IP Library › Granted Patent US 12,104,109
Granted Patent B2
US 12,104,109 · App. 18/213,024 · Granted Oct 1, 2024

Liquid-crystal medium

Inventors: Chi-Shun Huang (Taipei, TW); Sven Christian Laut (Darmstadt, DE); Hee-Kyu Lee (Shanghai, CN); Minghui Yang (Shanghai, CN); Harald Hirschmann (Darmstadt, DE); Kuang-Ting Chou (Taipei, TW); Shih-Chieh Hung (Taipei, TW); Alexander Hahn (Darmstadt, DE); Philipp Wucher (Darmstadt, DE)
Assignee: MERCK PATENT GMBH
C09K19/3491C09K19/3497C09K19/542C09K2019/548
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 12,104,109
App. No.
18/213,024
Granted
Oct 1, 2024
Kind
B2
Abstract

A liquid-crystal (LC) material having negative dielectric anisotropy and the use thereof for optical, electro-optical and electronic purposes, such as for example in LC displays, in particular energy saving displays based on the ECB, IPS or FFS effect, where the liquid crystal medium contains one or more compounds of formula I and one or more compounds compounds of formulae IIA, IIB, IIC and IID

Claims (64)

1. A liquid crystal medium comprising

a) one or more compounds of formula I

in which

R 1 and R 2 , identically or differently, denote H, halogen, straight chain alkyl or alkoxy having 1 to 15 C atoms, straight chain alkenyl or alkenyloxy having 2 to 15 C atoms or branched alkyl or alkoxy or alkenyl or alkenyloxy having 3 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, independently of one another, by

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

A 0 , A 1 , and A 2 , each, independently of one another, denote phenylene-1,4-diyl, in which one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 , CHF 2 , CH 2 F, CF 3 , OCH 3 , OCHF 2 or OCF 3 , or denote cyclohexane-1,4-diyl, in which one or two non-adjacent CH 2 groups may be replaced, independently of one another, by O and/or S and one or more H atoms may be replaced by F, or denote cyclohexene-1,4-diyl, bicyclo[1.1.1]-pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl,

Z 1 and Z 2 , each, independently of one another, denote —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 H 4 —, —C 2 F 4 , —CF 2 CH 2 —, —CH 2 CF 2 —, —CFHCFH—, —CFHCH 2 —, —CH 2 CFH—, —CF 2 CFH—, —CFHCF 2 —, —CH═CH—, —CF═CH—, —CH═CF—, —CF═CF—, —C≡C— or a single bond,

m denotes 0, 1, 2 or 3, and

n denotes 0, 1, 2 or 3;

and

b) one or more compounds selected from the group of compounds of formulae IIA, IIB, IIC and IID

in which

R 2A , R 2B , R 2C and R 2D identically or differently, denote H, straight chain alkyl or alkoxy having 1 to 15 C atoms, straight chain alkenyl or alkenyloxy having 2 to 15 C atoms or branched alkyl or alkoxy or alkenyl or alkenyloxy having 3 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, independently of one another, by

 —C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, by —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen,

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 , Z 2 B and Z 2 D each, independently of one another, denote 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—,

(O) denotes O or a single bond,

p denotes 0, 1 or 2,

q denotes 0 or 1, and

v denotes an integer from 1 to 6;

wherein the medium has negative dielectric anisotropy.

2. The liquid crystal medium according to claim 1 , wherein the total amount of the one or more compounds selected from the group of compounds of formulae IIA, IIB, IIC and IID is in the range of 9% to 70%.

3. The liquid crystal medium according to claim 1 , wherein the one or more compounds of formula I are selected from the group of compounds of formulae I-1 to I-6

in which R 1 and R 2 have the meanings given for formula I, L is halogen, CN, CH 3 , CHF 2 , CH 2 F, CF 3 , OCH 3 , OCHF 2 or OCF 3 , and r, s and t independently are 0, 1, 2, 3, or 4.

4. The liquid crystal medium according to claim 3 , wherein the group

in the formulae I-1 to I-6 denotes

5. The liquid crystal medium according to claim 1 , wherein the medium further comprises one or more compounds of formula III

in which

R 31 and R 32 each, independently of one another, denote H, an alkyl or alkoxy radical having 1 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, independently of one another, by

 —C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, by —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen,

A 31 on each occurrence, independently of one another, denotes

a) 1,4-cyclohexenylene or 1,4-cyclohexylene radical, in which one or two non-adjacent CH 2 groups may be replaced by —O— or —S—,

b) a 1,4-phenylene radical, in which one or two CH groups may be replaced by N, or

c) a radical selected from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl,

where the radicals a), b) and c) may be mono- or polysubstituted by halogen atoms,

n denotes 0, 1 or 2,

Z 31 on each occurrence independently of one another denotes —CO—O—, —O—CO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CH 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH═CH—CH 2 O—, —C 2 F 4 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CF═CF—, —CH═CF—, —CF═CH—, —CH═CH—, —C≡C— or a single bond,

L 31 and L 32 each, independently of one another, denote F, Cl, CF 3 or CHF 2 , and

W denotes O or S.

