TWI893109B - Polymerizable liquid crystal material and polymerized liquid crystal film - Google Patents

Abstract

The invention relates to a polymerizable LC material comprising one or more di- or multireactive mesogenic compounds and one or more compounds of formula I,

Description

Polymerizable liquid crystal material and polymerized liquid crystal film

The present invention relates to a polymerizable LC material comprising one or more bireactive or polyreactive mesogen compounds and one or more compounds of formula I, wherein the individual groups have one of the meanings given in the patent claims. Furthermore, the present invention relates to a method for preparing the polymerizable LC material; a polymer film with improved thermal and UV stability obtainable from the corresponding polymerizable LC material; a method for preparing such a polymer film; and the use of such a polymer film and the polymerizable LC material in optics, electro-optics, decoration, or security devices.

Polymerizable liquid crystal materials are known to be used in the prior art to prepare anisotropic polymer films with uniform orientation. These films are typically prepared by applying a thin layer of a polymerizable liquid crystal mixture to a substrate, aligning the mixture into a uniform orientation, and polymerizing the mixture. The film's orientation can be planar (i.e., in which the liquid crystal molecules are oriented substantially parallel to the layer), homeotropic (at right angles or perpendicular to the layer), or tilted.

Optical films of this type are described, for example, in EP 0 940 707 Bl, EP 0 888 565 Bl and GB 2 329 393 Bl.

Polymerizable liquid crystal (LC) materials that are stable at room temperature can degrade when subjected to elevated temperatures. For example, when heated for a period of time, optical properties such as dispersion or retardation degrade, and the performance of the optical film decreases over time. Specifically, this can result in a low degree of polymerization and a correspondingly high level of residual free radicals in the polymer, polymer shrinkage, and/or thermooxidative degradation.

Thermooxidative degradation is the disintegration of a polymer network catalyzed by oxidation reactions at high temperatures. As is generally known, antioxidant additives or short-term antioxidants can be used to reduce the thermooxidative degradation of polymers when they are subjected to elevated temperatures. This is particularly important when optical films are used in embedded applications due to the high temperatures. In particular, optical films must be resistant to annealing of polyimide layers in LC cells. In this regard, documents WO 2009/86911 A1 and JP 5354238 B1 describe polymerizable liquid crystal (LC) materials containing the commercially available antioxidant Irganox® 1076.

Due to the LC materials used, the above materials have obvious disadvantages, such as the UV stability or thermal durability of the resulting polymer films are still not high enough, their transmittance to VIS light is limited, they require the use of other additives, or their application bandwidth is limited.

Therefore, there is still a need for new and better improved polymerizable liquid crystal materials or mixtures which do not exhibit the disadvantages of the prior art materials, or if so, exhibit these disadvantages only to a lesser extent.

Advantageously, such polymerizable LC materials should be suitable for preparing different uniformly aligned polymer networks (e.g., polymer films) and should preferably simultaneously: - exhibit favorable adhesion to the substrate, - be highly transparent to VIS light, - exhibit reduced yellowing over time, and - exhibit favorable high-temperature stability or durability, and, in addition, - exhibit advantageously high UV stability or thermal durability, and, in addition, - the uniformly aligned polymer films should be producible by compatible, generally known methods for mass production.

Other objects of the present invention will become apparent to those skilled in the art from the following detailed description.

Surprisingly, the inventors of the present invention have found that one or more, preferably all, of the above-claimed objects can be achieved, preferably simultaneously, by using a polymerizable LC material as described in claim 1.

In general, the present invention relates to a polymerizable LC material comprising one or more bireactive or polyreactive mesogen compounds and one or more compounds of formula I in a concentration preferably in the range of 1 ppm to 2500 ppm, preferably to 2000 ppm, preferably to 1500 ppm, particularly preferably to 1000 ppm, preferably in the range of 1 ppm to 500 ppm, particularly preferably in the range of 1 ppm to 250 ppm, wherein R ¹¹ at each occurrence independently represents H, F, a linear or branched alkyl chain having 1 to 20 C atoms, wherein one -CH ₂ - group or, if present, a plurality of -CH ₂ - groups may be replaced by -O- or -C(=O)-, but two adjacent -CH ₂ - groups may not be replaced by -O-, and one or, if present, a plurality of -CH ₂ - groups may be replaced by -CH=CH- or -C≡C-, and wherein one H atom or a plurality of H atoms may be replaced by F, OR ¹³ , N(R ¹³ )(R ¹⁴ ) or R ¹⁵ , R ¹¹ preferably represents H or alkyl, particularly preferably alkyl, particularly preferably n-alkyl and very preferably n-butyl, R ¹² represents, independently at each occurrence, a linear or branched alkyl chain having 1 to 20 C atoms, wherein one or more -CH ₂ - groups may be replaced by -O- or -C(=O)-, but _{two adjacent -CH 2 -} groups may not be replaced by -O-; a alkyl group containing a cycloalkyl or alkylcycloalkyl unit, wherein one or more -CH ₂ - groups may be replaced by -O- or -C(=O)-, but _{two adjacent -CH 2 -} groups may not be replaced by -O-, and wherein one or more H atoms may be replaced by F, OR ¹³ , N(R ¹³ )(R ¹⁴ ) or R ¹⁵ is replaced; or an aromatic or heteroaromatic alkyl group, in which one H atom or multiple H atoms may be replaced by F, OR ¹³ , N(R ¹³ )(R ¹⁴ ) or R ¹⁵ , R ¹² preferably represents H, a non-branched alkyl group or a branched alkyl group, particularly preferably H or a non-branched alkyl group, R ¹³ at each occurrence independently represents a straight-chain or branched alkyl group or an acyl group having 1 to 10 C atoms, preferably an n-alkyl group or an aromatic alkyl group having 6 to 12 C atoms or a carboxylic acid group, R ¹⁴ at each occurrence independently represents a straight-chain or branched alkyl group or an acyl group having 1 to 10 C atoms, preferably an n-alkyl group or an aromatic alkyl group having 6 to 12 C atoms or a carboxylic acid group, R ¹⁵ represents, at each occurrence, independently of one another, a linear or branched alkyl group having 1 to 10 C atoms, wherein one -CH ₂ - group or multiple -CH ₂ - groups may be replaced by -O- or -C(=O)-, but two adjacent -CH ₂ - groups may not be replaced by -O-; S ¹¹ and S ¹² represent, at each occurrence, independently of one another, an alkylene group having 1 to 20 C atoms, which is branched or preferably linear, preferably -(CH ₂ -) _n having 1 to 20 C atoms, preferably 1 to 10 C atoms, particularly preferably 1 to 8 C atoms, wherein one -CH ₂ - group or, if present, multiple -CH ₂ - groups may be replaced by -O- or -C(=O)-, but two adjacent -CH ₂ - groups may not be replaced by -O-; - group cannot be replaced by -O-, and one or (if present) a plurality of -CH ₂ - groups may be replaced by -CH=CH- or -C≡C-, and one or a plurality of H atoms therein may be replaced by F, OR ¹³ , N(R ¹³ )(R ¹⁴ ) or R ¹⁵ , or represent a single bond, X ¹¹ represents C, Y ¹¹ to Y ¹⁴ each independently represent a methyl group or an ethyl group, particularly preferably all represent a methyl group or an ethyl group and most preferably a methyl group, Z ¹¹ to Z ¹⁴ each independently represent -O-, -(C=O)-, -O-(C=O)-, -(C=O)-O-, -O-(C=O)-O-, -(NR ¹³ )-, -NR ¹³ -(C=O)- or a single bond, if S If -X ¹¹ [-R ¹¹ ] o ^- is a single bond, Z ¹¹ and Z ¹² do not both represent -O-, and if -X ¹¹ [-R 11 ] _o - is a single bond, Z ¹³ and Z ¹⁴ do not both represent -O-, and if -X 11 [-R 11 ] o - is a single bond, Z ¹² and Z ¹³ do not both represent -O-, Z ¹¹ preferably represents -O-, Z ¹³ preferably represents a single bond, n * p represents an integer from 3 to 10, preferably to 8, p represents 1 or 2, o represents (3-p), in the case of p = 1, n represents 3, 4, 5, 6 or 8, particularly preferably 4, 6 or 8, very preferably 4 or 6, and m represents (10-n), and in the case of p = 2, n represents an integer from 2 to 4, preferably 2 or 3, particularly preferably 3, and m represents (4-n), represents an organic group having (m+n) bonding sites, preferably having up to 4 bonding sites, preferably an alkanediyl, alkanetriyl or alkanetetrayl unit having 1 to 30 C atoms, wherein, in addition to the m groups R ¹² present in the molecule (but independently thereof), another H atom can be replaced by R ¹² or a plurality of further H atoms can be replaced by R ¹² , preferably an alkanetetrayl unit having one or two valencies at each of the terminal C atoms, wherein one -CH ₂ - group or a plurality of -CH ₂ - groups can be replaced by -O- or -(C=O)- in such a way that two O atoms are not directly bonded to each other, or a substituted or unsubstituted aromatic or heteroaromatic hydrocarbon group having up to 10 valencies, wherein, in addition to the m groups R ¹² present in the molecule (but independently thereof), another H atom may be replaced by R ¹² or a plurality of other H atoms may be replaced by R ¹² , And in the case of p = 1, -X ¹¹ [-R ¹¹ ] _o - may alternatively represent a single bond.

Furthermore, the present invention also relates to a corresponding method for producing a polymerizable LC material, comprising at least the step of mixing one or more bireactive or polyreactive mesogen compounds and one or more compounds of formula I.

The invention further relates to a polymer network or polymer film obtainable, preferably obtainable, from a polymerizable LC material as described above and below, and to a method for producing a polymer film as described above and below.

The invention further relates to a method for increasing the UV stability of polymer films obtainable, preferably obtainable, from polymerizable LC materials as described above and below by adding a compound of formula I to the polymerizable LC material before polymerization.

The present invention further relates to the use of polymer films or polymerizable LC materials as described above and below for optical, electro-optical, information storage, decorative and security applications, such as liquid crystal displays, projection systems, polarizers, compensators, alignment layers, circular polarizers, color filters, decorative images, liquid crystal pigments, reflective films with spatially varying reflective colors, multicolor images, and unforgeable documents such as identity cards, credit cards or banknotes.

The present invention further relates to an optical component or device, a polarizer, a patterned retarder, a compensator, an alignment layer, a circular polarizer, a color filter, a decorative image, a liquid crystal lens, a liquid crystal pigment, a reflective film with spatially varying reflective color, and a multicolor image for decoration or information storage, comprising one or more polymer networks or polymer films or polymerizable LC materials as described above and below.

The invention further relates to a liquid crystal display comprising one or more polymer films or polymerizable LC materials or optical components as described above and below.

The invention further relates to a color or multicolor image for the identification, verification or security marking of an unforgeable article or document of value (such as an identity card or credit card or banknote) for security purposes, comprising a polymer network or polymer film or polymerizable LC material or optical component as described above and below.

As used herein, the term "polymer" is understood to mean a molecule comprising a backbone of one or more different types of repeating units (the smallest building block of a molecule), and includes the commonly known terms "oligomer,""copolymer,""homopolymer," and the like. Furthermore, it is understood that the term polymer includes, in addition to the polymer itself, residues from initiators, catalysts, and other elements accompanying the synthesis of the polymer, wherein such residues are understood to be not covalently incorporated into the polymer. Furthermore, such residues and other elements, while typically removed during post-polymerization purification processes, are typically mixed or blended with the polymer so that they typically remain with the polymer when it is transferred between containers or between solvents or dispersion media.

As used herein, the term "(meth)acrylic polymer" includes polymers obtained from acrylic monomers, polymers obtainable from methacrylic monomers, and corresponding copolymers obtainable from mixtures of such monomers.

The term "polymerization" refers to the chemical process of forming a polymer by bonding together a plurality of polymerizable groups or polymer precursors (polymerizable compounds) containing such polymerizable groups.

The terms "film" and "layer" include mechanically stable, rigid or flexible, self-supporting or freestanding films, as well as coatings or layers positioned on a supporting substrate or between two substrates.

The term "liquid crystal" or "LC" refers to materials that exhibit a liquid crystal phase in solution within a certain temperature range (thermotropic LC) or within a certain concentration range (lyotropic LC). These materials must contain a mesogen compound.

The terms "mesogenic compound" and "liquid crystal compound" refer to compounds containing one or more rod-shaped (rod-shaped or plate-shaped/lath-shaped) or disc-shaped (disc-shaped) mesogenic groups. The term "mesogenic group" refers to a group that is capable of inducing liquid crystal (or mesophase) behavior. A compound containing a mesogenic group may not exhibit a liquid crystal mesophase on its own. It may also exhibit a liquid crystal mesophase only in a mixture with other compounds or when polymerizing a mesogenic compound or material or a mixture thereof. This includes low molecular weight non-reactive liquid crystal compounds, reactive or polymerizable liquid crystal compounds, and liquid crystal polymers.

The rod-shaped mesogen group generally comprises a mesogen core composed of one or more aromatic or non-aromatic cyclic groups directly linked to each other or linked via a linker group, optionally comprising end groups linked to the ends of the mesogen core, and optionally comprising one or more pendant groups linked to the long sides of the mesogen core, wherein these end groups and pendant groups are generally selected from, for example, carbon or alkyl groups, polar groups (such as halogen, nitro, hydroxyl, etc.) or polymerizable groups.

The term "reactive mesogen" refers to a polymerizable mesogen or liquid crystal compound, preferably a monomeric compound. These compounds can be used as pure compounds or as mixtures of reactive mesogens with other compounds that act as photoinitiators, inhibitors, surfactants, stabilizers, chain transfer agents, non-polymerizable compounds, etc.

A polymerizable compound with one polymerizable group is also called a "monoreactive" compound, a compound with two polymerizable groups is called a "direactive" compound, and a compound with more than two polymerizable groups is called a "polyreactive" compound. A compound without a polymerizable group is also called a "non-reactive or non-polymerizable" compound.

The term "non-mesogenic compound or material" means a compound or material that does not contain a mesogenic group as defined above.

Visible light is electromagnetic radiation with a wavelength between about 400 nm and about 740 nm. Ultraviolet (UV) light is electromagnetic radiation with a wavelength between about 200 nm and about 450 nm.

Radiant intensity (E _e ) or radiant power is defined as the power per unit area (dA) of electromagnetic radiation (dθ) incident on a surface: E _e = dθ/dA.

Radiation exposure or radiation dose (H _e ) is the irradiance or radiation power (E _e ) per time instant (t): _He = E _e ∙ t.

All temperatures, such as the melting point of liquid crystals (T(C,N) or T(C,S), the transition from the smectic (S) phase to the nematic (N) phase (T(S,N), and the clearing point (T(N,I)), are given in degrees Celsius. All temperature differences are given in degrees.

The term "clearing point" refers to the temperature at which the transition occurs between the mesophase with the highest temperature range and the isotropic phase.

The term "director" is known in the art and refers to the preferred orientation direction of the long molecular axis (in the case of rod-shaped compounds) or the short molecular axis (in the case of discotic compounds) of liquid crystal or RM molecules. In the case of uniaxially aligned anisotropic molecules, the director is the axis of anisotropy.

The term "alignment" or "direction" refers to the alignment (directional ordering) of anisotropic units (such as small molecules or fragments of macromolecules) of a material along a common direction called the "alignment direction." In the alignment layer of a liquid crystal or RM material, the liquid crystal director is aligned with the alignment direction, so that the alignment direction corresponds to the direction of the anisotropy axis of the material.

For example, the term "homogeneously oriented" or "homogeneously aligned" of a liquid crystal or liquid crystal material means that the long molecular axes (in the case of rod-shaped compounds) or short molecular axes (in the case of discotic compounds) of the liquid crystal or liquid crystal molecules are oriented in substantially the same direction within a layer of material. In other words, the lines of the liquid crystal directors are parallel.

The term "vertical structure" or "vertical orientation" refers to a film in which the optical axis is substantially perpendicular to the plane of the film.

The terms "planar structure" or "planar orientation" refer to films in which the optical axis is substantially parallel to the plane of the film.

The term "negative (optical) dispersion" refers to a birefringent or liquid crystal material or layer that exhibits reverse birefringent dispersion, where the magnitude of the birefringence (Δn) increases with increasing wavelength (λ). That is, |Δn (450)| < |Δn (550)| or Δn (450)/Δn (550) < 1, where Δn (450) and Δn (550) are the birefringence of the material measured at wavelengths of 450 nm and 550 nm, respectively. Conversely, "positive (optical) dispersion" refers to a material or layer having |Δn (450)| > |Δn (550)| or Δn (450)/Δn (550) > 1. See also, for example, A. Uchiyama, T. Yatabe “Control of Wavelength Dispersion of Birefringence for Oriented Copolycarbonate Films Containing Positive and Negative Birefringent Units”. J. Appl. Phys. Vol. 42, pp. 6941-6945 (2003).

