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WO2017085127A1 - Système de résine époxyde, résine époxyde, utilisation d'un système de résine époxyde, composant comprenant une résine époxyde et procédé pour produire une résine époxyde - Google Patents

Système de résine époxyde, résine époxyde, utilisation d'un système de résine époxyde, composant comprenant une résine époxyde et procédé pour produire une résine époxyde Download PDF

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Publication number
WO2017085127A1
WO2017085127A1 PCT/EP2016/077862 EP2016077862W WO2017085127A1 WO 2017085127 A1 WO2017085127 A1 WO 2017085127A1 EP 2016077862 W EP2016077862 W EP 2016077862W WO 2017085127 A1 WO2017085127 A1 WO 2017085127A1
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WO
WIPO (PCT)
Prior art keywords
epoxy resin
component
resin system
weight
polyvinyl butyral
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2016/077862
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German (de)
English (en)
Inventor
Klaus Höhn
Christina Keith
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ams Osram International GmbH
Original Assignee
Osram Opto Semiconductors GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Osram Opto Semiconductors GmbH filed Critical Osram Opto Semiconductors GmbH
Publication of WO2017085127A1 publication Critical patent/WO2017085127A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
    • C08L29/14—Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols

Definitions

  • Epoxy resin system epoxy resin, using a
  • Epoxy resin system component with an epoxy resin
  • the invention relates to an epoxy resin system, an epoxy resin and the use of an epoxy resin system. Furthermore, the invention relates to an electronic, optoelectronic or optical component comprising the epoxy resin and a method for producing the epoxy resin.
  • Diodes and light modules, epoxy resins are often used as mounting and housing material, casting resin and as a matrix material for example, light conversion elements, reflection layers and optical filters as well as lens material.
  • silicones can be used, for example when the device is operated from a current of 30 mA.
  • silicones are not synonymous with all
  • SMD Surface Mounted Device
  • the low-stress properties include, for example, a high glass transition temperature T Q with a low storage modulus at the same time, a low one
  • improved properties can be produced.
  • improved properties include, in particular, increased resistance to aging, increased yellowing resistance, improved low-stress properties and low resistance
  • epoxy resin system there is a use for the epoxy resin system, an epoxy resin, which is available from the epoxy resin system, and an electronic, optoelectronic or optical
  • Component comprising such an epoxy resin, and a method for producing such an epoxy resin
  • the tasks are performed by the epoxy resin system, the
  • Epoxy resin the use of the epoxy resin system, the electronic, optoelectronic or optical component and solved by the method for producing an epoxy resin according to the independent claims.
  • Epoxy liquid resin system indicated.
  • the epoxy resin system comprises an A component and a B component.
  • Component includes a cycloaliphatic epoxy compound and a polyvinyl butyral.
  • the B component includes a
  • the epoxy resin system is preferably liquid and so easy to apply.
  • An epoxy resin which is produced from the epoxy resin system, in addition to very high glass transition temperatures, by the inventive addition of a polyvinyl butyral improved brittleness behavior and reduced crack susceptibility.
  • the epoxy resins also have a very low thermal expansion behavior. Compared to silicones or epoxy resins, which are produced without polyvinyl butyral, the epoxy resin thus has a
  • Epoxy resin according to the invention less susceptible to yellowing than casting compounds consisting of aromatic epoxy resins. Moreover, the epoxy resin systems of the invention and the resulting epoxy resins are surprisingly transparent to visible light and are resistant to light and light
  • the epoxy resins are particularly suitable for their use in optical and / or optoelectronic devices.
  • Epoxy compound at least two epoxide functions.
  • cycloaliphatic epoxide compound is preferably 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexylcarboxylate, which has the following structure (formula I):
  • the epoxy resin system does not comprise an aromatic epoxy compound.
  • Aromatic compound means that the corresponding compound contains at least one aromatic ring. Due to the fact that the epoxy resin system does not contain an aromatic epoxide compound,
  • the epoxy resin which is available from the epoxy resin system is much more light stable. This means that it is less susceptible to yellowing in the case of exposed radiation exposure in, for example, an optoelectronic component, such as a light-emitting diode (LED). Across from
  • Epoxy resins based on bisphenol A show an increased light stability.
  • the polyvinyl butyral has at least the following structural unit (formula IV)
  • the A component may include multiple polyvinyl butyrals
  • Polyvinyl butyrals can be obtained by acetalization of
  • Polyvinyl alcohol can be produced with butanal. Of the
  • Degree of acetalization is adjustable by the corresponding amount of butanal in the preparation.
