TWI516544B - Organic-inorganic hybrid resin, composition employing the same, and photoelectric device - Google Patents

Description

An organic-inorganic hybrid resin, a molding composition containing the same, and Photoelectric device

The present invention relates to an organic-inorganic hybrid resin, a molding composition comprising the same, and an optoelectronic device.

Light emitting diode (LED) has many advantages such as energy saving (power saving), small size, long life, fast response, low pollution, high reliability, and large module flexibility. Therefore, the application range is very wide. In recent years, the technology has continuously improved, and the efficiency and brightness of the light-emitting diodes have been continuously improved, so that the application range is gradually extended to the display backlight module and the vehicle light source. In the future, I hope to replace the existing fluorescent lamps and become the next generation of new lighting sources. High-power and high-brightness LEDs will become the mainstream of future development, and their demand will also increase.

In the case of the existing light-emitting diode package structure, a reflective cup is exemplified, which may be composed of a resin or a ceramic material. Although ceramic materials have good mechanical strength, ceramic materials are not easy to be used to make reflective cups with smaller sizes, and reflective cups formed of ceramic materials are not conducive to light reflection. Therefore, at present, a display device made of a resin material is used as a display device using a light-emitting diode as a light-emitting source.

Resin materials conventionally used for moldability compositions (for example, polyparaphenylene terephthalamide, PPA) have poor photothermal stability, so when subjected to long-time operation at higher operating temperatures, significant yellowing occurs. And problems such as material deterioration. Further, since a moldable composition using a conventional resin material is used, the reaction rate is slow and the fluidity is poor in the transfer molding process, which also causes problems such as long molding time and poor workability.

Based on the above, there is a need in the industry for a molded composition having high photothermal stability, good processability, and rapid formability to solve the problems encountered in the prior art.

According to an embodiment of the present invention, the present invention provides an organic-inorganic hybrid resin which is a reaction product of a composition, wherein the composition comprises: 0.1 to 10 parts by weight of the starting material (a), wherein the starting material ( a) is a silsesquioxane prepolymer having a metal oxide cluster, wherein the metal is titanium (Ti), zirconium (Zr), zinc (Zn), Or a combination of the above; and 100 parts by weight of the starting material (b), wherein the starting material (b) is an epoxy resin.

According to another embodiment of the present invention, the present invention also provides a molding composition. The molding composition comprises: the above organic-inorganic hybrid resin; an inorganic filler; a hardener; and, a white pigment.

According to other embodiments of the invention, the invention also provides an optoelectronic device. The photovoltaic device comprises: a reflective cup; and a photovoltaic element is disposed in the reflective cup, wherein the reflective cup is mixed by the molding composition A cured product obtained by a kneading process and a transfer molding process.

10‧‧‧Optoelectronic devices

12‧‧‧Optoelectronic components

14‧‧‧Reflection Cup

1 is a schematic view of an optoelectronic device according to an embodiment of the present invention.

The present invention discloses an organic-inorganic hybrid resin, a molding composition comprising the same, and an optoelectronic device. The organic-inorganic hybrid resin of the present invention is reacted with an epoxy resin by a silsesquioxane prepolymer having a metal oxide cluster having a rapidly reactive polyfunctional group. Forming wherein the weight fraction of the sesquioxane prepolymer having a metal oxide cluster is between about 0.1 and 10 (the epoxy resin is 100 parts by weight) to ensure the obtained organic and inorganic The mixed resin has a melt flowability (having a melt viscosity ranging from 100 to 10,000 mPa.s) at a temperature of less than 50 ° C as a no-flow solid (i.e., a melting point of more than 50 ° C) and heating to a temperature range of 80 to 150 ° C. On the other hand, the organic-inorganic hybrid resin of the present invention can be further mixed with other epoxy resins, hardeners, inorganic fillers, white pigments, and additives to form a molded composition. The kneaded product of the molding composition of the present invention has good processability due to high fluidity when subjected to a transfer molding process. Further, since the organic-inorganic hybrid resin still has an unreacted epoxy group, the molded composition can be made to have rapid reactivity (curing in 150 seconds) when subjected to a transfer molding process. Furthermore, the molded composition of the present invention can obtain a white cured product after the kneading process and the transfer molding process. The solid The compound can have a reflectance of about 90% for a light having a wavelength of 450 nm, and the cured product has high photothermal stability, and thus can be widely used as a molding material for a package structure of various photovoltaic devices.

