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WO2010110221A1 - 熱硬化膜形成用ポリエステル組成物 - Google Patents

熱硬化膜形成用ポリエステル組成物 Download PDF

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Publication number
WO2010110221A1
WO2010110221A1 PCT/JP2010/054862 JP2010054862W WO2010110221A1 WO 2010110221 A1 WO2010110221 A1 WO 2010110221A1 JP 2010054862 W JP2010054862 W JP 2010054862W WO 2010110221 A1 WO2010110221 A1 WO 2010110221A1
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Prior art keywords
group
component
formula
polyester composition
thermosetting film
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PCT/JP2010/054862
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English (en)
French (fr)
Japanese (ja)
Inventor
真 畑中
勲 安達
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日産化学工業株式会社
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Application filed by 日産化学工業株式会社 filed Critical 日産化学工業株式会社
Priority to KR1020117022522A priority Critical patent/KR101706177B1/ko
Priority to JP2011506030A priority patent/JP5574122B2/ja
Priority to CN2010800132693A priority patent/CN102361932B/zh
Publication of WO2010110221A1 publication Critical patent/WO2010110221A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/092—Polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • 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
    • G02F1/133519—Overcoatings
    • 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
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
    • G02F1/133715—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films by first depositing a monomer
    • 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
    • G02F2202/00—Materials and properties
    • G02F2202/02—Materials and properties organic material
    • G02F2202/022—Materials and properties organic material polymeric
    • G02F2202/023—Materials and properties organic material polymeric curable
    • G02F2202/025—Materials and properties organic material polymeric curable thermocurable

Definitions

  • the present invention relates to a polyester composition for forming a thermosetting film and a cured film obtained therefrom. More specifically, the present invention relates to a polyester composition for thermosetting film formation having high transparency and flatness, liquid crystal alignment ability, high solvent resistance and heat resistance, a cured film thereof, and application of the cured film. .
  • This polyester composition for forming a thermosetting film is particularly suitable for a color filter overcoat agent having a liquid crystal alignment function in a liquid crystal display.
  • a protective film is provided to prevent the element surface from being exposed to a solvent or heat during the manufacturing process.
  • This protective film requires not only high adhesion to the substrate to be protected and high solvent resistance, but also performance such as transparency and heat resistance.
  • a protective film When such a protective film is used as a protective film for a color filter used in a color liquid crystal display device or a solid-state imaging device, generally the performance of flattening the color filter or black matrix resin of the underlying substrate, that is, flattening It is required to have performance as a film.
  • flattening it is required to have performance as a film.
  • the planarizing film as the protective film needs to have high transparency.
  • acrylic resin is used for the overcoat of this color filter.
  • glycol solvents such as propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate and ester solvents such as ethyl lactate and butyl lactate are widely used from the viewpoint of safety and handling properties.
  • ester solvents such as ethyl lactate and butyl lactate are widely used from the viewpoint of safety and handling properties.
  • Such an acrylic resin imparts heat resistance and solvent resistance by thermosetting or photocuring (Patent Documents 1 and 2).
  • thermosetting and photo-curing acrylic resins show appropriate transparency and flattening properties, even if such a flattening film is rubbed, sufficient orientation cannot be shown.
  • a material made of solvent-soluble polyimide or polyamic acid is usually used for the liquid crystal alignment layer. It has been reported that these materials impart solvent resistance by being completely imidized at the time of post-baking and show sufficient orientation by rubbing treatment (Patent Document 3).
  • Patent Document 3 when viewed as a flattening film of a color filter, there are problems such as a significant decrease in flatness and transparency.
  • Polyimides and polyamic acids are soluble in solvents such as N-methylpyrrolidone and ⁇ -butyrolactone, but their solubility in glycol-based solvents and ester-based solvents is low, making it difficult to apply to flattened film production lines. .
  • the present invention has been made on the basis of the above circumstances, and the problems to be solved show high solvent resistance, liquid crystal orientation, heat resistance, high transparency and high flatness after forming a cured film.
  • thermosetting film containing polyester as the component (A), a crosslinking agent as the component (B), and at least one diester compound represented by the following formula (1) as the component (C)
  • the present invention relates to a forming polyester composition.
  • the component (C) reacts 1 mol of a diol compound represented by the following formula (iii) with 1.7 to 2 mol of a dicarboxylic acid anhydride represented by the following formula (iv). It is related with the polyester composition for thermosetting film formation as described in a 1st viewpoint which is a diester compound.
  • P represents an alicyclic group, a group composed of an alicyclic group and an aliphatic group or a structure represented by the formula (2)
  • Q represents an alicyclic group or an alicyclic group and an aliphatic group.
  • R represents an alkylene group.
  • P and Q each represent an arbitrary hydrogen atom contained in each group may be substituted with an aliphatic group.
  • P is related with the polyester composition for thermosetting film formation as described in a 2nd viewpoint in which P represents group represented by a following formula (1P1).
  • P 1 represents a cyclic saturated hydrocarbon group, and any hydrogen atom in P 1 group may be independently substituted with an aliphatic group.
  • R 11 represents a single bond, a carbonyl group, or an ether group.
  • a sulfonic acid group, a saturated hydrocarbon group having 1 to 8 carbon atoms or a saturated hydrocarbon group having 1 to 8 carbon atoms substituted with a fluorine atom, and R 12 and R 13 are each independently a single bond or Represents an alkylene group having 1 to 5 carbon atoms, and h represents 0 or 1.
