Patent Application
20250230360
The present invention relates to liquid-crystalline (LC) media having positive dielectric anisotropy and to liquid-crystal displays (LCDs) containing these media, especially to displays addressed by an active matrix and in particular to energy efficient LC displays of the TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-FFS, SA-HB-FFS, SA-XB-FFS, polymer stabilised SA-HB-FFS, polymer stabilised SA-XB-FFS, positive VA or positive PS-VA type. The media have an improved long-term stability against UV radiation and elevated temperatures.
Liquid-crystal displays (LCDs) are used in many areas for the display of information. LCDs are used both for direct-view displays and for 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 together with their various modifications, as well as others. All these modes utilise an electric field which generated substantially perpendicular to the substrates and the liquid-crystal layer.
Besides these modes, there are also electro-optical modes that utilise an electric field which is substantially parallel to the substrates or the liquid-crystal layer. For example, WO 91/10936 discloses a liquid-crystal display in which the electric signals are generated in such a way that the electric fields have a significant component parallel to the liquid-crystal layer, and which has since then become known as in-plane switching (IPS) display. The principles of operating such a display are described, for example, by R. A. Soref in Journal of Applied Physics, Vol. 45, No. 12, pp. 5466-5468 (1974).
IPS displays contain an LC layer between two substrates with planar orientation, where the two electrodes are arranged on only one of the two substrates and preferably have interdigitated, comb-shaped structures. On application of a voltage to the electrodes an electric field with a significant component parallel to the LC layer is generated between them. This causes realignment of the LC molecules in the layer plane.
EP 0 588 568, for example, discloses various possibilities for the design of the electrodes and for addressing an IPS display. DE 198 24 137 likewise describes various embodiments of such IPS displays.
Liquid-crystalline materials for IPS displays of this type are described, for example, in DE 195 28 104.
Furthermore, so-called “fringe-field switching” (FFS) displays have been reported (see, inter alia, S. H. Jung et al., Jpn. J. Appl. Phys., Volume 43, No. 3, 2004, 1028), which contain two electrodes on the same substrate, one of which is structured in a comb-shaped manner and the other is unstructured. A strong, so-called “fringe field” is thereby generated, i.e. a strong electric field close to the edge of the electrodes, and, throughout the cell, an electric field which has both a strong vertical component and also a strong horizontal component. FFS displays have a low viewing-angle dependence of the contrast. FFS displays usually contain an LC medium with positive dielectric anisotropy, and an alignment layer, usually of polyimide, which provides planar alignment to the molecules of the LC medium.
Liquid-crystal displays of the IPS and FFS electro-optical mode are in particular suitable for use in modern desktop monitors, TV sets and multimedia applications. The liquid-crystalline media according to the present invention are preferably used in displays of this type. In general, dielectrically positive liquid-crystalline media having rather lower values of the dielectric anisotropy are used in FFS displays, but in some cases liquid-crystalline media having a dielectric anisotropy of only about 3 or even less are also used in IPS displays.
A further improvement has been achieved by the HB-FFS mode. One of the unique features of the HB-FFS mode in contrast to the traditional FFS technology is that it enables higher transmittance which allows operation of the panel with less energy consumption.
Another recently developed mode is the XB-FFS mode, wherein the liquid-crystalline medium additionally contains a polar liquid crystal compound with low dielectric anisotropy.
Liquid-crystal compositions which are suitable for LCDs and especially for FFS and IPS displays are known in prior art, for example, from JP 07-181 439 (A), EP 0 667 555, EP 0 673 986, DE 195 09 410, DE 195 28 106 and DE 195 28 107. However, these compositions have certain disadvantages. Amongst other deficiencies, most of them result in disadvantageously long addressing times, have inadequate values of the resistivity and/or require excessively high operating voltages. Both an improvement in the operating properties and also in the shelf life are necessary here.
FFS and IPS displays can be operated as active-matrix displays (AMD) or passive-matrix displays (PMD). In the case of active-matrix displays individual pixels are usually addressed by integrated, non-linear active elements such as, for example, thin-film transistors (TFTs), while in the case of passive-matrix displays individual pixels are usually addressed by the multiplex method as known from the prior art.
The displays according to the present invention are preferably by an active matrix, preferably by a matrix of TFT. However, the liquid crystals according to the invention can also advantageously be used in displays having other known addressing means.
Typical applications of in-plane switching (IPS) and fringe field switching (FFS) technologies are monitors, notebooks, televisions, mobile telephones, tablet PCs, etc.
Both the IPS and the FFS technology have certain advantages over other LCD technologies, such as, for example, the vertical alignment (VA) technology, e.g. a broad viewing angle dependency of the contrast.
The provision of further liquid-crystalline media and the use thereof in a display having high transmission, a good black state and a high contrast ratio is a central challenge for modern FFS and IPS applications. In addition, modern applications also require good low-temperature stability and fast addressing times.
Matrix liquid crystal display (MFK) displays with full array LED backlighting, which have become increasingly common in recent years, include a large number of light-emitting diodes (LEDs) arranged directly behind the layer with the FK medium.
Modern high-performance InGaN LEDs sometimes reach operating temperatures of more than 70° C. and, depending on the design, can emit UV radiation as well as visible light. Direct contact between the LEDs and the FRP medium therefore places special demands on the UV stability and temperature resistance of the FRP medium. State-of-the-art MFK displays therefore do not meet today's requirements.
Recently, MFK displays have been increasingly used in outdoor applications such as PIDs (Public Information Displays) for displaying various types of information at train stations, roads, airports, hotels and shopping malls. Compared to conventional MFK displays, such as those used in TV applications, PIDs should have much higher long-term resistance to solar UV radiation and elevated temperatures, as well as a wider operating temperature range.
In case of FFS displays there is a need for further optimization of response time, contrast, brightness and reliability. However, it was found that the liquid-crystalline materials of the prior art do often not achieve all these requirements at the same time.
The prior art, for example WO 2010/099853 A1 and DE 10 2010 027 099 A1, discloses thiophene-containing LC media. WO 2010/099853 A1 teaches compounds containing a thiophene-2,5-diyl unit which is linked directly to a 2- and/or 6-substituted 1,4-phenylene unit. WO 2010/099853 A1 describes the devel-opment of novel materials for use in LC displays. This object was achieved by the provision of compounds of the general formula
where inter alia A0 denotes a 2,6-difluoro-1,4-phenylene unit, A1 and A2, besides other meanings, denote a 1,4-phenylene or 1,4-cyclohexylene unit, and Z1 and Z2 denote a bridging element or a single bond.
Specific examples described are, for example, the following compounds (see WO 2010/099853 A1):
For many practical applications in liquid-crystal displays, the known liquid-crystalline media comprising thiophene compounds are not sufficiently stable. In particular, exposure to UV radiation, but also even irradiation with the usual backlighting, results in an impairment, in particular of the electrical properties. Thus, for example, the conductivity increases significantly.
DE 10 2010 027 099 A1 describes LC media which comprise the compounds disclosed in WO 2010/099853 A1 and bithienyl derivatives of the formula
as stabiliser. These bithienyl derivatives are preferably employed in combination with thiophene 1,1-dioxide derivatives of the formula
In both the above formulae, A1 and A2 may denote 1,4-phenylene or 1,4-cyclohexylene and Z1 and Z2 denote a single bond. Specific examples described are the following compounds (see DE 10 2010 027 099 A1):
The present invention has the object of providing liquid-crystalline media, in particular for FFS and IPS displays, but also for TN, positive VA or STN displays, and in particular for active-matrix displays like those addressed by TFTs, which do not exhibit the disadvantages indicated above or only do so to a lesser extent and preferably have high specific resistance, low threshold voltage, high dielectric anisotropy, a good low temperature stability (LTS), fast response times and low rotational viscosities, an excellent long term stability against UV radiation and increased operating temperatures and enable high brightness.
This was achieved by providing liquid-crystalline media as described and claimed hereinafter.
It has now been surprisingly found that liquid-crystalline media according to the present invention which contain a combination of one or more compounds of Formula I and at least one compound of Formula ST show several improvements, especially when being used in FFS mode displays, like a good solubility and a low ratio of γ1/k11, and enable fast response times.