  • the polyvinyl butyral has at least the following structural unit (formula II):
  • Polyvinyl alcohol is, for example, by hydrolysis of
  • Polyvinyl butyral acetyl groups may be present.
  • the polyvinyl butyral has the following structural unit (formula III):
  • Polyvinyl butyral exhibits sufficiently good solubility in the cycloaliphatic epoxide compound of the A component.
  • carbonic anhydride of the B component takes place at Temperatures between 120 ° C and 190 ° C crosslinking of the polyvinyl butyral with the cycloaliphatic
  • Epoxy compound Due to this cross-linking, the epoxy resin system forms a solid duromer material, which is referred to here as an epoxy resin.
  • the carboxylic acid anhydride may be referred to as a curing agent.
  • the polyvinyl butyral is polyvinyl butyral
  • the polyvinyl butyral is present in particular at least 97.5% as a solid.
  • the polyvinyl butyral has an average molecular weight of from 10,000 g / mol to 80,000 g / mol, preferably from 20,000 g / mol to 70000 g / mol, for example 30,000 g / mol or 600,000 g / mol.
  • Polyvinyl butyral having such average molecular weights are available as epoxy resins which are based on conventional cycloaliphatic epoxy compounds
  • Epoxy resins a reduced brittleness, lower
  • the degree of acetalization of the polyvinyl butyral is between 30% and 80%, preferably between 40% and 75%.
  • the degree of acetalation indicates what percentage of the OH groups of a polyvinyl alcohol in the
  • Polyvinyl butyrate are acetalated.
  • the polyvinyl butyral is selected from a group consisting of PVB B 30 T, PVB B 30 M, PVB B 30 H, PVB B 30 S, PVB B 30 HH, PVB B 60 T, PVB B 60 M, PVB B 60 H , PVB B 60 S, PVB B 60 HH and combinations thereof.
  • the compounds are different from Polyvinyl butyrene types from Kuraray. This is the number "30" or "60" for the middle
  • the carboxylic acid anhydride of the B component is selected from the group comprising an anhydride of a cycloaliphatic dicarboxylic acid, a dianhydride of a cycloaliphatic tetracarboxylic acid, or a combination thereof.
  • the carboxylic acid anhydride serves to cure the epoxy resin system.
  • the carboxylic anhydride is
  • Methylhexahydrophthalic anhydride or a combination of these compounds are Compared to conventional
  • Hardener components turn out to be very successful in hexahydrophthalic anhydride and methylhexahydrophthalic anhydride
  • Cycloaliphatic carboxylic anhydrides have a low intrinsic color and lead to a better
  • the A component comprises from 2 to 40% by weight of the polyvinyl butyral based on the total weight of the A component.
  • the A component preferably comprises 2 to 20% by weight of the polyvinyl butyral, based on the total weight of the A component.
  • the epoxy resin system and the epoxy resin made therefrom are transparent to visible light.
  • the A component comprises 50 to 97% by weight, preferably 80 to 97% by weight of the cycloaliphatic
  • Epoxy compound based on the total weight of the A component. Such a content of the cycloaliphatic epoxy compound in the A component makes it possible
  • the B component contains 70 to 90% by weight of carboxylic acid anhydride based on the total weight of the B component.
  • carboxylic acid anhydride can impart the necessary strength to the epoxy resin molded article.
  • the weight ratio of the A component to the B component is 100: 70 to 100: 140, preferably 100: 90 to 100: 130, more preferably 100: 90 to
  • the weight ratio of the A component to the B component is 1: 1.
  • the B component additionally contains at least one dicarboxylic acid anhydride half ester. These may be reaction products of a reaction of hexahydrophthalic anhydride,
  • Methylhexahydrophthal Acidanhydrid or combinations thereof with alcohols such as ethanol, 1, 2-propanediol, trimethylpropanol or combinations of these alcohols.
  • the alcohol can be substoichiometrically used in comparison with hexahydrophthalic anhydride or methylhexahydrophthalic anhydride, so that the anhydride functions only
  • the B component contains from 5 to 30% by weight of one or more dicarboxylic acid anhydride half esters.
  • the B component additionally contains an organic phosphite and / or a metal salt.
  • Hardening process can be accelerated and it is especially a bubble-free curing at high temperatures
  • the organic compound is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • Phosphite a diphenyl phosphite or triphenyl phosphite.
  • Markphos TPP or MarkCH66 can be used.
  • the organic phosphite also increases the oxidation stability of the epoxy resin.