Since the optical retardation at a given wavelength is defined as the product of the birefringence and the layer thickness [R(λ) = Δn(λ) ^. d] as described above, the optical dispersion can be expressed as "birefringent dispersion" by the ratio Δn(450)/Δn(550), or as "retardation dispersion" by the ratio R(450)/R(550), where R(450) and R(550) are the retardations of the material measured at wavelengths of 450 nm and 550 nm, respectively. Since the layer thickness d does not vary with wavelength, R(450)/R(550) is equal to Δn(450)/Δn(550). Therefore, a material or layer with negative dispersion or reverse dispersion has R (450)/R (550)＜1 or |R (450)|＜|R (550)|, and a material or layer with positive dispersion or normal dispersion has R (450)/R (550)＞1 or |R (450)|＞|R (550)|.

In the present invention, unless otherwise stated, "optical dispersion" means delayed dispersion, that is, the ratio R(450)/R(550) or short R _450/550 .

The term "high dispersion" means that the absolute value of the dispersion exhibits a large deviation from 1, while the term "low dispersion" means that the absolute value of the dispersion exhibits a small deviation from 1. Thus, "high negative dispersion" means that the dispersion value is significantly less than 1, and "low negative dispersion" means that the dispersion value is only slightly less than 1.

The retardation of a material (R(λ)) can be measured using a spectroscopic elliptical polarimeter (e.g., the M2000 Spectroscopic Elliptical Polarimeter manufactured by J. A. Woollam Co.). This instrument is capable of measuring the optical retardation (in nanometers) of birefringent samples (e.g., quartz) over a wavelength range typically between 370 nm and 2000 nm. From this data, it is possible to calculate the dispersion of the material (R(450)/R(550) or Δn(450)/Δn(550)).

The method used to perform these measurements was presented by N. Singh at the National Physics Laboratory (London, UK) in October 2006, under the title "Spectroscopic Ellipsometry, Part 1 - Theory and Fundamentals, Part 2 - Practical Examples and Part 3 - Measurements." The measurement procedures described in Manual Retardation Measurement (RetMeas) (2002) and Guide to WVASE (2002) (Woollam Variable Angle Spectroscopic Ellipsometer ) were published by JA Woollam Co. Inc. ( Lincoln , NE, USA). Unless otherwise stated, this method was used to determine the retardation of the materials, films, and devices described in this invention.

The term "A-plate" refers to an optical retarder that uses a layer of uniaxial birefringent material with its extraordinary axis oriented parallel to the plane of the layer.

The term "C-plate" refers to an optical retarder using a layer of uniaxial birefringent material with its extraordinary axis oriented perpendicular to the plane of the layer.

In an A/C plate containing an optically uniaxial birefringent liquid crystal material with uniform orientation, the optical axis of the film is oriented in a direction other than the extraordinary axis. An A (or C) plate containing an optically uniaxial birefringent material with positive birefringence is also referred to as a "positive A (or C) plate" or a "+A (or +C) plate."

A (or C) plates made of films of optically uniaxial birefringent materials (such as anisotropic disc-shaped materials) with negative birefringence, depending on the orientation of the disc-shaped material, are also referred to as "negative A (or C) plates" or "-A (or C) plates." Films made of cholesteryl rod-shaped materials with a reflection band in the UV portion of the spectrum also exhibit the optical properties of negative C plates.

The birefringence Δn is defined as follows: Δn = _{ne -no} , where _ne is the extraordinary refractive index and _no is the ordinary refractive index, and ^the average effective refractive index _nav. is given by: _nav. = ( ⁽ _2n02 + _ne2 )/3) ^1/2

The average effective refractive index n _av. and the ordinary refractive index n _o can be measured using an Abbe refractometer. Δn can then be calculated using the above equation.

Unless the context clearly indicates otherwise, as used herein, plural forms of terms are to be understood as including the singular form and vice versa.

Unless expressly stated otherwise, all physical properties have been measured according to or in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals", Status Nov. 1997, Merck KGaA, Germany, and are given at 20° C. The optical anisotropy (Δn) is measured at a wavelength of 589.3 nm.

In case of doubt, the definition given in C. Tschierske, G. Pelzl and S. Diele, Angew. Chem. 2004, 116, 6340-6368 should be applied.

Unless expressly stated otherwise, in the given general formulae, the following terms have the following meanings: "Carbonyl" means a monovalent or polyvalent organic group containing one or more carbon atoms, which contains no other atoms (e.g., -C≡C-) or, if appropriate, contains one or more other atoms, such as N, O, S, P, Si, Se, As, Te, or Ge (e.g., carbonyl). "Hydrocarbonyl" means a carbonyl group which additionally contains one or more hydrogen atoms and, if appropriate, one or more impurity atoms (e.g., N, O, S, P, Si, Se, As, Te, or Ge).

A carbonyl or alkyl group can be saturated or unsaturated. Unsaturated groups are, for example, aryl, alkenyl, or alkynyl. Carbonyl or alkyl groups with more than three carbon atoms can be linear, branched, and/or cyclic and may contain spiro linkages or condensed rings.

Preferred carbon and alkyl groups are optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy groups having 1 to 40, preferably 1 to 25, and particularly preferably 1 to 18 C atoms; optionally substituted aryl or aryloxy groups having 6 to 40, preferably 6 to 25 C atoms; or optionally substituted alkylaryl, arylalkyl, alkylaryloxy, arylalkoxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy and aryloxycarbonyloxy groups having 6 to 40, preferably 6 to 25 C atoms.

More preferred carbon groups and alkyl groups are C1- _C40 alkyl, _C2 - _C40 alkenyl, _C2 - _C40 alkynyl, C3-C40 allyl, _C4 - _C40 alkyldienyl _{, C4} - _C40 polyalkenyl, C6- _C40 aryl, _C6 - _C40 alkylaryl, _{C6 - C40} arylalkyl, _C6 - _C40 alkylaryloxy, _C6 - _C40 arylalkoxy, _C2 - _C40 heteroaryl, _C4 - _C40 cycloalkyl, _{C4 - C40} cycloalkenyl, and _the like. Particularly preferred are C ₁ -C ₂₂ alkyl, C ₂ -C ₂₂ alkenyl, C ₂ -C ₂₂ alkynyl, C ₃ -C ₂₂ allyl, C ₄ -C ₂₂ alkyldienyl, C ₆ -C ₁₂ aryl, C ₆ -C ₂₀ arylalkyl and C ₂ -C ₂₀ heteroaryl.

More preferred carbon and alkyl groups are linear, branched or cyclic alkyl groups having 1 to 40, preferably 1 to 25, more preferably 1 to 12 C atoms, which are unsubstituted or mono- or polysubstituted with F, Cl, Br, I or CN, and in which one or more non-adjacent _CH2 groups can be independently replaced by -C( ^Rx )=C( ^Rx )-, -C≡C-, -N(Rx)-, -O-, -S-, -CO-, -CO- ^O- , -O-CO-, or -O-CO-O- in such a manner that the O and/or S atoms are not directly connected to each other.

In the above, ^Rx preferably represents H, a halogen, a linear, branched or cyclic alkyl chain having 1 to 25 C atoms, wherein in addition, one or more non-adjacent C atoms may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, and wherein one or more H atoms may be replaced by fluorine, an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms.

Preferred alkyl groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, di-butyl, tertiary butyl, 2-methylbutyl, n-pentyl, di-pentyl, n-hexyl, 2-ethylhexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, dodecyl, trifluoromethyl, perfluoro-n-butyl, 2,2,2-trifluoroethyl, perfluorooctyl, and perfluorohexyl.

Preferred alkenyl groups include ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, and cyclooctenyl.

Preferred alkynyl groups include ethynyl, propynyl, butynyl, pentynyl, hexynyl, octynyl and the like.

Preferred alkoxy groups include methoxy, ethoxy, 2-methoxyethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, di-butoxy, tertiary butoxy, 2-methylbutoxy, n-pentoxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy, and n-dodecyloxy.

Preferred amino groups include dimethylamino, methylamino, methylanilino, and anilino.

Aryl and heteroaryl groups can be monocyclic or polycyclic, i.e., they can have one ring (e.g., phenyl) or two or more rings, which can also be fused (e.g., naphthyl) or covalently linked (e.g., biphenyl), or contain a combination of fused and linked rings. Heteroaryl groups contain one or more heteroatoms, preferably selected from O, N, S, and Se.

Preferred are monocyclic, bicyclic or tricyclic aryl groups having 6 to 25 carbon atoms and monocyclic, bicyclic or tricyclic heteroaryl groups having 2 to 25 carbon atoms, which optionally contain fused rings and are optionally substituted. Furthermore, preferred are 5-, 6- or 7-membered aryl and heteroaryl groups, in which one or more CH groups may be replaced by N, S or O in such a way that the O atoms and/or S atoms are not directly connected to each other.

Preferred aryl groups include phenyl, biphenyl, terphenyl, [1,1':3',1'']terphenyl-2'-yl, naphthyl, anthracene, binaphthyl, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fused tetraphenyl, fused pentacene, benzopyrene, fluorene, indene, indenofluorene, and spirobifluorene.

Preferred heteroaryl groups are, for example, 5-membered rings such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, furan, thiophene, selenophene, oxadiazole, isoxadiazole, 1,2-thiazole, 1,3-thiazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole; 6-membered rings such as pyridine, pyrimidine, pyrimidine, pyridine, 1,3,5-triazole, 1,2,4-triazole, 1,2,3-oxadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole; triazole, 1,2,4,5-tetramethyleneimine, 1,2,3,4-tetramethyleneimine, 1,2,3,5-tetramethyleneimine; or condensed groups such as indole, isoindole, indolizole, indazole, benzimidazole, benzotriazole, purine, naphthalene imidazole, phenimidazole, pyridinimidazole, pyriimidazole, quinoxaline imidazole, benzotriazole, oxazole, naphthazole, anthraxazole, phenanthazole, isoazole, benzothiazole, benzofuran, isobenzofuran, dibenzofuran, quinoline, isoquinoline, pteridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, benzoisoquinoline, acridine, phenathiophene, phenanthiophene, benzopyrimidine, quinoxaline, phenanthiophene, azodiazole, benzocarboline, phenanthridine, phenanthroline, thieno[2,3b]thiophene, thieno[3,2b]thiophene, dithienothiophene, isobenzothiophene, dibenzothiophene, benzothiadiazolethiophene, or a combination of these groups. The heteroaryl group may also be substituted by an alkyl group, an alkoxy group, a sulfanyl group, a fluorine group, a fluoroalkyl group, or other aryl or heteroaryl groups.

(Non-aromatic) cycloaliphatic and heterocyclic groups include both saturated rings (i.e., those containing exclusively single bonds) and partially unsaturated rings (i.e., those containing multiple bonds). Heterocyclic rings contain one or more heteroatoms preferably selected from O, N, S and Se.

(Non-aromatic) alicyclic and heterocyclic groups can be monocyclic, i.e., containing only one ring (e.g., cyclohexane), or polycyclic, i.e., containing multiple rings (e.g., decahydronaphthalene or bicyclooctane). Saturated groups are particularly preferred. Furthermore, monocyclic, bicyclic, or tricyclic groups having 3 to 25 carbon atoms, optionally containing fused rings and optionally substituted, are preferred. Furthermore, 5-, 6-, 7-, or 8-membered carbocyclic groups are preferred, wherein one or more carbon atoms may be replaced by Si, and/or one or more CH groups may be replaced by N, and/or one or more non-adjacent _CH2 groups may be replaced by -O- and/or -S-.

Preferred alicyclic groups and heterocyclic groups include, for example, 5-membered groups such as cyclopentane, tetrahydrofuran, tetrahydrothiofuran, and pyrrolidine; 6-membered groups such as cyclohexane, cyclohexasilane, cyclohexene, tetrahydropyran, tetrahydrothiopyran, 1,3-dioxane, 1,3-dithiane, and piperidine; 7-membered groups such as cyclohexane, cyclohexasilane, cyclohexene, tetrahydropyran, tetrahydrothiopyran, 1,3-dioxane, and piperidine. such as cycloheptane; and fused groups such as tetrahydronaphthalene, decahydronaphthalene, indane, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, octahydro-4,7-methanoindan-2,5-diyl.

The aryl group, heteroaryl group, (non-aromatic) alicyclic group and heterocyclic group may have one or more substituents, preferably selected from the group consisting of a silyl group, a sulfonic acid group, a sulfonyl group, a formyl group, an amine, an imine, a nitrile, a hydroxyl group, a nitro group, a halogen group, a C _1-12 alkyl group, a C _6-12 aryl group, a C _1-12 alkoxy group, a hydroxyl group or a combination of these groups.

Preferred substituents are, for example, solubilizing groups such as alkyl or alkoxy groups; electron-withdrawing groups such as fluorine, nitro or nitrile; or substituents for increasing the glass transition temperature (Tg) of the polymer, in particular bulky groups such as tertiary butyl or optionally substituted aryl groups.

Preferred substituents (hereinafter also referred to as "L") are, for example, F, Cl, Br, _I , -OH, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N( ^Rx ) ₂ , -C(=O) ^Yx , -C(=O) ^Rx , -C(=O) ^ORx , -N( ^Rx ) ₂ , wherein ^Rx has the meanings mentioned above, and Y ^x represents a halogen, an optionally substituted silyl group, an optionally substituted aryl or heteroaryl group having 4 to 40, preferably 4 to 20 ring atoms, and a linear or branched alkyl group, alkenyl group, alkynyl group, alkoxy group, alkylcarbonyl group, alkoxycarbonyl group, alkylcarbonyloxy group or alkoxycarbonyloxy group having 1 to 25 carbon atoms, wherein one or more H atoms may be optionally replaced by F or Cl.

“Substituted silyl or aryl” preferably means substituted by halogen, -CN, R ^y , -OR ^y , -CO-R ^y , -CO-OR ^y , -O-CO-R ^y or -O-CO-OR ^y , wherein R ^y represents H, a linear, branched or cyclic alkyl chain having 1 to 12 carbon atoms.

In the formulae shown above and below, the substituted phenylene ring Better , in which L, at each occurrence, identically or differently, has one of the meanings given above and below, and is preferably F, Cl, CN, NO ₂ , CH ₃ , C ₂ H ₅ , C(CH ₃ ) ₃ , CH(CH ₃ ) ₂ , CH ₂ CH(CH ₃ )C ₂ H ₅ , OCH ₃ , OC ₂ H ₅ , COCH ₃ , COC ₂ H ₅ , COOCH ₃ , COOC ₂ H ₅ , CF ₃ , OCF ₃ , OCHF ₂ , OC ₂ F ₅ or P-Sp-, very preferably F, Cl, CN, CH ₃ , C ₂ H ₅ , OCH ₃ , COCH ₃ , OCF ₃ or P-Sp-, most preferably F, Cl, CH ₃ , OCH ₃ , COCH ₃ or OCF ₃ .

"Halogen" means F, Cl, Br or I, preferably F or Cl, more preferably F.

The "polymerizable group" (P) is preferably selected from groups containing a C=C double bond or a C≡C triple bond, and groups suitable for ring-opening polymerization, such as oxetane or epoxide groups.

Preferably, the polymerizable group (P) is selected from the group consisting of: CH ₂ =CW ¹ -COO-, CH ₂ =CW ¹ -CO-, , CH ₂ =CW ² -(O) _k3 -, CW ¹ =CH-CO-(O) _k3 -, CW ¹ =CH-CO-NH-, CH ₂ =CW ¹ -CO-NH-, CH ₃ -CH=CH-O-, (CH ₂ =CH) ₂ CH-OCO-, (CH ₂ =CH-CH ₂ ) ₂ CH-OCO-, (CH ₂ =CH) ₂ CH-O-, (CH ₂ =CH-CH ₂ ) ₂ N-, (CH ₂ =CH-CH ₂ ) ₂ N-CO-, CH ₂ =CW ¹ -CO-NH-, CH ₂ =CH-(COO) _k1 -Phe-(O) _k2 -, CH ₂ =CH-(CO) _k1 -Phe-(O) _k2 -, Phe-CH=CH-, where W ¹ represents H, F, Cl, CN, CF ₃ , phenyl or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH ₃ , W ² represents H or alkyl having 1 to 5 C atoms, in particular H, methyl, ethyl or n-propyl, W ³ and W ⁴ each independently represent H, Cl or alkyl having 1 to 5 C atoms, Phe represents 1,4-phenylene, which is optionally substituted by one or more groups L as defined above but different from P-Sp, preferably, preferred substituents L are F, Cl, CN, NO ₂ , CH ₃ , C ₂ H ₅ , OCH ₃ , OC ₂ H ₅ , COCH ₃ , COC ₂ H ₅ , COOCH ₃ , COOC ₂ H ₅ , CF ₃ , OCF ₃ , OCHF ₂ , OC ₂ F ₅ and phenyl, and k ₁ , k ₂ and k _{k 3} each independently represents 0 or 1, k ₃ preferably represents 1, and k ₄ is an integer from 1 to 10.

