LIQUID CRYSTAL MIXTURE AND LIQUID CRYSTAL DISPLAY

Abstract

The invention relates to a compound of formula I,

##STR00001##

wherein R.sup.11, R.sup.21, A.sup.11, A, Z, X.sup.11, X.sup.21, Y.sup.11, Y.sup.12, Sp.sup.11, Sp.sup.21, o and p have one of the meanings as given in claim 1. The invention further relates to method of production of a compound of formula I, to the use of said compounds in LC media and to LC media comprising one or more compounds of formula I. Further, the invention relates to a method of production of such LC media, to the use of such media in LC devices, and to LC device comprising a LC medium according to the present invention. The present invention further relates to a process for the fabrication such liquid crystal display and to the use of the liquid crystal mixtures according to the invention for the fabrication of such liquid crystal display.

Claims

1. Compound of formula I, ##STR00416## wherein A.sup.11 denotes a radical ##STR00417## where, in addition, one or more H atoms in these radical may be replaced by L, and/or one or more and/or one or more CH groups may be replaced by N, A denotes, independently of one another, in each occurrence a) the group consisting of 1,4-phenylene and 1,3-phenylene, wherein, in addition, one or two CH groups may be replaced by N and wherein, in addition, one or more H atoms may be replaced by L, b) the group consisting of saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radicals having 5 to 20 cyclic C atoms, one or more of which may, in addition, be replaced by heteroatoms, selected from the group consisting of ##STR00418## where, in addition, one or more H atoms in these radicals may be replaced by L, and/or one or more double bonds may be replaced by single bonds, and/or one or more CH groups may be replaced by N, c) group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, wherein, in addition, one or more non-adjacent CH.sub.2 groups may be replaced by O and/or S and wherein, in addition, one or more H atoms may be replaced by F, or d) a group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl and selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by L, L on each occurrence, identically or differently, denotes OH, F, Cl, Br, I, CN, NO.sub.2, SF.sub.5, NCO, NCS, OCN, SCN, C(O)N(R.sup.z).sub.2, C(O)R.sup.z, N(R.sup.z).sub.2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or straight-chain or branched or cyclic alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, preferably 1 to 12 C atoms, more preferably 1 to 6 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl, or X.sup.21-Sp.sup.21-R.sup.21, M denotes O, S, CH.sub.2, CHR.sup.z or CR.sup.yR.sup.z, and R.sup.y and R.sup.z each, independently of one another, denote H, CN, F or alkyl having 1-12 C atoms, wherein, in addition, one or more H atoms may be replaced by F, Y.sup.11 and Y.sup.12 each, independently of one another, denote H, F, phenyl or optionally fluorinated alkyl having 1-12 C atoms, Z denotes, independently of each other, in each occurrence, a single bond, COO, OCO, OCOO, OCH.sub.2, CH.sub.2O, OCF.sub.2, CF.sub.2O, (CH.sub.2).sub.n, CF.sub.2CF.sub.2, CHCH, CFCF, CHCHCOO, OCOCHCH, COS, SCO, CSS, SCS, SCSS or CC, n denotes an integer between 2 and 8, o and p denotes each and independently 0, 1 or 2, X.sup.11 and X.sup.21 denote independently from one another, in each occurrence a single bond, COO, OCO, OCOO, O, CHCH, CC, CF.sub.2O, OCF.sub.2, CF.sub.2CF.sub.2, CH.sub.2O, OCH.sub.2, COS, SCO, CSS, SCS, SCSS or S, Sp.sup.11 and Sp.sup.21 denote each and independently, in each occurrence a single bond or a spacer group comprising 1 to 20 C atoms, wherein one or more non-adjacent and non-terminal CH.sub.2 groups may also be replaced by O, S, NH, N(CH.sub.3), CO, OCO, SCO, OOCO, COS, COO, CF.sub.2, CF.sub.2O, OCF.sub.2 C(OH), CH(alkyl)-, CH(alkenyl)-, CH(alkoxyl)-, CH(oxaalkyl)-, CHCH or CC however in such a way that no two O-atoms are adjacent to one another and no two groups selected from OCO, SCO, OOCO, COS, COO and CHCH are adjacent to each other, R.sup.11 denotes P, R.sup.21 denotes P, or halogen, CN, optionally fluorinated alkyl or alkenyl with up to 15 C atoms in which one or more non adjacent CH.sub.2-groups may be replaced by O, S, CO, C(O)O, OC(O), OC(O)O, P each and independently from another in each occurrence a polymerisable group.

2. Compound according to claim 1, characterized in that the compound is selected selected from compounds of the sub-formulae I-1 to I-9; ##STR00419## wherein R.sup.11, R.sup.21, A.sup.11, X.sup.11, X.sup.12, Y.sup.11, Y.sup.12, Sp.sup.11, and Sp.sup.12 have one of the meanings as given above in claim 1, A.sup.12 to A.sup.23 have one of the meanings for A as given in claim 1, and Z.sup.11 to Z.sup.22 have one of the meanings for Z as given above in claim 1.

3. Compound according to claim 1, characterized in that the compound is selected from compounds of the following sub-formulae, ##STR00420## wherein R.sup.11, R.sup.21, X.sup.11, X.sup.21, Sp.sup.11 and Sp.sup.21 have one of the meanings as given above in claim 1, Z.sup.11 and Z.sup.21 have one of the meanings for Z as given above in claim 1 and the group ##STR00421## is each and independently ##STR00422## or denotes ##STR00423## furthermore ##STR00424## wherein L is F, Cl, CH.sub.3, OCH.sub.3 and COCH.sub.3 or alkylene having 1 to 6 C Atoms, or X.sup.21-Sp.sup.21-R.sup.21.

4. Compound according to claim 1, characterized in that it is selected from compounds of the following sub-formulae, ##STR00425## R.sup.11, R.sup.21, X.sup.21, and Sp.sup.21 have one of the meanings as given above in claim 1, Z.sup.21 has one of the meanings for Z as given above under claim 1, r, s, t and q denote each and independently from another an integer from 1 to 8, Y denotes each and independently from each other methyl or H, and the group ##STR00426## is each and independently ##STR00427## or denotes ##STR00428## furthermore ##STR00429## wherein L is F, Cl, CH.sub.3, OCH.sub.3 and COCH.sub.3 or alkylene having 1 to 6 C Atoms, or X.sup.21-Sp.sup.21-R.sup.21.

5. Compound according to claim 1, characterized in that it is selected from compounds of the following sub-formulae, ##STR00430## ##STR00431## wherein Sp.sup.21 has one of the meanings as given above in formula I and L denotes F, Cl, OCH.sub.3 and COCH.sub.3 or alkylene having 1 to 6 C Atoms.

6. Compound according to claim 1, characterized in that it is selected from compounds of the following sub-formulae, ##STR00432## wherein Sp.sup.21 has one of the meanings as given above in formula I and L denotes F, Cl, OCH.sub.3 and COCH.sub.3 or alkylene having 1 to 6 C Atoms.

7. Use of compounds of formula I according claim 1 in a liquid crystal mixture.

8. Liquid crystal mixture, characterised in that it comprises a component A) comprising one or more compounds of formula I according to claim 1, and a liquid-crystalline component B), comprising one or more mesogenic or liquid-crystalline compounds.

9. Liquid crystal mixture according to claim 8 characterised in that the total concentration of compounds of formula I in the mixture is in the range of from 0.01 to 10% by weight.

10. Liquid crystal mixture according to claim 8, characterised in that it additionally comprises a polymerizable component C) comprising one or more polymerizable mesogenic or polymerizable isotropic compounds.

11. Liquid crystal mixture according to claim 10, characterised in that the concentration of polymerizable mesogenic or polymerizable isotropic compounds is in the range of from 0.01 to 10% by weight.

12. Liquid crystal mixture according to claim 10, characterised in that it comprises one or more compounds of formula P
P.sup.a-(Sp.sup.a).sub.s1-A.sup.2-(Z.sup.1-A.sup.1).sub.n2-(Sp.sup.b).sub.s2P.sup.bP wherein P.sup.a, P.sup.b each, independently of one another, denote a polymerisable group, Sp.sup.a, Sp.sup.b on each occurrence, identically or differently, denote a spacer group, s1, s2 each, independently of one another, are 0 or 1, A.sup.1, A.sup.2 each, independently of one another, denote a radical selected from the following groups: a) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene and 4,4-bicyclohexylene, wherein, in addition, one or more non-adjacent CH.sub.2 groups may be replaced by O and/or S and wherein, in addition, one or more H atoms may be replaced by F, b) the group consisting of 1,4-phenylene and 1,3-phenylene, wherein, in addition, one or two CH groups may be replaced by N and wherein, in addition, one or more H atoms may be replaced by L, c) the group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl and selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by L, d) the group consisting of saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radicals having 5 to 20 cyclic C atoms, one or more of which may, in addition, be replaced by heteroatoms, that are selected from: ##STR00433## where, in addition, one or more H atoms in these radicals may be replaced by L, and/or one or more double bonds may be replaced by single bonds, and/or one or more CH groups may be replaced by N, n2 is 0, 1, 2 or 3, Z.sup.1 in each case, independently of one another, denotes COO, OCO, CH.sub.2O, OCH.sub.2, CF.sub.2O, OCF.sub.2, or (CH.sub.2).sub.n, where n is 2, 3 or 4, O, CO, C(R.sup.0R.sup.00), CH.sub.2CF.sub.2, CF.sub.2CF.sub.2 or a single bond, L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF.sub.5 or straight-chain or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having up to 12 C atoms, R.sup.0, R.sup.00 each, independently of one another, denote H, F or straight-chain or branched alkyl having 1 to 12 C atoms, wherein, in addition, one or more H atoms may be replaced by F, M denotes O, S, CH.sub.2, CHY.sup.1 or CY.sup.1Y.sup.2, and Y.sup.1 and Y.sup.2 each, independently of one another, have one of the meanings indicated above for R.sup.o or denote CI or CN.

13. Liquid crystal mixture according to claim 8, characterized in that the LC host mixture has negative dielectric anisotropy.

14. Liquid crystal mixture according to claim 13, characterised in that the LC host mixture comprises one or more compounds selected from the following formulae: ##STR00434## wherein a is 1 or 2, b is 0 or 1, ##STR00435## denotes ##STR00436## R.sup.1 and R.sup.2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH.sub.2 groups may be replaced by O, CHCH, CO, OCO or COO in such a way that O atoms are not linked directly to one another, Z.sup.x denotes CHCH, CH.sub.2O, OCH.sub.2, CF.sub.2O, OCF.sub.2, O, CH.sub.2, CH.sub.2CH.sub.2 or a single bond, L.sup.1-4 each, independently of one another, denote F, Cl, OCF.sub.3, CF.sub.3, CH.sub.3, CH.sub.2F, CH F2.

15. Liquid crystal mixture according to claim 8, characterised in that the LC host mixture has positive dielectric anisotropy.

16. Liquid crystal mixture according to claim 15, characterised in that the LC host mixture comprises one or more compounds selected from the group consisting of the compounds of the formulae II and III, ##STR00437## wherein R.sup.20 each, identically or differently, denote a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by CC, CF.sub.2O, CHCH, ##STR00438## O, COO or OCO in such a way that O atoms are not linked directly to one another, X.sup.20 each, identically or differently, denote 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, each having up to 6 C atoms, and Y.sup.20-24 each, identically or differently, denote H or F, W denotes H or methyl, ##STR00439## each, identically or differently, denote ##STR00440##

17. Liquid crystal mixture according to claim 15, characterised in that it comprises one or more compounds selected from the group consisting of compounds of formulae XI and XII ##STR00441## wherein R.sup.20 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by CC, CF.sub.2O, CHCH, ##STR00442## O, COO or OCO in such a way that O atoms are not linked directly to one another, X.sup.20 each, identically or differently, denote 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, each having up to 6 C atoms, Y.sup.20-23 each, identically or differently, denote H or F, W denotes H or methyl, and ##STR00443## each, independently of one another, denote ##STR00444## and ##STR00445## denotes ##STR00446##

18. Liquid crystal mixture according to claim 8, characterised in that the LC host mixture comprises one or more compounds of the following formula: ##STR00447## in which the individual radicals have the following meanings: ##STR00448## denotes ##STR00449## denotes ##STR00450## R.sup.3 and R.sup.4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which, in addition, one or two non-adjacent CH.sub.2 groups may be replaced by O, CHCH, CO, OCO or COO in such a way that O atoms are not linked directly to one another, Z.sup.y denotes CH.sub.2CH.sub.2, CHCH, CF.sub.2O, OCF.sub.2, CH.sub.2O, OCH.sub.2, COO, OCO, C.sub.2F.sub.4, CFCF, CHCHCH.sub.2O or a single bond.

19. Liquid crystal mixture according to claim 8, characterised in that the LC host mixture comprises one or more compounds of the following formula ##STR00451## wherein the propyl, butyl and pentyl groups are straight-chain groups.

20. Liquid crystal mixture according to claim 8, characterised in that the LC host mixture comprises one or more compounds selected from the following formulae: ##STR00452## 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.

21. Liquid crystal mixture according to claim 8, characterised in that the LC host mixture comprises one or more compounds selected from the following formulae: ##STR00453## in which alkyl* denotes an alkyl radical having 1-6 C atoms.

22. Use of the liquid crystal mixture according to claim 8, for the fabrication of a liquid crystal display.

23. Process for the fabrication of a liquid crystal display, comprising at least the steps of: providing a first substrate which includes a pixel electrode and a common electrode for generating an electric field substantially parallel to a surface of the first substrate in the pixel region; providing a second substrate, the second substrate being disposed opposite to the first substrate; interposing a liquid crystal mixture according to claim 8; irradiating the liquid crystal mixture with linearly polarised light causing photoalignment of the liquid crystal; curing the polymerizable compounds of the liquid crystal mixture by irradiation with ultraviolet light or visible light having a wavelength of 450 nm or below.

24. Process according to claim 23, characterised in that the linearly polarised light is ultraviolet light or visible light having a wavelength of 450 nm or below.

25. Display, obtainable by a process according to claim 23.

26. Display according to claim 25, wherein the LC host mixture is homogeneously aligned without the application of an electric field.

