Ferroelectric liquid crystal compounds having perfluoroether terminal portions

• US 5,262,082 A
• Filed: 04/28/1992
• Issued: 11/16/1993
• Est. Priority Date: 04/28/1992
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Company
• Inventors: Savu, Patricia M., Spawn, Terence D., Janulis, Eugene P., Johnson, Gilbert C.
• Primary Examiner(s): Stoll, Robert L.
• Assistant Examiner(s): WU, SHEAN CHIU
• Application Number:
  US07/875,223
• Time in Patent Office: 567 Days
• Field of Search: 252/299.01, 252/299.61, 252/299.62, 252/299.63, 252/299.67, 544/182, 544/298, 544/242, 544/335, 546/270, 546/272, 546/315, 546/322, 546/326, 549/369, 549/374, 549/380, 560/61, 560/64, 560/65, 560/73, 560/100, 560/102, 560/105, 568/325, 568/331, 568/632, 568/642, 570/129, 359/104
• US Class Current: 252/299.01
• CPC Class Codes: C07C 255/55 containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
• CPC Class Codes: C07C 309/65 of a saturated carbon skeleton
• CPC Class Codes: C07C 309/73 to carbon atoms of non-condensed six-membered aromatic rings
• CPC Class Codes: C07C 43/123 both carbon chains are substituted by halogen atoms
• CPC Class Codes: C07C 43/126 having more than one ether bond
• CPC Class Codes: C07C 43/137 containing halogen
• CPC Class Codes: C07C 43/178 containing hydroxy or O-metal groups
• CPC Class Codes: C07C 43/1786 containing halogen
• CPC Class Codes: C07C 69/92 with etherified hydroxyl groups
• CPC Class Codes: C07D 213/80 in position 3
• CPC Class Codes: C07D 239/26 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 239/36 as doubly bound oxygen atom or as unsubstituted hydroxy radical
• CPC Class Codes: C09K 19/04 characterised by the chemical structure of the liquid crystal components , e.g. by a specific unit
• CPC Class Codes: C09K 19/2007 the chain containing -COO- or -OCO- groups
• CPC Class Codes: C09K 19/32 containing condensed ring systems, i.e. fused, bridged or spiro ring systems
• CPC Class Codes: C09K 19/322 Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
• CPC Class Codes: C09K 19/3441 having nitrogen as hetero atom
• CPC Class Codes: C09K 19/3444 the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
• CPC Class Codes: C09K 19/3469 Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-
• CPC Class Codes: C09K 19/3491 having sulfur as hetero atom
• CPC Class Codes: C09K 2019/325 : containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)

Abstract

Fluorine-containing liquid crystal compounds are provided. The compounds comprise a fluorocarbon terminal portion having at least one catenary ether oxygen and a hydrocarbon terminal portion, the terminal portion being connected by a central core, the compounds having smectic mesophases or having latent smectic mesophases.

Claims

1. An achiral fluorine-containing liquid crystal compound of the general formula I:

##STR45## where M, N, and P are each independently ##STR46## a, b, and c are each independently zero or an integer of from 1 to 3 with the proviso that the sum of a+b+c be at least 2;

each A and B are non-directionally and independently a covalent bond, ##STR47## each X, Y, and Z are independently --H, --Cl, --F, --Br, --I, --OH, --OCH₃, --CN, or --NO₂ ;

each 1, m, and n are independently zero or an integer of 1 to 4, D is ##STR48## and q and q'"'"' are independently 1 to 20, and R can be straight chain or branched; and

R_f is (C_x F_2x O)_z C_y F_2y+1 where x is independently 1 to 10 for each C_x F_2x O group, y is 1 to 10 and z is 1 to 6.

2. A compound according to claim 1 wherein said compound can be represented by the formula ##STR49## where d is 5 to 10, x is independently 1 to 3 for each C_x F_2x O group, y is 1 to 4 and z is 1 to 3.

3. A compound according to claim 1 wherein said compound can be represented by the formula ##STR50## where t is 6, 8 or 10.

4. A compound according to claim 1 wherein said compound can be represented by the formula ##STR51## where t is 6, 8 or 10.

5. A compound according to claim 1 wherein said compound can be represented by the formula ##STR52## where t is 6, 8 or 10.

6. A compound according to claim 1 wherein said compound can be represented by the formula ##STR53##

7. A compound according to claim 1 wherein said compound can be represented by the formula ##STR54## where t is 6, 8 or 10.

8. A compound according to claim 1 wherein said compound can be represented by the formula ##STR55## where t is 6, 8 or 10.

9. A compound according to claim 1 wherein said compound can be represented by the formula ##STR56##

10. A compound according to claim 1 wherein said compound can be represented by the formula ##STR57##

11. A compound according to claim 1 wherein R_f is --CF₂ OCF₂ CF₂ OC₄ F₉.

12. Liquid crystal mixtures comprising at least one compound according to claim 1 and at least one chiral liquid crystal compound, said chiral liquid crystal compound being present in an amount sufficient to provide the mixture with ferroelectric properties.

13. A liquid crystal display device containing said compound of claim 1 wherein said compound has a smectic mesophase.