WO2020091450A1 - 점착제 조성물, 이를 포함하는 광학 필름, 이를 포함하는 유기 전자 소자 및 표시 장치 - Google Patents

점착제 조성물, 이를 포함하는 광학 필름, 이를 포함하는 유기 전자 소자 및 표시 장치 Download PDF

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Publication number
WO2020091450A1
WO2020091450A1 PCT/KR2019/014574 KR2019014574W WO2020091450A1 WO 2020091450 A1 WO2020091450 A1 WO 2020091450A1 KR 2019014574 W KR2019014574 W KR 2019014574W WO 2020091450 A1 WO2020091450 A1 WO 2020091450A1
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WIPO (PCT)
Prior art keywords
meth
pressure
sensitive adhesive
adhesive composition
acrylate
Prior art date
Application number
PCT/KR2019/014574
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English (en)
French (fr)
Korean (ko)
Inventor
이대혁
유동환
이상진
정세영
이주원
황규석
Original Assignee
주식회사 엘지화학
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Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2021518939A priority Critical patent/JP2022504418A/ja
Priority to CN201980064819.5A priority patent/CN112840005A/zh
Publication of WO2020091450A1 publication Critical patent/WO2020091450A1/ko

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/10—Homopolymers or copolymers of methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/40—OLEDs integrated with touch screens
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/87—Passivation; Containers; Encapsulations
    • H10K59/871—Self-supporting sealing arrangements
    • H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants

Definitions

  • OCAs Optically clear adhesives
  • the electronic display may be an organic light emitting device (OLED), a liquid crystal display (LCD), or the like.
  • the plastic substrate used as a substrate material of the flexible display has a problem in that gas barrier properties such as moisture and oxygen are remarkably low.
  • a barrier film to which various materials and structures are applied on a substrate, or protecting a process surface for protecting a thin film encapsulation (TFE) layer during the manufacturing process of a flexible optical device I have used film.
  • the process surface protective film is temporarily attached to the thin film encapsulation layer during the process and then removed, and then the electronic display and other components are adhered using an optically clear adhesive (OCA). It is a situation that uses the method.
  • OCA optically clear adhesive
  • This application protects the surface of the organic light emitting device during the manufacturing process of the organic electronic device, while the process has a low adhesive force during the process, such as a half-cut process. Want to provide.
  • One embodiment of the present application is the first (meth) acrylate resin; And a second (meth) acrylate resin, wherein the melting temperature (Tm) of the second (meth) acrylate resin is 20 than the glass transition temperature (Tg) of the first (meth) acrylate resin. It provides a pressure-sensitive adhesive composition that is higher than °C.
  • Another exemplary embodiment of the present application is a base layer; And an adhesive layer provided on one surface of the substrate layer, wherein the adhesive layer provides an optical film comprising the aforementioned adhesive composition or a cured product thereof.
  • An exemplary embodiment of the present application is an organic light emitting device; And an adhesive layer in contact with the organic light-emitting device, wherein the adhesive layer comprises the above-described adhesive composition; Or it provides an organic electronic device comprising a cured product.
  • Another embodiment of the present application is an organic light emitting device; touch screen; And an adhesive layer bonding the organic light emitting element and the touch screen, wherein the adhesive layer comprises the aforementioned adhesive composition; Or it provides a display device comprising a cured product thereof.
  • the pressure-sensitive adhesive layer before curing is low to 100 gf / in or less, and after curing, the pressure-sensitive adhesive layer is high to 800 gf / in or higher.
  • the optical film including the pressure-sensitive adhesive layer may protect the surface of the organic light emitting device during the manufacturing process of the organic electronic device.
  • the organic light emitting device and the touch screen can be laminated even without using a separate OCA film, thereby improving processability.
  • the term 'polymer' refers to a compound in which two or more monomers are polymerized, and a component commonly referred to as an oligomer may also be included in the monomer.
