WO2018062513A1 - Ｌｅｄ用封止材組成物 - Google Patents

Ｌｅｄ用封止材組成物 Download PDF

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WO2018062513A1
WO2018062513A1 PCT/JP2017/035565 JP2017035565W WO2018062513A1 WO 2018062513 A1 WO2018062513 A1 WO 2018062513A1 JP 2017035565 W JP2017035565 W JP 2017035565W WO 2018062513 A1 WO2018062513 A1 WO 2018062513A1
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group
carbon atoms
mol
led
organopolysiloxane
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PCT/JP2017/035565
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English (en)
French (fr)
Japanese (ja)
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圭介 首藤
加藤　拓
淳平 小林
正睦 鈴木
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日産化学工業株式会社
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Priority to CN201780057547.7A priority Critical patent/CN109716544B/zh
Priority to KR1020197010081A priority patent/KR102211570B1/ko
Priority to JP2018542951A priority patent/JP6764135B2/ja
Publication of WO2018062513A1 publication Critical patent/WO2018062513A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • C09K3/1018—Macromolecular compounds having one or more carbon-to-silicon linkages
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • 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
    • 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
    • H01L23/293—Organic, e.g. plastic
    • H01L23/296—Organo-silicon 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
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/068—Containing also other elements than carbon, oxygen or nitrogen in the polymer main chain
    • C09K2200/0685—Containing silicon

Definitions

  • the present invention relates to an LED sealing material composition, a cured product obtained by curing the composition, and an LED device in which an LED element is sealed with the cured product.
  • the silicone composition forms a cured product having excellent rubber properties such as weather resistance, heat resistance, hardness, and elongation, it is used for the purpose of protecting LED elements, electrodes, substrates and the like in LED devices. Further, silver or silver-containing alloys having good conductivity are used as electrodes in the LED device, and the substrate may be silver-plated in order to improve luminance.
  • a cured product made of a silicone composition has high gas permeability, and when this is used for a high-brightness LED with high light intensity and large heat generation, discoloration of the sealing material due to corrosive gas in the environment, There exists a subject that the brightness
  • Patent Document 1 discloses (A) a diorganopolysiloxane containing at least two alkenyl groups bonded to a silicon atom, (B) SiO 4/2 units, Vi (R 2 ) 2 SiO 1/2 units, and R 2. 3 Resin-structured organopolysiloxane composed of 3 1/2 SiO units, (C) organohydrogenpolysiloxane containing at least two hydrogen atoms bonded to silicon atoms in one molecule, and (D) platinum group metal catalyst There has been proposed an addition-curable silicone composition containing the above.
  • Patent Document 2 (A) an organopolysiloxane represented by an average unit formula, any (B) a straight chain having at least two alkenyl groups in one molecule and having no silicon-bonded hydrogen atom
  • a curable silicone composition comprising at least an organopolysiloxane, (C) an organopolysiloxane having at least two silicon-bonded hydrogen atoms in one molecule, and (D) a catalyst for hydrosilylation reaction.
  • the curable silicone composition described in Patent Document 2 is an organopolysiloxane that has a high hydrosilylation reactivity and forms a cured product having a low gas permeability, a high reactivity, and a low gas permeability. It is said that a curable silicone composition that forms a cured product and a cured product with low gas permeability are provided.
  • the object of the present invention was made in view of the above circumstances, and is an LED sealing that is excellent in heat-resistant transparency, adhesion to an LED substrate, and that does not corrode silver plating even in a harsh environment of 80 ° C. in a sulfur atmosphere.
  • the object is to provide a material composition, a cured product obtained by curing the composition, and an LED device in which an LED element is sealed with the cured product.
  • an LED encapsulant composition (A) 1 type of alkenyl group having three structural units and bonded to a silicon atom. Linear organopolysiloxane having at least two molecules in the molecule, (B) Linear organopolysiloxane having three structural units and having at least two hydrogen atoms bonded to silicon atoms in one molecule And (C) an organopolysiloxane having a structural unit having a biphenylyl group bonded to a silicon atom, at least one of the organopolysiloxane (A) and the organopolysiloxane (B) in the composition comprising the hydrosilylation reaction catalyst.
  • the LED encapsulant formed from the composition has excellent heat-resistant transparency, adhesion to the LED substrate, and 80 ° C. in a sulfur atmosphere. Cormorant found that silver plating is not corroded even in a severe environment, thereby completing the present invention.
