Liquid crystalline mixtures and method of making same

• US 5,102,578 A
• Filed: 08/03/1989
• Issued: 04/07/1992
• Est. Priority Date: 08/15/1988
• Status: Expired due to Fees

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Hoffmann-La Roche Incorporated (Roche Holding AG)
• Inventors: Schadt, Martin, Buchecker, Richard, Villiger, Alois
• Primary Examiner(s): Stoll, Robert L.
• Assistant Examiner(s): Wu, Shean C.
• Application Number:
  US07/389,095
• Time in Patent Office: 978 Days
• Field of Search: 252/299.01, 252/299.63, 359/103, 568/579
• US Class Current: 252/299.63
• CPC Class Codes: C07C 255/46 to carbon atoms of non-condensed rings
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 35/21 polycyclic, at least one hydroxy group bound to a non-condensed ring
• CPC Class Codes: C07C 43/115 containing carbocyclic rings
• CPC Class Codes: C07C 43/13 containing hydroxy or O-metal groups C07C43/11 takes precedence
• CPC Class Codes: C07C 43/162 containing rings other than six-membered aromatic rings
• CPC Class Codes: C09K 19/3003 Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
• CPC Class Codes: C09K 19/3028 in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
• CPC Class Codes: C09K 2019/3021 Cy-Ph-Ph-Cy

Abstract

A compound of the formula ##STR1## wherein Z represents a single covalent bond or --CH₂ --CH₂ --; R¹ denotes alkyl or 2-alkenyl and

R² is 1E-alkenyl, 3E-alkenyl, 4-alkenyl, (2-alkenyl)oxymethyl or, when R¹ denotes 2-alkenyl and/or Z represents --CH₂ --CH₂ --, R² also is alkyl, cyano or alkoxymethyl,

as well as the manufacture of the compounds of formula I. Also disclosed is the use of the compounds in liquid crystalline mixtures and for electro-optical purposes.

Claims

1. A compound of formula ##STR9## wherein Z is a single covalent bond or --CH₂ --CH₂ --;

R¹ is alkyl of 1 to 10 carbon atoms or 2-alkenyl of 3 to 10 carbon atoms; and

R² is 1E-alkenyl, 3E-alkenyl, 4-alkenyl, (2-alkenyl)oxymethyl, alkyl, or alkoxymethyl having from 1 to 12 carbon atoms;

with the proviso that R¹ is 2-alkenyl and Z is --CH₂ CH₂ -- when R² is alkyl or alkoxymethyl.

2. A compound according to claim 1, wherein R¹ and R² each are straight-chain residues.

3. A compound according to claim 1, wherein R¹ has a maximum of 10 carbon atoms.

4. A compound according to claim 3, wherein R¹ has a maximum of 5 carbon atoms.

5. A compound according to claim 1, wherein R² has a maximum of 12 carbon atoms.

6. A compound according to claim 5, wherein R² has a maximum of 7 carbon atoms.

7. A compound according to claim 1, wherein R¹ is 2-alkenyl.

8. A compound according to claim 7, wherein R² is 1E-alkenyl, 3E-alkenyl, 4-alkenyl or (2-alkenyl)oxymethyl.

9. A compound according to claim 1, wherein R² is 1E-alkenyl, 3E-alkenyl, 4-alkenyl or (2-alkenyl)oxymethyl.

10. A liquid crystalline mixture having at least two components, wherein at least one component is a compound of formula ##STR10## wherein Z is a single covalent bond or --CH₂ --CH₂ --;

R¹ is alkyl of 1 to 10 carbon atoms or 2-alkenyl of 3 to 10 carbon atoms; and

R² is 1E-alkenyl, 3E-alkenyl, 4-alkenyl, (2-alkenyl)oxymethyl, alkyl or alkoxymethyl having from 1 to 12 carbon atoms;

with the proviso that R¹ is 2-alkenyl and Z is --CH₂ CH₂ -- when R² is alkyl or alkoxymethyl.

11. A liquid crystalline mixture according to claim 10, comprising one or more of the compounds of formula I;

and one or more compounds having a positive dielectric anisotropy.

12. A liquid crystalline mixture according to claim 11, comprising one or more of the compounds of formula I;

and one or more compounds from a group of compounds of formula ##STR11## wherein R³ is alkyl, 3E-alkenyl or 4-alkenyl;

R⁴ is alkyl, cyano or fluorine;

R⁵ and R⁶ each independently are alkyl or alkoxy;

R⁷ and R¹⁰ each independently are alkyl, 1E-alkenyl, 3E-alkenyl or 4-alkenyl;

R⁸ is cyano, alkyl, 1E-alkenyl, 3E-alkenyl, 4-alkenyl, alkoxy, 2E-alkenyloxy or 3-alkenyloxy;

R⁹ is alkoxy, 2E-alkenyloxy or 3-alkenyloxy;

n stands for the number 0 or 1;

Z is a single covalent bond or --CH₂ CH₂ --;

X¹ is fluorine or chlorine; and

X² is hydrogen, fluorine or chlorine;

R¹¹ is alkyl, 3E-alkenyl, 4-alkenyl, alkoxy, 2E-alkenyloxy or 3-alkenyloxy;

one of the groups Y¹ and Y² is a single covalent bond, --COO--, --OOC--, --CH₂ CH₂ --, --CH₂ O-- or --OCH₂ -- and the other of the groups Y¹ and Y² is a single covalent bond; and

rings A¹ and A² each independently are unsubstituted trans-1,4-cyclohexylene, trans-1,4-cyclohexylene substituted with cyano, methyl, fluorine or chlorine, trans-1,4-cyclohexane wherein 2 non-adjacent CH₂ groups are replaced by oxygen, unsubstituted 1,4-phenylene, 1,4-phenylene substituted with cyano, methyl, fluorine or chlorine, or 1,4-phenylene having 1 CH group or 2 CH groups replaced by nitrogen.

13. A liquid crystalline mixture according to claim 10, wherein the compound of formula I is in the final mixture in an amount of about 1 to about 70 wt. % of the final mixture.

14. A liquid crystalline mixture according to claim 13, wherein the amount of the compound of formula I in the final mixture is about 3 to about 40 wt. %.

15. In a ferroelectric electro-optical indicating device of the type having a liquid crystalline mixture sandwiched between two transparent plates having polarizers and electrode-means, wherein the improvement comprises:

said liquid crystalline mixture having a positive dielectric anisotropy and containing at least two components wherein at least one component is a compound formula ##STR12## wherein Z is a single covalent bond or --CH₂ --CH₂ --;

R¹ is alkyl of 1 to 10 carbon atoms or 2-alkenyl of 3 to 10 carbon atoms; and

R² is 1E-alkenyl, 3E-alkenyl, 4-alkenyl, (2-alkenyl)oxymethyl, alkyl or alkoxymethyl having from 1 to 12 carbon atoms;

with the proviso that R¹ is 2-alkenyl and Z is --CH₂ CH₂ -- when R² is alkyl or alkoxymethyl.