WO2014112448A1 - 光学補償積層膜、電極基板、液晶表示装置用基板および液晶表示装置 - Google Patents

光学補償積層膜、電極基板、液晶表示装置用基板および液晶表示装置 Download PDF

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WO2014112448A1
WO2014112448A1 PCT/JP2014/050375 JP2014050375W WO2014112448A1 WO 2014112448 A1 WO2014112448 A1 WO 2014112448A1 JP 2014050375 W JP2014050375 W JP 2014050375W WO 2014112448 A1 WO2014112448 A1 WO 2014112448A1
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optical compensation
group
liquid crystal
film
substrate
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PCT/JP2014/050375
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English (en)
French (fr)
Japanese (ja)
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清久 中村
悟史 岡田
田原　慎哉
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旭硝子株式会社
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Priority to JP2014557447A priority Critical patent/JPWO2014112448A1/ja
Priority to CN201480004792.8A priority patent/CN104937454A/zh
Priority to KR1020157014710A priority patent/KR20150107716A/ko
Publication of WO2014112448A1 publication Critical patent/WO2014112448A1/ja

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3083—Birefringent or phase retarding elements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
    • G02B27/28—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00 for polarising
    • G02B27/288—Filters employing polarising elements, e.g. Lyot or Solc filters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/24—Homopolymers or copolymers of amides or imides
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics

Definitions

  • the present invention relates to an optical compensation laminated film including a first optical compensation film exhibiting negative uniaxial anisotropy and a second optical compensation film exhibiting positive uniaxial anisotropy.
  • the present invention also relates to an electrode substrate, a substrate for a liquid crystal display device, and a liquid crystal display device using the above-described optical compensation laminated film.
  • Some liquid crystal displays have an optical compensation film (also referred to as a retardation film) which has birefringence and controls the phase of light.
  • the above-mentioned optical compensation film is usually used by attaching it to a liquid crystal cell in the same manner as a polarizing film.
  • an external film is not used, and a film having an optical characteristic equivalent to that of the optical compensation film is provided inside the liquid crystal cell. By doing this, the entire liquid crystal display device can be made thin.
  • Patent Document 1 an optical compensation film exhibiting negative uniaxial anisotropy (hereinafter also referred to as negative C plate) functioning as an alignment film on glass or color filter and optical compensation exhibiting positive uniaxial anisotropy
  • negative C plate negative uniaxial anisotropy
  • positive A plate a color filter substrate in which a film (hereinafter also referred to as a positive A plate) is laminated
  • Patent Document 1 does not sufficiently disclose the material used for the optical compensation film.
  • a polyester resin is specifically described as a material of the optical compensation film exhibiting negative uniaxial anisotropy, and a transmittance suitable for a display device is not sufficiently achieved.
  • the present invention includes an optical compensation film (negative C plate) exhibiting negative uniaxial anisotropy and an optical compensation film (positive A plate) exhibiting positive uniaxial anisotropy, and is an optical having good transmittance and optical characteristics.
  • An object of the present invention is to provide a compensation laminated film.
  • An object of the present invention is to provide an electrode substrate, a substrate for a liquid crystal display device, and a liquid crystal display device, which have excellent optical characteristics and can be reduced in thickness and cost.
  • the present invention provides an optical compensation laminate film, an electrode substrate, a substrate for a liquid crystal display device, and a liquid crystal display device having the following structures [1] to [11].
  • An optical compensation laminated film comprising a first optical compensation film exhibiting negative uniaxial anisotropy and a second optical compensation film exhibiting positive uniaxial anisotropy
  • the first optical compensation film is made of at least one kind of polyimide containing a repeating unit represented by the following formula (1A) and / or a repeating unit represented by the following formula (1B), and has a film thickness of 5 ⁇ m or less
  • the birefringence (N) in the thickness direction is 0.02 to 0.20, and the average transmittance is 85% or more
  • the second optical compensation film is made of a photocured material of a photopolymerizable liquid crystal composition containing at least one photopolymerizable liquid crystal compound, and has a thickness of 5 ⁇ m or less.
  • Optical compensation multilayer film (In the above formula, each symbol has the following meaning.
  • m and n are composition ratios of the repeating unit represented by the above formula (1A) and the repeating unit represented by the above formula (1B).
  • the polyimide is a block polyimide including a block constituted by the above formula (1A) and a block constituted by the repeating unit represented by the above formula (1B).
  • R 1 and R 3 each independently represent a tetravalent group having 4 to 27 carbon atoms, and an aliphatic group, a monocyclic aliphatic group, a fused polycyclic aliphatic group, a monocyclic aromatic group Or a fused polycyclic aromatic group, or a non-fused polycyclic aliphatic group in which the cycloaliphatic groups are mutually or directly linked by a bridging member, or the aromatic group is directly or by a bridging member
  • R 2 is a divalent group having 4 to 51 carbon atoms, and is an aliphatic group, a monocyclic aliphatic group (but excluding a 1,4-cyclohexylene group), or a fused polycyclic aliphatic group A monocyclic aromatic group or a fused polycyclic aromatic group, or a non-fused polycyclic aliphatic group in which the cycloaliphatic
  • R 2 is a trans-1,4-bismethylenecyclohexane group or a bicyclo [2,2,1] heptylene group
  • R 3 is a tetravalent group having 4 to 27 carbon atoms, and is a monocyclic aromatic group or a fused polycyclic aromatic group, or the aromatic groups are linked to each other directly or by a crosslinking member Non-fused polycyclic aromatic group.
