WO2008010483A1 - Composition de résine pour film mince retard, substrat de filtre coloré pour un dispositif d'affichage à cristaux liquides, dispositif d'affichage à cristaux liquides, et procédé de fabrication d'un substrat de filtre coloré pour un dispositif d'affichage à cristaux liquides ayant un film - Google Patents

Composition de résine pour film mince retard, substrat de filtre coloré pour un dispositif d'affichage à cristaux liquides, dispositif d'affichage à cristaux liquides, et procédé de fabrication d'un substrat de filtre coloré pour un dispositif d'affichage à cristaux liquides ayant un film Download PDF

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Publication number
WO2008010483A1
WO2008010483A1 PCT/JP2007/064077 JP2007064077W WO2008010483A1 WO 2008010483 A1 WO2008010483 A1 WO 2008010483A1 JP 2007064077 W JP2007064077 W JP 2007064077W WO 2008010483 A1 WO2008010483 A1 WO 2008010483A1
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WIPO (PCT)
Prior art keywords
liquid crystal
thin film
crystal display
display device
color filter
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Application number
PCT/JP2007/064077
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English (en)
Japanese (ja)
Inventor
Satoshi Yoshida
Tetsuo Yamashita
Masuichi Eguchi
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Toray Industries, Inc.
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Application filed by Toray Industries, Inc. filed Critical Toray Industries, Inc.
Priority to CN2007800276433A priority Critical patent/CN101490607B/zh
Publication of WO2008010483A1 publication Critical patent/WO2008010483A1/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
    • G02B5/3083—Birefringent or phase retarding elements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G02F1/133638—Waveplates, i.e. plates with a retardation value of lambda/n
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F2413/00—Indexing scheme related to G02F1/13363, i.e. to birefringent elements, e.g. for optical compensation, characterised by the number, position, orientation or value of the compensation plates
    • G02F2413/14—Negative birefingence

Definitions

  • the present invention relates to a resin composition for a retardation film, a color filter substrate for a liquid crystal display device, a liquid crystal display device, and a method for producing a color filter substrate for a liquid crystal display device with a retardation film.
  • liquid crystal display devices are used in various applications such as notebook PCs, portable information terminals, desktop monitors, and digital cameras, taking advantage of characteristics such as light weight, thinness, and low power consumption. Liquid crystal display devices are required to have a wider viewing angle with the expansion of screens and monitor applications.
  • a liquid crystal display device generally has a structure in which a liquid crystal layer is sandwiched between two polarizing films. Therefore, the difference in the retardation of the liquid crystal layer resulting from the difference in the traveling direction of light affects the transmission intensity. That is, in the oblique direction, the retardation increases, so that the incident linearly polarized light becomes elliptically polarized light, and the amount of light leakage in the dark state increases, leading to a decrease in contrast.
  • VA Vertical Alignment
  • IPS In-plane Switching
  • a biaxially stretched retardation film is also used for the VA method in order to further increase the viewing angle.
  • the production of these films is not easy, and the orientation or Since the stretching process is indispensable, the process is troublesome.
  • Patent Document 1 a polyimide retardation film having an optically negative uniaxial anisotropy and having an optical axis perpendicular or substantially perpendicular to the thin film surface. A method for enlarging the field angle has been proposed.
  • Polyimide exhibits the function of a retardation film because it has an aromatic ring or aromatic heterocycle in the main chain direction of the polymer, and therefore has a refractive index in the main chain direction as compared to the direction perpendicular to the main chain. And the birefringence as a molecule increases, and the molecular chain easily aligns parallel to the substrate, so the difference in refractive index between the film thickness direction and the direction parallel to the film surface (birefringence as a film). Due to refraction).
  • the above-mentioned polyimide retardation thin film has a strong light absorption due to the aromatic molecular structure and cannot be said to have sufficient transparency.
  • the white display on the device was yellowish, and there was a problem in image display quality.
  • Patent Documents 2 to 4 In order to improve the transparency of the polyimide, an acid component having a non-aromatic group such as an alicyclic group is introduced into the polyimide resin to prevent intramolecular conjugation and charge transfer complex formation. It has been proposed (Patent Documents 2 to 4). In addition, it has been proposed to apply a polyimide resin having high transparency and low birefringence with improved transparency and reduced orientation birefringence and stress birefringence as an optical element. (Patent Documents 5 to 7).
  • Patent Document 1 Japanese Patent Laid-Open No. 2001-290023
  • Patent Document 2 Japanese Patent Laid-Open No. 7-56030
  • Patent Document 3 Japanese Patent Laid-Open No. 9-73172
  • Patent Document 4 Japanese Patent Laid-Open No. 2002-161136
  • Patent Document 5 Japanese Patent Laid-Open No. 10-221549
  • Patent Document 6 Japanese Patent Laid-Open No. 11-60732
  • Patent Document 7 Japanese Patent Laid-Open No. 2005-163012
  • the present invention does not require an orientation and stretching step, and can form a highly transparent and highly birefringent retardation film by coating on a substrate, the retardation film resin composition, and the retardation oen
  • the present invention provides a color filter substrate having a thin film, a wide viewing angle, high contrast liquid crystal display device, and a method for producing a color filter substrate for a liquid crystal display device with a retardation film.
  • the present invention has the following configuration.
  • a resin composition for forming a retardation film comprising: a polyimide precursor obtained by reacting at least one tetracarboxylic dianhydride and at least one diamine; and an organic solvent.
  • a resin composition for forming a retardation film wherein at least one of the at least one tetracarboxylic dianhydride and the at least one diamine is an alicyclic compound.
