WO2017003268A1 - Guest-host type liquid crystal composition - Google Patents

Guest-host type liquid crystal composition Download PDF

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Publication number
WO2017003268A1
WO2017003268A1 PCT/KR2016/007194 KR2016007194W WO2017003268A1 WO 2017003268 A1 WO2017003268 A1 WO 2017003268A1 KR 2016007194 W KR2016007194 W KR 2016007194W WO 2017003268 A1 WO2017003268 A1 WO 2017003268A1
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WO
WIPO (PCT)
Prior art keywords
liquid crystal
group
polarizing element
dye
crystal composition
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PCT/KR2016/007194
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French (fr)
Korean (ko)
Inventor
이지연
김신영
박문수
이대희
Original Assignee
주식회사 엘지화학
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Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2017506996A priority Critical patent/JP6500286B2/en
Priority to CN201680002662.XA priority patent/CN106715649B/en
Priority to US15/504,972 priority patent/US10495797B2/en
Priority claimed from KR1020160084188A external-priority patent/KR102118367B1/en
Publication of WO2017003268A1 publication Critical patent/WO2017003268A1/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/60—Pleochroic dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements

Definitions

  • the present application relates to the use of a guest host type liquid crystal composition, a polarizing element and a polarizing element.
  • the polarizing element used in the display device may be, for example, a polyvinyl alcohol (PVA) film in which iodine is salted and a protective film for protecting the same, for example, a triacetylcellulose (TAC) film. It is formed in a composite film structure.
  • PVA polyvinyl alcohol
  • TAC triacetylcellulose
  • a coated polarizing element using a dichroic dye has a poor heat resistance and therefore, a dye at a high temperature condition.
  • the absorption spectrum is changed due to the decomposition of molecules, which limits its use in display devices. Accordingly, in the field of display devices, research on the development of a coating type polarizing device capable of securing heat resistance has been increasing.
  • the present application provides the use of a guest host type liquid crystal composition, a polarizer and a polarizer.
  • the present application relates to a guest host type liquid crystal composition.
  • An exemplary guest host type liquid crystal composition may include a polymerizable liquid crystal compound and a dichroic dye that do not include an acryloyl based polymerizable functional group.
  • the guest host type liquid crystal composition may mean, for example, a liquid crystal composition having a characteristic capable of forming a polarizing element exhibiting an anisotropic light absorption effect.
  • the guest-host type liquid crystal composition is, for example, as described later, dichroic dyes are arranged together in accordance with the arrangement of the polymerizable liquid crystal compound to absorb light parallel to the alignment direction of the dye and transmit the vertical light, The polarizing element which shows an isotropic light absorption effect can be formed.
  • the liquid crystal composition of the present application may exhibit excellent heat resistance even after polymerization to the liquid crystal layer.
  • the liquid crystal composition may satisfy Equation 1 below.
  • W may mean the maximum absorption wavelength of the dye immediately after the polymerizable liquid crystal compound is polymerized
  • H is the dye of the dye after maintaining the liquid crystal composition polymerized with the liquid crystal compound at 100 ° C for 100 hours It may mean the maximum absorption wavelength. That is, in the liquid crystal composition, the absolute value of the maximum absorption wavelength change rate of the dye under the high temperature condition calculated by Equation 1 may be 20 or less.
  • the maximum absorption wavelength change rate of the dye calculated by Equation 1 may be, more specifically, within a range of ⁇ 17.5, a range of ⁇ 15, a range of ⁇ 12.5, or a range of ⁇ 10.
  • the rate of change of the maximum absorption wavelength of the dye can be calculated by measuring the absorption spectrum of the dye layer described in the Examples described later.
  • the "polymerizable liquid crystal compound” may mean a compound including a site capable of exhibiting liquid crystallinity, for example, a mesogen skeleton, and the like, and including one or more polymerizable functional groups.
  • the liquid crystal composition of the present application may include a polymerizable liquid crystal compound that does not include an acryloyl series polymerizable functional group as the polymerizable functional group.
  • the acryloyl-based polymerizable functional group may be, for example, a meaning representing a functional group polymerizable by a radical reaction, and for example, may include acryloyl group or methacryloyl group.
  • the liquid crystal composition of the present application may include, as a main component, a polymerizable liquid crystal compound that does not contain an acryloyl based polymerizable functional group.
  • a polymerizable liquid crystal compound that does not contain an acryloyl based polymerizable functional group.
  • the term “main ingredient” means that at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, or at least about 95% by weight of the composition is included in the composition. can do.
  • a cationically polymerizable liquid crystal compound As a polymerizable liquid crystal compound which does not contain an acryloyl type polymerizable functional group, a cationically polymerizable liquid crystal compound can be used, for example.
  • the cationic polymerizable liquid crystal compound may mean, for example, a liquid crystal compound having at least one or more functional groups polymerizable by a cationic polymerization reaction.
  • an epoxy group can be illustrated, for example.
  • the cationically polymerizable liquid crystal compound is, for example, a monofunctional polymerizable liquid crystal compound containing one epoxy group or two or more epoxy groups, for example, 2 to 10, 2 to 8, 2 It may be a multi-functional polymerizable liquid crystal compound containing 6 to 6, 2 to 5, 2 to 4, 2 to 3 or two.
  • the compound represented by following formula (1) can be used, for example.
  • A is a single bond, -COO- or -OCO-
  • R 1 to R 10 are each independently hydrogen, halogen, alkyl group, alkoxy group, alkoxycarbonyl group, nitro group, epoxy group, cyano group,- OQP or a substituent of Formula 2, wherein at least one of R 1 to R 10 is an epoxy group, a cyano group, -OQP or a substituent of Formula 2, or two adjacent substituents of R 1 to R 5 or R 6 to R 10 Two adjacent substituents are connected to each other to form a benzene substituted with -OQP, wherein Q is an alkylene group or an alkylidene group, and P is an epoxy group:
  • B is a single bond, -COO-, or -OCO-
  • R 11 To R 15 are each independently hydrogen, halogen, alkyl group, alkoxy group, alkoxycarbonyl group, nitro group, epoxy group, cyano group or -OQP, wherein at least one of R 11 to R 15 is an epoxy group, cyano group, or -OQP Or R 11 Two adjacent substituents of R to R 15 are connected to each other to form a benzene substituted with —OQP, wherein Q is an alkylene group or an alkylidene group, and P is an epoxy group.
  • adjacent two substituents may be linked to each other to form benzene substituted with -OQP, which may mean that two adjacent substituents are connected to each other to form a naphthalene skeleton substituted with -OQP as a whole. have.
  • single bond refers to a case in which a separate atom is not present in a portion represented by A or B.
  • A is a single bond in Formula 1
  • benzene on both sides of A may be directly connected to form a biphenyl structure.
  • alkyl group is a straight or branched chain alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, or 3 to 20 carbon atoms, It may mean a cycloalkyl group having 3 to 16 carbon atoms or 4 to 12 carbon atoms.
  • the alkyl group may be optionally substituted with one or more substituents.
  • alkoxy group may mean an alkoxy group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms.
  • the alkoxy group may be linear, branched or cyclic.
  • the alkoxy group may be optionally substituted with one or more substituents.
  • alkylene group or alkylidene group may mean an alkylene group or an alkylidene group having 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, unless otherwise specified.
  • the alkylene group or alkylidene group may be linear, branched or cyclic.
  • the alkylene group or alkylidene group may be optionally substituted with one or more substituents.
  • an alkenyl group in the present specification may mean an alkenyl group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms, unless otherwise specified.
  • the alkenyl group may be linear, branched or cyclic.
  • the alkenyl group may be optionally substituted with one or more substituents.
  • an alkyl group, an alkoxy group, an alkenyl group, an oxo group, an oxetanyl group, a thiol group, an epoxy group, or a cyano group, etc. can be illustrated, Preferably it is substituted by an epoxy group It is good to be
  • the liquid crystal composition may also include a dichroic dye as described above.
  • the dye may refer to a material capable of intensively absorbing and / or modifying light in at least part or the entire range, for example, in the visible light region, for example, in the 400 nm to 700 nm wavelength range
  • Dichroic dye may refer to a material capable of anisotropic absorption of light in at least part or the entire range of the visible light region.
  • the dichroic dye for example, a known dye known to be capable of forming a so-called guest host type liquid crystal device, for example, a known dye known to have a property that can be oriented according to the orientation of the polymerizable liquid crystal compound is selected. Can be used.
  • Such dichroic dyes may also be used, for example, dyes having a maximum absorbance in the visible region, for example 400 nm to 700 nm.
  • Such dyes may include, but are not limited to, for example, one or more dyes of cyan dye, anthraquinone dye, acridine dye, cyanine dye, and naphthalene dye.
  • a dichroic ratio that is, a value obtained by dividing the absorption of polarization parallel to the long axis direction of the anisotropic dye by the absorption of polarization parallel to the direction perpendicular to the long axis direction is 5 or more, 6 or more, Dye which is 7 or more, 8 or more, 9 or more, or 10 or more can be used.
  • the dye may satisfy the dichroic ratio at at least some of the wavelengths or at any one within the wavelength range of the visible region, for example, in the wavelength range of about 380 nm to 700 nm or about 400 nm to 700 nm.
  • the upper limit of the dichroic ratio may be, for example, about 20 or less, 18 or less, 16 or less, or about 14 or less.
  • the content of the dichroic dye in the liquid crystal composition may be appropriately selected within a range that does not impair the desired physical properties.
  • the dichroic dye may be included in a ratio within the range of 0.1 parts by weight to 20 parts by weight with respect to 100 parts by weight of the polymerizable liquid crystal compound.
  • the dichroic dye is 0.1 part by weight, 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight, or more, based on 100 parts by weight of the polymerizable compound, It may be included in the range of 7 parts by weight or more, 8 parts by weight, 9 parts by weight or 10 parts by weight or more, and 20 parts by weight or less, 19 parts by weight or less, 18 parts by weight or less, relative to 100 parts by weight of the polymerizable compound. It may be included in the range of up to 16 parts by weight, up to 15 parts by weight, up to 14 parts by weight, up to 13 parts by weight, up to 12 parts by weight or up to 11 parts by weight.
  • the liquid crystal composition may further include a cationic initiator when the cationic polymerizable liquid crystal compound is included as the polymerizable liquid crystal compound.
  • cation initiators include ionization cation initiators of onium salts or organometallic salts, or nonionization cation initiators such as organic silanes or latent sulfonic acid series or other non-ionizing compounds. Can be used.
  • onium salt-based initiator include a diaryliodonium salt, a triarylsulfonium salt, an aryldiazonium salt, and the like. As the zero, iron arene and the like can be exemplified.
  • organosilane-based initiator examples include o-nitrobenzyl triaryl silyl ether and triaryl silyl peroxide.
  • an acyl silane (acyl silane) may be exemplified
  • a latent sulfuric acid-based initiator may be exemplified by a-sulfonyloxy ketone or a-hydroxymethylbenzoin sulfonate, but is not limited thereto.
  • a mixture of an iodine-based initiator and a photosensitizer may be used as the cationic initiator.
  • photosensitizers include anthracene compounds, pyrene compounds, carbonyl compounds, organic sulfur compounds, persulfides, redox compounds, azo and diazo compounds, halogen compounds or photoreducing dyes.
  • the content of the cationic initiator may be appropriately adjusted according to the degree of polymerization desired, for example, it may be included in a ratio within the range of 0.1 parts by weight to 20 parts by weight of 100 parts by weight of the cationic polymerizable liquid crystal compound.
  • the ionic initiator is 0.1 part by weight, 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight or more, based on 100 parts by weight of the polymerizable compound, It may be included in the range of 7 parts by weight or more, 8 parts by weight, 9 parts by weight or 10 parts by weight or more, and 20 parts by weight or less, 19 parts by weight or less, 18 parts by weight or less, relative to 100 parts by weight of the polymerizable compound. It may be included in the range of up to 16 parts by weight, up to 15 parts by weight, up to 14 parts by weight, up to 13 parts by weight, up to 12 parts by weight or up to 11 parts by weight.
  • the present application also relates to a polarizing element.
  • the polarizing element may include, for example, the polymer layer of the guest host liquid crystal composition described above. That is, a polarizing element can contain the polymeric layer of the host guest type liquid crystal composition containing the polymeric liquid crystal compound and dichroic dye which do not contain an acryloyl type polymeric functional group. Therefore, the content of the polymerizable liquid crystal compound and the dichroic dye in the polarizing device may be the same as described in the item of the liquid crystal composition.
  • Such a polarizing element may exhibit excellent heat resistance.
  • the polarizer may satisfy Equation 1 below. Details of the following Equation 1 may also be applied in the same manner described in the item of the liquid crystal composition.