  • Q is related with the polyester composition for thermosetting film formation as described in a 2nd viewpoint or a 3rd viewpoint which represents group represented by a following formula (1Q1).
  • the present invention relates to the thermosetting film-forming polyester composition according to claim 1, wherein the component (C) contains at least one polyvalent ester compound represented by the following formula (1-a).
  • the (A) component is a polyester obtained by reacting a tetracarboxylic dianhydride represented by the following formula (i) with a diol compound represented by the formula (ii). It is related with the polyester composition for thermosetting film formation as described in any one of thru
  • A represents a tetravalent organic group in which four bonds are bonded to an alicyclic group or an aliphatic group
  • B is a divalent group in which two bonds are bonded to an alicyclic group or an aliphatic group.
  • A represents at least one group selected from the groups represented by the following formulas (A-1) to (A-8), and B represents the following formula (B- 1) to the polyester composition for forming a thermosetting film according to the sixth aspect or the seventh aspect, which represents at least one group selected from the groups represented by formula (B-5).
  • the weight average molecular weight of polyester which is (A) component is 1,000 thru
  • the present invention relates to a polyester composition.
  • a 10th viewpoint it is related with the polyester composition for thermosetting film formation as described in any one of the 1st viewpoint thru
  • the present invention further relates to the thermosetting film forming polyester composition according to any one of the first aspect to the eleventh aspect, which contains a bismaleimide compound as the component (F).
  • a bismaleimide compound as the component (F).
  • the polyester composition for thermosetting film formation as described in any one of them.
  • a 14th viewpoint based on 100 mass parts of (A) component, it is related with the polyester composition for thermosetting film formation as described in a 10th viewpoint containing 0.01 thru
  • the polyester composition for thermosetting film formation as described in an 11th viewpoint containing 0.5 thru
  • the polyester composition for thermosetting film formation as described in a 12th viewpoint containing 0.5 thru
  • the cured film obtained using the polyester composition for thermosetting film formation as described in any one of a 1st viewpoint thru
  • the polyester composition for forming a thermosetting film of the present invention can form a cured film having liquid crystal alignment ability in addition to high flatness, high transparency, high solvent resistance, and high heat resistance. It can be used as a material for forming a chemical film. In particular, it is possible to form the liquid crystal alignment film and the overcoat layer of the color filter, which have been conventionally formed independently, as a “liquid crystal alignment layer” having both characteristics at the same time, simplifying the manufacturing process and the number of processes. Cost reduction by reduction can be realized. Furthermore, since the polyester composition for forming a thermosetting film of the present invention is soluble in a glycol-based solvent, it can be suitably used in a production line for a flattened film that mainly uses these solvents.
  • FIG. 1 is a model diagram showing a cured film formed when a thermosetting polyester composition is applied to a stepped substrate. It is a model figure which compares and shows the liquid crystal cell (a) which formed the liquid crystal aligning film by the prior art, and the liquid crystal cell (b) which formed the planarization film
  • the conventionally proposed acrylic resin-based and polyimide-based cured films sufficiently satisfy all performances such as flatness, transparency, and orientation required for liquid crystal alignment films and flattening films. There was nothing I could do.
  • the use of polyester as an alignment material for liquid crystal display elements has been proposed (see Japanese Patent Application Laid-Open Nos. H5-158055 and 2002-229039).
  • the solvent resistance of the formed cured film was also inferior.
  • the present invention is characterized in that performances such as the above-described flatness, transparency and orientation are improved by using a thermosetting polyester. That is, the present invention provides a polyester as the component (A), a crosslinking agent as the component (B), and a diester compound represented by the following formula (1) as the component (C).
  • P represents an alicyclic group, a group containing a group composed of an alicyclic group and an aliphatic group, or a structure represented by the formula (2)
  • Q represents an alicyclic group or an alicyclic group.
  • R in formula (2) represents an alkylene group.
  • a silane coupling agent as component (E) a silane coupling agent as component (E)
  • F bismaleimide compound
  • the polyester of component (A) is preferably a polyester containing a structural unit represented by the following formula (3), more preferably a polyester comprising a structural unit represented by formula (3).
  • A represents a tetravalent organic group in which four bonds are bonded to an alicyclic group or an aliphatic group
  • B is a divalent organic group in which two bonds are bonded to an alicyclic or aliphatic group.
  • A is preferably a group represented by the following formula (3A1), formula (3A2) or formula (3A3).
  • a 1 in the formula represents a cyclic saturated hydrocarbon group, preferably a cyclic saturated hydrocarbon group having 4 to 8 carbon atoms, and more preferably a cyclic saturated hydrocarbon group having 4 to 6 carbon atoms.
  • any hydrogen atom contained in the A 1 group may be independently substituted with an aliphatic group, and two of them are bonded to each other to form a 4- to 6-membered ring. May be.
  • the aliphatic group as the substituent is preferably an aliphatic group having 1 to 5 carbon atoms, more preferably an aliphatic group having 1 to 3 carbon atoms.
  • R 1 represents a single bond, a carbonyl group, an ether group, a sulfonic acid group, a saturated hydrocarbon group having 1 to 8 carbon atoms, or a saturated hydrocarbon group having 1 to 8 carbon atoms substituted with a fluorine atom.
  • it represents a single bond, a carbonyl group, an ether group, a sulfonic acid group, a saturated hydrocarbon group having 1 to 5 carbon atoms, or a saturated hydrocarbon group having 1 to 5 carbon atoms substituted with a fluorine atom.
