WO2015099377A1 - Composition destinée à former un polariseur à base de colorant et polariseur à base de colorant - Google Patents

Composition destinée à former un polariseur à base de colorant et polariseur à base de colorant Download PDF

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Publication number
WO2015099377A1
WO2015099377A1 PCT/KR2014/012639 KR2014012639W WO2015099377A1 WO 2015099377 A1 WO2015099377 A1 WO 2015099377A1 KR 2014012639 W KR2014012639 W KR 2014012639W WO 2015099377 A1 WO2015099377 A1 WO 2015099377A1
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Prior art keywords
carbon atoms
dye
substituted
type polarizer
formula
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PCT/KR2014/012639
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English (en)
Korean (ko)
Inventor
유동우
전성호
서경창
장형빈
Original Assignee
주식회사 엘지화학
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Priority claimed from KR1020140184900A external-priority patent/KR101732687B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201480071044.1A priority Critical patent/CN105916943B/zh
Priority to JP2016534147A priority patent/JP6483688B2/ja
Priority to US15/033,450 priority patent/US10527758B2/en
Priority to EP14875541.6A priority patent/EP3048139A4/fr
Publication of WO2015099377A1 publication Critical patent/WO2015099377A1/fr

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
    • C09B31/043—Amino-benzenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
    • C09B31/062—Phenols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/16—Trisazo dyes
    • C09B31/18—Trisazo dyes from a coupling component "D" containing a directive amine group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/26—Reflecting filters

Definitions

  • Dye-type polarizer forming composition and dye-type polarizer
  • the present invention relates to a composition for forming a dye-type polarizer and a dye-type polarizer, which enables the provision of a dye-type polarizer having both excellent polarization degree, heat resistance and dichroic ratio.
  • Film polarizers also known as sheet polarizers, are generally optical members capable of polarizing light in a specific direction and are widely used in display elements such as liquid crystal displays.
  • a film polarizer is widely used to selectively transmit light in a specific direction among light incident from the backlight and light passing through the liquid crystal layer and to control polarization.
  • a polarizer in the form of a film a polarizer using a stretched polyvinyl alcohol (PVA) film previously dyed with a dichroic dye is most widely used in the liquid crystal display device and the like.
  • PVA stretched polyvinyl alcohol
  • such a polarizer using the stretched PVA film exhibits poor heat resistance and moisture resistance, and optical performance may be degraded due to moisture infiltration or relaxation of the polymer.
  • a polarizer is mainly contained between protective films, such as TAC, and adhere
  • an adhesive film for adhering such a polarizer to the liquid crystal display element or the like is required, and such a polarizer may cause a polarizer thickness of about 70 to 150 ⁇ as a whole.
  • a dye-type polarizer in the form of a thin film or a film including a dye layer whose main component is an oriented dichroic dye has been proposed and studied.
  • These dye-type polarizers are separate The dichroic dye in the said dye layer is orientated using an orientation layer, and the polarization degree excellent by the dichroic dye thus oriented can be shown.
  • the present invention provides a composition for forming a dye-type polarizer, which enables the provision of a dye-type polarizer having both excellent polarization degree, heat resistance and dichroic ratio.
  • the present invention is to provide a dye-type polarizer obtained by using the composition, showing excellent polarization degree, improved heat resistance and dichroic ratio.
  • This invention also provides the display element containing the said dye type polarizer.
  • the present invention is a curable anisotropic dye of the formula (1); And it provides a composition for forming a dye-type polarizer comprising an orientation aid of the formula (2), (3) or their radical polymers:
  • n is an integer of 2 to 5
  • At least one of Q, and Q 2 is a curable unsaturated functional group, and the rest are hydrogen, alkyl having 1 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, alkylester having 1 to 20 carbon atoms, or an amine group,
  • a ! And A 2 may be the same as or different from each other, and is substituted or unsubstituted arylene having 6 to 40 carbon atoms, or substituted or unsubstituted heteroarylene having 4 to 30 carbon atoms,
  • At least one of Q 3 and Q 4 is a curable unsaturated functional group, the remainder is hydrogen, alkyl having 1 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, alkyl ester having 1 to 20 carbon atoms, -CN, -N0 2 , halogen, Or an amine group unsubstituted or substituted with 1 to 2 carbon atoms of 1 to 6 carbon atoms,
  • a 3 and A 4 may be the same as or different from each other, and are substituted or unsubstituted arylene having 6 to 40 carbon atoms, or substituted or unsubstituted hetero arylene having 4 to 30 carbon atoms,
  • R 2 is hydrogen or alkyl of 1 to 20 carbon atoms,
  • At least one of Q 5 and Q 6 is a curable bubbling functional group, and the rest are hydrogen alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, aryl having 6 to 40 carbon atoms, alkoxy having 1 to 20 carbon atoms, and 1 carbon atom. It is an amine group unsubstituted or substituted with an alkyl ester of 20 to 20, CN, -N0 2 , halogen, ' or alkyl having 1 to 2 carbon atoms,
  • a 5 and A 6 may be the same or different from each other, and are substituted or unsubstituted arylene having 6 to 40 carbon atoms, or substituted or unsubstituted heteroarylene having 4 to 30 carbon atoms,
  • At least one member selected from the group consisting of NR 3 -and -PR 3 - is a combined divalent functional group
  • R 3 is hydrogen or alkyl having 1 to 20 carbon atoms.
  • the present invention also provides a dye-type polarizer comprising a dye layer containing a cured product of the composition for forming a dye-type polarizer.