  • the present invention provides the first aspect as follows: (A) a linear organopolysiloxane having three structural units represented by the following formula (1) and having at least two alkenyl groups bonded to silicon atoms in one molecule; (R 1 R 2 R 3 SiO 1/2 ) a (R 4 R 5 SiO 2/2 ) b (R 6 2 SiO 2/2 ) c (1) (Wherein R 1 represents an alkenyl group having 2 to 12 carbon atoms, R 2 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms, and R 3 represents the number of carbon atoms.
  • R 4 represents an aryl group or biphenylyl group having 6 to 20 carbon atoms
  • R 5 represents an aryl group having 6 to 20 carbon atoms or Represents an alkyl group having 1 to 12 carbon atoms
  • two R 6 s represent an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms
  • a, b and c are each an O.D.
  • two R 12 represent an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms
  • a hydrosilylation reaction catalyst wherein at least one of R 4 in the formula (1) and R 10 in the formula (2) represents a biphenylyl group.
  • an aryl group having 6 to 20 carbon atoms is defined as not including a biphenylyl group or a terphenylyl group.
  • R 4 in the formula (1) relates to the LED encapsulant composition according to the first aspect, which represents a phenyl group or a biphenylyl group.
  • R 10 represents a phenyl group or a biphenylyl group, LED encapsulating material composition according to the first aspect or the second aspect in.
  • the present invention relates to the LED encapsulant composition according to any one of the first aspect to the third aspect, further including (D) an adhesion-imparting agent.
  • a 5th viewpoint it is related with the hardened
  • a 6th viewpoint it is related with the LED apparatus by which the LED element was sealed with the hardened
  • the LED encapsulant composition of the present invention is characterized by forming a cured product excellent in heat-resistant transparency, sulfurization resistance and adhesion. Moreover, the LED element sealed with the hardened
  • the LED encapsulant composition of the present invention will be described in detail.
  • the linear organopolysiloxane of component (A) has three structural units represented by the following formula (1), and has at least two alkenyl groups bonded to silicon atoms in one molecule. (R 1 R 2 R 3 SiO 1/2 ) a (R 4 R 5 SiO 2/2 ) b (R 6 2 SiO 2/2 ) c (1)
  • R 1 represents an alkenyl group having 2 to 12 carbon atoms
  • examples of the alkenyl group include vinyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, A dodecenyl group is illustrated, Preferably it is a vinyl group.
  • R 2 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms. When R 2 represents an aryl group, the aryl group may be a phenyl group, a tolyl group, a xylyl group, a naphthyl group.
  • Examples of the substituted group include a phenyl group.
  • R 2 represents an alkyl group
  • the alkyl group may be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl.
  • Examples of the group include a methyl group.
  • R 3 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms.
  • the aryl group includes a phenyl group, a tolyl group, a xylyl group, a naphthyl group.
  • a substituted group is exemplified, and a phenyl group is preferable.
  • R 3 represents an alkyl group
  • the alkyl group may be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl.
  • Examples of the group include a methyl group.
  • R 4 represents an aryl group having 6 to 20 carbon atoms or a biphenylyl group, and the aryl group includes a phenyl group, a tolyl group, a xylyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, and an aryl group thereof.
  • R 4 is preferably a biphenylyl group.
  • R 5 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms, and when R 5 represents an aryl group, as the aryl group, a phenyl group, a tolyl group, a xylyl group, a naphthyl group An anthracenyl group, a phenanthryl group, a pyrenyl group, and an aryl group such as an alkyl group such as a methyl group or an ethyl group, an alkoxy group such as a methoxy group or an ethoxy group, or a halogen atom such as a chlorine atom or a bromine atom.
  • a substituted group is exemplified, and a phenyl group is preferable.
  • R 5 represents an alkyl group
  • the alkyl group may be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl. Examples of the group include a methyl group.
  • R 6 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms, and when R 6 represents an aryl group, the aryl group includes a phenyl group, a tolyl group, a xylyl group, a naphthyl group.
  • An anthracenyl group, a phenanthryl group, a pyrenyl group, and an aryl group such as an alkyl group such as a methyl group or an ethyl group, an alkoxy group such as a methoxy group or an ethoxy group, or a halogen atom such as a chlorine atom or a bromine atom.
  • a substituted group is exemplified, and a phenyl group is preferable.
  • R 6 represents an alkyl group
  • the alkyl group may be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl. Examples of the group include a methyl group.
  • the linear organopolysiloxane of the component (A) may further have a siloxane unit represented by SiO 4/2 as long as the object of the present invention is not impaired.