  • R 2 represents a saturated hydrocarbon group having 1 to 8 carbon atoms, preferably a saturated hydrocarbon group having 1 to 5 carbon atoms, more preferably a saturated hydrocarbon group having 1 to 3 carbon atoms. .
  • A which is a tetravalent organic group in the formula (3) are shown in the following formulas (A-1) to (A-8).
  • A is particularly preferably a group selected from the formula (A-1) or (A-2).
  • B represents a divalent organic group in which two bonds are bonded to an alicyclic group or an aliphatic group, preferably a group represented by the following formula (3B1) or formula (3B2) It is.
  • B 1 in the formula represents a cyclic saturated hydrocarbon group, preferably a cyclic saturated hydrocarbon group having 4 to 8 carbon atoms, more preferably a cyclic saturated hydrocarbon group having 4 to 6 carbon atoms.
  • Any hydrogen atom contained in the B 1 group may be independently substituted with an aliphatic group.
  • the aliphatic group as the substituent is preferably an aliphatic group having 1 to 5 carbon atoms, and more preferably an aliphatic group having 1 to 3 carbon atoms.
  • B 2 represents a phenylene group.
  • R 3 represents a single bond, a carbonyl group, an ether group, a sulfonic acid group, a saturated hydrocarbon group having 1 to 8 carbon atoms, or a saturated hydrocarbon group having 1 to 8 carbon atoms substituted with a fluorine atom.
  • it represents a single bond, a carbonyl group, an ether group, a sulfonic acid group, a saturated hydrocarbon group having 1 to 5 carbon atoms, or a saturated hydrocarbon group having 1 to 5 carbon atoms substituted with a fluorine atom.
  • R 4 and R 5 each independently represents a single bond or an alkylene group having 1 to 5 carbon atoms, preferably a single bond or an alkylene group having 1 to 3 carbon atoms.
  • R 6 and R 7 each independently represents an alkylene group having 1 to 5 carbon atoms, preferably an alkylene group having 1 to 3 carbon atoms.
  • K represents 0 or 1.
  • B which is a divalent organic group in the formula (3) are shown in the following formulas (B-1) to (B-5).
  • B is particularly preferably a group selected from (B-1) to (B-4).
  • the polyester of component (A) contains at least one structure selected from the group consisting of groups represented by formulas (3A1) to (3A3), wherein A is a structural unit represented by formula (3).
  • a structure other than the groups represented by formulas (3A1) to (3A3) may be included.
  • the structure is not particularly limited as long as the structure of the polyester is formed, but it is preferably at least one structure selected from the group consisting of groups represented by the following formulas (3A4) to (3A5). .
  • R 8 , R 9 and R 10 are each independently a single bond, a carbonyl group, an ether group, a sulfonic acid group, a saturated hydrocarbon group having 1 to 8 carbon atoms or a carbon atom substituted with a fluorine atom.
  • R 8 is a single bond, a carbonyl group, an ether group, a sulfonic acid group, a saturated hydrocarbon group having 1 to 5 carbon atoms, or a saturated hydrocarbon group having 1 to 5 carbon atoms substituted with a fluorine atom.
  • R 9 is preferably an ether group, a saturated hydrocarbon group having 1 to 5 carbon atoms or a saturated hydrocarbon group having 1 to 5 carbon atoms substituted with a fluorine atom
  • R 10 is a carbonyl group An ether group, a sulfonic acid group, a saturated hydrocarbon group having 1 to 5 carbon atoms, or a saturated hydrocarbon group having 1 to 5 carbon atoms substituted with a fluorine atom.
  • H represents 0 or 1.
  • At least A is selected from the group consisting of the groups represented by the above formulas (3A1) to (3A3). It is preferable that at least 60 mol% of one kind of structural unit is contained.
  • the weight average molecular weight of the component (A) polyester is preferably 1,000 to 30,000, more preferably 1,500 to 10,000.
  • the orientation and solvent resistance tend to decrease, and when it exceeds the above range, the flatness may decrease.
  • the polyester as component (A) can be obtained, for example, by polymerizing tetracarboxylic dianhydride and a diol compound. More preferably, a tetracarboxylic dianhydride containing a tetracarboxylic dianhydride represented by the following formula (i) (hereinafter also referred to as an acid component) and a diol compound represented by the following formula (ii) are included. It is obtained by reacting with a diol compound (hereinafter also referred to as a diol component).
  • a diol compound hereinafter also referred to as a diol component
  • the mixing ratio of the total amount of tetracarboxylic dianhydride (total amount of acid component) and the total amount of diol compound (total amount of diol component), that is, ⁇ total number of moles of diol compound > / ⁇ Total number of moles of tetracarboxylic dianhydride compound> is preferably 0.5 to 1.5. Similar to a normal polycondensation reaction, the closer the molar ratio is to 1, the higher the degree of polymerization of the polyester produced and the higher the molecular weight.
  • the terminal of the polyester (A) is an acid anhydride terminal.
  • the terminal of the polyester varies depending on the blending ratio of the acid component and the diol component. For example, when the acid component is reacted excessively, the terminal tends to be an acid anhydride. Moreover, when it superposes
  • carboxylic anhydrides examples include phthalic anhydride, trimellitic anhydride, maleic anhydride, naphthalic anhydride, hydrogenated phthalic anhydride, itaconic anhydride, tetrahydrophthalic anhydride, 1, 2-cyclohexanedicarboxylic acid anhydride, 4-methyl-1,2-cyclohexanedicarboxylic acid anhydride, 4-phenyl-1,2-cyclohexanedicarboxylic acid anhydride, methyl-5-norbornene-2,3-dicarboxylic acid anhydride Tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, bicyclo [2.2.2. And octene-2,3-dicarboxylic acid anhydride.