  • the B component can contain from 1 to 10% by weight of one or more organic phosphites
  • the metal salt is selected from a group comprising alkoxides and / or carboxylates of zinc, yttrium, zirconium or a combination of these salts. Most preferably, the metal salt is selected from a group comprising carboxylates of zinc, yttrium, zirconium or a combination of these carboxylates.
  • the metal salt used is preferably zinc octoate.
  • the B component may contain from 2 to 10% by weight, preferably from 2 to 8% by weight, of metal salt, preferably zinc, yttrium, and / or zirconium carboxylate, more preferably zinc octoate.
  • the metal salt acts as a reaction accelerator, resulting in a fast, bubble-free curing of the epoxy resin system
  • Conversion elements are not desirable bubbles or pores, since the light can be scattered undesirable and thus the light can not be decoupled from the component as intended.
  • the production of optical and / or optoelectronic components the
  • Epoxy resin system usually applied liquid and then
  • the B component contains less than 2% by weight of metal salt, preferably zinc, yttrium, and / or zirconium carboxylate, more preferably zinc octoate are cured to higher curing temperatures and / or longer curing times
  • the B component contains more than 10% by weight of metal salt, preferably zinc, yttrium, and / or zirconium carboxylate, particularly preferably zinc octoate, glass transition temperatures which are too low are achieved
  • Metal salt preferably zinc, yttrium, and / or zirconium carboxylate, particularly preferably zinc octoate flexibilizing acts.
  • the yellowing risk increases and it can lead to outgassing, ie the release of excess
  • the A component comprises at least one further constituent selected from a group consisting of polyhydric alcohol, a
  • Reactive thinner an adhesion promoter, a deaerator, a leveling agent, a release agent, an optical
  • Thickening agents, phosphors, pigments and a filler comprises.
  • the polyhydric alcohol is an aliphatic or cycloaliphatic
  • the alcohol may be selected from a group including ethanol, 1-2-propanediol, 1-4-butanediol, 1-6-hexaniol, cyclohexanedimethanol, 2-ethyl-2-hydroxymethyl) -1, 3-propanediol, diethylene glycol, triethylene glycol .
  • Monoalkyl ether, glycerol and isosorbitol may be 1-2-propanediol, butanediol or Be trimethylolpropane.
  • the rheological, mechanical and thermo-mechanical properties and the wetting and flow behavior of the epoxy resin system can by adding the alcohol to the desired application form and
  • the reactive diluent may comprise an epoxy compound.
  • it is an aliphatic
  • Epoxy compound The reactive diluent can affect the T G and the viscosity of the epoxy resin.
  • Reactive diluents may be selected, for example, a glycidyl ether, such as hexanediol diglycidyl ether.
  • the reactive diluent to> 0 to 10% by weight, preferably> 0 to 5% by weight with respect to
  • the coupling agent may be selected from a group comprising organofunctional silanes.
  • Organofunctional silanes may include, for example, trialkoxysilane compounds such as ⁇ -glycidoxypropyltrimethoxysilane.
  • the adhesion promoter is used at 0.2 to 5% by weight, preferably> 0.5 to 2% by weight, based on the total mass of the A component.
  • the deaerators and flow aids can be organic
  • Fluorine compounds esters or acrylates.
  • breathers and leveling agents are available under the trade designation from the BYK A series from Altana or compounds from Degussa under the TEGO brand.
  • the flow control agent to> 0 to 2% by weight, preferably> 0 to 1% by weight with respect to
  • the deaerator is used at> 0 to 2 wt%, preferably> 0 to 1 wt% with respect to the total mass of the ⁇ component.
  • a release agent for example, long-chain
  • Carboxylic acids are used. As long-chain is
  • Carboxylic acid with 12 to 22 carbon atoms understood.
  • the release agent is used at> 0 to 2% by weight, preferably> 0 to 1% by weight, based on the total weight of the A component.
  • optical brightener and / or dye comprise
  • anthraquinone dyes for example, anthraquinone dyes.
  • the optical brightener and / or the dye used to> 0 to 5% by weight, preferably> 0 to 0.2% by weight based on the total mass of the A component.
  • a light stabilizer for example, 1, 3-di-tert. Butyl 4-hydroxyphenol can be used. Sunscreens are also available under the trade name Tinuvin.
  • the light stabilizer is added to> 0 to 3 wt%, preferably> 0 to 1 wt% with respect to
  • the filler and / or pigment are calcium fluoride, titanium dioxide, fused silica,
  • Wollastonite and / or calcium carbonate selected.
  • fillers and / or pigments are used at> 0 to 40% by weight, preferably> 0 to 20% by weight, based on the total mass of the A component.
