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CN108218906A - A kind of organo-silicon compound and its preparation method and application and LED encapsulation material - Google Patents

A kind of organo-silicon compound and its preparation method and application and LED encapsulation material Download PDF

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CN108218906A
CN108218906A CN201611151119.4A CN201611151119A CN108218906A CN 108218906 A CN108218906 A CN 108218906A CN 201611151119 A CN201611151119 A CN 201611151119A CN 108218906 A CN108218906 A CN 108218906A
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silicon compound
encapsulation material
organosilicon compound
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CN108218906B (en
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王锐
张琛
李刚
王善学
卢绪奎
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BEIJING KEHUA NEW MATERIAL SCIENCE AND TECHNOLOGY CO LTD
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0834Compounds having one or more O-Si linkage
    • C07F7/0838Compounds with one or more Si-O-Si sequences
    • C07F7/0872Preparation and treatment thereof
    • C07F7/0874Reactions involving a bond of the Si-O-Si linkage
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/54Silicon-containing compounds
    • C08K5/544Silicon-containing compounds containing nitrogen
    • C08K5/5455Silicon-containing compounds containing nitrogen containing at least one group
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02Non-macromolecular additives
    • C09J11/06Non-macromolecular additives organic
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00Adhesives based on 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; Adhesives based on derivatives of such polymers
    • C09J183/04Polysiloxanes
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10HINORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
    • H10H20/00Individual inorganic light-emitting semiconductor devices having potential barriers, e.g. light-emitting diodes [LED]
    • H10H20/80Constructional details
    • H10H20/85Packages
    • H10H20/852Encapsulations
    • H10H20/854Encapsulations characterised by their material, e.g. epoxy or silicone resins

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)

Abstract

本发明涉及LED封装领域,公开了一种有机硅化合物及其制备方法和应用以及LED封装材料。所述LED封装材料含有硅胶和有机硅化合物,所述有机硅化合物具有式(I)所示的结构:其中,R1‑R8各自独立地为C1‑C5的烷基,R9和R10各自独立地为C1‑C8的亚烷基。将所述有机硅化合物加入封装硅胶中之后,可以显著提升硅胶的粘接力,并且封装硅胶固化后仍能长期保持较高的粘接力,从而能够显著提高LED灯珠的使用寿命。 The invention relates to the field of LED packaging, and discloses an organosilicon compound, a preparation method and application thereof, and an LED packaging material. The LED encapsulation material contains silica gel and an organosilicon compound, and the organosilicon compound has a structure shown in formula (I): wherein, R 1 -R 8 are each independently an alkyl group of C 1 -C 5 , R 9 and Each of R 10 is independently a C 1 -C 8 alkylene group. After the organosilicon compound is added to the encapsulating silica gel, the adhesive force of the silica gel can be significantly improved, and the encapsulating silica gel can still maintain a high adhesive force for a long time after curing, thereby significantly improving the service life of the LED lamp bead.

Description

一种有机硅化合物及其制备方法和应用以及LED封装材料A kind of organosilicon compound and its preparation method and application and LED encapsulation material

技术领域technical field

本发明涉及LED封装领域,具体地,涉及一种有机硅化合物、一种有机硅化合物的制备方法、由该方法制备得到的有机硅化合物、所述有机硅化合物作为粘结促进剂的应用以及一种LED封装材料。The present invention relates to the field of LED packaging, in particular to an organosilicon compound, a preparation method of an organosilicon compound, an organosilicon compound prepared by the method, an application of the organosilicon compound as an adhesion promoter and a A kind of LED encapsulation material.

背景技术Background technique

发光二极管(LED)是一种固态的半导体器件,其可以直接将电能转化为光能。LED照明灯具有能耗低、体积小、寿命长等特点,LED照明灯将取代白炽灯、荧光灯等传统光源而成为第四代照明光源。LED照明灯的心脏是半导体晶片(灯珠),该半导体晶片的一端附着在支架上,为负极,另一端连接电源的正极,整个半导体晶片被环氧树脂或硅胶封装起来。A light emitting diode (LED) is a solid-state semiconductor device that can directly convert electrical energy into light energy. LED lighting has the characteristics of low energy consumption, small size, and long life. LED lighting will replace traditional light sources such as incandescent lamps and fluorescent lamps and become the fourth-generation lighting source. The heart of the LED lighting lamp is a semiconductor chip (lamp bead). One end of the semiconductor chip is attached to the bracket as the negative pole, and the other end is connected to the positive pole of the power supply. The entire semiconductor chip is encapsulated by epoxy resin or silica gel.

近年来,LED封装行业发展迅猛,由于环氧树脂的抗臭氧能力较弱以致于容易导致胶体变黄,影响透光效果,而硅胶材料由于具有抗大气老化、紫外老化等优异性能,在高端产品应用上环氧树脂已经被硅胶材料所取代。然而,采用硅胶封装却存在与LED支架粘接力差的问题,这样会严重影响LED灯珠的长期可靠性和使用寿命。In recent years, the LED packaging industry has developed rapidly. Due to the weak anti-ozone ability of epoxy resin, it is easy to cause the colloid to turn yellow and affect the light transmission effect. Due to its excellent properties such as anti-atmospheric aging and ultraviolet aging, silicone materials are widely used in high-end products. Epoxy resins have been replaced by silicone materials in applications. However, the use of silica gel packaging has the problem of poor adhesion to the LED bracket, which will seriously affect the long-term reliability and service life of the LED lamp bead.

发明内容Contents of the invention

本发明是为了解决现有技术采用硅胶对LED灯珠进行封装时存在硅胶与LED支架粘接力差的问题,而提供一种能够显著提高硅胶与LED支架材料之间的粘接力的有机硅化合物、一种有机硅化合物的制备方法、由该方法制备得到的有机硅化合物、所述有机硅化合物作为粘结促进剂的应用以及一种LED封装材料。The present invention aims to solve the problem of poor adhesion between silica gel and LED brackets in the prior art when silica gel is used to package LED lamp beads, and provides a silicone that can significantly improve the adhesion between silica gel and LED bracket materials. Compound, a method for preparing an organosilicon compound, an organosilicon compound prepared by the method, an application of the organosilicon compound as an adhesion promoter, and an LED encapsulation material.

