WO2016158988A1 - 剥離層形成用組成物及び剥離層 - Google Patents
剥離層形成用組成物及び剥離層 Download PDFInfo
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- WO2016158988A1 WO2016158988A1 PCT/JP2016/060204 JP2016060204W WO2016158988A1 WO 2016158988 A1 WO2016158988 A1 WO 2016158988A1 JP 2016060204 W JP2016060204 W JP 2016060204W WO 2016158988 A1 WO2016158988 A1 WO 2016158988A1
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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
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Definitions
- the present invention relates to a release layer forming composition and 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 a laser is irradiated from the glass surface side to accompany crystallization of amorphous silicon.
- a method of peeling a plastic substrate from a glass substrate with generated hydrogen gas is disclosed.
- Patent Document 4 discloses a method for completing a liquid crystal display device by attaching a layer to be peeled (described as “transfer target layer” in Patent Document 4) to a plastic film using the techniques disclosed in Patent Documents 1 to 3. Is disclosed.
- Patent Documents 1 to 4 particularly the method disclosed in Patent Document 4, it is essential to use a substrate with high translucency, and hydrogen contained in amorphous silicon is allowed to pass through the substrate.
- hydrogen contained in amorphous silicon is allowed to pass through the substrate.
- it is necessary to irradiate a laser beam having a relatively large energy and there is a problem that the layer to be peeled is damaged.
- JP 10-125929 A Japanese Patent Laid-Open No. 10-125931 International Publication No. 2005/050754 JP-A-10-125930
- This invention is made
- the composition for peeling layer formation for forming the peeling layer which can peel without damaging the resin substrate of a flexible electronic device, and the said peeling layer are provided.
- the purpose is to provide.
- the present inventors have used a composition containing polyamic acid, an organic silane compound, and an organic solvent for excellent adhesion to a substrate and a flexible electronic device.
- the present invention has been completed by finding that a release layer having appropriate adhesion to a resin substrate to be obtained and appropriate release properties can be formed.
- a composition for forming a release layer comprising a polyamic acid, an organosilane compound, and an organic solvent; 2. 1. The composition for forming a release layer according to 1 above, wherein the organosilane compound is an alkoxysilane compound containing a reactive functional group, 3. The release layer according to 1 or 2, wherein the polyamic acid is a polyamic acid obtained by reacting a diamine component containing an aromatic diamine and an acid dianhydride containing an aromatic tetracarboxylic dianhydride. Forming composition, 4). 3. The composition for forming a release layer according to 3, wherein the aromatic diamine is an aromatic diamine containing 1 to 5 benzene nuclei, 5.
- composition for forming a release layer wherein the aromatic tetracarboxylic dianhydride is an aromatic tetracarboxylic dianhydride containing 1 to 5 benzene nuclei, 6).
- each L independently represents an alkanediyl group having 1 to 20 carbon atoms, an alkenediyl group having 2 to 20 carbon atoms, or an alkynediyl group having 2 to 20 carbon atoms
- each R ′ represents Each independently represents an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an alkynyl group having 2 to 20 carbon atoms.
- a method for producing a flexible electronic device comprising a resin substrate, characterized in that a release layer of 7 is used, 9. 8. The manufacturing method according to 8, wherein the resin substrate is a substrate made of polyimide.
- the release layer forming composition of the present invention By using the release layer forming composition of the present invention, it is possible to obtain a release layer having excellent adhesion to the substrate, moderate adhesion to the resin substrate, and moderate release with good reproducibility. Therefore, by using the composition for forming a release layer of the present invention, in the manufacturing process of the flexible electronic device, without damaging the resin substrate formed on the substrate, the circuit provided on the substrate, and the like. The resin substrate can be separated from the substrate together with the circuit and the like. Therefore, the composition for forming a release layer of the present invention can contribute to simplification of the production process of a flexible electronic device including a resin substrate, improvement of its yield, and the like.
- the composition for forming a release layer of the present invention includes a polyamic acid, an organic silane compound, and an organic solvent.
- the release layer in the present invention is a layer provided immediately above a glass substrate for a predetermined purpose.
- a flexible electronic made of a substrate and a resin such as polyimide is used.
- the resin substrate can be easily peeled from the substrate.
- a release layer may be used.
- the polyamic acid used in the present invention is not particularly limited and can be obtained by reacting a diamine component and a tetracarboxylic dianhydride component, but has a function as a release layer of the obtained film. From the viewpoint of improving, a polyamic acid obtained by reacting a diamine component containing an aromatic diamine and an acid dianhydride component containing an aromatic tetracarboxylic dianhydride is preferable.
- the aromatic diamine is not particularly limited as long as it has two amino groups in the molecule and has an aromatic ring, but an aromatic diamine containing 1 to 5 benzene nuclei is preferable. Specific examples thereof include 1,4-diaminobenzene (p-phenylenediamine), 1,3-diaminobenzene (m-phenylenediamine), 1,2-diaminobenzene (o-phenylenediamine), 2,4-diamino.
- Group diamines are preferred. Specifically, p-phenylenediamine, m-phenylenediamine, 2- (3-aminophenyl) -5-aminobenzimidazole, 2- (4-aminophenyl) -5-aminobenzooxol, 4,4 ′ '-Diamino-p-terphenyl and the like are preferred.
