Liquid crystal medium
By using LC media containing the compound of formula I in an LCD display, combined with antioxidants and light stabilizers, the problem of image residue and response time after light load and temperature load is solved, and better image quality and stability are achieved.
Patent Information
- Application Number
- CN202411854849.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-12-19
- Filing Date
- 2024-12-17
- Publication Date
- 2025-06-20
AI Technical Summary
The existing LCD technology is difficult to effectively reduce short-term and long-term image residues after optical loads and/or temperature loads, and at the same time, the response time is long and the requirements for low temperature stability and UV radiation stability are not high.
LC media using one or more compounds of formula I containing specific substituents in combination with antioxidants and light stabilizers, preferably for LCD displays in FFS and IPS modes.
Low short-term image residue and low long-term image residue, short response time, good low temperature stability and stability to UV radiation and temperature are achieved.
Smart Images

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Figure BDA0005191531720000041 
Figure BDA0005191531720000051
Abstract
Description
Technical Field
[0001] The present invention relates to liquid crystal (LC) media, and to energy-saving liquid crystal displays (LCDs) containing these media, in particular to high-contrast, fast-switching gaming displays and AR / VR headsets having reduced short-term image retention and reduced long-term image retention especially after light loading and / or temperature loading. In particular, it relates to the following types of LC displays: TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-FFS, SA-HB-FFS, SA-XB-FFS, polymer-stabilized SA-HB-FFS, polymer-stabilized SA-XB-FFS, positive VA or positive PS-VA types. In a preferred embodiment, the LC medium has positive dielectric anisotropy. Background Art
[0002] LCDs are used for displaying information in many fields. LCDs are used both in direct-view displays and in projection-type displays. The electro-optical modes used are, for example, the twisted nematic (TN), super-twisted nematic (STN), optically compensated bend (OCB) and electrically controlled birefringence (ECB) modes and their various variants, among others. All these modes utilize an electric field generated substantially perpendicular to the substrates and the LC layer.
[0003] In addition to these modes, there are electro-optical modes that utilize an electric field substantially parallel to the substrates or the LC layer. For example, WO91 / 10936 discloses an LC display in which an electrical signal is generated in such a way that the electric field has a significant component parallel to the LC layer, and since then this liquid crystal display has been called an "in-plane switching" (IPS) display. For example, the principle of operating such a display is described by R.A. Soref in Journal of Applied Physics, Vol. 45, No. 12, pp. 5466-5468 (1974).
[0004] An IPS display contains an LC layer between two substrates with planar alignment, where two electrodes are arranged on only one of the two substrates and preferably have an interdigitated comb-like structure. When a voltage is applied to the electrodes, an electric field is generated between them that has a significant component parallel to the LC layer. This causes the LC molecules to reorient in the layer plane.
[0005] For example, EP 0 588 568 discloses various possibilities for designing the electrodes and addressing IPS displays. DE 198 24137 likewise describes various embodiments of such IPS displays.
[0006] For example, LC materials for this type of IPS display are described in DE 195 28 104.
[0007] Furthermore, so-called "fringe field switching" (FFS) displays have been reported (see in particular S.H. Jung et al., Jpn. J. Appl. Phys., Vol. 43, No. 3, 2004, 1028), which contain two electrodes on the same substrate, one of which is structured in a comb-like manner and the other is unstructured. As a result, a strong so-called "fringe field", i.e., a strong electric field near the electrode edges, and an electric field with both strong vertical and strong horizontal components throughout the cell are generated. FFS displays have a low viewing angle dependence of contrast. FFS displays typically contain an LC medium with positive dielectric anisotropy and an alignment layer, usually made of polyimide, which provides planar alignment for the molecules of the LC medium.
[0008] IPS and FFS electro-optical mode LCDs are particularly suitable for modern desktop monitors, televisions and multimedia applications. The LC medium according to the invention is preferably used in this type of display. Generally, a dielectrically positive LC medium with a rather low value of dielectric anisotropy is used in FFS displays, but in some cases, an LC medium with a dielectric anisotropy of only about 3 or even less is also used in IPS displays.
[0009] The HB-FFS mode has achieved further improvement. One of the unique features of the HB-FFS mode compared to traditional FFS technology is that it can achieve higher transmittance, which allows the panel to operate with lower power consumption.
[0010] Another recently developed mode is the XB-FFS mode, in which the LC medium additionally contains a polar liquid crystal compound with low dielectric anisotropy.
[0011] FFS and IPS displays can be used as active matrix displays (AMD) or passive matrix displays (PMD). In the case of an active matrix display, individual pixels are typically addressed by integrated non-linear active elements, such as thin film transistors (TFT), while in the case of a passive matrix display, individual pixels are typically addressed by multiplex methods known in the prior art. The display according to the invention is preferably addressed by active matrix, preferably by a TFT matrix. However, the LC medium according to the invention can also be advantageously used in displays with other known addressing methods.
[0012] Typical applications of IPS and FFS technologies are monitors, laptops, TVs, mobile phones, tablets, etc. Both IPS and FFS technologies have certain advantages over other LCD technologies (such as vertical alignment (VA) technology), such as the wide viewing angle dependence of contrast ratio.
[0013] Providing an LC medium and its use in a display having a combination of particularly low short-term image retention and low long-term image retention and short response time is a core challenge for modern FFS and IPS applications. In addition, modern applications also require good low-temperature stability and stability against UV radiation and increased temperature. Summary of the Invention
[0014] The object of the present invention is to provide an LC medium, in particular for FFS and IPS displays, which is also used in TN, positive VA or STN displays, in particular for active matrix displays (such as those addressed by TFTs), which has low short-term image retention and low long-term image retention and short response time. This object is achieved by providing the LC medium as described and claimed below.
[0015] The LC medium according to the present invention is particularly suitable for LC displays in FFS, HB-FFS, XB-FFS and IPS modes based on dielectrically positive liquid crystals and their polymer-stabilized variants.
[0016] Surprisingly, the above technical problem is achieved by providing the LC medium as described and claimed below.
[0017] It has now surprisingly been found that the LC medium according to the present invention contains one or more compounds of formula I
[0018]
[0019] wherein each substituent is specifically defined in claim 1.
[0020] in combination with one or more antioxidants and optionally one or more light stabilizers,
[0021] The LC medium shows some excellent improvements, such as low short-term image retention and low long-term image retention, and is capable of achieving short response time, especially when used in an FFS mode display. The compounds of formula I themselves are known in the prior art.
[0022] Additionally, the LC medium according to the present invention has high-definition bright spots, excellent low-temperature stability (LTS), and provides the best moving picture quality and improved overall image quality, especially high contrast ratio.
[0023] The present invention relates to an LC medium, characterized in that it contains one or more compounds of formula I
[0024]
[0025] Each substituent, each time it occurs, is the same or different and each independently of the others has the following meanings:
[0026] R 0 is an alkyl group having 1 to 12 C atoms, or an alkenyl group having 2 to 12 C atoms, where one or more CH₂ groups are optionally replaced by -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O- or -O-CO- in such a way that O atoms are not directly linked to one another, and where one or more H atoms may be replaced by halogen atoms;
[0027] X 0 is a halogen atom, -CN, -SCN, -NCS or an alkyl or alkoxy group having 1 to 6 C atoms, or an alkenyl or alkenyloxy group having 2 to 6 C atoms, where one or more H atoms have been replaced by halogen atoms;
[0028] L 1 and L 2 each independently of the other is H, F or Cl, where L 1 and L 2 do not both represent H;
[0029] Y 0 is H or CH₃,
[0030] One or more antioxidants and optionally one or more light stabilizers.
[0031] The antioxidants used in the present invention are known per se in the prior art and are not particularly limited. The inventors have found that the combination of antioxidants described by formula ST shown below with the compounds of formula I allows particularly low rotational viscosities γ1 and low short-term and long-term image residues to be achieved, especially after high radiation exposure or thermal stress:
[0032]
[0033] where each substituent has the following meanings:
[0034] X 21 and X 22 each independently of the other represents -O-, -CH₂-, -CHR 23 - or -N-R 23 -;
[0035] R 21 and R 22each independently represents a H atom or an alkyl- or alkoxy group having 1 to 12 C atoms, an alkenyl, alkynyl, alkenyloxy or alkoxyalkyl group having 2 to 12 C atoms, or a cycloalkyl group having 3 to 12 C atoms, wherein one or more non-adjacent CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO-, and wherein one or more H atoms may be replaced by a halogen atom, or a cycloalkyl or cycloalkyloxy group having 3 to 12 C atoms, wherein one or more H atoms may be replaced by a halogen atom;
[0036] R 23 represents a H atom, an alkyl or alkoxy group having 1 to 10 C atoms;
[0037] r represents 0 or 1.
[0038] In addition to the compounds of formula I and the antioxidants, the LC media of the present invention may also contain a light stabilizer. The presence of the light stabilizer synergistically increases the stabilizing effect of the antioxidant in reducing short-term image retention and reducing long-term image retention, resulting in a significant reduction in non-uniformity (mura) defects such as star non-uniformity or edge non-uniformity. It has been shown to be particularly advantageous to use one or more light stabilizers of the following formula H:
[0039]
[0040] wherein
[0041] R 11 each independently represents a H atom, F, an alkyl group having 1 to 20 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, -O-CO-, -NR 13 -, -CO-NR 13 - or -NR 13 -CO- such that O and N atoms are not directly connected to each other, and wherein one H atom or more H atoms may be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 ;
[0042] R 12Each independently represents an H atom, an alkyl group having 1 to 20 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, -O-CO-, -NR 13 -, -CO-NR 13 - or -NR 13 -CO-, a hydrocarbon group containing a cycloalkyl or alkylcycloalkyl group, and wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, -O-CO-, -NR 13 -, -CO-NR 13 - or -NR 13 -CO-, and wherein one H atom or more H atoms may be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 substituted, or an aromatic or heteroaromatic hydrocarbon group, wherein one H atom or more H atoms may be replaced by OR 13 , N(R 13 )(R 14 ) or R 15 substituted;
[0043] R 13 , R 14 and R 15 each independently represents an alkyl or acyl group having 1 to 10 C atoms, or an aromatic hydrocarbon or carboxylic acid group having 6 to 12 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, -O-CO-, -NR 13 -, -CO-NR 13 - or -NR 13 -CO- replaced;
[0044] R 16 each independently represents an H atom, an alkyl or alkoxy group having 1 to 10 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, -O-CO-, -NR 13 -, -CO-NR 13 - or -NR 13 -CO- is replaced by an O-cycloalkyl having 3 to 12 C atoms, O · or OH;
[0045] R 17 each independently of one another represents an H atom, an alkyl or alkoxy group having 1 to 10 C atoms, or an alkylene group or a single bond, where R 17 and S 11 can together form a ring structure;
[0046] S 11 and S 12 each independently of one another represents an alkylene group having 1 to 20 C atoms, where one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH- in such a way that the O and N atoms are not directly connected to each other, -O-, -CO-O-, -O-CO-, -NR 13 -, -CO-NR 13 - or -NR 13 -CO-, and where one H atom or more H atoms can be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 substituted, or a single bond;
[0047] Y 11 to Y 14 each independently of one another represents a methyl or ethyl group;
[0048] X 11 represents C;
[0049] Z 11 to Z 14 each independently of one another represents -O-, -(C=O)-, -O-(C=O)-, -(C=O)-O-, -O-(C=O)-O-, -(NR 13 )-, -NR 13 -(C=O)-, -(C=O)-NR 13 - or a single bond, and if S 11 is a single bond, Z 11 and Z 12 do not both represent -O- at the same time; if S 12 is a single bond, Z 13 and Z 14 do not both represent -O- at the same time; and if q represents 0, Z12 and Z 13 They do not simultaneously represent -O-;
[0050] p represents 1 or 2;
[0051] q represents 0 or 1;
[0052] o represents (3 - p);
[0053] n represents an integer from 1 to 10;
[0054] m represents an integer from 0 to 8; wherein
[0055] n*p represents an integer from 1 to 10, preferably from 2 to 8, and
[0056] represents an organic moiety having (m + n) bonding sites.
[0057] The LC medium according to the invention is particularly suitable for energy-saving LC displays for FFS, HB-FFS, XB-FFS and IPS modes for gaming based on dielectrically positive liquid crystals and their polymer-stabilized variants.
[0058] The invention further relates to the use of an LC medium as described in the context for electro-optical purposes, in particular for LC displays, shutter glasses, LC windows, 3D applications, preferably for TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-HB-FFS, PS-XB-FFS, SA-HB-FFS, SA-XB-FFS, polymer-stabilized SA-HB-FFS, polymer-stabilized SA-XB-FFS, positive VA and positive PS-VA displays, very preferably for FFS, HB-FFS, IPS, PS-HB-FFS and PS-IPS displays.
[0059] The invention further relates to an electro-optical LC display containing an LC medium as described in the context, in particular a TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-HB-FFS, PS-XB-FFS, SA-HB-FFS, SA-XB-FFS, polymer-stabilized SA-HB-FFS, polymer-stabilized SA-XB-FFS, positive VA or positive PS-VA display, preferably an FFS, HB-FFS, IPS, PS-HB-FFS or PS-IPS display.
[0060] In the present application, all atoms may optionally include their isotopes. In some embodiments, one or more hydrogen atoms (H) may optionally be replaced by deuterium (D); a high degree of deuteration enables or simplifies the analytical determination of the compound, especially in the case of low concentrations.
[0061] In Formulas I, ST, and H, if R 0 , R 21 , R 22 , R 11 , R 12 or R 13 to R 17 represent an alkyl and / or an alkoxy group, which may be straight-chain or branched-chain. It is preferably straight-chain, having 2, 3, 4, 5, or 6 C atoms and preferably represents ethyl, propyl, butyl, pentyl, hexyl, ethoxy, propoxy, butoxy, pentyloxy, or hexyloxy, and in addition represents methyl, methoxy. R 0 preferably represents a straight-chain alkyl group having 1 to 6 C atoms, or an alkenyl group having 2 to 6 C atoms.
[0062] The oxaalkyl group preferably represents straight-chain 2-oxapropyl (=methoxymethyl), 2-oxabutyl (=ethoxymethyl) or 3-oxabutyl (=2-methoxyethyl), 2-, 3-, or 4-oxapentyl, 2-, 3-, 4-, or 5-oxahexyl.
[0063] If R 0 , R 21 , R 22 , R 11 , R 12 or R 13 to R 17 represent an alkoxy group or an oxaalkyl group, which may also contain one or more additional oxygen atoms, provided that the oxygen atoms are not directly connected to each other.
[0064] In another preferred embodiment, one or more of R 0 , R 21 , R 22 , R 11 , R 12 or R 13 to R 17 are selected from
[0065] -S 1 -F, -O-S 1 -F, -O-S1-O-S2, where S 1 is C 1-12 -alkylene or C 2-12 -alkenylene, and S 2is H, C 1-12 -alkyl or C 2-12 -alkenyl, and very preferably R 0 , R 21 , R 22 , R 11 , R 12 or R 13 to R 17 one or more of which are selected from
[0066] -OCH2OCH3, -O(CH2)2OCH3, -O(CH2)3OCH3, -O(CH2)4OCH3, -O(CH2)2F, -O(CH2)3F, -O(CH2)4F.
[0067] If R 0 , R 21 , R 22 , R 11 , R 12 or R 13 to R 17 represents an alkenyl which may be straight-chain or branched. It is preferably straight-chain and has 2 to 10 C atoms. Thus, it particularly represents vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, hept-1-, -2-, -3-, -4-, -5- or -6-enyl, oct-1-, -2-, -3-, -4-, -5-, -6- or -7-enyl, non-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-enyl, dec-1-, -2-, -3-, -4-, -5-, -6-, -7-, -8- or -9-enyl.
[0068] If R 0 , R 21 , R 22 , R 11 , R 12 or R 13 to R 17 represents an alkyl or alkenyl which is at least monosubstituted by halogen, this group is preferably straight-chain, and the halogen is preferably F or Cl. In the case of polysubstitution, the halogen is preferably F. The resulting group also includes perfluorinated groups. In the case of monosubstitution, the fluorine or chlorine substituent can be at any desired position, but is preferably at the ω-position.
[0069] Particularly preferably, R in formula I 0The group represents an alkyl, alkenyl, alkynyl or alkoxy group having at most 12, preferably at most 8 C atoms, each of which is optionally substituted by a halogen, in particular by F, and is particularly preferably H, F, an alkyl, alkenyl or alkenyl group having at most 8 C atoms.
[0070] Preferred alkyl groups are, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl and n-octyl. Preferred alkenyl groups are, for example, vinyl, propenyl, butenyl and pentenyl. Preferred alkynyl groups are, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl and octynyl. Preferred alkoxy groups are, for example, methoxy, ethoxy, n-propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy. The halogen preferably represents F or Cl, most preferably F.
[0071] One or more compounds of formula I are preferably selected from one of the following structures:
[0072]
[0073] wherein R 0 、X 0 and Y 0 have the meanings indicated in general formula I.
[0074] In a more preferred embodiment, R 0 、X 0 and Y 0 are as follows:
[0075] R 0 is an alkyl group having 1 to 6 C atoms, or an alkenyl group having 2 to 6 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO- in such a way that the O atoms are not directly connected to each other, and wherein one or more H atoms may be replaced by halogen atoms, very preferably methyl, ethyl or propyl, most preferably n-propyl;
[0076] X 0 is an F atom or an alkyl or alkoxy group having 1 to 3 C atoms, or an alkenyl or alkenyloxy group having 2 or 3 C atoms, wherein one or more H atoms are replaced by F atoms; and
[0077] Y 0 is H or CH3.
[0078] Particularly preferred compounds of formula I-1 are compounds selected from the following sub-formulas
[0079]
[0080]
[0081]
[0082]
[0083] Very preferably, the compounds of formula I-1-1, I-1-2, I-1-3 and I-1-4, and most preferably the compound of formula I-1-2.
[0084] Preferred compounds of formula I-2 and I-3 are as follows:
[0085]
[0086]
[0087]
[0088] The proportion of the compound of formula I or its sub-formula in the LC medium is preferably 2 to 35% by weight, very preferably 3 to 30% by weight, and most preferably 4 to 20% by weight.
[0089] Preferably, the LC medium contains 1, 2 or 3 compounds of formula I or its sub-formula.
[0090] Antioxidant
[0091] As used in this application, the term "antioxidant" is well known to those skilled in the art and refers to a compound that can retard autoxidation and is added to the LC medium. There is no particular limitation on the antioxidant used in the present invention as long as they do not substantially impair the physical properties of the LC medium, especially in terms of its voltage holding ratio and mesomorphic behavior.