  • thickening agents pyrogenic silicas can be used. These are available, for example, under the trade names Aerosil R202 or Aerosil 200.
  • the thickening agent is added to> 0 to 10% by weight, preferably> 0 to 5% by weight with respect to
  • rare earth doped garnets for example rare earth doped garnets, rare earth doped alkaline earth sulfides, rare earth doped thiogallates, rare earth doped aluminates, rare earth doped silicates, such as orthosilicates, metals of the rare earth doped chlorosilicates, rare earth doped alkaline earth silicon nitrides, rare earth doped oxynitrides, rare earth doped aluminum oxynitrides, rare earth doped silicon nitrides, sialons.
  • garnets such as
  • Yttrium aluminum oxide YAG
  • LuAG lutetium aluminum oxide
  • TAG terbium aluminum oxide
  • the phosphors are, for example, doped with one of the following activators: cerium, europium, terbium, praseodymium, samarium, manganese.
  • phosphors are used to> 0 to 40 Gewi, preferably> 0 to 20% by weight with respect to the total mass of the A component.
  • the phosphors are to
  • Convert radiation of another, in particular longer wavelength z can also be referred to as converter materials.
  • the A component consists of a cycloaliphatic epoxide compound, a
  • the A component consists of a cycloaliphatic epoxide compound, a
  • the A component consists of a cycloaliphatic epoxide compound, a
  • Polyvinyl butyral Polyvinyl butyral, a primer, a deaerator and an optical brightener.
  • the A component consists of a cycloaliphatic epoxide compound, a
  • Polyvinyl butyral a primer, a deaerator, a phosphor and an optical brightener.
  • the A component consists of a cycloaliphatic epoxide compound, a Polyvinyl butyral, an adhesion promoter, a deaerator, an optical brightener and a polyhydric alcohol and / or a reactive diluent and / or a deaerator and / or a flow control agent and / or a release agent and / or a dye and / or pigments and / or
  • Light stabilizer and / or a thickener and / or a filler and / or a phosphor are Light stabilizer and / or a thickener and / or a filler and / or a phosphor.
  • the B component consists of a carboxylic acid anhydride, a dicarboxylic acid anhydride
  • Half ester an organic phosphite and a metal salt.
  • the epoxy resin system can be cured at temperatures of more than 130 ° C. within a maximum of 30 minutes (so-called precuring).
  • the epoxy resin system can be cured in particular at temperatures between 160 ° C and 185 ° C within a period of one to ten minutes, in particular three to ten minutes.
  • Epoxy resin system is formed by a crosslinking in particular a no longer flowable molding material.
  • a complete curing or crosslinking to epoxy resin can in a subsequent curing step (so-called
  • Postcuring In this case, for example, heated to 155 ° C for four hours.
  • the epoxy resin system is included
  • the epoxy resin system has a chlorine content below 100 ppm, preferably below 50 ppm.
  • a low chlorine content is particularly desirable to reduce the formation of harmful compounds in thermal decomposition.
  • the A component is storage stable at room temperature. For example, it can be stored for at least six weeks at room temperature without degrading. Viscosity measurements show only a slight change even after ten weeks of storage of the A component.
  • the A component has a
  • Viscosity of the A component can thus be targeted to the
  • the A component and the B component are usually stored separately from each other and before hardening of the
  • Epoxy resin system is available a molding material, which is referred to here as epoxy resin.
  • the composition of the Epoxy resin system therefore largely or completely conditions the properties of the epoxy resin.
  • Epoxy resin system is produced, has on the one hand a very high resistance to aging and yellowing stability and on the other hand, very good low-stress properties.
  • Such an epoxy resin is characterized in particular by a high
  • the improved low-stress properties are accompanied by a high glass transition temperature TQ and a low storage modulus of the epoxy resin. Compared to aromatic epoxy resins, this results in an increased by about 40 ° C temperature range.
  • the epoxy resin is therefore solder resistant, so that the
  • Epoxy resin system is also suitable for use in SMD components, for example LEDs (light-emitting diodes). These improved compared to conventional epoxy resins
  • the invention is largely retained over the life of the device without changing significantly under temperature, radiation or moisture load. It is given an epoxy resin.
  • Epoxy resin may in particular comprise a hardened epoxy resin system according to at least one embodiment of the application, consist thereof or be obtainable therefrom.
  • the epoxy resin system may for this purpose have been cured as described above.
  • the composition and properties of the epoxy resin are therefore essentially or
  • the epoxy resin has a glass transition temperature TQ of greater than 180 ° C.
