IP Library Granted Patent US 9,701,903
Granted Patent B2
US 9,701,903 · App. 14/706,463 · Granted Jul 11, 2017

Liquid crystalline medium

Inventors: Melanie Klasen-Memmer (Heuchelheim, DE); Sabine Schoen (Herten, DE)
Assignee: Merck Patent GmbH
C09K19/3001C09K19/02C09K19/0208C09K19/0216C09K19/12C09K19/3003C09K19/3028C09K19/3048C09K19/3066C09K19/3068C09K19/3098C09K19/44C09K2019/0466C09K2019/122C09K2019/123C09K2019/181C09K2019/183C09K2019/301C09K2019/303C09K2019/3004C09K2019/304C09K2019/305C09K2019/3009C09K2019/3016C09K2019/3027
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Quick Facts
Patent No.
US 9,701,903
App. No.
14/706,463
Granted
Jul 11, 2017
Kind
B2
Abstract

The present invention relates to a liquid-crystalline medium based on a mixture of polar compounds having negative dielectric anisotropy (Δ∈), which is distinguished by the fact that it has a value for the ratio γ 1 /Δn 2 in the range 6-45 with a clearing point of >60° C. and a Δ∈ of ≦−2.3. Media of this type are particularly suitable for electro-optical displays having active-matrix addressing based on the ECB, PA LCD, FFS or IPS effect.

Claims (189)

1. A liquid-crystalline medium based on a mixture of polar compounds having negative dielectric anisotropy (Δ∈), which has a value for the ratio γ 1 /Δn 2 in the range 6-45 Pa·s with a clearing point of >60° C. and a Δ∈ of ≦−2.3, and comprises

at least one compound of formula B-4

and

at least one compound of formula IB

and

at least one compound of formula II

and

optionally at least one compound of formula IA

in which

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

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, in which one or more CH 2 groups are each, independently of one another, optionally replaced by —O—, —S—,

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

v denotes 1 to 6,

and

at least one of the following compounds from groups A, B, or C:

A)

one or more compounds of the following formulae T-1 to T-22

in which

R 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, in which one or more CH 2 groups are optionally replaced by —O—, —S—,

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

B)

one or more compounds of the following formulae To-1 and To-2

in which

R 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, in which one or more CH 2 groups are optionally replaced by —O—, —S—,

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

alkyl denotes a straight-chain alkyl radical having 1-6 C atoms;

C)

the following compound

wherein alkyl* denotes a straight-chain alkyl radical having 1-6 C atoms.

2. A liquid-crystalline medium according to claim 1 , which contains at least one compound of formula IA.

3. A liquid-crystalline medium according to claim 1 , which contains at least 10% of one or more compounds of formula IB and of formula II.

4. A liquid-crystalline medium according to claim 1 , which has a clearing point of 60-90° C.

5. A liquid-crystalline medium according to claim 1 , which has a Δ∈ value of −2.3 to −5.5.

6. A liquid-crystalline medium according to claim 1 , which having a clearing point of 70° C.±5° C. and a Δ∈ of −3.0±0.6 has the following rotational viscosities γ 1 at a defined Δn value:

Δn

γ 1

0.08 ± 0.005

≦125 mPa · s

0.09 ± 0.005

≦130 mPa · s

0.10 ± 0.005

≦135 mPa · s

0.11 ± 0.005

≦145 mPa · s

0.12 ± 0.005

≦150 mPa · s

0.13 ± 0.005

≦160 mPa · s

0.15 ± 0.01

≦170 mPa · s.

7. A liquid-crystalline medium according to claim 1 , which having a clearing point of 70° C.±5° C. and a Δ∈ of >−3.6 and ≦−4.4 has the following rotational viscosities γ 1 at a defined Δn value:

Δn

γ 1

0.08 ± 0.005

≦140 mPa · s

0.09 ± 0.005

≦165 mPa · s

0.10 ± 0.005

≦185 mPa · s

0.11 ± 0.005

≦190 mPa · s

0.12 ± 0.005

≦195 mPa · s

0.13 ± 0.005

≦205 mPa · s

0.15 ± 0.01

≦220 mPa · s.

8. A liquid-crystalline medium according to claim 1 , which having a clearing point of 70° C.±5° C. and a Δ∈ of >−4.4 and ≦−5.6 has the following rotational viscosities γ 1 at a defined Δn value:

Δn

γ 1

0.08 ± 0.005

≦185 mPa · s

0.09 ± 0.005

≦200 mPa · s

0.10 ± 0.005

≦210 mPa · s

0.11 ± 0.005

≦220 mPa · s

0.12 ± 0.005

≦230 mPa · s

0.13 ± 0.005

≦250 mPa · s

0.15 ± 0.01

≦270 mPa · s.

9. A liquid-crystalline medium according to claim 1 , which having a clearing point of 90° C.±5° C. and a Δ∈ of −3.0±0.6 has the following rotational viscosities γ 1 at a defined Δn value:

Δn

γ 1

0.08 ± 0.005

≦160 mPa · s

0.09 ± 0.005

≦170 mPa · s

0.10 ± 0.005

≦180 mPa · s

0.11 ± 0.005

≦190 mPa · s

0.12 ± 0.005

≦200 mPa · s

0.13 ± 0.005

≦210 mPa · s

0.15 ± 0.01

≦220 mPa · s.