6. The liquid crystal medium according to claim 5 , wherein W in formula III denotes S.

7. The liquid crystal medium according to claim 1 , wherein the medium further comprises one or more compounds of formula IV

in which

R 41 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkenyl radical having 2 to 7 C atoms, and

R 42 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkoxy radical having 1 to 6 C atoms, or an unsubstituted alkenyl radical having 2 to 7 C atoms.

8. The liquid crystal medium according to claim 1 , wherein the medium further comprises one or more compounds selected from the group consisting of compounds of formulae IV-3-1 and IV-3-2:

in which alkyl denotes n-alkyl having 1 to 7 C-atoms.

9. The liquid crystal medium according to claim 1 , wherein the medium further comprises one or more compounds of the formula V

in which

R 51 and R 52 denote, each independently, alkyl having 1 to 7 C atoms, alkoxy having 1 to 7 C atoms, or alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7 C atoms,

 identically or differently, denote

Z 51 and Z 52 , identically or differently, denote —CH 2 —CH 2 —, —CH 2 —O—, —CH═CH—, —C≡C—, —COO— or a single bond, and

n is 1 or 2.

10. The liquid crystal medium according to claim 1 , wherein the medium has a birefringence of 0.105 or more.

11. The liquid crystal medium according to claim 1 , wherein the medium comprises a polymerisable compound.

12. A liquid crystal display comprising the liquid crystal medium according to claim 1 .

13. The liquid crystal display of claim 12 , wherein the display is a VA, IPS, FFS, PS-VA, PS-IPS or PS-FFS type display.

14. An energy saving display for gaming comprising the liquid crystal medium according to claim 1 .

15. A process of preparing a liquid crystal medium according to claim 1 , comprising mixing one or more compounds of formula I with one or more compounds selected from the group consisting of compounds of formulae IIA, IIB, IIC and IID, and optionally with a polymerisable compound or further liquid crystal compounds or additives.

16. The liquid crystal medium according to claim 1 , wherein the medium has a dielectric anisotropy Δε of −1.8 to −5.0.

17. The liquid crystal medium according to claim 1 , wherein the medium has a dielectric anisotropy Δε of −2.0 to −3.9.

18. The liquid crystal medium according to claim 1 , wherein the medium has a dielectric anisotropy Δε of −2.3 to −3.4.

19. The liquid crystal medium according to claim 1 , wherein the medium has a dielectric anisotropy Δε of −2.8 to −3.2.

20. The liquid crystal medium according to claim 1 , wherein the medium has a ratio of γ 1 /K 11 [mPas/pN] of 5.4 to 5.5.

Assignments (8)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2024
From: LAUT, SVEN CHRISTIAN; HAHN, ALEXANDER; WUCHER, PHILIPP
To: MERCK ELECTRONICS KGAA
Reel/Frame 066021/0759 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2024
From: LEE, HEE-KYU; YANG, MINGHUI
To: MERCK DISPLAY MATERIALS (SHANGHAI) CO., LTD.
Reel/Frame 066021/0842 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2024
From: HUANG, CHI-SHUN; CHOU, KUANG-TING; HUNG, SHIH-CHIEH
To: MERCK PERFORMANCE MATERIALS LTD.
Reel/Frame 066021/0948 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2024
From: HIRSCHMANN, HARALD
To: MERCK KGAA
Reel/Frame 066022/0004 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2024
From: MERCK PERFORMANCE MATERIALS LTD.
To: MERCK ELECTRONICS KGAA
Reel/Frame 066022/0069 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2024
From: MERCK DISPLAY MATERIALS (SHANGHAI) CO., LTD.
To: MERCK ELECTRONICS KGAA
Reel/Frame 066022/0121 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2024
From: MERCK KGAA
To: MERCK ELECTRONICS KGAA
Reel/Frame 066022/0177 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2024
From: MERCK ELECTRONICS KGAA
To: MERCK PATENT GMBH
Reel/Frame 066022/0258 →
Priority Claims (1)
WO PCT/CN2022/100661 · Jun 23, 2022 · international
Continuity (1)
Related Publication 20240002728A1 · Jan 4, 2024
Cited By (2)
US 12,516,245 US 12,698,444