- aromatic tetracarboxylic dianhydride is not particularly limited as long as it has two dicarboxylic anhydride sites in the molecule and has an aromatic ring, but an aromatic tetracarboxylic dianhydride contains 1 to 5 benzene nuclei.
- aromatic tetracarboxylic dianhydrides are preferred.
- 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-2,3,3', 4'-tetracarboxylic dianhydride,
- aromatic carboxylic dianhydrides having one or two benzene nuclei are preferred from the viewpoint of improving the function of the resulting film as a release layer.
- an aromatic tetracarboxylic dianhydride represented by any one of formulas (C1) to (C12) is preferred, and any one of formulas (C1) to (C7) and (C9) to (C11)
- the aromatic tetracarboxylic dianhydride shown is more preferred.
- the diamine component of the present invention may contain a diamine other than an aromatic diamine, and a preferred example thereof is represented by the formula (S). Diamines.
- each L independently represents an alkanediyl group having 1 to 20 carbon atoms, an alkenediyl group having 2 to 20 carbon atoms, or an alkynediyl group having 2 to 20 carbon atoms
- each R ′ represents Independent of each other, it represents an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an alkynyl group having 2 to 20 carbon atoms.
- the carbon number of such alkanediyl group, alkenediyl group and alkynediyl group is preferably 10 or less, more preferably 5 or less.
- alkyl group having 1 to 20 carbon atoms may be linear, branched, or cyclic.
- Straight chain having 1 to 20 carbon atoms such as a group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group and n-decyl group.
- Chain or branched alkyl group cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, bicyclobutyl group, bicyclopentyl group, bicyclohexyl group, bicycloheptyl group
- cyclic alkyl groups having 3 to 20 carbon atoms such as a bicyclooctyl group, a bicyclononyl group, and a bicyclodecyl group.
- alkenyl group having 2 to 20 carbon atoms include ethenyl group, n-1-propenyl group, n-2-propenyl group, 1-methylethenyl group, n-1-butenyl group, n-2-butenyl group, n-3-butenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 1-ethylethenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, n- Examples thereof include a 1-pentenyl group, an n-1-decenyl group, and an n-1-eicosenyl group.
- alkynyl group having 2 to 20 carbon atoms examples include ethynyl group, n-1-propynyl group, n-2-propynyl group, n-1-butynyl group, n-2-butynyl group, and n-3-butynyl.
- R ′ is preferably an alkyl group having 1 to 20 carbon atoms, more preferably a methyl group or an ethyl group, in consideration of the balance between the solubility of the resulting polyamic acid in an organic solvent and the heat resistance of the obtained film. .
- 1,3-bis (3-aminopropyl) tetramethyldisiloxane is optimal as the diamine represented by the formula (S).
- the diamine represented by Formula (S) can be obtained as a commercial item, and can also be synthesize
- the amount of the aromatic diamine in the diamine component is preferably 70 mol% or more, more preferably 80 mol% or more, still more preferably 90 mol% or more, and further preferably 95 mol% or more.
- the amount of the aromatic diamine in the total amount of the aromatic diamine and the diamine represented by the formula (S) is preferably 80 mol. % Or more, more preferably 90 mol% or more, still more preferably 95 mol% or more, still more preferably 97 mol% or more.
- the amount of aromatic tetracarboxylic dianhydride used is preferably 70 mol% or more, more preferably 80 mol% or more, even more preferably 90 mol% or more, in the total tetracarboxylic dianhydride. More preferably, it is 95 mol% or more, and most preferably 100 mol%.
- the polyamic acid contained in the composition for forming a release layer of the present invention can be obtained by reacting the diamine component and the tetracarboxylic dianhydride 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-dimethylpropyl Amides, 3-propoxy-N, N-dimethylpropylamide, 3-isopropoxy-N, N-dimethylpropylamide, 3-butoxy-N, N-dimethylpropylamide, 3-sec-butoxy-N, N-dimethyl Propylamide, 3-tert-butoxy-N, N-dimethylpropylamide, ⁇ -butyrolactone, etc. That.
- the charging ratio of the diamine component and the tetracarboxylic dianhydride component is appropriately determined in consideration of the target molecular weight and molecular weight distribution, the type of diamine and the type of tetracarboxylic dianhydride, etc.
- the ratio of the tetracarboxylic dianhydride component to the diamine component 1 is about 0.7 to 1.3, preferably about 0.8 to 1.2.
- 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, it cannot be defined unconditionally, but is usually about 1 to 100 hours.
- 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 10,000 to 200,000. About 000, more preferably about 30,000 to 150,000.
- a weight average molecular weight is a polystyrene conversion value by a gel permeation chromatography (GPC) measurement.
- the organosilane compound contained in the composition for forming a release layer of the present invention is not particularly limited, and specific examples thereof include alkoxysilane compounds such as dialkoxysilane compounds and trialkoxysilane compounds. .
- the organosilane compound contained in the composition for forming a release layer of the present invention preferably contains a reactive functional group from the viewpoint of improving the function of the resulting film as a release layer.
