US 9,809,748 B2
Liquid-crystalline media having homeotropic alignment
Graziano Archetti, Darmstadt (DE); Izumi Saito, Darmstadt (DE); Rocco Fortte, Frankfurt am Main (DE); and Thorsten Kodek, Moerfelden-Walldorf (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Filed by Merck Patent GmbH, Darmstadt (DE)
Filed on Mar. 10, 2015, as Appl. No. 14/643,147.
Claims priority of application No. 14000831 (EP), filed on Mar. 10, 2014; and application No. 14003943 (EP), filed on Nov. 24, 2014.
Prior Publication US 2015/0252265 A1, Sep. 10, 2015
Int. Cl. G02F 1/1333 (2006.01); C09K 19/34 (2006.01); C09K 19/38 (2006.01); C09K 19/30 (2006.01); C09K 19/56 (2006.01); G02F 1/1337 (2006.01); G02F 1/1343 (2006.01); G02F 1/1341 (2006.01); C09K 19/04 (2006.01); C09K 19/14 (2006.01); C09K 19/12 (2006.01)
CPC C09K 19/3402 (2013.01) [C09K 19/04 (2013.01); C09K 19/14 (2013.01); C09K 19/3003 (2013.01); C09K 19/3068 (2013.01); C09K 19/3852 (2013.01); C09K 19/56 (2013.01); G02F 1/1337 (2013.01); G02F 1/1341 (2013.01); G02F 1/133788 (2013.01); G02F 1/134363 (2013.01); C09K 2019/0448 (2013.01); C09K 2019/122 (2013.01); C09K 2019/123 (2013.01); C09K 2019/301 (2013.01); C09K 2019/3004 (2013.01); C09K 2019/304 (2013.01); C09K 2019/3009 (2013.01); C09K 2019/3016 (2013.01); C09K 2019/3027 (2013.01); C09K 2019/3078 (2013.01); C09K 2019/3422 (2013.01); G02F 2001/133742 (2013.01)] 38 Claims
 
1. A liquid-crystal medium comprising a low-molecular-weight, non-polymerizable liquid-crystalline component and a polymerizable or polymerized component comprising one or more polymerizable compounds of formula I, where the polymerized component is obtainable by polymerization of the polymerizable component,
R1-[A3Z3]m-[A2]k-[Z2]n-A1-Ra  (I)
in which
A1, A2, A3 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which may also contain fused rings, and which is unsubstituted or mono- or polysubstituted by a group L or -Sp-P,
L in each case, independently of one another, denotes H, F, Cl, Br, I, —CN, —NO2, —NCO, —NCS, —OCN, —SCN, —C(═O)N(R0)2, —C(═O)R0, optionally substituted silyl, optionally substituted aryl or cycloalkyl having 3 to 20 C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having up to 25 C atoms, in which, in addition, one or more H atoms are each optionally replaced by F or Cl,
P denotes a polymerizable group,
Sp denotes a spacer group or a single bond,
Z2 in each case, independently of one another, denotes —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, —(CR0R00)n1—, —CH(-Sp-P)—, —CH2CH(-Sp-P)—, or —CH(-Sp-P)CH(-Sp-P)—,
Z3 in each case, independently of one another, denotes a single bond, —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, —(CR0R00)n1—, —CH(-Sp-P)—, —CH2CH(-Sp-P)—, or —CH(-Sp-P)CH(-Sp-P)—,
n1 denotes 1, 2, 3 or 4,
n denotes 0 or 1,
m denotes 0, 1, 2, 3, 4, 5 or 6,
k denotes 0 or 1,
R0 in each case, independently of one another, denotes alkyl having 1 to 12 C atoms,
R00 in each case, independently of one another, denotes H or alkyl having 1 to 12 C atoms,
R1, independently of one another, denotes H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups are each optionally 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 are each optionally replaced by F or Cl,
or a group -Sp-P,
Ra denotes an anchor group of the formula

OG Complex Work Unit Drawing
p denotes 1 or 2,
q denotes 2 or 3,
B denotes a substituted or unsubstituted ring system or condensed ring system,
Y, independently of one another, denotes —O—, —S—, —C(O)—, —C(O)O—, —OC(O)—, —NR11— or a single bond,
o denotes 0 or 1,
X1, independently of one another, denotes H, alkyl, fluoroalkyl, OH, NH2, NHR11, NR112, OR11, C(O)OH, —CHO,
where at least one group X1 denotes a radical selected from —OH, —NH2, NHR11, C(O)OH and —CHO,
R11 denotes alkyl having 1 to 12 C atoms,
Spa, Spc, Spd each, independently of one another, denote a spacer group or a single bond, and
Spb denotes a tri- or tetravalent group,
where the compound of formula I contains at least one polymerizable group P within at least one of the groups A1, A2, A3, Z2 and Z3, as are present.