IP Library › Granted Patent US 11,788,009
Granted Patent B2
US 11,788,009 · App. 16/770,302 · Granted Oct 17, 2023

Liquid-crystalline medium for use in a switching element

Inventors: Paul Verbunt (Roermond, NL); Ties De Jong (Utrecht, NL); Michael Junge (Pfungstadt, DE); Mila Fischer (Muehltal, DE)
Assignee: MERCK PATENT GMBH
C09K19/3003C09K19/12C09K19/3001C09K19/3402C09K19/542C09K19/588E06B9/24G02F1/13706G02F1/13775G02F1/133345G02F1/133742G02F1/134309C09K2019/3004C09K2019/3009C09K2019/3016C09K2019/3019C09K2019/3021C09K2019/3025C09K2019/3422C09K2019/548E06B2009/2464
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,788,009
App. No.
16/770,302
Granted
Oct 17, 2023
Kind
B2
Abstract

Liquid-crystalline media containing one or more mesogenic compounds, one or more chiral compounds, and one or more polymerizable mesogenic compounds, wherein the media exhibit a pitch of 0.55 μm or more and a clearing point of 80° C. or more and wherein the one or more polymerizable mesogenic compounds are contained in an amount, based on the overall contents of the media, of 5% by weight or less, are suitable as modulation materials. Such modulation materials can be used in switching layers and window elements.

Claims (60)

1. A window element, which is operable in and electrically switchable between an optically transparent state and a scattering state and which comprises a switching layer containing a material which comprises

a liquid-crystalline medium comprising one or more mesogenic compounds and one or more chiral compounds, wherein the liquid-crystalline medium has a clearing point of 95° C. or more, and

a polymeric component comprising one or more polymeric structures obtained by polymerization of one or more polymerizable mesogenic compounds in the liquid-crystalline medium, wherein the polymeric component is contained in the liquid-crystalline material in an amount, based on the overall contents of the material, of 5% by weight or less,

wherein the polymeric component comprises a polymer network in the liquid-crystalline medium, and

wherein in the optically transparent state the window element has a haze, determined according to ASTM D 1003, of less than 10%.

2. The window element according to claim 1 , wherein the liquid-crystalline medium contains, based on the overall contents of the medium, at least 15% by weight of one or more mesogenic compounds of formula I

wherein

R 1 and R 2 denote, independently of one another, a group selected from F, Cl, CF 3 , OCF 3 , and straight-chain or branched alkyl or alkoxy having up to 15 carbon atoms or straight-chain or branched alkenyl having up to 15 carbon atoms which is unsubstituted, monosubstituted by CN or CF 3 or mono- or polysubstituted by halogen and wherein one or more CH 2 groups may be, in each case independently of one another, replaced by —O—, —S—, —CO—, —COO—, —OCO—, —OCOO— or —C≡C— in such a manner that oxygen atoms are not linked directly to one another,

A 11 denotes

n denotes 0 or 1, and

A 21 , A 31 and A 41 denote, independently of one another,

wherein L is on each occurrence, identically or differently, halogen selected from F, Cl and Br.

3. The window element according to claim 1 , wherein the liquid-crystalline medium further comprises one or more mesogenic compounds selected from the group of compounds of formulae II and III

wherein

R 3 , R 4 , R 5 and R 6 denote, independently of one another, a group selected from F, CF 3 , OCF 3 , CN, and straight-chain or branched alkyl or alkoxy having up to 15 carbon atoms or straight-chain or branched alkenyl having up to 15 carbon atoms which is unsubstituted, monosubstituted by CN or CF 3 or mono- or polysubstituted by halogen and wherein one or more CH 2 groups may be, in each case independently of one another, replaced by —O—, —S—, —CO—, —COO—, —OCO—, —OCOO— or —C≡C— in such a manner that oxygen atoms are not linked directly to one another, and

L 1 , L 2 , L 3 , L 4 and L 5 denote, independently of one another, H or F.

4. The window element according to claim 1 , wherein the liquid-crystalline medium exhibits a positive dielectric anisotropy Δε and an optical anisotropy Δn, determined at 20° C. and 589 nm, of 0.13 or more, and wherein the one or more chiral compounds contained in the liquid-crystalline medium have an absolute value of the helical twisting power of 5 μm −1 or more.

5. A method for preparing a window element of claim 1 , comprising

(i) providing said liquid-crystalline medium which comprises one or more mesogenic compounds, said one or more chiral compounds, and said one or more polymerizable mesogenic compounds as a layer between two opposing transparent substrates which are each provided with an electrode,

wherein the liquid-crystalline medium has a clearing point of 95° C. or more and exhibits a pitch of 0.55 μm or more, and

wherein the one or more polymerizable mesogenic compounds are contained in the liquid-crystalline medium in an amount, based on the overall contents of the medium, of 5% by weight or less, and

(ii) polymerizing the one or more polymerizable mesogenic compounds in the presence of an applied electric field in the layer to form the polymer network, wherein the polymerizing is carried out by photopolymerization and wherein the applied electric field induces a homeotropic alignment,

wherein subsequent to step (ii) a thermal treatment is carried out in the presence or absence of an electric field.

