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WO2019162035A1 - Composition pour produire une masse adhésive, en particulier pour encapsuler un dispositif électronique - Google Patents

Composition pour produire une masse adhésive, en particulier pour encapsuler un dispositif électronique Download PDF

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Publication number
WO2019162035A1
WO2019162035A1 PCT/EP2019/051744 EP2019051744W WO2019162035A1 WO 2019162035 A1 WO2019162035 A1 WO 2019162035A1 EP 2019051744 W EP2019051744 W EP 2019051744W WO 2019162035 A1 WO2019162035 A1 WO 2019162035A1
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WIPO (PCT)
Prior art keywords
adhesive
weight
test
composition according
resin
Prior art date
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Ceased
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PCT/EP2019/051744
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German (de)
English (en)
Inventor
Jessika Gargiulo
Frank Lange
Thilo Dollase
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Tesa SE
Original Assignee
Tesa SE
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Publication of WO2019162035A1 publication Critical patent/WO2019162035A1/fr
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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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • 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
    • C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • 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]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/387—Block-copolymers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/02—Containers; Seals
    • H01L23/06—Containers; Seals characterised by the material of the container or its electrical properties
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293—Organic, e.g. plastic
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
    • H01L23/3107—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape the device being completely enclosed
    • H01L23/3135—Double encapsulation or coating and encapsulation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • 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
    • 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
    • C09J2301/302—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 the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
    • 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
    • C09J2453/00—Presence of block copolymer

Definitions

  • composition for producing an adhesive in particular for
  • the present invention relates to a composition for producing an adhesive, in particular a pressure-sensitive adhesive.
  • the adhesive is suitable inter alia for encapsulating an electronic device.
  • the invention further relates to an adhesive, in particular pressure-sensitive adhesive, which is obtainable from the abovementioned composition, and to an adhesive tape with such an adhesive.
  • the invention further relates to a method for encapsulating an electronic device using such a composition, adhesive or adhesive tape, their use as well as a composite of an electronic device and a composition applied thereon, an adhesive or an adhesive tape.
  • Electronic devices are increasingly used in commercial products or are about to be launched.
  • Such arrangements include inorganic or organic electronic structures, such as organic, organometallic or polymeric semiconductors or combinations thereof.
  • These arrangements and products are rigid or flexible depending on the desired application, whereby there is an increasing demand for flexible arrangements.
  • the production of such arrangements is effected, for example, by printing processes such as high-pressure, intaglio, screen printing, planographic printing or else so-called "non-impact printing” such as thermal transfer printing, inkjet printing or digital printing.
  • vacuum methods such as chemical vapor deposition (CVD), physical vapor deposition (PVD), plasma-enhanced chemical or physical deposition (PECVD), sputtering, (plasma) etching or vapor deposition, are used, the structuring usually by Masks done.
  • Electrophoretic or electrochromic structures or displays, organic or polymeric light-emitting diodes (OLEDs or PLEDs) in display and display devices or as illumination, electroluminescent lamps, light-emitting electrochemical devices may be mentioned as examples of (commercial) electronic applications which are already interesting in their market potential Cells (LEECs), organic solar cells, preferably dye or polymer solar cells, inorganic solar cells, preferably thin-film solar cells, in particular based on silicon, germanium, copper, indium and / or selenium, organic field effect transistors, organic switching elements, organic optical amplifiers, organic Laser diodes, organic or inorganic sensors or organically or inorganic based RFID transponder listed.
  • LECs Organic solar cells, preferably dye or polymer solar cells, inorganic solar cells, preferably thin-film solar cells, in particular based on silicon, germanium, copper, indium and / or selenium, organic field effect transistors, organic switching elements, organic optical amplifiers, organic Laser diodes, organic or inorganic sensors or
  • Permeates may be a variety of low molecular weight organic or inorganic compounds, especially water vapor and oxygen.
  • inorganic and / or organic (opto) electronics in particular in organic (opto) electronics, there is a particular need for flexible adhesive solutions that represent a permeation barrier for permeates, such as oxygen and / or water vapor.
  • the flexible adhesive solutions should therefore not just one achieve good adhesion between two substrates, but additionally fulfill properties such as high shear strength and peel strength, chemical resistance, aging resistance, high transparency, easy processability and high flexibility and flexibility.
  • a common approach in the art is therefore to place the electronic assembly between two water vapor and oxygen impermeable substrates. This is followed by a seal at the edges.
  • glass or metal substrates are used which offer a high permeation barrier but are very susceptible to mechanical stress. Furthermore, these substrates cause a relatively large thickness of the entire assembly. In the case of metal substrates, there is also no transparency.
  • surface substrates such as transparent or non-transparent films, are used, which can be multi-layered. Here, both combinations of different polymers, as well as inorganic or organic layers can be used. The use of such surface substrates allows a flexible, extremely thin structure.
  • substrates such as films, fabrics, nonwovens and papers or combinations thereof are possible for the various applications.
  • a good adhesive for the sealing of (opto) electronic components has a low permeability to oxygen and in particular to water vapor, has sufficient adhesion to the assembly and can flow well on this. Low infiltration on the assembly can reduce interfacial barrier performance by incomplete wetting of the assembly surface and by residual pores, since lateral entry of oxygen and water vapor is allowed independent of the adhesive properties. Only if the contact between mass and substrate is continuous, the mass properties are the determining factor for the barrier effect of the adhesive.
  • the oxygen transmission rate OTR Olygen Transmission Rate
  • the water vapor transmission rate WVTR Water Vapor Transmission Rate
  • the respective rate gives the area and time related flow of oxygen or water vapor through a film under specific conditions Temperature and partial pressure and optionally other measurement conditions such as relative humidity. The lower these values are, the better the respective material is suitable for encapsulation.
  • the specification of the permeation is based not only on the values for WVTR or OTR, but always includes an indication of the mean path length of the permeation such as the thickness of the material or a normalization to a certain path length.
  • the permeability P is a measure of the permeability of a body to gases and / or liquids. A low P value indicates a good barrier effect.
  • the permeability P is a specific value for a defined material and a defined permeate under steady state conditions at a certain permeation path length, partial pressure and temperature.
  • the solubility term S describes the affinity of the barrier adhesive to the permeate.
  • S the solubility term
  • D is a measure of the mobility of the permeate in the barrier material and is directly dependent on properties such as molecular mobility or free volume. Often relatively low values are achieved for strongly cross-linked or highly crystalline D materials. However, highly crystalline materials tend to be less transparent and greater crosslinking results in less flexibility.
  • the permeability P usually increases with an increase in molecular mobility, such as when the temperature is increased or the glass transition point is exceeded.
  • a low solubility term S is usually insufficient to achieve good barrier properties.
  • a classic example of this is in particular siloxane elastomers.
  • the materials are extremely hydrophobic (small solubility term), but have a comparatively low barrier to water vapor and oxygen due to their freely rotatable Si-O bond (large diffusion term). For a good barrier effect, a good balance between solubility term S and diffusion term D is necessary.
  • liquid adhesives and adhesives based on epoxides have hitherto been used (WO 98/21287 A1, US 4,051,195 A, US 4,552,604 A). These have a low diffusion term D due to strong cross-linking. Their main field of application is edge bonding of rigid arrangements, but also moderately flexible arrangements. Curing takes place thermally or by means of UV radiation. A full-surface bonding is hardly possible due to the shrinkage caused by the curing, since it comes to tensions between adhesive and substrate during curing, which in turn can lead to delamination.
  • liquid adhesives have a number of disadvantages.
  • low molecular weight components VOCs
  • VOCs low molecular weight components
  • the adhesive must be applied consuming each individual component of the arrangement.
  • the purchase of expensive dispensers and fixators is necessary to ensure accurate positioning.
  • the type of application also prevents a rapid continuous process and also by the subsequently required lamination step, the achievement of a defined layer thickness and bond width can be made difficult within narrow limits by the low viscosity.
  • thermal-crosslinking systems are limited in the low temperature range or in 2-component systems by the pot life, ie the processing time until a gelling has taken place.
  • the sensitive (opto) electronic structures limit the usability of such systems - the maximum applicable temperatures for (opto) electronic structures are often below 120 ° C, since too high temperatures can cause pre-damage .
  • flexible arrangements containing organic electronics and with transparent polymer films or composites of polymer films and inorganic layers are encapsulated, set here narrow limits. This also applies to laminating under high pressure. In order to achieve an improved durability, a waiver of a temperature-stressing step and lamination under lower pressure is advantageous here.
  • radiation-curing adhesives are also frequently used in the meantime (US 2004/0225025 A1, US 2010/0137530 A1, WO 2013/057265, WO 2008/144080 A1).
  • the use of radiation-curing adhesives avoids a long-lasting heat load on the (opto) electronic device.
  • DE 10 2008 060 1 13 A1 describes a method for encapsulating an electronic arrangement against permeates, in which a pressure-sensitive adhesive based on butylene block copolymers, in particular isobutylene block copolymers, is used, and the use of such an adhesive in an encapsulation method.
  • a pressure-sensitive adhesive based on butylene block copolymers, in particular isobutylene block copolymers
  • certain resins characterized by DACP and MMAP values are preferred.
  • the adhesive is also preferably transparent and can exhibit UV-blocking properties.
  • the adhesive preferably has a WVTR of ⁇ 40 g / m 2 * d and an OTR of ⁇ 5000 g / m 2 * d bar.
  • the PSA can be heated during and / or after the application.
  • the PSA can be crosslinked, for example by radiation or thermal. Substance classes are proposed by means of which such crosslinking can be advantageously carried out. However, no specific examples are given which lead
  • US 2006/100299 A1 discloses a pressure-sensitive adhesive which is a polymer having a softening temperature in the sense of US 2006/100299 A1 of greater than +60 ° C., a polymerizable resin having a softening temperature in the sense of US 2006/100299 A1 of less than + 30 ° Contains C and a latent reactive, in particular photoactivatable initiator, which can lead to a reaction between resin and polymer.
  • Reactively engineered polymers are not universally available, so one is limited in the choice of this polymer base when it comes to other properties and costs.
  • any kind of functionalization brings about an increase in basic polarity and thus an undesirable increase Water vapor permeability.
  • No copolymers based on isobutylene or butylene are mentioned, and no information is provided on the molar masses of the polymers. The document discusses various disadvantages of thermal curing for the encapsulation of OLEDs.
