KR101387739B1 - Transparent resin composition and encapsulant formed using the same and electronec device including the encapsulant - Google Patents

Abstract

It provides a light transmitting resin composition comprising a polysiloxane having a moiety represented by the following formula (1):
[Chemical Formula 1]
* -Si-Ar-Si- *
In Formula 1, Ar is a substituted or unsubstituted C6 to C30 arylene group.

Description

TRANSPARENT RESIN COMPOSITION AND ENCAPSULANT FORMED USING THE SAME AND ELECTRONEC DEVICE INCLUDING THE ENCAPSULANT}

The present invention relates to a light-transmissive resin composition, an encapsulant formed using the light-transmissive resin composition, and an electronic device including the encapsulant.

Light emitting diodes such as light emitting diodes (LEDs), solar cells, organic light emitting diode devices (OLED devices), and photoluminescence (PL) devices are used in home appliances. It is applied to various fields, such as a lighting apparatus, a display apparatus, and various automation devices.

These light emitting devices may display inherent colors of light emitting materials such as blue, red, and green using light emitters, and may display white by combining light emitters displaying different colors.

Such light emitting and semiconductor devices are generally manufactured in a packaged or encapsulated structure.

Such a packaging or sealing structure may include an encapsulant through which light emitted from the light emitter can pass, and the encapsulant may be made of a light transmitting resin composition.

One aspect of the present invention provides a light transmitting resin composition.

Another aspect of the invention provides an encapsulant formed using the light-transmissive resin composition.

Yet another aspect of the present invention provides an electronic device comprising the encapsulant.

According to an aspect of the present invention, there is provided a light transmitting resin composition comprising a polysiloxane having a moiety represented by the following Chemical Formula 1.

[Chemical Formula 1]

* -Si-Ar-Si- *

In Formula 1, Ar is a substituted or unsubstituted C6 to C30 arylene group.

The polysiloxane may include at least one of a moiety represented by Chemical Formula 2a, a moiety represented by Chemical Formula 2b, and a moiety represented by Chemical Formula 2c, Chemical Formula 2d, and Chemical Formula 2e.

(2a)

(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b

(2b)

R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c

[Chemical Formula 2c]

R ³ SiO _{(3-d) / 2} (OR ^IV ) _d

 (2d)

R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^V ) _e

[Formula 2e]

_{^{R 6 R 7 R 8 SiO 1}} /2

In Formulas 2a to 2e, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, substituted Or an unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C10 hydroxyalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group, a substituted or unsubstituted A C2 to C10 alkenyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a lactone group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, a, b and d is each independently 0-2, and c and e are each independently 0-1.

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

(3)

^{(R 6 R 7 R 8 SiO} 1/2) m [(OR I) a O (3-a) / 2 Si-Ar-SiO (3-b) / 2 (OR II) b] n [R 3 SiO _{(3-d) / 2} (OR ^IV ) _d ] _p [R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c ] _q [R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^III ) _e ] _r

In Formula 3, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted group C3 to C20 cycloalkyl group, substituted or unsubstituted C1 to C10 hydroxyalkyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C20 heteroaryl group, substituted or unsubstituted C2 to C10 Alkenyl group, substituted or unsubstituted C1 to C10 alkoxy group, lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, Ar is a C6 to C30 aryl group A, b and d are each independently 0 to 2, c and e are 0 to 1, 0 <m <0.9, 0 <n <0.2, 0≤p <0.9, 0 <q <0.9 and 0 <R <0.9 and m + n + p + q + r = 1.

The polysiloxane may be included in about 50% by weight or more based on the total content of the light transmitting resin composition.

The polysiloxane may be included in an amount of about 50 to 99.9% by weight based on the total content of the light transmitting resin composition.

According to another aspect of the present invention, there is provided an encapsulant obtained by curing a light-transmissive resin composition comprising a polysiloxane having a moiety represented by the following formula (1).

[Chemical Formula 1]

* -Si-Ar-Si- *

In Formula 1, Ar is a substituted or unsubstituted C6 to C30 arylene group

The polysiloxane may include at least one of a moiety represented by Chemical Formula 2a, a moiety represented by Chemical Formula 2b, and a moiety represented by Chemical Formula 2c, Chemical Formula 2d, and Chemical Formula 2e.

(2a)

(OR ^I ) _a O _{(3-a) / 2} Si- Ar-SiO _{(3-b) / 2} (OR ^II ) _b

(2b)

R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c

[Chemical Formula 2c]

R ³ SiO _{(3-d) / 2} (OR ^IV ) _d

 (2d)

R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^V ) _e

[Formula 2e]

_{^{R 6 R 7 R 8 SiO 1}} /2

In Formulas 2a to 2e, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, substituted Or an unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C10 hydroxyalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group, a substituted or unsubstituted A C2 to C10 alkenyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a lactone group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, a, b and d is each independently 0-2, and c and e are each independently 0-1.

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

(3)

^{(R 6 R 7 R 8 SiO} 1/2) m [(OR I) a O (3-a) / 2 Si-Ar-SiO (3-b) / 2 (OR II) b] n [R 3 SiO _{(3-d) / 2} (OR ^IV ) _d ] _p [R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c ] _q [R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^III ) _e ] _r

In Formula 3, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted group C3 to C20 cycloalkyl group, substituted or unsubstituted C1 to C10 hydroxyalkyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C20 heteroaryl group, substituted or unsubstituted C2 to C10 Alkenyl group, substituted or unsubstituted C1 to C10 alkoxy group, lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, Ar is a C6 to C30 aryl group A, b and d are each independently 0 to 2, c and e are each independently 0 to 1, and 0 <m <0.9, 0 <n <0.2, 0≤p <0.9, 0 <q < 0.9 and 0 ≦ r <0.9 and m + n + p + q + r = 1.

According to another aspect of the invention, the light emitting and semiconductor device and the encapsulation material surrounding the light emitting device, the encapsulation material is obtained by curing the light-transmissive resin composition comprising a polysiloxane having a part represented by the formula (1) Provided is an element.

[Chemical Formula 1]

* -Si-Ar-Si- *

In Formula 1, Ar is a substituted or unsubstituted C6 to C30 arylene group.

The polysiloxane may include at least one of a moiety represented by Chemical Formula 2a, a moiety represented by Chemical Formula 2b, and a moiety represented by Chemical Formula 2c, Chemical Formula 2d, and Chemical Formula 2e.