  • Diamine an alicyclic compound, has the following general formula (1)
  • R 1 represents a monovalent organic group or a hydrogen atom.
  • Tetracarboxylic dianhydride has the following general formula (2)
  • R 2 and R 3 each independently represent a monovalent organic group or a hydrogen atom.
  • the composition according to 2 which is a 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride compound represented by the formula:
  • composition according to item 3 wherein the polyimide precursor has at least a structural unit represented by the following general formula (3).
  • R 2 , R 4 and R 5 each independently represent a monovalent organic group or a hydrogen atom.
  • composition according to 1, wherein the compound is a tetracarboxylic dianhydride strength 1,2,3,4-cyclobutane tetraforce rubonic acid dianhydride which is an alicyclic compound.
  • composition according to 5, wherein the diamine is an aromatic diamine having a rigid molecular structure.
  • composition according to item 6 wherein the aromatic diamine having a rigid molecular structure is at least one selected from P-phenolenediamine, 4,4 and diaminobenza-lid force.
  • R 1 represents a monovalent organic group or a hydrogen atom.
  • R 2 and R 3 each independently represent a monovalent organic group or a hydrogen atom.
  • composition according to item 8 which has at least a structural unit represented by the following general formula (3):
  • R 4 and R 5 each independently represent a monovalent organic group or a hydrogen atom.
  • R 1 is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms
  • R 2 10.
  • composition according to item 9 or 10 further comprising at least one structural unit selected from the group consisting of structural unit forces represented by the following general formulas (4) to (8): object.
  • R 4 and R 5 each independently represent a monovalent organic group or a hydrogen atom.
  • R 1 is a hydrogen atom or a linear or branched chain having 1 to 4 carbon atoms.
  • the total content of structural units represented by the formula (3), (4), (5), (6), (7) or (8) is the total structural unit constituting the polyamic acid. 13.
  • composition according to item 14 wherein the dicarboxylic anhydride is at least one dicarboxylic anhydride in which maleic anhydride, phthalic anhydride, succinic anhydride, and nadic anhydride are also selected.
  • composition according to any one of items 1 to 15 for the manufacture of a resin composition for forming a retardation film.
  • the retardation film has the following general formula (8)
  • R 2 and R 3 each independently represent a monovalent organic group or a hydrogen atom.
  • a color filter substrate according to claim 17, comprising polyimide containing at least 50 mol% of the structural unit represented by
  • the liquid crystal display device is a liquid crystal display device in which the liquid crystal molecules are aligned in a direction substantially perpendicular to the liquid crystal cell surface, and the liquid crystal molecules are aligned in a direction substantially parallel to the liquid crystal cell surface when a voltage is applied.
  • the invention's effect [0042]
  • the phase difference thin film for a liquid crystal display device can be easily formed by using the resin composition for the phase difference thin film of this configuration, and further, the viewing angle characteristics and contrast of the liquid crystal display device can be further improved by the phase difference thin film. I can plan.
  • the resin composition for retardation film of the present invention is used in a liquid crystal display device, has optically negative uniaxial anisotropy, an optical axis is substantially perpendicular to the thin film surface, and the thickness direction
  • tetracarboxylic dianhydride and diamine is an alicyclic compound.
  • the polyimide precursor used in the present invention is a polyamic acid, polyamic acid ester, polyamic acid partial ester, polyamic acid silyl ester, polyamic acid salt, polyisoimide, or the like, which can be heated or chemically converted to polyimide. It's okay to make a difference.
  • trans-1,4-diaminocyclohexane compound represented by the following general formula (1) is preferable. .
  • R 1 represents a monovalent organic group or a hydrogen atom.
  • R 1 is preferably an organic group having 1 to 30 carbon atoms or a hydrogen atom, and more preferably a methyl group, an ethyl group, a ⁇ -propyl group, an isopropyl group, a ⁇ -butyl group, an isobutyl group. And a straight-chain or branched alkyl group having 1 to 4 carbon atoms such as sec-butyl group or a hydrogen atom.
  • trans-1,4-diaminocyclohexane, trans-1,4-diamino-2-methylcyclohexane, and trans-1,4-diamino-2,5-dimethylcyclohexane are particularly preferred.
  • Trans-1,4-diaminocyclohexane is preferred.
  • trans-1,4-diaminocyclohexane compound the configuration of the amino group at positions 1 and 4 is trans There are trans isomers that are cis configurations and cis isomers that are cis configurations.
  • trans-1,4-diaminocyclohexane compound is obtained by hydrogenating the precursor P-phenylenediamine compound, but the product of this reaction is trans form and cis form.
  • a suitable trans-1,4-diaminocyclohexane compound used in the present invention a product obtained by separating and purifying the hydrogenated compound according to a known method such as distillation, recrystallization or the like is used.
  • the cis-isomer content is not particularly limited as long as the effects of the present invention are not impaired. It is usually recommended to refine the cis-isomer content to 50% by weight or less, preferably 30% by weight or less, more preferably 10% by weight or less. By setting the cis-isomer content in the above range, it is possible to suppress a decrease in the orientation of the polyimide molecular chain due to the bent structure of the cis-isomer, and to obtain birefringence sufficient for practical use.
  • the trans-1,4-diaminocyclohexane compound can be used in combination with another diamine compound as long as the effects of the present invention are not impaired.
  • the proportion of the trans-1,4-diaminocyclohexane compound used is preferably 50 mol% or more, more preferably 70 mol% or more in the entire diamine, and 90 mol% or more. More preferably it is. If the proportion of trans 1,4-diaminocyclohexane compound used is lower than 50 mol%, the target characteristics of the present invention may not be obtained.
