WO2010113944A1 - 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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WO2010113944A1
WO2010113944A1 PCT/JP2010/055699 JP2010055699W WO2010113944A1 WO 2010113944 A1 WO2010113944 A1 WO 2010113944A1 JP 2010055699 W JP2010055699 W JP 2010055699W WO 2010113944 A1 WO2010113944 A1 WO 2010113944A1
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component
group
polyester
polyester composition
thermosetting film
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PCT/JP2010/055699
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English (en)
French (fr)
Japanese (ja)
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真 畑中
勲 安達
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日産化学工業株式会社
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Priority to JP2011507212A priority Critical patent/JP5641250B2/ja
Priority to KR1020117025356A priority patent/KR101736885B1/ko
Priority to CN201080014439.XA priority patent/CN102369230B/zh
Publication of WO2010113944A1 publication Critical patent/WO2010113944A1/ja

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    • 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
    • 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
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • 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
    • 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
    • C08G59/50—Amines
    • C08G59/54—Amino amides>
    • 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
    • C08G59/50—Amines
    • C08G59/56—Amines together with other curing agents
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers

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.
  • Polyimide and polyamic acid are soluble in solvents such as N-methyl-2-pyrrolidone and ⁇ -butyrolactone, but have low solubility in glycol-based solvents and ester-based solvents. Was difficult.
  • an object of the present invention is to provide a material that can be dissolved in a glycol-based solvent or a lactic acid ester-based solvent that can be applied in the production line of a color filter flattening film when forming a cured film.
  • the present inventors have found the present invention. That is, as a 1st viewpoint, it is related with the polyester composition for thermosetting film formation containing (A) component, (B) component, and (C) component.
  • (A) component polyester obtained by reacting a tetracarboxylic dianhydride and a diol compound
  • (B) component an epoxy compound having two or more epoxy groups
  • (C) Component An amino group-containing carboxylic acid compound obtained by reacting a diamine compound with a dicarboxylic acid anhydride.
  • the said (A) component is related with the polyester composition for thermosetting film formation as described in a 1st viewpoint which is polyester containing the structural unit represented by following formula (1).
  • the component (A) 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 a viewpoint or a 2nd viewpoint.
  • 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) It relates to a polyester composition for forming a thermosetting film according to the second aspect or the third aspect, which represents at least one group selected from the groups represented by formula (B-5).
  • thermosetting film formation according to any one of the first aspect to the fourth aspect, in which the weight average molecular weight of the polyester as the component (A) is 1,000 to 30,000 in terms of polystyrene.
  • the present invention relates to a polyester composition.
  • the (C) component is an amino group-containing carboxylic acid compound obtained by reacting 1 mol of a diamine compound with 1.7 to 2 mol of a dicarboxylic acid anhydride. It relates to the polyester composition for thermosetting film formation as described in any one of these.
  • the present invention further relates to the thermosetting film forming polyester composition according to any one of the first aspect to the seventh aspect, which contains a bismaleimide compound as the component (D).
  • the polyester composition for thermosetting film formation as described in an 8th viewpoint containing 0.5 thru
  • a 10th viewpoint it is related with the cured film obtained using the polyester composition for thermosetting film formation as described in any one of a 1st viewpoint thru
  • an 11th viewpoint it is related with the liquid crystal aligning layer obtained using the polyester composition for thermosetting film formation as described in any one among 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 solvent and a lactic acid ester solvent, it can be suitably used in a production line for a flattened film mainly using these solvents.
  • FIG. 1 is a model diagram showing a cured film formed when a thermosetting film forming polyester composition of the present invention 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.
  • polyester as an alignment material for liquid crystal display elements (see Japanese Patent Application Laid-Open Nos. 5-1558055 and 2002-229039). The film formed was inferior in solvent resistance.
  • the present invention is characterized in that the performance is improved by using a thermosetting polyester, that is, an epoxy compound having (A) component polyester and (B) two or more epoxy groups.
  • a thermosetting polyester that is, an epoxy compound having (A) component polyester and (B) two or more epoxy groups.
  • the polyester composition for thermosetting film formation containing the amino group containing carboxylic acid compound of a component.