(2a)

(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b

(2b)

R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c

[Chemical Formula 2c]

R ³ SiO _{(3-d) / 2} (OR ^IV ) _d

 (2d)

R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^V ) _e

[Formula 2e]

_{^{R 6 R 7 R 8 SiO 1}} /2

In Formulas 2a to 2e, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, substituted Or an unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C10 hydroxyalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group, a substituted or unsubstituted A C2 to C10 alkenyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a lactone group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, a, b and d is each independently 0-2, and c and e are each independently 0-1.

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

(3)

^{(R 6 R 7 R 8 SiO} 1/2) m [(OR I) a O (3-a) / 2 Si-Ar-SiO (3-b) / 2 (OR II) b] n [R 3 SiO _{(3-d) / 2} (OR ^IV ) _d ] _p [R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c ] _q [R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^III ) _e ] _r

In Formula 3, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted group C3 to C20 cycloalkyl group, substituted or unsubstituted C1 to C10 hydroxyalkyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C20 heteroaryl group, substituted or unsubstituted C2 to C10 Alkenyl group, substituted or unsubstituted C1 to C10 alkoxy group, lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, Ar is a C6 to C30 aryl group A, b and d are each independently 0 to 2, c and e are 0 to 1, 0 <m <0.9, 0 <n <0.2, 0≤p <0.9, 0 <q <0.9 and 0 <R <0.9 and m + n + p + q + r = 1.

The electronic device may include a light emitting diode, an organic light emitting device, a solar cell, and an optical luminescence.

The molecular weight, viscosity, vinyl content and hardness can be easily controlled.

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 a hydrogen atom in a compound is a halogen atom (F, Br, Cl, or I), a hydroxyl group, an alkoxy group, a carbonyl group, a carbamyl group, an ester group, a carboxyl group or Salt, alkyl group, C2 to C16 alkenyl group, C2 to C16 alkynyl group, aryl group, C7 to C13 arylalkyl group, C1 to C4 oxyalkyl group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, Substituted by a substituent selected from a cycloalkyl group, a cycloalkenyl group of C3 to C15, a cycloalkynyl group of C6 to C15, a heterocycloalkyl group and a combination thereof.

In addition, unless otherwise defined herein, "hetero" means containing 1 to 3 heteroatoms of O.

Hereinafter, the light transmitting resin composition will be described.

The light transmissive resin composition according to the embodiment of the present invention includes a polysiloxane having a moiety represented by the following Chemical Formula 1.

[Chemical Formula 1]

* -Si-Ar-Si- *

In Formula 1, Ar is a substituted or unsubstituted C6 to C30 arylene group.

The polysiloxane is a part represented by the formula (2a); A moiety represented by the following Chemical Formula 2b; And at least one of the moieties represented by Formula 2c, Formula 2d, and Formula 2e.

(2a)

(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b

(2b)

R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c

[Chemical Formula 2c]

R ³ SiO _{(3-d) / 2} (OR ^IV ) _d

 (2d)

R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^V ) _e

[Formula 2e]

_{^{R 6 R 7 R 8 SiO 1}} /2

In Formulas 2a to 2e, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, substituted Or an unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C10 hydroxyalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group, a substituted or unsubstituted A C2 to C10 alkenyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a lactone group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, a, b and d is each independently 0-2, and c and e are each independently 0-1.

The polysiloxane may be, for example represented by the following formula (3).

(3)

^{(R 6 R 7 R 8 SiO} 1/2) m [(OR I) a O (3-a) / 2 Si-Ar-SiO (3-b) / 2 (OR II) b] n [R 3 SiO _{(3-d) / 2} (OR ^IV ) _d ] _p [R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c ] _q [R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^III ) _e ] _r

In Formula 3, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted group C3 to C20 cycloalkyl group, substituted or unsubstituted C1 to C10 hydroxyalkyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C20 heteroaryl group, substituted or unsubstituted C2 to C10 Alkenyl group, substituted or unsubstituted C1 to C10 alkoxy group, lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, Ar is a C6 to C30 aryl group A, b and d are each independently 0 to 2, c and e are each independently 0 to 1, and 0 <m <0.9, 0 <n <0.2, 0≤p <0.9, 0 <q < 0.9 and 0 ≦ r <0.9 and m + n + p + q + r = 1.

The polysiloxane may be obtained by polymerizing a silyl monomer having an arylene group and a silicone monomer.

The silyl monomer having an arylene group may be represented by, for example, the following formula (4).

[Chemical Formula 4]

(X ¹ ) ₃ -Si-Ar-Si- (X ² ) ₃

In Formula 4, Ar is a substituted or unsubstituted C6 to C30 arylene group, X ¹ is each independently selected from C1 to C6 alkoxy group, hydroxy group, halogen group, carboxyl group and combinations thereof, X ² is each Independently one selected from a C1 to C6 alkoxy group, a hydroxyl group, a halogen group, a carboxyl group and a combination thereof.

The silicone monomer may be at least one selected from compounds represented by the following Chemical Formula 5, the following Chemical Formula 6, and the following Chemical Formula 7, for example.

[Chemical Formula 5]

SiX ³ X ⁴ R ¹⁴ R ¹⁵

[Chemical Formula 6]

SiX ⁵ X ⁶ X ⁷ R ¹⁶

[Formula 7]

SiX ⁸ X ⁹ X ¹⁰ X ¹¹

In Formulas 5 to 7, R ¹⁴ to R ¹⁶ are each bonded to silicon, and each independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or Unsubstituted C6 to C20 aryl group, substituted or unsubstituted C7 to C20 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C20 heterocycloalkyl group, substituted or unsubstituted A substituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C6 alkoxy group, a substituted or unsubstituted carbonyl group, a hydroxy group or a combination thereof, X ³ to X ¹¹ is each bonded to silicon and is each independently selected from a C1 to C6 alkoxy group, a hydroxy group, a halogen group, a carboxyl group, and a combination thereof.

The silyl monomer and the silicon monomer having the arylene group may be included in about 0.01 to 20% by weight and about 80 to 99.9% by weight, respectively.

When the monomers are polymerized, an end capping reagent may be further included. The terminal protecting agent may be a silicone compound, for example 1,3-divinyltetramethyldisiloxane, chlorodimethylvinylsilane.

The average weight molecular weight of the polysiloxane may be about 800 to 100,000 g / mol, of which may be about 3,000 to 15,000 g / mol.