  • the reaction temperature between the acid component and the diol component can be selected from 50 to 200 ° C., preferably 80 to 170 ° C.
  • the polyester can be obtained at a reaction temperature of 100 ° C. to 140 ° C. and a reaction time of 2 to 48 hours.
  • the reaction temperature for protecting the terminal hydroxyl group with an acid anhydride can be selected from 50 to 200 ° C., preferably 80 to 170 ° C.
  • the reaction between the acid component and the diol component is usually performed in a solvent.
  • the solvent that can be used in this case is not particularly limited as long as it does not contain a functional group that reacts with an acid anhydride, such as a hydroxyl group or an amino group.
  • solvents may be used alone or as a mixture, but propylene glycol monomethyl ether acetate is more preferable from the viewpoint of safety and applicability to a color filter overcoat agent line. Furthermore, even if it is a solvent which does not melt
  • a catalyst can also be used in the reaction of the acid component (formula (i)) and the diol component (formula (ii)).
  • Specific examples of the catalyst used during the polymerization of polyester include benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltriethylammonium chloride, benzyltriethylammonium bromide, benzyltripropylammonium chloride, benzyltripropylammonium bromide, tetramethylammonium chloride, tetraethyl.
  • Quaternary ammonium salts such as ammonium bromide, tetrapropylammonium chloride, tetrapropylammonium bromide, tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, benzyltriphenylphosphonium chloride, benzyltriphenylphosphonium bromide, ethyltriphenylphosphonium chloride, ethyltriphenyl Quaternary phosphonium salts such as Le bromide and the like.
  • the solution containing the polyester of the component (A) thus obtained can be used as it is for the preparation of the thermosetting film forming polyester composition.
  • the obtained polyester can also be used after being recovered by precipitation and isolation in a poor solvent such as water, methanol, ethanol, diethyl ether, and hexane.
  • (B) component of this invention is a crosslinking agent.
  • the crosslinking agent include compounds such as an epoxy compound and a methylol compound, and an epoxy compound having two or more epoxy groups is preferable. Examples of such compounds are tris (2,3-epoxypropyl) isocyanurate, 1,4-butanediol diglycidyl ether, 1,2-epoxy-4- (epoxyethyl) cyclohexane, glycerol triglycidyl ether, diethylene glycol diester.
  • Glycidyl ether 2,6-diglycidylphenyl glycidyl ether, 1,1,3-tris [p- (2,3-epoxypropoxy) phenyl] propane, 1,2-cyclohexanedicarboxylic acid diglycidyl ester, 4,4 ′ -Methylenebis (N, N-diglycidylaniline), 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, trimethylolethane triglycidyl ether and bisphenol-A-diglycidyl ether, and And pentaerythritol polyglycidyl ether.
  • epoxy resins having amino groups such as YH-434, YH434L (manufactured by Tohto Kasei Co., Ltd.); Epolide GT-401, Epoxy resins having a cyclohexene oxide structure such as GT-403, GT-301, GT-302, Celoxide 2021, Celoxide 3000, Celoxide P-2021 (manufactured by Daicel Chemical Industries, Ltd.); Epicoat 1001, 1002, and 1003, 1004, 1007, 1009, 1010, 1010, 828 (above, Yuka Shell Epoxy Co., Ltd.
  • a polymer having an epoxy group can be used as the compound having at least two epoxy groups.
  • any polymer having an epoxy group can be used without particular limitation.
  • the polymer having an epoxy group can be produced, for example, by addition polymerization using an addition polymerizable monomer having an epoxy group. Examples include addition polymerization polymers such as polyglycidyl acrylate, copolymers of glycidyl methacrylate and ethyl methacrylate, copolymers of glycidyl methacrylate and styrene and 2-hydroxyethyl methacrylate, and condensation polymerization polymers such as epoxy novolac. .
  • the polymer which has the said epoxy group can also be manufactured by reaction of the high molecular compound which has a hydroxyl group, and compounds which have epoxy groups, such as epichlorohydrin and glycidyl tosylate.
  • the weight average molecular weight of such a polymer is, for example, 300 to 200,000.
  • epoxy compounds having two or more epoxy groups can be used alone or in combination of two or more.
  • the content of the crosslinking agent as the component (B) in the polyester composition for forming a thermosetting film of the present invention is preferably 3 to 50 parts by mass, more preferably based on 100 parts by mass of the polyester as the component (A). 5 to 40 parts by mass, particularly preferably 10 to 30 parts by mass.
  • this ratio is too small, the solvent resistance and heat resistance of the cured film obtained from the polyester composition for thermosetting film formation are reduced. On the other hand, when the ratio is excessive, the solvent resistance is reduced and storage stability is decreased. May decrease.
  • a component is a diester compound represented by following formula (1).
  • a diester compound of (C) component not only one type but the compound represented by Formula (1) can be used.
  • P represents an alicyclic group, a group composed of an alicyclic group and an aliphatic group or a structure represented by the formula (2)
  • Q represents an alicyclic group or an alicyclic group or an aliphatic group and an aliphatic group.
  • P and Q may each be any hydrogen atom in the group substituted with an aliphatic group.