  • TQ Dynamic Scanning Calorimetry
  • thermogravimetric analysis at 300 ° C in air and a heating rate of 10 K / min, the
  • Weight loss of a sample less than 5.0%, in particular Kle ⁇ . 4.5%.
  • the epoxy resin has a
  • CTE Thermal expansion coefficient
  • the epoxy resin a thermal expansion coefficient of less than 200 ppm / K on.
  • the epoxy resin is one
  • Memory module at 20 ° C of less than 2500 MPa.
  • Memory module is determined according to the application in dynamic mechanical measurements (DMTA, dynamic-mechanical thermal analysis) in the tensile mode with a measuring frequency of 1 Hz.
  • DMTA dynamic mechanical measurements
  • the low memory module expresses the very good low-stress properties of the epoxy resin. It will be described
  • the epoxy resin according to the invention has an improved
  • Aging resistance in the device for example, with mechanically vulnerable LED chips, and in particular is insensitive to thermo-mechanical stress, such as occurs during soldering, so that the
  • Epoxy resin is also suitable for SMD-capable components.
  • the epoxy resin according to the application therefore does not tend to be brittle, cracked or cracked, so that, for example, an electronic component can be protected very well against air and moisture over a long period of time.
  • the epoxy resin shows a low moisture absorption.
  • Epoxy resin is therefore also suitable for use with components or components that can be used outside of enclosed spaces.
  • the epoxy resins are therefore less permeable to moisture than silicones.
  • MSL moisture sensitive level
  • the release of the components takes place after a climate load at 30 ° C and 60% relative humidity.
  • a processability is for 72 h after removal from the dry packaging
  • the epoxy is transparent to visible light.
  • the epoxy resin can also be colorless. This is particularly the case if no phosphors or pigments with a distinct body color in the
  • Epoxy resin is therefore also suitable for arrangement in
  • potting for example, as potting, conversion element, lens prism, filter or housing material.
  • the epoxy resin can be a very high
  • a process for producing an epoxy resin is given.
  • the specified embodiments of the epoxy resin can be prepared according to the following method. All of the features of the epoxy resin mentioned in the process may also have features of the above
  • the method comprises
  • Carboxylic anhydride comprises,
  • the epoxy resin system from process step C) can be applied in liquid form and can thus be applied to a substrate in liquid form before process step D).
  • curing in method step D) takes place at a temperature between 120 ° C. and 190 ° C., in particular between 140 ° C. and 180 ° C.
  • the hardening in process step D) can take place within one
  • method step D) comprises
  • the curing takes place in
  • Process step D1) at temperatures between 160 ° C and 185 ° C.
  • the hardening can take place over a period of one to 30 minutes, in particular over a period of three to ten minutes.
  • the use of an epoxy resin system is indicated.
  • An epoxy resin system according to at least one embodiment of the application can be used in the field of electronics as well as by its transparency for visible light for the production and / or attachment of optical components.
  • the epoxy resin system for example, for potting, covering, coating, wrapping, encapsulating, gluing,
  • optoelectronic components and optical components serve.
  • a component can also be referred to as a component.
  • a reflector element As a reflector element or
  • Reflector housing the epoxy resin or the
  • Epoxy resin system containing white pigments as fillers are based, for example, on CaF 2 , TiO 2 , Al 2 O 3 or ZrO 2.
  • white pigments are based, for example, on CaF 2 , TiO 2 , Al 2 O 3 or ZrO 2.
  • Epoxy resin is used is not limited. Because of the epoxy resin an aging and yellowing resistant Epoxy resin with very good low-stress properties can be produced, the application is appropriate.
  • Epoxy resin system for example, for SMD-capable electronic components, in particular optoelectronic components such as LEDs. It can, for example, as potting, housing,
  • Adhesive layer and / or used as a reflector of components such as LEDs are Adhesive layer and / or used as a reflector of components such as LEDs. Furthermore, the epoxy resin system can also be used in component applications as well as groups of
  • Outdoor application area can be used.
  • Epoxy resin for forming adhesive layers between elements in electronic devices at least one element contains a metal such as Ag or Au or Cu, or a liquid crystalline polymer (LCP).
  • a metal such as Ag or Au or Cu
  • LCP liquid crystalline polymer
  • the bonding of the two elements by the adhesive layer comprising or consisting of the epoxy resin is particularly good. Also, to the known hard-to-glue elements made of a liquid crystal polymer is a good adhesion with the epoxy resin. Due to the good bonding, premature delamination of the elements is prevented and thus the service life of the electronic component can be extended. Very high shear strengths can be achieved. For example, it may be at a
  • at least one element is ceramic modules in light-emitting components, such as conversion elements.