Particularly preferred polymerizable groups P are CH ₂ =CH-COO-, CH ₂ =C(CH ₃ )-COO-, CH ₂ =CF-COO-, CH ₂ =CH-, CH ₂ =CH-O-, (CH ₂ =CH) ₂ CH-OCO-, (CH ₂ =CH) ₂ CH-O-, , wherein W ² represents H or an alkyl group having 1 to 5 C atoms, in particular H, methyl, ethyl or n-propyl.

More preferred polymerizable groups (P) are vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxycarbonyl, and epoxide, with acrylate or methacrylate being most preferred, particularly acrylate.

Preferably, all polyreactive polymerizable compounds and subformulas thereof contain one or more branching groups containing two or more polymerizable groups P (polyreactive polymerizable groups) rather than one or more groups P-Sp-.

Suitable groups of this type and polymerizable compounds containing these groups are described, for example, in US 7,060,200 B1 or US 2006/0172090 A1.

Particularly preferred are multi-reactive polymerizable groups selected from _the ^following formulae: -X-alkyl-CHPx- ^CH2 _{- CH2Py} ^I *a -X-alkyl-C( _CH2Px ) ^{( CH2Py} )-CH2Pz ^I *b -X-alkyl-CHPxCHPy ^{- CH2Pz} _I * _{c -X} - ^alkyl -C( _CH2Px )(CH2Py) _{-CaaH2aa +1} ^I *d ^-X - _alkyl - ^CHPx -CH2Py I*e -X-alkyl-CHPxPy ^I *f ^-X - _alkyl - ^CPxPy _-CaaH2aa+1 I*g -X-alkyl- ^{C (CH2Pv} ₎ ( _{CH2Pw ) -CH2OCH2} - ^C(CH2Px ₎ ⁽ _CH2Py ) _CH2Pz ^I *h -X-alkyl-CH((CH ₂ ) _aa P ^x )((CH ₂ ) _bb P ^y ) I*i -X-alkyl-CHP ^x CHP ^y -C _aa H _2aa+1 I*k wherein alkyl represents a single bond or a linear or branched alkyl group having 1 to 12 C atoms, wherein one or more non-adjacent CH ₂ groups can each independently of one another be replaced by -C(R ^x )═C(R x )-, -C≡C-, -N(R ^x )-, -O-, -S-, -CO-, -CO- ^O- , -O-CO-, -O-CO-O- in such a way that the O and/or S atoms are not directly bonded to one another, and wherein in addition one or more H atoms can be replaced by F, Cl or CN, wherein R ^x has one of the meanings mentioned above, _aa and _bb each independently represent 0, 1, 2, 3, 4, 5 or 6, X has one of the meanings indicated for X′, and ^Pv to ^Pz each independently have one of the meanings indicated above for P.

Preferred spacer groups Sp are selected from the formula Sp'-X', such that the group "P-Sp-" conforms to the formula "P-Sp'-X'-", wherein Sp' represents an alkylene group having 1 to 20, preferably 1 to 12, C atoms, which is optionally monosubstituted or polysubstituted with F, Cl, Br, I or CN, and wherein in addition, one or more non-adjacent _CH2 groups may each be independently replaced by -O-, -S-, -NH-, -NRxx-, ^-SiRxxRyy- , -CO-, -COO-, -OCO-, -OCO ^- O-, -S ^- CO-, -CO-S-, -NRxx-CO-O-, -O-CO-NR0xx-, ^-NRxx -CO-NRyy-, -CH=CH- or -C≡C- in such a way that the ^{O and} /or S atoms are ^not directly connected to each other, and X' represents -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR xx -, -NR ^xx -CO-, -NR ^xx -CO-NR yy -, -OCH _{2 -, -CH 2} ^{O- ,} -SCH _{2 -, -CH 2 S-, -CF 2} O-, -OCF ₂ -, -CF ₂ S-, -SCF ₂ -, -CF ₂ CH ₂ -, -CH ₂ CF ₂ -, -CF ₂ CF ₂ -, -CH= _N- , -N=CH-, -N=N-, -CH=CR ^xx -, -CY ^xx =CY ^xx -, -C≡C- _, -CH=CH-COO-, -OCO-CH=CH-, or a single _bond , R ^xx and R ^yy each independently represent H or an alkyl group having 1 to 12 C atoms, and Y ^xx and Y ^yy each independently represents H, F, Cl or CN, and X' is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR ^xx -, -NR ^xx -CO-, -NR ^xx -CO-NR ^yy -, or a single bond.

Typical spacer groups Sp' are _, for example, -( _CH2 ) _p1- , -( _CH2CH2O ) _q1 - _CH2CH2- , -CH2CH2- _S - _CH2CH2- , _{-CH2CH2-NH-CH2CH2- , or - ( SiRxRxx} ^- _O ⁾ _p1- , wherein p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and ^Rxx and ^Ryy have the meanings mentioned above.

Particularly preferred groups -X'-Sp'- are -(CH ₂ ) _p1 -, -O-(CH ₂ ) _p1 -, -OCO-(CH ₂ ) _p1 -, and -OCOO-(CH ₂ ) _p1 -, wherein p1 is an integer from 1 to 12.

Particularly preferred radicals Sp' in each case are, for example, linear, methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, vinylene, propenylene and butenylene.

For the present invention, represents trans-1,4-cyclohexylene, and represents 1,4-phenylene.

For the present invention, the group -COO- or -CO ₂ - is represented by Ester group, and the group -OCO-, -O ₂ C- or -OOC- is represented by Ester group.

A "polymer network" is a network in which all polymer chains are interconnected by numerous cross-links to form a single macroscopic entity.

Polymer networks can exist in the following types: - Graft polymer molecules are branched polymer molecules in which one or more side chains differ structurally or conformationally from the main chain. - Star polymer molecules are branched polymer molecules in which a single branch point gives rise to multiple linear chains or arms. If the arms are identical, the star polymer molecule is called regular. If adjacent arms are composed of different repeating subunits, the star polymer molecule is called diversified. - Comb polymer molecules consist of a main chain with two or more three-way branch points and linear side chains. If the arms are identical, the comb polymer molecule is called regular. - Brush polymer molecules consist of a main chain with linear, unbranched side chains, and one or more of the branch points has four-way functionality or greater.

Throughout this specification and the claims, the words "comprise" and "contain" and variations thereof (e.g., "comprising" and "comprises") mean "including but not limited to," and are not intended to (and do not) exclude other components. On the other hand, the word "comprising" also encompasses the term "consisting of," but is not limited to that term.

Throughout the description and claims of this specification, the words "available" and "obtained" and variations thereof mean "including but not limited to," and are not intended to (and do not) exclude other components. On the other hand, the word "available" also encompasses the term "obtained," but is not limited to that term.

All concentrations are given as percentages by weight and relate to the respective mixture as a whole, all temperatures are given in degrees Celsius and all temperature differences are given in degrees.

Preferred compounds of formula I are selected from the following preferred examples.

In the compounds of formula I, the group N(R ¹³ )(R ¹⁴ ) may also preferably be an amine.

Another preferred compound is a compound of formula I, wherein p is 2, is an organic group having 4 bonding sites, preferably an alkanetetrayl unit having 1 to 30 C atoms, wherein, in addition to the m groups R ¹² present in the molecule (but independently thereof), another H atom can be replaced by R ¹² or a plurality of other H atoms can be replaced by R ¹² , preferably an alkanetetrayl unit having one or two valencies at each of the two terminal C atoms, wherein one -CH ₂ - group or a plurality of -CH ₂ - groups can be replaced by -O- or -(C=O)- in such a way that two O atoms are not directly bonded to each other, or a substituted or unsubstituted aromatic or heteroaromatic hydrocarbon group having up to 8 valencies, wherein, in addition to the m groups R ¹² present in the molecule (but independently thereof), another H atom can be replaced by R ¹² or a plurality of other H atoms can be replaced by R ¹² , express (biphenyl-1,1´,3,3´-tetrayl), (benzene-1,2,4,5-tetrayl) or -CH ₂ -(CH-)-[CH ₂ ] _q -(CH-)-CH ₂ - (wherein q ∈ {0, 1, 2, 3 to 16}) or >CH-[CH ₂ ] _r -CH< (wherein r ∈ {0, 1, 2, 3, 4, 5 to 18}), express (Benzene-1,3,5-triyl), (benzene-1,2,4-triyl) or >CH-[CH ₂ ] _r -CH ₂ - (wherein r ∈ {0, 1, 2, 3, 4, 5 to 18}) or represents _-CH2- [ _CH2 ] _r - _CH2- (wherein r∈{0, 1, 2, 3, 4, 5 to 18}), oct-1,8-diyl, hept-1,7-diyl, hex-1,6-diyl, pent-1,5-diyl, but-1,4-diyl, prop-1,3-diyl, ethyl-1,2-diyl, or (1,4-phenylene), (1,3-phenylene), (1,2-phenylene) or (1,4-cyclohexylene).

In a preferred embodiment of the present invention, in the compound of formula I, express 、 (biphenyl-1,1´,3,3´-tetrayl) or (Benzene-1,2,4,5-tetrayl) express (benzene-1,3,5-triyl) or (benzene-1,2,4-triyl), represents -(CH ₂ -) ₂ , -(CH ₂ -) ₃ , -(CH ₂ -) ₄ , -(CH ₂ -) ₅ , -(CH ₂ -) ₆ , -(CH ₂ -) ₇ , -(CH ₂ -) ₈ , that is, Ethyl-1,2-diyl, propan-1,3-diyl, butan-1,4-diyl, pentyl-1,5-diyl, hexyl-1,6-diyl, heptyl-1,7-diyl, octyl-1,8-diyl, (1,4-phenylene), (1,3-phenylene), (1,2-phenylene) or (trans-1,4-cyclohexylene) and/or -Z ¹² -S ¹¹ -Z ¹¹ -, at each occurrence, independently represents -O-, -S ¹¹ -O-, -OS ¹¹ -O-, -(C=O)-OS ¹¹ -O-, -O-(C=O)-S 11 -O-, -O-(C=O)-S ¹¹ -(C=O)-O-, -OS ¹¹ -(C=O)-O-, - ⁽ C=O)-OS ¹¹ -(C=O)-O-, or -(NR ¹³ )-S ¹¹ -O-, -NR ¹³ -(C=O)-S ¹¹ -(C=O)-O-, or a single bond, preferably -O-, -S ¹¹ -O-, -OS ¹¹ -O-, -(C=O)-OS ¹¹ -O-, -O-(C=O)-S ¹¹ -O- or -OS ¹¹ -(C=O)-O-, and/or R ¹¹ , if present, represents alkyl, alkoxy or H, preferably H or alkyl, and/or R ¹² represents H, methyl, ethyl, propyl, isopropyl or 3-heptyl, or cyclohexyl.

In one preferred embodiment of the present application, in the compound of formula I, represents a group selected from the group: .

In one preferred embodiment of the present application, in the compound of formula I, represents a group selected from the group: .

In one preferred embodiment of the present application, in the compound of formula I (wherein p preferably represents 1), express , preferably -OS ¹¹ -O-, -S ¹¹ -O- or -OS ¹¹ -, particularly preferably -OS ¹¹ -O-.

In one preferred embodiment of the present application, in the compound of formula I, the group Preferably, the group is selected from the group consisting of: .

In another preferred embodiment of the present application (which may be the same as or different from those described above), in the compound of formula I, Preferably, the group is selected from the group consisting of: .

In another preferred embodiment of the present invention (which may be the same as or different from those described above), in the compound of formula I, the group , which represent independently on each occurrence , Better .

In a particularly preferred embodiment of the present invention, in the compound of formula I, all the groups present are Meanings have the same meaning.

In a preferred embodiment of the present invention, the medium according to the present invention in each case comprises one or more compounds of the formula I selected from the group of compounds of the following formulae I-1 to I-13, preferably from the group of compounds of the formulae I-3, I-5, I-6, I-7, I-8, I-9, I-10, I-12 and I-13, particularly preferably from the group of compounds of the formulae I-6 to I-9 and very preferably from the group of compounds of the formula I-9, .

In an even better embodiment of the invention, the medium according to the invention comprises in each case one or more compounds of formula I selected from the group of compounds of the following formulae I-1 and/or I-3 to I-7 and/or I-8 and/or I-9.

In an even more preferred embodiment of the invention, the medium according to the invention comprises in each case one or more compounds of the formula I selected from the group of compounds of the following formulae I-8 and/or I-9.

In another preferred embodiment of the present invention, the medium according to the invention in each case comprises at least one or more compounds of the formula I, in which p is 1 and n is 3, 4, 5 or 6, preferably 4, and the group -Z ¹¹ -S ¹¹ -Z ¹² - represents ω-bisoxyalkylene, i.e. -OS ¹¹ -O-. Such mediators have excellent stability.

The compounds of formula I can advantageously and preferably be prepared according to the disclosure given in U.S. application Ser. No. 15/883,976.

Preferably, one or more bireactive or polyreactive mesogen compounds are selected from the formula DRM P ¹ -Sp ¹ -MG-Sp ² -P ² DRM wherein P ¹ and P ² independently represent a polymerizable group, Sp ¹ and Sp ² independently represent a spacer group or a single bond, and MG is a rod-shaped mesogen group, which is preferably selected from the formula MG -(A ¹ -Z ¹ ) _n -A ² - MG wherein A ¹ and A ² , when occurring multiple times, independently represent an aromatic or alicyclic group, which optionally contains one or more heteroatoms selected from N, O and S and is optionally monosubstituted or polysubstituted by L ¹ , L ¹ is P-Sp-, F, Cl, Br, I, -CN, -NO ₂ , -NCO, -NCS, -OCN, -SCN, -C(=O)NR ⁰⁰ R ⁰⁰⁰ , -C(=O)OR ⁰⁰ , -C(=O)R ⁰⁰ , -NR ⁰⁰ R ⁰⁰⁰ , -OH, -SF ₅ , an optionally substituted silyl group, an aryl group or heteroaryl group having 1 to 12, preferably 1 to 6, C atoms, and a linear or branched alkyl group, alkoxy group, alkylcarbonyl group, alkoxycarbonyl group, alkylcarbonyloxy group or alkoxycarbonyloxy group having 1 to 12, preferably 1 to 6, C atoms, wherein one or more H atoms are optionally replaced by F or Cl, R ⁰⁰ and R ⁰⁰⁰ independently represent H or an alkyl group having 1 to 12 C atoms, Z ¹ In the case of multiple occurrences, it represents -O-, -S-, -CO-, -COO-, -OCO-, -S-CO-, -CO-S-, -O-COO-, -CO-NR 00 -, -NR ⁰⁰ -CO-, -NR ⁰⁰ -CO-NR ⁰⁰⁰ , -NR ⁰⁰ -CO-O-, -O ^- CO-NR ⁰⁰ -, -OCH ₂ -, -CH ₂ O-, -SCH 2 -, -CH ₂ S-, -CF ₂ O-, -OCF 2 -, -CF ₂ S-, -SCF ₂ -, -CH ₂ CH ₂ -, -(CH ₂ ) _{n1 , -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - , -CH = N- ,} -N=CH-, -N=N-, -CH=CR ⁰⁰ -, -CY ¹ =CY ² -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, or a single bond; Y ¹ and Y ² independently represent H, F, Cl, or CN; n is 1, 2, 3, or 4, preferably 1 or 2, most preferably 2; and n1 is an integer from 1 to 10, preferably 1, 2, 3, or 4.

Preferred groups A ¹ and A ² include, but are not limited to, furan, pyrrole, thiophene, oxazole, thiazole, thiadiazole, imidazole, phenylene, cyclohexylene, dicyclooctylene, cyclohexenylene, pyridine, pyrimidine, pyrrolidone, azulene, indane, fluorene, naphthalene, tetrahydronaphthalene, anthracene, phenanthrene, and dithienothiophene, all of which are unsubstituted or substituted with 1, 2, 3, or 4 groups L as defined above.

Particularly preferred groups A ¹ and A ² are selected from 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, thiophene-2,5-diyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydro-naphthalene-2,6-diyl, indane-2,5-diyl, bicyclooctyl or 1,4-cyclohexylene, wherein one or two non-adjacent CH ₂ groups are optionally replaced by O and/or S, wherein these groups are unsubstituted or substituted by 1, 2, 3 or 4 groups L as defined above.

