IP Library › Granted Patent US 11,008,515
Granted Patent B2
US 11,008,515 · App. 16/196,488 · Granted May 18, 2021

Liquid-crystalline medium

Inventors: Harald Hirschmann (Darmstadt, DE); Monika Bauer (Seligenstadt, DE); Martina Windhorst (Muenster, DE); Marcus Reuter (Darmstadt, DE); Kristin Weiss (Gross-Zimmern, DE)
Assignee: Merck Patent GmbH
C09K19/3491C09K19/30C09K19/3001C09K19/3003C09K19/3066C09K19/3068C09K19/3098C09K19/32C09K19/322C09K19/3402C09K19/3405C09K19/542C09K19/56C09K19/58C09K19/586C09K19/588C09K2019/0411C09K2019/0466C09K2019/123C09K2019/301C09K2019/303C09K2019/3004C09K2019/305C09K2019/3009C09K2019/3015C09K2019/3016C09K2019/3021C09K2019/3027C09K2019/3071C09K2019/3078C09K2019/3096C09K2019/327C09K2019/3408C09K2019/3422C09K2019/3425C09K2019/548G02F1/1362
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Quick Facts
Patent No.
US 11,008,515
App. No.
16/196,488
Granted
May 18, 2021
Kind
B2
Abstract

A liquid-crystalline medium which comprises at least one compound selected from the group of compounds of the formulae IA to IH, in which Z 1 denotes a single bond, —CH 2 CH 2 —, —CH═CH—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —COO—, —OCO—, —C 2 F 4 —, —(CH 2 ) 4 —, —CHFCHF—, —CF 2 CH 2 —, —CH 2 CF 2 —, —C≡C—, —CF═CF—, —CH═CHCHO— or —CH 2 CF 2 O—, and the use thereof for an active-matrix display, in particular based on the VA, PSA, PS-VA, PALC, FFS, PS-FFS, SA-VA, PS-IPS or IPS effect.

Claims (71)

1. A liquid-crystalline medium comprising, at least one compound selected from the group of the compounds of the formulae IA to IH, and wherein the medium has a negative dielectric anisotropy, Δε:

in which

Z 1 denotes a single bond, —CH 2 CH 2 —, —CH═CH—, —CH 2 O—, —OCH 2 , —CF 2 O—, —OCF 2 —, —COO—, —OCO—, —C 2 F 4 —, —(CH 2 ) 4 —, —CHFCHF—, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF═CF—, —CH═CHCHO— or —CH 2 CF 2 O—, with the proviso that Z 1 does not denote a single bond in either the compound of formula IA or the compound of formula IB.

2. The liquid-crystalline medium according to claim 1 , which comprises at least one compound of at least one of the following formulae:

3. The liquid-crystalline medium according to claim 1 , wherein the proportion of the compound(s) of the formulae IA to IH in the medium as a whole is 1-50% by weight.

4. The liquid-crystalline medium according to claim 1 , which additionally comprises one or more compounds selected from the group of the compounds of the formulae IIA, IIB and IIC,

in which

R 2A , R 2B and R 2C each, independently of one another, denote H, an alkyl or alkenyl radical having up to 15 C atoms which is un-substituted, 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 be replaced by —O—, —S—,

—C≡C—, —CF 2 O—, —OCF 2 —, —OC—O— or —O—CO— i n such a way that O atoms are not linked directly to one another, a cyclopropyl ring, cyclobutyl ring or cyclopentyl ring,

L 1-4 each, independently of one another, denote F, Cl, CF 3 or CHF 2 ,

Z 2 and Z 2′ each, independently of one another, denote a single bond, —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —O CH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF—, —C≡C— or —CH═CHCH 2 O—,

p denotes 0, 1 or 2,

q denotes 0 or 1, and

v denotes 1 to 6.

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

in which

R 31 and R 32 each, independently of one another, denote a straight-chain alkyl, alkenyl, alkoxy, alkoxyalkyl or alkenyloxy radical having up to 12 C atoms,

denotes

and

Z 3 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 —, —C 4 H 9 -, —C≡C— or —CF═CF—.

6. The liquid-crystalline medium according to claim 1 , wherein the medium additionally comprises one or more compounds of the formulae L-1 to L-11,

in which

R, R 1 and R 2 each, independently of one another, denote 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 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, a cyclopropyl ring, cyclobutyl ring or cyclopentyl ring,

alkyl denotes an alkyl radical having 1-6 C atoms, and

s denotes 1 or 2.