27. Display according to claim 25, wherein the display is an IPS or FFS display.

Description

DETAILED DESCRIPTION

[0074] In detail, the present invention relates to photoreactive mesogens of formula I

##STR00015##

wherein [0075] A.sup.11 denotes a radical

##STR00016## [0076] where, in addition, one or more H atoms in these radical may be replaced by L, and/or one or more and/or one or more CH groups may be replaced by N, [0077] A denotes, independently of one another, in each occurrence [0078] a) the group consisting of 1,4-phenylene and 1,3-phenylene, wherein, in addition, one or two CH groups may be replaced by N and wherein, in addition, one or more H atoms may be replaced by L, [0079] b) the group consisting of saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radicals having 5 to 20 cyclic C atoms, one or more of which may, in addition, be replaced by heteroatoms, preferably selected from the group consisting of

##STR00017## [0080] where, in addition, one or more H atoms in these radicals may be replaced by L, and/or one or more double bonds may be replaced by single bonds, and/or one or more CH groups may be replaced by N, [0081] c) group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, wherein, in addition, one or more non-adjacent CH.sub.2 groups may be replaced by O and/or S and wherein, in addition, one or more H atoms may be replaced by F, or [0082] d) a group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl and selenophene-2,5-diyl, [0083] each of which may also be mono- or polysubstituted by L, [0084] L on each occurrence, identically or differently, denotes OH, F, Cl, Br, I, CN, NO.sub.2, SF.sub.5, NCO, NCS, OCN, SCN, C(O)N(R.sup.z).sub.2, C(O)R.sup.z, N(R.sup.z).sub.2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or straight-chain or branched or cyclic alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, preferably 1 to 12 C atoms, more preferably 1 to 6 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl, or X.sup.21-Sp.sup.21-R.sup.21, [0085] M denotes O, S, CH.sub.2, CHR.sup.z or CR.sup.yR.sup.z, and [0086] R.sup.y and R.sup.z each, independently of one another, denote H, CN, F or alkyl having 1-12 C atoms, wherein, in addition, one [0087] or more H atoms may be replaced by F, [0088] preferably H, methyl, ethyl, propyl, butyl, [0089] more preferably H or methyl, [0090] in particular H, [0091] Y.sup.11 and Y.sup.12 each, independently of one another, denote H, F, phenyl or optionally fluorinated alkyl having 1-12 C atoms, preferably H, methyl, ethyl, propyl, butyl, more preferably H or methyl, [0092] in particular H, [0093] Z denotes, independently of each other, in each occurrence, a single bond, OOC, OCO, OCOO, OCH.sub.2, CH.sub.2O, OCF.sub.2, CF.sub.2O, (CH.sub.2).sub.n, CF.sub.2CF.sub.2, CHCH, CFCF, CHCHOOC, OCOCHCH, COS, SCO, CSS, SCS, SCSS or CC, [0094] preferably a single bond, OOC, OOC, OCF.sub.2, CF.sub.2O, or (CH.sub.2).sub.n, [0095] more preferably a single bond, OOC, or OOC, [0096] n denotes an integer between 2 and 8, preferably 2, [0097] o and p denotes each and independently 0, 1 or 2, preferably 1, [0098] X.sup.11 and X.sup.21 denote independently from one another, in each occurrence a single bond, COO, OCO, OCOO, O, CHCH, CC, CF.sub.2O, OCF.sub.2, CF.sub.2CF.sub.2, CH.sub.2O, OCH.sub.2, COS, SCO, CSS, SCS, SCSS or S, [0099] preferably, a single bond, COO, OCO, OOOC, or O, [0100] more preferably a single bond or O, [0101] Sp.sup.11 and Sp.sup.21 denote each and independently, in each occurrence a single bond or a spacer group comprising 1 to 20 C atoms, wherein one or more non-adjacent and non-terminal CH.sub.2 groups may also be replaced by O, S, NH, N(CH.sub.3), CO, OCO, SCO, OCOO, COS, COO, CF.sub.2, CF.sub.2O, OCF.sub.2 C(OH), CH(alkyl)-, CH(alkenyl)-, CH(alkoxyl)-, CH(oxaalkyl)-, CHCH or CC, however in such a way that no two O-atoms are adjacent to one another and no two groups selected from OCO, SCO, OOOC, COS, COO and CHCH are adjacent to each other, [0102] preferably alkylene having 1 to 20, preferably 1 to 12, C atoms, which is optionally mono- or polysubstituted by F, Cl, Br, I or CN, [0103] more preferably straight-chain ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, [0104] R.sup.11 denotes P, [0105] R.sup.21 denotes P, or halogen, CN, optionally fluorinated alkyl or alkenyl with up to 15 C atoms in which one or more non-adjacent CH.sub.2-groups may be replaced by O, S, CO, C(O)O, OC(O), OC(O)O, preferably P, [0106] P each and independently from another in each occurrence a polymerizable group.

[0107] The polymerizable groups P are groups that are suitable for a polymerisation reaction, such as, for example, free-radical or ionic chain polymerisation, polyaddition or polycondensation, or for a polymer-analogous reaction, for example addition or condensation onto a main polymer chain. Particular preference is given to groups for chain polymerisation, in particular those containing a CC double bond or CC triple bond, and groups which are suitable for polymerisation with ring opening, such as, for example, oxetane or epoxide groups.

[0108] Preferred groups P are selected from the group consisting of

##STR00018##

CH.sub.2CW.sup.2(O).sub.k3, CW.sup.1CHCO(O).sub.k3, CW.sup.1CHCONH, CH.sub.2CW.sup.1CONH, CH.sub.3CHCHO, (CH.sub.2CH).sub.2CHOCO, (CH.sub.2CHCH.sub.2).sub.2CHOCO, (CH.sub.2CH).sub.2CHO, (CH.sub.2CHCH.sub.2).sub.2N, (CH.sub.2CHCH.sub.2).sub.2NCO, HOCW.sup.2W.sup.3, HSCW.sup.2W.sup.3, HW.sup.2N, HOCW.sup.2W.sup.3NH, CH.sub.2CW.sup.1CONH, CH.sub.2CH(COO).sub.k1-Phe-(O).sub.k2, CH.sub.2CH(CO).sub.k1-Phe-(O).sub.k2, Phe-CHCH, HOOC, OCN and W.sup.4W.sup.5W.sup.6Si, wherein W.sup.1 denotes H, F, Cl, CN, CF.sub.3, phenyl or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH.sub.3, W.sup.2 and W.sup.3 each, independently of one another, denote H or alkyl having 1 to 5 C atoms, in particular H, methyl, ethyl or n-propyl, W.sup.4, W.sup.5 and W.sup.6 each, independently of one another, denote Cl, oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, W.sup.7 and W.sup.8 each, independently of one another, denote H, Cl or alkyl having 1 to 5 C atoms, Phe denotes 1,4-phenylene, which is optionally substituted by one or more radicals L as defined above which are other than P-Sp-, k.sub.1, k.sub.2 and k.sub.3 each, independently of one another, denote 0 or 1, k.sub.3 preferably denotes 1, and k.sub.4 denotes an integer from 1 to 10.

[0109] Particularly preferred groups P and P.sup.a,b are selected from the group consisting of CH.sub.2CW.sup.1COO, in particular CH.sub.2CHCOO, CH.sub.2C(CH.sub.3)COO and CH.sub.2CFCOO, furthermore CH.sub.2CHO, (CH.sub.2CH).sub.2CHOCO, (CH.sub.2CH).sub.2CHO,

##STR00019##

[0110] Very particularly preferred groups P and P.sup.a,b are selected from the group consisting of acrylate, methacrylate, fluoroacrylate, furthermore vinyloxy, chloroacrylate, oxetane and epoxide groups, and of these preferably an acrylate or methacrylate group.

[0111] In another preferred embodiment, the polymerizable group P denotes the radical

##STR00020##

wherein [0112] Y denotes H, F, phenyl or optionally fluorinated alkyl having 1-12 C atoms, preferably H, methyl, ethyl, propyl, butyl, [0113] more preferably H or methyl, [0114] in particular H, [0115] q and r denotes each and independently an integer from 0 to 8, preferably q+r1 and 16, more preferably q and r each and independently denotes an integer from 1 to 8, and [0116] P denotes acrylate or methacrylate,

[0117] The compounds of formula I are preferably selected from compounds of the sub-formulae I-1 to I-9.

##STR00021##

wherein R.sup.11, R.sup.21, A.sup.11, X.sup.11, X.sup.12, Y.sup.11, Y.sup.12, Sp.sup.11, and Sp.sup.12 have one of the meanings as given above in formula I, A.sup.12 to A.sup.23 have one of the meanings for A, and Z.sup.11 to Z.sup.22 have one of the meanings for Z as given above under formula I.

[0118] Further preferred compounds of formula I are selected from the compounds of formulae I-1 to I-3.

[0119] Preferred compounds of formula I-1 to I-3 are selected from compounds of formulae I-1a to I-3a:

##STR00022##

wherein R.sup.11, R.sup.21, X.sup.11, X.sup.21, Sp.sup.11 and Sp.sup.21 have one of the meanings as given above in formula I, Z.sup.11 and Z.sup.21 have one of the meanings for Z as given above under formula I, and A.sup.12, A.sup.21 and A.sup.22 have one of the meanings for A, preferably A.sup.12, A.sup.21 and A.sup.22 denote each and independently a group consisting of 1,4-phenylene wherein one or two CH groups may be replaced by N and wherein, in addition, one or more H atoms may be replaced by L as given above under formula I, or a group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, wherein, in addition, one or more non-adjacent CH.sub.2 groups may be replaced by O and/or S and wherein, in addition, one or more H atoms may be replaced by F.

[0120] Further preferred compounds of formula I are compounds of the following sub-formula:

##STR00023##

[0121] R.sup.11, R.sup.21, X.sup.21, Sp.sup.11 and Sp.sup.21 have one of the meanings as given above in formula I, Z.sup.11 and Z.sup.21 have one of the meanings for Z as given above under formula I. In the above given preferred subformulae, the group

##STR00024##

is each and independently

##STR00025##

or denotes

##STR00026##

furthermore

##STR00027##

wherein L is preferably F, Cl, CH.sub.3, OCH.sub.3 and COCH.sub.3 or alkylene having 1 to 6 C Atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cylobutyl, cyclopentyl, cyclohexyl, or X.sup.21-Sp.sup.21-R.sup.21.

[0122] Further preferred compounds of formulae I-2a-1 are those wherein Z.sup.11 denotes a single bond.

[0123] Further preferred compounds of formulae I-1a-1 to I-3a-1 are those wherein X.sup.11 and X.sup.21 denote each and independently a single bond, O, COO or OCO, more preferably O or a single bond.

[0124] Further preferred compounds of formula I-1a-1 to I-3a-1 are those wherein Sp.sup.11 and Sp.sup.21 denote each and independently a single bond or (CH.sub.2).sub.n wherein n is an integer between 1 and 8, more preferably 2 and 6.

[0125] Further preferred compounds of formulae I-1a-1 to I-3a-1 are those wherein R.sup.11 and R.sup.21 denote each and independently acrylate, methacrylate or a group

##STR00028##

wherein [0126] Y denotes H, F, phenyl or optionally fluorinated alkyl having 1-12 C atoms, preferably H, methyl, ethyl, propyl, butyl, [0127] more preferably H or methyl, [0128] in particular H, [0129] q and r denotes each and independently an integer from 0 to 8, preferably q+r1 and 16, more preferably q and r each and independently denotes an integer from 1 to 8.
Further preferred compounds of formulae I-1a-1 to I-3a-1 are those wherein R.sup.11 denotes a group

##STR00029##

wherein [0130] Y denotes H or methyl, [0131] in particular H, [0132] q and r denotes each and independently an integer from 1 to 8, preferably 1 or 2, and
wherein R.sup.11 denotes acrylate or methacrylate.

[0133] Further preferred compounds of formulae I-1-1a-1 to I-3a-1 are those wherein both groups R.sup.11 and R.sup.21 denote acrylate or methacrylate. Preferred compounds of formulae I-3a-1 are compounds of the following sub-formulae:

##STR00030##

[0134] R.sup.11, R.sup.21, X.sup.21, and Sp.sup.21 have one of the meanings as given above in formula I, Z.sup.21 has one of the meanings for Z as given above under formula I, r, s, t and q denote each and independently from another an integer from 1 to 8, Y denotes each and independently from each other methyl or H, and

the group

##STR00031##

is each and independently

##STR00032##

or denotes

##STR00033##

furthermore

##STR00034##

[0135] Further preferred compounds of formulae I-3a-1a are compounds of the following sub-formulae:

##STR00035## ##STR00036## ##STR00037##

wherein Sp.sup.21 has one of the meanings as given above in formula I and L denotes F, Cl, OCH.sub.3 and COCH.sub.3 or alkylene having 1 to 6 C Atoms, preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cylobutyl, cyclopentyl, or cyclohexyl.

[0136] Further preferred compounds of formulae I-3a-1b are compounds of the following sub-formulae:

##STR00038##

[0137] Further preferred compounds of formulae I-3a-1c are compounds of the following sub-formulae:

##STR00039##

wherein L denotes F, Cl, OCH.sub.3 and COCH.sub.3 or alkylene having 1 to 6 C Atoms, preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cylobutyl, cyclopentyl, or cyclohexyl, and
s and t denotes each and independently an integer from 1 to 8, preferably s and t are identical.

[0138] The compounds of formula I and subformulae thereof are preferably synthesised according to or in analogy to the procedures described in WO 2017/102068 and JP 2006-6232809.

[0139] Preferred intermediate compounds (5) from which the compounds of formula I are preferably synthesised, are obtainable or obtained according to or in analogy to the procedure described in the following scheme:

##STR00040##

[0140] The compounds of formula I and subformulae thereof can be preferably utilized in a mixture comprising one or more mesogenic or liquid-crystalline compounds.

[0141] Therefore, the present invention relates to the use compounds of formula I and subformulae thereof in a liquid crystal mixture.

[0142] Further the present invention relates to liquid crystal mixtures comprising a photoalignment component A) comprising one or more photoreactive mesogens of formula I, and a liquid-crystalline component B), hereinafter also referred to as LC host mixture, comprising one or more mesogenic or liquid-crystalline compounds.

[0143] The media according to the invention preferably comprise from 0.01 to 10%, particularly preferably from 0.05 to 5% and most preferably from 0.1 to 3% of component A) comprising compounds of formula I according to the invention.

[0144] The media preferably comprise one, two or three, more preferably one or two and most preferably one compound of the formula I according to the invention.

[0145] In a preferred embodiment component A) consists of compounds of formula I.

[0146] In a preferred embodiment, the LC-host mixture (component B) according to the present invention comprises one or more, preferably two or more, low-molecular-weight (i.e. monomeric or unpolymerized) compounds. The latter are stable or unreactive with respect to a polymerisation reaction or photoalignment under the conditions used for the polymerisation of the polymerizable compounds or photoalignment of the photoreactive mesogen of formula I.

[0147] In principle, a suitable host mixture is any dielectrically negative or positive LC mixture which is suitable for use in conventional VA, IPS or FFS displays.

[0148] Suitable LC mixtures are known to the person skilled in the art and are described in the literature. LC media for VA displays having negative dielectric anisotropy are described in for example EP 1 378 557 A1.

[0149] Suitable LC mixtures having positive dielectric anisotropy which are suitable for LCDs and especially for IPS displays are known, for example, from JP 07-181 439 (A), EP 0 667 555, EP 0 673 986, DE 195 09 410, DE 195 28 106, DE 195 28 107, WO 96/23 851, WO 96/28 521 and WO2012/079676.

[0150] Preferred embodiments of the liquid-crystalline medium having negative or positive dielectric anisotropy according to the invention are indicated below and explained in more detail by means of the working examples.

[0151] The LC host mixture is preferably a nematic LC mixture, and preferably does not have a chiral LC phase.