The polysiloxane may be included in about 50% by weight or more based on the total content of the light-transmissive resin composition, and may be included in about 50 to 99.9% by weight.

The transparent resin composition for the encapsulant may further include a hydrosilylation catalyst in addition to the polysiloxane.

Hydrogensilicon catalysts may include, for example, platinum, rhodium, palladium, ruthenium, iridium or combinations thereof.

Hydrogensilicon catalyst may be included in about 0.1ppm to 1000ppm relative to the total content of the light-transmissive resin composition.

The light transmitting resin composition may further include a polyorganosiloxane represented by the following Formula 8.

[Chemical Formula 8]

^{(R 17 R 18 R 19 SiO} 1/2) M1 (R 20 R 21 SiO 2/2) D1 (R 22 SiO 3/2) T1 (SiO 4/2) Q1

R ¹⁷ to R ²² are each independently hydrogen, a substituted or unsubstituted C1 to C6 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 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C20 heterocycloalkyl group, substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted Or an unsubstituted C1 to C6 alkoxy group, a substituted or unsubstituted carbonyl group, a hydroxy group, or a combination thereof, 0 <M1 <1, 0≤D1 <1, 0≤T1 <1, 0≤Q1 <1 and M1 + D1 + T1 + Q1 = 1. Wherein M1, D1, T1 and Q1 are each molar ratios.

The polyorganosiloxane may be included in less than about 50% by weight based on the total content of the light transmitting resin composition.

The light-transmissive resin composition may further include an adhesion promoter on the above-described component, and the adhesion promoter may be, for example, glycidoxypropyltrimethoxysilane, vinyltriethoxysilane, glycidoxypropyltriethoxysilane, or the like. Can be mentioned.

Another aspect of the present invention provides a sealing material obtained by curing the above-mentioned light-transmissive resin composition.

The encapsulant can be obtained by curing the light-transmissive resin composition comprising a polysiloxane having a moiety represented by the following formula (1).

[Chemical Formula 1]

* -Si-Ar-Si- *

In Formula 1, Ar is a substituted or unsubstituted C6 to C30 arylene group

The polysiloxane is a moiety represented by Chemical Formula 2a as described above; A moiety represented by the following Chemical Formula 2b; And at least one of the moieties represented by Formula 2c, Formula 2d, and Formula 2e.

(2a)

(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b

(2b)

R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c

[Chemical Formula 2c]

R ³ SiO _{(3-d) / 2} (OR ^IV ) _d

(2d)

R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^V ) _e

[Formula 2e]

_{^{R 6 R 7 R 8 SiO 1}} /2

The polysiloxane may be, for example represented by the following formula (3).

(3)

^{(R 6 R 7 R 8 SiO} 1/2) m [(OR I) a O (3-a) / 2 Si-Ar-SiO (3-b) / 2 (OR II) b] n [R 3 SiO _{(3-d) / 2} (OR ^IV ) _d ] _p [R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c ] _q [R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^III ) _e ] _r

In Formulas 2a to 2e and 3, R ^I to R ^V , R ¹ To R ⁸ , a, b, c, d, e, m, n, p, q and r are as defined above.

Another aspect of the invention provides an electronic device comprising a light emitting device, a semiconductor device and an encapsulant surrounding the light emitting device.

The encapsulant may be obtained by curing a light-transmissive resin composition comprising a polysiloxane having a moiety represented by Formula 1 as described above.

[Chemical Formula 1]

* -Si-Ar-Si- *

In Formula 1, Ar is a substituted or unsubstituted C6 to C30 arylene group.

The polysiloxane is a moiety represented by Chemical Formula 2a as described above; A moiety represented by the following Chemical Formula 2b; And at least one of the moieties represented by Formula 2c, Formula 2d, and Formula 2e.

(2a)

(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b

(2b)

R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c

[Chemical Formula 2c]

R ³ SiO _{(3-d) / 2} (OR ^IV ) _d

 (2d)

R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^V ) _e

[Formula 2e]

_{^{R 6 R 7 R 8 SiO 1}} /2

The polysiloxane may be, for example represented by the following formula (3).

(3)

^{(R 6 R 7 R 8 SiO} 1/2) m [(OR I) a O (3-a) / 2 Si-Ar-SiO (3-b) / 2 (OR II) b] n [R 3 SiO _{(3-d) / 2} (OR ^IV ) _d ] _p [R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c ] _q [R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^III ) _e ] _r

In Formulas 2a to 2e and 3, R ^I to R ^V , R ¹ to R ⁸ , a, b, c, d, e, m, n, p, q and r are as described above.

The electronic device may include, for example, a light emitting diode, an organic light emitting device, an optical luminescence, and a solar cell, but is not limited thereto.

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

Polysiloxane  synthesis

Synthetic example  One

1822.5 g (9.998 mole) of phenylmethyldimethoxysilane and 1,4-bis (triethoxysilyl) benzene (1,4-bis) at room temperature (25 ° C.) in a 3 L reactor equipped with a stirrer, condenser and funnel 0.84 g (0.002 mole) of (triethoxysilyl) benzene) was added thereto. To this was added 0.46 g (0.005 mole) (25% solution diluted in water) of tetramethylammonium hydroxide (TMAH) with stirring over 10 minutes. The mixture was then heated to 50 ° C. and 180 g (10 mole) of water was added over 120 minutes. The mixture was then heated to 65 ° C. for 5 hours and then cooled to room temperature. The result was neutralized with acetic acid and washed with water. The resulting polymer was dried in vacuo and 372.8 g (2 mole) of 1,3-divinyltetramethyldisiloxane and 10 g of sulfuric acid (95-98%) were added and stirred at room temperature for 12 hours. The mixture was then washed with water and volatiles removed to give a polymer under reduced pressure.

The structure of the polymer was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is shown in Formula 9, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

[Chemical Formula 9]

_{(SiO 3/2 -Ph-SiO} 3/2) 0.002 (MePhSiO 2/2) 0.955 (ViMe 2 SiO 1/2) 0.043

Synthetic example  2

1821.9 g (9.995 mole) of phenylmethyldimethoxysilane and 2.1 g (0.005 mole) of 1,4-bis (triethoxysilyl) benzene at room temperature (25 ° C.) in a 3 L reactor equipped with a stirrer, condenser and funnel Put it. To this was added 0.46 g (0.005 mole) TMAH (25% solution diluted in water) over 10 minutes with stirring. The mixture was then heated to 50 ° C. and 180 g (10 mole) of water was added over 120 minutes. The mixture was then heated to 65 ° C. for 5 hours and then cooled to room temperature. The result was neutralized with acetic acid and washed with water. The resulting polymer was dried in vacuo and 372.8 g (2 mole) of 1,3-divinyltetramethyldisiloxane and 10 g of sulfuric acid (95-98%) were added and stirred at room temperature for 12 hours. The mixture was then washed with water and volatiles removed to give a polymer under reduced pressure.

