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WO2018025955A1 - Composition pour former une couche anti-adhésive - Google Patents

Composition pour former une couche anti-adhésive Download PDF

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Publication number
WO2018025955A1
WO2018025955A1 PCT/JP2017/028212 JP2017028212W WO2018025955A1 WO 2018025955 A1 WO2018025955 A1 WO 2018025955A1 JP 2017028212 W JP2017028212 W JP 2017028212W WO 2018025955 A1 WO2018025955 A1 WO 2018025955A1
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WIPO (PCT)
Prior art keywords
release layer
resin substrate
substrate
aromatic group
composition
Prior art date
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Ceased
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PCT/JP2017/028212
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English (en)
Japanese (ja)
Inventor
和也 進藤
江原　和也
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Nissan Chemical Corp
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Nissan Chemical Corp
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Publication date
Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to JP2018531974A priority Critical patent/JP7135857B2/ja
Priority to CN201780046632.3A priority patent/CN109476913B/zh
Priority to KR1020197004723A priority patent/KR102376154B1/ko
Publication of WO2018025955A1 publication Critical patent/WO2018025955A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
    • 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
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
    • C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) 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
    • 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
    • C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
    • 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
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
    • 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
    • C08G73/12—Unsaturated polyimide precursors
    • 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
    • C08K5/20—Carboxylic acid amides
    • 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
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino-carboxylic acids or of polyamines and polycarboxylic acids
    • G—PHYSICS
    • G06—COMPUTING OR CALCULATING; COUNTING
    • G06F—ELECTRIC DIGITAL DATA PROCESSING
    • G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
    • G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
    • G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
    • G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10D—INORGANIC ELECTRIC SEMICONDUCTOR DEVICES
    • H10D86/00—Integrated devices formed in or on insulating or conducting substrates, e.g. formed in silicon-on-insulator [SOI] substrates or on stainless steel or glass substrates

Definitions

  • the present invention relates to a release layer forming composition, and more particularly, to a release layer forming composition for forming a release layer provided on a substrate.
  • the resin substrate used for the touch panel is a polyimide resin substrate, an acrylic resin substrate, a polyethylene terephthalate (PET) resin substrate, a cycloolefin resin substrate having transparency equivalent to that of glass, like a TFT display panel.
  • PET polyethylene terephthalate
  • a cycloolefin resin substrate having transparency equivalent to that of glass, like a TFT display panel.
  • Patent Documents 1, 2, and 3 after an amorphous silicon thin film layer is formed on a glass substrate and a plastic substrate is formed on the thin film layer, laser irradiation is performed from the glass surface side to crystallize amorphous silicon.
  • a method of peeling a plastic substrate from a glass substrate with hydrogen gas generated along with the above is disclosed.
  • 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, thereby completing a liquid crystal display device. 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 can be peeled without damaging a resin substrate of a flexible electronic device, particularly a resin substrate formed of a polyimide resin, an acrylic resin, a cycloolefin polymer resin, or the like. It aims at providing the composition for peeling layer formation which gives the peeling layer used as this.
  • the inventors of the present invention have a composition comprising a polyamic acid or polyamide having a specific structure and an organic solvent, which has excellent adhesion to a substrate such as a glass substrate and the like.
  • the present invention has been completed by finding that a release layer having appropriate adhesion to a resin substrate used as a flexible electronic device and appropriate release properties can be provided.
  • a composition for forming a release layer comprising: (In the formula, X 1 represents a tetravalent aromatic group having no fluorine atom, X 2 represents a tetravalent aromatic group having a fluorine atom, and X 3 represents a divalent group having no fluorine atom. Y 1 represents a divalent aromatic group having a fluorine atom, Y 2 represents a divalent aromatic group having no fluorine atom, and m represents a natural number.) 2.
  • the release layer forming composition according to 1 wherein Y 1 is an aromatic group selected from the group consisting of the following formulas (5) to (9): 3.