  • 'parts by weight' means 'weight ratio'.
  • One embodiment of the present application is the first (meth) acrylate resin; And a second (meth) acrylate resin, wherein the melting temperature (Tm) of the second (meth) acrylate resin is 20 than the glass transition temperature (Tg) of the first (meth) acrylate resin. It provides a pressure-sensitive adhesive composition that is higher than °C.
  • the melting temperature (Tm) of the second (meth) acrylate resin contained in the pressure-sensitive adhesive composition is 20 ° C or higher than the glass transition temperature (Tg) of the first (meth) acrylate resin, the adhesion before curing is low, but the adhesion after curing is A high pressure-sensitive adhesive layer can be implemented.
  • the melting temperature (Tm) of the second (meth) acrylate resin is 20 ° C or higher than the glass transition temperature (Tg) of the first (meth) acrylate resin; 30 ° C or higher; 40 ° C or higher; Or higher than 50 °C.
  • the difference between the melting temperature (Tm) of the second (meth) acrylate resin and the glass transition temperature (Tg) of the first (meth) acrylate resin is not limited, but in one embodiment, 200 ° C. or less; 180 ° C. or less; Or 150 ° C or lower.
  • the adhesive strength (A) before curing of the pressure-sensitive adhesive composition is 100 gf / in or less.
  • the adhesive strength (A) before curing of the pressure-sensitive adhesive composition is 2 gf / in or more; 5 gf / in or more; Or 10 gf / in or more. If the adhesive strength (A) before curing of the pressure-sensitive adhesive composition is less than 2gf / in, the adhesive force between the surface of the adherend and the pressure-sensitive adhesive layer is low, and thus the optical film can be easily peeled off the surface of the adherend.
  • the adhesive strength (A) before curing of the adhesive composition is when the adhesive composition is coated on a polyethylene terephthalate (PET) film and dried at 110 ° C. for 2 minutes to form an adhesive layer having a thickness of 25 ⁇ m, the adhesive layer is made of stainless steel It is the peeling force when peeling from (JIS SUS 304) at a peeling speed of 0.3 m / min and a peeling angle of 180 °.
  • the adhesive force when peeling the pressure-sensitive adhesive layer from the stainless steel sheet is a value measured at 25 ° C. and 50% relative humidity.
  • the melting temperature (Tm) of the second (meth) acrylate resin is 50 ° C or higher than the glass transition temperature (Tg) of the first (meth) acrylate resin.
  • the glass transition temperature (Tg) of the second (meth) acrylate resin When the curing temperature is higher than the glass transition temperature (Tg) of the second (meth) acrylate resin, the mobility of the second (meth) acrylate resin increases during the curing process, so that it floats on the surface of the pressure-sensitive adhesive layer.
  • the second (meth) acrylate resin can permeate between the first (meth) acrylate resin.
  • the adhesive strength of the first (meth) acrylate resin can be realized on the surface of the pressure-sensitive adhesive layer after curing.
  • the curing temperature of the pressure-sensitive adhesive layer is higher than the melting temperature (Tm) of the second (meth) acrylate resin.
  • the mobility of the second (meth) acrylate resin may be further increased during the curing process, before curing of the pressure-sensitive adhesive layer. ⁇ The difference in adhesive force afterwards can be made larger.
  • the adhesive strength after curing of the first (meth) acrylate resin is greater than the adhesive strength before curing of the second (meth) acrylate resin
  • the adhesive strength before curing of the pressure-sensitive adhesive layer corresponds to the adhesive strength before curing of the second (meth) acrylate resin.
  • the adhesive strength after curing of the pressure-sensitive adhesive layer may be realized close to the adhesive strength after curing of the first (meth) acrylate resin.
  • the adhesive strength after curing may increase compared to the adhesive strength before curing of the pressure-sensitive adhesive layer.
  • the viscosity of the second (meth) acrylate resin is lower than that of the first (meth) acrylate resin.
