KR20160016417A - Compound and transparent resin composition and encapsulant - Google Patents

Abstract

At least two cyclic siloxane moieties in which a plurality of Si-O bonds are cyclically linked, and at least one linear siloxane moiety connecting between said at least two cyclic siloxane moieties, wherein said cyclic The siloxane moiety is a compound having at least one silicon-hydrogen bond (Si-H) at the terminal thereof, a light-transmitting resin composition containing the compound, and an encapsulant obtained by curing the light-transmitting resin composition.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound, a translucent resin composition,

A light transmitting resin composition and an encapsulating material.

BACKGROUND ART Optical devices such as light emitting diodes (LEDs), organic light emitting diode devices (OLED devices), and photoluminescence devices (PL devices) And various automation devices.

These optical elements can display an intrinsic color of a light emitting material such as blue, red, and green in a light emitting portion, and can display white by combining light emitting portions that display different colors.

Such optical elements generally include encapsulants of a packaging or encapsulated structure. Such an encapsulant may be made from a light transmitting resin composition capable of passing light emitted from the light emitting portion to the outside.

One embodiment provides a compound that can be used in a light transmitting resin composition.

Another embodiment provides a light transmitting resin composition capable of enhancing reliability.

Another embodiment provides an encapsulant obtained by curing the light-transmitting resin composition.

According to one embodiment, at least two cyclic siloxane moieties in which a plurality of Si-O bonds are cyclically linked, and at least one linear siloxane moiety connecting between the at least two cyclic siloxane moieties, Wherein the cyclic siloxane moiety provides a compound having at least one silicon-hydrogen bond (Si-H) at the terminus.

The cyclic siloxane moiety may be represented by the following formula (1), and the linear siloxane moiety may be represented by the following formula (2).

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁶ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 aryl group, A substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a halogen group, or a combination thereof, Lt; / RTI >

At least one of R ¹ to R ⁶ is hydrogen,

At least one of R ¹ to R ⁶ is a connecting point connecting with the following formula (2)

n is from 0 to 10,

(2)

In Formula 2,

R ⁷ to R ¹⁰ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 aryl group, Substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C2 to C20 heteroaryl group, Or an unsubstituted C1 to C10 alkoxy group, a halogen group or a combination thereof,

L ¹ and L ² are each independently a single bond or a C 1 to C 10 alkylene group,

m is from 1 to 10,

* Is a connecting point connecting with the above formula (1).

The compound may comprise two said cyclic siloxane moieties facing each other and two said linear siloxane moieties facing each other.

The compound may be represented by the following general formula (3).

(3)

In Formula 3,

R ^{1 ',} R ^{1 ",} R ^{2 '} , R ³ to R ⁵ , and R ⁷ to R ¹⁰ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, An unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a halogen group or a combination thereof,

R ^{1 ',} R ^{1 ",} R ^{2 '} , at least one of R ³ to R ⁵ is hydrogen,

m is 1 to 10;

According to another embodiment, at least one first siloxane compound having at least one silicon-hydrogen bond (Si-H) at the end and at least one first siloxane compound having at least one silicon-alkenyl bond (Si-Vi) Wherein the at least one first siloxane compound comprises at least two cyclic siloxane moieties in which a plurality of Si-O bonds are cyclically linked and a second siloxane compound having at least two cyclic siloxane moieties And a compound having at least one linear siloxane moiety connecting between the moieties.

The cyclic siloxane moiety may be represented by the formula (1) and the linear siloxane moiety may be represented by the formula (2).

The first siloxane compound may comprise a compound comprising two cyclic siloxane moieties facing each other and two linear siloxane moieties facing each other.

The first siloxane compound may include a compound represented by the general formula (3).

The at least one first siloxane compound may further comprise a compound represented by the following general formula (4).

[Chemical Formula 4]

^{(R 11 R 12 R 13 SiO} 1/2) M1 (R 14 R 15 SiO 2/2) D1 (R 16 SiO 3/2) T1 (SiO 3/2 -Y 1 -SiO 3/2) T2 (SiO _{4/2) Q1}

In Formula 4,

R ¹¹ to R ¹⁶ are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 aryl group, C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, Or an unsubstituted C1 to C30 carbonyl group, a hydroxy group or a combination thereof,

At least one of R < ¹¹ > to R < ¹⁶ >

Y ¹ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroaryl A substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,

1 < / RTI &gt; < 1, 0 <

M1 + D1 + T1 + T2 + Q1 = 1.

