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WO2018105675A1 - Procédé de fabrication de couche de pelage - Google Patents

Procédé de fabrication de couche de pelage Download PDF

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Publication number
WO2018105675A1
WO2018105675A1 PCT/JP2017/043911 JP2017043911W WO2018105675A1 WO 2018105675 A1 WO2018105675 A1 WO 2018105675A1 JP 2017043911 W JP2017043911 W JP 2017043911W WO 2018105675 A1 WO2018105675 A1 WO 2018105675A1
Authority
WO
WIPO (PCT)
Prior art keywords
release layer
group
substrate
bis
resin substrate
Prior art date
Application number
PCT/JP2017/043911
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English (en)
Japanese (ja)
Inventor
江原　和也
和也 進藤
Original Assignee
日産化学工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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 CN201780075575.1A priority Critical patent/CN110050013B/zh
Priority to JP2018555053A priority patent/JP7088023B2/ja
Priority to KR1020197019449A priority patent/KR102439479B1/ko
Publication of WO2018105675A1 publication Critical patent/WO2018105675A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B05D3/0254—After-treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Definitions

  • the present invention relates to a method for producing a release layer.
  • Patent Documents 1, 2, and 3 an amorphous silicon thin film layer is formed on a glass substrate, a plastic substrate is formed on the thin film layer, and then laser irradiation is performed from the glass substrate side to crystallize amorphous silicon.
  • a method of peeling a plastic substrate from a glass substrate by hydrogen gas generated along with the crystallization is disclosed.
  • Patent Document 4 a layer to be peeled (described as “transfer target layer” in Patent Document 4) is attached to a plastic film by using the techniques disclosed in Patent Documents 1 to 3, and a liquid crystal display device is formed. A method of completion is disclosed.
  • JP 10-125929 A Japanese Patent Laid-Open No. 10-125931 International Publication No. 2005/050754 JP-A-10-125930
  • the present invention has been made in view of the above circumstances, and an object thereof is to provide a method for producing a release layer that can be peeled without damaging a resin substrate of a flexible electronic device.
  • the inventors of the present invention made a tetracarboxylic dianhydride containing a specific tetracarboxylic dianhydride as a release layer formed on a substrate in the production of a resin substrate.
  • a composition for forming a release layer containing a polyamic acid obtained by reacting a physical component and an aromatic diamine component containing a specific aromatic diamine, and an organic solvent, and forming at a firing temperature of 400 ° C. or higher.
  • the inventors have found that a release layer having excellent adhesiveness with a substrate and appropriate adhesiveness with a resin substrate used as a flexible electronic device and appropriate peelability can be obtained, thereby completing the present invention.
  • a tetracarboxylic dianhydride component including a tetracarboxylic dianhydride represented by the following formula (1); an aromatic diamine having at least one hydroxy group at the ortho position of at least one amino group; and at least one amino
  • a polyamic acid obtained by reacting an aromatic diamine having at least one mercapto group at the ortho position of the group and a diamine component containing at least one aromatic diamine selected from aromatic diamines having a carboxy group, and organic
  • a method for producing a release layer comprising a step of applying a release layer-forming composition containing a solvent to a substrate and firing at a maximum temperature of 400 ° C.
  • X 1 is a tetravalent benzene ring, a tetravalent group formed by condensing two or more benzene rings, and two or more benzene rings are bonded via a single bond.
  • a method for producing one or two release layers, wherein the tetracarboxylic dianhydride represented by the formula (1) includes at least one selected from the group consisting of formulas (C1) to (C12); 4).
  • a method for producing a flexible electronic device comprising a resin substrate, comprising using a release layer formed by using any one of production methods 1 to 3, 5).
  • a flexible electronic device comprising a step of applying a composition for forming a resin substrate on a release layer formed using any one of the manufacturing methods 1 to 3 and then firing the resin substrate at a maximum temperature of 400 ° C. or more to form a resin substrate Manufacturing method, 6).
  • the production method of the release layer release layer of the present invention By adopting the production method of the release layer release layer of the present invention, a film having excellent adhesion to the substrate and appropriate adhesion to the resin substrate and appropriate release can be obtained with good reproducibility. .