Particularly preferred groups Z ¹ are preferably independently selected at each occurrence from -COO-, -OCO-, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -C≡C-, -CH=CH-, -OCO-CH=CH-, -CH=CH-COO- or a single bond.

The most preferred direactive mesogen compounds of the DRM type are selected from the following: wherein ^P0 is independently a polymerizable group in the case of multiple occurrences, preferably propenyl, methacryl, oxadiazol, epoxy, vinyl, heptadienyl, vinyloxy, propenyl ether or styryl, L has one of the meanings given for ^L1 in the formula DRM, the same or different on each occurrence, and is independently selected from F, Cl, CN or an optionally halogenated alkyl group having 1 to 5 C atoms, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy in the case of multiple occurrences, r is 0, 1, 2, 3 or 4, x and y are independently 0 or the same or different integers from 1 to 12, z is each and independently 0 or 1, wherein if adjacent x or y is 0, then z is 0.

Particularly preferred are compounds of formula DRMa1, DRMa2 and DRMa3, in particular those of formula DRMa1.

Preferably, the polymerizable LC material further comprises one or more monoreactive mesogen compounds, preferably selected from the formula MRM, ^P1 - ^Sp1 -MG-RMRM wherein ^P1 , ^Sp1 and MG have the meanings given in formula DRM, R is F, Cl, Br, I, -CN, _-NO2 , -NCO, -NCS, -OCN, -SCN, ^-C (=O) ^NRxRy , -C(=O)X, -C(=O) ^ORx , -C(=O) ^Ry , ^-NRxRy , ^-OH , _-SF5 , optionally substituted silyl, linear or branched alkyl having 1 to 12, preferably 1 to 6, C atoms, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, wherein one or more H atoms are optionally replaced by F or Cl, X is halogen, preferably F or Cl, and R ^x and R ^y are independently H or alkyl having 1 to 12 C atoms.

Preferably, one or more monoreactive mesogen compounds of formula MRM are selected from the following formulas: wherein P ⁰ , L, r, x, y and z are as defined in formulae DRMa-1 to DRMe, R ⁰ , R ⁰¹ and R ⁰² are alkyl, alkoxy, sulfanyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy groups having 1 or more, preferably 1 to 15, carbon atoms, or represent Y ⁰ , Y ⁰ is F, Cl, CN, NO ₂ , OCH ₃ , OCN, SCN, SF ₅ , or a monofluorinated, oligofluorinated or polyfluorinated alkyl or alkoxy group having 1 to 4 carbon atoms, Z ⁰ is -COO-, -OCO-, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CH-, -OCO-CH=CH-, -CH=CH-COO- or a single bond, A ^0, in the case of multiple occurrences, is independently 1,4-phenylene, which is unsubstituted or substituted with 1, 2, 3 or 4 groups L, or trans-1,4-cyclohexylene, u and v are independently 0, 1 or 2, w is 0 or 1, and the benzene ring and the naphthyl ring may be further substituted with one or more identical or different groups L.

More preferred are compounds of the formulae MRM1, MRM2, MRM3, MRM4, MRM5, MRM6, MRM7, MRM9 and MRM10, especially those of the formulae MRM1, MRM4, MRM6 and MRM7, and particularly those of the formulae MRM1 and MRM7.

Compounds of formula DRM, formula MRM and subformulae thereof can be prepared in a manner analogous to the procedures known to those skilled in the art and described in standard texts of organic chemistry, such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Thieme-Verlag, Stuttgart.

In a preferred embodiment, the proportion of the polymerizable liquid crystal primordial compound in the overall polymerizable liquid crystal material according to the present invention is in the range of 30 wt % to 99 wt %, more preferably in the range of 40 wt % to 97 wt %, and even more preferably in the range of 50 wt % to 95 wt %.

Preferably, the proportion of the monoreactive, bireactive or polyreactive liquid crystal compounds (preferably selected from the compounds of the formula DRM, MRM and/or ND as given above and below) in the overall polymerizable liquid crystal material according to the present invention is preferably in the range of 30 wt. % to 99.9 wt. %, more preferably in the range of 40 wt. % to 99.9 wt. %, and even more preferably in the range of 50 wt. % to 99.9 wt. %.

In a preferred embodiment, the proportion of the bireactive or polyreactive polymerizable liquid crystal primordium compound in the overall polymerizable liquid crystal material according to the present invention is preferably in the range of 5 wt % to 99 wt %, more preferably in the range of 10 wt % to 97 wt %, and even more preferably in the range of 15 wt % to 95 wt %.

In another preferred embodiment, the proportion of the monoreactive polymerizable mesogen compound (if present) in the overall polymerizable liquid crystal material according to the present invention is preferably in the range of 5 wt % to 80 wt %, more preferably in the range of 10 wt % to 75 wt %, and even more preferably in the range of 15 wt % to 70 wt %.

In another preferred embodiment, the proportion of the multi-reactive polymerizable mesogen compound (if present) in the overall polymerizable liquid crystal material according to the present invention is preferably in the range of 1 wt % to 30 wt %, more preferably in the range of 2 wt % to 20 wt %, and even more preferably in the range of 3 wt % to 10 wt %.

In another preferred embodiment, the polymerisable LC material does not contain a polymerisable mesogen compound having more than two polymerisable groups.

In another preferred embodiment, the polymerisable LC material does not contain a polymerisable mesogen compound having less than two polymerisable groups.

In another preferred embodiment, the polymerizable LC material is a non-chiral material, that is, it does not contain any chiral polymerizable mesogen compound or other chiral compound.

In another preferred embodiment, the polymerizable LC material comprises one or more monoreactive mesogen compounds preferably selected from formula MRM-1, one or more direactive mesogen compounds preferably selected from formula DRMa-1, and one or more compounds of formula I.

In another preferred embodiment, the polymerizable LC material comprises one or more monoreactive mesogen compounds preferably selected from formula MRM-7, one or more direactive mesogen compounds preferably selected from formula DRMa-1, and one or more compounds of formula I.

In another preferred embodiment, the polymerizable LC material comprises at least two monoreactive mesogen compounds (preferably selected from compounds of formula MRM-1 and/or MRM-7), one or more direactive mesogen compounds, preferably selected from formula DRMa-1, and one or more compounds of formula I.

In another preferred embodiment, the polymerizable LC material comprises at least two monoreactive mesogen compounds (preferably selected from compounds of formula MRM-1 and/or MRM-7), at least two direactive mesogen compounds (preferably selected from compounds of formula DRMa-1) and one or more compounds of formula I.

In another preferred embodiment, the polymerizable LC material comprises at least two bireactive mesogen compounds (preferably selected from compounds of formula DRMa-1) and one or more compounds of formula I.

In another preferred embodiment, in particular for negative optical dispersion applications, the polymerizable LC material as described above additionally comprises one or more ND compounds of the formula Where U ^{1 and U 2} are independently selected from: Including mirror images thereof, wherein the ring U ¹ and the ring U ² are each bonded to the group -(B) _q - via an axial bond, and one or two non-adjacent CH ₂ groups in these rings are optionally replaced by O and/or S, and the ring U ¹ and the ring U ² are optionally substituted by one or more groups L, Q ^{1 and 2} are independently CH or SiH, Q ³ is C or Si, B is independently -C≡C-, -CY ¹ =CY ² - or an optionally substituted aromatic or heteroaromatic group at each occurrence, Y ^{1 and 2} are independently H, F, Cl, CN or R ⁰ , q is an integer from 1 to 10, preferably 1, 2, 3, 4, 5, 6 or 7, A ^1-4 are independently selected from non-aromatic, aromatic or heteroaromatic carbocyclic or heterocyclic groups, which are optionally substituted by one or more groups R ⁵ , and each of -(A ¹ -Z ¹ ) _m -U ¹ -(Z ² -A ² ) _n - and -(A ³ -Z ³ ) _o -U ² -(Z ⁴ -A ⁴ ) _p - does not contain more aromatic groups than non-aromatic groups and preferably does not contain more than one aromatic group, and Z ^1-4 are independently -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR ⁰ -, -NR ^{0 -CO-, -NR 0 -CO-NR 00 - ,} -OCH ₂ -, -CH ₂ O-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, -CF ₂ S-, -SCF ₂ - _, -CH ₂ CH ₂ -, -(CH ₂ ) ₃ -, -(CH ₂ ) ₄ -, -CF _{2 CH 2 -, -CH 2} CF ₂ -, -CF ₂ CF _{2 -} , -CH=CH-, -CY ¹ =CY ² -, -CH=N-, -N=CH-, -N=N- _, -CH=CR ⁰ -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, CR ⁰ R ⁰⁰ or a single bond, R ⁰ and R ⁰⁰ are independently H or an alkyl group having 1 to 12 C atoms, m and n are independently 0, 1, 2, 3 or 4, o and p are independently 0, 1, 2, 3 or 4, R ^1-5 are independently the same or different groups selected from the following: H, halogen, -CN, -NC, -NCO, -NCS, -OCN, -SCN, -C(=O)NR ⁰ R ⁰⁰ , -C(=O)R ⁰ , -NH ₂ , -NR ⁰ R ⁰⁰ , -SH, -SR ⁰ , -SO ₃ H, -SO ₂ R ⁰ , -OH, -NO ₂ , -CF ₃ , -SF ₅ , P-Sp-, an optionally substituted silyl group or carbon group, or an optionally substituted alkyl group having 1 to 40 C atoms which optionally contains one or more heteroatoms, or represents P or P-Sp-, or is substituted with P or P-Sp-, wherein the compounds contain one or more groups R ^1-5 representing P or P-Sp- or substituted with P or P-Sp-, P is a polymerizable group, and Sp is a spacer group or a single bond.

Preferably, the subunit forming the bridging group B in formula ND is selected from groups having a bonding angle of 120° or greater, preferably within the range of 180°. Most preferably, it is a -C≡C- group or a divalent aromatic group linked to its neighboring group at the para position, such as 1,4-phenylene, naphthalene-2,6-diyl, indane-2,6-diyl, or thieno[3,2-b]thiophene-2,5-diyl.

Other possible subunits include -CH=CH-, -CY ¹ =CY ² -, -CH=N-, -N=CH-, -N=N- and -CH=CR ⁰ -, wherein Y ¹ , Y ² and R ⁰ have the meanings given above.

Preferably, the bridging group or -(B) _q- in Formula ND comprises one or more groups selected from the group consisting of -C≡C-, optionally substituted 1,4-phenylene, and optionally substituted 9H-fluorene-2,7-diyl. The subunit or B in Formula ND is preferably selected from the group consisting of -C≡C-, optionally substituted 1,4-phenylene, and optionally substituted 9H-fluorene-2,7-diyl, wherein the H atom at position 9 in the fluorene group is optionally replaced by a carbonyl or alkyl group.

Most preferably, the bridging group or -(B) _q - in formula ND is selected from -C≡C-, -C≡CC≡C-, -C≡CC≡CC≡C-, -C≡CC≡CC≡C-, wherein r is 0, 1, 2, 3 or 4, and L has the meaning described below.

Preferably, the non-aromatic ring of the mesogen group to which the bridging group is connected (such as U ¹ and U ² in formula ND) is preferably selected from , wherein R ⁵ is as defined in Formula ND.

Preferably, the aromatic groups A ^1-4 in formula ND are mononuclear, i.e., have only one aromatic ring (e.g., phenyl or phenylene), or polynuclear, i.e., have two or more fused rings (e.g., naphthyl or naphthylene). Particularly preferred are monocyclic, bicyclic, or tricyclic aromatic or heteroaromatic groups having up to 25 carbon atoms, which may also contain fused rings and are optionally substituted.

Preferably, the non-aromatic carbocyclic and heterocyclic rings A ^1-4 in the compounds of formula ND include those that are saturated (also referred to as "fully saturated"), i.e., they contain only carbon atoms or heteroatoms linked by single bonds; and those that are unsaturated (also referred to as "partially saturated"), i.e., they also contain carbon atoms or heteroatoms linked by double bonds. Non-aromatic rings may also contain one or more heteroatoms, preferably selected from Si, O, N, and S.

Preferably, the non-aromatic ring and the aromatic ring or A ^1-4 in formula ND are selected from trans-1,4-cyclohexylene and 1,4-phenylene optionally substituted with one or more groups L.

Very preferred are compounds of formula ND, wherein m and p are 1 and n and o are 1 or 2. More preferred are compounds of formula ND, wherein m and p are 1 or 2 and n and o are 0. Even more preferred are compounds wherein m, n, o and p are 2.

In the compound of formula ND, the linking group connecting the aromatic and non-aromatic cyclic groups in the mesogen group or Z ^1-4 is preferably selected from -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR ⁰ -, -NR ⁰ -CO-, -NR ⁰ -CO-NR ⁰ -, -OCH ₂ -, -CH ₂ O-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, -CF ₂ S-, -SCF ₂ -, -CH ₂ CH ₂ -, -(CH ₂ ) ₃ -, -(CH ₂ ) ₄ -, -CF ₂ CH ₂ -, -CH ₂ CF ₂ -, -CF ₂ CF ₂ -, -CH=CH-, -CY ¹ =CY ² -, -CH=N-, -N=CH-, -N=N-, -CH=CR ⁰ -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, CR ⁰ R ⁰⁰ or a single bond, preferably selected from -COO-, -OCO- and a single bond.

Preferably, in the compound of formula ND, the substituents on the ring (such as L) are preferably selected from P-Sp-, F, Cl, Br, I, -CN, _-NO2 , -NCO, -NCS, -OCN, ^-SCN , -C(=O) ^NR0R00 , -C(=O)X, -C(=O) ^OR0 , -C(=O ^{)R0, -NR0R00 , -OH} , _-SF5 , an optionally substituted silyl group, an aryl group or heteroaryl group having 1 to 12, preferably 1 to 6, C atoms, and a straight or branched alkyl group, alkoxy group, alkylcarbonyl group, alkoxycarbonyl group, alkylcarbonyloxy group or alkoxycarbonyloxy group having 1 to 12, preferably 1 to 6, C atoms, wherein one or more H atoms are optionally replaced by F or Cl, wherein R ⁰ and R ⁰⁰ are as defined in formula ND and X is a halogen.

Preferably, the compound of formula ND comprises one or more terminal groups (e.g., R ^1-4 ) or substituents (e.g., R ⁵ ) substituted with two or more polymerizable groups P or P-Sp- (multifunctional polymerizable groups). Suitable multifunctional polymerizable groups of this type are disclosed, for example, in US 7,060,200 B1 or US 2006/0172090 A1.

Very preferred compounds of formula ND are those of the following sub-formula: wherein R ^1-5 , A ^1-4 , Z ^1-4 , B, m, n, o, p and q have one of the meanings given above.

Particularly preferred are compounds of the following sub-formula: wherein Z has one of the meanings given above for Z ¹ , R has one of the meanings given above for R ¹ different from P-Sp-, and P, Sp, L and r are as defined above, and the benzene ring in the mesogen group is optionally substituted by one or more groups L as defined above.

Furthermore, preferred are polymerizable liquid crystal media wherein the compound of formula ND is selected from the group of compounds of formula ND 25 or ND 26, in particular wherein Z represents -COO-, r is 0 at each occurrence, and P, Sp are as defined above.

In these preferred compounds, P-Sp- is preferably P-Sp'-X', wherein X' is preferably -O-, -COO- or -OCOO-.

Compounds of formula ND, its subformulae and suitable methods for their synthesis are disclosed in WO 2008/119427 A1.

The amount of the compound of formula ND in the polymerizable LC material is preferably from 0% to 50%, very preferably from 0% to 40%.

In another preferred embodiment, the polymerizable LC material optionally comprises one or more additives selected from the group consisting of other polymerization initiators, antioxidants, surfactants, stabilizers, catalysts, sensitizers, inhibitors, chain transfer agents, co-reactive monomers, reactive thinners, surface-active compounds, lubricants, wetting agents, dispersants, hydrophobic agents, tackifiers, flow improvers, deaerators or defoamers, degassing agents, diluents, reactive diluents, auxiliary agents, colorants, dyes, pigments, and nanoparticles.

In another preferred embodiment, the polymerizable LC material optionally contains one or more additives selected from polymerizable non-mesogenic compounds (reactive viscosity reducing agents). The amount of such additives in the polymerizable LC material is preferably 0% to 30%, and most preferably 0% to 25%.

The reactive detackifier used is not only a substance that is actually called a reactive detackifier, but also the auxiliary compound mentioned above containing one or more complementary reactive units or polymerizable groups P (for example, hydroxyl groups, thiol groups or amine groups). The reaction with the polymerizable units of the liquid crystal compound can be carried out via these substances.

