Mesogenic media and liquid crystal display

Patent metadata

Field	Value
Publication number	US-9752075-B2
Application number	US-201415038592-A
Country	US
Kind code	B2
Filing date	Oct 23, 2014
Priority date	Nov 22, 2013
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

Mesogenic media comprising a first component, component A, consisting of bimesogenic compounds optionally a second component, component B, consisting of nematogenic compounds, and optionally a second or third component, component C, consisting of one or more chiral molecules, is suitable for use in flexoelectric liquid crystal devices.

First claim

The invention claimed is:

1. A mesogenic medium comprising:
a first component, component A, consisting of bimesogenic compounds and comprising one or more compounds of formula A-0 and one or more compounds selected from formulae A-I to A-III

wherein
R 01 and R 02 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, and wherein one or more non-adjacent CH 2 groups, in each occurrence independently from one another, are optionally replaced 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 01 is -A 01 -Z 01 -A 02 -,
MG 02 is -A 03 -Z 02 -A 04 -Z 03 -A 05 -,
Z 01 to Z 03 are, independently of each other in each occurrence, a single bond, —COO—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —CH═CH—COO—, —OCO—CH═CH— or —C≡C—, optionally substituted with one or more of F, S and/or Si,
A 01 to A 05 are each independently in each occurrence 1,4-phenylene, wherein in addition one or more CH groups may each be replaced by N, trans-1,4-cyclo-hexylene in which, in addition, one or two non-adjacent CH 2 groups may each be replaced by O 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, wherein each of these groups is unsubstituted or mono-, di-, tri- or tetrasubstituted by substituents selected from F, Cl, CN, and alkyl, alkoxy, alkylcarbonyl and alkoxycarbonyl groups with 1 to 7 C atoms, wherein one or more H atoms may each be substituted by F or Cl,
Sp 0 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 each 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, and
X 01 and X 02 are independently from one another a linking group selected from —CO—O—, —O—CO—, —CH═CH—, —C≡C—, —O—, —S—CO—, —CO—S—, —S— and —CO— or a single bond, and wherein X 01 and X 02 are different from each other,
however under the condition that in —X 01 -Sp 0 -X 02 — 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,

wherein
R 11 and R 12 , R 21 and R 22 and 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, in each occurrence independently from one another, are optionally replaced 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 , MG 21 and MG 22 and MG 31 and MG 32 are each independently a mesogenic group,
Sp 1 , Sp 2 and Sp 3 are each independently a spacer group comprising 5 to 40 C atoms, wherein one or more non-adjacent CH 2 groups, with the exception of the CH 2 groups of Sp 1 linked to O-MG 11 and/or O-MG 12 , of Sp 2 linked to MG 21 and/or MG 22 and of Sp 3 linked to X 31 and X 32 , may each 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 (in the molecules) 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, and
X 31 and X 32 are independently from one another a linking group selected from —CO—O—, —O—CO—, —CH═CH—, —C≡C— or —S—, and, alternatively, one of X 31 and X 32 may also be either —O— or a single bond, and, again alternatively, one of X 31 and X 32 may be —O— and the other one a single bond,
an optional second component, component B, consisting of nematogenic compounds,
and
an optional second or third component, component C, consisting of one or more chiral molecules.

2. The mesogenic medium according to claim 1 , wherein in said formulae A-I to A-III, MG 11 and MG 12 , MG 21 and MG 22 and MG 31 and MG 32 are independently of each other selected from formula II
-A 1 -(Z 1 -A 2 ) m -  II

wherein
Z 1 is —COO—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —CH═CH—COO—, —OCO—CH═CH—, —C≡C— or a single bond,
A 1 and A 2 are each independently in each occurrence 1,4-phenylene, wherein in addition one or more CH groups may each be replaced by N, trans-1,4-cyclohexylene in which, in addition, one or two non-adjacent CH 2 groups may each be replaced by O 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, wherein each of these groups is unsubstituted or mono-, di-, tri- or tetrasubstituted by substituents selected from F, Cl, CN, and alkyl, alkoxy, alkylcarbonyl and alkoxycarbonyl groups with 1 to 7 C atoms, wherein one or more H atoms may each be substituted by F or Cl, and
m is 0, 1, 2 or 3.

3. The mesogenic medium according to claim 1 , wherein in formulae A-I to A-III, MG 11 and MG 12 , MG 21 and MG 22 and MG 31 and MG 32 are each and independently selected from the following formulae and their mirror images

wherein L is in each occurrence independently of each other F, Cl, CN, OH, NO 2 or an optionally fluorinated alkyl, alkoxy or alkanoyl group with 1 to 7 C atoms, and r is in each occurrence independently of each other 0, 1, 2, 3 or 4.

4. The mesogenic medium according claim 1 , wherein said medium comprises component B, and component B comprises one or more compounds selected from the group of compounds of formulae B-I to B-III:

wherein
R B1 , R B21 and R B22 and R B31 and R B32 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, in each occurrence independently from one another, are optionally replaced by —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —COO—, —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,
X B1 is F, Cl, CN, NCS, preferably CN,
Z B1 , Z B2 and Z B3 are

Assignees

• Merck Patent Gmbh

Inventors

• Tuffin Rachel
• Proctor Rebecca
• Siemianowski Simon
• Snow Benjamin
• Parri Owain Llyr
• Adlem Kevin

Classifications

• C09K2019/3021

  Cy-Ph-Ph-Cy · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C09K2019/3004

  Cy-Cy · CPC title

• C09K2019/183

  Ph-Ph-C≡C-Ph · CPC title