  • the present invention provides a display device including the dye-type polarizer.
  • the composition for dye-type polarizer formation of the present invention contains a specific curable anisotropic dye and an orientation aid.
  • the curable anisotropic dye may include a curable unsaturated functional group at its end, and may be copolymerized with an orientation aid to form a crosslinked structure by curing after orientation. Therefore, since the orientation of the anisotropic dye and the dye layer can be stabilized by such a crosslinked structure, such an orientation can be prevented from being randomized even when exposed to high temperature heat.
  • the alignment assistant may exhibit excellent orientation, and may further improve the orientation and dichroic ratio of the dye layer as a component capable of forming a crosslinked structure in combination with the curable anisotropic dye.
  • the composition for forming a dye type polarizer it is possible to maintain a high degree of orientation and polarization degree of the dye layer even when exposed to high temperature heat, as a result can provide a dye type polarizer exhibiting high polarization degree and more improved heat resistance Will be.
  • the alignment aid may serve as a host in the dye layer, and at the same time may further improve the orientation of the anisotropic dye, and can also act as an anisotropic dye by itself, the polarization of the dye-type polarizer is also It can be further improved. Therefore, by using the composition for forming a dye-type polarizer, it is possible to provide a dye-type polarizer having excellent physical properties such as polarization degree, transmittance, heat resistance and dichroic ratio.
  • Such a dye type polarizer can replace the polarizer using a stretched PVA film that has been conventionally applied very effectively, and can exhibit excellent characteristics by overcoming the limitations of the existing dye type polarizer.
  • the curable anisotropic dye of the formula ⁇ 1 the curable anisotropic dye of the formula ⁇ 1; And an alignment aid of the following general formulas (2) and (3) or radical polymers thereof.
  • n is an integer of 2 to 5
  • A, and A 2 may be the same as or different from each other, and are substituted or unsubstituted arylene having 6 to 40 carbon atoms, or substituted or unsubstituted heteroarylene having 4 to 30 carbon atoms,
  • At least one of Q 3 and Q 4 is a curable unsaturated functional group, the remainder is hydrogen alkyl having 1 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, alkyl ester having 1 to 20 carbon atoms, —CN, —N0 2 , halogen, or 1 An amine group unsubstituted or substituted with 2 to 2 carbon atoms alkyl,
  • a 3 and A 4 may be the same as or different from each other, and are substituted or unsubstituted arylene having 6 to 40 carbon atoms, or substituted or unsubstituted hetero arylene having 4 to 30 carbon atoms,
  • At least one of Q 5 and 3 ⁇ 4 is a curable unsaturated functional group, and the other is hydrogen, Alkyl of 1 to 20 carbon atoms, cycloalkyl of 3 to 12 carbon atoms, aryl of 6 to 40 carbon atoms, alkoxy of 1 to 20 carbon atoms, alkyl ester of 1 to 20 carbon atoms, -CN, -N0 2 , halogen, or 1 to 2
  • An amine group unsubstituted or substituted with 1 to 6 carbon atoms, and
  • a 5 and A 6 may be the same or different from each other, and are substituted or unsubstituted arylene having 6 to 40 carbon atoms, or substituted or unsubstituted heteroarylene having 4 to 30 carbon atoms,
  • R 3 is hydrogen or alkyl having 1 to 20 carbon atoms.
  • composition of the above-described embodiment of the general formula (1) having a structure in which a curable unsaturated functional group is introduced at both ends by irradiation with heat or UV in the structure of a non-curable azo dye applied to a conventional dichroic dye or the like.
  • a curable anisotropic dye and an orientation aid of the above-mentioned general formulas (2) and (3) or their radical polymers are also included in the above-described embodiment of the general formula (1) having a structure in which a curable unsaturated functional group is introduced at both ends by irradiation with heat or UV in the structure of a non-curable azo dye applied to a conventional dichroic dye or the like.
  • a curable anisotropic dye and an orientation aid of the above-mentioned general formulas (2) and (3) or their radical polymers are examples of the above-mentioned general formulas (2) and (3) or their radical polymers.
  • the curable anisotropic dye of Chemical Formula 1 has one or more azo groups and (hetero) arylenes connected to each other to have a functional group which can be oriented by the lower alignment layer, and together with the chemically introduced curable unsaturated functional group at the terminal.
  • the alignment aid in the form of Formula 2 or the radical polymer thereof may also have a chemical structure in which an azo group and a (hetero) arylene are connected to have an oriented functional group, and a curable unsaturated functional group is introduced at an end thereof.
  • the alignment aid in the form of the formula (3) or the radical polymer thereof may also exhibit excellent orientation including the aromatic group of (hetero) arylene, and may further enhance the orientation of the anisotropic dye and the dye layer including the same. have.
  • the dye layer of the dye-type polarizer is formed using the composition of one embodiment including these curable anisotropic dyes and an alignment aid, and after the alignment is conducted, irradiation with heat or UV, the oriented anisotropic dye ends and the alignment aid Each contained at the end Unsaturated functional groups can be cured and / or polymerized with each other to form a crosslinked structure.
  • composition of this embodiment it is possible to maintain a high degree of orientation and polarization degree of the dye layer even when exposed to high temperature heat, resulting in a dye-type polarizer exhibiting a high dichroic ratio, polarization degree and improved heat resistance Will be.
  • the alignment aid may act as a host of the curable anisotropic dye in the dye layer, may further improve the orientation of the anisotropic dye, and may also act as an anisotropic dye by itself.