[0092] In a preferred embodiment, the antioxidant in the LC medium of the present invention is described by the above general formula ST. The LC medium containing the compounds of the following sub-formulas ST-1, ST-2 and ST-3 shows particularly high long-term stability and UV stability:
[0093]
[0094] wherein
[0095] R 21 and R 22 each independently represent an H atom or an alkyl or alkoxy group having 1 to 7 C atoms.
[0096] In a particularly preferred embodiment, the compounds of general formula ST can be selected from the following specific structures:
[0097]
[0098]
[0099]
[0100]
[0101]
[0102] In a further preferred embodiment, the LC medium according to the invention may comprise at least one other sterically hindered phenol as an additional antioxidant, which is mentioned in Table B below.
[0103] The preferred content of one or more compounds of formula ST in the LC medium depends in particular on the inherent chemical stability of the LC medium and on the nature of the compounds of formula ST. They are preferably used in a proportion in the range from 10 ppm to 10,000 ppm, more preferably from 20 ppm to 2,000 ppm, based on the weight of the LC medium.
[0104] Compound of formula H
[0105] The term "light stabilizer" used in the present application is well known to those skilled in the art and refers to a compound added to the LC medium which is capable of protecting the LC medium from degradation due to long-term exposure to UV radiation. Suitable light stabilizers include in particular hindered amine light stabilizers (HALS) and ultraviolet (UV) absorbers and combinations thereof. There is no particular limitation on the light stabilizers used in the present invention, provided that they do not substantially impair the physical properties of the LC medium, in particular with respect to the voltage holding ratio and the mesomorphic behavior.
[0106] In a preferred embodiment, the light stabilizer in the LC medium of the present invention is described by the general formula H as described above. In some preferred embodiments of the present invention, in the compounds of formula H,
[0107]
[0108]
[0109] wherein
[0110] -Z 12 -S 11 -Z 11 - each occurrence independently of one another represents -O-, -S 11 -O-, -O-S 11 -O-, -(C=O)-O-S 11 -O-, -O-(C=O)-S 11 -O-, -O-(C=O)-S 11-(C=O)-O-, -O-S 11 -(C=O)-O-, -(C=O)-O-S 11 -C, -(C=O)-O-S 11 -O-(C=O)- or -(N-R 13 )-S 11 -O-, -(N-R 13 -C(=O)-S 11 -(C=O)-O or a single bond, preferably -O-, -S 11 -O-, -O-S 11 -O-, -(C=O)-O-S 11 -O-, -O-(C=O)-S 11 -O- or -O-S 11 -(C=O)-O-, and / or
[0111] S 11 preferably represents an alkylene group having 1 to 20 C atoms, and / or
[0112] R 11 if present, represents an alkyl group, an alkoxy group or H, preferably H or an alkyl group, and / or
[0113] R 12 represents H, methyl, ethyl, propyl, isopropyl or 3-heptyl or cyclohexyl.
[0114] In a preferred embodiment of the present application, in the compound of formula H,
[0115]
[0116] represents a group selected from the groups of the following formulas:
[0117]
[0118] In a further preferred embodiment of the present application, in the compound of formula H,
[0119]
[0120] represents a group selected from the groups of the following formulas
[0121]
[0122]
[0123] In a still further preferred embodiment of the present application, in the compound of formula H in which p preferably represents 1,
[0124]
[0125] represents preferably -O-S 11 -O-, -S 11 -O- or -O-S 11 -, particularly preferably -O-S 11 -O- or -S 11 -O-.
[0126] In a further preferred embodiment of the present invention, in the compound of formula H, the group
[0127]
[0128] represents a group selected from the groups of the following formulas
[0129]
[0130]
[0131] In a further preferred embodiment of the present invention, where p is 2, which may be the same as or different from those above, in the compound of formula H,
[0132]
[0133] represents a group selected from the groups of the following formulas
[0134]
[0135]
[0136] In an even further preferred embodiment of the present invention, which may be the same as or different from those above, in the compound of formula H, the group
[0137]
[0138] each independently represents, each time it appears
[0139]
[0140] preferably
[0141]
[0142] The compounds of the following general formulas H-1-1, H-1-2 and H-1-3 show to be particularly effective UV stabilizers in the LC mixture, especially with respect to VHR stability:
[0143]
[0144] wherein ZG, R 16As defined above, n represents an integer from 1 to 8. These compounds are highly suitable for use as stabilizers in LC mixtures and for stabilizing the VHR of the mixture upon UV exposure.
[0145] In a particularly preferred embodiment, one or more compounds of formula H can be selected from the compounds of formulae H-2-1 to H-2-6 below:
[0146]
[0147]
[0148] wherein
[0149] R 11 each independently of the others represents an H atom, an alkyl group having 1 to 20 C atoms, where one -CH2- group or, if present, a plurality of -CH2- groups can be replaced by -O- or -C(=O)-, provided that two adjacent -CH2- groups cannot be replaced by -O-, and one or, if present, a plurality of -CH2- groups can be replaced by -CH=CH- or -C≡C-, and where one H atom or a plurality of H atoms can be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 .
[0150] R 16 represents an H atom or O · .
[0151] n represents an integer from 0 to 12, and
[0152] S 11 and S 12 each independently of the others represents an alkylene group having 1 to 20 C atoms, where one -CH2- group or, if present, a plurality of -CH2- groups can be replaced by -O- or -C(=O)-, provided that two adjacent -CH2- groups cannot be replaced by -O-, and where one H atom or a plurality of H atoms can be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 or represents a single bond.
[0153] In a preferred embodiment of the invention, the LC medium according to the invention contains in each case one or more compounds of formula H selected from the compounds of the following formulae:
[0154]
[0155]
[0156]
[0157]
[0158]
[0159]
[0160]
[0161]
[0162]
[0163] The preferred content of one or more compounds of formula H in the LC medium depends in particular on the inherent chemical stability of the LC medium and on the nature of the compounds of formula H. Wherein R 16 represents O · for the compound of formula H (referred to as NO radical type HALS), based on the weight of the LC medium, is preferably used in a proportion in the range of 50 ppm to 1000 ppm. Wherein R 16 represents a hydrogen atom for the compound of formula H (referred to as NH radical type HALS), based on the weight of the LC medium, is advantageously used in a proportion in the range of 50 ppm to 2000 ppm.
[0164] Other components
[0165] In a preferred embodiment, the LC medium may additionally comprise one or more compounds selected from the following formulas II and III:
[0166]
[0167] Wherein each substituent, independently of one another and each time it occurs, is the same or different and has the following meanings:
[0168]
[0169]
[0170] R 0 has one of the meanings given for R in formula I 0
[0171] X 0 are each independently F, Cl, an alkyl, alkenyl, alkoxy or alkenyloxy group having at most 6 carbon atoms, wherein one or more hydrogen atoms have been replaced by halogen atoms,
[0172] L 1-8 Each independently is H, F or Cl, and
[0173] Y 0 is H or CH3.
[0174] Preferred compounds of formulae II and III are those in which Y 0 is H.
[0175] Even more preferred compounds of formulae II and III are the following compounds: wherein R 0 represents an alkyl group having 1 to 6 C atoms, or a cycloalkyl group having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl, and X 0 represents F, CF3 or OCF3, and OCF═CF2, OCHFCF3 or Cl, very preferably F.
[0176] In a preferred embodiment, the LC medium comprises one or more compounds of formula II selected from the following sub-formulae:
[0177]
[0178]
[0179] wherein R 0 and X 0 have the meanings given in formula II.
[0180] Preferred compounds are the compounds of formulae II-1, II-2 and II-3, very preferably the compounds of formulae II-1 and II-2.
[0181] In the compounds of formulae II-1 to II-7, R 0 preferably represents an alkyl group having 1 to 6 C atoms or a cycloalkyl group having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl, and X 0 represents F, CF3 or OCF3, and OCF═CF2, OCHFCF3 or Cl, very preferably F.
[0182] In one embodiment, the LC medium contains one or more compounds of formula II or its sub-formulae as described in the context, wherein Y 0 is CH3. Very preferably, the LC medium according to this preferred embodiment comprises one or more compounds of formula II selected from the following sub-formulae:
[0183]
[0184] wherein R 0 and X 0 have the meanings given above in formula II.
[0185] Preferred compounds are the compounds of formulae IIA-1, IIA-2 and IIA-3, very preferably the compounds of formulae IIA-1 and IIA-2.
[0186] Among the compounds of formulae IIA-1 to IIA-7, R 0 preferably represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, very preferably ethyl, propyl, butyl or pentyl, and X 0 represents F, CF3 or OCF3, and OCF═CF2, OCHFCF3 or Cl, very preferably F.
[0187] The proportion of the compound of formula II in the LC medium is generally from 0 to 20% by weight, very preferably from 1 to 15% by weight, most preferably from 2 to 10% by weight.
[0188] In a further preferred embodiment, the LC medium comprises one or more compounds of formula III selected from the following sub-formulae:
[0189]
[0190]
[0191]
[0192]
[0193] wherein R 0 and X 0 have the meanings given in formula II.
[0194] Particularly preferred compounds are the compounds of formulae III-1, III-4, III-6, III-16, III-19 and III-20.
[0195] Among the compounds of formulae III-1 to III-22, R 0 represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, very preferably ethyl, propyl, butyl or pentyl, X 0 represents F, CF3 or OCF3, and OCF═CF2, OCHFCF3 or Cl, very preferably F, Y 0 preferably represents H.
[0196] The LC medium may contain one or more compounds of formula III or its sub-formulae as described in the context, wherein Y 0 is CH3. Very preferably, the LC medium according to this preferred embodiment comprises one or more compounds of formula III selected from the following sub-formulae:
[0197]
[0198]
[0199]
[0200]
[0201] wherein R 0 and X 0 have the meanings given above in formula III.
[0202] Preferred compounds are the compounds of formulae IIIA-1, IIIA-4, IIIA-6, IIIA-16, IIIA-19 and IIIA-20.
[0203] In the compounds of formulae IIIA-1 to IIIA-21, R 0 represents an alkyl group having 1 to 6 C atoms or a cycloalkyl group having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl, and X 0 represents F, CF3 or OCF3, and OCF═CF2, OCHFCF3 or Cl, very preferably F.
[0204] The proportion of the compound of formula III in the LC medium is preferably 5 to 60% by weight, very preferably 10 to 50% by weight, and most preferably 20 to 40% by weight.
[0205] In a further preferred embodiment, the LC medium may additionally comprise one or more compounds selected from the following formulae:
[0206]
[0207]
[0208] wherein
[0209] R 0 、X 0 、L 1-4 and Y 0 have the meanings indicated in formulae II and III,
[0210] Z 0 represents -C2H4-, -(CH2)4-, -CH═CH-, -CF═CF-, -C2F4-, -CH2CF2-, -CF2CH2-, -CH2O-, -OCH2-, -COO-, -CF2O- or -OCF2-, and also represents a single bond in formulae V and VI; and
[0211] s represents 0 or 1.
[0212] The compounds of formula IV are preferably selected from the following formulas:
[0213]
[0214]
[0215] wherein R 0 and X 0 have the meanings indicated in formulas II and III.
[0216] R 0 preferably represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, very preferably ethyl, propyl, butyl or pentyl. X 0 preferably represents F or OCF3, as well as OCF═CF2, OCHFCF3 or Cl.
[0217] The compounds of formula IVa are preferably represented by the following sub-formulas:
[0218]
[0219] The compounds of formula IVb are preferably represented by the following formula:
[0220]
[0221] The compounds of formula IVc are preferably represented by the following sub-formulas:
[0222]
[0223]
[0224] wherein R 0 has the meaning indicated in formula II, preferably an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, very preferably ethyl, n-propyl, n-butyl or n-pentyl.
[0225] The compound(s) of formula IVc (especially formula IVc-1) is / are preferably used in the LC medium according to the invention in an amount of 1-20% by weight, particularly preferably 2-15% by weight.
[0226] The compounds of formula V are preferably selected from the following sub-formulas:
[0227]
[0228]
[0229] wherein R 0 and X 0 have the meanings indicated in formula II.
[0230] R0 Preferably represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, very preferably ethyl, propyl, butyl or pentyl. X 0 Preferably represents F and OCF3, as well as OCHF2, CF3, OCF═CF2, OCHFCF3 and OCH═CF2.
[0231] The compounds of formula VI are preferably selected from the following sub-formulas:
[0232]
[0233]
[0234] wherein R 0 and X 0 have the meanings indicated in formula II.
[0235] R 0 Preferably represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, very preferably ethyl, n-propyl, n-butyl or n-pentyl. X 0 Preferably represents F, as well as OCF3, CF3, CF═CF2, OCHF2, OCHFCF3 and OCH═CF2;
[0236] The preferred compounds of formulas VIa to VIe are selected from the compounds of the following sub-formulas:
[0237]
[0238] "alkyl" is an alkyl group having 1 to 6 carbon atoms.
[0239] The compounds of formula VII are preferably selected from the following sub-formulas:
[0240]
[0241] wherein R 0 and X 0 have the meanings indicated in formula II.
[0242] R 0 Preferably represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, very preferably ethyl, propyl, butyl or pentyl. X 0 Preferably represents F, as well as OCF3, OCHF2, OCHFCF3 and OCH═CF2.
[0243] In some embodiments, the LC medium additionally comprises one or more compounds selected from the following formulas:
[0244]
[0245]
[0246] wherein
[0247] R 0 and X 0 each independently has one of the meanings indicated in formula II,
[0248] L 1-4 each independently represents H or F,
[0249] Y 0 represents H or CH3, preferably H,
[0250] X 0 is preferably F, Cl, CF3, OCF3 or OCHF2, OCF═CF2, OCHFCF3,
[0251] R 0 preferably represents alkyl, alkoxy, oxaalkyl, cycloalkyl, fluoroalkyl or alkenyl, each having up to 6 C atoms.
[0252] Very preferably, the LC medium according to the invention comprises one or more compounds of formula XXa:
[0253]
[0254] wherein R 0 represents alkyl having 1 to 6 C atoms or cycloalkyl having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl, and X 0 represents F, CF3 or OCF3, and OCF═CF2, OCHFCF3 or Cl, very preferably F. R 0 preferably represents a straight-chain alkyl, especially ethyl, n-propyl, n-butyl or n-pentyl and very particularly preferably n-propyl.
[0255] The compound(s) of formula XX (especially formula XXa) is / are preferably used in the LC medium according to the invention in an amount of 0 - 15% by weight, particularly preferably 1 - 10% by weight.
[0256] Very preferably, the LC medium according to the invention comprises one or more compounds of formula XXIa:
[0257]
[0258] wherein R 0 represents alkyl having 1 to 6 C atoms or cycloalkyl having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl. R 0Preferably represents a straight-chain alkyl group, especially ethyl, n-propyl, n-butyl or n-pentyl, very particularly preferably n-propyl.
[0259] The compound(s) of formula XXI (especially formula XXIa) is / are preferably used in the LC medium according to the invention in an amount of 1-15% by weight, particularly preferably 2-10% by weight.
[0260] Further preferably, the LC medium according to the invention comprises one or more compounds of formula XXIIIa:
[0261]
[0262] wherein R 0 represents an alkyl group having 1 to 6 C atoms or a cycloalkyl group having 3 to 6 C atoms. R 0 Preferably represents a straight-chain alkyl group, especially ethyl, n-propyl, n-butyl or n-pentyl, very particularly preferably n-propyl, or a cycloalkyl group, especially cyclopentyl.
[0263] Preferred specific compounds of formula XXIIIa include the following, especially
[0264]
[0265] The compound(s) of formula XXIII (especially formula XXIIIa) is / are preferably used in the LC medium according to the invention in an amount of 0.5-5% by weight, particularly preferably 0.5-2% by weight.
[0266] The LC medium may additionally comprise one or more compounds of formula XXIV:
[0267]
[0268] wherein R 0 、X 0 and L 1-6 have the meanings indicated in formula III, s represents 0 or 1, and represents
[0269] In formula XXIV, X 0 may also represent an alkyl group having 1 to 6 C atoms, or an alkoxy group having 1 to 6 C atoms. The alkyl or alkoxy group is preferably straight-chain.
[0270] R 0 Preferably represents an alkyl group having 1 to 6 C atoms. X 0 Preferably represents F.
[0271] The compounds of formula XXIV are preferably selected from the following sub-formulas:
[0272]
[0273]
[0274] wherein R 0 、X 0 and L 1 have the meanings indicated in formula III. R 0 preferably represents an alkyl group having 1 to 6 C atoms. X 0 preferably represents F, L 1 is preferably F;
[0275] is preferably
[0276]
[0277] R 0 is a straight-chain alkyl or alkenyl group having 2 to 6 C atoms;
[0278] The LC medium may further comprise one or more compounds of the following formula:
[0279]
[0280] wherein R 1 and X 0 have the meanings indicated for R 0 and X 0 respectively in formula II. R 1 preferably represents an alkyl group having 1 to 6 C atoms or a cycloalkyl group having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl. X 0 preferably represents F, CF3 or OCF3, and OCF=CF2, OCHFCF3 or Cl, very preferably F. In formula XXIV, X 0 very particularly preferably represents Cl.
[0281] The LC medium may also optionally comprise one or more compounds of the following formula:
[0282]
[0283] wherein
[0284] and R 1 、X 0 and Y 0 have the meanings indicated for R 0 、X 0 and Y 0 respectively in formula II. R 1Preferably represents an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms, very preferably ethyl, propyl, butyl or pentyl. X 0 Preferably represents F, CF3 or OCF3, as well as OCF═CF2, OCHFCF3 or Cl, very preferably F, and Y 0 Preferably represents H. In some embodiments, the LC medium according to the invention preferably comprises one or more compounds of formula XXIX, wherein X 0 Preferably represents F.
[0285] The compounds of formula XXVIII are preferably selected from sub-formula XXVIIIa, among which XXVIIIa-1 and XXVIIIa-2 are most preferred:
[0287]
[0288] "alkyl" is an alkyl group having 1 to 6 carbon atoms.
[0289] The compound(s) of formula XXVII - XXX is / are preferably used in the LC medium according to the invention in an amount of 1 - 20% by weight, particularly preferably 1 - 15% by weight. A particularly preferred LC medium comprises at least one compound of formula XXIX and / or formula XXX.
[0290] Very preferably, the LC medium according to the invention comprises one or more compounds of formula XXIXa and / or XXXa:
[0291]
[0292] wherein R 1 and Y 0 have the meanings indicated for R 0 and Y 0 in formula II, and preferably R 1 represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, very preferably ethyl, propyl, butyl or pentyl.
[0293] The compound(s) of formula XXIXa and / or XXXa is / are preferably used in the LC medium according to the invention in an amount of 1 - 15% by weight, particularly preferably 2 - 10% by weight.