  • the release layer forming composition according to any one of 1 to 6, wherein Y 2 is an aromatic group containing 1 to 5 benzene rings; 8). Any of 1 to 7, wherein the organic solvent includes at least one selected from amides represented by the formula (S1), amides represented by the formula (S2), and amides represented by the formula (S3)
  • S1 amides represented by the formula
  • S2 amides represented by the formula
  • S3 amides represented by the formula (S3)
  • a release layer forming composition (In the formula, 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. Represents.) 9.
  • a method for producing a flexible electronic device comprising a resin substrate, comprising using a release layer of 9; 11.
  • a method for producing a touch panel sensor comprising a resin substrate, comprising using a release layer of 9; 12 The manufacturing method according to 10 or 11, wherein the resin substrate is a polyimide resin substrate or a resin substrate having a light transmittance of 80% or more at a wavelength of 400 nm.
  • the composition for forming a release layer of the present invention By using the composition for forming a release layer of the present invention, it is possible to obtain a film having excellent adhesion to the substrate, moderate adhesion to the resin substrate, and moderate peelability with good reproducibility.
  • the composition of the present invention in the manufacturing process of the flexible electronic device, the resin substrate formed on the substrate and the circuit provided on the substrate are not damaged, and the resin substrate together with the circuit etc. Can be separated from the substrate. 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.
  • composition for forming a release layer of the present invention comprises a polyamic acid represented by the following formula (1), a polyamic acid represented by the following formula (2), a polyamic acid represented by the following formula (3), or the following formula ( 4)
  • the polyamide represented by 4) and an organic solvent are included.
  • the release layer is a layer provided immediately above a substrate (such as a glass substrate) on which a resin substrate is formed.
  • a substrate such as a glass substrate
  • the resin substrate is placed between the substrate and a resin substrate of the flexible electronic device formed of polyimide resin, acrylic resin, cycloolefin polymer resin, or the like.
  • Examples include a release layer that is provided for fixing inside and provided so that the resin substrate can be easily peeled from the substrate after an electronic circuit or the like is formed on the resin substrate.
  • X 1 represents a tetravalent aromatic group having no fluorine atom
  • X 2 represents a tetravalent aromatic group having a fluorine atom
  • X 3 represents Represents a divalent aromatic group having no fluorine atom
  • Y 1 represents a divalent aromatic group having a fluorine atom
  • Y 2 represents a divalent aromatic group having no fluorine atom
  • m Represents a natural number.
  • X 1 is preferably an aromatic group having no fluorine atom and containing 1 to 5 benzene rings.
  • X 1 may include either one or both of an ester bond and an ether bond.
  • Y 1 is preferably an aromatic group having a fluorine atom and containing 1 to 5 benzene rings, more preferably an aromatic group selected from the group consisting of the following formulas (5) to (9).
  • An aromatic group selected from (5) is more preferable, and an aromatic group represented by the following formula (10) is more preferable.
  • X 2 is preferably an aromatic group having a fluorine atom and containing 1 to 5 benzene rings, and more preferably an aromatic group represented by the following formula (11) or (12).
  • Y 2 is preferably an aromatic group having no fluorine atom and containing 1 to 5 benzene rings, and more preferably an aromatic group containing 1 to 3 benzene rings.
  • Y 2 may include either one or both of an ester bond and an ether bond.
  • X 3 is preferably an aromatic group having no fluorine atom and containing 1 to 5 benzene rings, more preferably an aromatic group containing 1 to 2 benzene rings, and still more preferably a biphenyl group.
  • M may be a natural number, but is preferably a natural number of 100 or less, more preferably a natural number of 2 to 100.
  • Polyamic acid 1 The polyamic acid represented by the above formula (1) is obtained by reacting an aromatic tetracarboxylic dianhydride having no fluorine atom with an aromatic diamine having a fluorine atom.
  • aromatic tetracarboxylic dianhydride and aromatic diamine that can be used for the synthesis of the polyamic acid represented by the above formula (1) will be described in detail.