  • an orientation aid may further improve the degree of polarization of the dye-type polarizer formed from the composition of one embodiment. Therefore, by using the composition for forming a dye-type polarizer of the embodiment, it is possible to provide a dye-type polarizer having excellent physical properties such as polarization degree, transmittance, heat resistance and dichroic ratio.
  • Such a dye type polarizer can replace the polarizer using a stretched PVA film that has been conventionally applied very effectively, and can exhibit excellent characteristics by overcoming the limitations of the existing dye type polarizer.
  • any of the Q, to Q 6 unsaturated functional groups known to be curable, crosslinked and / or polymerizable by heat or UV light irradiation It may be an unsaturated functional group of, representative examples of such an unsaturated functional group include a (meth) acrylate group, an epoxy group, a vinyl group or any functional group containing these at the terminal.
  • Each of the above to Q 6 may be independently the same or different unsaturated functional groups from each other, and may be suitably the same (meth) acrylate group or epoxy group.
  • the remaining Q 6 which are not unsaturated functional groups are each independently hydrogen, alkyl having 1 to 20 carbon atoms, aryl having 6 to 40 carbon atoms, alkoxy having 1 to 20 carbon atoms, alkyl ester having 1 to 20 carbon atoms, -CN, halogen, or 1 It is appropriate that the amine group or the like is substituted or unsubstituted with alkyl having 2 to 2 carbon atoms.
  • the A to 6 are each independently alkoxy having 1 to 20 carbon atoms, alkyl having 1 to 20 carbon atoms, halogen, -N ( aryl having 6 to 40 carbon atoms unsubstituted or substituted with 3 ⁇ 4 or alkyl ester of 1 to 6 carbon atoms Can be Ren.
  • the specific arylene structure of these to A 6 is included, and as the terminal Qi to Q 6 is the functional group described above, the anisotropic dye, the orientation aid and the dye layer including the same It can be oriented more effectively by the lower orientation layer etc., and can ensure the excellent orientation of a dye layer, and the outstanding polarization degree of a dye type polarizer.
  • divalent functional group that serves as a linker for connecting the (saturated) functional group of the terminal to the end and the linking structure of the oriented azo group and (hetero) arylene with each other.
  • Each divalent functional group listed above may be combined, or two or more selected from them may be combined and linked divalent functional groups.
  • these to B 8 may be the same as each other, in consideration of the kind of arylene or terminal functional groups to which such a linking group may be a different divalent functional group of course.
  • n may be an integer or an integer from 2 to 4, from 2 to 5. That is, as the linking structure of the oriented azo group and (hetero) arylene is properly included, the curable anisotropic dye may exhibit excellent orientation, while the orientation of the anisotropic dye is changed by the crosslinked structure of the terminal unsaturated functional group. More effectively stabilized It becomes possible to provide the dye-type polarizer showing the excellent heat resistance.
  • n is an integer of 2 or more, and two or more repeating unit structures of-(A! -NN)-are repeatedly included and the same unit structures may be repeated and included in anisotropic dye structure, but different from each other-(A Of course, the unit structure of ! -NN)-may be repeatedly included in the anisotropic dye structure.
  • examples of the substituent which may be further substituted with each substituent include —CN, —N0 2 , an amine group, an alkylester, halogen, nitrile, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, halo Alkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl or siloxy and the like.
  • curable anisotropic dye of the above-mentioned formula (1) include compounds selected from the group consisting of the following formula la to If, but not limited to these curable anisotropic dyes falling within the scope of the formula (1) It goes without saying that the dye-type polarizer showing excellent polarization degree and heat resistance can be provided.
  • the above-mentioned curable anisotropic dye can be prepared by a method of introducing an unsaturated functional group such as a (meth) acrylate group, an epoxy group or a vinyl group to a terminal of an uncured azo dye having anisotropic or dichroic properties.
  • an unsaturated functional group such as a (meth) acrylate group, an epoxy group or a vinyl group
  • such a manufacturing process may be in accordance with conventional reaction conditions and methods for introducing each functional group according to the type of the unsaturated functional group, and specific reaction conditions and methods are also described in the following examples, and thus, further description thereof will be omitted. Let's do it.
  • the above-mentioned curable anisotropic dye may be used by mixing one to five kinds of dyes to have an appropriate color according to the use.
  • Anisotropic dyes of the general formula (1) are generally rod-like or rod-like similar structure, even if used in combination with each other, the dye layer comprising the same can be easily oriented according to the orientation of the underlying alignment layer, formed from the composition Dye-type polarizer can exhibit more excellent degree of polarization.
  • composition of one embodiment further comprises an orientation aid in the form of Formula 2, 3 or radical polymer thereof, the specific functional group definition in the structure of Formula 2 or 3 (ie, A 3 to A 6 , ⁇ 3 to ⁇ 8 , and specific examples and definitions of Q 3 to 3 ⁇ 4) have been described together with Chemical Formula 1, and thus, further description thereof will be omitted.
  • the alignment aid is only in the form of the monomer of Formula 2 or 3
  • they may be radically polymerized and included as a radical polymer in a form in which terminal unsaturated groups of formula (2) or (3) are linked to each other.
  • the orientation of the curable anisotropic dye described above, the dichroic ratio and polarization degree of the polarizer obtained from the composition of one embodiment can be appropriately improved, and the orientation of the dye layer is more stabilized to provide heat resistance. Can be improved.