具体地,本发明提供了一种有机硅化合物,其中,所述有机硅化合物具有式(I)所示的结构:Specifically, the present invention provides an organosilicon compound, wherein the organosilicon compound has a structure shown in formula (I):

其中,R1-R8各自独立地为C1-C5的烷基,R9和R10各自独立地为C1-C8的亚烷基。Wherein, R 1 -R 8 are each independently a C 1 -C 5 alkyl group, and R 9 and R 10 are each independently a C 1 -C 8 alkylene group.

本发明还提供了一种有机硅化合物的制备方法,其中,该方法包括:The present invention also provides a method for preparing an organosilicon compound, wherein the method comprises:

(1)将式(II)所示的二苯基硅二醇与式(III)所示的脲基烷氧基硅烷在第一碱性催化剂和第一溶剂的存在下进行第一脱醇反应;(1) Carrying out the first dealcoholization reaction with diphenylsilanediol shown in formula (II) and ureidoalkoxysilane shown in formula (III) in the presence of the first basic catalyst and the first solvent ;

(2)将所述第一脱醇反应的产物与式(IV)所示的二乙烯基二硅氧烷在第二碱性催化剂和第二溶剂的存在下进行第二脱醇反应;(2) performing a second dealcoholation reaction with the product of the first dealcoholization reaction and divinyldisiloxane represented by formula (IV) in the presence of a second basic catalyst and a second solvent;

其中,R9为C1-C8的亚烷基,R11-R13各自独立地为C1-C5的烷基,R14-R17各自独立地为C1-C5的烷基。Wherein, R 9 is a C 1 -C 8 alkylene group, R 11 -R 13 are each independently a C 1 -C 5 alkyl group, R 14 -R 17 are each independently a C 1 -C 5 alkyl group .

本发明还提供了由上述方法制备得到的有机硅化合物。The present invention also provides the organosilicon compound prepared by the above method.

本发明还提供了所述有机硅化合物作为粘结促进剂的应用。The present invention also provides the use of the organosilicon compound as an adhesion promoter.

此外,本发明还提供了一种LED封装材料,所述LED封装材料含有硅胶,其中,所述LED封装材料还含有本发明提供的有机硅化合物。In addition, the present invention also provides an LED encapsulation material, which contains silica gel, wherein the LED encapsulation material also contains the organosilicon compound provided by the present invention.

本发明的发明人经过深入研究之后发现,将具有式(I)所示结构的有机硅化合物加入封装硅胶中之后,可以显著提升硅胶与LED支架材料之间的附着力,并且由此得到的封装材料固化后仍能长期保持与支架材料的粘接力,从而能够显著提高LED灯珠的使用寿命。After in-depth research, the inventors of the present invention found that after adding the organosilicon compound having the structure shown in formula (I) into the encapsulation silica gel, the adhesion between the silica gel and the LED bracket material can be significantly improved, and the encapsulation thus obtained After the material is cured, it can still maintain the adhesive force with the bracket material for a long time, so that the service life of the LED lamp bead can be significantly improved.

本发明的其它特征和优点将在随后的具体实施方式部分予以详细说明。Other features and advantages of the present invention will be described in detail in the detailed description that follows.

具体实施方式Detailed ways

以下对本发明的具体实施方式进行详细说明。应当理解的是,此处所描述的具体实施方式仅用于说明和解释本发明,并不用于限制本发明。Specific embodiments of the present invention will be described in detail below. It should be understood that the specific embodiments described here are only used to illustrate and explain the present invention, and are not intended to limit the present invention.

在本文中所披露的范围的端点和任何值都不限于该精确的范围或值,这些范围或值应当理解为包含接近这些范围或值的值。对于数值范围来说,各个范围的端点值之间、各个范围的端点值和单独的点值之间,以及单独的点值之间可以彼此组合而得到一个或多个新的数值范围,这些数值范围应被视为在本文中具体公开。Neither the endpoints nor any values of the ranges disclosed herein are limited to such precise ranges or values, and these ranges or values are understood to include values approaching these ranges or values. For numerical ranges, between the endpoints of each range, between the endpoints of each range and individual point values, and between individual point values can be combined with each other to obtain one or more new numerical ranges, these values Ranges should be considered as specifically disclosed herein.

本发明提供的有机硅化合物具有式(I)所示的结构:The organosilicon compound provided by the invention has the structure shown in formula (I):

其中,R1-R8各自独立地为C1-C5的烷基,R9和R10各自独立地为C1-C8的亚烷基。Wherein, R 1 -R 8 are each independently a C 1 -C 5 alkyl group, and R 9 and R 10 are each independently a C 1 -C 8 alkylene group.

所述C1-C5的烷基可以为直链或支链烷基,具体实例包括但不限于:甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、异戊基、叔戊基或新戊基。The C 1 -C 5 alkyl group can be straight chain or branched chain alkyl, specific examples include but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso Butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl or neopentyl.

所述C1-C8的亚烷基可以为直链或支链亚烷基,具体实例包括但不限于:亚甲基、亚乙基、亚正丙基、亚异丙基、亚正丁基、亚仲丁基、亚异丁基、亚叔丁基、亚正戊基、亚异戊基、亚叔戊基、亚新戊基、亚己基、亚异己基、亚庚基、亚异庚基、亚辛基或亚异辛基。The C 1 -C 8 alkylene group can be straight chain or branched chain alkylene group, specific examples include but not limited to: methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group Base, sec-butylene, isobutylene, tert-butylene, n-pentylene, isopentylene, tert-pentylene, neopentylene, hexylene, isohexylene, heptylene, iso- Heptyl, octylene or isooctylene.

根据本发明,从原料易得性的角度考虑,优选地,R1-R8各自独立地为C1-C3的烷基,R9和R10各自独立地为C2-C4的亚烷基。最优选地,R1-R8均为甲基,R9和R10均为亚丙基。According to the present invention, from the viewpoint of raw material availability, preferably, R 1 -R 8 are each independently a C 1 -C 3 alkyl group, R 9 and R 10 are each independently a C 2 -C 4 alkyl group. alkyl. Most preferably, R 1 -R 8 are all methyl groups, and R 9 and R 10 are both propylene groups.