  • the aromatic tetracarboxylic dianhydride is not particularly limited as long as it does not have a fluorine atom and has two dicarboxylic anhydride sites in the molecule.
  • Aromatic tetracarboxylic dianhydrides containing up to 5 are preferred.
  • aromatic tetracarboxylic dianhydride examples include pyromellitic dianhydride, benzene-1,2,3,4-tetracarboxylic dianhydride, naphthalene-1,2,3,4-tetracarboxylic Acid dianhydride, naphthalene-1,2,5,6-tetracarboxylic dianhydride, naphthalene-1,2,6,7-tetracarboxylic dianhydride, naphthalene-1,2,7,8-tetra Carboxylic 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'-t
  • the aromatic diamine is not particularly limited as long as it has two amino groups having a fluorine atom and directly bonded to the aromatic ring in the molecule. Aromatic diamines containing one are preferred. Moreover, what has a fluoroalkyl group or a perfluoroalkyl group is more preferable, and a perfluoroalkyl group is still more preferable. Examples of the perfluoroalkyl group include a trifluoromethyl group, a pentafluoroethyl group, an n-heptafluoropropyl group, and an i-heptafluoropropyl group.
  • aromatic diamine examples include 5-trifluoromethylbenzene-1,3-diamine, 5-trifluoromethylbenzene-1,2-diamine, 2-trifluoromethylbenzene-1,4-diamine, 3 , 5-bis (trifluoromethyl) benzene-1,2-diamine, 2,2′-bis (trifluoromethyl) -4,4′-diaminobiphenyl, 2,2-bis (3-aminophenyl) -1 , 1,1,3,3,3-hexafluoropropane, 2,2-bis (4-aminophenyl) -1,1,1,3,3,3-hexafluoropropane, 3,3′-bis ( Trifluoromethyl) biphenyl-4,4′-diamine, 3,3 ′, 5,5′-tetrafluorobiphenyl-4,4′-diamine, 4,4′-diaminooctafluorobiphenyl, bottom Although aromatic diamines of the formula (A1)
  • Polyamic acid 2 The polyamic acid represented by the above formula (2) is obtained by reacting an aromatic tetracarboxylic dianhydride having a fluorine atom with an aromatic diamine having no fluorine atom.
  • aromatic tetracarboxylic dianhydride and aromatic diamine which can be used for the synthesis
  • combination of the polyamic acid represented by the said Formula (2) are explained in full detail.
  • the aromatic tetracarboxylic dianhydride is not particularly limited as long as it has a fluorine atom and two dicarboxylic anhydride sites in the molecule. Moreover, what has a fluoroalkyl group or a perfluoroalkyl group is more preferable, and a perfluoroalkyl group is still more preferable. Examples of the perfluoroalkyl group include a trifluoromethyl group, a pentafluoroethyl group, an n-heptafluoropropyl group, and an i-heptafluoropropyl group.
  • aromatic tetracarboxylic dianhydride examples include 4,4 ′-(hexafluoroisopropylidene) diphthalic anhydride, N, N ′-[2,2′-bis (trifluoromethyl) biphenyl- 4,4′-diyl] bis (1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxamide), 3,6-difluoropyromellitic dianhydride, 3,6-bis (trifluoromethyl) Pyromellitic dianhydride, 3,6-bis (trifluoromethoxy) pyromellitic dianhydride, 3-fluoropyromellitic dianhydride, 3-trifluoromethylpyromellitic dianhydride, 3-trifluoro Methoxypyromellitic dianhydride, 9,9-bis- (trifluoromethyl) xanthenetetracarboxylic dianhydride, 9-phenyl-9- (trifluoro Chi
  • the aromatic diamine is not particularly limited as long as it does not have a fluorine atom and has two amino groups directly connected to the aromatic ring in the molecule.
  • An aromatic diamine containing 5 is preferred.