  • R 2 is a trans-1,4-bismethylenecyclohexane group or a bicyclo [2,2,1] heptylene group Compensated laminated film.
  • R 2 is a trans-1,4-bismethylenecyclohexane group or a bicyclo [2,2,1] heptylene group Compensated laminated film.
  • the first optical compensation film has its surface subjected to rubbing treatment, and the second optical compensation film is laminated in contact with the rubbing-treated surface of the first optical compensation film.
  • the optical compensation laminated film according to any one of [1] to [5].
  • the second optical compensation film is formed of a photocured material of a photopolymerizable liquid crystal composition containing a photopolymerizable liquid crystal compound represented by the following formula (B4-1): [1] to [7] The optical compensation laminated film according to any one of the above.
  • An electrode substrate comprising: a substrate body; and the optical compensation laminated film according to any one of [1] to [8] and an electrode formed on the substrate body.
  • a substrate for a liquid crystal display device comprising the electrode substrate according to the above [9] and an alignment film formed on the electrode substrate.
  • a liquid crystal display device comprising the liquid crystal display device substrate according to [10], an opposing substrate, and a liquid crystal layer sandwiched between the liquid crystal display substrate and the opposing substrate.
  • the optical compensation laminate film of the present invention includes an optical compensation film (negative C plate) exhibiting negative uniaxial anisotropy and an optical compensation film (positive A plate) exhibiting positive uniaxial anisotropy, The characteristics are good.
  • the electrode substrate, the substrate for liquid crystal display device, and the liquid crystal display device of the present invention are provided with the optical compensation laminate film of the present invention, and have excellent optical characteristics. In addition, thinning and cost reduction are possible.
  • FIG. 1 is a cross-sectional view schematically showing a liquid crystal display device according to a first embodiment. It is sectional drawing which shows the liquid crystal display device concerning 2nd Embodiment typically.
  • a compound represented by the formula (M) may be simply referred to as a compound (M).
  • the compound is any compound, and formula (M) is any formula.
  • the polyimide in the present invention is hereinafter referred to as polyimide (PI).
  • the long axis direction of rod-like molecules such as polyimide molecules or liquid crystal molecules is x
  • the direction perpendicular to the x direction in a plane parallel to the film surface is y direction
  • the film thickness direction is z direction
  • the refractive indices in the y and z directions be nx, ny and nz, respectively.
  • nx ny> nz.
  • nx> ny nz.
  • the retardation Rth which is an index of birefringence in the z direction in the negative C plate, and the retardation (hereinafter, also referred to as in-plane retardation) Re, which is an index of birefringence in the xy plane of the positive A plate, are defined by the following formula .
  • Rth P ⁇ da (Here, da is the thickness of the negative C plate.
  • birefringence data is data for light of wavelength 550 nm.
  • average transmittance is an average transmittance of light having a wavelength of 400 to 800 nm, and is a value measured according to JIS K 7361-1.
  • the repeating unit (1B) is the “main component” indicates that the amount of the repeating unit (1B) is 50% by mass or more with respect to the entire polyimide (PI).
  • the optical compensation laminate film of the present invention is A first optical compensation film (negative C plate) exhibiting negative uniaxial anisotropy; And a second optical compensation film (positive A plate) exhibiting positive uniaxial anisotropy.
  • the stacking order of the first optical compensation film and the second optical compensation film is arbitrary.
  • the first optical compensation film is made of at least one polyimide (PI) containing a repeating unit represented by the following formula (1A) and / or a repeating unit represented by the following formula (1B).
  • the repeating unit (1A) contributes to large birefringence
  • the repeating unit (1B) contributes to cost reduction although the birefringence is smaller than that of repeating unit 1 (A).
  • m and n are composition ratios of the repeating unit represented by the above formula (1A) and the repeating unit represented by the above formula (1B).
  • the polyimide (PI) is a block polyimide comprising a block constituted by the above formula (1A) and a block constituted by the repeating unit represented by the above formula (1B) (hereinafter referred to as Block polyimide (PI-1)).
  • R 1 and R 3 each independently represent a tetravalent group having 4 to 27 carbon atoms, and an aliphatic group, a monocyclic aliphatic group, or a fused polycyclic aliphatic group A monocyclic aromatic group or a fused polycyclic aromatic group, or a non-fused polycyclic aliphatic group in which the cycloaliphatic groups are mutually linked directly or by a bridge member, or aromatic A non-condensed polycyclic aromatic group in which the groups are linked to each other directly or by bridging members
  • R 2 is a divalent group having 4 to 51 carbon atoms, and is an aliphatic group, a monocyclic aliphatic group (but excluding a 1,4-cyclohexylene group), or a fused polycyclic aliphatic group A monocyclic aromatic group or a fused polycyclic aromatic group, or a non-fused polycyclic aliphatic group in which the cycloaliphatic groups
  • the polyimide (PI) is a polyimide which contains the repeating unit represented by the above formula (1B) and does not contain the repeating unit represented by the above formula (1A).
