DE3626318A1 - Optically transparent tapping compound of high temperature shock resistance - Google Patents

Optically transparent tapping compound of high temperature shock resistance

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Publication number
DE3626318A1
DE3626318A1 DE19863626318 DE3626318A DE3626318A1 DE 3626318 A1 DE3626318 A1 DE 3626318A1 DE 19863626318 DE19863626318 DE 19863626318 DE 3626318 A DE3626318 A DE 3626318A DE 3626318 A1 DE3626318 A1 DE 3626318A1
Authority
DE
Germany
Prior art keywords
optically transparent
shock resistance
high temperature
resin
mass
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.)
Withdrawn
Application number
DE19863626318
Other languages
German (de)
Inventor
Wolfhart Dr Seidel
Juergen Dr Schillgalies
Jutta Reinhardt
Martin Dipl Ing Mueller
Uwe Dipl Chem Sierk
Wolf Bucher
Alf Dipl Ing Treske
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.)
Leuna Werke GmbH
Original Assignee
Leuna Werke 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 Leuna Werke GmbH filed Critical Leuna Werke GmbH
Publication of DE3626318A1 publication Critical patent/DE3626318A1/en
Withdrawn legal-status Critical Current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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/681—Metal alcoholates, phenolates or carboxylates
    • C08G59/685—Carboxylates
    • 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

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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)
  • Epoxy Resins (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Optically transparent tapping compounds of high temperature shock resistance comprise epoxy resins which polycarboxylic anhydrides, polyalcohols and metal carboxylates as curing system, which contain 1-20% by weight of phthalic esters (phthalates) and/or polyoxyalkylene glycol. LED components encapsulated therewith are distinguished by very good alternating temperature resistance between 223 and 373 K.

Description

Die Erfindung betrifft optisch transparente Verkappungsmassen auf der Basis von Epoxidharzen mit Polycarbonsaeureanhydriden als Haerter zum Verguss von optoelektronischen Bauelementen wie Lumineszenzdioden, -displays, Phototransistoren, Photodioden und optoelektronischen Kopplern.The invention relates to optically transparent capping compounds based on epoxy resins with polycarboxylic acid anhydrides as hardener for potting optoelectronic components such as luminescent diodes, displays, phototransistors, photodiodes and optoelectronic couplers.

Fuer den Verguss optoelektronischer Bauelemente sind bisher verschiedene Giessharzsysteme auf der Basis von Epoxidharzen mit Polycarbonsaeureanhydriden als Haerter bekannt, deren wesentliches Merkmal die Art und Zusammensetzung der verwendeten Beschleuniger und Stabilisatoren ist (DE-OS 26 42 465, DE-OS 30 16 103, DD-PS 2 11 120, GB-PS 20 90 257). Als vorteilhafte Rezepturen fuer obengenanntes Anwendungsgebiet ergaben sich heisshaertende Zweikomponenten-Giessharzsysteme, bei denen die Komponente A aus einem Bisphenoldiglycidether, einem cyclophatischen Epoxidharz, einem Diglycidester von Dicarbonsaeuren oder Mischungen derselben und die Komponente B aus einem oder mehreren Polycarbonsaeureanhydriden, einem Zinkcarboxylat, einem Polyalkohol und gegebenenfalls einem organischen Phosphit bestehen. Diese bekannten Loesungen besitzen jedoch den Nachteil, dass die mit dem Giessharz nach dem Stand der Technik verkapselten LED-Bauelemente eine hohe Ausfallrate bei Temperatur-Wechselbestaendigkeits-Test zwischen 223 K und 373 K aufweisen.Various casting resin systems based on epoxy resins with polycarboxylic acid anhydrides are known as hardeners for the encapsulation of optoelectronic components, the essential feature of which is the type and composition of the accelerators and stabilizers used (DE-OS 26 42 465, DE-OS 30 16 103, DD- PS 2 11 120, GB-PS 20 90 257). Advantageous formulations for the abovementioned field of application have been found to be heat-curing two-component casting resin systems in which component A consists of a bisphenol diglycidyl ether, a cyclophatic epoxy resin, a diglycidyl ester of dicarboxylic acids or mixtures thereof, and component B consists of one or more polycarboxylic acid anhydrides, a zinc alcohol and a polyalkoxy an organic phosphite. However, these known solutions have the disadvantage that the LED components encapsulated with the casting resin according to the prior art have a high failure rate in the temperature change resistance test between 223 K and 373 K.