  • aromatic diamine examples include 1,4-diaminobenzene (p-phenylenediamine), 1,3-diaminobenzene (m-phenylenediamine), 1,2-diaminobenzene (o-phenylenediamine), 2, 4-diaminotoluene, 2,5-diaminotoluene, 2,6-diaminotoluene, 4,6-dimethyl-m-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, 2,6-dimethyl-p-phenylene 1 benzene ring such as diamine, 2,4,6-trimethyl-1,3-phenylenediamine, 2,3,5,6-tetramethyl-p-phenylenediamine, m-xylylenediamine, p-xylylenediamine, etc.
  • Polyamic acid 3 The polyamic acid represented by the above formula (3) is obtained by reacting an aromatic tetracarboxylic dianhydride having a fluorine atom with an aromatic diamine having a fluorine atom.
  • aromatic tetracarboxylic dianhydride an aromatic tetracarboxylic dianhydride having the same fluorine atom as that which can be used for the synthesis of the polyamic acid represented by the above formula (2) can be used.
  • aromatic diamine an aromatic diamine having the same fluorine atom as that used for the synthesis of the polyamic acid represented by the above formula (1) can be used.
  • polyamide The polyamide represented by the above formula (4) is obtained by reacting an aromatic dicarboxylic acid having no fluorine atom or a derivative thereof with an aromatic diamine having a fluorine atom.
  • aromatic dicarboxylic acid or derivative thereof and the aromatic diamine that can be used for the synthesis of the polyamide represented by the above formula (4) will be described in detail.
  • the aromatic dicarboxylic acid or derivative thereof is not particularly limited as long as it does not have a fluorine atom and has two carboxyl groups or derivatives thereof in the molecule.
  • Aromatic dicarboxylic acids or derivatives thereof containing ⁇ 5, especially 1-2, and even 2 are preferred.
  • aromatic dicarboxylic acids or derivatives thereof include o-phthalic acid, isophthalic acid, terephthalic acid, 5-methylisophthalic acid, 5-tert-butylisophthalic acid, 5-aminoisophthalic acid, 5-hydroxyisophthalic acid, 2,5-dimethylterephthalic acid, tetramethylterephthalic acid, 1,4-naphthalenedicarboxylic acid, 1,6-naphthalenedicarboxylic acid, 2,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalene Dicarboxylic acid, 1,4-anthracene dicarboxylic acid, 1,6-anthracene dicarboxylic acid, 2,6-anthracene dicarboxylic acid, 1,4-anthraquinone dicarboxylic acid, 2,5-biphenyl dicarboxylic acid, 4,4'-biphenyl dicarboxy
  • aromatic diamine an aromatic diamine having the same fluorine atom as that used for the synthesis of the polyamic acid represented by the above formula (1) can be used.
  • the tetracarboxylic acid component / diamine component is preferably 0.8 to 1.2.
  • the polyamic acid represented by the formula (1) contained in the composition for forming a release layer according to the present invention the formula (2) And a polyamic acid represented by the formula (3) can be obtained.
  • the polyamide represented by Formula (4) contained in the composition for peeling layer formation which concerns on this invention can be obtained by making said aromatic diamine and aromatic dicarboxylic acid react.
  • 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. In addition, you may use an organic solvent individually by
  • the organic solvent used in the reaction dissolves the diamine, tetracarboxylic dianhydride, dicarboxylic acid, polyamic acid and polyamide described above well, so that the amide represented by the formula (S1) is represented by (S2). And at least one selected from amides represented by the formula (S3).
  • 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 to be used, and is usually about 0 to 100 ° C., but for example, it prevents imidization in the solution of the resulting polyamic acid to prevent polyamic acid unit
  • the temperature is preferably about 0 to 70 ° C, more preferably about 0 to 60 ° C, and still more preferably about 0 to 50 ° C.
  • a polymerization catalyst may be used to increase the polymerization efficiency.
  • the polymerization catalyst include phosphoric acid, phosphorous acid, hypophosphorous acid or salts thereof, and pyridine.
