US 12,241,012 B2
Heterocyclic compounds for liquid crystals
Amir Hossain Parham, Darmstadt (DE); Constanze Brocke, Darmstadt (DE); Carsten Fritzsch, Darmstadt (DE); Dagmar Klass, Darmstadt (DE); and Matthias Jost, Darmstadt (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Filed by MERCK PATENT GMBH, Darmstadt (DE)
Filed on Aug. 25, 2023, as Appl. No. 18/238,331.
Prior Publication US 2024/0101903 A1, Mar. 28, 2024
Int. Cl. G02F 1/1333 (2006.01); C07D 285/14 (2006.01); C09K 19/34 (2006.01); H01Q 1/36 (2006.01)
CPC C09K 19/3497 (2013.01) [C07D 285/14 (2013.01); H01Q 1/36 (2013.01)] 17 Claims
 
1. A compound of formula I

OG Complex Work Unit Chemistry
in which
A13 is

OG Complex Work Unit Chemistry
wherein
m is 0 or 1,
W independently on each occurrence is N or CR3,
Y is S or O,
X1 independently on each occurrence is H, F, —CH3, C2H5 or Cl,
R3 is H, F, Cl, CH3 or C2H5,
R1 is H, a straight chain alkyl having 1 to 12 C atoms, a branched chain alkyl having 3 to 12 C atoms, a straight chain alkenyl having 2 to 12 C atoms or a branched chain alkenyl having 3 to 12 C atoms, in which one or more CH2-groups may be replaced by

OG Complex Work Unit Chemistry
where one or more non adjacent CH2-groups may be replaced by O and/or S, and where one or more H atoms may be replaced by F,
Z11, Z12 are, identically or differently and independently on each occurrence, a single bond, —C═C—, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH— or —C≡C—C≡C—,

OG Complex Work Unit Chemistry
each independently and independently on each occurrence are a radical selected from the following groups:
a) the group consisting of 1,4-phenylene, 1,4-naphthylene, 2,6-naphthylene, tetralin-5,8-diyl, and tetralin-2,6-diyl, 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 or alkyl having 1 to 6 C atoms,
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 independently, on each occurrence, is F, Cl, CN, SCN, SF5 or a straight-chain, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, or a branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 12 C atoms, and
n is 0, 1 or 2.