Liquid crystal mixture and liquid crystal display

文档序号：835023 发布日期：2021-03-30 浏览：11次中文

阅读说明：本技术 液晶混合物及液晶显示器 (Liquid crystal mixture and liquid crystal display ) 是由 S·希米安诺斯基 H·哈恩赛尔 N·格雷因特 J·斯普朗 M·赫尼尔于 2019-08-19 设计创作，主要内容包括：本发明涉及包含以下的液晶混合物：光配向组分A),其包含一种或多种式I的光反应性介晶,其中R～(11)、R～(21)、A～(11)、A、Z、X～(11)、X～(21)、Y～(11)、Y～(12)、Sp～(11)、Sp～(21)、o及p具有根据权利要求1中所给出的含义之一,液晶组分B),其包含一种或多种向列态化合物,及可聚合组分C),其包含一种或多种式P的可聚合化合物,P～a-Sp～a-P～b P其中P～a、P～b及Sp～a具有根据权利要求1中所给出的含义之一。此外,本发明涉及产生这样的LC介质的方法、这样的介质在LC装置中的用途及包含根据本发明的LC介质的LC装置。本发明进一步涉及用于制造此液晶显示器的方法及根据本发明的液晶混合物用于制造此液晶显示器的用途。(The invention relates to a liquid-crystal mixture comprising: a photoalignment component A) comprising one or more photoreactive mesogens of formula I, wherein R is 11 、R 21 、A 11 、A、Z、X 11 、X 21 、Y 11 、Y 12 、Sp 11 、Sp 21 O and P have one of the meanings given in claim 1, a liquid-crystalline component B) comprising one or more nematic compounds, and a polymerizable component C) comprising one or more polymerizable compounds of the formula P, P a ‑Sp a ‑P b P in which P a 、P b And Sp a Have one of the meanings given in claim 1. Furthermore, the invention relates to a method for producing such an LC medium, to the use of such a medium in an LC device and to an LC device comprising an LC medium according to the invention. The invention further relates to a method for producing such a liquid-crystal display and to the use of the liquid-crystal mixtures according to the invention for producing such a liquid-crystal display.)

1. A liquid crystal mixture comprising: a photoalignment component A) comprising one or more photoreactive mesogens of formula I,

wherein

A¹¹Represents a group selected from the group consisting of:

a) from the group consisting of 1, 4-phenylene and 1, 3-phenylene, in which furthermore one or two CH groups may be replaced by N and in which furthermore one or more H atoms may be replaced by L,

b) a group consisting of:

furthermore wherein one or more H atoms in these groups 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,

each A independently of one another at each occurrence has a meaning for A¹¹Is one of the meanings of (A) or (B)

a) Trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene, in which one or more non-adjacent CH's are furthermore present₂The radicals may be substituted by-O-and/or-S-and in addition one or more H atoms may be substituted by F, or

b) 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 with L,

l, equal or different at each occurrence, represents-OH, -F, -Cl, -Br, -I, -CN, -NO₂、SF₅、-NCO、-NCS、-OCN、-SCN、-C(＝O)N(R^z)₂、-C(＝O)R^z、-N(R^z)₂Optionally substituted silyl, optionally substituted aryl having 6 to 20C atoms or straight-chain or branched or cyclic alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25C atoms, or represents X²¹-Sp²¹-R²¹，

M represents-O-, -S-, -CH₂-、-CHR^z-or-CR^yR^z-，

R^yAnd R^zEach independently of the others, represents H, CN, F or an alkyl radical having 1 to 12C atoms, in which one or more H atoms may be replaced by F,

Y¹¹and Y¹²Each independently of the others, H, F, phenyl or an optionally fluorinated alkyl group having 1 to 12C atoms,

z represents, independently of one another at each occurrence, a single bond, -COO-, -OCO-, -O-CO-O-, -OCH₂-、-CH₂O-、-OCF₂-、-CF₂O-、-(CH₂)_n-、-CF₂CF₂-, -CH-, -CF-, -CH-COO-, -OCO-CH-, -CO-S-, -S-CO-, -CS-S-, -S-CS-, -S-CSS-or-C.ident.C-,

n represents an integer between 2 and 8,

o and p each and independently represent 0, 1 or 2,

X¹¹and X²¹Independently of one another at each occurrence, represents a single bond, -CO-O-, -O-CO-, -O-COO-, -O-, -CH ═ CH-, -C ≡ C-, -CF₂-O-、-O-CF₂-、-CF₂-CF₂-、-CH₂-O-、-O-CH₂-, -CO-S-, -S-CO-, -CS-S-, -S-CS-, -S-CSS-or-S-,

Sp¹¹and Sp²¹Each occurrence independently and independently represents a single bond or a spacer group comprising 1 to 20C atoms, wherein one or more non-adjacent and non-terminal CH₂The radicals may also be substituted by-O-, -S-, -NH-, -N (CH)₃)-、-CO-、-O-CO-、-S-CO-、-O-COO-、-CO-S-、-CO-O-、-CF₂-、-CF₂O-、-OCF₂-, -C (OH) -, -CH (alkyl) -, -CH (alkenyl) -, -CH (alkoxy) -, -CH (oxaalkyl) -, -CH ═ CH-or-C.ident.C-in place of, but in such a way that no two O atoms are adjacent to each other and no two radicals selected from the group consisting of-O-CO-, -S-CO-, -O-COO-, -CO-S-, -CO-O-and-CH ≡ CH-are adjacent to each other,

R¹¹the expression P is used to indicate that P,

R²¹represents P, halogen, CN, an optionally fluorinated alkyl or alkenyl group having up to 15C atoms,in which one or more non-adjacent CH₂The groups may be replaced by-O-, -S-, -CO-, -C (O) O-, -O-C (O) -, O-C (O) -O-,

p in each occurrence is each and independently of the other a polymerizable group

A liquid-crystalline component B) comprising one or more nematic compounds, and

a polymerizable component C) comprising one or more polymerizable compounds of the formula P,

P^a-Sp^a-P^b P

wherein the individual radicals have the following meanings:

P^a、P^beach independently of the other represents a polymerizable group,

Sp^arepresents a spacer group.

2. Liquid-crystal mixture according to claim 1, characterized in that the total concentration of the compounds of the formula I in the mixture is in the range from 0.01% to 10% by weight.

3. Liquid-crystal mixture according to claim 1 or 2, characterized in that the concentration of the polymerizable component C) is in the range from 0.1 to 5% by weight.

4. Liquid-crystal mixture according to one or more of claims 1 to 3, characterized in that it comprises one or more compounds of the formulae P-1 to P-10

5. Liquid-crystal mixture according to one or more of claims 1 to 5, characterized in that the LC host mixture has a negative dielectric anisotropy.

6. Liquid-crystal mixture according to claim 5, characterized in that the LC host mixture comprises one or more compounds of the formulae selected from:

wherein

a is a number of 1 or 2,

b is a number of 0 or 1,

to represent

R¹And R²Each independently of the other represents an alkyl radical having 1 to 12C atoms, in which furthermore one or two non-adjacent CH groups₂A group may be replaced by-O-, -CH ═ CH-, -CO-, -O-CO-, or-CO-O-in such a way that the O atoms are not directly attached to each other,

Z^xrepresents-CH-, -CH ═ CH-₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-O-、-CH₂-、-CH₂CH₂-or a single bond,

L^1-4each independently of the others represents F, Cl, OCF₃、CF₃、CH₃、CH₂F、CHF₂。

7. Liquid-crystal mixture according to one or more of claims 1 to 5, characterized in that the LC host mixture has a positive dielectric anisotropy.

8. Liquid-crystal mixture according to claim 7, characterized in that the LC host mixture comprises one or more compounds selected from the group consisting of compounds of formulae II and III:

wherein

R²⁰Each, identically or differently, represents a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15C atoms, and furthermore where one or more CH groups of these radicals₂The radicals may each, independently of one another, be-C.ident.C-, -CF in such a way that the O atoms are not directly linked to one another₂O-、-CH＝CH-、-O-, -CO-O-or-O-CO-substitution,

X²⁰each, the same or different, represents F, Cl, CN, SF₅SCN, NCS, halogenated alkyl, halogenated alkenyl, halogenated alkoxy or halogenated alkenyloxy each having up to 6C atoms, and

Y^20-24each of which is the same or different and represents H or F,

w represents H or a methyl group,

andeach being identical or different

9. Liquid-crystal mixture according to claim 7 or 8, characterized in that it comprises one or more compounds selected from the group consisting of the compounds of formulae XI and XII:

wherein R is²⁰、X²⁰W and Y^20-23Has the meaning indicated in formula III in claim 16, and

andeach independently of the other represent

And

to represent

10. Liquid-crystal mixture according to one or more of claims 1 to 9, characterized in that the LC host mixture comprises one or more compounds of the formula:

wherein the individual radicals have the following meanings:

to represent

To represent

R³And R⁴Each independently of the other represents an alkyl radical having 1 to 12C atoms, in which furthermore one or two non-adjacent CH groups₂A group may be replaced by-O-, -CH ═ CH-, -CO-, -O-CO-, or-CO-O-in such a way that the O atoms are not directly attached to each other,

Z^yrepresents-CH₂CH₂-、-CH＝CH-、-CF₂O-、-OCF₂-、-CH₂O-、-OCH₂-、-CO-O-、-O-CO-、-C₂F₄-、-CF＝CF-、-CH＝CH-CH₂O-or a single bond.

11. Liquid-crystal mixture according to one or more of claims 1 to 10, characterized in that the LC host mixture comprises one or more compounds of the following formulae:

wherein propyl, butyl and pentyl are linear groups.

12. Liquid-crystal mixture according to one or more of claims 1 to 11, characterized in that the LC host mixture comprises one or more compounds of the formulae selected from:

wherein alkyl and alkyl each independently of one another represent a straight-chain alkyl group having 1 to 6C atoms, and alkyl each independently of one another represent a straight-chain alkenyl group having 2 to 6C atoms.