  • the addition amount of the polymerization catalyst is preferably 2 mol% or less with respect to all monomers constituting the polyamide.
  • 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.
  • reaction solution containing the target polyamic acid or polyamide can be obtained.
  • the weight average molecular weight of the polyamic acid or polyamide is preferably 5,000 to 1,000,000, more preferably 6,000 to 500,000, and even more preferably 7,000 to 200,000 from the viewpoint of handling properties. .
  • the weight average molecular weight is an average molecular weight obtained in terms of standard polystyrene by gel permeation chromatography (GPC) analysis.
  • a solution obtained by directly or diluting or concentrating the filtrate can be used as the composition for forming a release layer of the present invention.
  • the composition for peeling layer formation can be obtained efficiently.
  • 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 in the above 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 are highly soluble in polyamic acid or polyamide.
  • -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
  • the concentration of the polyamic acid or polyamide 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, The amount is preferably 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 or polyamide is adjusted to adjust the amount of diamine and tetracarboxylic dianhydride or dicarboxylic acid used as these raw materials. After filtering the reaction solution, the filtrate is diluted or concentrated. When the separated polyamic acid or polyamide is dissolved in a solvent, the amount can be adjusted by adjusting the amount thereof.
  • the viscosity of the composition for forming the release layer is appropriately set in consideration of the thickness of the release layer to be produced, etc., but in particular, a film having a thickness of about 0.05 to 5 ⁇ m can be obtained with good reproducibility. 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 polyamic acid or polyamide and an organic solvent, for example, in order to improve film strength.
  • a component such as a crosslinking agent in addition to polyamic acid or polyamide and an organic solvent, for example, in order to improve film strength.
  • the release layer of the present invention When the release layer of the present invention is formed on a substrate, the release layer may be formed on a part of the substrate or 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, 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 obtained from the composition for peeling layer formation which concerns on 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.
  • the substrate surface is constituted by two or more materials
  • a certain range of the substrate surface is constituted by a certain material
  • the other surface is constituted by another material.
  • a dot pattern is formed on the entire substrate surface.
  • 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.).
  • the heating temperature for imidization is usually appropriately determined within the range of 50 to 550 ° C., but is preferably 200 ° C. or higher, and preferably 500 ° C. or lower. 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 raised stepwise as it is, and finally from 375 ° C. to 450 ° C. for 30 minutes to 4 hours.
  • the method of heating is mentioned.
  • 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, and preferably 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 according to 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 from the substrate. It can be suitably used for peeling.
  • a release layer is formed on a glass substrate by the method described above.
  • a resin solution for forming a resin substrate is applied, and this coating film is heated to form a resin substrate fixed to the glass substrate via the release layer according to the present invention.
  • the resin 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 a polyimide resin, an acrylic resin, or a cycloolefin polymer resin, which is typical as a resin substrate of a flexible electronic device.
  • Examples of a resin solution for forming the resin substrate include a polyimide solution, a polyamic resin, and the like. Examples include acid solutions, acrylic polymer solutions, and cycloolefin polymer solutions.
  • the method for forming the resin substrate may follow a conventional method.
  • a resin substrate with high transparency a resin substrate formed of an acrylic resin or a cycloolefin polymer resin can be exemplified, and in particular, a substrate having a light transmittance of 80% or more at a wavelength of 400 nm is preferable.
  • 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 polymer substrate can be suitably peeled from the glass carrier using the laser lift-off method (LLO method) that has been used in the manufacture of high-brightness LEDs, three-dimensional semiconductor packages, and the like.
  • LLO method laser lift-off method
  • JP 2013-147599 A In manufacturing a flexible display, a polymer substrate made of polyimide or the like is provided on a glass carrier, and then a circuit or the like including an electrode or the like is formed on the substrate. Finally, the substrate is peeled off from the glass carrier together with the circuit or the like. There is a need.