Typical photopolymerizable substances include monofunctional, difunctional, and polyfunctional compounds containing at least one olefinic double bond. Examples include vinyl esters of carboxylic acids (e.g., lauric acid, myristic acid, palmitic acid, and stearic acid) and vinyl esters of dicarboxylic acids (e.g., succinic acid and adipic acid); allyl and vinyl ethers, as well as methacrylates and acrylates, of monofunctional alcohols (e.g., lauryl alcohol, myristyl alcohol, palmitic acid, and stearyl alcohol); and diallyl and divinyl ethers of difunctional alcohols (e.g., ethylene glycol and 1,4-butanediol).

Also suitable are, for example, methacrylates and acrylates of polyfunctional alcohols, in particular those which, in addition to hydroxyl groups, do not contain any other functional groups or at most contain ether groups. Examples of such alcohols are difunctional alcohols such as ethylene glycol, propylene glycol and their more highly condensed representatives (e.g., diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, etc.), butanediol, pentanediol, hexanediol, neopentyl glycol, alkoxylated phenolic compounds (e.g., ethoxylated and propoxylated bisphenols), cyclohexanedimethanol; trifunctional and polyfunctional alcohols such as glycerol, trihydroxymethylpropane, butanetriol, trihydroxymethylethane, neopentyletrol, ditrihydroxymethylpropane, dipentatriol, sorbitol, mannitol and the corresponding alkoxylated alcohols, in particular ethoxylated and propoxylated alcohols.

Other suitable reactive detackifiers are polyester (meth)acrylates, which are (meth)acrylates of polyester alcohols.

Examples of suitable polyesterols are those that can be prepared by esterifying polycarboxylic acids (preferably dicarboxylic acids) with polyols (preferably diols). Starting materials for such hydroxyl-containing polyesters are known to those skilled in the art. Suitable dicarboxylic acids include succinic acid, glutaric acid, adipic acid, sebacic acid, phthalic acid, their isomers, and hydrogenated products, as well as their esterifiable and transesterifiable derivatives, such as anhydrides and dialkyl esters. Suitable polyols are the alcohols listed above, preferably ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, cyclohexanedimethanol, and polyglycols of the ethylene glycol and propylene glycol types.

In addition, suitable reactive viscosity reducers are 1,4-divinylbenzene, triallyl cyanurate, and the acrylate of tricyclodecenol of the following formula: , which is also known as dihydrodicyclopentadienyl acrylate, and allyl esters of acrylic acid, methacrylic acid, and cyanoacrylate.

With regard to the reactive viscosity reducers mentioned in the examples, in particular and in view of the preferred compositions described above, those containing photopolymerizable groups are used.

This group includes, for example, diols and polyols, such as ethylene glycol, propylene glycol and their more highly condensed representatives (e.g., diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, etc.), butanediol, pentanediol, hexanediol, neopentyl glycol, cyclohexanedimethanol, glycerol, trihydroxymethylpropane, butanetriol, trihydroxymethylethane, pentaerythritol, di(trihydroxymethylpropane), dipentaerythritol, sorbitol, mannitol and the corresponding alkoxylated alcohols, in particular ethoxylated and propoxylated alcohols.

This group further includes, for example, alkoxylated phenolic compounds, such as ethoxylated bisphenols and propoxylated bisphenols.

Such reactive detackifiers may additionally be, for example, epoxides or urethane (meth)acrylates.

Epoxide (meth)acrylates are, for example, those obtainable by reaction of epoxides or polyglycidyl ethers or diglycidyl ethers, such as bisphenol A diglycidyl ether, with (meth)acrylic acid, as is known to those skilled in the art.

Specifically, urethane (meth)acrylates are the products of the reaction of hydroxyalkyl (meth)acrylates with polyisocyanates or diisocyanates (also known to those skilled in the art).

Such epoxides and urethane (meth)acrylates are included in the compounds listed above as "mixed forms".

If reactive deviscosifiers are used, their amount and properties must be adapted to the respective conditions in such a way that, on the one hand, the desired effect is achieved (e.g., the desired color of the composition according to the invention), but on the other hand, the phase behavior of the liquid crystal composition is not excessively impaired. For example, low-crosslinked (highly crosslinked) liquid crystal compositions can be prepared using corresponding reactive deviscosifiers that have a relatively low (high) number of reactive units per molecule.

The group of diluents includes, for example: C1-C4 alcohols, such as methanol, ethanol, n-propanol, isopropanol, butanol, isobutanol, dibutanol; and specifically C5-C12 alcohols, n-pentanol, n-hexanol, n-heptanol, n-octanol, n-nonanol, n-decanol, n-undecanol, and n-dodecanol, and their isomers; diols, such as 1,2-ethanediol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butanediol, 2,3-butanediol, 1,4-butanediol, diethylene glycol, triethylene glycol, and dipropylene glycol and tripropylene glycol; ethers, such as methyl tert-butyl ether, 1,2-ethanediol monomethyl ether, and Dimethyl ether, 1,2-ethylene glycol monoethyl ether and diethyl ether, 3-methoxypropanol, 3-isopropoxypropanol, tetrahydrofuran, and dioxane; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and diacetone alcohol (4-hydroxy-4-methyl-2-pentanone); C1-C5 alkyl esters such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, and amyl acetate; aliphatic and aromatic hydrocarbons such as pentane, hexane, heptane, octane, isooctane, petroleum ether, toluene, xylene, ethylbenzene, tetrahydronaphthalene, decahydronaphthalene, dimethylnaphthalene, and white spirit; Shellsol® and Solvesso® mineral oils such as gasoline, kerosene, diesel, and heating oil; and natural oils such as olive oil, soybean oil, rapeseed oil, linseed oil, and sunflower oil.

It is of course also possible to use mixtures of these diluents in the compositions according to the invention.

These diluents can also be mixed with water as long as there is at least partial miscibility. Examples of suitable diluents here are C1-C4 alcohols, such as methanol, ethanol, n-propanol, isopropanol, butanol, isobutanol and dibutanol; diols, such as 1,2-ethanediol, 1,2-propylene glycol and 1,3-propylene glycol, 1,2-butanediol, 2,3-butanediol and 1,4-butanediol, diethylene glycol and triethylene glycol, as well as dipropylene glycol and tripropylene glycol; ethers, such as tetrahydrofuran and dioxane; ketones, such as acetone, methyl ethyl ketone and diacetone alcohol (4-hydroxy-4-methyl-2-pentanone); and C1-C4 alkyl esters, such as methyl acetate, ethyl acetate, propyl acetate and butyl acetate.

The diluent is optionally used in a proportion of about 0 wt% to 10.0 wt%, preferably about 0 wt% to 5.0 wt%, based on the total weight of the polymerizable LC material.

Defoamers and degassing agents (c1)), lubricants and flow aids (c2)), heat curing aids or radiation curing aids (c3)), substrate wetting aids (c4)), wetting aids and dispersing aids (c5)), hydrophobic agents (c6)), adhesion promoters (c7)), and agents for promoting anti-scratch properties (c8)) cannot be strictly defined as one another in terms of their effects.

For example, lubricants and flow aids often also function as defoamers and/or deaerators and/or as agents for improving scratch resistance. Radiation curing aids can also function as lubricants, flow aids, deaerators, and/or substrate wetting agents. In individual cases, some of these agents can also fulfill the function of adhesion promoters (c8).

Corresponding to the above situation, a certain additive can be classified into the multiple groups c1) to c8) described below.

The defoaming agents in group c1) include silicone-free polymers and silicone-containing polymers. Silicon-containing polymers are, for example, unmodified or modified polydialkylsiloxanes, or branched chain copolymers, comb copolymers, or block copolymers comprising polydialkylsiloxanes and polyether units, the latter being obtainable from ethylene oxide or propylene oxide.

Degassing agents in group c1) include, for example, organic polymers such as polyethers and polyacrylates, dialkylpolysiloxanes (particularly dimethylpolysiloxanes); organically modified polysiloxanes such as aralkyl-modified polysiloxanes and fluoropolysiloxanes.

The action of defoamers is essentially based on preventing the formation of foam or destroying already formed foam. Defoamers essentially work by promoting the coalescence of finely divided gases or bubbles to produce larger bubbles in the medium to be deaerated (e.g., the composition according to the invention) and thus accelerating the escape of the gas (air). Since defoamers can also frequently be used as deaerators, and vice versa, these additives are included together under group c1).

Such additives are commercially available, for example, from Tego, such as TEGO® Foamex 800, TEGO® Foamex 805, TEGO® Foamex 810, TEGO® Foamex 815, TEGO® Foamex 825, TEGO® Foamex 835, TEGO® Foamex 840, TEGO® Foamex 842, TEGO® Foamex 1435, TEGO® Foamex 1488, TEGO® Foamex 1495, TEGO® Foamex 3062, TEGO® Foamex 7447, TEGO® Foamex 8020, Tego® Foamex N, TEGO® Foamex K 3, TEGO® Antifoam 2-18, TEGO® Antifoam 2-18, TEGO® Antifoam 2-57, TEGO® Antifoam 2-80、TEGO® Antifoam 2-82, TEGO® Antifoam 2-89, TEGO® Antifoam 2-92, TEGO® Antifoam 14, TEGO® Antifoam 28, TEGO® Antifoam 81, TEGO® Antifoam D 90, TEGO® Antifoam 93, TEGO® Antifoam 200, TEGO® Antifoam 201, TEGO® Antifoam 202. TEGO® Antifoam 793, TEGO® Antifoam 1488, TEGO® Antifoam 3062, TEGOPREN® 5803, TEGOPREN® 5852, TEGOPREN® 5863, TEGOPREN® 7008, TEGO® Antifoam 1-60, TEGO® Antifoam 1-62, TEGO® Antifoam 1-85, TEGO® Antifoam 2-67, TEGO® Antifoam WM 20, TEGO® Antifoam 50, TEGO® Antifoam 105, TEGO® Antifoam 730, TEGO® Antifoam MR 1015, TEGO® Antifoam MR 1016, TEGO® Antifoam 1435, TEGO® Antifoam N, TEGO® Antifoam KS 6, TEGO® Antifoam KS 10. TEGO® Antifoam KS 53, TEGO® Antifoam KS 95, TEGO® Antifoam KS 100, TEGO® Antifoam KE 600, TEGO® Antifoam KS 911, TEGO® Antifoam MR 1000, TEGO® Antifoam KS 1100, Tego® Airex 900, Tego® Airex 910, Tego® Airex 931, Tego® Airex 935, Tego® Airex 936, Tego® Airex 960, Tego® Airex 970, Tego® Airex 980 and Tego® Airex 985, and are commercially available from BYK, such as BYK®-011, BYK®-019, BYK®-020, BYK®-021, BYK®-022, BYK®-023, BYK®-024, BYK®-025, BYK®-027, BYK®-031, BYK®-032, BYK®-033, BYK®-034, BYK®- 035, BYK®-036, BYK®-037, BYK®-045, BYK®-051, BYK®-052, BYK®-053, BYK®-055, B YK®-057, BYK®-065, BYK®-066, BYK®-070, BYK®-080, BYK®-088, BYK®-141 and BYK®-A 530.

The auxiliary agents from group c1) are optionally used in a proportion of about 0% to 3.0% by weight, preferably about 0% to 2.0% by weight, based on the total weight of the polymerizable LC material.

In group c2), lubricants and flow aids typically include silicone-free polymers and silicone-containing polymers such as polyacrylates or, as modified, low-molecular-weight polydialkylsiloxanes. These modifications involve the replacement of some alkyl groups with a wide variety of organic groups, such as polyethers, polyesters, or even long-chain (fluorinated) alkyl groups, with the former being the most commonly used.

The polyether groups in the corresponding modified polysiloxanes are typically constructed from ethylene oxide and/or propylene oxide units. Generally speaking, the higher the proportion of these ethylene oxide units in the modified polysiloxane, the more hydrophilic the resulting product.

Such additives are commercially available, for example, from Tego, such as TEGO® Glide 100, TEGO® Glide ZG 400, TEGO® Glide 406, TEGO® Glide 410, TEGO® Glide 411, TEGO® Glide 415, TEGO® Glide 420, TEGO® Glide 435, TEGO® Glide 440, TEGO® Glide 450, TEGO® Glide A 115, TEGO® Glide B 1484 (which can also be used as a defoamer and deaerator), TEGO® Flow ATF, TEGO® Flow 300, TEGO® Flow 460, TEGO® Flow 425 and TEGO® Flow ZFS 460. Suitable radiation-curable lubricants and flow aids (which can also be used to improve scratch resistance) are the products TEGO® Rad 2100, TEGO® Rad 2200, TEGO® Rad 2500, TEGO® Rad 2600 and TEGO® Rad 2700, also available from TEGO.

Such additives are also commercially available from BYK, for example, BYK®-300, BYK®-306, BYK®-307, BYK®-310, BYK®-320, BYK®-333, BYK®-341, Byk® 354, Byk® 361, Byk® 361N, BYK® 388.

Such additives are also available from 3M, for example, as FC4430®.

Such adjuvants are also available commercially, for example, from Cytonix, such as FluorN® 561 or FluorN® 562.

Such additives are also commercially available, for example, from Merck KGaA as Tivida® FL 2300 and Tivida® FL 2500.

The auxiliary agents from group c2) are optionally used in a proportion of about 0% to 3.0% by weight, preferably about 0% to 2.0% by weight, based on the total weight of the polymerizable LC material.

In group c3), radiation-curing additives include, in particular, polysiloxanes having terminal double bonds, such as acrylic groups. These additives can be crosslinked actinically or, for example, by electron beam irradiation. These additives often combine several properties. In the uncrosslinked state, they can act as defoamers, degassing agents, lubricants, flow aids, and/or substrate wetting agents. In the crosslinked state, they can, in particular, increase the scratch resistance of coatings or films produced using the compositions according to the invention. For example, the precise improvement of the gloss properties of such coatings or films is believed to be essentially due to the action of additives such as defoamers, deaerators and/or lubricants and flow aids (in the uncrosslinked state).

Examples of suitable radiation curing aids are the products TEGO® Rad 2100, TEGO® Rad 2200, TEGO® Rad 2500, TEGO® Rad 2600 and TEGO® Rad 2700 available from TEGO, and the product BYK®-371 available from BYK.

The heat-curing auxiliaries in group c3) contain, for example, primary OH groups which are capable of reacting with, for example, isocyanate groups of the binding agent.

Examples of thermal curing aids that can be used are the products BYK®-370, BYK®-373 and BYK®-375 available from BYK.

The auxiliary agents from group c3) are optionally used in a proportion of about 0% to 5.0% by weight, preferably about 0% to 3.0% by weight, based on the total weight of the polymerizable LC material.

The substrate wetting additives of group c4) are used in particular to increase the wettability of substrates printed or coated, for example, with printing inks or coating compositions (e.g., compositions according to the present invention). The generally accompanying improvement in the lubrication and flow behavior of such printing inks or coating compositions has an impact on the appearance of the processed (e.g., cross-linked) print or coating.

A wide variety of such additives is commercially available, for example, from Tego, such as TEGO® Wet KL 245, TEGO® Wet 250, TEGO® Wet 260 and TEGO® Wet ZFS 453, and from BYK, such as BYK®-306, BYK®-307, BYK®-310, BYK®-333, BYK®-344, BYK®-345, BYK®-346 and Byk®-348.

The auxiliary agent in group c4) is optionally used in a proportion of about 0 wt % to 3.0 wt %, preferably about 0 wt % to 1.5 wt %, based on the total weight of the liquid crystal composition.

In particular, the wetting and dispersing aids of group c5) serve to prevent overflow and flotation of the pigments as well as sedimentation and are therefore, if desired, suitable in particular for pigmented compositions.

These additives stabilize the pigment dispersion essentially by electrostatic repulsion and/or steric hindrance of the pigment particles containing these additives, wherein in the latter case the interaction of the additive with the surrounding medium (e.g., binder) plays a major role.

Since the use of such wetting and dispersing additives is customary, for example in the technical field of printing inks and coatings, the selection of suitable additives of this type, if used, generally does not present any difficulties to those skilled in the art.