  • the pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition of the present application can be used to bond an organic light emitting device (OLED) and a touch screen.
  • the pressure-sensitive adhesive layer is first adhered to the surface of the organic light emitting element, particularly the encapsulant layer.
  • the pressure-sensitive adhesive layer at this time is in a non-cured state.
  • the pressure-sensitive adhesive layer before curing has a low adhesive strength with the surface of the encapsulant layer, so a half-cut process of the adhesive portion is possible. Thereafter, laminating a touch screen on the pressure-sensitive adhesive layer and subsequently undergoing curing, the pressure-sensitive adhesive strength of the pressure-sensitive adhesive layer is increased. Accordingly, when mass-producing the organic light emitting diode panel, there is no need to use a protective film of the encapsulant layer, and there is an advantage in that a separate OCA (Optically Clear Adhesive) is not required.
  • OCA Optically Clear Adhesive
  • the glass transition temperature (Tg) of the first (meth) acrylate resin is 20 ° C. or less; 10 ° C or lower; 0 ° C or lower; Or -10 ° C or lower.
  • the lower limit of the glass transition temperature (Tg) of the first (meth) acrylate resin may be appropriately selected.
  • the glass transition temperature of the first (meth) acrylate resin is -80 ° C or higher; -70 ° C or higher; Or -60 ° C or higher, but is not limited thereto.
  • the melting temperature (Tm) of the second (meth) acrylate resin is 60 ° C or lower; 55 ° C or lower; Or 55 ° C or lower.
  • the melting temperature (Tm) of the second (meth) acrylate resin is 20 ° C or higher; 25 ° C or higher; 30 ° C or higher; Or 35 ° C or higher.
  • the glass transition temperature (Tg) of the second (meth) acrylate resin is 20 ° C or higher; 25 ° C or higher; Or 30 ° C or higher.
  • the second (meth) acrylate resin and the first (meth) acrylate resin can be used by appropriately selecting physical properties such as molecular weight within the limits satisfying the above-described conditions.
  • the weight average molecular weight of the first (meth) acrylate resin is 500,000 g / mol to 900,000 g / mol. If the molecular weight of the first (meth) acrylate resin is less than the above range, the adhesive strength before curing of the pressure-sensitive adhesive layer may be high, and if it exceeds the above range, the adhesive strength after curing of the pressure-sensitive adhesive layer may be low, so it is preferable to satisfy the above range. .
  • the weight average molecular weight of the first (meth) acrylate resin is 500,000 g / mol or more; 550,000 g / mol or more; Or 600,000 g / mol or more.
  • the weight average molecular weight may mean a converted value for standard polystyrene measured using Gel Permeation Chromatography (GPC) or the like.
  • the second (meth) acrylate resin is contained in 1 to 10 parts by weight compared to 100 parts by weight of the first (meth) acrylate resin. If the second (meth) acrylate resin is contained below the above content, the adhesive strength before curing of the pressure-sensitive adhesive layer may be high, and if it is included above the content, the adhesive strength after curing of the pressure-sensitive adhesive layer may be low.
  • the second (meth) acrylate resin is 10 parts by weight or less compared to 100 parts by weight of the first (meth) acrylate resin; 8 parts by weight or less; 5 parts by weight or less; Or 4 parts by weight or less.
  • the second (meth) acrylate resin is 1 part by weight or more compared to 100 parts by weight of the first (meth) acrylate resin; Or 2 parts by weight or more.
  • the melting temperature (Tm) of the second (meth) acrylate resin is the glass transition temperature of the first (meth) acrylate resin ( Any (meth) acrylate resin may be appropriately selected and used within a range that satisfies Tg) of 20 ° C or higher.
  • (meth) acrylate includes both acrylate and methacrylate.
  • the first and second (meth) acrylate resins are conventional polymerization methods in this field, for example, solution polymerization, photopolymerization, bulk polymerization, suspension polymerization. ) Or emulsion polymerization.