  • R 2 is a trans-1,4-bismethylenecyclohexane group or a bicyclo [2,2,1] heptylene group
  • R 3 is a tetravalent group having 4 to 27 carbon atoms, and is a monocyclic aromatic group or a fused polycyclic aromatic group, or the aromatic groups are linked to each other directly or by a crosslinking member Non-fused polycyclic aromatic group.
  • each of R 1 and R 3 is a tetravalent group obtained by removing a divalent anhydride residue (—CO—O—CO—) from tetracarboxylic acid dianhydride.
  • a divalent anhydride residue —CO—O—CO—
  • the non-fused polycyclic aliphatic group in which the above monocyclic aliphatic group, fused polycyclic aliphatic group or cycloaliphatic group is mutually connected directly or by a bridging member is generically referred to as aliphatic ring group hereinafter.
  • the non-condensed polycyclic aromatic group in which the above monocyclic aromatic group, fused polycyclic aromatic group or aromatic group are mutually connected directly or by a bridge member is hereinafter generally referred to as an aromatic ring group.
  • a tetracarboxylic acid having an aliphatic ring group is hereinafter referred to as an alicyclic tetracarboxylic acid
  • a tetracarboxylic acid having an aromatic ring group is hereinafter referred to as an aromatic tetracarboxylic acid.
  • both of tetracarboxylic acid dianhydride having R 1 and tetracarboxylic acid dianhydride having R 3 may be aromatic tetracarboxylic acid dianhydride or alicyclic tetracarboxylic acid dianhydride It is preferable that it is a thing.
  • the tetracarboxylic dianhydride having R 3 is an aromatic tetracarboxylic dianhydride.
  • the raw material tetracarboxylic dianhydride can be used 1 type or 2 types or more.
  • aromatic tetracarboxylic acid dianhydride pyromellitic acid dianhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic acid dianhydride, 3,3 ′, 4,4′-benzophenonetetracarboxylic acid Dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, bis (3,4-dicarboxyphenyl) sulfide dianhydride, bis (3,4-dicarboxyphenyl) sulfone dianhydride, bis (3,4-dicarboxyphenyl) methane dianhydride, 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride, 2,2-bis (3,4-dicarboxyphenyl) -1, 1,1,3,3,3-hexafluoropropane dianhydride, 1,3-bis (3,4-dicarboxyphenoxy) benzene dianhydride, 1,4-bis
  • cycloaliphatic tetracarboxylic acid dianhydride cyclobutanetetracarboxylic acid dianhydride, 1,2,3,4-cyclopentane tetracarboxylic acid dianhydride, 1,2,4,5-cyclohexanetetracarboxylic acid Anhydride, bicyclo [2.2.1] heptane-2,3,5,6-tetracarboxylic acid dianhydride, bicyclo [2.2.2] oct-7-ene-2,3,5,6- Tetracarboxylic acid dianhydride, bicyclo [2.2.2] octane-2,3,5,6-tetracarboxylic acid dianhydride, 2,3,5-tricarboxycyclopentylacetic acid dianhydride, bicyclo [2.
  • an aromatic tetracarboxylic acid dianhydride some or all of the hydrogen atoms on the aromatic ring are substituted with a group selected from a fluoro group, a methyl group, a methoxy group, a trifluoromethyl group and a trifluoromethoxy group etc. It may be In addition, it has a group to be a crosslinking point selected from ethynyl group, benzocyclobutene-4'-yl group, vinyl group, allyl group, cyano group, isocyanate group, nitrilo group, isopropenyl group etc. according to the purpose.
  • a group serving as a crosslinking point such as vinylene group, vinylidene group and ethynylidene group is incorporated into the main chain skeleton. Good.
  • tetracarboxylic dianhydride may be hexacarboxylic acid trianhydrides or octacarboxylic acid tetraanhydrides for the purpose of branched introduction.
  • R 2 represents a divalent group other than 1,4-cyclohexylene group.
  • R 2 is a divalent group obtained by removing two amino groups from diamine.
  • the diamine in which two amino groups are both bonded to carbon atoms constituting the ring of the aliphatic ring group is hereinafter referred to as alicyclic diamine, and both of the two amino groups constitute the ring of the aromatic ring group.
  • the diamine which is bonded to the carbon atom to be attached is hereinafter referred to as an aromatic diamine.
  • a diamine having two amino groups bonded to an aliphatic hydrocarbon group (such as an alkyl group) which does not constitute a ring is referred to as an aliphatic diamine.
  • the aliphatic diamine may have an aliphatic ring group or an aromatic ring group.
  • diamines having an amino group bonded to a carbon atom constituting a ring of an aliphatic ring group (or an aromatic ring group) and an amino group bonded to an aliphatic hydrocarbon group not constituting a ring.
  • an aromatic diamine having a benzene ring an aliphatic diamine having an aromatic ring group, an alicyclic diamine, an aliphatic diamine having an aliphatic ring group, and an aliphatic diamine other than the above Is preferred.