10. A liquid-crystalline medium according to claim 1 , which having a clearing point of 90° C.±5° C. and a Δ∈ of >−3.6 and ≦−4.4 has the following rotational viscosities γ 1 at a defined Δn value:

Δn

γ 1

0.08 ± 0.005

≦185 mPa · s

0.09 ± 0.005

≦195 mPa · s

0.10 ± 0.005

≦215 mPa · s

0.11 ± 0.005

≦215 mPa · s

0.12 ± 0.005

≦215 mPa · s

0.13 ± 0.005

≦235 mPa · s

0.15 ± 0.01

≦250 mPa · s.

11. A liquid-crystalline medium according to claim 1 , which having a clearing point of 90° C.±5° C. and a Δ∈ of >−4.4 and ≦−5.6 has the following rotational viscosities γ 1 at a defined Δn value:

Δn

γ 1

0.08 ± 0.005

≦280 mPa · s

0.09 ± 0.005

≦275 mPa · s

0.10 ± 0.005

≦275 mPa · s

0.11 ± 0.005

≦275 mPa · s

0.12 ± 0.005

≦280 mPa · s.

12. A liquid-crystalline medium according to claim 1 , which has thresholds (capacitive) in the range 1.8-2.3 V.

13. A liquid-crystalline medium according to claim 1 , which 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 alkenyl, alkyl, alkylalkoxy or alkoxy radical having up to 12 C atoms, and

denotes

and

Z denotes a single bond, —C 2 H 4 —, —CH═CH—, —(CH 2 ) 4 —, —(CH 2 ) 3 O—, —O(CH 2 ) 3 —, —CH═CHCH 2 CH 2 —, —CH 2 CH 2 CH═CH—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —COO—, —OCO—, —C 2 F 4 —, —CHFCF 2 —, —CF═CF—, —CH═CF—, —CF═CH—, or —CH 2 —.

14. A liquid-crystalline medium according to claim 1 , which further comprises in total four compounds of formulae

15. A liquid-crystalline medium according to claim 1 , which further comprises at least one compound of formula IIIa and/or IIIb and at least one compound of formula IIIe

in which

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

alkenyl denotes a straight-chain alkenyl radical having 2-6 C atoms.

16. A liquid-crystalline medium according to claim 1 , which further comprises one or more compounds of formulae IIIa to IIIj:

in which

denotes

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

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

17. A liquid-crystalline medium according to claim 1 , which further comprises one or more compounds of the following formulae

18. A liquid-crystalline medium according to claim 1 , which further comprises at least three compounds of the following formulae

wherein alkyl denotes C n H 2n+1 , where n=3, 4 or 5.

19. A liquid-crystalline medium according to claim 1 , wherein when R 1 denotes alkenyl, said group is CH 2 ═CH, CH 3 —CH═CH, C 3 H 7 —CH═CH, CH 2 ═CH—C 2 H 4 or CH 3 —CH═CH—C 2 H 4 .

20. A liquid-crystalline medium according to claim 1 , which comprises

10-40% by weight of one or more compounds of the formulae IA and IB, and

10-40% by weight of one or more compounds of the formula II.

21. A liquid-crystalline medium according to claim 1 , which further comprises one or more compounds of the following formulae, which compounds when present are each in an amount of at least 5% by weight

in which

R 13 -R 27 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, in which one or more CH 2 groups are optionally replaced by —O—, —S—,

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

z and m each, independently of one another, denote 1-6,

R E denotes H, CH 3 , C 2 H 5 or n-C 3 H 7 , and

x denotes 0, 1, 2 or 3.

22. A liquid-crystalline medium according to claim 1 , which comprises one or more compounds of the following formulae T-1 to T-22

in which

R 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, in which one or more CH 2 groups are optionally replaced by —O—, —S—,

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

23. A liquid-crystalline medium according to claim 1 , which further comprises one or more compounds of the following formulae B-1 to B-2

in which

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

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

24. A liquid-crystalline medium according to claim 1 , which further comprises one or more compounds of the following formulae

25. A liquid-crystalline medium according to claim 1 , which comprises one or more compounds of the following formulae To-1 and To-2

in which

R 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, in which one or more CH 2 groups are optionally replaced by —O—, —S—,

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

alkyl denotes a straight-chain alkyl radical having 1-6 C atoms.

26. A liquid-crystalline medium according to claim 1 , which comprises one or more compounds of the following formula

alkyl* denotes a straight-chain alkyl radical having 1-6 C atoms.

27. A liquid-crystalline medium according to claim 1 , which comprises at least one compound of the formulae

28. A liquid-crystalline medium according to claim 1 , which further comprises one or more compounds of the following formulae

wherein n=1-12.

29. A liquid-crystalline medium according to claim 1 , which comprises the following compound

wherein alkyl* denotes a straight-chain alkyl radical having 1-6 C atoms.

30. An electro-optical display having active-matrix addressing based on the ECB, PA LCD, FFS or the IPS effect, which contains, as dielectric, a liquid-crystalline medium according to claim 1 .

31. A liquid-crystalline medium according to claim 1 , which contains at least one compound of formula IA

in which

R 1 denotes straight-chain alkyl or straight-chain alkenyl having up to 15 C atoms,

and

v denotes 2-5.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 19, 2015
From: KLASEN-MEMMER, MELANIE; SCHOEN, SABINE
To: MERCK PATENT GMBH
Reel/Frame 036362/0943 →
Priority Claims (1)
DE 10 2004 032 326 · Jul 2, 2004 · national
Continuity (5)
Division 13968864 · Aug 16, 2013
Division 13524352 · Jun 15, 2012
Division 13170513 · Jun 28, 2011
Division 11631182
Related Publication 20150240157A1 · Aug 27, 2015