WO2015088163A1 - Composition d'agent d'encapsulation, agent d'encapsulation et dispositif électronique - Google Patents

Composition d'agent d'encapsulation, agent d'encapsulation et dispositif électronique Download PDF

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WO2015088163A1
WO2015088163A1 PCT/KR2014/011363 KR2014011363W WO2015088163A1 WO 2015088163 A1 WO2015088163 A1 WO 2015088163A1 KR 2014011363 W KR2014011363 W KR 2014011363W WO 2015088163 A1 WO2015088163 A1 WO 2015088163A1
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unsubstituted
substituted
group
formula
siloxane compound
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PCT/KR2014/011363
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English (en)
Korean (ko)
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유홍정
김영호
김우한
김하늘
송두리
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삼성에스디아이 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/5403—Silicon-containing compounds containing no other elements than carbon or hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
    • H01L33/52—Encapsulations
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
    • H01L33/52—Encapsulations
    • H01L33/56—Materials, e.g. epoxy or silicone resin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H01L2224/4805—Shape
    • H01L2224/4809—Loop shape
    • H01L2224/48091—Arched
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

Definitions

  • An encapsulant composition an encapsulant, and an electronic device comprising the encapsulant.
  • Light emitting devices such as light emitting diodes (LEDs), organic light emitting diode devices (OLED devices), and photoluminescence devices (PL devices) may be used in home appliances, lighting devices, and display devices. And it is applied in various fields, such as various automation devices.
  • LEDs light emitting diodes
  • OLED devices organic light emitting diode devices
  • PL devices photoluminescence devices
  • These light emitting devices can display inherent colors of light emitting materials such as blue, red, and green in the light emitting unit, and can display white by combining light emitting units displaying different colors.
  • Such light emitting devices generally include an encapsulant of a packaged or encapsulated structure.
  • the encapsulant may protect the light emitting device from external gas and moisture, and may pass light of various wavelengths emitted from the light emitting device to the outside.
  • One embodiment provides an encapsulant composition having improved high temperature properties, mechanical properties, and heat resistance.
  • Another embodiment provides an encapsulant obtained by curing the encapsulant composition.
  • Yet another embodiment provides an electronic device including the encapsulant.
  • composition for an encapsulant comprising at least one first siloxane compound having a silicon-bonded alkenyl group (Si-Vi), and a curing agent of Formula 1 below:
  • A is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 heterocycloalkylene group, a substituted or unsubstituted C2 to C20 alkenylene group , A substituted or unsubstituted C2 to C20 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
  • R 1 , R 2 , R 3 , and R 4 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C2 to C20 heterocycloalkyl group, substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C20 From an alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C1 to C30 acyl group, a hydroxyl group, a halogen, or a combination
  • A may be selected from a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof.
  • R 1 , R 2 , R 3 , and R 4 are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 cycloalkyl group, a substituted or unsubstituted C6 To C20 aryl group, substituted or unsubstituted C2 to C10 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C1 to C10 alkoxy group, hydroxy group, halogen, or these Can be selected from the combination of.
  • the compound of Formula 1 may be selected from compounds represented by the following Chemical Formulas 2 to 5:
  • R a , R b , R c , and R d are the same or different, each independently hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, k is 1 to Is an integer of three.
  • R a , R b , R c , and R d are the same or different, each independently hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, l is 1 to One of the integers of five.
  • R a , R b , R c , and R d are the same or different, each independently hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, m and n are Each independently is one of integers from 0 to 5, and o and p are each independently one of integers from 1 to 5.
  • R a , R b , R c , and R d are the same or different, each independently hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, q is 1 to Is an integer of three.
  • the first siloxane compound may be represented by the following Formula 6.
  • R 5 to R 10 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 arylalkyl group, substituted or unsubstituted C1 to C30 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group , A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 acyl group, a hydroxy group, or a combination thereof,
  • At least one of R 5 to R 10 includes a substituted or unsubstituted alkenyl group
  • 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 C2 to C20 heterocycloalkylene group, a substituted or unsubstituted C6 to C20
  • At least one of the R 5 To R 10 It may include a substituted or unsubstituted C6 to C30 aryl group.