  • the organopolysiloxane has an alkoxy group bonded to a silicon atom such as a methoxy group, an ethoxy group, or a propoxy group, or a hydroxyl group bonded to a silicon atom bond within a range not impairing the object of the present invention. Also good.
  • R 1 R 2 R 3 SiX 1 Is a raw material for introducing a siloxane unit represented by the formula: R 1 R 2 R 3 SiO 1/2 into organopolysiloxane.
  • R 1 represents an alkenyl group having 2 to 12 carbon atoms
  • R 2 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms
  • R 3 represents An aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms is represented.
  • X 1 represents an alkoxy group, an acyloxy group, a hydroxyl group or a —OSiR 1 R 2 R 3 group.
  • X 1 represents an alkoxy group
  • examples of the alkoxy group include a methoxy group, an ethoxy group, and a propoxy group.
  • X 1 represents an acyloxy group
  • an acetoxy group can be exemplified as the acyloxy group.
  • silane compounds include alkoxysilanes such as dimethylvinylmethoxysilane, dimethylvinylethoxysilane, methylphenylvinylmethoxysilane, and methylphenylvinylethoxysilane, acetoxysilane such as dimethylvinylacetoxysilane, and methylphenylvinylacetoxysilane, dimethyl
  • alkoxysilanes such as dimethylvinylmethoxysilane, dimethylvinylethoxysilane, methylphenylvinylmethoxysilane, and methylphenylvinylethoxysilane
  • acetoxysilane such as dimethylvinylacetoxysilane
  • methylphenylvinylacetoxysilane dimethyl
  • hydroxysilanes such as vinylhydroxysilane and methylphenylvinylhydroxysilane, and 1,3-divinyl-1,1,3,3-tetramethyldisi
  • R 4 R 5 Si (X 2 ) 2 Is a raw material for introducing a siloxane unit represented by the formula: R 4 R 5 SiO 2/2 into an organopolysiloxane.
  • R 4 represents an aryl group or a biphenylyl group having 6 to 20 carbon atoms
  • R 5 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms.
  • X 2 represents an alkoxy group, an acyloxy group, or a hydroxyl group.
  • X 2 represents an alkoxy group
  • examples of the alkoxy group include a methoxy group, an ethoxy group, and a propoxy group.
  • X 2 represents an acyloxy group, as the acyloxy group, acetoxy group and the like.
  • silane compounds include methylphenyldimethoxysilane, methylphenyldiethoxysilane, ethylphenyldimethoxysilane, ethylphenyldiethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, methylbiphenylyldimethoxysilane, methylbiphenylyldiethoxy.
  • Silanes alkoxysilanes such as phenylbiphenylyldimethoxysilane, phenylbiphenylyldiethoxysilane, methylphenyldiacetoxysilane, ethylphenyldiacetoxysilane, diphenyldiacetoxysilane, methylbiphenylyldiacetoxysilane, phenylbiphenylyldiacetoxysilane, etc.
  • alkoxysilanes such as phenylbiphenylyldimethoxysilane, phenylbiphenylyldiethoxysilane, methylphenyldiacetoxysilane, ethylphenyldiacetoxysilane, diphenyldiacetoxysilane, methylbiphenylyldiacetoxysilane, phenylbiphenylyldiacetoxysilane
  • Acetoxysilane, methylphenyldihydroxysilane, ethylphenyldihydroxysilane, diphenyldihydride Kishishiran, methyl biphenylyl dihydroxysilane, hydroxy silanes and phenyl biphenylyl dihydroxysilane are exemplified.
  • R 6 2 Si (X 3 ) 2 Is a raw material for introducing a siloxane unit represented by the formula: R 6 2 SiO 2/2 into an organopolysiloxane.
  • R 6 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms
  • X 3 represents an alkoxy group, an acyloxy group, a halogen atom, or a hydroxyl group.
  • examples of the alkoxy group include a methoxy group, an ethoxy group, and a propoxy group.
  • X 3 represents an acyloxy group, as the acyloxy group, acetoxy group and the like.
  • silane compounds examples include alkoxysilanes such as dimethyldimethoxysilane, dimethyldiethoxysilane, diphenyldimethoxysilane, and diphenyldiethoxysilane, acetoxysilanes such as dimethyldiacetoxysilane and diphenyldiacetoxysilane, dimethyldihydroxysilane, and diphenyldihydroxy. Examples include hydroxysilanes such as silane.