  • Thermally activated adhesive systems for encapsulation z. B. OLEDs are known (US 5,242,715, WO 2015/027393 A1, WO 2015/068454 A1, JP 2015/050143 A1, KR 2009-1 10132 A1, WO2014 / 199626 A1)
  • liquid adhesive systems are always described with the corresponding further above listed disadvantages.
  • US 2014/0367670 A1 teaches thermally initiated cationically curable formulations which can also be used for the encapsulation of OLEDs.
  • Curing temperatures are defined as a range between 70 ° C and 150 ° C, more specifically between 80 ° C and 110 ° C, and more specifically between 90 ° C and 100 ° C.
  • the formulations can also be applied in film form.
  • Polymers may be added to the reactive system. For this example, polymers are given with very different polarity. However, polymers with particularly good barrier action, such as polyisobutylene or polybutylene, are not specified. Rather, a passivation layer is introduced as an additional layer to produce barrier properties.
  • the combination of a thermally activatable epoxy system with low activation temperature and a polybutylene or polyisobutylene-containing matrix does not seem to be obvious or is considered to be difficult to achieve.
  • the adhesive should in particular after the application requires no post-crosslinking step.
  • composition for producing an adhesive preferably a pressure-sensitive adhesive, comprising or consisting of a) from 25 to 42% by weight, in particular from 30 to 38% by weight, preferably from 32 to 36% by weight, of at least one block copolymer comprising at least isobutylene and / or butylene as comonomer,
  • the present invention is based on the finding that adhesives can be produced from the compositions according to the invention which, even after curing, whether initiated thermally or by UV light, have such a degree of tack that they are still sufficient to withstand the Apply adhesive as a barrier layer on electronic components and protect them against the harmful effects of oxygen and water vapor.
  • the adhesive of the invention may be supplied in already cured form to the end user. This also eliminates the need for security systems for uncured systems such as exclusion of light and / or heat to prevent inadvertent release of the initiator.
  • composition according to the invention offers the further advantage that thermal hardeners can also be used, even if the later target substrate of the bond, that is to say for example an electronic arrangement, would be too temperature-sensitive or at least with regard to the initiator used.
  • thermal hardeners can also be used, even if the later target substrate of the bond, that is to say for example an electronic arrangement, would be too temperature-sensitive or at least with regard to the initiator used.
  • the curing and the application can run separately - but not in principle need.
  • UV initiators may be used in cases where the later target substrate would be likely to be sensitive to UV radiation or other radiation used for curing.
  • the at least one block copolymer is a triblock copolymer which is composed of two terminal hard blocks and one medium soft block.
  • Diblock copolymers are also well suited, especially in mixtures of tri- and diblock copolymers.
  • the component a) comprises or consists of at least one T riblockcopolymer, which is composed of two terminal hard blocks and a medium soft block, wherein at least one type of first polymer block having a softening temperature of less than -20 ° C as a soft block and at least one type of second polymer block having a softening temperature greater than + 40 ° C. is used as the hard block, the softening temperature being determined by differential scanning calorimetry according to DIN 53765: 1994-03 at a heating rate of 10 K / min. Smaller molecular weights are preferred because of their better processability.
  • the soft block is preferably constructed nonpolar and preferably contains butylene or isobutylene as Homopolymerblock or copolymer block, the latter preferably copolymerized with itself or with each other or with further particularly preferably nonpolar comonomers.
  • Suitable nonpolar comonomers are, for example, the (partially) hydrogenated polymerization product of butadiene, the (partially) hydrogenated polymerization product of isoprene and / or the polymerization product of olefins.
  • the hard block is preferably composed of vinylaromatics (also partially or fully hydrogenated variants), methyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate and / or isobornyl acrylate. Particularly preferred examples are styrene and ⁇ -methylstyrene, although this list is not exhaustive.
  • the hard block thus contains the at least one type of comonomer, which - considered as a hypothetical homopolymer - has a softening temperature of greater than 40 ° C.
  • the described preferred soft and hard blocks are realized simultaneously in the copolymer (s).
  • the aforementioned block copolymer is preferably a triblock copolymer such as polystyrene block polyisobutylene block polystyrene polymer or a diblock, star and / or graft copolymer, more preferably a polystyrene block polyisobutylene block polystyrene -Polymer.
  • triblock copolymers of the polystyrene-block-polyisobutylene block-polystyrene type are used.
  • Such systems have been made known under the names SIBStar by Kaneka and Oppanol IBS by BASF. Further advantageously usable systems are described in EP 1 743 928 A1.
  • copolymers contain a proportion of isobutylene or butylene as at least one comonomer type results in a nonpolar adhesive which advantageously offers low volume barrier properties, in particular with respect to water vapor.
  • the inventive use effectively controls the at least second comonomer grade with the own softening temperature of greater than 40 ° C. for a hypothetical homopolymer.
  • Component a) may comprise at least one diblock copolymer, component a) preferably containing from 40 to ⁇ 100% by weight of the triblock and> 0 to 60% by weight of the diblock copolymer, in particular from 50 to 82% by weight. of the triblock and 18 to 50% by weight of the diblock copolymer, in each case based on the total amount of elastomer used a).
  • the component a) may have a weight-average molecular weight M w of 1,000,000 g / mol or smaller as determined by gel permeation chromatography using tetrahydrofuran as the eluent and polystyrene as a standard, preferably 500,000 g / mol or smaller, more preferably 40,000 to 150,000 g / mol.
  • the proportion of block copolymer in the composition is preferably at least 25% by weight and at most 42% by weight, preferably at least 30% by weight and at most 38% by weight, very preferably 32 to 36% by weight.
  • the required barrier properties can be realized.
  • it acts as a film former, so that the curable formulation as an adhesive layer in adhesive tapes, such. B. as transfer adhesive tape, in any dimensions can be prefabricated.
  • the cured formulation also obtains flexibility / flexibility desired by many (opto) electronic composites by the (co) polymer.
  • composition according to the invention contains at least one adhesive resin b).
  • This adhesive resin b) may be at least 70%, based on the number of double bonds before the hydrogenation, hydrogenated, in particular fully hydrogenated.
  • the partially hydrogenated tackifier resins are advantageously those which are compatible with the copolymer or, if a copolymer composed of hard and soft blocks is used, are mainly compatible with the soft block.
  • the softening temperature of the adhesive resin b) is at least 80 ° C and at most 130 ° C, measured by Ring and Ball according to ASTM E28-14, preferably at least 90 ° C to at most 1 15 ° C. This can, if necessary, be fine-tuned on the one hand, the adhesive behavior, on the other hand, the Auffmony on the bonding substrate.
  • hydrocarbon resins in particular hydrogenated polymers of dicyclopentadiene, partially, selectively or completely hydrogenated hydrocarbon resins based on Cs, C 5 / C 9 or Cg monomer streams, polyterpene resins based on a-pinene and / or beta, may be used as resins in the pressure-sensitive adhesive.
  • Pinen and / or d-limonene, hydrogenated polymers of preferably pure Cs and Cg aromatics can be used.
  • the aforementioned adhesive resins can be used both alone and in admixture.
  • hydrogenated resins having a degree of hydrogenation of at least 70%, preferably at least 90%, are preferred.
  • the adhesive resin or the adhesive resins are at least partially compatible with the isobutylene or butylene-containing (co) polymer segments.
  • the adhesive resin b) is a nonpolar resin with a diacetone alcohol cloud point (DACP) value of above 25 ° C., in particular of at least 30 ° C., preferably of 35 to 80 ° C., and a MMAP Value (mixed methylcyclohexane aniline point) greater than 60 ° C, preferably from 65 to 90 ° C, is.
  • DCP diacetone alcohol cloud point
  • MMAP Value mixed methylcyclohexane aniline point
  • the proportion of adhesive resin (s) in the composition is preferably at least 15% by weight and at most 32% by weight, preferably at least 18% by weight and at most 30% by weight, very preferably from 20 to 28% by weight .-%.
  • the adhesive according to the invention further contains at least one kind of reactive resin.
  • resins based on a cyclic ether for thermal and / or radiation-chemical curing, ie via photoinitiators are those which have a softening temperature of less than 40 ° C. in the uncured state, measured by differential scanning calorimetry according to DIN 53765: 1994-03 at a heating rate of 10 K / min, preferably of less than 20 ° C.
  • the reactive resin c) is preferably cationically curable.
  • the reactive resins based on cyclic ethers are, in particular, epoxides, ie compounds which carry at least one oxirane group, or oxetanes. They may be aromatic or in particular aliphatic or cycloaliphatic nature, with cycloaliphatic epoxides being particularly preferred.
  • Useful reactive resins can be monofunctional, difunctional, trifunctional, tetrafunctional or higher functional to polyfunctional, with functionality relating to the cyclic ether group.
  • Examples are 3,4-epoxycyclohexylmethyl-3 ', 4'-epoxycyclohexanecarboxylate (EEC) and derivatives, dicyclopendadiene dioxide and derivatives, 3-ethyl-3-oxetanemethanol and derivatives, tetrahydrophthalic acid diglycidyl esters and derivatives, hexahydrophthalic acid diglycidyl esters and derivatives, 1,2-Ethanediglycidyl ethers and derivatives, 1,3-propanediglycidyl ethers and derivatives, 1,4-butanediol diglycidyl ethers and derivatives, higher 1,1-n-alkanediglycidyl ethers and derivatives, bis - [(3,4-epoxycyclohexyl) methyl] adipate and derivatives, Vinylcyclohexyl dioxide and derivatives, 1,4-cyclohexanedimethanol bis (3,4-cyclohexaned
  • Reactive resins can be used in their monomeric or dimeric, trimeric, etc., up to their oligomeric form.
  • the proportion of reactive resin (s) in the composition is at least 15 wt .-% and at most 32 wt .-%, preferably at least 20 wt .-% and at most 30% by weight.
  • the composition according to the invention contains an initiator d).
  • the initiator d) can be selected from thermally activatable initiators for the initiation of a cationic curing, photoinitiators, in particular UV initiators for the initiation of a cationic curing, and mixtures of these. Such initiators are known in principle.
  • the selection of suitable thermal initiators, if used, for the cationic curing of the reactive resins with respect to the present task presents a particular challenge.
  • the temperature required for activation of the thermal initiator should be within a range in which the adhesive can be cured in a sufficiently short time.
  • the activation temperature should be at most 150 ° C, preferably even at most 100 ° C.
  • the selection of suitable systems is hampered by the fact that for many applications high demands be placed on the optical quality of the adhesive product and the bonded composite. The adhesive products themselves must therefore already have high optical quality. This can usually only be achieved by solvent-based coatings of the adhesive formulation.