The organic-inorganic hybrid resin of the present invention may be a reaction product of a composition, wherein the composition comprises: about 0.1-10 parts by weight (for example, 1-10 parts by weight) of the starting material (a), wherein the starting material The starting material (a) is a sesquisesquioxane prepolymer having a metal oxide cluster, wherein the metal is titanium (Ti), zirconium (Zr), zinc (Zn), or a combination thereof; 100 parts by weight of the starting material (b), wherein the starting material (b) may be an epoxy resin. If the content of the starting material (a) (the sesquisesquioxane prepolymer having a metal oxide cluster) is too high, the melting temperature of the obtained organic-inorganic hybrid resin may be higher than 150 ° C due to excessive crosslinking, or even heating. When it is more than 200 ° C, it is not melted, and thus the reactivity, fluidity, and processability of the obtained molding material are lowered. Further, the organic-inorganic hybrid resin of the present invention is formed by reacting a specific proportion of a sesquioxane prepolymer having a metal oxide cluster with an epoxy resin, and has a melting between 80 and 120 ° C. The viscosity is between 100 and 10,000 mPa.s and still has an unreacted epoxy group.

According to the embodiment of the present invention, the fluidity and processability of the molding material obtained by the present invention can be adjusted in the subsequent transfer molding process by controlling the melt viscosity of the organic-inorganic hybrid resin of the present invention. The weight average molecular weight distribution of the starting material (a) metal oxide cluster of the sesquisesquioxane prepolymer of the present invention may be between 2,500 and 7,800 to ensure that the obtained molding material is subsequently molded. The process has sufficient fluidity and processability.

According to an embodiment of the present invention, the starting material (a) may be a reaction product of a composition, wherein the composition comprises: 1-10 parts by weight of the starting material (d), 100 parts by weight of the starting material (e) And 5-20 parts by weight of the starting material (f). Wherein, the starting material (d) may have the structure represented by the formula (I):

Wherein R ¹ is independently a C _1-10 alkyl group, and n is a positive integer selected from 4-31. The starting material (e) may be a titanium alkoxide, a zirconium alkoxide, a zinc alkoxide, or a combination thereof, such as zirconium ethoxide, zirconium isopropoxide, zirconium n-propoxide, zirconium n-butoxide, zirconium tert-butoxide. , zinc ethoxide, zinc isopropoxide, zinc n-propoxide, zinc n-butoxide, zinc d-butoxide, titanium ethoxide, titanium isopropoxide, titanium n-propoxide, titanium n-butoxide, titanium t-butoxide, or Combination of the above. The starting material (f) may have the structure represented by the formula (II):

Wherein R ² is independently a C _1-3 alkoxy group, and an R ³ system C _3-12 epoxy group, a C _3-12 acrylate group, a C _4-12 alkyl acrylate An alkylacryloxy group or a C _3-12 alkenyl group. According to an embodiment of the present invention, the starting material (f) may be, for example, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3- 3-Glycidoxypropyltrimethoxysilane, 3-Glycidoxypropyl methoxydiethoxysilane, 3-Glycidoxypropyl Triethoxysilane), 3-methacryloxypropyl trimethoxysilane, 3-Methacryloxypropyl triethoxysilane, or 3-acrylic propyltrimethoxysilane 3-acryloxypropyl trimethoxysilane. According to an embodiment of the present invention, the composition may further comprise: 3-10 parts by weight of the starting material (g), wherein the starting material (g) is water, ammonium hydroxide (NH ₄ OH), or a combination thereof .

According to an embodiment of the present invention, the starting material (a) may have a structure represented by the formula (III):

Wherein R ¹ is independently C _{1 -10} alkyl; n is a positive integer selected from 4-31; and, Y is (MO _4/2 ) _l [(MO) _(4-a)/2 M(OH _a/2 ] _m [MO _(4-b)/2 M(OZ) _b/2 ] _p , wherein M is a metal; l is a positive integer from 5-20; m is selected from 2-8 a positive integer; p is a positive integer selected from 2-5; a is a positive integer selected from 1-2; b is a positive integer selected from 1-2; and, Z-SiR ³ (R ⁴ ) ₂ , wherein R ³ is independently a C _3-12 epoxy group, a C _3-12 acrylate group, a C _4-12 alkylacryloxy group, or a C _3-12 alkenyl group ( Alkenyl group); and, R ⁴ is independently a hydroxyl group or a C _1-8 alkoxy group.