  • the manufacturing method of the present invention in the manufacturing process of the flexible electronic device, the resin together with the circuit or the like without damaging the resin substrate formed on the substrate or the circuit or the like provided on the substrate. The substrate can be separated from the substrate. Therefore, the manufacturing method of this invention can contribute to the simplification of the manufacturing process of a flexible electronic device provided with a resin substrate, the yield improvement, etc.
  • the method for producing a release layer according to the present invention includes a tetracarboxylic dianhydride component including a tetracarboxylic dianhydride represented by the following formula (1), and at least one hydroxy at the ortho position of at least one amino group.
  • a diamine component comprising at least one aromatic diamine selected from an aromatic diamine having a group, an aromatic diamine having at least one mercapto group at the ortho position of at least one amino group, and an aromatic diamine having a carboxy group;
  • a composition for forming a release layer containing a polyamic acid obtained by reacting an organic solvent and an organic solvent is applied to a substrate and baked at a maximum temperature of 400 ° C. or higher.
  • the release layer in the present invention is a layer provided directly on a glass substrate for a predetermined purpose, and a typical example thereof is a resin of a flexible electronic device comprising a substrate and a resin such as polyimide in a manufacturing process of the flexible electronic device. Provided between the substrate and the resin substrate in order to fix the resin substrate in a predetermined process, and after the electronic circuit or the like is formed on the resin substrate, the resin substrate can be easily separated from the substrate. The thing provided in order to do is mentioned.
  • X 1 is a tetravalent benzene ring, a tetravalent group formed by condensing two or more benzene rings, and two or more benzene rings bonded via a single bond.
  • Specific examples of the tetravalent group formed by condensing two or more benzene rings include a tetravalent naphthalene ring, a tetravalent anthracene ring, a tetravalent phenanthrene ring, a tetravalent tetracene ring, and the like.
  • Specific examples of the tetravalent group formed by bonding two or more benzene rings through a single bond include tetravalent biphenylene, tetravalent terphenylene and the like.
  • aromatic tetracarboxylic dianhydride represented by the above formula (1) examples include pyromellitic dianhydride, benzene-1,2,3,4-tetracarboxylic dianhydride, naphthalene- 1,2,3,4-tetracarboxylic dianhydride, naphthalene-1,2,5,6-tetracarboxylic dianhydride, naphthalene-1,2,6,7-tetracarboxylic dianhydride, naphthalene -1,2,7,8-tetracarboxylic dianhydride, naphthalene-2,3,5,6-tetracarboxylic dianhydride, naphthalene-2,3,6,7-tetracarboxylic dianhydride, Naphthalene-1,4,5,8-tetracarboxylic dianhydride, biphenyl-2,2 ′, 3,3′-tetracarboxylic dianhydride, biphenyl,2
  • the aromatic tetracarboxylic dianhydride represented by the formula (1) is preferably at least one selected from the group consisting of the formulas (C1) to (C12) from the viewpoint of ensuring heat resistance. At least one selected from the group consisting of formula (C1) and formula (C9) is more preferable.
  • Such a tetracarboxylic dianhydride is an aliphatic tetracarboxylic dianhydride or an aromatic tetracarboxylic dianhydride, and is preferably an aromatic tetracarboxylic dianhydride other than the above formula (1).
  • the aromatic tetracarboxylic acid represented by the formula (1) is used.
  • the amount of dianhydride used is preferably 70 mol% or more, more preferably 80 mol% or more, still more preferably 90 mol% or more, and still more preferably 95 mol% or more in the total tetracarboxylic dianhydride. . By adopting such a usage amount, a film having good peelability can be obtained with good reproducibility.
  • At least one aromatic diamine selected from the aromatic diamine having a hydroxy group at the ortho position of the amino group, the aromatic diamine having a mercapto group at the ortho position of the amino group, and the aromatic diamine having a carboxy group is an aromatic diamine having at least one group selected from the group consisting of a phenolic hydroxyl group, a carboxy group, and a thiophenol group.