  • the aromatic diamine having a benzene ring is a diamine having a benzene ring to which one or two amino groups are bonded, and may have a benzene ring to which no amino group is bonded.
  • Examples of the diamine having a benzene ring include diamines described in the following ⁇ 1> to ⁇ 7>.
  • Diamine having one benzene ring such as p-phenylenediamine and m-phenylenediamine.
  • Examples of the aliphatic diamine having an aromatic ring group include the following diamines. p-Xylylenediamine, m-Xylylenediamine
  • Examples of alicyclic diamines and aliphatic diamines having an aliphatic ring group include the following diamines. Cyclobutanediamine, di (aminomethyl) cyclohexane (trans-1,4-bis (aminomethyl) cyclohexane, 1,3-bis (aminomethyl) cyclohexane, etc.), diaminobicycloheptane, diaminomethylbicycloheptane (2,5-norbornane) Diamine, norbornane diamine such as 2,5-norbornane diamine, etc.), diaminooxybicycloheptane, diaminomethyl oxybicycloheptane (oxa norbornane diamine etc.), diaminotricyclodecane, diaminomethyl tricyclodecane, bis (aminocyclohexyl) Methane, bis (aminocyclohexyl) isopropylidene.
  • siloxane diamines are diamines in which an alkyl group having one or two amino groups is bonded to a silicon atom, and the following siloxane diamines can be mentioned.
  • Diamino ethers are aliphatic diamines having an etheric oxygen atom, and include the following diamino ethers.
  • alkylene diamines the following diamines may be mentioned.
  • Ethylenediamine 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane, 1,12-diaminododecane.
  • the 1,4-cyclohexylene group in the repeating unit (1A) is derived from 1,4-diaminocyclohexane.
  • the 1,4-cyclohexylene group may be a trans 1,4-cyclohexylene group or a cis 1,4-cyclohexylene group.
  • a part thereof may be a trans 1,4-cyclohexylene group and the others may be a cis 1,4-cyclohexylene group.
  • the number of trans 1,4-cyclohexylene groups relative to the total number of 1,4-cyclohexylene groups is preferably 50% or more, more preferably 90% or more, substantially Most preferably 100%.
  • R 2 is a trans-1,4-bismethylenecyclohexane group or a bicyclo [2,2,1] heptylene group.
  • the trans-1,4-bismethylenecyclohexane group is a group derived from trans-1,4-bis (aminomethyl) cyclohexane.
  • the bicyclo [2,2,1] heptylene group is a group derived from norbornane diamine.
  • R 2 is preferably a trans-1,4-bismethylenecyclohexane group or a bicyclo [2,2,1] heptylene group.
  • the polyimide (PI) may contain a repeating unit other than the above repeating units (1A) and / or (1B) without departing from the effects of the present invention.
  • the first optical compensation film is preferably made of at least one type of polyimide containing as a main component a repeating unit represented by the above formula (1B).
  • 1,4-diaminocyclohexane which is a raw material of the repeating unit represented by the above formula (1A) is generally expensive, cost reduction can be achieved by using other diamines.
  • the polyimide composed of the repeating unit (1B) is a polymer composed of k repeating units (1B) represented by the following formula (PI-2).
  • PI-2 each symbol is as defined above, and has the following meaning.
  • R 2 is a trans-1, 4-bismethylenecyclohexane group or a bicyclo [ 2, 2 , 1] heptylene group
  • R 3 is a tetravalent group having 4 to 27 carbon atoms, and a monocyclic aromatic ring It is a group or a fused polycyclic aromatic group, or a non-fused polycyclic aromatic group in which the aromatic groups are linked to each other directly or by a bridge member.
  • polyimides having high molecular linearity and planarity exhibit negative uniaxial anisotropy.
  • the polyimide has an unsaturated bond and / or a ring structure in the molecule to increase the linearity and planarity of the molecule.
  • Polyimide (PI) which is the material of the first optical compensation film, contains an aliphatic ring and has high molecular linearity and planarity, so it exhibits negative uniaxial anisotropy and is good when subjected to rubbing treatment. It develops an orientation function.
  • rubbing treatment refers to a process for wiping the surface of the optical compensation film using a rubbing means or a rubbing device (wipe means or wiping device).
  • polyimide has an aliphatic ring in the molecule, a film having a high transmittance can be obtained as compared to the case where all the rings are aromatic rings.
  • the first optical compensation film exhibits film thickness, transmittance, and birefringence suitable for a liquid crystal display device.
  • the film thickness da of the first optical compensation film is 5 ⁇ m or less, preferably 0.1 to 5 ⁇ m. A thickness of 0.1 ⁇ m or more is preferable in terms of film thickness control. When the thickness is 5 ⁇ m or less, the liquid crystal panel can be made thinner.
  • the first optical compensation film has a birefringence (N) in the thickness direction of 0.02 to 0.20, and an average transmittance of light with a wavelength of 400 to 800 nm of 85% or more. When the birefringence is 0.02 to 0.20, desired Rth can be expressed while securing transparency.
  • the average transmittance when the average transmittance is 85% or more, white display that does not have a yellowish color can be performed in the liquid crystal display device.
