (C 1 -C 4 )alkyls. 
       
     
     
         23 . An optical film according to  claim 22 , wherein Core1 and Core2, comprising ionogenic groups G, are same or different and independently selected from the structures having general formula 1 to 2: 
       
         
           
           
               
               
           
         
         wherein the ionogenic side-groups G are selected from the list comprising —COOH, —SO 3 H, and —H 2 PO 3 , k is equal to 0, 1 or 2, p is equal to 1, 2 or 3. 
       
     
     
         24 . An optical film according to  claim 15 , comprising the organic compound which is selected from structures 3-7: 
       
         
           
           
               
               
           
         
       
     
     
         25 . An optical film according to  claim 15 , wherein the organic compound further comprises additional side-groups independently selected from the list comprising linear and branched (C 1 -C 20 )alkyl, (C 2 -C 20 )alkenyl, and (C 2 -C 20 )alkinyl. 
     
     
         26 . An optical film according to  claim 25 , wherein at least one of the additional side-groups is connected with the Core via a bridging group A. 
     
     
         27 . An optical film according to  claim 26 , wherein the bridging group A is selected from the list comprising —C(O)—, —C(O)O—, —C(O)—NH—, —(SO 2 )NH—, —O—, —CH 2 O—, —NH—, >N—, and any combination thereof. 
     
     
         28 . An optical film according to  claim 15 , wherein the salt is selected from the list comprising alkali-metal salts and ammonium salt. 
     
     
         29 . An optical film according to  claim 15 , further comprising inorganic compounds which are selected from the list comprising hydroxides and salts of alkali metals. 
     
     
         30 . An optical film according to  claim 15 , wherein said solid retardation layer is generally an uniaxial retardation layer possessing two refractive indices (n x  and n y ) corresponding to two mutually perpendicular directions in the plane of the substrate and one refractive index (n z ) in the normal direction to the plane of the substrate, and wherein the refractive indices obey the following condition: n z =n y <n x . 
     
     
         31 . An optical film according to  claim 15 , wherein the substrate material is selected from the list comprising a polymer and a glass. 
     
     
         32 . A method of producing an optical film, comprising the steps of
 a) preparation of a nematic lyotropic liquid crystal solution of an organic compound of the general structural formula I or a salt thereof   
       
         
           
           
               
               
           
         
         where Core is a conjugated organic unit capable of forming a rod-like macromolecule, 
         n is a number of the conjugated organic units in the rod-like macromolecule, 
         G k  is a set of ionogenic side-groups, and 
         k is a number of the side-groups in the set G k ; 
         wherein the side-groups and the number k provide solubility of the organic compound and its salts and give rigidity to the rod-like macromolecule, and 
         the number n provides molecule anisotropy that promotes self-assembling of macromolecules in solution of the organic compound or its salt, forming lyotropic liquid crystal; 
         b) application of a liquid layer of the solution onto a substrate, 
         wherein the liquid layer is substantially transparent to electromagnetic radiation in the visible spectral range; 
         c) application of an external alignment action onto said liquid layer; and 
         d) drying to form a solid optical retardation layer. 
       
     
     
         33 . A method according to  claim 32 , wherein the number k is equal to 0, 1, 2, 3, 4, 5, 6, 7, or 8 and the number n belongs to the range from 10 to 100000. 
     
     
         34 . A method according to  claim 32 , wherein under the increased shear rate the viscosity of the solution decreases down to a value in the range from 10 to 200 mPa·s. 
     
     
         35 . A method according to  claim 32 , wherein the alignment step is performed simultaneously with the step of application of the liquid layer to the substrate. 
     
     
         36 . A method according to  claim 32 , wherein the rod-like macromolecule is a polymeric main rigid-chain, and wherein the conjugated organic units are the same. 
     
     
         37 . A method according to  claim 32 , wherein the rod-like macromolecule is a copolymeric main rigid-chain, and wherein at least one conjugated organic unit is different from others. 
     
     
         39 . A method according to  claim 32 , wherein the number k is more than 1, and the ionogenic side-groups are the same. 
     
     
         40 . A method according to  claim 32 , wherein the number k is more than 1, and at least one said side-group is different from others. 
     
     
         41 . A method according to  claim 32 , wherein at least one conjugated organic unit (Core) of the rod-like macromolecule has the general structural formula III: 
       
         
           
           
               
               
           
         
         wherein Core 1  and Core 2  are conjugated organic components, Z is selected from the list comprising —O— and —NR—, where R is a substituent selected from the list comprising hydrogen, linear and branched (C 1 -C 4 )alkyls, phenyl and substituted phenyl, wherein substituents on the phenyl include linear and branched (C 1 -C 4 )alkyls. 
       
     
     
         42 . A method according to  claim 41 , wherein Core1 and Core2, comprise ionogenic groups G, are same or different and independently selected from the structures having general formula 1 to 2: 
       
         
           
           
               
               
           
         
         wherein the ionogenic side-groups G are selected from the list comprising —COOH, —SO 3 H, and —H 2 PO 3 , k is equal to 0, 1 or 2, p is equal to 1, 2 or 3. 
       
     
     
         43 . A method according to  claim 32 , wherein the organic compound is selected from structures 3-7: 
       
         
           
           
               
               
           
         
       
     
     
         44 . A method according to  claim 32 , wherein the organic compound further comprises additional side-groups independently selected from the list comprising linear and branched (C 1 -C 20 )alkyl, (C 2 -C 20 )alkenyl, and (C 2 -C 20 )alkinyl. 
     
     
         45 . A method according to  claim 44 , wherein at least one of the additional side-groups is connected with the Core via a bridging group A. 
     
     
         46 . A method according to  claim 45 , wherein the bridging group A is selected from the list comprising —C(O)—, —C(O)O—, —C(O)—NH—, —(SO 2 )NH—, —O—, —CH 2 O—, —NH—, >N—, and any combination thereof. 
     
     
         47 . A method according to  claim 32 , wherein the salt is selected from the list comprising alkali-metal salts and ammonium salt. 
     
     
         48 . A method according to  claim 32 , further comprising inorganic compounds which are selected from the list comprising hydroxides and salts of alkali metals. 
     
     
         49 . A method according to  claim 32 , wherein the substrate is made of a material selected from the list comprising a polymer and a glass. 
     
     
         50 . A method according to  claim 32 , further comprising a post-treatment step with a solution of any aqueous-soluble inorganic salt with a cation selected from the list comprising H + , Ba 2+ , Pb 2+ , Ca 2+ , Mg 2+ , Sr 2+ , La 3+ , Zn 4+ , Zr 4+ , Ce 3+ , Y 3+ , Yb 3+ , Gd 3+  and any combination thereof. 
     
     
         51 . A method according to  claim 32 , wherein the alignment action on the deposited liquid layer is performed with use an equipment selected from the list comprising Mayer rod, slot die, extrusion, roll coating, curtain coating, knife coating and molding. 
     
     
         53 . A method according to  claim 32 , wherein the sequence of the steps are repeated two or more times and the solution used in the fabrication of each subsequent solid retardation layer is either the same or different from that used in the previous cycle.