[0294] The LC medium may also comprise one or more compounds of pyrimidine or pyridine compounds of the following formula:
[0295]
[0296] wherein R 1 、X 0 and Y0 has the meanings indicated for R in formula II 0 , X 0 and Y 0 respectively. R 1 preferably represents an alkyl group having 1 to 6 C atoms, or a cycloalkyl group having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl. X 0 preferably represents F, CF3 or OCF3, and OCF═CF2, OCHFCF3 or Cl, very preferably F, and Y 0 preferably represents H. The medium according to the invention may in particular optionally contain one or more compounds of formula XXXI-1, where X 0 preferably represents F. The compound(s) of formulae XXXI-1 to XXXI-3 may be used in the LC medium according to the invention in an amount of 1-20% by weight, particularly preferably 1-15% by weight.
[0297] Preferably, in addition to the compound of formula I, the antioxidant and optionally the light stabilizer, the LC medium further contains one or more compounds of formulae N1 and N2:
[0298]
[0299] where
[0300] R 41 and R 42 independently of one another have the meanings indicated above for R 0 under formula I, preferably R 41 represents alkyl and R 42 represents alkyl or alkoxy, or R 41 represents alkenyl and R 42 represents alkyl, where one -CH2- group may be replaced by cyclopropylidene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylidene or 1,3-cyclopentylene,
[0301]
[0302] independently of one another, and if
[0303] appears twice,
[0304] these also independently of one another represent
[0305]
[0306]
[0307] preferably
[0308] one or more of which represent
[0309]
[0310] Z 41 and Z 42 independently of one another, and if Z 41 appears twice, these also independently of one another represent -CH2CH2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O-, -CF2O-, -C≡C- or a single bond, preferably one or more of which represent a single bond, and
[0311] p represents 0, 1 or 2, preferably 0 or 1, and
[0312] R 51 and R 52 independently of one another, have one of the meanings given for R 41 and R 42 and preferably represent an alkyl group having 1 to 7 C atoms, preferably a normal alkyl group, particularly preferably a normal alkyl group having 1 to 5 C atoms, an alkoxy group having 1 to 7 C atoms, preferably a normal alkoxy group, particularly preferably a normal alkoxy group having 2 to 5 C atoms, an alkoxyalkyl, alkenyl or alkenyloxy group having 2 to 7 C atoms, preferably having 2 to 4 C atoms, preferably alkenyloxy,
[0313] wherein one -CH2- group may be replaced by cyclopropylidene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylidene or 1,3-cyclopentylene,
[0314]
[0315] if present, each independently of one another represent
[0316]
[0317]
[0318] preferably
[0319]
[0320] preferably
[0321] represent
[0322] and, if present
[0323] preferably represent
[0324] Z 51 to Z 53 each independently of the others represents -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO- or a single bond, preferably -CH2-CH2-, -CH2-O- or a single bond, particularly preferably a single bond.
[0325] i and j each independently of the others represent 0 or 1.
[0326] (i + j) preferably represents 0, 1 or 2, more preferably 0 or 1, most preferably 1, and
[0327] one or more, preferably one of the aromatic rings present may optionally be substituted by an alkyl group, preferably by a methyl group.
[0328] In some embodiments, the LC medium contains one or more compounds selected from the following formulas:
[0329]
[0330]
[0331] wherein
[0332] "alkyl" and "alkyl*" each independently of the others represent an alkyl group having 1 to 6 C atoms;
[0333] "alkenyl" and "alkenyl*" each independently of the others represent an alkenyl group having 2 to 6 C atoms.
[0334] Compounds of the formulas Z1 and Z2 are highly preferred.
[0335] Preferred compounds of the formulas Z1 to Z6 are compounds selected from the following sub-formulas:
[0336]
[0337]
[0338]
[0339] In another preferred embodiment, the LC medium contains one or more compounds of the formula Z1 or its preferred sub-formulas and / or one or more compounds selected from the formulas Z2, Z3, Z4 and Z5 or their preferred sub-formulas.
[0340] Preferably, the total proportion of the compounds of formulae Z1, Z2, Z3, Z4, Z5 and Z6 or their sub-formulae (such as CC-3-V) in the medium is 10 to 65% by weight, very preferably 20 to 60% by weight, and most preferably 25 to 55% by weight. In an even more preferred embodiment, the compound of formula Z1-1 is used in an amount in the range of 10% to 60% by weight, more preferably 25% to 50% by weight, based on the total weight of the LC medium. In a further preferred embodiment, the LC medium in total comprises 50% to 70% by weight of the compounds represented by formulae Z1-1 and Z4-2.
[0341] Preferably, the medium contains 1, 2 or 3 compounds selected from the compounds of formulae Z1, Z2, Z3 and Z4 or their sub-formulae.
[0342] The LC medium may additionally comprise one or more compounds of the following general formulae:
[0343]
[0344] wherein
[0345] R 1 and R 2 each independently of one another represents C 1-6 -alkyl, C 1-6 -alkoxy or C 2-6 -alkenyl.
[0346] The compounds of formula XII are preferably selected from the following sub-formulae:
[0347]
[0348] wherein "alkyl" and "alkyl*" each independently of one another represent methyl, ethyl, propyl, butyl, pentyl or hexyl.
[0349] Compounds of formula XIIa and XIIc are particularly preferred. In formula XIIb, "alkyl" preferably independently of one another represents n-C3H7, n-C4H9 or n-C5H 11 , especially n-C3H7. In formula XIIc, "alkyl" preferably represents n-C3H7 and "alkyl*" preferably is CH3 or n-C3H7.
[0350] Particularly preferred compounds of formula XII are described by the following structures:
[0351]
[0352] The LC medium may additionally comprise one or more compounds selected from the following formulae:
[0353]
[0354] wherein L 1 and L 2 have the meanings indicated in formula III, R 1 and R 2 each independently of one another represent a n-alkyl, cycloalkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl each having at most 6 C atoms, and preferably each independently of one another represent an alkyl having 1 to 6 C atoms; in the compounds of formula XIV, at least one of the substituents R 1 and R 2 preferably represents an alkenyl having 2 to 6 C atoms.
[0355] The LC medium may also optionally comprise one or more compounds of formula XIV, wherein at least one of the substituents R 1 and R 2 represents an alkenyl having 2 to 6 C atoms, preferably selected from the compounds of the following sub-formulas:
[0356]
[0357] wherein "alkyl" and "alkyl*" have the meanings indicated above and each independently of one another preferably represents methyl, ethyl or propyl.
[0358] The compounds of formula XIV are preferably selected from the following sub-formulas:
[0359]
[0360]
[0361] Very preferably the compounds of XIVd-1, XIVe-1, XIVe-2 and XIVe-3.
[0362] The LC medium may also optionally comprise one or more compounds of formula XV, wherein at least one of the substituents R 1 and R 2 represents an alkyl or alkoxy having 2 to 6 C atoms, preferably selected from the compounds of the following sub-formulas:
[0363]
[0364] wherein "alkyl" and "alkyl*" have the meanings indicated above and each independently of one another preferably represents methyl, ethyl or propyl.
[0365] In a still further embodiment, the LC medium comprises one or more compounds of formula XVI
[0366]
[0367] wherein R1 and R 2 In formula II, R 0 , L represents H or F.
[0368] Particularly preferred compounds of formula XVI are compounds of the following sub-formula:
[0369]
[0370]
[0371] in
[0372] "Alkyl" and "alkyl*" each independently of one another denote a straight-chain alkyl radical having 1 to 6 C atoms, in particular ethyl, propyl or pentyl, and
[0373] "Alkenyl" and "alkenyl*" each independently of one another denote straight-chain alkenyl having 2 to 6 C atoms, in particular CH2═CHC2H4, CH3CH═CHC2H4, CH2═CH and CH3CH═CH.
[0374] Particular preference is given to compounds of the formulae XVIb and XVIc. Very particular preference is given to compounds of the following sub-formulae:
[0375]
[0376]
[0377] In yet a further embodiment, the LC medium comprises one or more compounds of formula XIII:
[0378]
[0379] Where R 1 and R 2 With formula II, for R 0 The meanings indicated preferably each independently of one another denote an alkyl group having 1 to 6 C atoms. L denotes H, F or Cl.
[0380] Particularly preferred compounds of formula XIII are compounds of the following sub-formula:
[0381]
[0382] in
[0383] "Alkyl" and "alkyl*" each independently of one another denote a straight-chain alkyl radical having 1 to 6 C atoms, in particular ethyl, propyl or pentyl, and
[0384] "Alkenyl" and "alkenyl*" each independently of one another denote straight-chain alkenyl having 2 to 6 C atoms, in particular CH2═CHC2H4, CH3CH═CHC2H4, CH2═CH and CH3CH═CH.
[0385] Particular preference is given to compounds of the formulae XIIIa and XIIIb. Very particular preference is given to compounds of the following sub-formulae:
[0386]
[0387]
[0388] In yet a further embodiment, the LC medium comprises one or more compounds of formula XIII:
[0389]
[0390] Where R 1 and R 2 With formula II, for R 0 The meanings indicated preferably each independently of one another denote an alkyl group having 1 to 6 C atoms. L denotes H, F or Cl.
[0391] Particularly preferred compounds of formula XIII are compounds of the following sub-formula:
[0392]
[0393]
[0394] in
[0395] "Alkyl" and "alkyl*" each independently of one another denote a straight-chain alkyl radical having 1 to 6 C atoms, in particular ethyl, propyl or pentyl, and
[0396] "Alkenyl" and "alkenyl*" each independently of one another denote straight-chain alkenyl having 2 to 6 C atoms, in particular CH2═CHC2H4, CH3CH═CHC2H4, CH2═CH and CH3CH═CH.
[0397] Particular preference is given to compounds of the formulae XIIIa and XIIIb. Very particular preference is given to compounds of the following sub-formulae:
[0398]
[0399]
[0400] The LC medium may optionally comprise one or more compounds of the formula:
[0401]
[0402] wherein
[0403] R 1 and R 2 have the meanings indicated in formula G, and preferably each independently of the other represents an alkyl group having 1 to 6 C atoms. L represents H or F.
[0404] Very preferably, the compound of formula XVIIa, wherein L is H or F. Very preferably, the compound of formula XVIIb, wherein L is F.
[0405] The LC medium may additionally comprise one or more compounds of the following formula:
[0406]
[0407] wherein L, R 1 and R 2 have the meanings indicated for L 1 and R 0 respectively in formula I. R 1 and R 2 preferably represent an alkyl group, an alkoxy group, an oxaalkyl group, a fluoroalkyl group or an alkenyl group each having at most 6 C atoms.
[0408] Particularly preferred compounds of formula XXXII are compounds of the following sub-formulas:
[0409]
[0410] wherein
[0411] "alkyl" and "alkyl*" each independently of the other represent a straight-chain alkyl group having 1 to 6 C atoms, in particular ethyl, propyl or pentyl, and
[0412] "alkenyl" represents a straight-chain alkenyl group having 2 to 6 C atoms, in particular CH2=CHC2H4, CH3CH=CHC2H4, CH2=CH and CH3CH=CH.
[0413] Very particularly preferred are compounds of the following sub-formulas:
[0414]
[0415]
[0416] In some further embodiments, the LC medium comprises one or more compounds of the following formula:
[0417]
[0418] wherein R 1 and R 2 each independently of one another have the meaning indicated for R in formula I, and preferably each independently of one another represent an alkyl group having 1 to 6 C atoms. 0
[0419] Compounds of the following sub-formulae are very particularly preferred:
[0420]
[0421]
[0422] Advantageously, the LC medium according to the invention may comprise one or more compounds of formula LP1
[0423]
[0424] and / or one or more compounds of formula LP2
[0425]
[0426] where each substituent has the following meaning:
[0427] R 0 has one of the meanings given for R in formula I; 1
[0428] R 2 represents an alkyl or alkoxy group having 1 to 12 C atoms, or an alkenyl or alkenyloxy group having 2 or 12 C atoms, where one or more non-adjacent CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH═CH-, -O-, -CO-O- or -O-CO- such that the O atoms are not directly linked to one another, and where one or more H atoms may be replaced by a cycloalkyl or cycloalkoxy group having 3 to 12 C atoms;
[0429] X 0 has one of the meanings given for X in formula I; 0
[0430] Y 0 represents H or CH3; and
[0431] m and n represent 0 or 1.
[0432] One or more compounds of formulae LP1 and LP2 may preferably be described by the following formulae:
[0433]
[0434]
[0435] wherein
[0436] R 0 is an alkyl or alkoxy group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO- in such a way that the O atoms are not directly connected to each other, and wherein one or more H atoms may be replaced by halogen atoms;
[0437] R 2 is an alkyl group having 1 to 6 carbon atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO- in such a way that the O atoms are not directly connected to each other, and wherein one or more H atoms may be replaced by halogen atoms;
[0438] X 0 is an F atom or an alkyl or alkoxy group having 1 to 3 carbon atoms, or an alkenyl or alkenyloxy group having 2 or 3 carbon atoms, wherein one or more H atoms are replaced by F atoms; and
[0439] Y 0 is H or CH3.
[0440] The compounds of general formulas LP1 and LP2 can also be represented by one of the following structures:
[0441]
[0442]
[0443] wherein
[0444] R 0 is an alkyl or alkoxy group having 1 to 12 carbon atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -O-, -CO-O- or -O-CO- in such a way that the O atoms are not directly connected to each other, and wherein one or more H atoms may be replaced by halogen atoms, preferably an alkyl group having 1 to 4 carbon atoms, an alkenyl or alkenyloxy group having 2 to 6 carbon atoms, or a cycloalkyl or cycloalkoxy group having 3 to 6 carbon atoms, wherein vinyl, allyl or cyclopentyl is particularly preferred;
[0445] n represents 1, 2, 3, 4 or 5; and
[0446] m represents 1, 2, 3 or 4.
[0447] Particularly preferred compounds of formula LP1 are compounds selected from the following sub-formulas:
[0448]
[0449]
[0450]
[0451] wherein Y 0 is H or CH3, preferably H.
[0452] Particularly preferred compounds of formula LP2 are compounds selected from the following sub-formulas:
[0453]
[0454]
[0455] wherein Y 0 is H or CH3, preferably H.
[0456] Very preferred are compounds of formula LP2-1a, LP2-1b, LP2-1c, LP2-1d and LP2-1i, LP2-2b, LP2-3a, LP2-3c, and most preferred is compound of formula LP2-1b.
[0457] Preferably, the LC medium contains one or more compounds of formula LP1 and one or more compounds of formula LP2.
[0458] The total proportion of the compound of formula LP1 or its sub-formula in the LC medium is preferably 2 to 35% by weight, very preferably 3 to 25% by weight, and most preferably 4 to 15% by weight. The total proportion of the compound of formula LP2 or its sub-formula in the LC medium is preferably 2 to 35% by weight, very preferably 3 to 25% by weight, and most preferably 4 to 15% by weight.
[0459] Preferably, the LC medium contains 1, 2 or 3 compounds of formula LP1 or its sub-formula. In a particularly preferred embodiment, the LC medium contains at least one compound of formula LP1.
[0460] In addition to the compound of formula I, antioxidants and optionally light stabilizers, the LC medium may optionally contain one or more compounds selected from formulas Y and B:
[0461]
[0462] where each substituent, upon each occurrence, is the same or different and each independently has the following meanings:
[0463] represent
[0464] represent represent
[0465] wherein
[0466] R 1 and R 2 each independently of one another have one of the meanings given for R in formula I, R 0 has one of the meanings given for R 3 has one of the meanings given for R 1 one of the meanings given,
[0467] Z x and Z y is -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,
[0468] Z z is -CH2O-, -O-, -C2H4-, -OCH2- or a single bond,
[0469] Y 1 is -CH2-, -O- or -S-,
[0470] L 1-4 is H, F or Cl, preferably H or F, very preferably F,
[0471] x, y are 0, 1 or 2, where x + y ≤ 3,
[0472] z is 0 or 1,
[0473] wherein in formula B, the dibenzofuran or dibenzothiophene group may also be further substituted by methyl or methoxy, and
[0474] wherein the compound of formula Y contains at least one substituent L which is F or Cl (preferably F) 1-4 .
[0475] The LC medium according to this first preferred embodiment may contain one or more compounds of formula I, one or more antioxidants, one or more light stabilizers, one or more compounds selected from compounds of formulae Z1, Z2 and Z3 and one or more compounds selected from compounds of formulae Y and B.
[0476] The LC medium according to this first preferred embodiment is particularly suitable for LC displays in the HB-FFS or PS-HB-FFS mode.
[0477] In the compounds of formula Y and its sub-formulas, R 1 and R 2 preferably represent straight-chain alkyl or alkoxy groups having 1 to 6 C atoms, and alkenyl groups having 2 to 6 C atoms, in particular vinyl, 1E-propenyl, 1E-butenyl, 3-butenyl, 1E-pentenyl, 3E-pentenyl or 4-pentenyl.
[0478] In the compounds of formula Y and its sub-formulas, the substituents L 1 and L 2 both preferably represent F. In another preferred embodiment of the present invention, in the compounds of formula Y and its sub-formulas, one of the substituents L 1 and L 2 represents F and the other represents Cl.
[0479] In a preferred embodiment of the present invention, the LC medium contains one or more compounds of formula Y selected from the following sub-formulas:
[0480]
[0481] wherein R 1 、R 2 、Z x and Z y have the meanings given above for formula Y,
[0482] a represents 1 or 2,
[0483] b represents 0 or 1,
[0484] L 1 、L 2 represent F or Cl, preferably F, and
[0485] L 5 represents an H atom or CH3,
[0486] represents
[0487] represents
[0488] Preferably, in the compounds of formula Y1 and Y2, L 1 and L 2 both represent F, or one of L 1 and L 2 represents F and the other represents Cl, or L 1 and L2 Both represent F, or L 1 and L 2 One of them represents F and the other represents Cl.
[0489] Preferably, the LC medium comprises one or more compounds of formula Y1 selected from the following sub-formulas:
[0490]
[0491]
[0492]
[0493]
[0494]
[0495]
[0496]
[0497]
[0498]
[0499]
[0500]
[0501]
[0502]
[0503] wherein
[0504] a represents 1 or 2,
[0505] “alkyl” and “alkyl*” each independently of the other represent a straight-chain alkyl group having 1 to 6 C atoms,
[0506] “alkenyl” represents a straight-chain alkenyl group having 2 to 6 C atoms, and
[0507] L 5 represents an H atom or CH3.
[0508] “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-.
[0509] Very preferably, the LC medium contains one or more compounds of formula Y1 selected from formulae Y1-1, Y1-2, Y1-7, Y1-12, Y1-17, Y1-22, Y1-40, Y1-41, Y1-42, Y1-44, Y1-50 and Y1-68. L 5 Preferably represents an H atom.