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is shown in Formula 10, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical formula 10]

_{(SiO 3/2 -Ph-SiO} 3/2) 0.005 (MePhSiO 2/2) 0.95 (ViMe 2 SiO 1/2) 0.045

Synthetic example  3

1821.0 g (9.99 mole) of phenylmethyldimethoxysilane and 4.2 g (0.01 mole) of 1,4-bis (triethoxysilyl) benzene in a 3 L reactor equipped with a stirrer, a condenser and a funnel at room temperature (25 ° C.) Put it. To this was added 0.46 g (0.005 mole) TMAH (25% solution diluted in water) over 10 minutes with stirring. The mixture was then heated to 50 ° C. and 180 g (10 mole) of water was added over 120 minutes. The mixture was then heated to 65 ° C. for 5 hours and then cooled to room temperature. The result was neutralized with acetic acid and washed with water. The resulting polymer was dried in vacuo and 372.8 g (2 mole) of 1,3-divinyltetramethyldisiloxane and 10 g of sulfuric acid (95-98%) were added and stirred at room temperature for 12 hours. The mixture was then washed with water and volatiles removed to give a polymer under reduced pressure.

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is shown in Formula 11, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 (11)

_{(SiO 3/2 -Ph-SiO} 3/2) 0.01 (MePhSiO 2/2) 0.939 (ViMe 2 SiO 1/2) 0.051

Synthetic example  4

1820.0 g (9.985 mole) of phenylmethyldimethoxysilane and 6.3 g (0.015 mole) of 1,4-bis (triethoxysilyl) benzene in a 3 L reactor equipped with a stirrer, a condenser and a funnel at room temperature (25 ° C.) Put it. To this was added 0.46 g (0.005 mole) TMAH (25% solution diluted in water) over 10 minutes with stirring. The mixture was then heated to 50 ° C. and 180 g (10 mole) of water was added over 120 minutes. The mixture was then heated to 65 ° C. for 5 hours and then cooled to room temperature. The result was neutralized with acetic acid and washed with water. The resulting polymer was dried in vacuo and 372.8 g (2 mole) of 1,3-divinyltetramethyldisiloxane and 10 g of sulfuric acid (95-98%) were added and stirred at room temperature for 12 hours. The mixture was then washed with water and volatiles removed to give a polymer under reduced pressure.

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is shown in Formula 12, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical Formula 12]

_{(SiO 3/2 -Ph-SiO} 3/2) 0.014 (MePhSiO 2/2) 0.94 (ViMe 2 SiO 1/2) 0.046

Synthetic example  5

1093.0 g (6.00 mole) of phenylmethyldimethoxysilane and 5.82 g (0.015 mole) of 1,4-bis (trimethoxysilylethyl) benzene in a 3 L reactor equipped with a stirrer, a condenser and a funnel at room temperature (25 ° C.) ). To this was added 0.17 g (0.003 mole) (25% solution diluted in water) of KOH (potassium hydroxide) with stirring over 10 minutes. The mixture was then heated to 50 ° C. and 108 g (6.02 mole) of water was added over 120 minutes. The mixture was then heated to 65 ° C. for 5 hours and then cooled to room temperature. The result was neutralized with acetic acid and washed with water. The resulting polymer was dried in vacuo, and then 226.8 g (1.2 mole) of 1,3-divinyltetramethyldisiloxane and 6 g of sulfuric acid (95-98%) were added and stirred at room temperature for 12 hours. The mixture was then washed with water and volatiles removed to give a polymer under reduced pressure.

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is shown in Formula 13, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical Formula 13]

_{(SiO 3/2 CH 2 -Ph} -CH 2 SiO 3/2) 0.002 (MePhSiO 2/2) 0.95 (ViMe 2 SiO 1/2) 0.048

Synthetic example  6

1093.0 g (6.00 mole) of phenylmethyldimethoxysilane and 11.24 g (0.03 mole) of 1,4-bis (trimethoxysilylethyl) benzene in a 3 L reactor equipped with a stirrer, a condenser and a funnel at room temperature (25 ° C.) ). To this was added 0.17 g (0.003 mole) of KOH (25% solution diluted in water) over 10 minutes with stirring. The mixture was then heated to 50 ° C. and 108 g (6.02 mole) of water was added over 120 minutes. The mixture was then heated to 65 ° C. for 5 hours and then cooled to room temperature. The result was neutralized with acetic acid and washed with water. The resulting polymer was dried in vacuo, and then 226.8 g (1.2 mole) of 1,3-divinyltetramethyldisiloxane and 6 g of sulfuric acid (95-98%) were added and stirred at room temperature for 12 hours. The mixture was then washed with water and volatiles removed to give a polymer under reduced pressure.

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is shown in Formula 14, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical Formula 14]

_{(SiO 3/2 CH 2 -Ph} -CH 2 SiO 3/2) 0.005 (MePhSiO 2/2) 0.955 (ViMe 2 SiO 1/2) 0.04

Synthetic example  7

1093.0 g (6.00 mole) of phenylmethyldimethoxysilane and 22.47 g (0.06 mole) of 1,4-bis (trimethoxysilylethyl) benzene in a 3L reactor equipped with a stirrer, a condenser and a funnel at room temperature (25 ° C.) ). To this was added 0.17 g (0.003 mole) of KOH (25% solution diluted in water) over 10 minutes with stirring. The mixture was then heated to 50 ° C. and 108 g (6.02 mole) of water was added over 120 minutes. The mixture was then heated to 65 ° C. for 5 hours and then cooled to room temperature. The result was neutralized with acetic acid and washed with water. The resulting polymer was dried in vacuo, and then 226.8 g (1.2 mole) of 1,3-divinyltetramethyldisiloxane and 6 g of sulfuric acid (95-98%) were added and stirred at room temperature for 12 hours. The mixture was then washed with water and volatiles removed to give a polymer under reduced pressure.