  • the birefringence (N) and the average transmittance of the first optical compensation film in the thickness direction can be adjusted by the film thickness.
  • retardation Rth which is an index of retardation in the z direction, is preferably 100 to 500 nm, and particularly preferably 200 to 300 nm.
  • Patent Document 2 describes a polyimide optical compensation film obtained using aromatic acid dianhydride and aromatic diamine.
  • Patent Document 3 describes a polyimide optical compensation film containing a fluorene skeleton.
  • Patent Document 4 describes a polyimide optical compensation film containing cyclohexanetetracarboxylic acid dianhydride.
  • Patent Document 5 describes a polyimide optical compensation film containing trans-1,4-diaminocyclohexane or tetracyclobutanoic acid dianhydride.
  • the first optical compensation film has sufficiently high transmittance and sufficiently good birefringence as compared with the optical compensation films described in the above-mentioned Patent Documents 2 to 5.
  • polyimides block polyimides (PI-1) in which m ⁇ 0 and n ⁇ 0 are described in Patent Document 6 listed in the “Background Art” section.
  • This block polyimide (PI-1) has a lower amount of 1,4-diaminocyclohexane and lower cost than the polyimide described in Patent Document 5.
  • Patent Documents 6 to 8 neither describe nor suggest the application to an optical compensation film incorporated inside a liquid crystal cell of a liquid crystal display device.
  • the film thickness of the polyimide film of the examples described in these documents is as thick as 20 to 30 ⁇ m, which is unsuitable as an optical compensation film to be incorporated into the inside of a liquid crystal cell.
  • the second optical compensation film is a photocured product obtained by photocuring a photopolymerizable liquid crystal composition containing at least one photopolymerizable liquid crystal compound.
  • photopolymerizable liquid crystal compound one or more monofunctional photopolymerizable liquid crystal compounds (A) and / or one or more bifunctional photopolymerizable liquid crystal compounds (B) are used.
  • Examples of the monofunctional photopolymerizable liquid crystal compound (A) include compounds represented by the following formulas (A1-1) to (A1-5). In each of the following formulas, each symbol has the following meaning. Cy is a trans-1,4-cyclohexylene group. Ph is a 1,4-phenylene group. R 21 is an alkyl group having 1 to 10 carbon atoms. In addition, one or more hydrogen atoms of Cy and / or Ph may be substituted by a methyl group or a fluorine atom.
  • CH 2 CH-COO-Cy-OCO-Cy-Ph-R 21 (A1-1)
  • CH 2 CH-COO-Cy-COO-Cy-Ph-R 21 (A1-2)
  • CH 2 CH-COO-Ph -Cy-OCO-Cy-Ph-R 21 ⁇ (A1-3)
  • CH 2 CH-COO-Ph -Cy-COO-Cy-Ph-R 21 ⁇ (A1-4)
  • CH 2 C (CH 3 ) -COO-Cy-OCO-Cy-Ph-R 21 ⁇ (A1-5)
  • Examples of the monofunctional photopolymerizable liquid crystal compound (A) include compounds represented by the following formulas (A2-1) to (A2-13).
  • p2 is an integer of 4 to 6.
  • R 22 is a linear alkyl group having 2 to 6 carbon atoms.
  • the monofunctional photopolymerizable liquid crystal compound (A) compounds represented by the formulas (A2-1) to (A2-13) are preferable, and a compound represented by the formula (A2-6) is particularly preferable. Further, as the compound represented by the formula (A2-6), a compound represented by the following formula (A2-6a) is preferable.
  • Examples of the bifunctional photopolymerizable liquid crystal compound (B) include photopolymerizable liquid crystal compounds represented by the following formulas (B1) to (B4).
  • R 7 and R 8 are each independently a monovalent organic group, a fluorine atom or a hydrogen atom.
  • this organic group may have a substituent.
  • the organic group may contain an etheric oxygen atom between carbon-carbon bonds.
  • an alkyl group having 1 to 8 carbon atoms is preferable, and an alkyl group having 1 to 3 carbon atoms is particularly preferable. It is particularly preferred that both R 7 and R 8 are hydrogen atoms.
  • the bifunctional photopolymerizable liquid crystal compound (B) is preferably a photopolymerizable liquid crystal compound represented by the formula (B4).
  • a compound represented by the following formula (B4-1) is particularly preferable.
  • the photopolymerizable liquid crystal composition may contain, in addition to the photopolymerizable liquid crystal compound, a known photopolymerization initiator, a known surfactant, a known solvent or other optional components.
  • photopolymerization initiator examples include oxime esters, acetophenones, benzophenones, acyl phosphine oxides, benzoins, benzyls, Michler's ketones, benzoin alkyl ethers, and benzyl dimethyl ketals.
  • the species or two or more species can be appropriately selected and used.
  • oxime esters 1,2-octanedione, 1- [4- (phenylthio)-, 2- (ortho-benzoyloxime)], and ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) And -9H-carbazol-3-yl]-, 1- (ortho-acetyloxime).
  • Acylphosphine oxides include 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis (2,4,6-trimethylbenzoyl) -diphenyl-phosphine oxide.
