# US 9,752,075 B2 · Mesogenic media and liquid crystal display

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- Number: US 9,752,075 B2
- Document ID: US9752075B2
- Status: Granted
- Kind: B2
- Application number: 15/038,592
- Filed: 2014-10-23
- Published: 2016-10-13
- Granted: 2017-09-05
- Earliest claimed: 2013-11-22
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Rachel Tuffin; Rebecca Proctor; Simon Siemianowski; Benjamin Snow; Owain Llyr Parri; Kevin Adlem
- Web page: https://patentgrep.com/patent/US9752075B2

## CPC

- C09K 19/3068: {chain containing -COO- or -OCO- groups}
- C09K 19/0258: {Flexoelectric}
- C09K 19/062: {containing one non-condensed benzene ring}
- C09K 19/2021: {Compounds containing at least one asymmetric carbon atom}
- C09K 19/42: Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K 19/44: containing compounds with benzene rings directly linked
- C09K 19/586: {Optically active dopants; chiral dopants}
- C09K 19/588: {Heterocyclic compounds}
- G02F 1/134309: {characterised by their geometrical arrangement}
- C09K 2019/0444: {characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group}
- C09K 2019/122: {Ph-Ph}
- C09K 2019/123: {Ph-Ph-Ph}
- C09K 2019/181: {Ph-C≡C-Ph}
- C09K 2019/183: {Ph-Ph-C≡C-Ph}
- C09K 2019/3004: {Cy-Cy}
- C09K 2019/3009: {Cy-Ph}
- C09K 2019/301: {Cy-Cy-Ph}
- C09K 2019/3021: {Cy-Ph-Ph-Cy}
- C09K 2323/00: Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- G02F 1/133394: {Piezoelectric elements associated with the cells}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS

## 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.

## Claims

### Claim 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
R01 and R02 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 CH2 groups, in each occurrence independently from one another, are optionally replaced by —O—, —S—, —NH—, —N(CH3)—, —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,
MG01 is -A01-Z01-A02-,
MG02 is -A03-Z02-A04-Z03-A05-,
Z01 to Z03 are, independently of each other in each occurrence, a single bond, —COO—, —OCO—, —O—CO—O—, —OCH2—, —CH2O—, —OCF2—, —CF2O—, —CH2CH2—, —(CH2)4—, —CF2CF2—, —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,
A01 to A05 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 CH2 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,
Sp0 is a spacer group comprising 1, 3 or 5 to 40 C atoms, wherein one or more non-adjacent and non-terminal CH2 groups may each be replaced by —O—, —S—, —NH—, —N(CH3)—, —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
X01 and X02 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 X01 and X02 are different from each other,
however under the condition that in —X01-Sp0-X02— 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
R11 and R12, R21 and R22 and R31 and R32 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 CH2 groups, in each occurrence independently from one another, are optionally replaced by —O—, —S—, —NH—, —N(CH3)—, —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,
MG11 and MG12, MG21 and MG22 and MG31 and MG32 are each independently a mesogenic group,
Sp1, Sp2 and Sp3 are each independently a spacer group comprising 5 to 40 C atoms, wherein one or more non-adjacent CH2 groups, with the exception of the CH2 groups of Sp1 linked to O-MG11 and/or O-MG12, of Sp2 linked to MG21 and/or MG22 and of Sp3 linked to X31 and X32, may each be replaced by —O—, —S—, —NH—, —N(CH3)—, —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
X31 and X32 are independently from one another a linking group selected from —CO—O—, —O—CO—, —CH═CH—, —C≡C— or —S—, and, alternatively, one of X31 and X32 may also be either —O— or a single bond, and, again alternatively, one of X31 and X32 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.

### Claim 2 (depends on 1)

The mesogenic medium according to claim 1, wherein in said formulae A-I to A-III, MG11 and MG12, MG21 and MG22 and MG31 and MG32 are independently of each other selected from formula II
-A1-(Z1-A2)m- II
wherein
Z1 is —COO—, —OCO—, —O—CO—O—, —OCH2—, —CH2O—, —CH2CH2—, —(CH2)4—, —CF2CF2—, —CH═CH—, —CF═CF—, —CH═CH—COO—, —OCO—CH═CH—, —C≡C— or a single bond,
A1 and A2 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 CH2 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.

