IP Library › Granted Patent US 12,585,160
Granted Patent B2
US 12,585,160 · App. 17/376,702 · Granted Mar 24, 2026

Liquid-crystalline medium

Inventors: Hoo-Yong Lee (Pyeongtaek, KR); Hyun-Jin Yoon (Pyeongtaek, KR)
Assignee: MERCK PATENT GMBH
G02F1/13712B32B17/10504C09K19/2007C09K19/3003G02F1/133331G02F1/133742G02F1/133769G02F1/1397C09K2019/301
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Quick Facts
Patent No.
US 12,585,160
App. No.
17/376,702
Granted
Mar 24, 2026
Kind
B2
Abstract

A liquid-crystalline media having a negative dielectric anisotropy and a high clearing point as specified herein, is suitable for use of in switchable optical cells in window elements, in particular laminated window elements.

Claims (53)

1 . A process for the preparation of a window element, comprising

providing a switchable optical cell which comprises a switchable layer interposed between a first transparent substrate and a second transparent substrate, wherein the switchable optical cell is electrically switchable, and wherein the switchable optical cell has a layer structure comprising, in sequence, the first transparent substrate, a first electrode layer, a first alignment layer, the switchable layer, a second alignment layer, a second transparent electrode layer, and the second transparent substrate,

wherein the switchable layer comprises a liquid-crystalline medium having a negative dielectric anisotropy, a clearing point of greater than 140° C. to 170° C., and an optical anisotropy Δn in the range of from 0.075 to 0.1, and the switchable layer is a homeotropically aligned liquid crystal layer comprising the liquid-crystalline medium, wherein in the presence of an electric field the switchable layer has a twisted configuration or a supertwisted configuration, wherein the liquid-crystalline medium comprises three or more dichroic dyes, and wherein the switchable layer has a thickness in the range from 4 μm to 10 μm, and

laminating the switchable optical cell to a third substrate via a thermoplastic interlayer arranged between the first or second transparent substrate of the switchable optical cell and the third substrate, wherein, during the laminating, heating to a temperature of 110° C. or more is carried out; and

wherein the first transparent substrate and the second transparent substrate are made of plastic and are optically isotropic, and the third substrate is curved, made of glass, and is optically isotropic and transparent.

2 . The process according to claim 1 , wherein the thermoplastic interlayer is an interlayer of an ionoplast, ethylene vinyl acetate, polyvinyl butyral, or thermoplastic polyurethane.

3 . A window element, comprising a switchable optical cell having a layer structure comprising in this order:

a first transparent substrate,

a first electrode layer,

a first alignment layer,

a switchable layer,

a second alignment layer,

a second electrode layer, and

a second transparent substrate,

wherein the switchable layer comprises a liquid-crystalline medium having a negative dielectric anisotropy, a clearing point of greater than 140° C. to 170° C., and an optical anisotropy Δn in the range of from 0.075 to 0.1, wherein the liquid-crystalline medium comprises three or more dichroic dyes, and the switchable layer is a homeotropically aligned liquid crystal layer comprising the liquid-crystalline medium, and wherein the switchable layer has a thickness in the range from 4 μm to 10 μm,

wherein the switchable optical cell is laminated to a third substrate via a thermoplastic interlayer arranged between the first or second transparent substrate of the switchable optical cell and the third substrate, and wherein the switchable optical cell is electrically switchable, and

wherein the first transparent substrate and the second transparent substrate are made of plastic and are optically isotropic, and the third substrate is curved, made of glass, and is optically isotropic and transparent, and

wherein in the presence of an electric field the switchable layer has a twisted configuration or a supertwisted configuration.

4 . The window element according to claim 3 , wherein the switchable optical cell further comprises one or more polarizer layers and optionally one or more optical retarder layers.

5 . The window element according to claim 3 , wherein the liquid-crystalline medium comprises:

one or more compounds of formula IIA

wherein

R 2A denotes 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, where, in addition, one or more CH 2 groups in these radicals may each be 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,

L 1 and L 2 each, independently of one another, denote F, Cl, CF 3 or CHF 2 ,

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

Z 2 denotes 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 denotes 0, 1 or 2, and

V denotes 1 to 7.

6 . The window element according to claim 5 , wherein said one or more compounds of formula IIA are selected from the compounds of formulae IIA-1 and IIA-2

wherein

alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1 to 7 C atoms.