  • Orientation aids in the form of such radical polymers can be obtained by using a compound of Formula 2 or 3 as a monomer and radically polymerizing it in a conventional manner, for example, about 1000 to 30000, black about 2000 to 15000, or It may have a weight average molecular weight of about 3000 to 10000.
  • the alignment aid includes an unsaturated functional group of Q 3 to Q 6 at least at one end, so as to properly form a cured and crosslinked structure with the above-described curable anisotropic dye. It can be exposed even if the high temperature heat stability than ⁇ the orientation of the anisotropic dye and a dye-containing layer, it effectively suppress the screen orientation is such disorder.
  • the alignment aid may include an arylene structure of A 3 to A 6 may exhibit excellent orientation, further improves the orientation of the curable anisotropic dye, the dichroic ratio and polarization degree of the polarizer obtained from the composition of the embodiment You can.
  • the alignment aid of Formula 2 may include the same type of azo group as the curable anisotropic dye of Formula 1, and may exhibit excellent interaction therewith, thereby further improving the orientation of the anisotropic dye and the dichroic ratio and polarization degree of the polarizer. You can.
  • the specific divalent functional groups of B 3 to B 8 described above as linkers it is possible to appropriately control the electron density change of the orientation aid and the composition of one embodiment.
  • Orientation aids of the above-mentioned formulas (II) and (3) or their radical polymers may be prepared according to methods known to those skilled in the art or may be obtained commercially, which may be obtained by conventional methods.
  • alignment aid examples include a compound selected from the group consisting of the following Chemical Formulas 2a to 2d and 3a to 3f, or a radical polymer obtained by using at least one thereof as a monomer, but is not limited thereto.
  • Orienting aids falling within the category of formula (2) or (3) or their radical polymers It can be used without particular limitation, showing excellent dichroic ratio, polarization degree and heat resistance-to provide a dye type polarizer.
  • the composition for forming a dye-type polarizer according to the embodiment may further include a reactive mesogen together with the above-described curable anisotropic dye and an orientation aid.
  • a reactive mesogen such as “reactive mesogen” (RM), as previously known, may be polymerized, crosslinked or cured by light irradiation, including UV irradiation, including unsaturated groups that are polymerizable, crosslinked or curable in molecular buildup, As referring to a material exhibiting liquid crystal phase behavior including a mesogen group, this also has a curable unsaturated group.
  • Such reactive mesogens may also be cured together with the above-described curable anisotropic dye and an orientation aid to form a crosslinked structure, thereby further stabilizing the orientation of the anisotropic dye and suppressing disorder of such an orientation even when high temperature heat is applied.
  • the polarization degree and heat resistance of the dye type polarizer can be further improved.
  • a reactive mesogen it is polymerized by UV irradiation including an unsaturated group.
  • any material exhibiting liquid crystal phase behavior including mesogenic groups can be used without any particular limitation.
  • the polarizer has excellent heat resistance by forming a crosslinked structure more effectively with the curable anisotropic dye or an orientation aid, and further improves the orientation or dichroic ratio of the curable anisotropic dye and the dye dance including the same, thereby providing a polarizer having excellent characteristics.
  • a compound of formula 4 may be suitably used:
  • a and B are each independently arylene having 6 to 40 carbon atoms or cycloalkylene having 6 to 12 carbon atoms, black to 6 to 8 carbon atoms
  • R 15 to R 2 2 are each independently hydrogen, chlorine Or halogen of fluorine, —CN, alkyl having 1 to 12 carbon atoms, aryl having 6 to 40 carbon atoms, alkoxy having 1 to 12 carbon atoms, and alkoxycarbonyl having 1 to 12 carbon atoms
  • Z 2 are each independently a (meth) acrylate group
  • ⁇ ,, ⁇ 2 and , Q are each independently defined the same as A, Ei or, Xl and x 2 are Each independently represents an integer of
  • a and B in the formula (4) is phenylene, or cyclohexylene, at least one of the A and B is phenylene Is appropriate.
  • Semi-ungsogenic mesogens comprising such compounds of formula 4 may be prepared according to methods known to those skilled in the art or may be obtained commercially.
  • a composition for one embodiment dye type polarizing element is formed with the components described above: can further include a multi-functional binder that contains more than one curable unsaturated functional group.
  • the polyfunctional binder is further included, when the curing is performed after the orientation of the curable anisotropic dye described above, the unsaturated functional groups of the multifunctional binder may be cured, crosslinked or combined with the unsaturated functional groups contained in other components such as the anisotropic dye.
  • the polymerization may be performed to form a crosslinked structure, and a crosslinked copolymer of the curable anisotropic dye, an orientation aid, optionally a reactive mesogen and a multifunctional binder, and a dye layer including the same may be formed.
  • the degree of curing of the dye layer and the dye-type polarizer is further increased to further improve the mechanical properties.
  • the polyvalent (meth) acrylate type compound which has a bifunctional or more (meth) acrylate group can be used suitably. More specifically, examples of such a polyvalent (meth) acrylate-based compound include pentaerythryl triacrylate (pentaerythritol triacrylate), tri (2-acrylolyloxyethyl) isocinurate (tris (2-acrylolyloxyethyl) isocynurate) ,
  • Trimethylolpropane triacrylate and dipentaerythritol may be at least one selected from the group consisting of dipentaerythritol hexaacrylate, and two or more selected among them may be used together, of course. ⁇
  • composition of one embodiment described above comprises about 1 to 25 parts by weight of the curable anisotropic dye, about 50 to about 95 parts by weight of the orientation aid, and about 1 to about 1 part of the reactive mesogen based on 100 parts by weight of the solids content of the total composition. And 45 parts by weight. Further, with respect to 100 parts by weight of the solid content, it may further comprise about 0 to 49 parts by weight of the multifunctional binder.