  • Examples of diamines that can be used in combination with trans-1,4-diaminocyclohexane compound include 2,2'-bis (trifluoromethyl) benzidine, p-phenylenediamine, and m-phenylenediamine.
  • siloxane diamine When siloxane diamine is used as a part of diamine, adhesion to an inorganic substrate or the like can be improved. Siloxane diamine is usually preferably used in an amount of 1 to 20 mol% in the total diamine. A specific example of siloxane diamine is bis (3-aminopropyl) tetramethyldisiloxane.
  • the tetracarboxylic dianhydride to be reacted with diamine which is an alicyclic compound, includes 3,3 ', 4,4'-biphenyltetracarboxylic dianhydride, 2,3,3 ', 4'-biphenyltetracarboxylic dianhydride, 3,3', 4,4'-benzophenone tetracarboxylic dianhydride, pyromellitic anhydride, 3,4, 9, 10-perylene Tetracarboxylic dianhydride, 3,3 ', 4,4'-diphenylsulfone tetracarboxylic dianhydride, 4,4 oxydiphthalic dianhydride, 1,2,5,6-naphthalenetetracarboxylic Acid dianhydride, 3,3 ', 4,4'-paraterphenyl tetracarboxylic dianhydride, 3,3', 4,4 Aromatic tetracarboxylic dianhydrides such as
  • substituted or unsubstituted 3,3 ′, 4,4 biphenyltetracarboxylic dianhydrides represented by the following general formula (2) may be used. It is more preferable to use 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride.
  • R 2 and IT each represent a monovalent organic group or a hydrogen atom, and may be the same or different.
  • R 2 and R 3 include hydrogen, an alkyl group having 1 to 3 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a phenyl group, or a substituted phenyl group. In particular, hydrogen is preferable.
  • the proportion of 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride compound used is preferably at least 50 mol% in the total tetracarboxylic dianhydride 70 mol% More preferably, it is more preferably 90 mol% or more. This is because if the proportion of the 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride compound is less than 50 mol%, the target characteristics of the present invention may not be obtained.
  • the polyimide precursor obtained by reacting a physical compound preferably has a structural unit represented by the following general formula (3).
  • the structural unit represented by the general formulas (4) to (8) may be included. These structural units are converted into the same structural unit represented by the general formula (8) by heating or chemical imidization reaction.
  • R 2 , R 3 , R 4 and R 5 each represent a monovalent organic group or a hydrogen atom, and may be the same or different.
  • R 2 , R 3 , R 4 and R 5 each represent a monovalent organic group or a hydrogen atom, and may be the same or different.
  • R 1 and R 2 and R 3 are as described in the description of each of the above formulas (1) and formula (2), R 4 and R Preferred examples of 5 include a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a phenol group, or a substituted phenol group. .
  • the ratio of the structural units represented by the general formulas (3) to (8) in the polyimide precursor to the total structural units is preferably 50 mol% or more, more preferably 70 mol% or more. . If the proportion of the structural units represented by the general formulas (3) to (8) is lower than 50 mol%, the target characteristics of the present invention may not be obtained. As described above, after imidization by heating or the like, these structural units become structural units represented by the general formula (8). Therefore, in the polyimide after imidization, the structure represented by the general formula (8) is used.
  • the proportion of units to the total structural units is preferably 50 mol% or more, more preferably 70 mol% or more.
  • the present invention also provides a diamine component containing a trans-1,4-diaminocyclohexane compound represented by the general formula (1), and a 3,4-diaminocyclohexane compound represented by the general formula (2).
  • a diamine component containing a trans-1,4-diaminocyclohexane compound represented by the general formula (1) and a 3,4-diaminocyclohexane compound represented by the general formula (2).
  • a liquid crystal display device comprising a polyamic acid compound obtained by reacting a tetracarboxylic dianhydride component including a 3 ′, 4,4′-biphenyltetracarboxylic dianhydride compound and an organic solvent.
  • the polyamic acid compound has at least a structural unit represented by the general formula (3).
  • the birefringence ⁇ in the thickness direction of the phase difference thin film is preferably 0.01 to 0.3.
  • the trans-1,4-diaminocyclohexane compound represented by the general formula (1) and the 3,3 ′, 4,4′-biphenyltetracarboxylic acid represented by the general formula (2) The above explanation can be applied as it is to the explanation regarding the acid dianhydride compound and the preferred compounds included therein.
  • the polyimide precursor can be obtained by a known method by reacting tetracarboxylic dianhydride with diamine.
  • the polyamic acid ester is a tetracarboxylic acid diester obtained by esterifying a tetracarboxylic dianhydride with an organic substance having an alcoholic hydroxyl group, as described in, for example, JP-A-8-92496. Later, acid chloride, and then react with diamine.
  • Tetracarboxylic dianhydride is esterified with an organic substance having an alcoholic hydroxyl group to form a tetracarboxylic diester, reacted with carpositimides, and then reacted with diamine. Obtained by.
  • the polyamic acid partial ester is, for example, a method in which an organic substance having a glycidyl group or an isocyanate group is added to a carboxyl group of a polyamic acid obtained by reacting tetracarboxylic dianhydride and diamine. As described in 2000-212216, it can be obtained by a method of reacting an acetal compound with a carboxyl group of a polyamic acid obtained by reacting tetracarboxylic dianhydride and diamine.
  • the polyamic acid silyl ester is described in, for example, JP-A-64-63070, JP-A-2001-72768, JP-A-2005-146073, and the diamine is converted into bissilylidamine by a silylating agent. Thereafter, it is obtained by a method of reacting with tetracarboxylic dianhydride.