  • surfactant As surfactant, surfactant of the following anionic surfactant, nonionic surfactant, cationic surfactant, amphoteric surfactant etc. is mentioned.
  • Anionic surfactants sodium lauryl sulfate, ammonium lauryl sulfate, triethanolamine lauryl sulfate, polyoxyethylene alkyl ether sulfate, alkyl ether phosphate, sodium oleyl succinate, potassium myristate, coconut oil fatty acid potassium and sodium lauroyl sarkosi Nat.
  • Nonionic surfactants polyethylene glycol monolaurate, sorbitan stearate, glyceryl myristate, glyceryl dioleate, sorbitan stearate, sorbitan oleate and the like.
  • Stearyl trimethyl ammonium chloride behenyl trimethyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride and cetyl trimethyl ammonium chloride and the like.
  • Amphoteric surfactants alkyl betaines such as lauryl betaine, alkyl sulfobetaine, cocamidopropyl betaine and alkyl dimethylaminoacetic acid betaine, alkyl imidazolines, sodium lauroyl sarcosine and sodium cocoamphoacetate and the like.
  • alkyl betaines such as lauryl betaine, alkyl sulfobetaine, cocamidopropyl betaine and alkyl dimethylaminoacetic acid betaine, alkyl imidazolines, sodium lauroyl sarcosine and sodium cocoamphoacetate and the like.
  • BYK-361, BYK-306, BYK-307 manufactured by Bick Chemie Japan
  • Florard FC 430 manufactured by Sumitomo 3M
  • Megafuck registered trademark
  • F171, R08 manufactured by Dainippon Ink & Chemicals, Inc.
  • solvent cyclohexanone, ethyl cellosolve acetate, butyl cellosolve acetate, 1-methoxy-2-propyl acetate, diethylene glycol dimethyl ether, ethyl benzene, ethylene glycol diethyl ether, xylene, ethyl cellosolve, methyl-n amyl ketone, propylene glycol monomethyl ether, toluene, methyl ethyl ketone Ethyl acetate, methanol, ethanol, isopropyl alcohol, butanol and isobutyl ketone. Any of these solvents may be used alone, or two or more thereof may be used in combination.
  • antioxidants include antioxidants, ultraviolet light absorbers, silane coupling agents, light stabilizers and the like.
  • the film thickness and birefringence of the second optical compensation film suitable as a liquid crystal display device are shown.
  • the film thickness db of the second optical compensation film is 5 ⁇ m or less, preferably 0.1 to 5 ⁇ m. A thickness of 0.1 ⁇ m or more is preferable in terms of film thickness control. When the thickness is 5 ⁇ m or less, the liquid crystal panel can be made thinner.
  • the in-plane retardation Re of the second optical compensation film is preferably more than 0 nm and 100 nm or less, and particularly preferably 40 to 60 nm. An in-plane retardation Re of more than 0 nm and not more than 100 nm is preferable in view of viewing angle characteristics.
  • the optical compensation laminate film of the present invention is preferably, for example, a laminate film shown in FIG. 1 or FIG.
  • the optical compensation laminate film 12X of the first embodiment shown in FIG. 1 is a first optical compensation film 12A (negative C plate) exhibiting negative uniaxial anisotropy that functions as an alignment film, and a positive film laminated thereon. And a second optical compensation film 12B (positive A plate) exhibiting uniaxial anisotropy. Since the first optical compensation film 12A exhibits a good alignment function by rubbing treatment, it is not necessary to separately form an alignment film in this aspect, and the thickness can be reduced.
  • the step (S1) is a step of applying a composition containing a precursor of polyimide (PI) and a solvent on a substrate by a spin coating method or the like to form a coating film.
  • the substrate is a substrate body such as a glass substrate, or a substrate on which an arbitrary film is formed.
  • the composition may contain one or more optional components other than those described above.
  • the content of the precursor of polyimide (PI) is preferably 5 to 30% by mass with respect to the entire composition.
  • polyamic acid which is a precursor of polyimide
  • polyimide can be prepared by combining monomers diamine and acid dianhydride with N-methyl-2-pyrrolidone, N, N-dimethylacetamide or 1,3-dimethylimidazolidinone. It can be obtained by reacting in the presence of a protic polar solvent.
  • the polyimide is obtained by thermal imidization of a polyamic acid.
  • a polyamic acid imide which is a precursor of a polyimide oligomer composed of a repeating unit represented by the formula (1A) in an aprotic polar solvent.
  • the step (S2) is a step of removing the solvent in the coating film by heat drying (pre-baking) at about 100 ° C., reduced pressure drying, reduced pressure heat drying, or the like.
  • the step (S3) is a step (imidization step) of calcining (post-baking) the coated film preferably at 230 to 270 ° C. to imidize the precursor.
  • the step (S4) is a step of rubbing the surface of the obtained polyimide film.
  • the second optical compensation film 12B is formed.
  • a photopolymerizable liquid crystal composition containing a monofunctional photopolymerizable liquid crystal compound (A) and / or a bifunctional photopolymerizable liquid crystal compound (B) is coated on the first optical compensation film 12A.