  • R represents an alkylene group, preferably R represents an alkylene group having 1 to 6 carbon atoms, more preferably an alkylene group having 1 to 5 carbon atoms, and still more preferably a carbon atom. Represents an alkylene group of formulas 1 to 3;
  • P 1 represents a cyclic saturated hydrocarbon group, preferably a cyclic saturated hydrocarbon group having 4 to 8 carbon atoms, and more preferably a cyclic saturated hydrocarbon group having 4 to 6 carbon atoms. Any hydrogen atom in the group P 1 may be independently substituted with an aliphatic group.
  • the aliphatic group as the substituent is preferably an aliphatic group having 1 to 5 carbon atoms, and more preferably an aliphatic group having 1 to 3 carbon atoms.
  • R 11 represents a single bond, a carbonyl group, an ether group, a sulfonic acid group, a saturated hydrocarbon group having 1 to 8 carbon atoms, or a saturated hydrocarbon group having 1 to 8 carbon atoms substituted with a fluorine atom.
  • R 12 and R 13 each independently represents a single bond or an alkylene group having 1 to 5 carbon atoms, preferably a single bond or an alkylene group having 1 to 3 carbon atoms.
  • H represents 0 or 1.
  • Preferred examples of P in the above formula (1) are shown in the following formulas (P-1) to (P-5).
  • Q represents an alicyclic group or a group composed of an alicyclic group and an aliphatic group, preferably a group represented by the following formula (1Q1).
  • Q 1 represents a cycloalkylene group or cycloalkenylene group having 4 to 8 carbon atoms, preferably a cycloalkylene group or cycloalkenylene group having 4 to 6 carbon atoms. Any hydrogen atom in the group Q 1 may be substituted with an aliphatic group.
  • the aliphatic group as the substituent is preferably an aliphatic group having 1 to 5 carbon atoms, and more preferably an aliphatic group having 1 to 3 carbon atoms.
  • X represents a single bond or an alkylene group having 1 to 3 carbon atoms.
  • preferable Q 1 examples include a cyclobutane group, a methylcyclobutane group, a dimethylcyclobutane group, a cyclopentyl group, a cyclohexylene group, a methylcyclohexylene group, a tetrahydrophthaloyl group, and a methyltetrahydrophthaloyl group.
  • the diester compound which is the component (C) of the present invention contains 1 mol of a diol represented by the following formula (iii) and 1.7 to 2 mol of a dicarboxylic acid anhydride represented by the formula (iv), preferably 1.8. It is obtained by reacting with 2 mol.
  • P represents an alicyclic group, a group composed of an alicyclic group and an aliphatic group, or a structure represented by formula (2)
  • Q represents an alicyclic group or A group consisting of an alicyclic group and an aliphatic group is represented
  • R represents an alkylene group.
  • P, Q, and R are the same meaning as the definition of Formula (1) and Formula (2) mentioned above, and a preferable form is also the same as what was mentioned above.
  • each of the diol compound represented by the above formula (iii) and the dicarboxylic acid anhydride represented by the formula (iv) may be used alone or in combination.
  • diol compound represented by the formula (iii) include, for example, hydrogenated bisphenol A, 4,4′-bicyclohexanol, 1,4-cyclohexanediol, 1,3-cyclohexanediol, 1,4- Examples include cyclohexanedimethanol, 1,3-cyclohexanedimethanol, p-xylene glycol, and m-xylene glycol.
  • the component (C) may be a polyvalent ester compound represented by the following formula (1-a).
  • the polyvalent ester compound not only one kind of the compound represented by the formula (1-a) but also plural kinds thereof can be used.
  • Pa represents an alicyclic group or aliphatic alkyl group which may be interrupted by an oxygen atom or a nitrogen atom, or a structure represented by the formula (2-a), and Qa represents an alicyclic group.
  • T represents an integer of 1 to 5, and Pa and Qa may each have an arbitrary hydrogen atom in the group substituted with an aliphatic group.
  • Ra represents an alkylene group, preferably Ra represents an alkylene group having 1 to 6 carbon atoms, more preferably an alkylene group having 1 to 5 carbon atoms, and more preferably Represents an alkylene group having 1 to 3 carbon atoms.
  • the polyvalent ester compound is obtained by reacting a diol represented by the following formula (iii-a) with a dicarboxylic acid anhydride represented by the formula (iv-a).
  • Pa is an alicyclic group or aliphatic alkyl group which may be interrupted by an oxygen atom or a nitrogen atom, or represented by the formula (2-a).
  • T represents an integer of 1 to 5
  • Qa represents an alicyclic group
  • Ra represents an alkylene group. Note that Pa, Qa, and Ra have the same definitions as those in the above formulas (1-a) and (2-a), and preferred forms are also the same as those described above.
  • each of the polyhydric alcohol compound represented by the above formula (iii-a) and the dicarboxylic acid anhydride represented by the formula (iv-a) may be used alone or in combination. May be.
  • polyhydric alcohol compound represented by the above formula (iii-a) examples include compounds such as 1,3,5-cyclohexanetriol and pentaerythritol. Specific examples of the polyhydric alcohol compound represented by the above formula (iii-a) are shown below.
  • dicarboxylic acid anhydride represented by the above formula (iv) include, for example, 1,2-cyclohexanedicarboxylic acid anhydride, 4-methyl-1,2-cyclohexanedicarboxylic acid anhydride, tetrahydrophthalic acid anhydride. , Methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride and the like.
  • the reaction temperature between the diol compound (or polyhydric alcohol compound) and the dicarboxylic acid anhydride is 50 to 200 ° C., preferably 80 to 170 ° C. Any temperature can be selected.