  • the first (meth) acrylate resin may be a copolymer of (meth) acrylate monomers.
  • the crosslinkable functional group-containing monomer means, for example, a monomer capable of being polymerized with the (meth) acrylate monomer and capable of providing a crosslinkable functional group to the (meth) acrylate resin after polymerization.
  • the crosslinkable functional group-containing monomer is a hydroxyl group-containing monomer; Or it may be a carboxyl group-containing monomer.
  • the hydroxy group-containing monomer is 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate , 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate, 2-hydroxypropylene glycol (meth) acrylate, 2-hydroxy Hydroxyethylene glycol (meth) acrylate, 2-hydroxypropylene glycol (meth) acrylate, hydroxyalkylene glycol (meth) acrylate having 2 to 4 carbon atoms in the alkylene group, 4-hydroxybutyl vinyl ether, 5 -Hydroxypentyl vinyl ether, 6-hydroxyhexyl vinyl ether, 7-hydroxyheptyl vinyl ether, 8-hydroxyoctyl vinyl ether, 9-hydroxynonyl vinyl ether, 10-hydroxydecy
  • the carboxyl group-containing monomers include (meth) acrylic acid, 2- (meth) acryloyloxyacetic acid, 3- (meth) acryloyloxypropyl acid, 4- (meth) acryloyloxybutyl acid, acrylic acid doublets, ita Conic acid, maleic acid, maleic anhydride, and the like, but is not limited thereto.
  • the epoxy group-containing monomer is glycidyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, 4,5-epoxyhexyl (meth) acrylate, 6,7-epoxypeptyl (meth) acrylate 1 However, it is not limited thereto.
  • the amide group-containing monomer may be acrylamide, octadecyl acrylamide, isopropyl (meth) acrylamide, aminopropyl (meth) acrylamide, [(dimethylamino) propyl] (meth) acrylamide, but is not limited thereto. .
  • the amine group-containing monomer may be allylamine, 2-aminoethyl (meth) acrylate, N- (3-aminopropyl) (meth) acrylamide, and the like, but is not limited thereto.
  • the oxetanyl group-containing monomers are 3- (acryloyloxymethyl) -3-methyloxetane, 3- (methacryloyloxymethyl) -3-methyloxetane, 3- (acryloyloxymethyl)- 3-ethyloxetane, 3- (methacryloyloxymethyl) -3-ethyloxetane, 3- (acryloyloxymethyl) -3-butyloxetane, 3- (methacryloyloxymethyl)- 3-butyloxetane, 3- (acryloyloxymethyl) -3-hexyloxetane, 3- (methacryloyloxymethyl) -3-hexyloxetane, and the like, but is not limited thereto.
  • the isocyanate group-containing monomer may be 2-isocyanate ethyl (meth) acrylate, 2-isocyanate propyl (meth) acrylate, 4-isocyanate butyl (meth) acrylate, 4-isocyanate pentyl (meth) acrylate, etc. It is not limited.
  • the nitrogen-containing functional group-containing monomer may be (meth) acrylonitrile, N-vinyl pyrrolidone, N-vinyl caprolactam, and the like, but is not limited thereto.
  • the content of the crosslinkable functional group-containing monomer is not particularly limited, and the desired melting temperature (Tm) or glass transition temperature (Tg) of the first (meth) acrylate resin is determined. As long as it can be implemented, it can be appropriately selected.
  • the second (meth) acrylate-based resin may be a copolymer of a (meth) acrylate monomer and a polymerizable functional group-containing polyorganosiloxane.
  • the polymerizable functional group means an unsaturated functional group capable of polymerizing with other monomers constituting the resin.
  • the polymerizable functional group-containing polyorganosiloxane has one polymerizable functional group.
  • crosslinking may proceed too much during the polymerization reaction, resulting in a precipitate that does not dissolve in the solvent or it may be difficult to recover the resin from the reactor.