7. The liquid-crystalline medium according to claim 1 , wherein the medium additionally comprises one or more terphenyls of the formulae T-1 to T-22,

in which

R denotes a straight-chain alkyl or alkoxy radical having 1-7 C atoms,

m denotes 0, 1, 2, 3, 4, 5 or 6, and

n denotes 0, 1, 2, 3 or 4.

8. The liquid-crystalline medium according to claim 1 , wherein the medium additionally comprises one or more compounds of the formulae O—1 to O—17,

in which

R 1 and R 2 each, independently of one another, denote 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 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, a cyclopropyl ring, cyclobutyl ring or cyclopentyl ring.

9. The liquid-crystalline medium according to claim 1 , wherein the medium additionally comprises one or more compounds selected from the group of the compounds of the formulae BC, CR, PH-1, PH-2, BF-1, BF-2, BS-1 and BS-2,

in which

R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 each, independently of one another, denote 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 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, a cyclopropyl ring, cyclobutyl ring or cyclopentyl ring,

c denotes 0, 1 or 2

and d denotes 1 or 2.

10. The liquid-crystalline medium according to claim 1 , wherein the medium additionally comprises one or more compounds of the following formulae:

11. The liquid-crystalline medium according to claim 1 , characterised in that the medium comprises 5-60% of the compound of the following formula:

12. The liquid-crystalline medium according to claim 1 , wherein the medium additionally comprises one or more compounds selected from the group of the compounds of the formulae P-1 to P-5,

in which

R denotes straight-chain alkyl, alkoxy or alkenyl, each having 1 or 2 to 6 C atoms respectively, and

X denotes F, Cl, CF 3 , OCF 3 , OCHFCF 3 or CCF 2 CHFCF 3 .

13. The liquid-crystalline medium according to claim 1 , wherein the medium additionally comprises one or more compounds selected from the group of the compounds of the following formulae:

in which

R denotes a straight-chain alkyl or alkoxy radical having 1-7 C atoms,

m denotes 0, 1, 2, 3, 4, 5 or 6,

n denotes 0, 1, 2, 3 or 4,

R 1 , R 2 each, independently of one another, denote 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 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, a cyclopropyl ring, cyclobutyl ring or cyclopentyl ring,

c denotes 0, 1 or 2

d denotes 1 or 2,

R and R 10 each, independently of one another, denote 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 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, a cyclopropyl ring, cyclobutyl ring or cyclopentyl ring,

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

alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2-6 C atoms, and

x denotes 1 to 6.

14. The liquid-crystalline medium according to claim 1 , wherein the medium comprises the compound of the formula CC-4-V1 and the compound of the formula CC-3-V1:

15. The liquid-crystalline medium according to claim 1 , wherein the medium comprises at least one polymerisable compound.

16. The liquid-crystalline medium according to claim 1 , wherein the medium further comprises one or more additives.

17. The liquid-crystalline medium according to claim 16 , wherein the additive is a free-radical scavenger, antioxidant, dopant and/or UV stabiliser.

18. A process for the preparation of a liquid-crystalline medium according to claim 1 , comprising mixing at least one compound of the formulae IA to IH with at least one further compound wherein the further compound is a mesogenic compound, and optionally further mixing one or more additives and optionally further mixing at least one polymerisable compound.

19. An electro-optical display having active-matrix addressing, which comprises, as dielectric, a liquid-crystalline medium according to claim 1 .

20. The electro-optical display according to claim 19 , which is a VA, PSA, PA-VA, PS-VA, SA-VA, SS-VA, PALC, IPS, PS-IPS, FFS, UB-FFS or PS-FFS display.

21. The electro-optical display according to claim 20 , which is an IPS, PS-IPS, FFS or PS-FFS display which has a planar alignment layer.

22. The liquid-crystalline medium according to claim 1 , wherein the medium has a negative dielectric anisotropy, Δϑ, of less than −0.5.

23. The liquid-crystalline medium according to claim 1 , wherein the medium has a negative dielectric anisotropy, Δε, of −0.5 to −8.0.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 20, 2018
From: HIRSCHMANN, HARALD; BAUER, MONIKA; WINDHORST, MARTINA; REUTER, MARCUS; WEISS, KRISTIN
To: MERCK PATENT GMBH
Reel/Frame 047554/0809 →
Priority Claims (2)
DE 10 2017 010 883.8 · Nov 24, 2017 · national
EP 18197753 · Sep 28, 2018 · regional
Continuity (1)
Related Publication 20190161679A1 · May 30, 2019
Cited By (5)
US 12,305,103 US 12,325,817 US 12,595,416 US 12,624,290 US 12,735,641