  • composition of one embodiment may further include an organic solvent for dissolving or dispersing the above-described components, and optionally a thermal initiator or photoinitiator for assisting the curing of each component, such as the curable anisotropic dye It may further comprise the same initiator.
  • an organic solvent an appropriate organic solvent capable of effectively dissolving or dispersing each component such as the curable anisotropic dye and an orientation aid
  • the solvent can be obviously selected and used by those skilled in the art, and as the thermal initiator or the photoinitiator, an initiator capable of effectively curing it can be appropriately selected and used depending on the type of the unsaturated functional group such as the curable anisotropic dye or the orientation aid. .
  • organic solvents include methylene chloride (MC), chloroform, cyclopentanone, and cyclonucleic acid, toluene, xylene, dioxane, N-methylpyridone (NMP), propylene glycol monomethyl ether acetate (PGMEA).
  • MC methylene chloride
  • NMP N-methylpyridone
  • PMEA propylene glycol monomethyl ether acetate
  • Igacure series such as Igacure 184, 819, 907, 369, etc. are mentioned.
  • a dye-type polarizer comprising a cured product of the above-mentioned composition for forming a dye-type polarizer.
  • the cured product included in the dye layer is copolymerized with a curable anisotropic dye and an orientation aid to crosslink the curable unsaturated functional groups of each component. It may include a crosslinked copolymer forming a structure, at least a portion of the curable anisotropic dye may be in an oriented state. More specifically, in the cured product, the terminally unsaturated functional groups of the curable anisotropic dye and the orientation assistant may combine with each other to form a crosslinked structure, and as a result, the crosslinked copolymer and a dye layer including the same may be formed. have.
  • the dye layer of the dye-type polarizer is obtained from a composition further comprising a semi-ungogenic mesogen and / or a polyfunctional binder, together with a curable anisotropic dye and an orientation aid
  • the cargo may comprise a crosslinked copolymer in which a curable anisotropic dye, an orientation aid, optionally a reactive mesogen and a multifunctional binder comprising at least two curable unsaturated functional groups are copolymerized so that the curable functional groups of each component form a crosslinked structure. And at least an egg portion of the curable anisotropic dye may be in an oriented state.
  • the terminal unsaturated functional group of the curable anisotropic dye and the orientation aid, optionally the unsaturated group of the reactive mesogen and the unsaturated functional group of the multifunctional binder are cured.
  • the process may be bonded to each other to form a crosslinked structure, as a result can be formed the crosslinked copolymer and a dye layer including the same.
  • the dye-type polarizer of another embodiment exhibits improved heat resistance along with excellent polarization degree, thereby maintaining excellent polarization degree and other physical properties even when exposed to high temperature heat.
  • the dye layer may have a dichroic ratio of about 10 or more, black about 15 or more.
  • the polarizer may exhibit more improved orientation and dichroic ratio by the addition of an orientation aid or optional reactive mesogen.
  • the dichroic ratio may be defined as the ratio of absorbance (measured at vertical incidence) along the absorption axis and absorbance along the transmission axis.
  • the dye layer has excellent orientation and high dichroic ratio such as the anisotropic dye, the polarizer exhibits excellent polarization degree and can be suitably used as a polarizer for various fields or applications.
  • the dye layer may have a thickness of about 10 / im or less, for example, about 1 to 5 thicknesses.
  • the dye type polarizer may be more appropriately applied as an OLED antireflection film or the like, in which a stretched PVA film polarizer is difficult to apply.
  • the above-described curable anisotropic dyes and the like can be oriented during the manufacturing process of the polarizer, and can be oriented in accordance with conventional orientation methods known before, for example, rubbing orientation method or photoalignment method, etc. Can be.
  • the polarizer may further include an alignment layer for orienting the curable anisotropic dye under the dye layer and selectively aligning a reactive mesogen or an orientation aid together.
  • a photoalignment layer including a photoreactive polymer is further formed below the dye layer, and the photoreactive polymer is photoaligned, and then used to cure the curable anisotropic dye and optionally an orientation aid or reactive meso. Zen can be oriented.
  • the photo-alignment layer is a photo- semi-active polymer, for example, previously known
  • a vinyl polymer, a norbornene-based polymer or a (meth) acrylate-based polymer having a cinnamate group, a chalcone group, an azo group or a coumarin group photoreactive group can be formed without any particular limitations.
  • the said hardening type anisotropic dye etc. can be orientated suitably.
  • the photo-alignment layer is combined with at least one photoreactor selected from the group consisting of cinnamate-based photoreactor, chalcon photoreactor, coumarin-based photoreactor and azo photoreactor to the norbornene repeating unit It is more appropriate to include norbornene-based photoreactive polymers.
  • the photoalignment layer including the photoreactive polymer the curable anisotropic dye or the like can be more effectively oriented, and at the same time, the thermal stability and mechanical properties of the photoalignment and the dye type polarizer including the same are further improved. You can.
  • the dye-type polarizer may be a patterned dye-type polarizer having a predetermined pattern form, in this case, the dye layer is a cured product of the composition for forming a dye-type polarizer is selectively formed only in a predetermined region The remaining region may include the removed cured product pattern.
