US 12,359,128 B2
Heteroaromatic isothiocyanates
Constanze Brocke, Darmstadt (DE); Dagmar Klass, Darmstadt (DE); Carsten Fritsch, Darmstadt (DE); and Amir Hossain Parham, Darmstadt (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Appl. No. 18/266,657
Filed by MERCK PATENT GMBH, Darmstadt (DE)
PCT Filed Dec. 14, 2021, PCT No. PCT/EP2021/085647
§ 371(c)(1), (2) Date Jun. 12, 2023,
PCT Pub. No. WO2022/129018, PCT Pub. Date Jun. 23, 2022.
Claims priority of application No. 20215004 (EP), filed on Dec. 17, 2020.
Prior Publication US 2024/0124779 A1, Apr. 18, 2024
Int. Cl. C09K 19/12 (2006.01); C09K 19/16 (2006.01); C09K 19/18 (2006.01); C09K 19/30 (2006.01)
CPC C09K 19/12 (2013.01) [C09K 19/18 (2013.01); C09K 19/3003 (2013.01); C09K 19/3048 (2013.01); C09K 19/3059 (2013.01); C09K 2019/122 (2013.01); C09K 2019/123 (2013.01); C09K 2019/124 (2013.01); C09K 2019/163 (2013.01); C09K 2019/183 (2013.01); C09K 2019/3016 (2013.01); C09K 2019/3025 (2013.01); C09K 2019/305 (2013.01); C09K 2019/306 (2013.01); C09K 2019/3062 (2013.01); C09K 2019/3063 (2013.01); C09K 2219/17 (2013.01)] 17 Claims
 
1. A liquid-crystal medium comprising:
one or more compounds of formula N

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in which
RN denotes H, alkyl or alkoxy having 1 to 12 C atoms, or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12 C atoms, in which one or more CH2-groups may be replaced by,

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or denotes a group RP,
RP denotes halogen, CN, NCS, RF, RF—O—, or RF—S—, wherein RF denotes fluorinated alkyl having 1 to 9 C atoms or fluorinated alkenyl having 2 to 9 C atoms,
ZN1 and ZN2, identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —C≡C—C≡C—, or a single bond,
W denotes N, C—F or C—Cl,
X1 and X2, identically or differently, denote H, Cl, F, methyl, or ethyl,

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on each occurrence, identically or differently, denote a radical selected from:
a) the group consisting of 1,4-phenylene, 1,4-naphthylene, and 2,6-naphthylene, in which one or two CH groups may each be replaced by N and in which one or more H atoms may each be replaced by L,
b) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, bicyclo[1.1.1]pentane-1,3-diyl, 4,4′-bicyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, and spiro[3.3]heptane-2,6-diyl, in which one or more non-adjacent CH2 groups may each be replaced by —O— or —S— and in which one or more H atoms may each be replaced by F, and
c) the group consisting of thiophene-2,5-diyl, thieno[3,2-b]thiophene-2,5-diyl and selenophene-2,5-diyl, each of which may be mono- or polysubstituted by L,
L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF5, or straight-chain, in each case optionally fluorinated, alkyl having 1 to 12 C atoms, alkoxy having 1 to 12 C atoms, alkylcarbonyl having 2 to 12 C atoms, alkoxycarbonyl having 2 to 12 C atoms, alkylcarbonyloxy having 2 to 12 C atoms, or alkoxycarbonyloxy having 2 to 12 C atoms, or branched, in each case optionally fluorinated, alkyl having 3 to 12 C atoms, alkoxy having 3 to 12 C atoms, alkylcarbonyl having 4 to 12 C atoms, alkoxycarbonyl having 4 to 12 C atoms, alkylcarbonyloxy having 4 to 12 C atoms, or alkoxycarbonyloxy having h to 12 C atoms, and
n is 0, 1 or 2; and
one or more compounds selected from the group of compounds consisting of the compounds of formulae I, II and III,

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in which
R1 denotes H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH2-groups may each be replaced by,

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n is 0, 1 or 2,

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on each occurrence, independently of one another, denote

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in which RL, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms,
and wherein

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alternatively denotes

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R2 denotes H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH2-groups may each be replaced by,

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Z21 denotes trans-CH═CH—, trans-CF═CF— or —C≡C—, and

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independently of one another, denote

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in which RL, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms;
R3 denotes H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH2-groups may each be replaced by,

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one of Z31 and Z32, denotes trans-CH═CH—, trans-CF═CF—, or —C≡C— and the other one, independently thereof, denotes —C≡C—, trans-CH═CH—, trans-CF═CF—, or a single bond, and

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independently of one another, denote

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in which RL, on each occurrence identically or differently,
denotes H or alkyl having 1 to 6 C atoms,
and wherein

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alternatively denotes

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