Polymerizable liquid crystal material and polymerized liquid crystal film

Abstract

The present invention relates to polymerizable LC materials comprising one or more di- or multireactive mesogenic compounds and one or more compounds of formula UVI, where the individual residues have one of the meanings given in the claims. Furthermore, the present invention also relates to methods for their preparation, polymer films with improved heat resistance and UV stability obtained from the corresponding polymerizable LC materials, methods for preparing such polymer films, and the use of such polymer films and said polymerizable LC materials for optical, electro-optical, decorative or security devices.

Description

[Technical Field]

[0001] The present invention relates to a compound comprising one or more di- or multi-reactive mesogenic compounds and one or more compounds of formula UVI [ka] and a polymerizable LC material comprising a compound of the formula The invention also relates to polymerizable LC materials, the individual residues of which have one of the meanings given in the claims. Furthermore, the invention also relates to methods for their preparation, polymer films with improved heat resistance and UV stability obtained from the corresponding polymerizable LC materials, methods for preparing such polymer films, and the use of such polymer films and said polymerizable LC materials for optical, electro-optical, decorative or security devices.

[0002] Background of the Invention Polymerizable liquid crystal materials are known in the art for producing anisotropic polymer films with uniform orientation. These films are typically produced by coating a thin layer of a polymerizable liquid crystal mixture onto a substrate, orienting the mixture in a uniform direction, and polymerizing the mixture. The orientation of the film can be planar, i.e., the liquid crystal molecules are oriented substantially parallel to the layer, homeotropic (perpendicular or perpendicular to the layer), or tilted.

[0003] Such optical films are described, for example, in EP 0940707, EP 0888565 and GB 2329393.

[0004] Polymerizable liquid crystal (LC) materials are stable at room temperature but can degrade when exposed to elevated temperatures. For example, when heated for a certain period of time, optical properties such as dispersion or retardance deteriorate, and the performance of optical films therefore deteriorates over time. This can be attributed, inter alia, to a low degree of polymerization and the corresponding high content of residual free radicals in the polymer, polymer shrinkage, and / or thermo-oxidative degradation.

[0005] Thermo-oxidative degradation is the breakdown of polymer networks catalyzed by oxidation at high temperatures. As is commonly known, antioxidant additives, or simply antioxidants, can be used to reduce thermo-oxidative degradation of polymers when exposed to high temperatures. This is particularly important when utilizing optical films in in-cell applications due to the high temperatures they must withstand, particularly during annealing of polyimide layers in LC cells. In this regard, WO 2009 / 86911 and Japanese Patent Publication No. 5354238 describe polymerizable liquid crystal (LC) materials containing the commercially available antioxidant Irganox® 1076.

[0006] The above materials have clear drawbacks, such as the UV stability or heat resistance of the resulting polymer films still not being sufficiently high due to the LC materials used, limited transparency to VIS light, the need to use additional additives, or limited application bandwidth.

[0007] Thus, there remains a need for new, preferably improved, polymerizable liquid crystal materials or mixtures that do not exhibit, or exhibit to a lesser extent, the disadvantages of prior art materials.

[0008] Advantageously, such polymerizable LC materials should preferably be applicable to the production of different, uniformly oriented polymer networks, such as polymer films and polymer network LC applications, while at the same time being particularly - exhibits favorable adhesion to the substrate, - High transparency to VIS light, - exhibits reduced yellowing over time, and - should exhibit favorable high temperature stability or durability, and in addition: - should exhibit advantageously high thermal and / or UV stability or durability, and in addition - The uniformly oriented polymer film should be produced by commonly known methods compatible with mass production.

[0009] Further objects of the present invention will become readily apparent to those skilled in the art from the detailed description that follows.

[0010] Surprisingly, the inventors of the present invention have found that one or more, preferably all, of the above objectives can be achieved, preferably simultaneously, by using a polymerizable LC material according to claim 1.

[0011] Summary of the Invention The present invention relates to a compound comprising at least one direactive or multireactive mesogenic compound and one or more compounds of formula UVI [ka] and a polymerizable LC material comprising a compound of the formula The individual residues have the following meanings: R 1 ~R 5 are each independently selected from the group consisting of H, -alkyl, -OH, -alkylaryl, -alkylheteroaryl, -cycloalkyl, cycloheteroalkyl, alkenyl, aryl, and -SOH; R 6 and R 7 each independently represents a hydrogen atom, a hydroxy group, or a halogen atom, or R 6 and R 7 relates to polymerizable LC materials which form optionally substituted cycloalkyl or cycloheteroalkyl rings.

[0012] Furthermore, the present invention relates to a corresponding method for the preparation of the polymerizable LC material.

[0013] The invention further relates to a polymer network or a polymer film obtained, preferably obtained, from the polymerizable LC material as described above or below, as well as to a method for producing a polymer film as described above or below.

[0014] The present invention further relates to a method for increasing the UV stability of a polymer film obtained, preferably obtained, from a polymerizable LC material as described above or below, by adding a compound of formula UVI to the LC material before polymerization.

[0015] The present invention further relates to the use of the polymer networks or polymer films or polymerizable LC materials as described above or below in optical, electro-optical, information storage, decorative and security applications such as liquid crystal displays, projection systems, polarizers, compensation plates, alignment layers, circular polarizers, color filters, decorative images, liquid crystal pigments, reflective films with spatially varying reflected color, multicolor images, unforgeable documents such as identity cards, credit cards and banknotes.

[0016] The present invention further relates to an optical element 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 reflected color, a multicolor image for decoration or information storage, comprising at least one polymer network or polymer film or polymerizable LC material as described above or below.

[0017] The invention further relates to a liquid crystal display comprising at least one polymer network or polymer film or polymerizable LC material or optical element as described above or below.

[0018] The present invention further relates to an authentication, verification or security mark, a color or multicolor image for security applications, an uncounterfeitable object or document of value such as an identity card, credit card or banknote, comprising a polymer network or a polymer film or a polymerizable LC material or an optical element as described above or below.

[0019] Terms and Definitions The term "polymer," as used herein, is understood to mean a molecule comprising a backbone of one or more different types of repeating units (the smallest building blocks of a molecule), and encompasses the commonly known terms "oligomer," "copolymer," "homopolymer," and the like. Furthermore, the term polymer is understood to include, in addition to the polymer itself, residues from initiators, catalysts, and other elements incidental to the synthesis of such polymers, where such residues are not covalently incorporated therein. Furthermore, such residues and other elements, while usually removed during post-polymerization purification processes, are typically mixed or combined with the polymer, such that they usually remain with the polymer when transferred between containers or solvents or dispersion media.

[0020] As used herein, the term "(meth)acrylic polymer" includes polymers obtained from acrylic monomers, polymers obtained from methacrylic monomers, and the corresponding copolymers obtained from mixtures of such monomers.

[0021] The term "polymerization" refers to the chemical process of forming a polymer by linking together multiple polymerizable groups or polymer precursors (polymerizable compounds) containing such polymerizable groups.

[0022] The terms "film" and "layer" include rigid or flexible, self-supporting or free-standing films that have mechanical stability, as well as coatings or layers on a supporting substrate or between two substrates.

[0023] The terms "liquid crystal" or "LC" refer to materials that have a liquid crystal mesophase within a certain temperature range (thermotropic LC) or concentration range in solution (lyotropic LC). They necessarily contain mesogenic compounds.

[0024] The terms "mesogenic compound" and "liquid crystal compound" refer to compounds containing one or more calamitic (rod-like or plate-like / lamellar) or discotic (disk-shaped) mesogenic groups. The term "mesogenic group" refers to a group capable of inducing liquid crystal phase (or mesophase) behavior. Compounds containing mesogenic groups do not necessarily exhibit liquid crystal mesophases by themselves. They may also exhibit liquid crystal mesophases only in mixtures with other compounds, or when the mesogenic compound or material, or a mixture thereof, is polymerized. This includes low molecular weight non-reactive liquid crystal compounds, reactive or polymerizable liquid crystal compounds, and liquid crystal polymers.

[0025] Calamitic mesogenic groups typically comprise a mesogenic core consisting of one or more aromatic or non-aromatic cyclic groups connected to each other directly or via linking groups, optionally with terminal groups attached to the termini of the mesogenic core, and optionally with one or more side groups attached to the longitudinal sides of the mesogenic core, where these terminal and side groups are typically selected from, for example, carbyl or hydrocarbyl groups, polar groups such as halogen, nitro, hydroxy, or polymerizable groups.

[0026] The term "reactive mesogen" refers to polymerizable mesogenic or liquid crystal compounds, preferably monomeric compounds, which can be used as pure compounds or as mixtures of reactive mesogens with other compounds that function as photoinitiators, inhibitors, surfactants, stabilizers, chain transfer agents, non-polymerizable compounds, etc.

[0027] Polymerizable compounds with one polymerizable group are also called "monoreactive" compounds, compounds with two polymerizable groups are also called "direactive" compounds, and compounds with more than two polymerizable groups are also called "multireactive" compounds. Compounds with no polymerizable groups are also called "nonreactive or nonpolymerizable" compounds.

[0028] The term "non-mesogenic compound or material" means a compound or material that does not contain a mesogenic group as defined above.

[0029] Visible light is electromagnetic radiation having wavelengths ranging from about 400 nm to about 740 nm. Ultraviolet (UV) light is electromagnetic radiation having wavelengths ranging from about 200 nm to about 450 nm.

[0030] Irradiance (E e ) or radiated power is defined as the power (dθ) of electromagnetic radiation incident on a surface per unit area (dA): E e = dθ / dA.

[0031] Radiant exposure or radiation (H e ) is the irradiation or radiated power (E e ) is represented as: H e =E e ·t.

[0032] For example, all temperatures, such as the melting point T(C,N) or T(C,S), the smectic (S) to nematic (N) phase transition T(S,N), and the clearing point T(N,I), of a liquid crystal are given in degrees Celsius. All temperature differences are given in degrees.

[0033] The term "clearing point" means the temperature at which the transition occurs between the mesophase and the isotropic phase with the highest temperature range.

[0034] The term "director" is known in the prior art and refers to the preferred orientation direction of the long molecular axis (in the case of calamitic compounds) or the short molecular axis (in the case of discotic compounds) of liquid crystal or RM molecules. In the uniaxial ordering of such anisotropic molecules, the director is the axis of anisotropy.

[0035] The terms "alignment" or "orientation" refer to the alignment (orientational order) of anisotropic units of a material, such as fragments of small or large molecules, in a common direction called the "orientation direction". In an aligned layer of a liquid crystal or RM material, the liquid crystal directors coincide with the alignment direction, so that the alignment direction corresponds to the direction of the anisotropic axis of the material.

[0036] The term "uniform orientation" or "uniform alignment" of liquid crystal or RM materials, for example in a layer of material, means that the long molecular axes (in the case of calamitic compounds) or short molecular axes (in the case of discotic compounds) of the liquid crystal or RM molecules point in substantially the same direction. In other words, the lines of the liquid crystal directors are parallel.

[0037] The terms "homeotropic structure" or "homeotropic orientation" refer to a film in which the optic axis is substantially perpendicular to the film plane.

[0038] The terms "planar structure" or "planar orientation" refer to a film in which the optical axis is substantially parallel to the film plane.

[0039] The term "negative (optical) dispersion" refers to a birefringent or liquid crystalline material or layer that exhibits inverse birefringence dispersion, in which the magnitude of 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. In contrast, "positive (optical) dispersion" refers to a material or layer having |Δn(450)|>|Δn(550)|, or Δn(450) / Δn(550)>1. See, for example, A. Uchiyama and 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).

[0040] Since optical retardation at a given wavelength is defined as the product of birefringence and layer thickness, as noted above [R(λ) = Δn(λ) d], optical dispersion can be expressed as either the "birefringence dispersion" in terms of the ratio Δn(450) / Δn(550), or the "retardation dispersion" in terms of 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 change with wavelength, R(450) / R(550) is equal to Δn(450) / Δn(550). Thus, a material or layer with negative or inverse dispersion has R(450) / R(550)<1 or |R(450)|<|R(550)|, and a material or layer with positive or normal dispersion has R(450) / R(550)>1 or |R(450)|>|R(550)|.

