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WO2022216367A1 - Composition d'adhésif sensible à la pression et ses procédés de préparation et d'utilisation dans des applications de diodes électroluminescentes organiques flexibles - Google Patents

Composition d'adhésif sensible à la pression et ses procédés de préparation et d'utilisation dans des applications de diodes électroluminescentes organiques flexibles Download PDF

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WO2022216367A1
WO2022216367A1 PCT/US2022/016542 US2022016542W WO2022216367A1 WO 2022216367 A1 WO2022216367 A1 WO 2022216367A1 US 2022016542 W US2022016542 W US 2022016542W WO 2022216367 A1 WO2022216367 A1 WO 2022216367A1
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Prior art keywords
composition
sensitive adhesive
pressure sensitive
starting material
subscript
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English (en)
Inventor
Hanna Yang
Wonbum JANG
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Dow Silicones Corp
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Dow Silicones Corp
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Priority to JP2023560934A priority Critical patent/JP2024515526A/ja
Priority to KR1020237037864A priority patent/KR20230170009A/ko
Priority to CN202280019902.2A priority patent/CN116998005A/zh
Publication of WO2022216367A1 publication Critical patent/WO2022216367A1/fr
Anticipated expiration legal-status Critical
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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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • 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
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • 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
    • C09J2483/00—Presence of polysiloxane
    • 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
    • H10K59/873—Encapsulations

Definitions

  • This invention relates to a pressure sensitive adhesive composition that is useful in processes for fabricating flexible organic light emitting diode (OLED) displays.
  • the pressure sensitive adhesive composition cures to form a pressure sensitive adhesive with low initial adhesion, high adhesion stability over time, and low migration.
  • an OLED is formed on a relatively rigid substrate (e.g., glass or glass coated with a polyimide varnish), and a passivation layer is formed on the surface of the OLED opposite the substrate.
  • a relatively rigid substrate e.g., glass or glass coated with a polyimide varnish
  • a passivation layer is formed on the surface of the OLED opposite the substrate.
  • the rigid substrate is removed. Weak or brittle layers need to be protected from damage (e.g. , scratches or other shocks) during the further processing.
  • a protective film with low adhesion is desired to prevent delamination of a layer (e.g., passivation layer) on a surface of an OLED module during releasing of the protective film after use. If adhesion control fails and adhesion increase with time (/. ⁇ ? ., during the fabricating process), the layer may delaminate or be damaged when the protective film is removed. Therefore, there is an industry need to provide protective films with low adhesion and high adhesion stability (where adhesion does not increase during the time needed for the fabrication process to an extent that would cause delamination or damage).
  • a pressure sensitive adhesive composition comprises: a poly(dialkylsiloxane/alkylalkenylsiloxane) copolymer, where the poly(dialkylsiloxane/alkylalkenylsiloxane) copolymer has silicon bonded alkyl groups with 1 to 10 carbon atoms and silicon bonded alkenyl groups with 2 to 6 carbon atoms, and where the alkenyl groups are present in an amount 0.14% to ⁇ 0.3% based on the weight of the poly(dialkylsiloxane/alkylalkenylsiloxane) copolymer, polyalkylhydrogensiloxane having unit formula
  • each R1 is an independently selected alkyl group of 1 to 10 carbon atoms, subscript x > 0, subscript y > 0, and a quantity (x + y) is sufficient to give the polyalkylhydrogensiloxane a viscosity of ⁇ 20 mPa-s, a platinum group metal catalyst, and an acetylenic alcohol, and an organic solvent.
  • a method for preparing the pressure sensitive adhesive composition, a method of using the pressure sensitive adhesive composition to form a pressure sensitive adhesive tape, and a method for fabricating a flexible organic light emitting diode device using the pressure sensitive adhesive tape are also disclosed.
  • the pressure sensitive adhesive composition comprises:
  • G 10 weight % to 90 weight%, based on combined weights of all starting materials in the composition, of an organic solvent; with the proviso that all starting materials in the composition combined have a molar ratio of silicon bonded hydrogen atoms / silicon bonded alkenyl groups (SiH: Alkenyl ratio) of 0.5:1 to 2:1.
  • Starting Material A) Polyidialkylsiloxane/alkylalkenylsiloxane) Copolymer
  • Starting material A) in the pressure sensitive adhesive composition is a poly(dialkylsiloxane/alkylalkenylsiloxane) copolymer, which has silicon bonded alkyl groups with 1 to 10 carbon atoms and silicon bonded alkenyl groups with 2 to 6 carbon atoms, and where the alkenyl groups are present in an amount of 0.14% to ⁇ 0.3% based on the weight of the poly(dialkylsiloxane/alkylalkenylsiloxane) copolymer.
  • starting material A) may contain at least 0.15%, alternatively > 0.20%, alternatively at least 0.21%, and alternatively at least 0.22% alkenyl groups; while at the same time starting material A) may contain up to 0.29%, alternatively up to 0.28%, alternatively up to 0.27%, alternatively up to 0.26%, alternatively up to 0.25%, alternatively up to 0.24%, alternatively up to 0.23%, alternatively up to 0.22%, and alternatively up to 0.21% of alkenyl groups, on the same basis.
  • the poly(dialkylsiloxane/alkylalkenylsiloxane) copolymer may contain 0.14% to ⁇ 0.3%, alternatively > 0.20% to 0.26% alkenyl groups and alternatively 0.202% of alkenyl groups.
  • the pressure sensitive adhesive prepared from the composition may cause burrs, which cause damage to the passivation layer when the pressure sensitive adhesive film is removed during fabrication of an electronic device, such as a flexible organic light emitting diode device.
  • Starting material A may be free of silicon bonded aromatic hydrocarbyl groups.