  • diamine having a phenolic hydroxyl group, a carboxy group, and a thiophenol group, and aromatic diamines having no such group are shown below, but the present invention is not limited thereto, and these are one kind. It can use individually or in combination of 2 or more types.
  • Aromatic diamines having phenolic hydroxyl groups include 2,4-diaminophenol, 2,5-diaminophenol, 4,6-diaminoresorcinol, 2,5-diaminohydroquinone, bis (3-amino-4-hydroxyphenyl) Ether, bis (4-amino-3-hydroxyphenyl) ether, bis (4-amino-3,5-dihydroxyphenyl) ether, bis (3-amino-4-hydroxyphenyl) methane, bis (4-amino-3) -Hydroxyphenyl) methane, bis (4-amino-3,5-dihydroxyphenyl) methane, bis (3-amino-4-hydroxyphenyl) sulfone, bis (4-amino-3-hydroxyphenyl) sulfone, bis (4 -Amino-3,5-dihydroxyphenyl) sulfone, 2,2-bis ( -Amino-4-hydroxyphenyl) hex
  • aromatic diamine having a carboxy group examples include 2,4-diaminobenzoic acid, 2,5-diaminobenzoic acid, 3,5-diaminobenzoic acid, 4,6-diamino-1,3-benzenedicarboxylic acid, 5-diamino-1,4-benzenedicarboxylic acid, bis (4-amino-3-carboxyphenyl) ether, bis (4-amino-3,5-dicarboxyphenyl) ether, bis (4-amino-3-carboxy) Phenyl) sulfone, bis (4-amino-3,5-dicarboxyphenyl) sulfone, 4,4′-diamino-3,3′-dicarboxybiphenyl, 4,4′-diamino-3,3′-dicarboxy -5,5'-dimethylbiphenyl, 4,4'-diamino-3,3'-dicarboxy-5,5-
  • aromatic diamines having a thiophenol group examples include 1,3-diamino-4-mercaptobenzene, 1,3-diamino-5-mercaptobenzene, 1,4-diamino-2-mercaptobenzene, bis (4-amino- 3-mercaptophenyl) ether, 2,2-bis (3-amino-4-mercaptophenyl) hexafluoropropane, and the like.
  • aromatic diamines having two or more alkali-soluble groups include bis (4-amino-4-carboxy-5-hydroxyphenyl) ether and bis (4-amino-3-carboxy-5-hydroxyphenyl) methane.
  • At least one aromatic diamine selected from an aromatic diamine having a hydroxy group at the ortho position of the amino group and an aromatic diamine having a carboxy group at the ortho position is preferable.
  • ) To (B4) are more preferably one or more aromatic diamines.
  • an aromatic diamine having a carboxy group is preferred.
  • diamines can be used in addition to the above-described aromatic diamine containing an alkali-soluble group.
  • a diamine may be either an aliphatic diamine or an aromatic diamine, but an aromatic diamine containing neither an ester bond nor an ether bond is preferable from the viewpoint of ensuring the strength and heat resistance of the resulting thin film.
  • Examples of the other diamines include p-phenylenediamine, m-phenylenediamine, o-phenylenediamine, 2,4-diaminotoluene, 2,5-diaminotoluene, 2,6-diaminotoluene, 4,6-dimethyl-m.
  • '-Methylene-bis (2,6-diisopropylaniline), bis [4- (3-aminophenoxy) phenyl] sulfone, 2,2-bis [4- (3-aminophenoxy) phenyl] propane, 2,2- Bis [4- (3-aminophenoxy) phenyl] hexafluoropropane and the like are preferable.
  • the amount of the aromatic diamine having an alkali-soluble group is preferably 70 mol% or more, more preferably 80%, based on the total diamine. It is more than mol%, still more preferably more than 90 mol%, still more preferably more than 95 mol%.
  • the polyamic acid contained in the composition for forming a release layer according to the present invention can be obtained by reacting the tetracarboxylic dianhydride component and the diamine component described above.
  • the organic solvent used in such a reaction is not particularly limited as long as it does not adversely affect the reaction.