[0041] In the present invention, unless otherwise stated, "optical dispersion" means retardation dispersion, i.e. the ratio R(450) / R(550).

[0042] The term "large variance" means that the absolute value of the variance indicates a large deviation from 1, and the term "small variance" means that the absolute value of the variance indicates a small deviation from 1. Thus, a "large negative variance" means that the variance value is significantly less than 1, and a "small negative variance" means that the variance value is slightly less than 1.

[0043] The retardation (R(λ)) of a material can be measured using a spectroscopic ellipsometer, such as the M2000 spectroscopic ellipsometer manufactured by J.A. Woollam Co. This instrument can measure the optical retardance of a birefringent sample, such as quartz, over a range of wavelengths in nanometers, typically over light wavelengths from 370 nm to 2000 nm. From this data, the dispersion of the material (R(450) / R(550) or Δn(450) / Δn(550)) can be calculated.

[0044] The method for making 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 Retardation Measurement (RetMeas) Manual (2002) and Guide to WVASE (2002) published by J.A. Woollam Co. Inc. (Lincoln, Nebraska, USA) also provide a method for making these measurements. W oollam V Avaliable A ngle S pectroscopic EThe measurement procedure described in the ellipsometer is followed. Unless otherwise stated, this method is used to determine the retardation of the materials, films, and devices described in this invention.

[0045] The term "A-plate" refers to an optical retarder that utilizes a layer of uniaxially birefringent material with its extraordinary axis oriented parallel to the plane of the layer.

[0046] The term "C-plate" refers to an optical retarder that utilizes a layer of uniaxially birefringent material with its extraordinary axis oriented perpendicular to the plane of the layer.

[0047] In an A / C-plate containing optically uniaxial birefringent liquid crystal material with uniform orientation, the optic axis of the film is given by the direction of the extraordinary axis. An A (or C) plate containing optically uniaxial birefringent material with positive birefringence is also called a "positive A (or C) plate" or "+A (or +C) plate".

[0048] An A (or C) plate comprising a film of optically uniaxial birefringent material with negative birefringence, such as a discotic anisotropic material, is also called a "negative A (or C) plate" or "-A (or C) plate", depending on the orientation of the discotic material. Films made from cholesteric calamitic materials with reflection bands in the UV part of the spectrum also have the optics of a negative C plate.

[0049] The birefringence Δn is Δn=n e -n o where n e is the extraordinary refractive index, and n o is the ordinary refractive index, and the mean refractive index n av. is the following formula: n av. =((2n o 2 +n e 2 ) / 3) 1 / 2 is given by

[0050] Average refractive index n av. and the normal refractive index n o can be measured using an Abbe refractometer. Δn can then be calculated from the above formula.

[0051] Unless the context clearly dictates otherwise, as used herein plural forms of the terms herein are to be construed as including the singular form and vice versa.

[0052] All physical properties were or are determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals", Status Nov. 1997, Merck KGaA, Germany, and are stated for a temperature of 20° C. unless otherwise stated. The optical anisotropy (Δn) is determined at a wavelength of 589.3 nm.

[0053] In case of doubt, the definitions given in C. Tschierske, G. Pelzl and S. Diele, Angew. Chem. 2004, 116, 6340-6368 shall apply.

[0054] Unless expressly stated otherwise in a given general formula, the following terms have the following meanings: A "carbyl group" refers to a monovalent or polyvalent organic group containing at least one carbon atom, either without any additional atoms (e.g., -C≡C-) or optionally containing one or more additional atoms, such as N, O, S, P, Si, Se, As, Te, or Ge (e.g., carbonyl). A "hydrocarbyl group" refers to a carbyl group that additionally contains one or more H atoms and optionally contains one or more heteroatoms, such as N, O, S, P, Si, Se, As, Te, or Ge.

[0055] The carbyl or hydrocarbyl group may be saturated or unsaturated. Unsaturated groups are, for example, aryl, alkenyl, or alkynyl groups. Carbyl or hydrocarbyl groups with more than three carbon atoms may be linear, branched, and / or cyclic, and may contain spiro-linked or fused rings.

[0056] Preferred carbyl and hydrocarbyl groups are optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy having 1 to 40, preferably 1 to 25, particularly preferably 1 to 18 C atoms, optionally substituted aryl or aryloxy having 6 to 40, preferably 6 to 25 C atoms, or optionally substituted alkylaryl, arylalkyl, alkylaryloxy, arylalkyloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy and aryloxycarbonyloxy having 6 to 40, preferably 6 to 25 C atoms.

[0057] More preferred carbyl and hydrocarbyl groups are C1-C 40 Alkyl, C2-C 40 Alkenyl, C2-C 40 Alkynyl, C3-C 40 Allyl, C4~C 40 Alkyldienyl, C4-C 40 Polyenyl, C6-C 40 Aryl, C6-C 40 Alkylaryl, C6-C 40 Aryl alkyl, C6-C 40 Alkylaryloxy, C6-C 40 Arylalkyloxy, C2-C 40 Heteroaryl, C4-C 40 Cycloalkyl, C4-C 40 Cycloalkenyl, etc. C1-C 22 Alkyl, C2-C 22 Alkenyl, C2-C 22Alkynyl, C3-C 22 Allyl, C4~C 22 Alkyldienyl, C6-C 12 Aryl, C6-C 20 Aryl alkyl, and C2-C 20 Heteroaryl is particularly preferred.

[0058] Further preferred carbyl and hydrocarbyl groups are linear, branched or cyclic alkyl residues having 1 to 40, preferably 1 to 25, more preferably 1 to 12 C atoms, which are unsubstituted or mono- or polysubstituted by F, Cl, Br, I or CN, in which one or more non-adjacent CH groups are, independently of one another, -C(R x )=C(R x )-, -C≡C-, -N(R x )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- may be substituted by -, -O-, -S-, -CO-, -CO-O-, -O-CO-O-, respectively, so that the O and / or S atoms are not directly bonded to each other.

[0059] In the above, R x preferably represents H, halogen, a linear, branched, or cyclic alkyl chain having 1 to 25 C atoms, in which one or more non-adjacent C atoms may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, and in which one or more H atoms may be replaced by fluorine, an optionally substituted aryl group or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl group or heteroaryloxy group having 2 to 40 C atoms.

[0060] Preferred alkyl groups are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, n-hexyl, 2-ethylhexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, dodecanyl, trifluoromethyl, perfluoro-n-butyl, 2,2,2-trifluoroethyl, perfluorooctyl, perfluorohexyl, and the like.

[0061] Preferred alkenyl groups are, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, and the like.

[0062] Preferred alkynyl groups are, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, octynyl, and the like.

[0063] Preferred alkoxy groups are, for example, methoxy, ethoxy, 2-methoxyethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, 2-methylbutoxy, n-pentoxy, n-hexoxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy, n-dodecyloxy, and the like.

[0064] Preferred amino groups include, for example, dimethylamino, methylamino, methylphenylamino, phenylamino, and the like.

[0065] Aryl and heteroaryl groups can be monocyclic or polycyclic. That is, they can have one ring (e.g., phenyl) or two or more rings, which can be fused (e.g., naphthyl) or covalently linked (e.g., biphenyl), or can contain a combination of fused and linked rings. Heteroaryl groups contain one or more heteroatoms, preferably selected from O, N, S, and Se.

[0066] Particularly preferred are mono-, bi- or tricyclic aryl groups having 6 to 25 C atoms and optionally substituted mono-, bi- or tricyclic heteroaryl groups having 2 to 25 C atoms, optionally containing fused rings. Five-, six- or seven-membered aryl or heteroaryl groups are further preferred, in which one or more CH groups may be replaced by N, S, or O such that the O and / or S atoms are not directly bonded to each other.

[0067] Preferred aryl groups are, for example, phenyl, biphenyl, terphenyl, [1,1':3',1"]terphenyl-2'-yl, naphthyl, anthracene, binaphthyl, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzopyrene, fluorene, indene, indenofluorene, spirobifluorene, and the like.

[0068] Preferred heteroaryl groups are, for example, pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, furan, thiophene, selenophene, oxazole, isoxazole, 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, Five-membered rings such as 2,5-thiadiazole and 1,3,4-thiadiazole, six-membered rings such as pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine and 1,2,3,5-tetrazine, or indole, isoindole, indolizine, indazole, benzimidazole, benzotriazole, purine, naphthoimidazole, phenanthrene, Phenanthrimidazole, pyridoimidazole, pyrazineimidazole, quinoxalineimidazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, benzothiazole, benzofuran, isobenzofuran, dibenzofuran, quinoline, isoquinoline, pteridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8- and fused groups such as quinoline, benzoisoquinoline, acridine, phenothiazine, phenoxazine, benzopyridazine, benzopyrimidine, quinoxaline, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthridine, phenanthroline, thieno[2,3b]thiophene, thieno[3,2b]thiophene, dithienothiophene, isobenzothiophene, dibenzothiophene, benzothiadiazothiophene, or combinations of these groups. Heteroaryl groups may be substituted with alkyl, alkoxy, thioalkyl, fluorine, fluoroalkyl, or additional aryl or heteroaryl groups.

[0069] (Non-aromatic) alicyclic and heterocyclic groups include both saturated rings, i.e., those containing only single bonds, and partially unsaturated rings, i.e., those that may also contain multiple bonds. Heterocycles contain one or more heteroatoms, preferably selected from Si, O, N, S, and Se.

[0070] (Non-aromatic) alicyclic and heterocyclic groups may be monocyclic, i.e., containing only one ring (e.g., cyclohexane), or polycyclic, i.e., containing several rings (e.g., decahydronaphthalene or bicyclooctane). Saturated groups are particularly preferred. Mono-, bi-, or tricyclic groups having 3 to 25 C atoms are more preferred, which optionally contain fused rings and are optionally substituted. Five-, six-, seven-, or eight-membered carbocyclic groups are more preferred, in which one or more C 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 CH groups may be replaced by -O- and / or -S-.

[0071] Preferred alicyclic and heterocyclic groups are, for example, 5-membered groups such as cyclopentane, tetrahydrofuran, tetrahydrothiofuran, and pyrrolidine; 6-membered groups such as cyclohexane, silynan, cyclohexene, tetrahydropyran, tetrahydrothiopyran, 1,3-dioxane, 1,3-dithiane, and piperidine; 7-membered groups 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, and octahydro-4,7-methanoindan-2,5-diyl.

[0072] The aryl, heteroaryl, (non-aromatic) alicyclic and heterocyclic groups optionally have one or more substituents, which are preferably silyl, sulfo, sulfonyl, formyl, amine, imine, nitrile, mercapto, nitro, halogen, C 1~12 Alkyl, C6~12 Aryl, C 1~12 It is selected from groups including alkoxy, hydroxyl, or a combination of these groups.

[0073] Preferred substituents are, for example, solubility-promoting groups such as alkyl or alkoxy, electron-withdrawing groups such as fluorine, nitro, or nitrile, or substituents for increasing the glass transition temperature (Tg) of the polymer, especially bulky groups such as, for example, t-butyl or optionally substituted aryl groups.

[0074] 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(R x )2, -C(=O)Y x , -C(=O)R x , -C(=O)OR x , -N(R x )2, where R x has the above meaning, and the above Y x represents halogen, optionally substituted silyl, optionally substituted aryl or heteroaryl having 4 to 40, preferably 4 to 20, ring atoms, and straight-chain or branched alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy having 1 to 25 C atoms and in which one or more H atoms are optionally replaced by F or Cl.

[0075] "Substituted silyl or aryl" preferably includes halogen, -CN, -R y , -OR y , -CO-R y , -CO-OR y , -O-CO-R y , or -O-CO-OR y where R is the number of substituted y represents H, a linear, branched or cyclic alkyl chain having 1 to 12 C atoms.

[0076] In the formulae shown above and below, the substituted phenylene ring [ka] is preferably [ka] wherein L is the same or different in each occurrence and has one of the meanings given above and below, preferably F, Cl, CN, NO, CH, C, H, C(CH), CH(CH), CHCH(CH)C, H, OCH, OC, H, COCH, COC, H, COOCH, COOC, H, CF, OCF, OCHF, OC, F or P-Sp-, very preferably F, Cl, CN, CH, C, H, OCH, COCH, OCF or P-Sp-, most preferably F, Cl, CH, OCH, COCH, or OCF.