  • Starting material A contains no aromatic hydrocarbyl groups (such as phenyl, tolyl, xylyl or benzyl) or an amount of aromatic hydrocarbyl groups that is non-detectable by digestive gas chromatography mass spectrometry (GCMS) analysis.
  • aromatic hydrocarbyl groups such as phenyl, tolyl, xylyl or benzyl
  • GCMS digestive gas chromatography mass spectrometry
  • subscripts d, e, f, and g have values such that 2 > d > 0, 2 > e > 0, 70 > f > 0, 10,000 > g > 0.
  • subscript f may have a value such that 50 > f > 0, alternatively that 40 > f > 10 and alternatively that 37 > f > 20.
  • subscript g may have a value such that 9,500 > g > 0, alternatively 5,500 > g > 4,000, alternatively 5,000 > g > 4,500, and alternatively 4,950 > g > 4,450.
  • Subscripts d, e, f, and g have values selected such that the poly(dialkylsiloxane/alkylalkenylsiloxane) has the alkenyl content described above.
  • subscripts d, e, f, and g may have values such that number average molecular weight (Mn) of starting material A) is at least 200,000 g/mol; alternatively at least 250,000 g/mol; alternatively at least 300,000 g/mol, and alternatively at least 330,000 g/mol; while at the same time Mn may be up to 500,000 g/mol, alternatively up to 450,000 g/mol, alternatively up to 400,000 g/mol, and alternatively up to 370,000 g/mol, measured by Gel Permeation Chromatography according to the test method in U.S. Patent 9,593,209 at col. 31, Reference Example 1.
  • each R1 is independently an alkyl group of 1 to 10 carbon atoms and each is independently an alkenyl group of 2 to 6 carbon atoms.
  • Suitable alkyl groups include branched or unbranched, saturated monovalent hydrocarbon groups.
  • Alkyl is exemplified by, but not limited to, methyl, ethyl, propyl (e.g., iso-propyl and/or n-propyl), butyl (e.g., isobutyl, n-butyl, tert-butyl, and/or sec -butyl), pentyl (e.g., isopentyl, neopentyl, and/or tert-pentyl), hexyl, heptyl, octyl, nonyl, and decyl, as well as branched saturated monovalent hydrocarbon groups of 6 to 10 carbon atoms.
  • propyl e.g., iso-propyl and/or n-propyl
  • butyl e.g., isobutyl, n-butyl, tert-butyl, and/or sec -butyl
  • pentyl e.g.
  • each R1 may be selected from methyl, ethyl, and iso-propyl.
  • each R1 may be methyl.
  • Suitable alkenyl groups include branched or unbranched monovalent hydrocarbon groups having a terminal double bond.
  • Alkenyl is exemplified by, but not limited to, vinyl, allyl, butenyl (e.g., isobutenyl, n-butenyl, tert-butenyl and/or sec-butenyl), and hexenyl, including branched and linear groups of 6 carbon atoms.
  • each may be alkenyl.
  • each R ⁇ may be vinyl, allyl, or hexenyl.
  • each R ⁇ may be vinyl or hexenyl.
  • the alkenyl content of starting material A) may be calculated by calculating the total molecular weight of the poly(dialkylsiloxane/alkylalkenylsiloxane), calculating the molecular weights of each unit containing an alkenyl group, and dividing the combined molecular weights of each unit containing an alkenyl group by the total molecular weight.
  • starting material A is a dimethylvinylsiloxy-terminated poly(dimethylsiloxane/methylvinylsiloxane) copolymer ( M Vl 2D Vl 25 D4g29 ) with number average molecular weight (Mn) and alkenyl (vinyl) content calculated as follows:
  • Mw of M 93.20 g/mol
  • Mw of D 74.15 g/mol
  • Mw of D 86.17 g/mol g/mol
  • Starting material A) is exemplified by i) dimethyl vinylsiloxy-terminated poly (dimethylsiloxane/methylvinylsiloxane) , ii) dimethylvinylsiloxy-terminated polymethylvinylsiloxane, iii) trimethylsiloxy-terminated poly(dimethylsiloxane/methylvinylsiloxane), iv) trimethylsiloxy-terminated polymethylvinylsiloxane, v) dimethylvinylsiloxy-terminated poly (dimethylsiloxane/methylvinylsiloxane) , vi) dimethylhexenylsiloxy-terminated poly(dimethylsiloxane/methylhexenylsiloxane), vii) dimethylhexenylsiloxy-terminated polymethylhexenylsiloxane, viii) trimethylsiloxy-terminated poly (dimethylsimethyls
  • Starting material A) may be one poly(dialkylsiloxane/alkylalkenylsiloxane) copolymer or a combination of two or more poly(dialkylsiloxane/alkylalkenylsiloxane) copolymers that vary in at least one property such as selection of alkyl group, selection of alkenyl group, molecular weight, and number of dialkylsiloxane units and alkylalkenylsiloxane units.
  • the pressure sensitive adhesive composition may optionally further comprise starting material B) a polyalkylsiloxane resin.
  • the polyalkylsiloxane resin is an MQ resin consisting essentially of R ⁇ SiO ⁇ (M) units and S1O4/2 (Q) units, where each R3 is independently selected from the group consisting of an alkyl group of 1 to 10 carbon atoms such as that described for R1, and an alkenyl group of 2 to 6 carbon atoms such as that described above for R2.
  • Starting material B) may be free of silicon bonded aromatic hydrocarbon groups.
  • the polyorganosilicate resin comprises the M and Q units described above, and the polyorganosilicate resin further comprises units with silanol (silicon bonded hydroxyl) groups and may comprise neopentamer of formula S i t O S i R ⁇ 3 J4 , where R3 is as described above.
  • Si ⁇ 9 Nuclear Magnetic Resonance (NMR) spectroscopy as described in U.S. Patent 9,593,209 at col. 32, Reference Example 2, may be used to measure molar ratio of M and Q units, where said ratio is expressed as
  • Mn of the polyorganosilicate resin depends on various factors including the types of hydrocarbon groups represented by R ⁇ that are present.