Such wetting and dispersing aids are commercially available from Tego, for example, as TEGO® Dispers 610, TEGO® Dispers 610 S, TEGO® Dispers 630, TEGO® Dispers 700, TEGO® Dispers 705, TEGO® Dispers 710, TEGO® Dispers 720 W, TEGO® Dispers 725 W, TEGO® Dispers 730 W, TEGO® Dispers 735 W and TEGO® Dispers 740 W, and commercially available from BYK, such as Disperbyk®, Disperbyk®-107, Disperbyk®-108, Disperbyk®-110, Disperbyk®-111, Disperbyk®-115, D isperbyk®-130, Disperbyk®-160, Disperbyk®-161, Disperbyk®-162, Disperbyk®-163, Disperbyk®-164, Disperbyk® -165, Disperbyk®-166, Disperbyk®-167, Disperbyk®-170, Disperbyk®-174, Disperbyk®-180, Disperbyk®-181, Dis perbyk®-182, Disperbyk®-183, Disperbyk®-184, Disperbyk®-185, Disperbyk®-190, Anti-Terra®-U, Anti-Terra®-U 80. Anti-Terra®-P, Anti-Terra®-203, Anti-Terra®-204, Anti-Terra®-206, BYK®-151, BYK®-154, BYK®-155, BYK®-P 104 S, BYK®-P 105, Lactimon®, Lactimon®-WS and Bykumen®.

The amount of the auxiliary agent from group c5) used is based on the average molecular weight of the auxiliary agent. In any case, preliminary experiments are therefore advisable, but can only be carried out by those skilled in the art.

The hydrophobic agents in group c6) can be used to impart water-repellent properties to printed materials or coatings produced, for example, using the compositions according to the invention. This prevents or at least significantly suppresses swelling due to water absorption and thus prevents, for example, changes in the optical properties of such printed materials or coatings. Furthermore, when the compositions are used, for example, as printing inks in lithographic printing, water absorption can be prevented or at least significantly reduced.

Such hydrophobic agents are, for example, commercially available from Tego as Tego® Phobe WF, Tego® Phobe 1000, Tego® Phobe 1000 S, Tego® Phobe 1010, Tego® Phobe 1030, Tego® Phobe 1010, Tego® Phobe 1010, Tego® Phobe 1030, Tego® Phobe 1040, Tego® Phobe 1050, Tego® Phobe 1200, Tego® Phobe 1300, Tego® Phobe 1310 and Tego® Phobe 1400.

The auxiliary agents from group c6) are optionally used in a proportion of about 0% to 5.0% by weight, preferably about 0% to 3.0% by weight, based on the total weight of the polymerizable LC material.

Other adhesion promoters from group c7) are used to improve the adhesion of two contacting interfaces. It is immediately apparent that essentially the only effective adhesion promoter fraction is that which is located at one or the other or both interfaces. If, for example, a liquid or pasty printing ink, coating composition, or paint is to be applied to a solid substrate, this generally means that the adhesion promoter must be added directly to the solid substrate or that the substrate must be pretreated (also known as primed) with the adhesion promoter, i.e., provided with modified chemical and/or physical surface properties.

If the substrate has been primed with a primer beforehand, this means that the interfaces that come into contact are those of the primer on the one hand and the printing ink or coating composition or paint on the other. In this case, the adhesion properties not only between the substrate and the primer, but also between the substrate and the printing ink or coating composition or paint, play a role in the adhesion of the entire multi-layer structure on the substrate.

Mention may also be made of adhesion promoters in a broader sense, which are already listed under group c4) as substrate wetting agents, but these generally do not have the same adhesion promoting capabilities.

The diversity of adhesion promoter systems is not surprising given the wide variety of physical and chemical properties of substrates and of the printing inks, coating compositions and coatings that are intended, for example, to be used for printing or coating on these substrates.

Silane-based adhesion promoters include, for example, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, N-aminoethyl-3-aminopropyltrimethoxysilane, N-aminoethyl-3-aminopropylmethyldimethoxysilane, N-methyl-3-aminopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-glycidyloxypropyltrimethoxysilane, 3-butylpropyltrimethoxysilane, 3-chloropropyltrimethoxysilane, and vinyltrimethoxysilane. These and other silanes are commercially available, for example, from Hüls under the trade name DYNASILAN®.

Corresponding technical information from the manufacturers of such additives should usually be used, or this information can be easily obtained by a person skilled in the art through corresponding preliminary experiments.

However, if these additives are added as auxiliary agents from group c7) to the polymerizable LC material according to the present invention, their proportions, based on the total weight of the polymerizable LC material, may correspond to approximately 0% to 5.0% by weight. These concentrations are provided as a guide only, as the amount and identity of the additives will depend on the properties of the substrate and the printed/coated composition in each individual case. Corresponding technical information is generally available from the manufacturers of these additives or can be easily determined by those skilled in the art through preliminary experiments.

Additives from group c8) for improving scratch resistance include, for example, the above-mentioned products TEGO® Rad 2100, TEGO® Rad 2200, TEGO® Rad 2500, TEGO® Rad 2600 and TEGO® Rad 2700, which are commercially available from Tego.

For these additives, the amounts given for group c3) are also applicable, that is, these additives are used in a proportion of about 0 wt % to 5.0 wt %, preferably about 0 wt % to 3.0 wt %, based on the weight of the liquid crystal composition.

Examples of other light stabilizers, heat stabilizers and/or oxidation stabilizers that may be mentioned are: Alkylated monophenols, such as 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol; nonylphenols with linear or branched side chains, such as 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadecan-1'-yl)phenol, 2,4-dimethyl-6-(1'-methyltridecan-1'-yl)phenol and mixtures of these compounds; alkylthiomethylphenols, such as 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol and 2,6-didodecylthiomethyl-4-nonylphenol, Hydroquinone and alkylated hydroquinones, such as 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-pentylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, and bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate. Tocopherols, such as α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol and mixtures of these compounds; and tocopherol derivatives, such as tocopheryl acetate, tocopheryl succinate, tocopheryl nicotinate and polyoxyethylene tocopheryl succinate ("tocofersolate"), Hydroxylated diphenyl sulfides, such as 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-dipentylphenol) and 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl) disulfide, Alkylene bisphenols, such as 2,2′-methylenebis(6-tert-butyl-4-methylphenol), 2,2′-methylenebis(6-tert-butyl-4-ethylphenol), 2,2′-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol], 2,2′-methylenebis(4-methyl-6-cyclohexylphenol), 2,2′-methylenebis(6-nonyl-4-methylphenol), 2,2′-methylenebis(4,6-di-tert-butylphenol), 2,2-ethylenebis(4 ,6-di- and tri-butylphenol), 2,2′-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2′-methylenebis[6-(α-methylbenzyl)-4-nonylphenol], 2,2′-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4′-methylenebis(2,6-di- and tri-butylphenol), 4,4′-methylenebis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert-butyl-4-hydroxy-2- methylphenyl)butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecyl-butylbutane, ethylene glycol bis[3,3-bis(3′-tert-butyl-4′-hydroxyphenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methylphenyl)dicyclopentadiene, Bis[2-(3′-tert-butyl-2′-hydroxy-5′-methylbenzyl)-6-tert-butyl-4-methylphenyl] terephthalate, 1,1-bis(3,5-dimethyl-2-hydroxyphenyl)butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 2,2-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecyl-butylbutane, and 1,1,5,5-tetrakis(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane. O-Benzyl, N-Benzyl and S-Benzyl compounds, such as 3,5,3′,5′-tetrabutyl-4,4′-dihydroxybenzhydryl ether, 4-hydroxy-3,5-dimethylbenzyl alkyl octadecyl acetate, 4-hydroxy-3,5-di-tert-butylbenzyl alkyl tridecyl acetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide and isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl alkyl acetate. Aromatic hydroxybenzyl compounds, such as 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene and 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol, Trihydroxide compounds, such as 2,4-bis(octylbutyl)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-trihydroxide, 2-octylbutyl-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-trihydroxide, 2-octylbutyl-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-trihydroxide, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-trisoxide, 1,3,5-tris(3,5-di-tert-butyl- tributyl-4-hydroxyphenylpropionyl) hexahydro-1,3,5-tris(3,5-di- and tri-butyl-4-hydroxyphenylpropionyl) isocyanurate, 1,3,5-tris(3,5-di- and tri-butyl-4-hydroxyphenylpropionyl) isocyanurate, and 1,3,5-tris(2-hydroxyethyl) isocyanurate. Benzylphosphonates, such as dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, distearyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, and distearyl 5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate; Aminophenols, such as 4-hydroxylaurylanilide, 4-hydroxystearylanilide, and octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate; Propionates and acetates, for example, propionates and acetates of monohydric or polyhydric alcohols such as methanol, ethanol, n-octanol, isooctanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propylene glycol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trihydroxymethylpropane and 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]-octane, Amine-based propionamides, such as N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexanediamine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine, and N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine; Ascorbic acid (vitamin C) and ascorbic acid derivatives, such as ascorbyl palmitate, ascorbyl laurate, and ascorbyl stearate, as well as ascorbyl sulfate and ascorbyl phosphate; Antioxidants based on amine compounds, such as N,N′-diisopropyl-p-phenylenediamine, N,N′-dibutyl-p-phenylenediamine, N,N′-bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N′-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N′-bis(1-methylheptyl)-p-phenylenediamine, N,N′-dicyclohexyl-p-phenylenediamine, N,N′-diphenyl-p-phenylenediamine, N,N′-bis(2-naphthyl)-p-phenylenediamine, N-isopropyl-N′-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine, N-(1-methylheptyl)-N′-phenyl-p-phenylenediamine, N -Cyclohexyl-N'-phenyl-p-phenylenediamine, 4-(p-toluidinesulfonyl)diphenylamine, N,N'-dimethyl-N,N'-di-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine, N-phenyl-2-naphthylamine, octyl-substituted diphenylamines (such as p,p'-di-tert-octyldiphenylamine), 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonylaminophenol, 4-dodecylaminophenol, 4-octadecylaminophenol, bis(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol , 2,4-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, N,N,N′,N′-tetramethyl-4,4′-diaminodiphenylmethane, 1,2-bis[(2-methylphenyl)amino]ethane, 1,2-bis(anilino)propane, (o-tolyl)biguanidine, bis[4-(1′,3′-dimethylbutyl)phenyl]amine, tertiary octyl-substituted N-phenyl-1-naphthylamine, mixture of mono- and di-alkylated tertiary butyl/tertiary octyl diphenylamine, mixture of mono- and di-alkylated nonyl diphenylamine, mixture of mono- and di-alkylated dodecyl diphenylamine, mixture of mono- and di-alkylated isopropyl/isohexyl diphenylamine , a mixture of mono- and di-alkylated tertiary butyldiphenylamine, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiol, thiophenethiophene, a mixture of mono- and di-alkylated tertiary butyl/tertiary octylthiophenethiophene, a mixture of mono- and di-alkylated tertiary octylthiophenethiophene, N-allylthiophenethiophene, N,N,N′,N′-tetraphenyl-1,4-diaminobut-2-ene, N,N-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexanediamine, bis(2,2,6,6-tetramethylpiperidin-4-yl)sebacate, 2,2,6,6-tetramethylpiperidin-4-one and 2,2,6,6-tetramethylpiperidin-4-ol, Phosphine, phosphite and phosphite diesters, such as triphenylphosphine triphenyl phosphite, diphenyl alkyl phosphite, phenyl dialkyl phosphite, tris(nonylphenyl) phosphite, tris(dodecyl) phosphite, tris(octadecyl) phosphite, distearyl neopentyl acetate diphosphite, tris(2,4-di-tert-butylphenyl) phosphite, diisodecyl neopentyl acetate diphosphite, bis(2,4-di-tert-butylphenyl) neopentyl acetate diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl) neopentyl acetate diphosphite, diisodecyl neopentyl acetate diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl) neopentyl acetate diphosphite, Phosphites, bis(2,4,6-tris(tert-butylphenyl))pentylethoxyl diphosphite, tristearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)4,4′-diphenyl diphosphite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenzo[d,g]-1,3,2-dioxophosphine, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g]-1,3,2-dioxophosphine, bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite, and bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 2-(2'-Hydroxyphenyl)benzotriazole, such as 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)-5- Chlorobenzotriazole, 2-(3'-dibutyl-5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazole, 2-(3',5'-di-tert-pentyl-2'-hydroxyphenyl)benzotriazole, 2-(3,5'-bis-(α,α-dimethylbenzyl)-2'-hydroxyphenyl)benzotriazole; 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-5'-[2-( 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]- A mixture of 2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(3'-t-butyl-2'-hydroxy-5'-(2-isooctyloxycarbonylethyl)phenylbenzotriazole, 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-ylphenol]; and a fully esterified product of 2-[3'-t-butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazole and polyethylene glycol 300. Sulfur peroxide scavengers and sulfur antioxidants, such as esters of 3,3′-thiodipropionic acid, such as the dodecyl, octadecyl, tetradecyl, and tridecyl esters, zinc salts of alkylbenzimidazole and 2-alkylbenzimidazole, dibutylzinc dithiocarbamate, dioctadecyl disulfide, and pentaerythritol tetrakis(β-dodecylalkyl)propionate; 2-Hydroxybenzophenones, such as the 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2′,4′-trihydroxy, and 2′-hydroxy-4,4′-dimethoxy derivatives; Unsubstituted and substituted benzoic acid esters, such as 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, and 2-methyl-4,6-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate. Acrylates, such as ethyl α-cyano-β,β-diphenylacrylate, isooctyl α-cyano-β,β-diphenylacrylate, methyl α-methoxycarbonylcinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate, butyl-α-cyano-β-methyl-p-methoxycinnamate, and methyl-α-methoxycarbonyl-p-methoxycinnamate; hindered amines, such as bis(2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(2,2,6,6-tetramethylpiperidin-4-yl)succinate, bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis(1,2,2,6,6-pentamethylpiperidin-4-yl)-n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, condensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexanediamine and 4-tert-octylamine condensation products of 2,6-dichloro-1,3,5-triazolidine, tris(2,2,6,6-tetramethylpiperidin-4-yl)nitrilotriacetate, tetrakis(2,2,6,6-tetramethylpiperidin-4-yl)1,2,3,4-butanetetracarboxylate, 1,1′-(1,2-ethylidene)bis(3,3,5,5-tetramethylpiperidinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-octadecyloxy-2,2,6,6-tetramethylpiperidine, bis(1,2 ,2,6,6-pentamethylpiperidin-4-yl) 2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl) malonate, 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate, N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl) ) hexanediamine and 4-oxo-2,6-dichloro-1,3,5-trioxane condensation product, 2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidin-4-yl)-1,3,5-trioxane and 1,2-bis(3-aminopropylamino)ethane condensation product, 2-chloro-4,6-bis(4-n-butylamino-1,2,2,6,6-pentamethylpiperidin-4-yl)-1,3,5-trioxane and 1,2-bis(3-aminopropylamino)ethane condensation product, 8-acetyl-3-decyl Dialkyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]-decane-2,4-dione, 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione, 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione, a mixture of 4-hexadecyloxy-2,2,6,6-tetramethylpiperidine and 4-octadecyloxy-2,2,6,6-tetramethylpiperidine, N,N′-bis(2 ,2,6,6-tetramethylpiperidin-4-yl)hexanediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-tris(II) condensation product, 1,2-bis(3-aminopropylamino)ethane and 2,4,6-trichloro-1,3,5-tris(II) condensation product, 4-butylamino-2,2,6,6-tetramethylpiperidine, N-(2,2,6,6-tetramethylpiperidin-4-yl)-n-dodecylsuccinimide, N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-n-dodecylsuccinimide , 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro[4.5]-decane, condensation products of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxo-spiro[4.5]decane and epichlorohydrin, condensation products of 4-amino-2,2,6,6-tetramethylpiperidine, tetrahydroxymethylacetylene diurea and poly(methoxypropyl-3-oxy)-[4(2,2,6,6-tetramethyl)piperidinyl]-siloxane, Oxalic acid amides, such as 4,4′-dioctyloxyoxalanilide, 2,2′-diethoxyoxalanilide, 2,2′-dioctyloxy-5,5′-di- and tertiary-butyridine, 2,2′-di(dodecyloxy)-5,5′-di- and tertiary-butyridine, 2-ethoxy-2'-ethyloxalanilide, N,N′-bis(3-dimethylaminopropyl)oxalyl Amine, 2-ethoxy-5-tert-butyl-2'-acetophenidine and its mixture with 2-ethoxy-2'-ethyl-5,4'-di-tert-butyloxalylaniline, a mixture of o-methoxy-disubstituted oxalylaniline and p-methoxy-disubstituted oxalylaniline, and a mixture of o-ethoxy-disubstituted oxalylaniline and p-ethoxy-disubstituted oxalylaniline, and 2-(2-hydroxyphenyl)-1,3,5-trisinium, such as 2,4,6-trisinium-(2-hydroxy-4-octyloxyphenyl)-1,3,5-trisinium, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-trisinium, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-trisinium, 2,4-bis(2-hydroxy-4-propoxyphenyl)-6-(2,4-dimethylphenyl)- 1,3,5-trisinium, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-trisinium, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-trisinium, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-trisinium, 2-[2-hydroxy-4-(2-hydroxy-3-butoxypropoxy)phenyl]-4, 6-bis(2,4-dimethyl)-1,3,5-trisinium, 2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-trisinium, 2-[4-(dodecyloxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-trisinium, 2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6- Bis-(2,4-dimethylphenyl)-1,3,5-trisinium, 2-(2-hydroxy-4-hexyloxyphenyl)-4,6-diphenyl-1,3,5-trisinium, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-trisinium, 2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-trisinium, and 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-trisinium.