  • the step (S6) is a step of removing the solvent in the coating film by heat drying (pre-baking) at about 80 ° C., reduced-pressure drying, reduced-pressure heat drying, or the like.
  • Step (S7) is a step of irradiating the coating film with light such as ultraviolet light (UV) to photopolymerize the photopolymerizable liquid crystal compound (A) and / or (B).
  • UV ultraviolet light
  • Unreacted photopolymerizable liquid crystal compound (A) or (B) may remain only by light irradiation.
  • the step (S8) of firing at about 230 to 270 ° C. may be performed after the step (S7).
  • the optical compensation laminated film 12X is formed as described above.
  • the optical compensation laminate film 12Y includes an alignment film 12C and a second optical compensation film (positive A plate) 12B which is laminated on the alignment film 12C and exhibits positive uniaxial anisotropy. It consists of a first optical compensation film (negative C plate) 12A exhibiting negative uniaxial anisotropy laminated thereon.
  • the first optical compensation film 12A does not particularly need an orientation function.
  • the restriction on the shape and material composition of the negative C plate necessary for giving the orientation is relaxed, and the degree of freedom in design of the liquid crystal display device is improved.
  • both of the optical compensation laminated films 12X and 12Y have a film form, they can be formed in the liquid crystal cell, and can be thinner than the externally attached optical compensation film. Further, since the optical compensation laminated films 12X and 12Y have high transmittance, they are suitable for liquid crystal display devices such as VA (Vertical Alignment) mode.
  • VA Very Alignment
  • the thickness da of the first optical compensation film (negative C plate) exhibiting negative uniaxial anisotropy and the second optical compensation film exhibiting positive uniaxial anisotropy (positive A
  • the thickness db of the plate can be 5 ⁇ m or less in any case. Therefore, the thickness d of the optical compensation laminated film can be 10 ⁇ m or less.
  • the optical compensation laminate film of the present invention has a preferable average transmittance for light with a wavelength of 400 to 800 nm.
  • the average transmittance of such light is preferably 80% or more, and particularly preferably 85% or more.
  • the electrode substrate of the present invention is Substrate body, The optical compensation film of the present invention or the optical compensation laminate film of the present invention and an electrode are formed on a substrate body. Refer to reference numeral 19 in FIG. 3 and reference numeral 49 in FIG. 4 for a configuration example of the electrode substrate.
  • the liquid crystal display device substrate of the present invention is The electrode substrate of the present invention and an alignment film formed on the electrode substrate are provided.
  • a configuration example of a liquid crystal display device substrate refer to reference numeral 10 in FIG. 3 and reference numeral 40 in FIG.
  • the liquid crystal display device of the present invention comprises the liquid crystal display device substrate of the present invention, an opposing substrate, and a liquid crystal layer sandwiched between the pair of substrates.
  • the liquid crystal display device of the present embodiment is a VA mode color transmission TFT (thin film transistor) liquid crystal display device.
  • the present embodiment is also applicable to other active matrix type or passive matrix type such as monochrome liquid crystal display device, reflective or semi-transmissive reflective liquid crystal display device, TFD (thin film diode) liquid crystal display device and the like.
  • the liquid crystal display device 1 of the first embodiment shown in FIG. 3 includes a liquid crystal cell 1A, polarizers 51 and 52 attached to the outside of the liquid crystal cell 1A, and a backlight BL.
  • the liquid crystal cell 1A includes a color filter substrate 10, a TFT substrate 20 which is an opposite substrate, and a liquid crystal layer 30 sandwiched between the pair of substrates.
  • the color filter substrate (substrate for liquid crystal display device) 10 is A common electrode substrate 19 including a translucent substrate body 11, a black matrix layer BM sequentially stacked on the liquid crystal layer 30 side, a color filter layer CF, an optical compensation laminated film 12 and a common electrode 13; And an alignment film 14 formed on the liquid crystal layer 30 side.
  • reference numeral 19 is a common electrode substrate.
  • the TFT substrate 20 is A pixel electrode substrate 21 including a translucent substrate body, a plurality of pixel electrodes and a plurality of TFTs formed in a matrix on the liquid crystal layer 30 side thereof; And an alignment film 22 formed on the liquid crystal layer 30 side.
  • a glass substrate As a substrate body used for the color filter substrate 10 and the TFT substrate 20, a glass substrate is preferable.
  • a translucent conductive material such as ITO (indium tin oxide) is used.
  • the black matrix layer BM is a light shielding layer that shields light between adjacent dots.
  • the optical compensation laminate film 12 is the optical compensation laminate film 12X shown in FIG. 1 or the optical compensation laminate film 12Y shown in FIG. In the present embodiment, the common electrode 13 is formed directly on the optical compensation laminated film 12, and the alignment film 14 is formed thereon.
  • the laminated structure of the color filter substrate 10 can be changed in design as appropriate.
  • the optically compensatory laminated film 12 and the black matrix layer BM are formed on the light transmitting substrate body 11.
  • the color filter layer CF, the common electrode 13 and the alignment film 14 may be sequentially provided.
  • reference numeral 49 is a common electrode substrate.