[0077] "Halogen" represents F, Cl, Br, or I, preferably F or Cl, more preferably F.

[0078] The term "cycloheteroalkyl ring" or "cycloheteroalkyl" in the sense of the present invention is intended to mean a non-aromatic monocyclic or polycyclic alkyl ring containing at least one heteroatom, which may also be referred to as a heterocycloalkyl ring.

[0079] The term "alkylaryl" as used in the context of the present invention relates to a residue having an alkyl-aryl structure linked via an alkyl group. In this context, both alkyl and aryl groups include substituted residues. With regard to the term "substituted", reference is made to the above remarks.

[0080] The term "alkylheteroaryl" as used in the context of the present invention refers to a residue having an alkyl-heteroaryl structure linked via an alkyl group. In this context, both alkyl and heteroaryl groups include substituted residues. With regard to the term "substituted", reference is made to the above remarks.

[0081] 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 polymerization with ring opening, such as, for example, oxetane or epoxide groups.

[0082] Preferably, the polymerizable group (P) is CH2=CW 1 -COO-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -(O) k3 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-, CH2=CW 1 -CO-NH-, CH3-CH=CH-O-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH-, where: W 1 represents H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH3, 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 of one another, represent H, Cl or alkyl having 1 to 5 C atoms, Phe represents 1,4-phenylene, which is optionally substituted with one or more residues L as defined above but different from P-Sp, preferably preferred substituents L are F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5, further phenyl, k1, k2 and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 is an integer of 1-10.

[0083] Particularly preferred polymerizable groups P are CH2=CH-COO-, CH2=C(CH3)-COO-, CH2=CF-COO-, CH2=CH-, CH2=CH-O-, (CH2=CH)2CH-OCO-, (CH2=CH)2CH-O-, [ka] and [ka] where W 2 denotes H or alkyl having 1 to 5 C atoms, in particular H, methyl, ethyl or n-propyl.

[0084] More preferred polymerizable groups (P) are vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxide, most preferably acrylate or methacrylate, especially acrylate.

[0085] Preferably, all multireactive polymerizable compounds and subformulas thereof contain, instead of one or more residues P-Sp-, one or more branched residues containing two or more polymerizable groups P (multireactive polymerizable residues).

[0086] Suitable residues of this type, and polymerizable compounds containing them, are described, for example, in US Pat. No. 7,060,200 or US Patent Application Publication No. 2006 / 0172090.

[0087] A multireactive polymerizable residue selected from the following formulas: -X-Alkyl-CHP x -CH2-CH2P y I * a -X-Alkyl-C(CH2P x )(CH2P y )-CH2P z I * b -X-Alkyl-CHP x CHP y -CH2P z I * c -X-Alkyl-C(CH2P x )(CH2P y )-C aa H 2aa+1 I * d -X-Alkyl-CHP x -CH2P y I * e -X-Alkyl-CHP x P y I * f -X-Alkyl-CP x P y -C aa H 2aa+1 I * g -X-Alkyl-C(CH2P v )(CH2P w )-CH2OCH2-C(CH2P x )(CH2Py)CH2P z I * h -X-Alkyl-CH((CH2) aa P x )((CH2) bb P y ) I * i -X-Alkyl-CHPx CHP y -C aa H 2aa+1 I * k is particularly preferred, where: Alkyl represents a single bond or a straight-chain or branched alkylene having 1 to 12 C atoms, in which one or more non-adjacent CH groups may, independently of one another, be -C(R x )=C(R x )-, -C≡C-, -N(R x )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- may be substituted by -O-, -S-, -CO-, -CO-O-, -O-CO-O-, respectively, so that O atoms and / or S atoms are not directly bonded to each other, and further, one or more H atoms may be substituted by F, Cl or CN, and R x has one of the meanings given above, aa and bb each independently represents 0, 1, 2, 3, 4, 5 or 6; X has one of the meanings given for X', P v ~P z each independently of one another has one of the meanings given above for P.

[0088] Preferred spacer groups Sp are selected from the formula Sp'-X', such that the residue "P-Sp-" corresponds to the formula "P-Sp'-X'-", where: Sp' represents alkylene having 1 to 20, preferably 1 to 12, C atoms, optionally mono- or polysubstituted by F, Cl, Br, I or CN, wherein in addition, one or more non-adjacent CH groups are each independently of one another -O-, -S-, -NH-, -NR xx -, -SiR xx R yy -, -CO-, -COO-, -OCO-, -OCO-O-, -S-CO-, -CO-S-, -NR xx -CO-O-, -O-CO-NR 0xx -, -NR xx-CO-NR yy -, -CH=CH- or -C≡C- may be substituted so that the O and / or S atoms are not directly bonded to each other, X' is -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR xx -, -NR xx -CO-, -NR xx -CO-NR yy -, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR xx -, -CY xx =CY xx represents -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH- or a single bond; R xx and R yy each independently represent H or alkyl having 1 to 12 C atoms, Y xx and Y yy each independently represents H, F, Cl or CN, X' is preferably -O-, -S-CO-, -COO-, -OCO-, -O-COO-, or -CO-NR xx -, -NR xx -CO-, -NR xx -CO-NR yy - or a single bond.

[0089] A typical spacer group Sp' is, for example, -(CH2) p1 -, -(CH2CH2O) q1 -CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2-, or -(SiR xx R yy -O) p1 where p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R xx and R yy has the meaning given above.

[0090] Particularly preferred groups -X'-Sp'- are -(CH2) p1 -, -O-(CH2) p1 -, -OCO-(CH2) p1 -, -OCOO-(CH2) p1 -, where p1 is an integer from 1 to 12.

[0091] Particularly preferred radicals Sp′ are, for example, in each case linear methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, ethenylene, propenylene and butenylene.

[0092] In the present invention, [ka] represents trans-1,4-cyclohexylene, [ka] represents 1,4-phenylene.

[0093] In the present invention, the group -COO- or -CO2- is a group of the formula [ka] and the groups -OCO-, -OC- or -OOC- represent an ester group of the formula [ka] represents an ester group of the formula:

[0094] A "polymer network" is a network in which all polymer chains are interconnected to form a single macroscopic entity through many crosslinks.

[0095] The polymer networks can occur in the following types: - A graft polymer molecule is a branched polymer molecule in which one or more side chains are structurally or compositionally different from the main chain. - A star polymer molecule is a branched polymer molecule in which a single branch point gives rise to multiple linear chains or arms. If the arms are identical, the star polymer molecule is said to be regular. If adjacent arms are composed of different repeating subunits, the star polymer molecule is said to be mixed. - A comb polymer molecule consists 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 said to be regular. - Brush polymer molecules consist of a main chain with linear, unbranched side chains, where one or more branch points have four or more directional functional groups.

[0096] Throughout the description and claims of this specification, the words "comprise" and "contain," as well as variations of these words, such as "comprising" and "comprises," mean "including but not limited to," and are not intended to (and do not) exclude other elements. On the other hand, the word "comprise" also encompasses, but is not limited to, the word "consisting of."

[0097] Throughout the description and claims of this specification, the words "obtained" and "obtained," and variations of these words, mean "including but not limited to," and are not intended to (and do not) exclude other elements. On the other hand, the word "obtained" also encompasses, but is not limited to, the word "obtained."

[0098] All concentrations are given in weight percent and refer to the respective mixture as a whole. All temperatures are given in degrees Celsius and all temperature differences are given in degrees differential.

[0099] Detailed Description Preferred compounds of formula UVI are of the following sub-formula: [ka] is selected from where: R 1 ~R 5 are each independently selected from the group consisting of H, -alkyl, -OH, -alkylaryl, -alkylheteroaryl, -cycloalkyl, cycloheteroalkyl, alkenyl, aryl, and -SOH; R 6 and R 7 each independently represents a hydrogen atom, a hydroxy group, or a halogen atom; R 8 ~R 13 are each independently a residue selected from the group consisting of H, alkyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkenyl, and alkynyl; X 1 represents O or S, R 14 and R 15 is H, -C(=O)R 8 , alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heteroaryl and cycloheteroalkyl.

[0100] In a preferred embodiment, the compound of formula UVI is R 1 ~R 5 Preferably, at least one of R represents -OH. 1 represents —OH.

[0101] Thus, the compounds of formula UVI belong to the group of compounds of the following sub-formulae: [ka] is selected from where: R 2 ~R 5are each independently selected from the group consisting of H, -alkyl, -OH, -alkylaryl, -alkylheteroaryl, -cycloalkyl, cycloheteroalkyl, alkenyl, aryl, and -SOH; R 6 and R 7 each independently represents a hydrogen atom, a hydroxy group, or a halogen atom; R 8 ~R 13 are each independently a residue selected from the group consisting of H, alkyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkenyl, and alkynyl; X 1 represents O or S, and R 14 and R 15 is H, -C(=O)R 8 , alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heteroaryl and cycloheteroalkyl.

[0102] In a preferred embodiment, the compound of formula UVI is R 3 or R 5 and preferably selected from the group of compounds in which at least one of R 3 and R 5 Both represent -H.

[0103] Thus, the compounds of formula UVI belong to the group of compounds of the following sub-formulae: [ka] [ka] is selected from where: R 2 ~R 4are each independently selected from the group consisting of H, -alkyl, -OH, -alkylaryl, -alkylheteroaryl, -cycloalkyl, cycloheteroalkyl, alkenyl, aryl, and -SO3H; R 6 and R 7 each independently represents a hydrogen atom, a hydroxy group, or a halogen atom; R 8 ~R 13 are each independently a residue selected from the group consisting of H, alkyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkenyl, and alkynyl; X 1 represents O or S, and R 14 and R 15 is H, -C(=O)R 8 , alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heteroaryl and cycloheteroalkyl.

[0104] In a preferred embodiment, the compound of formula UVI is R 8 ~R 13 represents alkyl.

[0105] Thus, the compounds of formula UVI belong to the group of compounds of the following sub-formulae: [ka] is selected from where: R 2 and R 4 are each independently selected from the group consisting of H, -alkyl, -OH, -alkylaryl, -alkylheteroaryl, -cycloalkyl, cycloheteroalkyl, alkenyl, aryl, and -SO3H; R 6 and R 7 each independently represents hydrogen or halogen, preferably hydrogen; l, k, m, n, o, and p each independently represent an integer of 2 to 20, preferably 2 to 10, and more preferably 2 to 5; X 1 represents O or S, R 14 and R 15 is selected from the group consisting of H, -C(=O) alkyl, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heteroaryl, and cycloheteroalkyl.

[0106] In a preferred embodiment, the compound of formula UVI is R 2 and R 4 are preferably selected from the group of compounds in which each independently represents an alkylaryl group, in particular an alkylphenyl group, or an alkyl group, in particular a linear or branched alkyl group having 5 to 15 carbon atoms, in which one or more -(CH2)- groups may be replaced by -COO-, -OCO- so that the two oxygen atoms are not bonded to each other.

[0107] In a preferred embodiment, the compound of formula UVI is a compound of the group of compounds of the following sub-formulae: [ka] is selected from.

[0108] Preferably, the proportion of compounds of formula UVI in the LC medium is between 0.01 and 5% by weight, very preferably between 0.05 and 3% by weight, in particular between 0.1 and 2% by weight, of the total weight of the medium.

[0109] Compounds of formula UVI and its subformulas can be prepared analogously to processes described in standard works of organic chemistry known to those skilled in the art, such as, for example, Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Thieme-Verlag, Stuttgart. Some compounds are also commercially available under the trade name Tinuvin® (BASF, Germany), such as Tinuvin® 328, Tinuvin® 384, Tinuvin® 900, Tinuvin® 928, Tinuvin® 970, and Tinuvin® 1130.