  • Equation 1 W is the maximum absorption wavelength of the dye immediately after the polymerizable liquid crystal compound is polymerized, and H is the maximum absorption wavelength of the dye after holding the liquid crystal composition polymerized with the liquid crystal compound at 100 ° C. for 100 hours.
  • the polymerization layer may be, for example, a coating layer of a polarizing material including a polymerizable liquid crystal compound and a dichroic dye that do not include an acryloyl based polymerizable functional group.
  • the polymerizable liquid crystal compound may be, for example, a cationic polymerizable liquid crystal compound, more specifically, a liquid crystal compound having a cationically polymerizable functional group such as an epoxy group.
  • Such a polarizing device may be manufactured by, for example, a simple coating process, so that the polarizing device may be manufactured at low cost, and thinning of the device may be achieved through a simplified structure.
  • the thickness of the polymerization layer may be appropriately selected depending on the intended use of the polarizing element, and for example, 0.5 ⁇ m to 10 ⁇ m, 1 ⁇ m to 9 ⁇ m, 2 ⁇ m to 8 ⁇ m, 3 ⁇ m to 7 ⁇ m or 4 ⁇ m It may have a thickness of 6 ⁇ m, but is not limited thereto.
  • the polymerization layer may include, for example, a polymerizable liquid crystal compound in a polymerized state.
  • that the polymerizable liquid crystal compound is included in a polymerized state may mean a state in which the liquid crystal compound is polymerized to form a skeleton such as a main chain or a side chain of the liquid crystal polymer in the layer.
  • the polymerization layer may also contain a polymerizable liquid crystal compound in a horizontally aligned state.
  • the horizontal alignment indicates that the optical axis of the polymerized layer including the polymerized liquid crystal compound is about 0 degrees to about 25 degrees, about 0 degrees to about 15 degrees, about 0 degrees to about 10 degrees, about the plane of the polymerized layer.
  • the optical axis may mean, for example, a fast axis or a slow axis when incident light passes through the corresponding area.
  • the dichroic dye may also be included in the polymerized layer in a state oriented along the alignment direction of the polymerizable liquid crystal compound.
  • the polarizer may further include an alignment layer, and the alignment layer may be disposed adjacent to the polymerization layer.
  • FIG. 1 exemplarily shows a polarizing element including a polymerized layer 101 and an alignment layer 102 adjacent to the polymerized layer.
  • an oriented film if it has an orientation capability with respect to the liquid crystal compound and / or dichroic dye in an adjacent polymer layer, it can select and use without a restriction
  • the alignment layer may be, for example, a photoalignment layer, and the photoalignment layer may include a photoalignment compound.
  • the term photo-orientation compound may refer to a compound which is aligned in a predetermined direction through irradiation of light and orientates adjacent liquid crystal compounds and the like in the alignment direction in a predetermined direction.
  • the alignment compound may be a monomolecular compound, a monomeric compound, an oligomeric compound, or a high molecular compound.
  • the photoalignable compound may be a compound including a photosensitive moiety.
  • Various photo-alignment compounds that can be used for the alignment of the liquid crystal compound are known.
  • Photo-alignment compounds include, for example, compounds aligned by trans-cis photoisomerization; Compounds aligned by photo-destruction, such as chain scission or photo-oxidation; Compounds ordered by photocrosslinking or photopolymerization such as [2 + 2] addition cyclization ([2 + 2] cycloaddition), [4 + 4] addition cyclization or photodimerization; Compounds aligned by photo-Fries rearrangement or compounds aligned by ring opening / closure reaction may be used.
  • azo compounds or stilbenes such as sulfated diazo dyes or azo polymers
  • cyclobutane tetracarboxylic dianhydride cyclobutane-1,2,3,4-tetracarboxylic dianhydride
  • aromatic polysilane or polyester polystyrene or polyimide and the like
  • polystyrene or polyimide and the like can be exemplified.
  • a compound aligned by photocrosslinking or photopolymerization a cinnamate compound, a coumarin compound, a cinnanam compound, a tetrahydrophthalimide compound, a maleimide compound , Benzophenone compounds, diphenylacetylene compounds, compounds having chalconyl residues (hereinafter referred to as chalconyl compounds) or compounds having anthracenyl residues (hereinafter referred to as anthracenyl compounds) as photosensitive residues;
  • chalconyl compounds compounds having chalconyl residues
  • anthracenyl compounds compounds having anthracenyl residues
  • examples of the compounds aligned by the optical freeze rearrangement include aromatic compounds such as benzoate compounds, benzoamide compounds, and methacrylamidoaryl methacrylate compounds.
  • the compound aligned by the ring-opening / ring-closure reaction such as a spiropyran compound A [4 + 2] ⁇ electron system ([4 + 2] ⁇ electronic system), but may be exemplified by compounds such as sorting by a ring opening / ring-closure reaction of, without being limited thereto.
  • the photo-alignment compound may be a monomolecular compound, a monomeric compound, an oligomeric compound, or a high molecular compound, or may be in the form of a blend of the photo-alignment compound and the polymer.
  • the oligomeric or polymeric compound as described above may have a residue derived from the above-described photoalignable compound or a photosensitive residue described above in the main chain or in the side chain.
  • Polymers having residues or photosensitive residues derived from photo-alignment compounds or that can be mixed with the photo-alignment compounds include polynorbornene, polyolefins, polyarylates, polyacrylates, poly (meth) acrylates, poly Examples include mead, poly (amic acid), polymaleimide, polyacrylamide, polymethacrylamide, polyvinyl ether, polyvinyl ester, polystyrene, polysiloxane, polyacrylonitrile or polymethacrylonitrile It may be, but is not limited thereto.
  • Polymers that may be included in the oriented compound include, for example, polynorbornene cinnamate, polynorbornene alkoxy cinnamate, polynorbornene allylyloxy cinnamate, polynorbornene fluorinated cinnamate, polynorbornene chlorinated cinnamate or Polynorbornene discinnamate and the like can be exemplified, but is not limited thereto.
  • the polarizing element may further include a base layer, and the base layer may be formed on one surface of the polymerization layer, for example.
  • 2 exemplarily illustrates a polarizer including a polymer layer 101 and a base layer 201 formed on one surface of the polymer layer.
  • the polarizing element further includes both the base layer and the alignment layer, as shown in FIG. 3, the base layer 201, the alignment layer 102, and the polymerization layer 101 may be sequentially included.
  • a base material layer a well-known raw material can be used without a restriction
  • inorganic films, plastic films, etc. such as a glass film, a crystalline or amorphous silicon film, a quartz, or an Indium Tin Oxide (ITO) film, can be used.
  • an optically anisotropic base material layer such as an optically isotropic base material layer or a retardation layer can be used.
  • plastic substrate layer examples include triacetyl cellulose (TAC); COP (cyclo olefin copolymer) such as norbornene derivatives; Poly (methyl methacrylate); PC (polycarbonate); PE (polyethylene); PP (polypropylene); PVA (polyvinyl alcohol); DAC (diacetyl cellulose); Pac (Polyacrylate); PES (poly ether sulfone); PEEK (polyetheretherketon PPS (polyphenylsulfone), PEI (polyetherimide); PEN (polyethylenemaphthatlate); PET (polyethyleneterephtalate); PI (polyimide); PSF (polysulfone); PAR (polyarylate) or amorphous fluorine resin
  • the substrate layer may include a coating layer of a silicon compound such as gold, silver, silicon dioxide or silicon monoxide, or a coating layer such as an antireflection layer, if necessary.
  • This application also relates to a manufacturing method of a polarizing element.
  • the manufacturing method of the polarizing element may include, for example, polymerizing the above-described liquid crystal composition coated on one surface of the substrate layer.
  • the base layer and the liquid crystal composition in the manufacturing method the contents described in the items of the liquid crystal composition and the polarizing element may be equally applied.
  • the coating method of the liquid crystal composition on the substrate layer is not particularly limited, and known coating methods such as roll coating, printing, inkjet coating, slit nozzle method, bar coating, comma coating, spin coating or gravure coating, for example. By coating through.
  • the polymerization method of the liquid crystal composition is not particularly limited and may be carried out by a known liquid crystal compound polymerization method.
  • the polymerizable liquid crystal compound is a liquid crystal composition having a cationically polymerizable functional group
  • it may be polymerized by a known cation polymerization reaction.
  • it may be carried out by maintaining a suitable temperature or irradiating a suitable active energy ray so that the cationic polymerization reaction can be initiated. If the maintenance at the appropriate temperature and the irradiation of the active energy ray is required at the same time, the process can be carried out sequentially or simultaneously.
  • the irradiation of the active energy ray may be performed using, for example, a high pressure mercury lamp, an electrodeless lamp or a xenon lamp, and the like, and the conditions such as the wavelength, light intensity, or light quantity of the active energy ray to be irradiated are
  • the polymerization of the cationic polymerizable liquid crystal compound can be selected in a range that can be appropriately made.
  • polarizing element a liquid crystal display device, an organic electroluminescence (EL) display device, an inorganic EL display device, a field emission display device (FED), a surface field emission display device (SPED), an electronic paper Display device using (electronic ink or electrophoretic element), plasma display device, projection display device (for example, display having a diffraction light valve (GLV) display device, digital micro mirror device (Digital Light Processing)) Device] and a piezoelectric ceramic display device, but are not limited thereto.
  • a display device a liquid crystal display device, an organic electroluminescence (EL) display device, an inorganic EL display device, a field emission display device (FED), a surface field emission display device (SPED), an electronic paper Display device using (electronic ink or electrophoretic element), plasma display device, projection display device (for example, display having a diffraction light valve (GLV) display device, digital micro mirror device (Digital Light Processing)) Device] and a piezoelectric ceramic display device
  • the liquid crystal display may be, for example, a transmissive liquid crystal display, a transflective liquid crystal display, a reflective liquid crystal display, a direct view liquid crystal display, or a projection liquid crystal display.
  • a display device may be a display device for displaying a two-dimensional image or a stereoscopic display device for displaying a three-dimensional image.
  • the method of configuring such a display device is not particularly limited, and a conventional method may be applied as long as the polarizer is used.
  • the guest-host liquid crystal composition of the present application can manufacture a polarizing element by a simple coating process, thereby reducing manufacturing cost and making it possible to reduce the weight of the polarizing element, and excellent heat resistance without changing the transmission spectrum in the absorption spectrum even under severe conditions such as a high temperature environment.
  • the polarizing element which shows stability can be manufactured.
  • Such a polarizing element can be applied to various display devices such as a liquid crystal display device, an EL display device, a field emission display device, a display device using electronic paper, a projection display device, or a piezoelectric ceramic display device.
  • 1 to 3 are schematic diagrams of exemplary polarizing elements.
  • the composition for forming a photo-alignment film was coated so that the thickness after drying was about 200 mm 3, and dried in an oven at 80 ° C. for 2 minutes.
  • the composition for forming the photo-alignment film 2 parts by weight of poly (5-norbornene-2-methyl (4-methoxy cinnamate)), 1 part by weight of dipentaerythritol hexaacrylate as a polar binder, and a photoinitiator ( Igacure 907, manufactured by Ciba-Geigy Co., Ltd.) was used to prepare an alignment film precursor composition prepared by dissolving 0.5 parts by weight of the solvent (toluene) to about 96.8 parts by weight. After drying the composition for forming a photo-alignment film was irradiated with ultraviolet (100 mW / cm 2 ) at a rate of 3 m / min to perform an alignment treatment.
  • ultraviolet 100 mW / cm 2
  • a polarizing device was manufactured in the same manner as in Example 1, except that Acrylate RM (LC242, manufactured by BASF), which is a radical polymerizable liquid crystal compound, was used as the polymerizable liquid crystal compound.
  • Acrylate RM LC242, manufactured by BASF
  • Example 1 and Comparative Example 1 were cut into 10 mm ⁇ 10 mm (horizontal ⁇ vertical) sizes to prepare specimens, and then the absorbances of the polarizers were measured using N & K Analyer devices. After standing at 100 ° C. for 100 hours at 100 ° C., the absorbance according to the wavelength was measured again.
  • the absorption spectra of the polarizing elements of Example 1 and Comparative Example 1 thus measured are shown in FIG. 4.
  • Example 1 As shown in FIG. 4, before heat resistance, the polarizing elements of Example 1 and Comparative Example 1 exhibit similar absorption spectra. However, after heat resistance, the polarizing element of Example 1 maintains the absorption spectrum while the polarizing element of Comparative Example 1 can be seen that the wavelength showing the maximum absorbance is changed from about 580 nm to about 400 nm.