  • Specific examples thereof include m-cresol, 2-pyrrolidone, N-methyl-2-pyrrolidone, N-ethyl-2- Pyrrolidone, N-vinyl-2-pyrrolidone, N, N-dimethylacetamide, N, N-dimethylformamide, 3-methoxy-N, N-dimethylpropylamide, 3-ethoxy-N, N-dimethylpropylamide, 3- Propoxy-N, N-dimethylpropylamide, 3-isopropoxy-N, N-dimethylpropylamide, 3-butoxy-N, N-dimethylpropylamide, 3-sec-butoxy-N, N-dimethylpropylamide, 3 -Tert-butoxy-N, N-dimethylpropylamide, ⁇ -butyrolactone and the like.
  • amides represented by formula (S1), amides represented by formula (S2) and formula ( At least one selected from amides represented by S3) is preferred.
  • R 1 and R 2 each independently represent an alkyl group having 1 to 10 carbon atoms.
  • R 3 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
  • h represents a natural number, preferably 1 to 3, more preferably 1 or 2.
  • alkyl group having 1 to 10 carbon atoms examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, n- Examples include hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group and the like. Of these, alkyl groups having 1 to 3 carbon atoms are preferable, and alkyl groups having 1 or 2 carbon atoms are more preferable.
  • the reaction temperature may be appropriately set in the range from the melting point to the boiling point of the solvent used, and is usually about 0 to 100 ° C., but it prevents imidization in the solution of the resulting polyamic acid and contains a high content of polyamic acid units. In order to maintain the amount, it is preferably about 0 to 70 ° C, more preferably about 0 to 60 ° C, and still more preferably about 0 to 50 ° C.
  • the reaction time depends on the reaction temperature and the reactivity of the raw material, and cannot be specified unconditionally, but is usually about 1 to 100 hours.
  • a target reaction solution containing polyamic acid can be obtained.
  • the weight average molecular weight of the polyamic acid thus obtained is usually about 5,000 to 500,000. From the viewpoint of improving the function of the resulting film as a release layer, preferably 6,000 to It is about 200,000, more preferably about 7,000 to 150,000.
  • a weight average molecular weight is a polystyrene conversion value by a gel permeation chromatography (GPC) measurement.
  • the solution obtained by diluting or concentrating the reaction solution as it is ordinarily can be used as the release layer forming composition of the present invention.
  • the solvent in this case include organic solvents used in the above-described reaction.
  • the solvent used for dilution is not particularly limited, and specific examples thereof include those similar to the specific examples of the reaction solvent for the reaction.
  • the solvent used for dilution may be used singly or in combination of two or more.
  • N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, N-ethyl-2 are used because they dissolve polyamic acid well.
  • -Pyrrolidone and ⁇ -butyrolactone are preferred, and N-methyl-2-pyrrolidone is more preferred.
  • ethyl cellosolve, butyl cellosolve, ethyl carbitol, butyl carbitol, ethyl carbitol acetate ethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, 1-butoxy-2-propanol, 1-phenoxy -2-propanol, propylene glycol monoacetate, propylene glycol diacetate, propylene glycol-1-monomethyl ether-2-acetate, propylene glycol-1-monoethyl ether-2-acetate, dipropylene glycol, 2- (2-ethoxy A solvent having a low surface tension such as propoxy) propanol, methyl lactate, ethyl lactate, n-propyl lactate, n
  • the concentration of the polyamic acid in the composition for forming a release layer of the present invention is appropriately set in consideration of the thickness of the release layer to be produced, the viscosity of the composition, etc., but is usually about 1 to 30% by mass, preferably It is about 1 to 20% by mass. By setting such a concentration, a release layer having a thickness of about 0.05 to 5 ⁇ m can be obtained with good reproducibility.
  • the concentration of polyamic acid is adjusted to adjust the amount of diamine and tetracarboxylic dianhydride used as raw materials for polyamic acid, and after filtering the reaction solution, the filtrate is diluted or concentrated, and the isolated polyamic acid is used as a solvent. The amount can be adjusted by, for example, adjusting the amount when dissolved in the aqueous solution.
  • the viscosity of the release layer forming composition is appropriately set in consideration of the thickness of the release layer to be produced, and the like. When it is intended, it is usually about 10 to 10,000 mPa ⁇ s, preferably about 20 to 5,000 mPa ⁇ s at 25 ° C.