[0110] Preferably, the one or more di- or multi-reactive mesogenic compounds have the formula DRM P 1 -Sp 1 -MG-Sp 2 -P 2 DRM is selected from where: P 1 and P 2 each independently represents a polymerizable group, Sp 1 and Sp 2 are each independently a spacer group or a single bond, MG is a rod-shaped mesogenic group, which preferably has the formula MG -(A 1 -Z 1 ) n -A 2 -MG is selected from where: A 1 and A 2 When there are a plurality of groups, each independently represents an aromatic group or an alicyclic group, which optionally contains one or more heteroatoms selected from N, O and S, and optionally contains L 1 and L 1are P-Sp-, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)NR 00 R 000 , -C(=O)OR 00 , -C(=O)R 00 , -NR 00 R 000 , -OH, -SF5, optionally substituted silyl, aryl or heteroaryl having 1 to 12, preferably 1 to 6, C atoms, and linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12, preferably 1 to 6, C atoms, in which one or more H atoms are optionally replaced by F or Cl, R 00 and R 000 represent, independently of one another, H or alkyl having 1 to 12 C atoms, Z 1 When there are a plurality of groups, they are each independently -O-, -S-, -CO-, -COO-, -OCO-, -S-CO-, -CO-S-, -O-COO-, or -CO-NR 00 -, -NR 00 -CO-, -NR 00 -CO-NR 000 , -NR 00 -CO-O-, -O-CO-NR 00 -, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH2CH2-, -(CH2) n1 , -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 00 -, -CY 1 =CY 2 represents -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH- or a single bond; Y 1 and Y 2 represent, independently of one another, H, F, Cl or CN, n is 1, 2, 3 or 4, preferably 1 or 2, most preferably 2; n1 is an integer of 1 to 10, preferably 1, 2, 3 or 4.

[0111] Preferred Group A 1 and A 2 include, but are not limited to, furan, pyrrole, thiophene, oxazole, thiazole, thiadiazole, imidazole, phenylene, cyclohexylene, bicyclooctylene, cyclohexenylene, pyridine, pyrimidine, pyrazine, azulene, indane, fluorene, naphthalene, tetrahydronaphthalene, anthracene, phenanthrene, and dithienothiophene, all of which are unsubstituted or substituted with one, two, three, or four groups L as defined above.

[0112] Particular preferred groups A 1 and A 2 is 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, indan-2,5-diyl, bicyclooctylene or 1,4-cyclohexylene, in which one or two non-adjacent —CH groups are optionally replaced by O and / or S, and these groups are unsubstituted or substituted by 1, 2, 3 or 4 groups L as defined above.

[0113] Particularly preferred groups Z 1 are, in each occurrence independently of one another, preferably selected from -COO-, -OCO-, -CH2CH2-, -CF2O-, -OCF2-, -C≡C-, -CH=CH-, -OCO-CH=CH-, -CH=CH-COO-, or a single bond.

[0114] Highly preferred bireactive mesogenic compounds of formula DRM are of the following formula: [ka] is selected from where: P 0 when there are a plurality of them, each independently represents a polymerizable group, preferably an acrylic, methacrylic, oxetane, epoxy, vinyl, heptadiene, vinyloxy, propenyl ether, or styrene group, L may be the same or different in each occurrence, and in the formula DRM, L 1 and preferably, if several are present, independently selected from F, Cl, CN or alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 5 C atoms, which are optionally halogenated, r is 0, 1, 2, 3 or 4; x and y are each independently 0 or the same or different integers from 1 to 12; Each z is independently 0 or 1, provided that when the adjacent x or y is 0, z is 0.

[0115] Particularly preferred are compounds of formula DRMa1, DRMa2, and DRMa3, especially compounds of formula DRMa1.

[0116] Preferably, the polymerisable LC material further comprises at least one monoreactive mesogenic compound, which preferably has the formula MRM P 1 -Sp 1 -MG-R MRM is selected from where P 1 , Sp 1 and MG has the meaning given in formula DRM, R is F, Cl, Br, I, -CN, -NO2, -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, -SF5, optionally substituted silyl, straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12, preferably 1 to 6, C atoms, in which one or more H atoms are optionally replaced by F or Cl, X is a halogen, preferably F or Cl; R x and R y are independently of one another H or alkyl having 1 to 12 C atoms.

[0117] Preferably, the monoreactive mesogenic compound of formula MRM has the formula [ka] [ka] [ka] [ka] is selected from where: P 0 , L, r, x, y, and z are as defined in formulas DRMa-1 to DRMe, R 0 is alkyl, alkoxy, thioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having one or more, preferably 1 to 15, C atoms, or Y 0 represents Y 0 is F, Cl, CN, NO2, OCH3, OCN, SCN, SF5, or a mono-, oligo- or polyfluorinated alkyl or alkoxy having 1 to 4 C atoms, Z 0is -COO-, -OCO-, -CH2CH2-, -CF2O-, -OCF2-, -CH=CH-, -OCO-CH=CH-, -CH=CH-COO-, or a single bond, A 0 when there are several, they are each independently 1,4-phenylene or trans-1,4-cyclohexylene which is unsubstituted or substituted by 1, 2, 3 or 4 groups L, u and v are independently 0, 1 or 2; w is 0 or 1, The benzene and naphthalene rings may be further substituted with one or more groups L, which may be the same or different.

[0118] Further preferred are compounds of formula MRM1, MRM2, MRM3, MRM4, MRM5, MRM6, MRM7, MRM9 and MRM10, in particular compounds of formula MRM1, MRM4, MRM6 and MRM7, especially compounds of formula MRM1 and MRM7.

[0119] Compounds of formula DRM, MRM and subformulae thereof can be prepared analogously to processes described in standard works of organic chemistry known to those skilled in the art, e.g., Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Thieme-Verlag, Stuttgart.

[0120] Overall, the proportion of the monoreactive, direactive, or polyreactive liquid crystal compound in the polymerizable liquid crystal material according to the present invention is preferably in the range of 30 to 99.9 wt %, more preferably in the range of 40 to 99.9 wt %, and even more preferably in the range of 50 to 99.9 wt %.

[0121] In a preferred embodiment, the proportion of the direactive or multireactive polymerizable mesogenic compound in the polymerizable liquid crystal material according to the present invention as a whole is preferably in the range of 5 to 99% by weight, more preferably in the range of 10 to 97% by weight, and even more preferably in the range of 15 to 95% by weight.

[0122] In another preferred embodiment, the proportion of said monoreactive polymerizable mesogenic compound in the polymerizable liquid crystal material according to the present invention as a whole, if present, is preferably in the range of 5 to 80% by weight, more preferably in the range of 10 to 75% by weight, even more preferably in the range of 15 to 70% by weight.

[0123] In another preferred embodiment, the proportion of said multireactive polymerizable mesogenic compound in the polymerizable liquid crystal material according to the present invention as a whole, if present, is preferably in the range of 1 to 30% by weight, more preferably in the range of 2 to 20% by weight, even more preferably in the range of 3 to 10% by weight.

[0124] In another preferred embodiment the polymerisable LC material does not comprise polymerisable mesogenic compounds with more than two polymerisable groups.

[0125] In another preferred embodiment the polymerisable LC material does not comprise any polymerisable mesogenic compounds with less than two polymerisable groups.

[0126] In another preferred embodiment, the polymerizable LC material is an achiral material, i.e. it does not contain chiral polymerizable mesogenic compounds or other chiral compounds.

[0127] In a further preferred embodiment, the polymerizable LC material comprises at least one monoreactive mesogenic compound, preferably a compound selected from formula MRM-1, at least one direactive mesogenic compound, preferably a compound selected from formula DRMa-1, and one or more compounds of formula UVI.

[0128] In a further preferred embodiment the polymerisable LC material comprises at least one monoreactive mesogenic compound, preferably a compound selected from formula MRM-7, at least one direactive mesogenic compound, preferably a compound selected from formula DRMa-1 and one or more compounds of formula UVI.

[0129] In a further preferred embodiment, the polymerizable LC material comprises at least two monoreactive mesogenic compounds, preferably selected from compounds of formula MRM-1 and / or MRM-7, at least one direactive mesogenic compound, preferably selected from compounds of formula DRMa-1, and one or more compounds of formula UVI.

[0130] In a further preferred embodiment, the polymerizable LC material comprises at least two monoreactive mesogenic compounds, preferably selected from compounds of formula MRM-1 and / or MRM-7, at least two direactive mesogenic compounds, preferably selected from compounds of formula DRMa-1, and one or more compounds of formula UVI.

[0131] In a further preferred embodiment the polymerisable LC material comprises at least two direactive mesogenic compounds, preferably compounds selected from formula DRMa-1 and one or more compounds of formula UVI.

[0132] In a further preferred embodiment, especially for negative optical dispersion applications, the polymerizable LC material described above has the formula ND [ka] and additionally comprising one or more compounds of where: U 1,2 are independent of each other, [ka] (including their mirror images), where the ring U 1 and U 2 are connected to the group -(B) via an axial bond. q -, and one or two non-adjacent CH groups in these rings are optionally replaced by O and / or S, and the ring U 1 and U 2 is optionally substituted by one or more groups L; L may be the same or different in each occurrence, and in the formula DRM, L 1and preferably, if several are present, independently selected from F, Cl, CN or alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 5 C atoms, which are optionally halogenated, Q 1,2 are each independently CH or SiH, Q 3 is C or Si, B, in each occurrence, independently of each other, is -C≡C-, -CY 1 =CY 2 - or an optionally substituted aromatic or heteroaromatic group; Y 1,2 are, independently of one another, H, F, Cl, CN or R 0 and 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 joined by one or more groups R 5 and optionally substituted with -(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 each of - contains no more aromatic groups than non-aromatic groups, preferably no more than one aromatic group; Z 1~4 are, independently of one another, -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 00-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2- 、 -CH2CH2-, -(CH2)3-, -(CH2)4-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -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 of one another, H or alkyl having 1 to 12 C atoms, m and n are, independently of each other, 0, 1, 2, 3, or 4; o and p are, independently of each other, 0, 1, 2, 3, or 4; R 1~5 are, independently of each other, H, halogen, -CN, -NC, -NCO, -NCS, -OCN, -SCN, -C(=O)NR 0 R 00 , -C(=O)R 0 , -NH2, -NR 0 R 00 , -SH, -SR 0 , -SO3H, -SO2R 0 , -OH, -NO2, -CF3, -SF5, P-Sp-, optionally substituted silyl, or carbyl or hydrocarbyl having 1 to 40 C atoms, optionally containing one or more heteroatoms, or represent P or P-Sp- or are substituted by P or P-Sp-, wherein the compound contains at least one group R which represents or is substituted by P or P-Sp- 1~5 Including, P is a polymerizable group, Sp is a spacer group or a single bond.

[0133] Preferably, the subgroups forming the bridging group B in formula ND are selected from groups having bond angles in the range of 120° or more, preferably 180°. -C≡C- groups or divalent aromatic groups linked in the para position to adjacent groups, such as 1,4-phenylene, naphthalene-2,6-diyl, indan-2,6-diyl, or thieno[3,2-b]thiophene-2,5-diyl, are highly preferred.

[0134] Further possible subgroups include -CH=CH-, -CY 1 =CY 2 -, -CH=N-, -N=CH-, -N=N-, and -CH=CR 0 -, where Y 1 , Y 2 , R 0 has the meaning given above.

[0135] Preferably, the bridging group in formula ND or -(B) q - includes 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 subgroup in formula ND, or B, is preferably selected from the group consisting of -C≡C-, optionally substituted 1,4-phenylene, and optionally substituted 9H-fluorene-2,7-diyl, in which the H atom at the 9-position in the fluorene group is optionally replaced with a carbyl or hydrocarbyl group.

[0136] Highly preferably, the bridging group in formula ND, or -(B) q - is -C≡C-, -C≡CC≡C-, -C≡CC≡CC≡C-, -C≡CC≡CC≡CC≡C-, [ka] is selected from where r is 0, 1, 2, 3, or 4, and L has the same meaning as described below.

[0137] Preferably, U in formula ND1 and U 2 The non-aromatic ring of the mesogenic group to which the bridging group is attached is preferably [ka] is selected from where R 5 is as defined in formula ND.

[0138] Preferably, the aromatic group A in formula ND 1~4 may be mononuclear, i.e., have only one aromatic ring (such as, for example, phenyl or phenylene), or polynuclear, i.e., have two or more condensed rings (such as, for example, naphthyl or naphthylene). Particularly preferred are mono-, bi- or tricyclic aromatic or heteroaromatic groups with up to 25 C atoms, which may also contain condensed rings and which are optionally substituted.