  • the diester compound (or polyvalent ester compound) can be obtained at a reaction temperature of 100 ° C. to 140 ° C. and a reaction time of 2 to 48 hours.
  • the reaction of the diol compound (or polyhydric alcohol compound) and the dicarboxylic acid anhydride is usually performed in a solvent.
  • the solvent that can be used in this case is not particularly limited as long as it does not contain a functional group that reacts with an acid anhydride, such as a hydroxyl group or an amino group.
  • solvents may be used alone or as a mixture, but propylene glycol monomethyl ether acetate is more preferable from the viewpoint of safety and applicability to a color filter overcoat agent line. Furthermore, even if it is a solvent which does not melt
  • the catalyst used in this case include benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltriethylammonium chloride, benzyltriethylammonium bromide, benzyltripropylammonium chloride, benzyltripropylammonium bromide, tetramethylammonium chloride, tetraethylammonium bromide.
  • Quaternary ammonium salts such as tetrapropylammonium chloride, tetrapropylammonium bromide, tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, benzyltriphenylphosphonium chloride, benzyltriphenylphosphonium bromide, ethyltriphenylphosphonium chloride, ethyltriphenylphosphonium
  • a quaternary phosphonium salts such as Romido can be mentioned.
  • the content of the component (C) is preferably 1 to 100 parts by mass, more preferably 5 to 60, based on 100 parts by mass of the polyester of the component (A). Part by mass.
  • this ratio is too small, the orientation of the cured film obtained from the polyester composition for forming a thermosetting film is lowered or the flatness is lowered. On the other hand, when it is too large, the transmittance is lowered. Sometimes.
  • ⁇ (D) component> In this invention, you may contain antioxidant as (D) component.
  • This component (D) is effective in preventing discoloration of the film due to high-temperature firing assumed in the process after the thermosetting film is formed according to the present invention.
  • the antioxidant of the component (D) is particularly preferably a phenol compound.
  • a phenol compound examples thereof include 2,6-di-t-butyl-4-cresol, 2,6-di-t-butyl-phenol, 2,4. , 6-Tris (3 ′, 5′-di-t-butyl-4′-hydroxybenzyl) mesitylene, pentaerythritol tetrakis [3- (3 ′, 5′-di-t-butyl-4′-hydroxyphenyl) Propionate], acetone bis (3,5-di-t-butyl-4-hydroxyphenyl) mercaptol, 4,4′-methylenebis (2,6-di-t-butylphenol), 3- (3,5-di-) t-butyl-4-hydroxyphenyl) methyl propionate, 4,4′-thiodi (2,6-di-t-butylphenol), tris (3,5-di-t-butyl-4-
  • phenol compounds which are antioxidants are not particularly limited to those described above. These can be used alone or in combination of two or more components.
  • antioxidants 2,6-di-t-butyl-4-cresol, 2,4,6-tris (3 ′, 5′-di-t-butyl-4′-hydroxybenzyl) mesitylene, 4 , 4′-methylenebis (2,6-di-t-butylphenol) is particularly preferable because it does not lower the orientation and has high heat resistance.
  • the usage-amount of the phenolic compound which is antioxidant of (D) component is 0.01-5 mass parts with respect to 100 mass parts of polyester of (A) component, More preferably, it is 0.00. 1 to 3 parts by mass.
  • this ratio is too small, the effect as an antioxidant may not be sufficiently obtained, and when it is too large, the orientation may be deteriorated or the coating film may be roughened.
  • a silane coupling agent may be contained as the component (E).
  • the silane coupling agent as the component (E) is effective in improving the adhesion with a retardation material composed of a polymerizable liquid crystal.
  • silane coupling agents include chlorosilanes such as trimethylchlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, and chloromethyldimethylchlorosilane; trimethylmethoxysilane, dimethyldiethoxysilane, methyldimethoxysilane, and dimethylvinylethoxysilane.
  • Alkoxysilanes such as diphenyldimethoxysilane, phenyltriethoxysilane; silazanes such as hexamethyldisilazane, N, N′-bis (trimethylsilyl) urea, dimethyltrimethylsilylamine, trimethylsilylimidazole, vinyltrichlorosilane, ⁇ -aminopropyl Triethoxysilane, ⁇ -methacryloxypropyltrimethoxysilane, ⁇ -methacryloxypropyltriethoxysilane, ⁇ -glycyl Silanes such as doxypropyltriethoxysilane and ⁇ - (N-piperidinyl) propyltriethoxysilane; benzotriazole, benzimidazole, indazole, imidazole, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole And hetero
  • silane coupling agents one kind or a combination of two or more kinds can be used.
  • silane coupling agents ⁇ -methacryloxypropyltriethoxysilane is particularly preferred from the viewpoints of adhesion with a retardation material composed of a polymerizable liquid crystal and storage stability.
  • silane coupling agent for example, commercially available compounds such as those manufactured by Shin-Etsu Chemical Co., Ltd., MOMENTIVE, and Toray Dow Corning Co., Ltd. can be used, and these commercially available products can be easily obtained. It is.
  • the addition amount of these silane coupling agents is usually 0.5 to 30 parts by mass, more preferably 0.8 to 20 parts by mass with respect to 100 parts by mass of the component (A). If it is used in an amount of 20 parts by mass or more, the solvent resistance of the coating film may be lowered, and if it is less than 0.5 parts by mass, the sufficient effect of the silane coupling agent may not be obtained.
  • a bismaleimide compound may be contained as the component (F).
