Liquid crystalline compounds
Liquid-crystalline compounds with a terminal 5,6-difluoro-benzo[b]thiophene ring as provided by formula I, liquid crystal mixtures using the compounds, the use of the compounds in an electro-optical display, particularly in an active-matrix display based on the IPS or FFS effect, and liquid crystal displays that contain a liquid crystal material of this type.
1 . A compound of formula I
in which
R 1 is an alkyl radical having 1 to 15 C atoms, wherein one or more CH 2 groups in this radical may each be replaced, independently of one another, by —C≡C—, —CH═CH—,
—O—, —S—, —(CO)—O—, —O—(CO)— in such a way that O or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F or Cl,
A 0 independently of one another, on each appearance, denotes phenylene-1,4-diyl, in which, in addition, one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 , CHF 2 , CH 2 F, OCH 3 , OCHF 2 or OCF 3 , cyclohexane-1,4-diyl, in which, in addition, one or two non-adjacent CH 2 groups may be replaced, independently of one another, by O and/or S and one or more H atoms may be replaced by F, cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo-[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl,
Z 0 independently denotes a single bond, —CH 2 O—, —(CO)O—, —CF 2 O—, —CH 2 CH 2 CF 2 O—, —CF 2 CF 2 —, —CH 2 CF 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH═CH—, —CH═CF—, —CF═CF— or —C≡C—, wherein —CH 2 O—, —(CO)O—, —CF 2 O—, —CH 2 CH 2 CF 2 O—, —CH═CF—, and —CH 2 CF 2 — may be inserted in any orientation, and
n denotes 1, 2 or 3.
2 . The compound according to claim 1 , wherein A 0 is
A 0
L 1 , L 2 each, independently of one another, denote F, Cl, CH 3 or OCH 3 , and
Y CH 3 , CH 2 CH 3 .
3 . The compound according to claim 1 , wherein n is 1 or 2.
4 . The compound according to claim 1 , wherein Z 0 is a single bond.
5 . The compound according to claim 1 , wherein the compound of formula I is selected from the group consisting of the following formulae:
R 1 is an alkyl radical having 1 to 15 C atoms, wherein one or more CH 2 groups, including terminal C atoms, in this radical may each be replaced, independently of one another, by —C≡C—, —CH═CH—,
—O—, —S—, —(CO)—O—, —O—(CO)— in such a way that O or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F or Cl.
6 . A liquid crystal mixture, comprising a compound of formula I according to claim 1 .
7 . A process for the production of a compound of formula I according to claim 1 , comprising the steps of:
reacting a compound of formula I-S
in which
R 1 is an alkyl radical having 1 to 15 C atoms, wherein one or more CH 2 groups, including terminal C atoms, in this radical may each be replaced, independently of one another, by —C≡C—, —CH═CH—,
—O—, —S—, —(CO)—O—, —O—(CO)— in such a way that O or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F or Cl,
A 0 independently of one another, on each appearance, denotes phenylene-1,4-diyl, in which, in addition, one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 , CHF 2 , CH 2 F, OCH 3 , OCHF 2 or OCF 3 , cyclohexane-1,4-diyl, in which, in addition, one or two non-adjacent OH 2 groups may be replaced, independently of one another, by O and/or S and one or more H atoms may be replaced by F, cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo-[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl,
Z 0 independently denotes a single bond, —CH 2 O—, —(CO)O—, —CF 2 O—, —CH 2 CH 2 CF 2 O—, —CF 2 CF 2 —, —CH 2 CF 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH═CH—, —CH═CF—, —CF═CF— or —C≡C—, where asymmetrical bridges may be inserted in any orientation,
n denotes 1, 2 or 3, and
Lg is a leaving group,
with a base to give a compound of the formula I.
8 . A compound of formula I-S
in which
R 1 is an alkyl radical having 1 to 15 C atoms, wherein one or more CH 2 groups, including terminal C atoms, in this radical may each be replaced, independently of one another, by —C≡C—, —CH═CH—,
—O—, —S—, —(CO)—O—, —O—(CO)— in such a way that O or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F or Cl,
A 0 independently of one another, on each appearance, denotes phenylene-1,4-diyl, in which, in addition, one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 , CHF 2 , CH 2 F, OCH 3 , OCHF 2 or OCF 3 , cyclohexane-1,4-diyl, in which, in addition, one or two non-adjacent CH 2 groups may be replaced, independently of one another, by O and/or S and one or more H atoms may be replaced by F, cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo-[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl,
Z 0 independently denotes a single bond, —CH 2 O—, —(CO)O—, —CF 2 O—, —CH 2 CH 2 CF 2 O—, —CF 2 CF 2 —, —CH 2 CF 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH═CH—, —CH═CF—, —CF═CF— or —C≡C—, where asymmetrical bridges may be inserted in any orientation,
n denotes 1, 2 or 3, and
Lg is a leaving group.
9 . A liquid-crystalline medium, comprising one or more compounds of formula I according to claim 1 .
10 . The liquid-crystalline medium according to claim 9 , having a total concentration of the compounds of formula I in the medium as a whole of 1% by weight or more but less than 30% by weight.
11 . An electro-optical display or electro-optical component, comprising a liquid-crystalline medium according to claim 9 .
12 . The liquid-crystalline medium of claim 9 , further comprising one or more compounds of formula 1, 2, 3, 4, or 5:
in which
L and E, which may be identical or different, each, independently of one another, denote a divalent radical from the group formed by the structural elements -Phe-, -Cyc-, -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-, -Pyr-, -Dio-, -Py-, -G-Phe-, -G-Cyc- and their mirror images, where Phe denotes unsubstituted or fluorine-substituted 1,4-phenylene, Cyc denotes trans-1,4-cyclohexylene, Pyr denotes pyrimidine-2,5-diyl or pyridine-2,5-diyl, Dio denotes 1,3-dioxane-2,5-diyl, Py denotes tetrahydropyran-2,5-diyl and G denotes 2-(trans-1,4-cyclohexyl)ethyl,
R′ and/or R″ each, independently of one another, denote alkyl, alkoxy, alkoxyalkyl, alkenyloxy or alkanoyloxy having 1 to 8 C atoms, alkenyl having 2 to 8 C atoms, —F, —Cl, —CN, —NCS or —(O)iCH 3 -kFk,
i is 0 or 1, and
k is 1, 2 or 3.