[0139] Preferably, the non-aromatic carbocyclic and heterocyclic rings A in the compounds of formula ND 1~4 include saturated (also called "fully saturated") ones, i.e., they contain only C atoms or heteroatoms connected by single bonds, and unsaturated (also called "partially saturated") ones, i.e., they also contain C atoms or heteroatoms connected by double bonds. Non-aromatic rings may also contain one or more heteroatoms, preferably heteroatoms selected from Si, O, N and S.

[0140] Preferably, the non-aromatic ring and the aromatic ring in formula ND, or A 1~4 is selected from trans-1,4-cyclohexylene and 1,4-phenylene optionally substituted with one or more groups L.

[0141] Highly preferred are compounds of formula ND where m and p are 1 and n and o are 1 or 2. Even more preferred are compounds of formula ND where m and p are 1 or 2 and n and o are 0. Even more preferred are compounds where m, n, o and p are 2.

[0142] In the compound of formula ND, the linking group connecting the aromatic group and the non-aromatic cyclic group in the mesogenic group, or Z 1~4 is preferably —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, or —CO—NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 0 -, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH2CH2-, -(CH2)3-, -(CH2)4-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -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, very preferably selected from -COO-, -OCO- and a single bond.

[0143] Preferably, in compounds of formula ND, the substituents on the ring, such as L, are preferably P-Sp-, F, Cl, Br, I, -CN, -NO2, -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, -SF5, optionally substituted silyl, aryl or heteroaryl having 1 to 12, preferably 1 to 6, C atoms, and linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12, preferably 1 to 6, C atoms, wherein one or more H atoms are optionally replaced by F or Cl, and wherein R 0 and R 00 is as defined in formula ND and X is a halogen.

[0144] Preferably, the compound of formula ND has R substituted by two or more polymerizable groups P or P-Sp- (multifunctional polymerizable groups). 1~4 or an end group such as R 5 Suitable polyfunctional polymerizable groups of this type are disclosed, for example, in US Pat. No. 7,060,200 or US Patent Application Publication No. 2006 / 0172090.

[0145] Highly preferred compounds of formula ND are of the following sub-formula: [ka] [ka] [ka] [ka] [ka] [In the formula, R 1~5 , A 1~4 , Z 1~4 , B, m, n, o, p and q have the meanings given above.

[0146] The following sub-expressions: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [wherein Z is the Z 1 and R has one of the meanings of R shown above, which is different from P-Sp-. 1 and P, Sp, L and r are as defined above, and the benzene ring in the mesogenic group is optionally substituted by one or more groups L as defined above.

[0147] Further preferred are polymerizable liquid crystal media in which the compound of formula ND is selected from the group of compounds of formula ND25 or ND26, in particular in which Z represents -COO-, r is 0 in each occurrence and P, Sp are as defined above.

[0148] P-Sp- in these preferred compounds is preferably P-Sp'-X', where X' is preferably -O-, -COO-, or -OCOO-.

[0149] Compounds of formula ND, subformulas thereof, and suitable methods for their synthesis are disclosed in WO 2008 / 119427.

[0150] The amount of compounds of formula ND in the polymerisable LC material is preferably 1-50%, very preferably 1-40%.

[0151] In particular, the combination of a compound of formula UVI with a compound of formula ND provides a beneficial reduction in optical dispersion and also provides beneficial heat resistance of the optical dispersion and / or retardation compared to polymerizable LC materials that do not utilize that particular combination.

[0152] In a further preferred embodiment, the polymerizable LC material optionally comprises one or more additives selected from the group consisting of additional polymerization initiators, antioxidants, surfactants, stabilizers, catalysts, sensitizers, inhibitors, chain transfer agents, co-reactant monomers, reactive thinners, surface-active compounds, lubricants, wetting agents, dispersants, hydrophobizing agents, adhesives, flow improvers, defoamers or antifoaming agents, degassing agents, diluents, reactive diluents, auxiliaries, colorants, dyes, pigments, and nanoparticles.

[0153] In another preferred embodiment, the polymerizable LC material optionally comprises one or more additives selected from polymerizable non-mesogenic compounds (reactive thinners). The amount of these additives in the polymerizable LC material is preferably 0-30%, very preferably 0-25%.

[0154] The reactive thinners used include not only substances that are actually called reactive thinners, but also auxiliary compounds already mentioned above that contain one or more complementary reactive units or polymerizable groups P, such as, for example, hydroxyl, thiol or amino groups, that can undergo a reaction with the polymerizable units of the liquid crystal compound.

[0155] Typical photopolymerizable materials include, for example, mono-, di-, and polyfunctional compounds containing at least one olefinic double bond, such as vinyl esters of carboxylic acids, such as lauric, myristic, palmitic, and stearic acids, and vinyl esters of dicarboxylic acids, such as succinic and adipic acids, as well as allyl ethers, vinyl ethers, methacrylic esters, and acrylic esters of monofunctional alcohols, such as lauryl, myristyl, palmityl, and stearyl alcohol, and diallyl and divinyl ethers of difunctional alcohols, such as ethylene glycol and 1,4-butanediol.

[0156] Also suitable are, for example, methacrylic and acrylic esters of polyfunctional alcohols, especially those containing no additional functional groups other than hydroxyl groups, or only ether groups, if any. Examples of such alcohols are difunctional alcohols such as ethylene glycol, propylene glycol, and their more highly condensed representatives, such as diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, butanediol, pentanediol, hexanediol, neopentyl glycol, alkoxylated phenolic compounds, such as ethoxylated and propoxylated bisphenols, cyclohexanedimethanol, trifunctional and polyfunctional alcohols, such as glycerol, trimethylolpropane, butanetriol, trimethylolethane, pentaerythritol, ditrimethylolpropane, dipentaerythritol, sorbitol, mannitol, and the corresponding alkoxylated products, especially ethoxylated and propoxylated alcohols.

[0157] Other suitable reactive thinners are polyester(meth)acrylates, which are (meth)acrylic acid esters of polyesterols.

[0158] 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. Dicarboxylic acids that can be used include succinic acid, glutaric acid, adipic acid, sebacic acid, o-phthalic acid, and their isomers and hydrogenated products, as well as esterifiable and transesterifiable derivatives of the aforementioned acids, such as anhydrides and dialkyl esters. Suitable polyols are the aforementioned alcohols, preferably ethylene glycol, 1,2- and 1,3-propylene glycol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, cyclohexanedimethanol, and polyglycols of the ethylene glycol and propylene glycol type.

[0159] Suitable reactive thinners are further known as 1,4-divinylbenzene, triallyl cyanurate, dihydrodicyclopentadienyl acrylate, and the like, represented by the formula: [ka] and the acrylic acid esters of tricyclodecenyl alcohol, and the allyl esters of acrylic acid, methacrylic acid, and cyanoacrylic acid.

[0160] In particular, taking into consideration the above-mentioned preferred composition, among the reactive thinners given as examples, those containing a photopolymerizable group are used.

[0161] This group includes, for example, dihydric and polyhydric alcohols, such as ethylene glycol, propylene glycol and their more highly condensed representatives, such as diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, butanediol, pentanediol, hexanediol, neopentyl glycol, cyclohexanedimethanol, glycerol, trimethylolpropane, butanetriol, trimethylolethane, pentaerythritol, ditrimethylolpropane, dipentaerythritol, sorbitol, mannitol and the corresponding alkoxylated, especially ethoxylated and propoxylated, alcohols.

[0162] This group also includes, for example, alkoxylated phenolic compounds, such as ethoxylated and propoxylated bisphenols.

[0163] These reactive thinners may furthermore be, for example, epoxides or urethane (meth)acrylates.

[0164] Epoxide (meth)acrylates are, for example, those obtainable by reaction of epoxidized olefins or poly- or diglycidyl ethers, such as bisphenol A diglycidyl ether, with (meth)acrylic acid, as known to those skilled in the art.

[0165] Urethane (meth)acrylates are in particular products of the reaction of hydroxylalkyl (meth)acrylates with polyisocyanates or diisocyanates, which are likewise known to those skilled in the art.

[0166] Such epoxides and urethane (meth)acrylates are included among the compounds listed above as "mixed forms."

[0167] When reactive thinners are used, their amount and properties must be matched to the respective conditions so that, on the one hand, a satisfactory desired effect, such as the desired color of the composition according to the invention, is achieved, but, on the other hand, the phase behavior of the liquid crystal composition is not excessively impaired. Low-crosslinking (high-crosslinking) liquid crystal compositions can be prepared, for example, using corresponding reactive thinners with a relatively low (high) number of reactive units per molecule.

[0168] The group of diluents includes, for example: C1-C4 alcohols, such as methanol, ethanol, n-propanol, isopropanol, butanol, isobutanol, sec-butanol, in particular C5-C12 alcohols n-pentanol, n-hexanol, n-heptanol, n-octanol, n-nonanol, n-decanol, n-undecanol, and n-dodecanol, and their isomers; glycols, such as 1,2-ethylene glycol, 1,2- and 1,3-propylene glycol, 1,2-, 2,3-, and 1,4-butylene glycol, di- and triethylene glycol, and di- and tripropylene glycol; ethers, such as methyl tert-butyl ether, 1,2-ethylene glycol mono- and dimethyl ether, 1,2-ethylene glycol mono- and diethyl ether; 3-methoxypropanol; alcohol, 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, tetralin, decalin, dimethylnaphthalene, white spirit, Shellsol® and Solvesso® mineral oils such as gasoline, kerosene, diesel oil, and heating oil, but also natural oils such as olive oil, soybean oil, rapeseed oil, linseed oil, and sunflower oil.

[0169] It is of course also possible to use mixtures of these diluents in the compositions according to the invention.

[0170] These diluents can also be mixed with water, as long as they are at least partially miscible. Examples of suitable diluents herein are C1-C4 alcohols such as methanol, ethanol, n-propanol, isopropanol, butanol, isobutanol, and sec-butanol, glycols such as 1,2-ethylene glycol, 1,2- and 1,3-propylene glycol, 1,2-, 2,3-, and 1,4-butylene glycol, di- and triethylene glycol, and di- 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.

[0171] The diluent is optionally used in a proportion of about 0 to 10.0 wt %, preferably about 0 to 5.0 wt %, based on the total weight of the polymerizable LC material.

[0172] The antifoaming and degassing agents (c1)), lubricants and flow aids (c2)), heat-curing or radiation-curing aids (c3)), substrate-wetting aids (c4)), wetting and dispersing aids (c5)), hydrophobizing agents (c6)), adhesion promoters (c7)), and aids for promoting scratch resistance (c8)) cannot be strictly separated from one another in their action.

[0173] For example, lubricants and flow aids often also function as defoamers and / or degassing agents and / or as aids for improving scratch resistance. Radiation curing aids can also function as lubricants and flow aids and / or degassing agents and / or as substrate wetting aids. In individual cases, some of these aids can also function as adhesion promoters (c8)).

[0174] Therefore, in response to the above, specific additives can be classified into several groups c1) to c8) described below.

[0175] Antifoaming agents of group c1) include silicon-free polymers and silicon-containing polymers, such as unmodified or modified polydialkylsiloxanes or branched copolymers, comb polymers or block copolymers comprising polydialkylsiloxane units and polyether units, the latter units being derived from ethylene oxide or propylene oxide.

[0176] Degassing agents of group c1) include, for example, organic polymers such as polyethers and polyacrylates, dialkylpolysiloxanes, in particular dimethylpolysiloxanes, organomodified polysiloxanes, for example arylalkylmodified polysiloxanes, and fluorosilicones.

[0177] The action of antifoaming agents is essentially based on preventing the formation of foam or destroying already formed foam. Antifoaming agents essentially function by promoting the coalescence of finely divided gases or bubbles to produce larger bubbles in the degassed medium, e.g., the compositions according to the invention, and thus promoting the escape of the gas (air). Antifoaming agents can often also be used as degassing agents, and vice versa, so these additives are included together in group c1).

[0178] Such auxiliaries are available, for example, from TEGO: 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® Antifoam50, 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 from BYK under the trade names 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®- BYK®-035, BYK®-036, BYK®-037, BYK®-045, BYK®-051, BYK®-052, BYK®-053, BYK®-055, BYK®-057, BYK®-065, BYK®-066, BYK®-070, BYK®-080, BYK®-088, BYK®-141, and BYK®-A 530.