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is shown in Formula 15, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical Formula 15]

_{(SiO 3/2 CH 2 -Ph} -CH 2 SiO 3/2) 0.01 (MePhSiO 2/2) 0.945 (ViMe 2 SiO 1/2) 0.045

Synthetic example  8

1093.0 g (6.00 mole) of phenylmethyldimethoxysilane and 33.71 g (0.09 mole) of 1,4-bis (trimethoxysilylethyl) benzene in a 3 L reactor equipped with a stirrer, a condenser and a funnel at room temperature (25 ° C.) ). To this was added 0.17 g (0.003 mole) of KOH (25% solution diluted in water) over 10 minutes with stirring. The mixture was then heated to 50 ° C. and 108 g (6.02 mole) of water was added over 120 minutes. The mixture was then heated to 65 ° C. for 5 hours and then cooled to room temperature. The result was neutralized with acetic acid and washed with water. The resulting polymer was dried in vacuo, and then 226.8 g (1.2 mole) of 1,3-divinyltetramethyldisiloxane and 6 g of sulfuric acid (95-98%) were added and stirred at room temperature for 12 hours. The mixture was then washed with water and volatiles removed to give a polymer under reduced pressure.

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is shown in Formula 16, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical Formula 16]

_{(SiO 3/2 CH 2 -Ph} -CH 2 SiO 3/2) 0.014 (MePhSiO 2/2) 0.936 (ViMe 2 SiO 1/2) 0.05

Synthetic example  9

1093.0 g (6.00 mole) of phenylmethyldimethoxysilane and 44.95 g (0.12 mole) of 1,4-bis (trimethoxysilylethyl) benzene in a 3 L reactor equipped with a stirrer, a condenser and a funnel at room temperature (25 ° C.) ). To this was added 0.17 g (0.003 mole) of KOH (25% solution diluted in water) over 10 minutes with stirring. The mixture was then heated to 50 ° C. and 108 g (6.02 mole) of water was added over 120 minutes. The mixture was then heated to 65 ° C. for 5 hours and then cooled to room temperature. The result was neutralized with acetic acid and washed with water. The resulting polymer was dried in vacuo, and then 226.8 g (1.2 mole) of 1,3-divinyltetramethyldisiloxane and 6 g of sulfuric acid (95-98%) were added and stirred at room temperature for 12 hours. The mixture was then washed with water and volatiles removed to give a polymer under reduced pressure.

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is as shown in Formula 17, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical Formula 17]

_{(SiO 3/2 CH 2 -Ph} -CH 2 SiO 3/2) 0.02 (MePhSiO 2/2) 0.935 (ViMe 2 SiO 1/2) 0.045

Comparative Synthetic Example  One

Polysiloxane was prepared in the same manner as in Synthesis Example 1, except that phenylmethyldimethoxysilane and divinyltetramethyldisiloxane were used in a molar ratio of 96.9: 3.1 without using 1,4-bis (triethoxysilyl) benzene. .

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is shown in Formula 18, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical Formula 18]

_{(MePhSiO 2/2) 0.969 (} ViMe 2 SiO 1/2) 0.031

Comparative Synthetic Example  2

Polysiloxane was prepared in the same manner as in Synthesis Example 1, except that phenylmethyldimethoxysilane and divinyltetramethyldisiloxane were used in a 97.3: 2.7 molar ratio without using 1,4-bis (triethoxysilyl) benzene. .

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is as shown in Formula 19, where Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical Formula 19]

_{(MePhSiO 2/2) 0.973 (} ViMe 2 SiO 1/2) 0.027

Comparative Synthetic Example  3

Polysiloxane was prepared in the same manner as in Synthesis Example 1 except that phenylmethyldimethoxysilane and divinyltetramethyldisiloxane were used in a molar ratio of 97.6: 2.4 without using 1,4-bis (triethoxysilyl) benzene. .

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is shown in Formula 20, wherein Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical Formula 20]

_{(MePhSiO 2/2) 0.976 (} ViMe 2 SiO 1/2) 0.024

Comparative Synthetic Example  4

Polysiloxane was prepared in the same manner as in Synthesis Example 1 except that phenylmethyldimethoxysilane and divinyltetramethyldisiloxane were used in a 98.0: 2.0 molar ratio without using 1,4-bis (triethoxysilyl) benzene. .

The structure of the polysiloxane was confirmed using H-NMR, Si-NMR and elemental analyzer. The structure is as shown in Formula 21, where Me is methyl, Ph is phenyl, Vi is vinyl, Si is silicon, and O is oxygen.

 [Chemical Formula 21]

_{(MePhSiO 2/2) 0.980 (} ViMe 2 SiO 1/2) 0.020

Polysiloxane  Properties

The molecular weight, viscosity, and vinyl group content in the structures of the polysiloxanes according to Synthesis Examples 1 to 9 and Comparative Synthesis Examples 1 to 4 were measured. The molecular weight was measured using gel permeation chromatography, the viscosity was measured using a Brookfield viscometer, and the vinyl group equivalent in the structure was measured using ¹ H NMR.

The results are shown in Table 1.

Molecular Weight (Mw) Viscosity (25 ° C, cP) Vinyl equivalent
(mmol / g) Synthesis Example 1 7,709 7,742 0.51 Synthesis Example 2 8,238 9,963 0.53 Synthesis Example 3 9,462 11,327 0.60 Synthesis Example 4 11,161 14,470 0.54 Synthesis Example 5 5,057 3,205 0.56 Synthesis Example 6 6,195 6,390 0.47 Synthesis Example 7 7,177 8,100 0.53 Synthesis Example 8 8,133 8,900 0.59 Synthesis Example 9 10,945 19,053 0.54 Comparative Synthesis Example 1 7,000 6,000 0.286 Comparative Synthesis Example 2 8,000 7,200 0.250 Comparative Synthesis Example 3 9,000 8,500 0.222 Comparative Synthesis Example 4 11,000 10,000 0.182

Referring to Table 1, polysiloxanes according to Synthesis Examples 1 to 9 have a constant vinyl group equivalent regardless of molecular weight, whereas polysiloxanes according to Comparative Synthesis Examples 1 to 4 show that vinyl group equivalents change as the molecular weight increases. . Therefore, it can be seen that the polysiloxane according to Synthesis Examples 1 to 4 can maintain the vinyl group equivalent constant regardless of molecular weight, and thus the viscosity can be easily adjusted.