  • the linear organopolysiloxane of component (A) is composed of silane compound (I), silane compound (II), silane compound (III) and, if necessary, other silane compounds, cyclic silicone compounds, or silane oligomers. It is obtained by hydrolysis / condensation reaction in the presence of acid or alkali.
  • Examples of the acid that can be used include hydrochloric acid, acetic acid, formic acid, nitric acid, oxalic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, polyvalent carboxylic acid, trifluoromethanesulfonic acid, and ion exchange resin.
  • alkalis examples include inorganic alkalis such as potassium hydroxide and sodium hydroxide, triethylamine, diethylamine, monoethanolamine, diethanolamine, triethanolamine, aqueous ammonia, tetramethylammonium hydroxide, tetrabutylammonium hydroxide, amino
  • organic base compounds such as alkoxysilane having a group and aminopropyltrimethoxysilane.
  • an organic solvent can be used.
  • the organic solvent that can be used include ethers, ketones, alcohols, acetates, aromatic or aliphatic hydrocarbons, ⁇ -butyrolactone, and mixtures of two or more thereof.
  • Preferred organic solvents include diethyl ether, diisopropyl ether, tetrahydrofuran, 1,4-dioxane, acetone, methyl ethyl ketone, methyl isobutyl ketone, methanol, ethanol, isopropanol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether And propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol mono-t-butyl ether, ⁇ -butyrolactone, pentane, hexane, heptane, toluene and xylene.
  • water or a mixed solution of water and alcohols in order to promote the hydrolysis / condensation reaction of each of the above components.
  • this alcohol methanol, ethanol, and isopropanol are preferable. This reaction is accelerated by heating, and when an organic solvent is used, the reaction is preferably performed at the reflux temperature.
  • the linear organopolysiloxane of component (B) has three structural units represented by the following formula (2), and has at least two hydrogen atoms bonded to silicon atoms in one molecule. (R 7 R 8 R 9 SiO 1/2 ) d (R 10 R 11 SiO 2/2 ) e (R 12 2 SiO 2/2 ) f (2)
  • R 7 represents a hydrogen atom.
  • R 8 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms, and when R 8 represents an aryl group, as the aryl group, a phenyl group, a tolyl group, a xylyl group, a naphthyl group An anthracenyl group, a phenanthryl group, a pyrenyl group, and an aryl group such as an alkyl group such as a methyl group or an ethyl group, an alkoxy group such as a methoxy group or an ethoxy group, or a halogen atom such as a chlorine atom or a bromine atom.
  • a substituted group is exemplified, and a phenyl group is preferable.
  • R 8 represents an alkyl group
  • the alkyl group may be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl. Examples of the group include a methyl group.
  • R 9 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms, and when R 9 represents an aryl group, as the aryl group, a phenyl group, a tolyl group, a xylyl group, a naphthyl group An anthracenyl group, a phenanthryl group, a pyrenyl group, and an aryl group such as an alkyl group such as a methyl group or an ethyl group, an alkoxy group such as a methoxy group or an ethoxy group, or a halogen atom such as a chlorine atom or a bromine atom.
  • a substituted group is exemplified, and a phenyl group is preferable.
  • the alkyl group may be a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group. Examples of the group include a methyl group.
  • R 10 represents an aryl group having 6 to 20 carbon atoms or a biphenylyl group
  • the aryl group includes a phenyl group, a tolyl group, a xylyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, and an aryl group thereof.
  • Examples include a group in which a hydrogen atom is substituted with an alkyl group such as a methyl group or an ethyl group, an alkoxy group such as a methoxy group or an ethoxy group, or a halogen atom such as a chlorine atom or a bromine atom.
  • R 11 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms.
  • the aryl group may be a phenyl group, a tolyl group, a xylyl group, a naphthyl group.
  • a substituted group is exemplified, and a phenyl group is preferable.
  • R 11 represents an alkyl group
  • the alkyl group may be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl.
  • Examples of the group include a methyl group.
  • R 12 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms.
  • the aryl group includes a phenyl group, a tolyl group, a xylyl group, a naphthyl group.
  • a substituted group is exemplified, and a phenyl group is preferable.
  • R 12 represents an alkyl group
  • the alkyl group may be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl.
  • Examples of the group include a methyl group.
  • the organopolysiloxane of the component (B) may have a siloxane unit represented by SiO 4/2 as long as the object of the present invention is not impaired.
  • the organopolysiloxane may have a silicon atom-bonded alkoxy group such as a methoxy group, an ethoxy group, or a propoxy group, or a hydroxyl group bonded to a silicon atom, as long as the object of the present invention is not impaired.