[0510] Further preferably, the LC medium comprises one or more compounds of formula Y2 selected from the following sub-formulae:
[0511]
[0512]
[0513]
[0514]
[0515]
[0516]
[0517] wherein
[0518] “alkyl” and “alkyl*” each independently of the other represent a straight-chain alkyl group having 1 to 6 C atoms, and
[0519] “alkenyl” represents a straight-chain alkenyl group having 2 to 6 C atoms,
[0520] (O) represents an oxygen atom or a single bond, and
[0521] L 5 represents an H atom or CH3, preferably an H atom.
[0522] “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-.
[0523] Very preferably, the LC medium contains one or more compounds of formula Y2 selected from formulae Y2-2 and Y2-10.
[0524] The proportion of the compound of formula Y1 or its sub-formula in the LC medium is preferably 0 to 10% by weight.
[0525] The proportion of the compound of formula Y2 or its sub-formula in the LC medium is preferably 0 to 10% by weight.
[0526] The total proportion of the compounds of formula Y1 and Y2 or their sub-formulas in the medium is preferably 1 to 20% by weight, very preferably 2 to 15% by weight.
[0527] Preferably, the LC medium contains 1, 2 or 3 compounds of formula Y1 and Y2 or their sub-formulas, very preferably selected from formula Y1-2, Y1-22, Y1-66, Y1-70, Y2-6 and Y2-22.
[0528] In another preferred embodiment of the present invention, the LC medium contains one or more compounds of formula Y of the following sub-formulas:
[0529]
[0530] wherein L 1 、L 2 、L 5 、R 1 and R 2 have one of the meanings given for L 1 、L 2 、Y 0 and R 0 in formula I, respectively.
[0531] Preferred compounds of formula Y3 are selected from the following sub-formulas:
[0532]
[0533]
[0534]
[0535] wherein,
[0536] “alkyl” and “alkyl*” each independently of one another represent a straight-chain alkyl group having 1 to 6 C atoms;
[0537] “alkenyl” and “alkenyl*” each independently of one another represent a straight-chain alkenyl group having 2 to 6 C atoms; and
[0538] (O) represents an oxygen atom or a single bond.
[0539] "Alkenyl" and "alkenyl*" preferably represent 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-.
[0540] Compounds of formula Y3 are particularly preferably selected from the following sub-formulas:
[0541]
[0542] wherein "alkoxy" and "alkoxy*" each independently preferably represent a straight-chain alkoxy group having 3, 4 or 5 C atoms.
[0543] Preferably, in the compounds of formula Y3 and its sub-formulas, L 1 and L 2 both represent F. Further preferably, in the compounds of formula Y3, one of the substituents L 1 and L 2 represents F and the other represents Cl.
[0544] The proportion of the compounds of formula Y3 or its sub-formulas in the LC medium is preferably 0 to 10% by weight, very preferably 1 to 6% by weight.
[0545] Preferably, the LC medium contains 1, 2 or 3 compounds of formula Y3 or its sub-formulas, more preferably the compound of formula Y3-6, very preferably the compound of formula Y3-6A.
[0546] In yet another preferred embodiment of the present invention, the LC medium contains one or more compounds of formula Y of sub-formula Y4:
[0547]
[0548] wherein R 1 and R 2 each independently have one of the meanings indicated above in formula Y, and
[0549]
[0550] each independently represent
[0551]
[0552] wherein L 5 represents F or Cl, preferably F, and L 6represents F, Cl, OCF3, CF3, CH3, CH2F or CHF2, preferably F, and preferably at least one of rings G, I and K is different from unsubstituted benzene.
[0553] The most preferred compounds of formula Y4 are selected from the following sub-formulas:
[0554]
[0555]
[0556]
[0557] where
[0558] R represents a straight-chain alkyl or alkoxy group having 1 to 7 C atoms,
[0559] (O) represents an oxygen atom or a single bond, and
[0560] m represents an integer from 1 to 6.
[0561] R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy or pentyloxy.
[0562] The proportion of the compound of formula Y4 or its sub-formula in the medium is preferably 0 to 10% by weight, very preferably 1 to 6% by weight.
[0563] Particularly preferred compounds are compounds of the following sub-formulas
[0564]
[0565] where
[0566] "alkyl" and "alkyl*" each independently of one another represent a straight-chain alkyl group having 1 to 6 C atoms, in particular ethyl, propyl or pentyl.
[0567] Particularly advantageous use is made of the following compounds:
[0568]
[0569]
[0570] In another preferred embodiment of the invention, the LC medium contains one or more compounds of formula Y selected from the following sub-formulas:
[0571]
[0572] where R 5 has the meanings given above for R in formula Y 1One of the indicated meanings, "alkyl" means a straight-chain alkyl group having 1 to 6 C atoms, d represents 0 or 1, and z and m each independently represent an integer from 1 to 6.
[0573] R 5 Particularly preferred among these compounds are C 2-6 -alkyl or -alkoxy or C 2-6 -alkenyl, and d is preferably 1. The LC medium according to the invention preferably contains one or more compounds of the above-mentioned formula in an amount of ≥ 5% by weight.
[0574] Further preferred embodiments are indicated below:
[0575] The LC medium contains one or more compounds of formula Y of the following sub-formulas
[0576]
[0577] wherein R 1 、R 2 、L 1 、L 2 、X, x and Z x have the meanings given in formula Y, and wherein at least one of the rings X is cyclohexenylene.
[0578] Preferably, the substituents L 1 and L 2 both represent F. More preferably, one of the substituents L 1 and L 2 represents F and the other represents Cl.
[0579] The compounds of formula LY are preferably selected from the following sub-formulas:
[0580]
[0581]
[0582] wherein
[0583] R 1 has the meaning indicated above in formula Y,
[0584] (O) represents an oxygen atom or a single bond, and
[0585] v represents an integer from 1 to 6.
[0586] R 1 preferably represents a straight-chain alkyl group having 1 to 6 C atoms, or a straight-chain alkenyl group having 2 to 6 C atoms, especially CH3, C2H5, n-C3H7, n-C4H9, n-C5H 11, 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-.
[0587] Compounds of formula LY4 are very highly preferred.
[0588] Preferably, the medium contains 1, 2 or 3 compounds of formula LY, very highly preferably a compound of formula LY4.
[0589] The proportion of the compound of formula LY or its sub-formula in the medium is preferably 1 to 10% by weight.
[0590] - The medium comprises one or more compounds of formula Y represented by the following sub-formulas:
[0591]
[0592] wherein R 1 , R 2 , L 1 , L 2 , Y, y and Z y have the meanings given in formula Y, wherein at least one of the rings Y is tetrahydropyran.
[0593] Compounds of formula AY are preferably selected from the following sub-formulas:
[0594]
[0595]
[0596] wherein
[0597] R 1 has the meaning indicated above,
[0598] "alkyl" means a straight-chain alkyl having 1 to 6 C atoms,
[0599] (O) represents an oxygen atom or a single bond, and
[0600] v represents an integer from 1 to 6.
[0601] R 1 preferably represents a straight-chain alkyl having 1 to 6 C atoms, or a straight-chain alkenyl having 2 to 6 C atoms, especially CH3, C2H5, n-C3H7, n-C4H9, n-C5H 11, 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-.
[0602] In the compounds of formula B and its sub-formulas, R 1 and R 3 preferably represent a straight-chain alkyl or alkoxy group having 1 to 6 C atoms, in particular methoxy, ethoxy, propoxy or butoxy, and an alkenyl group having 2 to 6 C atoms, in particular vinyl, 1E-propenyl, 1E-butenyl, 3-butenyl, 1E-pentenyl, 3E-pentenyl or 4-pentenyl.
[0603] In a preferred embodiment of the invention, the medium contains one or more compounds of formula B selected from the following sub-formulas:
[0604]
[0605] where Y 1 , L 1 , L 2 , R 1 and R 3 have the meanings given in formula B.
[0606] Preferred compounds of formula B1 are selected from the following sub-formulas:
[0607]
[0608]
[0609] where R 1 and R 3 independently represent a straight-chain alkyl group having 1 to 6 C atoms, where one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO- in such a way that the O atoms are not directly connected to each other, and where one or more H atoms can be replaced by a halogen atom.
[0610] Very preferably, the compounds of formula B1-1 and B1-2, where the two groups (O) represent oxygen atoms, and R 1 and R 3 independently represent an alkyl group which is one of the following: methyl, ethyl, propyl, butyl, pentyl or hexyl, which is preferably straight-chain. Very preferably, one "alkyl" is ethyl and the other "alkyl*" is n-pentyl.
[0611] Particularly preferred are the compounds of formula B1-2.
[0612] Preferably, the compounds of formula B1-1 are selected from the compounds of formulae B1-1-1 to B1-1-11, preferably the compound of formula B1-1-6:
[0613]
[0614]
[0615] wherein
[0616] “alkyl” and “alkyl*” each independently of the other represent a straight-chain alkyl group having 1 to 6 C atoms,
[0617] “alkenyl” and “alkenyl*” each independently of the other represent a straight-chain alkenyl group having 2 to 6 C atoms,
[0618] “alkoxy” and “alkoxy*” each independently of the other represent a straight-chain alkoxy group having 1 to 6 C atoms.
[0619] Preferably, the compounds of formula B1-2 are selected from the compounds of formulae B1-2-1 to B1-2-10, preferably the compound of formula B1-2-6:
[0620]
[0621]
[0622] wherein
[0623] “alkyl” and “alkyl*” each independently of the other represent a straight-chain alkyl group having 1 to 6 C atoms,
[0624] “alkenyl” and “alkenyl*” each independently of the other represent a straight-chain alkenyl group having 2 to 6 C atoms,
[0625] “alkoxy” and “alkoxy*” each independently of the other represent a straight-chain alkoxy group having 1 to 6 C atoms.
[0626] Optionally, the LC medium comprises one or more compounds of formula B1-1A and / or B1-2A:
[0627]
[0628] wherein
[0629] (O) represents O or a single bond,
[0630] R IIIArepresents an alkyl or alkenyl group having at most 7 C atoms, or the group Cy-C m H 2m+1 -,
[0631] m and n are the same or different and are 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1,
[0632] Cy represents a cycloaliphatic group having 3, 4 or 5 ring atoms, which is optionally substituted by an alkyl or alkenyl group each having at most 3 C atoms, or by a halogen or CN, and preferably represents cyclopropyl, cyclobutyl or cyclopentyl.
[0633] The compounds of formula B1-1A and / or B1-2A replace the compounds of formula B1-1 and B1-2 or are contained in the medium together with the compounds of formula B1-1 and B1-2, preferably together.
[0634] Preferred compounds of formula B1-1A and / or B1-2A are also the following:
[0635]
[0636] where alkoxy represents a straight-chain alkoxy group having 1 to 6 C atoms or alternatively represents -(CH2) n F, where n is 2, 3, 4 or 5, preferably C2H4F.
[0637] The proportion of the compound of formula B1 or its sub-formula in the LC medium is preferably 1 to 20% by weight, very preferably 1 to 15% by weight.
[0638] Preferably, the LC medium contains 1, 2 or 3 compounds of formula B1 or its sub-formula.
[0639] In a preferred embodiment of the present invention, the LC medium may contain one or more compounds of formula B2-2
[0640]
[0641] wherein
[0642] R 1 、R 3 are the same or different and represent H, an alkyl or alkoxy group having 1 to 6 C atoms, wherein one or more CH2 groups in these groups are optionally independently replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO- in such a way that O atoms are not directly connected to each other, and wherein in addition, one or more H atoms may be replaced by a halogen.
[0643] The compounds of formula B2-2 are preferably selected from the compounds of formulae B2-2-1 to B2-2-10:
[0644]
[0645]
[0646] wherein R 3 represents an alkyl group having 1 to 6 C atoms, preferably ethyl, n-propyl or n-butyl, or alternatively represents cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl or alternatively represents -(CH2) n F, where n is 2, 3, 4 or 5, preferably C2H4F.
[0647] Particularly preferably, the compounds of formula B2 are selected from the following sub-formulae:
[0648]
[0649] The proportion of the compounds of formula B2 or its sub-formulae in the LC medium is preferably 1 to 20% by weight, very preferably 1 to 15% by weight.
[0650] Preferably, the LC medium contains 1, 2 or 3 compounds of formula B2 or its sub-formulae.
[0651] The preferred compounds of formula B3 are selected from the following sub-formulae:
[0652]
[0653] wherein R 1 has one of the meanings given in formula B3, preferably represents a straight-chain alkyl group having 1 to 6 C atoms, very preferably methyl, ethyl, propyl, butyl, pentyl or hexyl, more preferably ethyl or propyl, most preferably propyl, X 1 has one of the meanings given in formula B3, preferably represents CF3 or OCF3.
[0654] The preferred compounds of formula B3 are selected from the following sub-formulae:
[0655]
[0656] wherein R 1 has one of the meanings given in formula B3, preferably represents a straight-chain alkyl group having 1 to 6 C atoms, very preferably methyl, ethyl, propyl, butyl, pentyl or hexyl, more preferably ethyl or propyl, most preferably propyl.
[0657] Most preferably, the compounds of formula B3-1-1 and B3-2-2.
[0658] In a preferred embodiment, the LC medium contains one or more compounds of formula B or its sub-formulas B1, B2, B3, B1-1, B1-2, B2-1, B2-2, B2-3, B3-1, B3-2, B3-1-1, B3-1-2, B3-2-1 and B3-2-2, wherein the dibenzofuran or dibenzothiophene group is substituted by a methyl or a methoxy group, preferably by a methyl group, preferably in the para position of the substituent F, very preferably in the para position of the substituent F (i.e., in the meta position relative to the end group R 2 or X 1 .
[0659] The proportion of the compound of formula B3 or its sub-formula in the LC medium is preferably 1 to 20% by weight, very preferably 1 to 10% by weight.
[0660] Preferably, the LC medium contains 1, 2 or 3 compounds of formula B3 or its sub-formula.
[0661] Preferably, the total proportion of the compounds of formula Y and B or their sub-formulas in the LC medium is 2 to 25% by weight, very preferably 3 to 20% by weight.
[0662] Further preferred LC media are selected from the following preferred embodiments, including any combination thereof:
[0663] · A combination of a compound of formula I with compounds of formula ST, H and Z1 to Z7
[0664] · A combination of a compound of formula I with compounds of formula ST, Z1 to Z7 and II and / or III
[0665] · A combination of a compound of formula I with compounds of formula ST, LP1, IV to VIII and compounds of formula Z1 and Z4
[0666] · A combination of a compound of formula I with compounds of formula LP1 and / or LP2
[0667] · A combination of a compound of formula I with compounds of formula XXX and / or XXIX
[0668] · A combination of a compound of formula I with a compound of formula IVb-1
[0669] · A combination of a compound of formula I with a compound of formula IVc-1
[0670] · A combination of a compound of formula I with a compound of formula XXXV
[0671] · A combination of a compound of formula I with a compound of formula XIVc-1
[0672] · A combination of a compound of formula I with a compound of formula XIIa-1
[0673] · A combination of a compound of formula I and a compound of formula XVIc
[0674] · A combination of a compound of formula I and a compound of formula VIb
[0675] · A combination of a compound of formula I and a compound of formula XXVIIIa
[0676] - The LC medium comprises one or more compounds of formula I or its sub-formulas, ST, and optionally H, II, and / or III, and one or more compounds selected from formula Z1, Z2, Z3, Z4, Z5, V, VI, VII, VIII, XIV, XV, XVI, XVIIa, XVIIb, XVIIc, XVIII, XIX, XX, XXI, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII, XXIX, XXX, XXX-1, XXX-2, XXX-3, XXXII, XXXIII, and S and their sub-formulas.
[0677] - The LC medium comprises one or more compounds of formula I or its sub-formulas and ST and / or H, II, and / or III, and one or more compounds selected from formula Z1, Z2, Z3, Z4, Z5, IV, VI, XII, XIV, XVI, XVIIa, XVIIb, XVIIc, XX, LP1-1, XXIII, XXIX, and S and their sub-formulas.
[0678] - The LC medium comprises one or more compounds selected from formula II-1, II-2, and II-3, very preferably compounds selected from formula II-1 and II-2. The individual concentration of each of these compounds is preferably 2 to 15% by weight. The total concentration of these compounds is preferably 5 to 25% by weight.
[0679] - The LC medium comprises one or more compounds selected from formula III-1, III-4, III-6, III-16, III-19, and III-20, very preferably compounds selected from formula III-1, III-6, III-16, and III-20. The individual concentration of each of these compounds is preferably 2 to 15% by weight. The total concentration of these compounds is preferably 5 to 30% by weight.
[0680] - The LC medium comprises one or more compounds of formula IV, preferably compounds selected from formula IVa or IVc, very preferably compounds selected from formula IVa-1 or IVc-1, and most preferably formula IVc-1. The individual concentration of each of these compounds is preferably 2 to 15% by weight. The total concentration of these compounds is preferably 5 to 20% by weight.
[0681] - The LC medium contains one or more compounds of formula VI, preferably selected from the compounds of formula VIb. The individual concentration of each of these compounds is preferably 1 to 20% by weight. The total concentration of these compounds is preferably 5 to 20% by weight.
[0682] - The LC medium contains one or more compounds of formula Z1, preferably selected from the compounds of formula Z1-1. The total concentration of these compounds is preferably 1 to 60% by weight, more preferably 5 to 50% by weight.
[0683] - The LC medium contains one or more compounds of formula Z2, preferably selected from the compounds of formula Z2-1 and Z2-2. The total concentration of these compounds is preferably 2 to 35% by weight, very preferably 3 to 25% by weight.
[0684] - The LC medium contains 5 to 20% by weight of a compound of formula Z3, preferably the compound of formula Z3-1.
[0685] - The LC medium contains 5 to 20% by weight of a compound of formula Z4, preferably the compound of formula Z4-1.
[0686] - The LC medium contains 10 to 65% by weight, very preferably 20 to 60% by weight, of a compound of formula Z5.
[0687] - The LC medium contains one or more compounds of formula LP1-1, preferably the compound of formula LP1-1a, very preferably the compound of formula LP1-1a. The concentration of these compounds is preferably 2 to 15% by weight.
[0688] - The LC medium contains one or more compounds of formula XII, preferably the compounds of formula XIIa or XIIb, very preferably the compound of formula XIIa, most preferably the compound of formula XIIa-1. The concentration of these compounds is preferably 2 to 15% by weight.
[0689] - The LC medium contains 1 to 15% by weight of a compound of formula XIIb.
[0690] - The LC medium contains one or more compounds of formula XIV, preferably the compound of formula XIVd, very preferably the compound of formula XIVd-1. The concentration of these compounds is preferably 2 to 10% by weight.
[0691] - The LC medium contains one or more compounds of formula XVIb, preferably the compounds of formula XVIb-1, XVIb-2 and / or XVIb-3. The concentration of these compounds is preferably 2 to 15% by weight.