[0179] The auxiliaries of group c1) are optionally used in a proportion of about 0 to 3.0 wt. %, preferably about 0 to 2.0 wt. %, based on the total weight of the polymerizable LC material.

[0180] In group c2), lubricants and flow aids typically include silicon-free and silicon-containing polymers, such as polyacrylates or modifiers, such as low-molecular-weight polydialkylsiloxanes. The modification is the replacement of some of the alkyl groups with a wide variety of organic residues. These organic residues are, for example, polyethers, polyesters, or even longer-chain (fluorinated) alkyl residues, the former being the most frequently used.

[0181] The polyether residues in the correspondingly modified polysiloxanes are usually composed of ethylene oxide and / or propylene oxide units. Generally, the higher the proportion of these alkylene oxide units in the modified polysiloxane, the more hydrophilic the resulting product.

[0182] Such aids are commercially available, for example, from Tego 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 an antifoam and degassing agent), TEGO® Flow ATF, TEGO® Flow 300, TEGO® Flow 460, TEGO® Flow 425, and TEGO® Flow ZFS 460. Suitable radiation-curable lubricants and flow aids that 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.

[0183] Such auxiliaries are also available, for example, from BYK as BYK®-300, BYK®-306, BYK®-307, BYK®-310, BYK®-320, BYK®-333, BYK®-341, Byk® 354, Byk® 361, Byk® 361N, BYK® 388.

[0184] Such an auxiliary is also available, for example, from 3M as FC4430®.

[0185] Such agents are also available, for example, from Cytonix as FluorN® 561 or FluorN® 562.

[0186] Such auxiliaries are also available, for example, as Tivida® FL 2300 and Tivida® FL 2500 from Merck KGaA.

[0187] The auxiliaries of group c2) are optionally used in a proportion of about 0 to 3.0 wt. %, preferably about 0 to 2.0 wt. %, based on the total weight of the polymerizable LC material.

[0188] In group c3), radiation curing auxiliaries include, in particular, polysiloxanes having terminal double bonds, such as those constituting acrylate groups. Such auxiliaries can be crosslinked by actinic radiation or, for example, by electron radiation. These auxiliaries usually combine multiple properties. In the uncrosslinked state, they can act as defoamers, degassing agents, lubricants and flow aids, and / or substrate wetting aids, while in the crosslinked state, they particularly enhance the scratch resistance of coatings or films that can be produced using the compositions of the present invention. For example, the improvement in the gloss properties of these coatings or films is essentially a result of the action of these auxiliaries as defoamers, degassing agents, and / or lubricants and flow aids (in the uncrosslinked state).

[0189] Examples of suitable radiation curing coagents 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.

[0190] The heat-curing coagents of group c3) contain primary OH groups which can react with, for example, isocyanate groups of the binder.

[0191] Examples of usable thermal curing coagents are the products BYK®-370, BYK®-373, and BYK®-375 available from BYK.

[0192] The auxiliaries of group c3) are optionally used in a proportion of about 0 to 5.0 wt. %, preferably about 0 to 3.0 wt. %, based on the total weight of the polymerizable LC material.

[0193] The substrate wetting aids of group c4) function in particular to enhance the wetting of the substrate to be printed or coated, for example by a printing ink or coating composition, such as a composition according to the invention. The generally accompanying improvement in the lubrication and flow behavior of such a printing ink or coating composition influences the appearance of the finished (e.g. crosslinked) print or coating.

[0194] A wide variety of such auxiliaries are commercially available, for example from Tego as TEGO® Wet KL 245, TEGO® Wet 250, TEGO® Wet 260, and TEGO® Wet ZFS 453, and from BYK as BYK®-306, BYK®-307, BYK®-310, BYK®-333, BYK®-344, BYK®-345, BYK®-346, and Byk®-348.

[0195] The auxiliary agents of group c4) are optionally used in a proportion of about 0 to 3.0% by weight, preferably about 0 to 1.5% by weight, based on the total weight of the liquid crystal composition.

[0196] The wetting and dispersing auxiliaries of group c5) serve in particular to prevent pigments from running and from floating and settling and are therefore particularly suitable for pigmented compositions, if this is required.

[0197] These auxiliaries stabilize the pigment dispersions essentially via electrostatic repulsion and / or steric hindrance of the pigment particles containing these additives, in the latter case the interaction of the auxiliaries with the surrounding medium (e.g. binder) playing the major role.

[0198] The use of such wetting and dispersing aids is common practice in the art of printing, for example, inks and paints, so that the selection of suitable aids of this type, when used, is usually no problem for a person skilled in the art.

[0199] Such wetting and dispersing aids are available, for example, from TEGO, including 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 from BYK are also trade names Disperbyk®, Disperbyk®-107, Disperbyk®-108, Disperbyk®-110, Disperbyk®-111, Disperbyk®-115, Disperbyk®-130, Disperbyk®-160, Disperbyk®-161, Disperbyk®-162, Disperbyk®-163, Disperbyk®-164, Disperbyk®-165, Disperbyk®-166, Disperbyk®-167, Disperbyk®-168, Disperbyk®-169, Disperbyk®-170, Disperbyk®-171, Disperbyk®-172, Disperbyk®-173, Disperbyk®-174, Disperbyk®-175, Disperbyk®-176, Disperbyk®-177, Disperbyk®-178, Disperbyk®-179, Disperbyk®-180, Disperbyk®-181, Disperbyk®-182, Disperbyk®-183, Disperbyk®-184, Disperbyk®-185, Disperbyk®-186, Disperbyk®-187, Disperbyk®-188, Disperbyk®-189, Disperbyk®-190, Disperbyk®-200, Disperbyk®-201, Disperbyk®-202, Disperbyk®-203, Disperbyk®-204, Disperbyk®-205, Disperbyk®-206, Disperbyk®-207, Disperbyk®-208, Disperbyk®-209, Disperbyk®-210, Disperbyk®-211, Disperbyk® Disperbyk®-165, Disperbyk®-166, Disperbyk®-167, Disperbyk®-170, Disperbyk®-174, Disperbyk®-180, Disperbyk®-181, Disperbyk®-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®-P105, Lactimon®, Lactimon®-WS, and Bykumen®.

[0200] The amounts of auxiliary agents of group c5) were used relative to the average molecular weight of the auxiliary agent.Preliminary experiments are therefore recommended in each case, but can easily be carried out by a person skilled in the art.

[0201] The hydrophobizing agents of group c6) can be used, for example, to impart water repellency to prints or coatings produced using the compositions according to the invention. This prevents or at least significantly reduces swelling due to water absorption and, for example, the resulting change in the optical properties of such prints or coatings. In addition, when the composition is used as a printing ink, for example in offset printing, this can prevent or at least significantly reduce water absorption.

[0202] Such hydrophobizing agents are commercially available, for example, 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.

[0203] The auxiliaries of group c6) are optionally used in a proportion of about 0 to 5.0 wt. %, preferably about 0 to 3.0 wt. %, based on the total weight of the polymerizable LC material.

[0204] Further adhesion promoters from group c7) function to improve the adhesion of two interfaces in contact. From this it is immediately clear that essentially the only part of the adhesion promoter that is effective is the adhesion promoter located at one or the other or both interfaces. For example, if it is desired to apply a liquid or pasty printing ink, coating composition, or paint to a solid substrate, this generally means that the adhesion promoter must be added directly to the solid substrate or the substrate must be pre-treated (also known as priming) with the adhesion promoter. That is, the substrate is endowed with modified chemical and / or physical surface properties.

[0205] If the substrate has been previously primed with a primer, this means that the interfaces in contact are, on the one hand, the interface of the primer and, on the other hand, the interface of the printing ink or coating composition or paint, in which 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 are to some extent involved in the adhesion of the entire multilayer structure on the substrate.

[0206] Adhesion promoters which may be mentioned in the broader sense are also the substrate wetting aids already listed in group c4), although these do not usually have the same adhesion promoting capacity.

[0207] The variety of adhesion promoter systems is not surprising in view of the wide variety of physical and chemical properties of substrates and printing inks, coating compositions and paints, for example, for which they are printed or coated.

[0208] Examples of silane-based adhesion promoters include 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-mercaptopropyltrimethoxysilane, 3-chloropropyltrimethoxysilane, and vinyltrimethoxysilane. These and other silanes are commercially available, for example, from Huels under the trade name DYNASILAN®.

[0209] Corresponding technical information from the manufacturers of such additives should generally be used, or a person skilled in the art can obtain this information in a simple manner through corresponding preliminary experiments.

[0210] However, if these additives are added to the polymerizable LC material according to the invention as auxiliaries from group c7), their proportion optionally corresponds to about 0 to 5.0 wt. %, based on the total weight of the polymerizable LC material. These concentration data serve only as a guideline, since the amount and identity of the additives are determined in each individual case depending on the properties of the substrate and the printing / coating composition. Corresponding technical information in this case is usually available from the manufacturers of such additives or can be determined in a simple manner by those skilled in the art through corresponding preliminary experiments.

[0211] Auxiliaries for improving scratch resistance of group c8) include, for example, the above-mentioned products TEGO® Rad 2100, TEGO® Rad 2200, TEGO® Rad 2500, TEGO® Rad 2600, and TEGO® Rad 2700 available from Tego.

[0212] For these auxiliaries, the amount data shown for group c3) are also applicable, i.e., these additives are optionally used in a proportion of about 0 to 5.0 wt. %, preferably about 0 to 3.0 wt. %, based on the total weight of the liquid crystal composition.