In one embodiment, the sesquioxane prepolymer (starting material (a)) having a metal oxide cluster can be prepared according to the following procedure: First, the starting material (d) (with terminal hydrogen) An alkoxy sesquioxane prepolymer) is mixed with a starting material (e) (a metal alkoxide such as metal butoxide M (OBu) ₄ , M may be zirconium, titanium, or zinc) to carry out the reaction, A reaction intermediate is obtained. Next, the starting material (g) (ammonium hydroxide, and/or water) is added such that the reaction intermediate undergoes a sol-gel reaction to form a sol-gel product. Next, the starting material (f) (organofunctional decane) is added to react with the sol-gel product to obtain a sesquioxane prepolymer having a metal oxide cluster. The above reaction can be represented by the following reaction formula:

Here, the metal of the M-based metal alkoxide, for example, zirconium, titanium, zinc, or a combination thereof, and the definitions of R ¹ , R ³ , and n are the same as described above. In addition, the symbol This indicates that the bond is bonded to a ruthenium on the metal M or another organofunctional decyl group. That is, the oxygen on the ruthenium in the final product organic-inorganic hybrid resin is respectively attached to the metal M in the metal cluster structure or the lanthanum on the other organofunctional decyl group. However, it should be noted that the structures of the above reaction formulas are for illustrative purposes only, and those skilled in the art will understand the intermediate products, sol-gel products, and organic-inorganic hybrid resins formed in the various embodiments of the present invention. The size and bonding mode of the metal oxide cluster structure may be different.

According to an embodiment of the present invention, the starting material (b) may comprise a triglycidyl isocyanurate epoxy resin, a hydrogenated epoxy resin, a cycloaliphatic epoxy resin. Epoxy), silicon containing modified epoxy, or a combination thereof. In the embodiment of the present invention, the starting material (b) comprises at least a phthalate modified epoxy resin, and may further comprise a triglycidyl isocyanurate epoxy resin, a hydrogenated epoxy resin. A hydrogenated epoxy resin, a cycloaliphatic epoxy, or a combination thereof. The siloxane-modified epoxy resin of the present invention may have the structure represented by the formula (IV):

Wherein R ¹ is independently C _{1 -10} alkyl; R ⁵ is independently C _{1 -10} alkyl, or phenyl; R ⁶ is epoxycyclohexylethyl (structure is ) or epoxycyclohexylpropyl (epoxycyclohexylpropyl) R ⁷ is independently C _{1 -10} alkyl, epoxycyclohexylethyl, or epoxycyclohexylpropyl; and, 1≦c≦150, and 0≦d≦ 15, wherein, when d>0, the c/d system is between 1 and 10; and when d=0, at least one R ⁷ is an epoxycyclohexylethyl or an epoxycyclohexyl group. Epoxycyclohexylpropyl. According to an embodiment of the invention, the siloxane-modified epoxy resin may have a weight average molecular weight of between about 400 and 10,000.

According to another embodiment of the present invention, the composition for forming the organic-inorganic hybrid resin of the present invention may further comprise from about 0 to 35 parts by weight (for example, from 1 to 35 parts by weight, or from 3 to 3) to ensure that the obtained resin is in a solid state. 25 parts by weight of the starting material (c), wherein the starting material (c) is an anhydride, such as succinic anhydride, maleic anhydride, phthalic anhydride ( Phthalic anhydride, PA), tetrahydrophthalic anhydride (THPA), hexahydrophthalic anhydride (HHPA), methyltetrahydrophthalic anhydride (MTHPA), or methyl hexahydrophthalic acid (methyl hexahydrophthalic) Anhydride, MHHPA), or a combination of the above. Further, the equivalent ratio of the acid anhydride group of the starting material (c) to the epoxy group of the starting material (b) may be between about 0 and 0.5, for example, the equivalent ratio may be from 0.001 to 0.5, or 0.001 to Between 0.3 to ensure that the obtained resin prepolymer is solid, and the subsequent kneading process can be applied.

In one embodiment, the organic-inorganic hybrid resin of the present invention can be prepared according to the following steps: First, 100 parts by weight of epoxy resin (starting material (b)), 1-10 parts by weight of metal oxide a sulfonium sesquioxane prepolymer (starting material (a)), and/or 0-35 parts by weight of an acid anhydride (starting material (c)) is added to a reactor and dissolved in a solvent Medium (for example: toluene, xylene, hexane, methyl ethyl ketone, etc.). Next, after uniformly mixing and removing a part of the solvent, the resulting product is placed under vacuum for several minutes to several hours to remove residual solvent. Next, the obtained product is heated at 50 to 100 ° C for 60 to 240 minutes, and after cooling and aging, the organic-inorganic hybrid resin is obtained.