- reactive functional groups include vinyl groups, epoxy groups, styryl groups, methacryl groups, acrylic groups, amino groups, isocyanurate groups, ureido groups, mercapto groups, sulfide groups, and isocyanate groups.
- an epoxy group is preferred.
- an example of a preferred organosilane compound in the present invention is an alkoxysilane compound having an epoxy group.
- organic silane compound having a reactive functional group examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane, vinyltris (2-methoxyethoxy) silane, vinylmethyldimethoxysilane, allyltrimethoxysilane, 2 -(3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxydipropylmethyldimethoxysilane, 3-glycidoxydipropyltrimethoxysilane, 3-glycidoxydipropylmethyldiethoxysilane, 3-glycidoxydi Propyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethodiethoxysilane 3-methacryloxypropyltrie
- the ratio of the polyamic acid and the organosilane compound in the composition for forming a release layer of the present invention is about 0.001 to 0.2 organosilane compound with respect to polyamic acid 1 in terms of mass ratio, preferably It is about 0.005 to 0.1, more preferably about 0.007 to 0.07.
- the release layer forming composition of the present invention contains an organic solvent.
- this organic solvent the same thing as the specific example of the reaction solvent of the said reaction is mentioned.
- 2-Imidazolidinone, N-ethyl-2-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 Propoxy) propanol, methyl lactate, ethyl lactate, n-propyl lactate, n-butyl lactate, isoamyl lactate and other solvents
- the method for preparing the composition for forming a release layer of the present invention is arbitrary.
- a preferable example of the preparation method is a method of filtering the reaction solution containing the target polyamic acid obtained by the method described above, and adding an organosilane compound to the obtained filtrate.
- the filtrate may be diluted or concentrated if necessary for the purpose of adjusting the concentration.
- 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 above reaction.
- the solvent used for dilution may be used singly or in combination of two or more.
- 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 by adjusting the amount of diamine component and tetracarboxylic dianhydride component, which are raw materials for polyamic acid, and by adjusting the amount when dissolving isolated polyamic acid in a solvent. can do.
- the viscosity of 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, etc., but a film having a thickness of about 0.05 to 5 ⁇ m is particularly reproducible. When it is intended to obtain, 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 of the present invention may contain a crosslinking agent or the like in order to improve film strength, for example, in addition to the polyamic acid, the organic silane compound and the organic solvent.
- the release layer When such a release layer of the present invention is formed on a substrate, the release layer may be formed on a partial surface of the substrate, or may be formed 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 of this invention is applied to the surface.
- the substrate examples include glass, plastic (polycarbonate, polymethacrylate, polystyrene, polyester, polyolefin, epoxy, melamine, triacetyl cellulose, ABS, AS, norbornene resin, etc.), metal (silicon wafer, etc.), Although wood, paper, slate, etc. are mentioned, since the peeling layer of this invention has sufficient adhesiveness with respect to it, 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 composed of two or more materials, a certain range of the substrate surface is composed of a certain material, and the other surface is composed of other materials. A dot pattern is formed on the entire surface of the substrate. There is a mode in which a material in a pattern such as a line and space pattern is present in other materials.
- the method for applying the release layer-forming composition of the present invention to the substrate is not particularly limited, and examples thereof include cast coating, spin coating, blade coating, dip coating, roll coating, and bar coating.
- Method, die coating method, ink jet method, printing method eg, relief printing, intaglio printing, planographic printing, screen printing, etc.
- the heating temperature for imidization is usually appropriately determined within the range of 50 to 550 ° C., but is preferably more than 150 ° C. to 510 ° C. By setting the heating temperature in this way, it is possible to sufficiently advance the imidization reaction while preventing the obtained film from being weakened.
- the heating time varies depending on the heating temperature, and cannot be generally defined, but is usually 5 minutes to 5 hours.
- the imidization rate may be in the range of 50 to 100%.
- the heating temperature is gradually increased as it is, and finally from 150 ° C. to 510 ° C. for 30 minutes to 4 hours.
- the method of heating is mentioned. In particular, it is preferable that heating is performed at 50 to 150 ° C. for 5 minutes to 2 hours, followed by heating at 150 to 350 ° C. for 5 minutes to 2 hours, and finally heating at 350 to 450 ° C. for 30 minutes to 4 hours.
- Examples of the appliance 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, and preferably about 0.05 to 20 ⁇ m from the viewpoint of productivity.
- desired thickness is implement
- 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 of the present invention peels the resin substrate from the substrate together with the circuit formed on the resin substrate without damaging the resin substrate of the device in the manufacturing process of the flexible electronic device. Therefore, it can be suitably used.
- a release layer is formed on a glass substrate by the method described above.
- a resin solution for forming a resin substrate is applied on the release layer, and this coating film is heated to form a resin substrate fixed to the glass substrate via the release layer of the present invention.
- the substrate is formed with a larger area than the area of the release layer so as to cover the entire 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 of the present invention, and then the resin substrate is cut along the release layer, for example.