  • the polymerizable functional group-containing polyorganosiloxane includes a polymerizable functional group at the end of the polyorganosiloxane.
  • the polyorganosiloxane may be present in the side chain of the second (meth) acrylate-based resin.
  • R 1 to R 7 are the same as or different from each other, and each independently an alkyl group
  • the polymerizable functional group-containing polyorganosiloxane may use a commercially available compound, for example, X-24-8201, X-22-174DX, X-22-2426, X-22-2404, X of Shin-Etsu Chemical Industry Co., Ltd. -22-164A, X-22-164C; Toray Dow Corning Corporation BY16-152D, BY16-152, BY16-152C; Alternatively, Chisso FM-0711, FM-0721 and FM-0725 may be used.
  • a commercially available compound for example, X-24-8201, X-22-174DX, X-22-2426, X-22-2404, X of Shin-Etsu Chemical Industry Co., Ltd. -22-164A, X-22-164C; Toray Dow Corning Corporation BY16-152D, BY16-152, BY16-152C; Alternatively, Chisso FM-0711, FM-0721 and FM-0725 may be used.
  • the haze of the pressure-sensitive adhesive layer may be 0.5% to 2%, but is not limited thereto, for example, 1.7% or less; 1.5% or less; Or 1.3% or less.
  • the haze may be a value measured for light having a wavelength of 380 nm or more and 780 nm.
  • the (meth) acrylate monomers that may be included as monomer units in the first (meth) acrylate resin and the second (meth) acrylate resin include an alkyl (meth) acrylate; Aromatic hydrocarbon-containing (meth) acrylates; Hydroxyalkyl (meth) acrylate; Cyclohexyl (meth) acrylate, phenoxy (meth) acrylate, 2-ethylphenoxy (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, 2-ethylthiophenyl (meth) acrylic Rate, 2-phenylethyl (meth) acrylate, 3-phenylpropyl (meth) acrylate, 4-phenylbutyl (meth) acrylate, 2,2-methylphenylethyl (meth) acrylate, 2,3-methylphenylethyl (Meth) acrylate, 2,4-methylphenylethyl
  • the first (meth) acrylate resin is 40% to 80% by weight of alkyl (meth) acrylate relative to 100% by weight of the total monomer constituting the first (meth) acrylate-based resin; And 20% to 60% by weight of hydroxyalkyl (meth) acrylate.
  • the first (meth) acrylate resin is 50% to 70% by weight of the alkyl (meth) acrylate relative to 100% by weight of the total monomer constituting the first (meth) acrylate-based resin; And 30% to 50% by weight of hydroxyalkyl (meth) acrylate.
  • the second (meth) acrylate resin is 60% to 90% by weight of alkyl (meth) acrylate relative to 100% by weight of the total monomers constituting the second (meth) acrylate-based resin; And 10% to 40% by weight of a polyorganosiloxane containing a polymerizable functional group.
  • the concentration of the solid content of the pressure-sensitive adhesive composition is 15% to 50% by weight; 20% to 50% by weight; Or 25% to 50% by weight.
  • the concentration (% by weight) of the solid content of the pressure-sensitive adhesive composition means (weight of the solid content of the pressure-sensitive adhesive composition) / (weight of the pressure-sensitive adhesive composition) * 100.
  • the isocyanate-based crosslinking agent is tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate, naphthalene Diisocyanate, triphenylmethane triisocyanate, methylene bistriisocyanate, and the like, but is not limited thereto.
  • the epoxy-based crosslinking agent is ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol Diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, polytetramethylene glycol diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, Diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, resolcin diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol Poly
  • the aziridine crosslinking agent is N, N'-toluene-2,4-bis (1-aziridinecarboxamide), N, N'-diphenylmethane-4,4'-bis (1-aziridinecarboxamide) ), Bisisopropaloyl-1- (2-methylaziridine), tri-1-aziridinylphosphine oxide, and the like, but is not limited thereto.