  • Test Example 2 heat resistant Optical properties evaluation

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Abstract

The present application relates to a liquid crystal composition, a polarizing element, and a use of the polarizing element. A guest-host type liquid crystal composition of the present application can produce a polarizing element through a simple coating process, thereby reducing a manufacturing cost, enabling a polarizing element to be lightweight and thin, and producing a polarizing element exhibiting excellent heat-resistant stability without a change in the absorption spectrum or the transmission spectrum even under a harsh condition such as a high-temperature environment. The polarizing element can be applied to various display devices such as a liquid crystal display device, an EL display device, a field emission display device, a display device using electronic paper, a projection-type display device, or a piezoelectric ceramic display device.

Description

게스트호스트형 액정 조성물Guest Host Liquid Crystal Composition
관련 출원들과의 상호 인용　 Cross Citation with Related Applications
본 출원은 2015년 7월 2일자 한국 특허 출원 제10-2015-0094600호 및 2016년 7월 4일자 한국 특허 출원 제10-2016-0084188호에 기초한 우선권의 이익을 주장하며, 해당 한국 특허 출원들의 문헌에 개시된　모든 내용은 본 명세서의 일부로서 포함된다. This application claims the benefit of priority based on Korean Patent Application No. 10-2015-0094600 filed July 2, 2015 and Korean Patent Application No. 10-2016-0084188 filed July 4, 2016. All content disclosed in the literature is included as part of this specification.
기술분야Technical Field
본 출원은, 게스트호스트형 액정 조성물, 편광 소자 및 편광 소자의 용도에 관한 것이다. The present application relates to the use of a guest host type liquid crystal composition, a polarizing element and a polarizing element.
디스플레이 장치에서 이용되는 편광 소자는, 예를 들면, 요오드가 염착된 폴리비닐알코올(PVA; Poly Vinyl Alcohol) 필름과 이를 보호하는 보호필름, 예를 들어 트리아세틸셀룰로스(TAC; Tri Acetyl Cellulose) 필름의 복합 필름 구조로 형성되어 있다. The polarizing element used in the display device may be, for example, a polyvinyl alcohol (PVA) film in which iodine is salted and a protective film for protecting the same, for example, a triacetylcellulose (TAC) film. It is formed in a composite film structure.
최근, 상기 요오드 염착을 통한 필름형 다층소자의 대안으로서 간단한 코팅 공정으로 형성하는 새로운 개념의 박막형 고분자 편광 필름의 개발이 모색되고 있다. 이러한 구조 단순화를 통한 편광필름의 박막화와 저가 제조 공정기술은 LCD 원가 절감과 플렉시블 디스플레이 구현을 위한 핵심 기술로서, 특허문헌 1(일본 특허 공개 제2010-152351호 공보)과 같이 이색성 염료와 중합성 액정 화합물을 포함하는 염료층을 코팅하여 편광 소자를 제조하는 기술이 알려져 있다.Recently, development of a thin film type polymer polarizing film having a new concept of forming a simple coating process as an alternative to the film type multilayer device through iodine dyeing has been sought. The thinning and low-cost manufacturing process technology of the polarizing film through the simplification of the structure is a key technology for reducing the LCD cost and realizing the flexible display. As shown in Patent Document 1 (Japanese Patent Laid-Open No. 2010-152351), dichroic dye and polymerizable The technique of manufacturing a polarizing element by coating the dye layer containing a liquid crystal compound is known.
그러나, 편광 소자를 디스플레이 장치에 사용하기 위해서는 고온 조건과 같은 가혹한 조건 하에서도 흡수 스펙트럼을 유지할 수 있는 물성이 요구되는데, 이색성 염료를 이용한 코팅형 편광 소자는 내열 안정성이 떨어지기 때문에 고온 조건에서 염료 분자가 분해되어 흡수 스펙트럼이 변하는 문제점이 있어서 디스플레이 장치에 사용하는 것에 한계가 있다. 이에, 최근 디스플레이 장치 분야에서는 내열 안정성을 확보할 수 있는 코팅형 편광 소자의 개발에 대한 연구가 증가하고 있는 추세이다. However, in order to use a polarizing element in a display device, a physical property capable of maintaining an absorption spectrum even under severe conditions such as a high temperature condition is required. A coated polarizing element using a dichroic dye has a poor heat resistance and therefore, a dye at a high temperature condition. There is a problem in that the absorption spectrum is changed due to the decomposition of molecules, which limits its use in display devices. Accordingly, in the field of display devices, research on the development of a coating type polarizing device capable of securing heat resistance has been increasing.
본 출원은 게스트호스트형 액정 조성물, 편광 소자 및 편광 소자의 용도를 제공한다.The present application provides the use of a guest host type liquid crystal composition, a polarizer and a polarizer.
본 출원은 게스트호스트형 액정 조성물에 관한 것이다. 예시적인 게스트호스트형 액정 조성물은 아크릴로일계 중합성 관능기를 포함하지 않는 중합성 액정 화합물 및 이색성 염료를 포함할 수 있다. 본 출원에서 게스트호스트형 액정 조성물은, 예를 들어, 비등방성 광흡수 효과를 나타내는 편광 소자를 형성할 수 있는 특성을 가지는 액정 조성물을 의미할 수 있다. 게스트호스트형 액정 조성물은, 예를 들어, 후술하는 바와 같이, 중합성 액정 화합물의 배열에 따라 이색성 염료가 함께 배열되어 염료의 정렬 방향과 평행한 광은 흡수하고 수직한 광은 투과시킴으로써, 비등방성 광흡수 효과를 나타내는 편광 소자를 형성할 수 있다. The present application relates to a guest host type liquid crystal composition. An exemplary guest host type liquid crystal composition may include a polymerizable liquid crystal compound and a dichroic dye that do not include an acryloyl based polymerizable functional group. In the present application, the guest host type liquid crystal composition may mean, for example, a liquid crystal composition having a characteristic capable of forming a polarizing element exhibiting an anisotropic light absorption effect. The guest-host type liquid crystal composition is, for example, as described later, dichroic dyes are arranged together in accordance with the arrangement of the polymerizable liquid crystal compound to absorb light parallel to the alignment direction of the dye and transmit the vertical light, The polarizing element which shows an isotropic light absorption effect can be formed.
본 출원의 상기 액정 조성물은 액정층으로 중합된 후에도 우수한 내열성을 나타낼 수 있다. 예를 들어, 상기 액정 조성물은 하기 수식 1을 만족할 수 있다. The liquid crystal composition of the present application may exhibit excellent heat resistance even after polymerization to the liquid crystal layer. For example, the liquid crystal composition may satisfy Equation 1 below.
[수식 1] [Equation 1]
-20 ≤100 × (H - W)/W ≤ 20-20 ≤100 × (H-W) / W ≤ 20
수식 1에서 W는 상기 중합성 액정 화합물이 중합된 직후의 상기 염료의 최대 흡수 파장을 의미할 수 있고, H는 상기 액정 화합물이 중합된 액정 조성물을 100°C에서 100 시간 유지한 후의 상기 염료의 최대 흡수 파장을 의미할 수 있다. 즉, 액정 조성물은 상기 수식 1로 계산되는 고온 조건에서의 염료의 최대 흡수 파장 변화율의 절대값이 20 이하일 수 있다.In Equation 1, W may mean the maximum absorption wavelength of the dye immediately after the polymerizable liquid crystal compound is polymerized, H is the dye of the dye after maintaining the liquid crystal composition polymerized with the liquid crystal compound at 100 ° C for 100 hours It may mean the maximum absorption wavelength. That is, in the liquid crystal composition, the absolute value of the maximum absorption wavelength change rate of the dye under the high temperature condition calculated by Equation 1 may be 20 or less.
수식 1로 계산되는 염료의 최대 흡수 파장 변화율은, 보다 구체적으로, ±17.5 범위 내, ±15 범위 내, ±12.5 범위 내 또는 ±10 범위 내일 수 있다. 상기 염료의 최대 흡수 파장의 변화율은 후술하는 실시예에 기재된 염료층의 흡수 스펙트럼을 측정함으로써 계산될 수 있다. 이러한 염료의 최대 흡수 파장 변화율은 수치가 낮을수록 액정 조성물로부터 제조된 편광 소자의 내열 안정성을 보장하는 것으로서 그 하한 수치는 특별히 제한되지 않는다. The maximum absorption wavelength change rate of the dye calculated by Equation 1 may be, more specifically, within a range of ± 17.5, a range of ± 15, a range of ± 12.5, or a range of ± 10. The rate of change of the maximum absorption wavelength of the dye can be calculated by measuring the absorption spectrum of the dye layer described in the Examples described later. The lower the maximum absorption wavelength change rate of the dye, the lower the numerical value is to ensure the heat resistance stability of the polarizing element produced from the liquid crystal composition, the lower limit is not particularly limited.
본 명세서에서, 「중합성 액정 화합물」은, 액정성을 나타낼 수 있는 부위, 예를 들면 메조겐(mesogen) 골격 등을 포함하고, 중합성 관능기를 하나 이상 포함하는 화합물을 의미할 수 있다. 본 출원의 액정 조성물은, 전술한 바와 같이, 중합성 관능기로서, 아크릴로일계 중합성 관능기를 포함하지 않는 중합성 액정 화합물을 포함할 수 있다. 본 출원에서 아크릴로일계 중합성 관능기는, 예를 들어, 라디칼 반응에 의하여 중합 가능한 관능기를 대표하는 의미로서, 예를 들어, 아크릴로일기 또는 메타크릴로일기를 포함하는 의미일 수 있다. In the present specification, the "polymerizable liquid crystal compound" may mean a compound including a site capable of exhibiting liquid crystallinity, for example, a mesogen skeleton, and the like, and including one or more polymerizable functional groups. As described above, the liquid crystal composition of the present application may include a polymerizable liquid crystal compound that does not include an acryloyl series polymerizable functional group as the polymerizable functional group. In the present application, the acryloyl-based polymerizable functional group may be, for example, a meaning representing a functional group polymerizable by a radical reaction, and for example, may include acryloyl group or methacryloyl group.
본 출원의 액정 조성물은 아크릴로일계 중합성 관능기를 포함하지 않는 중합성 액정 화합물을 주성분으로 포함할 수 있다. 본 명세서에서, 용어 「주성분」은 조성물 내에 약 70 중량% 이상, 약 75 중량% 이상, 약 80 중량% 이상, 약 85 중량% 이상, 약 90 중량% 이상 또는 약 95 중량% 이상 포함되는 것을 의미할 수 있다. The liquid crystal composition of the present application may include, as a main component, a polymerizable liquid crystal compound that does not contain an acryloyl based polymerizable functional group. As used herein, the term “main ingredient” means that at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, or at least about 95% by weight of the composition is included in the composition. can do.
아크릴로일계 중합성 관능기를 포함하지 않는 중합성 액정 화합물로, 예를 들어, 양이온 중합성 액정 화합물을 사용할 수 있다. 본 출원에서 양이온 중합성 액정 화합물은, 예를 들어, 양이온 중합 반응에 의하여 중합 가능한 관능기를 적어도 하나 이상 가지는 액정 화합물을 의미할 수 있다. 이러한 양이온 중합성 관능기로는, 예를 들어, 에폭시기를 예시할 수 있다. 양이온 중합성 액정 화합물은, 예를 들어, 상기 에폭시기를 1개 포함하는 단관능성 중합성 액정 화합물이거나 또는 상기 에폭시기를 2개 이상, 예를 들어, 2개 내지 10개, 2개 내지 8개, 2개 내지 6개, 2개 내지 5개, 2개 내지 4개, 2개 내지 3개 또는 2개 포함하는 다관능성 중합성 액정 화합물일 수 있다. As a polymerizable liquid crystal compound which does not contain an acryloyl type polymerizable functional group, a cationically polymerizable liquid crystal compound can be used, for example. In the present application, the cationic polymerizable liquid crystal compound may mean, for example, a liquid crystal compound having at least one or more functional groups polymerizable by a cationic polymerization reaction. As such a cationically polymerizable functional group, an epoxy group can be illustrated, for example. The cationically polymerizable liquid crystal compound is, for example, a monofunctional polymerizable liquid crystal compound containing one epoxy group or two or more epoxy groups, for example, 2 to 10, 2 to 8, 2 It may be a multi-functional polymerizable liquid crystal compound containing 6 to 6, 2 to 5, 2 to 4, 2 to 3 or two.
중합성 액정 화합물로는, 예를 들어, 하기 화학식 1로 표시되는 화합물을 사용할 수 있다. As a polymerizable liquid crystal compound, the compound represented by following formula (1) can be used, for example.