6. The method according to claim 5 , wherein the electrodes are arranged as conductive layers above the inner surface of each substrate.

7. A window element for the modulation of the passage of light, wherein the window element is obtained by or obtainable from carrying out the method according to claim 5 .

8. The window element according to claim 1 , which is switchable into the optically transparent state by applying an AC voltage V1 and which is switchable into the scattering state by applying an AC voltage V2, wherein V1>V2.

9. The window element according to claim 1 , wherein the liquid-crystalline medium exhibits a pitch of 0.55 μm or more in the scattering state.

10. A liquid-crystalline medium, comprising

one or more mesogenic compounds,

one or more chiral compounds,

one or more polymerizable mesogenic compounds in an amount, based on the overall contents of the medium, of 5% by weight or less,

wherein the medium exhibits a pitch of 0.55 μm or more and a clearing point of 95° C. or more, and

wherein the medium comprises a compound having the formula

11. The medium according to claim 10 , which contains, based on the overall contents of the medium, at least 15% by weight of one or more mesogenic compounds of formula I,

wherein

R 1 and R 2 denote, independently of one another, a group selected from F, Cl, CF 3 , OCF 3 , and straight-chain or branched alkyl or alkoxy having up to 15 carbon atoms or straight-chain or branched alkenyl having up to 15 carbon atoms which is unsubstituted, monosubstituted by CN or CF 3 or mono- or polysubstituted by halogen and wherein one or more CH 2 groups may be, in each case independently of one another, replaced by —O—, —S—, —CO—, —COO—, —OCO—, —OCOO— or —C≡C— in such a manner that oxygen atoms are not linked directly to one another,

A 11 denotes

n denotes 0 or 1, and

A 21 , A 31 and A 41 denote, independently of one another,

wherein L is on each occurrence, identically or differently, halogen selected from F, Cl and Br,

which optionally further comprises one or more photoinitiators, and

which optionally further comprises one or more mesogenic compounds selected from the group of compounds of formulae II and Ill

wherein

R 3 , R 4 , R 5 and R 6 denote, independently of one another, a group selected from F, CF 3 , OCF 3 , CN, and straight-chain or branched alkyl or alkoxy having up to 15 carbon atoms or straight-chain or branched alkenyl having up to 15 carbon atoms which is unsubstituted, monosubstituted by CN or CF 3 or mono- or polysubstituted by halogen and wherein one or more CH 2 groups may be, in each case independently of one another, replaced by —O—, —S—, —CO—, —COO—, —OCO—, —OCOO— or —C≡C— in such a manner that oxygen atoms are not linked directly to one another, and

L 1 , L 2 , L 3 , L 4 and L 5 denote, independently of one another, H or F.

12. The medium according to claim 10 , wherein one or more of the one or more polymerizable mesogenic compounds comprise one, two or more acrylate and/or methacrylate groups.

13. A modulation material, comprising

a liquid-crystalline medium comprising one or more mesogenic compounds and one or more chiral compounds, wherein the liquid-crystalline medium has a clearing point of 95° C. or more and exhibits a pitch of 0.55 μm or more, and

a polymeric component comprising one or more polymeric structures obtained by or obtainable from polymerization of one or more polymerizable mesogenic compounds, wherein the polymeric component is contained in the material in an amount, based on the overall contents of the material, of 5% by weight or less,

wherein the polymeric component comprises a polymer network,

wherein the liquid-crystalline medium exhibits a positive dielectric anisotropy Δε and an optical anisotropy Δn, determined at 20° C. and 589 nm, of 0.13 or more, and

wherein the one or more chiral compounds contained in the liquid-crystalline medium have an absolute value of the helical twisting power of 5 μm −1 or more.

14. A switching layer, comprising the medium according to claim 10 .

15. A switching layer, comprising the medium according to claim 11 .

16. The method according to claim 6 , wherein the conductive layers are arranged on a passivation layer.

17. The method according to claim 6 , wherein the conductive layers are arranged between passivation layers.

18. The method according to claim 6 , wherein alignment layers are provided which are in direct contact with the liquid-crystalline medium.

19. The modulation material according to claim 13 , wherein the medium comprises a compound having the formula

20. The window element according to claim 1 , wherein the polymeric component stabilizes one or more states of the liquid-crystalline medium.

21. The window element according to claim 1 , wherein in the scattering state the window element has a haze, determined according to ASTM D 1003, of more than 75%.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2020
From: VERBUNT, PAUL; JUNGE, MICHAEL; FISCHER, MILA; DE JONG, TIES
To: MERCK PATENT GMBH
Reel/Frame 053802/0633 →
Priority Claims (1)
EP 17205698 · Dec 6, 2017 · regional
Continuity (1)
Related Publication 20210171830A1 · Jun 10, 2021
Cited By (1)
US 12,619,110