[0152] In a preferred embodiment of the present invention the LC medium contains an LC host mixture with negative dielectric anisotropy. Preferred embodiments of such an LC medium, and the corresponding LC host mixture, are those of sections a)-z) below: [0153] a) LC medium which comprises one or more compounds of the formulae CY and/or PY:

##STR00041## [0154] wherein [0155] a denotes 1 or 2, [0156] b denotes 0 or 1,

##STR00042##

denotes

##STR00043## [0157] R.sup.1 and R.sup.2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH.sub.2 groups may be replaced [0158] by O, CHCH, CO, OCO or COO in such a way that O atoms are not linked directly to one another, preferably alkyl or alkoxy having 1 to 6 C atoms, [0159] Z.sup.x and Z.sup.y each, independently of one another, denote CH.sub.2CH.sub.2, CHCH, CF.sub.2O, OCF.sub.2O, CH.sub.2O, O CH.sub.2, COO, OCO, C.sub.2F.sub.4, CFCF, CHCHCH.sub.2O or a single bond, preferably a single bond, [0160] L.sup.1-4 each, independently of one another, denote F, Cl, OCF.sub.3, CF.sub.3, CH.sub.3, CH.sub.2F, CHF.sub.2. [0161] Preferably, both L.sup.1 and L.sup.2 denote F or one of L.sup.1 and L.sup.2 denotes F and the other denotes Cl, or both L.sup.3 and L.sup.4 denote F or one of L.sup.3 and L.sup.4 denotes F and the other denotes Cl. [0162] The compounds of the formula CY are preferably selected from the group consisting of the following sub-formulae:

##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## [0163] wherein a denotes 1 or 2, 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, and (O) denotes an oxygen atom or a single bond. Alkenyl preferably denotes CH.sub.2CH, CH.sub.2CHCH.sub.2CH.sub.2, CH.sub.3CHCH, CH.sub.3CH.sub.2CHCH, CH.sub.3(CH.sub.2).sub.2CHCH, CH.sub.3(CH.sub.2).sub.3CHCH or CH.sub.3CHCH(CH.sub.2).sub.2. [0164] The compounds of the formula PY are preferably selected from the group consisting of the following sub-formulae:

##STR00049## [0165] wherein 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, and (O) denotes an oxygen atom or a single bond. Alkenyl preferably denotes CH.sub.2CH, CH.sub.2CHCH.sub.2CH.sub.2, CH.sub.3CHCH, CH.sub.3CH.sub.2CHCH, CH.sub.3(CH.sub.2).sub.2CHCH, CH.sub.3(CH.sub.2).sub.3CHCH or CH.sub.3CHCH(CH.sub.2).sub.2. [0166] b) LC medium which additionally comprises one or more compounds of the following formula:

##STR00050## [0167] in which the individual radicals have the following meanings:

##STR00051##

denotes

##STR00052##

##STR00053##

denotes

##STR00054## [0168] R.sup.3 and R.sup.4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which, in addition, one or two non-adjacent CH.sub.2 groups may be replaced [0169] by O, CHCH, CO, OCO or COO in such a way that O atoms are not linked directly to one another, [0170] Z.sup.y [0171] denotes CH.sub.2CH.sub.2, CHCH, CF.sub.2O, OCF.sub.2, CH.sub.2O, OCH.sub.2, COO, OCO, C.sub.2F.sub.4, CFCF, CHCHCH.sub.2O or a single bond, preferably a single bond. [0172] The compounds of the formula ZK are preferably selected from the group consisting of the following sub-formulae:

##STR00055## [0173] 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. Alkenyl preferably denotes CH.sub.2CH, CH.sub.2CHCH.sub.2CH.sub.2, CH.sub.3CHCH, CH.sub.3CH.sub.2CHCH, CH.sub.3(CH.sub.2).sub.2CHCH, CH.sub.3(CH.sub.2).sub.3CHCH or CH.sub.3CHCH(CH.sub.2).sub.2. [0174] Especially preferred are compounds of formula ZK1 and ZK3. [0175] Particularly preferred compounds of formula ZK are selected from the following sub-formulae:

##STR00056## [0176] wherein the propyl, butyl and pentyl groups are straight-chain groups. [0177] Most preferred are compounds of formula ZK1a and ZK3a. [0178] c) LC medium which additionally comprises one or more compounds of the following formula:

##STR00057## [0179] in which the individual radicals on each occurrence, identically or differently, have the following meanings: [0180] R.sup.5 and R.sup.6 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH.sub.2 groups may be replaced by O, CHCH, CO, OCO or COO in such a way that O atoms are not linked directly to one another, preferably alkyl or alkoxy having 1 to 6 C atoms,

##STR00058##

denotes

##STR00059##

denotes

##STR00060##

and [0181] e denotes 1 or 2. [0182] The compounds of the formula DK are preferably selected from the group consisting of the following sub-formulae:

##STR00061## [0183] 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. Alkenyl preferably denotes CH.sub.2CH, CH.sub.2CHCH.sub.2CH.sub.2, CH.sub.3CHCH, CH.sub.3CH.sub.2CHCH, CH.sub.3(CH.sub.2).sub.2CHCH, CH.sub.3(CH.sub.2).sub.3CHCH or CH.sub.3CHCH(CH.sub.2).sub.2. [0184] d) LC medium which additionally comprises one or more compounds of the following formula:

##STR00062## [0185] in which the individual radicals have the following meanings:

##STR00063## [0186] denotes

##STR00064## [0187] with at least one ring F being different from cyclohexylene, [0188] f denotes 1 or 2, [0189] R.sup.1 and R.sup.2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH.sub.2 groups may be replaced [0190] by O, CHCH, CO, OCO or COO in such a way that O atoms are not linked directly to one another, [0191] Z.sup.x [0192] denotes CH.sub.2CH.sub.2, CHCH, CF.sub.2O, OCF.sub.2, CH.sub.2O, O CH.sub.2, COO, OCO, C.sub.2F.sub.4, CFCF, CHCHCH.sub.2O or a single bond, preferably a single bond, [0193] L.sup.1 and L.sup.2 each, independently of one another, denote F, Cl, OCF.sub.3, CF.sub.3, CH.sub.3, CH.sub.2F, CHF.sub.2. [0194] Preferably, both radicals L.sup.1 and L.sup.2 denote F or one of the radicals L.sup.1 and L.sup.2 denotes F and the other denotes Cl. [0195] The compounds of the formula LY are preferably selected from the group consisting of the following sub-formulae:

##STR00065## ##STR00066## [0196] in which R.sup.1 has the meaning indicated above, alkyl denotes a straight-chain alkyl radical having 1-6 C atoms, (0) denotes an oxygen atom or a single bond, and v denotes an integer from 1 to 6. R.sup.1 preferably denotes straight-chain alkyl having 1 to 6 C atoms or straight-chain alkenyl having 2 to 6 C atoms, in particular CH.sub.3, C.sub.2H.sub.5, n-C.sub.3H.sub.7, n-C.sub.4H.sub.9, n-C.sub.5H.sub.11, CH.sub.2CH, CH.sub.2CHCH.sub.2CH.sub.2, CH.sub.3CHCH, CH.sub.3CH.sub.2CHCH, CH.sub.3(CH.sub.2).sub.2CHCH, CH.sub.3(CH.sub.2).sub.3CHCH or CH.sub.3CHCH(CH.sub.2).sub.2. [0197] e) LC medium which additionally comprises one or more compounds selected from the group consisting of the following formulae:

##STR00067## [0198] in which alkyl denotes C.sub.1-6-alkyl, L.sup.x denotes H or F, and X denotes F, Cl, OCF.sub.3, OCHF.sub.2 or OCHCF.sub.2. Particular preference is given to compounds of the formula G1 in which X denotes F. [0199] f) LC medium which additionally comprises one or more compounds selected from the group consisting of the following formulae:

##STR00068## [0200] in which R.sup.5 has one of the meanings indicated above for R.sup.1, alkyl denotes C1-6-alkyl, d denotes 0 or 1, and z and m each, independently of one another, denote an integer from 1 to 6. R.sup.5 in these compounds is particularly preferably C.sub.1-6-alkyl or -alkoxy or C.sub.2-6-alkenyl, d is preferably 1. The LC medium according to the invention preferably comprises one or more compounds of the above-mentioned formulae in amounts of 5% by weight. [0201] g) LC medium which additionally comprises one or more biphenyl compounds selected from the group consisting of the following formulae:

##STR00069## [0202] 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. Alkenyl and alkenyl* preferably denote CH.sub.2CH, CH.sub.2CHCH.sub.2CH.sub.2, CH.sub.3CHCH, CH.sub.3CH.sub.2CHCH, CH.sub.3(CH.sub.2).sub.2CHCH, CH.sub.3(CH.sub.2).sub.3CHCH or CH.sub.3CHCH(CH.sub.2).sub.2. [0203] The proportion of the biphenyls of the formulae B1 to B3 in the LC mixture is preferably at least 3% by weight, in particular 5% by weight. [0204] The compounds of the formula B2 are particularly preferred. [0205] The compounds of the formulae B1 to B3 are preferably selected from the group consisting of the following sub-formulae:

##STR00070## [0206] in which alkyl* denotes an alkyl radical having 1-6 C atoms. The medium according to the invention particularly preferably comprises one or more compounds of the formulae B1a and/or B2e. [0207] h) LC medium which additionally comprises one or more terphenyl compounds of the following formula:

##STR00071## [0208] in which R.sup.5 and R.sup.6 each, independently of one another, have one of the meanings indicated above, and

##STR00072## [0209] each, independently of one another, denote

##STR00073## [0210] in which L.sup.5 denotes F or Cl, preferably F, and L.sup.6 denotes F, Cl, OCF.sub.3, CF.sub.3, CH.sub.3, CH.sub.2F or CHF.sub.2, preferably F. [0211] The compounds of the formula T are preferably selected from the group consisting of the following sub-formulae:

##STR00074## ##STR00075## ##STR00076## [0212] in which R denotes a straight-chain alkyl or alkoxy radical having 1-7 C atoms, R* denotes a straight-chain alkenyl radical having 2-7 C atoms, (O) denotes an oxygen atom or a single bond, and m denotes an integer from 1 to 6. R* preferably denotes CH.sub.2CH, CH.sub.2CHCH.sub.2CH.sub.2, CH.sub.3CHCH, CH.sub.3CH.sub.2CHCH, CH.sub.3(CH.sub.2).sub.2CHCH, CH.sub.3(CH.sub.2).sub.3CHCH or CH.sub.3CHCH(CH.sub.2).sub.2. [0213] R preferably denotes methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy or pentoxy. [0214] The LC medium according to the invention preferably comprises the terphenyls of the formula T and the preferred sub-formulae thereof in an amount of 0.5-30% by weight, in particular 1-20% by weight. [0215] Particular preference is given to compounds of the formulae T1, T2, T3 and T21. In these compounds, R preferably denotes alkyl, furthermore alkoxy, each having 1-5 C atoms. [0216] The terphenyls are preferably employed in mixtures according to the invention if the n value of the mixture is to be 0.1. Preferred mixtures comprise 2-20% by weight of one or more terphenyl compounds of the formula T, preferably selected from the group of compounds T1 to T22. [0217] i) LC medium which additionally comprises one or more compounds selected from the group consisting of the following formulae:

##STR00077## [0218] in which R.sup.1 and R.sup.2 have the meanings indicated above and preferably each, independently of one another, denote straight-chain alkyl having 1 to 6 C atoms or straight-chain alkenyl having 2 to 6 C atoms. [0219] Preferred media comprise one or more compounds selected from the formulae O1, O3 and O4. [0220] k) LC medium which additionally comprises one or more compounds of the following formula:

##STR00078## [0221] in which

##STR00079##

denotes

##STR00080## [0222] R.sup.9 denotes H, CH.sub.3, C.sub.2H.sub.5 or n-C.sub.3H.sub.7, (F) denotes an optional fluorine substituent, and q denotes 1, 2 or 3, and R.sup.7 has one of the meanings indicated for R.sup.1, preferably in amounts of >3% by weight, in particular 5% by weight and very particularly preferably 5-30% by weight. [0223] Particularly preferred compounds of the formula FI are selected from the group consisting of the following sub-formulae:

##STR00081## [0224] in which R.sup.7 preferably denotes straight-chain alkyl, and R.sup.9 denotes CH.sub.3, C.sub.2H.sub.5 or n-C.sub.3H.sub.7. Particular preference is given to the compounds of the formulae FI1, FI2 and FI3. [0225] l) LC medium which additionally comprises one or more compounds selected from the group consisting of the following formulae:

##STR00082## [0226] in which R.sup.8 has the meaning indicated for R.sup.1, and alkyl denotes a straight-chain alkyl radical having 1-6 C atoms. [0227] m) LC medium which additionally comprises one or more compounds which contain a tetrahydronaphthyl or naphthyl unit, such as, for example, the compounds selected from the group consisting of the following formulae:

##STR00083## ##STR00084## [0228] in which [0229] R.sup.10 and R.sup.11 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH.sub.2 groups may be replaced [0230] by O, CHCH, CO, OCO or OOC in such a way that O atoms are not linked directly to one another, preferably alkyl or alkoxy having 1 to 6 C atoms, [0231] and R.sup.10 and R.sup.11 preferably denote straight-chain alkyl or alkoxy having 1 to 6 C atoms or straight-chain alkenyl having 2 to 6 C atoms, and [0232] Z.sup.1 and Z.sup.2 each, independently of one another, [0233] denote C.sub.2H.sub.4, CHCH, (CH.sub.2).sub.4, (CH.sub.2).sub.3O, O(CH.sub.2).sub.3, CHCH [0234] CH.sub.2CH.sub.2, CH.sub.2CH.sub.2CHCH, CH.sub.2O, OCH.sub.2, CO O, O [0235] CO, C.sub.2F.sub.4, CFCF, CFCH, CHCF, CH.sub.2 or a single bond. [0236] n) LC medium which additionally comprises one or more difluoro-dibenzochromans and/or chromans of the following formulae:

##STR00085## [0237] in which [0238] R.sup.11 and R.sup.12 each, independently of one another, have one of the meanings indicated above for R.sup.11 under formula N1 [0239] ring M is trans-1,4-cyclohexylene or 1,4-phenylene, [0240] Z.sup.m C.sub.2H.sub.4, CH.sub.2O, OCH.sub.2, COO or OCO, [0241] c is 0, 1 or 2, [0242] preferably in amounts of 3 to 20% by weight, in particular in amounts of 3 to 15% by weight. [0243] Particularly preferred compounds of the formulae BC, CR and RC are selected from the group consisting of the following sub-formulae:

##STR00086## ##STR00087## ##STR00088## [0244] in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, (O) denotes an oxygen atom or a single bond, c is 1 or 2, and alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2-6 C atoms. Alkenyl and alkenyl* preferably denote CH.sub.2CH, CH.sub.2CHCH.sub.2CH.sub.2, CH.sub.3CHCH, CH.sub.3CH.sub.2CHCH, CH.sub.3(CH.sub.2).sub.2CHCH, CH.sub.3(CH.sub.2).sub.3CHCH or CH.sub.3CHCH(CH.sub.2).sub.2. [0245] Very particular preference is given to mixtures comprising one, two or three compounds of the formula BC-2. [0246] o) LC medium which additionally comprises one or more fluorinated phenanthrenes and/or dibenzofurans of the following formulae:

##STR00089## [0247] in which R.sup.11 and R.sup.12 each, independently of one another, have one of the meanings indicated above for R.sup.11 under formula N1, b denotes 0 or 1, L denotes F, and r denotes 1, 2 or 3. [0248] Particularly preferred compounds of the formulae PH and BF are selected from the group consisting of the following sub-formulae:

##STR00090## [0249] in which R and R each, independently of one another, denote a straight-chain alkyl or alkoxy radical having 1-7 C atoms. [0250] p) LC medium which additionally comprises one or more monocyclic compounds of the following formula