  • the Mn of the polyorganosilicate resin refers to the number average molecular weight measured using gel permeation chromatography (GPC) according to the procedure in U.S. Patent 9,593,209 at col. 31,
  • the Mn of the polyorganosilicate resin may be greater than 2,000 g/mol, alternatively > 2,000 g/mol to 10,000 g/mol, and alternatively 3,000 g/mol to 8,000 g/mol. Alternatively, Mn of the polyorganosilicate resin may be 4,000 g/mol to 7,000 g/mol.
  • U.S. Patent 8,580,073 at col. 3, line 5 to col. 4, line 31, is hereby incorporated by reference for disclosing silicone resins, which are suitable polyorganosilicate resins for use herein.
  • the polyorganosilicate resin can be prepared by any suitable method, such as cohydrolysis of the corresponding silanes or by silica hydrosol capping methods.
  • the polyorganosilicate resin may be prepared by silica hydrosol capping processes such as those disclosed in U.S. Patent 2,676,182 to Daudt, et al.; U.S. Patent 4,611,042 to Rivers-Farrell et al.; and U.S. Patent 4,774,310 to Butler, et al.
  • the method of Daudt, et al. described above involves reacting a silica hydrosol under acidic conditions with a hydrolyzable triorganosilane such as trimethylchlorosilane, a siloxane such as hexamethyldisiloxane, or mixtures thereof, and recovering a copolymer having M units and Q units.
  • a hydrolyzable triorganosilane such as trimethylchlorosilane, a siloxane such as hexamethyldisiloxane, or mixtures thereof
  • the resulting copolymers generally contain from 2 to 5 percent by weight of silicon bonded hydroxyl (silanol) groups.
  • the intermediates used to prepare the polyorganosilicate resin may be triorganosilanes and silanes with four hydrolyzable substituents or alkali metal silicates.
  • the triorganosilanes may have formula R ⁇ SiXl, where R3 is as described above and c ⁇ represents a hydrolyzable substituent such as halogen, alkoxy, acyloxy, hydroxyl, oximo, or ketoximo; alternatively, halogen, alkoxy or hydroxyl.
  • Silanes with four hydrolyzable substituents may have formula SiX- ⁇ 4, where each is halogen, alkoxy or hydroxyl.
  • Suitable alkali metal silicates include sodium silicate.
  • the polyorganosilicate resin prepared as described above typically contains silicon bonded hydroxyl groups, e.g., in units of formulae, HOS13/2 and/or HOR- ⁇ SiO
  • the polyorganosilicate resin may comprise up to 2% of silicon bonded hydroxyl groups.
  • the concentration of silicon bonded hydroxyl groups present in the polyorganosilicate resin may be determined using Fourier Transform- Infra Red (FTIR) spectroscopy according to ASTM Standard E- 168- 16.
  • FTIR Fourier Transform- Infra Red
  • Silicon bonded hydroxyl groups formed during preparation of the polyorganosilicate resin can be converted to trihydrocarbyl-siloxy groups or to a different hydrolyzable group by reacting the polyorganosilicate resin with a silane, disiloxane, or disilazane containing the appropriate terminal group.
  • Silanes containing hydrolyzable groups may be added in molar excess of the quantity required to react with the silicon bonded hydroxyl groups on the polyorganosilicate resin.
  • the polyorganosilicate resin may further comprises 2% or less, alternatively 0.7% or less, and alternatively 0.3% or less, and alternatively 0.3% to 0.8% of units represented by formula XS1O3/2 and/or NXR- ⁇ SiO 1/2 where R ⁇ is as described above, and X represents a hydrolyzable substituent, as described above for c ⁇ .
  • the polyorganosilicate resin may have terminal aliphatically unsaturated groups.
  • the polyorganosilicate resin having terminal aliphatically unsaturated groups may be prepared by reacting the product of Daudt, et al. with an unsaturated organic group-containing endblocking agent and an endblocking agent free of aliphatic unsaturation, in an amount sufficient to provide from 3 to 30 mole percent of unsaturated organic groups in the final product.
  • endblocking agents include, but are not limited to, silazanes, siloxanes, and silanes. Suitable endblocking agents are known in the art and exemplified in U.S. Patents 4,584,355; 4,591,622; and 4,585,836. A single endblocking agent or a mixture of such agents may be used to prepare such resin.
  • the polyalkylsiloxane resin may comprise unit formula (II): are as described above, subscripts a, b, and c represent mole fractions with values such that subscript a > 0, subscript b > 0, subscript c > 0, a quantity (a+b) > 0, and subscripts a, b, and c have values such that 0.9 ⁇ (a+b)/c ⁇ 1.3.
  • the amount of starting material B) in the pressure sensitive adhesive composition depends on various factors including the desired form of the reaction product of the composition, the quantity and hydrosilylation reactivity of the alkenyl groups of starting material A), the type and amount of catalyst, and the content of silicon bonded hydrogen atoms of starting material C). However, the amount of starting material B) may range from 0 to 15 parts by weight, per 100 parts by weight of starting material A); alternatively > 0 to 15 parts by weight on the same basis.
  • the pressure sensitive adhesive composition further comprises starting material C) a polyalkylhydrogensiloxane.
  • the poly alky lhydrogensiloxane has unit formula (III): described above.
  • subscript x > 0, subscript y > 0, and a quantity (x + y) is sufficient to give the polyalkylhydrogensiloxane a viscosity of ⁇ 20 mPa-s, alternatively 8 mPa-s to 16 mPa-s, where viscosity is measured by capillary viscometer at 25 deg C.
  • Subscript x may be sufficient to give starting material C), the polyalkylhydrogensiloxane, an SiH content > 0 to ⁇ 1%, alternatively > 0 to 0.75%, based on weight of starting material C).