13. Liquid-crystal mixture according to one or more of claims 1 to 12, characterized in that the LC host mixture comprises one or more compounds of the formulae selected from:

wherein alkyl represents an alkyl group having 1 to 6C atoms.

14. Use of a liquid-crystal mixture according to one or more of claims 1 to 13 for the production of liquid-crystal displays.

15. Method for manufacturing a liquid crystal display, comprising at least the following steps:

providing a first substrate comprising pixel electrodes and a common electrode for generating an electric field in the pixel area substantially parallel to a surface of the first substrate;

providing a second substrate arranged opposite to the first substrate;

inserting a liquid-crystal mixture according to one or more of claims 1 to 13;

irradiating the liquid crystal mixture with linearly polarized light to cause photoalignment of the liquid crystal;

polymerizable compounds for curing the liquid-crystalline mixture by irradiation with ultraviolet light or visible light having a wavelength of 450nm or less.

16. The method according to claim 15, characterized in that the linearly polarized light is ultraviolet light or visible light with a wavelength of 450nm or less.

17. Display obtainable by a method according to claim 15 or 16.

18. A display according to claim 17, wherein the LC host mixture is aligned along a plane in the absence of an applied electric field.

19. A display according to claim 17 or 18, wherein the display is an IPS or FFS display.

Detailed Description

In particular, the present invention relates to compounds of formula I or photoreactive mesogens

Wherein

A¹¹Represents a group selected from the group consisting of:

a) from the group consisting of 1, 4-phenylene and 1, 3-phenylene, in which furthermore one or two CH groups may be replaced by N and in which furthermore one or more H atoms may be replaced by L,

b) selected from the group consisting of:

furthermore wherein one or more H atoms in these groups 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,

a has at each occurrence independently of one another A¹¹One of the meanings or

b) 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 with L,

M represents-O-, -S-, -CH₂-、-CHR^z-or-CR^yR^z-, and

R^yand R^zEach independently of the others, represents H, CN, F or an alkyl radical having 1 to 12C atoms, in which one or more H atoms may be replaced by F, preferably H, methyl, ethyl, propyl, butyl, more preferably H or methyl,

in particular, it is represented by the formula H,

Y¹¹and Y¹²Each independently of the others, H, F, phenyl or an optionally fluorinated alkyl group having 1 to 12C atoms, preferably H, methyl, ethyl, propyl, butyl, more preferably H or methyl,

in particular, it is represented by the formula H,

preferably represents a single bond, -COO-, -OCO-, -OCF₂-、-CF₂O-or- (CH)₂)_n-，

More preferably represents a single bond, -COO-or-OCO-,

n represents an integer between 2 and 8, preferably 2,

o and p each and independently represent 0, 1 or 2, preferably 1,

preferably represents a single bond, -CO-O-, -O-CO-, -O-COO-or-O-,

more preferably represents a single bond or-O-,

preferably represents alkylene having 1 to 20, preferably 1 to 12C atoms, which is optionally mono-or polysubstituted by F, Cl, Br, I or CN,

more preferably a linear ethylene group, propylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, undecylene group, dodecylene group,

R¹¹represents P

R²¹Represents P, halogen, CNOptionally fluorinated alkyl or alkenyl having up to 15C atoms, wherein one or more non-adjacent CH groups₂The groups may be replaced by-O-, -S-, -CO-, -C (O) O-, -O-C (O) -, O-C (O) -O-, preferably P,

p in each occurrence is each and independently of the other a polymerizable group.

In the present application, the polymerizable group (P) is a group suitable for polymerization reactions (e.g. radical or ionic chain polymerization, polyaddition or polycondensation) or for polymer-analogous reactions (e.g. addition or condensation onto the polymer backbone). Particularly preferred are groups for chain polymerization, especially those containing a C ≡ C double bond or a-C ≡ C-triple bond, and groups suitable for ring-opening polymerization (e.g. oxetanyl or epoxy).

Preferred groups P are selected from the group consisting of: CH (CH)₂＝CW¹-CO-O-、CH₂＝CW¹-CO-、CH₂＝CW²-(O)_k3-、CW¹＝CH-CO-(O)_k3-、CW¹＝CH-CO-NH-、CH₂＝CW¹-CO-NH-、CH₃-CH＝CH-O-、(CH₂＝CH)₂CH-OCO-、(CH₂＝CH-CH₂)₂CH-OCO-、(CH₂＝CH)₂CH-O-、(CH₂＝CH-CH₂)₂N-、(CH₂＝CH-CH₂)₂N-CO-、HO-CW²W³-、HS-CW²W³-、HW²N-、HO-CW²W³-NH-、CH₂＝CW¹-CO-NH-、CH₂＝CH-(COO)_k1-Phe-(O)_k2-、CH₂＝CH-(CO)_k1-Phe-(O)_k2-, Phe-CH ═ CH-, HOOC-, OCN-and W⁴W⁵W⁶Si-, in which W¹Represents H, F, Cl, CN, CF₃Phenyl or alkyl having 1 to 5C atoms, especially H, F, Cl or CH₃，W²And W³Each independently of the other, H or alkyl having 1 to 5C atoms, especiallyH, methyl, ethyl or n-propyl, W⁴、W⁵And W⁶Each independently of the others represents Cl, oxaalkyl or oxacarbonylalkyl having 1 to 5C atoms, W⁷And W⁸Each independently of the other H, Cl or alkyl having 1 to 5C atoms, Phe represents 1, 4-phenylene which is optionally substituted by one or more groups L as defined above, k₁、k₂And k₃Each independently of the other represents 0 or 1, k₃Preferably represents 1, and k₄Represents an integer of 1 to 10.

Further preferably P represents a group

Preferred groups

Y represents H, F, phenyl or an optionally fluorinated alkyl group having 1 to 12C atoms, preferably H, methyl, ethyl, propyl, butyl,

more preferably H or methyl, especially H.

Particularly preferred groups P are selected from the group consisting of: CH (CH)₂＝CW¹-CO-O-, in particular CH₂＝CH-CO-O-、CH₂＝C(CH₃) -CO-O-and CH₂CF-CO-O-and CH₂＝CH-O-、(CH₂＝CH)₂CH-O-CO-、(CH₂＝CH)₂CH-O-、Andor group

Y represents H or methyl, in particular H.

Very particularly preferred groups P are selected from the group consisting of: acrylate, methacrylate, fluoroacrylate, and vinyloxy, chloroacrylate, oxetane, epoxy, and the like

Y represents H or methyl, in particular H, and among these groups, preference is given to acrylate or methacrylate groups or the following groups:

wherein Y represents H or methyl.

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

Wherein R is¹¹、R²¹、A¹¹、X¹¹、X²¹、Y¹¹、Y¹²、Sp¹¹And Sp²¹Has one of the meanings given above in formula I, A¹²To A²³Has one of the meanings of A in the formula I, A¹¹Has one of the meanings as given above under formula I, and Z¹¹To Z²²Has one of the meanings of Z as given under formula I above.

Further preferred compounds of formula I-1 are selected from the group consisting of compounds of formulae I-1-1 to I-1-3

Wherein R is¹¹、R²¹、A¹¹、X¹¹、X²¹、Sp¹¹And Sp²¹Has one of the meanings given above in formula I, A²¹Has one of the meanings of A in formula I, preferably A²¹Represents the group consisting of 1, 4-phenylene, wherein furthermore one or two CH groups may be replaced by N, and wherein furthermore one or more H atoms may be replaced by L as given under formula I above or the group consisting of trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene, wherein furthermore one or more non-adjacent CH groups₂The radicals may be replaced by-O-and/or-S-, and wherein furthermore one or more H atoms may be replaced by F.

Preferably, the compound of formula I-2 is selected from the following sub-formulae I-2-1 to I-2-3:

r of which¹¹、R²¹、X¹¹、X²¹、Sp¹¹And Sp²¹Has one of the meanings as given in formula I above, and Z¹¹As one of the meanings given above for Z in formula I, A¹²、A²¹Has one of the meanings given above for A in formula I, A¹²、A²¹Preferably each and independently represent a group consisting of 1, 4-phenylene in which one or two further CH groups may be replaced by N and in which one or more further H atoms may be replaced by L as given in formula I above, or a group consisting of trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene in which one or more further non-adjacent CH groups₂The groups may be replaced by-O-and/or-S-and wherein one or more further H atoms may be replaced by F.

Preferred compounds of formula I-3 are selected from the following sub-formulae I-3-1 to I-3-3,

wherein R is¹¹、R²¹、X¹¹、X²¹、Sp¹¹And Sp²¹Has one of the meanings as given above in formula I, Z²¹Having one of the meanings given above for Z in formula I, A²¹And A²²Having one of the meanings given above for a in formula I. A. the²¹And A²²Preferably each and independently represent a group consisting of 1, 4-phenylene in which one or two further CH groups may be replaced by N and in which one or more further H atoms may be replaced by L as given in formula I above, or a group consisting of trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene in which one or more further non-adjacent CH groups₂The groups may be replaced by-O-and/or-S-and wherein one or more further H atoms may be replaced by F.

Preferred compounds of formula I-4 are selected from the following subformulae,

wherein R is¹¹、R²¹、X¹¹、X²¹、Sp¹¹And Sp²¹Having one of the meanings given above in formula I, A¹²、A²¹And A²²Having one of the meanings given above for A in formula I, Z¹¹And Z²¹Has one of the meanings given above for Z in formula I, r and q represent 1,2 or 3, s represents an integer from 1 to 6, and A¹²、A²¹And A²²Having one of the meanings given above for a in formula I. A. the¹²、A²¹And A²²Preferably each and independently represent the group consisting of 1, 4-phenylene in which one or two CH groups may be replaced by N and in which one or more further H atoms may be replaced by L as given in formula I aboveAlternatively, or in combination with trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene, wherein one or more non-adjacent CH groups are additionally present₂The groups may be replaced by-O-and/or-S-and wherein one or more further H atoms may be replaced by F.

