LC MEDIUM

Abstract

LC media and LC displays containing an LC medium with positive dielectric anisotropy, which contains one or more compounds of formula I in a concentration of >0 and 10%

##STR00001##

and displays addressed by an active matrix and in particular displays of the IPS, PS-IPS, FFS, PS-FFS, HB-FFS, U-IPS, TN, PS-TN, STN or TN-TFT mode.

Claims

1. An LC medium with positive dielectric anisotropy, comprising one or more compounds of formula I in a concentration of >0 and 10% ##STR00422## in which R.sup.1 and R.sup.2 independently of each other denote alkyl having 1 to 6 C atoms.

2. The LC medium according to claim 1, having a birefringence <0.15.

3. The LC medium according to claim 1, wherein the one or more compounds of formula I are of the following formulae ##STR00423##

4. The LC medium according to claim 1, wherein the concentration of the one or more compounds of formula I is 1.0 to 10%.

5. The LC medium according to claim 1, additionally comprising one or more compounds of the following formulae ##STR00424## wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings ##STR00425## R.sup.0 is an unsubstituted or halogenated alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH.sub.2 groups are each optionally replaced, independently of one another, by CC, CF.sub.2O, CHCH, ##STR00426## O, COO or OCO in such a way that O atoms are not linked directly to one another, or denotes ##STR00427## X.sup.0 is F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical having up to 6 C atoms, Y.sup.0 is H or CH.sub.3, and Y.sup.1-6 is H or F.

6. The LC medium according to claim 1, further comprising one or more compounds of the following subformulae ##STR00428## in which R.sup.0 is an unsubstituted or halogenated alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH.sub.2 groups are each optionally replaced, independently of one another, by CC, CF.sub.2O, CHCH, ##STR00429## O, COO or OCO in such a way that O atoms are not linked directly to one another, or denotes ##STR00430## and X.sup.0 is F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical having up to 6 C atoms.

7. The LC medium according to claim 1, further comprising one or more compounds of the following subformulae ##STR00431## ##STR00432## ##STR00433## in which R.sup.0 is an unsubstituted or halogenated alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH.sub.2 groups are each optionally replaced, independently of one another, by CC, CF.sub.2O, CHCH, ##STR00434## O, COO or OCO in such a way that O atoms are not linked directly to one another, or denotes ##STR00435## X.sup.0 is F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical having up to 6 C atoms, and Y.sup.2 is H or F.

8. The LC medium according to claim 1, further comprising one or more compounds of the following formulae ##STR00436## in which R.sup.0 is an unsubstituted or halogenated alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH.sub.2 groups are each optionally replaced, independently of one another, by CC, CF.sub.2O, CHCH, ##STR00437## O, COO or OCO in such a way that O atoms are not linked directly to one another, or denotes ##STR00438## X.sup.0 is F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical having up to 6 C atoms, Y.sup.1-4 is H or F, Z.sup.0 denotes C.sub.2H.sub.4, (CH.sub.2).sub.4, CHCH, CFCF, C.sub.2F.sub.4, CH.sub.2CF.sub.2, CF.sub.2CH.sub.2, CH.sub.2O, OCH.sub.2, COO or OCF.sub.2, and in formulae V and VI also a single bond, and in formulae V and VIII also CF.sub.2O, r denotes 0 or 1, and s denotes 0 or 1.

9. The LC medium according to claim 1, further comprising one or more compounds of the following formulae ##STR00439## in which R.sup.0 is an unsubstituted or halogenated alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH.sub.2 groups are each optionally replaced, independently of one another, by CC, CF.sub.2O, CHCH, ##STR00440## O, COO or OCO in such a way that O atoms are not linked directly to one another, or denotes ##STR00441##

10. The LC medium according to claim 1, additionally comprising one or more compounds of the following formulae: ##STR00442## in which X.sup.0 is F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical having up to 6 C atoms, alkyl denotes C.sub.1-6-alkyl, alkenyl denote C.sub.2-6-alkenyl, L denotes H or F, R denotes C.sub.1-6-alkyl, C.sub.1-6-alkoxy or C.sub.2-6-alkenyl, R.sup.a1, R.sup.b1 denote independently of each other CH.sub.3 or C.sub.2H.sub.5, and i, k are independently of each other 0, 1, 2 or 3,

11. The LC medium according to claim 1, further comprising one or more compounds of the following formulae ##STR00443## wherein alkyl denotes C.sub.1-6-alkyl.