  • the thermally activatable initiator for the cationic curing should advantageously lead to curing of the reactive resin in the temperature range of the drying process of the solvent-containing coating.
  • a series of thermally activatable initiators for the cationic curing of z For example, epoxides have been described in the past. In this context, the term (curing) catalyst is often used instead of initiator.
  • a large number of conventional curing systems for epoxides is not suitable for the purposes of the present invention. These include BF3-amine complexes, anhydrides, imidazoles, amines, DICY, dialkylphenylacylsulfonium salts, triphenylbenzylphosphonium salts and amine-blocked phenylsulfonium acids. Many of these curing systems require too much activation energy. In addition, the demands for high transparency, low haze and low yellowing tendency z. T. not feasible.
  • thermally activatable initiators for a cationic curing of cyclic ethers are in particular pyridinium, ammonium (especially anilinium) and sulfonium (especially thiolanium) salts and Metallaltsalztriflate as triflates of calcium, zinc, aluminum , the rare earth or the lanthanides.
  • N-benzylpyridinium salts and benzylpyridinium salts wherein aromatics z. B. with alkyl alkoxy, halogen or cyano groups may be substituted.
  • Lanthanoid triflates such as samarium III triflate, ytterbium II-triflate, erbium III-triflate, dysprosium III-triflate, which are available from Sigma Aldrich, and lanthanum-II-triflate, are also very advantageously usable available from Alfa Aesar.
  • Suitable anions for the initiators which can be used include hexafluoroantimonate, hexafluorophosphate, hexafluoroarsenate, tetrafluoroborate and
  • Tetra (pentafluorophenyl) borate and triflate are also usable are anions according to JP 2012-056915 A1 and EP 393893 A1.
  • Thermally activatable initiators for cationic curing are used uncombined or as a combination of two or more thermally curable initiators.
  • thermally activatable initiators having the activation temperature of at least 25 ° C and at most 150 ° C, preferably of at least 50 ° C and at most 100 ° C, at which a cationic curing of the reactive resins can be started.
  • the activation duration can be 15 s or more and 15 min or less, even if shorter or even longer activation times are not excluded.
  • the curing process may continue after the activation period.
  • the curing reaction of the adhesive tape is complete at the time of lamination substantially in view of the achievable conversion reaction. It is also possible that the curing process at the time of lamination has not yet been completed in view of the achievable turnover of the curing reaction.
  • photoinitiators which can be used are those which absorb UV light below 350 nm and allow cationic curing, the photoinitiator being selected in particular from sulfonium, iodonium and metallocene-based photoinitiators.
  • Trifluoromethylsulfonyl amides and tris (trifluoromethylsulfonyl) methide called.
  • chloride, bromide or iodide are also conceivable as anions, although initiators which are essentially free of chlorine and bromine are preferred.
  • usable systems include sulfonium salts (see for example US 4,231,951 A, US 4,256,828 A, US 4,058,401 A, US 4,138,255 A and US 2010/063221 A1) such as triphenylsulfonium hexafluoroarsenate, triphenylsulfonium hexafluoroborate,
  • T r is (dodecylphenyl) sulfonium tetrakis (3,5-bis-trifluoromethylphenyl) borate, 4-acetamidophenyldiphenylsulfonium tetrafluoroborate, 4-acetamidophenyldiphenylsulfonium tetrakis (pentafluorobenzyl) borate, dimethylnaphthylsulfonium hexafluorophosphate,
  • Examples of commercialized photoinitiators are Cyracure UVI-6990, Cyracure UVI-6992, Cyracure UVI-6974 and Cyracure UVI-6976 from Union Carbide, Optomer SP-55, Optomer SP-150, Optomer SP-151, Optomer SP-170 and Optomer SP-172 from Adeka, San-Aid SI-45L, San-Aid SL-60L, San-Aid SI-SOL, San-Aid SI-1 OOL, San-Aid SL-1 10L, San-Aid SI-150L and San-Aid SI-180L from Sanshin Chemical, SarCat CD-1010, SarCat CD-101 1 and SarCat CD-1012 from Sartomer, Degacure K185 from Degussa, Rhodorsil photoinitiator 2074 from Rhodia, CI-2481, CI 2624, Cl-2639, CI-2064, CI-2734, CI-2855, CI-2823
  • Photoinitiators can be used uncombined or as a combination of two or more photoinitiators and / or thermal initiators.
  • Advantageous are photoinitiators which have an absorption at less than 350 nm and advantageously at greater than 250 nm. Initiators that absorb above 350 nm, for example in the range of violet light, are also usable.
  • Sulfonium-based photoinitiators are particularly preferably used because they have an advantageous UV absorption characteristic.
  • the activation period is usually more than 1 s and typically less than 5 min, even if shorter or even longer activation times are not excluded.
  • the curing process may continue after the activation period.
  • the curing reaction of the adhesive tape at the time of lamination is substantially completed in view of the achievable conversion reaction. It is also possible that the curing process at the time of lamination has not yet been completed in view of the achievable turnover of the curing reaction.
  • the activation of the photoinitiator is advantageously carried out after the drying process, if a solvent-containing formulation is coated.
  • the proportion of the thermally activatable initiators with respect to the reactive resin use amount in the composition may typically be at least 0.3 wt% and at most 5.0 wt%, preferably at least 0.5 wt% and at most 2.5 Wt .-% and very preferably between 0.8 and 1, 5 wt .-% are.
  • the proportion of radiation-activatable initiators with respect to the reactive resin use amount in the composition typically at least 0.1 wt .-% and at most 2.5 wt .-%, preferably at least 0.2 wt .-% and at most 1, 5 wt .-% are, more preferably at least 0.3 wt .-% and at most 1, 0 wt .-%.
  • the composition contains at least one hydrocarbon-based plasticizer e).
  • Particularly suitable hydrocarbon-based plasticizers e) have a weight-average molecular weight M w of from 2,000 to 20,000 g / mol as determined by gel permeation chromatography using tetrahydrofuran as eluent and polystyrene as standard.
  • the use of plasticizers having a molecular weight well below 2,000 g / mol can lead to an adverse effect on the thermal resistance.
  • the hydrocarbon-based plasticizer e) consists in particular of at least 90% by weight of saturated hydrocarbons, preferably at least 95% by weight, based on the mass of the plasticizer e).
  • These plasticizers are particularly preferred because they contribute, in cooperation with the tackifying resins, to the fact that the adhesives according to the invention also have sufficient tack after curing that they can be adhered to an electronic component as a barrier layer even after curing.
  • plasticizers based on (co) polymers of isobutylene and / or butylene, of ethylene and of propylene, if appropriate in combination with further, in particular nonpolar, comonomers.
  • ter Pib 950 ter Pib 1300 and ter Pib 2600 from Ter Hell
  • Trilene CP80 Trilene CP1 100
  • Trilene 65 and Trilene 67 Forma Lion Elastomers
  • Oppanol B10N from Forma BASF and Indopol H25, Indopol H50, Indopol H100, Indopol H300, Indopol H1200, Indopol H1500, Indopol H1900, Indopol H2100, Indopol H6000 and Indopol H18000 from Ineos.
  • the proportion of component e) is 7 to 22 wt .-%, preferably 12 to 20% by weight.
  • the composition of the invention may contain one or more additives f).
  • the additive f) can be selected from conventional additives such as anti-aging agents (antiozonants, antioxidants, light stabilizers, etc.).
  • anti-aging agents antioxidants, light stabilizers, etc.
  • additives to the adhesive are typically used:
  • Sunscreens such as UV absorbers or hindered amines
  • correspondingly useful elastomers include, but are not limited to those based on pure hydrocarbons, for example, unsaturated polydienes such as natural or synthetically produced polyisoprene or polybutadiene, chemically substantially saturated elastomers such as saturated ethylene-propylene copolymers, ⁇ -olefin copolymers, ethylene-propylene rubber, and chemical functionalized hydrocarbons, such as, for example, halogen-containing, acrylate-containing, allyl- or vinyl ether-containing polyolefins
  • the additives or additives are not mandatory, the adhesive also works without these are added individually or in any combination. They are preferably selected so that they do not significantly stain or cloud the adhesive.
  • the composition according to the invention contains one or more fillers g) as an optional component.
  • the filler g) may for example be selected from nanoscale fillers, transparent fillers, getter and / or scavenger fillers.
  • Nanosized and / or transparent fillers are preferably used as fillers of the adhesive.
  • a filler is referred to herein as nanoscale if it has a maximum extent of about 100 nm, preferably of about 10 nm, in at least one dimension.
  • Particular preference is given to using mass-transparent fillers with platelet-shaped crystallite structure and a high aspect ratio with homogeneous distribution.
  • the fillers with platelet-like crystallite structure and aspect ratios well above 100 generally only have a thickness of a few nm, but the length or the width of the crystallites can be up to a few pm.
  • Such fillers are also referred to as nanoparticles.
  • the particulate configuration of the fillers with small dimensions is also particularly advantageous for a transparent design of the PSA.
  • these fillers can be surface-modified with organic compounds.
  • the use of such fillers per se is known, for example, from US 2007/0135552 A1 and WO 02/026908 A1.
  • fillers which can interact with oxygen and / or water vapor in a particular manner are also used.
  • penetrating oxygen or water vapor is then bound to these fillers chemically or physically.
  • These fillers are also referred to as getter, scavenger, desiccant or absorber.
  • Such fillers include, by way of example, titanium dioxide, bentonite, montmorillonite, hydrotalcite, diatomaceous earth, zeolites and oxides of (alkaline) alkali metals, such as barium oxide, calcium oxide, iron oxide and magnesium oxide or also carbon nanotubes.
  • organic absorbers such as, for example, polyolefin copolymers, polyamide copolymers, PET copolyesters or other absorbers based on hybrid polymers, which are mostly used in combination with catalysts such as, for example, cobalt.
  • the proportion is preferably at least 5 wt .-%, more preferably at least 10 wt .-% and most preferably at least 15 wt .-%, based on the composition. 20% by weight is a preferred upper limit for such fillers.
  • the finest possible distribution and the highest possible surface area of the fillers are advantageous. This allows a higher efficiency and a higher loading capacity and is achieved in particular with nanoscale fillers.
  • Another object of the present invention relates to an adhesive, in particular pressure-sensitive adhesive, obtainable or obtained by curing a composition according to the invention.
  • the adhesive is preferably transparent in the visible region of the spectrum from 400 nm to 800 nm.
  • PSAs are characterized in particular by their permanent tackiness and flexibility.