  • the crosslinking agent may be included in 0.5 parts by weight to 10 parts by weight, preferably 0.5 parts by weight to 5 parts by weight based on 100 parts by weight of the sum of the weights of the first and second (meth) acrylate resins. have.
  • the cohesive force of the pressure-sensitive adhesive may be increased to prevent steaming of the pressure-sensitive adhesive layer.
  • One embodiment of the present application is a base layer; And as an optical film comprising an adhesive layer provided on one surface of the base layer, provides an optical film comprising the above-described adhesive composition or a cured product thereof.
  • the pressure-sensitive adhesive layer includes a first (meth) acrylate resin and a second (meth) acrylate resin.
  • 10 mg of the pressure-sensitive adhesive layer is collected from the optical film, placed in an aluminum pan, mounted on a differential scanning calorimeter (DSC Q100, TA instrument), and heated at 20 ° C / min at -30 ° C to 100 ° C
  • DSC Q100 differential scanning calorimeter
  • Tg glass transition temperature
  • Tm melting temperatures
  • the optical film may further include a protective layer provided on the opposite side of the surface of the pressure-sensitive adhesive layer provided with the base layer.
  • One embodiment of the present application is a base layer; Protective layer; And an adhesive layer provided between the base layer and the protective layer, wherein the adhesive layer provides an optical film comprising the aforementioned adhesive composition or a cured product thereof.
  • One embodiment of the present application is a step of coating the pressure-sensitive adhesive composition on one surface of the base layer; It provides an optical film manufacturing method comprising the step of drying the coated pressure-sensitive adhesive composition to form a pressure-sensitive adhesive layer.
  • a known coating method such as a reverse coating method, a gravure coating method, a spin coating method, a screen coating method, a fountain coating method, a dipping method, or a spray method can be used, but is not limited thereto.
  • Drying of the coated pressure-sensitive adhesive composition may be performed at an appropriate temperature and time. In one embodiment, the drying of the coated pressure-sensitive adhesive composition may be performed for 30 seconds to 5 minutes at a temperature of 80 ° C to 150 ° C using an oven, but is not limited thereto.
  • the method for manufacturing the optical film may further include attaching a protective layer to the opposite side of the surface on which the base film of the pressure-sensitive adhesive layer is provided after the pressure-sensitive adhesive layer forming step.
  • the base layer includes a base film.
  • the protective layer includes a protective film.
  • the types of the base film and the protective film are not particularly limited.
  • the base film is, for example, polyethylene terephthalate film, polytetrafluoroethylene film, polyethylene film, polypropylene film, polybutene film, polybutadiene film, vinyl chloride copolymer film, polyurethane film, ethylene-vinyl acetate film , Ethylene-propylene copolymer film, ethylene-acrylic acid ethyl copolymer film, ethylene-acrylic acid methyl copolymer film or polyimide film may be used, but is not limited thereto.
  • the base film and the protective film may be polyethylene terephthalate (PET) film.
  • PET polyethylene terephthalate
  • the base film and the protective film may be composed of a single layer, or two or more layers may be laminated.
  • the thickness of the base film and the protective film may be appropriately selected in consideration of the purpose of the present application.
  • the thickness of the base film may be 50 ⁇ m or more and 125 ⁇ m or less, or 60 ⁇ m or more and 100 ⁇ m or less.
  • the thickness of the pressure-sensitive adhesive layer containing the above-described pressure-sensitive adhesive composition or a cured product thereof is 50 ⁇ m or less; 45 ⁇ m or less; Or 40 ⁇ m or less.
  • the thickness of the pressure-sensitive adhesive layer containing the pressure-sensitive adhesive composition or a cured product thereof means the thickness of the pressure-sensitive adhesive layer before curing.
  • the thickness of the pressure-sensitive adhesive layer comprising the above-described pressure-sensitive adhesive composition or a cured product thereof is 15 ⁇ m or more; 20 ⁇ m or more; Or it may be 25 ⁇ m or more.
