Liquid crystalline medium

Patent metadata

Field	Value
Publication number	US-10934487-B2
Application number	US-201314379793-A
Country	US
Kind code	B2
Filing date	Feb 12, 2013
Priority date	Feb 22, 2012
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

The invention relates to a liquid-crystalline medium which contains at least two polymerisable compounds or reactive mesogens (RM)
and
at least one compound selected from the group of compounds of the formula IIA, IIB and IIC,

in which
R 2A , R 2B , R 2C , L 1-6 , ring B, Z 2 , Z 2 , p, q and v have the meanings indicated in Claim 1,

and to the use thereof for an active-matrix display, in particular based on the VA, PSA, PS-VA, PALC, FFS, PS-FFS, IPS or PS-IPS effect, especially for the use in LC displays of the PS (polymer stabilised) or PSA (polymer sustained alignment) type.

First claim

The invention claimed is:

1. A liquid-crystalline medium based on a mixture of polar compounds having negative dielectric anisotropy, comprising
at least two reactive mesogens, at least two of said reactive mesogens having sufficiently different polymerization reactivity from one another allowing their polymerization by two separate polymerizations

and
at least one compound selected from the group of compounds consisting of the compounds of formulae IIA, IIB and IIC,

in which
R 2A , R 2B and R 2c each, independently of one another, denote H, an alkyl or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF 3 or at least monosubstituted by halogen, in which one or more CH 2 groups are optionally replaced by —O—, —S—,

—C≡C—, —CF 2 O—, —OCF 2 —, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another,

denotes

Y 1-6 each, independently of one another, denote H or F,
L 1 and L 2 each, independently of one another, denote F, Cl, CF 3 or CHF 2 ,
L 3-6 each, independently of one another, denote H, F, Cl, CF 3 or CHF 2 , but at least two of L 3-6 denote F, Cl, CF 3 or CHF 2 ,
Z 2 and Z 2′ each, independently of one another, denote a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —CF═CF—, or —CH═CHCH 2 O—,
p denotes 1 or 2, and, in the case where Z 2 =single bond, p also denotes 0,
q denotes 0 or 1,
y denotes 0 or 1, and
denotes 1 to 6.

2. The liquid-crystalline medium according to claim 1 , wherein the at least two reactive mesogens each having a polymerization reactivity that is different from the other of the at least two reactive mesogens are compounds of formula I
R Ma -A M1 -(Z M1 -A M2 ) m1 -R Mb   I

wherein
R M a and R Mb each, independently of one another, denote P, P-Sp-, H, halogen, SF 5 , NO 2 , an alkyl, alkenyl or alkynyl group,
P denotes a polymerizable group,
Sp denotes a spacer group or a single bond,
A M1 and A M2 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which optionally encompasses or contains fused rings, and which is optionally mono- or polysubstituted by L,
L denotes P, P-Sp-, OH, CH 2 OH, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(Rx) 2 , —C(═O)Y 1 , —C(═O)R x , —N(R x ) 2 , SF 5 , optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or straight-chain or branched alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which one or more H atoms are optionally replaced by F, Cl, P or P-Sp-,
Y 1 denotes halogen,
Z M1 denotes —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n1 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n1 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—, —COO—, —OCO—CH═CH—, CR 0 R 00 or a single bond,
R 0 and R 00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
R x denotes P, P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH 2 groups are 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 one or more H atoms are optionally replaced by F, Cl, P or P-Sp-, an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms,
m1 denotes 0, 1, 2, 3 or 4, and
n1 denotes 1, 2, 3 or 4,
where at least one of R Ma , R Mb and L denotes P or P-Sp- or contains at least one group P or P-Sp-.

3. The liquid-crystalline medium according to claim 2 , wherein one of R Ma and R Mb or both denote(s) P or P-Sp-.

4. The liquid-crystalline medium according to claim 1 , which contains at least two reactive mesogens selected from the group consisting of the compounds of formulae I-1 to I-44

wherein
P 1 and P 2 each, independently of one another, denote a polymerizable group,
Sp 1 and Sp 2 each, independently of one another, denote a single bond or a spacer group, where one of the radicals P 1 -Sp 1 - and P 2 —Sp 2 - optionally denotes R aa ,
R aa denotes H, F, Cl, CN or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH 2 groups are optionally each replaced, independently of one another, by —C(R 0 )═C(R 00 ))—, —C≡C—, N(R 0 )—, —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 one or more H atoms are optionally replaced by F, Cl, CN or P 1 -SP 1 -,
R 0 , R 00 each, independently of one another and on each occurrence identically or differently, denote H or alkyl having 1 to 12 C atoms,
R y and R z each, independently of one another, denote H, F, CH 3 or CF 3 ,
Z 1 denotes —O—, —CO—, —C(R y R z )— or —CF 2 CF 2 —,
Z 2 and Z 3 each, independently of one another, denote —CO—O—, —O—CO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 — or —(CH 2 ) n —,
n is 2, 3 or 4,
L on each occurrence, identically or differently, denotes F, Cl, CN, or straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl or alkylcarbonyloxy having 1 to 12 C atoms,
L′ and L″ each, independently of one another, denote H, F, Cl or CF 3 ,
r denotes 0, 1, 2, 3 or 4,
denotes 0, 1, 2 or 3,
t denotes 0, 1 or 2, and
x denotes 0 or 1.

5. The liquid-crystalline medium according to claim 1 , which contains at least two reactive mesogens selected from the group consisting of the compounds of formulae RM-1 to RM-86:

6. The liquid-crystalline medium according to claim 1 , wherein the at least o

Assignees

• Merck Patent Gmbh

Inventors

• Jeong Ji-Won
• Yun Yong-Kuk
• Song Dong-Mee
• Lee Jung-Min

Classifications

• C09K19/44 Primary

  containing compounds with benzene rings directly linked · CPC title

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• C09K19/542 Primary

  Macromolecular compounds · CPC title

• C09K19/3852 Primary

  Poly(meth)acrylate derivatives · CPC title

• C09K2019/548

  stabilizing the alignment; Polymer stabilized alignment · CPC title