The second siloxane compound may include a compound represented by the following general formula (5).

[Chemical Formula 5]

^{(R 17 R 18 R 19 SiO} 1/2) M2 (R 20 R 21 SiO 2/2) D2 (R 22 SiO 3/2) T3 (SiO 3/2 -Y 2 -SiO 3/2) T4 (SiO _{4/2) Q2}

In Formula 5,

R ¹⁷ to R ²² each independently represent a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 aryl Substituted or unsubstituted C1 to C30 heteroalkyl groups, substituted or unsubstituted C2 to C30 heterocycloalkyl groups, substituted or unsubstituted C2 to C30 alkenyl groups, substituted or unsubstituted C2 to C30 alkynyl groups, A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 carbonyl group, a hydroxy group or a combination thereof,

R ¹⁷ to R ²² At least one of them contains a substituted or unsubstituted C2 to C30 alkenyl group,

Y ² represents a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroaryl A substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,

0 < T2 < 1, 0 <

M2 + D2 + T3 + T4 + Q2 = 1.

The first siloxane compound may comprise less than about 50 wt.% Of the total amount of the first siloxane compound and the second siloxane compound, and the second siloxane compound may comprise less than about 50 wt.% Of the first siloxane compound and the second siloxane compound May be included in an amount greater than about 50% by weight relative to the total content.

The light-transmitting resin composition may further include a hydrogen silylation catalyst.

According to another embodiment, there is provided an encapsulant obtained by curing the light transmitting resin composition.

According to another embodiment, there is provided an electronic device comprising the encapsulant.

By increasing the hardness of the cured product, the inflow of gas and moisture can be effectively blocked and the heat resistance can be improved, thereby improving the reliability.

FIG. 1 is a cross-sectional view schematically showing a light emitting diode according to one embodiment,
Fig. 2 is a graph of gel permeation chromatography of the compound represented by formula 3aa of Synthesis Example 1. Fig.

Hereinafter, exemplary embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.

Unless otherwise defined herein, "substituted" means that the hydrogen atom in the compound is a halogen atom (F, Br, Cl, or I), a hydroxy group, an alkoxy group, a nitro group, a cyano group, A thio group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, A C 1 to C 30 arylalkyl group, a C 7 to C 30 arylalkyl group, a C 1 to C 30 alkoxy group, a C 1 to C 20 heteroalkyl group, a C 3 to C 20 heteroarylalkyl group, a C 3 to C 30 cycloalkyl group, a C 3 to C 15 cycloalkenyl group, C6 to C15 cycloalkynyl groups, C3 to C30 heterocycloalkyl groups, and combinations thereof.

In addition, unless otherwise defined herein, "hetero" means containing 1 to 3 heteroatoms selected from N, O, S and P.

Hereinafter, the compound for a light-transmitting resin composition according to one embodiment will be described.

A compound according to one embodiment comprises at least two cyclic siloxane moieties in which a plurality of Si-O bonds are cyclically linked and at least one cyclic siloxane moiety linking the at least two cyclic siloxane moieties Of a linear siloxane moiety, wherein the cyclic siloxane moiety has at least one silicon-hydrogen bond (Si-H) at the end.

The cyclic siloxane moiety may be included in the compound more than one, and each cyclic siloxane moiety may be represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁶ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 aryl group, A substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a halogen group, or a combination thereof, Lt; / RTI &gt;

At least one of R ¹ to R ⁶ is hydrogen,

At least one of R ¹ to R ⁶ is a connecting point connecting with the following formula (2)

n is from 0 to 10;

The cyclic siloxane moiety represented by Formula 1 is a moiety in which silicon (Si) and oxygen (O) are connected in a cyclic structure. For example, when n = 0, * -Si-O-Si- Si-O-Si-O- * is connected in a hexagonal ring structure when n = 1.

The cyclic siloxane moiety may include two or more of the above-mentioned compounds, for example, at positions facing each other.

The linear siloxane moiety may be included in one or more compounds, and each linear siloxane moiety may be represented by the following formula (2).

(2)

In Formula 2,

R ⁷ to R ¹⁰ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 aryl group, Substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C2 to C20 heteroaryl group, Or an unsubstituted C1 to C10 alkoxy group, a halogen group or a combination thereof,

L ¹ and L ² are each independently a single bond or a C 1 to C 10 alkylene group,

m is from 1 to 10,

* Is a connecting point connecting with the above formula (1).

