Compounds and mesogenic media

Patent metadata

Field	Value
Publication number	US-2016229795-A1
Application number	US-201415024066-A
Country	US
Kind code	A1
Filing date	Sep 8, 2014
Priority date	Sep 25, 2013
Publication date	Aug 11, 2016
Grant date	—

Abstract

Disclosed are compounds of formula I

the use of compounds of formula I in liquid crystal media and in particular to flexoelectric liquid crystal devices containing the liquid crystal media.

First claim

1 . Compounds of formula I

wherein
R 11 and R 12 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 11 and MG 12 are each independently a group, which is 6-atomic ring or comprises one, two or more 6-atomic rings, in case of comprising two or more 6-atomic rings at least two of these may be linked by a 2-atomic linking group, and wherein additionally
MG 11 is a or comprises one 1,3-phenylene, wherein optionally one or two non-adjacent CH groups each may be replaced by an N-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,
Sp 1 is a spacer group comprising 1, 2, 3, 4 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, wherein one or more H atoms in —(CH 2 ) n — may independently of each other optionally be replaced by F or CH 3 and/or one or more non-adjacent —CH 2 — groups may be replaced by —O—, and
X 11 and X 12 are each independently of one another a group selected from —CH═CH—, —C≡C—, —O—, —CF 2 —O—, —O—CF 2 —, —CO—O—, —O—CO—, —O—CO—O—, —S—, —CS—S—, —S—CS—, —CO—S—, —S—CO—, —S—CO—S— and —S—CS—S— or a single bond, however, under the condition that in —X 11 -Sp 1 -X 12 — 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.

2 . Compounds according to claim 1 , characterized in that MG 11 is selected of partial formula II* and MG 12 is selected of partial formula II
-A* 11 -(Z* 11 -A* 12 ) k -   II*
-A 11 -(Z 11 -A 12 ) l -   II
wherein Z 11 and Z* 11 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, Z 11 and Z* 11 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, preferably a single bond, one of A* 11 and A* 12 present in MG 11 is 1,3-phenylene, wherein optionally one or two non-adjacent CH groups each may be replaced by an N-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, the other A* 11 and A* 12 present in MG 11 and A 11 and A 12 are each independently of each other 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, and k and l are independently of each other 0, 1, 2, 3 or 4.

3 . Compounds according to claim 1 , characterized in that MG 11 is selected from the group of formulae II*-0 to II*-26 and their mirror images
-Phe*- II*-0 -PheL*- II*-0′ -Phe*-Z-Phe- II*-1 -Phe-Z-Phe*- II*-1 -Phe*-Z-Cyc- II*-2 -Phe*-Z-PheL- II*-4 -Phe*L-Z-Phe- II*-5 -Phe*L-Z-Cyc- II*-6 -Phe*L-Z-PheL- II*-7 -Phe*-Z-Phe-Z-Phe- II*-8 -Phe*-Z-Phe-Z-Cyc- II*-9 -Phe*-Z-Cyc-Z-Phe- II*-10 -Cyc-Z-Phe*-Z-Cyc- II*-11 -Phe*-Z-Cyc-Z-Cyc- II*-12 -Phe*-Z-Phe-Z-PheL- II*-13 -Phe-Z-Phe*-Z-PheL- II*-14 -Phe*-Z-PheL-Z-Phe- II*-15 -Phe*L-Z-Phe-Z-Phe- II*-16 -Phe*L-Z-Phe-Z-PheL- II*-17 -Phe*L-Z-PheL-Z-Phe- II*-18 -Phe*L-Z-PheL-Z-PheL- II*-19 -Phe*-Z-PheL-Z-Cyc- II*-20 -Phe*-Z-Cyc-Z-PheL- II*-21 -Cyc-Z-Phe*-Z-PheL- II*-22 -Phe*L-Z-Cyc-Z-PheL- II*-23 -Phe*L-Z-PheL-Z-Cyc- II*-24 -Phe*L-Z-Cyc-Z-Cyc- II*-25 -Cyc-Z-Phe*L-Z-Cyc- II*-26 wherein Cyc is 1,4-cyclohexlene, preferably trans-1,4-cyclohexlene, Phe* is 1,3-phenylene or alkyl-1,3-phenylene, Phe is 1,4-phenylene or alkyl-1,4-phenylene, Phe*L is 1,3-phenylene, which is substituted by one, two or three fluorine atoms, by one or two Cl atoms or by one Cl atom and one F atom, PheL is 1,4-phenylene, which is substituted by one, two or three fluorine atoms, by one or two Cl atoms or by one Cl atom and one F atom, and Z is selected from —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 — and —CH═CH—, —CF═CF—, —CH═CH—COO—, —OCO—CH═CH— or —C≡C—, optionally substituted with one or more of F.

4 . Compounds according to claim 1 , characterized in that MG 12 is selected from the group of formulae II-0, II-0′ and II-1 to II-26 and their mirror images
-Phe- II-0
-PheL- II-0′
-Phe-Z-Phe- II-1
-Phe-Z-Cyc- II-2
-Cyc-Z-Cyc- II-3
-Phe-Z-PheL- II-4
-PheL-Z-Phe- II-5
-PheL-Z-Cyc- II-6
-PheL-Z-PheL- II-7
-Phe-Z-Phe-Z-Phe- II-8
-Phe-Z-Phe-Z-Cyc- II-9
-Phe-Z-Cyc-Z-Phe- II-10
-Cyc-Z-Phe-Z-Cyc- II-11
-Phe-Z-Cyc-Z-Cyc- II-12
-Cyc-Z-Cyc-Z-Cyc- II-13
-Phe-Z-Phe-Z-PheL- II-14
-Phe-Z-PheL-Z-Phe- II-15
-PheL-Z-Phe-Z-Phe- II-16
-PheL-Z-Phe-Z-PheL- II-17
-PheL-Z-PheL-Z-Phe- II-18
-PheL-Z-PheL-Z-PheL- II-19
-Phe-Z-PheL-Z-Cyc- II-29
-Phe-Z-Cyc-Z-PheL- II-21
-Cyc-Z-Phe-Z-PheL- II-22
-PheL-Z-Cyc-Z-PheL- II-23
-PheL-Z-PheL-Z-Cyc- II-24
-PheL-Z-Cyc-Z-Cyc- II-25
-Cyc-Z-PheL-Z-Cyc- II-26
wherein
Cyc is 1,4-cyclohexlene, preferably trans-1,4-cyclohexlene,
Phe is 1,4-phenylene or alkyl-1,4-phenylene,
PheL is 1,4-phenylene, which is substituted by one, two or three fluorine atoms, by one or two Cl atoms, by one Cl atom and one F atom or by one alkyl or alkoxy group having 1 to 9 C-atoms, and
Z is 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,

5 . Compounds according to claim 1 , characterized in that R 11 and R 12 are independently of one another selected from OCF 3 , CF 3 , F, Cl and CN.

6 . Compounds according to claim 1 , characterized in that Sp 1 is —(CH 2 ) o — and o is

Assignees

• Merck Patent Gmbh

Inventors

• Adlem Kevin
• Parri Owain Llyr

Classifications

• C09K19/2007

  the chain containing -COO- or -OCO- groups · CPC title

• C09K19/588

  Heterocyclic compounds · CPC title

• C07C255/51

  containing at least two cyano groups bound to the carbon skeleton · CPC title

• C09K2019/0444

  characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group · CPC title

• C09K19/0258 Primary

  Flexoelectric · CPC title