The liquid-crystal media according to the present invention are especially suitable for use in liquid-crystal displays of the FFS, HB-FFS, XB-FFS and IPS mode based on dielectrically positive liquid crystals, and polymer stabilised variants thereof. The subject matter of the present invention is a liquid-crystalline medium, character-ised in that it comprises one or more compounds of Formula I
in which the individual substituents have the following meanings:
—O—, —CO—O— or —O—CO— in such a way that 0 atoms are not linked directly to one another, and in which one or more H atoms may be replaced by a halogen atom or a cycloalkyl or a cycloalkoxy group having 3 to 12 C atoms, in which one or more H atoms may be replaced by a halogen atom,
In addition, the LC medium of the present invention comprises one or more compounds of the following Formula ST:
—O—, —CO—O—or —O—CO— in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by a halogen atom or a cycloalkyl or a cycloalkoxy group having 3 to 12 C atoms, in which one or more H atoms may be replaced by a halogen atom,
The invention further relates to the use of a liquid-crystalline medium as described above and below for electro-optical purposes, in particular for the use in liquid-crystal displays, shutter glasses, LC windows, 3D applications, preferably in 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 stabilised SA-HB-FFS, polymer stabilised SA-XB-FFS, positive VA and positive PS-VA displays, very preferably in FFS, HB-FFS, IPS, PS-HB-FFS and PS-IPS displays.
The invention further relates to an electro-optical liquid-crystal display containing a liquid-crystalline medium as described above and below, 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 stabilised SA-HB-FFS, polymer stabilised SA-XB-FFS, positive VA or positive PS-VA display, preferably a FFS, HB-FFS, IPS, PS-HB-FFS or PS-IPS display.
In the present application, all atoms also include their isotopes. In some embodiments of the present invention one or more hydrogen atoms (H) may be replaced by deuterium (D); a high degree of deuteration enables or simplifies analytical determination of compounds, in particular in the case of low concentrations.
In the formulae above and below, if R0, R1, R21, R22 or R2 denotes an alkyl radical and/or an alkoxy radical, this may be straight-chain or branched. It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy. R0 preferably denotes straight-chain alkyl having 2 to 6 C atoms.
Oxaalkyl preferably denotes straight-chain 2-oxapropyl (=methoxymethyl), 2- (=ethoxymethyl) or 3-oxabutyl (=2-methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3, 4-, 5- or 6-oxaheptyl, 2-, 3, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, 2-, 3, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl.
If R0, R1, R21, R22 or R2 denotes an alkoxy or oxaalkyl group it may also contain one or more additional oxygen atoms, provided that oxygen atoms are not linked directly to one another.
In another preferred embodiment, one or more of R0, R1 and R2 are selected from the group consisting of
—S1—F, —O—S1—F, —O—S1—O—S2, wherein S1 is C1-12-alkylene or C2-12-alkenylene and S2 is H, C1-12-alkyl or C2-12-alkenyl, and very preferably one or more of R0, R1 and R2 are selected from the group consisting of
—OCH2OCH3, —O(CH2)2OCH3, —O(CH2)3OCH3, —O(CH2)4OCH3, —O(CH2)2F, —O(CH2)3F, —O(CH2)4F.
If R0, R1, R21, R22 or R2 denotes an alkyl radical in which one CH2 group has been replaced by —CH═CH—, this may be straight-chain or branched. It is preferably straight-chain and has 2 to 10 C atoms. Accordingly, it denotes, in particular, 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.
If R0, R1, R21, R22 or R2 denotes an alkyl or alkenyl radical which is at least monosubstituted by halogen, this radical is preferably straight-chain, and halogen is preferably F or Cl. In the case of polysubstitution, halogen is preferably F. The resultant radicals also include perfluorinated radicals. In the case of mono-substitution, the fluorine or chlorine substituent may be in any desired position, but is preferably in the (ω-position.
In the formulae above and below, X0 is preferably F, Cl or a mono- or poly-fluorinated alkyl or alkoxy radical having 1, 2 or 3 C atoms or a mono- or polyfluorinated alkenyl radical having 2 or 3 C atoms. X0 is particularly preferably F, Cl, CF3, CHF2, OCF3, OCHF2, OCFHCF3, OCFHCHF2, OCFHCHF2, OCF2CH3, OCF2CHF2, OCF2CHF2, OCF2CF2CHF2, OCF2CF2CHF2, OCFHCF2CF3, OCFHCF2CHF2, OCF2CF2CF3, OCF2CF2CClF2, OCClFCF2CF3, OCH═CF2 or CH═CF2, very particularly preferably F or OCF3, furthermore CF3, OCF═CF2, OCHF2 or OCH═CF2.
In the LC media according to the present invention the use of compounds of Formula I together with compounds of formulae Z1 to Z3 or their sub-formulae enables to achieve an increased value of ε⊥ and at the same time a decrease of the rotational viscosity and the ratios of γ1/k22 and γ1/k11, and thus fast response times.
Preference is given to LC media comprising the compounds of Formula I in which A0 denotes phenylene-1,4-diyl, in which, in addition, one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH3, CHF2, CH2F, OCH3, OCHF2, CF3 or OCF3. Particularly preferred are compounds in which A0 denotes
and very particularly preferably in which
A0 denotes
The preferred compounds of the Formula I result in media having a particularly high clearing point, low rotational viscosity, a broad nematic phase, high birefringence and an excellent long-term thermal and UV stability.
Preference is furthermore given to compounds of the Formula I in which m and n denote 0, 1 or 2, particularly preferably 0 or 1. Particular preference is given to compounds of the Formula I in which n denotes 0, i.e. the thiophene ring is a terminal ring. Preference is furthermore given to compounds of the Formula I in which m denotes 0, 1 or 2, preferably 1 or 2 and very particularly preferably 1.
A1 and A2 in Formula I particularly preferably denote phenylene-1,4-diyl, which may also be mono- or polysubstituted by F, furthermore cyclohexane-1,4-diyl, cyclohexenylene-1,4-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl.
Z1 and Z2 in Formula I particularly preferably denote —CF2O—, —OCF2— or a single bond, wherein a single bond is particularly preferred.
A1 and A2 in Formula I particularly preferably denote
preferably unsubstituted 1,4-phenylene, in which L denotes halogen, CF3 or CN, preferably F.
Preference is furthermore given to compounds of the Formula I in which R1 and R2 each, independently of one another, denote H, F, Cl, Br, —CN, —SCN, —NCS, SF5, halogen, or alkyl, alkenyl or alkynyl having 1 to 8, preferably 1 to 5, C atoms, each of which is optionally substituted by halogen, in particular by F.
Particularly preferred radicals R1 and R2 in Formula I denote H, halogen, or alkyl, alkenyl, alkynyl or alkoxy having 1 to 12, preferably 1 to 8, C atoms, each of which is optionally substituted by halogen, in particular by F, particularly preferred are H, F, alkyl, alkenyl or alkynyl having 1 to 8 C atoms. Preferably, at least one radical is not H, particularly preferably both radicals R1 and R2 are not H. R1 is very particularly preferably equal to alkyl. R2 is furthermore preferably H, alkyl or fluorine. Very particularly preferably, R1 is alkyl and R2 is H or alkyl. R1, R2 each, independently of one another, very particularly preferably denote unbranched alkyl having 1 to 5 C atoms. If R1 and R2 denote substituted alkyl, alkoxy, alkenyl or alkynyl, the total number of C atoms in the two groups R1 and R2 is preferably less than 10.
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, ethenyl, 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-pentoxy, n-hexoxy, n-heptoxy, n-octoxy.
Halogen preferably denotes F or Cl.
Particularly preferred compounds of the Formula I are those selected from the following sub-formulae:
in which R1 and R2 have the meanings indicated in Formula I, and L1 to L6 independently denote H or F. R1 and R2 therein preferably denote optionally fluorinated alkyl or alkoxy having 1 to 12 C atoms, optionally fluorinated alkenyl or alkynyl having 2 to 12 C atoms, optionally fluorinated cycloalkyl having 3 to 12 C atoms.