  • the epoxy resin system may contain phosphors for the conversion of light.
  • Conversion element may be formed as potting or layer and is in particular arranged in the beam path of an electromagnetic primary radiation.
  • an electronic, optoelectronic or optical component which comprises an epoxy resin according to at least one embodiment of the application. This can also consist of the epoxy resin.
  • the component is a light-emitting diode, a photodiode, a phototransistor, a photoarray, an optical coupler, an SMD component or an SMD-capable component.
  • the component is preferably an optoelectronic component.
  • the component can be used, for example, for the automotive sector and / or for Outdoor applications are suitable. It can also be one of the other components mentioned, for which the epoxy resin is used.
  • the optoelectronic device in one embodiment, the optoelectronic
  • Component a layer sequence with an active layer that emits electromagnetic primary radiation.
  • layer sequence is understood as meaning a layer sequence comprising more than one layer, for example a sequence of a p-doped and an n-doped semiconductor layer, the layers being arranged one above the other. Construction and materials of such
  • the optoelectronic device in one embodiment, the optoelectronic
  • a housing In the housing, a recess may be present in the middle.
  • the layer sequence can be mounted in the recess. It is also possible that the recess is filled with a potting.
  • the housing is made of a liquid crystal polymer or
  • Housings made of a liquid crystal polymer are particularly suitable for applications at high temperatures and housing
  • polycyclohexyldimethylene terephthalate Due to its radiation resistance, polycyclohexyldimethylene terephthalate is suitable for use in optoelectronic components.
  • the potting comprises or consists of the epoxy resin. If a phosphor is present in the epoxy resin, the casting can be used as a conversion element
  • the potting can fill the recess in the housing. Is the potting in contact with the Environment, the diffusion rate of H 2 O and ambient gases is very low. Particularly in comparison with encapsulants comprising silicone, the diffusion rate of H 2 O and gases from the environment is markedly reduced. In addition, there is a very good adhesion to the housing material, especially if the housing of a liquid crystal polymer or
  • Polycyclohexyldimethylenterephthalat is produced, which show straight to silicones no good adhesion. According to a further embodiment, the optical
  • Component or component a lens, a prism, a filter, an optical window, a diffuser element, a reflector element, that is, a light-reflecting element, a housing, a reflector housing, that is a
  • the epoxy resin is stable to light and temperature influences, so that the optical components are less yellowed or cloudy due to these influences.
  • the optical component that is, for example, a lens, a prism, a filter, an optical window, a reflector element, a housing or reflector housing or a conversion element can in particular be part of an optoelectronic component
  • the optical component is in
  • FIG. 1 shows physical and chemical properties of various embodiments of an epoxy resin
  • Figure 7 is a schematic side view of a
  • n D denote the
  • Optical brightener 0.015 wt% mixed with a B component and cured for four hours at 155 ° C.
  • the ratio of the A component to the B component is 1: 1.
  • Araldite CY179 is 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexylcarboxylate.
  • PVB B 30 H is the trade name of a
  • Polyvinyl butyrals wherein 30 for the average molecular weight of 30,000 g / mol and H indicates the degree of acetalization.
  • the B component contains between 70 and 90% by weight
  • Methylhexahydrophthalic anhydride between 5 and 30% by weight of a dicarboxylic anhydride half ester, between 2 and 10% by weight of an accelerator and between 1 and 10% by weight of an organic phosphite.
  • the viscosity at 25 ° C one
  • Component is at its production at 8150 mPas. Tests have shown that after 10 weeks of storage of the A component at room temperature, the viscosity is 9160 mPas. After six months storage, the A component has a viscosity at 25 ° C of 8260 mPas. The viscosity of the mixture of the A component and the B component immediately after mixing is 2890 mPas at 25 ° C.
  • Optical brightener 0.015 wt% mixed with a B component and cured for four hours at 155 ° C.
  • the ratio of the A component to the B component is 1: 1.
  • Araldite CY179 is 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexylcarboxylate.
  • PVB B 30 H is the trade name of a
  • Polyvinyl butyrals wherein 30 for the average molecular weight of 30,000 g / mol and H indicates the degree of acetalization.
  • the B component contains between 70 and 90% by weight
  • Methylhexahydrophthalic anhydride between 5 and 30% by weight of dicarboxylic anhydride half ester, between 2 and 10% by weight of an accelerator and between 1 and 10% by weight of an organic phosphite.