  • R 7 R 8 R 9 SiX 1 Is a raw material for introducing a siloxane unit represented by the formula: R 7 R 8 R 9 SiO 1/2 into the organopolysiloxane.
  • R 7 represents a hydrogen atom
  • R 8 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms
  • R 9 represents a carbon atom having 6 to 20 carbon atoms.
  • An aryl group or an alkyl group having 1 to 12 carbon atoms is represented
  • X 1 represents an alkoxy group, an acyloxy group, a hydroxyl group, or a —OSiR 7 R 8 R 9 group.
  • examples of the alkoxy group include a methoxy group, an ethoxy group, and a propoxy group.
  • examples of the acyloxy group include an acetoxy group.
  • silane compounds include alkoxysilanes such as dimethylmethoxysilane, dimethylethoxysilane, methylphenylmethoxysilane, and methylphenylethoxysilane, acetoxysilanes such as dimethylacetoxysilane and methylphenylacetoxysilane, dimethylhydroxysilane, and methylphenylhydroxy. Examples thereof include hydroxysilane such as silane and 1,1,3,3-tetramethyldisiloxane.
  • R 10 R 11 Si (X 2 ) 2 Is a raw material for introducing a siloxane unit represented by the formula: R 10 R 11 SiO 2/2 into an organopolysiloxane.
  • R 10 represents an aryl group or biphenylyl group having 6 to 20 carbon atoms
  • R 11 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms
  • X 2 represents an alkoxy group, an acyloxy group, or a hydroxyl group.
  • examples of the alkoxy group include a methoxy group, an ethoxy group, and a propoxy group.
  • X 2 represents an acyloxy group, as the acyloxy group, acetoxy group and the like.
  • silane compounds include methylphenyldimethoxysilane, methylphenyldiethoxysilane, ethylphenyldimethoxysilane, ethylphenyldiethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, methylbiphenylyldimethoxysilane, methylbiphenylyldiethoxy.
  • Silanes alkoxysilanes such as phenylbiphenylyldimethoxysilane, phenylbiphenylyldiethoxysilane, methylphenyldiacetoxysilane, ethylphenyldiacetoxysilane, diphenyldiacetoxysilane, methylbiphenylyldiacetoxysilane, phenylbiphenylyldiacetoxysilane, etc.
  • alkoxysilanes such as phenylbiphenylyldimethoxysilane, phenylbiphenylyldiethoxysilane, methylphenyldiacetoxysilane, ethylphenyldiacetoxysilane, diphenyldiacetoxysilane, methylbiphenylyldiacetoxysilane, phenylbiphenylyldiacetoxysilane
  • Acetoxysilane, methylphenyldihydroxysilane, ethylphenyldihydroxysilane, diphenyldihydride Kishishiran, methyl biphenylyl dihydroxysilane, hydroxy silanes and phenyl biphenylyl dihydroxysilane are exemplified.
  • R 12 2 Si (X 2 ) 2 Is a raw material for introducing a siloxane unit represented by the formula: R 12 2 SiO 2/2 into an organopolysiloxane.
  • R 12 represents an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 12 carbon atoms
  • X 2 represents an alkoxy group, an acyloxy group, or a hydroxyl group.
  • examples of the alkoxy group include a methoxy group, an ethoxy group, and a propoxy group.
  • X 2 represents an acyloxy group, as the acyloxy group, acetoxy group and the like.
  • silane compounds examples include alkoxysilanes such as dimethyldimethoxysilane, dimethyldiethoxysilane, diphenyldimethoxysilane, and diphenyldiethoxysilane, acetoxysilanes such as dimethyldiacetoxysilane and diphenyldiacetoxysilane, dimethyldihydroxysilane, and diphenyldihydroxy Examples include hydroxysilanes such as silane.
  • the organopolysiloxane of component (B) is composed of silane compound (IV), silane compound (V), silane compound (VI), and, if necessary, other silane compounds, cyclic silicone compounds, or silane oligomers. It is obtained by hydrolysis / condensation reaction in the presence.
  • Examples of the acid that can be used include hydrochloric acid, acetic acid, formic acid, nitric acid, oxalic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, polyvalent carboxylic acid, trifluoromethanesulfonic acid, and ion exchange resin.
  • R 4 of the silane compound represented by the general formula (II) used in the synthesis of the linear organopolysiloxane of the component (A) and the linear organopolysiloxane of the component (B).
  • At least one of R 10 of the silane compound represented by the general formula (V) represents a biphenylyl group.
  • an organic solvent can be used.