  • 1,2,3,4-cyclobutanetetracarboxylic dianhydride is an alicyclic compound used for obtaining a polyimide precursor.
  • 1,2,3,4-Cyclobutanetetracarboxylic dianhydride can be obtained by a known method (for example, Japanese Patent Publication No. 2-619 56, Japanese Patent Laid-Open No. 3-137125, J. Polym. Sci .: Part A: Polymer Chemistry, 38 ⁇ , 108 (2000)).
  • 1,2,3,4-cyclobutanetetracarboxylic dianhydride and other tetracarboxylic dianhydrides.
  • the proportion of 1,2,3,4-cyclobutanetetracarboxylic dianhydride used is preferably 50 mol% or more in the total tetracarboxylic dianhydride, and more preferably 70 mol% or more. It is more preferable that it is 90 mol% or more preferable. If the proportion of 1,2,3,4-cyclobutanetetracarboxylic dianhydride used is as low as 50 mol%, the intended characteristics of the present invention may not be obtained.
  • the tetracarboxylic dianhydride used together with 1,2,3,4-cyclobutanetetracarboxylic dianhydride includes 3,3 ', 4,4'-biphenyltetracarboxylic dianhydride, 2 , 3,3 ', 4'-biphenyltetracarboxylic dianhydride, 3,3', 4,4'-benzophenone tetracarboxylic dianhydride, pyromellitic anhydride, 3,4,9, 10-perylenetetracarboxylic dianhydride, 3,3 ', 4,4'-diphenylsulfonetetracarboxylic dianhydride, 4,4'-oxydiphthalic dianhydride, 1,2,5,6- Naphthalenetetracarboxylic dianhydride, 3,3 ', 4,4'-paraterphenyl tetracarboxylic acid dianhydride, 3,3', 4,4'-metatertetrac
  • an aromatic diamine having a rigid molecular structure is a structure in which the change in the relative position of the two amino groups constituting the diamine is small, the conformation change due to the thermal motion of the molecule is small.
  • an aromatic diamine having a rigid molecular structure is a structure in which the change in the relative position of the two amino groups constituting the diamine is small, the conformation change due to the thermal motion of the molecule is small.
  • a benzene ring, an aromatic heterocyclic ring, or a condensed ring force of them is selected.
  • Examples of the aromatic diamine having a rigid molecular structure include compounds represented by the following formulas (9) to (11).
  • R 6 , R 7 , R °, R 9 and R 1Q are -H, -CH, -OH, -CF, -SO H, -COOH, respectively.
  • Each group may be the same or different.
  • aromatic diamine having a rigid molecular structure examples include 4,4'-diaminobenzanilide, benzidine, 3, 3, -dimethylbenzidine, 3,3, -dihydroxybenzidine, 3, 3'— Dimethoxybenzidine, 2,2'-dimethylbenzidine, 2,2'-bis (trifluoromethyl) benzidine, p-ferylenediamine, 2,5 diaminotoluene, 3,6 diaminodurene, m-phenylenediamine, 2,4 diaminotoluene, 2, 4 Diaminoxylene I can get lost.
  • 4,4,1-diaminobenzaldehyde, p-phenylenediamine, 2,2,1-dimethylbenzidine and 2,2'-bis (trifluoromethyl) benzidine can be preferably used.
  • -Lido and p-phenoldiamine are more preferred.
  • a retardation film containing a polyimide obtained by reacting these diamines with 1,2,3,4 cyclobutanetetracarboxylic dianhydride is preferably used because it has particularly high transparency and high birefringence. .
  • the above diamine can be used alone or in combination of two or more.
  • an aromatic diamine having a rigid molecular structure may be used in combination with another diamine.
  • the proportion of aromatic diamine having a rigid molecular structure is preferably 50 mol% or more, more preferably 70 mol% or more, more preferably 90 mol% or more of the total diamine. More preferably. If the use ratio of the aromatic diamine having a rigid molecular structure is lower than 50 mol%, the intended characteristics of the present invention may not be obtained.
  • Aliphatics such as ndecylenedimethyldiamine, 4,4'-methylenebis (cyclohexylamine), 2,5 norbornanebis (methylamine), 2,6 norbornanebis (methylamine), 2,7 norbornanebis (methylamine) and Alicyclic diamines can also be used.
  • siloxane diamine When siloxane diamine is used as a part of diamine, adhesion with an inorganic substrate or the like can be improved. Siloxane diamine is usually preferably used in an amount of 1 to 20 mol% in the total diamine. Specific examples of siloxane diamine include bis (3-aminopropyl) tetramethyldisiloxane.
  • the reaction of tetracarboxylic dianhydride and diamine can be carried out by mixing in a polar organic solvent. At this time, the degree of polymerization of the resulting polyamic acid can be adjusted by the mixing ratio of tetracarboxylic dianhydride and diamine.
  • the proportion of tetracarboxylic dianhydride and diamine used in the polyamic acid synthesis reaction is 0.2 mol of tetracarboxylic dianhydride acid anhydride group with respect to 1 equivalent of amino group contained in diamine. A ratio of ⁇ 2 equivalents is preferable, and a ratio of 0.8 to 1.2 equivalents is more preferable.
  • the degree of polymerization of polyamic acid has a reduced viscosity (also referred to as r? SpZC) of 0.05 to 5. Odl / g (measured at a concentration of 0.5 g / dl in N-methylpyrrolidone at a temperature of 30 ° C). Preferred 0.1-2. OdlZg is more preferred.
  • dicarboxylic acid anhydride in order to seal part or all of the amino group or carboxyl group of the polyamic acid molecule for the purpose of improving heat resistance and workability, dicarboxylic acid anhydride, monoamine compound, monoisocyanate are used. It is also possible to add a compound or the like to the reaction system.