- the resin substrate and the substrate are separated by peeling from the release layer. 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 composition for forming a release layer according to the present invention has a feature of sufficiently absorbing light having a specific wavelength (for example, 308 nm) that enables application of the LLO method, and can therefore be used as a sacrificial layer for 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
- Mw weight average molecular weight
- Mw molecular weight
- eluent dimethylformamide / LiBr.H 2 O (29.6 mM) / H 3 PO 4 (29.6 mM) / THF (0.1 wt%)
- flow rate 1.0 mL / min
- column temperature 40 ° C
- Mw standard polystyrene equivalent value
- composition for forming release layer [Example 1-1] Using the reaction solution obtained in Synthesis Example L1, the silane solution obtained in Preparation Example 3, BCS and NMP, the polymer concentration was 5% by mass, the LS-4668 concentration was 1% by mass, and the BCS concentration was 20%. A composition for forming a release layer having a mass% was obtained.
- 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 1-6 Using the reaction solution obtained in Synthesis Example L1, the silane solution obtained in Preparation Example 3, BCS and NMP, the polymer concentration was 5% by mass, the LS-4668 concentration was 0.25% by mass, and the BCS concentration A release layer-forming composition having a content of 20% by mass was obtained.
- Comparative Example 1 The reaction solution obtained in Comparative Synthesis Example 1 was diluted with NMP so that the polymer concentration was 5 wt% to obtain a composition.
- Example 2-1 Formation of release layer [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 placed on a 100 mm ⁇ 100 mm glass substrate (hereinafter the same) as a glass substrate. It was applied to. 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. And then heated at 400 ° C. for 30 minutes to form a release layer having a thickness of about 0.1 ⁇ m on the glass substrate. During the temperature increase, the film-coated substrate was not removed from the oven but heated in the oven.
- a spin coater condition: about 3,000 rpm for about 30 seconds
- Example 2-1 was used except that the composition for forming a release layer obtained in Examples 1-2 to 1-6 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.
- Comparative Example 2 A resin thin film was formed in the same manner as in Example 2-1, except that the composition obtained in Comparative Example 1 was used instead of the release layer forming composition obtained in Example 1-1. .