  • the first siloxane compound may be a mixture of a siloxane compound in which D1 is 0, and a siloxane compound in which T1 and T2 are 0.
  • the curing agent of Formula 1 in the composition may be included in less than about 50% by weight relative to the total content of the curing agent and the first siloxane compound, wherein the first siloxane compound is the total content of the curing agent and the first siloxane compound Greater than about 50% by weight relative to the total weight of the composition.
  • the encapsulant composition may further include a second siloxane compound represented by Formula 7 below.
  • 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 arylalkyl group, substituted or unsubstituted C1 to C30 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group , A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 acyl group, a hydroxy group or a combination thereof,
  • At least one of R 11 to R 16 includes hydrogen
  • Y 2 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 ethylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,
  • the second siloxane compound represented by Chemical Formula 7 may be included in the range of 5% by weight to 95% by weight based on the weight of the curing agent of Chemical Formula 1.
  • the total content of the curing agent and the second siloxane compound is less than 50% by weight based on the total content of the first siloxane compound, the curing agent, and the second siloxane compound, wherein the first siloxane compound is the Greater than 50% by weight based on the total content of the first siloxane compound, the curing agent, and the second siloxane compound.
  • an encapsulant obtained by curing the encapsulant composition is provided.
  • an electronic device including the encapsulant is provided.
  • an encapsulant obtained by curing the encapsulant composition is provided.
  • an electronic device including the encapsulant is provided.
  • composition for an encapsulant including the curing agent of Formula 1 has an effect of remarkably improving the mechanical properties, heat resistance, and high temperature properties of the encapsulant obtained by curing it.
  • FIG. 1 is a schematic cross-sectional view of a light emitting diode according to an embodiment.
  • '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 nitro group, a cyano group, an amino group, an azido group, an amino group Dino group, hydrazino group, hydrazono group, carbonyl group, carbamyl group, thiol group, ester group, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 C20 to C20 alkynyl group, C6 to C30 aryl group, C7 to C30 arylalkyl group, C1 to C30 alkoxy group, C1 to C20 heteroalkyl group, C3 to C20 heteroarylalkyl group, C3 to C30 cycloalkyl group, C
  • hetero means containing 1 to 3 heteroatoms selected from N, O, S and P.
  • composition for an encapsulant comprising at least one first siloxane compound having a silicon-bonded alkenyl group (Si-Vi), and a curing agent of Formula 1 below:
  • A is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,
  • R 1 , R 2 , R 3 , and R 4 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C2 to C20 heterocycloalkyl group, substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C20 Selected from an alkynyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C1 to C10 alkoxy group, substituted or unsubstituted C1 to C30 acyl group, hydroxy group, halogen, or a combination thereof do.
  • the encapsulant is a material having the property of protecting the LED chip and the phosphor from external air, moisture, contaminants, in particular, sulfur compounds, etc., and emitting light to various wavelengths generated therefrom.
  • the external contaminant penetrates through the encapsulant, thereby causing the metal material to corrode and discolor, thereby reducing the brightness and light transmittance of the optical component.
  • the primary protection is possible only if it has a physical hardness, and the improvement of the hardness and the film density are additionally involved in the improvement of the moisture permeability and gas permeability of the encapsulant. Therefore, it is due to the improvement of reliability (discoloration resistance and chemical resistance) which are important physical properties of the encapsulant.
  • a curing agent of Formula 1 has been found to confer properties and low permeability.
  • the sealing material is manufactured using the silicone resin composition containing such a curing agent, the discoloration of the sealing material does not occur even in an operation test under a contaminant exposure condition, and the curable organo silicone resin composition with less reduction in the LED package brightness. It has been found that the present invention can be provided.
  • the encapsulant composition including the curing agent of Chemical Formula 1 has excellent physical strength with respect to various organic resin substrates and compatibility with existing silicone-based compositions, and the backbone in the silicone encapsulant composition is not a simple siloxane repeating unit. By introducing a silicon-carbon repeating unit has the advantage of improving the mechanical properties.