[0692] - The LC medium contains one or more compounds of formula XVIc, preferably compounds of formula XVIc-1, XVIc-2 and / or XVIc-3. The concentration of these compounds is preferably 2 to 20% by weight.
[0693] - The LC medium contains one or more compounds selected from the group consisting of formulas XVIIa, XVIIb and XVIIc, very preferably a compound of formula XVIIa in which L is H and a compound of formula XVIIb in which L is F. The total concentration of these compounds is preferably 0.5 to 5% by weight.
[0694] - The LC medium contains one or more compounds of formula XX, preferably a compound of formula XXa. The concentration of these compounds is preferably 2 to 10% by weight.
[0695] - The LC medium contains one or more compounds of formula XXI, preferably a compound of formula XXIa. The concentration of these compounds is preferably 2 to 10% by weight.
[0696] - The LC medium contains one or more compounds of formula XXIII, preferably a compound of formula XXIIIa. The concentration of these compounds is preferably 0.5 to 5% by weight.
[0697] - The LC medium contains one or more compounds of formula XXIX, preferably a compound of formula XXIXa. The concentration of these compounds is preferably 2 to 10% by weight.
[0698] - The LC medium contains one or more compounds of formula XXX. The concentration of these compounds is preferably 2 to 10% by weight.
[0699] - The LC medium contains one or more compounds of formula XII. The concentration of these compounds is preferably 2 to 10% by weight.
[0700] - The LC medium contains one or more compounds of formulas I, ST, H, II and / or III, one or more compounds selected from formulas Z1, Z2 and Z3 or their sub-formulas, one or more compounds selected from formula XIV, one or more compounds selected from formulas IV, VI, XX, XXIII and XXIX or their sub-formulas, and one or more compounds selected from formulas XVI, XVIIa, XVIIb, XVIIc or their sub-formulas.
[0701] - The LC medium contains one or more compounds of formula I, ST, II, and / or III, one or more compounds selected from formulae Z1, Z2, Z3, Z4, and Z5 or their sub-formulae, one or more compounds selected from formula XIVd or its sub-formulae, one or more compounds selected from formulae IVc, VIb, XXa, XXIIIa, and XXIXa or their sub-formulae, and one or more compounds selected from formulae LP1-1b, XVIb, XVIc, XVIIa, XVIIb, XVIIc or their sub-formulae.
[0702] - The LC medium contains one or more compounds of formula I, ST, II, and / or III, one or more compounds selected from formulae Z1, Z2, and Z3 or their sub-formulae, one or more compounds of formula Y, preferably compounds selected from formulae Y1 and Y2, one or more compounds selected from formula XIV, one or more compounds selected from formulae II, III, IV, VI, XX, XXIII, and XXIX or their sub-formulae, and one or more compounds selected from formulae XVI, XVIIa, XVIIb, XVIIc or their sub-formulae.
[0703] - The LC medium contains one or more compounds of formula I, one or more compounds selected from formulae Z1, Z2, Z3, Z4, and Z5 or their sub-formulae, one or more compounds of formula B, preferably compounds selected from formulae B1, B2, and B3, one or more compounds of formula XIVd or its sub-formulae, one or more compounds selected from formulae II, III, IVc, VIb, XXa, XXIIIa, and XXIXa or their sub-formulae, and one or more compounds selected from formulae LP1-1b, XVIb, XVIc, XVIIa, XVIIb, XVIIc or their sub-formulae.
[0704] - In addition to the compound of formula I, the LC medium further contains other compounds selected from formulae Z1, Z2, Z3, IV, LP1-1, XIV, XVI, XVIIa, XVIIb, XVIIc, XXI, XXIII, XXIX, XXX, and XXIV or their sub-formulae.
[0705] - In addition to the compound of formula I, the LC medium further contains other compounds selected from formulae Z1, Z2, Z3, IV, XIV, XVI, XVIIa, XVIIb, XVIIc, XXI, XXIII, XXIX, XXX, and XXIV or their sub-formulae.
[0706] - The proportion of the compound of formula I or its sub-formula in the LC medium is 1 to 30% by weight, very preferably 2 to 25% by weight, and most preferably 2 to 20% by weight.
[0707] - The proportion of the compounds of formula Z1, Z2, Z3, Z4 and Z5 or their sub-formulas is 10 to 65% by weight, very preferably 20 to 60% by weight, in the LC medium as a whole.
[0708] - The proportion of the compounds of formula Y or its sub-formulas is 0 to 15% by weight, very preferably 2 to 10% by weight, in the LC medium as a whole.
[0709] - The proportion of the compounds of formula B or its sub-formulas is 0 to 15% by weight, very preferably 2 to 10% by weight, in the LC medium as a whole.
[0710] - The proportion of the compounds of formula II, III, IV - VIII, XVIII - XXIII and XXVII - XXX is 30 to 60% by weight in the LC medium as a whole.
[0711] - The proportion of the compounds of formula XIV and XV is 40 to 70% by weight in the LC medium as a whole.
[0712] - The proportion of the compounds of formula XIV, XVIIa - c and XXXII is 0.5 to 15% by weight in the LC medium as a whole.
[0713] The term "alkyl" or "alkyl*" in this application encompasses straight-chain and branched alkyl groups having 1 to 6 carbon atoms, especially the straight-chain groups methyl, ethyl, propyl, butyl, pentyl and hexyl. Groups having 2 to 5 carbon atoms are generally preferred.
[0714] The term "alkenyl" or "alkenyl*" encompasses straight-chain and branched alkenyl groups having 2 to 6 carbon atoms, especially straight-chain groups. Preferred alkenyl groups are C2 - C7-1E-alkenyl, C4 - C6-3E-alkenyl, especially C2 - C6-1E-alkenyl. Examples of particularly preferred alkenyl groups are vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl and 5-hexenyl. Groups having at most 5 carbon atoms are generally preferred, especially CH2=CH, CH3CH=CH.
[0715] The term "fluoroalkyl" preferably encompasses straight-chain groups having a terminal fluorine, i.e., fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl and 7-fluoroheptyl. However, other positions of fluorine are not excluded.
[0716] The term "oxaalkyl" or "alkoxy" preferably encompasses the formula C n H 2n+1 -O-(CH2) ma straight-chain group, where n and m each independently of one another represent from 1 to 6. m can also represent 0. Preferably, n = 1 and m = 1 to 6, or m = 0 and n = 1 to 3. Further preferably, the alkoxy or oxaalkyl group can also contain one or more additional O atoms in such a way that the O atoms are not directly connected to one another.
[0717] By a suitable choice of R in formulas II and III 0 and X 0 the addressing time, the threshold voltage, the steepness of the transmission characteristic curve, etc. can be modified in a desired manner. For example, compared with alkyl and alkoxy groups, 1E-alkenyl, 3E-alkenyl, 2E-alkenyloxy groups, etc. generally result in shorter addressing times, improved nematic tendency and a higher ratio between the elastic constants K3 (bending) and K1 (splay). Compared with alkyl and alkoxy groups, 4-alkenyl, 3-alkenyl, etc. generally give a lower threshold voltage and a lower K3 / K1 value. The mixtures according to the invention are characterized in particular by high Δε values and thus have significantly faster response times compared with LC dielectrics of the prior art.
[0718] The optimum mixing ratio of the compounds of the above formulas essentially depends on the desired properties, the choice of the components of the above formulas and the choice of any other components that may be present.
[0719] The suitable mixing ratios within the ranges indicated above can be easily determined according to the specific circumstances.
[0720] The total amount of the compounds of the above formulas in the LC dielectric according to the invention is not critical. Thus, the LC dielectric can contain one or more other components for optimizing various properties. However, the higher the total concentration of the compounds of the above formulas, the greater the effect of the desired improvement in the properties of the dielectric that is generally observed.
[0721] In a particularly preferred embodiment, the LC dielectric according to the invention contains compounds of formulas IV to VIII (preferably IV and V), where X 0 represents F, OCF3, OCHF2, OCH=CF2, OCF=CF2 or OCF2-CF2H. A favorable synergistic effect with the compounds of formula I, antioxidants and, if present, light stabilizers results in particularly favorable properties. In particular, an LC dielectric containing the compounds of formula I, antioxidants, light stabilizers, the compounds of formula II and / or III is characterized by its low threshold voltage.
[0722] The individual compounds of the above formulas and their sub-formulas that can be used in the LC dielectric according to the invention are either known or can be prepared analogously to known compounds.
[0723] The present invention also relates to a method for preparing an LC medium as described in the context, by mixing one or more compounds of formula I, an antioxidant, a light stabilizer, and one or more compounds selected from formulae II, III, Z1, Z2, Z3, Z4, IV, VI, XIV, XVI, XVIIa, XVIIb, XVIIc, XX, XXIII, XXIX.
[0724] The LC medium of the present invention may optionally contain one or more polymerizable compounds. The polymerizable compound is preferably selected from formula M
[0725] R a -B 1 -(Z b -B 2 ) m -R b M
[0726] where each substituent is the same or different each time it appears and each independently of one another has the following meanings:
[0727] R a and R b represent P, P-Sp-, H, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, SF5 or a straight-chain or branched alkyl having 1 to 25 C atoms, where in addition, one or more non-adjacent CH2 groups may each independently of one another be replaced by -C(R 0 )=C(R 00 )-, -C≡C-, -N(R 00 )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- such that O and / or S atoms are not directly connected to each other, and where in addition, one or more H atoms may be replaced by F, Cl, Br, I, CN, P or P-Sp-, where if B 1 and / or B 2 contains saturated C atoms, R a and / or R b may also represent a group spiro-linked to this saturated C atom,
[0728] where at least one of the substituents R a and R b represents or contains the group P or P-Sp-,
[0729] P represents a polymerizable group,
[0730] Sp represents a spacer group or a single bond,
[0731] B 1 and B 2is an aromatic, heteroaromatic, alicyclic or heterocyclic group, preferably having 4 to 25 ring atoms, which may also contain fused rings, and which is unsubstituted or mono- or polysubstituted by L,
[0732] Z b represents -O-, -S-, -CO-, -CO-O-, -OCO-, -O-CO-O-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2-, -(CF2) n1 -, -CH=CH-, -CF=CF-, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, CR 0 R 00 or a single bond,
[0733] R 0 and R 00 each independently of one another represent H or an alkyl group having 1 to 12 C atoms,
[0734] m represents 0, 1, 2, 3 or 4,
[0735] n1 represents 1, 2, 3 or 4,
[0736] L represents P, P-Sp-, OH, CH2OH, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R x )2, -C(=O)Y 1 , -C(=O)R x , -N(R x )2, an optionally substituted silyl group, an optionally substituted aryl group having 6 to 20 C atoms, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy group having 1 to 25 C atoms, where additionally one or more H atoms may be replaced by F, Cl, P or P-Sp-,
[0737] P and Sp have the meanings indicated above in formula M,
[0738] Y 1 represents halogen,
[0739] R xdenote P, P-Sp-, H, halogen, a straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein furthermore, one or more non-adjacent CH2 groups may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that O and / or S atoms are not directly connected to each other, and wherein furthermore, one or more H atoms may be replaced by F, Cl, P or P-Sp-, an optionally substituted aryl or aryloxy having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy having 2 to 40 C atoms.
[0740] Further preferably, the LC medium according to the invention comprises one or more polymerizable compounds selected from Table H below.
[0741] Preferably, the proportion of the polymerizable compounds preferably selected from formula M and Table H in the LC medium is 0.01 to 5%, very preferably 0.05 to 1%, and most preferably 0.1 to 0.5%.
[0742] It has been observed that adding one or more polymerizable compounds (such as those selected from formula M and Table H) to the LC medium results in advantageous properties such as a fast response time. Such an LC medium is particularly suitable for PSA displays, in which the LC medium exhibits low image retention, fast and complete polymerization, rapid generation of a low pretilt angle (which is stable after UV exposure), high reliability, a high VHR value after UV exposure, and a high birefringence. By appropriately selecting the polymerizable compounds, it is possible to increase the absorption of the LC medium at longer UV wavelengths, such that it is possible to use such longer UV wavelengths for polymerization, which is advantageous for display manufacturing methods.
[0743] The polymerizable group P is a group suitable for a polymerization reaction (such as free radical or ionic chain polymerization, addition polymerization or condensation polymerization) or suitable for a polymer-analogous reaction (such as addition or condensation onto the main polymer chain). 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, such as oxetanyl or epoxy groups.
[0744] Preferred groups P are selected from CH2═CW 1 -CO-O-, CH2═CW 1 -CO-,
[0745]
[0746] CH2═CW 2 -(O) k3 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-,
[0747] CH2=CW 1 -CO-NH-, CH3-CH=CH-O-, (CH2=CH)2CH-OCO-,
[0748] (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, HO-CW 2 W 3 -, HS-CW 2 W 3 -, HW 2 N-, HO-CW 2 W 3 -NH-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH-, HOOC-, OCN- and W 4 W 5 W 6 Si-, where W 1 represents H, F, Cl, CN, CF3, phenyl or an alkyl group having 1 to 5 C atoms, especially H, F, Cl or CH3, W 2 and W 3 each independently of one another represent H or an alkyl group having 1 to 5 C atoms, especially H, methyl, ethyl or n-propyl, W 4 , W 5 and W 6 each independently of one another represent Cl, an oxaalkyl group or an oxacarbonylalkyl group having 1 to 5 C atoms, W 7 and W 8 each independently of one another represent H, Cl or an alkyl group having 1 to 5 C atoms, Phe represents 1,4-phenylene, which is optionally substituted by one or more substituents L as defined above for formula M, said L group not being P-Sp-, k1, k2 and k3 each independently of one another represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.
[0749] Very preferably, the group P is selected from CH2=CW 1 -CO-O-, CH2=CW 1 -CO-,
[0750]
[0751] CH2=CW 2 -O-, CH=CW 2 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-, CH2=CW 1 -CO-NH-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH- and W 4 W 5 W 6 Si-, where W 1 represents H, F, Cl, CN, CF3, phenyl or an alkyl group having 1 to 5 C atoms, especially H, F, Cl or CH3, W 2 and W 3 each independently of one another represents H or an alkyl group having 1 to 5 C atoms, especially H, methyl, ethyl or n-propyl, W 4 , W 5 and W 6 each independently of one another represents Cl, an oxaalkyl group or an oxacarbonylalkyl group having 1 to 5 C atoms, W 7 and W 8 each independently of one another represents H, Cl or an alkyl group having 1 to 5 C atoms, Phe represents 1,4-phenylene, k1, k2 and k3 each independently of one another represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.
[0752] Very particularly preferred groups P are selected from CH2=CW 1 -CO-O-, especially CH2=CH-CO-O-, CH2=C(CH3)-CO-O- and CH2=CF-CO-O-, and also from CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-,
[0753]
[0754] Further preferably, the polymerizable group P is selected from vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetanyl and epoxy group, and most preferably acrylate and methacrylate groups.
[0755] If Sp is different from a single bond, it preferably has the formula Sp"-X", such that the corresponding substituent P-Sp- conforms to the formula P-Sp"-X"-, where
[0756] Sp" represents an alkylene group 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 furthermore, one or more non-adjacent CH2 groups may each independently of one another be replaced by -O-, -S-, -NH-, -N(R 0 )-, -Si(R 0 R 00 )-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -S-CO-, -CO-S-, -N(R 00 )-CO-O-, -O-CO-N(R 0 )-, -N(R 0 )-CO-N(R 00 )-, -CH=CH- or -C≡C- so that
[0757] X" represents -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R 0 )-, -N(R 0 )-CO-, -N(R 0 )-CO-N(R 00 )-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 0 -, -CY 2 =CY 3 -, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH- or a single bond,
[0758] R 0 and R 00 each independently of one another represent H or an alkyl group having 1 to 20 C atoms, and
[0759] Y 2 and Y 3 each independently of one another represent H, F, Cl or CN.
[0760] X is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 00 - or a single bond.
[0761] Typical spacer groups Sp and -Sp"-X"- are, for example, -(CH2) p1 -, -(CH2CH2O) q1 -CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR 0 R 00 -O) p1 -, where p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, R 0 and R 00 have the meanings indicated above in formula M.
[0762] Particularly preferred groups Sp and -Sp”-X”- are -(CH2) p1 -, -(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO-O-, where p1 and q1 have the meanings indicated above.
[0763] Particularly preferred groups Sp" are in each case a straight-chain ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutyl, ethylenethioethylene, ethyl-N-methyliminoethylene, 1-methylalkylene, vinyl, propenyl and butenyl.
[0764] For the production of a PSA display, the polymerizable compounds contained in the LC medium are polymerized or crosslinked (if a compound contains two or more polymerizable groups) by in-situ polymerization in the LC medium between the substrates of the LC display, optionally while applying a voltage to the electrodes.
[0765] The structure of the PSA display according to the invention corresponds to the usual geometry of the PSA display as described in the prior art cited at the beginning. A geometry without protrusions is preferred, especially those in which, furthermore, the electrodes on the color filter side are unstructured and only the electrodes on the TFT side have grooves. For example, a particularly suitable and preferred electrode structure for a PS-VA display is described in US2006 / 0066793 A1.
[0766] The combination of the compounds of the above preferred embodiments with the above polymeric compounds in the LC medium according to the invention results in a low threshold voltage, a low rotational viscosity and very good low-temperature stability in the LC medium according to the invention, while resulting in constant high-definition bright points and a high VHR value.
[0767] Using an LC medium containing a polymerizable compound allows for a particularly low pretilt angle to be established quickly in a PSA display. In particular, compared to the media of the prior art, in a PSA display, this LC medium shows a significantly shortened response time, especially also the gray-scale response time.
[0768] An LC medium having a nematic LC phase is generally preferred, preferably without a chiral liquid crystal phase.
[0769] The invention also relates to the use of the LC medium according to the invention as described above for electro-optical purposes, in particular for use in shutter glasses, for 3D applications, for use in TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-FFS, positive VA and positive PS-VA displays, and to electro-optical displays, in particular electro-optical displays of the above types, which contain the LC medium according to the invention as described above, in particular TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-FFS, positive VA (vertical alignment) or positive PS-VA displays.
[0770] The invention also relates to an electro-optical display, such as an STN or matrix LC (MLC) display, having two plane-parallel outer plates that together with a frame form a cell, integrated non-linear elements for switching individual pixels on the outer plates, and a nematic LC medium having a positive dielectric anisotropy and a high specific resistance located in the cell, wherein the nematic LC medium is the LC medium according to the invention as described above.
[0771] The LC medium according to the invention is able to significantly broaden the available parameter range. The achievable combination of the clearing point, rotational viscosity, thermal stability and UV stability, as well as a high optical anisotropy, is far superior to the previous materials in the prior art.