  • the viscosity can be measured using a commercially available liquid viscosity measurement viscometer, for example, with reference to the procedure described in JIS K7117-2 at a temperature of the composition of 25 ° C. .
  • a conical plate type (cone plate type) rotational viscometer is used as the viscometer, and preferably the composition temperature is 25 ° C. using 1 ° 34 ′ ⁇ R24 as a standard cone rotor. It can be measured under the condition of ° C.
  • An example of such a rotational viscometer is TVE-25L manufactured by Toki Sangyo Co., Ltd.
  • composition for forming a release layer according to the present invention may contain a component such as a crosslinking agent in addition to the polyamic acid and the organic solvent, for example, in order to improve the film strength.
  • a component such as a crosslinking agent in addition to the polyamic acid and the organic solvent, for example, in order to improve the film strength.
  • the adhesiveness to the substrate is excellent by thermally imidizing polyamic acid by a baking method including a step of baking at a maximum temperature of 400 ° C. or higher.
  • a baking method including a step of baking at a maximum temperature of 400 ° C. or higher.
  • the maximum temperature at the time of firing is not particularly limited as long as it is in the range of 400 ° C. or higher and not higher than the heat resistant temperature of polyimide.
  • 450 ° C. or higher is preferable, and 500 ° C. or higher is more preferable.
  • the upper limit is usually about 550 ° C., preferably about 510 ° C.
  • the temperature at the time of the said baking may include the process baked at the temperature below it.
  • the heating mode in the present invention there is a method of heating at 50 to 150 ° C., then raising the heating temperature stepwise as it is, and finally heating at 400 ° C. or higher.
  • a method of heating at 50 to 100 ° C., heating at a temperature exceeding 100 ° C. to less than 400 ° C., and heating at 400 ° C. or higher can be mentioned.
  • heating mode after heating at 50 to 150 ° C., heating at 150 to 350 ° C., then heating at 350 to 400 ° C., and finally, 400 to 510 ° C.
  • a method of heating at 0 ° C. can be mentioned.
  • the heating mode in consideration of the firing time, after heating at 50 to 150 ° C. for 1 minute to 2 hours, the heating temperature is increased stepwise and finally at 400 ° C. or higher for 30 minutes.
  • a method of heating for up to 4 hours can be mentioned.
  • heating is performed at 50 to 100 ° C. for 1 minute to 2 hours, heating is performed above 100 ° C. to less than 400 ° C. for 5 minutes to 2 hours, and heating is performed at 400 ° C. or higher for 30 minutes to 4 hours.
  • the technique to do is mentioned.
  • after heating at 50 to 150 ° C. for 1 minute to 2 hours after exceeding 150 ° C. to 350 ° C. for 5 minutes to 2 hours, then, exceeding 350 ° C. to 400 ° C. for 30 minutes.
  • the release layer when the release layer is formed on the substrate, the release layer may be formed on a part of the surface of the substrate or on the entire surface.
  • a release layer As an aspect of forming a release layer on a part of the surface of the substrate, an embodiment in which the release layer is formed only within a predetermined range of the substrate surface, a release layer is formed in a pattern such as a dot pattern or a line and space pattern on the entire surface of the substrate.
  • substrate means what is used for manufacture of a flexible electronic device etc. by which the composition for peeling layer formation concerning this invention is applied to the surface.
  • the substrate examples include glass, metal (silicon wafer, etc.), slate, etc.
  • a release layer obtained using the release layer forming composition according to the present invention is sufficient. Since it has adhesiveness, glass is preferable.
  • substrate surface may be comprised with the single material and may be comprised with two or more materials. As an aspect in which the substrate surface is constituted by two or more materials, a certain range of the substrate surface is constituted by a certain material, and the other surface is constituted by another material. A dot pattern is formed on the entire substrate surface. There is a mode in which a material in a pattern such as a line and space pattern is present in other materials.
  • the coating method is not particularly limited.