Preferred compounds of formula I-5 are selected from the following subformulae,

wherein R is¹¹、R²¹、X¹¹、X²¹、Sp¹¹And Sp²¹Has one of the meanings as given above in formula I, Z¹¹、Z¹²And Z²¹Has one of the meanings given above for Z in formula I, and A¹²、A¹³、A²¹And A²²Having one of the meanings given above for a in formula I. Preferably, A¹²、A¹³、A²¹And A²²Each independently represent a group consisting of 1, 4-phenylene in which one or two CH groups may be replaced by N and in which one or more further H atoms may be replaced by L as given in formula I above, or a group consisting of trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene in which one or more further non-adjacent CH groups₂The groups may be replaced by-O-and/or-S-and wherein one or more further H atoms may be replaced by F.

Preferred compounds of formula I-2-1 are those of the following sub-formula,

wherein R is¹¹、R²¹、X¹¹、X²¹、Sp¹¹And Sp²¹Has one of the meanings as given above in formula I, Z¹¹Has one of the meanings given above for Z in formula I, and

radical (I)Each independently isOr

To representAnd

wherein L has one of the meanings given above for formula I, and preferably denotes F, Cl, OCH₃、COCH₃Or an alkyl group having 1 to 6C atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or X²¹-Sp²¹-R²¹。

Preferred compounds of formulae I-3-1 to I-3-3 are of the following sub-formulae:

wherein R is¹¹、R²¹、X¹¹、X²¹、Sp¹¹And Sp²¹Has one of the meanings as given above in formula I, Z²¹Has one of the meanings given above for Z in formula I, and

radical (I)Each independently isOr

To representAnd

wherein L has one of the meanings given above for formula I, and is preferably F, Cl, OCH₃、COCH₃Or an alkyl group having 1 to 6C atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or X²¹-Sp²¹-R²¹。

Preferred compounds of formula I-4-1 are those of the following sub-formula:

wherein R is¹¹、R²¹、X¹¹、X²¹、Sp¹¹And Sp²¹Has one of the meanings as given above in formula I, Z¹¹And Z²¹Has one of the meanings given above for Z in formula I, r and q represent 1,2 or 3 and s represents an integer from 1 to 6, and

radical (I)Each independently isOr

To representAnd

Preferred compounds of formula I-5-1 are those of the following sub-formula:

wherein R is¹¹、R²¹、X¹¹、X²¹、Sp¹¹And Sp²¹Has one of the meanings as given above in formula I, Z¹¹、Z¹²And Z²¹Each and independently having one of the meanings given above for Z in formula I, r and q represent 1,2 or 3 and s represents an integer from 1 to 6, and the radicalsEach independently isOr

To representAnd

wherein L is provided withHas one of the meanings given above in formula I, and is preferably F, Cl, OCH₃、COCH₃Or an alkyl group having 1 to 6C atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or X²¹-Sp²¹-R²¹。

More preferred compounds of formula I-2-1a are compounds of the following sub-formula:

wherein R is¹¹、R²¹、X¹¹、X²¹、Sp¹¹And Sp²¹Has one of the meanings given above in formula I and L represents F, Cl, OCH₃、COCH₃Or an alkyl group having 1 to 6C atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or X²¹-Sp²¹-R²¹。

More preferred compounds of formulae I-3-1a to I-3-1c are of the following sub-formulae:

wherein R is¹¹、R²¹、X¹¹、X²¹、Sp¹¹And Sp²¹Has one of the meanings given above in formula I, and L represents F, Cl, OCH₃、COCH₃Or an alkyl group having 1 to 6C atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or X²¹-Sp²¹-R²¹。

Further preferred compounds of formula I-4-1 are compounds of the following sub-formula:

More preferred compounds of formula I-5-1 are those of the following sub-formula:

Further preferred compounds of formula I-2-1a are compounds of the following sub-formula:

wherein

X each independently represents methyl or H, preferably methyl

Y represents a methyl group or a hydrogen atom,

Sp¹¹and Sp²¹Has one of the meanings as given above in formula I, and preferably each and independently preferably represents an alkylene radical having 1 to 20, preferably 1 to 12C atoms, which is optionally mono-or polysubstituted by F, Cl, Br, I or CN,

l represents F, Cl, OCH₃、COCH₃Or alkylene having 1 to 6C atoms, preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

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

wherein

X each and independently represents methyl or H, preferably methyl,

y represents a methyl group or a hydrogen atom,

l represents F, Cl, OCH₃、COCH₃Or alkylene having 1 to 6C atoms, preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Further preferred compounds of formula I-4-1 are compounds of the following sub-formula:

wherein

X each independently represents methyl or H, preferably methyl

Y represents a methyl group or a hydrogen atom,

l represents F, Cl, OCH₃、COCH₃Or alkylene having 1 to 6C atoms, preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Further preferred compounds of formula I-5-1 are compounds of the following sub-formula:

wherein

X each and independently represents methyl or H, preferably methyl,

y represents a methyl group or a hydrogen atom,

Sp¹¹and Sp²¹Having one of the meanings as given above in formula I, and preferably each and independently represents an alkylene group having 1 to 20, preferably 1 to 12C atoms, which is optionally mono-or polysubstituted with F, Cl, Br, I or CN,

l represents F, Cl, OCH₃、COCH₃Or alkylene having 1 to 6C atoms, preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

The compounds of formula I and their subformulae are preferably synthesized according to or similar to the procedures described in WO 2017/102068 and JP 2006-6232809:

the media of 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 a component A) comprising a compound of the formula I according to the invention.

The medium preferably comprises one, two or three, more preferably one or two and most preferably one compound of the formula I according to the invention.

In a preferred embodiment, component A) consists of a compound of the formula I.

In a preferred embodiment, the LC-host mixture (component B) of the invention comprises one or more, preferably two or more, low molecular weight (i.e. monomeric or unpolymerized) compounds. The latter are stable or non-reactive to polymerization or photoalignment under conditions for polymerization of polymerizable compounds or photoalignment of the photoreactive mesogens of formula I.

Suitable host mixtures are in principle any dielectrically negative or positive LC mixtures suitable for use in conventional VA, IPS or FFS displays.

Suitable LC mixtures are known to the person skilled in the art and are described in the literature. LC media with negative dielectric anisotropy for VA displays are described, for example, in EP 1378557 a 1.

Suitable LC mixtures with positive dielectric anisotropy suitable for LCDs, and in particular for IPS displays, are known, for example, from JP 07-181439 (a), EP 0667555, EP 0673986, DE 19509410, DE 19528106, DE 19528107, WO 96/23851, WO 96/28521 and WO 2012/079676.

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

The LC host mixture is preferably a nematic LC mixture and preferably has no chiral LC phase.

In a preferred embodiment of the present invention, the LC medium contains an LC host mixture with negative dielectric anisotropy. Preferred embodiments of such LC media and corresponding LC host mixtures are those of the following sections a) -z):

a) an LC medium comprising one or more compounds of formula CY and/or formula PY:

wherein

a represents a number of 1 or 2,

b represents a number of 0 or 1,

to represent

R¹And R²Each independently of the other represents an alkyl radical having 1 to 12C atoms, one or two non-adjacent CH groups₂The radicals may be replaced by-O-, -CH ═ CH-, -CO-, -OCO-or-COO-in such a way that the O atoms are not directly linked to one another, preferably alkyl or alkoxy having 1 to 6C atoms,

Z^xand Z^yEach independently of the other represents-CH₂CH₂-、-CH＝CH-、-CF₂O-、-OCF₂-、-CH₂O-、-OCH₂-、-CO-O-、-O-CO-、-C₂F₄-、-CF＝CF-、-CH＝CH-CH₂O-or a single bond, preferably a single bond,

L^1-4each independently of the others represents F, Cl, OCF₃、CF₃、CH₃、CH₂F、CHF₂。

Preferably, L¹And L²Both represent F, or L¹And L²One represents F and the other represents Cl, or L³And L⁴Both represent F or L³And L⁴One represents F and the other represents Cl.

The compound of formula CY is preferably selected from the group consisting of the following subformulae:

wherein a represents 1 or 2, alkyl and alkyl each independently of the other represents a straight-chain alkyl group having 1 to 6C atoms, and alkyl represents a straight-chain alkenyl group having 2 to 6C atoms, and (O) represents an oxygen atom or a single bond. alkenyl preferably represents CH₂＝CH-、CH₂＝CHCH₂CH₂-、CH₃-CH＝CH-、CH₃-CH₂-CH＝CH-、CH₃-(CH₂)₂-CH＝CH-、CH₃-(CH₂)₃-CH ═ CH-or CH₃-CH＝CH-(CH₂)₂-。

The compound of formula PY is preferably selected from the group consisting of the following subformulae:

wherein alkyl and alkyl^*Each independently of the other represents a linear alkyl group having 1 to 6C atoms, and alkinyl represents a linear alkenyl group having 2 to 6C atoms, and (O) represents an oxygen atom or a single bond. alkenyl preferably represents CH₂＝CH-、CH₂＝CHCH₂CH₂-、CH₃-CH＝CH-、CH₃-CH₂-CH＝CH-、CH₃-(CH₂)₂-CH＝CH-、CH₃-(CH₂)₃-CH ═ CH-or CH₃-CH＝CH-(CH₂)₂-。

b) An LC medium further comprising one or more compounds of the formula:

wherein the individual radicals have the following meanings:

to represent

To represent

R³And R⁴Each independently of the other represents an alkyl radical having 1 to 12C atoms, one or two non-adjacent CH groups₂The radicals may be replaced by-O-, -CH ═ CH-, -CO-, -O-CO-or-CO-O-in such a way that the O atoms are not directly linked to one another,

Z^yrepresents-CH₂CH₂-、-CH＝CH-、-CF₂O-、-OCF₂-、-CH₂O-、-OCH₂-、-CO-O-、-O-CO-、-C₂F₄-、-CF＝CF-、-CH＝CH-CH₂O-or a single bond, preferably a single bond.