本发明提供的有机硅化合物的制备方法包括:The preparation method of organosilicon compound provided by the invention comprises:

(1)将式(II)所示的二苯基硅二醇与式(III)所示的脲基烷氧基硅烷在第一碱性催化剂和第一溶剂的存在下进行第一脱醇反应;(1) Carrying out the first dealcoholization reaction with diphenylsilanediol shown in formula (II) and ureidoalkoxysilane shown in formula (III) in the presence of the first basic catalyst and the first solvent ;

(2)将所述第一脱醇反应的产物与式(IV)所示的二乙烯基二硅氧烷在第二碱性催化剂和第二溶剂的存在下进行第二脱醇反应;(2) performing a second dealcoholation reaction with the product of the first dealcoholization reaction and divinyldisiloxane represented by formula (IV) in the presence of a second basic catalyst and a second solvent;

其中,R9为C1-C8的亚烷基,R11-R13各自独立地为C1-C5的烷基,R14-R17各自独立地为C1-C5的烷基。其中,所述C1-C8的亚烷基以及C1-C5的烷基的具体选择已经在上文中有所描述,在此不作赘述。Wherein, R 9 is a C 1 -C 8 alkylene group, R 11 -R 13 are each independently a C 1 -C 5 alkyl group, R 14 -R 17 are each independently a C 1 -C 5 alkyl group . Wherein, the specific selection of the C 1 -C 8 alkylene group and the C 1 -C 5 alkyl group has been described above, and will not be repeated here.

根据本发明,从原料易得性的角度考虑,优选地,R9为C2-C4的亚烷基,R11-R13各自独立地为C1-C3的烷基,R14-R17各自独立地为C1-C3的烷基。最优选地,R9为亚丙基,R11-R13为C1-C3的烷基,R14-R17为甲基。According to the present invention, from the viewpoint of availability of raw materials, preferably, R 9 is a C 2 -C 4 alkylene group, R 11 -R 13 are each independently a C 1 -C 3 alkyl group, R 14 - Each of R 17 is independently a C 1 -C 3 alkyl group. Most preferably, R 9 is a propylene group, R 11 -R 13 are C 1 -C 3 alkyl groups, and R 14 -R 17 are methyl groups.

根据本发明,从便于描述的角度出发,将步骤(1)中所采用的碱性催化剂称为“第一碱性催化剂”,所采用的溶剂称为“第一溶剂”,所对应的脱醇反应称为“第一脱醇反应”;将步骤(2)中所采用的碱性催化剂称为“第二碱性催化剂”,所采用的溶剂称为“第二溶剂”,所对应的脱醇反应称为“第二脱醇反应”。According to the present invention, from the viewpoint of convenience of description, the basic catalyst adopted in step (1) is called "the first basic catalyst", and the solvent adopted is called "the first solvent", and the corresponding dealcoholization The reaction is called "the first dealcoholization reaction"; the basic catalyst adopted in step (2) is called "the second basic catalyst", and the solvent adopted is called "the second solvent", and the corresponding dealcoholization The reaction is called "the second dealcoholation reaction".

根据本发明,步骤(1)中,式(III)所示的脲基烷氧基硅烷在第一溶剂的存在下与式(II)所示的二苯基硅二醇在第一碱性催化剂的催化作用下进行脱醇反应。步骤(2)中,式(IV)所示的二乙烯基二硅氧烷在第二碱性催化剂的作用下与水反应形成硅羟基,之后与所述第一脱醇反应的产物进行脱醇反应。According to the present invention, in step (1), in the presence of the first solvent, the ureidoalkoxysilane shown in the formula (III) is mixed with the diphenylsilanediol shown in the formula (II) in the first basic catalyst The dealcoholation reaction is carried out under the catalysis. In step (2), the divinyldisiloxane represented by formula (IV) reacts with water under the action of the second basic catalyst to form silanol, and then deals with the product of the first dealcoholization reaction reaction.

本发明对所述有机硅化合物制备过程中各物质的用量没有特别的限定。例如,所述二苯基硅二醇的用量与所述脲基烷氧基硅烷的用量的摩尔比可以为(0.2-2)∶1,优选为(0.5-1.5)∶1,最优选为(0.5-1)∶1。所述二乙烯基二硅氧烷的用量与所述脲基烷氧基硅烷的用量的摩尔比可以为(0.5-2)∶1,优选为(1-2)∶1,最优选为(1.5-2)∶1。In the present invention, there is no special limitation on the amount of each substance used in the preparation process of the organosilicon compound. For example, the molar ratio of the amount of diphenylsilanediol to the amount of ureidoalkoxysilane can be (0.2-2): 1, preferably (0.5-1.5): 1, most preferably ( 0.5-1):1. The molar ratio of the amount of divinyldisiloxane to the amount of ureidoalkoxysilane can be (0.5-2): 1, preferably (1-2): 1, most preferably (1.5 -2): 1.

本发明对所述第一碱性催化剂和第二碱性催化剂的种类没有特别的限定,可以为现有的各种能够催化脱醇反应的物质,例如,所述第一碱性催化剂和第二碱性催化剂优选各自独立地为三乙胺、三乙烯二胺、吡啶和二氮杂二环中的至少一种。此外,相对于1mol的所述式(II)所示的二苯基硅二醇,所述第一碱性催化剂的用量可以为0.5-8g,优选为1-5g,最优选为2.5-4.5g;所述第二碱性催化剂的用量可以为1-7g,优选为2-5g,最优选为2.5-4.5g。The present invention is not particularly limited to the type of the first basic catalyst and the second basic catalyst, which can be various existing substances capable of catalyzing the dealcoholization reaction, for example, the first basic catalyst and the second basic catalyst The basic catalysts are preferably each independently at least one of triethylamine, triethylenediamine, pyridine and diazabicycle. In addition, relative to 1 mol of the diphenylsilanediol represented by the formula (II), the amount of the first basic catalyst can be 0.5-8g, preferably 1-5g, most preferably 2.5-4.5g ; The amount of the second basic catalyst can be 1-7g, preferably 2-5g, most preferably 2.5-4.5g.