  • dicarboxylic acid anhydrides include maleic anhydride, phthalic anhydride, 4-methyl phthalic anhydride, 4-tert butyl phthalic anhydride, itaconic anhydride, and nadic anhydride.
  • monoamine compounds include a-line, cyclohexylamine, n-butylamine, n-pentylamine, and n-hexylamine.
  • monoisocyanate compounds include phenol isocyanate and naphthyl isocyanate.
  • some or all of the amine end groups Preferably end-capped by amic acid formation reaction with rubonic anhydride.
  • Maleic anhydride, phthalic anhydride, succinic anhydride, and dianhydric acid power are selected from dicarboxylic anhydrides.
  • the dicarboxylic acid anhydride is preferably used.
  • the polyamic acid synthesis reaction is preferably carried out in an organic solvent under a temperature condition of -20 to 200 ° C, more preferably 0 to 150 ° C.
  • the organic solvent is not particularly limited as long as it can dissolve the synthesized polyamic acid.
  • Examples include aprotic polar solvents such as petit-mouth rataton, tetramethinoreurea, 1,3 dimethyl-2-imidazolidinone, and hexamethylphosphoramide.
  • the amount of the organic solvent used is preferably such that the concentration of the solid content including tetracarboxylic dianhydride and diamine is 0.1 to 30% by weight based on the total amount of the reaction solution. Yes.
  • organic solvent alcohol, ketone, ester, ether, halogenated hydrocarbon and hydrocarbon, which are poor solvents for polyamic acid, can be used in combination as long as the polyamic acid to be produced does not precipitate. .
  • strong anti-solvents include, for example, methylanolenoleole, ethenoreanoreconolele, isopropinoleanoreconole, cyclohexanolenole, ethylene glycol, propylene glycol, 1,4 butanediol, diethyleneglycolene, triethylene Ethylene glycol, 3-methyl-3-methoxybutanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl lactate, butyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl 3-methoxypropionate, 3- Methyl-3-methoxybutyl acetate, ethyl ethoxypropionate, cetyl oxalate, methyl malonate, jetyl ether, tetrahydrofuran, ethylene
  • the resin composition for retardation film can be produced by adding an organic solvent to a polyimide precursor or a solution thereof and mixing them uniformly by a conventional method.
  • the temperature at which the rosin composition is prepared is preferably 0 ° C to 200 ° C, more preferably 20 ° C to 60 ° C.
  • the organic solvent include those exemplified as those used in the polyamic acid synthesis reaction.
  • the poor solvents exemplified as those that can be used together in the synthesis reaction of the polyamic acid can be appropriately selected and used together.
  • the solid content concentration in the rosin composition is selected in consideration of viscosity, volatility, etc., but is preferably in the range of 1 to 10% by weight. That is, the resin composition is applied to the substrate surface to form a coating film that becomes a retardation film, but when the solid content concentration is less than 1% by weight, the coating film thickness is too small. Thus, a good retardation film cannot be obtained, and if the solid concentration exceeds 10% by weight, the film thickness of the coating becomes excessive and a good retardation film cannot be obtained. In addition, the viscosity of the rosin composition is increased and the coating properties are inferior.
  • the resin composition includes 3-aminopropyltrimethoxysilane, 3- (2-aminoethyl) aminopropyltrimethoxysilane, and N-phenyl-3-amide.
  • non-ionic surfactants such as polyoxyethylene lauryl ether and polyoxyethylene dilaurate, fluorine-based surfactants, and silane-based surfactants.
  • a surfactant such as a surfactant and an acrylic acid copolymer-based surfactant may be contained.
  • the content of these additives is such that the effects of the present invention are not adversely affected, and is usually 20% by weight or less, preferably 10% by weight or less, based on the total composition.
  • the resin composition is applied on a substrate by a dipping method, a roll coater method, a spinner method, a die coating method, a method using a wire bar, etc., and then air-dried, vacuum-dried, or oven hot plate is used.
  • a coating film is formed by heating and drying. The heating conditions vary depending on the resin, solvent, and coating amount used. It is preferable to heat at 50 to 400 ° C for 1 to 300 minutes.
  • the substrate to be coated may be a liquid crystal display substrate, that is, a color filter substrate or a TFT substrate itself.
  • the resin composition may be applied to the base film and then pasted on the liquid crystal display substrate through an adhesive layer. These are formed on the substrate surface opposite to the liquid crystal layer.
  • it may be formed on the surface of the substrate for a liquid crystal display device that is in contact with the liquid crystal layer.
  • the above-mentioned resin composition may be applied to the surface on the side where pixels are formed on a color filter substrate for a liquid crystal display device in which pixels of each color of red, blue, and green are two-dimensionally arranged on a transparent substrate. It is also possible to apply so as to cover the surface.
  • covering the pixel means that the pixel is formed closer to the liquid crystal layer than the pixel, and the pixel and the retardation film made of the above resin composition may be in direct contact with each other.
  • the retardation film made of the above resin composition can be formed on the liquid crystal layer side of the overcoat layer. Yes, it can be formed on the substrate side of the overcoat layer.
  • a retardation film made of the above resin composition is formed on a substrate, and a color filter for a liquid crystal display device in which pixels of each color of red, blue, and green are two-dimensionally arranged thereon is formed. It is also possible.
  • the above-mentioned resin composition contains coloring components such as pigments and dyes, which are used as varnishes for each color pixel of the color filter, and provide a retardation compensation function to each color pixel itself. It is also possible to do.