- the resin substrates of Examples 3-1 to 3-12 and Comparative Example 3 were formed by the following method. Using a bar coater (gap: 250 ⁇ m), either the resin substrate forming composition W or X was applied on the release layer (resin thin film) on the glass substrate. The obtained coating film was heated at 80 ° C. for 30 minutes using a hot plate, and then heated at 140 ° C. for 30 minutes using an oven, and the heating temperature was raised to 210 ° C. (10 ° C./min. The same applies to the following, and the heating temperature was raised to 210 ° C. for 30 minutes, the heating temperature was raised to 300 ° C., the heating temperature was raised to 300 ° C.
- the heating temperature was raised to 400 ° C., and the heating temperature was raised to 400 ° C. for 60 minutes.
- a polyimide substrate having a thickness of about 20 ⁇ m was formed. During the temperature increase, the film-coated substrate was not removed from the oven but heated in the oven.
- the release layers of the examples are excellent in adhesion to the glass substrate and excellent in peelability from the resin substrate.
- the resin thin film of the comparative example was excellent in the peelability with the resin substrate, since it had low adhesiveness with glass, it peeled off in the crosscut test.
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Abstract
Description
1. ポリアミック酸と、有機シラン化合物と、有機溶媒とを含む剥離層形成用組成物、
2. 前記有機シラン化合物が、反応性官能基を含むアルコキシシラン化合物であることを特徴とする1の剥離層形成用組成物、
3. 前記ポリアミック酸が、芳香族ジアミンを含むジアミン成分と芳香族テトラカルボン酸二無水物を含む酸二無水物とを反応させて得られたポリアミック酸であることを特徴とする1又は2の剥離層形成用組成物、
4. 前記芳香族ジアミンが、ベンゼン核を1~5つ含む芳香族ジアミンであることを特徴とする3の剥離層形成用組成物、
5. 前記芳香族テトラカルボン酸二無水物が、ベンゼン核を1~5つ含む芳香族テトラカルボン酸二無水物であることを特徴とする3又は4の剥離層形成用組成物、
6. 前記ジアミン成分が、更に式(S)で表されるジアミンを含む3~5のいずれかの剥離層形成用組成物、
7. 1~6のいずれかの剥離層形成用組成物を用いて形成される剥離層、
8. 7の剥離層を用いることを特徴とする、樹脂基板を備えるフレキシブル電子デバイスの製造方法、
9. 前記樹脂基板が、ポリイミドからなる基板であることを特徴とする8の製造方法
を提供する。
本発明の剥離層形成用組成物は、ポリアミック酸と、有機シラン化合物と、有機溶媒とを含む。ここで、本発明における剥離層とは、所定の目的でガラス基体直上に設けられる層であって、その典型例としては、フレキシブル電子デバイスの製造プロセスにおいて、基体と、ポリイミドといった樹脂からなるフレキシブル電子デバイスの樹脂基板との間に当該樹脂基板を所定のプロセス中において固定するために設けられ、かつ、当該樹脂基板上に電子回路等の形成した後において当該樹脂基板が当該基体から容易に剥離できるようにするために設けられる剥離層が挙げられる。
その具体例としては、1,4-ジアミノベンゼン(p-フェニレンジアミン)、1,3-ジアミノベンゼン(m-フェニレンジアミン)、1,2-ジアミノベンゼン(o-フェニレンジアミン)、2,4-ジアミノトルエン、2,5-ジアミノトルエン、2,6-ジアミノトルエン、4,6-ジメチル-m-フェニレンジアミン、2,5-ジメチル-p-フェニレンジアミン、2,6-ジメチル-p-フェニレンジアミン、2,4,6-トリメチル-1,3-フェニレンジアミン、2,3,5,6-テトラメチル-p-フェニレンジアミン、m-キシリレンジアミン、p-キシリレンジアミン、5-トリフルオロメチルベンゼン-1,3-ジアミン、5-トリフルオロメチルベンゼン-1,2-ジアミン、3,5-ビス(トリフルオロメチル)ベンゼン-1,2-ジアミン等のベンゼン核が1つのジアミン;1,2-ナフタレンジアミン、1,3-ナフタレンジアミン、1,4-ナフタレンジアミン、1,5-ナフタレンジアミン、1,6-ナフタレンジアミン、1,7-ナフタレンジアミン、1,8-ナフタレンジアミン、2,3-ナフタレンジアミン、2,6-ナフタレンジアミン、4,4’-ビフェニルジアミン、2,2’-ビス(トリフルオロメチル)-4,4’-ジアミノビフェニル、3,3’-ジメチル-4,4’-ジアミノジフェニルメタン、3,3’-ジカルボキシ-4,4’-ジアミノジフェニルメタン、3,3’,5,5’-テトラメチル-4,4’-ジアミノジフェニルメタン、4,4’-ジアミノベンズアニリド、3,3’-ジクロロベンジジン、3,3’-ジメチルベンジジン、2,2’-ジメチルベンジジン、3,3’-ジアミノジフェニルメタン、3,4’-ジアミノジフェニルメタン、4,4’-ジアミノジフェニルメタン、2,2-ビス(3-アミノフェニル)プロパン、2,2-ビス(4-アミノフェニル)プロパン、2,2-ビス(3-アミノフェニル)-1,1,1,3,3,3-ヘキサフルオロプロパン、2,2-ビス(4-アミノフェニル)-1,1,1,3,3,3-ヘキサフルオロプロパン、3,3’-ジアミノジフェニルスルホキシド、3,4’-ジアミノジフェニルスルホキシド、4,4’-ジアミノジフェニルスルホキシド、3,3’-