7 . The window element according to claim 5 , wherein the liquid-crystalline further comprises one or more compounds of formula V

in which

R 51 and R 52 each, independently of one another, denotes 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, where, in addition, one or more CH 2 groups in these radicals may each be 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,

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.

8 . The window element according to claim 5 , wherein the liquid-crystalline medium further comprises one or more compounds of formula V-1

wherein

R 1 and R 2 each, independently of one another, have one of the meanings indicated for R 2A in claim 5 .

9 . The window element according to claim 5 , wherein the liquid-crystalline medium further comprises a chiral dopant.

10 . The window element according to claim 5 , wherein the liquid-crystalline medium does not contain compounds of the formulae

in which

n and m each, independently of one another, denote 1 to 7.

11 . The window element according to claim 3 , wherein the liquid crystalline medium has an optical anisotropy Δn of from 0.075 to 0.095.

12 . The window element according to claim 3 , wherein the liquid crystalline medium has an optical anisotropy Δn in the range of from 0.075 to 0.090.

13 . The window element according to claim 3 , wherein the liquid-crystalline medium contains a compound of formula CCOC-n-m

wherein n and m are each independently 1, 2, 3, 4, 5, 6, 7, 8 or 9, and/or

a compound of formula CCOC-n-m

wherein n and m are each independently 1, 2, 3, 4, 5, 6, 7, 8 or 9.

14 . A building window or a vehicle window comprising the window element according to claim 3 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2023
From: LEE, HOO-YONG; YOON, HYUN-JIN
To: MERCK PERFORMANCE MATERIALS LTD
Reel/Frame 062418/0527 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2023
From: MERCK PERFORMANCE MATERIALS LTD
To: MERCK PERFORMANCE MATERIALS GERMANY GMBH
Reel/Frame 062418/0772 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2023
From: MERCK PERFORMANCE MATERIALS GERMANY GMBH
To: MERCK PATENT GMBH
Reel/Frame 062419/0058 →
Priority Claims (1)
EP 20186240 · Jul 16, 2020 · regional
Continuity (1)
Related Publication 20220025265A1 · Jan 27, 2022
References Cited (29)
US 9238775B2 · Junge · 2016 [cited by applicant]
US 10626666B2 · Junge et al. · 2020 [cited by applicant]
US 10655067B2 · Junge et al. · 2020 [cited by applicant]
US 10723950B2 · Junge et al. · 2020 [cited by applicant]
US 11762241B2 · Junge · 2023 [cited by examiner]
US 11841591B2 · Junge · 2023 [cited by applicant]
US 20100045924A1 · Powers · 2010 [cited by examiner]
US 20110007255A1 · Yaroshchuk · 2011 [cited by examiner]
US 20160319592A1 · Junge · 2016 [cited by examiner]
US 20170361575A1 · Kusudou · 2017 [cited by examiner]
US 20190016955A1 · Junge · 2019 [cited by examiner]
US 20190031959A1 · Junge · 2019 [cited by examiner]
US 20190162991A1 · Hagiwara · 2019 [cited by examiner]
US 20190227357A1 · Williams · 2019 [cited by examiner]
US 20200055281A1 · Yoon · 2020 [cited by examiner]
US 20210165284A1 · Lim · 2021 [cited by examiner]
US 20210181585A1 · Junge · 2021 [cited by examiner]
US 20220105710A1 · Ishii · 2022 [cited by examiner]
CN 103180409A · 2013 [cited by applicant]
WO 2012052100A1 · 2012 [cited by applicant]
WO 2015090506A1 · 2015 [cited by applicant]
WO 2017118464A1 · 2017 [cited by applicant]
WO 2017118465A1 · 2017 [cited by applicant]
WO 17118464A1 · 2017 [cited by applicant]
WO 2020120533A1 · 2020 [cited by applicant]
Search report in corresponding EP 21185184 dated Dec. 22, 2021 (pp. 1-6). [cited by applicant]
R. Baetens et al., “Properties, Requirements and Possibilities of Smart Windows for Dynamic Daylight and Solar Energy Control in Buildings: A State-of-the-Art Review”, Solar Energy Materials & Solar Cells, vol. 94 (2010… [cited by applicant]
China National Intellectual Property Administration Office Action dated Apr. 14, 2025 issued in corresponding application 202110798210 and English translation. [cited by applicant]
Japan Patent Office Office Action dated Apr. 22, 2025 issued in corresponding application 2021-117126 and English translation. [cited by applicant]