  • the curing agent of Formula 1 is a novel curing agent, and the curable organosiloxane composition containing the curing agent has excellent hardness for various organic resin substrates and can form a dense structure, thereby lower gas permeability and superior mechanical strength than existing curing agents of siloxane structure. It is characterized by showing physical properties.
  • the encapsulant including the composition according to the embodiment is a structure capable of replacing a phenyl group in a more stable form than the conventional curing agent structure, it is suitable to form a cured product having a high heat resistance while maintaining a high refractive index. While this curable organosiloxane composition has a dense structure, as demonstrated by the examples described below, it has a high hardness and low gas permeability, and at the same time the effect of increasing the adhesion, additionally lower coefficient of thermal expansion, and low modulus It shows that cracks and peeling off after curing is reduced.
  • a of Formula 1 is a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof Can be selected.
  • R 1 , R 2 , R 3 , and R 4 are each independently hydrogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 cycloalkyl group, substituted Or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C10 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C1 to C10 alkoxy group, hydroxy group , Halogen, or a combination thereof.
  • the compound of Formula 1 may be selected from compounds represented by the following Formula 2 to Formula 5:
  • R a , R b , R c , and R d are the same or different, each independently hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, k is 1 to Is an integer of three.
  • R a , R b , R c , and R d are the same or different, each independently hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, l is 1 to One of the integers of five.
  • R a , R b , R c , and R d are the same or different, each independently hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, m and n are Each independently is one of integers from 0 to 5, and o and p are each independently one of integers from 1 to 5.
  • R a , R b , R c , and R d are the same or different, each independently hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C5 alkyl group or a substituted or unsubstituted C6 to C10 aryl group, q is 1 to 3 Is one of the integers.
  • the curing agent of Formula 1 and Formula 2 to Formula 5 has silicon-bonded hydrogen (Si-H)
  • the silicon-bonded hydrogen (Si-H) has the silicon-bonded alkenyl group (Si-Vi) React with the silicon-bonded alkenyl groups of at least one first siloxane compound.
  • the first siloxane compound and the curing agent of Chemical Formula 1 may undergo a hydrogen siliconization reaction, thus forming a denser polysiloxane structure with a higher molecular weight when curing the encapsulant composition, thereby forming a light emitting device from external moisture and gas. Can protect.
  • At least one first siloxane compound having the silicon-bonded alkenyl group (Si-Vi) may be represented by the following Chemical Formula 6.
  • R 5 to R 10 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 arylalkyl group, substituted or unsubstituted C1 to C30 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group , A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 acyl group, a hydroxy group, or a combination thereof,
  • At least one of R 5 to R 10 includes a substituted or unsubstituted alkenyl group
  • 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 C2 to C20 heterocycloalkylene group, a substituted or unsubstituted C6 to C20
  • the first siloxane compound is a compound having a silicon-bonded alkenyl group (Si-Vi), for example, may have an average of two or more silicon-bonded alkenyl groups (Si-Vi) per molecule.
  • the silicon-bonded alkenyl group (Si-Vi) may react with hydrogen located at the terminal of the hardener of Chemical Formula 1.
  • the first siloxane compound is, for example, a monomer represented by R 5 R 6 R 7 SiZ 11 , a monomer represented by R 8 R 9 SiZ 12 Z 13 , a monomer represented by R 10 SiZ 14 Z 15 Z 16 , Z 17 Z At least one selected from a monomer represented by 18 Z 19 Si-Y 1 -SiZ 20 Z 21 Z 22 and a monomer represented by SiZ 23 Z 24 Z 25 Z 26 can be obtained by hydrolysis and polycondensation.
  • the definitions of R 5 to R 10 are as described above, and Z 11 to Z 26 are each independently a C1 to C6 alkoxy group, a hydroxyl group, a halogen group, a carboxyl group, or a combination thereof.
  • At least one of the R 5 To R 10 may include a substituted or unsubstituted C6 to C30 aryl group.