  • the retardation R is adjusted so that the phase difference RZ ⁇ is approximately the same as the main wavelength ⁇ for each color pixel, that is, the red, green, and blue pixels. It is preferable for aligning the phase difference compensation effect in
  • the retardation film for a liquid crystal display device of the present invention is formed by applying a resin composition on a substrate and performing a heat treatment.
  • the retardation film has a retardation, and has a function of correcting birefringence generated in the process of light passing through the liquid crystal layer in the liquid crystal display device. Since the molecular chain of polyimide resin is easily oriented parallel to the substrate surface, a difference in refractive index (birefringence as a film) occurs between the film thickness direction and the direction parallel to the film surface. In addition, since the molecular orientation in the film plane is random, there is no anisotropy of the refractive index in the direction parallel to the film plane.
  • the refractive index in each direction of the thin film containing the polyimide-based resin is nx ⁇ ny> nz, which is a retardation thin film (negative C plate) that has optically negative uniaxial anisotropy and whose optical axis is substantially perpendicular to the film surface.
  • optically negative uniaxial anisotropy means that the refractive index of the remaining one axis is small compared to the refractive index of the two axes that are equal to each other, and the optical axis is relative to the film surface.
  • the thickness of the retardation film is preferably 0.5 to 20 ⁇ m! /.
  • the retardation film of the present invention is generally effective for liquid crystal display devices.
  • the optical axis is substantially perpendicular to the retardation film surface
  • the liquid crystal molecules in the liquid crystal display device particularly when no voltage is applied, to the liquid crystal cell surface.
  • Display method in which liquid crystal molecules are aligned in a direction substantially parallel to the liquid crystal cell surface when a voltage is applied specifically, MVA (Multi-domain Vertical Alignment) method. It is more preferably used in a liquid crystal display device of a vertical alignment method such as a PVA (Patterned Vertical Alignment) method or a CPA (Continuous Pinwheel Alignment) method.
  • the retardation compensation effect is obtained when the screen is viewed vertically.
  • the phase difference of the liquid crystal layer is almost zero in the vertical direction when no voltage is applied, so that compensation for the phase difference is not necessary. That is, when no voltage is applied, good black display can be obtained without compensating for the phase difference.
  • the retardation film of the present invention has a remarkable effect in improving the contrast in the oblique direction and thus in widening the viewing angle in the vertical alignment method.
  • a solution obtained by dissolving and diluting the polyimide precursor with N-methylpyrrolidone to a concentration of 0.5 gZdl was measured at 30 ° C. using an Ubbelohde viscometer.
  • the polyimide precursor solution After applying the polyimide precursor solution on a glass substrate with a spinner so that the finished thickness is 2.0 m, it is dried at 120 ° C for 20 minutes and then at 240 ° C for 30 minutes or 270 ° C for 40 minutes.
  • a polyimide resin thin film was obtained by heat treatment. The refractive index anisotropy in the direction parallel to the film surface of this polyimide resin thin film and the refractive index anisotropy in the direction perpendicular to the film surface were measured.
  • ⁇ and Ay are preferably 0.005 or less, and more preferably 0.003 or less.
  • a 2 liter internal-irradiation glass reaction flask equipped with a Neurex (registered trademark) glass water-cooled lamp jacket was charged with 255 g (2.60 mol) maleic anhydride and 1,445 g ethyl acetate, and the flask was filled with nitrogen. Then, the solution was stirred and dissolved at room temperature. The reaction solution was cooled to 5 ° C with continuous stirring, and then irradiation with a 400 W high-pressure mercury lamp was started and light irradiation was continued for 96 hours. During the irradiation, the reaction solution temperature was kept at 3-5 ° C. After completion of the reaction, the crystals and the filtrate were separated by filtration.
  • Neurex registered trademark
  • the crude crystals were washed with ethyl acetate and then dried in a vacuum dryer at 40 ° C. for 10 hours to obtain 194 g of 1,2,3,4-cyclobutanetetracarboxylic dianhydride crystals.
  • Polyamic acid solution A was applied on a glass substrate to a thickness of 2.0 m with a spinner, dried at 120 ° C for 20 minutes, and further heat-treated to obtain a polyimide resin film.
  • nx> nz and negative uniaxiality was shown. That is, the obtained polyimide resin thin film had optically negative uniaxial anisotropy and the optical axis was substantially perpendicular to the thin film surface.
  • nx> nz and negative uniaxiality was shown. That is, the obtained polyimide resin thin film had optically negative-axis anisotropy and the optical axis was substantially perpendicular to the thin film surface.
  • Example 4 Under a dry nitrogen stream, 11.42 g (0.100 mol) of trans-1,4 diaminocyclohexane was dissolved in 174.42 g of N-methylol-2-pyrrolidone. Then, 3, 3 ', 4, 4, 1-biphenyltetracarboxylic dianhydride 29.42g (0.100mol) and N-methyl-2-pyrrolidone 40.00g were added and stirred at 60 ° C for 5 hours. . After cooling to room temperature, 85.07 g of N-methyl-2 pyrrolidone was added to obtain a transparent and viscous polyamic acid solution D (polymer concentration: 12% by weight). The viscosity of Solution D measured at 25 ° C was 5,878 mPa's. Reduced viscosity is 1.68dl / g, 7 pieces.
  • nx ny.
  • nx> nz and negative uniaxiality was exhibited. That is, the obtained polyimide resin thin film had optically negative uniaxial anisotropy and the optical axis was substantially perpendicular to the thin film surface.