The compound of formula ZK is preferably selected from the group consisting of the following subformulae:

wherein alkyl and alkyl^*Each independently of the others, represents a linear alkyl group having 1 to 6C atoms, and alkenyl represents a linear alkenyl group having 2 to 6C atoms. alkenyl preferably represents CH₂＝CH-、CH₂＝CHCH₂CH₂-、CH₃-CH＝CH-、CH₃-CH₂-CH＝CH-、CH₃-(CH₂)₂-CH＝CH-、CH₃-(CH₂)₃-CH ═ CH-or CH₃-CH＝CH-(CH₂)₂-。

Especially preferred are compounds of formulae ZK1 and ZK 3.

Particularly preferred compounds of formula ZK are selected from the following subformulae:

wherein propyl, butyl and pentyl are linear groups.

Most preferred are compounds of formulae ZK1a and ZK3 a.

c) An LC medium further comprising one or more compounds of the formula:

wherein the individual radicals, identically or differently on each occurrence, have the following meanings:

R⁵and R⁶Each independently of the other represents an alkyl radical having 1 to 12C atoms, one or two non-adjacent CH groups₂The radicals may be replaced by-O-, -CH ═ CH-, -CO-, -OCO-or-COO-in such a way that the O atoms are not directly linked to one another, preferably alkyl or alkoxy having 1 to 6C atoms,

to represent

To representAnd e represents 1 or 2.

The compound of formula DK is preferably selected from the group consisting of the following subformulae:

d) An LC medium further comprising one or more compounds of the formula:

wherein the individual radicals have the following meanings:

to represent

Wherein at least one ring F is different from cyclohexylene,

f represents a number of 1 or 2,

R¹and R²Each independently of the other represents an alkyl radical having 1 to 12C atoms, one or two non-adjacent CH groups₂A group may be replaced by-O-, -CH ═ CH-, -CO-, -OCO-, or-COO-in such a way that the O atoms are not directly linked to each other,

Z^xrepresents-CH₂CH₂-、-CH＝CH-、-CF₂O-、-OCF₂-、-CH₂O-、-OCH₂-、-CO-O-、-O-CO-、-C₂F₄-、-CF＝CF-、-CH＝CH-CH₂O-or a single, preferably single,

L¹and L²Each independently of the others represents F, Cl, OCF₃、CF₃、CH₃、CH₂F、CHF₂。

Preferably, the group L¹And L²Both represent F, or a group L¹And L²One represents F and the other represents Cl.

The compound of formula LY is preferably selected from the group consisting of the following subformulae:

wherein R is¹Having the meaning indicated above, alkyl representsA straight-chain alkyl group having 1 to 6C atoms, (O) represents an oxygen atom or a single bond, and v represents an integer of 1 to 6. R¹Preferably represents a straight-chain alkyl group having 1 to 6C atoms or a straight-chain alkenyl group having 2 to 6C atoms, in particular CH₃、C₂H₅、n-C₃H₇、n-C₄H₉、n-C₅H₁₁、CH₂＝CH-、CH₂＝CHCH₂CH₂-、CH₃-CH＝CH-、CH₃-CH₂-CH＝CH-、CH₃-(CH₂)₂-CH＝CH-、CH₃-(CH₂)₃-CH ═ CH-or CH₃-CH＝CH-(CH₂)₂-。

e) An LC medium further comprising one or more compounds selected from the group consisting of:

wherein alkyl represents C_1-6-alkyl, L^xRepresents H or F, and X represents F, Cl, OCF₃、OCHF₂Or OCH ═ CF₂. Especially preferred are compounds of formula G1, wherein X represents F.

f) An LC medium further comprising one or more compounds selected from the group consisting of:

wherein R is⁵Having the above for R¹Alkyl represents one of the meanings indicated, C_1-6-alkyl, d represents 0 or 1, and z and m each, independently of the others, represent an integer from 1 to 6. R in these compounds⁵Particularly preferably C_1-6-alkyl or C_1-6-alkoxy or C_2-6-alkenyl, d is preferably 1. The LC medium according to the invention preferably comprises one or more compounds of the formulae mentioned above in an amount of > 5% by weight.

g) An LC medium further comprising one or more biphenyl compounds selected from the group consisting of the following respective formulae:

wherein alkyl and alkyl^*Each independently of the others represents a straight-chain alkyl group having 1 to 6C atoms, and alkinyl^*Each independently of the others, represents a linear alkenyl group having 2 to 6C atoms. alkinyl and alkinyl^*Preferably represents CH₂＝CH-、CH₂＝CHCH₂CH₂-、CH₃-CH＝CH-、CH₃-CH₂-CH＝CH-、CH₃-(CH₂)₂-CH＝CH-、CH₃-(CH₂)₃-CH ═ CH-or CH₃-CH＝CH-(CH₂)₂-。

The proportion of biphenyls of the formulae B1 to B3 in the LC mixture is preferably at least 3% by weight, in particular ≧ 5% by weight.

Compounds of formula B2 are particularly preferred.

The compounds of formulae B1 to B3 are preferably selected from the group consisting of the following subformulae:

wherein alkyl^*Represents an alkyl group having 1 to 6C atoms. The media according to the invention particularly preferably comprise one or more compounds of the formulae B1a and/or B2 e.

h) An LC medium further comprising one or more terphenyl compounds of the formula:

wherein R is⁵And R⁶Each independently of the other having one of the meanings indicated above, and

each independently of the other represent

Wherein L is⁵Represents F or Cl, preferably F, and L⁶Represents F, Cl, OCF₃、CF₃、CH₃、CH₂F or CHF₂Preferably F.

The compound of formula T is preferably selected from the group consisting of the following subformulae:

wherein R represents a linear alkyl or alkoxy group having 1 to 7C atoms, R^*Represents a linear alkenyl group having 2 to 7C atoms, (O) represents an oxygen atom or a single bond, and m represents an integer of 1 to 6. R^*Preferably represents CH₂＝CH-、CH₂＝CHCH₂CH₂-、CH₃-CH＝CH-、CH₃-CH₂-CH＝CH-、CH₃-(CH₂)₂-CH＝CH-、CH₃-(CH₂)₃-CH ═ CH-or CH₃-CH＝CH-(CH₂)₂-。

R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy or pentoxy.

The LC media according to the invention preferably comprise from 0.5 to 30% by weight, in particular from 1 to 20% by weight, of the terphenyl of the formula T and its preferred subformulae.

Especially preferred are compounds of formulae T1, T2, T3 and T21. In these compounds, R preferably represents an alkyl group and an alkoxy group, each having 1 to 5C atoms.

If the Δ n value of the mixture is to be ≥ 0.1, it is preferred to use terphenyl in the mixture of the invention. Preferred mixtures comprise 2-20% by weight of one or more terphenyl compounds of formula T, preferably selected from the group of compounds T1 to T22.

i) An LC medium further comprising one or more compounds selected from the group consisting of:

wherein R is¹And R²Have the meaning indicated above and preferably each independently of one another denote a straight-chain alkyl group having 1 to 6C atoms or a straight-chain alkenyl group having 2 to 6C atoms.

Preferred media comprise one or more compounds selected from the group consisting of the compounds of the formulae O1, O3 and O4.

k) An LC medium further comprising one or more compounds of the formula:

wherein

To represent

R⁹Representation H, CH₃、C₂H₅Or n-C₃H₇(F) represents an optional fluoro substituent, and q represents 1,2 or 3, and R⁷Having a function of R¹In one of the indicated meanings, the amount is preferably > 3% by weight, in particular ≧ 5% by weight and very particularly preferably 5 to 30% by weight.

Particularly preferred compounds of formula FI are selected from the group consisting of the following subformulae:

wherein R is⁷Preferably represents a straight-chain alkyl group, and R⁹Represents CH₃、C₂H₅Or n-C₃H₇. Especially preferred is the formula FI1. FI2 and FI 3.

l) an LC medium additionally comprising one or more compounds selected from the group consisting of:

wherein R is⁸Having a function of R¹Indicated and alkyl represents a straight-chain alkyl group having 1 to 6C atoms.

m) an LC medium additionally comprising one or more compounds containing tetrahydronaphthyl or naphthyl units, e.g., a compound selected from the group consisting of:

wherein

R¹⁰And R¹¹Each independently of the other represents an alkyl radical having 1 to 12C atoms, one or two non-adjacent CH groups₂The radicals may be replaced by-O-, -CH ═ CH-, -CO-, -OCO-or-COO-in such a way that the O atoms are not directly linked to one another, preferably alkyl or alkoxy having 1 to 6C atoms,

and R is¹⁰And R¹¹Preferably represents a straight-chain alkyl or alkoxy group having 1 to 6C atoms or a straight-chain alkenyl group having 2 to 6C atoms, and

Z¹and Z²Each independently of the other represents-C₂H₄-、-CH＝CH-、-(CH₂)₄-、-(CH₂)₃O-、-O(CH₂)₃-、-CH＝CH-CH₂CH₂-、-CH₂CH₂CH＝CH-、-CH₂O-、-OCH₂-、-CO-O-、-O-CO-、-C₂F₄-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CH₂-or a single bond.

n) an LC medium which additionally comprises one or more difluorodibenzochromans and/or chromans of the formulae:

wherein

R¹¹And R¹²Each independently of the others, having the above formula N1 for R¹¹One of the indicated meanings.