  • it is a polyester composition for thermosetting film formation which can also contain a bismaleimide compound as (D) component in addition to (A) component, (B) component, and (C) component.
  • the polyester of component (A) is preferably a polyester containing a structural unit represented by the following formula (1), more preferably a polyester comprising a structural unit represented by formula (1).
  • 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 (1A1), formula (1A2) or formula (1A3).
  • 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 sulfonyl 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 sulfonyl 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 (1) 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 (1B1) or formula (1B2) 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 sulfonyl 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, Preferably, it represents a single bond, a carbonyl group, an ether group, a sulfonyl 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 (1) 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 (1A1) to (1A3) in which A is a structural unit represented by formula (1).
  • a structure other than the groups represented by the formulas (1A1) to (1A3) 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 (1A4) to (1A5). .
  • R 8 , R 9 and R 10 are each independently a single bond, a carbonyl group, an ether group, a sulfonyl group, a saturated hydrocarbon group having 1 to 8 carbon atoms, or the number of carbon atoms substituted with a fluorine atom.
  • R 8 is a single bond, a carbonyl group, an ether group, a sulfonyl 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 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
  • H represents 0 or 1.
  • At least A is selected from the group consisting of groups represented by the above formulas (1A1) to (1A3). 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
  • a and B are synonymous with the definition in Formula (1) mentioned above, and a preferable form is also the same as what was mentioned above.
  • the tetracarboxylic dianhydride represented by the formula (i) and the diol compound represented by the formula (ii) may be used independently or in combination of two or more. Can do.
  • the polyester as the component (A) is not only a tetracarboxylic dianhydride represented by the above formula (i) as an acid component, but also other tetracarboxylic dianhydrides (hereinafter referred to as other acid dianhydrides). Can also be used in combination. At that time, other acid dianhydrides are not particularly limited as long as the effects of the present invention are not impaired.
  • a tetracarboxylic dianhydride represented by the following formula (i2) is preferable.
  • W in the above formula (i2) is at least one structure selected from the group consisting of groups represented by the formula (1A4) and the formula (1A5) defined in the above formula (1), and R 8 , R 9 , R 10 , and h are as defined above.
  • preferable specific examples of the formula (1A4) and the formula (1A5) are also represented by the above-described formula (al) to formula (a7).
  • the tetracarboxylic dianhydride represented by Formula (i) contains at least 60 mol% or more in an acid 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 in combination, but propylene glycol monomethyl ether acetate is more preferable from the viewpoint of safety and applicability to the 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 formula (i2)) with 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.
  • Examples of the epoxy compound having two or more epoxy groups as the component (B) of the present invention include tris (2,3-epoxypropyl) isocyanurate, 1,4-butanediol diglycidyl ether, and 1,2-epoxy.
  • a commercially available compound may be used because it is easily available.
  • Specific examples are listed below, but are not limited to these: epoxy resins having amino groups such as YH-434, YH434L (manufactured by Tohto Kasei Co., Ltd.); Epolide GT-401, Epoxy resin having a cyclohexene oxide structure such as GT-403, GT-301, GT-302, Celoxide 2021, Celoxide 3000 (manufactured by Daicel Chemical Industries, Ltd.); Epicoat 1001, 1002, 1003, 1004, Bisphenol A type epoxy resins such as 1007, 1009, 1010, and 828 (manufactured by 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 having an epoxy group can also be produced by a reaction between a polymer compound having a hydroxyl group and a compound having an epoxy group such as epichlorohydrin or glycidyl tosylate.
  • a polymer compound having a hydroxyl group a compound having an epoxy group such as epichlorohydrin or glycidyl tosylate.
  • a compound having an epoxy group such as epichlorohydrin or glycidyl tosylate.
  • the weight average molecular weight of such a polymer 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 epoxy compound having two or more epoxy groups as the component (B) in the polyester composition for forming a thermosetting film of the present invention is 3 to 50 parts by mass based on 100 parts by mass of the polyester as the component (A). It is preferably 5 to 40 parts by mass, more 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.
