IP Library Granted Patent US 9,267,078
Granted Patent B2
US 9,267,078 · App. 13/524,352 · Granted Feb 23, 2016

Liquid crystalline medium

Inventors: Melanie Klasen-Memmer (Heuchelheim, DE); Sabine Schoen (Herten, DE)
Assignee: Merck Patent GmbH
C09K19/3001C09K19/02C09K19/0208C09K19/12C09K19/3003C09K19/3028C09K19/3048C09K19/3066C09K19/3068C09K19/3098C09K19/44C09K19/0216C09K19/322C09K2019/122C09K2019/123C09K2019/181C09K2019/183C09K2019/301C09K2019/3004C09K2019/3009C09K2019/3016C09K2019/3027C09K2019/325Y10T428/10
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Quick Facts
Patent No.
US 9,267,078
App. No.
13/524,352
Granted
Feb 23, 2016
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 (182)

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 10% by weight of at least one compound of formula B-4

in which

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

and

at least two compounds of formulae IA, IB and/or II

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, 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 wherein at least one of conditions A) or B) applies:

condition A):

the liquid-crystalline medium 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≡—, —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 condition B):

the liquid-crystalline medium comprises one or more compounds of formulae N-1 to N-5

in which

R 1 and R 2 each, independently of one another, have the above-mentioned meanings and

Z, Z 1 and Z 2 each, independently of one another, denote —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 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF—, —CF═CH—, —CH═CF—, —CH 2 — or a single bond.

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

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

4. 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.

5. 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.

6. 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.

7. 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.

8. 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.

9. 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.

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

11. A liquid-crystalline medium according to claim 1 , which comprises a compound of each of the compounds of the formulae IA, IB and II

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

v denotes 1 to 6.

12. 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

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 —.

13. 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 .

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 12 , which comprises one or more compounds of formulae IIIa to IIIj:

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.

17. A liquid-crystalline medium according to claim 12 , which comprises one or more compounds of the following formulae

18. A liquid-crystalline medium according to claim 12 , which 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 , which comprises a compound of formulae IA and/or IB

in which

R 1 is a straight-chain alkenyl or alkyl, and

v denotes 1 to 6.

20. A liquid-crystalline medium according to claim 19 , 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 .

21. A liquid-crystalline medium according to claim 11 , 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.

22. 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— or —O—CO— 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.

23. A liquid-crystalline medium according to claim 1 , which further 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.

24. 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.

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

26. A liquid-crystalline medium according to claim 1 , wherein condition A) applies, wherein the liquid-crystalline medium 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.

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

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

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

29. A liquid-crystalline medium according to claim 1 , wherein condition B) applies, wherein the liquid-crystalline medium comprises one or more compounds of formulae N-1 to N-5

in which

R 1 and R 2 each, independently of one another, denote straight-chain alkyl, straight-chain alkoxy or straight-chain alkenyl, and

Z, Z 1 and Z 2 each, independently of one another, denote —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 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF—, —CF═CH—, —CH═CF—, —CH 2 — or a single bond.

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

wherein n=1-12.

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

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

Priority Claims (1)
DE 10 2004 032 326 · Jul 2, 2004 · national
Continuity (3)
Division 13170513 · Jun 28, 2011
Division 11631182
Related Publication 20120248374A1 · Oct 4, 2012