[0772] In particular, the combination of a compound of formula I with at least one antioxidant, at least one light stabilizer and optionally a compound selected from formulae II - XXXII or their sub-formulae results in an LC medium that exhibits reduced short-term image retention and reduced long-term image retention and a low rotational viscosity that results in a fast response time. This enables a fast energy-saving LC display, especially liquid crystal displays in FFS, HB-FFS, XB-FFS and IPS modes.
[0773] The LC medium according to the invention is suitable for mobile applications and TFT applications, such as mobile phones and PDAs. In addition, the LC medium according to the invention is particularly suitable for FFS, HB-FFS, XB-FFS and IPS displays based on dielectrically positive liquid crystals.
[0774] The LC medium according to the invention allows for the achievement of a rotational viscosity γ1 of ≤120 mPa·s, particularly preferably ≤100 mPa·s, while maintaining a nematic phase down to -20 °C, preferably down to -30 °C, particularly preferably down to -40 °C, and a clearing point ≥75 °C, preferably ≥80 °C, enabling an excellent MLC display with a fast response time. The rotational viscosity is measured at 20 °C.
[0775] The dielectric anisotropy Δε of the LC medium according to the invention at 20 °C and 1 kHz is preferably ≥ +1.5, very preferably +3 to +18, and most preferably +5 to +15.
[0776] The birefringence Δn of the LC medium according to the invention at 20 °C is preferably 0.08 to 0.2, very preferably 0.09 to 0.15.
[0777] The rotational viscosity γ1 of the LC medium according to the invention is preferably ≤120 mPa·s, more preferably ≤110 mPa·s, and very preferably ≤90 mPa·s.
[0778] The γ1 / K1 ratio of the LC medium according to the invention (where γ1 is the rotational viscosity and K1 is the elastic constant of splay deformation) is preferably ≤7 mPa·s / pN, very preferably ≤6 mPa·s / pN, and most preferably ≤5.5 mPa·s / pN.
[0779] The average elastic constant ratio K of the LC medium according to the invention av is preferably at least 14.0 pN, very preferably at least 15.0 pN, and most preferably at least 16.0 pN. K av can be calculated according to the following formula: K av =(K1 + K2 + K3) / 3 ≈ (K1 + 1 / 2*K1 + K3) / 3.
[0780] The nematic range of the LC medium according to the invention preferably has a width of at least 90 °C, more preferably at least 100 °C, especially at least 110 °C. This range preferably extends at least from -25 °C to +90 °C.
[0781] It goes without saying that by appropriately selecting the components of the LC medium according to the invention, it is also possible to obtain a higher clearing point (for example above 100 °C) at a higher threshold voltage, or a lower clearing point at a lower threshold voltage, while maintaining other favorable properties. It is also possible to obtain an LC medium with a higher Δε and thus a low threshold while the viscosity only increases slightly accordingly. The MLC display according to the invention preferably operates at the first Gooch and Tarry transmission minimum [C.H. Gooch and H.A. Tarry, Electron. Lett. 10, 2 - 4, 1974; C.H. Gooch and H.A. Tarry, Appl. Phys., Vol. 8, 1575 - 1584, 1975], where, in addition to particularly favorable electro-optical properties (such as a high steepness of the characteristic line and a low angular dependence of the contrast (German Patent 30 22 818)), a lower dielectric anisotropy is sufficient at the same threshold voltage as in a similar display at the second minimum. Compared with the case of an LC medium containing a cyano compound, this enables a significantly higher resistivity value to be achieved at the first minimum when using the LC medium according to the invention. By appropriately selecting the components and their weight ratios, a person skilled in the art can set the necessary birefringence for a predetermined layer thickness of the MLC display using simple conventional methods.
[0782] Measurement of the voltage holding ratio (VHR) [S. Matsumoto et al., Liquid Crystals 5 , 1320 (1989); K. Niwa et al., Proc. SID Conference, San Francisco, June 1984, p. 304 (1984); G. Weber et al., Liquid Crystals 5 , 1381 (1989)] has shown that the LC medium according to the invention shows a significantly smaller reduction in VHR upon UV exposure compared to a similar LC medium containing a cyanophenylcyclohexane of the formula or an ester of the formula .
[0783] The LC medium according to the invention has much better light stability and UV stability, that is, they show a significantly smaller reduction in HR when exposed to light, heat or UV.
[0784] The structure of the MLC display according to the present invention consists of a polarizer, an electrode substrate, and a surface-treated electrode, which conforms to the general design of this type of display. The term "general design" is used here in a broad sense and also covers all derivatives and modifications of the MLC display, especially including matrix display elements based on polysilicon TFTs or MIMs.
[0785] However, the significant difference between the display according to the present invention and the conventional displays based on twisted nematic cells to date lies in the selection of the LC parameters of the LC layer.
[0786] The LC medium that can be used according to the present invention is prepared in a conventional manner per se, for example, by mixing the compound of claim 1 with one or more compounds of formulas II - XXXII or with other LC compounds and / or additives. Generally, the required amounts of the components used in smaller amounts are dissolved in the components constituting the main component, advantageously at an elevated temperature. It is also possible to mix solutions of the components in an organic solvent (such as in acetone, chloroform, or methanol) and then remove the solvent again after thorough mixing, for example, by distillation.
[0787] The LC medium can also contain other additives known to those skilled in the art and described in the literature, such as polymerization initiators, inhibitors, surface-active substances, microparticles, radical scavengers, nanoparticles, etc. For example, 0 to 15% of a polychromatic dye or a chiral dopant or an initiator can be added, such as 651 or 907. Suitable stabilizers and dopants are mentioned in Tables F and G below. In a preferred embodiment, the LC medium contains one or more stabilizers selected from Table G. Preferably, the proportion of antioxidants and light stabilizers (such as those of formulas ST and H) as described above or listed in Table G is 10 to 2000 ppm, very preferably 30 to 1000 ppm in the LC medium.
[0788] In addition, for example, 0 to 15% by weight of a polychromatic dye, as well as nanoparticles and conductive salts (preferably ethyl dimethyl dodecyl ammonium 4 - hexoxybenzoate, tetrabutyltetraphenylborate ammonium, or a complex salt of a crown ether (see, for example, Haller et al., Mol. Cryst. Liq. Cryst. 24 , 249 - 258 (1973))) can be added to the LC medium to improve conductivity, or substances for changing the dielectric anisotropy, viscosity, and / or nematic alignment can be added. Substances of this type are described, for example, in DE - A 22 09127, 22 40 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430, and 28 53 728.
[0789] For the present invention and in the following examples, the structures of the LC compounds are indicated by acronyms and are converted into chemical formulas according to Tables A to C below. All substituents C m H 2m+1 、C n H 2n+1 and C l H 2l+1 or C m H 2m-1 、C n H 2n-1 and C l H 2l-1 are straight-chain alkyl or alkylene groups having n, m, and l carbon atoms, respectively, in each case. Preferably, n, m, and l are each independently 1, 2, 3, 4, 5, 6, or 7. Table A shows the codes for the ring elements of the core of the compounds, Table B lists the bridging units, and Table C lists the meanings of the symbols for the left- and right-hand end groups of the molecule. The acronyms consist of the code for the ring element with an optional linking group, followed by the first hyphen and the code for the left-hand end group, and the second hyphen and the code for the right-hand end group. Table D shows the schematic structures of the compounds and their corresponding abbreviations.
[0790] Table A: Ring elements
[0791]
[0792]
[0793]
[0794] Table B: Bridging units
[0795]
[0796] Table C: End groups
[0797]
[0798]
[0799] where n and m are each integers and the three dots "…" are placeholders for other abbreviations from the table.
[0800] The following abbreviations are used:
[0801] (n, m, k, and l are each independently integers, preferably from 1 to 12, more preferably from 1 to 6, k and l can also be 0, preferably from 0 to 4, more preferably 0 or 2, most preferably 2, n is preferably 1, 2, 3, 4, or 5, and in the combination "-nO-", it is preferably 1, 2, 3, or 4, more preferably 2 or 4, m is preferably 1, 2, 3, 4, or 5, and in the combination "-Om", it is preferably 1, 2, 3, or 4, more preferably 2 or 4. The combination "-lVm" is preferably "2V1".)
[0802] The components of the preferred LC medium are shown in Tables D and E
[0803] Table D
[0804]
[0805]
[0806]
[0807]
[0808] Table E
[0809] In the following formula, n and m each independently represent 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, especially 2, 3, 5, and also 0, 4, 6.
[0810]
[0811]
[0812]
[0813]
[0814]
[0815]
[0816]
[0817]
[0818]
[0819]
[0820]
[0821]
[0822]
[0823] Particularly preferred are such LC dielectrics which, in addition to the compounds of formula I, antioxidants, and light stabilizers, further contain at least one, two, three, four or more compounds selected from Table E.
[0824] Table F
[0825] Table F indicates the possible dopants which are usually added to the LC dielectrics according to the invention. The LC dielectric preferably contains 0 to 10% by weight, in particular 0.01 to 5% by weight, particularly preferably 0.01 to 3% by weight of dopants.
[0826]
[0827]
[0828] Table G
[0829] Antioxidants and light stabilizers which can be additionally added in an amount of 0 to 10% by weight, for example, to the LC dielectrics according to the invention are mentioned below.
[0830]
[0831]
[0832]
[0833]
[0834]
[0835] Table H
[0836] Table H shows exemplary reactive mesogenic compounds (RM) which can be used in the LC dielectrics according to the invention.
[0837]
[0838]
[0839]
[0840]
[0841]
[0842]
[0843]
[0844]
[0845]
[0846]
[0847]
[0848]
[0849]
[0850]
[0851]
[0852]
[0853]
[0854]
[0855]
[0856]
[0857]
[0858] The LC medium according to the invention may optionally comprise one or more polymerizable compounds, preferably selected from the polymerizable compounds of formulae RM-1 to RM-184. Among these, the compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-52, RM-54, RM-57, RM-58, RM-64, RM-74, RM-76, RM-88, RM-91, RM-102, RM-103, RM-109, RM-116, RM-117, RM-120, RM-121, RM-122, RM-139, RM-140, RM-142, RM-143, RM-145, RM-146, RM-147, RM-149, RM-156 to RM-163, RM-169, RM-170 and RM-171 to RM-184 are particularly preferred.
[0859] Table I
[0860] Table I shows the self-aligning additives for vertical alignment, which can be used in the LC media of SA-FFS, SA-HB-FFS and SA-XB-FFS displays according to the present invention:
[0861]
[0862]
[0863]
[0864]
[0865]
[0866]
[0867]
[0868]
[0869]
[0870]
[0871]
[0872] In a preferred embodiment, the LC media, SA-VA and SA-FFS displays according to the present invention contain one or more SA additives selected from Formulas SA-1 to SA-49, preferably Formulas SA-14 to SA-49, very preferably Formulas SA-20 to SA-34 and SA-44, in combination with one or more RMs.
[0873] The following examples are intended to illustrate the invention and not to limit the invention.
[0874] In the context, percentage data represents weight percentage. All temperatures are indicated in degrees Celsius. m.p. represents melting point, cl.p. = clearing point. Further, C = crystalline, N = nematic, S = smectic and I = isotropic phase. The data between these symbols represent transition temperatures. Further, the following symbols are also used
[0875] V0 represents the Freedericks threshold voltage at 20 °C, capacitance [V],
[0876] V 10 represents the voltage [V] for 10% transmittance,
[0877] n e represents the extraordinary refractive index at 20 °C and 589 nm,
[0878] n0 represents the ordinary refractive index at 20 °C and 589 nm,
[0879] Δn represents the optical anisotropy measured at 20 °C and 589 nm,
[0880] ε ⊥ represents the dielectric susceptibility (or "dielectric constant") perpendicular to the longitudinal axis of the molecule at 20 °C and 1 kHz,
[0881] ε || represents the dielectric susceptibility (or "dielectric constant") parallel to the longitudinal axis of the molecule at 20 °C and 1 kHz,
[0882] Δε represents the dielectric anisotropy at 20 °C and 1 kHz,
[0883] cl.p. or T(N,I) represents the clearing point [°C],
[0884] υ represents the kinematic viscosity measured at 20 °C [mm 2 ·s -1 ,
[0885] γ1 represents the rotational viscosity measured at 20 °C [mPa·s],
[0886] K1 represents the elastic constant at 20 °C, "splay" deformation [pN],
[0887] K2 represents the elastic constant at 20 °C, "twist" deformation [pN],
[0888] K3 represents the elastic constant at 20 °C, "bend" deformation [pN], and
[0889] VHR represents the voltage holding ratio.
[0890] Unless otherwise explicitly indicated, all physical properties are determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals", November 1997 status, Merck KGaA, Germany, and apply to a temperature of 20 °C. Examples
[0891] Example M1
[0892] A nematic LC medium was formulated as follows:
[0893]
[0894] Mixture Example S1 (stabilized with compounds of formula ST-2-3 and H-3-3) A nematic LC mixture according to the invention was formulated as follows:
[0895] Mixture M1 99.935 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-3 150 ppm
[0896]
[0897] Example M2
[0898] The nematic LC medium is formulated as follows:
[0899]
[0900]
[0901] Mixture Example S2 (stabilized with compounds of formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[0902] Mixture M2 99.935 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-3 150 ppm
[0903] Example M3
[0904] The nematic LC medium is formulated as follows:
[0905]
[0906] Mixture Example S3 (stabilized with compounds of formula ST-2-3) The nematic LC mixture according to the present invention is formulated as follows:
[0907] Mixture M3 99.95 wt% Compound of formula ST-2-3 500 ppm
[0908] Mixture Example S3a (stabilized with compounds of formula ST-1-8) The nematic LC mixture according to the present invention is formulated as follows:
[0909] Mixture M3 99.95 wt% Compound of formula ST-1-8 500 ppm
[0910]
[0911] Example M4
[0912] The nematic LC medium is formulated as follows:
[0913]
[0914]
[0915] Mixture Example S4 (stabilized with compounds of formula ST-2-3 and H-3-11) The nematic LC mixture according to the present invention is formulated as follows:
[0916] Mixture M4 99.955 wt% Compound of formula ST-2-3 400 ppm Compound of formula H-3-11 50 ppm
[0917]
[0918] Example M5
[0919] The nematic LC medium is prepared as follows:
[0920]
[0921] Mixture Example S5 (stabilized with compounds of formula ST-2-3 and H-3-11) The nematic LC mixture according to the present invention is prepared as follows:
[0922] Mixture M5 99.955 wt% Compound of formula ST-2-3 400 ppm Compound of formula H-3-11 50 ppm
[0923] Example M6
[0924] The nematic LC medium is prepared as follows:
[0925]
[0926]
[0927] Mixture Example S6 (stabilized with compounds of formula ST-2-3 and H-3-11) The nematic LC mixture according to the present invention is prepared as follows:
[0928] Mixture M6 99.955 wt% Compound of formula ST-2-3 400 ppm Compound of formula H-3-11 50 ppm
[0929] Example M7
[0930] The nematic LC medium is prepared as follows:
[0931]
[0932]
[0933] Mixture Example S7 (stabilized with compounds of formula ST-1-3) The nematic LC mixture according to the present invention is prepared as follows:
[0934] Mixture M7 99.97 wt% Compound of formula ST-1-3 300 ppm
[0935]
[0936] Example M8
[0937] The nematic LC medium is prepared as follows:
[0938]
[0939]
[0940] Mixture Example S8 (stabilized with compounds of formula ST-1-3) The nematic LC mixture according to the present invention is prepared as follows:
[0941] Mixture M8 99.97 wt% Compound of formula ST-1-3 300 ppm
[0942] Example M9
[0943] The nematic LC medium is formulated as follows:
[0944]
[0945]
[0946] Mixture Example S9 (stabilized with compounds of formula ST-1-3) The nematic LC mixture according to the present invention is formulated as follows:
[0947] Mixture M9 99.97 wt% Compound of formula ST-1-3 300 ppm
[0948] Example M10
[0949] The nematic LC medium is formulated as follows:
[0950]
[0951] Mixture Example S10 (stabilized with compounds of formula ST-1-3) Nematic LC mixture according to the invention Is formulated as follows:
[0952]
[0953]
[0954] Example M11
[0955] The nematic LC medium is formulated as follows:
[0956]
[0957] Mixture Example S11 (stabilized with compounds of formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[0958] Mixture M11 99.92 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-3 300 ppm
[0959] Example M12
[0960] The nematic LC medium is formulated as follows:
[0961]
[0962]
[0963] Mixture Example S12 (stabilized with compounds of formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[0964] Mixture M12 99.92 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-3 300 ppm
[0965] Example M13
[0966] The nematic LC medium is formulated as follows:
[0967]
[0968]
[0969] Mixture Example S13 (Stabilized with Compounds of Formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[0970] Mixture M13 99.935 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-3 150 ppm
[0971] Mixture Example S13a (Stabilized with Compound of Formula ST-2-3)
[0972] The nematic LC mixture according to the present invention is formulated as follows:
[0973] Mixture M13 99.95 wt% Compound of Formula ST-2-3 500 ppm
[0974] Example M14
[0975] The nematic LC medium is formulated as follows:
[0976]
[0977]
[0978] Mixture Example S14 (Stabilized with Compounds of Formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[0979] Mixture M14 99.935 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-3 150 ppm
[0980] Example M15
[0981] The nematic LC medium is formulated as follows:
[0982]
[0983]
[0984]
[0985] Mixture Example S15 (Stabilized with Compounds of Formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[0986] Mixture M15 99.935 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-3 150 ppm
[0987] Example M16
[0988] The nematic LC medium is formulated as follows:
[0989]
[0990]
[0991] Mixture Example S16 (Stabilized with Compounds of Formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[0992] Mixture M16 99.92 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-3 300 ppm
[0993] Example M17
[0994] The nematic LC medium is formulated as follows:
[0995]
[0996] Mixture Example S17 (Stabilized with Compounds of Formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[0997] Mixture M17 99.92 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-3 300 ppm
[0998] Example M18
[0999] The nematic LC medium is formulated as follows:
[1000]
[1001] Mixture Example S18 (Stabilized with Compound of Formula ST-2-3)
[1002] The nematic LC mixture according to the present invention is formulated as follows:
[1003] Mixture M18 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1004] Example M19
[1005] The nematic LC medium is formulated as follows:
[1006]
[1007]
[1008] Mixture Example S19 (Stabilized with Compound of Formula ST-2-3) The nematic LC mixture according to the present invention is formulated as follows:
[1009] Mixture M19 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1010] Example M20
[1011] The nematic LC medium is formulated as follows:
[1012]
[1013]
[1014] Mixture Example S20 (Stabilized with Compound of Formula ST-2-3) The nematic LC mixture according to the present invention is formulated as follows:
[1015] Mixture M20 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1016] Example M21
[1017] The nematic LC medium is formulated as follows:
[1018]
[1019]
[1020] Mixture Example S21 (Stabilized with Compound of Formula ST-2-3) The nematic LC mixture according to the present invention is formulated as follows:
[1021] Mixture M21 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1022] Example M22
[1023] The nematic LC medium is formulated as follows:
[1024]
[1025]
[1026] Mixture Example S22 (Stabilized with Compounds of Formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[1027] Mixture M22 99.935 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-3 150 ppm
[1028] Example M23
[1029] The nematic LC medium is formulated as follows:
[1030]
[1031] Mixture Example S23 (Stabilized with Compound of Formula ST-2-3)