  • a material that exhibits permanent tack must have a suitable combination of adhesive and cohesive properties at all times. For good adhesion properties, it is necessary to adjust pressure-sensitive adhesives so that there is an optimum balance of adhesive and cohesive properties.
  • the adhesive is preferably a pressure-sensitive adhesive, ie a viscoelastic composition which remains permanently tacky and adhesive at room temperature in a dry state. The bonding takes place by light pressure immediately on almost all substrates.
  • the adhesive is as transparent as possible in the visible light of the spectrum (wavelength range of about 400 nm to 800 nm). This applies in particular to the scope of the encapsulation of electronic components. It is thus preferred that the adhesive has a haze of less than 5.0%, measured according to ASTM D 1003-13, preferably less than 2.5%.
  • the desired transparency can be achieved in particular by the use of colorless tackifier resins and by adjusting the compatibility of copolymer (in microphase-separated systems such as block and graft copolymers with their soft block) and tackifier resin but also with the reactive resin. Reactive resins are advantageously selected for this purpose from aliphatic and cycloaliphatic systems.
  • Such a pressure-sensitive adhesive is therefore also particularly well suited for full-surface use over an (opto) electronic structure.
  • a full-surface bonding offers, with an approximately central arrangement of the electronic structure over an edge seal, the advantage that the permeate would have to diffuse through the entire surface before it reaches the structure.
  • the permeation path is thus significantly increased.
  • the permeation paths extended in this embodiment compared to edge sealing, for example by liquid adhesives, have a positive effect on the overall barrier, since the permeation path is inversely proportional to the permeability.
  • "transparency” means an average transmission of the adhesive in the visible range of the light of at least 75%, preferably higher than 90%, whereby this consideration refers to uncorrected transmission, that is, without loss of interfacial reflection.
  • the adhesive formulation For many applications in the (opto) electronic sector, it is necessary for the adhesive formulation to hardly yellow or even yellow. This can be quantified by the Ab * value (Test G) of the CIE Lab system. Therefore, preferred adhesives are characterized by a yellowness Ab * from 0.0 to 1.0, measured according to DIN 6174: 1979-01 at a layer thickness of 50 pm, preferably from 0, 1 to 0.9. These values refer to the cured adhesive.
  • the invention further relates to an adhesive tape comprising at least one planar support and a layer of an adhesive according to the invention applied thereon.
  • the carrier is a coated plastic film or a layer of flexible thin glass having a layer thickness of at most 1 mm, preferably at most 100 pm, wherein the thin glass is preferably a borosilicate glass or a alkali-free aluminoborosilicate glass.
  • the support has a permeation barrier of WVTR ⁇ 0.1 g / (m 2 d) according to ASTM F-1249: 2013.
  • the preparation and processing of the PSA into an adhesive tape is very preferably carried out from solution.
  • a solvent mixture
  • Such solvents even in mixtures, having a boiling point at ambient pressure (assumed to be normal pressure) of at most 200 ° C., preferably of not more than 150 ° C., very preferably of not more than 120 ° C., are very advantageous.
  • the constituents of the PSA are dissolved in a suitable solvent, for example an alkane or cycloalkane or mixtures of alkane, cycloalkane and ketone and / or aromatic, and applied to the support by generally known methods.
  • a suitable solvent for example an alkane or cycloalkane or mixtures of alkane, cycloalkane and ketone and / or aromatic
  • processes of solution coatings are known with doctor blades, knives, rollers or nozzles, just to name a few.
  • the person skilled in the art knows the process parameters in order to obtain transparent adhesive layers.
  • solvent coating processes the choice of solvent or solvent mixture may influence the coating result.
  • the person skilled in the art is also familiar with the choice of suitable solvents. Combinations of, in particular, nonpolar solvents boiling below 100 ° C.
  • solvents boiling above 100 ° C. in particular aromatic ones, are also conceivable. Since the drying properties of solvents not only depend on their boiling point, in principle, mixtures with solvents with boiling temperatures above 100 ° C such. As toluene can be used.
  • the adhesive of the invention can be used particularly advantageously in a single-sided or double-sided adhesive tape. This mode of administration allows a particularly simple and uniform application of the adhesive.
  • the general term "adhesive tape” encompasses a carrier material which is provided on one or both sides with an (adhesive) adhesive.
  • the carrier material comprises all flat structures, for example films or film sections which are expanded in two dimensions, strips of extended length and limited width, strip sections, diecuts (for example in the form of borders or boundaries of an (opto) electronic arrangement), multilayer arrangements and the like. Different carriers such as films, fabrics, nonwovens and papers can be combined with the adhesives for various applications.
  • the term “adhesive tape” also includes so-called “transfer tapes", that is, an adhesive tape without a carrier.
  • the adhesive is applied before application between flexible liners, which are provided with a release layer and / or have anti-adhesive properties.
  • a liner is first removed, the adhesive is applied and then the second liner is removed.
  • the adhesive can thus be used directly for the connection of two surfaces in (opto) electronic arrangements.
  • film composites or films or film composites provided with organic and / or inorganic layers are preferably used.
  • films / film composites can consist of all common plastics used for film production, but are not to be mentioned as examples by way of non-limiting example:
  • Polyethylene polypropylene - especially the oriented polypropylene (OPP) produced by mono- or biaxial stretching, cyclic olefin copolymers (COC), polyvinyl chloride (PVC), polyesters - in particular polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), ethylene vinyl alcohol (EVOH), polyvinylidene chloride (PVDC), polyvinylidene fluoride (PVDF), polyacrylonitrile (PAN), polycarbonate (PC), polyamide (PA), polyethersulfone (PES) or polyimide (PI).
  • OPP oriented polypropylene
  • COC cyclic olefin copolymers
  • PVC polyvinyl chloride
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • EVOH ethylene vinyl alcohol
  • PVDC polyvinylidene chloride
  • PVDF polyvinylidene fluoride
  • PAN polyacrylonit
  • the support may also be combined with organic or inorganic coatings or layers. This can be done by conventional methods such as painting, printing, evaporation, sputtering, co-extrusion or lamination.
  • organic or inorganic coatings or layers This can be done by conventional methods such as painting, printing, evaporation, sputtering, co-extrusion or lamination.
  • oxides or nitrides of silicon and of aluminum, indium-tin oxide (ITO) or sol-gel coatings may be mentioned here.
  • carrier films are those made of thin glasses. These are in layer thicknesses of less than 1 mm and even in 30 pm for example. D 263 T from Schott or Willow Glass from Corning available. Thin glass sheets can be further stabilized by the addition of a plastic film (for example polyester) by means of a transfer adhesive tape, if desired.
  • a plastic film for example polyester
  • those or other types of support materials having a thickness of from 15 to 200 ⁇ m, preferably from 20 to 100 ⁇ m, more preferably from 25 to 75, particularly preferably from 30 to 50 ⁇ m.
  • a borosilicate glass such as D263 T eco from Schott, an alkali-alkaline-earth silicate glass or an aluminoborosilicate glass such as AF 32 eco also from Schott are used for thin glasses.
  • An alkali-free thin glass like AF32 eco is advantageous because the UV transmission is higher.
  • An alkali-containing thin glass such as D263 T eco is advantageous because the coefficient of thermal expansion is higher and more compatible with the polymeric components of the other OLED structure.
  • Such glasses can be prepared in the down-draw process as referenced in WO 00/41978 A1 or in processes as disclosed, for example, in EP 1 832 558 A1.
  • WO 00/41978 A1 furthermore discloses processes for producing composites of thin glass and polymer layers or films.
  • these films / film composites in particular the polymer films provided with a permeation barrier for oxygen and water vapor, the permeation barrier exceeds the requirements for the packaging area (WVTR ⁇ 10 1 g / (m 2 d) and OTR ⁇ 10 1 cm 3 / ( m 2 d bar) according to test H).
  • Thin glass sheets or thin glass sheet composites are preferably provided, as usually also polymer films, as a tape from a roll.
  • Corresponding glasses are already offered by the company Corning under the name Willow Glass. This form of delivery can be excellently laminated with a preferably also tape-provided adhesive.
  • the films / film composites may be made transparent so that the overall structure of such an adhesive article is also transparent.
  • Transparency here also means an average transmission in the visible range of light of at least 75%, preferably higher than 90%.
  • adhesives of the same or different types and / or identical or different layer thicknesses according to the invention may be used as upper and lower layers.
  • the carrier can be pretreated on one or both sides according to the prior art, so that, for example, an improvement of the adhesive mass anchorage is achieved.
  • one or both sides may be provided with a functional layer which may act as a barrier layer, for example.
  • the pressure-sensitive adhesive layers can optionally covered with release papers or release liners. Alternatively, only one adhesive layer can be covered with a double-sided separating liner.
  • an adhesive according to the invention is provided in the double-sided (self-adhesive) adhesive tape and any other material, for example one which adheres particularly well to a cover substrate or exhibits particularly good repositionability.
  • the adhesive and any adhesive tape formed therewith are outstandingly suitable for encapsulating an electronic arrangement against permeates by applying the adhesive or the adhesive tape to and / or around the regions of the electronic assembly to be encapsulated.
  • Encapsulation in the present case is not only a complete enclosure with said (adhesive) adhesive but also a regional application of the (adhesive) adhesive on the areas of the (opto) electronic device to be encapsulated, for example a one-sided overlap or a frame an electronic structure.
  • two types of encapsulation can be carried out with adhesive tapes. Either the adhesive tape is first punched out and glued only around the areas to be encapsulated, or it is glued over the entire area to be encapsulated areas.
  • An advantage of the second variant is the easier handling and often better protection.
  • Another object of the present invention relates to a method for encapsulating an electronic device in which a composition of the invention is applied to the electronic device and then cured.
  • the composition hardens in this case so only after application to the electronic device.
  • curing may, however, be activated shortly before application of the composition.
  • a method for encapsulating an electronic device in which an inventive already cured adhesive or an inventive already cured adhesive tape is applied to the electronic device.
  • the cured adhesive of the invention or the cured adhesive tape according to the invention as already explained above, despite such hardening, has such a degree of tack that it is still sufficient to apply the adhesive as a barrier layer to electronic components and thus protect them against damaging influences of oxygen and water vapor ,
  • the end user thus does not perform the activation, ie the start of the crosslinking reaction, in a tight temporal context with the lamination process of the electronic components.
  • the adhesive of the invention or the adhesive tape according to the invention can rather be supplied in already hardened form to the end user.