Particularly preferred are optionally fluorinated alkyl, alkenyl or alkynyl having 1 to 5 C atoms. L2 in the Formulae I-1-1 to I-1-6 preferably denotes F. In the Formulae I-1-4 to I-1-6, L3 and L4 preferably denote H. In the Formulae I-1-4 to I-1-6 L3 and L4 preferably denote F.
In a particularly preferred embodiment the compounds of Formula I are selected from the following structures:
—O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by a halogen atom, in which one or more H atoms may be replaced by a halogen atom.
LC media according to the invention having a particularly high long-term stability against UV radiation and elevated temperatures and a low rotational viscosity are obtainable with the following compounds of the general Formula I:
wherein R1 and R2 are as defined above.
Additionally, LC media comprising the following compounds of Formula I are particularly preferred:
Mostly preferred compounds of Formula I include, in particular, one or more of the following:
As a further possibility, the following compounds of Formula I can be used:
The compounds of the Formula I can be prepared analogously to processes known to the person skilled in the art and described in standard works of organic chemistry, such as, for example, in Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Thieme-Verlag, Stuttgart.
In addition to thiophene derivatives of general Formula I, the LC medium of the present invention comprises one or more compounds of general Formula ST:
in which the individual substituents A2, R21, R22, X21, X22 and r are specified in Claim 1.
LC media comprising compounds of the following sub-formulae ST-1, ST-2 and ST-3 showed a particularly high long-term thermal and UV stability:
In particularly preferred embodiments, the compounds of general Formula ST can be selected from the following specific structures:
In a further preferred embodiment, the LC medium according to the present invention may comprise at least one further sterically hindered phenol, which is mentioned in Table B below.
In addition to one or more compounds of Formulae I and ST as defined above the medium may optionally comprise one or more compounds of the Formula H
denotes an organic moiety having (m+n) bonding sites,
In some preferred embodiments of the present invention, in the compounds of the Formula H,
(biphenyl-1,1′,3,3′-tetrayl) or
(benzene-1,2,4,5-tetrayl)
denotes
denotes (benzene-1,3,5-triyl) or
(benzene-1,2,4-triyl),
R2-denotes —(CH2—)2, —(CH2—)3, —(CH2—)4, —(CH2—)5, —(CH2—)6, —(CH2—)7, —(CH2—)8, i.e.
(1,4-phenylene),
(1,3-phenylene),
(1,2-phenylene) or
(trans-1,4-cyclohexylene) and/or
In a preferred embodiment of the present application, in the compounds of the Formula H,
denotes a group selected from the group of the formulae
In a further preferred embodiment of the present application, in the compounds of the Formula H,
denotes a group selected from the group of the formulae
In yet a further preferred embodiment of the present invention, in the compounds of the Formula H in which p preferably denotes 1,
denotes —Z12—S11—Z11—, preferably —O—S11—O—, —S11—O— or —O—S11—, particularly preferably —O—S11—O— or —S11—O—.
In a further preferred embodiment of the present invention, in the compounds of the Formula H, the group
In a further preferred embodiment of the present invention in which p is 2, which may be identical to or different from those described above, in the compounds of the Formula H,
denotes a group selected from the group of the formulae
In yet a further preferred embodiment of the present invention, which may be identical to or different from those described above, in the compounds of the Formula H, the group
on each occurrence, independently of one another, denotes
Compounds of the following general Formulae H-1-1, H-1-2 and H-1-3, showed to be particularly efficient UV stabilisers in liquid-crystal mixtures, in particular, in terms of VHR stability:
In a particularly preferred embodiment, the one or more compounds of the Formula H may be selected from the group consisting of the compounds the following Formulae H-2-1 to H-2-6:
In a preferred embodiment of the present invention, the media according to the invention comprise in each case one or more compounds of the Formula H selected from the following group of the compounds of the formulae
The preferred content of the one or more compounds of Formula H in the LC medium depends inter alia on the inherent chemical stability of the LC medium as well as on the nature of the compound of Formula H. Compounds of Formula H in which R16 denotes O*, which are known as NO radical type HALS are preferably used in proportion ranging from 50 ppm to 1000 ppm, based on the weight of the LC medium. Compounds of Formula H in which R16 denotes an H atom, which are known as NH radical type HALS are advantageously used in proportion ranging from 50 ppm to 2000 ppm, based on the weight of the LC medium.
Preferably the LC medium of the present invention contains, in addition to the compounds of Formulae I and ST, one or more compounds selected from the following formulae:
Preferred compounds of Formula Z1 to Z6 are those selected from the following subformulae
In another preferred embodiment the medium contains one or more compounds of Formula Z1 or its preferred subformulae and/or one or more compounds selected from Formulae Z2, Z3, Z4 and Z5 or their preferred subformulae.
Preferably the total proportion of compounds of Formula Z1, Z2, Z3, Z4, Z5 and Z6 or their subformulae, such as CC-3-V in the medium is from 10 to 65%, very preferably from 20 to 60%, most preferably from 25 to 55% by weight. In yet a more preferred embodiment, the compound of Formula Z1-1 is used in concentrations ranging from 10 wt.-% to 60 wt.-%, more preferably 10 wt.-% to 40 wt.-%, based on the total weight of the LC medium.
Preferably the medium contains 1, 2 or 3 compounds selected from the Formulae Z1, Z2, Z3 and Z4 or their subformulae.
The medium may additionally comprise one or more compounds of the following general formulae:
Particular preference is given to the compounds of the Formula XIIa. In the Formula XIIb, “alkyl” preferably, independently of one another, denotes n-C3H7, n-C4H9 or n-C5H11, in particular n-C3H7.
Preferred compounds of subformula XIIa are selected from the following group:
The medium may additionally comprise one or more compounds selected from the following formulae:
The medium may further comprise one or more compounds of the Formula XIV in which at least one of the radicals R1 and R2 denotes alkenyl having 2 to 6 C atoms, preferably those selected from the following subformulae:
The compounds of the Formula XIV are preferably selected from the following subformulae:
Very preferred are compounds of Formula XIVd1.
In yet a further embodiment the medium comprises one or more compounds of the Formula XVI,
Particularly preferred compounds of the Formula XVI are those of the subformulae
Particular preference is given to the compounds of the Formulae XVIb and XVIc. Very particular preference is given to the compounds of the following subformulae
Very preferred are compounds of Formula XVIc2.
The medium comprises one or more compounds of the following formulae:
Very preferred are compounds of Formula XVIIa wherein L is H. Very preferred are compounds of Formula XVIlI wherein L is F.
In one preferred embodiment according to the present invention, the LC medium contains, in addition to the compounds of Formula I and H, one or more compounds selected from the Formulae Y and B
Preferably the LC medium according to this first preferred embodiment contains one or more compounds of Formula I and H, one or more compounds selected from Formulae Z1, Z2 and Z3, and one or more compounds selected from Formulae Y and B.
The LC media according to this first preferred embodiment are especially suitable for use in LC displays of the HB-FFS or PS-HB-FFS mode.
In a second preferred embodiment according to the present invention, the LC medium does not contain a compound of the Formulae Y or B.
In the compounds of Formula Y and its subformulae, R1 and R2 preferably denote straight-chain alkyl or alkoxy having 1 to 6 C atoms, furthermore alkenyl having 2 to 6 C atoms, in particular vinyl, 1E-propenyl, 1E-butenyl, 3-butenyl, 1E-pentenyl, 3E-pentenyl or 4-pentenyl.
In the compounds of Formula Y and its subformulae, preferably both radicals L1 and L2 denote F. In another preferred embodiment of the present invention, in the compounds of Formula Y and its subformulae one of the radicals L1 and L2 denotes F and the other denotes Cl.
In a preferred embodiment of the present invention the medium contains one or more compounds of Formula Y selected from the following subformulae
Preferably, in the compounds of Formula Y1 and Y2 both L1 and L2 denote F or one of L1 and L2 denotes F and the other denotes Cl, or both L3 and L4 denote F or one of L3 and L4 denotes F and the other denotes Cl.
Preferably the medium comprises one or more compounds of the Formula Y1 selected from the group consisting of the following subformulae
Very preferably the 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. L5 preferably denotes a H atom.
Further preferably the medium comprises one or more compounds of the Formula Y2 selected from the group consisting of the following subformulae:
Very preferably the medium contains one or more compounds of Formula Y2 selected from Formulae Y2-2 and Y2-10.