[화학식 1][Formula 1]
Figure PCTKR2016007194-appb-I000001
Figure PCTKR2016007194-appb-I000001
상기 화학식 1에서 A는 단일 결합, -COO- 또는 -OCO-이고, R1 내지 R10은, 각각 독립적으로 수소, 할로겐, 알킬기, 알콕시기, 알콕시카보닐기, 니트로기, 에폭시기, 시아노기, -O-Q-P 또는 하기 화학식 2의 치환기이되, R1 내지 R10 중 적어도 하나는 에폭시기, 시아노기, -O-Q-P 또는 하기 화학식 2의 치환기이거나, R1 내지 R5 중 인접하는 2개의 치환기 또는 R6 내지 R10 중 인접하는 2개의 치환기는 서로 연결되어 -O-Q-P로 치환된 벤젠을 형성하고, 상기에서 Q는 알킬렌기 또는 알킬리덴기이며, P는 에폭시기이다:In Formula 1, A is a single bond, -COO- or -OCO-, and R 1 to R 10 are each independently hydrogen, halogen, alkyl group, alkoxy group, alkoxycarbonyl group, nitro group, epoxy group, cyano group,- OQP or a substituent of Formula 2, wherein at least one of R 1 to R 10 is an epoxy group, a cyano group, -OQP or a substituent of Formula 2, or two adjacent substituents of R 1 to R 5 or R 6 to R 10 Two adjacent substituents are connected to each other to form a benzene substituted with -OQP, wherein Q is an alkylene group or an alkylidene group, and P is an epoxy group:
[화학식 2][Formula 2]
Figure PCTKR2016007194-appb-I000002
Figure PCTKR2016007194-appb-I000002
상기 화학식 2에서 B는 단일 결합, -COO- 또는 -OCO-이고, R11 내지 R15는, 각각 독립적으로 수소, 할로겐, 알킬기, 알콕시기, 알콕시카보닐기, 니트로기, 에폭시기, 시아노기 또는 -O-Q-P이되, R11 내지 R15 중 적어도 하나는 에폭시기, 시아노기, 또는 -O-Q-P이거나, R11 내지 R15 중 인접하는 2개의 치환기는 서로 연결되어 -O-Q-P로 치환된 벤젠을 형성하고, 상기에서 Q는 알킬렌기 또는 알킬리덴기이며, P는 에폭시기이다.In Formula 2, B is a single bond, -COO-, or -OCO-, and R 11 To R 15 are each independently hydrogen, halogen, alkyl group, alkoxy group, alkoxycarbonyl group, nitro group, epoxy group, cyano group or -OQP, wherein at least one of R 11 to R 15 is an epoxy group, cyano group, or -OQP Or R 11 Two adjacent substituents of R to R 15 are connected to each other to form a benzene substituted with —OQP, wherein Q is an alkylene group or an alkylidene group, and P is an epoxy group.
상기 화학식 1 및 2에서 인접하는 2개의 치환기는 서로 연결되어 -O-Q-P로 치환된 벤젠을 형성한다는 것은, 인접하는 2개의 치환기가 서로 연결되어 전체적으로 -O-Q-P로 치환된 나프탈렌 골격을 형성하는 것을 의미할 수 있다.In Formulas 1 and 2, adjacent two substituents may be linked to each other to form benzene substituted with -OQP, which may mean that two adjacent substituents are connected to each other to form a naphthalene skeleton substituted with -OQP as a whole. have.
상기 화학식 2에서 B의 좌측의 "-"은 B가 화학식 1의 벤젠에 직접 연결되어 있음을 의미할 수 있다."-" Of the left side of B in Formula 2 may mean that B is directly connected to the benzene of Formula 1.
상기 화학식 1 및 2에서 용어 "단일 결합"은 A 또는 B로 표시되는 부분에 별도의 원자가 존재하지 않는 경우를 의미한다. 예를 들어, 화학식 1에서 A가 단일 결합인 경우, A의 양측의 벤젠이 직접 연결되어 비페닐(biphenyl) 구조를 형성할 수 있다.In Formulas 1 and 2, the term “single bond” refers to a case in which a separate atom is not present in a portion represented by A or B. For example, when A is a single bond in Formula 1, benzene on both sides of A may be directly connected to form a biphenyl structure.
상기 화학식 1 및 2에서 할로겐으로는, 염소, 브롬 또는 요오드 등이 예시될 수 있다. As the halogen in Chemical Formulas 1 and 2, chlorine, bromine or iodine may be exemplified.
본 명세서에서 용어 알킬기는, 특별히 달리 규정하지 않는 한, 탄소수 1 내지 20, 탄소수 1 내지 16, 탄소수 1 내지 12, 탄소수 1 내지 8 또는 탄소수 1 내지 4의 직쇄 또는 분지쇄 알킬기 또는 탄소수 3 내지 20, 탄소수 3 내지 16 또는 탄소수 4 내지 12의 시클로알킬기를 의미할 수 있다. 상기 알킬기는 임의적으로 하나 이상의 치환기에 이해 치환될 수 있다.As used herein, unless otherwise specified, the term alkyl group is a straight or branched chain alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, or 3 to 20 carbon atoms, It may mean a cycloalkyl group having 3 to 16 carbon atoms or 4 to 12 carbon atoms. The alkyl group may be optionally substituted with one or more substituents.
본 명세서에서 용어 알콕시기는, 특별히 달리 규정하지 않는 한, 탄소수 1 내지 20, 탄소수 1 내지 16, 탄소수 1 내지 12, 탄소수 1 내지 8 또는 탄소수 1 내지 4의 알콕시기를 의미할 수 있다. 상기 알콕시기는, 직쇄, 분지쇄 또는 고리형일 수 있다. 또한, 상기 알콕시기는 임의적으로 하나 이상의 치환기에 이해 치환될 수 있다.As used herein, unless otherwise specified, the term alkoxy group may mean an alkoxy group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms. The alkoxy group may be linear, branched or cyclic. In addition, the alkoxy group may be optionally substituted with one or more substituents.
또한, 본 명세서에서 용어 알킬렌기 또는 알킬리덴기는, 특별히 달리 규정하지 않는 한, 탄소수 1 내지 12, 탄소수 1 내지 8 또는 탄소수 1 내지 4의 알킬렌기 또는 알킬리덴기를 의미할 수 있다. 상기 알킬렌기 또는 알킬리덴기는, 직쇄, 분지쇄 또는 고리형일 수 있다. 또한, 상기 알킬렌기 또는 알킬리덴기는 임의적으로 하나 이상의 치환기에 이해 치환될 수 있다.In the present specification, the term alkylene group or alkylidene group may mean an alkylene group or an alkylidene group having 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, unless otherwise specified. The alkylene group or alkylidene group may be linear, branched or cyclic. In addition, the alkylene group or alkylidene group may be optionally substituted with one or more substituents.
또한, 본 명세서에서 알케닐기는, 특별히 달리 규정하지 않는 한, 탄소수 2 내지 20, 탄소수 2 내지 16, 탄소수 2 내지 12, 탄소수 2 내지 8 또는 탄소수 2 내지 4의 알케닐기를 의미할 수 있다. 상기 알케닐기는, 직쇄, 분지쇄 또는 고리형일 수 있다. 또한, 상기 알케닐기는 임의적으로 하나 이상의 치환기에 이해 치환될 수 있다.In addition, an alkenyl group in the present specification may mean an alkenyl group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms, unless otherwise specified. The alkenyl group may be linear, branched or cyclic. In addition, the alkenyl group may be optionally substituted with one or more substituents.
본 명세서에서 특정 관능기에 치환되어 있을 수 있는 치환기로는, 알킬기, 알콕시기, 알케닐기, 옥소기, 옥세타닐기, 티올기, 에폭시기 또는 시아노기 등이 예시될 수 있고, 바람직하게는 에폭시기로 치환되어 있는 것이 좋다 As a substituent which may be substituted in the specific functional group in this specification, an alkyl group, an alkoxy group, an alkenyl group, an oxo group, an oxetanyl group, a thiol group, an epoxy group, or a cyano group, etc. can be illustrated, Preferably it is substituted by an epoxy group It is good to be
액정 조성물은 또한, 전술한 바와 같이 이색성 염료를 포함할 수 있다. 본 출원에서 염료는, 예를 들어, 가시광 영역, 예를 들면, 400 nm 내지 700 nm 파장 범위 내에서 적어도 일부 또는 전체 범위 내의 광을 집중적으로 흡수 및/또는 변형시킬 수 있는 물질을 의미할 수 있으며, 이색성 염료는 가시광 영역의 적어도 일부 또는 전체 범위에서 광의 이방성 흡수가 가능한 물질을 의미할 수 있다.The liquid crystal composition may also include a dichroic dye as described above. In the present application, the dye may refer to a material capable of intensively absorbing and / or modifying light in at least part or the entire range, for example, in the visible light region, for example, in the 400 nm to 700 nm wavelength range, , Dichroic dye may refer to a material capable of anisotropic absorption of light in at least part or the entire range of the visible light region.
이색성 염료로는, 예를 들어, 소위 게스트호스트형 액정 소자를 형성할 수 있는 것으로 알려진 것, 예를 들어, 중합성 액정 화합물의 배향에 따라 배향될 수 있는 특성을 가지는 것으로 알려진 공지의 염료을 선택하여 사용할 수 있다. 이러한 이색성 염료로는 또한, 예를 들어, 가시광 영역, 예를 들면, 400 nm 내지 700 nm 내에서 최대 흡광도를 가지는 염료를 사용할 수 있다. 이러한 염료는, 예를 들면, 시안 염료, 안트라퀴논 염료, 아크리딘 염료, 시아닌 염료 및 나프탈렌 염료 중 하나 이상의 염료를 사용할 수 있으나, 이에 제한되는 것은 아니다. As the dichroic dye, for example, a known dye known to be capable of forming a so-called guest host type liquid crystal device, for example, a known dye known to have a property that can be oriented according to the orientation of the polymerizable liquid crystal compound is selected. Can be used. Such dichroic dyes may also be used, for example, dyes having a maximum absorbance in the visible region, for example 400 nm to 700 nm. Such dyes may include, but are not limited to, for example, one or more dyes of cyan dye, anthraquinone dye, acridine dye, cyanine dye, and naphthalene dye.
이색성 염료로는 또한, 이색비(dichroic ratio), 즉 이방성 염료의 장축 방향에 평행한 편광의 흡수를 상기 장축 방향에 수직하는 방향에 평행한 편광의 흡수로 나눈 값이 5 이상, 6 이상, 7 이상, 8 이상, 9 이상 또는 10 이상인 염료를 사용할 수 있다. 상기 염료는 가시광 영역의 파장 범위 내, 예를 들면, 약 380 nm 내지 700 nm 또는 약 400 nm 내지 700 nm의 파장 범위 내에서 적어도 일부의 파장 또는 어느 한 파장에서 상기 이색비를 만족할 수 있다. 상기 이색비의 상한은, 예를 들면 20 이하, 18 이하, 16 이하 또는 14 이하 정도일 수 있다. As the dichroic dye, a dichroic ratio, that is, a value obtained by dividing the absorption of polarization parallel to the long axis direction of the anisotropic dye by the absorption of polarization parallel to the direction perpendicular to the long axis direction is 5 or more, 6 or more, Dye which is 7 or more, 8 or more, 9 or more, or 10 or more can be used. The dye may satisfy the dichroic ratio at at least some of the wavelengths or at any one within the wavelength range of the visible region, for example, in the wavelength range of about 380 nm to 700 nm or about 400 nm to 700 nm. The upper limit of the dichroic ratio may be, for example, about 20 or less, 18 or less, 16 or less, or about 14 or less.
액정 조성물 내의 이색성 염료의 함량은, 목적하는 물성을 손상시키지 않는 범위 내에서 적절히 선택될 수 있다. 예를 들어, 이색성 염료는 중합성 액정 화합물 100 중량부 대비 0.1 중량부 내지 20 중량부 범위 내의 비율로 포함될 수 있다. 보다 구체적으로, 이색성 염료는 중합성 화합물 100 중량부 대비 0.1 중량부 이상, 1 중량부 이상, 2 중량부 이상, 3 중량부 이상, 4 중량부 이상, 5 중량부 이상, 6 중량부 이상, 7 중량부 이상, 8 중량부 이상, 9 중량부 이상 또는 10 중량부 이상의 범위로 포함될 수 있고, 또한, 중합성 화합물 100 중량부 대비 20 중량부 이하, 19 중량부 이하, 18 중량부 이하, 17 중량부 이하, 16 중량부 이하, 15 중량부 이하, 14 중량부 이하, 13 중량부 이하, 12 중량부 이하 또는 11 중량부 이하의 범위로 포함될 수 있다. The content of the dichroic dye in the liquid crystal composition may be appropriately selected within a range that does not impair the desired physical properties. For example, the dichroic dye may be included in a ratio within the range of 0.1 parts by weight to 20 parts by weight with respect to 100 parts by weight of the polymerizable liquid crystal compound. More specifically, the dichroic dye is 0.1 part by weight, 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight, or more, based on 100 parts by weight of the polymerizable compound, It may be included in the range of 7 parts by weight or more, 8 parts by weight, 9 parts by weight or 10 parts by weight or more, and 20 parts by weight or less, 19 parts by weight or less, 18 parts by weight or less, relative to 100 parts by weight of the polymerizable compound. It may be included in the range of up to 16 parts by weight, up to 15 parts by weight, up to 14 parts by weight, up to 13 parts by weight, up to 12 parts by weight or up to 11 parts by weight.