  • the procedure may be to mix the ingredients of the composition, coat a substrate, such as a liner, and then subject the layer to a curing step.
  • the lamination of the layer to a first target substrate to be bonded, such as an electronic array, is independent of time and usually at least 24 hours, more preferably even a few days or even weeks after this cure.
  • the curing is thus preferably carried out during the production of the adhesive tapes and very preferably during and / or immediately after drying of a solvent-based formulation in the coating process.
  • the adhesive according to the invention or the adhesive tape according to the invention has already been cured prior to application by activation of the initiator, for example at least 1 day before application, preferably at least 3 days or even at least one week before application.
  • the conversion of reactive resin curing with respect to the reactive groups in the reactive resin molecules is typically not 100%. In particular, it can be between 20% and 96% or between 40% and 80%.
  • the invention additionally relates to the use of a composition according to the invention, an adhesive according to the invention or an adhesive tape according to the invention for encapsulating an electronic device, in particular an organic electronic device, preferably an optoelectronic device, in particular an OLED display.
  • the invention relates to a composite of an electronic arrangement, in particular an organic electronic arrangement, and a composition of the invention applied thereto, an adhesive according to the invention or an adhesive tape according to the invention.
  • composition according to the invention allows the production of pressure-sensitive adhesives which fulfill all requirements, such as those applied to an adhesive used to encapsulate an (opto) electronic device:
  • a low volume permeation of water vapor and oxygen in the hardened state which manifests itself in a value for WVTR (Mocon) of less than 15 g / (m 2 d), preferably of less than 10 g / (m 2 d),
  • the invention relates to a composition for producing an adhesive, preferably a pressure-sensitive adhesive, comprising or consisting of
  • a hydrocarbon-based plasticizer having a weight-average molecular weight Mw of from 1,000 to 60,000 g / mol, determined by gel permeation chromatography using tetrahydrofuran as eluent and polystyrene as standard,
  • the invention relates to a composition according to embodiment 1, characterized in that component a) contains or consists of at least one triblock copolymer, which is composed of two terminal hard blocks and a medium soft block, wherein as soft block at least one kind of a first polymer block with a softening temperature of less than -20 ° C and as a hard block at least one grade of a second polymer block having a softening temperature greater than +40 ° C is used, wherein the softening temperature differential scanning calorimetry according to DIN 53765: 1994-03 with a heating rate of 10 K. / min is determined.
  • the triblock copolymer is a polystyrene block polyisobutylene block polystyrene polymer.
  • the invention relates to a composition according to embodiment 1 or 2, characterized in that component a) contains or consists of at least one diblock, star and / or graft copolymer.
  • the invention relates to a composition according to embodiment 2 or 3, characterized in that the component a) at least a diblock copolymer, wherein component a) contains from 40 to ⁇ 100% by weight of the triblock and> 0 to 60% by weight of the diblock copolymer, in particular from 50 to 82% by weight of the triblock and 18 to 50 Wt .-% of Diblockcopolymers.
  • the invention relates to a composition according to any one of the preceding embodiments, characterized in that component a) has a weight-average molecular weight M w of 1,000,000 g / mol or smaller as determined by gel permeation chromatography using tetrahydrofuran as eluent and polystyrene as a standard, preferably 500,000 g / mol or smaller, in particular from 40,000 to 150,000 g / mol.
  • the invention relates to a composition according to one of the preceding embodiments, characterized in that the adhesive resin is at least 70%, preferably at least 90%, based on the number of double bonds before the hydrogenation, hydrogenated, in particular fully hydrogenated.
  • the invention relates to a composition according to one of the preceding embodiments, characterized in that the softening temperature of the adhesive resin b) at least 80 ° C and at most 130 ° C, measured according to Ring and Ball according to ASTM E28-14, preferably at least 90 ° C is at most 1 15 ° C.
  • the invention relates to a composition according to one of the preceding embodiments, characterized in that the adhesive resin resin b) is a nonpolar resin having a DACP value (diacetone alcohol cloud point) of above 25 ° C, in particular of at least 30 ° C, preferably from 35 to 80 ° C, and a MMAP value (mixed methylcyclohexane aniline point) greater than 60 ° C, preferably from 65 to 90 ° C, is.
  • DACP value diacetone alcohol cloud point
  • MMAP value mixed methylcyclohexane aniline point
  • the invention relates to a composition according to one of the preceding embodiments, characterized in that the reactive resin c) is cationically curable.
  • the invention relates to a composition according to one of the preceding embodiments, characterized in that the Reactive resin c) based on a cyclic ether, in particular cycloaliphatic epoxide.
  • the invention relates to a composition according to one of the preceding embodiments, characterized in that the reactive resin c) in the uncured state has a softening temperature of less than 40 ° C, measured by differential scanning calorimetry according to DIN 53765: 1994- 03 with a Heating rate of 10 K / min, preferably less than 20 ° C.
  • the invention relates to a composition according to one of the preceding embodiments, characterized in that the initiator d) is selected from thermally activatable initiators for the initiation of a cationic curing, radiation-mixed initiators for the initiation of a cationic curing, in particular UV initiators, and Mixtures of these.
  • the invention relates to a composition according to embodiment 12, characterized in that the activation temperature of the thermally activatable initiator is at most 150 ° C, preferably at most 100 ° C.
  • the invention relates to a composition according to embodiment 12 or 13, characterized in that the thermally activatable initiator is selected from the group comprising pyridinium, ammonium, anilinium, sulfonium, thiolanium salts and metal salt triflates, in particular triflates of Calcium, zinc, aluminum, rare earth or lanthanides and mixtures of these.
  • the invention relates to a composition according to any one of embodiments 12 to 14, characterized in that the photoinitiator below 350 nm absorbs UV light and allows cationic curing, wherein the photoinitiator is selected in particular from sulfonium, iodonium and Metallocene-based photoinitiators.
  • the invention relates to a composition according to one of the embodiments 12 to 15, characterized in that the proportion of thermally activatable initiators with respect to the reactive resin use amount at least 0.3 wt .-% and at most 5.0 wt .-%, preferably at least 0.5 wt .-% and at most 2.5 wt .-% and very preferably between 0.8 and 1, 5 wt .-% and / or the proportion of radiation-activatable initiators in relation to the reactive resin use amount at least 0.1 wt .-% and at most 2.5 wt .-%, preferably at least 0.2 wt .-% and at most 1, 5 wt .-%, very preferably at least 0.3 wt .-% and at most 1, 0 wt .-%, is.
  • the invention relates to a composition according to one of the preceding embodiments, characterized in that the hydrocarbon-based plasticizer e) has a weight-average molecular weight M w of 2,000 to 20,000 g / mol, determined by means of gel permeation chromatography using tetrahydrofuran as eluent and Polystyrene as standard, and / or that the hydrocarbon-based plasticizer e) consists of at least 90 wt .-% of saturated hydrocarbons, preferably at least 95 wt .-%, based on the mass of the plasticizer e).
  • the invention relates to a composition according to one of the preceding embodiments, characterized in that the additive f) is selected from the group consisting of primary antioxidants, secondary antioxidants, process stabilizers, light stabilizers, processing aids, Endblockverorgrharzen and polymers, in particular of an elastomeric nature.
  • the invention relates to a composition according to one of the preceding embodiments, characterized in that the filler g) is selected from nanoscale fillers, transparent fillers, getter and / or scavenger fillers.
  • the invention relates to an adhesive, in particular a pressure-sensitive adhesive, obtainable or obtained by curing a composition according to one of embodiments 1 to 19, wherein the adhesive is preferably transparent in the visible region of the spectrum from 400 nm to 800 nm.
  • the invention relates to an adhesive according to embodiment 20, characterized in that the adhesive has a haze of less than 5.0%, measured according to ASTM D 1003-13, preferably less than 2.5%.
  • the invention relates to an adhesive according to embodiment 20 or 21, characterized in that the adhesive has a yellowness Ab * from 0.0 to 1.0, measured according to DIN 6174: 1979-01 at a layer thickness of 50 mhh, preferably from 0.1 to 0.9.
  • the invention relates to an adhesive tape comprising at least one flat support and a layer of an adhesive applied thereto according to one of embodiments 20 to 22, wherein the support comprises in particular a coated plastic film or a layer of flexible thin glass with a layer thickness of at most 1 mm, preferably at most 100 mhh, wherein the thin glass is preferably a borosilicate glass or a alkali-free aluminoborosilicate glass.
  • the invention relates to an adhesive tape according to embodiment 23, characterized in that the support has a permeation barrier of WVTR ⁇ 0.1 g / (m 2 d) according to ASTM F-1249: 2013.
  • the invention relates to a transfer adhesive tape comprising a layer of an adhesive according to one of embodiments 20 to 22, wherein a siliconized liner is preferably arranged on at least one, in particular on both sides of the layer.
  • the invention relates to a method for encapsulating an electronic device, characterized in that a composition according to one of embodiments 1 to 19 applied to the electronic device and then cured, or an adhesive according to any of embodiments 20 to 22 or an adhesive tape according to one of the embodiments 23 to 25 is applied to the electronic device.
  • the invention relates to the use of a composition according to one of embodiments 1 to 19, an adhesive according to one of the embodiments 20 to 22 or an adhesive tape according to one of the embodiments 23 to 25 for encapsulating an electronic device.
  • the invention relates to a composite of an electronic arrangement, in particular an organic electronic arrangement, and a composition applied thereto according to one of embodiments 1 to 19, an adhesive according to one of embodiments 20 to 22 or an adhesive tape according to one of embodiments 23 to 25.
  • FIG. 1 shows a first (opto) electronic arrangement in a schematic representation
  • Fig. 3 shows a third (opto) electronic arrangement in a schematic representation.
  • This arrangement 1 shows a first embodiment of an (opto) electronic device 1.
  • This arrangement 1 has a substrate 2 on which an electronic structure 3 is arranged.
  • the substrate 2 itself is formed as a barrier for permeates and thus forms part of the encapsulation of the electronic structure 3.
  • another cover 4 designed as a barrier is arranged above the electronic structure 3, in the present case also spatially spaced therefrom.
  • a pressure-sensitive adhesive 5 is provided circumferentially next to the electronic structure 3 on the substrate 2.
  • the encapsulation does not take place with a pure pressure-sensitive adhesive 5 but with an adhesive tape 5 which contains at least one pressure-sensitive adhesive of the invention.
  • the pressure-sensitive adhesive 5 connects the cover 4 to the substrate 2.
  • the pressure-sensitive adhesive 5 also allows the spacing of the cover 4 from the electronic structure 3 by means of a correspondingly thick embodiment.