The compound can be obtained, for example, by hydrogen silylation of a cyclic siloxane compound represented by the following formula (1a) and a linear siloxane compound represented by the following formula (2a).

[Formula 1a]

In formula (1a)

R ³¹ to R ³⁶ are each independently hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, A substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a halogen group, or a combination thereof,

At least two of R ³¹ to R ³⁶ are hydrogen,

n is from 0 to 10;

(2a)

In the above formula (2a)

R ⁷ to R ¹⁰ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 aryl group, Substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C2 to C20 heteroaryl group, Or an unsubstituted C1 to C10 alkoxy group, a halogen group or a combination thereof,

L ¹ and L ² are each independently a single bond or a C 1 to C 10 alkylene group,

m is 1 to 10;

The above-mentioned compounds can be obtained by reacting a part of the silicon-hydrogen bond part of the compound represented by the above formula (1a) with the terminal double bond of the compound represented by the above formula (2a) in the presence of, for example, a hydrogen silylation catalyst. At this time, the carbon-carbon double bond at the end of the compound represented by Formula 2a may be loosened and connected with ethylene.

The compound may be, but is not limited to, a structure comprising, for example, two of the cyclic siloxane moieties facing each other and two of the linear siloxane moieties facing each other.

Such a compound can be represented, for example, by the following formula (3).

(3)

In Formula 3,

R ^{1 ',} R ^{1 ",} R ^{2 '} , R ³ to R ⁵ , and R ⁷ to R ¹⁰ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, An unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a halogen group or a combination thereof,

R ^{1 ',} R ^{1 ",} R ^{2 '} , at least one of R ³ to R ⁵ is hydrogen,

m is 1 to 10;

The compound can provide a curing agent in a three-dimensional structure, such as, for example, a cage type, by including a plurality of cyclic siloxane moieties and at least one linear siloxane moiety connecting the plurality of cyclic siloxane moieties Thus, the crosslinking density can be increased and the hardness can be imparted during curing. Accordingly, it is possible to enhance the heat resistance of the cured product formed from the composition containing the compound and reduce the inflow of moisture and / or gas from the outside, thereby remarkably improving the moisture permeability and oxygen permeability, thereby improving the reliability.

Such a compound can be used, for example, as one component of a light-transmitting resin composition.

Hereinafter, the light-transmitting resin composition according to one embodiment will be described.

The light-transmitting resin composition according to an embodiment includes at least one first siloxane compound having at least one silicon-hydrogen bond (Si-H) at the terminal and at least one silicon-alkenyl bond (Si-Vi) The branch comprises at least one second siloxane compound.

The first siloxane compound may include at least one compound having at least one silicon-hydrogen bond (Si-H) at the terminal.

The at least one first siloxane compound is a compound having at least two cyclic siloxane moieties in which a plurality of Si-O bonds are cyclically linked and at least two cyclic siloxane moieties A compound having at least one linear siloxane moiety.

As described above, the cyclic siloxane moiety may be contained in the compound more than one, and each cyclic siloxane moiety may be represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1), R ¹ to R ⁶ and n are as described above.

The linear siloxane moiety may be included in one or more compounds, and each linear siloxane moiety may be represented by the following formula (2).

(2)

In the general formula (2), R ⁷ to R ¹⁰ , L ¹ , L ² , m and * have the same meanings as described above.

The compound may be, for example, a structure comprising two cyclic siloxane moieties facing each other and two linear siloxane moieties facing each other, and may be represented by, for example, the following formula (3).

(3)

In Formula 3, R ^{1 '} , R ^{1 "} R ^{2 '} , R ³ to R ⁵ , R ⁷ to R ¹⁰ and m are as described above.

The at least one first siloxane compound may further include, for example, a compound represented by the following general formula (4).

[Chemical Formula 4]

^{(R 11 R 12 R 13 SiO} 1/2) M1 (R 14 R 15 SiO 2/2) D1 (R 16 SiO 3/2) T1 (SiO 3/2 -Y 1 -SiO 3/2) T2 (SiO _{4/2) Q1}

In Formula 4,

R ¹¹ to R ¹⁶ are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 aryl group, C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, Or an unsubstituted C1 to C30 carbonyl group, a hydroxy group or a combination thereof,

At least one of R &lt; ¹¹ &gt; to R &lt; ¹⁶ &gt;

Y ¹ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroaryl A substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,

1 < / RTI &gt; < 1, 0 <

M1 + D1 + T1 + T2 + Q1 = 1.