ビス(トリフルオロメチル)ビフェニル-4,4’-ジアミン、3,3’,5,5’-テトラフルオロビフェニル-4,4’-ジアミン、4,4’-ジアミノオクタフルオロビフェニル、2-(3-アミノフェニル)-5-アミノベンズイミダゾール、2-(4-アミノフェニル)-5-アミノベンゾオキゾール等のベンゼン核が2つのジアミン;1,5-ジアミノアントラセン、2,6-ジアミノアントラセン、9,10-ジアミノアントラセン、1,8-ジアミノフェナントレン、2,7-ジアミノフェナントレン、3,6-ジアミノフェナントレン、9,10-ジアミノフェナントレン、1,3-ビス(3-アミノフェニル)ベンゼン、1,3-ビス(4-アミノフェニル)ベンゼン、1,4-ビス(3-アミノフェニル)ベンゼン、1,4-ビス(4-アミノフェニル)ベンゼン、1,3-ビス(3-アミノフェニルスルフィド)ベンゼン、1,3-ビス(4-アミノフェニルスルフィド)ベンゼン、1,4-ビス(4-アミノフェニルスルフィド)ベンゼン、1,3-ビス(3-アミノフェニルスルホン)ベンゼン、1,3-ビス(4-アミノフェニルスルホン)ベンゼン、1,4-ビス(4-アミノフェニルスルホン)ベンゼン、1,3-ビス〔2-(4-アミノフェニル)イソプロピル〕ベンゼン、1,4-ビス〔2-(3-アミノフェニル)イソプロピル〕ベンゼン、1,4-ビス〔2-(4-アミノフェニル)イソプロピル〕ベンゼン、4,4’’-ジアミノ-p-ターフェニル、4,4’’-ジアミノ-m-ターフェニル等のベンゼン核が3つのジアミン等を挙げることができるが、これらに限定されない。これらは単独でも、2種以上を組み合わせて用いることもできる。
なお、式(S)で表されるジアミンは、市販品として入手できるし、公知の方法(例えば国際公開第2010/108785号に記載の方法)で合成することもできる。
このような使用量を採用することで、基体との優れた密着性及び樹脂基板との適度な密着性と適度な剥離性を有する膜を再現性よく得ることができる。
反応時間は、反応温度や原料物質の反応性に依存するため一概に規定できないが、通常1~100時間程度である。
また、本発明の剥離層形成用組成物が含む有機シラン化合物は、得られる膜の剥離層としての機能を向上させる観点から、好ましくは反応性官能基を含む。
このような反応性官能基の具体例としては、ビニル基、エポキシ基、スチリル基、メタクリル基、アクリル基、アミノ基、イソシアヌレート基、ウレイド基、メルカプト基、スルフィド基、イソシアネート基が挙げられるが、中でも、エポキシ基が好ましい。
このような事情から、本発明における好ましい有機シラン化合物の一例としては、エポキシ基を有するアルコキシシラン化合物が挙げられる。
本発明の剥離層形成用組成物を用いて、上述の方法によって、ガラス基体上に剥離層を形成する。この剥離層の上に、樹脂基板を形成するための樹脂溶液を塗布し、この塗膜を加熱することで、本発明の剥離層を介して、ガラス基体に固定された樹脂基板を形成する。この際、剥離層を全て覆うようにして、剥離層の面積と比較して大きい面積で、基板を形成する。樹脂基板としては、フレキシブル電子デバイスの樹脂基板として代表的なポリイミドからなる樹脂基板が挙げられ、それを形成するための樹脂溶液としては、ポリイミド溶液やポリアミック酸溶液が挙げられる。当該樹脂基板の形成方法は、常法に従えばよい。
[1]略語の説明
p-PDA:p-フェニレンジアミン
m-PDA:m-フェニレンジアミン
DATP:4,4’’-ジアミノ-p-ターフェニル
H-PAM:1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン
6FAP:2,2-ビス(3-アミノ-4-ヒドロキシフェニル)ヘキサフルオロプロパン
PMDA:ピロメリット酸二無水物
BPDA:3,3’,4,4’-ビフェニルテトラカルボン酸二無水物
NTCDA:ナフタレン-2,3,6,7-テトラカルボン酸二無水物
IHPA:イソフタルアルデヒド
NMP:N-メチル-2-ピロリドン
BCS:ブチルセロソルブ
LS-4668:3-グリシドキシプロピルトリエトキシシラン
ポリマーの重量平均分子量(以下Mwと略す)及び分子量分布の測定は、日本分光株式会社製GPC装置(カラム:Shodex製 OHpak SB803-HQ、及びOHpak SB804-HQ;溶離液:ジメチルホルムアミド/LiBr・H2O(29.6mM)/H3PO4(29.6mM)/THF(0.1wt%);流量:1.0mL/分;カラム温度:40℃;Mw:標準ポリスチレン換算値)を用いて行った
<合成例S1 ポリアミック酸(S1)の合成>
p-PDA 20.261g(187mmol)とDATP 12.206g(47mmol)をNMP 617.4gに溶解させた。得られた溶液を15℃に冷却し、そこへPMDA 50.112g(230mmol)を加え、窒素雰囲気下、50℃まで昇温し48時間反応させた。得られたポリマーのMwは82,100、分子量分布は2.7であった。
p-PDA 3.218g(30mmol)をNMP 88.2gに溶解させた。得られた溶液にBPDA 8.581g(29mmol)を加え、窒素雰囲気下、23℃で24時間反応させた。得られたポリマーのMwは107,300、分子量分布4.6であった。
p-PDA 10.078g(93mmol)をNMP 220.0gに溶解させた。得られた溶液に、PMDA 19.922g(91mmol)を加え、窒素雰囲気下、23℃で24時間反応させた。得られたポリマーのMwは55,900、分子量分布3.1であった。
p-PDA 9.934g(92mmol)とH-PAM 0.042g(93mmol)をNMP 220.0gに溶解させた。得られた溶液にPMDA 19.835g(91mmol)を加え、窒素雰囲気下、23℃で24時間反応させた。得られたポリマーのMwは48,000、分子量分布2.9であった。
p-PDA 1.474g(14mmol)とDATP 0.843g(3mmol)とH-PAM 0.042g(0.2mmol)をNMP 34.0gに溶解させた。得られた溶液にPMDA 3.641g(17mmol)を加え、窒素雰囲気下、23℃で24時間反応させた。得られたポリマーのMwは45,100、分子量分布2.5であった。
p-PDA 1.588g(15mmol)をNMP 35.2gに溶解させた。得られた溶液にPMDA 2.818g(13mmol)とNTCDA 0.393g(2mmol)を加え、窒素雰囲気下、23℃で24時間反応させた。得られたポリマーのMwは21,000、分子量分布2.7であった。
