CN116179127A - Organosilicon modified epoxy resin adhesive - Google Patents
Organosilicon modified epoxy resin adhesive Download PDFInfo
- Publication number
- CN116179127A CN116179127A CN202211698173.6A CN202211698173A CN116179127A CN 116179127 A CN116179127 A CN 116179127A CN 202211698173 A CN202211698173 A CN 202211698173A CN 116179127 A CN116179127 A CN 116179127A
- Authority
- CN
- China
- Prior art keywords
- modified epoxy
- epoxy resin
- parts
- organosilicon modified
- antioxidant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 38
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 38
- 239000000853 adhesive Substances 0.000 title claims abstract description 14
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 14
- 239000004593 Epoxy Substances 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 9
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 8
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- 239000010703 silicon Substances 0.000 claims description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 7
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical group C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 claims description 5
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 claims description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims 4
- 239000008393 encapsulating agent Substances 0.000 claims 3
- 238000002834 transmittance Methods 0.000 abstract description 5
- 230000032683 aging Effects 0.000 abstract description 3
- 238000004806 packaging method and process Methods 0.000 abstract description 3
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 239000000314 lubricant Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 15
- 238000001816 cooling Methods 0.000 description 5
- 239000000498 cooling water Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000005022 packaging material Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002210 silicon-based material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4215—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof cycloaliphatic
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices with at least one potential-jump barrier or surface barrier 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 with at least one potential-jump barrier or surface barrier 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
Abstract
The invention relates to an organosilicon modified epoxy resin adhesive which is prepared from the following raw materials in parts by weight: 20-30 parts of organosilicon modified epoxy A, 30-40 parts of organosilicon modified epoxy resin B and an anhydride curing agent: 30-50 parts of a lubricant; 0.05-0.1 part of antioxidant and 0.06-0.1 part of curing accelerator, has high hardness, high light transmittance (more than 90% in the visible light wavelength range), high refractive index (about 1.51), low moisture absorption, high bonding strength with a substrate, excellent heat aging resistance and ultraviolet irradiation resistance, and is suitable for the field of LED packaging.
Description
Technical Field
The invention belongs to the technical field of LED packaging materials, and particularly relates to an organosilicon modified epoxy resin adhesive.
Background
The silicone-modified epoxy resin refers to a high-performance polymer resin obtained by dealcoholizing or dehydrating polymerization of a silicone material for resin modification, that is, a silicone resin intermediate (silicone oligomer) and an epoxy resin at high temperature. The organic silicon modified epoxy resin can reduce the internal stress of the epoxy resin, increase the toughness, high temperature resistance, flame retardance and the like of the epoxy resin, and is favorable for realizing the high performance and multifunction of the material.
Disclosure of Invention
In view of the above deficiencies of the prior art, it is an object of the present invention to provide an organosilicon modified epoxy adhesive.
In order to achieve the above purpose, the following technical scheme is adopted:
the organic silicon modified epoxy resin adhesive is characterized by comprising the following raw materials in parts by weight: 40-60 parts of organic silicon modified epoxy resin A, 60-40 parts of organic silicon modified epoxy resin B and 30-50 parts of anhydride curing agent; 0.05-0.1 part of antioxidant and 0.06-0.1 part of curing accelerator;
the structure of the organosilicon modified epoxy resin A is shown as a formula 1:
the structure of the organosilicon modified epoxy resin B is shown as a formula 2:
n=100-500。
further, the antioxidant is one or a mixture of both of the antioxidant 1010 and the antioxidant 264.
Further, the acid anhydride curing agent is methyl tetrahydrophthalic anhydride or methyl hexahydrophthalic anhydride.
Further, the curing accelerator is triphenylphosphine.
Further, the molar ratio of epoxy groups to anhydride was 1: (0.85-1.1).