The compound represented by the formula (4) can be obtained, for example, by hydrolysis and condensation polymerization of a silane monomer. For example, a monomer represented by R ¹¹ R ¹² R ¹³ SiZ ¹ , a monomer represented by R ¹⁴ R ¹⁵ SiZ ² Z ³ , a monomer represented by R ¹⁶ SiZ ⁴ Z ⁵ Z ⁶ , Z ⁷ Z ⁸ Z ⁹ Si-Y ¹ -SiZ ¹⁰ Z ¹¹ Z ¹² and at least one monomer selected from SiZ ¹³ Z ¹⁴ Z ¹⁵ Z ¹⁶ , by hydrolysis and condensation polymerization. Wherein R ¹¹ To R ¹⁶ are as defined above, and Z ¹ to Z ¹⁶ each independently may be a C ¹ to C 6 alkoxy group, a hydroxy group, a halogen group, a carboxyl group, or a combination thereof.

The second siloxane compound may include at least one compound having at least one silicon-alkenyl bond (Si-Vi) at the terminal.

The second siloxane compound may include a compound represented by the following general formula (5).

[Chemical Formula 5]

^{(R 17 R 18 R 19 SiO} 1/2) M2 (R 20 R 21 SiO 2/2) D2 (R 22 SiO 3/2) T3 (SiO 3/2 -Y 2 -SiO 3/2) T4 (SiO _{4/2) Q2}

In Formula 5,

R ¹⁷ to R ²² each independently represent a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 aryl Substituted or unsubstituted C1 to C30 heteroalkyl groups, substituted or unsubstituted C2 to C30 heterocycloalkyl groups, substituted or unsubstituted C2 to C30 alkenyl groups, substituted or unsubstituted C2 to C30 alkynyl groups, A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 carbonyl group, a hydroxy group or a combination thereof,

R ¹⁷ to R ²² At least one of them contains a substituted or unsubstituted C2 to C30 alkenyl group,

Y ² represents a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroaryl A substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,

0 < T2 < 1, 0 <

M2 + D2 + T3 + T4 + Q2 = 1.

The compound represented by the formula (5) can be obtained, for example, by hydrolysis and condensation polymerization of a silane monomer. For example, a monomer represented by R ¹⁷ R ¹⁸ R ¹⁹ SiZ ¹⁷ , a monomer represented by R ²⁰ R ²¹ SiZ ¹⁸ Z ¹⁹ , a monomer represented by R ²² SiZ ²⁰ Z ²¹ Z ²² , a monomer represented by Z ²³ Z ²⁴ Z ²⁵ Si-Y ² -SiZ ²⁶ Z ²⁷ Z ²⁸ and at least one monomer selected from the group consisting of SiZ ²⁹ Z ³⁰ Z ³¹ Z ³² . Here, the definitions of R ¹⁷ to R ²² are as defined above, and Z ¹⁷ to Z ³² each independently represent a C 1 to C 6 alkoxy group, a hydroxy group, a halogen group, a carboxyl group, or a combination thereof.

The first siloxane compound may comprise less than about 50 wt.% Of the total amount of the first siloxane compound and the second siloxane compound, and the second siloxane compound may comprise less than about 50 wt.% Of the first siloxane compound and the second siloxane compound May be included in an amount greater than about 50% by weight relative to the total content.

As described above, a compound having at least one linear siloxane moiety linking two cyclic siloxane moieties and the at least two cyclic siloxane moieties may have a three-dimensional structure, such as, for example, a cage type It can serve as a curing agent to increase the cross-linking density and give the hardness at the time of curing. Accordingly, it is possible to improve the heat resistance of the cured product formed from the light transmitting resin composition containing the compound and to reduce the inflow of moisture and / or gas from the outside, thereby remarkably improving the moisture permeability and oxygen permeability, and thus improving the reliability.

The light transmitting resin composition may further include a filler.

The filler may be made of, for example, an inorganic oxide, and may include, for example, silica, alumina, titanium oxide, zinc oxide, or a combination thereof.

The light-transmitting resin composition may further include a hydrogen silylation catalyst.

The hydrogen silylation catalyst may promote the hydrogen silylation reaction of the first siloxane compound and the second siloxane compound, and may include, for example, platinum, rhodium, palladium, ruthenium, iridium or a combination thereof.

