Liquid crystal compounds having perfluoroether terminal portions

• US 5,482,650 A
• Filed: 11/14/1994
• Issued: 01/09/1996
• Est. Priority Date: 04/28/1992
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Company
• Inventors: Spawn, Terence D., Savu, Patricia M., Radcliffe, Marc D., Janulis, Eugene P., Snustad, Daniel C., Johnson, Gilbert C.
• Primary Examiner(s): WU, SHEAN CHIU
• Application Number:
  US08/338,957
• Time in Patent Office: 421 Days
• Field of Search: 252/299.01, 252/299.61, 252/299.62, 252/299.63, 252/299.64, 252/299.65, 252/299.66, 568/681
• 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 19/3497 the heterocyclic ring containing sulfur and nitrogen atoms
• CPC Class Codes: C09K 2019/325 : containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)

Abstract

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

Claims

1. Fluorine-containing intermediate compounds which can be represented by the formula ##STR100## wherein N and P are each independently phenyl, napthyl, or pyrimidinyl;

b and c are each independently zero or an integer of 1 to 2, with the proviso that the sum of b+c be at least 1;

B is a covalent bond;

A" is --OH or --COOH;

each Y and Z are independently --H, --Cl, --F, --OCH₃, --OH, --CH₃, --CF₃, --OCF₃, --NO₂, --Br, --I, or --CN;

m and n are zero;

D is --OCH₂ --; 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 10.

2. Fluorine-containing intermediate compounds which can be represented by the formula

3. Fluorine-containing liquid crystal compounds represented by the formula ##STR101## where M, N, and P are each independently ##STR102## 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, ##STR103## --(CH₂ CH₂)_k -- where k is 1 to 4, --CH═

CH--, --C.tbd.C--, --CH═

N--, --CH₂ --O--, ##STR104## or --O--;

each X, Y, and Z are independently --H, --Cl, --F, --Br, --I, --OH, --OCH₃, --CH₃, --CF₃, --OCF₃ --CN, or --NO₂ ;

each l, m, and n are independently zero or an integer of 1 to 4,

D is a covalent bond, ##STR105## where r and r'"'"' are independently 1 to 20, s is independently 1 to 10 for each (C_s H_2s O), t is 1 to 6 and where r and r'"'"' are independently 1 to 20, and p is 0 to 4;

R is ##STR106## where R'"'"' is --Cl, --F, --CF₃, --NO₂, --CN, --H, ##STR107## and q and q'"'"' are independently 1 to 20, w is 1 to 10 and R can be straight chain or branched; and

R_f is --(CF₂)_w,O(C_x F_2x O)_z C_y F_2y+1 where w'"'"' is an integer of 5 to 16, x is independently an integer of 1 to 10 for each C_x F_2x O, y is an integer of 1 to 10, and z is an integer of 1 to 10.

4. The compounds of claim 3 which can be represented by the formula ##STR108## wherein d is an integer of 4 to 8, t'"'"' is an integer of 1 to 5, w'"'"' is an integer of 5 to 9, x is an integer of 2, y is an integer of 1 to 6, and z is an integer of 1 to 3.

5. The compounds of claim 3 wherein said d is an integer of 4, 7, or 8;

said t'"'"' is an integer of 1;

said w'"'"' is an integer of 5;

said y is an integer of 1; and

said z is an integer of 3.

6. The compounds of claim 3 wherein said d is an integer of 4 or 8;

said t'"'"' is an integer of 1;

said w'"'"' is an integer of 9;

said y is an integer of 4; and

said z is an integer of 1.

7. The compounds of claim 3 wherein said d is an integer of 4, 6, 7, or 8;

said t'"'"' is an integer of 1;

said w'"'"' is an integer of 5;

said y is an integer of 4; and

said z is an integer of 1 or 2.

8. The compounds of claim 3 wherein said d is an integer of 6 or 8;

said t'"'"' is an integer of 1;

said w'"'"' is an integer of 7;

said y is an integer of 4; and

said z is an integer of 1.

9. The compounds of claim 4 wherein said d is an integer of 8;

said t'"'"' is an integer of 1;

said w'"'"' is an integer of 7;

said y is an integer of 1; and

said z is an integer of 2.

10. The compounds of claim 4 wherein said d is an integer of 8;

said t'"'"' is an integer of 3;

said w'"'"' is an integer of 5;

said y is an integer of 4; and

said z is an integer of 1.