액정 조성물은, 중합성 액정 화합물로서 양이온 중합성 액정 화합물을 포함하는 경우, 양이온 개시제를 추가로 포함할 수 있다. 이러한 양이온 개시제로는, 오늄 염(onium salt) 또는 유기금속염(organometallic salt) 계열의 이온화 양이온 개시제 또는 유기 실란 또는 잠재성 황산(latent sulfonic acid) 계열이나 그 외의 비이온화 화합물 등과 같은 비이온화 양이온 개시제를 사용할 수 있다. 오늄염 계열의 개시제로는, 디아릴이오도늄 염(diaryliodonium salt), 트리아릴술포늄 염(triarylsulfonium salt) 또는 아릴디아조늄 염(aryldiazonium salt) 등이 예시될 수 있고, 유기금속 염 계열의 개시제로는 철 아렌(iron arene) 등이 예시될 수 있으며, 유기 실란 계열의 개시제로는, o-니트릴벤질 트리아릴 실리 에테르(o-nitrobenzyl triaryl silyl ether), 트리아릴 실리 퍼옥시드(triaryl silyl peroxide) 또는 아실 실란(acyl silane) 등이 예시될 수 있고, 잠재성 황산 계열의 개시제로는 a-설포닐옥시 케톤 또는 a-히드록시메틸벤조인 설포네이트 등이 예시될 수 있으나, 이에 제한되는 것은 아니다. 또한, 상기 양이온 개시제로는 요오드 계열의 개시제와 광증감제의 혼합물을 사용할 수도 있다. 이러한 광증감제로는 안트라센 화합물, 피렌 화합물, 카르보닐 화합물, 유기 황화합물, 과황화물, 레독스 화합물, 아조 및 디아조 화합물, 할로겐 화합물 또는 광환원성 색소 등이 예시될 수 있다. The liquid crystal composition may further include a cationic initiator when the cationic polymerizable liquid crystal compound is included as the polymerizable liquid crystal compound. Examples of such cation initiators include ionization cation initiators of onium salts or organometallic salts, or nonionization cation initiators such as organic silanes or latent sulfonic acid series or other non-ionizing compounds. Can be used. Examples of the onium salt-based initiator include a diaryliodonium salt, a triarylsulfonium salt, an aryldiazonium salt, and the like. As the zero, iron arene and the like can be exemplified. Examples of the organosilane-based initiator include o-nitrobenzyl triaryl silyl ether and triaryl silyl peroxide. Or an acyl silane (acyl silane) may be exemplified, a latent sulfuric acid-based initiator may be exemplified by a-sulfonyloxy ketone or a-hydroxymethylbenzoin sulfonate, but is not limited thereto. . In addition, a mixture of an iodine-based initiator and a photosensitizer may be used as the cationic initiator. Examples of such photosensitizers include anthracene compounds, pyrene compounds, carbonyl compounds, organic sulfur compounds, persulfides, redox compounds, azo and diazo compounds, halogen compounds or photoreducing dyes.
양이온 개시제의 함량은 목적하는 중합 정도에 따라 적절히 조절될 수 있으며, 예를 들면, 양이온 중합성 액정 화합물 100 중량부 0.1 중량부 내지 20 중량부 범위 내의 비율로 포함될 수 있다. 보다 구체적으로, 야이온 개시제는 중합성 화합물 100 중량부 대비 0.1 중량부 이상, 1 중량부 이상, 2 중량부 이상, 3 중량부 이상, 4 중량부 이상, 5 중량부 이상, 6 중량부 이상, 7 중량부 이상, 8 중량부 이상, 9 중량부 이상 또는 10 중량부 이상의 범위로 포함될 수 있고, 또한, 중합성 화합물 100 중량부 대비 20 중량부 이하, 19 중량부 이하, 18 중량부 이하, 17 중량부 이하, 16 중량부 이하, 15 중량부 이하, 14 중량부 이하, 13 중량부 이하, 12 중량부 이하 또는 11 중량부 이하의 범위로 포함될 수 있다.The content of the cationic initiator may be appropriately adjusted according to the degree of polymerization desired, for example, it may be included in a ratio within the range of 0.1 parts by weight to 20 parts by weight of 100 parts by weight of the cationic polymerizable liquid crystal compound. More specifically, the ionic initiator is 0.1 part by weight, 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight or more, based on 100 parts by weight of the polymerizable compound, It may be included in the range of 7 parts by weight or more, 8 parts by weight, 9 parts by weight or 10 parts by weight or more, and 20 parts by weight or less, 19 parts by weight or less, 18 parts by weight or less, relative to 100 parts by weight of the polymerizable compound. It may be included in the range of up to 16 parts by weight, up to 15 parts by weight, up to 14 parts by weight, up to 13 parts by weight, up to 12 parts by weight or up to 11 parts by weight.
본 출원은 또한, 편광 소자에 관한 것이다. 편광 소자는, 예를 들어, 전술한 게스트호스트형 액정 조성물의 중합층을 포함할 수 있다. 즉, 편광 소자는, 아크릴로일계 중합성 관능기를 포함하지 않는 중합성 액정 화합물 및 이색성 염료를 포함하는 호스트 게스트형 액정 조성물의 중합층을 포함할 수 있다. 따라서, 편광 소자에서 중합성 액정 화합물 및 이색성 염료에 대한 내용은 상기 액정 조성물의 항목에서 기술한 내용이 동일하게 적용될 수 있다. The present application also relates to a polarizing element. The polarizing element may include, for example, the polymer layer of the guest host liquid crystal composition described above. That is, a polarizing element can contain the polymeric layer of the host guest type liquid crystal composition containing the polymeric liquid crystal compound and dichroic dye which do not contain an acryloyl type polymeric functional group. Therefore, the content of the polymerizable liquid crystal compound and the dichroic dye in the polarizing device may be the same as described in the item of the liquid crystal composition.
이러한 편광 소자는 우수한 내열성을 나타낼 수 있다. 예를 들어, 편광 소자는 하기 수식 1을 만족할 수 있다. 하기 수식 1에 대한 구체적인 내용도 상기 액정 조성물의 항목에서 기술한 내용이 동일하게 적용될 수 있다. Such a polarizing element may exhibit excellent heat resistance. For example, the polarizer may satisfy Equation 1 below. Details of the following Equation 1 may also be applied in the same manner described in the item of the liquid crystal composition.
[수식 1][Equation 1]
-20 ≤100 × (H - W)/W = 20-20 ≤100 × (H-W) / W = 20
수식 1에서 W는 상기 중합성 액정 화합물이 중합된 직후의 상기 염료의 최대 흡수 파장이고, H는 상기 액정 화합물이 중합된 액정 조성물을 100℃에서 100 시간 유지한 후의 상기 염료의 최대 흡수 파장이다.In Equation 1, W is the maximum absorption wavelength of the dye immediately after the polymerizable liquid crystal compound is polymerized, and H is the maximum absorption wavelength of the dye after holding the liquid crystal composition polymerized with the liquid crystal compound at 100 ° C. for 100 hours.
중합층은, 예를 들어, 아크릴로일계 중합성 관능기를 포함하지 않는 중합성 액정 화합물 및 이색성 염료를 포함하는 편광 물질의 코팅층일 수 있다. 상기 중합성 액정 화합물은, 예를 들어, 양이온 중합성 액정 화합물, 보다 구체적으로 에폭시기와 같은 양이온 중합성 관능기를 가지는 액정 화합물일 수 있다. 이러한 편광 소자는, 예를 들어, 간단한 코팅 공정으로 제조될 수 있으므로 저가로 제조할 수 있을 뿐만 아니라 구조 단순화를 통한 소자의 박막화가 가능하다. The polymerization layer may be, for example, a coating layer of a polarizing material including a polymerizable liquid crystal compound and a dichroic dye that do not include an acryloyl based polymerizable functional group. The polymerizable liquid crystal compound may be, for example, a cationic polymerizable liquid crystal compound, more specifically, a liquid crystal compound having a cationically polymerizable functional group such as an epoxy group. Such a polarizing device may be manufactured by, for example, a simple coating process, so that the polarizing device may be manufactured at low cost, and thinning of the device may be achieved through a simplified structure.
중합층의 두께는, 목적하는 편광 소자의 용도에 따라 적절히 선택될 수 있고, 예를 들어, 0.5㎛ 내지 10㎛, 1㎛ 내지 9㎛, 2㎛ 내지 8㎛, 3㎛ 내지 7㎛ 또는 4㎛ 내지 6㎛의 두께를 가질 수 있으나, 이에 제한되는 것은 아니다. The thickness of the polymerization layer may be appropriately selected depending on the intended use of the polarizing element, and for example, 0.5 µm to 10 µm, 1 µm to 9 µm, 2 µm to 8 µm, 3 µm to 7 µm or 4 µm It may have a thickness of 6㎛, but is not limited thereto.
중합층은, 예를 들어, 중합성 액정 화합물을 중합된 상태로 포함할 수 있다. 본 출원에서 중합성 액정 화합물이 중합된 상태로 포함되어 있다는 것은 상기 액정 화합물이 중합되어 층 내에서 액정 고분자의 주쇄 또는 측쇄와 같은 골격을 형성하고 있는 상태를 의미할 수 있다. 중합층은 또한, 중합성 액정 화합물을 수평 배향된 상태로 포함할 수 있다. 본 출원에서 수평 배향은, 중합된 액정 화합물을 포함하는 중합층의 광축이 중합층의 평면에 대하여 약 0도 내지 약 25도, 약 0도 내지 약 15도, 약 0도 내지 약 10도, 약 0도 내지 약 5도 또는 약 0도의 경사각을 가지는 경우를 의미할 수 있다. 본 출원에서 광축은, 예를 들어, 입사광이 해당 영역을 투과할 때의 진상축 또는 지상축을 의미할 수 있다. 또한, 이색성 염료도, 상기 중합성 액정 화합물의 배향 방향에 따라 배향된 상태로 중합층 내에 포함될 수 있다. The polymerization layer may include, for example, a polymerizable liquid crystal compound in a polymerized state. In the present application, that the polymerizable liquid crystal compound is included in a polymerized state may mean a state in which the liquid crystal compound is polymerized to form a skeleton such as a main chain or a side chain of the liquid crystal polymer in the layer. The polymerization layer may also contain a polymerizable liquid crystal compound in a horizontally aligned state. In the present application, the horizontal alignment indicates that the optical axis of the polymerized layer including the polymerized liquid crystal compound is about 0 degrees to about 25 degrees, about 0 degrees to about 15 degrees, about 0 degrees to about 10 degrees, about the plane of the polymerized layer. It may mean a case having an inclination angle of 0 degrees to about 5 degrees or about 0 degrees. In the present application, the optical axis may mean, for example, a fast axis or a slow axis when incident light passes through the corresponding area. The dichroic dye may also be included in the polymerized layer in a state oriented along the alignment direction of the polymerizable liquid crystal compound.
편광 소자는, 배향막을 추가로 포함할 수 있고, 상기 배향막은 중합층과 인접하게 배치될 수 있다. 도 1는 중합층(101) 및 상기 중합층과 인접하는 배향막(102)를 포함하는 편광 소자를 예시적으로 나타낸다. 배향막으로는, 인접하는 중합층 내의 액정 화합물 및/또는 이색성 염료에 대하여 배향능을 가지는 것이라면 특별한 제한 없이 선택하여 사용할 수 있다. 예를 들어, 러빙 배향막과 같이 접촉식 배향막이거나 또는 광배향막 화합물을 포함하여, 예를 들면, 직선 편광의 조사 등과 같은 비접촉식 방식에 의해 배향 특성을 나타낼 수 있는 것으로 공지된 배향막을 사용할 수 있다. The polarizer may further include an alignment layer, and the alignment layer may be disposed adjacent to the polymerization layer. FIG. 1 exemplarily shows a polarizing element including a polymerized layer 101 and an alignment layer 102 adjacent to the polymerized layer. As an oriented film, if it has an orientation capability with respect to the liquid crystal compound and / or dichroic dye in an adjacent polymer layer, it can select and use without a restriction | limiting in particular. For example, it is possible to use an alignment film known to be capable of exhibiting orientation characteristics by a contactless alignment film such as a rubbing alignment film or a non-contact method such as, for example, irradiation of linearly polarized light, including a photoalignment film compound.