The hydrogen sacylation catalyst may be included in an amount of about 0.1 ppm to 1000 ppm based on the total amount of the light-transmitting resin composition.

The light-transmitting resin composition can be used as an encapsulant by heat-treating at a predetermined temperature to be cured. The encapsulant can be applied to electronic devices such as light emitting diodes and organic light emitting devices.

Hereinafter, a light emitting diode according to one embodiment will be described with reference to FIG. 1 as an example of an electronic device to which a sealing material is applied.

1 is a cross-sectional view schematically illustrating a light emitting diode according to one embodiment.

1, the light emitting diode includes a mold 110; A lead frame 120 disposed within the mold 110; A light emitting diode chip 140 mounted on the lead frame 120; A bonding wire 150 connecting the lead frame 120 and the light emitting diode chip 140; And an encapsulant 200 covering the light emitting diode chip 140.

The sealing material 200 is obtained by curing the above-mentioned light-transmitting resin composition. The encapsulant 200 is formed from the above-mentioned light-transmitting resin composition, thereby effectively protecting the LED chip 140 and preventing the performance of the LED from being deteriorated.

The encapsulant 200 may have the phosphor 190 dispersed therein. The phosphor 190 includes a material that is stimulated by light and emits light of a specific wavelength range by itself, and broadly includes a quantum dot such as a semiconductor nanocrystal. The phosphor 190 may be, for example, a blue phosphor, a green phosphor, or a red phosphor, and may be a mixture of two or more types.

The phosphor 190 may display a color of a predetermined wavelength region by the light supplied from the light emitting diode chip 140 as a light emitting portion. At this time, the light emitting diode chip 140 has a shorter wavelength region Can be displayed. For example, when the phosphor 190 displays a red color, the light emitting diode chip 140 can supply blue or green light having a shorter wavelength region than the red color.

The color emitted from the light emitting diode chip 140 and the color emitted from the phosphor 190 may be combined to display a white color. For example, when the light emitting diode chip 140 supplies blue light and the phosphor 190 includes a red phosphor and a green phosphor, the electronic device may display a white color by combining blue, red, and green.

The phosphor 190 may be omitted.

Hereinafter, embodiments of the present invention will be described in detail with reference to examples. The following examples are for illustrative purposes only and are not intended to limit the scope of the invention.

Synthetic example

Synthetic example  One:

A four-necked flask equipped with a stirrer, a temperature controller, a nitrogen gas injector and a condenser was charged with 2,4,6,8-tetramethylcyclotetrasiloxane (2,4,6,8,8) -tetramethylcyclotetrasiloxane, sigma-aldrich) and 1,3-divinyltetramethyldisiloxane (sigma-aldrich) represented by the following formula (2aa) in a molar ratio of 2: 1, hydrogen silylation PS-CS-2.0CS (Unicore) as a catalyst was added so that the Pt content was 20 ppm, followed by stirring for 24 hours.

(1aa)

[Formula 2aa]

The reaction was then carried out at 50 &lt; 0 &gt; C for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the hydrogenation catalyst was removed, and the filtrate was distilled under reduced pressure to remove the unreacted material.

[Formula 3aa]

The compound represented by Formula 3aa was analyzed by gel permeation chromatography (GPC) to find that the molecular weight in terms of polystyrene was about 890 g / mol.

2 is a graph of gel permeation chromatography of a compound represented by formula 3aa.

Synthetic example  2

1 kg of a mixed solvent in which water and toluene were mixed at a weight ratio of 5: 5 was charged into a three-necked flask, and dimethylchlorosilane and phenylmethyldichlorosilane were added to the monomer at a molar ratio of 10:90 Was added dropwise over 2 hours. After completion of the dropwise addition, condensation polymerization reaction was carried out while refluxing at 90 ° C for 3 hours. After cooling to room temperature, the water layer was removed to prepare a polymer solution dissolved in toluene. The resulting polymer solution was washed with water to remove chlorine as a by-product of the reaction. Subsequently, the neutral polymer solution was distilled under reduced pressure to remove toluene to obtain a liquid polysiloxane represented by the following chemical formula 4aa.