[1032] The nematic LC mixture according to the present invention is formulated as follows:
[1033] Mixture M23 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1034] Example M24
[1035] The nematic LC medium is formulated as follows:
[1036]
[1037] Mixture Example S24 (Stabilized with Compounds of Formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[1038] Mixture M24 99.955 wt% Compound of Formula ST-2-3 300 ppm Compound of Formula H-3-3 150 ppm
[1039] Example M25
[1040] The nematic LC medium is formulated as follows:
[1041]
[1042]
[1043] Mixture Example S25 (Stabilized with Compounds of Formula ST-2-3 and H-3-3) The nematic LC mixture according to the present invention is formulated as follows:
[1044] Mixture M25 99.955 wt% Compound of Formula ST-2-3 300 ppm Compound of Formula H-3-3 150 ppm
[1045] Example M26
[1046] The nematic LC medium is formulated as follows:
[1047]
[1048]
[1049] Mixture Example S26 (Stabilized with Compound of Formula ST-2-3) The nematic LC mixture according to the present invention is formulated as follows:
[1050] Mixture M26 99.96 wt% Compound of Formula ST-2-3 400 ppm
[1051] Example M27
[1052] The nematic LC medium is formulated as follows:
[1053]
[1054]
[1055] Mixture Example S27 (Stabilized with Compound of Formula ST-2-3) The nematic LC mixture according to the present invention is formulated as follows:
[1056] Mixture M26 99.96 wt% Compound of Formula ST-2-3 400 ppm
[1057] Example M28
[1058] The nematic LC medium is formulated as follows:
[1059]
[1060]
[1061] Mixture Example S28 (Stabilized with Compound of Formula ST-2-3)
[1062] The nematic LC mixture according to the present invention is formulated as follows:
[1063] Mixture M28 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1064] Mixture Example S28a (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1065] Mixture M28 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1066]
[1067] Example M29
[1068] The nematic LC medium is formulated as follows:
[1069]
[1070]
[1071] Mixture Example S29 (Stabilized with Compound of Formula ST-2-3)
[1072] The nematic LC mixture according to the present invention is formulated as follows:
[1073] Mixture M29 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1074] Mixture Example S29a (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1075] Mixture M29 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1076] Example M30
[1077] The nematic LC medium is formulated as follows:
[1078]
[1079]
[1080] Mixture Example S30 (Stabilized with Compound of Formula ST-2-3)
[1081] The nematic LC mixture according to the present invention is formulated as follows:
[1082] Mixture M30 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1083] Mixture Example S30a (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1084] Mixture M30 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1085] Example M31
[1086] The nematic LC medium is formulated as follows:
[1087]
[1088]
[1089] Mixture Example S31 (Stabilized with Compound of Formula ST-2-3)
[1090] The nematic LC mixture according to the present invention is formulated as follows:
[1091] Mixture M31 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1092] Mixture Example S31a (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1093] Mixture M31 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1094] Example M32
[1095] The nematic LC medium is formulated as follows:
[1096]
[1097]
[1098] Mixture Example S32 (Stabilized with Compound of Formula ST-2-3)
[1099] The nematic LC mixture according to the present invention is formulated as follows:
[1100] Mixture M32 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1101] Mixture Example S32a (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1102] Mixture M32 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1103] Example M33
[1104] The nematic LC medium is formulated as follows:
[1105]
[1106]
[1107] Mixture Example S33 (Stabilized with Compound of Formula ST-2-3)
[1108] The nematic LC mixture according to the present invention is formulated as follows:
[1109] Mixture M33 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1110] Mixture Example S33a (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1111] Mixture M33 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1112] Example M34
[1113] The nematic LC medium is formulated as follows:
[1114]
[1115]
[1116] Mixture Example S34 (stabilized with compound of formula ST-2-3)
[1117] The nematic LC mixture according to the present invention is formulated as follows:
[1118] Mixture M34 99.95 wt% Compound of formula ST-2-3 500 ppm
[1119] Mixture Example S34a (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1120] Mixture M34 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1121] Example M35
[1122] The nematic LC medium is formulated as follows:
[1123]
[1124]
[1125] Mixture Example S35 (stabilized with compound of formula ST-2-3)
[1126] The nematic LC mixture according to the present invention is formulated as follows:
[1127] Mixture M35 99.95 wt% Compound of formula ST-2-3 500 ppm
[1128] Mixture Example S35a (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1129] Mixture M35 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1130] Example M36
[1131] The nematic LC medium is formulated as follows:
[1132]
[1133] Mixture Example S36 (stabilized with compound of formula ST-2-3)
[1134] The nematic LC mixture according to the present invention is formulated as follows:
[1135] Mixture M36 99.95 wt% Compound of formula ST-2-3 500 ppm
[1136] Mixture Example S36a (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1137] Mixture M36 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1138] Example M37
[1139] The nematic LC medium is formulated as follows:
[1140]
[1141] Mixture Example S37 (stabilized with compound of formula ST-2-3)
[1142] The nematic LC mixture according to the present invention is formulated as follows:
[1143] Mixture M37 99.95 wt% Compound of formula ST-2-3 500 ppm
[1144] Mixture Example S37a (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1145]
[1146]
[1147] Example M38
[1148] The nematic LC medium is formulated as follows:
[1149]
[1150] Mixture Example S38 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1151] Mixture M38 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1152] Example M39
[1153] The nematic LC medium is formulated as follows:
[1154]
[1155] Mixture Example S39 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1156] Mixture M39 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1157] Example M40
[1158] The nematic LC medium is prepared as follows:
[1159]
[1160]
[1161] Mixture Example S40 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1162] Mixture M40 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1163] Example M41
[1164] The nematic LC medium is prepared as follows:
[1165]
[1166]
[1167] Mixture Example S41 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1168] Mixture M41 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1169] Example M42
[1170] The nematic LC medium is prepared as follows:
[1171]
[1172]
[1173] Mixture Example S42 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1174] Mixture M42 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1175] Example M43
[1176] The nematic LC medium is prepared as follows:
[1177]
[1178]
[1179] Mixture Example S43 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1180] Mixture M43 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1181] Example M44
[1182] The nematic LC medium is prepared as follows:
[1183]
[1184]
[1185] Mixture Example S44 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1186] Mixture M44 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1187] Example M45
[1188] The nematic LC medium is prepared as follows:
[1189]
[1190] Mixture Example S45 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1191] Mixture M45 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1192] Example M46
[1193] The nematic LC medium is prepared as follows:
[1194]
[1195] Mixture Example S46 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1196] Mixture M46 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1197] Example M47
[1198] The nematic LC medium is prepared as follows:
[1199]
[1200] Mixture Example S47 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) Nematic according to the invention LC mixture is formulated as follows:
[1201]
[1202]
[1203] Example M48
[1204] The nematic LC medium is prepared as follows:
[1205]
[1206] Mixture Example S48 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1207] Mixture M48 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1208] Example M49
[1209] The nematic LC medium is formulated as follows:
[1210]
[1211] Mixture Example S49 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1212] Mixture M49 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1213] Example M50
[1214] The nematic LC medium is formulated as follows:
[1215]
[1216]
[1217] Mixture Example S50 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1218] Mixture M50 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1219] Example M51
[1220] The nematic LC medium is formulated as follows:
[1221]
[1222]
[1223] Mixture Example S51 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1224] Mixture M51 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1225] Example M52
[1226] The nematic LC medium is formulated as follows:
[1227]
[1228]
[1229] Mixture Example S52 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1230] Mixture M52 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1231] Example M53
[1232] The nematic LC medium is formulated as follows:
[1233]
[1234]
[1235] Mixture Example S53 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1236] Mixture M53 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1237] Example M54
[1238] The nematic LC medium is formulated as follows:
[1239]
[1240]
[1241] Mixture Example S54 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1242] Mixture M54 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1243] Example M55
[1244] The nematic LC medium is formulated as follows:
[1245]
[1246]
[1247] Mixture Example S55 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1248] Mixture M55 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1249] Example M56
[1250] The nematic LC medium is formulated as follows:
[1251]
[1252]
[1253] Mixture Example S56 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1254] Mixture M56 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1255] Example M57
[1256] The nematic LC medium is formulated as follows:
[1257]
[1258] Mixture Example S57 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1259] Mixture M57 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1260] Example M58
[1261] The nematic LC medium is formulated as follows:
[1262]
[1263] Mixture Example S58 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1264] Mixture M58 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1265] Example M59
[1266] The nematic LC medium is formulated as follows:
[1267]
[1268] Mixture Example S59 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1269] Mixture M59 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1270] Example M60
[1271] The nematic LC medium is formulated as follows:
[1272]
[1273] Mixture Example S60 (stabilized with compounds of formula ST-2-3 and H-3-1) Nematic according to the invention The LC mixture is formulated as follows:
[1274]
[1275]
[1276] Example M61
[1277] The nematic LC medium is prepared as follows:
[1278]
[1279] Mixture Example S61 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1280] Mixture M61 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1281] Example M62
[1282] The nematic LC medium is prepared as follows:
[1283]
[1284]
[1285] Mixture Example S62 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1286] Mixture M62 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1287] Mixture Example S62a (stabilized with compounds of formula ST-2-3 and H-3-7) The nematic LC mixture according to the present invention is prepared as follows:
[1288] Mixture M62 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-7 1000 ppm
[1289]
[1290] Mixture Example S62b (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1291] Mixture M62 99.925 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 250 ppm
[1292] Mixture Example S62c (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1293] Mixture M62 99.9 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 500 ppm
[1294] Mixture Example S62d (stabilized with compounds of formula ST-2-3 and H-3-22) The nematic LC mixture according to the present invention is prepared as follows:
[1295] Mixture M62 99.925 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-22 250 ppm
[1296]
[1297] Mixture Example S62e (stabilized with compounds of formula ST-2-3 and H-3-22) The nematic LC mixture according to the present invention is prepared as follows:
[1298] Mixture M62 99.9 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-22 500 ppm
[1299] Mixture Example S62f (stabilized with compounds of formula ST-2-3 and H-3-22) The nematic LC mixture according to the present invention is formulated as follows:
[1300] Mixture M62 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-22 1000 ppm
[1301] Mixture Example S62g (stabilized with compounds of formula ST-2-3 and H-3-23) The nematic LC mixture according to the present invention is formulated as follows:
[1302] Mixture M62 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-23 1000 ppm
[1303]
[1304] Mixture Example S62h (stabilized with compound of formula ST-2-3)
[1305] The nematic LC mixture according to the present invention is formulated as follows:
[1306] Mixture M62 99.95 wt% Compound of formula ST-2-3 500 ppm
[1307] Mixture Example S62i (stabilized with compounds of formula ST-2-3 and H-3-1 )The nematic LC mixture according to the present invention is formulated as follows:
[1308] Mixture M62 99.875 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 750 ppm
[1309] Example M63
[1310] The nematic LC medium is formulated as follows:
[1311]
[1312]
[1313] Mixture Example S63 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1314] Mixture M63 99.875 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 750 ppm
[1315] Mixture Example S63a (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1316] Mixture M63 99.9 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 500 ppm
[1317] Mixture Example S63b (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1318] Mixture M63 99.925 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 250 ppm
[1319] Mixture Example S63c (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1320] Mixture M63 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1321] Mixture Example S63d (stabilized with compound of formula ST-2-3)
[1322] The nematic LC mixture according to the present invention is formulated as follows:
[1323] Mixture M63 99.95 wt% Compound of formula ST-2-3 500 ppm
[1324] Mixture Example S63e (stabilized with compounds of formula ST-2-3 and H-3-23) The nematic LC mixture according to the present invention is formulated as follows:
[1325] Mixture M63 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-23 1000 ppm
[1326] Mixture Example S63f (stabilized with compounds of formula ST-2-3 and H-3-22) The nematic LC mixture according to the present invention is formulated as follows:
[1327] Mixture M63 99.85% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-22 1000 ppm
[1328] Mixture Example S63g (stabilized with compounds of formula ST-2-3 and H-3-22) The nematic LC mixture according to the present invention is formulated as follows:
[1329] Mixture M63 99.9% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-22 500 ppm
[1330] Mixture Example S63h (stabilized with compounds of formula ST-2-3 and H-3-22) The nematic LC mixture according to the present invention is formulated as follows:
[1331] Mixture M63 99.925% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-22 250 ppm
[1332] Mixture Example S63i (stabilized with compounds of formula ST-2-3 and H-3-7) The nematic LC mixture according to the present invention is formulated as follows:
[1333] Mixture M63 99.85% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-7 1000 ppm
[1334] Example M64
[1335] The nematic LC medium is formulated as follows:
[1336]
[1337] Mixture Example S64 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1338] Mixture M64 99.85% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1339] Example M65
[1340] The nematic LC medium is formulated as follows:
[1341]
[1342] Mixture Example S65 (stabilized with compounds of formula ST-2-3 and H-3-1)The nematic LC mixture according to the present invention is formulated as follows:
[1343] Mixture M65 99.85% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1344] Example M66
[1345] The nematic LC medium is formulated as follows:
[1346]
[1347]
[1348] Mixture Example S66 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1349] Mixture M66 99.85% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1350] Example M67
[1351] The nematic LC medium is formulated as follows:
[1352]
[1353]
[1354] Mixture Example S67 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1355] Mixture M67 99.85% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1356] Example M68
[1357] The nematic LC medium is formulated as follows:
[1358]
[1359]
[1360] Mixture Example S68 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1361] Mixture M68 99.85% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1362] Mixture Example S68a (stabilized with compound of formula ST-2-3)
[1363] The nematic LC mixture according to the present invention is formulated as follows:
[1364] Mixture M68 99.95% by weight Compound of formula ST-2-3 500 ppm
[1365] Example M69
[1366] The nematic LC medium is formulated as follows:
[1367]
[1368]
[1369] Mixture Example S69 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1370] Mixture M69 99.85% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1371] Mixture Example S69a (stabilized with compound of formula ST-2-3)
[1372] The nematic LC mixture according to the present invention is formulated as follows:
[1373] Mixture M69 99.95% by weight Compound of formula ST-2-3 500 ppm
[1374] Example M70
[1375] The nematic LC medium is formulated as follows:
[1376]
[1377]
[1378] Mixture Example S70 (stabilized with compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1379] Mixture M70 99.85% by weight Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1380] Mixture Example S70a (stabilized with the compound of formula ST-2-3)
[1381] The nematic LC mixture according to the present invention is formulated as follows:
[1382] Mixture M70 99.95 wt% Compound of formula ST-2-3 500 ppm
[1383] Example M71
[1384] The nematic LC medium is formulated as follows:
[1385]
[1386] Mixture Example S71 (stabilized with the compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1387] Mixture M71 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1388] Mixture Example S71a (stabilized with the compound of formula ST-2-3) The nematic LC mixture according to the present invention is formulated as follows:
[1389] Mixture M71 99.95 wt% Compound of formula ST-2-3 500 ppm
[1390] Example M72
[1391] The nematic LC medium is formulated as follows:
[1392]
[1393] Mixture Example S72 (stabilized with the compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1394] Mixture M72 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1395] Mixture Example S72a (stabilized with the compound of formula ST-2-3)
[1396] The nematic LC mixture according to the present invention is formulated as follows:
[1397] Mixture M72 99.95 wt% Compound of formula ST-2-3 500 ppm
[1398] Example M73
[1399] The nematic LC medium is formulated as follows:
[1400]
[1401]
[1402] Mixture Example S73 (stabilized with the compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1403] Mixture M73 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1404] Mixture Example S73a (stabilized with the compound of formula ST-2-3)
[1405] The nematic LC mixture according to the present invention is formulated as follows:
[1406] Mixture M73 99.95 wt% Compound of formula ST-2-3 500 ppm
[1407] Example M74
[1408] The nematic LC medium is formulated as follows:
[1409]
[1410]
[1411] Mixture Example S74 (stabilized with the compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1412] Mixture M74 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1413] Mixture Example S74a (stabilized with the compound of formula ST-2-3)
[1414] The nematic LC mixture according to the present invention is formulated as follows:
[1415] Mixture M74 99.95 wt% Compound of formula ST-2-3 500 ppm
[1416] Example M75
[1417] The nematic LC medium is formulated as follows:
[1418]
[1419]
