KR101454798B1 - Siloxane cross linker for sealing material of light emitting diode - Google Patents

Siloxane cross linker for sealing material of light emitting diode Download PDF

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KR101454798B1
KR101454798B1 KR1020120056087A KR20120056087A KR101454798B1 KR 101454798 B1 KR101454798 B1 KR 101454798B1 KR 1020120056087 A KR1020120056087 A KR 1020120056087A KR 20120056087 A KR20120056087 A KR 20120056087A KR 101454798 B1 KR101454798 B1 KR 101454798B1
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group
emitting diode
formula
siloxane
composition
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KR1020120056087A
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Korean (ko)
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KR20130132028A (en
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채규윤
김병희
김영찬
최복열
신세라
이덕희
황희민
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다미폴리켐 주식회사
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Abstract

The present invention relates to a siloxane crosslinking agent for light-emitting diodes. The encapsulant to which the siloxane crosslinking agent of the present invention is applied is excellent in high refractive index, heat resistance and flexibility, and has an effect of not damaging the wires and chips of the light emitting diode device due to high hardness.

Description

Technical Field [0001] The present invention relates to a siloxane crosslinking agent for a sealing material of a light emitting diode,

The present invention relates to a siloxane crosslinking agent for an encapsulating material of a light emitting diode device.

Epoxy resin has been used as a conventional encapsulating material for protecting light emitting diode devices. Epoxy resin can damage wires and chips of diode elements due to lack of thermal stability at a long time when used at high temperatures. In addition, The chemical resistance is lowered and the lifetime of the encapsulant is significantly lower than the lifetime of the consumer product.

In recent years, development of a high-refractive index siloxane resin has progressed actively, and Korean Patent Application No. 10-2010-0040615 discloses a method using an organopolysiloxane resin having a fluorenylalkyl group and a phenyl group, 10-2008-7020666 discloses a process using an alkenyl functional phenyl-containing polyorganosiloxane, a Si-H functionalized phenyl-containing polyorganosiloxane, and the methods disclosed in the above document include hydrogendioganosiloxy terminated oligo- This is a method of warming a phenolic siloxane prepared by heating trifluoromethanesulfonic acid as a catalyst in the production of phenylsiloxane, which is relatively toxic to the catalyst and expensive.

Korean Patent Application No. 10-2004-25063 discloses a method of preparing and applying an organic-inorganic hybrid by the sol-gel method, and in Korean Patent Publication No. 10-2011-0013891, a sol-gel method Based hybrid siloxane resin was used. In the above patent documents, the structure of the siloxane resin is changed to realize high hardness and high refractive index, but the siloxane crosslinking composition that crosslinks with the siloxane resin may damage the light emitting diode due to its high hardness after curing by the trifunctional functional group , When using a high viscosity siloxane resin, the flowability is poor and there is a problem in workability. When the platinum catalyst is used, there is a problem that the full curing time is slow and it may affect the productivity in actual production. Since the volatile solvent is contained in the catalyst, There was a possibility of air bubbles.

Therefore, there is a strong demand for research for solving the above-mentioned problems and for reducing the damage of light emitting diode devices due to high hardness.

Therefore, the inventors of the present invention have continued studies to improve the physical properties of the encapsulant using the siloxane crosslinking agent for light-emitting diodes. As a result, they have found that a cured product obtained by mixing and curing a siloxane crosslinking agent having a specific structure, a platinum catalyst having a specific structure and an organosiloxane resin High transparency, high refractive index, heat resistance and flexibility, and completed the present invention.

The present invention provides a siloxane crosslinking agent for an encapsulating material of a light emitting diode device.

The present invention also provides an encapsulant composition comprising the siloxane crosslinking agent, a platinum catalyst, and an organosiloxane resin, and a method for producing the same.

The present invention also provides an encapsulant comprising the encapsulant composition.

The present invention provides a siloxane crosslinking agent for an encapsulating material of a light emitting diode device.

The present invention also provides an encapsulant composition comprising the siloxane crosslinking agent, a platinum catalyst, and an organosiloxane resin, and a method for producing the same.

The present invention also provides an encapsulant comprising the encapsulant composition.

The encapsulant to which the siloxane crosslinking agent of the present invention is applied is excellent in high refractive index, heat resistance and flexibility, and has an effect of not damaging the wires and chips of the light emitting diode device due to high hardness.