  • the LLO method is adopted, that is, when a glass carrier is irradiated with a light beam having a wavelength of 308 nm from the surface opposite to the surface on which a circuit or the like is formed, the light beam with the wavelength passes through the glass carrier, Only the nearby polymer (polyimide resin) absorbs this light and evaporates (sublimates). As a result, it has been reported that peeling of the substrate from the glass carrier can be performed selectively without affecting the circuit or the like provided on the substrate, which determines the performance of the display.
  • the composition for forming a release layer of the present invention has a feature of sufficiently absorbing light having a specific wavelength (for example, 308 nm) that can be applied by the LLO method, and thus can be used as a sacrificial layer for the LLO method.
  • Mw weight average molecular weight
  • Mw molecular weight distribution of a polymer
  • GPC apparatus manufactured by JASCO Corporation (column: KD801 and KD805 manufactured by Shodex; eluent: Dimethylformamide / LiBr.H 2 O (29.6 mM) / H 3 PO 4 (29.6 mM) / THF (0.1% by mass); Flow rate: 1.0 mL / min; Column temperature: 40 ° C .; Mw: Standard (Polystyrene equivalent value).
  • resin substrate forming composition A resin substrate forming composition was prepared by the following method.
  • 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% by mass and BCS was 20% by mass to obtain a release layer forming composition L1.
  • Examples 1-2 to 1-10 Except for using the reaction solutions obtained in Synthesis Examples L2 to L10, respectively, instead of the reaction solution obtained in Synthesis Example L1, the release layer forming compositions L2 to L were prepared in the same manner as in Example 1-1. L10 was obtained.
  • Example 1-11 BCS and NMP were added and dissolved in 0.5 g of the polyamide obtained in Synthesis Example P1, and diluted such that the polymer concentration was 5% by mass and BCS was 20% by mass to obtain a release layer forming composition P1. .
  • Example 2-1 Production of release layer and resin substrate [Example 2-1] Using a spin coater (condition: about 3,000 rpm for about 30 seconds), the release layer forming composition L1 obtained in Example 1-1 was applied to a 100 mm ⁇ 100 mm glass substrate (hereinafter the same). 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. 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, thereby obtaining a glass substrate with a release layer.
  • the glass substrate was not removed from the oven, but heated in the oven.
  • the resin substrate forming composition F1 was applied on the release layer (resin thin film) on the glass substrate.
  • the obtained coating film is heated at 80 ° C. for 10 minutes using a hot plate, and then heated at 230 ° C. for 30 minutes using a hot plate to form a resin substrate having a thickness of about 5 ⁇ m on the release layer.
  • a glass substrate with a resin substrate and a release layer was obtained.
  • the light transmittance was measured using an ultraviolet-visible spectrophotometer (UV-2600 manufactured by Shimadzu Corporation). As a result, the resin substrate showed a transmittance of 80% or more at 400 nm.
  • Example 2-2 to 2-5 Example except that the release layer forming compositions L2 to L5 obtained in Examples 1-2 to 1-5 were used in place of the release layer forming composition L1 obtained in Example 1-1.
  • a release layer and a resin substrate were formed in the same manner as in 2-1, and a glass substrate with a release layer and a glass substrate with a resin substrate and a release layer were produced.
  • Example 2-6 Using the release layer forming composition L6 obtained in Example 1-6 instead of the release layer forming composition L1 obtained in Example 1-1, the same method as in Example 2-1. A release layer was formed to obtain a glass substrate with a release layer.
  • the resin substrate forming composition F2 was applied on the release layer (resin thin film) on the glass substrate obtained above.
  • 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 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. for 30 minutes, the heating temperature was raised to 400 ° C.
  • a resin substrate having a thickness of about 20 ⁇ m was formed to obtain a glass substrate with a resin substrate and a release layer. During the temperature increase, the glass substrate was not removed from the oven, but heated in the oven.
  • Example 2-7 Using the release layer forming composition L7 obtained in Example 1-7 instead of the release layer forming composition L1 obtained in Example 1-1, the same method as in Example 2-1. A release layer was formed to obtain a glass substrate with a release layer.