  • the refractive index of the encapsulant including the first siloxane compound may be increased to ensure optical characteristics.
  • the first siloxane compound may be used alone or in combination of two or more thereof.
  • the first siloxane compound may be a mixture of a siloxane compound having D 1 of 0 and a siloxane compound having T 1 and T 2 of 0.
  • the curing agent of Formula 1 in the composition may be included in less than about 50% by weight relative to the total content of the curing agent and the first siloxane compound, wherein the first siloxane compound is the total content of the curing agent and the first siloxane compound Greater than about 50% by weight relative to the total weight of the composition.
  • the encapsulant composition may further include a second siloxane compound represented by Formula 7 below.
  • 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 arylalkyl group, substituted or unsubstituted C1 to C30 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group , A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 acyl group, a hydroxy group or a combination thereof,
  • At least one of R 11 to R 16 includes hydrogen
  • Y 2 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 ethylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, or a combination thereof,
  • the second siloxane compound is a compound having silicon-bonded hydrogen (Si-H), and may have, for example, two or more silicon-bonded hydrogens (Si-H) per molecule.
  • the silicon-bonded hydrogen (Si-H) may react with the silicon-bonded alkenyl group (Si-Vi) of the first siloxane compound.
  • the second siloxane compound is, for example, a monomer represented by R 11 R 12 R 13 SiZ 27 , a monomer represented by R 14 R 15 SiZ 28 Z 29 , a monomer represented by R 16 SiZ 30 Z 31 Z 32 , and Z 33 Z At least one selected from a monomer represented by 34 Z 35 Si-Y 1 -SiZ 36 Z 37 Z 38 and a monomer represented by SiZ 39 Z 40 Z 41 Z 42 can be obtained by hydrolysis and polycondensation.
  • the definitions of R 11 to R 16 are as described above, and Z 27 to Z 42 are each independently a C1 to C6 alkoxy group, a hydroxy group, a halogen group, a carboxyl group, or a combination thereof.
  • At least one of the R 11 to R 16 may include a substituted or unsubstituted C6 to C30 aryl group. Accordingly, the refractive index of the encapsulant including the second siloxane compound may be increased to ensure optical characteristics.
  • the second siloxane compound represented by Chemical Formula 7 may be included in the range of 5% by weight to 95% by weight based on the weight of the curing agent of Chemical Formula 1.
  • the total content of the curing agent and the second siloxane compound is less than about 50% by weight based on the total content of the first siloxane compound, the curing agent, and the second siloxane compound, wherein the first siloxane compound is It is included in more than 50% by weight based on the total content of the first siloxane compound, the curing agent, and the second siloxane compound.
  • the weight average molecular weight of the first siloxane and the second siloxane compound may be about 100 to 30,000 ⁇ g / mol, respectively.
  • the encapsulant 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 combinations thereof.
  • the encapsulant composition may further include a hydrogen siliconization catalyst.
  • the hydrogen silicide catalyst includes the first siloxane, the curing agent of Formula 1, and the second siloxane
  • the hydrogen silicide reaction of the first siloxane, the curing agent, and the second siloxane may be promoted.
  • the hydrogen siliconization catalyst may be included in about 0.1 ppm to 1000 ppm relative to the total content of the encapsulant composition.
  • the encapsulant composition may be used as an encapsulant by curing by heat treatment at a predetermined temperature.
  • the encapsulant may be applied to electronic devices such as light emitting diodes and organic light emitting devices.
  • FIG. 1 is a schematic cross-sectional view of a light emitting diode according to an embodiment.
  • the light emitting diode may include a mold 110; A lead frame 120 disposed in 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 LED chip 140 to each other; The encapsulant 200 covering the light emitting diode chip 140 is included.
  • the encapsulant 200 is obtained by curing the encapsulant composition described above.
  • the encapsulant 200 may be formed from the encapsulant composition described above to effectively protect the LED chip 140 and prevent the performance of the LED from deteriorating.
  • the phosphor 190 may be dispersed in the encapsulant 200.