### Claim 3 (depends on 1)

The mesogenic medium according to claim 1, wherein in formulae A-I to A-III, MG11 and MG12, MG21 and MG22 and MG31 and MG32 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, NO2 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.

### Claim 4 (depends on 1)

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
RB1, RB21 and RB22 and RB31 and RB32 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 CH2 groups, in each occurrence independently from one another, are optionally replaced by —O—, —S—, —NH—, —N(CH3)—, —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,
XB1 is F, Cl, CN, NCS, preferably CN,
ZB1, ZB2 and ZB3 are in each occurrence independently —CH2—CH2—, —CO—O—, —O—CO—, —CF2—O—, —O— CF2—, —CH═CH— or a single bond,
are in each occurrence independently
alternatively one or more of
are
and
n is 1, 2 or 3.

### Claim 5 (depends on 1)

The mesogenic medium according to claim 1, wherein said medium comprises one or more compounds of formula A-II.

### Claim 6 (depends on 1)

The mesogenic medium according to claim 1, wherein said medium comprises one or more compounds of formula A-III.

### Claim 7 (depends on 4)

The mesogenic medium according claim 4, wherein said medium comprises one or more compounds of formula B-I.

### Claim 8 (depends on 4)

The mesogenic medium according to claim 4, wherein said medium comprises one or more compounds of formula B-II.

### Claim 9 (depends on 4)

The mesogenic medium according to claim 4, wherein said medium comprises one or more compounds of formula B-III.

### Claim 10 (depends on 4)

The mesogenic medium according to claim 4, wherein component B consists of compounds selected from the group of compounds of formulae B-I to B-III in a concentration of 40% or less based on the medium as a whole.

### Claim 11 (depends on 1)

The mesogenic medium according to claim 1, wherein said medium exhibits a first nematic phase and a second nematic phase.

### Claim 12 (depends on 1)

A method of generating an electro-optical effect comprising applying a voltage across a liquid crystal cell in a liquid crystal device, wherein said cell contains a mesogenic medium according to claim 1.

### Claim 13 (depends on 1)

A liquid crystal device comprising a mesogenic medium according to claim 1.

### Claim 14 (depends on 13)

The liquid crystal device according to claim 13, wherein said device is a flexoelectric device.

### Claim 15 (depends on 13)

The liquid crystal device according to claim 13, wherein said device comprises two plane parallel electrodes the inner surfaces of which exhibit planar, anti-parallel alignment conditions.

### Claim 16 (depends on 1)

The mesogenic medium according to claim 1, wherein said medium comprises one or more compounds of formula A-I.

### Claim 17 (depends on 1)

The mesogenic medium according to claim 1, wherein Z01 to Z03 are each a single bond.

### Claim 18 (depends on 1)

The mesogenic medium according to claim 1, wherein R01 and R02 are each independently F, Cl, CN, OCF3, or CF3.

### Claim 19 (depends on 1)

The mesogenic medium according to claim 1, wherein A01 to A05 are each unsubstituted or mono-, di-, tri- or tetrasubstituted by substituents selected from F, Cl, CH3 and CF3.

### Claim 20 (depends on 1)

The mesogenic medium according to claim 1, wherein Sp0 is —(CH2)n— wherein n is an integer from 3 to 19.

### Claim 21 (depends on 1)

The mesogenic medium according to claim 1, wherein Sp0 is —(CH2)n— wherein n is 3, 5, 7, 9 or 11.

### Claim 22 (depends on 1)

The mesogenic medium according to claim 1, wherein: (a) X01 is —CO—O— or —O— and X02 is a single bond, or (b) X01 is —CO—O— and X02 is —O—.

### Claim 23 (depends on 1)

The mesogenic medium according to claim 1, wherein X01 is —CO—O— and X02 is a single bond.

### Claim 24 (depends on 4)

The mesogenic medium according to claim 4, wherein XB1 is CN.

### Claim 25 (depends on 1)

The mesogenic medium according to claim 1, wherein:
the compounds of formula A-I are selected from the group of compounds of formulae A-I-1 to A-I-3
wherein n is an integer from 3 to 19;
the compounds of formula A-II are selected from the group of compounds of formulae A-II-1 to A-II-4
wherein n is an integer from 3 to 19; and
the compounds of formula A-III are selected from the group of compounds of formulae A-III-1 to A-III-11
wherein n is an integer from 3 to 19.