##STR00091## [0251] wherein [0252] R.sup.1 and R.sup.2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH.sub.2 groups may be replaced [0253] by O, CHCH, CO, OCO or OOC in such a way that O atoms are not linked directly to one another, preferably alkyl or alkoxy having 1 to 6 C atoms, [0254] L.sup.1 and L.sup.2 each, independently of one another, denote F, Cl, OCF.sub.3, CF.sub.3, CH.sub.3, CH.sub.2F, CHF.sub.2. [0255] Preferably, both L.sup.1 and L.sup.2 denote F or one of L.sup.1 and L.sup.2 denotes F and the other denotes Cl, [0256] The compounds of the formula Y are preferably selected from the group consisting of the following sub-formulae:

##STR00092## [0257] in which, Alkyl and Alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, Alkoxy denotes a straight-chain alkoxy 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 O denotes an oxygen atom or a single bond. Alkenyl and Alkenyl* preferably denote CH.sub.2CH, CH.sub.2CHCH.sub.2CH.sub.2, CH.sub.3CHCH, CH.sub.3CH.sub.2CHCH, CH.sub.3(CH.sub.2).sub.2CHCH, CH.sub.3(CH.sub.2).sub.3CHCH or CH.sub.3CHCH(CH.sub.2).sub.2. [0258] Particularly preferred compounds of the formula Y are selected from the group consisting of the following sub-formulae:

##STR00093## [0259] wherein Alkoxy preferably denotes straight-chain alkoxy with 3, 4, or 5 C atoms. [0260] q) LC medium which, apart from the stabilisers according to the invention, in particular of the formula I or sub-formulae thereof and the comonomers, comprises no compounds which contain a terminal vinyloxy group (OCHCH.sub.2). [0261] r) LC medium which comprises 1 to 5, preferably 1, 2 or 3, stabilisers, preferably selected from stabilisers according to the invention, in particular of the formula I or sub-formulae thereof. [0262] s) LC medium in which the proportion of stabilisers, in particular of the formula I or sub-formulae thereof, in the mixture as a whole is 1 to 1500 ppm, preferably 100 to 1000 ppm. [0263] t) LC medium which comprises 1 to 8, preferably 1 to 5, compounds of the formulae CY1, CY2, PY1 and/or PY2. The proportion of these compounds in the mixture as a whole is preferably 5 to 60%, particularly preferably 10 to 35%. The content of these individual compounds is preferably in each case 2 to 20%. [0264] u) LC medium which comprises 1 to 8, preferably 1 to 5, compounds of the formulae CY9, CY10, PY9 and/or PY10. The proportion of these compounds in the mixture as a whole is preferably 5 to 60%, particularly preferably 10 to 35%. The content of these individual compounds is preferably in each case 2 to 20%. [0265] v) LC medium which comprises 1 to 10, preferably 1 to 8, compounds of the formula ZK, in particular compounds of the formulae ZK1, ZK2 and/or ZK6. The proportion of these compounds in the mixture as a whole is preferably 3 to 25%, particularly preferably 5 to 45%. The content of these individual compounds is preferably in each case 2 to 20%. [0266] w) LC medium in which the proportion of compounds of the formulae CY, PY and ZK in the mixture as a whole is greater than 70%, preferably greater than 80%. [0267] x) LC medium in which the LC host mixture contains one or more compounds containing an alkenyl group, preferably selected from the group consisting of formula CY, PY and LY, wherein one or both of R.sup.1 and R.sup.2 denote straight-chain alkenyl having 2-6 C atoms, formula ZK and DK, wherein one or both of R.sup.3 and R.sup.4 or one or both of R.sup.5 and R.sup.6 denote straight-chain alkenyl having 2-6 C atoms, and formula B2 and B3, very preferably selected from formulae CY15, CY16, CY24, CY32, PY15, PY16, ZK3, ZK4, DK3, DK6, B2 and B3, most preferably selected from formulae ZK3, ZK4, B2 and B3. The concentration of these compounds in the LC host mixture is preferably from 2 to 70%, very preferably from 3 to 55%. [0268] y) LC medium which contains one or more, preferably 1 to 5, compounds selected of formula PY1-PY8, very preferably of formula PY2. The proportion of these compounds in the mixture as a whole is preferably 1 to 30%, particularly preferably 2 to 20%. The content of these individual compounds is preferably in each case 1 to 20%. [0269] z) LC medium which contains one or more, preferably 1, 2 or 3, compounds of formula T2. The content of these compounds in the mixture as a whole is preferably 1 to 20%.

[0270] In another preferred embodiment of the present invention the LC medium contains an LC host mixture with positive dielectric anisotropy. Preferred embodiments of such an LC medium, and the corresponding LC host mixture, are those of sections aa)-mmm) below: [0271] aa) LC-medium, characterised in that it comprises one or more compounds selected from the group of compounds of the formulae II and III

##STR00094## [0272] wherein [0273] R.sup.20 each, identically or differently, denote a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by CC, CF.sub.2O, CHCH, , , O, COO or OCO in such a way that O atoms are not linked directly to one another, [0274] X.sup.20 each, identically or differently, denote 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, each having up to 6 C atoms, and [0275] Y.sup.20-24 each, identically or differently, denote H or F; [0276] W denotes H or methyl,

##STR00095##

each, independently of one another, denote

##STR00096## [0277] The compounds of the formula II are preferably selected from the following formulae:

##STR00097## [0278] wherein R.sup.20 and X.sup.20 have the meanings indicated above. [0279] R.sup.20 preferably denotes alkyl having 1 to 6 C atoms. X.sup.20 preferably denotes F. Particular preference is given to compounds of the formulae IIa and IIb, in particular compounds of the formulae IIa and IIb wherein X denotes F. [0280] The compounds of the formula III are preferably selected from the following formulae:

##STR00098## [0281] wherein R.sup.20 and X.sup.20 have the meanings indicated above. [0282] R.sup.20 preferably denotes alkyl having 1 to 6 C atoms. X.sup.20 preferably denotes F. Particular preference is given to compounds of the formulae IIIa and IIIe, in particular compounds of the formula IIIa; [0283] bb) LC-medium additionally comprising one or more compounds selected from the following formulae:

##STR00099## [0284] wherein [0285] R.sup.20, X.sup.20, W and Y.sup.20-23 have the meanings indicated above under formula II, and [0286] Z.sup.20 denotes C.sub.2H.sub.4, (CH.sub.2).sub.4, CHCH, [0287] CFCF, C.sub.2F.sub.4, CH.sub.2CF.sub.2, CF.sub.2CH.sub.2, CH.sub.2O, OCH.sub.2, OOC or OCF.sub.2, in formulae V and VI also a single bond, in formulae V and VIII also CF.sub.2O, [0288] r denotes 0 or 1, and [0289] s denotes 0 or 1; [0290] The compounds of the formula IV are preferably selected from the following formulae:

##STR00100## [0291] wherein R.sup.20 and X.sup.20 have the meanings indicated above. [0292] R.sup.20 preferably denotes alkyl having 1 to 6 C atoms. X.sup.20 preferably denotes F or OCF.sub.3, furthermore OCFCF.sub.2 or Cl; [0293] The compounds of the formula V are preferably selected from the following formulae:

##STR00101## [0294] wherein R.sup.20 and X.sup.20 have the meanings indicated above. [0295] R.sup.20 preferably denotes alkyl having 1 to 6 C atoms. X.sup.20 preferably denotes F and OCF.sub.3, furthermore OCHF.sub.2, CF.sub.3, OCFCF.sub.2 and OCHCF.sub.2; [0296] The compounds of the formula VI are preferably selected from the following formulae:

##STR00102## [0297] wherein R.sup.20 and X.sup.20 have the meanings indicated above. [0298] R.sup.20 preferably denotes alkyl having 1 to 6 C atoms. X.sup.20 preferably denotes F, furthermore OCF.sub.3, CF.sub.3, CFCF.sub.2, OCHF.sub.2 and OCHCF.sub.2; [0299] The compounds of the formula VII are preferably selected from the following formulae:

##STR00103## [0300] wherein R.sup.20 and X.sup.20 have the meanings indicated above. [0301] R.sup.20 preferably denotes alkyl having 1 to 6 C atoms. X.sup.20 preferably denotes F, furthermore OCF.sub.3, OCHF.sub.2 and OCHCF.sub.2. [0302] cc) The medium additionally comprises one or more compounds selected from the formulae ZK1 to ZK10 given above. Especially preferred are compounds of formula ZK1 and ZK3. Particularly preferred compounds of formula ZK are selected from the sub-formulae ZK1a, ZK1 b, ZK1c, ZK3a, ZK3b, ZK3c and ZK3d. [0303] dd) The medium additionally comprises one or more compounds selected from the formulae DK1 to DK12 given above. Especially preferred compounds are DK3. [0304] ee) The medium additionally comprises one or more compounds selected from the following formulae:

##STR00104## [0305] wherein X.sup.20 has the meanings indicated above, and [0306] L denotes H or F, [0307] alkenyl denotes C.sub.2-6-alkenyl. [0308] ff) The compounds of the formulae DK-3a and IX are preferably selected from the following formulae:

##STR00105## [0309] wherein alkyl denotes C.sub.1-6-alkyl, preferably n-C.sub.3H.sub.7, n-C.sub.4H.sub.9 or n-C.sub.5H.sub.11, in particular n-C.sub.3H.sub.7. [0310] gg) The medium additionally comprises one or more compounds selected from the formulae B1, B2 and B3 given above, preferably from the formula B2. The compounds of the formulae B1 to B3 are particularly preferably selected from the formulae B1a, B2a, B2b and B2c. [0311] hh) The medium additionally comprises one or more compounds selected from the following formula:

##STR00106## [0312] wherein L.sup.20 denotes H or F, and R.sup.21 and R.sup.22 each, identically or differently, denote n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 C atoms, and preferably each, identically or differently, denote alkyl having 1 to 6 C atoms. [0313] ii) The medium comprises one or more compounds of the following formulae:

##STR00107## [0314] Wherein W, R.sup.20, X.sup.20 and Y.sup.20-23 have the meanings indicated in formula III, and

##STR00108##

each, independently of one another, denote

##STR00109## [0315] and

##STR00110##

denotes

##STR00111## [0316] The compounds of the formulae XI and XII are preferably selected from the following formulae:

##STR00112## ##STR00113## [0317] wherein R.sup.20 and X.sup.20 have the meaning indicated above and preferably R.sup.20 denotes alkyl having 1 to 6 C atoms and X.sup.20 denotes F. [0318] The mixture according to the invention particularly preferably comprises at least one compound of the formula XIIa and/or XIIe. [0319] jj) The medium comprises one or more compounds of formula T given above, preferably selected from the group of compounds of the formulae T21 to T23 and T25 to T27. [0320] Particular preference is given to the compounds of the formulae T21 to T23. Very particular preference is given to the compounds of the formulae

##STR00114## [0321] kk) The medium comprises one or more compounds selected from the group of formulae DK9, DK10 and DK11 given above. [0322] ll) The medium additionally comprises one or more compounds selected from the following formulae:

##STR00115## [0323] wherein R.sup.20 and X.sup.20 each, independently of one another, have one of the meanings indicated above, and Y.sup.20-23 each, independently of one another, denote H or F. X.sup.20 is preferably F, Cl, CF.sub.3, OCF.sub.3 or OCHF.sub.2. R.sup.20 preferably denotes alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 C atoms. [0324] The mixture according to the invention particularly preferably comprises one or more compounds of the formula XVIII-a,

##STR00116## [0325] wherein R.sup.20 has the meanings indicated above. R.sup.20 preferably denotes straight-chain alkyl, in particular ethyl, n-propyl, n-butyl and n-pentyl and very particularly preferably n-propyl. The compound(s) of the formula XVIII, in particular of the formula XVIII-a, is (are) preferably employed in the mixtures according to the invention in amounts of 0.5-20% by weight, particularly preferably 1-15% by weight. [0326] mm) The medium additionally comprises one or more compounds of the formula XIX,

##STR00117## [0327] wherein R.sup.20, X.sup.20 and Y.sup.20-25 have the meanings indicated in formula I, s denotes 0 or 1, and

##STR00118##

denotes

##STR00119## [0328] In the formula XIX, X.sup.20 may also denote an alkyl radical having 1-6 C atoms or an alkoxy radical having 1-6 C atoms. The alkyl or alkoxy radical is preferably straight-chain. [0329] R.sup.20 preferably denotes alkyl having 1 to 6 C atoms. X.sup.20 preferably denotes F; [0330] The compounds of the formula XIX are preferably selected from the following formulae:

##STR00120## [0331] wherein R.sup.20, X.sup.20 and Y.sup.20 have the meanings indicated above. R.sup.20 preferably denotes alkyl having 1 to 6 C atoms. X.sup.20 preferably denotes F, and Y.sup.20 is preferably F;

##STR00121##

is preferably

##STR00122## [0332] R.sup.20 is straight-chain alkyl or alkenyl having 2 to 6 C atoms; [0333] nn) The medium comprises one or more compounds of the formulae G1 to G4 given above, preferably selected from G1 and G2 wherein alkyl denotes C.sub.1-6-alkyl, L.sup.x denotes H and X denotes F or Cl. In G2, X particularly preferably denotes Cl. [0334] oo) The medium comprises one or more compounds of the following formulae:

##STR00123## [0335] wherein R.sup.20 and X.sup.20 have the meanings indicated above. R.sup.20 preferably denotes alkyl having 1 to 6 C atoms. X.sup.20 preferably denotes F. The medium according to the invention particularly preferably comprises one or more compounds of the formula XXII wherein X.sup.20 preferably denotes F. The compound(s) of the formulae XX-XXII is (are) preferably employed in the mixtures according to the invention in amounts of 1-20% by weight, particularly preferably 1-15% by weight. Particularly preferred mixtures comprise at least one compound of the formula XXII. [0336] pp) The medium comprises one or more compounds of the following pyrimidine or pyridine compounds of the formulae

##STR00124## [0337] wherein R.sup.20 and X.sup.20 have the meanings indicated above. R.sup.20 preferably denotes alkyl having 1 to 6 C atoms. X.sup.20 preferably denotes F. The medium according to the invention particularly preferably comprises one or more compounds of the formula M-1, wherein X.sup.20 preferably denotes F. The compound(s) of the formulae M-1-M-3 is (are) preferably employed in the mixtures according to the invention in amounts of 1-20% by weight, particularly preferably 1-15% by weight.