  • the viscosity is 1860 mPas at 25 ° C, four hours after mixing at 2170 mPas, six hours after mixing at 2980 mPas and eight hours after mixing at 3760 mPas.
  • Optical brightener 0.015 wt% mixed with a B component and cured for four hours at 155 ° C.
  • the ratio of the A component to the B component is 1: 1.
  • Araldite CY179 is 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexylcarboxylate.
  • PVB B 60 HH is the trade name of a
  • Polyvinyl butyrals wherein 60 is the average molecular weight of 60000 g / mol and HH indicates the degree of acetalization.
  • the B component contains between 70 and 90% by weight
  • Methylhexahydrophthalic anhydride between 5 and 30% by weight of dicarboxylic anhydride half ester, between 2 and 10% by weight of an accelerator and between 1 and 10% by weight of an organic phosphite.
  • the viscosity at 25 ° C of the A component is in its preparation at 7660 mPas. After four months storage, the A component has a viscosity at 25 ° C of 7730 mPas.
  • the viscosity of the mixture of the A component and the B component immediately after mixing at 25 ° C at 2140 mPas. Two hours after that
  • the viscosity is 2760 mPas at 25 ° C, four hours after mixing at 3550 mPas, six hours after mixing at 5180 mPas and eight hours after mixing at 5850 mPas.
  • the epoxy has a
  • Optical brightener 0.015 wt% mixed with a B component and cured for four hours at 155 ° C.
  • the ratio of the A component to the B component is 1: 1.
  • Araldite CY179 is 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexylcarboxylate.
  • PVB B 60 H is the trade name of a
  • Polyvinyl butyrals wherein 60 is the average molecular weight of 60000 g / mol and H indicates the degree of acetalization.
  • the B component contains between 70 and 90% by weight
  • Methylhexahydrophthalic anhydride between 5 and 30% by weight of dicarboxylic acid anhydride half ester, between 2 and 10% by weight of an accelerator and between 1 and 10% by weight of an organic phosphite
  • the viscosity at 25 ° C. of the A component is 8800 mPas in its preparation , After six months of storage, the A component has a viscosity at 25 ° C of 8630 mPas.
  • the viscosity of the mixture of the A component and the B component immediately after mixing at 25 ° C at 2560 mPas. Two hours after that
  • the viscosity is 3110 mPas at 25 ° C, 4 hours after mixing at 3920 mPas, 6 hours after mixing at 5490 mPas and 8 hours after mixing at 6220 mPas.
  • Figure 2 shows a DMTA measurement for epoxy resins made according to the first to fourth embodiments (reference numerals I, II, III and IV) in comparison with a conventional epoxy resin (R) prepared using
  • Methylhexahydrophthalic anhydride produced as a hardener has been.
  • the curves 1 show the course of the storage module as the temperature rises, heating at a heating rate of 3 K / min.
  • the curves 2 describe the Tan Delta (Tan ⁇ ), after which the glass transition temperature T G can be determined. As can be seen in the maxima of the curves 2, the exemplary embodiments
  • Embodiment (I to IV) thus have a high
  • FIG. 3 the DMTA measurement already shown in FIG. 2 is shown only for the third exemplary embodiment III and the reference R.
  • Figure 4a shows the viscosity at 25 ° C for epoxy resins, according to the first to fourth embodiments
  • Viscosity over 6000 mPas and the embodiment with the reference numeral II an approximately constant viscosity over 4000 mPas.
  • the first embodiment (I) shows, in the A component 10 wt% PVB B 30 H templates a higher viscosity as the second embodiment (II), in which in the A component 5 wt% PVB B 30 H were present.
  • PVB B 60 ie a polyvinyl butyrate having an average molecular weight of 60000 g / mol to a higher viscosity than PVB B 30, ie a polyvinyl butyrate having an average molecular weight of 60,000 g / mol leads.
  • FIG. 5a shows adhesion strengths of inert silicon elements on different substrate materials, wherein a between the silicon elements and the respective substrates
  • Epoxy resin is arranged, which according to the first to fourth embodiment (reference I, II, III and IV)
  • the specified bond strengths are average values from ten measurements each. All silicon elements have an area of 2 ⁇ 2 mm, wherein over the respective substrate materials over the entire surface of a layer of the
  • Epoxy resin and above the silicon elements are applied.
  • the y-axis indicates the adhesive strength at room temperature.
  • Embodiment with an adhesive strength of about 60 MPa Embodiment with an adhesive strength of about 60 MPa.
  • the corresponding bond strengths are listed in FIG. 5b in the table.