12. The LC medium according to claim 1, which does not contain any compounds of the following formulae: ##STR00444## in which L.sup.1 and L.sup.2 denote independently of one another H or F, R denotes on each occurrence identically or differently alkyl or alkoxy with 1 to 12 C atoms, R denotes on each occurrence identically or differently alkenyl with 2 to 7 C atoms which contains a terminal vinyl group, and R denotes R or R.

13. The LC medium according to claim 1, further comprising one or more compounds of the following formula ##STR00445## in which R.sup.3 and R.sup.4 each, independently of one another, denote n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 C atoms, and preferably each, independently of one another, denote alkyl having 1 to 6 C atoms or alkenyl having 2 to 6 C atoms.

14. The LC medium according to claim 1, further comprising one or more compounds of the following formulae ##STR00446## in which alkyl denotes C.sub.1-6-alkyl.

15. The LC medium according to claim 1, further comprising one or more compounds of formula XVI ##STR00447## in which R.sup.3 and R.sup.4 each, independently of one another, denote n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 C atoms, and L denotes H or F.

16. The LC medium according to claim 1, further comprising a compound of formula XVIc2 ##STR00448##

17. The LC medium according to claim 1, comprising one or more compounds of formula IA1 ##STR00449## in which R.sup.0 is ethyl or propyl and X.sup.0 is F.

18. The LC medium according to claim 1, further comprising one or more compounds of the following formulae ##STR00450## in which R.sup.0 is an unsubstituted or halogenated alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH.sub.2 groups are each optionally replaced, independently of one another, by CC, CF.sub.2O, CHCH, ##STR00451## O, COO or OCO in such a way that O atoms are not linked directly to one another, or denotes ##STR00452## X.sup.0 is F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical having up to 6 C atoms, and Y.sup.1-4 is H or F.

19. The LC medium according to claim 1, further comprising one or more compounds of formula XXIa ##STR00453## in which R.sup.0 denotes ethyl, n-propyl, n-butyl or n-pentyl.

20. The LC medium according to claim 1, further comprising one or more compounds of the following formulae ##STR00454## in which R.sup.3 denotes n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 C atoms, and X.sup.0 is F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical having up to 6 C atoms.

21. The LC medium according to claim 1, further comprising one or more compounds of formula XXIXa ##STR00455## in which R.sup.3 denotes ethyl, n-propyl, n-butyl or n-pentyl.

22. A process for preparing an LC medium according to claim 1, comprising mixing one or more compounds of formula I with further LC compounds.

23. An electro-optical application, shutter glasses, a 3D application, or an LC display or an IPS, PS-IPS, FFS, PS-FFS, HB-FFS, U-IPS, TN, PS-TN, STN or TN-TFT display, comprising the LC medium according to claim 1.

Description

EXAMPLE 1

[0271] The LC mixture N1 is formulated as follows:

TABLE-US-00009 CPGP-5-2 1.0% cl.p. 110.5 C. CPGU-3-OT 1.5% n 0.1105 CCG-V-F 8.5% +5.8 CCP-3-1 5.0% .sub. 8.9 CCP-3FFF 10.0% K.sub.1 17.2 CCP-V-1 16.0% K.sub.3 19.7 CCP-V2-1 9.0% K.sub.3/K.sub.1 1.14 CCQU-2-F 5.0% V.sub.0 1.82 V CCQU-3-F 10.0% LTS 20 C. 1000 h CDU-2-F 10.0% PGP-2-2V 5.5% CC-3-V1 10.0% PP-1-2V1 7.0% PP-1-3 1.5%

[0272] The mixture contains 1.0% of the compound CPGP-5-2 of formula I.