本发明对所述第一溶剂和第二溶剂的种类没有特别的限定,可以为现有的各种使得烷氧基水解成羟基并能够作为反应媒介的液态惰性物质,例如,所述第一溶剂和第二溶剂优选各自独立地为四氢呋喃、二氧六环、二甲基甲酰胺和二甲基乙酰胺中的至少一种。此外,相对于1mol的所述式(II)所示的二苯基硅二醇,所述第一溶剂的用量可以为100-300g,优选为150-250g,最优选为200-250g;所述第二溶剂的用量可以为100-300g,优选为150-250g,最优选为200-250g。The present invention has no particular limitation on the types of the first solvent and the second solvent, which may be various existing liquid inert substances that hydrolyze alkoxy groups into hydroxyl groups and can be used as reaction media, for example, the first solvent and the second solvent are preferably each independently at least one of tetrahydrofuran, dioxane, dimethylformamide and dimethylacetamide. In addition, relative to 1 mol of diphenylsilanediol represented by the formula (II), the amount of the first solvent may be 100-300g, preferably 150-250g, most preferably 200-250g; The amount of the second solvent may be 100-300 g, preferably 150-250 g, most preferably 200-250 g.

本发明对所述第一脱醇反应和第二脱醇反应的条件均没有特别的限定,两者可以相同,也可以不同,优选地,两者各自独立地包括依次进行的低温聚合反应和高温聚合反应,且所述低温聚合反应的条件包括温度为0-5℃且时间为2-8h,所述高温聚合反应的条件包括温度为40-80℃且时间为2-10h;更优选地,两者各自独立地包括依次进行的低温聚合反应和高温聚合反应,且所述低温聚合反应的条件包括温度为0-5℃且时间为2-4h,所述高温聚合反应的条件包括温度为50-60℃且时间为2-6h。In the present invention, the conditions of the first dealcoholization reaction and the second dealcoholization reaction are not particularly limited, and both may be the same or different. Preferably, both independently include low-temperature polymerization and high-temperature polymerization carried out sequentially. Polymerization, and the conditions of the low-temperature polymerization include a temperature of 0-5°C and a time of 2-8h, the conditions of the high-temperature polymerization include a temperature of 40-80°C and a time of 2-10h; more preferably, The two independently include a low-temperature polymerization reaction and a high-temperature polymerization reaction carried out in sequence, and the conditions of the low-temperature polymerization reaction include a temperature of 0-5° C. and a time of 2-4 h, and the conditions of the high-temperature polymerization reaction include a temperature of 50 ° C. -60°C and the time is 2-6h.

本发明对步骤(1)和步骤(2)中各物质的加入顺序没有特别的限定,可以按照现有的各种顺序将反应产物进行混合。根据本发明的一种具体实施方式,步骤(1)中,可以先将式(III)所示的脲基烷氧基硅烷与第一碱性催化剂进行混合,并将式(II)所示的二苯基硅二醇与第一溶剂进行混合,之后再将后者滴加到前者中。步骤(2)中,可以先将式(IV)所示的二乙烯基二硅氧烷、第二碱性催化剂以及部分第二溶剂进行混合,并将所述第一脱醇反应的产物与剩余第二溶剂进行混合,之后再将后者滴加到前者中。The present invention has no special limitation on the order of adding the substances in step (1) and step (2), and the reaction products can be mixed according to various existing orders. According to a specific embodiment of the present invention, in step (1), the ureidoalkoxysilane shown in formula (III) can be mixed with the first basic catalyst first, and the ureidoalkoxysilane shown in formula (II) Diphenylsilanediol is mixed with the first solvent, and then the latter is added dropwise to the former. In step (2), the divinyldisiloxane shown in formula (IV), the second basic catalyst and part of the second solvent can be mixed first, and the product of the first dealcoholization reaction can be mixed with the remaining The second solvent is mixed before the latter is added dropwise to the former.

根据本发明,优选地,所述有机硅化合物的制备方法还包括在步骤(1)和/或步骤(2)完成之后,采用酸中和反应产物中的碱性催化剂,之后加入醇以分层去除中和所得的盐,最后再进行减压蒸馏去除溶剂以得到目标产物。其中,所述酸可以为甲酸、乙酸、丙酸、丁酸、乙二酸、丙二酸、丁二酸、苯甲酸、苯乙酸中的至少一种。所述醇可以为甲醇、乙醇、乙二醇、异丙醇、正丁醇中的至少一种。According to the present invention, preferably, the preparation method of the organosilicon compound further comprises using an acid to neutralize the basic catalyst in the reaction product after step (1) and/or step (2), and then adding alcohol to separate the layers The neutralized salt was removed, and finally the solvent was distilled off under reduced pressure to obtain the target product. Wherein, the acid may be at least one of formic acid, acetic acid, propionic acid, butyric acid, oxalic acid, malonic acid, succinic acid, benzoic acid, and phenylacetic acid. The alcohol may be at least one of methanol, ethanol, ethylene glycol, isopropanol, and n-butanol.

本发明还提供了由上述方法制备得到的有机硅化合物。The present invention also provides the organosilicon compound prepared by the above method.

本发明还提供了所述有机硅化合物作为粘结促进剂的应用。The present invention also provides the use of the organosilicon compound as an adhesion promoter.

此外,本发明还提供了一种LED封装材料,所述LED封装材料含有硅胶,其中,所述LED封装材料还含有本发明提供的有机硅化合物。In addition, the present invention also provides an LED encapsulation material, which contains silica gel, wherein the LED encapsulation material also contains the organosilicon compound provided by the present invention.

本发明对所述有机硅化合物的用量没有特别的限定,优选地,所述有机硅化合物与硅胶的重量比为(0.005-0.05)∶1,更优选为(0.005-0.025)∶1,最优选为(0.01-0.02)∶1。此外,以所述LED封装材料的总重量为基准,所述硅胶的含量优选为95-99.5重量%,更优选为97.5-99.5重量%,最优选为98-99重量%;所述有机硅化合物的含量优选为0.5-5重量%,更优选为0.5-2.5重量%,最优选为1-2重量%。The amount of the organosilicon compound used in the present invention is not particularly limited. Preferably, the weight ratio of the organosilicon compound to silica gel is (0.005-0.05): 1, more preferably (0.005-0.025): 1, most preferably It is (0.01-0.02):1. In addition, based on the total weight of the LED packaging material, the content of the silica gel is preferably 95-99.5% by weight, more preferably 97.5-99.5% by weight, most preferably 98-99% by weight; the organosilicon compound The content of is preferably 0.5-5% by weight, more preferably 0.5-2.5% by weight, most preferably 1-2% by weight.