  • the component (C) is an amino group-containing carboxylic acid compound obtained by reacting a diamine compound with dicarboxylic dianhydride. Specifically, 1 mol of a diamine compound represented by the following formula (iii) is reacted with 1.7 to 2 mol, preferably 1.8 to 2 mol of a dicarboxylic acid anhydride represented by the formula (iv). The resulting amino group-containing carboxylic acid compound.
  • each of the diamine compound and the dicarboxylic acid anhydride may be used alone or in combination. Therefore, as the amino group-containing carboxylic acid compound of the component (C) of the present invention, not only one type of compound represented by the formula (2) but also a plurality of types can be used.
  • P and Q are preferably divalent organic groups each independently having a ring structure.
  • examples of the ring structure include a benzene ring, an alicyclic ring, and a condensed polycyclic hydrocarbon.
  • the ring structure of P is preferably a benzene ring, an alicyclic group having 4 to 8 carbon atoms, or a condensed polycyclic hydrocarbon having 7 to 16 carbon atoms.
  • specific examples of the diamine compound having such a ring structure include the following: p-phenylenediamine, m-phenylenediamine, 2,4-diaminotoluene, 2,5-diaminotoluene, 2,6- Diaminotoluene, 2,4-dimethyl-1,3-diaminobenzene, 2,5-dimethyl-1,4-diaminobenzene, 2,3,5,6-tetramethyl-1,4-diaminobenzene, 2,4 -Diaminophenol, 2,5-diaminophenol, 4,6-diaminoresorcinol, 2,5-diaminobenzoic acid, 3,5-diaminobenzoic acid,
  • the ring structure of Q is preferably a benzene ring, an alicyclic group having 4 to 8 carbon atoms, or a condensed polycyclic hydrocarbon having 7 to 16 carbon atoms. More preferable Q is a benzene ring, an alicyclic group having 4 to 8 carbon atoms, or a condensed polycyclic hydrocarbon having 7 to 16 carbon atoms.
  • dicarboxylic anhydride having such a ring structure examples include phthalic anhydride, trimellitic anhydride, maleic anhydride, naphthalic anhydride, hydrogenated phthalic anhydride, methyl-5-norbornene- 2,3-dicarboxylic anhydride, itaconic anhydride, tetrahydrophthalic anhydride and the like can be mentioned.
  • the reaction temperature between the diamine compound and the dicarboxylic anhydride can be selected from 5 to 80 ° C., preferably 10 to 50 ° C.
  • the above reaction 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.
  • an acid anhydride such as a hydroxyl group or an amino group.
  • solvents may be used alone or in combination, but from the viewpoint of solubility, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylimidazole Is preferred. Furthermore, even if it is a solvent which does not melt
  • the content of the component (C) in the polyester composition for forming a thermosetting film of the present invention is preferably 3 to 50 parts by weight, more preferably 5 to 40 based on 100 parts by weight of the polyester of the component (A). Part by mass.
  • this ratio is excessively small, the orientation of the cured film obtained from the polyester composition for thermosetting film formation is reduced.
  • the transmittance is decreased or the flatness is decreased.
  • ⁇ (D) component In this invention, you may contain the bismaleimide compound shown by following formula (3) as (D) component.
  • the bismaleimide compound as the component (D) is effective in further improving the flatness.
  • 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.
  • bismaleimide compounds include N, N′-3,3-diphenylmethane bismaleimide, N, N ′-(3,3-diethyl-5,5-dimethyl) -4,4-diphenyl-methane.
  • aromatic bismaleimides those having a molecular weight of 1,000 or less are preferable in order to obtain higher flatness.
  • the ratio of the component (D) bismaleimide compound used is preferably 0.5 to 50 parts by weight, more preferably 1 to 30 parts by weight, based on 100 parts by weight of the polyester (A). Yes, particularly preferably 2 to 20 parts by mass.
  • this ratio is too small, the flatness of the cured film obtained from the polyester composition for thermosetting film formation is reduced, and when it is excessive, the transmittance of the cured film is reduced or the coating film is roughened.
  • the polyester composition for forming a thermosetting film of the present invention is often used in a solution state dissolved in a solvent.
  • the solvent used in that case is a component that dissolves the components (A) to (C), and if necessary, the component (D) and / or other additives described later, and has such solubility. If it is a solvent, the kind and structure thereof are not particularly limited.