p-PDA 1.432g(13mmol)とm-PDA 0.159g(2mmol)をNMP 35.2gに溶解させた。得られた溶液にPMDA 3.209g(15mmol)を加え、窒素雰囲気下、23℃で24時間反応させた。得られたポリマーのMwは106,100、分子量分布3.6であった。
6FAP 3.18g(0.059モル)をNMP70gに溶解させた。得られた溶液にIHPA 7.92g(0.060モル)を加え、窒素雰囲気下、23℃で24時間反応させた。得られたポリマーのMwは107,300、分子量分布4.6であった。
[調製例1,2]
合成例S1,S2で得られた反応液を、それぞれ、そのまま樹脂基板形成用組成物W,Xとして用いた。
LS-4668及びNMPを用いて、LS-4668の濃度が10質量%であるシラン溶液を調製した。
[実施例1-1]
合成例L1で得られた反応液、調製例3で得られたシラン溶液、BCS及びNMPを用い、ポリマー濃度が5質量%であり、LS-4668濃度が1質量%であり、BCS濃度が20質量%である剥離層形成用組成物を得た。
合成例L1で得られた反応液の代わりに、それぞれ合成例L2~L5で得られた反応液を用いた以外は、実施例1-1と同様の方法で、剥離層形成用組成物を得た。
合成例L1で得られた反応液、調製例3で得られたシラン溶液、BCS及びNMPを用い、ポリマー濃度が5質量%であり、LS-4668濃度が0.25質量%であり、BCS濃度が20質量%である剥離層形成用組成物を得た。
比較合成例1で得られた反応液を、ポリマー濃度が5wt%となるようにNMPで希釈して、組成物を得た。
[実施例2-1]
スピンコータ(条件:回転数3,000rpmで約30秒)を用いて、実施例1-1で得られた剥離層形成用組成物を、ガラス基体としての100mm×100mmガラス基板(以下同様)の上に塗布した。
そして、得られた塗膜を、ホットプレートを用いて80℃で10分間加熱し、その後、オーブンを用いて、300℃で30分間加熱し、加熱温度を400℃まで昇温(10℃/分)し、更に400℃で30分間加熱し、ガラス基板上に厚さ約0.1μmの剥離層を形成した。なお、昇温の間、膜付き基板をオーブンから取り出すことはせず、オーブン内で加熱した。
実施例1-1で得られた剥離層形成用組成物の代わりに、それぞれ実施例1-2~1-6で得られた剥離層形成用組成物を用いた以外は、実施例2-1と同様の方法で、剥離層を形成した。
実施例1-1で得られた剥離層形成用組成物の代わりに、比較例1で得られた組成物を用いた以外は、実施例2-1と同様の方法で、樹脂薄膜を形成した。
[実施例3-1~3-12,比較例3]
以下の方法により、表1に示した剥離層と樹脂基板の組み合わせとなるよう基板を作製し、剥離性の評価をした。
実施例2-1~2-6で得られた剥離層とガラス基板の剥離性及び当該剥離層(樹脂薄膜)と樹脂基板の剥離性を確認した。なお、樹脂基板としては、ポリイミドからなる樹脂基板を用いた。
まず、実施例2-1~2-6で得られた剥離層付きガラス基板上の剥離層のクロスカット(縦横1mm間隔、以下同様)、並びに、樹脂基板・剥離層付きガラス基板上の樹脂基板・剥離層のクロスカットを行うことにより、100マスカットを行った。すなわち、このクロスカットにより、1mm四方のマス目を100個形成した。
そして、この100マスカット部分に粘着テープを張り付けて、そのテープを剥がし、以下の基準(5B~0B,B,A,AA)に基づき、剥離の程度を評価した(実施例3-1~3-12)。また、上記手法に準じて、比較例2で得られた樹脂薄膜付きガラス基板を用いて、同様の試験を行った(比較例3)。結果を表1に示す。
4B:5%未満の剥離
3B:5~15%未満の剥離
2B:15~35%未満の剥離
1B:35~65%未満の剥離
0B:65%~80%未満の剥離
B:80%~95%未満の剥離
A:95%~100%未満の剥離
AA:100%剥離(すべて剥離)
バーコーター(ギャップ:250μm)を用いて、ガラス基板上の剥離層(樹脂薄膜)の上に樹脂基板形成用組成物W又はXのいずれかを塗布した。そして、得られた塗膜を、ホットプレートを用いて80℃で30分間加熱し、その後、オーブンを用いて、140℃で30分間加熱し、加熱温度を210℃まで昇温(10℃/分、以下同様)し、210℃で30分間、加熱温度を300℃まで昇温し、300℃で30分間、加熱温度を400℃まで昇温し、400℃で60分間加熱し、剥離層上に厚さ約20μmのポリイミド基板を形成した。昇温の間、膜付き基板をオーブンから取り出すことはせず、オーブン内で加熱した。
Claims (9)
- ポリアミック酸と、有機シラン化合物と、有機溶媒とを含む剥離層形成用組成物。
- 前記有機シラン化合物が、反応性官能基を含むアルコキシシラン化合物であることを特徴とする請求項1記載の剥離層形成用組成物。
- 前記ポリアミック酸が、芳香族ジアミンを含むジアミン成分と芳香族テトラカルボン酸二無水物を含む酸二無水物とを反応させて得られたポリアミック酸であることを特徴とする請求項1又は2記載の剥離層形成用組成物。
- 前記芳香族ジアミンが、ベンゼン核を1~5つ含む芳香族ジアミンであることを特徴とする請求項3記載の剥離層形成用組成物。
- 前記芳香族テトラカルボン酸二無水物が、ベンゼン核を1~5つ含む芳香族テトラカルボン酸二無水物であることを特徴とする請求項3又は4記載の剥離層形成用組成物。
- 請求項1~6のいずれか1項記載の剥離層形成用組成物を用いて形成される剥離層。
- 請求項7記載の剥離層を用いることを特徴とする、樹脂基板を備えるフレキシブル電子デバイスの製造方法。
- 前記樹脂基板が、ポリイミドからなる基板であることを特徴とする請求項8に記載の製造方法。
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH024201A (ja) * | 1988-06-23 | 1990-01-09 | Toray Ind Inc | カラーフィルタ用耐熱着色ペースト |
JP2000306441A (ja) * | 1999-04-19 | 2000-11-02 | Kyodo Printing Co Ltd | 透明導電膜の転写方法 |
JP2001056406A (ja) * | 1999-08-19 | 2001-02-27 | Toray Ind Inc | カラーフィルター |
WO2013125193A1 (ja) * | 2012-02-23 | 2013-08-29 | 日立化成デュポンマイクロシステムズ株式会社 | 樹脂組成物、及びこれを用いたポリイミド樹脂膜、ディスプレイ基板とその製造方法 |