  • the organic solvent that can be used include ethers, ketones, alcohols, acetates, aromatic hydrocarbons, aliphatic hydrocarbons, ⁇ -butyrolactone, and mixtures of two or more thereof.
  • Preferred organic solvents include diethyl ether, diisopropyl ether, tetrahydrofuran, 1,4-dioxane, acetone, methyl ethyl ketone, methyl isobutyl ketone, methanol, ethanol, isopropanol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether And propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol mono-t-butyl ether, ⁇ -butyrolactone, pentane, hexane, heptane, toluene and xylene.
  • water or a mixed solution of water and alcohols in order to promote the hydrolysis / condensation reaction of each of the above components.
  • this alcohol methanol, ethanol, and isopropanol are preferable. This reaction is accelerated by heating, and when an organic solvent is used, the reaction is preferably performed at the reflux temperature.
  • the content of component (B) is such that the silicon-bonded hydrogen atoms in this component are within the range of 0.1 to 5 moles per mole of alkenyl groups in component (A). Yes, and preferably in an amount in the range of 0.5 to 2 moles. This is because if the content of the component (B) is less than the lower limit of the above range, the composition does not sufficiently cure, and if it exceeds the above range, the heat-resistant transparency of the cured product will be adversely affected. The cured product is gradually discolored in a high temperature state, and cannot be used as an LED sealing material. When it is within the above range, the composition is sufficiently cured, exhibits sufficient sulfidation resistance, and the reliability of the LED device manufactured using the composition of the present invention is improved.
  • the component (C) is a hydrosilylation reaction catalyst for accelerating the curing of the composition, and examples thereof include a platinum-based catalyst, a rhodium-based catalyst, and a palladium-based catalyst.
  • the component (C) is preferably a platinum-based catalyst because curing of the composition can be significantly accelerated.
  • the platinum-based catalyst include fine platinum powder, chloroplatinic acid, an alcohol solution of chloroplatinic acid, a platinum-alkenylsiloxane complex, a platinum-olefin complex, and a platinum-carbonyl complex, preferably a platinum-alkenylsiloxane complex. is there.
  • the content of the component (C) is an effective amount for accelerating the curing of the present composition.
  • the total amount of the component (A) and the component (B) is 100 parts by mass in the component (C).
  • the amount of the catalyst metal is preferably in the range of 0.000001 to 0.05 parts by mass, more preferably 0.000001 to 0.03 parts by mass.
  • the amount is preferably in the range of 000001 to 0.01 parts by mass.
  • the organopolysiloxane of component (A) and the organopolysiloxane of component (B), or an organopolysiloxane having a biphenylyl group in one of them it is preferable that the organopolysiloxane having a biphenylyl group in one of them.
  • the organopolysiloxane having a biphenylyl group is contained, the sulfurization resistance of the cured product of the present composition is remarkably improved.
  • the component (D) is preferably an organosilicon compound having at least one alkoxy group bonded to a silicon atom in one molecule.
  • the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a methoxyethoxy group, and a methoxy group is particularly preferable in terms of excellent adhesion to a substrate.
  • Examples of the group other than the alkoxy group bonded to the silicon atom of the organosilicon compound include substituted or unsubstituted monovalent hydrocarbon groups such as alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and halogenated alkyl groups, 3 -Glycidoxyalkyl groups such as glycidoxypropyl group and 4-glycidoxybutyl group, epoxies such as 2- (3,4-epoxycyclohexyl) ethyl group and 3- (3,4-epoxycyclohexyl) propyl group Epoxy group-containing monovalent organic groups such as cyclohexylalkyl group, 4-oxiranylbutyl group, 8-oxiranyloctyl group and the like, and acrylic group-containing monovalent organic groups such as 3-methacryloxypropyl group Examples thereof include a hydrogen atom.
  • This organosilicon compound preferably has an alkenyl group bonded to a silicon atom or a hydrogen atom bonded to a silicon atom. Moreover, since it can provide favorable adhesiveness to various types of substrates, the organosilicon compound preferably has at least one epoxy group-containing monovalent organic group in one molecule.
  • organosilicon compounds include organosilane compounds, organosiloxane oligomers, and alkyl silicates.
  • Examples of the molecular structure of the organosiloxane oligomer or alkyl silicate include linear, partially branched linear, branched, cyclic, and network, particularly linear, branched, and network. Preferably there is.