[0338] Further preferred embodiments are indicated below: [0339] qq) The medium comprises two or more compounds of the formula XII, in particular of the formula XIIe; [0340] rr) The medium comprises 2-30% by weight, preferably 3-20% by weight, particularly preferably 3-15% by weight, of compounds of the formula XII; [0341] ss) Besides the compounds of the formulae XII, the medium comprises further compounds selected from the group of the compounds of the formulae II, III, IX-XIII, XVII and XVIII; [0342] tt) The proportion of compounds of the formulae II, III, IX-XI, XIII, XVII and XVIII in the mixture as a whole is 40 to 95% by weight; [0343] uu) The medium comprises 10-50% by weight, particularly preferably 12-40% by weight, of compounds of the formulae II and/or III; [0344] vv) The medium comprises 20-70% by weight, particularly preferably 25-65% by weight, of compounds of the formulae IX-XIII; [0345] ww) The medium comprises 4-30% by weight, particularly preferably 5-20% by weight, of compounds of the formula XVII; [0346] xx) The medium comprises 1-20% by weight, particularly preferably 2-15% by weight, of compounds of the formula XVIII; [0347] yy) The medium comprises at least two compounds of the formulae

##STR00125## [0348] zz) The medium comprises at least two compounds of the formulae

##STR00126##

aaa) The medium comprises at least two compounds of the formula XIIa and at least two compounds of the formula XIIe. [0349] bbb) The medium comprises at least one compound of the formula XIIa and at least one compound of the formula XIIe and at least one compound of the formula IIIa. [0350] ccc) The medium comprises at least two compounds of the formula XIIa and at least two compounds of the formula XIIe and at least one compound of the formula IIIa. [0351] ddd) The medium comprises in total 25% by weight, preferably 30% by weight, of one or more compounds of the formula XII. [0352] eee) The medium comprises 20% by weight, preferably 24% by weight, preferably 25-60% by weight, of compounds of the formula ZK3, in particular the compound of the formula ZK3a,

##STR00127## [0353] fff) The medium comprises at least one compound selected from the group of compounds ZK3a, ZK3b and ZK3c, preferably ZK3a, in combination with compound ZK3d

##STR00128## [0354] ggg) The medium comprises at least one compound of the formula DPGU-n-F. [0355] hhh) The medium comprises at least one compound of the formula CDUQU-n-F. [0356] iii) The medium comprises at least one compound of the formula CPU-n-OXF. [0357] jjj) The medium comprises at least one compound of the formula CPGU-3-OT. [0358] kkk) The medium comprises at least one compound of the formula PPGU-n-F. [0359] lll) The medium comprises at least one compound of the formula PGP-n-m, preferably two or three compounds. [0360] mmm) The medium comprises at least one compound of the formula PGP-2-2V having the structure

##STR00129## [0361] In a preferred embodiment, the liquid crystal mixture according to the present invention further comprises a polymerizable component C) comprising one or more polymerizable compounds. [0362] The polymerizable compounds can be selected from isotropic or mesogenic polymerizable compounds known to the skilled person in the art. [0363] Preferably, the polymerizable component C) comprises one or more polymerizable compounds of formula P,

P.sup.a-(Sp.sup.a).sub.s1-A.sup.2-(Z.sup.a-A.sup.1).sub.n2-(Sp.sup.b).sub.s2PbP

wherein the individual radicals have the following meanings: [0364] P.sup.a, P.sup.b each, independently of one another, denote a polymerizable group, [0365] Sp.sup.a, Sp.sup.b on each occurrence, identically or differently, denote a spacer group, [0366] s1, s2 each, independently of one another, denote 0 or 1, [0367] A.sup.1, A.sup.2 each, independently of one another, denote a radical selected from the following groups: [0368] a) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene and 4,4-bicyclohexylene, wherein, in addition, one or more non-adjacent CH.sub.2 groups may be replaced by O and/or S and wherein, in addition, one or more H atoms may be replaced by F, [0369] b) the group consisting of 1,4-phenylene and 1,3-phenylene, wherein, in addition, one or two CH groups may be replaced by N and wherein, in addition, one or more H atoms may be replaced by L, [0370] c) the group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl and selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by L, [0371] d) the group consisting of saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radicals having 5 to 20 cyclic C atoms, one or more of which may, in addition, be replaced by heteroatoms, preferably selected from the group consisting of

##STR00130## [0372] where, in addition, one or more H atoms in these radicals may be replaced by L, and/or one or more double bonds may be replaced by single bonds, and/or one or more CH groups may be replaced by N, [0373] n2 denotes 0, 1, 2 or 3, [0374] Z.sup.a in each case, independently of one another, denotes COO, OCO, CH.sub.2O, OCH.sub.2, CF.sub.2O, OCF.sub.2, or (CH.sub.2).sub.n, where n is 2, 3 or 4, O, CO, C(R.sup.yR.sup.z), CH.sub.2CF.sub.2, CF.sub.2CF.sub.2 or a single bond, [0375] L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF.sub.5 or straight-chain or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or al koxycarbonyloxy having 1 to 12 C atoms, [0376] R.sup.y, R.sup.z each, independently of one another, denote H, F or straight-chain or branched alkyl having 1 to 12 C atoms, wherein, in addition, one or more H atoms may be replaced by F, [0377] M denotes O, S, CH.sub.2, CHY.sup.1 or CY.sup.1Y.sup.2, and [0378] Y.sup.1 and Y.sup.2 each, independently of one another, have one of the meanings indicated above for RY or denote Cl or CN.

[0379] Preferred spacer groups Sp.sup.a,b are selected from the formula Sp-X, so that the radicals P-Sp and P.sup.a/b-Sp.sup.a/b conforms to the formulae P-Sp-X and P.sup.a/b-Sp-X, respectively, wherein [0380] Sp denotes alkylene having 1 to 20, preferably 1 to 12, C atoms, which is optionally mono- or polysubstituted by F, Cl, Br, I or CN and wherein, in addition, one or more non-adjacent CH.sub.2 groups may each be replaced, independently of one another, by O, S, NH, N(R.sup.0), Si(R.sup.00R.sup.000), CO, COO, OCO, OCOO, SCO, COS, N(R.sup.00)COO, OCON(R.sup.00), N(R.sup.00)CON(R.sup.00), CHCH or CC in such a way that O and/or S atoms are not linked directly to one another, [0381] X denotes O, S, CO, COO, OCO, OCOO, CON(R.sup.00), N(R.sup.00)CO, N(R.sup.00)CON(R.sup.00), OCH.sub.2, CH.sub.2O, SCH.sub.2, CH.sub.2S, CF.sub.2O, OCF.sub.2, CF.sub.2S, SCF.sub.2, CF.sub.2CH.sub.2, CH.sub.2CF.sub.2, CF.sub.2CF.sub.2, CHN, NCH, NN, CHCR.sup.0, CY.sup.3CY.sup.4, CC, CHCHCOO, OCOCHCH or a single bond, [0382] R.sup.0, R.sup.00 [0383] and R.sup.000 each, independently of one another, denote H or alkyl having 1 to 12 C atoms, and [0384] Y.sup.3 and Y.sup.4 each, identically or differently, denote H, F, Cl or CN.

[0385] X is preferably O, S, CO, C(O)O, OC(O), OC(O)O, CONR.sup.0, NR.sup.0CO, NR.sup.0CONR.sup.0 or a single bond.

[0386] Typical spacer groups Sp are, for

[0387] example, (CH.sub.2).sub.p1, (CH.sub.2CH.sub.2O).sub.q1CH.sub.2CH.sub.2, CH.sub.2CH.sub.2SCH.sub.2CH.sub.2, CH.sub.2CH.sub.2NHCH.sub.2CH.sub.2 or (SiR.sup.00R.sup.000O).sub.p1, wherein p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R.sup.00 and R.sup.000 have the meanings indicated above. [0388] Particularly preferred groups -Sp-X are (CH.sub.2).sub.p1, (CH.sub.2).sub.p1O, (CH.sub.2).sub.p1OCO, (CH.sub.2).sub.p1OCOO, wherein p1 and q1 have the meanings indicated above. [0389] Particularly preferred groups Sp are, for example, in each case straight-chain ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, ethenylene, propenylene and butenylene. [0390] Particularly preferred monomers of formula P are the following:

##STR00131## ##STR00132## ##STR00133## ##STR00134##

wherein the individual radicals have the following meanings: [0391] P.sup.1 to P.sup.3 each, independently of one another, denote a polymerizable group as defined for formula P, preferably an acrylate, methacrylate, fluoroacrylate, oxetane, vinyloxy or epoxide group, [0392] Sp.sup.1 to Spa each, independently of one another, denote a single bond or a spacer group, preferably having one of the meanings indicated above and below for Spa, and particularly preferably (CH.sub.2).sub.p1, (CH.sub.2).sub.p1O, (CH.sub.2).sub.p1COO or (CH.sub.2).sub.p1OCOO, wherein p1 is an integer from 1 to 12, and where the linking to the adjacent ring in the last-mentioned groups takes place via the O atom, [0393] where, in addition, one or more of the radicals P.sup.1-Sp.sup.1, P.sup.2-Sp.sup.2 and P.sup.3-Sp.sup.3 may denote a radical R.sup.aa, with the proviso that at least one of the radicals P.sup.1-Sp.sup.1, P.sup.2-Sp.sup.2 and P.sup.3-Sp.sup.3 present does not denote R.sup.aa, [0394] R.sup.aa denotes H, F, Cl, CN or straight-chain or branched alkyl having 1 to 25 C atoms, wherein, in addition, one or more non-adjacent CH.sub.2 groups may each be replaced, independently of one another, by [0395] C(R.sup.0)C(R.sup.00), CC, N(R.sup.0), O, S, CO, COO, OCO, OCOO in such a way that O and/or S atoms are not linked directly to one another, and wherein, in addition, one or more H atoms may be replaced by F, Cl, CN or P.sup.1-Sp.sup.1, particularly preferably straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl or alkylcarbonyloxy having 1 to 12 C atoms (where the alkenyl and alkynyl radicals have at least two C atoms and the branched radicals have at least three C atoms), [0396] R.sup.0, R.sup.00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms, [0397] R.sup.y and R.sup.z each, independently of one another, denote H, F, CH.sub.3 or CF.sub.3, [0398] Z.sup.p1 denotes O, CO, C(R.sup.yR.sup.z) or CF.sub.2CF.sub.2, [0399] Z.sup.p2 and Z.sup.p3 each, independently of one another, denote COO, OCO, CH.sub.2O, OCH.sub.2, CF.sub.2O, OCF.sub.2 or (CH.sub.2).sub.n3, where n3 is 2, 3 or 4, [0400] L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF.sub.5 or straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, preferably F, [0401] L and L each, independently of one another, denote H, F or Cl, [0402] r denotes 0, 1, 2, 3 or 4, [0403] s denotes 0, 1, 2 or 3, [0404] t denotes 0, 1 or 2, and [0405] x denotes 0 or 1.

[0406] In a particularly preferred embodiment of the present invention the LC mixture, or component C), comprises one or more compounds of formula P10-1.

##STR00135##

wherein the parameters are defined as described above and P.sup.1 and P.sup.2 preferably denote acrylate or methacrylate. [0407] Particularly preferred compounds of formula P10-1 are selected from the group of the following subformulae

##STR00136##

wherein each n4 denote independently of each other an integer between 2 and 10, preferably 3,4,5 or 6.

[0408] The polymerizable compounds of formulae I and P are also suitable for polymerisation without an initiator, which is associated with considerable advantages, such as, for example, lower material costs and, in particular, reduced contamination of the LC medium by possible residual amounts of the initiator or degradation products thereof. The polymerisation can thus also be carried out without addition of an initiator. The LC medium thus, in a preferred embodiment, comprises no polymerisation initiator.

[0409] The polymerizable component C) or the LC medium as a whole may also comprise one or more stabilisers in order to prevent undesired spontaneous polymerisation of the RMs, for example during storage or transport. Suitable types and amounts of stabilisers are known to the person skilled in the art and are described in the literature. Particularly suitable are, for example, the commercially available stabilisers from the Irganox series (BASF SE), such as, for example, Irganox 1076. If stabilisers are employed, their proportion, based on the total amount of the RMs or the polymerizable component, is preferably 10-10,000 ppm, particularly preferably 50-1000 ppm.

[0410] The media according to the invention preferably comprise from 0.01 to 10%, particularly preferably from 0.05 to 7.5% and most preferably from 0.1 to 5% of the compounds of component C) comprising compounds of formula P according to the invention. The media preferably comprise one, two or three, more preferably one or two and most preferably one compound of the formula P according to the invention.

[0411] By means of suitable additives, the liquid-crystalline phases of the present invention can be modified in such a way that they can be used in all types of liquid-crystal display element that have been disclosed hitherto. Additives of this type are known to the person skilled in the art and are described in detail in the literature (H. Kelker/R. Hatz, Handbook of Liquid Crystals, Verlag Chemie, Weinheim, 1980). For example, pleochroic dyes can be added for the production of coloured guest-host systems or substances can be added in order to modify the dielectric anisotropy, the viscosity and/or the alignment of the nematic phases.

[0412] The media according to the invention are prepared in a manner conventional per se. In general, the components are dissolved in one another, preferably at elevated temperature.

[0413] Accordingly the present invention relates further to method for the production of an LC medium according to the present invention, comprising the step of mixing one or more compounds of formula I with a liquid-crystalline component B) comprising one or more mesogenic or liquid-crystalline compounds as described above.

[0414] The present invention further relates to a process for the fabrication of liquid crystal displays comprising at least the steps of: [0415] providing a first substrate which includes a pixel electrode and a common electrode for generating an electric field substantially parallel to a surface of the first substrate in the pixel region; [0416] providing a second substrate, the second substrate being disposed opposite to the first substrate; [0417] interposing a liquid crystal mixture between the first substrate and the second substrate, the liquid crystal mixture comprising one or more compounds of formula I, component B) and optionally component C); [0418] irradiating the liquid crystal mixture with linearly polarised light causing photoalignment of the liquid crystal; [0419] curing the polymerizable compounds of the liquid crystal mixture by irradiation with ultraviolet light or visible light having a wavelength of 450 nm or below.

[0420] The present invention further relates to the use of the liquid crystal mixtures according to the invention for the fabrication of a liquid crystal display.

[0421] The present invention further relates to liquid crystal displays fabricated by the process described above.

[0422] In the following, the production process according to the present invention is described in greater detail.

[0423] The first substrate includes a pixel electrode and a common electrode for generating an electric field substantially parallel to a surface of the first substrate in the pixel region. Various kinds of displays having at least two electrodes on one substrate are known to the skilled person wherein the most significant difference is that either both the pixel electrode and the common electrode are structured, as it is typical for IPS displays, or only the pixel electrode is structured and the common electrode is unstructured, which is the case for FFS displays.

[0424] It has to be understood that the present invention refers to any kind of electrode configurations suitable for generating an electric field substantially parallel to a surface of the first substrate in the pixel region; mentioned above, i.e. IPS as well as FFS displays.

[0425] The process according to the present invention is independent of the kind of substrate or material of the surface which is in contact with the liquid crystal mixture according to the invention, during and after this process. Examples of materials used for the substrates or surfaces are organic polymers including polyimide, indium tin oxide (ITO), indium zinc oxide (IZO), silicon nitride (SiN.sub.x) and silicon dioxide (SiO.sub.2). The process is especially suitable for the use in displays containing substrates that do not have a polyimide layer on one or more of the surfaces that are in contact with the liquid crystal.

[0426] In case one or more substrates contain a polyimide layer, the polyimide can be rubbed or not rubbed, preferably not rubbed.

[0427] Hence, the invention relates to a display produced by the process according to the invention in which the substrates contain a rubbed or unrubbed polyimide layer, preferably an unrubbed polyimide layer.

[0428] The invention further relates to a display produced by the process according to the invention in which none or only one of the top and bottom substrates contains a polyimide layer.