  • Polyalkylhydrogensiloxanes for starting material C) are exemplified by: a) dimethylhydrogensiloxy-terminated polydimethylsiloxane, b) dimethylhydrogensiloxy-terminated poly (dimethylsiloxane/methy lhydrogensiloxane) , c) dimethylhydrogensiloxy-terminated polymethylhydrogensiloxane, and d) a combination of two or more of a), b), and c).
  • the exact amount of starting material C) in the composition depends on various factors including reactivity of starting material A), whether starting material B) is present, and the type and amount of any additional starting materials (e.g., starting material D)), if present.
  • the amount of starting material C) in the pressure sensitive adhesive composition may be 0.1 % to 5%, alternatively 0.5% to 3%, and alternatively 0.5% to 2% based on combined weights of all starting materials in the composition.
  • starting material A alkenyl content of starting material A) and any other starting materials in the composition that contain silicon bonded alkenyl groups (e.g., starting material B) and starting material C), when alkenyl functional) and the SiH content of starting material B) and any other SiH containing materials in the pressure sensitive adhesive composition (e.g., starting material
  • Starting material D is an anchorage additive that may optionally be included in the pressure sensitive adhesive composition.
  • the anchorage additive will facilitate bonding to a substrate by a pressure sensitive adhesive prepared by curing the pressure sensitive adhesive composition described herein.
  • the presence of the anchorage additive will not detrimentally affect the desired peel force allowing the pressure sensitive adhesive to be removed from an electronic device without damaging the device or leaving significant residue.
  • Suitable anchorage additives include silane coupling agents such as methyltrimethoxysilane, vinyltrimethoxysilane, allyltrimethoxysilane, 3- methacryloxypropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3- aminopropyltrimethoxysilane, bis(trimethoxysilyl)propane, and bis(trimethoxysilyl)hexane; and mixtures or reaction mixtures of said silane coupling agents.
  • silane coupling agents such as methyltrimethoxysilane, vinyltrimethoxysilane, allyltrimethoxysilane, 3- methacryloxypropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3- aminopropyltrimethoxysilane, bis(trimethoxysilyl)propan
  • the anchorage additive may be tetramethoxysilane, tetraethoxysilane, dimethyldimethoxysilane, methylphenyldimethoxysilane, methylphenyldiethoxysilane, phenyltrimethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, vinyltriethoxysilane, allyltriethoxysilane, 3- glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, -(3,4- epoxycyclohexyl)ethyltrimethoxysilane or 3-methacryloxypropyl trimethoxysilane.
  • the anchorage additive may be exemplified by a reaction product of an alkenyl-functional alkoxysilane (e.g., a vinyl alkoxysilane) and an epoxy-functional alkoxysilane; a reaction product of an alkenyl-functional acetoxysilane (such as vinyl acetoxysilane) and epoxy-functional alkoxysilane; and a combination (e.g., physical blend and/or a reaction product) of a polyorganosiloxane having at least one aliphatically unsaturated hydrocarbon group and at least one hydrolyzable group per molecule and an epoxy-functional alkoxysilane (e.g., a combination of a hydroxy-terminated, vinyl functional polydimethylsiloxane with glycidoxypropyl trimethoxysilane).
  • an alkenyl-functional alkoxysilane e.g., a vinyl alkoxysilane
  • Suitable anchorage additives and methods for their preparation are disclosed, for example, in U.S. Patent 9,562,149; U.S. Patent Application Publication Numbers 2003/0088042, 2004/0254274, 2005/0038188, 2012/0328863 at paragraph [0091], and U.S. Patent Publication 2017/0233612 at paragraph [0041]; and EP 0 556023.
  • Anchorage additives are commercially available.
  • SYL-OFFTM 297, SYF-OFFTM 397, and SYF-OFFTM 9176 are available from Dow Silicones Corporation of Midland, Michigan, USA.
  • Other exemplary anchorage additives include D-l) vinyltriacetoxysilane, D-2) glycidoxypropyltrimethoxysilane, D-3) 2-(3,4- epoxycyclohexyl)ethyltrimethoxysilane, D-4) a combination of two or more of D-l), D-2) and D-3); and D-5) a combination of any of D-l), D-2), D-3) and/or D-4), and a polydimethylsiloxane terminated with hydroxyl groups, methoxy groups, or terminated with both a hydroxy group and a methoxy group.
  • the combinations D-4) and D-5) may be physical blends and/or reaction products.
  • the amount of anchorage additive depends on various factors including the type of substrate to which the composition will be applied and whether a primer or other surface treatment will be used before application of the composition. However, the amount of anchorage additive may be 0 to 5%, alternatively 1% to 5%, alternatively 1% to 3%, and alternatively 0 to 1%, based on combined weights of all starting materials in the composition.
  • the anchorage additive may be free of silicon bonded aromatic hydrocarbon groups.
  • the pressure sensitive adhesive composition further comprises starting material E) an acetylenic alcohol.
  • the acetylenic alcohol may be added as an inhibitor or stabilizer for the pressure sensitive adhesive composition.
  • Suitable acetylenic alcohols are exemplified by methyl butynol, ethynyl cyclohexanol (ETCH), dimethyl hexynol, and 3,5-dimethyl-l-hexyn-3-ol, 1- butyn-3-ol, l-propyn-3-ol, 2-methyl-3-butyn-2-ol, 3 -methyl- l-butyn-3-ol, 3-methyl- l-pentyn-3- ol, 3-phenyl- l-butyn-3-ol, 4-ethyl-l-octyn-3-ol, 3,5-dimethyl- l-hexyn-3-ol, and 1-ethynyl-l- cyclohexano
  • starting material E) may be selected from the group consisting of (E-l) 1 -ethynyl- 1 -cyclohexanol, (E-2) methyl butynol, (E-3) diallyl maleate, and (E-4) a combination of two or more of (E-l), (E-2) and (E-3).