[Chemical Formula 4aa]

_{(Me 2 HSiO 1/2)} 0.1 (PhMeSiO 2/2) 0.9

Synthetic example  3

1 kg of a mixed solvent in which water and toluene were mixed at a weight ratio of 5: 5 was introduced into a three-necked flask, and vinyldimethylchlorosilane and phenylmethyldichlorosilane were mixed at a molar ratio of 10:90 Was added dropwise over 2 hours. After completion of the dropwise addition, condensation polymerization reaction was carried out while refluxing at 90 ° C for 3 hours. After cooling to room temperature, the water layer was removed to prepare a polymer solution dissolved in toluene. The resulting polymer solution was washed with water to remove chlorine as a by-product of the reaction. Subsequently, the neutral polymer solution was distilled under reduced pressure to remove toluene to obtain a liquid polysiloxane represented by the following chemical formula 5aa.

[Chemical Formula 5aa]

_{(Me 2 ViSiO 1/2)} 0.1 (PhMeSiO 2/2) 0.9

Synthetic example  4

1 kg of a mixed solvent in which water and toluene were mixed at a weight ratio of 5: 5 was charged into a three-necked flask, and vinyldimethylchlorosilane and phenyltrichlorosilane were mixed as a monomer at a molar ratio of 10:90 Was added dropwise over 2 hours. After completion of the dropwise addition, condensation polymerization reaction was carried out while refluxing at 90 ° C for 3 hours. After cooling to room temperature, the water layer was removed to prepare a polymer solution dissolved in toluene. The resulting polymer solution was washed with water to remove chlorine as a by-product of the reaction. Subsequently, the neutral polymer solution was distilled under reduced pressure to remove toluene to obtain a liquid polysiloxane represented by the following chemical formula 5aa.

[Chemical Formula 5ab]

_{(Me 2 ViSiO 1/2)} 0.1 (PhSiO 3/2) 0.9

Translucency  Preparation of resin composition

Example  One

5% by weight of the siloxane compound obtained in Synthesis Example 1, 17% by weight of the siloxane compound obtained in Synthesis Example 2, 20% by weight of the siloxane compound obtained in Synthesis Example 3, 58% by weight of the siloxane compound obtained in Synthesis Example 4, CS 2.0 (manufactured by Umicore) (added so that the content of Pt became 5 ppm) were mixed and defoamed in vacuo to prepare a light transmitting resin composition.

Example  2

10% by weight of the siloxane compound obtained in Synthesis Example 1, 15% by weight of the siloxane compound obtained in Synthesis Example 2, 20% by weight of the siloxane compound obtained in Synthesis Example 3, 55% by weight of the siloxane compound obtained in Synthesis Example 4, CS 2.0 (manufactured by Umicore) (added so that the content of Pt became 5 ppm) were mixed and defoamed in vacuo to prepare a light transmitting resin composition.

Example  3

20% by weight of the siloxane compound obtained in Synthesis Example 1, 10% by weight of the siloxane compound obtained in Synthesis Example 2, 20% by weight of the siloxane compound obtained in Synthesis Example 3, and 50% by weight of the siloxane compound obtained in Synthesis Example 4, CS 2.0 (manufactured by Umicore) (added so that the content of Pt became 5 ppm) were mixed and defoamed in vacuo to prepare a light transmitting resin composition.

Comparative Example  One

20% by weight of the siloxane compound obtained in Synthesis Example 2, 20% by weight of the siloxane compound obtained in Synthesis Example 3, 60% by weight of the siloxane compound obtained in Synthesis Example 4, and hydrogen saccharification catalyst Pt-CS 2.0 (manufactured by Umicore) Was added so as to be 5 ppm) was mixed and defoamed in vacuo to prepare a light transmitting resin composition.

evaluation

Rating 1

The hardness, thermal expansion coefficient, moisture permeability and oxygen permeability of the translucent resin compositions according to Examples 1 to 3 and Comparative Example 1 were evaluated.

The light transmitting resin compositions of Examples 1 to 3 and Comparative Example 1 were fed into a mold (2.5 cm (width) x 7.5 cm (length) x 1 cm (thickness)) coated with Teflon and heated at 80 DEG C for 1 hour, 120 DEG C For 1 hour and at 160 DEG C for 1 hour, then cooled to room temperature and the hardness was measured using a Shore A hardness tester.

The coefficient of thermal expansion was measured by a TMA instrument (manufactured by TA Corporation) with a cured specimen (1 cm * 1 cm * 0.4 cm) of the encapsulating material composition.

For the moisture permeability, a cured specimen of 10 mm in thickness of the light transmitting resin composition according to Examples 1 to 3 and Comparative Example 1 was prepared and cured at 130 캜 for 5 minutes and at 170 캜 for 4 hours. Then, a moisture permeability meter (ASTM F-1249 ).