本发明的主要改进之处在于在现有的LED封装用硅胶中添加了本发明所述的有机硅化合物,以提高粘接性能,而硅胶的种类可以与现有技术相同,具体可以为现有的各种能够用作LED封装材料的硅胶,对此本领域技术人员均能知悉,在此不作赘述。The main improvement of the present invention is that the organic silicon compound described in the present invention is added to the existing silica gel for LED packaging to improve the adhesive performance, and the type of silica gel can be the same as that of the prior art, specifically, it can be the existing Various silica gels that can be used as LED packaging materials are known to those skilled in the art, and will not be repeated here.

以下将通过实施例对本发明进行详细描述。The present invention will be described in detail below by way of examples.

以下实施例和对比例中,硅胶购自北京科化新材料科技有限公司,牌号为SK6130。In the following examples and comparative examples, silica gel was purchased from Beijing Kehua New Material Technology Co., Ltd., and the brand name was SK6130.

制备例1Preparation Example 1

该制备例用于说明本发明提供的有机硅化合物及其制备方法。This preparation example is used to illustrate the organosilicon compound provided by the present invention and its preparation method.

(1)第一脱醇反应:(1) The first dealcoholization reaction:

将油浴温度设定为0℃,向三口烧瓶中加入22.2g(0.1mol)脲丙基三甲氧基硅烷与0.2g吡啶,并开启搅拌。称取10g(0.05mol)二苯基硅二醇溶解于10g四氢呋喃中,接着将所得溶液倒入恒压滴液漏斗,20分钟内滴加到上述三口烧瓶中,滴加完毕之后继续在0℃下搅拌反应2h,之后升温至60℃继续反应3h,停止反应。用甲酸中和吡啶,加少量无水甲醇,分层去除吡啶-甲酸盐,接着在减压下蒸除目标产物中的溶剂四氢呋喃,得到含有端甲氧基的脲基预聚体,干燥保存,产率为90%。Set the temperature of the oil bath to 0° C., add 22.2 g (0.1 mol) of ureapropyltrimethoxysilane and 0.2 g of pyridine into the three-necked flask, and start stirring. Weigh 10g (0.05mol) of diphenylsilanediol and dissolve it in 10g of tetrahydrofuran, then pour the resulting solution into a constant pressure dropping funnel, and drop it into the above-mentioned three-necked flask within 20 minutes. The reaction was stirred under low temperature for 2h, and then the temperature was raised to 60°C to continue the reaction for 3h, and the reaction was stopped. Neutralize pyridine with formic acid, add a small amount of anhydrous methanol, remove pyridine-formate by layering, and then distill off the solvent tetrahydrofuran in the target product under reduced pressure to obtain a urea-based prepolymer containing methoxy-terminated, dry and store , the yield was 90%.

(2)第二脱醇反应:(2) The second dealcoholization reaction:

将油浴温度设定为50℃,向三口烧瓶中加入0.2g吡啶、37.2g(0.2mol)四甲基二乙烯基二硅氧烷和0.36g水,搅拌反应3h后降温至0℃。称取上述预聚体28g溶于15g四氢呋喃,接着将所得溶液置于恒压滴液漏斗中,40分钟内滴加到三口烧瓶中,滴加完毕之后继续在0℃下搅拌反应3h,之后升温至60℃继续反应5h,停止反应。用甲酸中和吡啶,加少量无水甲醇,分层去除吡啶-甲酸盐,接着在减压下蒸除目标产物中的溶剂四氢呋喃,得到有机硅化合物(记为G1),产率为90%。Set the temperature of the oil bath to 50°C, add 0.2g of pyridine, 37.2g (0.2mol) of tetramethyldivinyldisiloxane and 0.36g of water into the three-necked flask, stir the reaction for 3h and cool down to 0°C. Weigh 28g of the above-mentioned prepolymer and dissolve it in 15g of tetrahydrofuran, then place the obtained solution in a constant pressure dropping funnel, and drop it into a three-necked flask within 40 minutes. Continue to react at 60°C for 5h, then stop the reaction. Neutralize pyridine with formic acid, add a small amount of anhydrous methanol, separate layers to remove pyridine-formate, and then distill off the solvent tetrahydrofuran in the target product under reduced pressure to obtain an organosilicon compound (denoted as G1), with a yield of 90% .

经红外和核磁检测可知,该有机硅化合物具有式(I)所示的结构,其中,R1-R8均为甲基,R9和R10均为亚丙基。According to infrared and nuclear magnetic detection, the organosilicon compound has the structure shown in formula (I), wherein, R 1 -R 8 are all methyl groups, and R 9 and R 10 are all propylene groups.

制备例2Preparation example 2

该制备例用于说明本发明提供的有机硅化合物及其制备方法。This preparation example is used to illustrate the organosilicon compound provided by the present invention and its preparation method.

(1)第一脱醇反应:(1) The first dealcoholization reaction:

将油浴温度设定为5℃,向三口烧瓶中加入22.2g(0.1mol)脲丙基三甲氧基硅烷与0.2g二氮杂二环,并开启搅拌。称取10g(0.05mol)二苯基硅二醇溶解于10g四氢呋喃中,接着将所得溶液倒入恒压滴液漏斗,30分钟内滴加到上述三口烧瓶中,滴加完毕之后继续在5℃下搅拌反应2h,之后升温至60℃继续反应3h,停止反应。用甲酸中和二氮杂二环,加少量无水甲醇,分层去除二氮杂二环-甲酸盐,接着在减压下蒸除目标产物中的溶剂四氢呋喃,得到含有端甲氧基的脲基预聚体,干燥保存,产率为95%。Set the temperature of the oil bath to 5° C., add 22.2 g (0.1 mol) of ureapropyltrimethoxysilane and 0.2 g of diazabicyclo into the three-necked flask, and start stirring. Weigh 10g (0.05mol) of diphenylsilanediol and dissolve it in 10g of tetrahydrofuran, then pour the resulting solution into a constant pressure dropping funnel, and drop it into the above-mentioned three-necked flask within 30 minutes. The reaction was stirred under low temperature for 2h, and then the temperature was raised to 60°C to continue the reaction for 3h, and the reaction was stopped. Neutralize the diazabicyclo with formic acid, add a small amount of anhydrous methanol, remove the diazabicyclo-formate by layering, and then distill off the solvent tetrahydrofuran in the target product under reduced pressure to obtain the compound containing the terminal methoxy group. Urea-based prepolymer, stored dry, with a yield of 95%.