The proportion of the compounds of Formula Y1 or its subformulae in the medium is preferably from 0 to 10% by weight.
The proportion of the compounds of Formula Y2 or its subformulae in the medium is preferably from 0 to 10% by weight.
The total proportion of the compounds of Formula Y1 and Y2 or their subformulae in the medium is preferably from 1 to 20%, very preferably from 2 to 15% by weight.
Preferably the medium contains 1, 2 or 3 compounds of Formula Y1 and Y2 or their subformulae, very preferably selected from Formulae Y1-2, Y1-22, Y1-66, Y1-70, Y2-6 and Y2-22.
In another preferred embodiment of the present invention the medium contains one or more compounds of Formula Y selected from the following subformula
Preferred compounds of the Formula Y3 are selected from the group consisting of the following subformulae:
Particularly preferred compounds of the Formula Y3 are selected from the group consisting of following subformulae:
Preferably in the compounds of Formula Y3 and its subformulae both L1 and L2 denote F. Further preferably in the compounds of Formula Y3 one of the radicals L1 and L2 denotes F and the other denotes Cl.
The proportion of the compounds of Formula Y3 or its subformulae in the medium is preferably from 1 to 10%, very preferably from 1 to 6% by weight.
Preferably the medium contains 1, 2 or 3 compounds of Formula Y3 or its subformulae, preferably of Formula Y3-6, very preferably of Formula Y3-6A.
In another preferred embodiment the present invention the medium contains one or more compounds of Formula Y selected from the subformula Y4
Preferred compounds of the Formula Y4 are selected from the group consisting of the following subformulae:
R* preferably denotes CH2═CH—, CH2═CHCH2CH2—, CH3—CH═CH—, CH3—CH2— CH═CH—, CH3—(CH2)2—CH═CH—, CH3—(CH2)3—CH═CH— or CH3—CH═CH—(CH2)2—.
R preferably denotes methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy or pentoxy.
The proportion of the compounds of Formula Y4 or its subformulae in the medium is preferably from 1 to 10%, very preferably from 1 to 6% by weight.
Particularly preferred compounds are those of the subformulae
Use of the following compounds is particularly advantageous:
In another preferred embodiment the present invention the medium contains one or more compounds of Formula Y selected from the group consisting of the following subformulae
R5 in these compounds is particularly preferably C2-6-alkyl or -alkoxy or C2-6-alkenyl, d is preferably 1. X in these compounds is particularly preferably F. The LC medium according to the invention preferably comprises one or more compounds of the above-mentioned formulae in amounts of ≥5% by weight.
In the compounds of Formula B and its subformulae, R1 and R3 preferably denote straight-chain alkyl or alkoxy having 1 to 6 C atoms, in particular methoxy, ethoxy, propoxy or butoxy, furthermore alkenyl having 2 to 6 C atoms, in particular vinyl, 1E-propenyl, 1E-butenyl, 3-butenyl, 1E-pentenyl, 3E-pentenyl or 4-pentenyl.
In a preferred embodiment of the present invention the medium contains one or more compounds of Formula B selected from the following subformulae
Preferred compounds of Formula B1 are selected from the following subformulae:
—O—, —CO—O— or —O—CO— in such a way that 0 atoms are not linked directly to one another, and in which one or more H atoms may be replaced by a halogen atom. Very preferred are compounds of Formula E1-1 and B1-2 wherein both groups (O) denote an oxygen atom and R1 and R3 independently denote an alkyl group being methyl, ethyl, propyl, butyl, pentyl or hexyl, which are preferably straight-chained. Very preferably one “alkyl” is ethyl and the other “alkyl” is n-pentyl.
Very preferred are compounds of Formula B1-2.
Preferably, the compounds of the Formula E1-1 are selected from the group of compounds of Formulae B1-1-1 to B1-1-11, preferably of Formula B1-1-6,
Preferably, the compounds of the Formula B1-2 are selected from the group of compounds of Formulae B1-2-1 to B1-2-10, preferably of Formula B1-2-6,
Optionally the medium comprises one or more compounds of the Formula B1-1A and/or B1-2A
The compounds of Formulae B1-1A and/or B1-2A are contained in the medium either alternatively or in addition to the compounds of Formulae E1-1 and B1-2, preferably additionally.
Very preferred compounds of the Formulae B1-1A and/or B1-2A are the following:
The proportion of the compounds of Formula B1 or its subformulae in the medium is preferably from 1 to 20%, very preferably from 1 to 15% by weight.
Preferably the medium contains 1, 2 or 3 compounds of Formula B1 or its subformulae.
In a preferred embodiment of the present invention, the medium may comprise one or more compounds of Formula B2-2
—O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by halogen.
The compounds of Formula B2-2 are preferably selected from the group of compounds of the Formulae B2-2-1 to B2-2-10:
Particularly preferred compounds of Formula B2 are selected from the following subformulae:
The proportion of the compounds of Formula B2 or its subformulae in the medium is preferably from 1 to 20%, very preferably from 1 to 15% by weight.
Preferably the LC medium contains 1, 2 or 3 compounds of Formula B2 or its subformulae.
Preferred compounds of Formula B3 are selected from the following subformulae:
Preferred compounds of Formula B3 are selected from the following subformulae:
Most preferred are compounds of Formulae B3-1-1 and B3-2-2.
In a preferred embodiment the medium contains one or more compounds of Formula B or its subformulae 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 methoxy group, preferably by a methyl group, preferably in p-position to the substituent F, very preferably in p-position to the substituent F (i.e. in m-position to the terminal group R2 or X1).
The proportion of the compounds of Formula B3 or its subformulae in the LC medium is preferably from 1 to 20%, very preferably from 1 to 10% by weight.
Preferably the LC medium contains 1, 2 or 3 compounds of Formula B3 or its subformulae.
Preferably the total proportion of compounds of Formula Y and B or their subformulae in the medium is from 2 to 25%, very preferably from 3 to 20% by weight.
Further preferred embodiments are indicated below:
Preferably, both radicals L1 and L2 denote F. Further preferably one of the radicals L1 and L2 denotes F and the other denotes Cl.
The compounds of the Formula LY are preferably selected from the group consisting of the following subformulae:
Very preferred are compounds of Formula LY4.
Preferably the medium contains 1, 2 or 3 compounds of Formula LY, very preferably of Formula LY4.
The proportion of the compounds of Formula LY or its subformulae in the medium is preferably from 1 to 10% by weight.
The compounds of the Formula AY are preferably selected from the group consisting of the following subformulae:
Preferred compounds of Formula II and III are those wherein Y0 is H.
Further preferred compounds of Formula II and III are those wherein R0 denotes alkyl having 1 to 6 C atoms, very preferably ethyl or propyl, and X0 denotes F or OCF3, very preferably F.
The medium comprises one or more compounds of Formula II selected from the following subformulae:
Preferred compounds are those of Formula II, II2 and II3, very preferred those of Formula II1 and II2.
In the compounds of Formulae III to 117 R0 preferably denotes alkyl having 1 to 6 C atoms, very preferably ethyl or propyl, and X0 preferably denotes F or OCF3, very preferably F.
The medium contains one or more compounds of Formula II or their subformulae as described above and below wherein Y0 is CH3, Very preferably the medium according to this preferred embodiment comprises one or more compounds of Formula II selected from the following subformulae:
Preferred compounds are those of Formula IIA1, IIA2 and IIA3, very preferred those of Formula IIA1 and IIA2.
In the compounds of Formulae IIA1 to IIA7 R0 preferably denotes alkyl having 1 to 6 C atoms, very preferably ethyl or propyl, and X0 preferably denotes F or OCF3, very preferably F.
Preferred compounds are those of Formula III1, III4, III6, III16, III19 and III20.
In the compounds of Formulae III1 to III21 R0 preferably denotes alkyl having 1 to 6 C atoms, very preferably ethyl or propyl, X0 preferably denotes F or OCF3, very preferably F, and Y2 preferably denotes F.
The medium contains one or more compounds of Formula III or their subformulae as described above and below wherein Y0 is CH3. Very preferably, the medium according to this preferred embodiment comprises one or more compounds of Formula III selected from the following subformulae:
Preferred compounds are those of Formula IIIA1, IIIA4, IIIA6, IIIA16, IIIA19 and IIIA20.