Translucency  Resin Composition Preparation-1

Example  One

90 parts by weight of polysiloxane according to Synthesis Example 1 and 10 parts by weight of vinyl-protected polyphenylsilsequioxane (vinyl group content of 1.000 mmol / g) were blended, and hydrogen to vinyl group ratio (H / Vi) was added. Hydrogen capped polyphenylmethylsiloxane (hydrogen content 5.0 mmol / g) was added to maintain 1. After degassing in vacuum to prepare a liquid resin composition.

Example  2

A liquid resin composition was prepared in the same manner as in Example 1, except that polysiloxane according to Synthesis Example 2 was used instead of polysiloxane according to Synthesis Example 1.

Example  3

A liquid resin composition was prepared in the same manner as in Example 1, except that polysiloxane according to Synthesis Example 3 was used instead of polysiloxane according to Synthesis Example 1.

Example  4

A liquid resin composition was prepared in the same manner as in Example 1, except that polysiloxane according to Synthesis Example 4 was used instead of polysiloxane according to Synthesis Example 1.

Comparative Example  One

A liquid resin composition was prepared in the same manner as in Example 1, except that polysiloxane according to Comparative Synthesis Example 1 was used instead of polysiloxane according to Synthesis Example 1.

Comparative Example  2

A liquid resin composition was prepared in the same manner as in Example 1, except that polysiloxane according to Comparative Synthesis Example 2 was used instead of polysiloxane according to Synthesis Example 1.

Comparative Example  3

A liquid resin composition was prepared in the same manner as in Example 1, except that polysiloxane according to Comparative Synthesis Example 3 was used instead of polysiloxane according to Synthesis Example 1.

Comparative Example  4

A liquid resin composition was prepared in the same manner as in Example 1, except that polysiloxane according to Comparative Synthesis Example 4 was used instead of polysiloxane according to Synthesis Example 1.

Translucency  Physical Properties of Resin Compositions-1

In the resin compositions according to Examples 1 to 4 and Comparative Examples 1 to 4, the amount of hydrogen-protected polyphenylmethylsiloxane (HC-PS) added to maintain the hydrogen to vinyl group ratio (H / Vi) at 1 is shown in Table 2 Same as

HC-PS (part by weight) Example 1 8.03 Example 2 8.03 Example 3 8.03 Example 4 8.03 Comparative Example 1 7.15 Comparative Example 2 6.50 Comparative Example 3 6.00 Comparative Example 4 5.28

In addition, the hardness and viscosity of the resin composition according to Examples 1 to 4 and Comparative Examples 1 to 4 are shown in Table 3. The hardness was measured using a Ueshima Brooks hardness tester, and the viscosity was measured using a Brookfield viscometer.

Hardness (Shore A) Viscosity (cP) Example 1 50 1500 Example 2 50 1850 Example 3 51 2130 Example 4 51 2420 Comparative Example 1 48 1700 Comparative Example 2 43 1800 Comparative Example 3 41 1820 Comparative Example 4 39 2000

As shown in Tables 2 and 3, the resin compositions according to Examples 1-4 had a constant content of hydrogen-protected polyphenylmethylsiloxane added when the hydrogen to vinyl group ratio (H / Vi) was kept at 1 , The resin composition according to Comparative Examples 1 to 4 can be seen that the content of the hydrogen-protected polyphenylmethylsiloxane is reduced. In addition, the resin compositions according to Examples 1 to 4 have a nearly constant hardness and a nearly constant rise in viscosity, whereas the resin compositions according to Comparative Examples 1 to 4 have a low hardness and a rise in viscosity is also not constant.

Accordingly, it can be seen that the resin composition according to the embodiments can adjust the viscosity, whereas the resin composition according to the comparative examples is not easy to adjust the viscosity.

Translucency  Resin Composition Preparation-2

Example  5

90 parts by weight of polysiloxane according to Synthesis Example 1, 10 parts by weight of vinyl-protected polyphenylsilsesquioxane (vinyl group content 1.000 mmol / g) and 8.03 parts by weight of hydrogen-protected polyphenylmethylsiloxane (hydrogen content 5.0 mmol / g) After blending, defoaming was performed in vacuo to prepare a liquid resin composition.

Example  6

A liquid resin composition was prepared in the same manner as in Example 5, except that polysiloxane according to Synthesis Example 2 was used instead of polysiloxane according to Synthesis Example 1.

Example  7

A liquid resin composition was prepared in the same manner as in Example 5 except that the polysiloxane according to Synthesis Example 3 was used instead of the polysiloxane according to Synthesis Example 1.

Example  8

A liquid resin composition was prepared in the same manner as in Example 5, except that polysiloxane according to Synthesis Example 4 was used instead of polysiloxane according to Synthesis Example 1.

Comparative Example  5

A liquid resin composition was prepared in the same manner as in Example 5, except that polysiloxane according to Comparative Synthesis Example 1 was used instead of polysiloxane according to Synthesis Example 1.

Comparative Example  6

A liquid resin composition was prepared in the same manner as in Example 5, except that polysiloxane according to Comparative Synthesis Example 2 was used instead of polysiloxane according to Synthesis Example 1.

Comparative Example  7

A liquid resin composition was prepared in the same manner as in Example 5, except that polysiloxane according to Comparative Synthesis Example 3 was used instead of polysiloxane according to Synthesis Example 1.

Comparative Example  8

A liquid resin composition was prepared in the same manner as in Example 5 except for using the polysiloxane according to Comparative Synthesis Example 4 instead of the polysiloxane according to Synthesis Example 1.

Translucency  Physical properties of the resin composition-2

The hydrogen to vinyl group ratio (H / Vi), hardness and viscosity of the resin compositions according to Examples 5 to 8 and Comparative Examples 5 to 8 were measured. Hardness was measured with a Ueshima Brooks hardness meter and viscosity was measured using a Brookfield viscometer. Heat resistance measurement measured the permeability before and after heating each liquid resin composition of Examples 5-8 at 150 degreeC for 1000 hours, and judged heat resistance as the rate of permeability reduction. The transmittance | permeability was measured at 450 nm wavelength using the UV-spectrophotometer (Shimadzu Corporation UV-3600) with respect to each liquid resin composition of Examples 5-8.

The results are shown in Table 4.