  • the PSA 5 is based on the PSA according to the invention as described above in a general form and is described in more detail below in exemplary embodiments. In the present case, the PSA 5 not only performs the function of bonding the substrate 2 to the cover 4, but also forms a barrier layer for permeates so as to encapsulate the electronic structure 2 also from the side against permeates such as water vapor and oxygen.
  • the PSA 5 is presently also provided in the form of a diecut from a double-sided adhesive tape. Such a punched product enables a particularly simple application.
  • the pressure-sensitive adhesive 5 has already been cured by the manufacturer and, even in this state, still has sufficient tack to be adhered to the electronic structure 3.
  • the curing temperatures - in this case, a thermal initiator was used - are between 60 ° C and 125 ° C.
  • Fig. 2 shows an alternative embodiment of an (opto) electronic device 1. Shown again is an electronic structure 3, which is arranged on a substrate 2 and encapsulated by the substrate 2 from below. Above and to the side of the electronic structure, the pressure-sensitive adhesive 5 is now arranged over its entire surface. The electronic structure 3 is thus completely encapsulated from above by the pressure-sensitive adhesive 5. On the PSA 5, a cover 4 is then applied. In contrast to the previous embodiment, this cover 4 does not necessarily have to meet the high barrier requirements, since the barrier is already provided by the pressure-sensitive adhesive. The cover 4 may, for example, only perform a mechanical protective function, but it may also be additionally provided as a permeation barrier.
  • FIG. 3 shows a further alternative embodiment of an (opto) electronic device 1.
  • two pressure-sensitive adhesives 5a, 5b are now provided, which in the present case are of identical design.
  • the first pressure-sensitive adhesive 5a is arranged over the entire surface of the substrate 2.
  • the electronic structure 3 is provided, which is fixed by the PSA 5a.
  • the composite of pressure-sensitive adhesive 5a and electronic structure 3 is then covered over the entire area with the further pressure-sensitive adhesive 5b, so that the electronic structure 3 of all Pages by the pressure-sensitive adhesives 5a, b is encapsulated.
  • the cover 4 is provided above the PSA 5b again the cover 4 is provided.
  • neither the substrate 2 nor the cover 4 necessarily have barrier properties. However, they can still be provided to further restrict the permeation of permeates to the electronic structure 3.
  • the pressure-sensitive adhesive 5 is here and preferably applied in each case with a homogeneous layer thickness.
  • the transition is fluid and it may remain small un-filled or gas-filled areas.
  • the PSA is locally compressed to different degrees, so that by flow processes a certain compensation of the height difference can be made to the edge structures.
  • the dimensions shown are not to scale, but rather serve only a better representation.
  • the electronic structure itself is usually relatively flat (often less than 1 pm thick).
  • the application of the PSA 5 takes place in all embodiments shown in the form of an already cured pressure-sensitive adhesive tape.
  • This can basically be a double-sided pressure-sensitive adhesive tape with a carrier or a transfer adhesive tape.
  • an embodiment is selected as a transfer adhesive tape.
  • the thickness of the PSA which is present either as a transfer adhesive tape or coated on a flat structure, is preferably between about 1 pm and about 150 pm, more preferably between about 5 pm and about 75 pm and particularly preferably between about 12 pm and 50 pm.
  • High layer thicknesses between 50 pm and 150 pm are used when an improved adhesion to the substrate and / or a damping effect within the (opto) electronic structure is to be achieved.
  • the disadvantage here however, the increased permeation cross section.
  • Low layer thicknesses between 1 pm and 12 pm reduce the permeation cross-section, so that the lateral permeation and the total thickness of the (opto) electronic structure. However, it does happen a reduction of adhesion from the substrate.
  • the particularly preferred thickness ranges there is a good compromise between a small mass thickness and the consequent low permeation cross section, which reduces lateral permeation, and a sufficiently thick mass film for producing a sufficiently adherent compound.
  • the optimum thickness depends on the (opto) electronic structure, the end use, the type of execution of the PSA and optionally the sheet substrate.
  • the thickness of the individual pressure-sensitive adhesive layer (s) also preferably lies between about 1 ⁇ m and about 150 ⁇ m, more preferably between about 5 ⁇ m and about 75 ⁇ m, and particularly preferably between about 12 ⁇ m and 50 ⁇ m for the barrier adhesive composition (s) pm is. If, in addition to one barrier adhesive according to the invention, another is used in double-sided adhesive tapes, then it may also be advantageous if its thickness is above 150 ⁇ m.
  • a suitable method for bonding the adhesive products with the PSAs according to the invention involves the removal of the first adhesive surface from a protective liner layer and the lamination of the adhesive product onto a first target substrate. This can be done by lamination by means of (rubber) rollers or in presses. Due to the pressure-sensitive tackiness, a particularly high pressure during lamination is not always necessary. You get a Vorverbund. Subsequently, the second adhesive surface is freed from the protective liner layer and placed on the second target substrate. This can also be done by lamination by means of (rubber) rollers or in presses. The selection of the lamination process depends on the nature of the pre-bond (rigid or flexible) and the second target substrate (rigid or flexible). Again, a particularly high pressure when laminating by the pressure-sensitive adhesive is not required in every case. Further curing is not necessary because the adhesive is already largely cured and at most subsequently postcrosslinked to a small extent by itself.
  • the lamination result can be further improved by a subsequent autoclaving step in its quality.
  • TestA softening temperature
  • the softening temperature of copolymers, hard and soft blocks and uncured reactive resins is determined calorimetrically by differential scanning calorimetry (DSC) according to DIN 53765: 1994-03. Heating curves run at a heating rate of 10 K / min. The samples are measured in Al crucibles with perforated lid and nitrogen atmosphere. The second heating curve is evaluated. In the case of amorphous materials, glass transition temperatures occur; in the case of (semi) crystalline materials, melting temperatures. A glass transition is recognizable as a step in the thermogram. The glass transition temperature is evaluated as the center of this stage. A melting temperature can be recognized as a peak in the thermogram. The melting temperature is the temperature at which the highest heat of reaction occurs.
  • the adhesive resin softening temperature is carried out according to the relevant method known as Ring and Ball, which is standardized according to ASTM E28-14.
  • a Ring-Kugel-Automat HRB 754 from Herzog is used to determine the adhesive resin softening temperature of the resins. Resin samples are first finely ground. The resulting powder is placed in a brass cylinder with bottom opening (inner diameter at the upper part of the cylinder 20 mm, diameter of the bottom opening of the cylinder 16 mm, height of the cylinder 6 mm) and melted on a heating table. The filling amount is chosen so that the resin after melting completely fills the cylinder without supernatant.
  • the resulting specimen including the cylinder, is inserted in the sample holder of the HRB 754.
  • Glycerol is used to fill the tempering bath, provided that the adhesive resin softening temperature is between 50 ° C and 150 ° C. At lower Klebharzerweichungstemperaturen can also be used with a water bath.
  • the test balls have a diameter of 9.5 mm and weigh 3.5 g.
  • the ball is placed above the specimen in the temperature control bath and deposited on the specimen. 25 mm below the cylinder bottom there is a catch plate, 2 mm above this a light barrier. During the measuring process, the temperature is increased at 5 ° C / min.
  • the ball In the temperature range of the adhesive resin softening temperature, the ball begins to move through the bottom opening of the cylinder until it eventually stops on the catch plate. In this position, it is detected by the photocell and registered at this time, the temperature of the bath. There is a double determination.
  • the adhesive resin softening temperature is the average of the two individual measurements.
  • the determination of the permeability to water vapor is carried out in accordance with ASTM F-1249: 2013.
  • the pressure-sensitive adhesive is applied to a permeable membrane with a layer thickness of 50 ⁇ m.
  • the water vapor permeability is determined at 37.5 ° C and a relative humidity of 90%.
  • the determination of the bond strength was carried out as follows: Glass plates (float glass) were used as a defined primer.
  • the bonded surface element to be tested which was provided on the back with a 23 ⁇ m PET film for stabilization, was cut to a width of 20 mm and a length of about 25 cm, provided with a handling section and immediately thereafter five times with a steel roller of 4 kg at a feed of 10 m / min pressed on the selected adhesion (glass, air side).
  • the previously bonded surface element at an angle of 180 ° at room temperature and at 30 mm / min was removed from the primer with a tensile tester (Zwick) and measured the force required for this purpose.
  • the measured value (in N / cm) was the average of three individual measurements.
  • a calcium test was used.
  • a 10 ⁇ 10 mm 2 large, thin calcium layer is deposited on a glass plate in a vacuum and then stored under a nitrogen atmosphere.
  • the thickness of the calcium layer is about 100 nm.
  • an adhesive tape 23 ⁇ 23 mm 2
  • a thin-glass disc 35 ⁇ m, Schott
  • the thin glass pane was laminated with a 100 ⁇ m thick PET film by means of a 50 ⁇ m thick transfer adhesive tape of an optically highly transparent acrylic PSA.
  • the adhesive is applied to the glass plate in such a way that the adhesive covers the calcium level with an all-round protruding edge of 6.5 mm (AA). Due to the opaque glass carrier only the permeation through the pressure-sensitive adhesive or along the interfaces is determined.
  • the test is based on the reaction of calcium with water vapor and oxygen, as described for example by AG Erlat et. al. in the 47th Annual Technical Conference Proceedings Society of Vacuum Coaters, 2004, pp. 654-659, and by ME Gross et al. in "46th Annual Technical Conference Proceedings Society of Vacuum Coaters", 2003, pages 89 to 92.
  • the light transmission of the calcium layer is monitored, which increases by the conversion into calcium hydroxide and calcium oxide. This takes place in the described test setup from the edge, so that the visible surface of the Calcium level decreased. It is called the time to halving the light absorption of the calcium level as a lifetime.
  • the method captures both the degradation of the surface of the calcium level from the edge and the selective reduction in the area as well as the homogeneous reduction of the layer thickness of the calcium level due to full-scale degradation.
  • the measurement conditions selected were 85 ° C. and 85% relative humidity.
  • the samples were glued with a layer thickness of the PSA of 50 pm over the entire surface and without bubbles.
  • the degradation of the Ca level is monitored by transmission measurements.
  • the lag time is defined as the time it takes for moisture to travel the distance to the Ca.
  • This test serves to quickly test the shear strength of adhesive tapes under temperature load.
  • the test was carried out according to DIN EN 10088-2: 2014.
  • the adhesive tape to be examined is glued to a temperature-controllable steel plate, loaded with a weight (50 g) and recorded the shear distance.