  • the resin substrate forming composition F3 was applied on the release layer (resin thin film) on the glass substrate obtained above.
  • 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. (2 ° C./min.
  • 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. for 30 minutes, the heating temperature was raised to 400 ° C., and the heating temperature was raised to 400 ° C. for 60 minutes.
  • a resin substrate having a thickness of about 20 ⁇ m was formed to obtain a glass substrate with a resin substrate and a release layer. During the temperature increase, the glass substrate was not removed from the oven, but heated in the oven.
  • Example 2-6 was the same as Example 2-6 except that release layer forming composition L8 obtained in Example 1-8 was used instead of release layer forming composition L1 obtained in Example 1-1.
  • a release layer and a resin substrate were formed by the method, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were produced.
  • Example 2-7 was the same as Example 2-7, except that the release layer forming composition L8 obtained in Example 1-8 was used instead of the release layer forming composition L1 obtained in Example 1-1.
  • a release layer and a resin substrate were formed by the method, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were produced.
  • Example 2-7 was the same as Example 2-7 except that the release layer forming composition L9 obtained in Example 1-9 was used instead of the release layer forming composition L1 obtained in Example 1-1.
  • a release layer and a resin substrate were formed by the method, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were produced.
  • Example 2-6 was the same as Example 2-6 except that release layer forming composition L10 obtained in Example 1-10 was used instead of release layer forming composition L1 obtained in Example 1-1.
  • a release layer and a resin substrate were formed by the method, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were produced.
  • Example 2-7 was the same as Example 2-7 except that the release layer forming composition L10 obtained in Example 1-10 was used instead of the release layer forming composition L1 obtained in Example 1-1.
  • a release layer and a resin substrate were formed by the method, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were produced.
  • Example 2-13 Using a spin coater (condition: about 3,000 rpm at about 30 seconds), the release layer forming composition P1 obtained in Example 1-11 was applied onto a 100 mm ⁇ 100 mm glass substrate as a glass substrate. . 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 a release layer having a thickness of about 0.1 ⁇ m was formed on the glass substrate. To obtain a glass substrate with a release layer.
  • Example 2-1 a resin substrate was formed in the same manner as in Example 2-1, to obtain a resin substrate and a glass substrate with a release layer.
  • Example 2-14 Using the release layer forming composition L8 obtained in Example 1-8, a release layer was formed in the same manner as in Example 2-1, to obtain a glass substrate with a release layer. Immediately thereafter, using a spin coater (condition: about 15 seconds at 200 rpm), the resin substrate forming composition F4 was applied on the release layer (resin thin film) on the glass substrate. The obtained coating film was heated at 80 ° C. for 2 minutes using a hot plate, and then heated at 230 ° C. for 30 minutes using a hot plate to form a resin substrate having a thickness of about 3 ⁇ m on the release layer. A glass substrate with a resin substrate and a release layer was obtained. Thereafter, the light transmittance was measured using an ultraviolet-visible spectrophotometer (UV-2600 manufactured by Shimadzu Corporation). As a result, the resin substrate showed a transmittance of 80% or more at 400 nm.
  • UV-2600 ultraviolet-visible spectrophotometer
  • Example 2-14 was the same as Example 2-14 except that the release layer forming composition L9 obtained in Example 1-9 was used instead of the release layer forming composition L8 obtained in Example 1-8.
  • a release layer and a resin substrate were prepared, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were obtained.
  • Example 2-16 Using the release layer forming composition L8 obtained in Example 1-8, a release layer was formed in the same manner as in Example 2-1, to obtain a glass substrate with a release layer. Then, immediately using a spin coater (condition: about 15 seconds at a rotation speed of 200 rpm), the resin substrate forming composition F5 was applied on the release layer (resin thin film) on the glass substrate. The obtained coating film was heated at 80 ° C. for 2 minutes using a hot plate, and then heated at 230 ° C. for 30 minutes using a hot plate to form a resin substrate having a thickness of about 3 ⁇ m on the release layer. A glass substrate with a resin substrate and a release layer was obtained. Thereafter, the light transmittance was measured using an ultraviolet-visible spectrophotometer (UV-2600 manufactured by Shimadzu Corporation). As a result, the resin substrate showed a transmittance of 80% or more at 400 nm.
