US 12,077,703 B2
Heteroaromatic isothiocyanates
Amir Hossain Parham, Darmstadt (DE); Constanze Brocke, Darmstadt (DE); Carsten Fritzsch, Darmstadt (DE); and Dagmar Klass, Darmstadt (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Appl. No. 18/267,661
Filed by MERCK PATENT GMBH, Darmstadt (DE)
PCT Filed Dec. 13, 2021, PCT No. PCT/EP2021/085371
§ 371(c)(1), (2) Date Jun. 15, 2023,
PCT Pub. No. WO2022/128845, PCT Pub. Date Jun. 23, 2022.
Claims priority of application No. 20214400 (EP), filed on Dec. 16, 2020.
Prior Publication US 2024/0124780 A1, Apr. 18, 2024
Int. Cl. G02F 1/1333 (2006.01); C07D 213/72 (2006.01); C07D 213/73 (2006.01); C07D 239/42 (2006.01); C07D 405/10 (2006.01); C09K 19/34 (2006.01); H01Q 23/00 (2006.01)
CPC C09K 19/3469 (2013.01) [C07D 213/72 (2013.01); C07D 213/73 (2013.01); C07D 239/42 (2013.01); C07D 405/10 (2013.01); C09K 19/3444 (2013.01); H01Q 23/00 (2013.01)] 17 Claims
 
1. A compound of formula N

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

OG Complex Work Unit Chemistry
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,
X denotes C—H, N, C—F or C—Cl,
Y1 and Y2, identically or differently, denote H, Cl, F, methyl or ethyl,

OG Complex Work Unit Chemistry
denote a radical selected from the following groups:
a) the group consisting of 1,4-phenylene, 1,4-naphthylene and 2,6-naphthylene, in which one or two CH groups may be replaced by N and in which one or more H atoms may 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 be replaced by —O— and/or —S— and in which one or more H atoms may be replaced by F,
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 also be mono- or polysubstituted by L,
L on each occurrence, identically or differently, denotes F, CI, CN, SCN, SF5 or straight-chain, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 12 C atoms, and
t is 0, 1 or 2.