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WO2015115340A1 - Composition de matériau polysilsesquioxane de scellement pour del uv et utilisation de solvant à cet effet - Google Patents

Composition de matériau polysilsesquioxane de scellement pour del uv et utilisation de solvant à cet effet Download PDF

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Publication number
WO2015115340A1
WO2015115340A1 PCT/JP2015/051942 JP2015051942W WO2015115340A1 WO 2015115340 A1 WO2015115340 A1 WO 2015115340A1 JP 2015051942 W JP2015051942 W JP 2015051942W WO 2015115340 A1 WO2015115340 A1 WO 2015115340A1
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WIPO (PCT)
Prior art keywords
polysilsesquioxane
solvent
group
sealing material
led
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Ceased
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PCT/JP2015/051942
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English (en)
Japanese (ja)
Inventor
岳 吉川
高島　正之
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10H—INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
    • H10H20/00—Individual inorganic light-emitting semiconductor devices having potential barriers, e.g. light-emitting diodes [LED]
    • H10H20/80—Constructional details
    • H10H20/85—Packages
    • H10H20/852—Encapsulations
    • H10H20/854—Encapsulations characterised by their material, e.g. epoxy or silicone resins

Definitions

  • the present invention relates to a polysilsesquioxane-based encapsulant composition for UV-LED and the use of a solvent therefor.
  • the polysilsesquioxane-based sealing material composition is used for sealing elements contained in UV-LEDs.
  • a solvent for a polysilsesquioxane-based encapsulant composition for UV-LEDs particularly an encapsulant composition suitable for encapsulating a device that emits light in the UV-C region (200-280 nm) provide.
  • the present invention includes the inventions described in [1] and [2] below.
  • [1] Use of the following solvent a as a solvent for a polysilsesquioxane-based encapsulant for UV-LED, wherein the cured product has a light transmittance at 260 nm of 65% or more;
  • a polysilsesquioxane encapsulant composition for UV-LED comprising a polysilsesquioxane encapsulant and the following solvent a.
  • solvent a A solvent having an ester bond and / or an ether bond, having no hydroxy group, and having a boiling point under 1 atm of 100 ° C. or higher and 200 ° C. or lower
  • the present invention provides a polysilsesquioxane-based encapsulant composition suitable for encapsulating an element that emits light in the ultraviolet region (particularly the UV-C region) and the use of a solvent therefor.
  • FIG. 1 shows the results of measuring the ultraviolet-visible transmittance of the cured product obtained in Example 1.
  • polysilsesquioxane-based sealing material for example, Amax Co., Ltd. website “polysilsesquioxane / T-resin” ⁇ URL: http: // www. azmax. co. jp / cnt_catalog_chemical / pdf / attach — 201010517 — 135825. pdf> and the like.
  • Examples of the polysilsesquioxane-based sealing material include a sealing material containing the resin A having an organopolysiloxane structure represented by the formula (1).
  • each R 1 independently represents an alkyl group
  • each R 2 independently represents an alkoxy group, an alkenyl group, a hydrogen atom, or a hydroxyl group
  • p 1 , q 1 , a 1 , and b 1 are [P 1 + b 1 ⁇ q 1 ]:
  • [a 1 ⁇ q 1 ] 1: represents a positive number that satisfies 0.25 to 9.
  • the oligomer B which has the organopolysiloxane structure represented by Formula (2) may be included.
  • the alkyl group represented by R 1 may be linear or branched, and may have a cyclic structure, but may be a linear or branched alkyl group. Are preferable, and a linear alkyl group is more preferable.
  • the number of carbon atoms of the alkyl group is not limited, but is preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 3, and particularly preferably 1.
  • R 2 independently represents an alkoxy group, an alkenyl group, a hydrogen atom, or a hydroxyl group, preferably an alkoxy group or a hydroxyl group.
  • the alkoxy group may be linear or branched, and may have a cyclic structure, but may be linear or branched. Are more preferable, and a linear alkoxy group is more preferable.
  • the number of carbon atoms of the alkoxy group is not limited, but is preferably 1 to 3, more preferably 1 to 2, and particularly preferably 1.
  • R 2 is an alkenyl group
  • the alkenyl group may be linear or branched, and may have a cyclic structure, but may be linear or branched. Are more preferable, and a linear alkenyl group is more preferable. Further, the number of carbon atoms of the alkenyl group is not limited, but 2 to 4 is preferable.
  • the alkenyl group represented by R 1 is preferably a vinyl group (ethenyl group), an allyl group (2-propenyl group), a 1-propenyl group, an isopropenyl group, or a butenyl group, and more preferably a vinyl group. preferable.
  • the plurality of R 1 and R 2 may be the same type of group or different from each other.
  • the resin A has at least one selected from the group consisting of a methyl group and an ethyl group as R 1 , and R 2 from the group consisting of a methoxy group, an ethoxy group, an isopropoxy group, and a hydroxyl group Those having one or more selected are preferable, R 1 has one or more selected from the group consisting of a methyl group and an ethyl group, and R 2 has a methoxy group, an ethoxy group, And those having one or more selected from the group consisting of isopropoxy groups and a hydroxyl group are more preferred.