[0429] In one embodiment of the present invention the liquid crystal composition is injected between the first and second substrates or is filled into the cell by capillary force after combining the first and second substrates. In an alternative embodiment, the liquid crystal composition may be interposed between the first and second substrates by combining the second substrate to the first substrate after loading the liquid crystal composition on the first substrate. Preferably, the liquid crystal is dispensed dropwise onto a first substrate in a process known as one drop filling (ODF) process, as disclosed in for example JPS63-179323 and JPH10-239694, or using the Ink Jet Printing (IJP) method.

[0430] In a preferred embodiment, the process according to the invention contains a process step where the liquid crystal inside the display panel is allowed to rest for a period of time in order to evenly redistribute the liquid crystal medium inside the panel (herein referred to as annealing).

[0431] However it is likewise preferred that the annealing step is combined with a previous step, such as edge sealant pre-curing. In which case a separate annealing step may not be necessary at all.

[0432] For the production of the displays according to the present invention, the photoreactive mesogen of formula I is preferably allowed to redistribute in the panel. After filling and assembly, the display panel is annealed for a time between 1 min and 3 h, preferably between 2 min and 1 h and most preferably between 5 min and 30 min. The annealing is preferably performed at room temperature.

[0433] In an alternative embodiment, the annealing is performed at elevated temperature, preferably at above 20 C. and below 140 C., more preferably above 40 C. and below 100 C. and most preferably above 50 C. and below 80 C.

[0434] In a preferred embodiment, one or more of the process steps of filling the display, annealing, photoalignment and curing of the polymerizable compound is performed at a temperature above the clearing point of the liquid crystal host mixture.

[0435] During the photoalignment of the liquid crystal inside the liquid crystal panel, anisotropy is induced by exposing the display or the liquid crystal layer to linearly polarised light.

[0436] In a preferred embodiment of the present invention the photoreactive component A) comprising one or more compounds of formula I, is photoaligned in a first step using linearly polarised light and in a second step further cured using linearly polarized or unpolarised UV light. In the second step the optional component C) is also further cured.

[0437] In another preferred embodiment, the linearly polarised light applied according to the inventive process is ultraviolet light which enables simultaneous photoalignment and photocuring of the photoreactive component A) comprising one or more compounds of formula I, and, if present, photocuring of the polymerizable component C).

[0438] Photoalignment of the photoreactive compounds of formula I and curing of the polymerizable groups of compounds of formula I and the curing of the optional polymerizable compounds of formula P can be performed simultaneously or stepwise. In case the process is split into different steps, the individual steps can be performed at the same temperature or at different temperatures.

[0439] After the photoalignment and curing step(s) a so-called post-curing step can optionally be performed by irradiation with UV-light and/or visible light (both either linearly or unpolarised) at reduced temperature in order to remove unreacted polymerizable compounds. The post-curing is preferably performed at above 0 C. and below the clearing point of the utilized LC mixture, preferably 20 C. and below 60 C. C., and most preferably above 20 C. and below 40 C.

[0440] The polymerizable compounds are optionally polymerised or crosslinked (if a polymerizable compound contains two or more polymerizable groups) with the application of an electrical field. The polymerisation can be carried out in one or more steps.

[0441] Suitable and preferred polymerisation methods for component C) are, for example, thermal or photopolymerization, preferably photopolymerization, in particular UV photopolymerization. One or more initiators can optionally also be added here. Suitable conditions for the polymerisation and suitable types and amounts of initiators are known to the person skilled in the art and are described in the literature. Suitable for free-radical polymerisation are, for example, the commercially available photoinitiators Irgacure651, Irgacure184, Irgacure907, Irgacure369 or Darocure1173 (BASF SE). If an initiator is employed, its proportion is preferably 0.001 to 5% by weight, particularly preferably 0.001 to 1% by weight.

[0442] The present invention also relates to electro-optical liquid-crystal display elements containing a liquid-crystalline medium according to the invention, which is preferably homogeneously aligned. In a preferred embodiment the liquid crystal display is of the IPS or FFS mode.

[0443] Further combinations of the embodiments and variants of the invention in accordance with the description arise from the claims.

[0444] The invention is explained in greater detail below with reference to working examples, but without intending to be restricted thereby. The person skilled in the art will be able to glean from the examples working details that are not given in detail in the general description, generalise them in accordance with general expert knowledge and apply them to a specific problem.

[0445] Besides the usual and well-known abbreviations, the following abbreviations are used:

[0446] C: crystalline phase; N: nematic phase; Sm: smectic phase; I: isotropic phase. The numbers between these symbols show the transition temperatures of the substance concerned.

[0447] Temperature data are in C., unless indicated otherwise.

[0448] Physical, physicochemical or electro-optical parameters are determined by generally known methods, as described, inter alia, in the brochure Merck Liquid CrystalsLicristalPhysical Properties of Liquid CrystalsDescription of the Measurement Methods, 1998, Merck KGaA, Darmstadt.

[0449] Above and below, n denotes the optical anisotropy (589 nm, 20 C.) and denotes the dielectric anisotropy (1 kHz, 20 C.). The dielectric anisotropy is determined at 20 C. and 1 kHz. The optical anisotropy n is determined at 20 C. and a wavelength of 589.3 nm.

[0450] The and n values and the rotational viscosity (.sub.1) of the compounds according to the invention are obtained by linear extrapolation from liquid-crystalline mixtures consisting of 5 to 10% of the respective compound according to the invention and 90-95% of the commercially available liquid-crystal mixture ZLI-2857 (for ) or ZLI-4792 (for n, .sub.1) (mixtures, Merck KGaA, Darmstadt).

[0451] The compounds used in the present invention are prepared by methods known per se, as described in the literature (for example in the standard works, such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart), to be precise under reaction conditions which are known and suitable for the said reactions. Use can also be made here of variants known per se, which are not mentioned here in greater detail.

[0452] In the present invention and especially in the following examples, the structures of the mesogenic compounds are indicated by means of abbreviations, also called acronyms. In these acronyms, the chemical formulae are abbreviated as follows using Tables A to C below. All groups C.sub.nH.sub.2n+1, C.sub.mH.sub.2m+1 and C.sub.1H.sub.2l+1 or C.sub.nH.sub.2n1, C.sub.mH.sub.2m1 and C.sub.1H.sub.2l1 denote straight-chain alkyl or alkenyl, preferably 1E-alkenyl, each having n, m and l C atoms respectively. Table A lists the codes used for the ring elements of the core structures of the compounds, while Table B shows the linking groups. Table C gives the meanings of the codes for the left-hand or right-hand end groups. The acronyms are composed of the codes for the ring elements with optional linking groups, followed by a first hyphen and the codes for the left-hand end group, and a second hyphen and the codes for the right-hand end group. Table D shows illustrative structures of compounds together with their respective abbreviations.

TABLE-US-00001 TABLE A Ring elements [00137] embedded image C [00138] P [00139] D [00140] DI [00141] A [00142] AI [00143] G [00144] GI [00145] U [00146] UI [00147] Y [00148] M [00149] MI [00150] N [00151] NI [00152] Np [00153] dH [00154] N3f [00155] N3fl [00156] tH [00157] tHI [00158] tH2f [00159] tH2fl [00160] K [00161] KI [00162] L [00163] LI [00164] embedded image F [00165] FI [00166] Nf [00167] Nfl

TABLE-US-00002 TABLE B Linking groups E CH.sub.2CH.sub.2 Z COO V CHCH ZI OCO X CFCH O CH.sub.2O XI CHCF OI OCH.sub.2 B CFCF Q CF.sub.2O T CC QI OCF.sub.2 W CF.sub.2CF.sub.2 T CO

TABLE-US-00003 TABLE C End groups Left-hand side Right-hand side Use alone -n- C.sub.nH.sub.2n+1 -n C.sub.nH.sub.2n+1 nO C.sub.nH.sub.2n+1O nO OC.sub.nH.sub.2n+1 V CH.sub.2CH V CHCH.sub.2 nV C.sub.nH.sub.2n+1CHCH nV C.sub.nH.sub.2nCHCH.sub.2 Vn CH.sub.2CHC.sub.nH.sub.2n+1 Vn CHCHC.sub.nH.sub.2n+1 nVm C.sub.nH.sub.2n+1CHCHC.sub.mH.sub.2m nVm C.sub.nH.sub.2nCHCHC.sub.mH.sub.2m+1 N NC N CN S SCN S NCS F F F F CL Cl CL Cl M CFH.sub.2 M CFH.sub.2 D CF.sub.2H D CF.sub.2H T CF.sub.3 T CF.sub.3 MO CFH.sub.2O OM OCFH.sub.2 DO CF.sub.2HO OD OCF.sub.2H TO CF.sub.3O OT OCF.sub.3 FXO CF.sub.2CHO OXF OCHCF.sub.2 A HCC A CCH nA C.sub.nH.sub.2n+1CC An CCC.sub.nH.sub.2n+1 NA NCCC AN CCCN Use together with one another and with others . . . A . . . C . . . A . . . C . . . V . . . CHCH . . . V . . . CHCH . . . Z . . . COO . . . Z . . . COO . . . ZI . . . OCO . . . ZI . . . OCO . . . K . . . CO . . . K . . . CO . . . W . . . CFCF . . . W . . . CFCF
wherein n and m each denote integers, and the three dots . . . are placeholders for other abbreviations from this table.

[0453] The following table shows illustrative structures together with their respective abbreviations. These are shown in order to illustrate the meaning of the rules for the abbreviations. They furthermore represent compounds which are preferably used.

TABLE-US-00004 TABLE D Illustrative structures [00168] embedded image CC-n-m [00169] CC-n-Om [00170] CC-n-V [00171] CC-n-Vm [00172] CC-n-mV [00173] CC-n-mVI [00174] CC-V-V [00175] CC-V-mV [00176] CC-V-Vm [00177] CC-Vn-mV [00178] CC-nV-mV [00179] CC-nV-Vm [00180] CP-n-m [00181] CP-nO-m [00182] CP-n-Om [00183] CP-V-m [00184] CP-Vn-m [00185] CP-nV-m [00186] embedded image CP-V-V [00187] CP-V-mV [00188] CP-V-Vm [00189] CP-Vn-mV [00190] CP-nV-mV [00191] CP-nV-Vm [00192] PP-n-m [00193] PP-nO-m [00194] PP-n-Om [00195] PP-n-V [00196] PP-n-Vm [00197] PP-n-mV [00198] PP-n-mVI [00199] CCP-n-m [00200] CCP-nO-m [00201] CCP-n-Om [00202] CCP-n-V [00203] CCP-n-Vm [00204] embedded image CCP-n-mV [00205] CCP-n-mVI [00206] CCP-V-m [00207] CCP-nV-m [00208] CCP-Vn-m [00209] CCP-nVm-I [00210] CPP-n-m [00211] CPG-n-m [00212] CGP-n-m [00213] CPP-nO-m [00214] CPP-n-Om [00215] CPP-V-m [00216] CPP-nV-m [00217] CPP-Vn-m [00218] CPP-nVm-I [00219] PGP-n-m [00220] PGP-n-V [00221] PGP-n-Vm [00222] embedded image PGP-n-mV [00223] PGP-n-mVI [00224] CCEC-n-m [00225] CCEC-n-Om [00226] CCEP-n-m [00227] CCEP-n-Om [00228] CPPC-n-m [00229] CGPC-n-m [00230] CCPC-n-m [00231] CCZPC-n-m [00232] CPGP-n-m [00233] CPGP-n-mV [00234] CPGP-n-mVI [00235] PGIGP-n-m [00236] CP-n-F [00237] CP-n-CL [00238] GP-n-F [00239] embedded image GP-n-CL [00240] CCP-n-OT [00241] CCG-n-OT [00242] CCP-n-T [00243] CCG-n-F [00244] CCG-V-F [00245] CCG-V-F [00246] CCU-n-F [00247] CDU-n-F [00248] CPG-n-F [00249] CPU-n-F [00250] CGU-n-F [00251] PGU-n-F [00252] GGP-n-F [00253] GGP-n-CL [00254] PGIGI-n-F [00255] PGIGI-n-CL [00256] CCPU-n-F [00257] embedded image CCGU-n-F [00258] CPGU-n-F [00259] CPGU-n-OT [00260] DPGU-n-F [00261] PPGU-n-F [00262] CCZU-n-F [00263] CCQP-n-F [00264] CCQG-n-F [00265] CCQU-n-F [00266] PPQG-n-F [00267] PPQU-n-F [00268] PGQU-n-F [00269] GGQU-n-F [00270] PUQU-n-F [00271] MUQU-n-F [00272] NUQU-n-F [00273] CDUQU-n-F [00274] embedded image CPUQU-n-F [00275] CGUQU-n-F [00276] PGPQP-n-F [00277] PGPQG-n-F [00278] PGPQU-n-F [00279] PGUQU-n-F [00280] APUQU-n-F [00281] DGUQU-n-F [00282] CY-n-Om [00283] CY-n-m [00284] CY-V-Om [00285] CY-nV-(O)m [00286] CVC-n-m [00287] CVY-V-m [00288] CEY-V-m [00289] PY-n-(O)m [00290] CCY-n-m [00291] embedded image CCY-n-Om [00292] CCY-V-m [00293] CCY-Vn-m [00294] CCY-V-Om [00295] CCY-n-OmV [00296] CCY-n-zOm [00297] CCOC-n-m [00298] CPY-n-(O)m [00299] CPY-V-Om [00300] CQY-n-(O)m [00301] CQIY-n-(O)m [00302] CCQY-n-(O)m [00303] CCQIY-n-(O)m [00304] CPQY-n-(O)m [00305] CPQIY-n-Om [00306] CLY-n-(O)m [00307] embedded image CYLI-n-m [00308] LYLI-n-m [00309] LY-n-(O)m [00310] PGIGI-n-F [00311] PGP-n-m [00312] PYP-n-(O)m [00313] PYP-n-mV [00314] YPY-n-m [00315] YPY-n-mV [00316] BCH-nm [00317] BCH-nmF [00318] CPYP-n-(O)m [00319] CPGP-n-m [00320] CPYC-n-m [00321] CYYC-n-m [00322] CCYY-n-m [00323] CPYG-n-(O)m [00324] embedded image CBC-nm [00325] CBC-nmF [00326] CNap-n-Om [00327] CCNap-n-Om [00328] CENap-n-Om [00329] CTNap-n-Om [00330] CETNap-n-Om [00331] CK-n-F [00332] DFDBC-n(O)-(O)m [00333] C-DFDBF-n-(O)m
wherein n, m and l preferably, independently of one another, denote 1 to 7.

[0454] The following table, Table E, shows illustrative compounds which can be used as additional stabilisers in the mesogenic media according to the present invention.

TABLE-US-00005 TABLE E Table E shows possible stabilisers which can be added to the LC media according to the invention. (n here denotes an integer from 1 to 12, preferably 1, 2, 3, 4, 5, 6, 7 or 8, terminal methyl groups are not shown). [00334] embedded image [00335] [00336] [00337] [00338] [00339] [00340] [00341] [00342] [00343] [00344] [00345] [00346] [00347] [00348] [00349] [00350] [00351] [00352] [00353] [00354] [00355] [00356] [00357] [00358] [00359] [00360] [00361] [00362] [00363] [00364] [00365] [00366] [00367] [00368] [00369] [00370] embedded image [00371] [00372] [00373] [00374] [00375] [00376] [00377] [00378]

[0455] The LC media preferably comprise 0 to 10% by weight, in particular 1 ppm to 5% by weight, particularly preferably 1 ppm to 1% by weight, of stabilisers.