  • starting material E) is exemplified by ETCH.
  • the amount of acetylenic alcohol added to the composition will depend on various factors including the desired pot life of the pressure sensitive adhesive composition, whether the composition will be a one part composition or a multiple part composition, the particular acetylenic alcohol used, and the selection and amount of starting material C). However, when present, the amount of starting material E) may range from 0.01 to 0.5 parts by weight.
  • the pressure sensitive adhesive composition further comprises starting material F) a hydrosilylation reaction catalyst.
  • Suitable hydrosilylation reaction catalysts are known in the art and are commercially available.
  • the hydrosilylation catalysts can be a platinum group metal selected from platinum, rhodium, ruthenium, palladium, osmium, and iridium.
  • the hydrosilylation catalyst may be a compound of such a metal, for example, chloroplatinic acid, chloroplatinic acid hexahydrate, platinum dichloride, and complexes of said compounds with low molecular weight organopolysiloxanes or platinum compounds microencapsulated in a matrix or core/shell type structure.
  • Complexes of platinum with low molecular weight organopolysiloxanes include l,3-diethenyl-l,l,3,3 -tetramethyldisiloxane complexes with platinum. These complexes may be microencapsulated in a resin matrix.
  • Exemplary hydrosilylation catalysts are described in U.S. Patents 3,159,601; 3,220,972; 3,296,291; 3,419,593; 3,516,946; 3,814,730; 3,989,668; 4,784,879; 5,036,117; and 5,175,325 and EP 0347 895 B.
  • Microencapsulated hydrosilylation catalysts and methods of preparing them are known in the art, as exemplified in U.S. Patents 4,766,176 and 5,017,654.
  • the hydrosilylation reaction catalyst is added to the pressure sensitive adhesive composition in an amount sufficient to catalyze hydrosilylation reaction, typically an amount sufficient to provide 10 ppm to 5,000 ppm by weight of platinum group metal.
  • the pressure sensitive adhesive composition further comprises a solvent.
  • the solvent can be an organic solvent.
  • the organic solvent can be an alcohol such as methanol, ethanol, isopropanol, butanol, or n-propanol; a ketone such as acetone, methylethyl ketone, or methyl isobutyl ketone; an aromatic hydrocarbon such as benzene, toluene, or xylene; an aliphatic hydrocarbon such as heptane, hexane, or octane; a glycol ether such as propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n- propyl ether, or ethylene glycol n-butyl ether, a halogenated hydrocarbon such as dichloromethane, 1,1,1-trichloroethane or methylene chloride; chloroform;
  • the amount of solvent will depend on various factors including the type of solvent selected and the amount and type of other starting materials selected for the pressure sensitive adhesive composition. However, the amount of solvent may range from 10% to 90%, alternatively 20% to 60%, based on combined weights of all starting materials in the pressure sensitive adhesive composition.
  • the solvent can be added during preparation of the pressure sensitive adhesive composition, for example, to aid mixing and delivery. All or a portion of the solvent may be added with one of the other starting materials. For example, starting material A), and when present starting material B), may be dissolved in a solvent, such as an aromatic hydrocarbon, before combination with the other starting materials in the composition. All or a portion of the solvent may optionally be removed after the pressure sensitive adhesive composition is prepared.
  • the pressure sensitive adhesive composition may optionally further comprise up to 20%, based on weight of starting material C), of starting material H) an additional polyalkylhydrogensiloxane having unit formula ( R 13S101/2)2! R * HSi02/2) / , where R1 is as described above, and subscript z is 200 to 250.
  • starting material H may be used to adjust SiH: Alkenyl ratio to the ranges described herein.
  • Suitable additional polyalkylhydrognesiloxnaes for starting material H) include H-
  • H-2) trimethylsiloxy-terminated poly(dimethylsiloxane/methylhydrogensiloxane), and H-3) a combination of both H-l) and H-2).
  • starting materials for the pressure sensitive adhesive composition described above there may be overlap between types of starting materials because certain starting materials described herein may have more than one function.
  • certain alkoxy silanes may be useful as filler treating agents and as adhesion promoters.
  • Certain particulates may be useful as fillers and as pigments, and even as flame retardants, e.g., carbon black.
  • the additional starting materials are distinct from one another and from the required starting materials in the composition.
  • the pressure sensitive adhesive composition can be prepared by a method comprising combining all starting materials by any convenient means such as mixing at ambient or elevated temperature.
  • Starting material E) the acetylenic alcohol may be added before starting material F) the platinum group metal catalyst, for example, when the pressure sensitive adhesive composition will be prepared at elevated temperature and/or the composition will be prepared as a one part composition.
  • the pressure sensitive composition may be prepared as a multiple part composition, for example, when the composition will be stored for a long period of time before use.
  • starting material F) the platinum group metal catalyst is stored in a separate part from any starting material having a silicon bonded hydrogen atom, for example starting material C) the polyalkylhydrogensiloxane and starting material H) (when present) and the parts are combined shortly before use of the pressure sensitive adhesive composition.
  • a two part composition may be prepared by combining starting materials comprising A) the alkenyl-containing polydialkylsiloxane, C) the polyalkylhydrogensiloxane (and starting material H), when present) and G) the organic solvent, and optionally one or more other additional starting materials described above to form a base part, by any convenient means such as mixing.
  • a curing agent may be prepared by combining starting materials comprising A) the alkenyl-containing polydialkylsiloxane, F) the platinum group metal catalyst and G) the organic solvent, and optionally one or more other additional starting materials described above by any convenient means such as mixing.
  • the starting materials may be combined at ambient or elevated temperature.
  • Starting material E) the acetylenic alcohol may be included in one or more of the base part, the curing agent part, or a separate additional part.