Ring M is trans-1, 4-cyclohexylene or 1, 4-phenylene,

Z^mis-C₂H₄-、-CH₂O-、-OCH₂-, -CO-O-or-O-CO-,

c is 0, 1 or 2,

preferably, it is present in an amount of from 3 to 20% by weight, especially in an amount of from 3 to 15% by weight.

Particularly preferred compounds of formulae BC, CR and RC are selected from the group consisting of the following subformulae:

wherein alkyl and alkyl^*Each independently of the others, represents a straight-chain alkyl group having 1 to 6C atoms, (O) represents an oxygen atom or a single bond, C is 1 or 2, and alkylAnd alkenyl^*Each independently of the others, represents a linear alkenyl group having 2 to 6C atoms. alkinyl and alkinyl^*Preferably represents CH₂＝CH-、CH₂＝CHCH₂CH₂-、CH₃-CH＝CH-、CH₃-CH₂-CH＝CH-、CH₃-(CH₂)₂-CH＝CH-、CH₃-(CH₂)₃-CH ═ CH-or CH₃-CH＝CH-(CH₂)₂-。

Very particular preference is given to mixtures comprising one, two or three compounds of the formula BC-2.

o) an LC medium additionally comprising one or more fluorinated phenanthrenes and/or dibenzofurans of the following formulae:

wherein R is¹¹And R¹²Each independently of the others, having the above formula N1 for R¹¹One of the indicated meanings, b represents 0 or 1, L represents F and r represents 1,2 or 3.

Particularly preferred compounds of formulae PH and BF are selected from the group consisting of the following subformulae:

wherein R and R' each independently of one another represent a straight-chain alkyl or alkoxy radical having 1 to 7C atoms.

p) an LC medium which additionally comprises one or more monocyclic compounds of the formula

Wherein

R¹And R²Each independently of the other represents an alkyl radical having 1 to 12C atoms, one or two non-adjacent CH groups₂The radicals canSubstituted by-O-, -CH ═ CH-, -CO-, -OCO-or-COO-in such a way that the O atoms are not directly linked to one another, preferably alkyl or alkoxy having 1 to 6C atoms,

L¹and L²Each independently of the others represents F, Cl, OCF₃、CF₃、CH₃、CH₂F、CHF₂。

Preferably, L¹And L²Both represent F, or L¹And L²One represents F and the other represents Cl,

the compound of formula Y is preferably selected from the group consisting of the following subformulae:

among them, Alkyl and Alkyl^*Each independently of the others, a straight-chain alkyl group having 1 to 6C atoms, Alkoxy a straight-chain Alkoxy group having 1 to 6C atoms, alkinyl and alkinyl^*Each independently of the others, represents a linear alkenyl group having 2 to 6C atoms, and O represents an oxygen atom or a single bond. Alkinyl and alkinyl^*Preferably represents CH₂＝CH-、CH₂＝CHCH₂CH₂-、CH₃-CH＝CH-、CH₃-CH₂-CH＝CH-、CH₃-(CH₂)₂-CH＝CH-、CH₃-(CH₂)₃-CH ═ CH-or CH₃-CH＝CH-(CH₂)₂-。

Particularly preferred compounds of formula Y are selected from the group consisting of the following subformulae:

wherein Alkoxy preferably denotes a linear Alkoxy group having 3,4 or 5C atoms.

q) LC media which, apart from the stabilizers according to the invention, in particular the stabilizers of the formula I or subformulae thereof, and comonomers, do not contain a compound containing a terminal vinyloxy group (-O-CH ═ CH)₂) The compound of (1).

r) an LC medium comprising 1 to 5, preferably 1,2 or 3 stabilizers, preferably selected from the stabilizers according to the invention, in particular of the formula I or its subformulae.

s) an LC medium, wherein the proportion of the stabilizer, in particular of the formula I or its subformulae, in the overall mixture is from 1 to 1500ppm, preferably from 100 to 1000 ppm.

t) an LC medium comprising 1 to 8, preferably 1 to 5 compounds of formula CY1, CY2, PY1 and/or PY 2. The proportion of these compounds in the overall mixture is preferably from 5% to 60%, particularly preferably from 10% to 35%. The content of these individual compounds is preferably from 2% to 20% in each case.

u) an LC medium comprising 1 to 8, preferably 1 to 5 compounds of formula CY9, CY10, PY9 and/or PY 10. The proportion of these compounds in the overall mixture is preferably from 5% to 60%, particularly preferably from 10% to 35%. The content of these individual compounds is preferably from 2% to 20% in each case.

v) an LC medium comprising 1 to 10, preferably 1 to 8 compounds of the formula ZK, in particular compounds of the formulae ZK1, ZK2 and/or ZK 6. The proportion of these compounds in the overall mixture is preferably from 3% to 25%, particularly preferably from 5% to 45%. The content of these individual compounds is preferably from 2% to 20% in each case.

w) an LC medium in which the proportion of the compounds of the formulae CY, PY and ZK in the overall mixture is greater than 70%, preferably greater than 80%.

x) an LC medium, wherein the LC host mixture contains one or more compounds containing alkenyl groups, preferably selected from the group consisting of: formula CY, PY and LY wherein R¹And R²One or both of (a) and (b) represent a linear alkenyl group having 2 to 6C atoms; the formulae ZK and DK, wherein R³And R⁴One or both of (1) or R⁵And R⁶One or both of (a) and (b) represent a linear alkenyl group having 2 to 6C atoms; and formulae B2 and B3; very preferably from formulae CY15, CY16, CY24, CY32, PY15, PY16, ZK3, ZK4, DK3, DK6, B2 and B3, most preferably 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%.

y) an LC medium containing one or more, preferably 1 to 5, compounds selected from the group of the formulae PY1-PY8, very preferably of the formula PY 2. The proportion of these compounds in the overall mixture is preferably from 1% to 30%, particularly preferably from 2% to 20%. The content of these individual compounds is preferably from 1% to 20% in each case.

z) an LC medium containing one or more, preferably 1,2 or 3, compounds of the formula T2. The content of these compounds in the overall mixture is preferably from 1 to 20%.

In another preferred embodiment of the present invention, the LC medium contains an LC host mixture with positive dielectric anisotropy. Preferred embodiments of such LC media and corresponding LC host mixtures are those of the following aa) -mmm):

aa) an LC medium, characterized in that it comprises one or more compounds selected from the group of compounds of formula II and III

Wherein

R²⁰Each, identically or differently, denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15C atoms, where in addition one or more CH groups of these radicals₂The radicals may each, independently of one another, consist of-C.ident.C-, -CF in such a way that the O atoms are not directly linked to one another₂O-, -CH-, -O-, -CO-O-or-O-CO-substitution,

X²⁰each, the same or different, represents F, Cl, CN, SF₅SCN, NCS, halogenated alkyl, halogenated alkenyl, halogenated alkoxy or halogenated alkenyloxy each having up to 6C atoms, and

Y^20-24each represents H or F, the same or different;

w represents H or a methyl group,

each independently of the other represent

The compound of formula II is preferably selected from the following formulae:

wherein R is²⁰And X²⁰Have the meaning indicated above.

R²⁰Preferably represents an alkyl group having 1 to 6C atoms. X²⁰Preferably represents F. Particularly preferred are compounds of formula IIa and formula IIb, especially compounds of formula IIa and formula IIb wherein X represents F.

The compound of formula III is preferably selected from the following formulae:

wherein R is²⁰And X²⁰Have the meaning indicated above.

R²⁰Preferably represents an alkyl group having 1 to 6C atoms. X²⁰Preferably represents F. Especially preferred are compounds of formula IIIa and IIIe, especially of formula IIIa;

bb) an LC medium which additionally comprises one or more compounds of the formulae selected from:

wherein

R²⁰、X²⁰W and Y^20-23Has the meaning indicated above under formula II, and

Z²⁰represents-C₂H₄-、-(CH₂)₄-、-CH＝CH-、-CF＝CF-、-C₂F₄-、-CH₂CF₂-、-CF₂CH₂-、-CH₂O-、-OCH₂-, -COO-or-OCF₂-, also represents a single bond in formula V and formula VI and also represents-CF in formula V and formula VIII₂O-，

r represents 0 or 1, and

s represents 0 or 1;

the compound of formula IV is preferably selected from the following formulae:

wherein R is²⁰And X²⁰Have the meaning indicated above.

R²⁰Preferably represents an alkyl group having 1 to 6C atoms. X²⁰Preferably represents F or OCF₃And OCF ═ CF₂Or Cl;

the compound of formula V is preferably selected from the following formulae:

wherein R is²⁰And X²⁰Have the meaning indicated above.

R²⁰Preferably represents an alkyl group having 1 to 6C atoms. X²⁰Preferably F and OCF₃And OCHF₂、CF₃、OCF＝CF₂And OCH ═ CF₂；

The compound of formula VI is preferably selected from the following formulae:

wherein R is²⁰And X²⁰Have the meaning indicated above.

R²⁰Preferably represents an alkyl group having 1 to 6C atoms. X²⁰Preferably represents F, and OCF₃、CF₃、CF＝CF₂、OCHF₂And OCH ═ CF₂；

The compound of formula VII is preferably selected from the following formulae:

wherein R is²⁰And X²⁰Have the meaning indicated above.