[0456] Table F below shows illustrative compounds which can preferably be used as chiral dopants in the mesogenic media according to the present invention.

TABLE-US-00006 TABLE F [00379] embedded image [00380] [00381] [00382] [00383] [00384] [00385] [00386] [00387] [00388] [00389] [00390] [00391] [00392]

[0457] In a preferred embodiment of the present invention, the mesogenic media comprise one or more compounds selected from the group of the compounds from Table F.

[0458] The mesogenic media according to the present application preferably comprise two or more, preferably four or more, compounds selected from the group consisting of the compounds from the above tables.

[0459] The liquid-crystal media according to the present invention preferably comprise [0460] seven or more, preferably eight or more, individual compounds, preferably of three or more, particularly preferably of four or more, different formulae, selected from the group of the compounds from Table D.

[0461] Hereinafter, the present invention is described in more detail and specifically with reference to the Examples, which however are not intended to limit the present invention.

EXAMPLES

Compound Examples

1.1 Synthesis of diethyl 3-(2-benzyloxyethyl)pentanedioate (1)

[0462] ##STR00393##

[0463] Under reflux 13.8 ml (90 mmol) of the diethyl malonate are added to mixture of 34.5 ml of a solution of sodium methylate in ethanol (20%, 50 mmol) and 40 ml ethanol. After 2h 10 g (50 mmol) of 2-bromoethoxymethylbenzene are added and heating was continued overnight. Water and MTB ether are poured into the cooled reaction mixture. The aqueous layer is extracted with MTB ether. The combined organic layers are washed with brine and dried over sodium sulfate. The solvent is evaporated. The residue is purified by silica chromatography (toluene; toluene/MTB ether 9:1). The isolated material is distilled under vacuum (0.1 mbar, 116-121 C.).

1.2 Synthesis of 2-(2-benzyloxyethyl)propane-1,3-diol (2)

[0464] ##STR00394##

[0465] A solution of 5 g (20 mmol) of the malonate 1 in 60 ml toluene is added to a suspension of 930 mg (24 mmol) Lithium aluminum hydride in 8 ml Toluene. After 3h reflux the cooled reaction mixture is quenched with ethyl acetate. The mixture is acidified with 2 mol/l hydrochloric acid (pH 3-4). The aqueous layer is extracted with MTB ether. The combined organic layers are washed with water and dried over sodium sulfate. The solvent is evaporated. The residue is purified by silica chromatography (ethyl acetate.

1.3 Synthesis of [4-benzyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]butoxy]-tert-butyl-dimethyl-silane (3)

[0466] ##STR00395##

[0467] At room temperature 3.4 ml (25 mmol) triethyl amine are added to a mixture of 2.1 g (10 mmol) of the diol 2 and 120 mg DMAP dissolved in 30 ml dichloro methane. Afterwards a solution of 4.5 g (30 mmol) TBDMS-Cl in 15 ml dichloro methane are added to the reaction mixture at 3-4 C. After stirring 16h at room temperature the mixture is quenched with water. The combined organic layers are washed with brine and dried over sodium sulfate. The solvent is evaporated. The residue is purified by silica chromatography (n-heptane/ethyl acetate 19:1).

1.4 Synthesis of 4-[tert-butyl(dimethyl)silyl]oxy-3-[[tert-butyl(dimethyl)silyl]oxy-methyl]-butan-1-ol (4)

[0468] ##STR00396##

[0469] A solution of 500 mg (1 mmol) of 3 in 13 ml ethyl acetate is hydrogenated using Pd/C-5% at room temperature. The solvent is evaporated. The residue is purified by silica chromatography (n-heptane/ethyl acetate (gradient)).

1.5 Synthesis of [4-[(6-bromo-2-naphthyl)oxy]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]butoxy]-tert-butyl-dimethyl-silane (5)

[0470] ##STR00397##

[0471] A solution of 10 g (43 mmol) 2-hydroxy-6-bromo naphthalene, 17.1 g (49 mmol) 5 and 13.1 g triphenylphosphine in 80 ml THF is treated with 10.2 ml (52 mmol) diisopropyl carboxylate at room temperature. The mixture is stirred overnight. The solvent is evaporated. The residue is purified by silica chromatography (toluene).

1.6 Synthesis of butyl (E)-3-[6-[4-[tert-butyl(dimethyl)silyl]oxy-3-[[tert-butyl(dimethyl)silyl]oxymethyl]butoxy]-2-naphthyl]prop-2-enoate (6)

[0472] ##STR00398##

[0473] A solution of 24.8 g (84% pure, 38 mmol) 5, 6.4 ml (45 mmol) butyl acrylate and 10.5 ml triethyl amine in 150 ml acetonitrile is treated with 250 mg Palladium(II)acetate and 570 mg tri-(o-tolyl) phosphine and refluxed overnight. The solvent is evaporated. The residue is filtrated through silica gel (n-heptane/toluene 1:1; toluene).

1.7 Synthesis of (E)-3-[6-[4-[tert-butyl(dimethyl)silyl]oxy-3-[[tert-butyl(dimethyl)silyl]oxymethyl]butoxy]-2-naphthyl]prop-2-enoic acid (7)

[0474] ##STR00399##

[0475] A solution of 20.5 g (33 mmol) 6 in 100 ml THF and 16 ml methanol is treated with 34 ml 2N sodium hydroxide and stirred at 30 C. overnight. The mixture is added to 1.5 l aqueous saturated ammonia hydrochloride solution and acidified with 1N hydrochloric acid (pH 5). The aqueous layer is extracted with MTB ether. The organic layer is dried with sodium sulfate. The solvent is evaporated. The residue is dried under low pressure.

1.8 Synthesis of 1-[4-(benzyloxy)-3-methylphenyl]ethan-1-one 8

[0476] ##STR00400##

[0477] 12.7 g (85.0 mmol) of 1-(4-hydroxy-3-methyl-phenyl)-ethanone, 12.7 mL (107 mmol) benzyl bromide and 7.62 g (55.0 mmol) potassium carbonate are dissolved/suspended in methyl(ethyl)ketone and stirred for 18 h under reflux. The reaction mixture is cooled down to room temperature (RT) and the precipitating solid is filtered and washed with methyl tertiary-butyl ether (MTB-E). The product is further crystallized out of heptane at 5 C. and is directly used in the next synthesis step.

1.9 Synthesis of 4-(benzyloxy)-3-methylphenyl acetate 9

[0478] ##STR00401##

[0479] 39.1 mL (0.165 mmol) m-chloroperbenzoic acid are suspended in in 102 mL methylene chloride and a solution of 19.3 g (80.0 mmol) of ketone 8 in 72 mL methylene chloride is added dropwise to the reaction mixture. The yellow reaction mixture is then stepwise heated up to reflux and stirred for 16 h. The reaction mixture is cooled to room temperature (RT) and poured onto ice water. The phases are separated and the organic layer is filtered off from precipitated 3-chlorobenzoic acid, washed with sodium hydrogen carbonate, tested for peroxide remnants (with ammonia iron(II) sulfate solution), dried over sodium sulfate, filtered and evaporated under vacuum. The crude product is filtered through 900 g silica gel with toluene and ethyl acetate (95:5) to give the product as a yellow oil.

1.10 Synthesis of 4-(benzyloxy)-3-methylphenol 10

[0480] ##STR00402##

[0481] 23.4 g (91.0 mmol) acetate 9 are solved in 181.0 mL ethanol and 5.84 mL (197.0 mmol) sodium hydroxide solution (32%) are added dropwise to the solution (the reaction solution turned to red color). The reaction mixture is stirred for 2h at ambient temperature and then poured onto ice water and treated with HCl solution till a pH value of 1 is achieved. The reaction mixture is extracted with methyl tertiary-butyl ether (MTB-E), the organic layer dried over sodium sulfate, filtered and evaporated under vacuum. The black oil is filtered over silica gel with methylene chloride and the obtained solid is then crystallized out of heptane at 25 C. to give slightly brown colored crystals.

[0482] .sup.1H NMR (500 MHz, DMSO-d6)

[0483] =2.13 ppm (s, 3H, CH.sub.3), 4.99 (s, 2H, CH.sub.2O), 6.51 (dd, J=2.86, 8.62 Hz, 1H), 6.58 (d, J=2.49 Hz, 1H), 6.81 (d, J=8.70 Hz, 1H), 7.32 (d, J=7.23 Hz, 1H), 7.39 (t, J=7.71 Hz, 2H), 7.44 (d, J=8.70 Hz, 2H).

1.11 Synthesis of benzyl 4-triisopropylsilyloxybenzoate (11)

[0484] ##STR00403##

[0485] A mixture of 400 ml DMF, 75 g (328 mmol) benzyl-4-hydroxybenzoate and 45 g (661 mmol) imidazole was treated with a solution of 77.5 ml (361 mmol) chloro triisopropyl silane in 200 ml DMF at room temperature. After 5h stirring the reaction mixture is diluted with toluene and n-heptane and poured ice cold water. The aqueous layer is extracted with toluene, the combined organic layers are dried with sodium sulfate and filtrated through silica gel (n-heptane/toluene 1:1). The solvent of the product containing fractions is evaporated. Yield: 116 g 11

1.12 Synthesis of 4-triisopropylsilyloxybenzoic acid (12)

[0486] ##STR00404##

[0487] A solution of 116 g (296 mmol) 11 in ethanol is hydrogenated with Pd-C5% (51.4% water) at room temperature. The reaction mixture is diluted with MTB ether. Silica gel and Celite are added. The obtained mixture is filtrated through silica gel/Celite (MTB ether). The solvent of the product containing fraction is evaporated. The residue is crystallized from n-heptane (6 C.).

1.13 Synthesis of (4-benzyloxy-3-methyl-phenyl) 4-triisopropylsilyloxybenzoate (13)

[0488] ##STR00405##

[0489] A solution of 21.1 g (98 mmol) 10 and 29 g (98 mmol) 12 in 900 ml dichloro methane is treated with 600 mg DMAP and 22.6 g (118 mmol) N-(3-dimethylamino propyl)-N-ethyl carbodiimide hydrochloride and stirred overnight at room temperature. The mixture was filtered through silica gel (dichloromethane). The solvent of the product containing fraction is evaporated.

1.14 Synthesis of (4-hydroxy-3-methyl-phenyl) 4-triisopropylsilyloxybenzoate (14)

[0490] ##STR00406##

[0491] A solution of 35 g (71 mmol) 13 in 350 ml THF is hydrogenated with Pd-C5% (51.4% water) at room temperature. The solvent is evaporated.

1.15 Synthesis of [4-[(E)-3-[6-[4-[tert-butyl(dimethyl)silyl]oxy-3-[[tert-butyl(dimethyl)silyl]oxymethyl]butoxy]-2-naphthyl]prop-2-enoyl]oxy-3-methyl-phenyl] 4-triisopropylsilyloxybenzoate (15)

[0492] ##STR00407##

[0493] A solution of 3.9 g (6.9 mmol) 7 and 2.7 g (6.7 mmol) 14 in 40 ml dichloro methane is treated with 40 mg DMAP and 1.5 g (7.8 mmol) N-(3-dimethylamino propyl)-N-ethyl carbodiimide hydrochloride and stirred overnight at room temperature. The mixture was filtered through silica gel (dichloro methane). The solvent of the product containing fraction is evaporated. Yield 5.4 g 15

1.18 Synthesis of [4-[(E)-3-[6-[4-hydroxy-3-(hydroxymethyl)butoxy]-2-naphthyl]prop-2-enoyl]oxy-3-methyl-phenyl] 4-hydroxybenzoate (16)

[0494] ##STR00408##

[0495] A solution of 4.9 g (5.3 mmol) 15 in 60 ml THF is treated with 6.5 ml (40 mmol) triethylamine trishydrofluoride at a temperature below 5 C. The reaction mixture is stirred overnight at room temperature, and filtered through silica gel collecting fractions (THF). The product containing fraction are combined and the solvent is evaporated. The residue is suspended in 12 ml acetonitrile and heated to reflux. The mixture is cooled to 6 C. The precipitate is isolated.

1.17 Synthesis of [3-methyl-4-[(E)-3-[6-[4-(2-methylprop-2-enoyloxy)-3-(2-methylprop-2-enoyloxymethyl)butoxy]-2-naphthyl]prop-2-enoyl]oxy-phenyl] 4-(2-methylprop-2-enoyloxy)benzoate (17)

[0496] ##STR00409##

[0497] A mixture of 1.3 g (2.4 mmol) 16 and 15 ml dichloro methane is treated with 1.0 ml (12 mmol) methacrylic acid and 30 mg DMAP. At 5 C. 2.4 ml (14 mmol) N-(3-dimethylamino propyl)-N-ethyl are added. After 1 h stirring at this temperature stirring is continued at room temperature overnight. The reaction mixture is purified by silica chromatography (dichloro methane/THF gradient 2%). Further purification by chromatography on reversed phase silica gel (acetonitrile) and crystallization from acetonitrile.

[0498] .sup.1H NMR (700 MHz, Chloroform-d) =8.25 (d, J=8.4 Hz, 2H), 8.03 (d, J=15.9 Hz, 1H), 7.94 (s, 1H), 7.78 (d, J=8.9 Hz, 1H), 7.77-7.70 (m, 2H), 7.29 (d, J=8.6 Hz, 2H), 7.19-7.08 (m, 5H), 6.73 (d, J=15.9 Hz, 1H), 6.40 (s, 1H), 6.12 (s, 2H), 5.85-5.79 (m, 1H), 5.60-5.54 (m, 2H), 4.30 (d, J=5.7 Hz, 4H), 4.23 (t, J=6.2 Hz, 2H), 2.51 (p, J=6.2 Hz, 1H), 2.27 (s, 3H), 2.09 (s, 3H), 2.02 (q, J=6.4 Hz, 2H), 1.95 (s, 6H).