WO2014050933A1 (ja) * | 2012-09-27 | 2014-04-03 | 新日鉄住金化学株式会社 | 表示装置の製造方法 |
WO2014073591A1 (ja) * | 2012-11-08 | 2014-05-15 | 旭化成イーマテリアルズ株式会社 | フレキシブルデバイス用基板、フレキシブルデバイス及びその製造方法、積層体及びその製造方法、並びに、樹脂組成物 |
JP2014218056A (ja) * | 2013-05-10 | 2014-11-20 | ユニチカ株式会社 | フレキシブルデバイス用積層体 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3809681B2 (ja) | 1996-08-27 | 2006-08-16 | セイコーエプソン株式会社 | 剥離方法 |
JP4619461B2 (ja) | 1996-08-27 | 2011-01-26 | セイコーエプソン株式会社 | 薄膜デバイスの転写方法、及びデバイスの製造方法 |
JP4619462B2 (ja) | 1996-08-27 | 2011-01-26 | セイコーエプソン株式会社 | 薄膜素子の転写方法 |
CN100384622C (zh) * | 2003-04-02 | 2008-04-30 | Tdk株式会社 | 剥离膜及其制造方法 |
GB0327093D0 (en) | 2003-11-21 | 2003-12-24 | Koninkl Philips Electronics Nv | Active matrix displays and other electronic devices having plastic substrates |
TWI444114B (zh) * | 2011-12-26 | 2014-07-01 | Chi Mei Corp | 具有離型層的基板結構及其製造方法 |
TWI479000B (zh) * | 2013-02-07 | 2015-04-01 | Sumika Technology Co Ltd | 接著性高分子組成物及其應用 |
-
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Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH024201A (ja) * | 1988-06-23 | 1990-01-09 | Toray Ind Inc | カラーフィルタ用耐熱着色ペースト |
JP2000306441A (ja) * | 1999-04-19 | 2000-11-02 | Kyodo Printing Co Ltd | 透明導電膜の転写方法 |
JP2001056406A (ja) * | 1999-08-19 | 2001-02-27 | Toray Ind Inc | カラーフィルター |
WO2013125193A1 (ja) * | 2012-02-23 | 2013-08-29 | 日立化成デュポンマイクロシステムズ株式会社 | 樹脂組成物、及びこれを用いたポリイミド樹脂膜、ディスプレイ基板とその製造方法 |
WO2014050933A1 (ja) * | 2012-09-27 | 2014-04-03 | 新日鉄住金化学株式会社 | 表示装置の製造方法 |
WO2014073591A1 (ja) * | 2012-11-08 | 2014-05-15 | 旭化成イーマテリアルズ株式会社 | フレキシブルデバイス用基板、フレキシブルデバイス及びその製造方法、積層体及びその製造方法、並びに、樹脂組成物 |
JP2014218056A (ja) * | 2013-05-10 | 2014-11-20 | ユニチカ株式会社 | フレキシブルデバイス用積層体 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018181496A1 (ja) * | 2017-03-30 | 2018-10-04 | 日産化学株式会社 | 剥離層形成用組成物及び剥離層 |
KR20190129103A (ko) * | 2017-03-30 | 2019-11-19 | 닛산 가가쿠 가부시키가이샤 | 박리층 형성용 조성물 및 박리층 |
CN110520478A (zh) * | 2017-03-30 | 2019-11-29 | 日产化学株式会社 | 剥离层形成用组合物和剥离层 |
JPWO2018181496A1 (ja) * | 2017-03-30 | 2020-02-06 | 日産化学株式会社 | 剥離層形成用組成物及び剥離層 |
CN110520478B (zh) * | 2017-03-30 | 2022-05-17 | 日产化学株式会社 | 剥离层形成用组合物和剥离层 |
JP7092114B2 (ja) | 2017-03-30 | 2022-06-28 | 日産化学株式会社 | 剥離層形成用組成物及び剥離層 |
KR102574758B1 (ko) * | 2017-03-30 | 2023-09-06 | 닛산 가가쿠 가부시키가이샤 | 박리층 형성용 조성물 및 박리층 |
JP2019099697A (ja) * | 2017-12-04 | 2019-06-24 | ユニチカ株式会社 | ガラス基板への塗工用溶液 |
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JP6705444B2 (ja) | 2020-06-03 |
JPWO2016158988A1 (ja) | 2018-02-15 |
TW201706363A (zh) | 2017-02-16 |
KR20170132803A (ko) | 2017-12-04 |
TW202037640A (zh) | 2020-10-16 |
CN107960094B (zh) | 2021-03-12 |
KR102534510B1 (ko) | 2023-05-19 |
TWI758244B (zh) | 2022-03-21 |
CN107960094A (zh) | 2018-04-24 |
TWI742701B (zh) | 2021-10-11 |
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