(2)第二脱醇反应:(2) The second dealcoholization reaction:

将油浴温度设定为50℃,向三口烧瓶中加入0.2g二氮杂二环、37.2g(0.2mol)四甲基二乙烯基二硅氧烷和0.36g水,搅拌反应3h后降温至5℃。称取上述预聚体28g溶于15g二甲基甲酰胺,接着将所得溶液置于恒压滴液漏斗中,35分钟内滴加到三口烧瓶中,滴加完毕之后继续在5℃下搅拌反应3h,之后升温至60℃继续反应5h停止反应。用甲酸中和二氮杂二环,加少量无水甲醇,分层去除二氮杂二环-甲酸盐,接着在减压下蒸除目标产物中的溶剂二甲基甲酰胺,得到有机硅化合物(记为G2),产率为93%。Set the temperature of the oil bath to 50°C, add 0.2g of diazabicyclo, 37.2g (0.2mol) of tetramethyldivinyldisiloxane and 0.36g of water into the three-necked flask, stir and react for 3 hours, then cool down to 5°C. Weigh 28g of the above-mentioned prepolymer and dissolve it in 15g of dimethylformamide, then place the resulting solution in a constant pressure dropping funnel, drop it into a three-necked flask within 35 minutes, and continue to stir and react at 5°C after the dropwise addition is completed After 3h, the temperature was raised to 60°C to continue the reaction for 5h to stop the reaction. Neutralize the diazabicyclo with formic acid, add a small amount of anhydrous methanol, remove the diazabicyclo-formate by layering, and then distill off the solvent dimethylformamide in the target product under reduced pressure to obtain organosilicon Compound (denoted as G2), the yield was 93%.

经红外和核磁检测可知,该有机硅化合物具有式(I)所示的结构,其中,R1-R8均为甲基,R9和R10均为亚丙基。According to infrared and nuclear magnetic detection, the organosilicon compound has the structure shown in formula (I), wherein, R 1 -R 8 are all methyl groups, and R 9 and R 10 are all propylene groups.

制备例3Preparation example 3

该制备例用于说明本发明提供的有机硅化合物及其制备方法。This preparation example is used to illustrate the organosilicon compound provided by the present invention and its preparation method.

(1)第一脱醇反应:(1) The first dealcoholization reaction:

将油浴温度设定为3℃,向三口烧瓶中加入22.2g(0.1mol)脲丙基三甲氧基硅烷与0.2g三乙烯四胺,并开启搅拌。称取10g(0.05mol)二苯基硅二醇溶解于10g四氢呋喃中,接着将所得溶液倒入恒压滴液漏斗,25分钟内滴加到上述三口烧瓶中,滴加完毕之后继续在3℃下搅拌反应2h,之后升温至60℃继续反应3h,停止反应。用甲酸中和三乙烯四胺,加少量无水甲醇,分层去除三乙烯四胺-甲酸盐,接着在减压下蒸除目标产物中的溶剂四氢呋喃,得到含有端甲氧基的脲基预聚体,干燥保存,产率为89%。Set the temperature of the oil bath to 3° C., add 22.2 g (0.1 mol) of ureapropyltrimethoxysilane and 0.2 g of triethylenetetramine into the three-necked flask, and start stirring. Weigh 10g (0.05mol) of diphenylsilanediol and dissolve it in 10g of tetrahydrofuran, then pour the resulting solution into a constant pressure dropping funnel, and drop it into the above-mentioned three-necked flask within 25 minutes. The reaction was stirred under low temperature for 2h, and then the temperature was raised to 60°C to continue the reaction for 3h, and the reaction was stopped. Neutralize triethylenetetramine with formic acid, add a small amount of anhydrous methanol, remove triethylenetetramine-formate by layering, and then distill off the solvent tetrahydrofuran in the target product under reduced pressure to obtain a ureido group containing a methoxy-terminal The prepolymer was stored dry, with a yield of 89%.

(2)第二脱醇反应:(2) The second dealcoholization reaction:

将油浴温度设定为50℃,向三口烧瓶中加入0.2g三乙烯四胺、37.2g(0.2mol)四甲基二乙烯基二硅氧烷和0.36g水,搅拌反应3h后降温至3℃。称取上述预聚体28g溶于15g二氧六环,接着将所得溶液置于恒压滴液漏斗中,38分钟内滴加到三口烧瓶中,滴加完毕之后继续在3℃下搅拌反应3h,之后升温至60℃继续反应5h,停止反应。用甲酸中和三乙烯四胺,加少量无水甲醇,分层去除三乙烯四胺-甲酸盐,接着在减压下蒸除目标产物中的溶剂二氧六环,得到有机硅化合物(记为G3),产率为87%。Set the temperature of the oil bath at 50°C, add 0.2g of triethylenetetramine, 37.2g (0.2mol) of tetramethyldivinyldisiloxane and 0.36g of water into the three-necked flask, stir the reaction for 3h and cool down to 3 ℃. Weigh 28g of the above prepolymer and dissolve it in 15g of dioxane, then place the obtained solution in a constant pressure dropping funnel, drop it into a three-necked flask within 38 minutes, and continue to stir and react at 3°C for 3h after the dropwise addition is completed , then the temperature was raised to 60° C. to continue the reaction for 5 h, and the reaction was stopped. Neutralize triethylenetetramine with formic acid, add a small amount of anhydrous methanol, remove triethylenetetramine-formate by layering, then distill off the solvent dioxane in the target product under reduced pressure to obtain organosilicon compound (note is G3), the yield was 87%.