  • the (B) component bismaleimide compound is effective in further improving the flatness, and examples thereof include a compound represented by the following formula (4). These bismaleimide compounds are not particularly limited to those described above. These can be used alone or in combination of two or more components.
  • Y is an organic group selected from the group consisting of an aliphatic group, an aliphatic group containing a cyclic structure and an aromatic group, or an organic group consisting of a combination of a plurality of organic groups selected from these groups.
  • Y may contain a bond such as an ester bond, an ether bond, an amide bond, or a urethane bond.
  • Examples of the bismaleimide compound represented by the above formula (4) include N, N′-3,3-diphenylmethane bismaleimide, N, N ′-(3,3-diethyl-5,5-dimethyl) -4. , 4-Diphenyl-methane bismaleimide, N, N′-4,4-diphenylmethane bismaleimide, 3,3-diphenylsulfone bismaleimide, 4,4-diphenylsulfone bismaleimide, N, N′-p-benzophenone bismaleimide N, N′-diphenylethane bismaleimide, N, N′-diphenyl ether bismaleimide, N, N ′-(methylenedi-ditetrahydrophenyl) bismaleimide, N, N ′-(3-ethyl) -4,4- Diphenylmethane bismaleimide, N, N '-(3,3-dimethyl) -4,4-dipheny
  • aromatic bismaleimides those having a molecular weight of 1,000 or less are preferable in order to obtain higher flatness.
  • the use ratio of the (F) component bismaleimide compound is preferably 0.5 to 50 parts by mass, more preferably 1 to 30 parts by mass with respect to 100 parts by mass of the component (A) polyester. Yes, particularly preferably 2 to 20 parts by mass. If this ratio is too small, it may be difficult to obtain the effect of improving the flatness of the cured film obtained from the polyester composition for thermosetting film formation. If it is too large, the transmittance of the cured film may be obtained. May decrease or the coating film may become rough.
  • the polyester composition for forming a thermosetting film of the present invention is often dissolved in a solvent and used in a solution state.
  • the solvent used in that case is a component that dissolves the components (A) to (C), and if necessary, the components (D) to (F) and / or other additives described below.
  • the solvent is not particularly limited in its type and structure as long as it has a good solubility.
  • polymerization of (A) component and the following solvent can be mentioned.
  • These solvents can be used singly or in combination of two or more.
  • polyester composition for forming a thermosetting film of the present invention may be used as necessary as long as it does not impair the effects of the present invention.
  • Adhesive aids such as surfactants and rheology modifiers, pigments, dyes, storage stability Agents, antifoaming agents, dissolution accelerators such as polyhydric phenols and polycarboxylic acids, and the like.
  • the polyester composition for forming a thermosetting film of the present invention comprises (A) component polyester, (B) component cross-linking agent, (C) component diester (or polyvalent ester), and optionally (D) component. (E) component silane coupling agent, (F) component bismaleimide compound, and a composition that can further contain one or more other additives. Usually, they are often used as a solution in which they are dissolved in a solvent.
  • the preferable example of the polyester composition for thermosetting film formation of this invention is as follows.
  • the blending ratio, preparation method, etc. when the polyester composition for forming a thermosetting film of the present invention is used as a solution will be described in detail below.
  • the ratio of the solid content in the polyester composition for forming a thermosetting film of the present invention is not particularly limited as long as each component is uniformly dissolved in a solvent, but is 1 to 80% by mass, preferably 5 to 60% by mass, more preferably 10 to 50% by mass.
  • solid content means what remove
  • the preparation method of the polyester composition for thermosetting film formation of this invention is not specifically limited, As the preparation method, (A) component is melt
  • a polyester solution obtained by a polymerization reaction in a solvent can be used as it is.
  • (B) component, (C) component, (D) component, (E) component, (F) component, etc. are put into the solution of this (A) component similarly to the above, it is set as a uniform solution.
  • an additional solvent may be added.
  • the solvent used in the polyester production process may be the same as or different from the solvent used for adjusting the concentration when preparing the polyester composition for thermosetting film formation.
  • the prepared solution of the polyester composition for forming a thermosetting film is preferably used after being filtered using a filter having a pore size of about 0.2 ⁇ m.
  • the polyester composition for forming a thermosetting film of the present invention is a substrate (for example, a silicon / silicon dioxide-coated substrate, a silicon nitride substrate, a substrate coated with a metal such as aluminum, molybdenum, or chromium, a glass substrate, a quartz substrate, Rotating coating, flow coating, roll coating, slit coating, rotary coating following slit, inkjet coating, etc. on ITO substrate etc.) and film (for example, resin film such as triacetyl cellulose film, polyester film, acrylic film)
  • the coating film can be formed by coating by printing or the like and then pre-drying (pre-baking) with a hot plate or oven. Then, a coating film is formed by heat-processing this coating film.
  • a heating temperature and a heating time appropriately selected from the range of a temperature of 70 ° C. to 160 ° C. and a time of 0.3 to 60 minutes are adopted.
  • the heating temperature and heating time are preferably 80 to 140 ° C. and 0.5 to 10 minutes.
  • the film thickness of the film formed from the thermosetting film-forming polyester composition is, for example, 0.1 to 30 ⁇ m, and can be appropriately selected in consideration of the level difference of the substrate to be used and the optical and electrical properties. .
  • the post-bake is generally processed at a heating temperature selected from the range of 140 ° C. to 250 ° C. for 5 to 30 minutes when on a hot plate and 30 to 90 minutes when in an oven. The method is taken.
  • the step of the substrate can be sufficiently flattened, and a cured film having high transparency can be formed.