The present invention provides a siloxane crosslinking agent for an encapsulating material of a light emitting diode device, which is represented by the following formula (1).

[Chemical Formula 1]

HMe 2 SiO (R 1 R 2 SiO) n SiMe 2 H

Wherein R 1 and R 2 are the same or different from each other and are a trimethylsiloxy group, a triethylsiloxy group, a tripropylsiloxy group, a tributylsiloxy group, a trihexylsiloxy group, a trioctylsiloxy group or a phenyl group, n = 1.

Preferably, the siloxane crosslinker of Formula 1 is selected from the group consisting of HMe 2 SiOSiPh (OSi (CH 3 ) 3 ) OSiMe 2 H; HMe 2 SiOSiPh (OSi (CH 2 CH 3 ) 3 ) OSiMe 2 H; HMe 2 SiOSiPh (OSi (CH 2 CH 2 CH 3 ) 3 ) OSiMe 2 H; HMe 2 SiOSiPh (OSi (CH 2 CH 2 CH 2 CH 3 ) 3 ) OSiMe 2 H; HMe 2 SiOSiPh (OSi (CH 2 CH 2 CH 2 CH 2 CH 3 ) 3 ) OSiMe 2 H; HMe 2 SiOSiPh (OSi (CH 2 CH 2 CH 2 CH 2 CH 2 CH 3) 3) OSiMe 2 H; And HMe 2 SiOSiPh 2 OSiMe 2 H.

The siloxane crosslinking agent is a compound having a three-dimensional structure or a bifunctional group of organohydrogensilicones, which can impart flexibility and hardness structurally to a trifunctional organohydrogensilicon compound having a three-dimensional structure, The viscosity after mixing with the resin can be lowered, which is preferable for controlling the viscosity at the time of molding.

The present invention also provides an encapsulant composition for a light emitting diode device comprising the siloxane crosslinking agent of Formula 1, the platinum catalyst of Formula 2 or 3, and the organosiloxane resin.

(2)

Pt 0揃 1.5 [(CH 2 ═CH (Me) 2 Si) 2 O]

(3)

Pt 0 - [CH 2 = CH (Me) SiO] 4

The organosiloxane resin includes, but is not limited to, a siloxane resin having a vinyl group, a phenyl group or an allyl group.

The encapsulant composition of the present invention may further contain additives such as an inorganic filler, a curing retarder, a heat resistance improving agent, and an organic solvent within a range that does not impair the purpose of use.

The inorganic filler is used for improving the mechanical strength or the refractive index of the composition in the bag and is preferably selected from silica, alumina, aluminum hydroxide, titanium oxide, alkoxytitanium, calcium carbonate, magnesium carbonate, aluminum nitride, magnesium oxide, zirconium oxide, Silicon nitride and the like can be used. At this time, silica may be used for increasing the mechanical strength of the composition, and titanium oxide or alkoxytitanium may be selected for improving the refractive index.

The curing retarder is not particularly limited, but acetylene series may be used. Preferably, 2-methyl-3-butyn-2-ol or 1-ethynyl- And 1-ethynyl-1-cyclohexanol.

As the heat resistance improver, a metal oxide, a metal organic acid salt, a transition metal, and the like which are usually used can be used without any limitation, preferably, cerium oxide can be used.

Examples of the organic solvent include, but are not limited to, benzene solvents such as toluene and xylene; Or an alcohol-based solvent such as 1-butanol, 2-butanol, isobutyl alcohol, isopentyl alcohol, isopropyl alcohol and the like can be preferably used.

The encapsulant composition may additionally contain at least one selected from the group consisting of an inorganic phosphor, an antioxidant, a radical inhibitor, an ultraviolet absorber, an adhesion improver, a flame retardant, a surfactant, a storage stability improver, an ozone deterioration inhibitor, a light stabilizer, a thickener, An auxiliary additive selected from the group consisting of an antioxidant, a heat stabilizer, a conductivity imparting agent, an antistatic agent, a radiopaque agent, a nucleating agent, a phosphorus peroxide dissolution agent, a lubricant, a pigment, a metal deactivator and a physical property modifier.

In addition,

(a) mixing and stirring the siloxane crosslinking agent of Formula 1, the platinum catalyst of Formula 2 or 3 and the organosiloxane resin; And

(b) curing the reactant in step (a) at 150 to 200 ° C for 2 to 24 hours to obtain a cured product.