经红外和核磁检测可知,该有机硅化合物具有式(I)所示的结构,其中,R1-R8均为甲基,R9和R10均为亚丙基。According to infrared and nuclear magnetic detection, the organosilicon compound has the structure shown in formula (I), wherein, R 1 -R 8 are all methyl groups, and R 9 and R 10 are all propylene groups.

实施例1Example 1

该实施例用于说明本发明提供的LED封装材料的制备方法。This embodiment is used to illustrate the preparation method of the LED encapsulation material provided by the present invention.

将99g硅胶与1g有机硅化合物G1搅拌共混均匀,得到LED封装材料,记为C1。Stir and blend 99g of silica gel and 1g of organosilicon compound G1 evenly to obtain an LED packaging material, which is denoted as C1.

实施例2Example 2

该实施例用于说明本发明提供的LED封装材料的制备方法。This embodiment is used to illustrate the preparation method of the LED encapsulation material provided by the present invention.

将98g硅胶与2g有机硅化合物G2搅拌共混均匀,得到LED封装材料,记为C2。Stir and blend 98g of silica gel and 2g of organosilicon compound G2 evenly to obtain an LED encapsulation material, denoted as C2.

实施例3Example 3

该实施例用于说明本发明提供的LED封装材料的制备方法。This embodiment is used to illustrate the preparation method of the LED encapsulation material provided by the present invention.

将98.5g硅胶与1.5g有机硅化合物G3搅拌共混均匀,得到LED封装材料,记为C3。Stir and blend 98.5g of silica gel and 1.5g of organosilicon compound G3 evenly to obtain an LED packaging material, which is denoted as C3.

实施例4Example 4

该实施例用于说明本发明提供的LED封装材料的制备方法。This embodiment is used to illustrate the preparation method of the LED encapsulation material provided by the present invention.

将99.8g硅胶与0.2g有机硅化合物G1搅拌共混均匀,得到LED封装材料,记为C4。Stir and blend 99.8g of silica gel and 0.2g of organosilicon compound G1 evenly to obtain an LED packaging material, which is denoted as C4.

对比例1Comparative example 1

该对比例用于说明参比的LED封装材料的制备方法。This comparative example is used to illustrate the preparation method of the reference LED encapsulation material.

采用空白硅胶样品作为对比样品,不添加有机硅化合物,得到参比LED封装材料,记为DC1。A blank silica gel sample was used as a comparative sample, and no organic silicon compound was added to obtain a reference LED packaging material, which was denoted as DC1.

测试例test case

测试例用于说明LED封装材料粘接力的测试。The test example is used to illustrate the test of the adhesive force of the LED encapsulation material.

取两片规格均为长80mm、宽20mm、厚0.65mm的表面镀有银的铜片,在两银面之间分别采用封装材料C1-C4以及参比封装材料DC1均匀涂布厚度为1mm的涂层,两银片平行摆放且相互搭接长度为20mm。随后在150℃下后固化4小时,冷却至室温,试样刚制备完成后以及在85℃/85%RH条件下放置100小时之后分别进行粘接力测试。具体地,采用粘接力测试仪(购自深圳三思纵横科技股份有限公司,型号为CMT4503)在5mm/min的速度下沿两银片表面反向拉伸,测试拉伸过程中拉伸力的最大值,粘接力测试时每个实施例及对比例平行测试5个样品,将5个样品的测试结果取平均值作为该实施例及对比例的粘接力测试结果。结果见表1。Take two pieces of silver-plated copper sheets with specifications of 80mm in length, 20mm in width, and 0.65mm in thickness, and use packaging materials C1-C4 and reference packaging material DC1 to evenly coat the copper sheets with a thickness of 1mm between the two silver surfaces. Coating, two silver sheets are placed in parallel and the overlapping length is 20mm. Then post-cured at 150°C for 4 hours, cooled to room temperature, and the adhesion test was carried out immediately after the sample was prepared and after being placed under the condition of 85°C/85%RH for 100 hours. Specifically, an adhesion tester (purchased from Shenzhen Sansi Zongheng Technology Co., Ltd., model CMT4503) was used to reversely stretch the surfaces of the two silver sheets at a speed of 5mm/min, and the tensile force during the test was tested. Maximum value, during the adhesion test, 5 samples were tested in parallel in each embodiment and comparative example, and the test results of the 5 samples were averaged as the adhesion test results of the embodiment and comparative example. The results are shown in Table 1.

表1Table 1

编号Numbering 粘接力(放置0小时,MPa)Adhesive force (placed for 0 hours, MPa) 粘接力(放置100小时,MPa)Adhesive force (placed for 100 hours, MPa) 实施例1Example 1 3.553.55 3.483.48 实施例2Example 2 3.643.64 3.603.60 实施例3Example 3 3.823.82 3.833.83 实施例4Example 4 3.133.13 3.063.06 对比例1Comparative example 1 2.892.89 2.562.56

从以上结果可以看出,将具有式(I)所示的结构的有机硅化合物加入封装硅胶中之后,可以显著提升硅胶的粘接力,并且封装硅胶固化后仍能长期保持较高的粘接力,从而能够显著提高LED灯珠的使用寿命。It can be seen from the above results that after adding the organosilicon compound with the structure shown in formula (I) into the encapsulation silica gel, the adhesive force of the silica gel can be significantly improved, and the encapsulation silica gel can still maintain high adhesion for a long time after curing. Force, which can significantly improve the service life of LED lamp beads.

以上详细描述了本发明的优选实施方式,但是,本发明并不限于上述实施方式中的具体细节,在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,这些简单变型均属于本发明的保护范围。The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solutions of the present invention. These simple modifications All belong to the protection scope of the present invention.

另外需要说明的是,在上述具体实施方式中所描述的各个具体技术特征,在不矛盾的情况下,可以通过任何合适的方式进行组合。为了避免不必要的重复,本发明对各种可能的组合方式不再另行说明。In addition, it should be noted that the various specific technical features described in the above specific implementation manners may be combined in any suitable manner if there is no contradiction. In order to avoid unnecessary repetition, various possible combinations are not further described in the present invention.