  • the cured film thus formed can be made to function as a liquid crystal alignment layer, that is, a layer for aligning liquid crystal compounds by rubbing.
  • a liquid crystal alignment layer that is, a layer for aligning liquid crystal compounds by rubbing.
  • conditions for the rubbing treatment generally, conditions of a rotational speed of 300 to 1000 rpm, a feed speed of 3 to 200 mm / second, and an indentation amount of 0.1 to 1 mm are used. Thereafter, the residue generated by rubbing is removed by ultrasonic cleaning using pure water or the like.
  • the retardation material After coating the retardation material on the liquid crystal alignment layer thus formed, the retardation material can be photocured in a liquid crystal state to form a layer having optical anisotropy.
  • the retardation material for example, a liquid crystal monomer having a polymerizable group or a composition containing the same is used.
  • liquid crystal is injected between the substrates, and the liquid crystal
  • the liquid crystal display element can be oriented.
  • the substrate for forming the liquid crystal alignment layer is a film, it is a material useful as an optically anisotropic film.
  • thermosetting film forming polyester composition of the present invention can be suitably used for various optical anisotropic films and liquid crystal display elements.
  • the polyester composition for forming a thermosetting film of the present invention has at least a necessary level of flatness, a protective film, a flattening film, etc. It is also useful as a material for forming a cured film such as an insulating film, and is particularly suitable as a material for forming an overcoat material for a color filter, an interlayer insulating film for a TFT liquid crystal element, an insulating film for an organic EL element, and the like. .
  • the number average molecular weight and weight average molecular weight of the polyester, polyimide precursor, and acrylic copolymer obtained according to the following synthesis examples are eluted using a GPC apparatus (Shodex (registered trademark) columns KF803L and KF804L) manufactured by JASCO Corporation. The measurement was performed under the condition that the solvent tetrahydrofuran was allowed to flow through the column at a flow rate of 1 ml / min (column temperature 40 ° C.) for elution.
  • Mn number average molecular weight
  • Mw weight average molecular weight
  • or Comparative Example 3 were prepared with the composition shown in Table 1, and about each cured film obtained from this composition, planarization property and solvent resistance, respectively. , Orientation, adhesion, transparency and heat resistance (transmittance) were evaluated.
  • DOP flattening ratio
  • the flattening rate was obtained using the formula of substrate height (1.0 ⁇ m) ⁇ ].
  • it is desirable that the film has a flattening rate of at least 60%.
  • a retardation material composed of a liquid crystal monomer was applied onto the substrate using a spin coater, and then prebaked on a hot plate at 80 ° C. for 60 seconds to form a coating film having a thickness of 1.4 ⁇ m.
  • This substrate was exposed at 1,000 mJ in a nitrogen atmosphere.
  • the produced substrate was sandwiched between deflection plates, and the orientation was confirmed visually.
  • the case where the light transmittance changed significantly when the substrate was tilted at 45 degrees and the case where the substrate was not tilted was evaluated as ⁇ , and the case where the substrate did not change as x.
  • a retardation material composed of a liquid crystal monomer was applied onto this substrate using a spin coater, and then prebaked on a hot plate at 80 ° C. for 60 seconds to form a coating film having a thickness of 1.4 ⁇ m.
  • This substrate was exposed at 1,000 mJ in a nitrogen atmosphere.
  • an adhesive tape peeling test (used tape: cello tape (registered trademark)) was performed. Of the 25 cuts, those that were not peeled off at all were marked with ⁇ , and those that were even peeled off were marked with x.
  • Examples 1 to 9 were resistant to any of the flattening rate, PGMEA, and NMP. In addition, both showed good orientation, and achieved high transmittance (transparency) after high-temperature baking and further high-temperature baking, as well as heat resistance. Furthermore, in any of the examples, the adhesion with the retardation material was good.
  • Comparative Example 1 no cured film was formed. Further, Comparative Example 2 had good solvent resistance, heat resistance, and orientation, but resulted in problems with transparency, and resulted in a very low flattening rate and poor adhesion. It was. And although the result which made the flattening rate, solvent tolerance, and transparency favorable was obtained for the comparative example 3, it became a result which is inferior to orientation and adhesiveness.
  • the polyester composition for forming a thermosetting film of the present invention can use a glycol-based solvent such as propylene glycol monomethyl ether acetate at the time of forming the cured film, and the obtained cured film has excellent light properties. Good results were obtained for all the properties of permeability, solvent resistance, heat resistance, planarization, adhesion and orientation.
  • a glycol-based solvent such as propylene glycol monomethyl ether acetate
  • the polyester composition for forming a thermosetting film according to the present invention is very useful as an optically anisotropic film or a liquid crystal alignment layer of a liquid crystal display element, and further various types such as a thin film transistor (TFT) type liquid crystal display element and an organic EL element.
  • TFT thin film transistor
  • Materials for forming a cured film such as a protective film, a planarizing film, and an insulating film in a display, especially as a material for forming an interlayer insulating film for a TFT liquid crystal element, a protective film for a color filter, an insulating film for an organic EL element, etc. Is preferred.

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JP2012194538A (ja) * 2011-02-28 2012-10-11 Jsr Corp 液晶配向剤、液晶配向膜及び液晶表示素子
WO2023238515A1 (ja) * 2022-06-07 2023-12-14 日東電工株式会社 組成物、液晶ポリマーシート、低誘電基板材、及び配線回路基板

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JPWO2010110221A1 (ja) 2012-09-27
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