  • the weight average molecular weight (Mw) of the resin A is usually 1500 or more and 8000 or less. When the weight average molecular weight of the resin A satisfies this range, the moldability at the time of curing is improved.
  • the weight average molecular weight of the resin A is preferably 1500 or more and 7000 or less, and more preferably 2000 or more and 5000 or less.
  • Resin A can be synthesized using, for example, an organosilicon compound having a functional group capable of forming a siloxane bond corresponding to each of the above-described repeating units. Examples of the “functional group capable of generating a siloxane bond” include a halogen atom, a hydroxyl group, and an alkoxy group.
  • organosilicon compound examples include organotrihalosilane and organotrialkoxylane.
  • Resin A can be synthesized by reacting these starting materials by a hydrolysis-condensation method at a ratio corresponding to the abundance ratio of each repeating unit.
  • resin A those commercially available as a silicone resin or an alkoxy oligomer can also be used.
  • the oligomer B has at least one selected from the group consisting of a methyl group and an ethyl group as R 1 , and R 2 is selected from the group consisting of a methoxy group, an ethoxy group, an isopropoxy group, and a hydroxyl group
  • R 1 has a methyl group
  • R 2 has a methoxy group or a hydroxyl group, and more preferably.
  • the weight average molecular weight of the oligomer B is usually less than 1500. When the weight average molecular weight of the oligomer B satisfies such a range, the moldability at the time of curing is improved.
  • the weight average molecular weight of the oligomer B is preferably 200 or more and less than 1500, and more preferably 250 to 1000.
  • the oligomer B can be synthesized using, for example, an organosilicon compound having a functional group capable of generating a siloxane bond corresponding to each of the above-described repeating units constituting the oligomer B. “Functional group capable of forming a siloxane bond” has the same meaning as described above. Examples of organosilicon compounds include organotrihalosilanes and organotrialkoxylanes.
  • the oligomer B can be synthesized by reacting these starting materials at a ratio corresponding to the abundance ratio of each repeating unit by a hydrolytic condensation method.
  • the difference in weight average molecular weight from the resin A can be controlled, for example, by controlling the reaction temperature at the time of subjecting the starting material to hydrolysis condensation reaction, the addition rate of the starting material into the reaction system, and the like.
  • the oligomer B those commercially available as a silicone resin, an alkoxy oligomer and the like can also be used.
  • the weight average molecular weights of the resin A and the oligomer B can be measured using polystyrene as a standard using a commercially available GPC apparatus. Polysilsesquioxane-based sealing materials may be used alone or in combination of two or more.
  • the solvent a used in the present invention is a solvent that has an ester bond and / or an ether bond, does not have a hydroxy group, and has a boiling point of 100 ° C. or more and 200 ° C. or less under 1 atm.
  • the boiling point of the solvent a under 1 atm is preferably 130 ° C. or higher and 200 ° C. or lower. If the boiling point is 100 ° C. or higher, preferably 130 ° C. or higher, the solvent is less likely to volatilize during operations such as weighing, mixing, and potting, and the operability tends to be improved.
  • the solvent does not easily remain afterward and tends to transmit light in the ultraviolet region (particularly the UV-C region).
  • the solubility of the polysilsesquioxane-based sealing material can be increased, but light in the ultraviolet region (particularly the UV-C region) can be transmitted.
  • the functional group containing other heteroelements or an aromatic ring structure is not used.
  • the solvent a include ester solvents such as butyl acetate and butyl butyrate; ether solvents such as dioxane; ethylene glycol diethyl ether and diethylene glycol.
  • glycol ether solvents such as diethyl ether
  • glycol ester solvents such as 2-ethoxyethyl acetate and 2-butoxyethyl acetate.
  • the solvent a may be used in an amount that facilitates potting on the element placed on the substrate, and may be adjusted so that the viscosity of the resulting solution is 10 mPa ⁇ s to 10000 mPa ⁇ s at 25 ° C.
  • the amount used varies depending on the type of polysilsesquioxane-based encapsulant used, but is, for example, in the range of 10 to 60% by weight, preferably in the range of 10 to 45% by weight, and more preferably in the range of 10 to It is in the range of 30% by weight.
  • the solvent a may be used alone or in combination of two or more.
  • a curing catalyst that is, the polysilsesquioxane-based encapsulant contains a curing catalyst.
  • the curing catalyst it is preferable to prepare a solution separate from the resin A and the oligomer B, and mix these solutions before use.