  • P-Phenylenediamine 10.38 g (0.096 mol) and bis (3 aminopropyl) tetramethyldisiloxane 0.99 g (0.004 mol) to 24.79 g of N-methyl-2-pyrrolidone 1 under dry nitrogen flow Dissolved. Then, 1, 2, 3, 4-cyclobutanetetracarboxylic dianhydride 1 8.83 g (0.096 mol) and N-methyl-2 pyrrolidone 40.00 g were added. Stir at C for 3 hours. Further, 1.18 g (0.008 mol) of phthalic anhydride was added and stirred at 60 ° C. for 3 hours to obtain a transparent and viscous polyamic acid solution F (polymer concentration: 16% by weight). The viscosity of Solution F measured at 25 ° C was 384 mPa's. The reduced viscosity was 0.56 dlZg.
  • nx ny.
  • nx> nz and negative uniaxiality was exhibited. That is, the obtained polyimide resin thin film had optically negative uniaxial anisotropy and the optical axis was substantially perpendicular to the thin film surface.
  • the obtained polyimide resin thin film had optically negative uniaxial anisotropy and the optical axis was substantially perpendicular to the thin film surface.
  • the obtained polyimide resin thin film had optically negative uniaxial anisotropy and the optical axis was substantially perpendicular to the thin film surface.
  • nx ny.
  • nx> nz and negative uniaxiality was exhibited. That is, the obtained polyimide resin thin film had optically negative uniaxial anisotropy and the optical axis was substantially perpendicular to the thin film surface.
  • nx ny.
  • nx> nz and negative uniaxiality was shown. That is, the obtained polyimide resin thin film had optically negative uniaxial anisotropy and the optical axis was substantially perpendicular to the thin film surface.
  • nx> nz and negative uniaxiality was shown. That is, the obtained polyimide resin thin film had optically negative uniaxial anisotropy and the optical axis was substantially perpendicular to the thin film surface.
  • nx> nz and negative uniaxiality was exhibited. That is, the obtained polyimide resin thin film had optically negative uniaxial anisotropy and the optical axis was substantially perpendicular to the thin film surface.
  • nx ny.
  • nx> nz and negative uniaxiality was shown. That is, the obtained polyimide resin thin film has optically negative uniaxial anisotropy and the optical axis is substantially perpendicular to the thin film surface.
  • a method for producing a color filter having a retardation film is described below.
  • Pigment Red 177 (Anthraquinone Red) 4g, ⁇ -Butaguchi Rataton 40g, Ethylene glycol butyl ether 6g together with 100g of glass beads and dispersed at 7000rpm for 30 minutes, glass beads are removed by filtration Thus, a pigment dispersion having a pigment concentration of 8% by weight was obtained.
  • a red paste was applied on a substrate on which a black resin black matrix was formed, and pre-beta treatment was performed to form a polyamic acid red colored film.
  • pre-beta treatment was performed to form a polyamic acid red colored film.
  • red pixels were formed by the same means as described above, and heated to 290 ° C. for thermal curing.
  • Pigment Green 7 (Phthalocyanine Green) 3.6 g, Pigment Yellow 83 (Benzidine Yellow) 0.4 g, ⁇ -Butyl Ratatone 32 g, Ethylene Glyco-Lebutinoleate Tenole 4 g with Glass Beads 120 g at 7000 rpm After 30 minutes of dispersion treatment, the glass beads were removed by filtration to obtain a pigment dispersion having a pigment concentration of 10% by weight.
  • a green color paste was used to form a green pixel, which was then heated to 290 ° C and thermally cured.
  • the pixel for the polyamic acid solution 60g of the polymer concentration of 10 wt 0/0, Pigment Blue 1 5 (Futaroshia - Nburu) 2. 8 g, N-methyl-2-pyrrolidone 30g, glass beads 150g of ethylene glycol butyl ether 10g And a homogenizer for 30 minutes at 7000 rpm for dispersion treatment, and then the glass beads were removed by filtration to obtain a blue color paste.
  • a polyimide thin film was formed on the color filter in the same manner as in Example 13 except that the polyamic acid solution F (polymer concentration: 16% by weight) prepared in Example 6 was used.
  • a color filter having an anisotropic retardation film could be obtained.
  • Polyamic acid solution K prepared in Example 11 (polymer concentration 15% by weight) 200. Og, 0.25 g of surfactant “Disparon” LC951 (manufactured by Enomoto Isei), N-methyl-2 pip Lidon 205.8 g, 3-methoxy-1-methyl 1-butanol 94. Add Og, polymer A coating solution having a concentration of 6% by weight was prepared. As in Example 13, the color filter substrate was coated on the surface on which the pixels were formed by the slit die coating method, dried at 120 ° C for 10 minutes, and then heat treated at 240 ° C for 30 minutes to obtain a film thickness of 4. A 0 m polyimide film was formed on the color filter.
  • a color filter having a retardation film having an optically negative refractive index anisotropy with a retardation of 204 nm and an optical axis perpendicular to the thin film. could get.
  • a transparent electrode made of indium oxide was formed on the color filter with a retardation film produced in Example 13. Separately, a substrate in which TFT elements, pixel electrodes, reflectors, etc. were formed on alkali-free glass was prepared as a counter substrate.
  • test liquid crystal display device simulating the MVA (Multi-domain Vertical Alignment) method was fabricated.
  • the cell electrode spacing was about 5 m using a bead spacer.
  • a test liquid crystal display element (sample B) that differs only in that no polyimide retardation film was provided was prepared as a comparative product.
  • Example C Similar to Example 16 using the color filter with retardation film prepared in Example 14, Thus, a test liquid crystal display element (sample C) was produced.
  • the transmitted light intensity ratio (contrast) of sample C was 18, and the effect of improving the contrast by the polyimide retardation film was recognized. A good white display without yellowing was also obtained.