R²⁰Preferably represents an alkyl group having 1 to 6C atoms. X²⁰Preferably represents F, and OCF₃、OCHF₂And OCH ═ CF₂。

cc) medium further comprises one or more compounds selected from the group of compounds of formulae ZK1 to ZK10 given above. Especially preferred are compounds of formulae ZK1 and ZK 3. Particularly preferred compounds of formula ZK are selected from the group consisting of sub-formulae ZK1a, ZK1b, ZK1c, ZK3a, ZK3b, ZK3c, and ZK3 d.

dd) medium additionally comprises one or more compounds selected from the formulae DK1 to DK12 given above. A particularly preferred compound is DK 3.

ee) medium further comprises one or more compounds of the formula selected from:

wherein X²⁰Have the meaning indicated above, an

L represents H or F, and L represents hydrogen or F,

"alkenyl" means C_2-6-alkenyl.

ff) the compounds of the formulae DK-3a and IX are preferably selected from the following formulae:

wherein "alkyl" represents C_1-6Alkyl, preferably n-C₃H₇、n-C₄H₉Or n-C₅H₁₁In particular n-C₃H₇。

gg) medium further comprises one or more compounds selected from the group of formulae B1, B2 and B3 given above, preferably selected from formula B2. The compounds of the formulae B1 to B3 are particularly preferably selected from the formulae B1a, B2a, B2B and B2 c.

hh) medium further comprises one or more compounds selected from the group consisting of:

wherein L is²⁰Represents H or F, and R²¹And R²²Each, identically or differently, denotes n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6C atoms, and preferably each, identically or differently, denotes alkyl having 1 to 6C atoms.

ii) the medium comprises one or more compounds of the formula:

w, R therein²⁰、X²⁰And Y^20-23Have the meaning indicated in the formula III, and

each independently of the other represent

And is

To represent

The compounds of formulae XI and XII are preferably selected from the following formulae:

wherein R is²⁰And X²⁰Have the meaning indicated above, and preferably R²⁰Represents an alkyl group having 1 to 6C atoms, and X²⁰Represents F.

The mixtures according to the invention particularly preferably comprise at least one compound of the formulae XIIa and/or XIIe.

jj) the medium comprises one or more compounds of the formula T given above, preferably selected from the group of compounds of the formulae T21 to T23 and T25 to T27.

Especially preferred are compounds of formula T21 to T23. Very particularly preferred are compounds of the formula:

kk) the medium comprises one or more compounds selected from the group of formulae DK9, DK10 and DK11 given above.

ll) the medium additionally comprises one or more compounds of the formulae selected from:

wherein R is²⁰And X²⁰Each independently of the other having one of the meanings indicated above, and Y^20-23Each independently of the other represents H or F. X²⁰Preferably F, Cl, CF₃、OCF₃Or OCHF₂。R²⁰Preferably represents alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6C atoms.

The mixtures according to the invention particularly preferably comprise one or more compounds of the formula XVIII-a,

wherein R is²⁰Have the meaning indicated above. R²⁰Preferably straight-chain alkyl radicals, in particular ethyl, n-propyl, n-butyl and n-pentyl radicals, and very particularly preferably n-propyl radicals. The compounds of the formula XVIII, in particular of the formula XVIII-a, are preferably used in the mixtures according to the invention in amounts of from 0.5 to 20% by weight, particularly preferably from 1 to 15% by weight.

mm) medium additionally comprises one or more compounds of the formula XIX,

wherein R is²⁰、X²⁰And Y^20-25Has the meaning indicated in formula I, s represents 0 or 1, and

to represent

In formula XIX, X²⁰It may also represent an alkyl group having 1 to 6C atoms or an alkoxy group having 1 to 6C atoms. The alkyl or alkoxy groups are preferably straight-chain.

R²⁰Preferably represents an alkyl group having 1 to 6C atoms. X²⁰Preferably represents F;

the compounds of formula XIX are preferably selected from the following formulae:

wherein R is²⁰、X²⁰And Y²⁰Have the meaning indicated above. R²⁰Preferably represents an alkyl group having 1 to 6C atoms. X²⁰Preferably represents F, and Y²⁰Preferably F;

preferably is

-R²⁰Is a straight chain alkyl or alkenyl group having 2 to 6C atoms;

nn) medium comprises one or more compounds of the formulae G1 to G4 given above, preferably selected from G1 and G2, wherein alkyl represents C_1-6-alkyl, L^xRepresents H, and X represents F or Cl. In G2, X particularly preferably represents Cl.

oo) medium comprises one or more compounds of the following formulae:

wherein R is²⁰And X²⁰Have the meaning indicated above. R²⁰Preferably represents an alkyl group having 1 to 6C atoms. X²⁰Preferably represents F. The media according to the invention particularly preferably comprise one or more compounds of the formula XXII, in which X²⁰Preferably represents F. The compounds of the formulae XX to XXII are preferably used in the mixtures according to the invention in amounts of from 1 to 20% by weight, particularly preferably from 1 to 15% by weight. Particularly preferred mixtures comprise at least one compound of the formula XXII.

pp) medium comprises one or more compounds of the following formulae of pyrimidine or pyridine compounds:

wherein R is²⁰And X²⁰Have the meaning indicated above. R²⁰Preferably represents an alkyl group having 1 to 6C atoms. X²⁰Preferably represents F. The media according to the invention particularly preferably comprise one or more compounds of the formula M-1, in which X²⁰Preferably represents F. The compounds of the formula M-1-M-3 are preferably represented by 1Amounts of from 20% by weight, particularly preferably from 1 to 15% by weight, are used in the mixtures according to the invention.

Other preferred embodiments are indicated below:

qq) the medium comprises two or more compounds of formula XII, in particular XIIe;

rr) medium contains 2 to 30% by weight, preferably 3 to 20% by weight, particularly preferably 3 to 15% by weight, of a compound of the formula XII;

ss) the medium comprises, in addition to the compound of the formula XII, a further compound selected from the group of compounds of the formulae II, III, IX to XIII, XVII and XVIII;

tt) the proportion of the compounds of the formulae II, III, IX-XI, XIII, XVII and XVIII in the overall mixture is from 40 to 95% by weight;

uu) medium comprises 10 to 50% by weight, particularly preferably 12 to 40% by weight, of a compound of the formula II and/or III;

vv) the medium contains 20 to 70% by weight, particularly preferably 25 to 65% by weight, of a compound of the formulae IX to XIII;

ww) the medium contains from 4 to 30% by weight, particularly preferably from 5 to 20% by weight, of a compound of the formula XVII;

xx) the medium comprises from 1 to 20% by weight, particularly preferably from 2 to 15% by weight, of a compound of the formula XVIII;

yy) media comprises at least two compounds of the following formulae:

zz) media comprise at least two compounds of the formula:

aaa) medium comprises at least two compounds of formula XIIa and at least two compounds of formula XIIe.

bbb) the medium comprises at least one compound of formula XIIa and at least one compound of formula XIIe and at least one compound of formula IIIa.

ccc) medium contains at least two compounds of formula XIIa and at least two compounds of formula XIIe and at least one compound of formula IIIa.

ddd) medium contains a total of > 25% by weight, preferably > 30% by weight, of one or more compounds of the formula XII.

eee) medium comprises ≥ 20% by weight, preferably ≥ 24% by weight, preferably 25-60% by weight, of a compound of formula ZK3, especially of formula ZK3a,

fff) medium comprising at least one compound selected from the group of compounds ZK3a, ZK3b and ZK3c, preferably ZK3a, in combination with compound ZK3d

ggg) the medium comprises at least one compound of formula DPGU-n-F.

hhh) medium comprises at least one compound of the formula CDUQU-n-F.

iii) the medium comprises at least one compound of the formula CPU-n-OXF.

jjj) the medium comprises at least one compound of formula CPGU-3-OT.

kkk) medium comprises at least one compound of the formula PPGU-n-F.

lll) medium comprises at least one compound of the formula PGP-n-m, preferably two or three compounds.

mmm) medium comprising at least one compound of formula PGP-2-2V having the structure

In a preferred embodiment, the liquid-crystalline mixtures according to the invention further comprise a polymerizable component C) comprising one or more polymerizable compounds.

The polymerizable component C) according to the invention comprises, preferably consists of: one or more polymerizable compounds of the formula P,

P^a-Sp^a-P^b P

wherein the individual radicals have the following meanings:

P^a、P^beach independently of the other represents a polymerizable group,

Sp^arepresents a spacer group.

Preference is given to the group P^a/bEach and independently selected from the group consisting of: acrylate, methacrylate, fluoroacrylate, vinyloxy, chloroacrylate, oxetane or epoxide groups.

Preferably a spacer group Sp^aSelected from the formula-X ' -Sp ' -X ' -

Sp "represents an alkylene group having 1 to 25, preferably 1 to 20, C atoms, which is optionally mono-or polysubstituted with F, Cl, Br, I or CN, and wherein, in addition, one or more non-adjacent CH' s₂The groups may each be replaced independently of one another by the following in such a way that the O and/or S atoms are not directly connected to one another: -O-, -S-, -NH-, -N (R)⁰)-、-Si(R⁰⁰R⁰⁰⁰)-、-CO-、-CO-O-、-O-CO-、-O-CO-O-、-S-CO-、-CO-S-、-N(R⁰⁰)-CO-O-、-O-CO-N(R⁰⁰)-、-N(R⁰⁰)-CO-N(R⁰⁰) -, -CH-or-C.ident.C-,

x' each independently represents-O-, -S-, -CO-O-, -O-CO-O-, -CO-N (R)⁰⁰)-、-N(R⁰⁰)-CO-、-N(R⁰⁰)-CO-N(R⁰⁰)-、-OCH₂-、-CH₂O-、-SCH₂-、-CH₂S-、-CF₂O-、-OCF₂-、-CF₂S-、-SCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-、-CH＝N-、-N＝CH-、-N＝N-、-CH＝CR⁰-、-CY³＝CY⁴-, -C.ident.C-, -CH-CO-O-, -O-CO-CH-or a single bond,

R⁰、R⁰⁰and R⁰⁰⁰Each independently of the other represents H orAn alkyl group having 1 to 12C atoms, and

Y³and Y⁴Each representing H, F, Cl or CN, the same or different.

X' is preferably-O-, -S-, -CO-, -C (O) O-, -OC (O) -, -O-C (O) O-, -CO-NR-⁰-、-NR⁰-CO-、-NR⁰-CO-NR⁰-or a single bond.