  • the phosphor 190 includes a material that is stimulated by light to emit light of its own wavelength range, and broadly also 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 two or more kinds thereof may be mixed.
  • the phosphor 190 may display a color of a predetermined wavelength region by light supplied from the light emitting diode chip 140, which is a light emitting unit, and the light emitting diode chip 140 may have a shorter wavelength region than the color displayed by the phosphor 190.
  • the color of the can be displayed. For example, when the phosphor 190 displays red, the LED chip 140 may supply blue or green light, which is a shorter wavelength region than the red.
  • the white color may be displayed by combining the color emitted from the light emitting diode chip 140 and the color emitted from the phosphor 190.
  • the electronic device may display white by combining blue, red, and green.
  • the phosphor 190 may be omitted.
  • the siloxane compound obtained in Synthesis Example 1 and the siloxane compound obtained in Synthesis Example 2 are mixed in a weight ratio as shown in Table 1 below, and the first compound includes two kinds of compounds having a silicon-bonded alkenyl group (Si-Vi) at the terminal.
  • the siloxane compound includes two kinds of compounds having a silicon-bonded alkenyl group (Si-Vi) at the terminal.
  • the siloxane compound As a curing agent, a mixture including the compounds represented by the following formulas (8) to (11) in the same amounts as in Table 1 is prepared (mixtures of Examples 1 to 4, respectively).
  • a mixture comprising a mixture of the compound of formula 8 and the siloxane compound of formula 7a obtained in Synthesis Example 3 as a curing agent in the amount shown in Table 1 is prepared (mixture of Example 5 ).
  • a mixture including the siloxane compound of Formula 7a obtained in Synthesis Example 3 as a curing agent in the first siloxane compound without the compound represented by the following Formulas 8 to 11 as a curing agent (comparatively) A mixture of Example 1).
  • the viscosity and refractive index of the prepared encapsulant composition were measured in the same manner as described below, and each composition was prepared as an encapsulant through curing at 120 ° C. for 30 minutes and 170 ° C. for 1 hour, and then the hardness of each encapsulant. (shorer A and shore D), modulus, thermal shock characteristics, moisture permeability, and gas permeability, respectively, were measured using the same method as described below, and the results are shown together in Table 1 below.
  • Viscosity was determined based on the viscosity at 90% of Torque at 23 ° C using a Brookfield (DV-II + pro) spindle No. 52.
  • Refractive Index The mixture of liquid phases before curing was measured under a D-line (589 nm) wavelength using an Abbe refractometer.
  • the hardness is a polysiloxane composition according to Examples 1 to 5 and Comparative Example 1 in a mold (2.5 cm x 7.5 cm x 1 cm) coated with Teflon for 2 hours at 150 ° C. After heat curing, the mixture was cooled to room temperature and the hardness was measured using a Shore A hardness tester.
  • Modulus is a polysiloxane composition according to Examples 1 to 5 and Comparative Example 1 in a teflon-coated mold (35 mm (width) x 10 mm (length) x 4 mm (thickness)) for 2 hours at 150 ° C. After thermosetting, the temperature was cooled to room temperature, and the elastic modulus at 125 ° C. was recorded by measuring a temperature increase rate of 2 ° C./min at ⁇ 50 ° C. to 150 ° C. using DMA (Dynamic Mechanical Analysis) equipment.
  • DMA Dynamic Mechanical Analysis
  • Adhesive force was measured by the following method.
  • -Moisture permeability and gas permeability The encapsulant is produced in the form of a film using a mold and cured at 130 ° C / 5 minutes and 170 ° C / 4 hours, and then moisture permeability (ASTM F-1249) / permeability (ASTM D-) of MOCON 3985) was measured using equipment.
  • the viscosity of the encapsulant composition can be adjusted by only changing the type of the curing agent, that is, the structure of the curing agent, without adjusting the content of the siloxane compound having the T structure, that is, the siloxane compound according to Synthesis Example 1. . It can be seen that the refractive indices of the encapsulant compositions of Examples 1 to 5 and Comparative Example 1 are all higher than 1.5.