[0273] To 99.9% of the mixture N1 are added 0.1% of the stabiliser S3-1 to give the mixture N11.

EXAMPLE 2

[0274] The LC mixture N2 is formulated as follows:

TABLE-US-00010 CPGP-5-2 1.0% cl.p. 109.7 C. CPGU-3-OT 2.5% n 0.1115 DGUQU-4-F 3.0% +5.8 CCG-V-F 9.0% .sub. 8.8 CCP-3-1 6.0% K.sub.1 17.2 CCP-2FFF 5.0% K.sub.3 19.4 CCP-3FFF 10.0% K.sub.3/K.sub.1 1.13 CCP-5FFF 8.0% V.sub.0 1.81 V CCP-V-1 16.0% LTS 20 C. 1000 h CCP-V2-1 4.5% CCQU-3-F 10.0% PGP-2-2V 4.5% CC-3-V1 11.0% PP-1-2V1 4.5% PP-1-3 5.0%

[0275] The mixture contains 1.0% of the compound CPGP-5-2 of formula I.

[0276] To 99.9% of the mixture N2 are added 0.1% of the stabiliser S3-1 to give the mixture N22.

VHR Values

[0277] The VHR values of mixtures C11, N11 and N22 are measured at 100C, 3 Hz and 1V in VHR test cell before and after light exposure using a LED lamp.

[0278] The results are shown in Table 1.

TABLE-US-00011 TABLE 1 VHR values before and after BL load, 3 Hz/100 C. C11 N11 N22 VHR/% Initial 61.5 74.9 79.6 After BL 144 h 75.4 78.9 82.7

[0279] From Table 1 it can be seen that the mixtures N11 and N22 according to the present invention, which contain a compound of formula I, show significantly higher VHR values that mixture C11, both before and after backlight stress.

COMPARISON EXAMPLE 2

[0280] The LC mixture C2 is formulated as follows:

TABLE-US-00012 CPGU-3-OT 2.0% cl.p. 109.9 C. DGUQU-4-F 2.5% n 0.1116 CCG-V-F 11.0% +5.6 CCP-3-1 5.0% .sub. 8.6 CCP-3FFF 10.0% K.sub.1 17.5 CCP-5FFF 8.0% K.sub.3 19.2 CCP-V-1 12.0% K.sub.3/K.sub.1 1.10 CCP-V2-1 6.0% V.sub.0 1.85 V CCQU-2-F 5.0% CCQU-3-F 10.0% PGP-2-2V 8.0% CC-3-2V1 2.5% CC-3-V1 11.0% PP-1-2V1 2.5% PP-1-3 4.5%

[0281] The mixture does not show satisfying LTS.

EXAMPLE 3

[0282] The LC mixture N3 is formulated as follows:

TABLE-US-00013 CPGP-5-2 0.5% cl.p. 110.0 C. CPGU-3-OT 2.0% n 0.1107 DGUQU-4-F 3.0% +5.7 CCG-V-F 9.5% .sub. 8.7 CCP-3-1 5.0% K.sub.1 17.6 CCP-3FFF 10.0% K.sub.3 19.2 CCP-5FFF 6.5% K.sub.3/K.sub.1 1.09 CCP-V-1 14.0% V.sub.0 CCP-V2-1 5.5% CCQU-2-F 6.0% CCQU-3-F 10.0% PGP-2-2V 6.5% CC-3-2V1 3.0% CC-3-V1 11.0% PP-1-2V1 2.5% PP-1-3 5.0%

[0283] The mixture contains 0.5% of the compound CPGP-5-2 of formula I.

