Bimesogenic compounds and mesogenic media

Patent metadata

Field	Value
Publication number	US-10450508-B2
Application number	US-201515326204-A
Country	US
Kind code	B2
Filing date	Jun 19, 2015
Priority date	Jul 17, 2014
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

The invention relates to bimesogenic compounds of formula I

wherein R 11 , R 12 , MG 11 , MG 12 , X 11 , X 12 and Sp 1 have the meaning given in claim 1 , to the use of bimesogenic compounds of formula l in liquid crystal media and particular to flexoelectric liquid crystal devices comprising a liquid crystal medium according to the present invention.

First claim

The invention claimed is:

1. Bimesogenic compounds of formula

wherein
R 11 and R 12 are each independently H, halogen, CN, NO 2 or a straight-chain or branched alkyl group with 1 to 25 C atoms which may be unsubstituted, mono-or polysubstituted by halogen or CN, wherein one or more non-adjacent CH 2 groups may be replaced, in each occurrence independently from one another, by —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —O—CO—O—, —S—CO—, —CO—S—, —CH═CH—, —CH═CF—, —CF═CF— or —C≡C— in such a manner that oxygen atoms are not linked directly to one another,
MG 11 and MG 12 are each independently a mesogenic group,
at least one of
MG 11 and MG 12 contains at least one fused ring group selected from alicyclic, aromatic and condensed groups made up of 7 to 23 carbon atoms, wherein one or two non-adjacent CH groups each may be replaced by an N-atom and/or one or two non-adjacent CH 2 groups, independently of each other, may be replaced by an O- or an S-atom, and which optionally is substituted by one or more halogen atoms, and/or by one or more alkyl group(s) each independently having 1 to 9 C atoms, and/or by one more alkoxy group(s) each independently having 1 to 9 C atoms, wherein the mesogenic group can also contain 0 to 3 six membered rings selected from 1,4-phenylene, wherein in addition one or more CH groups may be replaced by N, trans-1,4-cyclo-hexylene in which, in addition, one or two non-adjacent CH 2 groups may be replaced by O and/or S, 1,4-cyclohexenylene, 1,4-bicyclo-(2,2,2)-octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydro-naphthalene-2,6-diyl, 1,2,3,4-tetrahydro-naphthalene-2,6-diyl, cyclobutane-1,3-diyl, spiro[3.3]heptane-2,6-diyl or dispiro[3.1.3.1] decane-2,8-diyl, it being possible for all these groups to be unsubstituted, mono-, di-, tri- or tetrasubstituted with F, Cl, CN or alkyl, alkenyl, alkoxy, alkenyloxy, alkylcarbonyl or alkoxycarbonyl groups, wherein one or more H atoms may be substituted by F or Cl,
Sp 1 is a spacer group comprising 1, 3 or 5 to 40 C atoms, wherein one or more non-adjacent and non-terminal CH 2 groups may also be replaced by —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —O—CO—, —S—CO—, —O—COO—, —CO—S—, —CO—O—, —CH(halogen)-, —CH(CN)—, —CH═CH— or —C≡C—, however in such a way that no two O-atoms are adjacent to one another, no two —CH═CH— groups are adjacent to each other and no two groups selected from —O—CO—, —S—CO—, —O—COO—, —CO—S—, —CO—O— and —CH═CH— are adjacent to each other,
X 11 and X 12 are independently from one another a linking group selected from —CO—, —CO—O—, —O—CO—, —O—, —CH═CH—, —C≡C—, —CO—S—, —S—CO—, —CS—S—, —S—, —CF 2 —, —CF 2 —O—, —O—CF 2 —and a single bond,
however under the condition that X 11 and X 12 are not both —O— and under the condition that X 11 and X 12 are both not a single bond, and under the condition that in —X 11 -Sp 1 —X 12 — no two O-atoms are adjacent to one another, no two —CH═CH— groups are adjacent to each other and no two groups selected from —O—CO—, —S—CO—, —O—CO—O—, —CO—S—, —CO—O—, —CF 2 —O—, —O—CF 2 — and —CH═CH— are adjacent to each other.

2. Bimesogenic compounds according to claim 1 , characterized in that at least one of MG 11 and MG 12 comprises one fused ring structure, two or more fused ring structures, at least part of which fused ring structure or fused ring structures is aromatic.

3. Bimesogenic compounds according to claim 1 , characterized in that both MG 11 and MG 12 comprise one, two or more ring structures.

4. Bimesogenic compounds according to claim 1 , characterized in that R 12 is selected from OCF 3 , CF 3 , F, Cl, CN and NO 2 .

5. Bimesogenic compounds according to claim 1 , characterized in that Sp 1 is —(CH 2 ) o — and o is 1, 3 or an integer from 5 to 15.

6. A method which comprises including one or more bimesogenic compounds according to claim 1 in a liquid crystalline medium.

7. Liquid-crystalline medium, characterised in that it comprises one or more bimesogenic compounds according to claim 1 .

8. Liquid-crystalline medium according to claim 7 , characterised in that it additionally comprises one or more compounds selected from the group of the compounds of the formulae III
R 31 -MG 31 -X 31 -Sp 3 -X 32 -MG 32 -R 32   III

wherein
R 31 and R 32 are each independently H, F, Cl, CN, NCS or a straight-chain or branched alkyl group with 1 to 25 C atoms which may be unsubstituted, mono-or polysubstituted by halogen or CN, wherein one or more non-adjacent CH 2 groups may be replaced, in each case independently from one another, by —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —O—CO—O—, —S—CO—, —CO—S—, —CH═CH—, —CH═CF—, —CF═CF— or —C≡C— in such a manner that oxygen atoms are not linked directly to one another,
MG 31 and MG 32 are each independently a mesogenic group,
Sp 3 is a spacer group comprising 5 to 40 C atoms, wherein one or more non-adjacent CH 2 groups may also be replaced by —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —O—CO—, —S—CO—, —O—COO—, —CO—S—, —CO—O—, —CH(halogen)-, —CH(CN)—, —CH═CH— or —C≡C—, and
X 31 and X 32 are each independently —O—, —S—, —CO—, —COO—, —OCO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CH═CH—, —CH═CH—COO—, —OCO—CH═CH—, —C≡C— or a single bond, and
with the condition that compounds of formula I are excluded.

9. A method comprising including a liquid crystal medium according to claim 7 , in a liquid crystal device.

10. Liquid crystal device comprising a liquid crystalline medium comprising two or more components, one or more of which is a bimesogenic compound of formula I according to claim 1 .

11. Liquid crystal device according to claim 10 , characterized in that it is a flexoelectric device.

Assignees

• Merck Patent Gmbh

Inventors

• Adlem Kevin
• Parri Owain Llyr
• Tuffin Rachel
• Arasi Hassan
• Snow Benjamin

Classifications

• C07C255/55

  containing cyano groups and esterified hydroxy groups bound to the carbon skeleton · CPC title

• C07D333/54

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring · CPC title

• C07D241/42

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring · CPC title

• C07C323/38

  with the sulfur atom of the thio group bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system · CPC title

• C09K19/322 Primary

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title