  • the adhesive tape to be examined (50 ⁇ m transfer tape) is stuck with one of the adhesive sides onto a 50 ⁇ m thick aluminum foil.
  • the thus prepared adhesive tape is cut to a size of 10 mm * 50 mm.
  • the sample to be measured is loaded at the lower end with a weight of 50 g.
  • the steel test plate with the bonded sample is heated starting at 25 ° C at a rate of 9 K / min to the final temperature of 200 ° C.
  • the slip path of the sample is monitored by means of a distance sensor as a function of temperature and time.
  • the maximum sliding distance is set to 1000 pm (1 mm), if exceeded, the test is stopped and the failure temperature recorded.
  • Test climate room temperature 23 +/- 3 ° C, relative humidity 50 +/- 5%. The result is the average of two individual measurements and is given in ° C.
  • Tack measurement is performed according to the relevant methodology, which is standardized in accordance with ASTM D2979-01.
  • the tester is the Texture Analyzer TA.XT from Stable Micro Systems Ltd ..
  • a probe with a cylindrical stamp made of stainless steel is driven at a predetermined test speed up to a defined contact force perpendicular to the adhesive and withdrawn again at a predetermined speed after a defined contact time. During this process, the force applied for pressing or releasing is registered as a function of the path.
  • the variable test parameters which must be specified with the test characteristic were adjusted according to the samples to be examined: stamp geometry: 0 2 mm, pressure force 1 N, contact time 1 s and take-off speed 1, 5 mm / s.
  • the steel stamp is cleaned in acetone and conditioned for 30 minutes at room temperature before testing an adhesive pattern. During the individual measurements at different points of a test pattern, the stamp is not cleaned.
  • the base test plate used was a steel plate with a polished stainless steel surface onto which the samples to be examined were laminated.
  • Test climate room temperature 23 +/- 3 ° C, relative humidity 50 +/- 5%.
  • the result is the mean value of the maximum force of each individual curve determined from 10 individual measurements and is given in N.
  • the color measurement is carried out on the respective pure adhesive layer in a layer thickness of 50 ⁇ m after it has been freed from the release liners.
  • Ab * is the difference between the color value determination for the adhesive film pattern applied to the substrate tile and the color value determination of the pure substrate tile.
  • a 50 ⁇ m transfer adhesive tape was applied bubble-free to a polycarbonate film (125 ⁇ m Lexan 8010 with freshly covered surfaces, haze of this film alone 0.09%).
  • the samples were measured by method J1 and J2.
  • the transmission of the adhesive was determined via the VIS spectrum.
  • the images of the VIS spectrum were carried out on a UVIKON 923 from Kontron.
  • the wavelength range of the measured spectrum covers all wavelengths between 800 nm and 400 nm with a resolution of 1 nm.
  • An empty channel measurement was carried out as a reference over the entire wavelength range. For the indication of the result, the transmission measurements in the specified range were averaged. A correction of interfacial reflection losses is not made.
  • the haze value describes the proportion of the transmitted light, which is scattered by the irradiated sample forward at a large angle. Thus, the haze value quantifies material defects in the surface or structure that interfere with the clear view.
  • the method for measuring the Haze value is described in the standard ASTM D 1003. The standard requires the measurement of four transmission measurements. For each transmission measurement, the light transmittance is calculated. The four transmittances are calculated as the percentage Haze value. The Haze value is measured with a Haze-gard Dual from Byk-Gardner GmbH. Unless otherwise stated, all quantities in the following examples are percentages by weight or parts by weight based on the total composition.
  • test substance the adhesive resin sample to be investigated
  • xylene mixture of isomers, CAS [1330-20-7],> 98.5%, Sigma-Aldrich # 320579 or similar
  • the test substance is dissolved and then cooled to 80 ° C. Any escaped xylene is filled in with additional xylene, so that again 5.0 g of xylene are present.
  • diacetone alcohol (4-hydroxy-4-methyl-2-pentanone, CAS [123-42-2], 99%, Aldrich # H41544 or comparable
  • the sample glass is shaken until the test substance has completely dissolved.
  • the solution is heated to 100 ° C.
  • the sample glass with the resin solution is then introduced into a cloud point measuring device Chemotronic Cool from Novomatics and tempered there to 1 10 ° C. With a cooling rate of 1, 0 K / min is cooled.
  • the cloud point is optically detected.
  • the temperature is recorded at which the turbidity of the solution is 70%. The result is given in ° C.
  • the lower the DACP value the higher the polarity of the test substance.
  • test substance the adhesive resin sample to be examined
  • 10 mL of dry aniline CAS [62-53-3],> 99.5%, Sigma-Aldrich # 51788 or equivalent
  • 5 mL dry methylcyclohexane CAS [108-87-2],> 99%, Sigma-Aldrich # 300306 or equivalent
  • the sample glass is shaken until the test substance has completely dissolved.
  • the solution is heated to 100 ° C.
  • the sample glass with the resin solution is then introduced into a cloud point measuring device Chemotronic Cool from Novomatics and tempered there to 1 10 ° C. With a cooling rate of 1, 0 K / min is cooled.
  • the cloud point is optically detected.
  • the temperature is recorded at which the turbidity of the solution is 70%. The result is given in ° C.
  • the lower the MMAP value the higher the aromaticity of the test substance. Used raw materials
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (162.5 g) and Sibstar 62M UBP (162.5 g) were used.
  • the adhesive used was Eastotac H100-W from Eastman, a fully hydrogenated hydrocarbon resin (275 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • a thermally activatable initiator was added to the formulation.
  • 2.5 g of K-Pure CXC 1613 from King Industries was weighed out as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements
  • Test G specimens for the thermal shear strength test
  • the sample tack (Test H) of the sample was 2.6N.
  • the 50 g / m 2 thick transfer tape without prior lamination was used for WVTR measurements (Mocon, Test D).
  • the result from the WVTR measurement was 9.3 g / m 2 * d.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (217.5 g) and Sibstar 62M UBP (137.5 g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (195 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • a polybutene plasticizer, Ter Pib 950 (200 g) from Ter Hell GmbH & Co. KG was added.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements.
  • Test G specimens for the thermal shear strength test
  • test H The sample tack (test H) of the sample was 3.6 N.
  • the 50 g / m 2 thick transfer tape without prior lamination was used for WVTR measurements (Mocon, Test D).
  • the result from the WVTR measurement was 9.4 g / m 2 * d.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (172.5 g) and Sibstar 62M UBP (172.5 g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (255 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • a polyisobutylene plasticizer, the Oppanol B10N (150 g) from BASF was added.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements
  • Test G specimens for the thermal shear strength test
  • test H The sample tack (test H) of the sample was 3.3 N.
  • the yellowness value Ab * (test I) on the substrate tile was +0.07.
  • the 50 g / m 2 thick transfer tape without prior lamination was used for WVTR measurements (Mocon, Test D).
  • the result from the WVTR measurement was 6.4 g / m 2 * d.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (227.5 g) and Sibstar 62M UBP (177.5 g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (265 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • a polybutene plasticizer, Ter Pib 950 (80 g) from Ter Hell GmbH & Co. KG was added.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements
  • Test G specimens for the thermal shear strength test
  • test H The sample tack (test H) of the sample was 3.1N.
  • the yellowness value Ab * (test I) on the substrate tile was +0.06.
  • the 50 g / m 2 thick transfer tape without prior lamination was used for WVTR measurements (Mocon, Test D).
  • the result from the WVTR measurement was 10.6 g / m 2 * d.
  • (co) polymer a polystyrene-block-polyisobutylene block copolymer from Kaneka was selected. Sibstar 103T UL (325 g) was used. The adhesive used was Eastotac H100W from Eastman, a fully hydrogenated hydrocarbon resin (275 g). The reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g). In addition, a polybutene plasticizer, Ter Pib 950 (150 g) from Ter Hell GmbH & Co. KG, was added.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements
  • Test G specimens for the thermal shear strength test
  • the sample tack (Test H) of the sample was 3.0N.
  • the 50 g / m 2 thick transfer tape without prior lamination was used for WVTR measurements (Mocon, Test D).
  • the result from the WVTR measurement was 7.1 g / m 2 * d.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (142.5 g) and Sibstar 62M UBP (142.5 g) were used.
  • the adhesive used was Eastotac H 100W from Eastman, a fully hydrogenated hydrocarbon resin (215 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • a polybutene plasticizer containing Ter Pib 950 (250 g) from Ter Hell GmbH & Co. KG was added.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements
  • Test G specimens for the thermal shear strength test
  • test H The sample tack (test H) of the sample was 3.3 N.
  • the yellowness value Ab * (test I) on the substrate tile was +0.08.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (177.5 g) and Sibstar 62M UBP (247.5 g) were used.
  • the adhesive used was Eastotac H100W from Eastman, a fully hydrogenated hydrocarbon resin (275 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • a polybutene plasticizer, Ter Pib 950 (50g) from Ter Hell GmbH & Co. KG was added. These raw materials were dissolved in a mixture of Siedbenzin 60/95 (1050 g) and toluene (450 g), so that a 40 wt .-% solution is formed.
  • a thermally activatable initiator was added to the formulation.
  • 2.5 g of K-Pure CXC 1613 from King Industries was weighed out as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements.
  • the bond strength to glass after equilibration at 23 ° C and 50% rel. Humidity determined and was 1, 1 N / cm.
  • Test G specimens for the thermal shear strength test
  • the sample tack (Test H) of the sample was 1, 4N.
  • the yellowness value Ab * (test I) on the substrate tile was +0.04.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (172.5 g) and Sibstar 62M UBP (172.5 g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (255 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • the Wingtack 10 150 g) from Total Cray Valley was added. These raw materials were dissolved in a mixture of Siedbenzin 60/95 (1200 g) and toluene (300 g), so that a 40 wt .-% solution is formed.
  • a thermally activatable initiator was added to the formulation.
  • 2.5 g of K-Pure CXC 1613 from King Industries was weighed out as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner. From these samples test specimens for adhesion measurements (Test E) were produced. The bond strength to glass after equilibration at 23 ° C and 50% rel. Humidity determined and was 2.0 N / cm.
  • Test G specimens for the thermal shear strength test
  • test H The sample tack (test H) of the sample was 3.9 N.