  • UV-2600 ultraviolet-visible spectrophotometer
  • Example 2-16 was the same as Example 2-16 except that the release layer forming composition L9 obtained in Example 1-9 was used instead of the release layer forming composition L8 obtained in Example 1-8.
  • a release layer and a resin substrate were prepared, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were obtained.
  • Example 2-1 The same procedure as in Example 2-1 except that the release layer forming composition HL1 obtained in Comparative Example 1-1 was used instead of the release layer forming composition L1 obtained in Example 1-1. A release layer and a resin substrate were formed by the method, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were obtained.
  • Example 2-7 was the same as Example 2-7, except that the release layer forming composition HL1 obtained in Comparative Example 1-1 was used instead of the release layer forming composition L1 obtained in Example 1-1.
  • a release layer and a resin substrate were formed by the method, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were obtained.
  • Example 2-3 The same procedure as in Example 2-1 except that the release layer forming composition HL2 obtained in Comparative Example 1-2 was used instead of the release layer forming composition L1 obtained in Example 1-1. A release layer and a resin substrate were formed by the method, and a glass substrate with a release layer and a glass substrate with a resin substrate / release layer were obtained.

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Abstract

L'invention concerne une composition pour former une couche anti-adhésive, ladite composition comprenant un acide polyamique représenté par la formule (1), un acide polyamique représenté par la formule (2), un acide polyamique représenté par la formule (3), ou un polyamide représenté par la formule (4), et un solvant organique. (Dans les formules, X1 représente un groupe aromatique tétravalent ne comprenant pas d'atome de fluor, X2 représente un groupe aromatique tétravalent comprenant un atome de fluor, X3 représente un groupe aromatique divalent ne comprenant pas d'atome de fluor, Y1 représente un groupe aromatique divalent comprenant un atome de fluor, Y2 représente un groupe aromatique divalent comprenant un atome de fluor et m représente un nombre naturel.)
PCT/JP2017/028212 2016-08-03 2017-08-03 Composition pour former une couche anti-adhésive Ceased WO2018025955A1 (fr)

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WO2020226118A1 (fr) * 2019-05-07 2020-11-12 積水化学工業株式会社 Composé ester actif multifonctionnel, composition de résine, produit durci et film d'accumulation
JPWO2020226118A1 (fr) * 2019-05-07 2020-11-12
JP7480040B2 (ja) 2019-05-07 2024-05-09 積水化学工業株式会社 多官能活性エステル化合物、樹脂組成物、硬化物、及び、ビルドアップフィルム
JPWO2021153379A1 (fr) * 2020-01-31 2021-08-05
JP7647589B2 (ja) 2020-01-31 2025-03-18 三菱瓦斯化学株式会社 ポリイミド樹脂、ポリイミドワニス及びポリイミドフィルム
WO2022054765A1 (fr) * 2020-09-10 2022-03-17 三菱瓦斯化学株式会社 Composition de polymère, vernis, et film de polyimide
JPWO2022054765A1 (fr) * 2020-09-10 2022-03-17
JP2022136498A (ja) * 2021-03-08 2022-09-21 日産化学株式会社 剥離層形成用組成物及び剥離層
CN118561762A (zh) * 2024-05-17 2024-08-30 齐齐哈尔大学 一种多芳环桥连双苯并咪唑类pH荧光传感器及其制备方法和应用

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KR102376154B1 (ko) 2022-03-18
CN109476913B (zh) 2022-03-01
TWI746611B (zh) 2021-11-21
JPWO2018025955A1 (ja) 2019-06-13
TW201835158A (zh) 2018-10-01
JP7135857B2 (ja) 2022-09-13

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