[0213] Examples that may be mentioned of further light, heat and / or oxidation stabilizers 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, linear or branched chain-containing nonylphenols, such as 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methyltridec-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-amylhydroclaynone, 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, as well as tocopherol derivatives, such as tocopheryl acetate, succinate, nicotinate, and polyoxyethylene succinate ("tocofersolate"); hydroxylated diphenyl thioethers, 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-di-sec-amylphenol), and 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl) disulfide; Alkylidenebisphenols, 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-ethylidenebis(4,6-di -tert-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-tert-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-mercaptobutane, 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-mercaptobutane, and 1,1,5,5-tetrakis(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane, O-, N- and S-benzyl compounds, such as 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl 4-hydroxy-3,5-dimethylbenzyl mercaptoacetate, tridecyl 4-hydroxy-3,5-di-tert-butylbenzyl mercaptoacetate, 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 mercaptoacetate, aromatic hydroxybenzyl compounds, such as 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethyl-benzene, 1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethyl-benzene, and 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol; triazine compounds, such as 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-tris(3,5-di-tert-butyl 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 1,3,5-tris-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexahydro-1,3,5-triazine, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate, and 1,3,5-tris(2-hydroxyethyl)isocyanurate, benzyl phosphonates, such as dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, and dioctadecyl 5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate; acylaminophenols, such as 4-hydroxylauroylanilide, 4-hydroxystearoylanilide, and octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate; propionic and acetic acid esters of mono- or polyhydric alcohols such as methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, and 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]-octane; propionamides based on amine derivatives, such as N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine, 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'-di-sec-butyl-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 Diamine, 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-toluenesulfamoyl)diphenylamine, N,N'-dimethyl-N,N'-di-sec-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-nonanoylaminophenol, 4-dodecanoylaminophenol, aminophenol, 4-octadecanoylaminophenol, 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(phenylamino)propane, (o-tolyl)biguanide, bis[4-(1',3'-dimethylbutyl)phenyl]amine, tert-octyl-substituted N-phenyl-1-naphthylamine, mixtures of mono- and dialkylated tert-butyl / tert-octyldiphenylamines, mixtures of mono- and dialkylated nonyldiphenylamines, mixtures of mono- and dialkylated dodecyldiphenylamines, mixtures of mono- and dialkylated isopropyl / isohexyldiphenylamines, mixtures of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine phenothiazine, a mixture of mono- and dialkylated tert-butyl / tert-octylphenothiazines, a mixture of mono- and dialkylated tert-octylphenothiazines, N-allylphenothiazine, N,N,N',N'-tetraphenyl-1,4-diaminobut-2-ene, N,N-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine, bis(2,2,6,6-tetramethylpiperidin-4-yl)sebacate, 2,2,6,6-tetramethylpiperidin-4-one, and 2,2,6,6-tetramethylpiperidin-4-ol, Phosphines, phosphites, and phosphonites, such as triphenylphosnine triphenyl phosphite, diphenyl alkyl phosphite, phenyl dialkyl phosphite, tris(nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl) phosphite, diisodecyl pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, bis(2,4,6-tris(tert-butylphenyl))pentaerythritol diphosphite, bis(2,4,6-tris(tert-butylphenyl))pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)4,4'-biphenylene diphosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioxaphosphocin, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz[d,g]-1,3,2-dioxaphosphocin, bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite, and bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 2-(2'-hydroxyphenyl)benzotriazoles, 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'-te rt-butyl-2'-hydroxy-5'-methylphenyl)-5-chlorobenzotriazole, 2-(3'-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazole, 2-(3',5'-di-tert-amyl-2'-hydroxyphenyl)benzotriazole, 2-(3,5'-bis-(α,α-dimethylbenzyl)-2'-hydroxyphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole, and 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole. a mixture of 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)benzotriazole, 2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl)benzotriazole and 2-(3'-tert-butyl-2'-hydroxy-5'-(2-isooctyloxycarbonylethyl)phenylbenzotriazole, 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-ylphenol]; 2-[3'-tert-butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazole fully esterified with polyethylene glycol 300; sulfur-containing peroxide scavengers and sulfur-containing antioxidants, such as esters of 3,3'-thiodipropionic acid, such as the lauryl, stearyl, myristyl, and tridecyl esters, mercaptobenzimidazole, and zinc salts of 2-mercaptobenzimidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, and pentaerythritol tetrakis(β-dodecylmercapto)propionate; 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; sterically hindered amines such as bis(2,2,6,6-tetramethylpiperidin-4-yl) 1-(2-hydroxyethyl)-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-hydroxybenzyl malonate, 1-(2-hydroxyethyl)-2,2,6,6 -Condensation products of tetramethyl-4-hydroxypiperidine and succinic acid, condensation products of N,N'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, 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-ethylene)bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-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, condensation products of N,N'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, 2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidin-4-yl)-1, Condensation products of 3,5-triazine and 1,2-bis(3-aminopropylamino)ethane, condensation products of 2-chloro-4,6-di(4-n-butylamino-1,2,2,6,6-pentamethylpiperidin-4-yl)-1,3,5-triazine and 1,2-bis(3-aminopropylamino)ethane, 8-acetyl-3-dodecyl-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- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine, condensation products of N,N'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, 1,2-bis(3-aminopropylamino)ethane and 2,4,6-trichloro-1,3,5-triazine Condensation products with riazine, 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, 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro-[4.5] Condensation products of decane and epichlorohydrin, condensation products of 4-amino-2,2,6,6-tetramethylpiperidine and tetramethylolacetylenediurea, and poly(methoxypropyl-3-oxy)-[4(2,2,6,6-tetramethyl)piperidinyl]-siloxane. Oxalamides, such as 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxalamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and mixtures thereof with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, and mixtures of ortho-, para-methoxy-disubstituted oxanilides, and mixtures of ortho- and para-ethoxy-disubstituted oxanilides, and 2-(2-hydroxyphenyl)-1,3,5-triazines, such as 2,4,6-tris-(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)- 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4 ,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[4-(dodecyloxy / tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis -(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-hexyloxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazine, and 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine.

[0214] In another preferred embodiment, the polymerizable LC material comprises one or more specific antioxidant additives, preferably selected from the Irganox® series, such as the antioxidants Irganox® 1076 and Irganox® 1010, available commercially from Ciba (Switzerland).

[0215] In another preferred embodiment, the polymerizable LC material comprises one or more, more preferably one or two, photoinitiators, such as those selected 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 2022, Irgacure 2100, Irgacure 2959, or Darcure TPO, as well as those selected from the commercially available OXE02 (Ciba AG), NCI 930, N1919T (Adeka), SPI-03 or SPI-04 (Samyang), or preferably combinations thereof, such as SPI-03 and NCI-930.

[0216] The overall concentration of the polymerization initiator in the polymerizable LC material is preferably 0.5-5%, very preferably 0.5-3%, more preferably 1-2%.

[0217] Preferably, the polymerisable LC material contains in addition to one or more compounds of formula UVI a) one or more di- or multi-reactive 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 mono-, di- or multi-reactive polymerizable non-mesogenic compounds; g) optionally, one or more dyes that exhibit an absorption maximum at the wavelength used to initiate photopolymerization; h) optionally one or more chain transfer agents; i) optionally one or more stabilizers; j) optionally one or more lubricants and flow aids; and k) optionally one or more diluents; l) Optional Non-Polymerizable Nematic Component Includes.

[0218] More preferably, the polymerizable LC material is a) one or more compounds of formula UVI, b) preferably, if present at all, in an amount of 10 to 90% by weight, very preferably 15 to 75% by weight, of one or more, preferably two or more, direactive polymerizable mesogenic compounds, preferably selected from compounds of formula DRMa-1, c) optionally one or more, preferably two or more, monoreactive polymerizable mesogenic compounds, preferably selected from compounds of formula MRM-1 and / or MRM-7, preferably in an amount of 10 to 95% by weight, very preferably 25 to 85%, d) optionally one or more compounds of formula ND, preferably in an amount of 1 to 50%, very preferably 1 to 40%, e) if present, optionally one or more antioxidant additives, preferably in an amount of 0.01 to 2% by weight, very preferably 0.05 to 1% by weight, preferably an antioxidant additive chosen from unsubstituted or substituted esters of benzoic acid, in particular Irganox® 1076, f) if present, preferably 0.1 to 5 wt. %, very preferably 0.2 to 3 wt. %, of one or more optional lubricants and flow aids, preferably selected from BYK® 388, FC 4430, Fluor N 561 and / or Fluor N 562; and g) optional one or more photoinitiators Includes.

[0219] The present invention further comprises: - providing a layer of a polymerizable LC material as described above and below on a substrate, - polymerizing the 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. The present invention relates to a method for producing a polymer film according to the present invention.

[0220] The polymerizable LC material can also be dissolved in a suitable solvent.

[0221] 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 acetoacetate; alcohols such as methanol, ethanol, or isopropyl alcohol; aromatic solvents such as toluene or xylene; alicyclic hydrocarbons such as cyclopentane or cyclohexane; halogenated hydrocarbons such as dichloromethane or trichloromethane; glycols or their esters, such as PGMEA (propyl glycol monomethyl ether acetate) or γ-butyrolactone. It is also possible to use binary, ternary, or more mixtures of the above solvents.

[0222] When the polymerizable LC material contains one or more solvents, the total concentration of all solids, including the RM, in the solvent is preferably 10-60%.

[0223] The solution is then coated or printed onto a substrate, for example by spin coating, printing, or other known techniques, and the solvent is allowed to evaporate before polymerization. In most cases, it is appropriate to heat the mixture to facilitate evaporation of the solvent.

[0224] The polymerizable LC material can be applied to the substrate by conventional coating techniques such as spin coating, bar coating or blade coating. It can also be applied to the substrate by conventional printing techniques known to those skilled in the art, such as screen printing, offset printing, reel-to-reel printing, letterpress printing, gravure printing, rotogravure printing, flexographic printing, intaglio printing, pad printing, heat seal printing, inkjet printing or printing by stamp or printing plate.

[0225] Suitable substrate materials and substrates are known to those skilled in the art and are described in the literature, for example, as conventional substrates used in 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 commonly known color filter materials, particularly triacetyl cellulose (TAC), cycloolefin polymers (COP), or commonly known color filter materials.

[0226] The polymerizable LC material preferably exhibits uniform alignment throughout the layer, preferably uniform planar or uniform homeotropic alignment.

[0227] The Friedel-Creagh-Kmetz law can be used to predict whether a mixture will adopt a planar or homeotropic alignment by comparing the surface energies of the RM layer and the substrate.

[0228] gamma RM >γ s In the case of γ, the reactive mesogenic compound exhibits homeotropic alignment, RM <γ s In this case, the reactive mesogenic compound exhibits uniform alignment.

[0229] 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, and therefore the reactive mesogens align perpendicular to the substrate (homeotropic alignment) to maximize the intermolecular forces.

[0230] 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, and the hydrocarbon tail is oriented perpendicular to the substrate. Intermolecular interactions between the amphiphile and the RM promote homeotropic alignment. Commonly used amphiphilic surfactants are listed above.

[0231] Another method used to promote homeotropic alignment is to apply a corona discharge treatment to plastic substrates to generate alcohol or ketone functional groups on the substrate surface. These polar groups can interact with polar groups present in RMs or surfactants to promote homeotropic alignment.

[0232] When the surface tension of the substrate is greater than that of the RM, the forces across the interface dominate. When the reactive mesogens are oriented parallel to the substrate, the interfacial energy is minimized, allowing the long axis of the RM to interact with the substrate. One method that can promote planar alignment is to coat the substrate with a polyimide layer and then rub the alignment layer with a velvet cloth.

[0233] Other suitable planar alignment layers are known in the art, such as rubbed polyimides or alignment layers produced by photoalignment as described, for example, in U.S. Pat. No. 5,602,661, U.S. Pat. No. 5,389,698, or U.S. Pat. No. 6,717,644.

[0234] In general, reviews of alignment techniques are given, for example, by I. Sage in "Thermotropic Liquid Crystals", G. W. Gray, John Wiley & Sons, 1987, pp. 75-77; and by T. Uchida and H. Seki in "Liquid Crystals - Applications and Uses Vol. 3", B. Bahadur, World Scientific Publishing, Singapore, 1992, pp. 1-63. A further review of alignment materials and techniques is given in J. Cognard, Mol. Cryst. Liq. Cryst. 78, Supplement 1 (1981), pp. 1-77.

[0235] For the preparation of the polymer film according to the present invention, the polymerizable compounds in the polymerizable LC material are polymerized or crosslinked (if one compound contains two or more polymerizable groups) by in situ photopolymerization.

[0236] Photopolymerization can be carried out in one step. Compounds that did not react in the first step can also be photopolymerized or crosslinked in a second step ("final cure").

[0237] In a preferred method of preparation, the polymerizable LC material is coated onto a substrate and subsequently photopolymerized, e.g. by exposure to actinic radiation, as described, e.g., in WO 01 / 20394, GB 2315072 or WO 98 / 04651.

[0238] Photopolymerization of the LC material is preferably achieved by exposing it to actinic radiation. Actinic radiation refers to irradiation with light, such as UV, IR, or visible light, or irradiation with X-rays or gamma rays, or irradiation with high-energy particles, such as ions or electrons. Preferably, polymerization is carried out by photoirradiation, especially with UV light. A single UV lamp or a series of UV lamps can be used as a source of actinic radiation. Using high lamp power can shorten the curing time. Another possible source of photoradiation is a laser, such as a UV laser, an IR laser, or a visible laser.

[0239] The curing time depends, inter alia, 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. The curing time is preferably within 5 minutes, very preferably within 3 minutes, and most preferably within 1 minute. For mass production, short curing times of 30 seconds or less are preferred.

[0240] Suitable UV radiation power is preferably between 5 and 200 mW cm -2 More preferably, it is in the range of 50 to 175 mWcm -2 The range is most preferably 100 to 150 mWcm -2 The range is.

[0241] In relation to the applied UV radiation and as a function of time, a suitable UV dose is preferably between 25 and 7200 mJ cm -2 More preferably, it is in the range of 500 to 7200 mJcm -2 and most preferably in the range of 3000 to 7200 mJcm -2 The range is.

[0242] Photopolymerization is preferably carried out under an inert gas atmosphere, preferably a heated nitrogen atmosphere, although polymerization in air is also possible.

[0243] The photopolymerization is carried out at a temperature of preferably 1 to 70°C, more preferably 5 to 50°C, and even more preferably 15 to 30°C.

[0244] The polymerized LC films according to the present invention have good adhesion to plastic substrates, especially TAC, COP, and color filters, and can therefore be used as adhesives or base coatings for subsequent LC layers that would otherwise not adhere well to the substrate.