  • the patterned polarizer is formed on the substrate by forming the dye-type polarizer forming composition on a substrate, and then selectively irradiated with heat or UV to only a portion of the region through a mask, thereby selectively selecting only the region. It can form by advancing hardening by the process. Thereafter, the composition may be removed from the remaining uncured region to easily form a patterned polarizer having a desired pattern.
  • the cured product pattern may be in the form of a line pattern having a predetermined pitch, line width, or the like, and the aspect ratio of the cross section in each pattern included in the cured product pattern is about 0.002 to 1 Can be
  • the dye-type polarized light may further include a substrate, and may have a film form in which the alignment layer, the dye layer, and the like are formed on the substrate.
  • Cellulose-based substrates such as TAC
  • polyester-based substrates such as PET
  • acrylate-based substrates such as COP or COC
  • substrates in the form of unstretched films can be suitably used.
  • the above-described dye-type polarizer has a high degree of polarization of about 90 or more, and after the heat treatment for 100 hours at a silver of about 80 ° C., the degree of polarization decrease is about 10% or less, or about 0.1 to 5% is excellent A low degree of polarization deterioration due to heat resistance and high temperature heat can be exhibited.
  • the polarizing element comprises: forming the composition for the above-described one embodiment dye type polarizing member formed on a substrate; Orienting the curable anisotropic dye and optionally an orientation aid or reactive mesogen; And curing the composition for forming a dye-type polarizer including the oriented anisotropic dye and the like.
  • the polarizer by a method of orienting and curing a curable anisotropic dye, which is a component of the composition, etc. It can be manufactured easily.
  • the alignment step may be performed using a rubbing orientation or photoalignment according to a conventional alignment method as described above.
  • an optical alignment layer including a photo-reflective polymer is further formed between the substrate and the thin film of the composition for forming a dye-type polarizer, such optical response
  • the photo-alignment of the polymer it can be used to orient the curable anisotropic dye.
  • the curable anisotropic dye and orientation aid and optionally semi-ungular mesogen and / or polyfunctional binder can be cured by applying heat or by irradiation with UV or the like.
  • the above-described dye type polarizer may be included in various display devices such as a liquid crystal optical film or an OLED device, and may be applied to an antireflection film or a smarter shade of the OLED device.
  • preferred embodiments will be presented to aid in understanding the invention.
  • the following examples are only to illustrate the invention, not limited to the invention only.
  • a curable anisotropic dye of the formula la to If was synthesized and these were used in the examples.
  • known non-curable anisotropic dyes of the formulas lg and lh were used:
  • This intermediate 2 was placed in IN NaOH (8eq) solution and stirred at 70 ° C for 16 h. The reaction solution was cooled to room temperature and then filtered again after maintaining the temperature at 0 ° C for 30 minutes. The filtered crude product was extracted with distilled water and ethyl acetate to obtain intermediate product 3.
  • This intermediate 2 was placed in IN NaOH (8eq) solution and stirred at 70 ° C for 16 h. The reaction solution is cooled to room temperature, and then the silver is brought back to 0 ° C.
  • This intermediate 2 was placed in IN NaOH (8eq) solution and stirred at 70 ° C for 16 h.
  • the reaction solution is cooled to room temperature and the temperature is set back to 0 ° C. After maintaining for 30 minutes, it was filtered.
  • the filtered crude product was extracted with distilled water and ethyl acetate to obtain intermediate product 3.
  • the intermediate product 5 was dissolved in DMAc and stirred at 0 ° C., then slowly added acryloyl chloride (3eq) and stirred at room temperature for 4 hours. Then, the mixture was diluted with diethyl ether, washed with IN HC1 and NaHC0 3 aqueous solution, extracted with MC, MC was used as a developing solution, and subjected to column chromatography to prepare Chemical Formula lc.
  • 1-naphthylamine is used instead of aniline in the synthesis of intermediate 1
  • 4-hydroxyethyl benzoate aniline is used in place of 4-hydroxyethylaniline in the synthesis of intermediate 2
  • N-phenyl-N in the synthesis of intermediate 5 -ethyl-amine instead of N- (3- methylphenyl) - N- ethyl-ethane, except for using the amine, in the same manner as in synthesis example 3 Formula I d was synthesized.
  • Compound of formula la curable anisotropic dye; concentration in solution: 2 weight 0 radical polymer of the compound of formula 2c (orientation aid; Mw: 8000; concentration in solution: 15 weight 0 /.), And Igacure 907 (solution) increased concentration: QJ were prepared by weight 0/0), and the composition is a dye-type polarizing element in the same manner as in example 1 except for using the.
  • the compounds of the formula ic (curable anisotropic dyes; a solution of concentration 2 weight 0/0), the compound of Formula 2b (orientation aids; concentration in the solution: 15 parts by weight 0/0), and Irgacure 907 (concentration of the solution: A dye-type polarizer was prepared in the same manner as in Example 1 except that the composition of 0.7 wt%) was used.
  • the compound of Formula lc (curable anisotropic dyes; solution increased concentration: 2 wt. 0/0), a radical polymer of the compound of Formula 2c (orientation aids; Mw: 8000; concentration of the solution: 15 wt%), and Irgacure 907
  • a dye-type polarizer was prepared in the same manner as in Example 1, except that the composition (concentration in solution: 7 weight 0 / ° ) was used.