EXAMPLE 4

[0284] The LC mixture N4 is formulated as follows:

TABLE-US-00014 CPGP-5-2 1.0% cl.p. 109.4 C. CPGU-3-OT 2.0% n 0.1109 DGUQU-4-F 3.0% +5.8 CCG-V-F 10.0% .sub. 8.7 CCP-3-1 5.0% K.sub.1 17.5 CCP-3FFF 10.0% K.sub.3 19.4 CCP-5FFF 8.0% K.sub.3/K.sub.1 1.11 CCP-V-1 12.5% V.sub.0 1.83 V CCP-V2-1 5.5% LTS 20 C. 1000 h CCQU-2-F 5.0% CCQU-3-F 10.0% PGP-2-2V 6.0% CC-3-2V1 3.0% CC-3-V1 11.0% PP-1-2V1 3.0% PP-1-3 5.0%

[0285] The mixture contains 1.0% of the compound CPGP-5-2 of formula I, and shows good LTS at 20 C.

EXAMPLE 5

[0286] The LC mixture N5 is formulated as follows:

TABLE-US-00015 CPGP-5-2 2.0% cl.p. 109.3 C. CPGU-3-OT 1.5% n 0.1104 DGUQU-4-F 3.0% +5.7 CCG-V-F 9.5% .sub. 8.7 CCP-3-1 5.0% K.sub.1 17.5 CCP-3FFF 10.0% K.sub.3 19.3 CCP-5FFF 7.5% K.sub.3/K.sub.1 1.10 CCP-V-1 14.0% V.sub.0 1.84 V CCP-V2-1 4.0% LTS 20 C. 1000 h CCQU-2-F 6.0% CCQU-3-F 10.0% PGP-2-2V 5.0% CC-3-2V1 3.0% CC-3-V1 11.0% PP-1-2V1 3.5% PP-1-3 5.0%

[0287] The mixture contains 2.0% of the compound CPGP-5-2 of formula I, and shows good LTS at 20 C.

EXAMPLE 6

[0288] The LC mixture N6 is formulated as follows:

TABLE-US-00016 CPGP-5-2 4.0% cl.p. 109.3 C. CPGU-3-OT 1.5% n 0.1100 DGUQU-4-F 3.0% +5.7 CCG-V-F 9.5% .sub. 8.7 CCP-3-1 5.0% K.sub.1 17.5 CCP-3FFF 10.0% K.sub.3 19.6 CCP-5FFF 8.0% K.sub.3/K.sub.1 1.12 CCP-V-1 14.0% V.sub.0 1.83 V CCP-V2-1 2.5% LTS 20 C. 1000 h CCQU-2-F 6.0% LTS 30 C. 1000 h CCQU-3-F 10.0% PGP-2-2V 2.5% CC-3-2V1 3.0% CC-3-V1 11.0% PP-1-2V1 5.0% PP-1-3 5.0%

[0289] The mixture contains 4.0% of the compound CPGP-5-2 of formula I, and shows good LTS at 20 C. and 30 C.

EXAMPLE 7

[0290] The LC mixture N7 is formulated as follows:

TABLE-US-00017 CPGP-5-2 6.0% cl.p. 110.0 C. CPGU-3-OT 1.5% n 0.1094 DGUQU-4-F 2.0% +5.8 CCG-V-F 10.0% .sub. 8.8 CCP-3-1 4.5% K.sub.1 17.5 CCP-3FFF 10.0% K.sub.3 19.6 CCP-5FFF 9.5% K.sub.3/K.sub.1 1.12 CCP-V-1 6.0% V.sub.0 1.83 V CCP-V2-1 6.5% LTS 20 C. 1000 h CCQU-2-F 8.0% LTS 30 C. 1000 h CCQU-3-F 10.0% LTS 40 C. 1000 h PGP-2-2V 1.5% CC-3-2V1 4.0% CC-3-V1 10.5% PP-1-2V1 5.0% PP-1-3 5.0%

[0291] The mixture contains 6.0% of the compound CPGP-5-2 of formula I, and shows good LTS at 20 C., 30 C. and 40 C.

VHR values

[0292] The VHR values of mixtures C.sub.2, N4, N5, N6 and N7 are measured at 60C, 60 Hz/3 Hz and 1V in VHR test cell before and after light exposure for varying using a LED lamp.

