US 9,726,933 B2Granted

Liquid-crystal displays and liquid-crystalline media having homeotropic alignment

AssigneeMerck Patent GmbH

InventorsGraziano Archetti, Andreas Taugerbeck, Renate Bender, Rocco Fortte, Peer Kirsch, Izumi Saito

Life of this patent

Estimating the term…

Loading patent…

Abstract

The present invention relates to liquid-crystalline media (LC media) having negative or positive dielectric anisotropy comprising self-alignment additives (SAMs) with an at least one bifunctional or polyfunctional anchor group, which effects the homeotropic (vertical) alignment of the LC media at a surface or the cell walls of a liquid-crystal display (LC display). The invention therefore also encompasses LC displays having homeotropic alignment of the liquid-crystalline medium (LC medium) without conventional imide alignment layers. The LC media may be supplemented by a polymerizable or polymerized component, which serves for stabilization of the alignment, for adjustment of the tilt angle and/or as passivation layer.

Claims24

Dependent claims

A LC medium comprising a low-molecular-weight liquid-crystalline mixture and one or more self-aligning additives of formula I:

R1-A1-(Z2-A2)m1-R2 (I)
R2 denotes a group
Sp1, Sp3, Sp5 independently of each other, denotes a spacer group or a single bond,
Sp2 denotes a trivalent, acyclic spacer group,
Sp4 denotes a tetravalent, acyclic spacer group,
Y is independently of each other O, S, (CO), NR0 or a single bond,
X1 and X2 independently of each other a group —OH, —NH2, —NHR11, —SH, —SR11, —NR112, —OR11 or —(CO)OH,
R11 in each case independently denotes a halogenated or unsubstituted alkyl chain having 1 to 15 C atoms, in which one or more CH2 groups are each optionally replaced, independently of one another, by —C≡C—, —CH═CH—, —(CO)O—, —O(CO)—, —(CO)— or —O— in such a way that O or N atoms are not linked directly to one another, and where two radicals R11 are optionally linked to one another to form a ring,
B a ring or condensed ring, optionally substituted by one, two or three RL,
p is 2, 3, 4 or 5,
A1 and A2 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which optionally contains fused rings, and which is optionally mono- or polysubstituted by RL,
RL in each case, independently of one another, denotes OH, SH, SR0, —(CH2)n1—OH, F, Cl, Br, I, —CN, —NO2, —NCO, —NCS, —OCN, —SCN, —C(═O)N(R0)2, —C(═O)R0, —N(R0)2, —(CH2)n1—N(R0)2, optionally substituted silyl, optionally substituted aryl or cycloalkyl having 6 to 20 C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which one or more H atoms are optionally replaced by F or Cl, and two vicinal RL together are optionally ═O,
n1 denotes 1, 2, 3, 4 or 5,
Z2 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— or CR0R00,
R0 and R00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
R1 denotes H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced by —C≡C, —CH═CH, —NR0—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— in such a way that N, O and/or S atoms are not linked directly to one another, and in which one or more tertiary carbon atoms (CH groups) are optionally replaced by N, and in which one or more H atoms are optionally replaced by F or Cl, and
m1 denotes 0, 1, 2, 3, 4 or 5.