  • the color filter substrates (substrates for liquid crystal display devices) 10 and 40 and the liquid crystal display devices 1 and 2 are provided with the optical compensation laminated film 12 in the liquid crystal cells 1A and 2A, so that thinning and cost reduction are possible. And optical properties are good.
  • Example 1 is an example.
  • Example 1 ⁇ Preparation of Coating Solution (X1) for Negative C Plate>
  • X1 Coating Solution (X1) for Negative C Plate>
  • CHDA trans-1,4-diaminocyclohexane
  • NMP N-methylpyrrolidone
  • the obtained block polyamic acid imide is obtained by block polymerizing a polyamic acid oligomer and a polyimide oligomer without being randomized respectively, and the number of polyamic acid blocks: the number of imide blocks is approximately 1: 1. Met.
  • a coating solution for negative C plate comprising a precursor of block polyimide (PI-1a) which is one kind of block polyimide (PI-1) of m ⁇ 0 and n ⁇ 0 in polyimide (PI) I got (X1).
  • NCP1 ⁇ Preparation of Negative C Plate (NCP1)>
  • the coating solution (X1) was applied onto a glass substrate by die coating. It was dried on a hot plate at 80 ° C. for 10 minutes. After further heating at 230 ° C. for 30 minutes, rubbing was performed to prepare a negative C plate (NCP1) comprising the block polyimide (PI-1a) and having the function of an alignment film.
  • the film thickness da of the obtained negative C plate (NCP1) was 2.7 ⁇ m.
  • the thickness direction birefringence index N for light of a wavelength of 550 nm was 0.075, and Rth was 216 nm. The average transmittance was 88%.
  • a negative C plate (NCP1) with high transmittance and good birefringence was prepared.
  • C1 photopolymerization initiator
  • D1 surfactant
  • the coating solution (Y1) was coated on the negative C plate (NCP1) with a spin coater and dried at 80 ° C. for 2 minutes to adjust the orientation. Thereafter, ultraviolet rays were irradiated for 30 seconds from the direction perpendicular to the substrate surface to cure the coating film.
  • the illuminance of the high pressure mercury lamp used for photocuring was 40 mW / cm 2 at a wavelength of 365 nm. Further, baking was performed at a temperature of 230 ° C. for 30 minutes to prepare a positive A plate (PAP1).
  • the film thickness db of the obtained positive A plate (PAP1) was 0.38 ⁇ m.
  • the Re for light at a wavelength of 550 nm was 60 nm, and the Rth was 30 nm.
  • a positive A plate (PAP1) having high transmittance and good birefringence was produced.
  • an optical compensation laminated film composed of the negative C plate (NCP1) and the positive A plate (PAP1) was obtained.
  • An optically-compensated laminated film having high transmittance and good optical characteristics was obtained.
  • Main production conditions and evaluation results of Example 1 are shown in Tables 1 to 3.
  • the optical compensation laminate film of the present invention can be preferably used for a liquid crystal display device or the like.

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  • Polymers & Plastics (AREA)
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  • Medicinal Chemistry (AREA)
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PCT/JP2014/050375 2013-01-15 2014-01-10 光学補償積層膜、電極基板、液晶表示装置用基板および液晶表示装置 WO2014112448A1 (ja)

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CN201480004792.8A CN104937454A (zh) 2013-01-15 2014-01-10 光学补偿层叠膜、电极基板、液晶显示装置用基板及液晶显示装置
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JP2008107766A (ja) * 2006-07-21 2008-05-08 Toray Ind Inc 位相差薄膜用樹脂組成物、液晶表示装置用カラーフィルター基板、および液晶表示装置、並びに位相差薄膜付き液晶表示装置用カラーフィルター基板の製造方法
JP2010197921A (ja) * 2009-02-27 2010-09-09 Fujifilm Corp 液晶表示装置用基板および液晶表示装置
JP2012256005A (ja) * 2011-06-10 2012-12-27 Mitsui Chemicals Inc 液晶配向膜、およびそれを具備する液晶表示装置
JP2012255985A (ja) * 2011-06-10 2012-12-27 Mitsui Chemicals Inc 液晶配向剤、液晶配向膜および該液晶配向膜を有する液晶表示素子

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JPS63191129A (ja) * 1986-09-02 1988-08-08 Canon Inc カイラルスメクチック液晶素子
JPH0344625A (ja) * 1989-07-12 1991-02-26 Matsushita Electric Ind Co Ltd アクティブマトリクス型液晶表示パネル
JP2007004120A (ja) * 2005-03-02 2007-01-11 Nitto Denko Corp 光学フィルムおよびその製造方法、ならびに該光学フィルムを用いた画像表示装置
JP2007199257A (ja) * 2006-01-25 2007-08-09 Nippon Oil Corp 液晶表示装置
JP2008107766A (ja) * 2006-07-21 2008-05-08 Toray Ind Inc 位相差薄膜用樹脂組成物、液晶表示装置用カラーフィルター基板、および液晶表示装置、並びに位相差薄膜付き液晶表示装置用カラーフィルター基板の製造方法
JP2010197921A (ja) * 2009-02-27 2010-09-09 Fujifilm Corp 液晶表示装置用基板および液晶表示装置
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