  • a cast coating method for example, a cast coating method, a spin coating method, a blade coating method, a dip coating method, a roll coating method, a bar coating method, a die coating method, an ink jet method, a printing method (a relief plate, an intaglio plate, a planographic plate). , Screen printing, etc.).
  • Examples of equipment used for heating include a hot plate and an oven.
  • the heating atmosphere may be under air or under an inert gas, and may be under normal pressure or under reduced pressure.
  • the thickness of the release layer is usually about 0.01 to 50 ⁇ m, preferably from about 0.05 to 20 ⁇ m, more preferably about 0.05 to 5 ⁇ m from the viewpoint of productivity. To achieve the desired thickness.
  • the release layer described above has excellent adhesion to a substrate, particularly a glass substrate, moderate adhesion to a resin substrate, and moderate release. Therefore, the release layer produced in the present invention, in the manufacturing process of the flexible electronic device, without damaging the resin substrate of the device, the resin substrate, together with the circuit and the like formed on the resin substrate, It can be suitably used for peeling from the substrate.
  • a release layer is formed on a glass substrate by the method described above.
  • a resin substrate forming solution for forming a resin substrate is applied, and this coating film is baked, so that the resin substrate fixed to the glass substrate via the release layer of the present invention is obtained.
  • the firing temperature of the coating film is appropriately set according to the type of resin, etc., in the present invention, the maximum temperature during firing is preferably 400 ° C. or higher, and 450 ° C. or higher.
  • the heating mode at the time of preparing the resin substrate there is a method of heating at 50 to 150 ° C., then increasing the heating temperature step by step, and finally heating at 400 ° C. or higher.
  • a method of heating at 50 to 100 ° C., heating at a temperature higher than 100 ° C. to less than 400 ° C., and heating at 400 ° C. or higher can be mentioned.
  • the heating mode after heating at 50 to 100 ° C., heating at over 100 ° C. to 200 ° C., and then heating at over 200 ° C. to less than 300 ° C. And heating at 400 to 450 ° C., and finally heating at 450 to 510 ° C.
  • the heating mode in consideration of the firing time, after heating at 50 to 150 ° C. for 1 minute to 2 hours, the heating temperature is increased stepwise and finally at 400 ° C. or higher for 30 minutes.
  • a method of heating for up to 4 hours can be mentioned.
  • heating is performed at 50 to 100 ° C. for 1 minute to 2 hours, heating is performed above 100 ° C. to less than 400 ° C. for 5 minutes to 2 hours, and heating is performed at 400 ° C. or higher for 30 minutes to 4 hours.
  • the technique to do is mentioned.
  • the resin substrate covers the entire release layer, and the substrate is formed with an area larger than the area of the release layer.
  • the resin substrate include a resin substrate made of polyimide, which is a typical resin substrate for flexible electronic devices, and examples of the resin solution for forming the resin substrate include a polyimide solution and a polyamic acid solution.
  • the method for forming the resin substrate may follow a conventional method.
  • a desired circuit is formed on the resin substrate fixed to the base via the release layer according to the present invention, and then, for example, the resin substrate is cut along the release layer. Is peeled from the release layer to separate the resin substrate and the substrate. At this time, a part of the substrate may be cut together with the release layer.
  • the LLO method is characterized in that light having a specific wavelength, for example, light having a wavelength of 308 nm, is irradiated from the surface opposite to the surface on which a circuit or the like is formed from the glass substrate side.
  • the irradiated light passes through the glass substrate, and only the polymer (polyimide) in the vicinity of the glass substrate absorbs this light and evaporates (sublimates).
  • the polymer polyimide
  • the release layer of the present invention has a feature of sufficiently absorbing light having a specific wavelength (for example, 308 nm) that enables application of the above LLO method, and therefore can be used as a sacrificial layer of the LLO method. Therefore, when a desired circuit is formed on a resin substrate fixed to a glass substrate through a release layer formed by using the composition according to the present invention, and then an LLO method is performed to irradiate a light beam of 308 nm. Only the release layer absorbs this light and evaporates (sublimates). Thereby, the release layer is sacrificed (acts as a sacrifice layer), and the resin substrate can be selectively peeled from the glass substrate.