The oxygen permeability was measured by coating a composition on a polyimide film-coated glass substrate (10 x 10 cm) with a thickness of about 15 μm and separating the polyimide film from the polyimide film to obtain a gas permeability measuring device (GTR-20XAMDE, GTR Tech The gas permeation coefficient was measured using a gas chromatograph.

The results are shown in Table 1.

Hardness
(Shorea) Coefficient of thermal expansion
(CTE) Moisture permeability
(gm / m2day) Oxygen permeability
(cc / m2day) Example 1 90 95 6.7 360 Example 2 91 93 6.3 320 Example 3 93 87 6.0 280 Comparative Example 1 85 100 7.5 380

Referring to Table 1, it can be confirmed that the light transmitting resin composition according to Examples 1 to 3 has a remarkably improved hardness, thermal expansion coefficient, moisture permeability and oxygen permeability as compared with the light transmitting resin composition according to Comparative Example 1.

Rating 2

The viscosity of the light transmitting resin composition according to Examples 1 to 3 and Comparative Example 1 was evaluated. The viscosity was measured using a Brookfield (DV-II + pro) spindle 52 at a torque of 90% at 25 ° C.

Further, the translucent resin compositions according to Examples 1 to 3 and Comparative Example 1 were cured by heating in an oven at 150 캜 for 2 hours, and initial transmittance at 450 nm was measured using a UV-spectrophotometer (Shimazu UV-3600).

Subsequently, the cured resin was allowed to stand at 120 DEG C for 1000 hours, and then the transmittance at 450 nm was measured using a UV-spectrophotometer (Shimazu UV-3600).

The results are shown in Table 2.

Viscosity (cP) Initial permeability (%) (%) After curing at 120 占 폚 for 1000 hours Example 1 3300 98 96 Example 2 3100 98 97 Example 3 2700 98 97 Comparative Example 1 3500 98 96

Referring to Table 2, it can be confirmed that the translucent resin compositions according to Examples 1 to 3 have the same or improved viscosity and transparency as compared with the translucent resin composition according to Comparative Example 1. [

When synthesizing the above evaluation results, the translucent resin compositions of Examples 1 to 3 were improved in viscosity and transmittance to be equal to or higher than those of the translucent resin composition of Comparative Example 1, and at the same time, the hardness was increased, It can be confirmed that the oxygen permeability is remarkably improved. Furthermore, it can be confirmed that the above effect is more remarkable as the content of the siloxane compound according to Synthesis Example 1 is increased.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, And falls within the scope of the invention.

110: mold 120: frame
140: light emitting diode chip 150: bonding wire
200: sealing material

Claims (14)

At least two cyclic siloxane moieties in which a plurality of Si-O bonds are cyclically linked, and
At least one linear siloxane moiety connecting between the at least two cyclic siloxane moieties
Lt; / RTI &gt;
The cyclic siloxane moiety has at least one silicon-hydrogen bond (Si-H)
compound.
The method of claim 1,
Wherein the cyclic siloxane moiety is represented by the following general formula (1)
Wherein the linear siloxane moiety is represented by the formula
compound:
[Chemical Formula 1]

In Formula 1,
R ¹ to R ⁶ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 aryl group, A substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a halogen group, or a combination thereof, Lt; / RTI &gt;
At least one of R ¹ to R ⁶ is hydrogen,
At least one of R ¹ to R ⁶ is a connecting point connecting with the following formula (2)
n is from 0 to 10,
(2)

In Formula 2,
R ⁷ to R ¹⁰ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 aryl group, Substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C2 to C20 heteroaryl group, Or an unsubstituted C1 to C10 alkoxy group, a halogen group or a combination thereof,
L ¹ and L ² are each independently a single bond or a C 1 to C 10 alkylene group,
m is from 1 to 10,
* Is a connecting point connecting with the above formula (1).
The method of claim 1,
And two said cyclic siloxane moieties facing each other and two said linear siloxane moieties facing each other.
The method of claim 1,
A compound represented by the formula (3):
(3)