此外,本发明的各种不同的实施方式之间也可以进行任意组合,只要其不违背本发明的思想,其同样应当视为本发明所公开的内容。In addition, various combinations of different embodiments of the present invention can also be combined arbitrarily, as long as they do not violate the idea of the present invention, they should also be regarded as the disclosed content of the present invention.

Claims (11)

1. a kind of organo-silicon compound, which is characterized in that the organo-silicon compound have the structure shown in formula (I):
Wherein, R1-R8It is each independently C1-C5Alkyl, R9And R10It is each independently C1-C8Alkylidene.
2. organo-silicon compound according to claim 1, wherein, R1-R8It is each independently C1-C3Alkyl, R9And R10 It is each independently C2-C4Alkylidene.
3. a kind of preparation method of organo-silicon compound, which is characterized in that this method includes:
(1) by the urea groups alkoxy silane shown in the diphenyl silanediol shown in formula (II) and formula (III) in the first base catalysis The first dealcoholization is carried out in the presence of agent and the first solvent;
(2) by the divinyl disiloxane shown in the product of first dealcoholization and formula (IV) in the second basic catalyst With the second dealcoholization is carried out in the presence of the second solvent;
Wherein, R9For C1-C8Alkylidene, R11-R13It is each independently C1-C5Alkyl, R14-R17It is each independently C1-C5 Alkyl.
4. according to the method described in claim 3, wherein, R9For C2-C4Alkylidene, R11-R13It is each independently C1-C3's Alkyl, R14-R17It is each independently C1-C3Alkyl.
5. method according to claim 3 or 4, wherein, the dosage of the diphenyl silanediol and the urea groups alkoxy The molar ratio of the dosage of silane is (0.2-2): 1;The dosage of the divinyl disiloxane and the urea groups alkoxy silane Dosage molar ratio be (0.5-2): 1.
6. method according to claim 3 or 4, wherein, first basic catalyst and the second basic catalyst are respectively It independently is at least one of triethylamine, triethylene diamine, pyridine and diazabicylo;First solvent and the second solvent It is each independently at least one of tetrahydrofuran, dioxane, dimethylformamide and dimethylacetylamide.
7. method according to claim 3 or 4, wherein, the condition phase of first dealcoholization and the second dealcoholization It is same or different, and the low temperature polymerization reaction for including carrying out successively each independently is reacted, and the low temperature polymerization with high temperature polymerization The condition of reaction is 0-5 DEG C including temperature and the time is 2-8h, and it is 40-80 DEG C that the condition of the high temperature polymerization reaction, which includes temperature, And the time is 2-10h.
8. the organo-silicon compound being prepared as the method described in any one in claim 3-7.
9. application of the organo-silicon compound described in claim 1,2 or 8 as adhesive accelerant.
10. a kind of LED encapsulation material, the LED encapsulation material contains silica gel, which is characterized in that the LED encapsulation material also contains The organo-silicon compound having the right described in requirement 1,2 or 8.
11. LED encapsulation material according to claim 10, wherein, on the basis of the total weight of the LED encapsulation material, The content of the silica gel is 95-99.5 weight %, and the content of the organo-silicon compound is 0.5-5 weight %.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019077855A1 (en) * 2017-10-16 2019-04-25 信越化学工業株式会社 Urea group-containing organopolysiloxane, method for producing urea group-containing organopolysiloxane, and cosmetic preparation

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0507727A2 (en) * 1991-03-06 1992-10-07 Ciba-Geigy Ag Glass coating with improved adhesion and weather resistance
EP0406160B1 (en) * 1989-06-13 1994-02-02 Ciba-Geigy Ag Primer
CN1788038A (en) * 2003-05-13 2006-06-14 德古萨公司 Organofunctional siloxane mixtures
CN1806025A (en) * 2003-06-13 2006-07-19 陶氏康宁东丽株式会社 Silicone-based pressure-sensitive adhesive and adhesive tape
CN102329336A (en) * 2010-06-02 2012-01-25 信越化学工业株式会社 Ureido silane compound and room temperature curable organopolysiloxane composition
CN102898651A (en) * 2012-10-25 2013-01-30 浙江润禾有机硅新材料有限公司 Preparation method of vinylphenyl silicon resin for LED (light-emitting diode) packaging
CN104768996A (en) * 2012-09-07 2015-07-08 温科莱斯法国公司 Composition of allophanate and hydrophobic resin
CN105778101A (en) * 2014-12-18 2016-07-20 北京科化新材料科技有限公司 Phenyl vinyl silicone oil and preparation method thereof
CN105778099A (en) * 2014-12-18 2016-07-20 北京科化新材料科技有限公司 Phenyl hydrogen-containing silicone oil and preparation method thereof

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0406160B1 (en) * 1989-06-13 1994-02-02 Ciba-Geigy Ag Primer
EP0507727A2 (en) * 1991-03-06 1992-10-07 Ciba-Geigy Ag Glass coating with improved adhesion and weather resistance
CN1788038A (en) * 2003-05-13 2006-06-14 德古萨公司 Organofunctional siloxane mixtures
CN1806025A (en) * 2003-06-13 2006-07-19 陶氏康宁东丽株式会社 Silicone-based pressure-sensitive adhesive and adhesive tape
CN102329336A (en) * 2010-06-02 2012-01-25 信越化学工业株式会社 Ureido silane compound and room temperature curable organopolysiloxane composition
CN104768996A (en) * 2012-09-07 2015-07-08 温科莱斯法国公司 Composition of allophanate and hydrophobic resin
CN102898651A (en) * 2012-10-25 2013-01-30 浙江润禾有机硅新材料有限公司 Preparation method of vinylphenyl silicon resin for LED (light-emitting diode) packaging
CN105778101A (en) * 2014-12-18 2016-07-20 北京科化新材料科技有限公司 Phenyl vinyl silicone oil and preparation method thereof
CN105778099A (en) * 2014-12-18 2016-07-20 北京科化新材料科技有限公司 Phenyl hydrogen-containing silicone oil and preparation method thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019077855A1 (en) * 2017-10-16 2019-04-25 信越化学工業株式会社 Urea group-containing organopolysiloxane, method for producing urea group-containing organopolysiloxane, and cosmetic preparation

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