  • the curing catalyst that can be used include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid, and organic acids such as formic acid, acetic acid, succinic acid, citric acid, propionic acid, butyric acid, lactic acid, and succinic acid.
  • the amount of the curing catalyst used is usually in the range of 0.01% by weight to 10% by weight, preferably 0.01% by weight to 5.0% by weight with respect to the polysilsesquioxane-based sealing material. More preferably, it is in the range of 0.01% by weight to 1.0% by weight.
  • the curing catalyst may be used alone or in combination of two or more.
  • the use of the present invention is usually performed by potting an unsealed encapsulant composition containing the polysilsesquioxane-based encapsulant and the solvent a onto an element placed on a substrate, and then curing.
  • the sealing method of the element for UV-LED by use of the present invention is the first step of installing the element on the substrate, the polysilsesquioxane-based sealing material and the following solvent on the element installed on the substrate in the first step.
  • a second step of potting a polysilsesquioxane-based encapsulant composition containing a and a third step of curing the polysilsesquioxane-based encapsulant potted in the second step.
  • the element is placed on the substrate by a conventional method. You may install other structures normally required for a semiconductor light-emitting device, such as an electrode and wiring.
  • the potting is usually performed by supplying a sealing material before curing onto a substrate with a dedicated dispenser.
  • the amount of the sealing material to be supplied before curing varies depending on the structure of the substrate, element, etc., area, volume, and other structures such as electrodes, wire wiring, etc., but these elements and wire wiring are embedded and on the light emitting element. It is preferable that the thickness of the sealing material covering the thickness is as small as possible, and more preferable that the thickness is 2 mm or less.
  • the thickness of the sealing material on the light emitting element is Thinning is effective.
  • a temperature and a time at which a normal polycondensation reaction occurs may be set.
  • the temperature is preferably 100 to 200 ° C. and more preferably 130 to 200 ° C. in air at atmospheric pressure.
  • the time is preferably 1 to 5 hours.
  • the curing temperature may be increased stepwise to be cured.
  • the light transmittance at 260 nm of the cured product is 65% or more, preferably 67% or more, more preferably 70 to 93%.
  • Example 1 In a flask placed in a water bath, 100 g of the resin (A-1) and 31.4 g of 2-ethoxyethyl acetate (boiling point 156 ° C.) are added and stirred while heating until the internal temperature reaches 85 ° C. Resin (A-1) was dissolved to obtain a polysilsesquioxane-based encapsulant composition ( ⁇ 1).
  • polysilsesquioxane-based encapsulant composition ( ⁇ 1) containing 15% by weight of phosphoric acid and the balance being methoxy group dimethylpolysiloxane at both ends (repeating units 3 to 5) 2 parts by mass of the catalyst was added and sufficiently stirred and mixed to obtain a polysilsesquioxane-based sealing material composition ( ⁇ 1-1). Thereafter, about 3.8 g of the composition ( ⁇ 1-1) was put into an aluminum cup, and the temperature was raised from room temperature to 150 ° C. at a rate of 3.7 ° C./min in an oven and left at 150 ° C. for 5 hours.
  • Example 1 shows the results of measuring the ultraviolet and visible transmittance of the cured product.
  • Example 2 In Example 1, polysilsesquioxane-based encapsulant composition ( ⁇ 1) was used in the same procedure as in Example 1 except that 2-butoxyethyl acetate (boiling point 192 ° C.) was used instead of 2-ethoxyethyl acetate. -2) and a cured product thereof.
  • Example 3 In Example 1, polysilsesquioxane-based sealing material composition ( ⁇ 1-3) was used in the same procedure as in Example 1 except that diethylene glycol dimethyl ether (boiling point 162 ° C.) was used instead of 2-ethoxyethyl acetate. And a cured product thereof.
  • Example 4 A polysilsesquioxane encapsulant composition ( ⁇ 1-4) was prepared in the same procedure as in Example 1 except that butyl acetate (boiling point: 126 ° C.) was used instead of 2-ethoxyethyl acetate in Example 1. And a cured product thereof. Table 2 shows the results of measuring the ultraviolet and visible transmittance of the cured products obtained in Examples 1 to 4, respectively.
  • the present invention is useful, for example, as a sealing material for UV-LED.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Led Device Packages (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne : une utilisation d'un solvant (a) comme solvant d'un matériau de scellement polysilsesquioxane pour une DEL UV d'un produit durci laissant passer au moins 65% de la lumière à 260nm ; et d'une composition de matériau polysilsesquioxane de scellement pour une DEL UV comprenant le matériau polysilsesquioxane de scellement et le solvant (a). Le solvant (a) qui comprend une liaison ester et/ou une liaison éther, n'a pas de groupe hydroxy, et a un point d'ébullition à 1atm de 100°C à 200°C.
PCT/JP2015/051942 2014-01-31 2015-01-20 Composition de matériau polysilsesquioxane de scellement pour del uv et utilisation de solvant à cet effet Ceased WO2015115340A1 (fr)