[0245] The preferred thickness of the polymerized LC film according to the present invention is determined by the optical properties desired from the film or the final product, for example, if the polymerized LC film does not function primarily as an optical layer but functions, for example, as an adhesive, alignment layer, or protective layer, its thickness is preferably 1 μm or less, in particular 0.5 μm or less, very preferably 0.2 μm or less.

[0246] For example, the uniformly homeotropically or planarly oriented polymer films of the present invention can be used as retardation films or compensation films, for example, in LCDs, to improve contrast and brightness at large viewing angles and reduce chromaticity. They can be used outside the switchable liquid crystal cell in LCDs, or between substrates, usually glass substrates, that form the switchable liquid crystal cell and contain the switchable liquid crystal medium (in cell applications).

[0247] For optical applications of the polymer film, this preferably has a thickness of 0.5 to 10 μm, very preferably 0.5 to 5 μm, in particular 0.5 to 3 μm.

[0248] The optical retardation (δ(λ)) of a polymer film as a function of the wavelength (λ) of the incident beam is given by the following equation (7): δ(λ)=(2πΔn d) / λ (7) is given by where (Δn) is the birefringence of the film, (d) is the thickness of the film, and λ is the wavelength of the incident beam.

[0249] According to Snell's law, birefringence as a function of incident beam direction is defined as: Δn=sinΘ / sinΨ (8) where sin Θ is the angle of incidence or tilt of the optical axis within the film, and sin Ψ is the corresponding angle of reflection.

[0250] Based on these laws, the birefringence and therefore the optical retardation depend on the film thickness and the tilt angle of the optical axis within the film (see Berek's compensator). Therefore, those skilled in the art recognize that adjusting the orientation of the liquid crystal molecules in the polymer film can result in different optical retardations or different birefringences.

[0251] 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.

[0252] The optical retardation as a function of thickness of the polymer films according to the invention is less than 200 nm, preferably less than 180 nm, more preferably less than 150 nm.

[0253] The polymer films of the present invention can also be used as alignment films for other liquid crystal or RM materials. For example, they can be used in LCDs to induce or improve the alignment of switchable liquid crystal media or to align subsequent layers of polymerizable LC materials coated on them. In this way, stacks of polymerized LC films can be produced.

[0254] In summary, the polymerized LC films and polymerizable LC materials according to the present invention are useful in optical elements such as polarizers, compensators, alignment layers, circular polarizers or color filters in liquid crystal displays or projection systems, in decorative images for the production of liquid crystal or effect pigments, and in particular in reflective films with spatially varying reflected color, as multicolor images for decoration, information storage or security applications, e.g. in unforgeable documents such as identity cards, credit cards or banknotes.

[0255] The polymerized LC films according to the present invention can be used in transmissive or reflective displays, such as conventional OLED displays or LCDs, in particular DAP (aligned phase transformation) or VA (vertically aligned) LCDs, such as ECB (electrically controlled birefringence), CSH (color super homeotropic), VAN or VAC (vertically aligned nematic or cholesteric) displays, MVA (multi-domain vertical alignment) or PVA (patterned vertical alignment) displays, bend mode displays or hybrid displays, such as OCB (optically compensated bend cell or optically compensated birefringence), R-OCB (reflective OCB), HAN (hybrid aligned nematic) or pi-cell (π-cell) displays, as well as TN (twisted nematic), HTN (highly twisted nematic) or STN (super twisted nematic) displays, AMD-TN (active matrix driven TN) displays, or IPS (in-plane switching) displays (also known as "super TFT" displays). VA, MVA, PVA, OCB, and pi-cell displays are particularly preferred.

[0256] The polymerizable LC materials and polymer films according to the present invention are particularly useful for 3D displays as described in EP 0829744, EP 0887666, EP 0887692, US 6046849, US 6437915 and in "Proceedings of the SID 20th International Display Research Conference, 2000", page 280. 3D displays of this type comprising polymer films according to the present invention are another subject of the present invention.

[0257] The present invention has been described above and hereinafter with particular reference to preferred embodiments. It is to be understood that various changes and modifications can be made therein without departing from the spirit and scope of the invention.

[0258] Many of the compounds or mixtures thereof mentioned above and below are commercially available. All of these compounds are known or can be prepared by methods known per se and under known and suitable reaction conditions as described in the literature (e.g., standard treatises such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart) precisely under known reaction conditions suitable for the reaction. Variants known per se but not mentioned here can also be used here.

[0259] It will be understood that variations to the above-described embodiments of the invention may be made while remaining within the scope of the invention. Alternative features serving the same, equivalent, or similar purpose may replace each feature disclosed herein, unless otherwise stated. Thus, unless otherwise stated, each feature disclosed is only one example of a generic series of equivalent or similar features.

[0260] All features disclosed herein can be combined in any combination, except combinations in which at least some of such features and / or steps are mutually exclusive. In particular, preferred features of the invention are applicable to all aspects of the invention and can be used in any combination. Similarly, features described in non-essential combinations can be used separately (not in combination).

[0261] It will be appreciated that many of the features described above, particularly the preferred embodiments, are inventive in their own right and are not merely part of one embodiment of the present invention, and independent protection may be sought for these features in addition to, or as an alternative to, the full invention as recited in the claims.

[0262] The present invention will now be further described by reference to the following examples, which are illustrative only and are not intended to limit the scope of the invention.

[0263] Example Basic steps The mixture was dissolved in toluene / cyclohexanone (7 / 3) to a solids content of 33.3%. The solution was spin-coated at 2000 rpm onto a rubbed PI-coated glass substrate. The film was annealed at 68 °C for 120 s and then heated on a Fusion conveyor with an H bulb (power 95%, 10 m / min, approximately 300 mJ / cm). 2 , UV B) under N2 atmosphere.

[0264] The film is laminated to the pressure sensitive adhesive, leaving an open surface. The resulting overall film laminate is glass / polymer film / pressure sensitive adhesive. Durability testing is performed on this film.

[0265] To measure the difference in retardation and dispersion of the cured film depending on thermal stress, an Axoscan ellipsometer is used to determine the initial retardation and dispersion. The film is then irradiated with a Suntest XLS+ (350 W / m 2 ) for up to 120 hours. After the test, the retardation profile and dispersion are measured again. Durability is evaluated by measuring the retardation (ΔR in ) and / or variance (R 450 / 550 ) is quantified by the difference.

[0266] The compound of formula UVI was used [ka]

[0267] Example 1 The following mixture M1 RMM is prepared according to the table below: [Table 1]

[0268] Mixture M1 is divided into two parts: one is mixed with 1.5% w / w UVI-a and the other is left unchanged.

[0269] Each mixture is dissolved, coated and cured as described above and the change in retardation and dispersion is determined before and after stress testing. The results are summarized in the following table.

[0270] [Table 2]

Claims

1. at least one direactive mesogenic compound, at least one monoreactive mesogenic compound, and one or more compounds of formula UVI 【Chemistry 1】 and a polymerizable LC material comprising a compound of the formula The individual residues have the following meanings: R １ ~R ５ are each independently H, -alkyl, -OH, -alkylaryl, -alkylheteroaryl, -cycloalkyl, cycloheteroalkyl, alkenyl, aryl, and -SO ３ H, R ６ and R ７ forms an optionally substituted cycloalkyl or cycloheteroalkyl ring; The compound of formula UVI has the following sub-formula: 【Chemistry 2】 is a compound of The at least one direactive mesogenic compound has the following formula: 【Transformation 3】 [In the formula, P ０ when there are a plurality of them, each independently represents an acrylic, methacrylic, oxetane, epoxy, vinyl, heptadiene, vinyloxy, propenyl ether or styrene group; L is the same or different in each occurrence and is 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 , optionally substituted silyl, aryl or heteroaryl having 1 to 12 C atoms, linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl, R ００ and R ０００ represent, independently of one another, H or alkyl having 1 to 12 C atoms, r is 0, 1, 2, 3 or 4; x and y are each independently 0 or the same or different integers from 1 to 12; z is independently 0 or 1, and when adjacent x or y is 0, z is 0; and The at least one monoreactive mesogenic compound is represented by the formula 【Chemistry 4】 [In the formula, P ０ is an acrylic, methacrylic, oxetane, epoxy, vinyl, heptadiene, vinyloxy, propenyl ether or styrene group; x is 0 or an integer from 1 to 12; z is 0 or 1, and when the adjacent x is 0, z is 0; R ０ is an alkyl, alkoxy, thioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having one or more C atoms, or Y ０ represents Y ０ are F, Cl, CN, NO ２ , OCH ３ , OCN, SCN, SF ５ or a mono-, oligo- or polyfluorinated alkyl or alkoxy having 1 to 4 C atoms, wherein said benzene ring may be further substituted with one or more identical or different groups L.

2. One or more compounds of formula ND: 【Transformation 5】 [In the formula, U １，２ are independent of each other, 【Transformation 6】 (including mirror images thereof), wherein said ring U １ and U ２ are each connected to the group -(B) via an axial bond. ｑ -, and one or two non-adjacent CH ２ The group is optionally replaced by O and / or S, and the ring U １ and U ２ is optionally substituted by one or more groups L, L is the same or different in each occurrence and 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 , optionally substituted silyl, aryl or heteroaryl having 1 to 12 C atoms, linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl, P represents a polymerizable group; Sp is a spacer group or a single bond; R ００ and R ０００ represent, independently of one another, H or alkyl having 1 to 12 C atoms, Q １，２ are each independently CH or SiH, Q ３ is C or Si, B, in each occurrence, independently of each other, is -C≡C-, -CY １ =CY ２ - or an optionally substituted aromatic or heteroaromatic group; Y １，２ are each independently H, F, Cl, CN or R ０ and 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 joined by one or more groups R ５ Optionally substituted with -(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 each of - does not contain more aromatic groups than non-aromatic groups; Z １～４ are each independently —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, or —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 of one another, H or alkyl 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 each independently H, halogen, —CN, —NC, —NCO, —NCS, —OCN, —SCN, or —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-, optionally substituted silyl, or carbyl or hydrocarbyl having 1 to 40 C atoms, optionally substituted and optionally containing one or more heteroatoms, or represent P or P-Sp- or are substituted by P or P-Sp-, wherein the compound contains at least one group R １～５ Including, P is a polymerizable group, Sp is a spacer group or a single bond; The polymerizable LC material according to claim 1 , wherein the polymerizable group is selected from a group containing a C═C double bond or a C≡C triple bond, and an oxetane group or an epoxide group.

3. 3. The polymerizable LC material according to claim 1 or 2, wherein the proportion of the at least one direactive mesogenic compound is in the range of 5 to 99% by weight.

4. 3. The polymerizable LC material according to claim 1 or 2, wherein the proportion of said at least one monoreactive mesogenic compound is in the range of 5 to 80 wt.%.

5. 5. The polymerizable LC material according to any one of claims 1 to 4, optionally comprising one or more additives selected from the group consisting of surfactants, further stabilizers, catalysts, sensitizers, inhibitors, chain transfer agents, co-reactant monomers, reactive thinners, surface-active compounds, lubricants, wetting agents, dispersants, hydrophobizing agents, adhesives, flow improvers, defoamers or antifoaming agents, degassing agents, diluents, reactive diluents, auxiliaries, colorants, dyes, pigments and nanoparticles.

6. A method for producing a polymerizable LC material according to any one of claims 1 to 5, comprising a step of mixing the one or more compounds of formula UVI with the at least one direactive mesogenic compound and the at least one monoreactive mesogenic compound.

7. A method for producing a polymer film, comprising: - providing a layer of a polymerizable LC material according to any one of claims 1 to 5 on a substrate, - photopolymerising said polymerisable LC material, and - optionally removing the polymerized LC material from the substrate and / or optionally providing it on another substrate. A method for producing a polymer film.

8. 6. Use of the polymerizable LC material according to any one of claims 1 to 5 in optical, electro-optical, information storage, decorative and security applications.

9. 6. An optical element or device, polarizer, patterned retarder, compensator, alignment layer, circular polarizer, color filter, decorative image, liquid crystal lens, liquid crystal pigment, reflective film with spatially varying reflected color, multicolor image for decoration or information storage, comprising a polymerizable LC material according to any one of claims 1 to 5.

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