  • Starting material D) anchorage additive, when used, may be added to the base part, or may be added as a separate additional part.
  • Starting material B) the polyalkylsiloxane resin, when used, may be added to the base part, the curing agent part, or a separate additional part.
  • the weight ratio of amounts of base part to curing agent part may range from 1:1 to 10:1.
  • the pressure sensitive adhesive composition will cure via hydrosilylation reaction to form a pressure sensitive adhesive.
  • the method described above may further comprise one or more additional steps.
  • the pressure sensitive adhesive composition prepared as described above may be used to form an adhesive article, e.g. , a pressure sensitive adhesive (prepared by curing the pressure sensitive adhesive composition described above) on a substrate.
  • the method described above may, therefore, further comprise comprises applying the pressure sensitive adhesive composition to a substrate.
  • Applying the pressure sensitive adhesive curable composition to the substrate can be performed by any convenient means.
  • the pressure sensitive adhesive curable composition may be applied onto a substrate by gravure coater, offset coater, offset-gravure coater, roller coater, reverse-roller coater, air-knife coater, or curtain coater.
  • the substrate can be any material that can withstand the curing conditions (described below) used to cure the pressure sensitive adhesive curable composition to form the pressure sensitive adhesive on the substrate.
  • any substrate that can withstand heat treatment at a temperature equal to or greater than 120°C, alternatively 150°C is suitable.
  • materials suitable for such substrates including plastic films such as polyimide (PI), polyetheretherketone (PEEK), polyethylene naphthalate (PEN), liquid-crystal polyarylate, polyamideimide (PAI), poly ether sulfide (PES), or polyethylene terephthalate (PET), or PE (polyethylene), or PP (polypropylene).
  • the substrate may be a metal foil such as aluminum foil or copper foil.
  • the thickness of the substrate is not critical, however, the thickness may range from 5 micrometers to 300 micrometers.
  • the method may optionally further comprise treating the substrate before applying the pressure sensitive adhesive composition. Treating the substrate may be performed by any convenient means, such as applying a primer, or subjecting the substrate to corona-discharge treatment, etching, or plasma treatment before applying the pressure sensitive adhesive composition to the substrate.
  • An adhesive article such as a protective film may be prepared by applying the pressure sensitive adhesive composition described above onto the substrate described above. The method may optionally further comprise removing all, or a portion, of the solvent before and/or during curing.
  • Removing solvent may be performed by any convenient means, such as heating at a temperature that vaporizes the solvent without fully curing the pressure sensitive adhesive composition, e.g., heating at a temperature of 70°C to 120°C, alternatively 50°C to 100°C, and alternatively 70°C to 80°C for a time sufficient to remove all or a portion of the solvent (e.g., 30 seconds to 1 hour, alternatively 1 minute to 5 minutes).
  • heating at a temperature that vaporizes the solvent without fully curing the pressure sensitive adhesive composition e.g., heating at a temperature of 70°C to 120°C, alternatively 50°C to 100°C, and alternatively 70°C to 80°C for a time sufficient to remove all or a portion of the solvent (e.g., 30 seconds to 1 hour, alternatively 1 minute to 5 minutes).
  • the method then further comprises curing the pressure sensitive adhesive composition (which may have some or all of the solvent removed when the drying step is performed) room temperature or by heating at a temperature of 140°C to 220°C, alternatively 150°C to 220°C, alternatively 160°C to 200°C, and alternatively 165°C to 180°C for a time sufficient to cure the pressure sensitive adhesive curable composition (e.g., for 30 seconds to an hour, alternatively 1 to 5 minutes). This forms a pressure sensitive adhesive on the substrate. Drying and/or curing may be performed by placing the substrate in an oven.
  • the amount of the pressure sensitive adhesive composition to be applied to the substrate depends on the specific application, however, the amount may be sufficient such that after curing thickness of the pressure sensitive adhesive may be 5 micrometers to 200 micrometers, and for protective film the thickness may be 10 micrometers to 50 micrometers, alternatively 20 micrometers to 40 micrometers, and alternatively 30 micrometers.
  • the method described herein may optionally further comprise applying a removable release liner to the pressure sensitive adhesive opposite the substrate, e.g., to protect the pressure sensitive adhesive before use of the adhesive article.
  • the adhesive article (e.g., protective film) prepared as described above is suitable for use in flexible OLED device fabrication processes as a protective film with low adhesion, high adhesion stability, and/or low migration.
  • a method for fabricating a flexible OLED device may include forming an OLED module on a surface of a substrate, e.g. , a passivation layer on a surface of the OLED module opposite the substrate, and applying a protective film prepared as described herein to a surface of the passivation layer opposite the OLED module.
  • N/A means not applicable
  • Me means methyl.
  • DOWSILTM, SILASTICTM, and SYL-OFFTM products are commercially available from Dow Silicones Corporation of Midland, Michigan, USA.
  • Pressure sensitive adhesive composition samples were prepared by combining the starting materials shown in Table 1. First, 100 parts by weight of starting material Al) dimethylvinylsiloxy-terminated poly(dimethylsiloxane/methylvinylsiloxane) copolymer was mixed with starting material Gl) toluene solvent to make a 25 weight % solution. A poly alky lhydrogensiloxane (one or more of HI) to H4) and Cl)) was added to the mixture in amounts shown below in Table 2 and Table 3.
  • the amount of polyalky lhydrogensiloxane was sufficient to make the SiH/Vi molar ratio in the mixture 0.5, 1 or 2. This ratio included vinyl present in the vinyl containing siloxane complexed platinum catalyst FI), which was added at the end of this procedure. An inhibitor El) was added, and the resulting combination was mixed well. After homogenizing the mixture, starting material (FI) was added to the mixture. The mixture was immediately mixed again carefully not to generate heat. The resulting pressure sensitive adhesive composition sample was then ready for use. The amount of each starting material (in weight parts) in the samples are shown in Table 2 (comparative) and Table 3 (Working), below. Tables 2 and 3 also show SiH/Vi ratio, total Pt content, and % solids (based on weight of all starting materials excluding solvent).
