IP Library › Granted Patent US 12,163,081
Granted Patent B2
US 12,163,081 · App. 18/204,621 · Granted Dec 10, 2024

Liquid-crystal medium

Inventors: Harald Hirschmann (Darmstadt, DE); Sabine Schoen (Darmstadt, DE); Philipp Wucher (Darmstadt, DE)
Assignee: MERCK PATENT GMBH
C09K19/3491
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Quick Facts
Patent No.
US 12,163,081
App. No.
18/204,621
Granted
Dec 10, 2024
Kind
B2
Abstract

A liquid-crystal (LC) medium based on a mixture of polar compounds, its use for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the vertically aligned mode, to an LC display of the vertically aligned mode containing the LC medium, especially an energy-saving LC display and a process of manufacturing the LC display.

Claims (64)

1. An LC medium having negative dielectric anisotropy and comprising

one or more compounds of formula IA

in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:

R 1A is an alkyl or alkoxy group having 1 to 12, wherein one or more non-adjacent CH 2 -groups are replaced by cyclopropyl, cyclobutyl or cyclopentyl,

R 2A is a straight chain alkyl having 1 to 25 C atoms or a branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR 0 ═CR 00 —, —C≡C—,

 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,

L 1A , L 2A are F, Cl, CF 3 or CHF 2 ,

Y is H, F, Cl, CF 3 , CHF 2 or CH 3 , and

n 0 or 1,

and

at least one compound selected from the group of compounds of formulae IID-4, IID-10, PH-1 and Q

wherein

alkyl each, independently of one another, denotes a straight-chain alkyl radical having 1-6 C atoms,

Y denotes, for formula IID-10, H or CH 3 , and

(O) denotes an oxygen atom or a single bond,

wherein

R 71 , R 72 are H, an alkyl or alkoxy radical having 1 to 15 C atoms or an or alkenyl radical having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted by F, Cl, CN or CF 3 and in which one or more CH 2 groups may be replaced by —O—, —S—, —C≡C—, —CF 2 O—, —OCF 2 —, —OC—O—, —O—CO—

 in such a way that O- and/or S-atoms are not linked directly to one another,

wherein

R Q is alkyl, alkoxy, oxaalkyl or alkoxyalkyl having 1 to 9 C atoms or alkenyl or alkenyloxy having 2 to 9 C atoms, all of which are optionally fluorinated,

X Q is F, Cl, halogenated alkyl or alkoxy having 1 to 6 C atoms or halogenated alkenyl or alkenyloxy having 2 to 6 C atoms, and

L Q1 to L Q6 independently of each other are H or F, with at least one of L Q1 to L Q6 being F.

2. The LC medium according to claim 1 , wherein the one or more compounds of formula IA are selected from the following formulae:

wherein “(O)” denotes an oxygen atom or a single bond and “alkyl” denotes an alkyl group with 1 to 6 C atoms.

3. The LC medium according to claim 1 , further comprising one or more compounds selected from the group consisting of compounds of formulae IIA, IIB, IIC and IID, wherein the compounds of formulae IID-4 and IID-10 are excluded from the compounds of formula IID,

in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:

R 21 , R 22 are H, an alkyl or alkoxy radical having 1 to 15 C atoms or an or alkenyl radical having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted by F, Cl, CN or CF 3 and in which one or more CH 2 groups may be replaced by —O—, —S—, —C≡C—, —CF 2 O—, —OCF 2 —, —OC—O—, —O—CO—

 in such a way that O- and/or S-atoms are not linked directly to one another,

L 1 to L 4 are F, Cl, CF 3 or CHF 2 ,

Y is H, F, Cl, CF 3 , CHF 2 or CH 3 ,

Z 1 , Z 2 are a single bond, —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF—, or —CH═CHCH 2 O,

p is 0, 1 or 2, and

q is 0 or 1,

wherein in formula IID, if Z 1 and Z 2 denote a single bond, then R 21 is different from cyclic alkyl or alkoxy.