14 more elements

A compound of formula I′

R1-A1-(Z2-A2)m1-R2 (I′)
in which
R2 denotes
n independently denotes 1, 2, 3 or 4,
Sp1, Sp3, Sp5 independently of each other, denotes a spacer group or a single bond,
Sp2 denotes a trivalent, acyclic spacer group,
Sp4 denotes a tetravalent, acyclic spacer group,
Y is independently of each other O, S, (CO), NR0 or a single bond,
X1 and X2 independently of each other a group —OH, —NH2, —NHR11, —SH, —SR11, —NR112, —OR11 or —(CO)OH,
R11 in each case independently denotes a halogenated or unsubstituted alkyl chain having 1 to 15 C atoms, in which one or more CH2 groups are each optionally replaced, independently of one another, by —C≡C—, —CH═CH—, —(CO)O—, —O(CO)—, —(CO)— or —O— in such a way that O or N atoms are not linked directly to one another, and where two radicals R11 are optionally linked to one another to form a ring,
B a ring or condensed ring, optionally substituted by one, two or three RL,
p is 2, 3, 4 or 5,
A1 and A2 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which optionally contains fused rings, and which is optionally mono- or polysubstituted by RL,
RL in each case, independently of one another, denotes OH, SH, SR0, —(CH2)n1—OH, F, Cl, Br, I, —CN, —NO2, —NCO, —NCS, —OCN, —SCN, —C(═O)N(R0)2, —C(═O)R0, —N(R0)2, —(CH2)n1—N(R0)2, optionally substituted silyl, optionally substituted aryl or cycloalkyl having 6 to 20 C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which one or more H atoms are optionally replaced by F or Cl, and two vicinal RL together are optionally ═O,
n1 denotes 1, 2, 3, 4 or 5,
Z2 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— or CR0R00,
R0 and R00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
R1 denotes H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced by —C≡C—, —CH═CH, —NR0—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— in such a way that N, O and/or S atoms are not linked directly to one another, and in which one or more tertiary carbon atoms (CH groups) are optionally replaced by N, and in which one or more H atoms are optionally replaced by F or Cl, and
m1 denotes 1, 2, 3 or 4.

16 more elements

A compound of formula I′

R1-A1-(Z2-A2)m1-R2 (I′)
in which
R2 denotes a group
Sp1, Sp3, Sp5 independently of each other, denotes a spacer group or a single bond,
Sp2 denotes a trivalent, acyclic spacer group,
Sp4 denotes a tetravalent, acyclic spacer group,
Y is independently of each other O, S, (CO), NR0 or a single bond,
X1 and X2 independently of each other a group —OH, —NH2, —NHR11, —SH, —SR11, —NR112, —OR11 or —(CO)OH,
R11 in each case independently denotes a halogenated or unsubstituted alkyl chain having 1 to 15 C atoms, in which one or more CH2 groups are each optionally replaced, independently of one another, by —C≡C—, —CH═CH—, —(CO)O—, —O(CO)—, —(CO)— or —O— in such a way that O or N atoms are not linked directly to one another, and where two radicals R11 are optionally linked to one another to form a ring,
B a ring or condensed ring, optionally substituted by one, two or three RL,
p is 2, 3, 4 or 5,
A1 and A2 each, independently of one another, denote 1,4-phenylene and/or cyclohexane-1,4-diyl, which is optionally mono- or polysubstituted by RL,
RL in each case, independently of one another, denotes OH, SH, SR0, —(CH2)n1—OH, F, Cl, Br, I, —CN, —NO2, —NCO, —NCS, —OCN, —SCN, —C(═O)N(R0)2, —C(═O)R0, —N(R0)2, —(CH2)n1—N(R0)2, optionally substituted silyl, optionally substituted aryl or cycloalkyl having 6 to 20 C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which one or more H atoms are optionally replaced by F or Cl, and two vicinal RL together are optionally ═O,
n1 denotes 1, 2, 3, 4 or 5,
Z2 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— or CR0R00,
R0 and R00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
R1 denotes H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced by —C≡C—, —CH═CH—, —NR0—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— in such a way that N, O and/or S atoms are not linked directly to one another, and in which one or more tertiary carbon atoms (CH groups) are optionally replaced by N, and in which one or more H atoms are optionally replaced by F or Cl, and
m1 denotes 2, 3 or 4.

15 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/652,568Filed 26 Nov 2013
Priority: EP 1200838917 Dec 2012
Published: US 2015/0301368 A122 Oct 2015
Granted: 8 Aug 2017
Term ends: Not estimatedThe source records don’t support an estimate.

Classification28 codes

G02F 1/1337
Constructional arrangements; Manufacturing methods: surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
C07C 31/27
Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms: polyhydroxylic alcohols containing saturated rings
C07C 31/276
Monocyclic: with a six-membered ring
C07C 33/26
Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms: polyhydroxylic alcohols containing only six-membered…