  • the pressure sensitive adhesive composition samples were prepared as described in Reference Example 1 were applied onto a 50 um polyethylene terephthalate (PET) film to form a pressure-sensitive adhesive layer (which after curing had a thickness of 30 um).
  • a pressure-sensitive adhesive sheet was produced by heating the coated film for 2 min. at 150°C.
  • the substrate film (PET) was commercially available; sold under the trade name of Toray Advanced Material Korea (Trade name SH-86, TAMK).
  • Pressure sensitive adhesive tapes were formed by cutting the sheet obtained according to Reference Example 2 into 1 inch-wide strips. Adhesion strength to a stainless-steel plate (SUS304) was measured according to a 180-degree peel test specified in ASTM D1000. Each tape was peeled from the peelable polyethylene terephthalate films and adhered under pressure of 2 kgf developed by rubber rollers to an adherend in the form of a mirror- surface stainless steel plate (SUS304). Initial adhesion higher than 2 gf/inch was defined as Fail.
  • Pressure sensitive adhesive tapes were formed by cutting the sheet obtained according to Reference Example 2 into 1 inch- wide strips.
  • Adhesion strength to a stainless steel plate (SUS304) was measured according to a 180-degree peel test specified in the ASTM D1000 after aging, as follows. Each tape was peeled from the peelable polyethylene terephthalate films and adhered under pressure of 2 kgf developed by rubber rollers to an adherend in the form of a mirror-surface stainless steel plate (SUS304). The tapes were aged for 1 day (24hr) and 3 days (72hr) in an oven at 85°C /85% moisture.
  • the adhesion force was measured by pulling the pressure-sensitive adhesive tape off from the adherend at an angle of 180° relative to the surface of the adherend with the use of a tensile tester at a constant speed of 12inch/min. (Test equipment; AR-1000 (Cheminstrument Company)). Results are shown in Tables 2 and 3, below. For some applications, it may be desirable for adhesion after 24 h to be ⁇ 9 gf/in, and ⁇ 15 gf/ in after 72 h.
  • a pressure sensitive adhesive sheet was prepared according to Reference Example 2.
  • a pressure sensitive adhesive coated on PET was prepared according to Reference Example 2, and anchorage of the pressure sensitive adhesive was evaluated as follows. A cut was made: cross-mark lOcmXIOcm only on PSA by cutter (being careful not to cut PET on bottom). The marked surface was rubbed vigorously by finger. After rubbing 30 sec., the surface was observed to determine whether the PSA was rubbed off or not. If PSA was rubbed off, the result was Fail.
  • Pressure sensitive adhesive tapes were formed by cutting the sheet obtained according to Reference Example 2 into 1 inch- wide strips. Each tape was peeled from the peelable polyethylene terephthalate films and adhered under pressure of 2 kgf developed by rubber rollers to an adherend in the form of a mirror-surface stainless steel plate (SUS304). They are aged for 1 day (24hrs) and 3 days (72hrs) in an oven at 85°C/85%. After cooling to room temperature, PSA tapes were removed from a mirror-surface stainless steel plate. Adhere Nitto 3 IB by 2KG roller on the place that Si tape removed.
  • a pressure sensitive adhesive sheet sample prepared according to Reference Example 2 was used. A cutter was used to make a cut on the pressure sensitive adhesive surface, which was visually observed by naked eye and microscope. If the edge of the cut looked clean and no particle was generated, the sample passed. If a particle or fragment was generated in the edge or a burr was observed, the sample failed. Results for each sample are also shown below in Tables 2 and 3.
  • N/D means Not detected due to adhesive transfer
  • AF means Adhesive failure, i.e., that adhesive is transferred to substrate
  • RF means Rubbing failure, i.e., that adhesive is rubbed off by stress
  • RF means result is 'not applicable' to invention.
  • a silicone pressure sensitive adhesive prepared by curing this composition failed the burr test when tested according to Reference Example 8. Without wishing to be bound by theory, it is thought that when vinyl content of starting material A) in the pressure sensitive adhesive composition was too high, pressure sensitive adhesives prepared therefrom failed the burr test.
  • the pressure sensitive adhesive composition described herein cures to form a pressure sensitive adhesive suitable for use in flexible OLED device fabrication processes.
  • the examples above show that the pressure sensitive adhesive prepared by curing the pressure sensitive adhesive composition described above may have initial adhesion of ⁇ 2 gf/ inch on stainless steel (SUS) (as tested according to Reference Example 3); adhesion after 24 h ⁇ 9 gf/in and adhesion after 72 h ⁇ 15 gf/in as tested according to Reference Example 4.
  • the pressure sensitive adhesive composition described herein may also cure to form a pressure sensitive adhesive with residual adhesion on SUS > 300 gf/in after 24 h and > 250 g/in after 72 h (as tested according to Reference Example 7).
  • SUS represents an industry standard to develop and test pressure sensitive adhesives. Therefore, without wishing to be bound by theory, it is thought that adhesion properties on SUS will provide comparable results on substrates used in OLED fabrication processes, such as passivation layers, and it is expected that this combination of properties allows a pressure sensitive adhesive film to be used as a protective film on a passivation layer during fabrication of a flexible OLED device.
  • the pressure sensitive adhesive composition contained an poly(dialkylsiloxane/alkylalkenylsiloxane) copolymer with an alkenyl content of 0.14% to ⁇ 0.3%
  • the resulting pressure sensitive adhesive passed the burr test (when comparative pressure sensitive adhesives containing alternative functional polydialkylsiloxanes with alkenyl content > 0.3% failed the burr test, as shown in Example 8).