Das Ziel der Erfindung sind optisch transparente Verkappungsmassen auf der Basis von Epoxidharzen und Polycarbonsaeureanhydriden als Haerter, die eine hohe Temperaturschockbestaendigkeit aufweisen.The aim of the invention is optically transparent capping compounds based on epoxy resins and polycarboxylic acid anhydrides as hardener, which has a high temperature shock resistance exhibit.

Der Erfindung liegt die Aufgabe zugrunde, optisch transparente Verkappungsmassen auf der Basis von Epoxidharzen und Polycarbonsaeureanhydriden als Haerter zu schaffen, die Endprodukte mit ausgezeichneten optischen und thermomechanischen Eigenschaften ergeben, insbesondere mit einer solchen Temperaturschockbestaendigkeit, dass die Ausfallrate bei verkapselten Bauelementen nach 100 Zyklen des Temperaturwechsels zwischen 223 und 373 K unter 10% liegt. Diese Aufgabe wird durch eine Verkappungsmasse auf Basis von Epoxidharzen und Polycarbonsaeureanhydriden, Polyalkoholen und Metallcarboxylaten geloest, die erfindungsgemaess Phthalsaeureester und/oder Polyoxyalkylenglykol enthaelt. The invention has for its object to be optically transparent Capping compounds based on epoxy resins and to create polycarboxylic acid anhydrides as hardeners which End products with excellent optical and thermomechanical Properties result, especially with a such temperature shock resistance that the failure rate with encapsulated components after 100 cycles of Temperature change between 223 and 373 K is less than 10%. This task is based on a capping compound of epoxy resins and polycarboxylic acid anhydrides, polyalcohols and dissolved metal carboxylates, which according to the invention Contains phthalate and / or polyoxyalkylene glycol.  

Vorzugsweise enthaelt das Harz-Haerter-Gemisch 1 bis 10 Masse-% Dibutylphthalat oder 1 bis 20 Masse-% Polyethylenglykol oder Polypropylenglykol, bezogen auf Harz-Haerter-Gemisch. Besonders gute Eigenschaften erhaelt man, wenn das Gemisch 1 bis 20 Masse-% Phthalsaeureester und Polyoxyalkylenglykol enthaelt. Das Glykol hat vorzugsweise ein mittleres Molekulargewicht von 300 bis 1000.The resin-hardener mixture preferably contains 1 to 10 % By mass of dibutyl phthalate or 1 to 20% by mass of polyethylene glycol or polypropylene glycol based on Resin-hardener mixture. Particularly good properties are obtained when the mixture 1 to 20% by mass of phthalic acid ester and polyoxyalkylene glycol contains. The glycol preferably has an average molecular weight from 300 to 1000.

Beispiel 1example 1

Eine optisch transparente Verkappungsmasse wird hergestellt aus (alle Angaben in Masseteilen):An optically transparent capping compound is produced off (all details in parts by mass):

Diandiglycidether mit einem Epoxidaequivalentgewicht von 175 und einer Jodfarbzahl von 133,0 3,4-Epoxicyclohexylmethyl-(3,4-epoxi)-Cyclohexancarboxylat mit einem Epoxidaequivalentgewicht von 14017,0 Hexahydrophthalsaeureanhydrid43,25
Zink-Carboxylat-Phosphit-Komplex aus Zink-2- ethylhexanoat und Diphenyldecylphosphit 4,0 Aethylenglykol 0,75Dibutylphthalat 2,0 Diandiglycidyl ether with an epoxide equivalent weight of 175 and an iodine color number of 133.0 3,4-epoxicyclohexylmethyl (3,4-epoxy) cyclohexane carboxylate with an epoxide equivalent weight of 14017.0 hexahydrophthalic anhydride 43.25
Zinc-carboxylate-phosphite complex of zinc 2-ethylhexanoate and diphenyldecylphosphite 4.0 ethylene glycol 0.75dibutylphthalate 2.0

Die Komponenten werden bei 313 K gemischt und in 2 Stunden bei 398 K und 2 Stunden bei 423 K ausgehaertet. Die Kenndaten der Reaktionsharzformstoffe sind fuer alle Beispiele in der Tab. 1 zusammengestellt. The components are mixed at 313 K and in 2 hours cured at 398 K and 2 hours at 423 K. The key data of the reaction resin molding materials are for all examples compiled in Tab. 1.  