In another preferred embodiment, the polymerizable LC material comprises one or more specific antioxidant additives, which are preferably selected from the Irganox® range, such as the antioxidants Irganox® 1076 and Irganox® 1010 commercially available from Ciba, Switzerland.

In another preferred embodiment, the polymerizable LC material comprises a combination of one or more, more preferably two or more photoinitiators, selected, for example, from the commercially available Irgacure® or Darocure® (Ciba AG) series, in particular Irgacure 127, Irgacure 184, Irgacure 369, Irgacure 651, Irgacure 817, Irgacure 907, Irgacure 1300, Irgacure, Irgacure 2022, Irgacure 2100, Irgacure 2959 or Darcure TPO, further selected from the commercially available OXE02 (Ciba AG), NCI 930, N1919T (Adeka), SPI-03 or SPI-04. (Samyang).

The overall concentration of the polymerization initiator in the polymerizable LC material is preferably 0.5 to 10%, very preferably 0.8 to 8%, and more preferably 1 to 6%.

Preferably, the polymerizable LC material comprises, in addition to one or more compounds of formula I: a) one or more direactive or polyreactive polymerizable mesogenic compounds, b) optionally one or more monoreactive polymerizable mesogenic compounds, c) optionally one or more antioxidant additives, d) optionally one or more adhesion promoters, e) optionally one or more surfactants, f) optionally one or more monoreactive, direactive or polyreactive polymerizable non-mesogenic compounds, g) optionally one or more dyes which exhibit an absorption maximum at the wavelength used to initiate photopolymerization, h) Optionally, one or more chain transfer agents, i) Optionally, one or more other stabilizers, j) Optionally, one or more lubricants and flow aids, and k) Optionally, one or more diluents, l) Optionally, a non-polymerizable nematic component.

More preferably, the polymerizable LC material comprises: a)     one or more compounds of formula I, b)     one or more, preferably two or more, direactive polymerizable mesogen compounds, if present, preferably in an amount of 10% to 90% by weight, very preferably 15% to 75% by weight, preferably selected from compounds of formula DRMa-1, c)     optionally one or more, preferably two or more, monoreactive polymerizable mesogen compounds, preferably in an amount of 10% to 95% by weight, very preferably 25% to 85%, preferably selected from compounds of formula MRM-1 and/or MRM-7, d)     optionally one or more compounds of formula ND, preferably in an amount of 0 to 50%, very preferably 0 to 40%, e)    Optionally, one or more antioxidant additives, preferably selected from unsubstituted and substituted benzoic acid esters, in particular Irganox® 1076, and if present, preferably in an amount of 0.01 to 2 wt%, particularly 0.05 to 1 wt%, f) Optionally, one or more lubricants and flow aids, preferably selected from BYK® 388, FC 4430 and/or Fluor N 562, and if present, preferably in an amount of 0.1 to 5 wt%, particularly 0.2 to 3 wt%, and g) One or more diluents are optionally used, preferably selected from n-dodecanol. If present, the amount is preferably 0.1 wt% to 5 wt%, and most preferably 0.2 wt% to 3 wt%.

The present invention further relates to a method for preparing a polymer film by: - providing a layer of a polymerizable LC material as described above and below on a substrate, - polymerizing a polymerizable component of the polymerizable LC material by photopolymerization, and - optionally removing the polymerized LC material from the substrate and/or optionally providing it on another substrate.

It is also possible to dissolve the polymerizable LC material in a suitable solvent.

In another preferred embodiment, the polymerizable LC material comprises one or more solvents, preferably selected from organic solvents. The solvent is preferably selected from ketones such as acetone, methyl ethyl ketone, methyl propyl ketone, methyl isobutyl ketone, or cyclohexanone; acetates such as methyl acetate, ethyl acetate, butyl acetate, or methyl acetylacetate; alcohols such as methanol, ethanol, or isopropanol; aromatic solvents such as toluene or xylene; alicyclic hydrocarbons such as cyclopentane or cyclohexane; hydrocarbon halides such as dichloromethane or trichloromethane; and glycols or their esters such as PGMEA (propyl glycol monomethyl ether acetate) and γ-butyrolactone. It is also possible to use binary, ternary, or higher-order mixtures of the above solvents.

In case the polymerisable LC material contains one or more solvents, the total concentration of all solids (including RMs) in the solvents is preferably from 10% to 60%.

The solution is then applied or printed onto a substrate, for example, by spin coating, printing or other known techniques, and the solvent is evaporated before polymerization. In most cases, it is appropriate to heat the mixture to assist in evaporation of the solvent.

The polymerizable LC material can be applied to the substrate by conventional coating techniques such as spin coating, rod coating, or doctor blade coating. It can also be applied to the substrate by conventional printing techniques known to experts, such as, for example, screen printing, lithographic printing, reel-to-reel printing, printer printing, gravure printing, rotogravure printing, flexographic printing, intaglio printing, pad printing, heat seal printing, inkjet printing, or printing with the aid of a stamp or printing plate.

Suitable substrate materials and substrates are known to experts and described in the literature, for example, substrates known from the optical film industry, such as glass or plastic. Particularly suitable and preferred substrates for polymerization are polyesters, such as polyethylene terephthalate (PET) or polyethylene naphthalate (PEN), polyvinyl alcohol (PVA), polycarbonate (PC), triacetyl cellulose (TAC) or cycloolefin polymers (COP), or generally known color filter materials, in particular triacetyl cellulose (TAC), cycloolefin polymers (COP) or generally known color filter materials.

The polymerizable LC material preferably exhibits uniform alignment throughout the entire layer. Preferably, the polymerizable LC material exhibits uniform planar alignment or uniform homeotropic alignment.

The Friedel-Creagh-Kmetz law can be used to predict whether the mixture will adopt planar or homeotropic alignment by comparing the surface energies of the RM layer and the substrate: if γ _RM > γ _s , the reactive mesogen compound will exhibit homeotropic alignment; if γ _RM < γ _s , the reactive mesogen compound will exhibit homogeneous alignment.

When the surface energy of the substrate is relatively low, the intermolecular forces between the reactive mesogens are stronger than the forces across the RM-substrate interface. Therefore, the reactive mesogens align perpendicular to the substrate (homeotropic alignment) to maximize the intermolecular forces.

Homeotropic alignment can also be achieved by using amphiphilic materials; these can be added directly to the polymerizable LC material, or the substrate can be treated with these materials in the form of a homeotropic alignment layer. The polar head of the amphiphilic material is chemically bonded to the substrate, with the carbon tail oriented perpendicular to the substrate. Intermolecular interactions between the amphiphilic material and the RM promote homeotropic alignment. Commonly used amphiphilic surfactants are described above.

Another method for promoting vertical alignment is to apply a corona discharge treatment to the plastic substrate, thereby generating alcohol or ketone functional groups on the substrate surface. These polar groups can interact with polar groups present in RMs or surfactants to promote vertical alignment.

When the surface tension of the substrate is greater than that of the RM, the forces across the interface dominate. If the reactive mesogens are aligned parallel to the substrate, the interfacial energy is minimized, allowing the long axis of the RM to interact with the substrate. One way to promote planar alignment is by coating the substrate with a polyimide layer and then rubbing the alignment layer with velvet fabric.

Other suitable planar alignment layers are known in the art, such as, for example, rubbed polyimides or alignment layers prepared by photoalignment, as described in US 5,602,661, US 5,389,698 or US 6,717,644.

In general, alignment techniques are reviewed, for example, in I. Sage, "Thermotropic Liquid Crystals," edited by G. W. Gray, John Wiley & Sons, 1987, pp. 75-77; and in T. Uchida and H. Seki, "Liquid Crystals - Applications and Uses Vol. 3," edited by B. Bahadur, World Scientific Publishing, Singapore 1992, pp. 1-63. Another review of alignment materials and techniques is provided by J. Cognard, Mol. Cryst. Liq. Cryst. 78, Supplement 1 (1981), pp. 1-77.

To produce the polymer film according to the invention, the polymerisable compounds in the polymerisable LC material are polymerised or cross-linked (in the case of a compound containing two or more polymerisable groups) by in situ photopolymerisation.

Photopolymerization can be carried out in one step. It is also possible to photopolymerize or crosslink the compounds that did not react in the first step in a second step ("final curing").

In a preferred preparation method, a polymerisable LC material is coated onto a substrate and subsequently photopolymerised, for example by exposure to actinic radiation, as described in, for example, WO 01/20394, GB 2,315,072 or WO 98/04651.

Photopolymerization of the LC material is preferably achieved by exposing it to actinic radiation. Actinic radiation means irradiation with light such as UV light, IR light, or visible light, irradiation with X-rays or gamma rays, or irradiation with high-energy particles such as ions or electrons. Preferably, polymerization is carried out by irradiation with light, in particular with UV light. As a light source for actinic radiation, for example, a single UV lamp or a system of UV lamps can be used. When using high-power lamps, the curing time can be reduced. Another possible light source for irradiation is a laser, such as, for example, a UV laser, an IR laser, or a visible laser.

Curing time depends, among other things, on the reactivity of the polymerizable LC material, the thickness of the coated layer, the type of polymerization initiator, and the power of the UV lamp. Curing times are preferably ≤ 5 minutes, very preferably ≤ 3 minutes, and optimally ≤ 1 minute. For high-volume production, a short curing time of ≤ 30 seconds is preferred.

Suitable UV radiation power is preferably in the range of 5 to 200 mWcm-2, more preferably in the range of 50 to 175 mWcm ^-2 , and most preferably in the range of 100 to 150 mWcm ^-2 .

Depending on the applied UV radiation and varying over time, the suitable UV dose is preferably in the range of 25 to 7200 mJcm ^-2 , more preferably in the range of 500 to 7200 mJcm ^-2 , and most preferably in the range of 3000 to 7200 mJcm ^-2 .

Photopolymerization is preferably carried out in an inert gas atmosphere, preferably in a heated nitrogen atmosphere, but polymerization in air is also possible.

The photopolymerization is preferably carried out at a temperature of 1 to 70°C, more preferably 5 to 50°C, even more preferably 15 to 30°C.

The polymerized LC film according to the present invention has good adhesion to plastic substrates, in particular to TAC, COP, and color filters. Therefore, it can be used as an adhesive or base coating for subsequent LC layers that would otherwise not adhere well to the substrate.

The preferred thickness of the polymerized LC film according to the present invention is determined by the desired optical properties of the film or final product. For example, if the polymerized LC film does not primarily serve as an optical layer, but rather serves as an adhesive layer, alignment layer, or protective layer, its thickness is preferably no more than 1 μm, particularly no more than 0.5 μm, and most preferably no more than 0.2 μm.

For example, the polymer films of the present invention with uniform homeotropic or planar alignment can be used as retardation films or compensation films in LCDs, for example, to improve contrast and brightness at wide viewing angles and reduce chromaticity. They can be used outside of a switchable liquid crystal cell in an LCD, or between substrates (typically glass substrates) to form a switchable liquid crystal cell containing a switchable liquid crystal medium (in cell applications).

For optical applications of polymer films, the thickness is preferably 0.5 to 10 μm, most preferably 0.5 to 5 μm, and particularly 0.5 to 3 μm.

The optical delay (δ(λ)) of the polymer film as a function of the wavelength (λ) of the incident light beam is given by the following equation (7): δ(λ)=(2πΔn∙d)/λ                                                      (7) where (Δn) is the birefringence of the film, (d) is the thickness of the film and λ is the wavelength of the incident light beam.

According to Snellius's law, the birefringence as a function of the direction of the incident light beam is defined as: Δn = sinΘ/sinΨ (8) where sinΘ is the angle of incidence or tilt of the optical axis in the film, and sinΨ is the corresponding reflection angle.

Based on these laws, the birefringence and, accordingly, the optical retardation depend on the film thickness and the tilt angle of the optical axis in the film (see Berek's compensator). Therefore, skilled experts recognize that different optical retardations or different birefringence can be induced by adjusting the orientation of the liquid crystal molecules in the polymer film.

The birefringence (Δn) of the polymer film according to the present invention is preferably in the range of 0.01 to 0.30, more preferably in the range of 0.01 to 0.25, and even more preferably in the range of 0.01 to 0.16.

The optical retardation as a function of the thickness of the polymer film according to the invention is less than 200 nm, preferably less than 180 nm and even better less than 150 nm.

The polymer films of the present invention can also be used as alignment films for other liquid crystal or liquid crystal materials. For example, they can be used in LCDs to induce or modify the alignment of switchable liquid crystal media, or to align subsequent layers of polymerizable LC materials coated thereon. In this way, stacks of polymerized LC films can be prepared.

In general, the polymerized LC films and polymerizable LC materials according to the present invention are suitable for use in optical components such as polarizers, compensators, alignment layers, circular polarizers or color filters in liquid crystal displays or projection systems, decorative images, for preparing liquid crystals or effect pigments, and are particularly suitable for use in reflective films with spatially varying reflective colors, such as multicolor images for decoration, information storage, or security purposes (e.g., unforgeable documents such as ID cards, credit cards, banknotes, etc.).

The polymerized LC film according to the invention can be used in transmissive or reflective displays. They can be used in conventional OLED displays or LCDs, in particular LCDs in DAP (alignment phase change) or VA (vertical alignment) mode, such as, for example, ECB (electrically controlled birefringence), CSH (color super vertical), VAN or VAC (vertical alignment nematic or cholesteric) displays, MVA (multi-domain vertical alignment) or PVA (patterned vertical alignment) displays; in bend mode displays or hybrid type displays, such as, for example, OCB (optically compensated bend cell or optically compensated birefringence), R-OCB (reflective OCB), HAN (hybrid alignment nematic) or pi cell (π cell) displays; and in TN (twisted nematic), HTN (highly twisted nematic) or STN displays. Displays using TFT-LCD (Super Twisted Nematic) mode; displays using AMD-TN (Active Matrix Driven TN) mode; or displays using IPS (In-Plane Switching) mode (also known as "Super TFT" displays). Particularly preferred are VA, MVA, PVA, OCB, and pi cell displays.

The polymerizable LC materials and polymer films according to the present invention are particularly suitable for use in 3D displays, as described in EP 0 829 744, EP 0 887 666 A2, EP 0 887 692, US Pat. No. 6,046,849, US Pat. No. 6,437,915, and in "Proceedings of the SID ^20th International Display Research Conference, 2000," page 280. A 3D display of this type comprising the polymer film according to the present invention is another object of the present invention.

The present invention is described above and below with specific reference to preferred embodiments thereof. It should be understood that various changes and modifications can be made therein without departing from the spirit and scope of the present invention.

Many of the compounds mentioned above and below, or mixtures thereof, are commercially available. All of these compounds are known or can be prepared by methods known per se, specifically under reaction conditions known and suitable for these reactions, as described in the literature (e.g., in standard works such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart). Variants known per se but not mentioned here may also be used.

It should be understood that variations can be made to the embodiments described above and still fall within the scope of the present invention. Unless otherwise stated, alternative features serving the same, equivalent, or similar purpose may be substituted for each feature disclosed herein. Therefore, unless otherwise stated, each feature disclosed is merely one example of a generic series of equivalent or similar features.

Except for at least some mutually exclusive combinations of such features and/or steps, all features disclosed in this specification may be combined in any combination. In particular, preferred features of the present invention apply to all aspects of the present invention and may be used in any combination. Similarly, features described in non-essential combinations may be used separately (not in combination).

It will be appreciated that many of the features described above, particularly the preferred embodiments, are inventive in their own right and not merely as part of embodiments of the present invention. Independent protection may be sought for these features in addition to or in lieu of any presently claimed invention.

The present invention will now be described in more detail with reference to the following examples, which are merely illustrative and do not limit the scope of the present invention.

Example General Procedure : The mixture was dissolved in toluene/cyclohexanone (7/3) to 30% solids. The solution was bar-coated onto a TAC substrate coated with a photoalignment layer (HSPA-156, Nissan) using a Mayer Bar No. 7. The film was annealed at 60°C for 120 seconds and cured in an N2 atmosphere using a Fusion conveyor and H-shaped bulb (95% power, 10 m/min, approximately 400 mJ/ ^cm2 , UV B).