Typical spacer groups Sp "are; for example- (CH)₂)_p1-、-(CH₂CH₂O)_q1-CH₂CH₂-、-CH₂CH₂-S-CH₂CH₂-、-CH₂CH₂-NH-CH₂CH₂-or- (SiR)⁰⁰R⁰⁰⁰-O)_p1-, where p1 and q1 are integers from 1 to 20, and R⁰⁰And R⁰⁰⁰Have the meaning indicated above.

A particularly preferred group X ' -Sp ' -X ' -is- (CH)₂)_p1-、-(CH₂CH₂O)_q1-CH₂CH₂--(CH₂)_p1-O-、-(CH₂)_p1-O-CO-、-(CH₂)_p1-O-CO-O-、-O-(CH₂)_p1-O-、-O-CO-(CH₂)_p1-O-CO-、-O-CO-O-(CH₂)_p1-O-CO-O-、-O-(CH₂)_p1-、-O-CO-(CH₂)_p1-、-O-CO-O-(CH₂)_p1-, wherein p1 and q1 have the meanings indicated above.

In each case, the radical Sp "is particularly preferably, for example, a linear ethylene radical, propylene radical, butylene radical, pentylene radical, hexylene radical, heptylene radical, octylene radical, nonylene radical, decylene radical, undecylene radical, dodecylene radical, octadecylene radical, ethyleneoxyethylene radical, methyleneoxybutylene radical, ethylenethioethylene radical, ethylene-N-methyliminoethylene radical, 1-methylalkylene radical, ethylene radical, propylene radical and butylene radical,

furthermore- (CH)₂CH₂O)_q1-(CH₂CH₂)_p1-、-(CH₂CH₂)_p1-(OCH₂CH₂)_q1-or- (CH)₂CH₂)_p1-(CH₂CH₂O)_q1-(CH₂CH₂)r₁Wherein p1, q1 and r1 each and independently represent 1,2,3,4, 5,6, 7,8, 9, 10, 11 or 12.

Particularly preferred monomers of formula P are the following:

if only photoreactive components A) without any polymerizable component C) are used, a known problem of these materials is that they form very thin layers of about 5-20nm thickness. For some applications, such thin layers may not be sufficient to pass the stringent reliability tests required by the display industry. Typically, these tests may include, but are not limited to, pressure or drop tests and/or thermal stress. Such tests were conducted on PI-based alignment layers such that they were in some cases subjected to a coating and two-step thermal curing process to give thick (60-80nm) layers with robust mechanical properties.

Another common test in the display industry is surface "hardness". In which the abrasive object is moved over the entire surface in order to see if deformation or visible damage is caused. Passing such hardness tests is extremely difficult for thin layers, as they are generally more susceptible to contact damage. In addition to hardness, another consideration is long-term reliability testing of parameters such as Voltage Holding Ratio (VHR). Since surfactants and other chemicals are used in the glass cleaning process, there is a risk that these may "leak" through the (photo) alignment layer during the lifetime of the product. This can lead to a reduction in VHR and a reduction in the visible display quality. In this respect, the use of LC mixtures comprising a photoreactive component a) comprising one or more compounds of formula I in combination with a polymerizable component C) comprising one or more compounds of formula P shows significant advantages with respect to reliability problems over LC mixtures comprising only a photoreactive component a) comprising one or more compounds of formula I or even in combination with a polymerizable component C) comprising one or more polymerizable liquid crystal compounds.

The total amount of polymerizable component C) in the LC mixture is preferably in the range from 0.1% to 5%, more preferably in the range from 0.3% to 3%, in particular in the range from 0.5% to 2%.

The overall amount of the compound or compounds of the formula P in the polymerizable component C) is preferably in the range from 90% to 100%, more preferably in the range from 95% to 100%, in particular in the range from 99% to 100%, in particular the polymerizable component C consists of one, two, three or more compounds of the formula P.

The polymerisable compounds of the formulae I and P are also suitable for polymerisation without initiator, which is accompanied by a number of advantages, such as lower material costs and in particular reduced contamination of the LC medium by possible residual amounts of initiator or degradation products thereof. Thus, the polymerization can also be carried out without adding an initiator. Thus, in a preferred embodiment, the LC medium does not comprise a polymerization initiator.

The polymerisable component C) or the LC medium as a whole may also comprise one or more stabilisers to prevent unwanted spontaneous polymerisation of the RM, for example during storage or transport. Suitable types and amounts of stabilizers are known to the person skilled in the art and are described in the literature. Particularly suitable are, for example, those fromCommercial stabilizers of the series (BASF SE), e.g.1076. If stabilizers are used, the proportion thereof is preferably from 10ppm to 10,000ppm, particularly preferably from 50ppm to 1000ppm, based on the total amount of RM or polymerizable components.

The media of 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 the compounds of the formula P of the invention. The medium preferably comprises one, two or three, more preferably one or two and most preferably one compound of the formula P according to the invention.

With the aid of suitable additives, the liquid-crystalline phases of the invention can be modified so that they can be used in all types of liquid-crystal display components which 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 producing colored guest-host systems or substances can be added to improve the dielectric anisotropy, viscosity and/or alignment of the nematic phase.

The media of the invention are prepared in a manner conventional per se. In general, it is preferred to dissolve the components in each other at elevated temperature.

The present invention therefore further relates to a process for producing the LC media of the invention, which comprises the step of mixing one or more compounds of the formula I with a liquid-crystalline component B) comprising one or more mesogenic or liquid-crystalline compounds as set forth above.

The invention further relates to a method for manufacturing a liquid crystal display, comprising at least the following steps:

providing a first substrate comprising pixel electrodes and a common electrode for generating an electric field in the pixel area substantially parallel to a surface of the first substrate;

providing a second substrate arranged opposite to the first substrate;

interposing between the first substrate and the second substrate a liquid-crystal mixture comprising one or more compounds of formula I, component B) and component C);

irradiating the liquid crystal mixture with linearly polarized light to cause photoalignment of the liquid crystals;

polymerizable compounds for curing the liquid-crystalline mixture by irradiation with ultraviolet light or visible light having a wavelength of 450nm or less.

The invention further relates to the use of the liquid-crystal mixtures according to the invention for producing liquid-crystal displays.

The invention further relates to a liquid crystal display manufactured by the method set forth above.

Hereinafter, the production method of the present invention is explained in more detail.

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 a pixel region. Different kinds of displays with at least two electrodes on one substrate are known to the person skilled in the art, the most significant difference being that both the pixel and common electrodes are structured (as is typical for IPS displays) or that only the pixel electrode is structured and the common electrode is not structured (as is the case for FFS displays).

It has to be understood that the invention relates to any kind of electrode configuration suitable for generating an electric field in the pixel area substantially parallel to the first substrate surface; as mentioned above, i.e. IPS and FFS displays.

The method according to the invention is independent of the type of substrate or surface substance which is in contact with the liquid-crystal mixture according to the invention during and after the method. Examples of substances for the substrate or surface include polyimide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), silicon nitride (SiN)_x) And silicon dioxide (SiO)₂) The organic polymer of (1). The method is particularly suitable for use in displays containing substrates that do not have a polyimide layer on one or more of the surfaces in contact with the liquid crystal.

In the case where one or more of the substrates contains a polyimide layer, then the polyimide may be rubbed or ungrasped, preferably ungrasped.

The invention therefore relates to a display prepared by the method according to the invention, wherein the substrate contains a rubbed or non-rubbed polyimide layer, preferably a non-rubbed polyimide layer.

The invention further relates to a display prepared by the method according to the invention, wherein one or only one of the top and bottom substrates contains a polyimide layer.

In one embodiment of the present invention, the liquid crystal composition is injected between the first and second substrates or filled into the cell by capillary force after the first and second substrates are combined. 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 the first substrate in a method called "one drop filling" (ODF) method described in, for example, JPS63-179323 and JPH10-239694, or using an inkjet printing (IJP) method.

In a preferred embodiment, the method according to the invention contains a method step in which the liquid crystal inside the display panel is left for a period of time in order to redistribute the liquid crystal medium uniformly inside the panel (herein referred to as "annealing").

However, it is also preferred to combine the annealing step with a previous step, e.g. edge sealant pre-cure. In this case, a "separate" annealing step may not be required at all.

For the production of the displays of the invention, it is preferred to redistribute the photoreactive mesogens of formula I in the panel. After filling and assembly, the display panel is annealed for a time between 1min and 3h, preferably between 2min and 1h and most preferably between 5min and 30 min. Annealing is preferably performed at room temperature.

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

In a preferred embodiment, one or more of the method steps of filling the display, annealing, photoaligning and curing the polymerizable compound are carried out at a temperature above the clearing point of the liquid crystal host mixture.

During photoalignment of the liquid crystals inside the liquid crystal panel, anisotropy is induced by exposing the display or the liquid crystal layer to linearly polarized light.

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 polarized light and further cured in a second step using linearly polarized or unpolarized UV light. In a second step, component C) is also further cured.

In another preferred embodiment, the linearly polarized light applied according to the process of the invention is ultraviolet light, which enables simultaneous photoalignment and photocuring of the photoreactive component a) comprising one or more compounds of formula I and photocuring of the polymerizable component C).

Photoalignment of the photoreactive compound of formula I and curing of the polymerizable group of the compound of formula I and curing of the optional polymerizable compound of formula P can be performed simultaneously or stepwise. In the case of a process divided into different steps, the individual steps can be carried out at the same temperature or at different temperatures.

After the photo-alignment and curing step, a so-called "post-curing" step may be carried out to remove unreacted polymerizable compounds, optionally at reduced temperature, by irradiation with UV light and/or visible light (both linear or unpolarized). The post-curing is preferably carried out at above 0 ℃ and below the clearing point of the LC mixture utilized, preferably at 20 ℃ and below 60 ℃ and most preferably at above 20 ℃ and below 40 ℃.