If the thermal curing temperature is less than 150 ° C, the curing time is long and hard to be cured. If the thermal curing temperature is more than 250 ° C, the problem of yellowing due to heat is generated. If the thermosetting time is shorter than 2 hours, hardening does not occur. If the thermosetting time exceeds 24 hours, the physical strength of the cured product is lowered.

The present invention also provides an encapsulant for a light emitting diode device comprising the encapsulation material composition.

The encapsulating material of the light emitting diode device can be manufactured by a conventional method known in the art, and the form and the kind thereof are not particularly limited either.

The encapsulant to which the siloxane crosslinking agent according to the present invention is applied is excellent in transparency, high refractive index, heat resistance and flexibility, and has an effect of not damaging wires and chips of light emitting diode elements due to high hardness.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are provided only for the purpose of easier understanding of the present invention, and the present invention is not limited by the examples.

< Example 1 > Light Emitting Diodes For bag material Siloxane Cross-linking  Manufacturing HMe 2 SiOSiPh (OSi (CH 3 ) 3 ) OSiMe 2 H (in Formula 1, R One = Ph , R 2 = OSi ( CH 3 ) 3 )

In a 1 L four-necked flask equipped with a stirrer, a dropping funnel and a thermometer, 58.38 g (0.36 mol) of hexamethyldisiloxane and 80.58 g (0.6 mol) of 1,1,3,3-tetramethyldisiloxane ), 82.86 g (1.38 mol) of acetic acid and 11.76 g (0.12 mol) of sulfuric acid were added. While the reaction mixture was stirred at a constant rate, 71.4 g (0.36 mol) of phenyltrimethoxysilane was added thereto over 30 minutes Lt; / RTI &gt; Then, the reaction mixture was stirred for 5 hours while maintaining the temperature below 0 캜, the reaction mixture was raised to 25 캜 and stirred for 12 hours. The reaction mixture was transferred to a separatory funnel and washed repeatedly with water until the reaction was neutral. Water was removed using magnesium sulfate and the remaining unreacted material was evaporated to obtain 66 g of the title compound as a colorless liquid.

< Example 2 > Light Emitting Diodes For bag material Siloxane Cross-linking  Manufacturing HMe 2 SiOSiPh 2 OSiMe 2 H (in Formula 1, R One = Ph , R 2 = Ph )

In a 1 L four-necked flask equipped with a stirrer, a dropping funnel and a thermometer, 161.18 g (1.2 mol) of 1,1,3,3-tetramethyldisiloxane, 108.09 g (1.8 mol) of acetic acid, 23.54 g Mol) was added and the reaction mixture was cooled to 0 ° C while stirring at a constant rate, and then 175.93 g (0.72 mol) of diphenyldimethoxysilane was gradually added over 30 minutes. Then, the reaction mixture was stirred for 5 hours while maintaining the temperature below 0 캜, the reaction mixture was raised to 25 캜 and stirred for 12 hours. The reaction mixture was transferred to a separatory funnel and washed repeatedly with water until the reaction was neutral. Water was removed using magnesium sulfate and the remaining unreacted material was evaporated to obtain 175.8 g of the title compound as a colorless liquid.

< Comparative Example 1 > HMe 2 SiOSiPh ( OSi (H ( CH3 ) 2 ) OSiMe 2 Manufacture of H

In a 1 L four-necked flask equipped with a stirrer, a dropping funnel and a thermometer, 257.89 g (1.92 mol) of 1,1,3,3-tetramethyldisiloxane, 165.74 g (2.76 mol) of acetic acid, 23.54 g Mol) was added and the reaction mixture was cooled to 0 캜 while stirring at a constant rate. Then, 142.76 g (0.72 mol) of phenyltrimethoxysilane was gradually added over 30 minutes. Then, the reaction mixture was stirred for 5 hours while maintaining the temperature below 0 캜, the reaction mixture was raised to 25 캜 and stirred for 12 hours. The reaction mixture was transferred to a separatory funnel and washed repeatedly with water until the reaction was neutral. Water was removed using magnesium sulfate and the remaining unreacted material was evaporated to obtain 230 g of the title compound as a colorless liquid.