In the compounds of Formulae IIIA1 to IIIA21 R0 preferably denotes alkyl having 1 to 6 C atoms, very preferably ethyl or propyl, X0 preferably denotes F or OCF3, very preferably F, and Y2 preferably denotes F.
The medium additionally comprises one or more compounds selected from the following formulae:
The compounds of the Formula IV are preferably selected from the following formulae:
R0 preferably denotes alkyl having 1 to 6 C atoms. X0 preferably denotes F or OCF3, furthermore OCF═CF2 or Cl.
The compounds of the Formula IVa are preferably selected from the following subformula:
The compounds of the Formula IVb are preferably represented by the following formula:
The compounds of the Formula IVc are preferably selected from the following subformula:
The compound(s) of the Formula IVc, in particular of the Formula IVc1, is (are) preferably employed in the mixtures according to the invention in amounts of 1-20% by weight, particularly preferably 2-15% by weight.
The compounds of the Formula V are preferably selected from the following subformulae:
R0 preferably denotes alkyl having 1 to 6 C atoms. X0 preferably denotes F and OCF3, furthermore OCHF2, CF3, OCF═CF2 and OCH═CF2.
R0 preferably denotes alkyl having 1 to 6 C atoms. X0 preferably denotes F, furthermore OCF3, CF3, CF═CF2, OCHF2 and OCH═CF2.
The compounds of the Formula VII are preferably selected from the following subformulae:
R0 preferably denotes alkyl having 1 to 6 C atoms. X0 preferably denotes F, furthermore OCF3, OCHF2 and OCH═CF2.
In some embodiments, the medium additionally comprises one or more compounds selected from the following formulae:
Very preferably the medium according to the invention comprises one or more compounds of the Formula XXa,
The compound(s) of the Formula XX, in particular of the Formula XXa, is (are) preferably employed in the mixtures according to the invention in amounts of 0-15% by weight, particularly preferably 1-10% by weight.
Very preferably the medium according to the invention comprises one or more compounds of the Formula XXIa,
The compound(s) of the Formula XXI, in particular of the Formula XXIa, is (are) preferably employed in the mixtures according to the invention in amounts of 1-15% by weight, particularly preferably 2-10% by weight.
Further preferably the medium according to the invention comprises one or more compounds of the Formula XXIIIa,
The compound(s) of the Formula XXIII, in particular of the Formula XXIIIa, is (are) preferably employed in the mixtures according to the invention in amounts of 0.5-5% by weight, particularly preferably 0.5-2% by weight.
The medium additionally comprises one or more compounds of the Formula XXIV,
In the Formula XXIV, X0 may also denote an alkyl radical having 1 to 6 C atoms or an alkoxy radical having 1 to 6 C atoms. The alkyl or alkoxy radical is preferably straight-chain.
R0 preferably denotes alkyl having 1 to 6 C atoms. X0 preferably denotes F.
The compounds of the Formula XXIV are preferably selected from the following subformulae:
is preferably
R0 is straight-chain alkyl or alkenyl having 2 to 6 C atoms.
The medium may further comprise one or more compounds of the following formulae:
The medium comprises one or more compounds of the following formulae:
R1 preferably denotes alkyl having 1 to 6 C atoms. X0 preferably denotes F. The medium according to the invention particularly preferably comprises one or more compounds of the Formula XXIX in which X0 preferably denotes F.
The compound of general Formula XXX may be advantageously selected from one of the following Formulae XXX1 to XXX3, wherein use of the compound of Formula XXX1 is particularly preferred:
The compound(s) of the Formulae XXVI-XXIX is (are) preferably employed in the mixtures according to the invention in amounts of 1-20% by weight, particularly preferably 1-15% by weight. Particularly preferred mixtures comprise at least one compound of the Formula XXIX.
In some further embodiments, the medium comprises one or more compounds of the following formulae:
Very preferably the medium according to the invention comprises one or more compounds of the Formula XXIXa:
The compound(s) of the Formula XXIXa is (are) preferably employed in the mixtures according to the invention in amounts of 1-15% by weight, particularly preferably 2-10% by weight.
The medium may further comprise one or more compounds of the following pyrimidine or pyridine compounds of the formulae
The medium may additionally comprise one or more compounds of the following formulae:
Very preferably the medium according to the invention comprises one or more compounds of the Formula XXXVa
The compound(s) of the Formula XXXV, in particular of the Formula XXXVa, is (are) preferably employed in the mixtures according to the invention in amounts of 0.5-10% by weight, particularly preferably 1-5% by weight.
Further preferred LC media are selected from the following preferred embodiments, including any combination thereof:
The total content of compounds of the Formula I in the LC medium is preferably 2 to 80% by weight, preferably 5 to 70% by weight, and particularly preferably 10 to 60% by weight, based on the weight of the LC medium.
It has proved surprisingly advantageous to select the compounds of Formula I in such a way that they can be described in the LC medium of the invention by a single formula selected from I-1-1 to I-1-17 and I-2-1 to I-2-53. It is particularly preferred that all compounds of Formula I can be described in the LC medium of the invention by a single structure selected from the following list:
In some embodiments of the present invention the medium may in particular comprise a combination of at least two different compounds of the general Formula I selected from the following compounds:
It has been shown that a combination of at least two different compounds of Formula I in the LC medium of the present invention not only has much better solubility than a single compound of Formula I but also exhibits significantly improved stability to UV radiation and elevated temperatures. The stabilizing effect of the compounds of the general Formula ST and, if present, H is thereby synergistically enhanced.
Preferably, the proportion of compounds of Formula ST, as described above or listed in Table G, in the LC medium is from 10 to 2000 ppm, very preferably from 30 to 1000 ppm by weight.
Preferred content of the one or more compounds of Formula H in the LC medium depends inter alia on the inherent chemical stability of the LC medium as well as on the nature of the compound of Formula H. Compounds of Formula H in which R16 denotes O*, which are known as NO radical type HALS are preferably used in proportion ranging from 50 ppm to 1000 ppm by weight, based on the weight of the LC medium. Compounds of Formula H in which R16 denotes a H atom, which are known as NH radical type HALS are advantageously used in proportion ranging from 50 ppm to 2000 ppm by weight, based on the weight of the LC medium.
If two compounds of Formula I are present in the LC medium of the invention, their weight ratio is preferably between 10:90 and 90:10, particularly preferably between 20:80 and 80:20, even more preferably between 30:70 and 70:30, based on the total weight of the two compounds of Formula I.
The individual concentration of each of these compounds is preferably from 2 to 15% by weight. The total concentration of these compounds is preferably from 5 to 30% by weight.
The term “alkyl” or “alkyl*” in this application encompasses straight-chain and branched alkyl groups having 1 to 6 carbon atoms, in particular the straight-chain groups methyl, ethyl, propyl, butyl, pentyl and hexyl. Groups having 2 to 5 carbon atoms are generally preferred.
The term “alkenyl” or “alkenyl*” encompasses straight-chain and branched alkenyl groups having 2 to 6 carbon atoms, in particular the straight-chain groups.
Preferred alkenyl groups are C2-C7-1E-alkenyl, C4-C6-3E-alkenyl, in particular 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 up to 5 carbon atoms are generally preferred, in particular CH2═CH, CH3CH═CH.
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 the fluorine are not excluded.
The term “oxaalkyl” or “alkoxy” preferably encompasses straight-chain radicals of the formula CnH2n+1—O—(CH2)m, in which n and m each, independently of one another, denote 1 to 6. m may also denote 0. Preferably, n=1 and m=1-6 or m=0 and n=1-3. Further preferably the alkoxy or oxaalkyl group can also contain one or more further O atoms such that oxygen atoms are not directly linked to one another.
Through a suitable choice of the meanings of R0 and X0, the addressing times, the threshold voltage, the steepness of the transmission characteristic lines, etc., can be modified in the desired manner. For example, 1E-alkenyl radicals, 3E-alkenyl radicals, 2E-alkenyloxy radicals and the like generally result in shorter addressing times, improved nematic tendencies and a higher ratio between the elastic constants k33 (bend) and k11 (splay) compared with alkyl and alkoxy radicals. 4-Alkenyl radicals, 3-alkenyl radicals and the like generally give lower threshold voltages and lower values of k33/k11 compared with alkyl and alkoxy radicals. The mixtures according to the invention are distinguished, in particular, by high Δε values and thus have significantly faster response times than the mixtures from the prior art.