4. The LC medium according to claim 1 , additionally comprising one or more compounds selected from the group of compounds of formulae IV-1 to IV-4,

in which

alkyl and alkyl′ denote, independently of one another, alkyl having 1 to 7 C atoms,

alkenyl denotes an alkenyl radical having 2 to 5 C atoms,

alkenyl′ denotes an alkenyl radical having 2 to 5 C atoms, and

alkoxy denotes alkoxy having 1 to 5 C atoms.

5. The LC medium according to claim 1 , additionally comprising one or more compounds of formula V

in which

R 51 , R 52 denote, independently of one another, H, an alkyl or alkoxy radical having 1 to 15 C atoms or an alkenyl radical having 2 to 15 C atoms, each of which is unsubstituted, monosubstituted by F, Cl, CN or CF 3 or at least monosubstituted by halogen, and in which one or more CH 2 groups may be replaced by —O—, —S—, —C≡C—, —CF 2 O—, —OCF 2 —, —OC—O—, —O—CO—

 in such a way that O atoms are not linked directly to one another,

identically or differently, denote

Z 51 , Z 52 each, independently of one another, denote —CH 2 —CH 2 —, —CH 2 —O—, —CH═CH—, —C≡C—, —COO— or a single bond, and

n is 1 or 2.

6. The LC medium according to claim 1 , additionally comprising one or more additives selected from the group consisting of polymerizable compounds, stabilisers, chiral dopants, polymerization initiators and self alignment additives.

7. A process for preparing the LC medium according to claim 1 , comprising mixing one or more compounds of formula IA with at least one compound selected from the group of compounds of formulae IID-4, IID-10, PH-1 and Q and optionally with one or more additives.

8. An LC display comprising the LC medium as defined in claim 1 .

9. The LC display of claim 8 , which is an LC display of the VA, IPS, FFS, UB-FFS or UV 2 A mode.

10. An energy-saving LC display comprising the LC medium as defined in claim 1 .

11. The LC medium according to claim 1 , which comprises a compound of formula IID-4.

12. The LC medium according to claim 1 , which comprises a compound of formula IID-10.

13. The LC medium according to claim 1 , which further comprises a compound of formula BC

wherein

R 71 , R 72 are H, an alkyl or alkoxy radical having 1 to 15 C atoms or an or alkenyl radical having 2 to 15 C atoms, each of which is unsubstituted or monosubstituted by F, Cl, CN or CF 3 and in which one or more CH 2 groups may be replaced by —O—, —S—, —C≡C—, —CF 2 O—, —OCF 2 —, —OC—O—, —O—CO—

 in such a way that O- and/or S-atoms are not linked directly to one another.

14. The LC medium according to claim 1 , which comprises a compound of formula PH-1.

15. The LC medium according to claim 1 , which comprises a compound of formula Q.

16. The LC medium according to claim 1 , which comprises at least three compounds selected from the group of compounds of formulae IID-4, IID-10, PH-1 and Q.

17. The LC medium according to claim 1 , which has a dielectric anisotropy Δε of −1.5 to −8.0.

18. The LC medium according to claim 1 , which has a dielectric anisotropy Δε of −2.0 to −4.0.

19. The LC medium according to claim 1 , which has a dielectric anisotropy Δε of −2.5 to −3.6.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2024
From: HIRSCHMANN, HARALD; SCHOEN, SABINE
To: MERCK KGAA
Reel/Frame 068596/0311 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2024
From: WUCHER, PHILIPP
To: MERCK ELECTRONICS KGAA
Reel/Frame 068596/0382 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2024
From: MERCK KGAA
To: MERCK ELECTRONICS KGAA
Reel/Frame 068596/0405 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2024
From: MERCK ELECTRONICS KGAA
To: MERCK PATENT GMBH
Reel/Frame 068596/0529 →
Priority Claims (1)
EP 22176907 · Jun 2, 2022 · regional
Continuity (1)
Related Publication 20230392077A1 · Dec 7, 2023