The film layers were pressed onto the pressure-sensitive adhesive leaving the surface open so that the entire film stack was glass/polymer film/pressure-sensitive adhesive and subjected to durability testing.

To measure the difference in retardation and dispersion of the cured film based on UV stress, an Axoscan ellipsoidal polarimeter was used to measure initial retardation and dispersion. The film was then stressed at 63°C for 202 hours using a Suntest XLS+ (430 W/ ^m² ). After testing, the retardation profile and dispersion were measured again. Durability was quantified by the difference in R _in and/or dispersion (R ₄₅₀ / ₅₅₀ ) before and after UV testing.

Example 1 The following mixture M1 was prepared: Compound %-w/w BYK-310 0.850 Irganox 1076 0.120 29.095 16,000 19.890 29.500 SPI-03 0.500 Tinuvin 970 2.000 LA-F70 1.000 NCI-930 1.000 0.045

Compounds SPI-03 (Samyng Corp.), Tinuvin 970 (BASF), LA-F70 (Adeka), NCI-930 (Adeka), BYK-310 (BYK), and Irganox 1076 (BASF) are commercially available from the designated suppliers.

M1 was dissolved, applied and cured as described above, and the dispersion was determined before and after the sunlight test and quantified as the difference ΔR _(450/550) (in [%). Main mixture ΔR _(450/550) [%] M1 0.8

Comparative Example 1 The following mixture CM1 was prepared: Compound %-w/w BYK-310 0.850 Irganox 1076 0.120 29.095 16,000 19.890 29.500 SPI-03 0.500 Tinuvin 970 2.000 LA-F70 1.000 NCI-930 1.000 Tinuvin 770 0.045 Compounds SPI-03 (Samyang Corp.), Tinuvin 970 (BASF), LA-F70 (Adeka), NCI-930 (Adeka), BYK-310 (BYK), Tinuvin 770 (BASF), and Irganox 1076 (BASF) are commercially available from the designated suppliers.

CM1 was dissolved, coated and cured as described above, and the dispersion was measured before and after the sunlight test and quantified as the difference ΔR _(450/550) (in [%). Main mixture ΔR _(450/550) [%] CM1 2.0

As can be seen from a comparison between Example 1 and Comparative Example 1, the durability of the optical dispersion is significantly improved by using the compound of Formula I in the reactive mesogen mixture.

Claims (13)

A polymerizable LC material comprising one or more bireactive or polyreactive mesogen compounds and one or more compounds of formula I, wherein R ¹¹ at each occurrence independently represents H, F, a linear or branched alkyl chain having 1 to 20 C atoms, wherein one -CH ₂ - group or, if present, a plurality of -CH ₂ - groups may be replaced by -O- or -C(=O)-, but two adjacent -CH ₂ - groups may not be replaced by -O-, and one or, if present, a plurality of -CH 2 - groups may be replaced by -CH=CH- or -C≡C-, and wherein one or a plurality of H atoms may be replaced by F, OR ¹³ , N(R ¹³ )(R ¹⁴ ) or R 15, and R ¹² at each occurrence independently represents a linear or branched alkyl chain having 1 to 20 C atoms, wherein one -CH ₂ - group or a plurality of -CH 2 - groups may be replaced by -O- or -C(=O)-, but ^two adjacent -CH ₂ - groups may not be replaced by -O-, and one or, if present, a plurality of -CH ₂ - groups may be replaced by -CH=CH- or -C≡C-. -group may be replaced by -O- or -C(=O)-, but two adjacent -CH ₂ -groups may not be replaced by -O-; a alkyl group containing a cycloalkyl or alkylcycloalkyl unit, wherein one or more -CH _{2 -groups} may be replaced by -O- or -C(=O)-, but two adjacent -CH ₂ -groups may not be replaced by -O-, and wherein one or more H atoms may be replaced by OR ¹³ , N(R ¹³ )(R ¹⁴ ) or R ¹⁵ ; or an aromatic or heteroaromatic alkyl group, wherein one or more H atoms may be replaced by F, OR ¹³ , N(R ¹³ )(R ¹⁴ ) or R ¹⁵ , R R ¹³ represents, at each occurrence, a linear or branched alkyl or acyl group having 1 to 10 C atoms, or an aromatic hydrocarbon having 6 to 12 C atoms, or a carboxylic acid group; R ¹⁴ represents, at each occurrence, a linear or branched alkyl or acyl group having 1 to 10 C atoms, or an aromatic hydrocarbon having 6 to 12 C atoms, or a carboxylic acid group; R ¹⁵ represents, at each occurrence, a linear or branched alkyl group having 1 to 10 C atoms, wherein _{one or more -CH 2 -} groups may be replaced by -O- or -C(=O)-, but two adjacent -CH ₂ - groups may not be replaced by -O-; S ¹¹ and S ¹² represents, at each occurrence, independently of one another, an alkylene group having 1 to 20 C atoms, which may be branched or straight, wherein one -CH ₂ - group or, if present, a plurality of -CH ₂ - groups may be replaced by -O- or -C(=O)-, but two adjacent -CH ₂ - groups may not be replaced by -O-, and one or, if present, a plurality of -CH ₂ - groups may be replaced by -CH=CH- or -C≡C- and wherein one H atom or a plurality of H atoms may be replaced by F, OR ¹³ , N(R ¹³ )(R ¹⁴ ) or R ¹⁵ , or represents a single bond, X ¹¹ represents C, Y ¹¹ to Y ¹⁴ each independently of one another represent methyl or ethyl, Z ¹¹ to Z ¹⁴ represents -O-, -(C=O)-, -O-(C=O)-, -(C=O)-O-, -O-(C=O)-O-, -(NR ¹³ )-, -NR ¹³ -(C=O)- or a single bond at each occurrence, if S ¹¹ is a single bond, then both Z ¹¹ and Z ¹² do not represent -O- at the same time, and if S ¹² is a single bond, then both Z 13 and Z ¹⁴ do not represent -O- ^at the same time, and if -X ¹¹ [-R ¹¹ ] _o - is a single bond, then both Z ¹² and Z ¹³ do not represent -O- at the same time, p represents 1 or 2, o represents (3-p), n*p represents an integer from 3 to 10, and when p=1, m represents (10-n), and in the case of p=2, n represents an integer from 2 to 4, and m represents (4-n), represents an organic group having (m+n) bonding sites, and when p=1, -X ¹¹ [-R ¹¹ ] _o - may alternatively represent a single bond, wherein the one or more bireactive or polyreactive mesogen compounds include one or more bireactive mesogen compounds selected from the following formulae: wherein ^P0 is independently, at multiple occurrences, propenyl, methacryl, oxetane, epoxy, vinyl, heptadiene, vinyloxy, propenyl ether, or styryl; and L is, at each occurrence, the same or different, P-Sp-, F, Cl, Br, I, -CN, -NO ₂ , -NCO, -NCS, -OCN, -SCN, -C(=O)NR ⁰⁰ R ⁰⁰⁰ , -C(=O)OR ⁰⁰ , -C(=O)R ⁰⁰ , -NR ⁰⁰ R ⁰⁰⁰ , -OH, -SF ₅ , an optionally substituted silyl group, an aryl or heteroaryl group having 1 to 12 C atoms, a straight-chain or branched alkyl group having 1 to 12 C atoms, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group or an alkoxycarbonyloxy group, wherein one or more H atoms are optionally replaced by F or Cl, r is 0, 1, 2, 3 or 4, x and y are independently 0 or the same or different integers from 1 to 12, and z is each and independently 0 or 1, wherein if the adjacent x or y is 0, then z is 0. The polymerizable LC material of claim 1, comprising one or more monoreactive mesogen compounds selected from the formula MRM, ^P1 - ^Sp1 -MG-RMRM, wherein ^P1 represents a polymerizable group, ^Sp1 represents a spacer group or a single bond, MG is a rod-shaped mesogen group selected from the formula MG-( ^A1 - ^Z1 ) _n - ^A2 -MG, wherein ^A1 and ^A2 , in the case of multiple occurrences, independently represent an aromatic or alicyclic group, which optionally contains one or more heteroatoms selected from N, O and S and is optionally monosubstituted or polysubstituted by ^L1 , and ^L1 is P-Sp-, F, Cl, Br, I, -CN, -NO2, _-NCO , -NCS, -OCN, -SCN, -C(=O) ^{NR00R000 ,} -C(=O)OR ⁰⁰ , -C(=O)R ⁰⁰ , -NR ⁰⁰ R ⁰⁰⁰ , -OH, -SF ₅ , optionally substituted silyl, aryl or heteroaryl having 1 to 12 C atoms, straight-chain or branched alkyl having 1 to 12 C atoms, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, wherein one or more H atoms are optionally replaced by F or Cl, R ⁰⁰ and R ⁰⁰⁰ independently represent H or an alkyl group having 1 to 12 C atoms, and Z ^1, in the case of multiple occurrences, independently represents -O-, -S-, -CO-, -COO-, -OCO-, -S-CO-, -CO-S-, -O-COO-, -CO-NR ⁰⁰ -, -NR ⁰⁰ -CO-, -NR ⁰⁰ -CO- ⁰⁰⁰ , -NR ⁰⁰ -CO-O-, -O-CO-NR ^00- , -OCH ₂ -, -CH ₂ O-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF 2 -, -CF ₂ S-, -SCF ₂ -, -CH ₂ CH ₂ -, -(CH ₂ ) _n1 , -CF ₂ CH ₂ -, -CH 2 CF ₂ -, -CF ₂ CF ₂ -, -CH= _N- , - N=CH-, -N=N-, -CH=CR ^00- _, -CY ¹ =CY ² -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, or a single bond, Y ¹ and Y ² independently represent H, F, Cl or CN, n is 1, 2, 3 or 4, and n1 is an integer from 1 to 10, R is F, Cl, Br, I, -CN, -NO ₂ , -NCO, -NCS, -OCN, -SCN, -C(=O)NR ^x R ^y , -C(=O)X, -C(=O)OR ^x , -C(=O)R ^y , -NR ^x R ^y , -OH, -SF ₅ , optionally substituted silyl, straight-chain or branched alkyl having 1 to 12 C atoms, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, wherein one or more H atoms are optionally replaced by F or Cl, X is halogen, and R ^x and R ^y are independently H or alkyl having 1 to 12 C atoms. The polymerizable LC material of claim 1, comprising one or more monoreactive mesogen compounds selected from the following formulae: wherein P ⁰ , L, r, x, y and z are as defined in claim 1 , R ⁰ , R ⁰¹ and R ⁰² are alkyl, alkoxy, sulfanyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy groups having 1 to 15 carbon atoms, or represent Y ⁰ , Y ⁰ is F, Cl, CN, NO ₂ , OCH ₃ , OCN, SCN, SF ₅ , or a monofluorinated, oligofluorinated or polyfluorinated alkyl or alkoxy group having 1 to 4 carbon atoms, Z ⁰ is -COO-, -OCO-, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH=CH-, -OCO-CH=CH-, -CH=CH-COO- or a single bond, and A ^0, in the case of multiple occurrences, is independently 1,4-phenylene which is unsubstituted or substituted with 1, 2, 3 or 4 groups L, or is trans-1,4-cyclohexylene, u and v are independently 0, 1 or 2, w is 0 or 1, and the benzene ring and the naphthyl ring may be further substituted with one or more identical or different groups L. A polymerisable LC material as claimed in any one of claims 1 to 3, comprising one or more compounds of formula ND, Where U ^1, 2 are independently selected from: Including mirror images thereof, wherein the ring U ¹ and the ring U ² are each bonded to the group -(B) _q - via an axial bond, and one or two non-adjacent CH ₂ groups in these rings are optionally replaced by O and/or S, and the ring U ¹ and the ring U ² are optionally substituted by one or more groups L, Q ^{1 and 2} are independently CH or SiH, Q ³ is C or Si, B is independently -C≡C-, -CY ¹ =CY ² - or an optionally substituted aromatic or heteroaromatic group at each occurrence, Y ^{1 and 2} are independently H, F, Cl, CN or R ⁰ , q is an integer from 1 to 10, A ^1-4 are independently selected from non-aromatic, aromatic or heteroaromatic carbocyclic or heterocyclic groups, which are optionally substituted by one or more groups R ⁵ , and each of -(A ¹ -Z ¹ ) _m -U ¹ -(Z ² -A ² ) _n - and -(A ³ -Z ³ ) _o -U ² -(Z ⁴ -A ⁴ ) _p - does not contain more aromatic groups than non-aromatic groups, and Z ^1-4 are independently -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR ⁰ -, -NR ⁰ -CO-, -NR ⁰ -CO-NR ⁰⁰ -, -OCH ₂ -, -CH ₂ O-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, -CF ₂ S-, _-SCF2- , _{-CH2CH2- ,} -(CH2) _3- , -( _CH2 ) _4- , -CF2CH2-, -CH2CF2-, -CF2CF2- ^{, -CH=CH-, -CY1=CY2-, -CH=N-, -N=CH-, -N=N-} _{, -CH} ⁼ CR0- _, -C≡C- _, -CH ₌ CH _- COO-, -OCO-CH=CH-, ^CR0R00 or _a single bond, ^R0 and ^R00 are independently H or an alkyl group having 1 to 12 C atoms, m and n are independently 0, 1, 2, ³ or ⁴ , o and p are independently 0, 1, 2, 3 or 4, R ^1-5 are independently the same or different groups selected from the following: H, halogen, -CN, -NC, -NCO, -NCS, -OCN, -SCN, -C(=O)NR ⁰ R ⁰⁰ , -C(=O)R ⁰ , -NH ₂ , -NR ⁰ R ⁰⁰ , -SH, -SR ⁰ , -SO ₃ H, -SO ₂ R ⁰ , -OH, -NO ₂ , -CF ₃ , -SF ₅ , P-Sp-, an optionally substituted silyl or carbonyl group, or an optionally substituted alkyl group having 1 to 40 C atoms which optionally contains one or more heteroatoms, or represents P or P-Sp-, or is substituted with P or P-Sp-, wherein the compounds contain one or more groups R ^1-5 representing P or P-Sp- or substituted with P or P-Sp-. , P is a polymerizable group, Sp is a spacer group or a single bond, and L are independently P-Sp-, F, Cl, Br, I, -CN, -NO ₂ , -NCO, -NCS, -OCN, -SCN, -C(=O)NR ⁰ R ⁰⁰ , -C(=O)X, -C(=O)OR ⁰ , -C(=O)R ⁰ , -NR ⁰ R ⁰⁰ , -OH, -SF ₅ , an optionally substituted silyl group, an aryl or heteroaryl group having 1 to 12 C atoms, and a linear or branched alkyl group, alkoxy group, alkylcarbonyl group, alkoxycarbonyl group, alkylcarbonyloxy group or alkoxycarbonyloxy group having 1 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl, wherein R ⁰ and R ⁰⁰ is as defined above and X is a halogen. The polymerizable LC material according to any one of claims 1 to 3, wherein the proportion of the bireactive or multireactive polymerizable mesogen compound is in the range of 5 wt % to 99 wt %. In the polymerizable LC material of claim 2 or 3, the proportion of the monoreactive mesogen compound is in the range of 5 wt% to 80 wt%. The polymerizable LC material of any one of claims 1 to 3, comprising one or more additives selected from the group consisting of a surfactant, a stabilizer, a catalyst, a sensitizer, an inhibitor, a chain transfer agent, a co-reactive monomer, a reactive thinner, a surface-active compound, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, a tackifier, a flow improver, a deaerator or defoamer, a diluent, a colorant, a dye, a pigment, and nanoparticles. A method for preparing a polymerizable LC material according to any one of claims 1 to 7, comprising the step of mixing one or more compounds of formula I with one or more bireactive or polyreactive mesogen compounds. A method for preparing a polymer film, comprising providing a layer of a polymerizable LC material according to one or more of claims 1 to 7 on a substrate, photopolymerizing the polymerizable LC material, and optionally removing the polymerized LC material from the substrate and/or optionally providing it on another substrate. A polymer film obtainable from a polymerizable LC material according to any one of claims 1 to 7 by a method comprising providing a layer of the polymerizable LC material on a substrate, photopolymerizing the LC material, and optionally removing the polymerized LC material from the substrate and/or optionally providing it on another substrate. The polymer film of claim 10, wherein the LC material is uniformly aligned. A use of the polymer film of claim 10 or 11 or the polymerizable LC material of any one of claims 1 to 7 for optical, electro-optical, information storage, decorative and security applications. The use of claim 12, wherein the application includes a liquid crystal display, a 3D display, a projection system, a polarizer, a compensator, an alignment layer, a color filter, a decorative image, a liquid crystal pigment, a reflective film having spatially varying reflective color, a multi-color image, an unforgeable document, and a banknote.