US 12,227,688 B2
Dye-doped liquid-crystal medium comprising polymerizable compounds
Hyun-Woo Bae, Pyeongtaek (KR); Jung-Min Lee, Pyeongtaek (KR); Hyun-Jin Yoon, Pyeongtaek (KR); and Yong-Kuk Yun, Darmstadt (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Filed by Merck Patent GmbH, Darmstadt (DE)
Filed on May 3, 2022, as Appl. No. 17/735,165.
Claims priority of application No. 21171926 (EP), filed on May 4, 2021.
Prior Publication US 2022/0389321 A1, Dec. 8, 2022
Int. Cl. C09K 19/46 (2006.01); C09K 19/04 (2006.01); C09K 19/60 (2006.01); G02F 1/1333 (2006.01); G02F 1/13357 (2006.01); G02F 1/1341 (2006.01)
CPC C09K 19/46 (2013.01) [C09K 19/601 (2013.01); G02F 1/133365 (2013.01); G02F 1/133617 (2013.01); G02F 1/1341 (2013.01); C09K 2019/0448 (2013.01); G02F 2202/36 (2013.01)] 21 Claims
 
1. An LC medium, comprising
0.01 to 3.0% by weight of one or more polymerizable compounds of formula I
P-Sp-Aa-(Za-Ab)z-Rb
wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
Rb is P-Sp- or R,
R is F, Cl, —CN or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR0═CR00—, —C≡C—

OG Complex Work Unit Chemistry
in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl or P-Sp-,
P is a polymerizable group,
Sp is a spacer group which is optionally substituted by P, or is a single bond,
Aa, Ab is an alicyclic, heterocyclic, aromatic or heteroaromatic group with 4 to 20 ring atoms, which is monocyclic or polycyclic and which is optionally substituted by one or more groups L or P-Sp-,
Za is —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —CH═CH—CO—O—, —O—CO—CH═CH—, —CH2—CH2—CO—O—, —O—CO—CH2—CH2—, —CR0R00—, or a single bond,
R0, R00 is H or alkyl having 1 to 12 C atoms,
L is F, Cl, —CN, P-Sp- or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR0═CR00—, —C≡C—

OG Complex Work Unit Chemistry
in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by P-Sp-, F or Cl,
z is 0, 1, 2, 3 or 4,
n1 is 1, 2, 3 or 4,
and further comprising one or more compounds of formula II

OG Complex Work Unit Chemistry
wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
R1, R2 is H or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR0═CR00—, —C≡C—,

OG Complex Work Unit Chemistry
in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by CN, CF3, F or Cl,
A1, A2 is selected from the following formulae

OG Complex Work Unit Chemistry
Z1, Z2 is —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —CO—O—, —O—CO—, —C2F4—, —CF═CF—, —CH═CH—CH2O— or a single bond,
L1, L2, L3, L4 is F, Cl, OCF3, CF3, CH3, CH2F or CHF2,
Y H, F, Cl, CF3, CHF2 or CH3,
LC CH3 or OCH3,
a1 0, 1 or 2, and
a2 0 or 1,
and further comprising at least one dichroic dye absorbing green light and/or at least one dichroic dye absorbing red light,
wherein the LC comprises one or more dichroic dyes of formulae I*

OG Complex Work Unit Chemistry
wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings

OG Complex Work Unit Chemistry
are independently of each other

OG Complex Work Unit Chemistry
and, in case i is 2 or more, the terminal

OG Complex Work Unit Chemistry
may also be

OG Complex Work Unit Chemistry
and, in case j is 2 or more, the terminal

OG Complex Work Unit Chemistry
may also be

OG Complex Work Unit Chemistry
Z11 and Z12 denote a single bond, —N═N—, —OCO— or —COO—,
R11 and R12 denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 20 C-atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 20 C-atoms, or alkylaminyl, dialkylaminyl, alkylcarbonyl, alkyloxycarbonyl, alkylcarbonyloxy or alkyloxycarbonyloxy with 3 to 20 C-atoms, or alkylcyclohexylalkyl with 8 to 25 C-atoms,
i and j are independently of each other 1, 2, 3 or 4.