Beispiel 2Example 2

Diandiglycidether mit einem Epoxidaequivalentgewicht von 175 und einer Jodfarbzahl von 133,0 3,4-Epoxicyclohexylmethyl-(3,4-epoxi)-Cyclohexancarboxylat mit einem Epoxidaequivalentgewicht von 14017,0 Hexahydrophthalsaeureanhydrid39,5 Diphenyldecylphosphit 2,0 Zinkcarboxylat mit einem Zinkgehalt von 11,0 Masse-% auf der Basis von 2-Ethylhexansaeure und Ethylenglykolmonohexahydrophthalsaeureester im Molverhaeltnis 1:1 3,5 Polypropylenglykol, mittleres Molekulargewicht 700 5  Diandiglycidether with an epoxide equivalent weight of 175 and an iodine color number of 133.0 3,4-epoxicyclohexylmethyl (3,4-epoxy) cyclohexane carboxylate with an epoxy equivalent weight of 14017.0 hexahydrophthalic anhydride 39.5 diphenyldecyl phosphite 2.0 zinc carboxylate with a zinc content of 11.0% by mass based on 2-ethylhexanoic acid and ethylene glycol monohexahydrophthalic acid ester in a molar ratio of 1: 1 3.5 polypropylene glycol, average molecular weight 700 5

Verarbeitung wie im Beispiel 1 angegeben, zusaetzlich jedoch 5 Stunden bei 373 K vorgehaertet.Processing as indicated in example 1, but additionally 5 hours pre-hardened at 373 K.

Beispiel 3Example 3

3,4-Epoxicyclohexylmethyl-(3,4-epoxi)-Cyclohexancarboxylat mit einem Epoxidaequivalentgewicht von 14045,0 Hexahydrophthalsaeureanhydrid41,0 Trimethylolpropan 2,0 Zink-Carboxylat-Phosphit-Komplex aus Zink-2-ethylhexanoat und Diphenyldecylphosphit 4,0 Dibutylphthalat 3,0 Polyethylenglykol mit einem mittleren Molekulargewicht von 400 5,0 3,4-epoxy cyclohexylmethyl (3,4 epoxy) cyclohexane carboxylate with an epoxy equivalent weight of 14045.0 hexahydrophthalic anhydride 41.0 trimethylolpropane 2.0 zinc carboxylate phosphite complex from zinc 2-ethylhexanoate and diphenyl decyl phosphite 4.0 dibutyl phthalate 3.0 polyethylene glycol with an average molecular weight of 400 5.0

Verarbeitung wie im Beispiel 1 angegeben. Processing as indicated in Example 1.  

Beispiel 4 (Vergleichsbeispiel)Example 4 (comparative example)

Diandiglycidether mit einem Epoxidaequivalentgewicht von 175 und einer Jodfarbzahl von 150  Hexahydrophthalsaeureanhydrid45,5 Ethylenglykol 0,5 Zink-Carboxylat-Phosphit-Komplex aus Zink-2- ethylhexanoat und Diphenyldecylphosphit 4,0 Diandiglycidether with an epoxide equivalent weight of 175 and an iodine color number of 150 hexahydrophthalic anhydride 45.5 ethylene glycol 0.5 zinc carboxylate phosphite complex from zinc 2 ethyl hexanoate and diphenyl decyl phosphite 4.0

Verarbeitung wie im Beispiel 1 angegeben.Processing as indicated in Example 1.

Beispiel 5 (Vergleichsbeispiel)Example 5 (comparative example)

3,4-Epoxicyclohexylmethyl-(3,4-epoxi) Cyclohexancarboxylat mit einem Epoxidaequivalentgewicht von 14043,00Hexahydrophthalsaeureanhydrid48,003-Methylpentandiol-1,5 2,75Ethanol 2,22Zinkoctoat 1,83Diphenyldecylphosphit 2,303,4-epoxy cyclohexylmethyl (3,4 epoxy) cyclohexane carboxylate with an epoxide equivalent weight of 14043.00 hexahydrophthalic anhydride 48.003-methylpentanediol-1.5 2.75 ethanol ethanol 2.22 zinc octoate 1.83 diphenyldecyl phosphite 2.30

Die Verarbeitung erfolgt wie im Beispiel 2 angegeben. Processing is carried out as indicated in Example 2.  