In Formula 3,
R ^{1 ',} R ^{1 ",} R ^{2 '} , R ³ to R ⁵ , and R ⁷ to R ¹⁰ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, An unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a halogen group or a combination thereof,
R ^{1 ',} R ^{1 ",} R ^{2 '} , at least one of R ³ to R ⁵ is hydrogen,
m is 1 to 10;
At least one first siloxane compound having at least one silicon-hydrogen bond (Si-H) at its end, and
At least one second siloxane compound having at least one silicon-alkenyl bond (Si-Vi) at the end thereof
/ RTI &gt;
The at least one first siloxane compound
A compound having at least two cyclic siloxane moieties in which a plurality of Si-O bonds are cyclically linked and at least one linear siloxane moiety linking between said at least two cyclic siloxane moieties
Transparent resin composition.
The method of claim 5,
Wherein the cyclic siloxane moiety is represented by the following Formula 1 and the linear siloxane moiety is represented by the following Formula 2:
[Chemical Formula 1]

In Formula 1,
R ¹ to R ⁶ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 aryl group, A substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a halogen group, or a combination thereof, Lt; / RTI &gt;
At least one of R ¹ to R ⁶ is hydrogen,
At least one of R ¹ to R ⁶ is a connecting point connecting with the following formula (2)
n is from 0 to 10,
(2)

In Formula 2,
R ⁷ to R ¹⁰ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 aryl group, Substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C2 to C20 heteroaryl group, Or an unsubstituted C1 to C10 alkoxy group, a halogen group or a combination thereof,
L ¹ and L ² are each independently a single bond or a C 1 to C 10 alkylene group,
m is from 1 to 10,
* Is a connecting point connecting with the above formula (1).
The method of claim 5,
Wherein said first siloxane compound comprises a compound comprising two said cyclic siloxane moieties facing each other and two said linear siloxane moieties facing each other.
The method of claim 5,
Wherein the first siloxane compound comprises a compound represented by the following formula (3): &lt; EMI ID =
(3)

In Formula 3,
R ^{1 ',} R ^{1 ",} R ^{2 '} , R ³ to R ⁵ , and R ⁷ to R ¹⁰ are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, An unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a halogen group or a combination thereof,
R ^{1 ',} R ^{1 ",} R ^{2 '} , at least one of R ³ to R ⁵ is hydrogen,
m is 1 to 10;
The method of claim 5,
Wherein said at least one first siloxane compound further comprises a compound represented by the following general formula (4): < EMI ID =
[Chemical Formula 4]
^{(R 11 R 12 R 13 SiO} 1/2) M1 (R 14 R 15 SiO 2/2) D1 (R 16 SiO 3/2) T1 (SiO 3/2 -Y 1 -SiO 3/2) T2 (SiO _{4/2) Q1}
In Formula 4,
R ¹¹ to R ¹⁶ are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 aryl group, C30 arylalkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C30 alkoxy group, Or an unsubstituted C1 to C30 carbonyl group, a hydroxy group or a combination thereof,
At least one of R < ¹¹ &gt; to R < ¹⁶ &gt;
Y ¹ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroaryl A substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,
1 &lt; / RTI &gt;&lt; 1, 0 &lt;
M1 + D1 + T1 + T2 + Q1 = 1.
The method of claim 5,
Wherein the second siloxane compound comprises a compound represented by the following general formula (5): < EMI ID =
[Chemical Formula 5]
^{(R 17 R 18 R 19 SiO} 1/2) M2 (R 20 R 21 SiO 2/2) D2 (R 22 SiO 3/2) T3 (SiO 3/2 -Y 2 -SiO 3/2) T4 (SiO _{4/2) Q2}
In Formula 5,
R ¹⁷ to R ²² each independently represent a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 aryl Substituted or unsubstituted C1 to C30 heteroalkyl groups, substituted or unsubstituted C2 to C30 heterocycloalkyl groups, substituted or unsubstituted C2 to C30 alkenyl groups, substituted or unsubstituted C2 to C30 alkynyl groups, A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 carbonyl group, a hydroxy group or a combination thereof,
R ¹⁷ to R ²² At least one of them contains a substituted or unsubstituted C2 to C30 alkenyl group,
Y ² represents a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroaryl A substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,
0 < T2 < 1, 0 <
M2 + D2 + T3 + T4 + Q2 = 1.
The method of claim 5,
The first siloxane compound may include less than 50 wt% of the total amount of the first siloxane compound and the second siloxane compound, and the second siloxane compound may include less than 50 wt% of the total of the first siloxane compound and the second siloxane compound, By weight based on the weight of the light-transmitting resin composition.
The method of claim 5,
And a hydrogen silylation catalyst.
An encapsulating material obtained by curing the light transmitting resin composition according to any one of claims 5 to 12.
An electronic device comprising an encapsulant according to claim 13.

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