[1420] Mixture Example S75 (stabilized with the compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1421] Mixture M75 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1422] Example M76
[1423] The nematic LC medium is formulated as follows:
[1424]
[1425]
[1426] Mixture Example S76 (stabilized with the compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1427] Mixture M76 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1428] Example M77
[1429] The nematic LC medium is formulated as follows:
[1430]
[1431] Mixture Example S77 (stabilized with the compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1432] Mixture M77 99.85 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 1000 ppm
[1433] Example M78
[1434] The nematic LC medium is formulated as follows:
[1435]
[1436] Mixture Example S78 (stabilized with the compounds of formula ST-2-3 and H-3-1) Nematic according to the invention The LC mixture is formulated as follows:
[1437]
[1438]
[1439] Example M79
[1440] The nematic LC medium is prepared as follows:
[1441]
[1442] Mixture Example S79 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1443] Mixture M79 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1444] Example M80
[1445] The nematic LC medium is prepared as follows:
[1446]
[1447] Mixture Example S80 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1448] Mixture M80 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1449] Example M81
[1450] The nematic LC medium is prepared as follows:
[1451]
[1452]
[1453] Mixture Example S81 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1454] Mixture M81 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 1000 ppm
[1455] Example M82
[1456] The nematic LC medium is prepared as follows:
[1457]
[1458]
[1459] Mixture Example S82 (Stabilized with Compound of Formula ST-2-3) The nematic LC mixture according to the present invention is prepared as follows:
[1460] Mixture M82 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1461] Example M83
[1462] The nematic LC medium is prepared as follows:
[1463]
[1464]
[1465] Mixture Example S83 (Stabilized with Compound of Formula ST-2-3) The nematic LC mixture according to the present invention is prepared as follows:
[1466] Mixture M83 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1467] Example M84
[1468] The nematic LC medium is prepared as follows:
[1469]
[1470]
[1471] Mixture Example S84 (Stabilized with Compound of Formula ST-2-3)
[1472] The nematic LC mixture according to the present invention is prepared as follows:
[1473] Mixture M84 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1474] Mixture Example S84a (Stabilized with Compounds of Formula ST-2-3 and H-3-22) The nematic LC mixture according to the present invention is prepared as follows:
[1475] Mixture M84 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-22 1000 ppm
[1476] Mixture Example S84b (Stabilized with Compounds of Formula ST-2-3 and H-3-22) The nematic LC mixture according to the present invention is prepared as follows:
[1477] Mixture M84 99.925 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-22 250 ppm
[1478] Example M85
[1479] The nematic LC medium is prepared as follows:
[1480]
[1481]
[1482] Mixture Example S85 (Stabilized with Compound of Formula ST-2-3)
[1483] The nematic LC mixture according to the present invention is prepared as follows:
[1484] Mixture M85 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1485] Mixture Example S85a (Stabilized with Compounds of Formula ST-2-3 and H-3-22) The nematic LC mixture according to the present invention is formulated as follows:
[1486] Mixture M85 99.85 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-22 1000 ppm
[1487] Mixture Example S85b (Stabilized with Compounds of Formula ST-2-3 and H-3-22) The nematic LC mixture according to the present invention is formulated as follows:
[1488] Mixture M85 99.925 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-22 250 ppm
[1489] Example M86
[1490] The nematic LC medium is formulated as follows:
[1491]
[1492]
[1493] Mixture Example S86 (Stabilized with Compound of Formula ST-2-3) The nematic LC mixture according to the present invention is formulated as follows:
[1494] Mixture M86 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1495] Example M87
[1496] The nematic LC medium is formulated as follows:
[1497]
[1498]
[1499] Mixture Example S87 (Stabilized with Compound of Formula ST-2-3) The nematic LC mixture according to the present invention is formulated as follows:
[1500] Mixture M87 99.95 wt% Compound of Formula ST-2-3 500 ppm
[1501] Example M88
[1502] The nematic LC medium is formulated as follows:
[1503]
[1504]
[1505] Mixture Example S88 (Stabilized with the compound of formula ST-1-3) The nematic LC mixture according to the present invention is formulated as follows:
[1506] Mixture M88 99.97 wt% Compound of formula ST-1-3 300 ppm
[1507] Example M89
[1508] The nematic LC medium is formulated as follows:
[1509]
[1510]
[1511] Mixture Example S89 (Stabilized with the compounds of formula ST-1-3 and H-3-7) The nematic LC mixture according to the present invention is formulated as follows:
[1512] Mixture M89 99.85 wt% Compound of formula ST-1-3 500 ppm Compound of formula H-3-7 1000 ppm
[1513] Example M90
[1514] The nematic LC medium is formulated as follows:
[1515]
[1516]
[1517] Mixture Example S90 (Stabilized with the compounds of formula ST-1-3 and H-3-22) The nematic LC mixture is formulated as follows:
[1518]
[1519]
[1520] Example M91
[1521] The nematic LC medium is formulated as follows:
[1522]
[1523]
[1524] Mixture Example S91 (Stabilized with the compounds of formula ST-1-3 and H-3-23) The nematic LC mixture is formulated as follows:
[1525]
[1526]
[1527] Example M92
[1528] The nematic LC medium is formulated as follows:
[1529]
[1530]
[1531] Mixture Example S92 (Stabilized with the compounds of formula ST-1-3 and H-3-7) The nematic LC mixture according to the present invention is formulated as follows:
[1532] Mixture M92 99.85 wt% Compound of formula ST-1-3 500 ppm Compound of formula H-3-7 1000 ppm
[1533] Example M93
[1534] The nematic LC medium is prepared as follows:
[1535]
[1536] Mixture Example S93 (Stabilized with the compounds of formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is prepared as follows:
[1537] Mixture M93 99.925 wt% Compound of formula ST-2-3 500 ppm Compound of formula H-3-1 250 ppm
[1538] Example M94
[1539] The nematic LC medium is prepared as follows:
[1540]
[1541]
[1542] Mixture Example S94 (Stabilized with the compounds of formula ST-1-3 and H-3-1) The nematic LC mixture is formulated as follows:
[1543]
[1544]
[1545] Example M95
[1546] The nematic LC medium is prepared as follows:
[1547]
[1548]
[1549] Mixture Example S95 (Stabilized with the compounds of formula ST-2-3 and H-3-23) The nematic LC mixture is formulated as follows:
[1550]
[1551]
[1552] Example M96
[1553] The nematic LC medium is prepared as follows:
[1554]
[1555]
[1556] Mixture Example S96 (Stabilized with the compound of formula ST-1-3)The nematic LC mixture according to the present invention is formulated as follows:
[1557] Mixture M96 99.95 wt% Compound of formula ST-1-3 500 ppm
[1558] Example M97
[1559] The nematic LC medium is formulated as follows:
[1560]
[1561]
[1562] Mixture Example S97 (Stabilized with the compound of formula ST-2-3) The nematic LC mixture according to the present invention is formulated as follows:
[1563] Mixture M97 99.96 wt% Compound of formula ST-2-3 400 ppm
[1564] Example M98
[1565] The nematic LC medium is formulated as follows:
[1566]
[1567]
[1568] Mixture Example S98 (Stabilized with the compound of formula ST-4-1) The nematic LC mixture according to the present invention is formulated as follows:
[1569] Mixture M98 99.96 wt% Compound of formula ST-4-1 400 ppm
[1570]
[1571] Example M99
[1572] The nematic LC medium is formulated as follows:
[1573]
[1574] Mixture Example S99 (Stabilized with the compound of formula ST-4-2) The nematic LC mixture according to the present invention is formulated as follows:
[1575] Mixture M99 99.96 wt% Compound of formula ST-4-2 400 ppm
[1576]
[1577] Example M100
[1578] The nematic LC medium is formulated as follows:
[1579]
[1580]
[1581] Mixture Example S100 (Stabilized with the compounds of formula ST-4-2 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1582] Mixture M100 99.85 wt% Compound of formula ST-4-2 500 ppm Compound of formula H-3-1 1000 ppm
[1583] Example M101
[1584] The nematic LC medium is formulated as follows:
[1585]
[1586]
[1587] Mixture Example S101 (Stabilized with the compounds of formula ST-4-1 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1588] Mixture M101 99.85 wt% Compound of formula ST-4-1 500 ppm Compound of formula H-3-1 1000 ppm
[1589] Example M102
[1590] The nematic LC medium is formulated as follows:
[1591]
[1592]
[1593] Mixture Example S102 (Stabilized with Compounds of Formula ST-1-3 and H-3-7) The nematic LC mixture according to the present invention is formulated as follows:
[1594] Mixture M102 99.85 wt% Compound of Formula ST-1-3 500 ppm Compound of Formula H-3-7 1000 ppm
[1595] Example M103
[1596] The nematic LC medium is formulated as follows:
[1597]
[1598] Mixture Example S103 (Stabilized with Compounds of Formula ST-4-1 and H-3-7) The nematic LC mixture according to the present invention is formulated as follows:
[1599] Mixture M103 99.85 wt% Compound of Formula ST-4-1 500 ppm Compound of Formula H-3-7 1000 ppm
[1600] Example M104
[1601] The nematic LC medium is formulated as follows:
[1602]
[1603]
[1604] Mixture Example S104 (Stabilized with Compounds of Formula ST-2-3 and H-3-1) The nematic LC mixture according to the present invention is formulated as follows:
[1605] Mixture M104 99.925 wt% Compound of Formula ST-2-3 500 ppm Compound of Formula H-3-1 250 ppm
Claims
1. A liquid crystal medium, characterized in that It comprises one or more compounds of formula I where the individual substituents have the following meanings, identically or differently on each occurrence and independently of one another: R 0 represents an alkyl group having 1 to 12 C atoms, or an alkenyl group having 2 to 12 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡O-, -OCF2-, -CH=CH-, -C≡C-, -C≡O-, -C≡C-, -C≡O-, -C≡CH-, -C≡C-, -C≡O-, -C≡CH-, -C≡C-, -C≡O-, -C≡C ... -O-, -CO-O- or -O-CO-, wherein one or more H atoms may be substituted by halogen atoms; X 0 represents a halogen atom, -CN, -SCN, -NCS or an alkyl or alkoxy group having 1 to 6 C atoms, or an alkenyl or alkenyloxy group having 2 to 6 C atoms, in which one or more H atoms have been replaced by a halogen atom; L 1 and L 2 Each independently represents H, F or Cl, wherein L 1 and L 2 Not at the same time means H; Y 0 Indicates H or CH3; one or more antioxidants, and optionally One or more light stabilizers.
2. The medium according to claim 1, characterized in that The one or more antioxidants are compounds of formula ST: The substituents have the following meanings: X 21 and X 22 Each independently represents -O-, -CH2-, -CHR 23 -or-NR 23 -; R 21 and R 22 each independently of one another represents an H atom or an alkyl or alkoxy group having 1 to 12 C atoms, an alkenyl, alkynyl, alkenyloxy or alkoxyalkyl group having 2 to 12 C atoms, or a cycloalkyl group having 3 to 12 C atoms, wherein one or more non-adjacent CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡O-, -C≡C-, -C≡O-, -C≡CH ...C-, -C≡O-, -C≡CH-, -C≡C-, -C -O-, -CO-O- or -O-CO-, in which one or more H atoms may be substituted by halogen atoms, or cycloalkyl or cycloalkoxy having 3 to 12 C atoms, in which one or more H atoms may be substituted by halogen atoms; R 23 represents an H atom, an alkyl group having 1 to 10 C atoms, or an alkoxy group; r represents 0 or 1.
3. The medium according to claim 1 or 2, characterized in that The one or more light stabilizers are compounds of formula H: in R 11 each independently of one another represents an H atom, F, an alkyl group having 1 to 20 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡ ... -O-, -CO-O-, -O-CO-, -NR 13 -、-CO-NR 13 -or-NR 13 -CO- is replaced, and one or more of the H atoms can be replaced by F, OR 13 、N(R 13 )(R 14 ) or R 15 replace; R 12 each independently of one another represents an H atom, an alkyl group having 1 to 20 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡ ...C-, -C≡O-, -C≡C-, -C≡C-, -C≡O-, -C≡C-, -C≡C-, -C≡C-, -C≡O-, -C≡ -O-, -CO-O-, -O-CO-, -NR 13 -、-CO-NR 13 -or-NR 13 -CO-substituted, a hydrocarbon group containing a cycloalkyl group or an alkylcycloalkyl group, and wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡O ...CH-, -C≡C-, -C≡O-, -C≡C-, -C� -O-, -CO-O-, -O-CO-, -NR 13 -、-CO-NR 13 -or-NR 13 -CO- is replaced, and one or more of the H atoms can be replaced by F, OR 13 、N(R 13 )(R 14 ) or R 15 substituted, or aromatic or heteroaromatic hydrocarbon radicals in which one or more H atoms may be replaced by OR 13 、N(R 13 )(R 14 ) or R 15 replace; R 13 , R 14 and R 15 Each independently of one another represents an alkyl or acyl group having 1 to 10 C atoms, or an aromatic hydrocarbon group or a carboxylic acid group having 6 to 12 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡O-, -OCF2-, -CH=CH-, -C≡C-, -C≡O-, -C≡C ...C-, -C≡C-, -C≡C- -O-, -CO-O-, -O-CO-, -NR 13 -、-CO-NR 13 -or-NR 13 -CO- substitution; R 16 each independently of one another represents an H atom, an alkyl or alkoxy group having 1 to 10 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡ ...C-, -C≡O-, -C≡C-, -C -O-, -CO-O-, -O-CO-, -NR 13 -、-CO-NR 13 -or-NR 13 -CO-substituted, O-cycloalkyl with 3 to 12 C atoms, O · or OH; R 17 each independently of one another represents an H atom, an alkyl or alkoxy radical having 1 to 10 C atoms, or an alkylene radical or a single bond, wherein R 17 Can be used with S 11 Together they form a ring structure; S 11 and S 12 each independently of one another represents an alkylene group having 1 to 20 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡O-, -OCF2-, -CH=CH-, -C≡C-, -C≡O-, -C≡C-, -C≡O-, -C≡O-, -C≡CH-, -C≡C-, -C≡O ...C-, -C≡O-, -C≡C-, -C -O-, -CO-O-, -O-CO-, -NR 13 -、-CO-NR 13 -or-NR 13 -CO- is replaced, and one or more of the H atoms can be replaced by F, OR 13 、N(R 13 )(R 14 ) or R 15 Substitution, or single bond; Y 11 To Y 14 each independently of one another represents a methyl group or an ethyl group; X 11 Indicates C; Z 11 To Z 14 Each independently represents -O-, -(C=O)-, -O-(C=O)-, -(C=O)-O-, -O-(C=O)-O-, -(NR 13 )-、-NR 13 -(C=O)-, -(C=O)-NR 13 - or a single bond, and if S 11 is a single bond, Z 11 and Z 12 If the two are different, it means -O-; if S 12 is a single bond, Z 13 and Z 14 If both do not represent -O-, and if q represents 0, Z 12 and Z 13 The two are not the same, which means -O-; p means 1 or 2; q represents 0 or 1; o represents (3-p); n represents an integer from 1 to 10; m represents an integer from 0 to 8; wherein n*p represents an integer from 1 to 10, preferably an integer from 2 to 8, and represents an organic moiety having (m+n) bonding sites.
4. A medium according to one or more of claims 1 to 3, characterized in that The one or more compounds of formula I are selected from one of the following: in R 0 represents an alkyl group having 1 to 6 C atoms, or an alkenyl group having 2 to 6 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡ ... -O-, -CO-O- or -O-CO-, wherein one or more H atoms may be substituted by halogen atoms; X 0 represents an F atom or an alkyl or alkoxy group having 1 to 3 C atoms, or an alkenyl or alkenyloxy group having 2 or 3 C atoms, wherein one or more H atoms are replaced by an F atom; and Y 0 It represents H or CH3.
5. The medium according to claim 3, characterized in that The one or more compounds of formula H are selected from one of the following: R 11 each independently of one another represents an H atom, an alkyl group having 1 to 20 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡ ...C-, -C≡O-, -C≡C-, -C≡C-, -C≡O-, -C≡C-, -C≡C-, -C≡C-, -C≡O-, -C≡ -O-, -CO-O- or -O-CO-, and one or more of the H atoms may be replaced by F, OR 13 、N(R 13 )(R 14 ) or R 15 replace; R 16 Represents H atom or O · ; S 11 and S 12 each independently of one another represents an alkylene group having 1 to 20 C atoms, wherein one or more CH2 groups are optionally replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -C≡C-, -C≡ ...C≡C-, -C≡O-, -C≡C-, - -O-, -CO-O- or -O-CO-, and one or more of the H atoms may be replaced by F, OR 13 、N(R 13 )(R 14 ) or R 15 substitution, or a single bond; and n represents an integer from 0 to 8.
6. A medium according to one or more of claims 1 to 5, characterized in that It comprises one or more compounds selected from the following formulae: The substituents have the following meanings: "alkyl" and "alkyl*" each independently represent an alkyl group having 1 to 6 C atoms; "Alkenyl" and "alkenyl*" each independently of one another represent alkenyl having 2 to 6 C atoms.
7. A medium according to one or more of claims 1 to 6, characterized in that The medium comprises one or more compounds selected from the following formulae: in R 1 and R 2 each independently of one another represents n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 C atoms, and L 1 represents H, F or Cl.
8. A medium according to one or more of claims 1 to 7, characterized in that It comprises one or more compounds selected from the following formulae: The substituents have the following meanings: express express in R 0 , L 1 To L 6 , X 0 and Y 0 respectively have the following characteristics for R in claim 1 0 , L 1 , L 2 , X 0 and Y 0 The meaning given.
9. The medium according to claim 8, wherein the one or more compounds of formula II are selected from the following subformulae: Where R 0 and X 0 has the meaning given in formula II.
10. The medium according to claim 8, wherein the one or more compounds of formula III are selected from the following subformulae: Where R 0 and X 0 has the meaning given in formula III.
11. A medium according to one or more of claims 1 to 10, characterized in that It additionally comprises one or more compounds selected from the following formulae: Where R 0 , X 0 , L 1 , L 2 and Y 0 has the meaning given in claim 1; L 3 and L 4 Each independently has a 1 the meaning given; Z 0 represents -C2H4-, -(CH2)4-, -CH=CH-, -CF=CF-, -C2F4-, -CH2CF2-, -CF2CH2-, -CH2O-, -OCH2-, -COO-, -CF2O- or -OCF2-, also representing a single bond in Formulas V and VI; and s represents 0 or 1.
12. A medium according to one or more of claims 1 to 11, characterized in that It contains one or more compounds selected from the following formula Where R 0 , L 1 To L 4 , X 0 and Y 0 respectively have the following characteristics for R in claim 1 0 , L 1 , L 2 , X 0 and Y 0 The meaning given.
13. A medium according to one or more of claims 1 to 12, characterized in that It comprises one or more compounds selected from the following formulae: in express Where R 1 and X 0 respectively have the following characteristics for R in claim 1 0 and X 0 The meaning given.
14. A medium according to one or more of claims 1 to 13, characterized in that It comprises one or more compounds of formula I, one or more antioxidants, and optionally, one or more light stabilizers, and one or more compounds selected from formula Z1, Z2, Z3, Z4, Z5, II, III, IV, VI, XIV, XX, XII, XXIII, XXIX, XVI, XVIIa, XVIIb, and XVIIc.
15. A medium according to one or more of claims 1 to 14, characterized in that It comprises one or more compounds of formula I, one or more antioxidants, and optionally, one or more light stabilizers, and one or more compounds selected from formula LP1 and / or LP2.
16. A medium according to one or more of claims 1 to 15, characterized in that It comprises one or more compounds of formula I, one or more antioxidants, and optionally, one or more light stabilizers, and one or more compounds selected from the group consisting of formulae XXIX, XXX and XXVIIIa.
17. Process for preparing a liquid-crystalline medium according to one or more of claims 1 to 16, characterized in that One or more antioxidants and one or more light stabilizers are mixed with one or more mesogenic compounds, and optionally one or more polymerizable compounds and / or one or more additives.
18. Use of a liquid-crystalline medium according to one or more of claims 1 to 16 for electro-optical purposes.
19. An electro-optical liquid crystal display or an AR / VR headset comprising a liquid crystal medium according to one or more of claims 1 to 16.
20. The electro-optical liquid crystal display according to claim 19, characterized in that It is a TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-HB-FFS, PS-XB-FFS, SA-HB-FFS, SA-XB-FS, polymer-stabilized SA-HB-FFS, polymer-stabilized SA-XB-FFS, positive VA or positive PS-VA display.
Citation Information
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