배향막은, 예를 들어, 광배향막일 수 있고, 상기 광배향막은 광배향성 화합물을 포함할 수 있다. 본 출원에서 용어 광배향성 화합물은, 광의 조사를 통하여 소정 방향으로 정렬(orientationally ordered)되고, 상기 정렬 상태에서 인접하는 액정 화합물 등을 역시 소정 방향으로 배향시킬 수 있는 화합물을 의미할 수 있다. 배향성 화합물은, 단분자 화합물, 단량체성 화합물, 올리고머성 화합물 또는 고분자성 화합물일 수 있다.The alignment layer may be, for example, a photoalignment layer, and the photoalignment layer may include a photoalignment compound. In the present application, the term photo-orientation compound may refer to a compound which is aligned in a predetermined direction through irradiation of light and orientates adjacent liquid crystal compounds and the like in the alignment direction in a predetermined direction. The alignment compound may be a monomolecular compound, a monomeric compound, an oligomeric compound, or a high molecular compound.
광배향성 화합물은, 광감응성 잔기(photosensitive moiety)를 포함하는 화합물일 수 있다. 액정 화합물의 배향에 사용될 수 있는 광배향성 화합물은 다양하게 공지되어 있다. 광배향성 화합물로는, 예를 들면, 트랜스-시스 광이성화(trans-cis photoisomerization)에 의해 정렬되는 화합물; 사슬 절단(chain scission) 또는 광산화(photo-oxidation) 등과 같은 광분해(photo-destruction)에 의해 정렬되는 화합물; [2+2] 첨가 환화([2+2] cycloaddition), [4+4] 첨가 환화 또는 광이량화(photodimerization) 등과 같은 광가교 또는 광중합에 의해 정렬되는 화합물; 광 프리즈 재배열(photo-Fries rearrangement)에 의해 정렬되는 화합물 또는 개환/폐환(ring opening/closure) 반응에 의해 정렬되는 화합물 등을 사용할 수 있다. 트랜스-시스 광이성화에 의해 정렬되는 화합물로는, 예를 들면, 술포화 디아조 염료(sulfonated diazo dye) 또는 아조고분자(azo polymer) 등의 아조 화합물이나 스틸벤 화합물(stilbenes) 등이 예시될 수 있고, 광분해에 의해 정렬되는 화합물로는, 시클로부탄 테트라카복실산 이무수물(cyclobutane-1,2,3,4-tetracarboxylic dianhydride), 방향족 폴리실란 또는 폴리에스테르, 폴리스티렌 또는 폴리이미드 등이 예시될 수 있다. 또한, 광가교 또는 광중합에 의해 정렬되는 화합물로는, 신나메이트(cinnamate) 화합물, 쿠마린(coumarin) 화합물, 신남아미드(cinnamamide) 화합물, 테트라히드로프탈이미드(tetrahydrophthalimide) 화합물, 말레이미드(maleimide) 화합물, 벤조페논 화합물 또는 디페닐아세틸렌(diphenylacetylene) 화합물이나 광감응성 잔기로서 찰코닐(chalconyl) 잔기를 가지는 화합물(이하, 찰콘 화합물) 또는 안트라세닐(anthracenyl) 잔기를 가지는 화합물(이하, 안트라세닐 화합물) 등이 예시될 수 있고, 광 프리즈 재배열에 의해 정렬되는 화합물로는 벤조에이트(benzoate) 화합물, 벤조아미드(benzoamide) 화합물, 메타아크릴아미도아릴 (메타)아크릴레이트(methacrylamidoaryl methacrylate) 화합물 등의 방향족 화합물이 예시될 수 있으며, 개환/폐환 반응에 의해 정렬하는 화합물로는 스피로피란 화합물 등과 같이 [4+2] π 전자 시스템([4+2] π electronic system)의 개환/폐환 반응에 의해 정렬하는 화합물 등이 예시될 수 있으나, 이에 제한되는 것은 아니다.The photoalignable compound may be a compound including a photosensitive moiety. Various photo-alignment compounds that can be used for the alignment of the liquid crystal compound are known. Photo-alignment compounds include, for example, compounds aligned by trans-cis photoisomerization; Compounds aligned by photo-destruction, such as chain scission or photo-oxidation; Compounds ordered by photocrosslinking or photopolymerization such as [2 + 2] addition cyclization ([2 + 2] cycloaddition), [4 + 4] addition cyclization or photodimerization; Compounds aligned by photo-Fries rearrangement or compounds aligned by ring opening / closure reaction may be used. As the compound aligned by trans-cis photoisomerization, for example, azo compounds or stilbenes, such as sulfated diazo dyes or azo polymers, may be exemplified. And, as the compound aligned by photolysis, cyclobutane tetracarboxylic dianhydride (cyclobutane-1,2,3,4-tetracarboxylic dianhydride), aromatic polysilane or polyester, polystyrene or polyimide and the like can be exemplified. In addition, as a compound aligned by photocrosslinking or photopolymerization, a cinnamate compound, a coumarin compound, a cinnanam compound, a tetrahydrophthalimide compound, a maleimide compound , Benzophenone compounds, diphenylacetylene compounds, compounds having chalconyl residues (hereinafter referred to as chalconyl compounds) or compounds having anthracenyl residues (hereinafter referred to as anthracenyl compounds) as photosensitive residues; This may be exemplified, and examples of the compounds aligned by the optical freeze rearrangement include aromatic compounds such as benzoate compounds, benzoamide compounds, and methacrylamidoaryl methacrylate compounds. It may be exemplified, the compound aligned by the ring-opening / ring-closure reaction, such as a spiropyran compound A [4 + 2] π electron system ([4 + 2] π electronic system), but may be exemplified by compounds such as sorting by a ring opening / ring-closure reaction of, without being limited thereto.
광배향성 화합물은, 단분자 화합물, 단량체성 화합물, 올리고머성 화합물 또는 고분자성 화합물이거나, 상기 광배향성 화합물과 고분자의 블랜드(blend) 형태일 수 있다. 상기에서 올리고머성 또는 고분자성 화합물은, 상기 기술한 광배향성 화합물로부터 유도된 잔기 또는 상기 기술한 광감응성 잔기를 주쇄 내 또는 측쇄에 가질 수 있다. The photo-alignment compound may be a monomolecular compound, a monomeric compound, an oligomeric compound, or a high molecular compound, or may be in the form of a blend of the photo-alignment compound and the polymer. The oligomeric or polymeric compound as described above may have a residue derived from the above-described photoalignable compound or a photosensitive residue described above in the main chain or in the side chain.
광배향성 화합물로부터 유도된 잔기 또는 광감응성 잔기를 가지거나, 상기 광배향성 화합물과 혼합될 수 있는 고분자로는, 폴리노르보넨, 폴리올레핀, 폴리아릴레이트, 폴라아크릴레이트, 폴리(메타)아크릴레이트, 폴리이미드, 폴리암산(poly(amic acid)), 폴리말레인이미드, 폴리아크릴아미드, 폴리메타크릴아미드, 폴리비닐에테르, 폴리비닐에스테르, 폴리스티렌, 폴리실록산, 폴리아크릴니트릴 또는 폴리메타크릴니트릴 등이 예시될 수 있으나, 이에 제한되는 것은 아니다. Polymers having residues or photosensitive residues derived from photo-alignment compounds or that can be mixed with the photo-alignment compounds include polynorbornene, polyolefins, polyarylates, polyacrylates, poly (meth) acrylates, poly Examples include mead, poly (amic acid), polymaleimide, polyacrylamide, polymethacrylamide, polyvinyl ether, polyvinyl ester, polystyrene, polysiloxane, polyacrylonitrile or polymethacrylonitrile It may be, but is not limited thereto.
배향성 화합물에 포함될 수 있는 고분자로는, 대표적으로는 폴리노르보넨 신나메이트, 폴리노르보넨 알콕시 신나메이트, 폴리노르보넨 알릴로일옥시 신나메이트, 폴리노르보넨 불소화 신나메이트, 폴리노르보넨 염소화 신나메이트 또는 폴리노르보넨 디신나메이트 등이 예시될 수 있지만, 이에 제한되는 것은 아니다.Polymers that may be included in the oriented compound include, for example, polynorbornene cinnamate, polynorbornene alkoxy cinnamate, polynorbornene allylyloxy cinnamate, polynorbornene fluorinated cinnamate, polynorbornene chlorinated cinnamate or Polynorbornene discinnamate and the like can be exemplified, but is not limited thereto.
편광 소자는 또한, 기재층을 추가로 포함할 수 있고, 상기 기재층은, 예를 들어, 중합층의 일면에 형성되어 있을 수 있다. 도 2는 중합층(101) 및 상기 중합층의 일면에 형성된 기재층(201)을 포함하는 편광 소자를 예시적으로 나타낸다. 또는, 편광 소자가 기재층 및 배향막을 모두 추가로 포함할 경우, 도 3에 나타낸 바와 같이, 기재층(201), 배향막(102) 및 중합층(101)을 순차로 포함할 수 있다. The polarizing element may further include a base layer, and the base layer may be formed on one surface of the polymerization layer, for example. 2 exemplarily illustrates a polarizer including a polymer layer 101 and a base layer 201 formed on one surface of the polymer layer. Alternatively, when the polarizing element further includes both the base layer and the alignment layer, as shown in FIG. 3, the base layer 201, the alignment layer 102, and the polymerization layer 101 may be sequentially included.
기재층으로는, 특별한 제한 없이 공지의 소재를 사용할 수 있다. 예를 들면, 유리 필름, 결정성 또는 비결정성 실리콘 필름, 석영 또는 ITO(Indium Tin Oxide) 필름 등의 무기계 필름이나 플라스틱 필름 등을 사용할 수 있다. 기재층으로는, 또한, 광학적으로 등방성인 기재층 또는 위상차층과 같이 광학적으로 이방성인 기재층을 사용할 수 있다. As a base material layer, a well-known raw material can be used without a restriction | limiting in particular. For example, inorganic films, plastic films, etc., such as a glass film, a crystalline or amorphous silicon film, a quartz, or an Indium Tin Oxide (ITO) film, can be used. As the base material layer, an optically anisotropic base material layer such as an optically isotropic base material layer or a retardation layer can be used.
플라스틱 기재층으로는, TAC(triacetyl cellulose); 노르보르넨 유도체 등의 COP(cyclo olefin copolymer); PMMA(poly(methyl methacrylate); PC(polycarbonate); PE(polyethylene); PP(polypropylene); PVA(polyvinyl alcohol); DAC(diacetyl cellulose); Pac(Polyacrylate); PES(poly ether sulfone); PEEK(polyetheretherketon); PPS(polyphenylsulfone), PEI(polyetherimide); PEN(polyethylenemaphthatlate); PET(polyethyleneterephtalate); PI(polyimide); PSF(polysulfone); PAR(polyarylate) 또는 비정질 불소 수지 등을 포함하는 기재층을 사용할 수 있지만 이에 제한되는 것은 아니다. 기재층에는, 필요에 따라서 금, 은, 이산화 규소 또는 일산화 규소 등의 규소 화합물의 코팅층이나, 반사 방지층 등의 코팅층이 존재할 수도 있다. Examples of the plastic substrate layer include triacetyl cellulose (TAC); COP (cyclo olefin copolymer) such as norbornene derivatives; Poly (methyl methacrylate); PC (polycarbonate); PE (polyethylene); PP (polypropylene); PVA (polyvinyl alcohol); DAC (diacetyl cellulose); Pac (Polyacrylate); PES (poly ether sulfone); PEEK (polyetheretherketon PPS (polyphenylsulfone), PEI (polyetherimide); PEN (polyethylenemaphthatlate); PET (polyethyleneterephtalate); PI (polyimide); PSF (polysulfone); PAR (polyarylate) or amorphous fluorine resin The substrate layer may include a coating layer of a silicon compound such as gold, silver, silicon dioxide or silicon monoxide, or a coating layer such as an antireflection layer, if necessary.
본 출원은, 또한, 편광 소자의 제조 방법에 관한 것이다. 편광 소자의 제조 방법은, 예를 들어, 기재층의 일면에 코팅된 전술한 액정 조성물을 중합시키는 것을 포함할 수 있다. 상기 제조 방법에서 기재층 및 액정 조성물에 대한 내용은, 상기 액정 조성물 및 편광 소자의 항목에서 기술한 내용이 동일하게 적용될 수 있다. This application also relates to a manufacturing method of a polarizing element. The manufacturing method of the polarizing element may include, for example, polymerizing the above-described liquid crystal composition coated on one surface of the substrate layer. As for the base layer and the liquid crystal composition in the manufacturing method, the contents described in the items of the liquid crystal composition and the polarizing element may be equally applied.
