US 11,939,512 B2
Dichroic dye composition
Michael Junge, Pfungstadt (DE); Ewa Ptak, Weiterstadt (DE); and Christoph Wetzel, Darmstadt (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Appl. No. 17/295,913
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Nov. 21, 2019, PCT No. PCT/EP2019/082006
§ 371(c)(1), (2) Date May 21, 2021,
PCT Pub. No. WO2020/104563, PCT Pub. Date May 28, 2020.
Claims priority of application No. 18208072 (EP), filed on Nov. 23, 2018; and application No. 19196906 (EP), filed on Sep. 12, 2019.
Prior Publication US 2023/0053362 A1, Feb. 23, 2023
Int. Cl. G02F 1/1333 (2006.01); C09K 19/30 (2006.01); C09K 19/34 (2006.01); C09K 19/60 (2006.01); C09K 19/04 (2006.01)
CPC C09K 19/608 (2013.01) [C09K 19/30 (2013.01); C09K 19/3003 (2013.01); C09K 19/3068 (2013.01); C09K 19/3402 (2013.01); C09K 2019/0466 (2013.01); C09K 2019/3004 (2013.01); C09K 2019/3009 (2013.01); C09K 2019/301 (2013.01); C09K 2019/3016 (2013.01); C09K 2019/3019 (2013.01); C09K 2019/3021 (2013.01); C09K 2019/3025 (2013.01); C09K 2019/3071 (2013.01); C09K 2019/3078 (2013.01); C09K 2019/3422 (2013.01)] 21 Claims
 
1. A liquid-crystalline medium comprising:
two or more compounds of formula I

OG Complex Work Unit Chemistry
and two or more compounds of formula II

OG Complex Work Unit Chemistry
wherein
R1 on each occurrence, identically or differently, denotes H, F, CN, N(Rz)2, Si(Rz)3, or a straight-chain having 1 to 20 C atoms or branched alkyl or alkoxy having 3 to 20 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by —C(Rz)═C(Rz)—, —C≡C—,

OG Complex Work Unit Chemistry
—N(Rz)—, —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may each be replaced by F or CN,
X on each occurrence, identically or differently, denotes CRa or N,
Ra on each occurrence, identically or differently, denotes H, straight-chain alkyl having 1 to 12 C atoms, branched alkyl having 3 to 12 C atoms, F, Cl, N(Rz)2 or CN,
R2 and Rz on each occurrence, identically or differently, denote H, halogen, or straight-chain alkyl having 1 to 12 C atoms, branched alkyl having 3 to 12 C atoms, or cyclic alkyl having 3 to 12 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may each be replaced by F or Cl,
Ar1 and Ar2 on each occurrence, identically or differently, denote an aryl or heteroaryl group, which may be substituted by one or more radicals L,
L on each occurrence, identically or differently, denotes F, Cl, CN, OH, SCN, SF5, N(Rz)2, straight-chain, optionally fluorinated, alkyl or alkoxy having 1 to 12 C atoms, branched, optionally fluorinated, alkyl or alkoxy having 3 to 12 C atoms, straight-chain alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, optionally fluorinated, having 2 to 12 C atoms, or branched alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, optionally fluorinated, having 4 to 12 C atoms
Z1 on each occurrence, identically or differently, denotes a single bond, —O—, —S—, —C(O)—, —CRy1Ry2—, —CF2O—, —OCF2—, —C(O)—O—, —O—C(O)—, —OCH2—, —CH2O—, —CRx1═CRx2—, —C≡C—, —CRx1═CRx2—CO—, —CO—CRx1═CRx2—, —CRx1═CRx2—COO—, —OCO—CRx1═CRx2— or —N═N—,
Z2 on each occurrence, identically or differently, denotes a single bond, —CF2O—, —OCF2— or —C≡C—,
a, b, c and d independently of one another, denote 0 or 1,
Rx1, Rx2 independently of one another, denote H, F, Cl, CN or alkyl having 1 to 12 C atoms,
Ry1 denotes H or alkyl having 1 to 12 C atoms, and
Ry2 denotes alkyl having 1 to 12 C atoms, and
one or more mesogenic compounds,
wherein the composition comprises at least one purple dye, at least one blue dye, at least one yellow dye, at least one red dye and at least one near-infrared dye.