Applications Claiming Priority (2)

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JP2014-016592 2014-01-31
JP2014016592A JP6213270B2 (ja) 2014-01-31 2014-01-31 Ｕｖ−ｌｅｄ用ポリシルセスキオキサン系封止材組成物及びそのための溶媒の使用

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3281923A1 (fr) * 2016-08-03 2018-02-14 Shin-Etsu Chemical Co., Ltd. Couvercle en verre de quartz synthétique et boîtier de dispositif optique

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017075203A (ja) * 2015-10-13 2017-04-20 日本タングステン株式会社 深紫外光用封止材料、深紫外発光装置および深紫外発光装置の製造方法
EP3395905A4 (fr) * 2015-12-21 2019-08-14 Sumitomo Chemical Company, Limited Composition de résine de silicone et matériau d'étanchéité pour élément semi-conducteur électroluminescent

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006013863A1 (fr) * 2004-08-04 2006-02-09 Toagosei Co., Ltd. Polyorganosiloxane et composition durcissable renfermant celui-ci
JP2006169391A (ja) * 2004-12-16 2006-06-29 Hitachi Chem Co Ltd 放射線硬化性樹脂組成物及びこれを用いた光導波路並びに光導波路の製造方法
WO2008066116A1 (fr) * 2006-12-01 2008-06-05 Kaneka Corporation Composition de polysiloxane
JP2008202008A (ja) * 2007-02-22 2008-09-04 Nagase Chemtex Corp 光素子用封止樹脂組成物
WO2009025017A1 (fr) * 2007-08-17 2009-02-26 Panasonic Electric Works Co., Ltd. Dispositif optoélectronique semi-conducteur et élément optique transparent
JP2009211033A (ja) * 2008-02-06 2009-09-17 Hitachi Chem Co Ltd 感光性樹脂組成物、シリカ系被膜の形成方法、シリカ系被膜を備える装置及び部材、並びに感光性樹脂組成物の製造方法
US20130209754A1 (en) * 2012-02-09 2013-08-15 Az Electronic Materials Usa Corp. Low dielectric photoimageable compositions and electronic devices made therefrom

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006013863A1 (fr) * 2004-08-04 2006-02-09 Toagosei Co., Ltd. Polyorganosiloxane et composition durcissable renfermant celui-ci
JP2006169391A (ja) * 2004-12-16 2006-06-29 Hitachi Chem Co Ltd 放射線硬化性樹脂組成物及びこれを用いた光導波路並びに光導波路の製造方法
WO2008066116A1 (fr) * 2006-12-01 2008-06-05 Kaneka Corporation Composition de polysiloxane
JP2008202008A (ja) * 2007-02-22 2008-09-04 Nagase Chemtex Corp 光素子用封止樹脂組成物
WO2009025017A1 (fr) * 2007-08-17 2009-02-26 Panasonic Electric Works Co., Ltd. Dispositif optoélectronique semi-conducteur et élément optique transparent
JP2009211033A (ja) * 2008-02-06 2009-09-17 Hitachi Chem Co Ltd 感光性樹脂組成物、シリカ系被膜の形成方法、シリカ系被膜を備える装置及び部材、並びに感光性樹脂組成物の製造方法
US20130209754A1 (en) * 2012-02-09 2013-08-15 Az Electronic Materials Usa Corp. Low dielectric photoimageable compositions and electronic devices made therefrom

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3281923A1 (fr) * 2016-08-03 2018-02-14 Shin-Etsu Chemical Co., Ltd. Couvercle en verre de quartz synthétique et boîtier de dispositif optique

Also Published As

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JP2015143293A (ja) 2015-08-06
TW201540781A (zh) 2015-11-01
JP6213270B2 (ja) 2017-10-18
TWI653294B (zh) 2019-03-11

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