  • Figure 6a shows adhesion strengths of inert silicon elements on different substrate materials, wherein between the silicon elements and the respective substrates
  • Epoxy resin is arranged, which according to the first to fourth embodiment (reference I, II, III and IV)
  • the specified bond strengths are average values from ten measurements each. All silicon elements have an area of 2 ⁇ 2 mm, wherein over the respective substrates over the entire surface of a layer of the epoxy resin and over the entire surface of the silicon elements are applied. The y-axis indicates the adhesive strength at room temperature. There were substrates out
  • High temperature materials often used as a housing for
  • Adhesive strengths are listed in FIG. 5b in the table.
  • the optoelectronic component 11 according to FIG. 7 shows a carrier 5 with a lead frame 6 and a housing 8.
  • the housing 8 has in the center a recess in which the layer sequence 2 is arranged, which is arranged with the lead frame 6 electrically connected.
  • the housing 8 is made of a
  • the encapsulation 4 comprises an inventive epoxy resin comprising particles of a phosphor.
  • the encapsulation 4 is arranged in the beam path of the electromagnetic primary radiation, which is emitted by an active layer (not shown here) in the layer sequence 2.
  • the phosphor is adapted to the operation of the device, the primary radiation of the active
  • the secondary radiation has a longer wavelength than the primary radiation. As already shown in FIGS. 6a and 6b, this indicates
  • Polycyclohexyldimethylenterephthalat the housing 8 has a very good adhesion, which is far better than a conventional potting material.
  • the lead frame 6 may have an Ag or Au metallization. It has been found that the epoxy resin of the invention is very good
  • Lead frame 6 is also against moisture and thus before
  • the optoelectronic device Preferably, the optoelectronic
  • Device 11 to an LED, wherein the radiation is coupled up via a transparent layer sequence 2 and the transparent encapsulation 4.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Led Device Packages (AREA)

Abstract

La présente invention concerne un système de résine époxyde comprenant un constituant A et un constituant B. Le constituant A comprend un composé époxyde cycloaliphatique et un polyvinylbutyral et le constituant B comprend un anhydride d'acide carboxylique et un sel métallique, le sel métallique étant choisi dans un groupe comprenant des carboxylates de zinc, d'yttrium, de zirconium ou une combinaison de ces carboxylates.
PCT/EP2016/077862 2015-11-16 2016-11-16 Système de résine époxyde, résine époxyde, utilisation d'un système de résine époxyde, composant comprenant une résine époxyde et procédé pour produire une résine époxyde Ceased WO2017085127A1 (fr)

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DE102015119775.8A DE102015119775A1 (de) 2015-11-16 2015-11-16 Epoxidharzsystem, Epoxidharz, Verwendung eines Epoxidharzsystems, Bauelement mit einem Epoxidharz und Verfahren zur Herstellung eines Epoxidharzes
DE102015119775.8 2015-11-16

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020225249A1 (fr) * 2019-05-09 2020-11-12 Osram Opto Semiconductors Gmbh Composition de résine, utilisation de cette composition de résine, composant optoélectronique et procédé de fabrication d'un composant optolectronique

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0174510A2 (fr) * 1984-08-23 1986-03-19 Kabushiki Kaisha Toshiba Composition de résine époxy pour encapsulation de dispositifs semi-conducteurs
WO2007036194A1 (fr) * 2005-09-28 2007-04-05 Osram Opto Semiconductors Gmbh Systeme de resine epoxyde, matiere moulable produite a partir de ce systeme de resine epoxyde et composant optoelectronique comprenant cette matiere moulable

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH483467A (de) * 1967-12-08 1969-12-31 Ciba Geigy Härtbare Mischungen aus Epoxidharzen, Polycarbonsäureanhydriden und Aminbeschleunigern
GB9120078D0 (en) * 1991-09-20 1991-11-06 Ciba Geigy Ag Resin formulation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0174510A2 (fr) * 1984-08-23 1986-03-19 Kabushiki Kaisha Toshiba Composition de résine époxy pour encapsulation de dispositifs semi-conducteurs
WO2007036194A1 (fr) * 2005-09-28 2007-04-05 Osram Opto Semiconductors Gmbh Systeme de resine epoxyde, matiere moulable produite a partir de ce systeme de resine epoxyde et composant optoelectronique comprenant cette matiere moulable

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020225249A1 (fr) * 2019-05-09 2020-11-12 Osram Opto Semiconductors Gmbh Composition de résine, utilisation de cette composition de résine, composant optoélectronique et procédé de fabrication d'un composant optolectronique

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