[0293] The results are shown in Tables 2 and 3.

TABLE-US-00018 TABLE 2 VHR values before and after BL load, 60 Hz/60 C. C2 N4 N5 N6 N7 VHR/% Initial 99.2 99.1 99.3 99.3 99.4 After BL 24 h 93.8 94.0 94.1 94.3 94.5 After BL 120 h 76.7 76.6 76.7 77.5 78.8

TABLE-US-00019 TABLE 3 VHR values before and after BL load, 3 Hz/60 C. C2 N4 N5 N6 N7 VHR/% Initial 93.0 93.6 94.5 94.4 94.8 After BL 24 h 70.7 71.0 72.3 73.6 74.8 After BL 120 h 21.6 21.7 22.0 23.0 24.5

[0294] From Tables 2 and 3 it can be seen that the mixtures N4-N7 according to the present invention, which contain a compound of formula I, show higher VHR values than mixture C.sub.2 after backlight stress.

EXAMPLE 8

[0295] To 99.95% of the LC mixture of Example 7 are added 0.05% of stabiliser S1-1.

##STR00408##

EXAMPLE 9

[0296] To 99.65% of the LC mixture of Example 7 are added 0.05% of stabiliser S1-1 and 0.3% of the monomer RM-1.

##STR00409##

EXAMPLE 10

[0297] To 99.7% of the LC mixture of Example 7 are added 0.3% of the monomer RM-35.

##STR00410##

EXAMPLE 11

[0298] To 99.65% of the LC mixture of Example 7 are added 0.05% of stabiliser S2-1 and 0.3% of the monomer RM-64.

##STR00411##

EXAMPLE 12

[0299] To 99.7% of the LC mixture of Example 6 are added 0.3% of the monomer RM-120.

##STR00412##

EXAMPLE 13

[0300] To 99.699% of the LC mixture of Example 5 are added 0.3% of the monomer RM-19 and 0.001% of Irgacure 651.

##STR00413##

EXAMPLE 14

[0301] To 99.7% of the LC mixture of Example 4 are added 0.3% of the monomer RM-121.

##STR00414##

EXAMPLE 15

[0302] To 99.7% of the LC mixture of Example 6 are added 0.3% of the monomer RM-122.

##STR00415##

EXAMPLE 16

[0303] To 99.7% of the LC mixture of Example 7 are added 0.3% of the monomer RM-91.

##STR00416##

EXAMPLE 17

[0304] To 99.98% of the LC mixture of Example 7 are added 0.02% of stabiliser S1-1.

EXAMPLE 18

[0305] To 99.99% of the LC mixture of Example 7 are added 0.01% of stabiliser S2-1.

##STR00417##

EXAMPLE 19

[0306] To 99.98% of the LC mixture of Example 3 are added 0.02% of stabiliser stabiliser S3-1.

##STR00418##

EXAMPLE 20

[0307] To 99.95% of the LC mixture of Example 6 are added 0.05% of stabiliser S3-2.

##STR00419##

EXAMPLE 21

[0308] To 99.98% of the LC mixture of Example 7 are added 0.02% of stabiliser S3-3.

##STR00420##

EXAMPLE 22

[0309] To 99.7% of the LC mixture of Example 4 are added 0.3% of the monomer RM-39.

##STR00421##

[0310] The preceding examples can be repeated with similar success by substituting the generically or specifically described reactants and/or operating conditions of this invention for those used in the preceding examples.

[0311] Without further elaboration, it is believed that one skilled in the art can, using the preceding description, utilize the present invention to its fullest extent. The preceding preferred specific embodiments are, therefore, to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any way whatsoever. From the description, one skilled in the art can easily ascertain the essential characteristics of this invention and, without departing from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various usages and conditions.

[0312] The entire disclosures of all applications, patents and publications, cited herein and of corresponding European Application No. EP 19183112.2, filed Jun. 28, 2019, are incorporated by reference herein.