  • Example 7 Preparation of Dye Type Polarizer
  • Example 8> Preparation of a dye type polarizing member ⁇ the compounds of Formula lc (curable anisotropic dyes; concentration in the solution: 2 parts by weight 0/0), the compound (alignment aids of the above formula 3a; concentration in the solution: 15 parts by weight 0 / 0 ), and a dye-type polarizer was prepared in the same manner as in Example 1 except for using the composition of Igacure 907 (concentration in solution: eq 7 weight 0 /.).
  • Formula lc compound (curable anisotropic dyes; concentration in the solution: 2 parts by weight 0/0), a radical polymer of the compound of Formula 3c (orientation aids; Mw: 10000; the concentration of the solution: 15 parts by weight 0 / o), and a divalent Thing using the composition of Cure 907 (concentration in solution: 0.7 weight 0 /.) Except for producing a dye-type polarizer in the same manner as in Example 1. ⁇ Example 10>: Preparation of dye type polarizer
  • Formula lc compound (curable anisotropic dyes; concentration in the solution: 2% by weight) a radical polymer of the compound of Formula 3d (orientation aids; Mw: 8000; concentration of the solution: 15 parts by weight 0/0), and Irgacure 907 (solution concentration of 0.7 wt. 0/0) was prepared in example 1 and the dye-type polarizing element in the same manner except that the composition of the.
  • the compound of Formula Id (curable anisotropic dyes; concentration in the solution: 2 parts by weight 0 /), a radical increase incorporation of the compound of Formula 2c (orientation aids; Mw: 8000; concentration of the solution: 15 parts by weight 0/0), and A dye-type polarizer was prepared in the same manner as in Example 1 except that the composition of Igacure 907 (concentration in solution: 0.7 weight 0 / ° ) was used.
  • the compounds of the formula le (curable anisotropic dyes; concentration in the solution: 2% by weight) a radical polymer of the compound of formula 2c, (orientation aids; Mw: 8000; concentration of the solution: 15 parts by weight 0/0), and Irgacure 907 (solution concentration of 0.7 wt. 0/0) was prepared in example 1 and the dye-type polarizing element in the same manner except that the composition of the.
  • the compound of Formula If (curable anisotropic dyes; solution increased concentration: 2 wt. 0/0), a radical polymer of the compound of Formula 2c (orientation aids; Mw: 8000; concentration of the solution: 15 parts by weight 0/0), and a divalent Thing using the composition of Cure 907 (concentration in solution: 0.7 weight 0 /.) Except for producing a dye-type polarizer in the same manner as in Example 1.
  • the compound of formula lb (curable anisotropic dye; concentration in solution: 2% by weight), the compound of formula 2a (orientation aid; concentration in solution: 15 weight 0 /.), RM257 (concentration in solution: 5 weight 0 /. ), And a dye-type polarizer was prepared in the same manner as in Example 1 except that the composition of Igacure 907 (concentration in solution: 1% by weight) was used.
  • the compound of Formula lc (curable anisotropic dyes; concentration in the solution: 2 parts by weight 0/0),
  • the compounds of Formula 2b (orientation aids; concentration in the solution: 15 parts by weight 0/0) for using the composition of, RM257 (concentration in the solution: 5 parts by weight 0/0), and Irgacure 907 (1 wt% solution concentration in) Except for producing a dye-type polarizer in the same manner as in Example 1.
  • Example 20> Preparation of dye type polarizer
  • the compound of Formula lc (curable anisotropic dyes; concentration in the solution: 2 parts by weight 0/0), a radical polymer of the compound of Formula 2c (orientation aids; Mw: 8000; concentration of the solution: 15 parts by weight 0/0), RM257 ( solution of concentration: 5 wt. 0/0), and Irgacure 907 (concentration of the solution: was prepared in example 1 as a dye-type polarizing in the same manner except that the composition of the 1% increase) form.
  • the compound of Formula lc (curable anisotropic dyes; concentration in the solution: 2 parts by weight 0/0), a radical polymer of the compound of formula 2d (orientation aids; Mw:; 7000 concentration in the solution 15 increased 0/0), RM257 ( Concentration in solution: 5 weight 0 /. And Irgacure 907 (solution increased concentration: 1 wt. 0/0) was prepared in the dye type polarizing element in the same manner as in Example 1, except that the composition of the.
  • the compound of Formula lc (curable anisotropic dyes; concentration in the solution: 2 parts by weight 0/0), the compound of formula 3a (orientation aids; concentration in the solution: 15 parts by weight 0/0), RM257 (concentration in the solution: 5 parts by weight 0 / 0 ), and a dye-type polarizer was prepared in the same manner as in Example 1 except that the composition of Igacure 907 (concentration in solution: 1 weight 0 /.) was used.
  • Example 23> Preparation of dye type polarizer
  • Radical polymer of the compound of Formula 3e:; (2 parts by weight 0/0 concentration in the solution-curing anisotropic dye) Formula lc compound of formula (orientation aids; Mw:. 6000; solution in concentration: 15 weight 0 /), and teeth Cure 907 (concentration in the solution: 1 weight 0/0) was prepared in example 1 and the dye-type polarizing element in the same manner except that the composition of the.
  • the compounds of formula le curable anisotropic dyes; concentration in the solution: 2 parts by weight 0/0
  • a radical polymer of the compound of Formula 2c orientation aids; Mw: 8000; concentration of the solution: 15 parts by weight 0 / o
  • RM257 Concentration in solution: 5% by weight
  • Igacure 907 Concentration in solution: 1% by weight
  • Radical polymer of the compound of Formula 2c ; (2 parts by weight 0/0 solution of the concentration of curable anisotropic dye) the compound of formula If (orientation aids; Mw:. 8000; concentration of the solution: 15 parts by weight 0 /), and teeth Using a composition of Cure 907 (concentration in solution: 1% by weight) Except for producing a dye-type polarizer in the same manner as in Example 1.