  • the stepped portion of the panel may not be overcome, and if it exceeds the above range, cohesion of the pressure-sensitive adhesive layer may be weak and steaming may occur.
  • the adhesive strength (A) of the pressure-sensitive adhesive layer containing the pressure-sensitive adhesive composition or a cured product thereof is 100 gf / in or less.
  • the organic light emitting device sequentially includes a back plate, a plastic substrate, a thin film transistor, an organic light emitting diode, and an encapsulation layer.
  • the pressure-sensitive adhesive layer is provided on the sealing layer of the organic light emitting device.
  • the pressure-sensitive adhesive layer is provided in contact with the sealing layer of the organic light emitting device.
  • An exemplary embodiment of the present application provides a method of manufacturing an organic electronic device comprising attaching the pressure-sensitive adhesive layer of the optical film to the encapsulation layer of the organic light-emitting device.
  • the method of manufacturing the organic electronic device may further include removing the protective layer from the optical film prior to attaching the adhesive layer to the organic light emitting device.
  • the method of manufacturing the organic electronic device may further include attaching a touch screen on the adhesive layer after attaching the adhesive layer to the organic light emitting device.
  • the method of manufacturing an organic electronic device further comprises removing a base layer from the optical film between attaching the adhesive layer to the organic light emitting device and attaching a touch screen on the adhesive layer. It can contain.
  • the method of manufacturing the organic electronic device may further include curing the pressure-sensitive adhesive layer after attaching a touch screen on the pressure-sensitive adhesive layer.
  • the method of curing the pressure-sensitive adhesive composition is not particularly limited, and for example, a curing method through an appropriate heating, drying and / or aging process may be employed.
  • curing of the pressure-sensitive adhesive layer may be achieved by pressing at 0.3Mpa to 0.6Mpa for 10 minutes to 30 minutes at a temperature of 40 ° C to 60 ° C using an autoclave.
  • the pressure-sensitive adhesive layer may further undergo an appropriate aging process after the curing step. In one embodiment, the aging process of the pressure-sensitive adhesive layer may be performed for 4 to 6 days at 30 °C to 50 °C. In one embodiment, the aging process of the pressure-sensitive adhesive layer may be performed at 40 ° C for 5 days.
  • An exemplary embodiment of the present application is an organic light emitting device; touch screen; And an adhesive layer bonding the organic light emitting element and the touch screen, wherein the adhesive layer includes the aforementioned adhesive composition; Or it provides a display device comprising a cured product thereof.
  • the cured product of the pressure-sensitive adhesive composition is a mixture of the first (meth) acrylate and the second (meth) acrylate resin using an autoclave (Autoclave) at any one of the temperature of 40 °C to 60 °C It means a material pressurized at a pressure of 0.3Mpa to 0.6Mpa for any one of 10 to 30 minutes.
  • Autoclave Autoclave
  • the light transmittance of the visible light region of the pressure-sensitive adhesive layer containing the cured product of the pressure-sensitive adhesive composition is 50% or more, 60% or more, 70% or more, 80% or more, or 90% or more.
  • the light transmittance may be measured using a spectrophotometer (n & k spectrometer, manufactured by n & k Technology).
  • a spectrophotometer n & k spectrometer, manufactured by n & k Technology.
  • the thickness after curing of the pressure-sensitive adhesive composition is ⁇ 0.1% or less compared to the thickness before curing.
  • the adhesive strength (B) of the pressure-sensitive adhesive layer containing a cured product of the pressure-sensitive adhesive composition is 800 gf / in or more; 1,000 gf / in or more; 1,500 gf / in or more; 2,000 gf / in or more; Or 2,500 gf / in or more.
  • the usage form of the adhesive composition to an organic light emitting element was demonstrated.
  • the use of the pressure-sensitive adhesive composition of the present invention is not limited to the above use, and may be used for surface protection of the adherend in the manufacturing process of other organic photoelectric devices, organic transistors, organic solar cells, etc. or for bonding with other members. .
