US 11,939,511 B2
Liquid crystal mixture and liquid crystal display
Lars Lietzau, Rossdorf (DE); Simon Siemianowski, Rossdorf (DE); and Izumi Saito, Darmstadt (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Appl. No. 17/049,516
Filed by MERCK PATENT GMBH, Darmstadt (DE)
PCT Filed Apr. 18, 2019, PCT No. PCT/EP2019/060042
§ 371(c)(1), (2) Date Oct. 21, 2020,
PCT Pub. No. WO2019/206788, PCT Pub. Date Oct. 31, 2019.
Claims priority of application No. 18168775 (EP), filed on Apr. 23, 2018.
Prior Publication US 2021/0292652 A1, Sep. 23, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. G02F 1/1333 (2006.01); C07C 13/28 (2006.01); C07C 25/18 (2006.01); C07C 25/24 (2006.01); C07C 43/184 (2006.01); C07C 43/21 (2006.01); C07C 43/225 (2006.01); C07C 69/753 (2006.01); C07D 213/30 (2006.01); C07D 239/26 (2006.01); C07D 307/91 (2006.01); C07D 309/06 (2006.01); C07D 311/80 (2006.01); C07D 319/06 (2006.01); C09K 19/30 (2006.01); C09K 19/34 (2006.01); C09K 19/56 (2006.01); G02F 1/1337 (2006.01); G02F 1/1341 (2006.01); C09K 19/04 (2006.01)
CPC C09K 19/56 (2013.01) [C07C 13/28 (2013.01); C07C 25/18 (2013.01); C07C 25/24 (2013.01); C07C 43/184 (2013.01); C07C 43/21 (2013.01); C07C 43/225 (2013.01); C07C 69/753 (2013.01); C07D 213/30 (2013.01); C07D 239/26 (2013.01); C07D 307/91 (2013.01); C07D 309/06 (2013.01); C07D 311/80 (2013.01); C07D 319/06 (2013.01); C09K 19/3003 (2013.01); C09K 19/3066 (2013.01); C09K 19/3098 (2013.01); C09K 19/3402 (2013.01); C09K 19/3491 (2013.01); G02F 1/133738 (2021.01); G02F 1/133788 (2013.01); G02F 1/1341 (2013.01); C07C 2601/14 (2017.05); C07C 2602/10 (2017.05); 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 2019/3025 (2013.01); C09K 2019/3422 (2013.01); C09K 2019/3425 (2013.01)] 25 Claims
 
1. A compound of formula I,

OG Complex Work Unit Chemistry
wherein
A11 denotes
a) 1,4-phenylene or 1,3-phenylene, in which one or two CH groups may be replaced by N and wherein one or more H atoms may be replaced by L,
or
b) one of the following radicals

OG Complex Work Unit Chemistry
wherein one or more H atoms in these radicals may be replaced by L, and/or one or more double bonds may be replaced by single bonds, and/or one or more CH groups may be replaced by N,
A have each, independently of one another, in each occurrence one of the meanings for A11 or
a) trans-1,4-cyclohexylene, 1,4-cyclohexenylene, in which one or more non-adjacent CH2 groups may be replaced by —O— and/or —S— and wherein one or more H atoms may be replaced by F, or
b) tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl or selenophene-2,5-diyl, each of which may be mono- or polysubstituted by L,
L denotes, independently of one another, in each occurrence, —OH, —F, —Cl, —Br, —I, —CN, —NO2, SF5, —NCO, —NCS, —OCN, —SCN, —C(═O)N(Rz)2, —C(═O)Rz, —N(Rz)2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or straight-chain alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms or branched or cyclic alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 25 C atoms, in which one or more H atoms may be replaced by F or Cl, or X21—Sp21—R21,
M denotes —O—, —S—, —CH2—, —CHRz— or —CRYRz—,
Ry and Rz denote each, independently of one another, in each occurrence, H, CN, F or alkyl having 1-12 C atoms, wherein one or more H atoms may be replaced by F,
Y11 and Y12 denote each, independently of one another, in each occurrence, H, F, phenyl or optionally fluorinated alkyl having 1-12 C atoms,
Z denotes in each occurrence and each independently from another a single bond, —COO—, —OCO—, —O—CO—O—, —OCH2—, —CH2O—, —OCF2—, —CF2O—, —(CH2)n—, —CF2CF2—, —CH═CH—, —CF═CF—, —CH═CH—COO—, —OCO—CH═CH—, —CO—S—, —S—CO—, —CS—S—, —S—CS—, —S—CSS— or —CC—,
n denotes an integer between 2 and 8,
o and p denotes independently from another 0, 1 or 2,
X11 and X21 denote, independently from one another, in each occurrence a single bond, —CO—O—, —O—CO—, —O—COO—, —O—, —CH═CH—, —C≡C—, —CF2—O—, —O—CF2—, —CF2—CF2—, —CH2—O—, —O—CH2—, —CO—S—, —S—CO—, —CS—S—, —S—CS—, —S—CSS— or —S—,
Sp11 and Sp21 denote each independently, in each occurrence a single bond or a spacer group containing 1 to 20 C atoms, in which one or more non-adjacent and non-terminal CH2 groups may also be replaced by —O—, —S—, —NH—, —N(CH3)—, —CO—, —O—CO—, —S—CO—, —O—COO—, —CO—S—, —CO—O—, —CF2—, —CF2O—, —OCF2——C(OH)—, —CH(alkyl)-, —CH(alkenyl)-, —CH(alkoxyl)-, —CH(oxaalkyl)-, —CH═CH— or —C≡C—, in such a way that no two are adjacent to one another and no two groups selected from —O—CO—, —S—CO—, —O—COO—, —CO—S—, —CO—O— and —CH═CH— are adjacent to each other,
R11 denotes a group

OG Complex Work Unit Chemistry
Y denotes H, F, phenyl or optionally fluorinated alkyl having 1-12 C atoms,
R21 denotes R11, P, halogen, CN, optionally fluorinated alkyl with 1 to 15 C atoms or optionally fluorinated alkenyl with 2 to 15 C atoms, in which one or more non adjacent CH2-groups may be replaced by —O—, —S—, —CO—, —C(O)O—, —O—C(O)—, or O—C(O)—O—,
P each independently from another in each occurrence a polymerizable group,
q and r denotes each independently an integer from 0 to 8.