[0499] In accordance or in analogy to the above described procedures, the following compounds are obtained:

TABLE-US-00007 No. Structure RM-1 [00410] embedded image RM-2 [00411] RM-3 [00412] RM-4 [00413] RM-5 [00414]

Comparative Compounds

[0500] ##STR00415##

Nematic Host Mixtures

[0501] The nematic LC host mixture are prepared as indicated in the following tables:

Mixture N1:

[0502]

TABLE-US-00008 Composition [%-w/w] Physical properties CC-3-V 36.00 Clearing Point [ C.]: 78 CC-3-V1 5.00 n.sub.e [589 nm, 20 C.]: 1.5907 CCP-V-1 8.00 n [589 nm, 20 C.]: 0.1095 PGP-2-2V 3.00 .sub. [1 kHz, 20 C.]: 16.6 CCQU-3-F 9.5 .sub. [1 kHz, 20 C.]: 3.7 PUQU-3-F 8.5 [1 kHz, 20 C.]: 12.9 APUQU-2-F 5.00 K.sub.1 [pN, 20 C.]: 12.1 APUQU-3-F 8.00 K.sub.3 [pN, 20 C.]: 13.4 PGUQU-3-F 4.00 K.sub.3/K.sub.1 [pN, 20 C.]: 1.11 PGUQU-4-F 8.00 V.sub.0 [V, 20 C.]: 1.01 PGUQU-5-F 5.00 LTS bulk [h, 20 C.]: 1000 100.0

Mixture N2:

[0503]

TABLE-US-00009 Composition [%-w/w] Physical properties CC-3-V 44.00 Clearing Point [ C.]: 80.5 CC-3-V1 12.00 n.sub.e [589 nm, 20 C.]: 1.5865 CCP-V-1 11.00 n [589 nm, 20 C.]: 0.0991 CCP-V2-1 9.00 .sub. [1 kHz, 20 C.]: 5.3 PGP-2-3 6.00 .sub. [1 kHz, 20 C.]: 2.6 PGUQU-3-F 6.00 [1 kHz, 20 C.]: 2.7 APUQU-3-F 4.5 K.sub.1 [pN, 20 C.]: 14.6 PP-1-2V1 7.00 K.sub.3 [pN, 20 C.]: 15.9 PPGU-3-F 0.5 K.sub.3/K.sub.1 [pN, 20 C.]: 1.09 100.0 V.sub.0 [V, 20 C.]: 2.46 LTS bulk [h, 20 C.]: 1000

Mixture N3:

[0504]

TABLE-US-00010 Composition [%-w/w] Physical properties CY-3-O2 12.00 Clearing Point [ C.]: 85.2 CY-5-O2 10.5 n.sub.e [589 nm, 20 C.]: 1.5956 CCY-3-O1 6.00 n [589 nm, 20 C.]: 0.1120 CCY-3-O2 7.00 .sub. [1 kHz, 20 C.]: 3.7 CCY-5-O2 5.00 .sub. [1 kHz, 20 C.]: 7.9 CPY-2-O2 12.00 [1 kHz, 20 C.]: 4.2 CPY-3-O2 12.00 PYP-2-3 7.5 CC-3-V1 4.00 CC-3-V 24.00 100.0

Mixture N4:

[0505]

TABLE-US-00011 Composition [%-w/w] Physical properties CC-3-V 50.00 Clearing Point [ C.]: 79.4 CC-3-V1 4.5 n.sub.e [589 nm, 20 C.]: 1.5981 CCP-V-1 13.5 n [589 nm, 20 C.]: 0.1094 CPGU-3-OT 6.00 .sub. [1 kHz, 20 C.]: 8.1 PGP-2-2V 6.5 .sub. [1 kHz, 20 C.]: 2.9 PGU-2-F 10.00 [1 kHz, 20 C.]: 5.2 PGUQU-3-F 7.00 K.sub.1 [pN, 20 C.]: 12.6 PPGU-3-F 1.00 K.sub.3 [pN, 20 C.]: 14.2 PUQU-2-F 1.5 K.sub.3/K.sub.1 [pN, 20 C.]: 1.13 100.0 V.sub.0 [V, 20 C.]: 1.64 LTS bulk [h, 20 C.]: 240

Mixture N5:

[0506]

TABLE-US-00012 Composition [%-w/w] Physical properties CC-3-V 30.00 Clearing Point [ C.]: 87 CC-3-V1 10.00 n.sub.e [589 nm, 20 C.]: 1.5829 CCH-34 2.5 n [589 nm, 20 C.]: 0.1019 CCP-V-1 1.5 .sub. [1 kHz, 20 C.]: 3.5 PGIY-2-O4 4.00 .sub. [1 kHz, 20 C.]: 7.1 CCY-3-O2 10.00 [1 kHz, 20 C.]: 3.7 CCY-5-O2 2.00 K.sub.1 [pN, 20 C.]: 15.2 CLY-3-O2 8.00 K.sub.3 [pN, 20 C.]: 18.0 CPY-2-O2 6.00 K.sub.3/K.sub.1 [pN, 20 C.]: 1.19 CPY-3-O2 10.00 V.sub.0 [V, 20 C.]: 2.35 CY-3-O2 12.00 LTS bulk [h, 20 C.]: 0 B-2O-O5 4.00 100.0

Mixture N6:

[0507]

TABLE-US-00013 Composition [%-w/w] Physical properties CC-3-V 21.75 Clearing Point [ C.]: 91 CC-3-V1 10.45 n.sub.e [589 nm, 20 C.]: 1.5970 CPP-V-3 9.52 n.sub.o [589 nm, 20 C.]: 1.4865 BCH-32 4.74 n [589 nm, 20 C.]: 0.1105 BCH-52 3.55 .sub. [1 kHz, 20 C.]: 3.8 PYP-2-3 9.76 .sub. [1 kHz, 20 C.]: 8.1 COY-3-O1 3.19 [1 kHz, 20 C.]: 4.3 COY-3-O2 6.53 K.sub.1 [pN, 20 C.]: 15.8 COY-1V-O2 3.22 K.sub.3 [pN, 20 C.]: 19.0 CCOY-3-O2 8.74 K.sub.3/K.sub.1 [pN, 20 C.]: 1.20 CCOY-2-O2 8.89 V.sub.0 [V, 20 C.]: 2.21 CCOY-V-O2 2.67 CCOY-V-O3 2.64 CCOY-1V-O2 4.35 100.0

Mixture N7:

[0508]

TABLE-US-00014 Composition [%-w/w] Physical properties CC-3-V 29.0 Clearing Point [ C.]: 70 CC-3-V1 10.0 n.sub.e [589 nm, 20 C.]: 1.5976 CCP-V-1 12.0 n.sub.o [589 nm, 20 C.]: 1.4894 CCP-V2-1 4.0 n [589 nm, 20 C.]: 0.1082 CCY-V-O2 8.0 .sub. [1 kHz, 20 C.]: 3.4 COY-3-O2 2.0 .sub. [1 kHz, 20 C.]: 5.5 CCOY-3-O2 4.0 [1 kHz, 20 C.]: 2.2 PY-3-O2 8.0 K.sub.1 [pN, 20 C.]: 12.7 PY-V2-O2 14.0 K.sub.3 [pN, 20 C.]: 14.5 PYP-2-3 9.0 K.sub.3/K.sub.1 [pN, 20 C.]: 1.14 100.0 V.sub.0 [V, 20 C.]: 2.73 .sub.1 [mPa s, 20 C.]: 66 LTS bulk [h, 20 C.]: 0

Mixture N8:

[0509]

TABLE-US-00015 Composition [%-w/w] Physical properties CC-3-V 29.0 Clearing Point [ C.]: 70.5 CC-3-V1 9.0 n.sub.e [589 nm, 20 C.]: 1.5976 CCP-V-1 13.0 n.sub.o [589 nm, 20 C.]: 1.4889 CCY-V-O2 10.0 n [589 nm, 20 C.]: 0.1087 COY-3-O2 2.0 .sub. [1 kHz, 20 C.]: 3.5 CCOY-3-O2 6.0 .sub. [1 kHz, 20 C.]: 6.0 PY-3-O2 8.0 [1 kHz, 20 C.]: 2.5 PY-V2-O2 14.0 K.sub.1 [pN, 20 C.]: 12.6 PYP-2-3 9.0 K.sub.3 [pN, 20 C.]: 14.6 100.0 K.sub.3/K.sub.1 [pN, 20 C.]: 1.16 V.sub.0 [V, 20 C.]: 2.55 .sub.1 [mPa s, 20 C.]: 70 LTS bulk [h, 20 C.]: 96

Mixture N9:

[0510]

TABLE-US-00016 Composition [%-w/w] Physical properties CC-3-V 29.0 Clearing Point [ C.]: 81 PP-1-3 2.0 n.sub.e [589 nm, 20 C.]: 1.5909 CC-3-V1 4.0 n.sub.o [589 nm, 20 C.]: 1.4840 CEY-3-O2 4.0 n [589 nm, 20 C.]: 0.1069 COY-3-O2 7.0 .sub. [1 kHz, 20 C.]: 3.8 CAIY-3-O2 10.0 .sub. [1 kHz, 20 C.]: 8.4 PYP-2-3 17.0 [1 kHz, 20 C.]: 4.6 CCOY-2-O2 16.0 K.sub.1 [pN, 20 C.]: 14.4 CCOY-3-O2 11.0 K.sub.3 [pN, 20 C.]: 16.8 100.0 K.sub.3/K.sub.1 [pN, 20 C.]: 1.17 V.sub.0 [V, 20 C.]: 2.03 .sub.1 [mPa s, 20 C.]: 134 LTS bulk [h, 20 C.]: 264

[0511] Fabrication of Display Cells

[0512] Unless explicitly stated otherwise, the display cells are made with Corning AF glass of 0.7 mm thickness using 6.4 m spacer beads and XN-1500T sealant.

[0513] For measurement of electro-optics 3 m thick PI-free IPS cells are made of substrates commercially available from SD-tech and constructed into cells using ITO electrodes having 5 m electrode spacing and a 3 m electrode width.

[0514] The cells are assembled by hand and then cured using a Omnicure 2000 Mercury lamp with with 35 mW/cm.sup.2 the irradiation power is thereby measured by an Opsytec UV pad-e spectroradiometer.

Mixture Examples

[0515] Nematic LC mixtures M-1 to M-24 according to the invention are prepared from the nematic host mixtures N-1 to N-9 listed above and photoalignment additives of formula I, according to the compositions given in the following table.

TABLE-US-00017 c [%] of Photoalignment Mixture Host Host additive example Mixture Mixture Compound c [%] M-1 N-1 99.70 RM-1 0.30 M-2 N-1 99.50 RM-1 0.50 M-3 N-1 99.00 RM-1 1.00 M-4 N-1 99.50 RM-2 0.50 M-5 N-1 99.00 RM-2 1.00 M-6 N-1 99.70 RM-3 0.30 M-7 N-1 99.50 RM-3 0.50 M-8 N-1 99.00 RM-3 1.00 M-9 N-2 99.50 RM-2 0.50 M-10 N-2 99.00 RM-2 1.00 M-11 N-3 99.50 RM-2 0.50 M-12 N-3 99.00 RM-2 1.00 M-13 N-4 99.50 RM-2 0.50 M-14 N-4 99.00 RM-2 1.00 M-15 N-5 99.70 RM-1 0.30 M-16 N-5 99.50 RM-1 0.50 M-17 N-6 99.70 RM-1 0.30 M-18 N-6 99.50 RM-1 0.50 M-19 N-7 99.70 RM-1 0.30 M-20 N-7 99.50 RM-1 0.50 M-21 N-8 99.70 RM-1 0.30 M-22 N-8 99.50 RM-1 0.50 M-23 N-9 99.70 RM-1 0.30 M-24 N-9 99.50 RM-1 0.50

[0516] Additionally comparable nematic LC mixtures CM-1 to CM-6 to the invention are prepared from the nematic host mixtures N-1 listed above and photoalignment additives according to the prior art. The compositions are given in the following table.

TABLE-US-00018 Comparative c [%] of Photoalignment Mixture Host Host additive example Mixture Mixture Compound c [%] CM-1 N-1 99.70 CRM-1 0.30 CM-2 N-1 99.50 CRM-1 0.50 CM-3 N-1 99.00 CRM-1 1.00 CM-4 N-1 99.70 CRM-2 0.30 CM-5 N-1 99.50 CRM-2 0.50 CM-6 N-1 99.00 CRM-2 1.00

[0517] Cell Filling and Curing

[0518] Unless explicitly stated otherwise, the selected LC mixtures are capillary filled using capillary action at room temp., annealed for 1 h at 100 C. and then irradiated at the same temperature with linearly polarised UV light (35 mW/cm.sup.2) for the given time. The cells are then cooled to room temperature. Next, the alignment quality is studied between crossed polarisers on a light box.

TABLE-US-00019 Curing Host mixture Compound time Example [%] [%] [s] Alignment M-1 N-1 99.70 RM-1 0.30 300 ++ M-2 N-1 99.50 RM-1 0.50 180 ++ M-3 N-1 99.00 RM-1 1.00 60 ++ M-6 N-1 99.70 RM-3 0.30 180 + M-7 N-1 99.50 RM-3 0.50 120 + M-8 N-1 99.00 RM-3 1.00 60 ++ M-9 N-2 99.50 RM-2 0.50 180 ++ M-10 N-2 99.00 RM-2 1.00 60 ++ M-11 N-3 99.50 RM-2 0.50 180 + M-12 N-3 99.00 RM-2 1.00 120 ++ M-13 N-4 99.50 RM-2 0.50 180 + M-14 N-4 99.00 RM-2 1.00 120 ++ M-15 N-5 99.70 RM-1 0.30 300 + M-16 N-5 99.50 RM-1 0.50 180 + CM-2 N-1 99.50 CRM-1 0.50 120 + CM-3 N-1 99.00 CRM-1 1.00 120 ++ CM-5 N-1 99.50 CRM-2 0.50 120 ++ CM-6 N-1 99.00 CRM-2 1.00 60 ++ CM-7 N-1 100.00 Alignment quality: (++) excellent, (+) good, (o) acceptable, () poor

[0519] At least good uniform planar alignment is achieved with all mixtures despite from comparison mixture example CM-7. With mixtures comprising CRM-1 is it not possible to reach the optimum dark state level at below 1% concentration.

[0520] VHR Measurements

[0521] Unless explicitly stated otherwise, the selected LC mixtures are capillary filled using capillary action at room temp., annealed for 1 h at 100 C. and then irradiated at the same temperature with linearly polarised UV light (35 mW/cm2) from an Omnicure S2000 mercury lamp with a built in 320-500 nm filter either utilizing an additional 360 nm long pass filter (cuts off shorter wavelengths from 320-360 nm) or without such filter. The cells are then cooled to room temperature. Next, the VHR is studied using Toyo LCM-1 LC Material Characteristics Measurement System. Unless described otherwise, the measurement of the VHR is carried out as described in T. Jacob, U. Finkenzeller in Merck Liquid CrystalsPhysical Properties of Liquid Crystals, 1997.

[0522] VHR measured at 100 C., 60 Hz and 1 V after curing without 360 nm cut off filter

TABLE-US-00020 Host mixture Photoalignment compound VHR Example [%] [%] [%] M-1 N-1 99.70 RM-1 0.30 18.5 M-4 N-1 99.50 RM-2 0.50 23.5

[0523] VHR measured at 100 C., 60 Hz and 1 V after curing without 360 nm cut off filter

TABLE-US-00021 Host mixture Photoalignment compound VHR Example [%] [%] [%] M-1 N-1 99.70 RM-1 0.30 92.6 M-4 N-1 99.50 RM-2 0.50 93.8

TABLE-US-00022 Host mixture Photoalignment compound Example [%] [%] Alignment CM-1 N-1 99.70 CRM-1 0.30 No alignment CM-2 N-1 99.50 CRM-1 0.50 No alignment CM-3 N-1 99.00 CRM-1 1.00 No alignment CM-4 N-1 99.70 CRM-2 0.30 No alignment CM-5 N-1 99.50 CRM-2 0.50 No alignment CM-6 N-1 99.00 CRM-2 1.00 No alignment

[0524] As can be seen from the above-given tables the VHR of test cells in accordance with the present invention can be significantly improved by utilizing a 360 nm cut off filter while irradiating the test cells. In comparison to the test cells according to the present invention, the test cells utilizing the comparative mixtures CM-1 to CM-6 do not show any uniform alignment after curing utilizing a 360 nm cut off filter.

LIQUID CRYSTAL MIXTURE AND LIQUID CRYSTAL DISPLAY

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Abstract

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