  • the hardness, modulus, and thermal shock characteristics of the prepared encapsulant were measured.
  • the hardness (Shore A and Shore D) of the encapsulant of Examples 1 to 5 including the curing agent of Formula 8 to Formula 11 is generally higher or equivalent to the hardness of the encapsulant of Comparative Example 1 Level, and the modulus can be seen that the encapsulant according to Examples 1 to 5 is much lower than the encapsulant of Comparative Example 1.
  • the composition for the encapsulant including the curing agent according to the embodiment of the present invention the viscosity in the liquid phase before curing is relatively high, when it is cured to produce the encapsulant, the film density is higher and the hardness is made of encapsulant It can be seen that.
  • the encapsulant serves to protect the light emitting device, and therefore, it can be said that the increase in mechanical properties such as hardness meets the first requirement that the encapsulant can protect the light emitting device.
  • modulus modulus
  • the encapsulant according to Examples 1 to 5 has a significantly lower modulus than the encapsulant of Comparative Example 1. This is consistent with the thermal shock test results for these encapsulants. That is, in the case of the encapsulant according to Examples 1 to 5, all 100 of the 100 light emitting elements were operable after 1000 cycles, whereas the light emitting element including the encapsulant according to Comparative Example 1 was 1000 cycles. After that, only 65 light emitting devices of the total 100 appear to operate, and it can be seen that the thermal shock characteristics are about 35% lower than those of the encapsulants of Examples 1 to 5.
  • an increase in the viscosity of the liquid encapsulant composition results in an increase in the film density, which has an effect of effectively preventing the encapsulant from introducing moisture or gas from the outside.
  • the moisture permeability of the encapsulant according to Examples 1 to 5 is significantly lower than that of the encapsulant of Comparative Example 1, and the gas permeability is also significantly low. That is, when using a curing agent having a silicon-carbon bond of the formula 8 to 11, not only does not merely increase the mechanical properties such as hardness due to the increase in film density, but also can significantly reduce moisture and gas permeability, It can be seen that it is suitable for use as an encapsulant for the prevention of contaminants from.
  • the encapsulant composition according to the embodiment of the present invention has excellent hardness and mechanical properties, and a water and oxygen permeability reduction effect, and thus, adhesives, binders, and protective agents for electronic devices, electronic parts, electrical devices, and electrical parts. It can be used as a coating agent, an underfiller, etc., in particular, the cured product of the composition is characterized by having a high refractive index and a high light transmittance, such as sealants, adhesives, binders, coatings, It can be used as an underfiller or the like. As a preferred embodiment, the composition of the present invention is suitable for use as an encapsulant such as an LED display.

Abstract

L'invention concerne: une composition d'agent d'encapsulation contenant au moins un type d'un premier composé siloxane ayant un groupe alcényle lié à du silicium (Si-Vi) et un composé carbonsilane comprenant de l'hydrogène lié à du silicium (Si-H) en tant qu'agent de durcissement; un agent d'encapsulation obtenu par durcissement de la composition d'agent d'encapsulation; et un dispositif électronique incluant l'agent d'encapsulation.
PCT/KR2014/011363 2013-12-09 2014-11-25 Composition d'agent d'encapsulation, agent d'encapsulation et dispositif électronique WO2015088163A1 (fr)

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KR20120078606A (ko) * 2010-12-31 2012-07-10 제일모직주식회사 봉지재 및 상기 봉지재를 포함하는 전자 소자
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KR20040052362A (ko) * 2002-12-16 2004-06-23 제일모직주식회사 반도체 봉지용 실리콘 수지 조성물
JP2004339482A (ja) * 2003-04-23 2004-12-02 Shin Etsu Chem Co Ltd 硬化性シリコーン樹脂組成物
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KR20120078606A (ko) * 2010-12-31 2012-07-10 제일모직주식회사 봉지재 및 상기 봉지재를 포함하는 전자 소자
KR20120139614A (ko) * 2011-06-17 2012-12-27 주식회사 엘지화학 경화성 조성물

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