< Evaluation Example 1 -12 and Comparative Evaluation Example  1-6> Fabrication of encapsulant for light emitting diode device

The siloxane crosslinking agent prepared in Examples 1 and 2 and Comparative Example 1, the siloxane resin having vinyl group, and the platinum catalyst of Chemical Formula 2 or 3 were mixed and stirred and then cured at 180 ° C to obtain a transparent cured product. The content (g) of each constituent is shown in Tables 1 to 3.

< Experimental Example 1 > Measurement of physical properties of encapsulant

The hardness, refractive index and transparency of each of the cured products prepared in the evaluation examples 1 to 12 and the comparative evaluation examples 1 to 6 were measured. The evaluation method is as follows.

The refractive index was measured using an Abbe refractometer (1T-1212) at 25 degrees and 600 nm.

The hardness was measured using a Shore D type hardness meter and the hardness was measured according to ASTM D2240D.

The heat resistance was measured after standing for 96 hours in an oven at 180 ° C.

The results are shown in Tables 1 to 3 below.

Evaluation Example One 2 3 4 5 6 Vinyl siloxane resin 100 100 100 100 100 100 The siloxane crosslinker of Example 1 36 36 45 36 36 45 The platinum catalyst of formula (2) 0.025 0.040 0.025 - - - The platinum catalyst of formula (3) - - - 0.015 0.025 0.025 Refractive index 1.54 1.54 1.55 1.54 1.54 1.55 Hardness (180 degrees * 2 hours) 20 31 28 18 19 32 Hardness (180 degrees * 24 hours) 28 31 32 26 26 32 Hardness (180 degrees * 96 hours) 34 43 40 35 40 34

Evaluation Example 7 8 9 10 11 12 Vinyl siloxane resin 100 100 100 100 100 100 The siloxane crosslinker of Example 2 36 36 45 36 36 45 The platinum catalyst of formula (2) 0.025 0.040 0.025 - - - The platinum catalyst of formula (3) - - - 0.015 0.025 0.025 Refractive index 1.54 1.54 1.55 1.54 1.54 1.55 Hardness (180 degrees * 2 hours) 26 29 24 31 32 30 Hardness (180 degrees * 24 hours) 28 29 24 31 30 32 Hardness (180 degrees * 96 hours) 36 38 52 32 32 45

Comparative Evaluation Example One 2 3 4 5 6 Vinyl siloxane resin 100 100 100 100 100 100 The siloxane crosslinker of Comparative Example 1 36 36 45 36 36 45 The platinum catalyst of formula (2) 0.025 0.040 0.025 - - - The platinum catalyst of formula (3) - - - 0.015 0.025 0.025 Refractive index 1.54 1.54 1.55 1.54 1.54 1.55 Hardness (180 degrees * 2 hours) 40 45 48 35 32 52 Hardness (180 degrees * 24 hours) 49 55 60 47 50 60 Hardness (180 degrees * 96 hours) 54 60 65 50 52 67

As shown in Tables 1 to 3, it was confirmed that the sealing material to which the siloxane crosslinking agent according to the present invention was applied had excellent refractive index, heat resistance and curability.

Claims (12)