  • a specific wavelength for example, 308 nm
  • NMP N-methylpyrrolidone
  • BCS butyl cellosolve
  • p-PDA p-phenylenediamine
  • TPDA 4,4 "-diamino-p-terphenyl
  • DBA 3,5-diaminobenzoic acid
  • HAB 3, 3 '-Dihydroxybenzidine
  • 6FAP 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane
  • TFMB 2,2'-bis (trifluoromethyl) benzidine
  • BPDA 3,3-4,4-biphenyl Tetracarboxylic dianhydride
  • PMDA pyromellitic dianhydride
  • PA phthalic anhydride
  • CBDA 1,2,3,4-cyclobutanetetracarboxylic acid-1,2: 3,4-dianhydride
  • Mw polymer weight average molecular weight
  • Mw polymer weight average molecular weight
  • Mw molecular weight distribution
  • a GPC apparatus Shidex (registered trademark) columns KF803L and KF805L
  • dimethylformamide was measured under the conditions of a flow rate of 1 ml / min and a column temperature of 50 ° C.
  • Mw was made into the polystyrene conversion value.
  • composition for forming release layer [Example 1-1] BCS and NMP were added to the reaction solution obtained in Synthesis Example L1, and diluted such that the polymer concentration was 5 wt% and BCS was 20 mass%, to obtain a release layer forming composition.
  • Examples 1-2 to 1-5 A release layer-forming composition was obtained in the same manner as in Example 1-1 except that the reaction solutions obtained in Synthesis Examples L2 to L5 were used instead of the reaction solution obtained in Synthesis Example L1. It was.
  • Example 2-1 Production of release layer and resin substrate [Example 2-1] Using a spin coater (conditions: about 3,000 rpm for about 30 seconds), the release layer forming composition obtained in Example 1-1 was applied to a 100 mm ⁇ 100 mm glass substrate (hereinafter the same) as a glass substrate. It was applied on top.
  • the obtained coating film was heated at 80 ° C. for 10 minutes using a hot plate, and then heated at 300 ° C. for 30 minutes using an oven, and the heating temperature was raised to 400 ° C. (10 ° C./min.
  • the film was further heated at 400 ° C. for 30 minutes to form a release layer having a thickness of about 0.1 ⁇ m on the glass substrate to obtain a glass substrate with a release layer. During the temperature increase, the film-coated substrate was not removed from the oven but heated in the oven.
  • the resin substrate forming composition S1 was applied on the release layer (resin thin film) on the glass substrate obtained above. Then, the obtained coating film was heated at 80 ° C. for 30 minutes using a hot plate, and then the atmosphere was changed to a nitrogen atmosphere using an oven, followed by heating at 140 ° C. for 30 minutes, and the heating temperature was raised to 210 ° C. (2 ° C / min, the same applies hereinafter), heated at 210 ° C for 30 minutes, heated to 300 ° C, heated to 300 ° C for 30 minutes, heated to 400 ° C, and heated to 400 ° C for 60 minutes.
  • a polyimide resin substrate having a thickness of about 20 ⁇ m was formed on the release layer to obtain a glass substrate with a resin substrate / release layer.
  • the film-coated substrate was not removed from the oven but heated in the oven.
  • Example 2-2 A release layer and a polyimide resin substrate were formed in the same manner as in Example 2-1, except that the resin substrate formation composition S2 was used instead of the resin substrate formation composition S1. A glass substrate with a resin substrate and a release layer was obtained.
  • Example 2-3 The same method as in Example 2-2, except that the release layer forming composition L2 obtained in Example 1-2 was used instead of the release layer forming composition obtained in Example 1-1. Thus, a release layer and a polyimide resin substrate were formed, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were obtained.
  • Example 2-4 The same method as in Example 2-1, except that the release layer forming composition L3 obtained in Example 1-3 was used instead of the release layer forming composition obtained in Example 1-1. Thus, a release layer and a polyimide resin substrate were formed, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were obtained.
  • Example 2-5 The same method as in Example 2-2, except that the release layer forming composition L3 obtained in Example 1-3 was used instead of the release layer forming composition obtained in Example 1-1. Thus, a release layer and a polyimide resin substrate were formed, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were obtained.