  • organosilicon compounds examples include 3-glycidoxypropyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, silane compounds such as 3-methacryloxypropyltrimethoxysilane, A siloxane compound having at least one silicon atom-bonded alkenyl group or silicon atom-bonded hydrogen atom and silicon atom-bonded alkoxy group, a silane compound having at least one silicon atom-bonded alkoxy group, or a siloxane compound in one molecule Examples thereof include a mixture of a silicon atom-bonded hydroxyl group and a siloxane compound having at least one silicon atom-bonded alkenyl group, methyl polysilicate, ethyl polysilicate, and epoxy group-containing ethyl polysilicate.
  • the content of the component (D) is not limited, but it adheres favorably to the substrate that is in contact with the curing process, so the components (A), (B), (C)
  • the content is preferably in the range of 0.01 to 10 parts by mass with respect to 100 parts by mass in total of the components.
  • other optional components include 3-butyn-2-ol, 2-methyl-3-butyn-2-ol, 1-pentyn-3-ol, and 3,4-dimethyl-1-pentyne.
  • -3-ol 3-methyl-1-pentyn-3-ol, 3-ethyl-1-pentyn-3-ol, 1-heptin-3-ol, 5-methyl-1-hexyn-3-ol, -Octin-3-ol, 4-ethyl-1-octin-3-ol, 3,5-dimethyl-1-hexyn-3-ol, 3-ethyl-1-heptin-3-ol, 1-ethynyl-1 Alkyne compounds such as cyclohexanol, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5, 7-tetrahexenylcyclo Siloxane compound
  • a phosphor can be contained as another optional component.
  • This phosphor is, for example, yellow made of oxide phosphors, oxynitride phosphors, nitride phosphors, sulfide phosphors, oxysulfide phosphors and the like widely used in LEDs. , Red, green, and blue light emitting phosphors.
  • Oxide-based phosphors include yttrium, aluminum, garnet-based YAG-based green to yellow light-emitting phosphors containing cerium ions, terbium, aluminum, garnet-based TAG-based yellow light-emitting phosphors including cerium ions, and cerium And silicate green to yellow light emitting phosphors containing europium ions.
  • Examples of the oxynitride-based phosphor include silicon, aluminum, oxygen, and nitrogen-based sialon-based red to green light-emitting phosphors containing europium ions.
  • nitride-based phosphors include calcium, strontium, aluminum, silicon, and nitrogen-based casoon-based (CASN and S-CASN) red-emitting phosphors containing europium ions.
  • sulfide-based phosphors include ZnS-based green coloring phosphors including copper ions and aluminum ions.
  • the oxysulfide phosphor is exemplified by a Y 2 O 2 S red light-emitting phosphor containing europium ions.
  • These phosphors may use one kind or a mixture of two or more kinds.
  • the content of the phosphor is not particularly limited, but is within the range of 1 to 20 parts by mass with respect to 100 parts by mass in total of the components (A), (B), and (C). It is preferable.
  • the LED encapsulant composition of the present invention can contain additives as necessary within the range not impairing the object and effect of the present invention in addition to the above components.
  • additives include inorganic fillers, antioxidants, ultraviolet absorbers, thermal light stabilizers, dispersants, antistatic agents, polymerization inhibitors, antifoaming agents, solvents, inorganic phosphors, radical inhibitors, and surface active agents.
  • Agents, conductivity imparting agents, pigments, dyes, metal deactivators are exemplified, and various additives are not particularly limited.
  • the organopolysiloxane of the component (A), the organopolysiloxane of the component (B), and the hydrosilylation reaction catalyst of the component (C) are separated from liquids containing one or more of these components.
  • the LED encapsulant composition according to the present invention may be prepared by mixing a plurality of liquids immediately before use. For example, the first liquid containing the organopolysiloxane (A) and the second liquid containing the organopolysiloxane (B) are prepared separately, and the first liquid The LED encapsulant composition according to the present invention may be prepared by mixing with the second liquid. At least one of the first liquid and the second liquid contains the hydrosilylation reaction catalyst of the component (C).
  • the first liquid preferably contains a hydrosilylation reaction catalyst.
  • the LED encapsulant composition of the present invention can be cured by heating.
  • the temperature for curing the LED sealing material composition of the present invention is preferably about 80 to 200 ° C.
  • the method for the heat treatment is not particularly limited, and examples thereof include a method of using a hot plate or an oven in an appropriate atmosphere, that is, in the atmosphere, an inert gas such as nitrogen, or in a vacuum.
  • the LED encapsulant composition of the present invention can be used for LED encapsulation.
  • the LED element to which the LED encapsulant composition of the present invention can be applied is not particularly limited.