  • the yellowness value Ab * (test I) on the substrate tile was +0.39.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (212.5 g) and Sibstar 62M UBP (212.5 g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (125 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • a polybutene plasticizer, Ter Pib 950 (200 g) from Ter Hell GmbH & Co. KG was added. These raw materials were dissolved in a mixture of Siedbenzin 60/95 (1050 g) and toluene (450 g), so that a 40 wt .-% solution is formed.
  • a thermally activatable initiator was added to the formulation.
  • 2.5 g of K-Pure CXC 1613 from King Industries was weighed out as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements
  • the bond strength to glass after equilibration at 23 ° C and 50% rel. Humidity determined and was 1, 5 N / cm.
  • specimens for the thermal shear strength test (Test G) were prepared from these samples. The result of the SAFT test was> 200 ° C.
  • test H The sample tack (test H) of the sample was 2.2 N.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (140g) and Sibstar 62M UBP (140g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (350 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • a polybutene plasticizer, Ter Pib 950 (120 g) from Ter Hell GmbH & Co. KG was added. These raw materials were dissolved in a mixture of Siedbenzin 60/95 (1200 g) and toluene (300 g), so that a 40 wt .-% solution is formed.
  • a thermally activatable initiator was added to the formulation.
  • 2.5 g of K-Pure CXC 1613 from King Industries was weighed out as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements
  • Test G specimens for the thermal shear strength test
  • Sample Tack (Test H) of the sample was 4.7N.
  • the yellowness value Ab * (test I) on the substrate tile was +0.08.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (110 g) and Sibstar 62M UBP (110 g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (280 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (280 g).
  • a polybutene plasticizer, Ter Pib 950 (220g) from Ter Hell GmbH & Co. KG was added. These raw materials were dissolved in a mixture of Siedbenzin 60/95 (1050 g) and toluene (450 g), so that a 40 wt .-% solution is formed.
  • a thermally activatable initiator was added to the formulation.
  • 3 g of K-Pure CXC 1613 from King Industries was weighed out as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements
  • Test G specimens for the thermal shear strength test
  • test H The sample tack (test H) of the sample was 3.9 N.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (220g) and Sibstar 62M UBP (220g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (260 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (200 g).
  • a polybutene plasticizer, Ter Pib 950 (100 g) from Ter Hell GmbH & Co. KG was added. These raw materials were dissolved in a mixture of Siedlebenzin 60/95 (1200 g), isopropanol (150 g) and toluene (150 g), so that a 40 wt .-% solution is formed.
  • a thermally activatable initiator was added to the formulation.
  • 3 g of K-Pure CXC 1613 from King Industries was weighed out as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements
  • Test G specimens for the thermal shear strength test
  • test H The sample tack (test H) of the sample was 3.6 N.
  • the yellowness value Ab * (test I) on the substrate tile was +0.04.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. There were Sibstar 103T UL (140 g) and Sibstar 62M UBP (140g) used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (220 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (350 g).
  • a polybutene plasticizer, Ter Pib 950 (150 g) from Ter Hell GmbH & Co. KG was added. These raw materials were dissolved in a mixture of Siedbenzin 60/95 (1050 g) and toluene (450 g), so that a 40 wt .-% solution is formed.
  • a thermally activatable initiator was added to the formulation.
  • 3.5 g of K-Pure CXC 1613 from King Industries was weighed out as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements.
  • Test G specimens for the thermal shear strength test
  • test H The sample tack (test H) of the sample was 2.2 N.
  • the yellowness value Ab * (test I) on the substrate tile was +0.08.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (195 g) and Sibstar 62M UBP (195 g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (290 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (120 g).
  • a polybutene plasticizer, Ter Pib 950 (200 g) from Ter Hell was used GmbH & Co.KG, added. These raw materials were dissolved in a mixture of Siedbenzin 60/95 (1050 g) and toluene (450 g), so that a 40 wt .-% solution is formed.
  • a thermally activatable initiator was added to the formulation.
  • 1, 5 g of K-Pure CXC 1613 King Industries was considered as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements.
  • the bond strength to glass after equilibration at 23 ° C and 50% rel. Humidity determined and was 1, 1 N / cm.
  • Test G specimens for the thermal shear strength test
  • test H The sample tack (test H) of the sample was 4.2N.
  • the yellowness value Ab * (test I) on the substrate tile was +0.04.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (177.5 g) and Sibstar 62M UBP (177.5 g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (265 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • a polybutene plasticizer, Ter Pib 950 (80 g) from Ter Hell GmbH & Co. KG was added.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • the samples were cured without prior lamination by UV light through the PET liner (dose: 80 mJ / cm 2 , lamp type: undoped mercury emitter).
  • Test E test specimens for adhesion measurements
  • Test G specimens for the thermal shear strength test
  • test F a life test
  • lag time 100 h.
  • (co) polymer a mixture of two polystyrene-block-polyisobutylene block copolymers from Kaneka was selected. Sibstar 103T UL (177.5 g) and Sibstar 62M UBP (177.5 g) were used.
  • the adhesive resin used was Regalite R1090 from Eastman, a fully hydrogenated hydrocarbon resin (265 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (250 g).
  • a polybutene plasticizer, the Ter Pib 950 (80 g) from Ter Hell GmbH & Co.KG added.
  • the formulation was added to a thermal activatable initiator, K-Pure CXC 1612 from King Industries.
  • a thermal activatable initiator K-Pure CXC 1612 from King Industries.
  • 7.5 g CXC 1612 were weighed as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • Test E test specimens for adhesion measurements.
  • Test G specimens for the thermal shear strength test
  • test F a life test
  • lag time 100 h.
  • (co) polymer a polystyrene block polyisobutylene block copolymer from Kaneka was selected. Sibstar 62M UBP (375 g) was used.
  • the adhesive resin used was Regalite R1 100 from Eastman, a fully hydrogenated hydrocarbon resin (350 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (275 g). An additional plasticizer was not added. These raw materials were dissolved in a mixture of Siedbenzin 60/95 (1050 g) and toluene (450 g), so that a 40 wt .-% solution is formed.
  • a thermally activatable initiator was added to the formulation.
  • 2.75 g of K-Pure CXC 1614 from King Industries was weighed out as initiator / hardener.
  • the amount of initiator was prepared as a 20 wt .-% solution in acetone and added to the above mixture.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • the sample tack (Test H) of the sample was 0.002 N.
  • Adhesive test specimens (Test E) or Heat Resistance Tests (Test G) could not be produced due to lack of tack / tack.
  • (co) polymer a polystyrene block polyisobutylene block copolymer from Kaneka was selected. Sibstar 62M UBP (375 g) was used.
  • the adhesive resin used was Regalite R1 100 from Eastman, a fully hydrogenated hydrocarbon resin (350 g).
  • the reactive resin selected was Uvacure 1500 from Allnex, a cycloaliphatic diepoxide (275 g). An additional plasticizer was not added. These raw materials were dissolved in a mixture of Siedbenzin 60/95 (1050 g) and toluene (450 g), so that a 40 wt .-% solution is formed.
  • a thermally activatable initiator was added to the formulation.
  • 2.75 g of K-Pure CXC 1613 from King Industries was weighed out as initiator / hardener.
  • the formulation was coated from solution onto a siliconized PET liner and dried at 120 ° C for 10 min. The application was then at 50 g / m 2 . The pattern was covered with another layer of a siliconized but more easily separating PET liner.
  • the sample tack (Test H) of the sample was 0.002 N.
  • Adhesive test specimens (Test E) or Heat Resistance Tests (Test G) could not be produced due to lack of tack / tack.
  • Comparative Example 17 and 18 (based on DE 10 2015 212 058 A1) lead to processible adhesives, however, subsequent lamination on an electronic component would not be possible in these formulations since the tackiness which has already occurred is so low in that sufficient substrate adhesion can not be achieved.
  • inventive examples show in comparison with the reference examples that only in compliance with the inventive proportions of components a) to e) functioning PSAs can be produced already sent in the (pre-) cured state to the end user and there as a barrier layer for electronic Components can be used. This applies in particular to the thermal shear strength and the pressure-sensitive tackiness in the cured state, as well as the yellowness value (Reference Example 8).

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition pour produire une masse adhésive, de préférence une masse adhésive fixante, comprenant ou constituée de a) 25 à 42 % en poids d'au moins un copolymère à blocs contenant au moins de l'isobutylène et/ou du butylène en tant que comonomère, b) 15 à 30 % en poids d'au moins une résine adhésive partiellement hydrogénée, c) 7 à 22 % en poids d'au moins une résine réactive, d) 0,1 à 5 % en poids d'au moins un initiateur, e) 15 à 30 % en poids d'un plastifiant à base d'hydrocarbures ayant une masse moléculaire moyenne en poids Mw de 1000 à 60 000 g/mol, déterminée par chromatographie par perméation de gel en utilisant du tétrahydrofurane comme éluant et du polystyrène comme étalon, f) 0 à 5,0 % en poids d'au moins un additif ainsi que g) 0 à 20,0 % en poids d'au moins une charge. La masse adhésive est adaptée entre autres pour encapsuler un dispositif électronique. L'invention concerne en outre une masse adhésive, en particulier une masse adhésive fixante, qui peut être obtenue à partir de ladite composition, ainsi qu'un ruban adhésif muni de ce type de masse adhésive. L'invention concerne en outre un procédé pour encapsuler un dispositif électronique à l'aide de ce type de composition, masse adhésive ou ruban adhésif, leur utilisation ainsi qu'une structure composite constituée d'un dispositif électronique et d'une composition appliquée sur celui-ci, d'une masse adhésive ou d'un ruban adhésif.
PCT/EP2019/051744 2018-02-20 2019-01-24 Composition pour produire une masse adhésive, en particulier pour encapsuler un dispositif électronique Ceased WO2019162035A1 (fr)

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DE102018202545.2A DE102018202545A1 (de) 2018-02-20 2018-02-20 Zusammensetzung zur Erzeugung einer Klebemasse insbesondere zur Kapselung einer elektronischen Anordnung

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US12468182B2 (en) 2021-04-16 2025-11-11 E Ink Corporation Electrophoretic display with low profile edge seal

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Publication number Priority date Publication date Assignee Title
DE102018215062A1 (de) 2018-09-05 2020-03-05 Tesa Se Haftklebemasse für flexibles Display
DE102021201094A1 (de) 2021-02-05 2022-08-11 Tesa Se Polyvinylaromat-Polydien-Blockcopolymer basierende Haftklebemassen mit gesteigerter Wärmescherfestigkeit

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12468182B2 (en) 2021-04-16 2025-11-11 E Ink Corporation Electrophoretic display with low profile edge seal

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