H / Vi Hardness (Shore A) Viscosity (cP) Transparency (T%)
@ 450nm, 0 hours
@ 150 ℃ Transparency (T%)
@ 450nm, 1000 hours
@ 150 ℃ Example 5 1.00 50 1500 98.3% 94.1% Example 6 1.00 50 1850 98.2% 94.0% Example 7 1.00 51 2130 98.3% 93.5% Example 8 1.00 51 2420 98.0% 93.0% Comparative Example 5 1.12 53 1310 98.0% 90.3% Comparative Example 6 1.24 56 1400 97.8% 89.5% Comparative Example 7 1.34 59 1750 97.7% 85.3% Comparative Example 8 1.52 65 202 97.7% 82.1%

As shown in Table 4, the resin compositions according to Examples 5 to 8 exhibit a constant hydrogen to vinyl group ratio (H / Vi) relative to a certain amount of hydrogen protected polyphenylmethylsiloxane, while according to Comparative Examples 5 to 8 The resin composition can be seen that the hydrogen-to-vinyl group ratio (H / Vi) changes. Here, the ratio of hydrogen to vinyl group (H / Vi) is a factor for determining physical properties such as hardness and modulus after curing. The resin compositions according to Examples 5 to 8 are easy to control, whereas Comparative Examples 5 to 8 It can be seen that the resin composition according to 8 has difficulty in controlling physical properties.

In addition, while the resin compositions according to Examples 5 to 8 had a nearly constant hardness and a nearly constant rise in viscosity, the resin compositions according to Comparative Examples 5 to 8 had a large change in hardness and a rise in viscosity was also not constant. have. Therefore, it can be seen that the resin composition according to Examples 5 to 8 is easier to control the viscosity while maintaining a constant hardness than the resin composition according to Comparative Examples 5 to 8.

In the case of heat resistance, the transmittance (T%) was observed at 450 nm after 1000 hours at 150 ° C., and compared with the transmittance of the initial resin composition before heating. As a result of observing transmittance (T%) of 450 nm wavelength after 1000 hours at 150 ° C., the resin composition according to Comparative Examples 5 to 8 showed a decrease within 8 to 15% compared to the initial transmittance, whereas according to Examples 5 to 8 The resin composition shows a decrease within 5% of the initial permeability, and it can be seen that the composition has excellent heat resistance by maintaining the initial permeability relatively well even after long exposure at high temperature.

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.

Claims (12)

To include a polysiloxane having a part represented by the formula (1),
The polysiloxane is
A moiety represented by the following Chemical Formula 2a,
The moiety represented by Formula 2b, and
At least one of the moieties represented by the following formula (2c), (2d) and (2e)
Translucent resin composition comprising:
[Chemical Formula 1]
* -Si-Ar-Si- *
(2a)
(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b
(2b)
R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c
[Chemical Formula 2c]
R ³ SiO _{(3-d) / 2} (OR ^IV ) _d
(2d)
R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^V ) _e
[Formula 2e]
R ⁶ R ⁷ R ⁸ SiO _1/2
In Formula 1, Formula 2a to Formula 2e,
Ar is a substituted or unsubstituted C6 to C30 arylene group,
R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycle Alkyl group, substituted or unsubstituted C1 to C10 hydroxyalkyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C20 heteroaryl group, substituted or unsubstituted C2 to C10 alkenyl group, substituted or Unsubstituted C1 to C10 alkoxy group, lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, a, b and d are each independently 0 to 2 C and e are each independently 0 to 1,
Substituted herein means that the hydrogen atom in the compound is a halogen atom, a hydroxy group, an alkoxy group, a carbonyl group, a carbamyl group, an ester group, a carboxyl group or a salt thereof, an alkyl group, an alkenyl group of C2 to C16, an alkynyl group of C2 to C16, an aryl group, or C7 to C13 arylalkyl group, C1 to C4 oxyalkyl group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, cycloalkyl group, C3 to C15 cycloalkenyl group, C6 to C15 cycloalkynyl group, heterocycloalkyl group and Substituted with a substituent selected from a combination thereof.


delete In claim 1,
The polysiloxane is a light transmitting resin composition represented by the following formula (3).
(3)
(R ⁶ R ⁷ R ⁸ SiO _1/2 ) _m [(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b ] _n [R ³ SiO _{(3-d) / 2} (OR ^IV ) _d ] _p [R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c ] _q [R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^III ) _e ] _r
In Formula 3, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted group C3 to C20 cycloalkyl group, substituted or unsubstituted C1 to C10 hydroxyalkyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C20 heteroaryl group, substituted or unsubstituted C2 to C10 Alkenyl group, substituted or unsubstituted C1 to C10 alkoxy group, lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, Ar is a C6 to C30 aryl group A, b and d are each independently 0 to 2, c and e are 0 to 1, 0 <m <0.9, 0 <n <0.2, 0≤p <0.9, 0 <q <0.9 and 0 ≤ r <0.9, m + n + p + q + r = 1,
Substituted herein means that the hydrogen atom in the compound is a halogen atom, a hydroxy group, an alkoxy group, a carbonyl group, a carbamyl group, an ester group, a carboxyl group or a salt thereof, an alkyl group, an alkenyl group of C2 to C16, an alkynyl group of C2 to C16, an aryl group, or C7 to C13 arylalkyl group, C1 to C4 oxyalkyl group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, cycloalkyl group, C3 to C15 cycloalkenyl group, C6 to C15 cycloalkynyl group, heterocycloalkyl group and Substituted with a substituent selected from a combination thereof.
4. The method of claim 3,
The polysiloxane is translucent resin composition is contained in 50% by weight or more based on the total content of the translucent resin composition.
5. The method of claim 4,
The polysiloxane is a light-transmissive resin composition containing 50 to 99.9% by weight relative to the total content of the light-transmissive resin composition.
It is obtained by hardening the translucent resin composition containing polysiloxane which has a part represented by following General formula (1),
The polysiloxane is a part represented by the formula (2a),
The moiety represented by Formula 2b, and
At least one of the moieties represented by Formula 2c, Formula 2d, and Formula 2e:
Encapsulant.
[Chemical Formula 1]
* -Si-Ar-Si- *
(2a)
(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b
(2b)
R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c
[Chemical Formula 2c]
R ³ SiO _{(3-d) / 2} (OR ^IV ) _d
(2d)
R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^V ) _e
[Formula 2e]
R ⁶ R ⁷ R ⁸ SiO _1/2
In Formula 1, Formula 2a to Formula 2e,
Ar is a substituted or unsubstituted C6 to C30 arylene group,
R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycle Alkyl group, substituted or unsubstituted C1 to C10 hydroxyalkyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C20 heteroaryl group, substituted or unsubstituted C2 to C10 alkenyl group, substituted or Unsubstituted C1 to C10 alkoxy group, lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, a, b and d are each independently 0 to 2 C and e are each independently 0 to 1,
Substituted herein means that the hydrogen atom in the compound is a halogen atom, a hydroxy group, an alkoxy group, a carbonyl group, a carbamyl group, an ester group, a carboxyl group or a salt thereof, an alkyl group, an alkenyl group of C2 to C16, an alkynyl group of C2 to C16, an aryl group, or C7 to C13 arylalkyl group, C1 to C4 oxyalkyl group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, cycloalkyl group, C3 to C15 cycloalkenyl group, C6 to C15 cycloalkynyl group, heterocycloalkyl group and Substituted with a substituent selected from a combination thereof.