  • methyl methacrylate (MMA) 8 middle portion and 2-ethylhexyl acrylate (2-EHA) 22 Ethyl Acetate (EAc) was added so that the solid content concentration was 27% by weight after the monomer mixture composed of the middle portion was introduced.
  • the reactor temperature was maintained at 80 ° C.
  • azobisisobutyronitrile (AIBN: Azobisisobutronitrile) was added as a reaction initiator in 3 parts by weight relative to 100 parts by weight of the monomer mixture, and the mixture was reacted.
  • AIBN Azobisisobutronitrile
  • An adhesive composition was prepared by mixing 30 parts by weight of resin 1-1, 1 part by weight of resin 2-1 and 20 parts by weight of toluene.
  • a 75 ⁇ m thick polyethylene terephthalate (PET) film (AF34V, SKCHMT) was prepared as a base film. Subsequently, the pressure-sensitive adhesive composition was coated on the base film and then dried in an oven at 110 ° C. for 2 minutes to prepare a 25 ⁇ m thick pressure-sensitive adhesive layer.
  • PET polyethylene terephthalate
  • SKCHMT polyethylene terephthalate
  • the optical film was cut to a width of 25 mm and a length of 210 mm to prepare a specimen.
  • the protective layer was peeled at a peel angle of 180 ° and a peel rate of 1.8 m / min, and the pressure-sensitive adhesive layer of the specimen was attached to a stainless steel sheet (JIS SUS 304) with a 2 kg roller.
  • the optical film was cut to a width of 25 nm and a length of 210 mm to prepare a specimen.
  • the protective layer was peeled at a peel angle of 180 ° and a peel rate of 1.8 m / min, and the pressure-sensitive adhesive layer of the specimen was attached to a stainless steel sheet (JIS standard SUS 304) with a 2 kg roller. Subsequently, an autoclave was used for 20 minutes at a temperature of 50 ° C. and a pressure of 0.5 Mpa.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Laminated Bodies (AREA)
PCT/KR2019/014574 2018-10-31 2019-10-31 점착제 조성물, 이를 포함하는 광학 필름, 이를 포함하는 유기 전자 소자 및 표시 장치 WO2020091450A1 (ko)

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JP2021518939A JP2022504418A (ja) 2018-10-31 2019-10-31 粘着剤組成物、これを含む光学フィルム、これを含む有機電子素子および表示装置
CN201980064819.5A CN112840005A (zh) 2018-10-31 2019-10-31 粘合剂组合物、包含其的光学膜、以及均包含其的有机电子元件和显示装置

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KR1020180132596A KR102324617B1 (ko) 2018-10-31 2018-10-31 점착제 조성물 및 상기 조성물 또는 상기 조성물의 경화물을 포함하는 광학 부재

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JP2016155942A (ja) * 2015-02-25 2016-09-01 東洋インキＳｃホールディングス株式会社 粘着剤組成物、およびそれを用いてなる粘着シート
KR20170114861A (ko) * 2016-04-06 2017-10-16 주식회사 엘지화학 점착 조성물, 이의 제조방법 및 점착제
JP2018027996A (ja) * 2016-08-15 2018-02-22 日東電工株式会社 フレキシブル画像表示装置用粘着剤層、フレキシブル画像表示装置用積層体、及び、フレキシブル画像表示装置
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JP2016155942A (ja) * 2015-02-25 2016-09-01 東洋インキＳｃホールディングス株式会社 粘着剤組成物、およびそれを用いてなる粘着シート
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JP2018027996A (ja) * 2016-08-15 2018-02-22 日東電工株式会社 フレキシブル画像表示装置用粘着剤層、フレキシブル画像表示装置用積層体、及び、フレキシブル画像表示装置
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CN112840005A (zh) 2021-05-25
KR102324617B1 (ko) 2021-11-09

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