A siloxane crosslinking agent for an encapsulating material of a light-emitting diode element represented by the following formula (1)
[Chemical Formula 1]
HMe 2 SiO (R 1 R 2 SiO) n SiMe 2 H
In Formula 1, R 1 = a phenyl group; R 2 = trimethylsiloxy group, triethylsiloxy group, tripropylsiloxy group, tributylsiloxy group, trihexylsiloxy group, or trioctylsiloxy group; n = 1.
delete A siloxane crosslinker of claim 1; A platinum catalyst of formula (2) or (3); And an organosiloxane resin. &Lt; IMAGE &gt;
(2)
Pt 0揃 1.5 [(CH 2 ═CH (Me) 2 Si) 2 O]
(3)
Pt 0 - [CH 2 = CH (Me) SiO] 4
4. The encapsulating material composition of claim 3, wherein the organosiloxane resin is a siloxane resin having a vinyl group, a phenyl group or an allyl group.
The encapsulating material composition of claim 3, wherein the composition further comprises at least one additive selected from the group consisting of an inorganic filler, a curing retarder, a heat resistance enhancer, and an organic solvent.
The inorganic filler according to claim 5, wherein the inorganic filler is at least one selected from the group consisting of silica, alumina, aluminum hydroxide, titanium oxide, alkoxytitanium, calcium carbonate, magnesium carbonate, aluminum nitride, magnesium oxide, zirconium oxide, boron nitride and silicon nitride Wherein the light-emitting diode element is a thermosetting resin.
6. The composition of claim 5, wherein the cure retardant is selected from the group consisting of 2-methyl-3-butyn-2-ol or 1- ethynyl- -1-cyclohexanol). &Lt; / RTI &gt;
The encapsulating material composition for a light emitting diode device according to claim 5, wherein the heat resistance improving agent is cerium oxide.
The organic electroluminescent device according to claim 5, wherein the organic solvent is at least one selected from the group consisting of toluene, xylene, 1-butanol, 2-butanol, isobutyl alcohol, isopentyl alcohol, and isopropyl alcohol. / RTI &gt;
The composition according to claim 3, wherein the composition is at least one selected from the group consisting of an inorganic phosphor, an antioxidant, a radical inhibitor, an ultraviolet absorber, an adhesion improver, a flame retardant, a surfactant, a storage stability improver, an ozone deterioration inhibitor, a light stabilizer, a thickener, And further comprising at least one auxiliary additive selected from the group consisting of an antistatic agent, a heat stabilizer, a conductivity imparting agent, an antistatic agent, a radiation shielding agent, a nucleating agent, a phosphorus peroxide decomposer, a lubricant, a pigment, a metal deactivator, Composition.
(a) mixing and stirring the siloxane crosslinking agent of the formula (1), the platinum catalyst of the formula (2) or (3) and the organosiloxane resin; And
(b) curing the reaction product of step (a) at 150 to 200 ° C for 2 to 24 hours to obtain a cured product; Wherein the light-emitting diode element is a light-emitting diode.
[Chemical Formula 1]
HMe 2 SiO (R 1 R 2 SiO) n SiMe 2 H
In Formula 1, R 1 = a phenyl group; R 2 = trimethylsiloxy group, triethylsiloxy group, tripropylsiloxy group, tributylsiloxy group, trihexylsiloxy group, or trioctylsiloxy group; n = 1.
(2)
Pt 0揃 1.5 [(CH 2 ═CH (Me) 2 Si) 2 O]
(3)
Pt 0 - [CH 2 = CH (Me) SiO] 4
An encapsulant of a light emitting diode element comprising the encapsulation material composition of claim 3.

KR1020120056087A 2012-05-25 2012-05-25 Siloxane cross linker for sealing material of light emitting diode KR101454798B1 (en)

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KR102224233B1 (en) * 2014-08-05 2021-03-08 엘지이노텍 주식회사 Light emitting device package and lighting system having the same
EP3556795B1 (en) * 2016-12-13 2021-10-27 Mitsubishi Chemical Corporation Polyorganosiloxane, polyorganosiloxane composition, cured product, polyorganosiloxane-containing electrolytic solution for electrolytic capacitor, and electrolytic capacitor using same
CN107021976B (en) * 2017-02-27 2019-08-27 广东省稀有金属研究所 A kind of preparation method of two hydrogen-based diphenyl trisiloxanes of tetramethyl
CN108084220B (en) * 2018-01-08 2020-08-07 广东省稀有金属研究所 Preparation method of tetramethyldivinyldiphenyltrisiloxane
CN109280536B (en) * 2018-09-12 2021-05-04 烟台德邦科技股份有限公司 LED packaging silica gel with high cohesiveness and high sulfuration resistance and preparation method thereof

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JP2002338833A (en) 2001-02-23 2002-11-27 Kanegafuchi Chem Ind Co Ltd Composition for optical material, optical material, its manufacturing method, and liquid crystal display device and light-emitting diode obtained using the same
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JP2010043136A (en) * 2008-08-08 2010-02-25 Yokohama Rubber Co Ltd:The Silicone resin composition, silicone resin using the same and optical semiconductor sealed-body
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Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
JP2002338833A (en) 2001-02-23 2002-11-27 Kanegafuchi Chem Ind Co Ltd Composition for optical material, optical material, its manufacturing method, and liquid crystal display device and light-emitting diode obtained using the same
KR20080104279A (en) * 2006-02-24 2008-12-02 다우 코닝 코포레이션 Light emitting device encapsulated with silicones and curable silicone compositions for preparing the silicones
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JP2010043136A (en) * 2008-08-08 2010-02-25 Yokohama Rubber Co Ltd:The Silicone resin composition, silicone resin using the same and optical semiconductor sealed-body

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