delete The method of claim 6,
The polysiloxane is an encapsulant represented by the following formula (3).
(3)
(R ⁶ R ⁷ R ⁸ SiO _1/2 ) _m [(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b ] _n [R ³ SiO _{(3-d) / 2} (OR ^IV ) _d ] _p [R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c ] _q [R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^III ) _e ] _r
In Formula 3, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted group C3 to C20 cycloalkyl group, substituted or unsubstituted C1 to C10 hydroxyalkyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C20 heteroaryl group, substituted or unsubstituted C2 to C10 Alkenyl group, substituted or unsubstituted C1 to C10 alkoxy group, lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, Ar is a C6 to C30 aryl group A, b and d are each independently 0 to 2, c and e are 0 to 1, 0 <m <0.9, 0 <n <0.2, 0≤p <0.9, 0 <q <0.9 and 0 ≤ r <0.9, m + n + p + q + r = 1,
Substituted herein means that the hydrogen atom in the compound is a halogen atom, a hydroxy group, an alkoxy group, a carbonyl group, a carbamyl group, an ester group, a carboxyl group or a salt thereof, an alkyl group, an alkenyl group of C2 to C16, an alkynyl group of C2 to C16, an aryl group, or C7 to C13 arylalkyl group, C1 to C4 oxyalkyl group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, cycloalkyl group, C3 to C15 cycloalkenyl group, C6 to C15 cycloalkynyl group, heterocycloalkyl group and Substituted with a substituent selected from a combination thereof.
Light emitting devices, semiconductor devices, and
Encapsulation material surrounding the light emitting element
Lt; / RTI &gt;
The encapsulant is obtained by curing a light-transmissive resin composition comprising a polysiloxane having a portion represented by the following formula (1),
The polysiloxane is a part represented by the formula (2a),
The moiety represented by Formula 2b, and
At least one of the moieties represented by Formula 2c, Formula 2d, and Formula 2e:
Electronic device:
[Chemical Formula 1]
* -Si-Ar-Si- *
(2a)
(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b
(2b)
R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c
[Chemical Formula 2c]
R ³ SiO _{(3-d) / 2} (OR ^IV ) _d
(2d)
R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^V ) _e
[Formula 2e]
R ⁶ R ⁷ R ⁸ SiO _1/2
In Formula 1, Formula 2a to Formula 2e,
Ar is a substituted or unsubstituted C6 to C30 arylene group,
R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycle Alkyl group, substituted or unsubstituted C1 to C10 hydroxyalkyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C20 heteroaryl group, substituted or unsubstituted C2 to C10 alkenyl group, substituted or Unsubstituted C1 to C10 alkoxy group, lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, a, b and d are each independently 0 to 2 C and e are each independently 0 to 1,
Substituted herein means that the hydrogen atom in the compound is a halogen atom, a hydroxy group, an alkoxy group, a carbonyl group, a carbamyl group, an ester group, a carboxyl group or a salt thereof, an alkyl group, an alkenyl group of C2 to C16, an alkynyl group of C2 to C16, an aryl group, or C7 to C13 arylalkyl group, C1 to C4 oxyalkyl group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, cycloalkyl group, C3 to C15 cycloalkenyl group, C6 to C15 cycloalkynyl group, heterocycloalkyl group and Substituted with a substituent selected from a combination thereof.
delete The method of claim 9,
The polysiloxane is an electronic device represented by the following formula (3).
(3)
(R ⁶ R ⁷ R ⁸ SiO _1/2 ) _m [(OR ^I ) _a O _{(3-a) / 2} Si-Ar-SiO _{(3-b) / 2} (OR ^II ) _b ] _n [R ³ SiO _{(3-d) / 2} (OR ^IV ) _d ] _p [R ¹ R ² SiO _{(2-c) / 2} (OR ^III ) _c ] _q [R ⁴ R ⁵ SiO _{(2-e) / 2} (OR ^III ) _e ] _r
In Formula 3, R ^I to R ^V are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, and R ¹ to R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted group C3 to C20 cycloalkyl group, substituted or unsubstituted C1 to C10 hydroxyalkyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C20 heteroaryl group, substituted or unsubstituted C2 to C10 Alkenyl group, substituted or unsubstituted C1 to C10 alkoxy group, lactone group, substituted or unsubstituted carboxyl group, substituted or unsubstituted glycidyl ether group, hydroxy or a combination thereof, Ar is a C6 to C30 aryl group A, b and d are each independently 0 to 2, c and e are each independently 0 to 1, and 0 <m <0.9, 0 <n <0.2, 0≤p <0.9, 0 <q < 0.9 and 0 ≦ r <0.9, m + n + p + q + r = 1,
Substituted herein means that the hydrogen atom in the compound is a halogen atom, a hydroxy group, an alkoxy group, a carbonyl group, a carbamyl group, an ester group, a carboxyl group or a salt thereof, an alkyl group, an alkenyl group of C2 to C16, an alkynyl group of C2 to C16, an aryl group, or C7 to C13 arylalkyl group, C1 to C4 oxyalkyl group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, cycloalkyl group, C3 to C15 cycloalkenyl group, C6 to C15 cycloalkynyl group, heterocycloalkyl group and Substituted with a substituent selected from a combination thereof.
The method of claim 9,
The electronic device includes a light emitting diode, an organic light emitting device, a solar cell and an optical luminescence.