  • the method for applying the LED sealing material composition of the present invention to an LED element is not particularly limited.
  • the LED sealing material composition of the present invention can be used as, for example, an optical lens in addition to LED sealing.
  • the characteristics of the cured product obtained from the LED encapsulant composition of the present invention were measured as follows.
  • the LED encapsulant composition of the present invention was baked in an oven at 100 ° C for 1 hour, and then at 150 ° C, 3 ° C. After baking for a time, a cured product having a thickness of 1 mm was prepared on an alkali-free glass substrate.
  • the LED encapsulant composition of the present invention was applied to an LED substrate provided with a silver-plated electrode, and 100% in an oven. After baking at 1 degreeC for 1 hour, it baked at 150 degreeC for 3 hours, and produced the LED device.
  • Example 1 Component (A), organopolysiloxane P-1 (10 g), component (B), organopolysiloxane P-15 (10 g), and component (C), 1,3-divinyl-1,1,3 A 3-tetramethyldisiloxane complex (amount in which platinum metal was 10 ppm by weight with respect to the entire composition) was mixed to obtain an LED encapsulant composition.
  • Example 2 Component (A) Organopolysiloxane P-2 (10 g), Component (B) Organopolysiloxane P-16 (10 g) and Component (C) 1,3-divinyl-1,1,3 A 3-tetramethyldisiloxane complex (amount in which platinum metal was 10 ppm by weight with respect to the entire composition) was mixed to obtain an LED encapsulant composition.
  • Example 3 Component (A) Organopolysiloxane P-3 (10 g), Component (B) Organopolysiloxane P-17 (10 g) and Component (C) 1,3-divinyl-1,1,3 A 3-tetramethyldisiloxane complex (amount in which platinum metal was 10 ppm by weight with respect to the entire composition) was mixed to obtain an LED encapsulant composition.
  • Example 4 Component (A) Organopolysiloxane P-4 (10 g), Component (B) Organopolysiloxane P-18 (10 g) and Component (C) 1,3-divinyl-1,1,3 A 3-tetramethyldisiloxane complex (amount in which platinum metal was 10 ppm by weight with respect to the entire composition) was mixed to obtain an LED encapsulant composition.
  • Example 5 Component (A) Organopolysiloxane P-5 (10 g), Component (B) Organopolysiloxane P-19 (10 g) and Component (C) 1,3-divinyl-1,1,3 A 3-tetramethyldisiloxane complex (amount in which platinum metal was 10 ppm by weight with respect to the entire composition) was mixed to obtain an LED encapsulant composition.
  • Example 6 Component (A) Organopolysiloxane P-1 (10 g), Component (B) Organopolysiloxane P-28 (10 g) and Component (C) 1,3-divinyl-1,1,3 A 3-tetramethyldisiloxane complex (amount in which platinum metal was 10 ppm by weight with respect to the entire composition) was mixed to obtain an LED encapsulant composition.
  • Example 7 Component (A) Organopolysiloxane P-14 (10 g), Component (B) Organopolysiloxane P-15 (10 g) and Component (C) 1,3-divinyl-1,1,3 A 3-tetramethyldisiloxane complex (amount in which platinum metal was 10 ppm by weight with respect to the entire composition) was mixed to obtain an LED encapsulant composition.
  • the cured products obtained from the LED encapsulant compositions prepared in Examples 1 to 7 are all heat-resistant and transparent, have high sulfidation resistance, and discoloration of the silver substrate. I could't. Moreover, the high adhesiveness with respect to the LED board was shown.
  • the cured product obtained from the composition prepared in Comparative Example 1 did not satisfy all of heat-resistant transparency, sulfidation resistance, and adhesion. Specifically, in Comparative Example 1 using a polyorganosiloxane that does not contain a biphenylyl group, the resistance to sulfuration was insufficient. Therefore, it was judged that it could not be used as a sealing material composition for LED.
  • the LED encapsulant composition of the present invention has heat-resistant transparency and high sulfidation resistance, so that it does not corrode the silver-plated electrode of the LED substrate and exhibits high adhesion to the LED substrate. It turned out that it was suitable as a sealing material of the LED element in an LED device.
  • the LED encapsulant composition of the present invention has heat-resistant transparency and high resistance to sulfurization, it does not corrode the silver-plated electrode of the LED substrate, and exhibits high adhesion to the LED substrate. It is suitable as a sealing material for LED elements in the above, or as a silver plating protective agent for silver electrodes and substrates at liquid crystal edges.

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  • Computer Hardware Design (AREA)
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  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
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