기재층 상에 액정 조성물의 코팅 방법은, 특별히 제한되지 않고, 예를 들면, 롤 코팅, 인쇄법, 잉크젯 코팅, 슬릿 노즐법, 바 코팅, 콤마 코팅, 스핀 코팅 또는 그라비어 코팅 등과 같은 공지의 코팅 방식을 통한 코팅에 의해 수행될 수 있다. The coating method of the liquid crystal composition on the substrate layer is not particularly limited, and known coating methods such as roll coating, printing, inkjet coating, slit nozzle method, bar coating, comma coating, spin coating or gravure coating, for example. By coating through.
액정 조성물의 중합 방법은, 특별히 제한되지 않고, 공지의 액정 화합물 중합 방법에 의하여 수행될 수 있다. 예를 들어, 중합성 액정 화합물이 양이온 중합성 관능기를 가지는 액정 조성물일 경우, 공지의 양이온 중합 반응에 의하여 중합될 수 있다. 예를 들어, 양이온 중합 반응이 개시될 수 있도록 적정 온도를 유지하는 방식이나 적절한 활성 에너지선을 조사하는 방식에 의하여 수행될 수 있다. 적정 온도에서의 유지 및 활성 에너지선의 조사가 동시에 요구되는 경우, 상기 공정은 순차적 또는 동시에 진행될 수 있다. 상기에서 활성 에너지선의 조사는, 예를 들면, 고압수은 램프, 무전극 램프 또는 크세논 램프(xenon lamp) 등을 사용하여 수행할 수 있으며, 조사되는 활성 에너지선의 파장, 광도 또는 광량 등의 조건은 상기 양이온 중합성 액정 화합물의 중합이 적절히 이루어질 수 있는 범위에서 선택될 수 있다. The polymerization method of the liquid crystal composition is not particularly limited and may be carried out by a known liquid crystal compound polymerization method. For example, when the polymerizable liquid crystal compound is a liquid crystal composition having a cationically polymerizable functional group, it may be polymerized by a known cation polymerization reaction. For example, it may be carried out by maintaining a suitable temperature or irradiating a suitable active energy ray so that the cationic polymerization reaction can be initiated. If the maintenance at the appropriate temperature and the irradiation of the active energy ray is required at the same time, the process can be carried out sequentially or simultaneously. The irradiation of the active energy ray may be performed using, for example, a high pressure mercury lamp, an electrodeless lamp or a xenon lamp, and the like, and the conditions such as the wavelength, light intensity, or light quantity of the active energy ray to be irradiated are The polymerization of the cationic polymerizable liquid crystal compound can be selected in a range that can be appropriately made.
본 출원은, 또한 편광 소자의 용도에 관한 것이다. 예시적인 편광 소자는 디스플레이 장치에 포함되어 유용하게 사용될 수 있다. 디스플레이 장치로는, 액정 표시 장치, 유기 EL(Electroluminescence) 표시 장치, 무기 EL 표시 장치, 전계 방출 표시 장치(FED; Field Emission Display), 표면 전계 방출 표시 장치(SPED; Surface Field Emission Display), 전자 페이퍼(전자 잉크나 전기 영동 소자)를 이용한 표시 장치, 플라즈마 표시 장치, 투사형 표시 장치[예를 들면, 회절 광 밸브 (GLV; grating light valve) 표시 장치, 디지털 마이크로 미러 디바이스(Digital Light Processing)를 갖는 표시 장치] 및 압전 세라믹 표시 장치 등을 예시할 수 있으나, 이에 제한되는 것은 아니다. 액정 표시 장치는, 예를 들면, 투과형 액정 표시 장치, 반투과형 액정 표시 장치, 반사형 액정 표시 장치, 직시형 액정 표시 장치 또는 투사형 액정 표시 장치일 수 있다. 또한, 이러한 디스플레이 장치는 2차원 화상을 표시하는 표시 장치이거나 또는 3차원 화상을 표시하는 입체 표시 장치일 수도 있다. 상기와 같은 디스플레이 장치를 구성하는 방식은 특별히 제한되지 않고, 상기 편광 소자가 사용되는 한 통상적인 방식이 적용될 수 있다.The present application also relates to the use of the polarizing element. Exemplary polarizers may be usefully included in display devices. As a display device, a liquid crystal display device, an organic electroluminescence (EL) display device, an inorganic EL display device, a field emission display device (FED), a surface field emission display device (SPED), an electronic paper Display device using (electronic ink or electrophoretic element), plasma display device, projection display device (for example, display having a diffraction light valve (GLV) display device, digital micro mirror device (Digital Light Processing)) Device] and a piezoelectric ceramic display device, but are not limited thereto. The liquid crystal display may be, for example, a transmissive liquid crystal display, a transflective liquid crystal display, a reflective liquid crystal display, a direct view liquid crystal display, or a projection liquid crystal display. Also, such a display device may be a display device for displaying a two-dimensional image or a stereoscopic display device for displaying a three-dimensional image. The method of configuring such a display device is not particularly limited, and a conventional method may be applied as long as the polarizer is used.
본 출원의 게스트호스트형 액정 조성물은, 간단한 코팅 공정으로 편광 소자를 제조할 수 있으므로 제조 비용을 줄이고 편광 소자의 경량 박형화가 가능할 뿐만 아니라 고온 환경과 같은 가혹한 조건에서도 흡수 스펙트럼 내가 투과 스펙트럼 변화없이 우수한 내열 안정성을 나타내는 편광 소자를 제조할 수 있다. 이러한 편광 소자는, 액정 표시 장치, EL 표시 장치, 전계 방출 표시 장치, 전자 페이퍼를 이용한 표시 장치, 투사형 표시 장치 또는 압전 세라믹 표시 장치 등과 같은 다양한 디스플레이 장치에 적용될 수 있다. The guest-host liquid crystal composition of the present application can manufacture a polarizing element by a simple coating process, thereby reducing manufacturing cost and making it possible to reduce the weight of the polarizing element, and excellent heat resistance without changing the transmission spectrum in the absorption spectrum even under severe conditions such as a high temperature environment. The polarizing element which shows stability can be manufactured. Such a polarizing element can be applied to various display devices such as a liquid crystal display device, an EL display device, a field emission display device, a display device using electronic paper, a projection display device, or a piezoelectric ceramic display device.
도 1 내지 도 3은 예시적인 편광 소자의 모식도이다.1 to 3 are schematic diagrams of exemplary polarizing elements.
도 4는 실시예 및 비교예의 내열 안정성 평가 결과를 나타낸다.4 shows the results of evaluation of heat stability of Examples and Comparative Examples.
이하 실시예 및 비교예를 통하여 상기 편광 소자를 보다 구체적으로 설명하지만, 본 출원의 범위가 하기 제시된 내용에 의해 제한되는 것은 아니다.Hereinafter, the polarizing device will be described in more detail with reference to Examples and Comparative Examples, but the scope of the present application is not limited by the following contents.
실시예 1Example 1
플라스틱 기판(TAC) 일면에 광배향막 형성용 조성물을 건조 후의 두께가 약 200 Å이 되도록 코팅하고, 80℃의 오븐에서 2 분 동안 건조시켰다. 상기에서 광배향막 형성용 조성물로는, 폴리(5-노보넨-2-메틸(4-메톡시 신나메이트)) 2 중량부, 극성 바인더로서 디펜타에리쓰리톨헥사아크릴레이트 1 중량부 및 광개시제(Igacure 907, Ciba-Geigy 社제, 스위스) 0.5 중량부를 용매 (톨루엔) 약 96.8 중량부에 용해시켜 제조한 배향막 전구체 조성물을 사용하였다. 상기 광배향막 형성용 조성물을 건조한 후 자외선(100 mW/cm2)을 3 m/min의 속도로 조사하여 배향 처리를 수행하였다. On one surface of the plastic substrate (TAC), the composition for forming a photo-alignment film was coated so that the thickness after drying was about 200 mm 3, and dried in an oven at 80 ° C. for 2 minutes. As the composition for forming the photo-alignment film, 2 parts by weight of poly (5-norbornene-2-methyl (4-methoxy cinnamate)), 1 part by weight of dipentaerythritol hexaacrylate as a polar binder, and a photoinitiator ( Igacure 907, manufactured by Ciba-Geigy Co., Ltd.) was used to prepare an alignment film precursor composition prepared by dissolving 0.5 parts by weight of the solvent (toluene) to about 96.8 parts by weight. After drying the composition for forming a photo-alignment film was irradiated with ultraviolet (100 mW / cm 2 ) at a rate of 3 m / min to perform an alignment treatment.
이어서, 배향 처리된 배향층 상에 아조계 시안 염료(G-472, 하야바라 社제, 흡수파장: 600 nm) 1 중량부, 중합성 액정 화합물 p -phenylene-di[4-(2,3-epoxypropyloxy)benzoate] 20 중량부 및 양이온 개시제 Triarylsulfonium hexafluorophosphate salts, mixed 50% in propylene carbonate (Sigma-Aldrich 社제) 1 중량부를 포함하는 액정 조성물을 약 1.5㎛ 의 건조 두께가 되도록 도포하고, 하부의 배향층에 배향에 따라 배향시킨 후에, 자외선(300 mW/cm2)을 10 m/min의 속도로 조사하여 액정을 가교 및 중합시켜 편광 소자를 제조하였다. Subsequently, 1 part by weight of an azo cyan dye (G-472, manufactured by Hayabara, absorbing wavelength: 600 nm) on the alignment-treated alignment layer, the polymerizable liquid crystal compound p- phenylene-di [4- (2,3- epoxypropyloxy) benzoate] 20 parts by weight and a cationic initiator Triarylsulfonium hexafluorophosphate salts, mixed 50% in propylene carbonate (Sigma-Aldrich Co., Ltd.) a liquid crystal composition is applied to a dry thickness of about 1.5㎛, the lower alignment layer After aligning according to the orientation, ultraviolet rays (300 mW / cm 2 ) were irradiated at a rate of 10 m / min to crosslink and polymerize the liquid crystal to prepare a polarizing element.
비교예 1Comparative Example 1
중합성 액정 화합물로서 라디칼 중합성 액정 화합물인 Acrylate RM(LC242, BASF社제)을 사용한 것을 제외하고는 실시예 1과 동일한 방법을 수행하여 편광 소자를 제조하였다.A polarizing device was manufactured in the same manner as in Example 1, except that Acrylate RM (LC242, manufactured by BASF), which is a radical polymerizable liquid crystal compound, was used as the polymerizable liquid crystal compound.
시험예 1: 내열 안정성 평가Test Example 1: Evaluation of heat stability
실시예 1 및 비교예 1에서 제조된 편광 소자에 대하여, 10mm×10mm (가로×세로) 크기로 재단하여 시편을 제작한 후 N&K Analyer 장치를 이용하여 파장에 따른 흡광도를 측정하였고, 상기 편광 소자를 100 ℃에서 100 시간 동안 고온 조건에 방치한 후에 다시 파장에 따른 흡광도를 측정하였다. 이렇게 측정된 실시예 1 및 비교예 1의 편광 소자의 흡수 스펙트럼을 도 4에 나타내었다. The polarizers manufactured in Example 1 and Comparative Example 1 were cut into 10 mm × 10 mm (horizontal × vertical) sizes to prepare specimens, and then the absorbances of the polarizers were measured using N & K Analyer devices. After standing at 100 ° C. for 100 hours at 100 ° C., the absorbance according to the wavelength was measured again. The absorption spectra of the polarizing elements of Example 1 and Comparative Example 1 thus measured are shown in FIG. 4.
도 4에 나타낸 바와 같이, 내열 전에는 실시예 1 및 비교예 1의 편광 소자 모두 유사한 흡수 스펙트럼을 나타낸다. 그러나, 내열 후, 실시예 1의 편광 소자는 흡수 스펙트럼을 유지하는 반면 비교예 1의 편광 소자는 최대 흡광도를 나타내는 파장이 약 580 nm에서 약 400 nm로 변하는 것을 확인할 수 있다. 비교예 1과 같이 아크릴로일계 중합성기를 포함하는 액정 화합물을 사용하는 경우, 라디칼 중합 반응을 일으키는 과정에서 남아있는 라디칼이 고온 조건에서 아조계 염료의 취약한 부분을 공격하여 염료 분자를 분해시켜 흡광도가 단파장 쪽으로 이동하게 되는 반면, 실시예 1과 같이 양이온 중합성기를 가지는 액정 화합물을 사용하는 경우, 라디칼에 의한 염료 분해가 없기 때문에 아조계 염료를 사용했을 경우, 안정한 고온 내구성을 확보할 수 있다. 이로부터, 실시예에 따른 편광 소자는 고온 조건에서도 흡수 스펙트럼의 변화 없이 내열 안정성이 우수하다는 점을 알 수 있다. As shown in FIG. 4, before heat resistance, the polarizing elements of Example 1 and Comparative Example 1 exhibit similar absorption spectra. However, after heat resistance, the polarizing element of Example 1 maintains the absorption spectrum while the polarizing element of Comparative Example 1 can be seen that the wavelength showing the maximum absorbance is changed from about 580 nm to about 400 nm. In the case of using a liquid crystal compound including an acryloyl polymerizable group as in Comparative Example 1, the radicals remaining in the course of causing the radical polymerization reaction attack the vulnerable portion of the azo dye under high temperature conditions to decompose the dye molecules and thus absorb On the other hand, when the liquid crystal compound having a cationically polymerizable group is used as in Example 1, since no dye decomposition is caused by radicals, stable high temperature durability can be secured when an azo dye is used. From this, it can be seen that the polarizing element according to the embodiment is excellent in heat resistance even without changing the absorption spectrum even at high temperature.