The polymerizable compound is optionally polymerized or crosslinked under the application of an electric field (if the polymerizable compound contains two or more polymerizable groups). The polymerization may be carried out in one or more steps.

Suitable and preferred polymerization methods for component C) are, for example, thermal polymerization or photopolymerization, preferably photopolymerization, in particular UV photopolymerization. One or more initiators may also optionally be added here. Suitable conditions for the polymerization 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 polymerization are, for example, the commercially available photoinitiatorsOr(BASF SE). If an initiator is used, the proportion thereof is preferably from 0.001 to 5% by weight, particularly preferably 0.001 to 1 wt%.

The invention also relates to electro-optical liquid-crystal display elements containing the liquid-crystalline media according to the invention, preferably with planar alignment. In a preferred embodiment, the liquid crystal display has an IPS or FFS mode.

Other combinations of embodiments and variations of the invention according to the present description are produced by the claims.

The invention is explained in more detail below with reference to working examples, without intending to be limited thereby. The person skilled in the art will be able to gather from the working examples working details that are not given in the general description, to summarize them and to apply them to specific problems according to the general expert knowledge.

In addition to the common and well-known abbreviations, the following abbreviations are used:

c: a crystalline phase; n: a nematic phase; sm: a smectic phase; i: an isotropic phase. The numbers between these symbols show the transition temperature of the relevant substance.

Unless otherwise indicated, temperature data are expressed in degrees celsius.

The physical, physicochemical or electro-optical parameters are determined by generally known methods, such as, inter alia, the manual "Merck Liquid Crystals--Physical Properties of Liquid Crystals-Description of the Measurement Methods ", 1998, Merck KGaA, Darmstadt.

In the above and below, Δ n represents optical anisotropy (589nm,20 ℃) and Δ ε represents dielectric anisotropy (1kHz,20 ℃). The dielectric anisotropy. DELTA.. di-elect cons.was measured at 20 ℃ and 1 kHz. The optical anisotropy Δ n was measured at 20 ℃ and a wavelength of 589.3 nm.

The values of Δ ε and Δ n and the rotational viscosity (. gamma.) of the compounds of the present invention₁) By free 5% to 10% of the respective compounds of the invention and 90% to 95% of the commercially available liquid-crystal mixtures ZLI-2857 (for. DELTA.. epsilon.) or ZLI-4792 (for. DELTA.n,. gamma.)₁) (mixture, Merck KGaA, Darmstadt)Linear extrapolation.

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

In the present invention and in particular in the following examples, the structure of the mesogenic compounds is indicated by means of abbreviations (also known as acronyms). Among these acronyms, the chemical formulae are abbreviated as follows using the following tables a to C. All radicals C_nH_2n+1、C_mH_2m+1And C_lH_2l+1Or C_nH_2n-1、C_mH_2m-1And C_lH_2l-1Represents a straight-chain alkyl or alkenyl group, preferably a 1E-alkenyl group, each having n, m and l C atoms, respectively. Table a lists the codes for the ring elements of the core structure of the compounds, while table B shows the linking groups. Table C gives the meaning of the codes for the left-hand or right-hand end groups. The acronym is comprised of the code for the ring element with the optional linker, followed by the code for the first hyphen and left hand end group, and the code for the second hyphen and right hand end group. Table D shows illustrative structures of the compounds and their corresponding abbreviations.

Table a: ring element

Table B: linking group

Table C: terminal group

For use with each other or otherwise

Where n and m each represent an integer and the three points are placeholders for other abbreviations from this table.

The following table shows illustrative structures and their corresponding abbreviations. These are shown to illustrate the meaning of the abbreviation rules. Furthermore, it represents a compound which is preferably used.

Table D: illustrative structures

CC-n-m

CC-n-Om

CC-n-V

CC-n-Vm

CC-n-mV

CC-n-mVl

CC-V-V

CC-V-mV

CC-V-Vm

CC-Vn-mV

CC-nV-mV

CC-nV-Vm

CP-n-m

CP-nO-m

CP-n-Om

CP-V-m

CP-Vn-m

CP-nV-m

CP-V-V

CP-V-mV

CP-V-Vm

CP-Vn-mV

CP-nV-mV

CP-nV-Vm

PP-n-m

PP-nO-m

PP-n-Om

PP-n-V

PP-n-Vm

PP-n-mV

PP-n-mVl

CCP-n-m

CCP-nO-m

CCP-n-Om

CCP-n-V

CCP-n-Vm

CCP-n-mV

CCP-n-mVl

CCP-V-m

CCP-nV-m

CCP-Vn-m

CCP-nVm-l

CPP-n-m

CPG-n-m

CGP-n-m

CPP-nO-m

CPP-n-Om

CPP-V-m

CPP-nV-m

CPP-Vn-m

CPP-nVm-l

PGP-n-m

PGP-n-V

PGP-n-Vm

PGP-n-mV

PGP-n-mVl

CCEC-n-m

CCEC-n-Om

CCEP-n-m

CCEP-n-Om

CPPC-n-m

CGPC-n-m

CCPC-n-m

CCZPC-n-m

CPGP-n-m

CPGP-n-mV

CPGP-n-mVl

PGIGP-n-m

CP-n-F

CP-n-CL

GP-n-F

GP-n-CL

CCP-n-OT

CCG-n-OT

CCP-n-T

CCG-n-F

CCG-V-F

CCU-n-F

CDU-n-F

CPG-n-F

CPU-n-F

CGU-n-F

PGU-n-F

GGP-n-F

GGP-n-CL

PGIGI-n-F

PGIGI-n-CL

CCPU-n-F

CCGU-n-F

CPGU-n-F

CPGU-n-OT

DPGU-n-F

PPGU-n-F

CCZU-n-F

CCQP-n-F

CCQG-n-F

CCQU-n-F

PPQG-n-F

PPQU-n-F

PGQU-n-F

GGQU-n-F

PUQU-n-F

MUQU-n-F

NUQU-n-F

CDUQU-n-F

CPUQU-n-F

CGUQU-n-F

PGPQP-n-F

PGPQG-n-F

PGPQU-n-F

PGUQU-n-F

APUQU-n-F

DGUQU-n-F

Wherein n, m and l preferably represent, independently of one another, 1 to 7.

The following table (table E) shows illustrative compounds that can be used as additional stabilizers in the mesogenic media of the present invention.

TABLE E

Table E shows possible stabilizers that may be added to the LC media of the present invention.

(where n represents an integer of 1 to 12, preferably 1,2,3,4, 5,6, 7 or 8, the terminal methyl group not being shown).

The LC medium preferably comprises from 0 to 10% by weight, in particular from 1ppm to 5% by weight, particularly preferably from 1ppm to 1% by weight, of stabilizer.

Table F below shows illustrative compounds that can be preferably used as chiral dopants in the mesogenic media of the present invention.

TABLE F

C 15

CB 15

CM 21

CM 44

CM 45

CM 47

R/S-811

R/S-1011

R/S-2011

R/S-3011

R/S-4011

R/S-5011

In a preferred embodiment of the invention, the mesogenic medium comprises one or more compounds selected from the group of compounds of table F.

The mesogenic medium according to the present application preferably comprises two or more, preferably four or more compounds selected from the group consisting of the compounds of the tables above.

The liquid-crystalline medium according to the invention preferably comprises

-7 or more, preferably 8 or more, individual compounds of different formulae, preferably 3 or more, particularly preferably 4 or more, selected from the group of compounds of table D.

Hereinafter, the present invention will be explained in more detail and specifically with reference to examples, which, however, are not intended to limit the present invention.

Examples

The photoreactive compound of formula I utilized:

polymerizable Compounds utilized for comparison

The polymerizable compound of formula P utilized:

nematic host mixture

Nematic LC host mixtures N-1 to N-15 were prepared as indicated in the following table:

mixture N-1:

condition

All examples detailed in this working example were subjected to the standard conditions for SA-IPS/FFS materials. In detail, 35mWcm after wire grid polarizer^-2The exposure power of (2) was used with a UV source of an Omnicure S2000 mercury lamp. Photoreactive compound I-1 required exposure with a 320nm cut-off filter, and all other additives required a 360nm cut-off filter. As stated in the data sheet, the exposure time is typically in the range of 30 seconds to 180 seconds. All samples were exposed with the same cassette (cell) held at 100 ℃. The cassette used was a 6um PI-free 1cm x 1cm ITO electrode area and the glass type was Corning's Eagle XG AF glass (0.7mm thick).

Examples of mixtures

The nematic LC mixtures M-1 to M-64 according to the invention are prepared from the nematic host mixtures N-1 to 15 listed above, and the given amounts of photoreactive compound (I) and polymerizable compound (P) are mixed according to the compositions given in the table below.

Alignment quality

Alignment quality after a given exposure time was studied on a lamp box between crossed polarizers. The results are shown in the following table.

Examples of mixtures	Exposure time (seconds)	Alignment quality

M 30	60	++
			M 31	60	++
M 32	120	++
			M 33	120	++
M 34	60	++
			M 35	60	++
M 36	120	++
			M 37	120	++
M 38	120	+
			M 39	120	+
M 40	120	++
			M 41	120	+
M 42	60	++
			M 43	60	++
M 44	60	++
			M 45	60	++
M 46	120	++
			M 47	120	++

Alignment quality: (+) Excellent, (+) good, (o) acceptable, (-) poor

The results clearly show that there are advantages in using the polymerizable compound of formula P. This is especially attractive when concentrations above 0.5% are required, and especially when concentrations above 0.7%. Since these materials are isotropic, it is very surprising that the polymerizable compound of formula P does not show any negative impact on the dark state or alignment quality even at a concentration of 2.0%. These findings allow the formation of layers with much greater thicknesses than previously possible with the SA-IPS/FFS system, e.g. a system that yields layer thicknesses measured by AFM above 15nm, preferably above 20nm and more preferably above 25 nm.

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