  • the compound of Formula lg (conventional non-curable anisotropic dyes; solution increased concentration: 2 increased 0 /), a radical polymer of the compound of Formula 2c (orientation aids; Mw:;: 15 parts by weight 0/0 8000 concentration in the solution) , and Irgacure 907 (concentration of the solution: 0.7 parts by weight 0/0) was prepared in example 1 and the dye-type polarizing element in the same manner except that the composition of the.
  • the compound of Formula lg (conventional non-curable anisotropic dyes; solution increased concentration: 2 wt. 0/0) radical polymer of the compound of Formula 2c (orientation aids; Mw: 8000; solution of concentration 15% by weight) and divalent Cure 907 (concentration in the solution: 1 weight 0/0) was prepared in example 1 and the dye-type polarizing element in the same manner except that the composition of the.
  • the compounds of the formula lh (conventional non-curable anisotropic dyes; a solution concentration: 2 wt. 0/0), a radical polymer of the compound of Formula 2c (orientation aids; Mw:;: 15 parts by weight 0/0 8000 concentration in the solution)
  • a dye-type polarizer was prepared in the same manner as in Example 1 except that the composition of Igacure 907 (concentration in solution: 1 weight 0 /.) was used.
  • composition of Example 1 Carried out without the use of the alignment aids of the composition of Example 1, formula la compound (curable anisotropic dyes; concentration in the solution: 2 parts by weight 0 /), and Irgacure 907 (a solution of concentration 0.7 wt 0/0), the composition of the In the same manner as in Example 1 except that used Dye type polarizer was prepared.
  • Compound of formula la (curable anisotropic dye; concentration in solution: 2 weight 0 /.), RM257 (concentration in solution: 5 weight 0 / (»), and igacure, without using an orientation aid in the composition of Example 15
  • a dye-type polarizer was prepared in the same manner as in Example 15 except that the composition of 907 (concentration in solution: 1 weight 0 / ° ) was used.
  • Example 1 Dichroic ratio (DR) and heat resistance evaluation of dye type polarizer
  • the dichroic ratio (measured at the wavelength of 380 to 780 nm to obtain an average value) was measured using a Jasco Polarimeter, and heat resistance evaluation was performed. After the heat treatment for 100 hours in an oven at 80 ° C, the degree of dichroic ratio decrease compared to the dichroic ratio before the heat treatment was summarized in Table 1 below.
  • Example 1 9.2 8.5 7.6
  • Example 2 1 1.8 10.9 7.6
  • Example 3 8.4 8.0 4.8
  • Example 4 13.9 13.8 0.7
  • Example 5 13.5 13.1 3.0
  • Example 6 15.1 14.6 3.3
  • Example 7 14.9 14.5 2.7
  • Example 8 9.6 9.4 2.1
  • Example 9 14.1 13.2 6.4
  • Example 10 14.6 14.3 2.0
  • Example 11 15.1 14.2 6.0
  • Example 12 13.8 13.4 2.9
  • Example 13 7.7 7.1 7.8
  • Example 14 9.8 9.7 1.0
  • Example 15 9.4 9.2 2.1
  • Example 16 1 1.5 1 1.6 0
  • Example 17 7.5 7.3 2.7
  • Example 18 13.5 13.5
  • Example 19 13.0 12.8 1.5
  • Example 20 14.1 14.2 0
  • Example 21 15.0 14.6 2.7
  • Example 22 9.0 9.2 0
  • Example 23 14.5 14.4 0.7
  • Example 24 14.0 14.0 0
  • Example 25 15.0 14.7 0.7
  • Example 26 13.2 13.1

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polarising Elements (AREA)

Abstract

Cette invention concerne une composition pour former un polariseur à base de colorant et le polariseur à base de colorant ainsi obtenu, la composition permettant au polariseur à base de colorant de manifester simultanément une excellente polarisabilité, résistance à la chaleur, et un excellent rapport dichroïque. La composition pour former un polariseur à base de colorant selon l'invention comprend : un colorant anisotrope de type solide ayant une structure chimique particulière ; et un auxiliaire d'orientation ayant une certaine structure chimique.
PCT/KR2014/012639 2013-12-27 2014-12-22 Composition destinée à former un polariseur à base de colorant et polariseur à base de colorant WO2015099377A1 (fr)

Priority Applications (4)

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CN201480071044.1A CN105916943B (zh) 2013-12-27 2014-12-22 用于形成染料型偏振片的组合物及染料型偏振片
JP2016534147A JP6483688B2 (ja) 2013-12-27 2014-12-22 染料型偏光体形成用組成物および染料型偏光体
US15/033,450 US10527758B2 (en) 2013-12-27 2014-12-22 Composition for forming dye type polarizer and dye type polarizer
EP14875541.6A EP3048139A4 (fr) 2013-12-27 2014-12-22 Composition destinée à former un polariseur à base de colorant et polariseur à base de colorant

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WO2017195833A1 (fr) * 2016-05-12 2017-11-16 富士フイルム株式会社 Composition colorée, composé colorant dichroïque, film d'anisotropie par absorption de lumière, produit stratifié, et dispositif d'affichage d'image
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