  • disclosure of a range of, for example, 0.15 to ⁇ 0.3 includes the subsets of, for example, 0.15 to 0.21, 0.15 to 0.26, 0.202 to 0.26, and 0.202 to ⁇ 0.3 as well as any other subset subsumed in the range.
  • disclosure of Markush groups includes the entire group and also any individual members and subgroups subsumed therein.
  • disclosure of the Markush group a vinyl, allyl or hexenyl includes the member vinyl individually; the subgroup vinyl and hexenyl; and any other individual member and subgroup subsumed therein.
  • a method for fabricating a flexible organic light emitting diode device comprises:
  • G 10 weight % to 90 weight%, based on combined weights of all starting materials in the composition, of an organic solvent; with the proviso that all starting materials in the composition combined have a molar ratio of silicon bonded hydrogen atoms / silicon bonded alkenyl groups (SiH: Alkenyl ratio) of 0.5:1 to 2:1.
  • starting material A) has a property selected from the group consisting of: i) number average molecular weight of 200,000 g/mol to 500,000 g/mol, ii) alkenyl group content 0.20% to 0.26%, and iii) both i) and ii).
  • starting material C) has a property selected from the group consisting of i) viscosity at 25 deg C of 8 mPa-s to 16 mPa-s, ii) SiH content of > 0% to ⁇ 1%, iii) both i) and ii).
  • starting material F) is selected from the group consisting of (F-l) a platinum group metal selected from platinum, rhodium, ruthenium, palladium, osmium, and iridium; (F-2) a compound of the platinum group metal; (F-3) a complex of the compound with a low molecular weight organopolysiloxane; and (F-4) the compound (F-2), or the complex (F-3), microencapsulated in a matrix or core/shell type structure.
  • a platinum group metal selected from platinum, rhodium, ruthenium, palladium, osmium, and iridium
  • F-2 a compound of the platinum group metal
  • F-3) a complex of the compound with a low molecular weight organopolysiloxane
  • F-4 the compound (F-2), or the complex (F-3), microencapsulated in a matrix or core/shell type structure.
  • starting material E) is selected from the group consisting of (E-l) 1-ethynyl-l-cyclohexanol, (E- 2) methyl butynol, (E-3) diallyl maleate, and (E-4) a combination of two or more of (E-l), (E-2) and (E-3).
  • starting material E) comprises ethynyl cyclohexanol.
  • starting material G) is selected from the group consisting of benzene, toluene, heptane, ethylbenzene, xylene, and a combination of two or more thereof.
  • the pressure sensitive adhesive composition further comprises up to 20%, based on weight of starting material C), of H) an additional polyalkylhydrogensiloxane having unit formula (Rl3Si0]y2)2(R HSi02/2)z’ where subscript z is 200 to 250.
  • the pressure sensitive adhesive composition further comprises up to 15 parts by weight of B) a polyalkylsiloxane resin comprising units of formula (R R3 ⁇ 4i0]y2)a(R Si0]y2)b(Si04/2)o where each R1 is independently an alkyl group of 1 to 10 carbon atoms; each R ⁇ is independently selected from R1, OH, and alkenyl groups of 2 to 6 carbon atoms; subscript a > 0, subscript b > 0, subscript c > 0, a quantity (a+b) > 0, and subscripts a, b, and c have values such that 0.9 ⁇ (a+b)/c ⁇ 1.2.
  • a polyalkylsiloxane resin comprising units of formula (R R3 ⁇ 4i0]y2)a(R Si0]y2)b(Si04/2)o where each R1 is independently an alkyl group of 1 to 10 carbon atoms; each R ⁇ is independently selected from R1, OH, and alkenyl groups of 2
  • the pressure sensitive adhesive composition further comprises up to 1 part by weight of D) an anchorage additive.
  • starting material D) is selected from the group consisting of (D-l) vinyltriacetoxysilane, (D-2) glycidoxypropyltrimethoxysilane, (D-3) a combination of (D-l) and (D-2), and (D-4) a combination of (D-3) and a polydimethylsiloxane terminated with hydroxyl groups, methoxy groups, or terminated with both a hydroxy group and a methoxy group.
  • the method of any one of the first to eleventh embodiments further comprises: removing all or a portion of the solvent from the pressure sensitive adhesive composition before step 2).
  • the method of any one of the first to twelfth embodiments further comprises: treating the substrate before step 1).
  • starting material A) is free of silicon bonded aromatic hydrocarbyl groups
  • starting material B) when present, is free of silicon bonded aromatic hydrocarbyl groups
  • starting material C) is free of silicon bonded aromatic hydrocarbyl groups
  • starting material D when present, is free of silicon bonded aromatic hydrocarbyl groups or two or more thereof in the nineteenth embodiment.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesive Tapes (AREA)
  • Electroluminescent Light Sources (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)

Abstract

L'invention concerne une composition d'adhésif sensible à la pression qui peut durcir par l'intermédiaire d'une hydrosilylation pour former un adhésif sensible à la pression. La composition d'adhésif sensible à la pression peut être appliquée sur un substrat et durcie pour former un film protecteur. Le film protecteur est utile dans des processus de fabrication de dispositifs DELO flexibles, par exemple, pour la protection de couches de passivation.
PCT/US2022/016542 2021-04-09 2022-02-16 Composition d'adhésif sensible à la pression et ses procédés de préparation et d'utilisation dans des applications de diodes électroluminescentes organiques flexibles Ceased WO2022216367A1 (fr)

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KR1020237037864A KR20230170009A (ko) 2021-04-09 2022-02-16 감압성 접착제 조성물, 이의 제조 방법 및 플렉시블 유기 발광 다이오드 응용에서의 이의 용도
CN202280019902.2A CN116998005A (zh) 2021-04-09 2022-02-16 压敏粘合剂组合物及其制备方法和在柔性有机发光二极管应用中的用途

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