Mesogenic media and liquid crystal display

Patent metadata

Field	Value
Publication number	US-2016298031-A1
Application number	US-201415038592-A
Country	US
Kind code	A1
Filing date	Oct 23, 2014
Priority date	Nov 22, 2013
Publication date	Oct 13, 2016
Grant date	—

Abstract

The invention relates to mesogenic media comprising a first component, component A, consisting of bimesogenic compounds optionally a second component, component B, consisting of nematogenic compounds, preferably selected from the group of compounds of formulae B-I to B-III

and

optionally a second or third component, component C, consisting of one or more chiral molecules,

wherein the parameters have the meaning given in claim 1 , to the use of mesogenic media in flexoelectric liquid crystal devices and to those devices comprising a liquid crystal medium according to the present invention.

First claim

1 . 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 the group of compounds of 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, it being also possible for one or more non-adjacent CH 2 groups to 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, preferably a polar group, more preferably F, Cl, CN, OCF 3 , CF 3 ,

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,
preferably a single bond,

A 01 to A 05 are each independently in each occurrence 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, alkoxy, alkylcarbonyl or alkoxycarbonyl groups with 1 to 7 C atoms, wherein one or more H atoms may be substituted by F or Cl, preferably F, Cl, CH 3 or CF 3 ,
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 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, now 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, preferably —CH 2 ) n — (i.e. 1,n-alkylene with n C atoms), with n an integer, preferably from 3 to 19, more preferably from 3 to 11, most preferably an odd integer (i.e. 3, 5, 7, 9 or 11),

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, preferably they are different from each another and preferably X 01 is —CO—O— or —O— and X 02 is a single bond or X 01 is —CO—O— and X 02 is —O—, most preferably X 01 is
—CO—O— and X 02 is a single bond,

however under the condition that in —X 01 -Sp 0 -X 02 — no two O-atoms are adjacent to one another, now 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, it being also possible for one or more non-adjacent CH 2 groups to 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 , 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 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 (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 them may also be either —O— or a single bond, and, again alternatively, one of them may be —O— and the other one a single bond,
a optionally second component, component B, consisting of nematogenic compounds, preferably 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, it being also possible for one or more non-adjacent CH 2 groups to 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,

X B1 is F, Cl, CN, NCS, preferably CN,
Z B1 , Z B2 , and Z B3 are in each occurrence independently —CH 2 —CH 2 —, —CO—O—, —O—CO—, —CF 2 —O—, —O—CF 2 —, —CH═CH— or a single bond,

are in each occurrence independently

alternatively one or more of

are

and
n is 1, 2 or 3,
and
optionally a second or third component, component C, consisting of one or more chiral molecules.

2 . Mesogenic medium according to claim 1 comprising one or more compounds selected from formulae A-I to A-III, characterized in that MG 11 and MG 12 , MG 21 and MG 22 and MG 31 and MG 32 are independently of each other selected of 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 be replaced by N, trans-1,4-cyclohexylene 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-diy

Assignees

• Merck Patent Gmbh

Inventors

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

Classifications

• C09K19/44

  containing compounds with benzene rings directly linked · CPC title

• C09K19/588

  Heterocyclic compounds · CPC title

• C09K19/0258 Primary

  Flexoelectric · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C09K19/586

  Optically active dopants; chiral dopants · CPC title