Further, the synthesis steps of the organic silicon resin modified epoxy resin A are as follows:
further, the synthesis steps of the organic silicon resin modified epoxy resin B are as follows:
the preparation method of the organosilicon modified epoxy resin adhesive comprises the following steps: 40-60 parts of organosilicon modified epoxy A, 60-40 parts of organosilicon modified epoxy resin B and 0.05-0.1 part of antioxidant; adding the mixture into a stirring kettle, heating to 100-140 ℃, stirring for 5 hours, cooling to below 20 ℃ by cooling water, and adding 30-50 parts of anhydride curing agent; and (3) 0.06-0.1 part of curing accelerator, and uniformly stirring to obtain the organosilicon modified epoxy resin adhesive.
Compared with the prior art, the invention has the beneficial effects that:
the epoxy modified organic silicon material integrates the excellent performances of the epoxy resin and the organic silicon resin, and is more suitable for the development requirement of LED packaging. The invention aims to synthesize a high-performance LED packaging material, and modifies the organic silicon packaging material on the molecular structure level to prepare the epoxy modified organic silicon base sizing material with excellent comprehensive performance. The LED packaging material has the advantages of high hardness, high light transmittance (more than 90% in the visible light wavelength range), high refractive index (about 1.51), low moisture absorption, high bonding strength with a substrate, excellent heat aging resistance and ultraviolet irradiation resistance, and suitability for the field of LED packaging.
Detailed Description
The invention is described below in connection with examples which are given solely for the purpose of illustration and are not intended to limit the scope of the invention.
The present invention will be further described in detail with reference to the following examples in order to better understand the technical solution of the present invention and to make the above objects, features and advantages of the present invention more obvious.
Example 1
40g of organosilicon modified epoxy A, 60g of organosilicon modified epoxy resin B and 0.05g of antioxidant 1010; adding the mixture into a stirring kettle, heating to 100 ℃, stirring for 5 hours, cooling to below 20 ℃ by cooling water, adding 50g of anhydride curing agent methyl hexahydrophthalic anhydride and 0.1g of curing accelerator triphenylphosphine, and stirring uniformly to obtain the organosilicon modified epoxy resin adhesive.
Example 2
40g of organosilicon modified epoxy A, 40g of organosilicon modified epoxy resin B and 0.1g of antioxidant 1010; adding the mixture into a stirring kettle, heating to 140 ℃, stirring for 5 hours, cooling to below 20 ℃ by cooling water, and adding an anhydride curing agent methyl tetrahydrophthalic anhydride: 50g of curing accelerator triphenylphosphine 0.1g, and uniformly stirring to obtain the organosilicon modified epoxy resin adhesive.
Example 3
60g of organosilicon modified epoxy A, 55g of organosilicon modified epoxy resin B and 264.08 g of antioxidant; adding the mixture into a stirring kettle, heating to 120 ℃, stirring for 5 hours, cooling to below 20 ℃ by cooling water, and adding an anhydride curing agent methyl tetrahydrophthalic anhydride: 40g of curing accelerator triphenylphosphine 0.1g, and uniformly stirring to obtain the organosilicon modified epoxy resin adhesive.
Example 4
50g of organosilicon modified epoxy A, 50g of organosilicon modified epoxy resin B and 264.09 g of antioxidant; adding the mixture into a stirring kettle, heating to 120 ℃, stirring for 5 hours, cooling to below 20 ℃ by cooling water, adding 48g of anhydride curing agent methyl tetrahydrophthalic anhydride and 0.06g of curing accelerator triphenylphosphine, and stirring uniformly to obtain the organosilicon modified epoxy resin adhesive.
Comparative example 1
And (3) a commercially available epoxy resin packaging material.
Comparative example 2
Silicone encapsulation materials are commercially available.
And (3) testing:
the materials prepared in examples 1 to 4 and comparative examples 1 to 2 were subjected to light transmittance and 500h light transmittance after double 85 test, and the test results are shown in Table 1.
TABLE 1 comparison of the Performance test data for examples 1-4 and comparative examples 1-2
The data in Table 1 show that the transmittance of the adhesive prepared by the invention is about 95% at 450nm, and the adhesive is still not attenuated after double-85 ageing. In conclusion, the material prepared by the invention has the air tightness and the adhesiveness of the traditional epoxy, and well maintains the light transmission yield and the light attenuation performance of the organic silicon material.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and scope of the invention are intended to be included within the scope of the invention.