The optimum mixing ratio of the compounds of the above-mentioned formulae depends substantially on the desired properties, on the choice of the components of the above-mentioned formulae and on the choice of any further components that may be present.
Suitable mixing ratios within the range indicated above can easily be determined from case to case.
The total amount of compounds of the above-mentioned formulae in the liquid-crystalline media according to the invention is not crucial. The mixtures can therefore comprise one or more further components for the purposes of optimisation of various properties. However, the observed effect on the desired improvement in the properties of the medium is generally greater, the higher the total concentration of compounds of the above-mentioned formulae.
In a particularly preferred embodiment, the liquid-crystalline media according to the invention comprise compounds of the Formulae IV to VIII (preferably IV and V) in which X0 denotes F, OCF3, OCHF2, OCH═CF2, OCF═CF2 or OCF2—CF2H. A favourable synergistic action with the compounds of the Formulae I, II and III results in particularly advantageous properties. In particular, mixtures comprising compounds of the Formulae I, ST, II and III are distinguished by their low threshold voltage.
The individual compounds of the above-mentioned formulae and the sub-formulae thereof which can be used in the liquid-crystalline media according to the invention are either known or can be prepared analogously to the known compounds.
The invention also relates to a process for the preparation of a liquid-crystalline medium as described above and below, by mixing one or more compounds of the Formula I with one or more compounds of the Formula ST, and, optionally, one or more compounds of Formula H, and one or more compounds selected from the group consisting of Formulae II, III, IV, VI, XIV, XII, XVI, XVIIa, XVIIb, XVIIc, XX, XXIII, XXIX, XXXII and XXXV.
In another preferred embodiment of the present invention the liquid-crystalline medium additionally comprises one or more polymerizable compounds. The polymerizable compounds are preferably selected from Formula M
Ra—B1—(Zb—B2)m—Rb M
Particularly preferred compounds of the Formula M are those in which B1 and B2 each, independently of one another, denote 1,4-phenylene, 1,3-phenylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, phenanthrene-2,7-diyl, 9,10-dihydro-phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7-diyl, coumarine, flavone, where, in addition, one or more CH groups in these groups may be replaced by N, cyclohexane-1,4-diyl, in which, in addition, one or more non-adjacent CH2 groups may be replaced by 0 and/or S, 1,4-cyclohexenylene, bicycle[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, piperidine-1,4-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, indane-2,5-diyl or octahydro-4,7-methanoindane-2,5-diyl, where all these groups may be unsubstituted or mono- or polysubstituted by L as defined above.
Particularly preferred compounds of the Formula M are those in which B1 and B2 each, independently of one another, denote 1,4-phenylene, 1,3-phenylene, naphthalene-1,4-diyl or naphthalene-2,6-diyl.
Very preferred compounds of Formula M are selected from the following formulae:
Especially preferred are compounds of Formulae M2 and M13.
Further preferred are trireactive compounds M15 to M31, in particular M17, M18, M19, M22, M23, M24, M25, M30 and M31.
In the compounds of Formulae M1 to M31 the group
is preferably,
Preferred compounds of Formulae M1 to M31 are those wherein P1, P2 and P3 denote an acrylate, methacrylate, oxetane or epoxy group, very preferably an acrylate or methacrylate group.
Further preferred compounds of Formulae M1 to M31 are those wherein Sp1, Sp2 and Sp3 are a single bond.
Further preferred compounds of Formulae M1 to M31 are those wherein one of Sp1, Sp2 and Sp3 is a single bond and another one of Sp1, Sp2 and Sp3 is different from a single bond.
Further preferred compounds of Formulae M1 to M31 are those wherein those groups Sp1, Sp2 and Sp3 that are different from a single bond denote —(CH2)s1—X″—, wherein s1 is an integer from 1 to 6, preferably 2, 3, 4 or 5, and X″ is X″ is the linkage to the benzene ring and is —O—, —O—CO—, —CO—O—, —O—CO—O— or a single bond.
Particular preference is given to liquid-crystalline media comprising one, two or three polymerizable compounds of Formula M, preferably selected from Formulae M1 to M31.
Further preferably the liquid-crystalline media according to the present invention comprise one or more polymerizable compounds selected from Table E below.
Preferably the proportion of polymerizable compounds in the liquid-crystalline medium, preferably selected from Formula M and Table E, is from 0.01 to 5%, very preferably from 0.05 to 1%, most preferably from 0.1 to 0.5%.
It was observed that the addition of one or more polymerizable compounds to the liquid-crystalline medium, like those selected from Formula M and Table E, leads to advantageous properties like fast response times. Such a liquid-crystalline medium is especially suitable for use in PSA displays where it shows low image sticking, a quick and complete polymerisation, the quick generation of a low pretilt angle which is stable after UV exposure, a high reliability, high VHR value after UV exposure, and a high birefringence. By appropriate selection of the polymerizable compounds it is possible to increase the absorption of the liquid-crystalline medium at longer UV wavelengths, so that it is possible to use such longer UV wavelengths for polymerisation, which is advantageous for the display manufacturing process.
The polymerizable group P is a group which is suitable for a polymerisation reaction, such as, for example, free-radical or ionic chain polymerisation, polyaddition or polycondensation, or for a polymer-analogous reaction, for example addition or condensation onto a main polymer chain. Particular preference is given to groups for chain polymerisation, in particular those containing a C═C double bond or —C≡C— triple bond, and groups which are suitable for polymerisation with ring opening, such as, for example, oxetane or epoxide groups.
Preferred groups P are selected from the group consisting of CH2═CW1—CO—O—, CH2═CW1—CO—,
CH2═CW2—(O)k3—, CW1═CH—CO—(O)k3—, CW1═CH—CO—NH—, CH2═CW1—CO—NH—, CH3—CH═CH—O—, (CH2═CH)2CH—OCO—, (CH2═CH—CH2)2CH—OCO—, (CH2═CH)2CH—O—, (CH2═CH—CH2)2N—, (CH2═CH—CH2)2N—CO—, HO—CW2W3—, HS—CW2W3—, HW2N—, HO—CW2W3—NH—, CH2═CW1—CO—NH—, CH2═CH—(COO)k1-Phe-(O)k2—, CH2═CH—(CO)k1-Phe-(O)k2—, Phe-CH═CH—, HOOC—, OCN—and W4W5W6Si—, in which W1 denotes H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, in particular H, F, C or CH3, W2 and W3 each, independently of one another, denote H or alkyl having 1 to 5 C atoms, in particular H, methyl, ethyl or n-propyl, W4, W5 and W6 each, independently of one another, denote Cl, oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, W7 and W8 each, independently of one another, denote H, C or alkyl having 1 to 5 C atoms, Phe denotes 1,4-phenylene, which is optionally substituted by one or more radicals L as defined above which are other than P-Sp-, k1, k2 and k3 each, independently of one another, denote 0 or 1, k3 preferably denotes 1, and k4 denotes an integer from 1 to 10.
Very preferred groups P are selected from the group consisting of CH2═CW1—CO—O—CH2═CW1—CO—,
CH2═CW2—O—, CH2═CW2—, CW1═CH—CO—(O)k3—, CW1═CH—CO—NH—, CH2═CW1—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═CW1—CO—NH—, CH2═CH—(COO)k1-Phe-(O)k2—, CH2═CH—(CO)k1-Phe-(O)k2—, Phe-CH═CH— and W4W5W6Si—, in which W1 denotes H, F, C, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, in particular H, F, C or CH3, W2 and W3 each, independently of one another, denote H or alkyl having 1 to 5 C atoms, in particular H, methyl, ethyl or n-propyl, W4, W5 and W6 each, independently of one another, denote Cl, oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, W7 and W8 each, independently of one another, denote H, C1 or alkyl having 1 to 5 C atoms, Phe denotes 1,4-phenylene, k1, k2 and k3 each, independently of one another, denote 0 or 1, k3 preferably denotes 1, and k4 denotes an integer from 1 to 10.