Tabelle 1 Table 1

Kenndaten der Reaktionsharzformstoffe und Ergebnisse der Zuverlaessigkeitspruefung von verkapselten LED-BauelementenCharacteristic data of reaction resin molding materials and results of Reliability testing of encapsulated LED components

Claims (4)

1. Optisch transparente Verkappungsmasse mit hoher Temperaturschockbestaendigkeit auf der Basis von Epoxidharzen und Polycarbonsaeureanhydriden, Polyalkoholen und Metallcarboxylat als Haertersystem, dadurch gekennzeichnet, dass das Giessharz einen Phthalsaeureester und/oder Polyoxyalkylenglykol enthaelt.1. Optically transparent capping compound with high thermal shock resistance on the basis of epoxy resins and polycarboxylic acid anhydrides, polyalcohols and metal carboxylate as hardener system, characterized in that the casting resin contains a phthalic acid ester and / or polyoxyalkylene glycol. 2. Optisch transparente Verkappungsmasse nach Punkt 1, dadurch gekennzeichnet, dass das Giessharz 1 bis 20 Masse-% Phthalsaeureester und Polyalkylenglykol enthaelt.2. Optically transparent capping compound according to item 1, thereby characterized that the casting resin 1 to 20 mass% Contains phthalic acid ester and polyalkylene glycol. 3. Optisch transparente Verkappungsmasse nach Punkt 1, dadurch gekennzeichnet, dass das Giessharz 1 bis 10 Masse-% Dibutylphthalat, bezogen auf Harz-Haerter-Gemisch, enthaelt.3. Optically transparent capping compound according to item 1, thereby characterized that the casting resin 1 to 10 mass% Dibutyl phthalate, based on resin-hardener mixture, contains. 4. Optisch transparente Verkappungsmasse nach Punkt 1, dadurch gekennzeichnet, dass das Giessharz 1 bis 20 Masse-% Polyethylenglykol oder Polypropylenglykol, bezogen auf Harz-Haerter-Gemisch enthaelt.4. Optically transparent capping compound according to item 1, thereby characterized that the casting resin 1 to 20 mass% Polyethylene glycol or polypropylene glycol, based on Resin-hardener mixture contains.
DE19863626318 1985-08-29 1986-08-02 Optically transparent tapping compound of high temperature shock resistance Withdrawn DE3626318A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DD28008885A DD240554A1 (en) 1985-08-29 1985-08-29 OPTICAL TRANSPARENT COVERING MASS WITH HIGH TEMPERATURE SHOCK RESISTANCE

Publications (1)

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DE3626318A1 true DE3626318A1 (en) 1987-03-05

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DE19863626318 Withdrawn DE3626318A1 (en) 1985-08-29 1986-08-02 Optically transparent tapping compound of high temperature shock resistance

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DD (1) DD240554A1 (en)
DE (1) DE3626318A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0738759A1 (en) * 1994-11-09 1996-10-23 Nitto Denko Corporation Epoxy resin composition for sealing photosemiconductor device
US8198382B2 (en) * 2007-05-17 2012-06-12 Nitto Denko Corporation Epoxy resin composition for photosemiconductor element encapsulation and cured product thereof, and photosemiconductor device using the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0738759A1 (en) * 1994-11-09 1996-10-23 Nitto Denko Corporation Epoxy resin composition for sealing photosemiconductor device
EP0738759A4 (en) * 1994-11-09 1998-09-09 Nitto Denko Corp Epoxy resin composition for sealing photosemiconductor device
US8198382B2 (en) * 2007-05-17 2012-06-12 Nitto Denko Corporation Epoxy resin composition for photosemiconductor element encapsulation and cured product thereof, and photosemiconductor device using the same

Also Published As

Publication number Publication date
DD240554A1 (en) 1986-11-05

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