시험예Test Example 2: 내열  2: heat resistant 광특성Optical properties 평가 evaluation
실시예 1 및 비교예 1에서 제조된 편광 소자를 10mm×10mm (가로×세로) 크기로 재단하여 시편을 제작한 후 Jasco Spectrophotometer V-7100 장비를 이용하여 내열 전과 후의 파장에 따른 투과 스펙트럼을 측정함으로써 내열 광 특성을 평가하였고, 그 결과를 하기 표 1에 정리하였다. After fabricating a specimen by cutting the polarizers manufactured in Example 1 and Comparative Example 1 to a size of 10mm × 10mm (width × length), by measuring the transmission spectrum according to the wavelength before and after heat resistance using the Jasco Spectrophotometer V-7100 equipment Heat-resistant optical properties were evaluated and the results are summarized in Table 1 below.
표 1에 나타낸 바와 같이, 아크릴로일계 중합성기를 포함하는 액정 화합물을 코팅한 비교예 1의 편광 소자의 경우, 단판 투과도 단판 투과도(Ts: 1개의 편광판의 투과율)가 600nm 파장에서 초기 31.5%에서 100℃ 및 100시간 이후 67.1%로 약 53% 변화하였고, 최소 투과를 나타내는 파장이 600nm에서 460nm로 이동하였다. 반면에 에폭시계 중합성기를 포함하는 액정 화합물을 코팅한 실시예 1의 편광 소자의 경우, Ts가 동일한 600nm 영역에서 초기 39.6%에서 내열 후 42.6%로 약 7%의 변화율을 보였다. 또한 중심 파장이 기존 600nm에서 이동이 전혀 없는 것을 확인하였다. 이로써 편광 소자의 내열 광특성도 양이온 중합성 액정 화합물을 사용한 경우가 더 우수하다는 점을 알 수 있다.As shown in Table 1, in the polarizing element of Comparative Example 1 coated with a liquid crystal compound containing an acryloyl series polymerizable group, single plate transmittance single plate transmittance (Ts: transmittance of one polarizing plate) at an initial 31.5% at a wavelength of 600 nm. After about 100 ° C. and 100 hours, the change was about 53% to 67.1%, and the wavelength showing the minimum transmission shifted from 600 nm to 460 nm. On the other hand, the polarizing device of Example 1 coated with a liquid crystal compound including an epoxy-based polymerizable group showed a change rate of about 7% to 42.6% after heat resistance at an initial 39.6% in the same 600 nm region of Ts. In addition, it was confirmed that the center wavelength is no shift at the existing 600nm. Thereby, it turns out that the heat resistance optical characteristic of a polarizing element is more excellent when a cationically polymerizable liquid crystal compound is used.
Ts(초기)(%)Ts (initial) (%) Ts(100℃-100hr)(%)Ts (100 ° C-100hr) (%) △Ts (%)△ Ts (%) △λ(nm)Λλ (nm)
비교예 1Comparative Example 1 31.531.5 67.167.1 5353 120120
실시예 1Example 1 39.639.6 42.642.6 77 00

Claims (16)

  1. 양이온 중합성 액정 화합물 및 이색성 염료를 포함하고, 하기 수식 1을 만족하는 게스트 호스트형 액정 조성물:A guest-host type liquid crystal composition comprising a cationically polymerizable liquid crystal compound and a dichroic dye and satisfying the following formula (1):
    [수식 1][Equation 1]
    -20 ≤100 × (H - W)/W ≤ 20-20 ≤100 × (H-W) / W ≤ 20
    수식 1에서 W는 상기 중합성 액정 화합물이 중합된 직후의 상기 염료의 최대 흡수 파장이고, H는 상기 액정 화합물이 중합된 액정 조성물을 100°C에서 100 시간 유지한 후의 상기 염료의 최대 흡수 파장이다.In Equation 1, W is the maximum absorption wavelength of the dye immediately after the polymerizable liquid crystal compound is polymerized, and H is the maximum absorption wavelength of the dye after maintaining the liquid crystal composition polymerized with the liquid crystal compound at 100 ° C. for 100 hours. .
  2. 제 1 항에 있어서, 상기 양이온 중합성 액정 화합물은 양이온 중합성 관능기로서 에폭시기를 가지는 게스트 호스트형 액정 조성물.The guest host liquid crystal composition according to claim 1, wherein the cationically polymerizable liquid crystal compound has an epoxy group as the cationically polymerizable functional group.
  3. 제 1 항에 있어서, 중합성 액정 화합물은 하기 화학식 1의 화합물인 게스트 호스트형 액정 조성물: The guest host liquid crystal composition of claim 1, wherein the polymerizable liquid crystal compound is a compound represented by the following Chemical Formula 1:
    [화학식 1][Formula 1]
    Figure PCTKR2016007194-appb-I000003
    Figure PCTKR2016007194-appb-I000003
    상기 화학식 1에서 A는 단일 결합, -COO- 또는 -OCO-이고, R1 내지 R10은, 각각 독립적으로 수소, 할로겐, 알킬기, 알콕시기, 알콕시카보닐기, 니트로기, 에폭시기, 시아노기, -O-Q-P 또는 하기 화학식 2의 치환기이되, R1 내지 R10 중 적어도 하나는 에폭시기, 시아노기, -O-Q-P 또는 하기 화학식 2의 치환기이거나, R1 내지 R5 중 인접하는 2개의 치환기 또는 R6 내지 R10 중 인접하는 2개의 치환기는 서로 연결되어 -O-Q-P로 치환된 벤젠을 형성하고, 상기에서 Q는 알킬렌기 또는 알킬리덴기이며, P는 에폭시기이다In Formula 1, A is a single bond, -COO- or -OCO-, and R 1 to R 10 are each independently hydrogen, halogen, alkyl group, alkoxy group, alkoxycarbonyl group, nitro group, epoxy group, cyano group,- OQP or a substituent of Formula 2, wherein at least one of R 1 to R 10 is an epoxy group, a cyano group, -OQP or a substituent of Formula 2, or two adjacent substituents of R 1 to R 5 or R 6 to R 10 Two adjacent substituents are connected to each other to form a benzene substituted with -OQP, wherein Q is an alkylene group or an alkylidene group, and P is an epoxy group.
    [화학식 2][Formula 2]
    Figure PCTKR2016007194-appb-I000004
    Figure PCTKR2016007194-appb-I000004
    상기 화학식 2에서 B는 단일 결합, -COO- 또는 -OCO-이고, R11 내지 R15는, 각각 독립적으로 수소, 할로겐, 알킬기, 알콕시기, 알콕시카보닐기, 니트로기, 에폭시기, 시아노기 또는 -O-Q-P이되, R11 내지 R15 중 적어도 하나는 에폭시기, 시아노기, 또는 -O-Q-P이거나, R11 내지 R15 중 인접하는 2개의 치환기는 서로 연결되어 -O-Q-P로 치환된 벤젠을 형성하고, 상기에서 Q는 알킬렌기 또는 알킬리덴기이며, P는 에폭시기이다.In Formula 2, B is a single bond, -COO-, or -OCO-, and R 11 To R 15 are each independently hydrogen, halogen, alkyl group, alkoxy group, alkoxycarbonyl group, nitro group, epoxy group, cyano group or -OQP, wherein at least one of R 11 to R 15 is an epoxy group, cyano group, or -OQP Or R 11 Two adjacent substituents of R to R 15 are connected to each other to form a benzene substituted with —OQP, wherein Q is an alkylene group or an alkylidene group, and P is an epoxy group.
  4. 제 1 항에 있어서, 이색성 염료의 최대 흡수 파장이 400 nm 내지 700 nm의 파장 범위 내에 있는 게스트 호스트형 액정 조성물. The guest host liquid crystal composition according to claim 1, wherein the maximum absorption wavelength of the dichroic dye is within a wavelength range of 400 nm to 700 nm.
  5. 제 1 항에 있어서, 이색성 염료는 시안 염료, 안트라퀴논 염료, 아크리딘 염료, 시아닌 염료 및 나프탈렌 염료 중 하나 이상의 염료를 포함하는 게스트 호스트형 액정 조성물.The guest host liquid crystal composition of claim 1, wherein the dichroic dye comprises at least one of cyan dye, anthraquinone dye, acridine dye, cyanine dye, and naphthalene dye.
  6. 제 1 항에 있어서, 이색성 염료는 중합성 액정 화합물 100 중량부 대비 0.1 중량부 내지 20 중량부 비율로 포함되는 게스트 호스트형 액정 조성물.The guest host liquid crystal composition of claim 1, wherein the dichroic dye is included in an amount of 0.1 part by weight to 20 parts by weight with respect to 100 parts by weight of the polymerizable liquid crystal compound.
  7. 제 2 항에 있어서, 양이온 개시제를 추가로 포함하는 게스트 호스트형 액정 조성물.The guest host liquid crystal composition according to claim 2, further comprising a cationic initiator.
  8. 양이온 중합성 액정 화합물 및 이색성 염료를 포함하는 게스트 호스트형 액정 조성물의 중합층을 포함하고, 하기 수식 1을 만족하는 편광 소자:A polarizing element comprising a polymerized layer of a guest-hosted liquid crystal composition comprising a cationically polymerizable liquid crystal compound and a dichroic dye, and satisfying the following formula (1):
    [수식 1][Equation 1]
    -20 ≤100 × (H - W)/W = 20-20 ≤100 × (H-W) / W = 20
    수식 1에서 W는 상기 중합성 액정 화합물이 중합된 직후의 상기 염료의 최대 흡수 파장이고, H는 상기 액정 화합물이 중합된 액정 조성물을 100℃에서 100 시간 유지한 후의 상기 염료의 최대 흡수 파장이다.In Equation 1, W is the maximum absorption wavelength of the dye immediately after the polymerizable liquid crystal compound is polymerized, and H is the maximum absorption wavelength of the dye after holding the liquid crystal composition polymerized with the liquid crystal compound at 100 ° C. for 100 hours.
  9. 제 8 항에 있어서, 중합층은 양이온 중합성 액정 화합물 및 이색성 염료를 포함하는 편광 물질의 코팅층인 편광 소자.The polarizing element of claim 8, wherein the polymerization layer is a coating layer of a polarizing material including a cationically polymerizable liquid crystal compound and a dichroic dye.
  10. 제 8 항에 있어서, 중합층은 두께가 0.5㎛ 내지 10㎛ 의 범위 내에 있는 편광 소자. The polarizing element of claim 8, wherein the polymer layer has a thickness in a range of 0.5 μm to 10 μm.
  11. 제 8 항에 있어서, 중합성 액정 화합물은 수평 배향된 상태로 중합층에 포함되어 있는 편광 소자. The polarizing element according to claim 8, wherein the polymerizable liquid crystal compound is contained in the polymerized layer in a horizontally oriented state.
  12. 제 8 항에 있어서, 중합층과 인접하는 배향막을 추가로 포함하는 편광 소자.The polarizing element according to claim 8, further comprising an alignment film adjacent to the polymerization layer.
  13. 제 12 항에 있어서, 배향막은 광배향막인 편광 소자. The polarizing element according to claim 12, wherein the alignment layer is a photoalignment layer.
  14. 제 8 항에 있어서, 중합층의 일면에 형성되는 기재층을 추가로 포함하는 편광 소자.The polarizing element according to claim 8, further comprising a base layer formed on one surface of the polymerization layer.
  15. 기재층의 일면에 코팅된 제 1 항의 액정 조성물을 중합시키는 것을 포함하는 편광 소자의 제조 방법. A method of manufacturing a polarizing element comprising polymerizing the liquid crystal composition of claim 1 coated on one surface of a base layer.
  16. 제 8 항의 편광 소자를 포함하는 디스플레이 장치.A display device comprising the polarizing element of claim 8.
PCT/KR2016/007194 2015-07-02 2016-07-04 Guest-host type liquid crystal composition WO2017003268A1 (en)

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WO2018213819A1 (en) * 2017-05-19 2018-11-22 Kent State University Photostable alignment layer via bleaching
CN111149048A (en) * 2017-10-31 2020-05-12 株式会社Lg化学 Variable transmittance device

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