Very particularly preferred groups P are selected from the group consisting of CH2═CW1—CO—O—, in particular CH2═CH—CO—O—, CH2═C(CH3)—CO—O— and CH2═CF—CO—O—, furthermore CH2═CH—O—, (CH2═CH)2CH—O—CO—, (CH2═CH)2CH—O—
Further preferred polymerizable groups P are selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide, most preferably from acrylate and methacrylate.
If Sp is different from a single bond, it is preferably of the formula Sp″-X″, so that the respective radical P-Sp- conforms to the formula P-Sp″-X″—, wherein
X″ is preferably —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—NR0—, —NR0—CO—, —NR0—CO—NR00— or a single bond.
Typical spacer groups Sp and -Sp″-X″— are, for example, —(CH2)p1—, —(CH2CH2O)1—CH2CH2—, —CH2CH2—S—CH2CH2—, —CH2CH2—NH—CH2CH2— or —(SiR0R00—O)p1—, in which p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R0 and R00 have the meanings indicated above.
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—, in which p1 and q1 have the meanings indicated above.
Particularly preferred groups Sp″ are, in each case straight-chain, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutyl-ene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, ethenylene, propenylene and butenylene.
For the production of PSA displays, the polymerizable compounds contained in the liquid-crystalline medium are polymerised or crosslinked (if one compound contains two or more polymerizable groups) by in-situ polymerisation in the liquid-crystalline medium between the substrates of the LC display, optionally while a voltage is applied to the electrodes.
The structure of the PSA displays according to the invention corresponds to the usual geometry for PSA displays, as described in the prior art cited at the outset. Geometries without protrusions are preferred, in particular those in which, in addition, the electrode on the colour filter side is unstructured and only the electrode on the TFT side has slots. Particularly suitable and preferred electrode structures for PS-VA displays are described, for example, in US 2006/0066793 A1.
The combination of compounds of the preferred embodiments mentioned above with the polymerised compounds described above causes low threshold voltages, low rotational viscosities and very good low-temperature stabilities in the liquid-crystalline media according to the invention at the same time as constantly high clearing points and high VHR values.
The use of liquid-crystalline media containing polymerizable compounds allows the rapid establishment of a particularly low pretilt angle in PSA displays. In particular, the liquid-crystalline media exhibit significantly shortened response times, in particular also the grey-shade response times, in PSA displays compared with the media from the prior art.
Preference is generally given to liquid-crystalline media which have a nematic liquid-crystalline phase, and preferably have no chiral liquid crystal phase.
The invention also relates to the use of a liquid-crystalline medium according to the present invention as described above and below for electro-optical purposes, in particular for the use is in shutter glasses, for 3D applications, 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 of the aforementioned types, containing a liquid-crystalline medium according to the present invention as described above and below, in particular a TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-FFS, positive VA (vertically aligned) or positive PS-VA display.
The invention also relates to electro-optical displays, such as, for example, STN or MLC displays, having two plane-parallel outer plates, which, together with a frame, form a cell, integrated non-linear elements for switching individual pixels on the outer plates, and a nematic liquid-crystal medium having positive dielectric anisotropy and high specific resistance located in the cell, wherein the a nematic liquid-crystal medium is a liquid-crystalline medium according to the present invention as described above and below.
The liquid-crystalline media according to the invention enable a significant broadening of the available parameter latitude. The achievable combinations of clearing point, viscosity at low temperature, thermal and UV stability and high optical anisotropy are far superior to previous materials from the prior art.
In particular, the combination of compounds of Formula I with compounds of Formula Y and/or B, and additionally with compounds selected from Formulae II-XXXV or their sub-formulae, leads to liquid-crystalline media which show a moderate positive dielectric anisotropy and at the same time an increased dielectric constant ε⊥ perpendicular to the longitudinal axes of the liquid-crystalline molecules, while maintaining a low rotational viscosity and a low value of the ratio γ1/k11. This enables liquid-crystalline displays, especially of the FFS, HB-FFS, XB-FFS and IPS mode, with high brightness and transmission and low response times.
The liquid-crystalline media according to the invention are suitable for mobile applications and TFT applications, such as, for example, mobile telephones and PDAs. Furthermore, the liquid-crystalline media according to the invention are particularly suitably for use in FFS, HB-FFS, XB-FFS and IPS displays based on dielectrically positive liquid crystals.
The liquid-crystalline media according to the invention, while retaining the nematic phase down to −20° C. and preferably down to −30° C., particularly preferably down to −40° C., and the clearing point ≥75° C., preferably ≥80° C., at the same time allow rotational viscosities γ1 of ≤110 mPa-s, particularly preferably ≤100 mPa·s, to be achieved, enabling excellent MLC displays having fast response times to be achieved. The rotational viscosities are determined at 20° C.
The dielectric anisotropy Δε of the liquid-crystalline media according to the invention at 20° C. and 1 kHz is preferably ≥+1.5, very preferably from +2 to +6.
The birefringence Δn of the liquid-crystalline media according to the invention at 20° C. is preferably from 0.08 to 0.15, very preferably from 0.1 to 0.14.
The rotational viscosity γ1 of the liquid-crystalline media according to the invention is preferably ≤80 mPa s, more preferably ≤70 mPa s, very preferably ≤60 mPa s.
The ratio γ1/k11 (wherein γ1 is the rotational viscosity γ1 and k11 is the elastic constant for splay deformation) of the liquid-crystalline media according to the invention is preferably ≤4.6 mPa·s/pN, very preferably ≤4.2 mPa·s/pN, most preferably ≤4.0 mPa·s/pN.
The nematic phase range of the liquid-crystalline media according to the invention preferably has a width of at least 90° C., more preferably of at least 100° C., in particular at least 110° C. This range preferably extends at least from −25° C. to +80° C.
It goes without saying that, through a suitable choice of the components of the liquid-crystalline media according to the invention, it is also possible for higher clearing points (for example above 100° C.) to be achieved at higher threshold voltages or lower clearing points to be achieved at lower threshold voltages with retention of the other advantageous properties. At viscosities correspondingly increased only slightly, it is likewise possible to obtain liquid-crystalline media having a higher Δε and thus low thresholds. The MLC displays according to the invention preferably operate 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, besides particularly favourable electro-optical properties, such as, for example, high steepness of the characteristic line and low angle dependence of the contrast (German patent 30 22 818), lower dielectric anisotropy is sufficient at the same threshold voltage as in an analogous display at the second minimum. This enables significantly higher specific resistance values to be achieved using the mixtures according to the invention at the first minimum than in the case of liquid-crystalline media comprising cyano compounds. Through a suitable choice of the individual components and their proportions by weight, the person skilled in the art is able to set the birefringence necessary for a pre-specified layer thickness of the MLC display using simple routine methods.
Measurements of the voltage holding ratio (HR) [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)] have shown that liquid-crystalline media according to the invention comprising compounds of the Formulae ST-1, ST-2, RV, IA and IB exhibit a significantly smaller decrease in the HR on UV exposure than analogous mixtures comprising cyanophenylcyclohexanes of the formula
or esters of the formula
instead of the compounds of the Formulae I ST-1, ST-2, RV, IA and IB.
The light stability and UV stability of the liquid-crystalline media according to the invention are considerably better, i.e. they exhibit a significantly smaller decrease in the HR on exposure to light, heat or UV.
The construction of the MLC display according to the invention from polarisers, electrode base plates and surface-treated electrodes corresponds to the usual design for displays of this type. The term usual design is broadly drawn here and also encompasses all derivatives and modifications of the MLC display, in particular including matrix display elements based on poly-Si TFTs or MIM.
A significant difference between the displays according to the invention and the hitherto conventional displays based on the twisted nematic cell consists, however, in the choice of the liquid-crystal parameters of the liquid-crystal layer.
The liquid-crystalline media which can be used in accordance with the invention are prepared in a manner conventional per se, for example by mixing one or more compounds of Claim 1 with one or more compounds of the Formulae II-XXXV or with further liquid-crystalline compounds and/or additives. In general, the desired amount of the components used in lesser amount is dissolved in the components making up the principal constituent, advantageously at elevated temperature. It is also possible to mix solutions of the components in an organic solvent, for example in acetone, chloroform or methanol, and to remove the solvent again, for example by distillation, after thorough mixing.