Claims (5)
1. The organic silicon modified epoxy resin adhesive is characterized by comprising the following raw materials in parts by weight: 40-60 parts of organic silicon modified epoxy resin A, 60-40 parts of organic silicon modified epoxy resin B and 30-50 parts of anhydride curing agent; 0.05-0.1 part of antioxidant and 0.06-0.1 part of curing accelerator;
the structure of the organosilicon modified epoxy resin A is shown as a formula 1:
the structure of the organosilicon modified epoxy resin B is shown as a formula 2:
n=100-500。
2. the silicone-modified epoxy optical encapsulant composition according to claim 1, wherein the antioxidant is one or a mixture of both of antioxidant 1010 and antioxidant 264.
3. The silicone-modified epoxy resin optical encapsulant composition according to claim 1, wherein the acid anhydride curing agent is methyltetrahydrophthalic anhydride or methylhexahydrophthalic anhydride.
4. The silicone-modified epoxy resin optical encapsulant composition according to claim 1, wherein the curing accelerator is triphenylphosphine.
5. The silicone-modified epoxy resin optical encapsulating material composition according to claim 1, wherein the molar ratio of epoxy groups to acid anhydride is 1: (0.85-1.1).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211698173.6A CN116179127A (en) | 2022-12-28 | 2022-12-28 | Organosilicon modified epoxy resin adhesive |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211698173.6A CN116179127A (en) | 2022-12-28 | 2022-12-28 | Organosilicon modified epoxy resin adhesive |
Publications (1)
Publication Number | Publication Date |
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CN116179127A true CN116179127A (en) | 2023-05-30 |
Family
ID=86448089
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202211698173.6A Pending CN116179127A (en) | 2022-12-28 | 2022-12-28 | Organosilicon modified epoxy resin adhesive |
Country Status (1)
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02147620A (en) * | 1988-11-30 | 1990-06-06 | Sumitomo Bakelite Co Ltd | Epoxy resin composition |
CN102532900A (en) * | 2010-12-20 | 2012-07-04 | 常州化学研究所 | Organosilicon lens material for power type light-emitting diode (LED) packaging |
CN106751877A (en) * | 2016-11-21 | 2017-05-31 | 烟台德邦先进硅材料有限公司 | A kind of modifying epoxy resin by organosilicon optical packaging material composition |
CN109762299A (en) * | 2018-11-30 | 2019-05-17 | 纳晶科技股份有限公司 | A kind of encapsulating material, organic barrier solidfied material and quantum dot device |
CN112341755A (en) * | 2019-08-07 | 2021-02-09 | 北京科化新材料科技有限公司 | Yellowing-resistant transparent epoxy resin packaging material and preparation method and application thereof |
CN113348204A (en) * | 2018-12-26 | 2021-09-03 | 迈图高新材料公司 | Silicone-based curable compositions and their use cross-reference to related applications |
-
2022
- 2022-12-28 CN CN202211698173.6A patent/CN116179127A/en active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02147620A (en) * | 1988-11-30 | 1990-06-06 | Sumitomo Bakelite Co Ltd | Epoxy resin composition |
CN102532900A (en) * | 2010-12-20 | 2012-07-04 | 常州化学研究所 | Organosilicon lens material for power type light-emitting diode (LED) packaging |
CN106751877A (en) * | 2016-11-21 | 2017-05-31 | 烟台德邦先进硅材料有限公司 | A kind of modifying epoxy resin by organosilicon optical packaging material composition |
CN109762299A (en) * | 2018-11-30 | 2019-05-17 | 纳晶科技股份有限公司 | A kind of encapsulating material, organic barrier solidfied material and quantum dot device |
CN113348204A (en) * | 2018-12-26 | 2021-09-03 | 迈图高新材料公司 | Silicone-based curable compositions and their use cross-reference to related applications |
CN112341755A (en) * | 2019-08-07 | 2021-02-09 | 北京科化新材料科技有限公司 | Yellowing-resistant transparent epoxy resin packaging material and preparation method and application thereof |
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