Liquid Crystals Comprising Cyclopentane Groups

Abstract

Provided are liquid crystal compounds and mixtures incorporating the same. The liquid crystal compounds of the invention generally comprise a cyclopentane group and at least two other rings. In one embodiment, the liquid crystal compounds of the invention comprise a cyclopentane group and at least two other rings, one of which is a fused ring system.

1 .- 19 . (canceled) 
     
     
         20 . A compound having the formula: 
       
         
           
           
               
               
           
         
         wherein: 
         R is selected from the group consisting of H and unsubstituted or substituted alkyl each having I-12 carbon atoms, wherein the substitutions are independently one or more of halogen or CN, and wherein one or more CH 2  groups of the alkyl groups are optionally independently replaced with —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or —CH═CH—, provided that heteroatoms are not connected directly, except as permitted in the listed groups; 
         A and B rings are each independently selected from the group consisting of: 1,4-cyclohexyl, in which one CH 2  or two not directly linked CH 2  are optionally replaced by O or S; 1,4-cyclohexenyl; piperidine-1,4-diyl; 1,4-bicyclo[2,2,2]octylene; 1,4-phenyl, which is optionally substituted with one or more halogens; pyridin-5,2-dyl; pyrimidin-5,2-diyl; naphthalene-2,6-diyl; trans-decahydronaphthalene-2,6-diyl; tetrahydronaphthalene-2,6-diyl; indane; indene; phenanthryl; and dibenzofuran, which each independently in each instance are optionally independently substituted with one or more halogens and/or one or more X 1 -X 4  substituents; 
         Z 1  is a single bond or CI-7 unsubstituted or substituted alkylene, wherein the substitutions are independently one or more of halogen or CN, wherein one or more CH 2  group of the alkylene are independently optionally replaced by —O—, —S—, —CO—O—, —O—CO—, —O—CO—O— or —CH═CH—, provided that heteroatoms are not connected directly to each other except as permitted in the listed groups; 
         Z 2  and Z 3  are each independently selected from the group consisting of: a single bond, —(CH 2 ) 2 —, —(CH 2 ) 4 —, —CH═CHCH 2 CH 2 —, —CH 2 CH 2 CH═CH—, —CF 2 O—, —OCF 2 —, —CF 2 CF 2 —, —CF═CF—, —CH 2 CF 2 , —CF 2 CH 2 —, —OCF 2 CF 2 O—, —C 2 H 4 CF 2 O—, —CH 2 CF 2 OCH 2 —, —CH 2 OCF 2 CH 2 —, —OCF 2 C 2 H 4 —, —C 3 H 6 O—, —OC 3 H 6 —, —C 2 H 4 OCH 2 —, —CH 2 OC 2 H 4 —, —CH 2 O—, —OCH 2 —, —CH═CH—, —C≡C—, and —COO—; 
         n, m and K are each independently 0, 1, or 2, and m+K+n≥2; 
         X 1 , X 2 , X 3 , and X 4  are each independently selected from the group consisting of: H, F, Cl, CF 3 , CHF 2 , OCF 3  or OCF 2 H and CN; 
         Y is independently selected from the group consisting of: H, F, Cl, CN, NCS, OCHF 2 , CHF 2 , OCF 3 , OCF 2 CF 3 , CF 3 , C 1-20  alkyl, C 1-20  alkoxy, C 1-20  alkenyl, and C 1-20  alkenyloxy, wherein the alkyl, alkoxy, alkenyl, and alkenyloxy groups independently are optionally substituted by one or more halogens; 
         wherein one or more hydrogen atoms in Formula I are optionally replaced with deuterium; 
         provided that: 
         (1) when R═H and Y has less than 2 carbon atoms and both X 3  and X 4  are H or when R═H and Y has two or more carbon atoms and Z 1  has more than 3 carbon atoms, 
         then: 
         there is a fused ring system in the compound or 
         one of Z 1 , Z 2  and Z 3  is selected from the group consisting of: C1-C3 alkylene, —CH═CHCH 2 CH 2 —, —CH 2 CH 2 CH═CH—, —CF 2 O—, —OCF 2 —, —CF 2 CF 2 —, —CF═CF—, —CH 2 CF 2 , —CF 2 CH 2 —, —OCF 2 CF 2 O—, —C 2 H 4 CF 2 O—, —CH 2 CF 2 OCH 2 —, —CH 2 OCF 2 CH 2 —, —OCF 2 C 2 H 4 —, —C 3 H 6 O—, —OC 3 H 6 —, —C 2 H 4 OCH 2 —, —CH 2 OC 2 H 4 —, and —CH═CH—; and 
         (2) when R is not H and Y does not contain a —CF2- group, 
         then: 
         either one of the A or B ring is selected from the group consisting of: 1,4-cyclohexene, in which one or two not directly linked CH 2  groups are optionally replaced by O or S; pyridin-5,2-dyl; pyrimidin-5,2-diyl; indane; indene; phenanthryl, or dibenzofuran; or 
         one of Z 1 , Z 2  and Z 3  is selected from the group consisting of: —(CH 2 ) 4 —, —CH═CHCH 2 CH 2 —, —CH 2 CH 2 CH═CH—, —CF 2 O—, —OCF 2 —, —CF 2 CF 2 —, —CF═CF—, —CH 2 CF 2 , —CF 2 CH 2 —, —OCF 2 CF 2 O—, —C 2 H 4 CF 2 O—, —CH 2 CF 2 OCH 2 —, —CH 2 OCF 2 CH 2 —, —OCF 2 C 2 H 4 —, —C 3 H 6 O—, —OC 3 H 6 —, —C 2 H 4 OCH 2 —, —CH 2 OC 2 H 4 —, —CH═CH—, and —C≡C—. 
       
     
     
         21 . The compound of  claim 20 , wherein Y is H. 
     
     
         22 . The compound of  claim 20 , wherein K is 0. 
     
     
         23 . The compound of  claim 20 , wherein m+K+n is 2. 
     
     
         24 . The compound of  claim 20 , wherein m+K+n is 3. 
     
     
         25 . The compound of  claim 20  having a negative dielectric constant. 
     
     
         26 . The compound of  claim 20 , having any one of formulas I-18 through I-47: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         and wherein one, two three, four, five or six of X 1 -X 6 , are F and the others of X 1 -X 6  are H. 
       
     
     
         27 . A compound of  claim 26 , wherein R′ is H. 
     
     
         28 . A compound of  claim 27  having formula: 
       
         
           
           
               
               
           
         
       
     
     
         29 . A compound of  claim 26  having formula I-22 to I-27, I-29-I33 or I-38-1-40. 
     
     
         30 . A liquid crystal mixture having comprising a compound of  claim 20  and having a negative dielectric constant. 
     
     
         31 . The mixture of  claim 30 , wherein the mixture further comprises at least one compound of formula XXIV-XLIV as shown herein. 
     
     
         32 . The mixture of  claim 30 , wherein the mixture further comprises at least one compound of formula XLV-XLVIII as shown herein. 
     
     
         33 . The mixture of  claim 30 , wherein the mixture comprises at least one compound of formula XXIV-XLIV as shown herein and at least one compound of formula XLV-XLVIII as shown herein. 
     
     
         34 . A device comprising a compound of  claim 20 . 
     
     
         35 . A device comprising a mixture of  claim 30 .