  • sample D A test liquid crystal display element (sample D) was produced in the same manner as in Example 16 using the color filter with a retardation film produced in Example 15.
  • Sample D had a transmitted light intensity ratio (contrast) of 18, and the contrast enhancement effect of the polyimide retardation film was confirmed.
  • a good white display without yellowing was also obtained.
  • a polyimide thin film was formed on the color filter in the same manner as in Example 13 except that the polyamic acid solution O (polymer concentration: 16% by weight) prepared in Comparative Example 3 was used.
  • a color filter having an anisotropic retardation film was obtained.
  • sample E A test liquid crystal display element (sample E) was produced in the same manner as in Example 16 using the produced color filter with retardation film.
  • Sample E had a transmitted light intensity ratio (contrast) of 15. However, the white display is yellowish and the image display quality is poor.
  • Table 1 shows the results of Examples 1 to 12 and Comparative Examples 1 to 5. As shown in Table 1, in Examples 1 to 12, it can be seen that retardation films with little coloring and good birefringence are obtained. In Table 1, each abbreviation represents the following compound.
  • BPDA 3, 3, 4, 4, 4-biphenyltetracarboxylic dianhydride
  • CBDA 1, 2, 3, 4-cyclobutanetetracarboxylic dianhydride
  • PA phthalic anhydride
  • DABA 4, 4,-Gaminobensanilide
  • t-DACH trans 1,4-diaminocyclohexane
  • DDE 4,4'-diaminodiphenyl ether
  • SiDA Bis (3-aminopropyl) tetramethyldisiloxane m-TB-HG: 2, 2'-Dimethenolevenedidine

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Abstract

L'invention concerne une composition de résine pour un film mince retard, qui peut former un film mince retard ayant une transparence élevée et une biréfringence élevée, par application de la composition sur un substrat sans qu'un procédé d'alignement ou d'étirage ne soit nécessaire. La composition comprend un précurseur de polyimide obtenu par la réaction d'au moins un dianhydride d'acide tétracarboxylique avec au moins une diamine et un solvant organique, au moins l'un des dianhydrides d'acide tétracarboxylique et des diamines étant un composé alicyclique. La composition peut être utilisée dans un dispositif d'affichage à cristaux liquides pour former un film mince retard ayant une anisotropie uniaxiale optiquement négative, un axe optique approximativement perpendiculaire à la surface du film mince et une biréfringence (Δn) dans la direction de l'épaisseur 0,01 à 0,3.
PCT/JP2007/064077 2006-07-21 2007-07-17 Composition de résine pour film mince retard, substrat de filtre coloré pour un dispositif d'affichage à cristaux liquides, dispositif d'affichage à cristaux liquides, et procédé de fabrication d'un substrat de filtre coloré pour un dispositif d'affichage à cristaux liquides ayant un film WO2008010483A1 (fr)

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WO2011033751A1 (fr) * 2009-09-18 2011-03-24 三井化学株式会社 Polyimide thermoplastique transparent et substrat transparent le contenant
WO2013051213A1 (fr) * 2011-10-05 2013-04-11 日立化成デュポンマイクロシステムズ株式会社 Polyimide très transparent
JP2014084355A (ja) * 2012-10-22 2014-05-12 Jnc Corp 光配向性を有する熱硬化性組成物
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WO2018062190A1 (fr) * 2016-09-30 2018-04-05 大日本印刷株式会社 Film de polyimide, stratifié et matériau de surface d'affichage
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JP2018104682A (ja) * 2016-12-22 2018-07-05 大日本印刷株式会社 ポリイミドフィルム、ポリイミド、ポリイミド前駆体、積層体、及びディスプレイ用表面材
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WO2015122032A1 (fr) * 2014-02-14 2015-08-20 旭化成イーマテリアルズ株式会社 Précurseur de polyimide et composition de résine le contenant
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JP6350045B2 (ja) * 2014-07-07 2018-07-04 Jsr株式会社 液晶配向剤、液晶配向膜及び液晶表示素子
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WO2009045537A1 (fr) * 2007-10-04 2009-04-09 Akron Polymer Systems Poly(arylétherimides) pour des films à biréfringence négative pour des dispositifs d'affichage à cristaux liquides
JP2010116476A (ja) * 2008-11-12 2010-05-27 Jsr Corp ポリイミド系材料、フィルム及びその製造方法
WO2011033751A1 (fr) * 2009-09-18 2011-03-24 三井化学株式会社 Polyimide thermoplastique transparent et substrat transparent le contenant
JP2018024886A (ja) * 2011-10-05 2018-02-15 日立化成デュポンマイクロシステムズ株式会社 高透明ポリイミド
WO2013051213A1 (fr) * 2011-10-05 2013-04-11 日立化成デュポンマイクロシステムズ株式会社 Polyimide très transparent
JPWO2013051213A1 (ja) * 2011-10-05 2015-03-30 日立化成デュポンマイクロシステムズ株式会社 高透明ポリイミド
JP2014084355A (ja) * 2012-10-22 2014-05-12 Jnc Corp 光配向性を有する熱硬化性組成物
WO2018062190A1 (fr) * 2016-09-30 2018-04-05 大日本印刷株式会社 Film de polyimide, stratifié et matériau de surface d'affichage
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JP2017049596A (ja) * 2016-10-20 2017-03-09 富士フイルム株式会社 近赤外線カットフィルターおよび近赤外線カットフィルターの製造方法
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JP7281887B2 (ja) 2017-10-19 2023-05-26 日鉄ケミカル＆マテリアル株式会社 ポリイミド前駆体及びポリイミド
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