  • Example 2-6 The same method as in Example 2-1, except that the release layer forming composition L4 obtained in Example 1-4 was used instead of the release layer forming composition obtained in Example 1-1. Thus, a release layer and a polyimide resin substrate were formed, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were obtained.
  • Example 2-7 The same method as in Example 2-2, except that the release layer forming composition L4 obtained in Example 1-4 was used instead of the release layer forming composition obtained in Example 1-1. Thus, a release layer and a polyimide resin substrate were formed, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were obtained.
  • Example 2-8 Using a spin coater (conditions: about 3,000 rpm for about 30 seconds), the release layer forming composition L5 obtained in Example 1-5 was used as a glass substrate of 100 mm ⁇ 100 mm glass substrate (hereinafter the same) It was applied on top.
  • the obtained coating film was heated at 100 ° C. for 2 minutes using a hot plate, and then heated at 300 ° C. for 30 minutes using an oven, and the heating temperature was raised to 400 ° C. (10 ° C./min. And then heated to 400 ° C. for 30 minutes, further heated to 500 ° C. (10 ° C./min), and heated at 500 ° C. for 10 minutes to form a release layer having a thickness of about 0.1 ⁇ m on the glass substrate.
  • a glass substrate with a release layer was obtained. During the temperature increase, the film-coated substrate was not removed from the oven but heated in the oven.
  • the resin substrate forming composition S2 was applied on the release layer (resin thin film) on the glass substrate obtained above. Then, the obtained coating film was heated at 80 ° C. for 30 minutes using a hot plate, and then the atmosphere was changed to a nitrogen atmosphere using an oven, followed by heating at 140 ° C. for 30 minutes, and the heating temperature was raised to 210 ° C. (2 ° C / min, the same applies hereinafter), heated at 210 ° C for 30 minutes, heated to 300 ° C, heated at 300 ° C for 30 minutes, heated to 400 ° C, heated to 400 ° C For 30 minutes, raising the heating temperature to 500 ° C. and heating at 500 ° C.
  • Example 2-2 was used except that the composition for forming a release layer obtained in Comparative Examples 1-1 to 1-2 was used instead of the composition for forming a release layer obtained in Example 1-1. A release layer was formed in the same manner as described above.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Non-Metallic Protective Coatings For Printed Circuits (AREA)
  • Electroluminescent Light Sources (AREA)
  • Apparatuses And Processes For Manufacturing Resistors (AREA)

Abstract

L'invention fournit un procédé de fabrication de couche de pelage selon lequel une composition pour formation de couche de pelage contenant un acide polyamique et un solvant organique, est appliquée sur un corps de base, et cuite à une température maximale de 400°C ou plus. Ledit acide polyamique est obtenu par réaction : d'un composant dianhydride d'acide tétracarboxylique contenant un dianhydride d'acide tétracarboxylique représenté par la formule (1); et d'un composant diamine qui contient un diamine aromatique possédant au moins un groupe hydroxy en position ortho d'au moins un groupe amino, un diamine aromatique possédant au moins un groupe mercapto en position ortho d'au moins un groupe amino, et au moins une sorte de diamine aromatique choisi parmi des diamines aromatiques possédant un groupe carboxy. (Dans la formule (1), Ｘ1 représente un cycle benzène tétravalent, un groupe tétravalent constitué par condensation d'au moins deux cycles benzène entre eux, et un groupe tétravalent choisi parmi des groupes tétravalents constitués par liaison d'au moins deux cycles benzène entre eux par l'intermédiaire d'une liaison simple.)
PCT/JP2017/043911 2016-12-08 2017-12-07 Procédé de fabrication de couche de pelage WO2018105675A1 (fr)

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JP2018555053A JP7088023B2 (ja) 2016-12-08 2017-12-07 剥離層の製造方法
KR1020197019449A KR102439479B1 (ko) 2016-12-08 2017-12-07 박리층의 제조 방법

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JP7088023B2 (ja) 2022-06-21
KR102439479B1 (ko) 2022-09-05
CN110050013A (zh) 2019-07-23
TW201831621A (zh) 2018-09-01

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