  • polymerization of (A) component and the following solvent can be mentioned.
  • examples include methyl cellosolve acetate, ethyl cellosolve acetate, methyl cellosolve, ethyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, propylene glycol propyl ether, ethyl lactate, butyl lactate, cyclohexanol, ethyl acetate, and butyl acetate.
  • These solvents can be used singly or in combination of two or more.
  • the polyester composition for forming a thermosetting film of the present invention is, as necessary, an adhesion aid such as a surfactant, a rheology modifier, a silane coupling agent, a pigment, as long as the effects of the present invention are not impaired. It can contain dyes, storage stabilizers, antifoaming agents, dissolution accelerators such as polyphenols and polycarboxylic acids, and antioxidants.
  • Phenols are particularly preferred as the antioxidant, and specific 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-hydroxybenzyl) isocyanuri
  • the polyester composition for forming a thermosetting film of the present invention comprises (A) component polyester, (B) component epoxy compound having two or more epoxy groups, and (C) component amino group-containing carboxylic acid compound, If desired, the composition may contain one or more of the (D) component bismaleimide compound and 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.
  • a polyester composition for forming a thermosetting film [4]: Based on 100 parts by weight of component (A), 3 to 50 parts by weight of component (B), 3 to 50 parts by weight of component (C), 0.5 to 50 parts by weight of component (D), A polyester composition for forming a thermosetting film containing a solvent.
  • the blending ratio, preparation method, etc. when the polyester composition for forming a thermosetting film of the present invention is in the form of 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.
  • a solvent is further added for the purpose of adjusting the concentration. You may throw it in.
  • 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 material alignment layer, that is, a layer for aligning a compound having liquid crystallinity, by performing a rubbing treatment.
  • a rotational speed of 300 to 1,000 rpm, a feed speed of 3 to 200 mm / second, and a pushing 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.
  • the base material which forms a liquid crystal aligning layer is a film, it is useful as an optically anisotropic film.
  • liquid crystal is injected between the substrates, and the liquid crystal
  • the liquid crystal display element can be oriented.
  • the polyester composition for forming a thermosetting film 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. .
  • Celoxide P-2021 product name (compound name: 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexene carboxylate) ⁇ Bismaleimide compound>
  • BMI1 N, N ′-(3,3-diethyl-5,5-dimethyl) -4,4-diphenyl-methane bismaleimide ⁇ solvent>
  • PGMEA Propylene glycol monomethyl ether acetate
  • PGME Propylene glycol monomethyl ether
  • DMAc N, N-dimethylacetamide
  • NMP N-methyl-2-pyrrolidone
  • 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 planarization property, solvent tolerance, the transmittance
  • DOP flattening ratio
  • 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 100 ° C. for 40 seconds and at 55 ° C. for 30 seconds to form a coating film having a thickness of 1.1 ⁇ m. .
  • This substrate was exposed at 2,000 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.
  • Examples 1 to 9 had a high flattening rate and heat resistance, and were resistant to both PGMEA and NMP. Moreover, all showed favorable orientation and achieved high transmittance (transparency) even after high-temperature firing.
  • Comparative Example 1 no cured film was formed.
  • Comparative Example 2 the solvent resistance, heat resistance and orientation were good, but the flattening rate was very low. And although the result which made the flattening rate, heat resistance, solvent tolerance, and the transmittance
  • 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 of the properties of permeability, solvent resistance, heat resistance, planarization and orientation.
  • 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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JP5626536B2 (ja) * 2009-04-14 2014-11-19 日産化学工業株式会社 熱硬化膜形成用感光性ポリエステル組成物
WO2022270209A1 (ja) * 2021-06-23 2022-12-29 富士フイルム株式会社 樹脂組成物、膜、光学フィルタ、固体撮像素子および画像表示装置

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CN113308091B (zh) * 2020-02-26 2023-04-07 广东生益科技股份有限公司 一种液晶聚酯树脂组合物及其应用

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WO2022270209A1 (ja) * 2021-06-23 2022-12-29 富士フイルム株式会社 樹脂組成物、膜、光学フィルタ、固体撮像素子および画像表示装置

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