The LC media may also comprise further additives known to the person skilled in the art and described in the literature, such as, for example, polymerisation initiators, inhibitors, surface-active substances, light stabilisers, antioxidants, e.g. BHT, TEMPOL, microparticles, free-radical scavengers, nanoparticles, etc. For example, 0-15% of pleochroic dyes or chiral dopants or initiators like Irgacure® 651 or Irgacure® 907 can be added. Suitable stabilisers and dopants are mentioned below in Tables C and D.
In a preferred embodiment of the present invention the LC media contain one or more further stabilisers, preferably selected from the group consisting of the following Formulae H and ST as described above.
In a preferred embodiment the LC medium comprises one or more stabilisers selected from Table D.
Preferably the proportion of stabilisers, like those of Formula S1-S3, in the LC medium is from 10 to 2000 ppm, very preferably from 30 to 1000 ppm.
In another preferred embodiment the LC medium according to the present invention contains a self-aligning (SA) additive, preferably in a concentration of 0.1 to 2.5%. An LC medium according to this preferred embodiment is especially suitable for use in polymer stabilised SA-FFS, SA-HB-FFS or SA-XB-FFS displays.
In a preferred embodiment the SA-FFS, SA-HB-FFS or SA-XB-FFS display according to the present invention does not contain a polyimide alignment layer. In another preferred embodiment the SA-FFS, SA-HB-FFS or SA-XB-FFS display according to preferred embodiment contains a polyimide alignment layer.
Preferred SA additives for use in this preferred embodiment are selected from compounds comprising a mesogenic group and a straight-chain or branched alkyl side chain that is terminated with one or more polar anchor groups selected from hydroxy, carboxy, amino or thiol groups.
Further preferred SA additives contain one or more polymerizable groups which are attached, optionally via spacer groups, to the mesogenic group. These polymerizable SA additives can be polymerised in the LC medium under similar conditions as applied for the RMs in the PSA process.
Suitable SA additives to induce homeotropic alignment, especially for use in SA-VA mode displays, are disclosed for example in US 2013/0182202 A1, US 2014/0138581 A1, US 2015/0166890 A1 and US 2015/0252265 A1.
In another preferred embodiment an LC medium or a polymer stabilised SA-FFS, SA-HB-FFS or SA-XB-FFS display according to the present invention contains one or more self-aligning additives selected from Table F below.
Furthermore, it is possible to add to the liquid-crystalline media, for example, 0 to 15% by weight of pleochroic dyes, furthermore nanoparticles, conductive salts, preferably ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutyl-ammonium tetraphenylborate or complex salts of crown ethers (cf., for example, Haller et al., Mol. Cryst. Liq. Cryst. 24, 249-258 (1973)), for improving the conductivity, or substances for modifying the dielectric anisotropy, the viscosity and/or the alignment of the nematic phases. Substances of this type are described, for example, in DE-A 22 09 127, 22 40 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430 and 28 53 728.
For the present invention and in the following examples, the structures of the liquid-crystal compounds are indicated by means of acronyms, with the transformation into chemical formulae taking place in accordance with Tables A to C below. All radicals CmH2m+1, CnH2n+1, and ClH2l+1 or CmH2m−1, CnH2n−1 and ClH2l−1 are straight-chain alkyl radicals or alkylene radicals, in each case having n, m and l C atoms respectively. Preferably n, m and l are independently of each other 1, 2, 3, 4, 5, 6, or 7. Table A shows the codes for the ring elements of the nuclei of the compound, 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 molecules. The acronyms are composed of the codes for the ring elements with optional linking groups, followed by a first hyphen and the codes for the left-hand end group, and a second hyphen and the codes for the right-hand end group. Table D shows illustrative structures of compounds together with their respective abbreviations.
The following abbreviations are used:
Preferred mixture components are shown in Tables D and E.
In the following formulae, n and m each, independently of one another, denote 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, in particular 2, 3, 5, furthermore 0, 4, 6.
Particular preference is given to liquid-crystalline media which, besides the compounds of the Formulae IA, IIA, IB and IIB, comprise at least one, two, three, four or more compounds from Table E.
Table F indicates possible dopants which are generally added to the liquid-crystalline media according to the invention. The liquid-crystalline media preferably comprise 0-10% by weight, in particular 0.01-5% by weight and particularly preferably 0.01-3% by weight of dopants.
Stabilisers, which can additionally be added, for example, to the liquid-crystalline media according to the invention in amounts of 0-10% by weight, are mentioned below.
Table H shows illustrative reactive mesogenic compounds (RMs) which can be used in the liquid-crystalline media in accordance with the present invention.
In a preferred embodiment, the liquid-crystalline media according to the invention comprise one or more polymerizable compounds, preferably selected from the polymerizable compounds of the Formulae RM-1 to RM-143. Of these, 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-64, RM-74, RM-76, RM-88, RM-102, RM-103, RM-109, RM-117, RM-120, RM-121 and RM-122 are particularly preferred.
Table I shows self-alignment additives for vertical alignment which can be used in LC media for SA-FFS, SA-HB-FFS and SA-XB-FFS displays according to the present invention:
In a preferred embodiment, the LC media, SA-FFS, SA-HB-FFS and SA-XB-FFS displays according to the present invention comprise one or more SA additives selected from Formulae SA-1 to SA-34, preferably from Formulae SA-14 to SA-34, very preferably from Formulae SA-20 to SA-28, most preferably of Formula SA-20, in combination with one or more RMs of Formula I.
The following mixture examples are intended to explain the invention without limiting it.
Above and below, percentage data denote percent by weight. All temperatures are indicated in degrees Celsius. m.p. denotes melting point, cl.p.=clearing point. Furthermore, C=crystalline state, N=nematic phase, S=smectic phase and I=isotropic phase. The data between these symbols represent the transition temperatures. Furthermore, the following symbols are used
All physical properties are determined in accordance with “Merck Liquid Crystals, Physical Properties of Liquid Crystals”, status November 1997, Merck KGaA, Germany, and apply for a temperature of 20° C., unless explicitly indicated otherwise.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 500 ppm of the compound of Formula ST-2-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M1, without affecting the remaining physical properties of the mixture M1.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-2-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M2, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-2-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M3, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 300 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M4, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 300 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M5, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 300 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M6, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 300 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M7, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-2-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M8, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-2-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M9, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M10, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M11, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M12, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M13, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 300 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M14, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-2-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M15, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M16, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M17, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 300 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M18, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 300 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M19, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 300 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M20, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-2-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M21, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 400 ppm of the compound of Formula ST-2-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M22, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 350 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M23, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 350 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M24, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 350 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M25, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 500 ppm of the compound of Formula ST-2-3 in combination with 1000 ppm of the compound of Formula H-3-1 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M26, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 350 ppm of the compound of Formula ST-1-3 in combination with 400 ppm of the compound of Formula ST-2-3 and 1000 ppm of the compound of Formula H-3-7 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M27, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture is formulated as follows:
A nematic LC mixture is formulated as follows:
A nematic LC mixture is formulated as follows:
A nematic LC mixture is formulated as follows:
A nematic LC mixture is formulated as follows:
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 300 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M34, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 300 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M35, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 500 ppm of the compound of Formula ST-2-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M36, without affecting the remaining physical properties of the mixture.
A nematic LC mixture is formulated as follows:
A nematic LC mixture according to the invention is formulated as follows:
Addition of 350 ppm of the compound of Formula ST-1-3 significantly improves the VHR100 after UV exposure compared to the non-stabilized mixture M37, without affecting the remaining physical properties of the mixture.
| Number | Date | Country | Kind |
|---|---|---|---|
| 22167891.5 | Apr 2022 | EP | regional |
This application is a U.S. national stage application filed and claiming priority under 35 U.S.C. §§ 120 and 365(a) of International Application No. PCT/EP2023/059377, filed Apr. 11, 2023, and claiming priority under 35 U.S.C. § 119 of and to European Patent Application No. 22167891.5, filed Apr. 12, 2022, each of which applications is incorporated herein by reference in its entirety and for all purposes.
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/EP2023/059377 | 4/11/2023 | WO |