According to an embodiment of the present invention, the present invention also provides a molding composition comprising: the above organic-inorganic hybrid resin; an inorganic filler; a hardener; and a white pigment. The inorganic filler and the white pigment may have a total weight of from about 30 to 84% by weight (e.g., from about 45 to 70% by weight) based on the total weight of the molding composition. If the weight percentage of the inorganic filler and the white pigment is too low, the resulting molding material has poor mechanical properties; if the inorganic filler and the white pigment are too high in weight, the resulting molding material has poor properties. Mobility and reactivity. Further, the weight ratio of the white pigment to the inorganic filler may be between about 0.1 and 0.5, such as between 0.1 and 0.3. The organic-inorganic hybrid resin may have a weight percentage of from about 11 to 55 wt% (for example, about 15 to 40 wt%), and the hardener may have a weight percentage of from about 3 to 15 wt% to the molded composition. The total weight is the benchmark. If the weight of the organic-inorganic hybrid resin If the percentage is too low or the weight percentage of the hardener is too high, the resulting molding material has poor reactivity and excessive fluidity; if the inorganic filler and the white pigment are too high in weight or the hardener If the weight percentage is too low, the resulting molding material may cause poor workability in the transfer molding process due to poor fluidity.

According to an embodiment of the present invention, the inorganic filler may comprise cerium oxide, aluminum hydroxide, magnesium hydroxide, magnesium carbonate, cerium carbonate, or a combination thereof. The inorganic filler may be, for example, inorganic particles (for example, cerium oxide particles) having a particle diameter of between about 0.01 and 50 μm. According to another embodiment of the present invention, the inorganic filler may be composed of at least two inorganic particles of different particle size ranges to increase the fluidity and processability of the resulting molding material. The white pigment may comprise titanium oxide, aluminum oxide, magnesium oxide, zirconium oxide, calcium carbonate, zinc sulfide, zinc oxide, or a combination thereof, and the white pigment may have a particle size of between about 0.01 and 100 μm. It is to be noted that, in order to make the molded composition of the present invention into a solid state after the kneading process, and is suitable for processing in a transfer molding process, the hardener used in the molding composition is solid non- The aromatic acid anhydride is, for example, tetrahydrophthalic anhydride (THPA), hexahydrophthalic anhydride (HHPA), maleic anhydride, or a combination thereof.

According to an embodiment of the present invention, the molding composition of the present invention may further comprise an additive such as a coupling agent and/or a releasing agent. The weight percentage of the additive may be between about 0.5 and 1.5 wt% based on the total weight of the molding composition. The coupling agent may be a decane compound having a reactive functional group, such as 2-(3,4-epoxycyclohexyl)ethyltrimethyldecane. (2-(3,4-Epoxycyclohexyl)-ethyltrimethoxysilane), 3-Glycidoxypropyltrimethoxysilane, 3-Glycidoxypropyl methyldiethoxysilane, 3-Glycidoxypropyl triethoxysilane, 3-Methacryloxypropyl methyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane 3-Methacryloxypropyl trimethoxysilane, 3-Methacryloxypropyl methyldiethoxysilane, 3-Methacryloxypropyl triethoxysilane , N-2-(Aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(Aminoethyl)-3-amine N-2-(Aminoethyl)-3-aminopropyltrimethoxysilane, 3-Aminopropyltrimethoxysilane, 3-Aminopropyltriethoxysilane N-phenyl-3aminopropyltrimethoxy N-Phenyl-3-aminopropyltrimethoxysilane, 3-Ureidopropyltriethoxysilane, 3-Isocyanatepropyltriethoxysilane, 3-Chlorine 3-Chloropropyltrimethoxysilane, 1 hydrogen, 1 hydrogen, 2 hydrogen, 2H-perfluorooctyltriethoxysilane (1H, 1H, 2H, 2H-perfluorooctyltriethoxysilane), fluorohexyl 1.1.2.2-Tetrahydro sunflower triethoxy decane ((Heptadecafluoro-1,1,2,2-tetrahydrodecyl)triethoxysilane), 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, Bis(triethoxysilylpropyl)tetrasulfide, decyltrimethoxysilane, Hexyltriethoxysilane, 3-acryloxypropyl trimethoxysilane, or a combination thereof; and The release agent can be, for example, an alkylphosphonic acid, an arylphosphonic acid, a fluoroalkylnonane, a perfluorochloromethane, a fluorinated alkyl group and an arylphosphonic acid, a fatty acid ester, or a combination thereof.

The molding composition of the present invention can form a molding material via a kneading process. According to an embodiment of the present invention, the molding composition may be sufficiently stirred and uniformly mixed by an amalgamator before performing the kneading process. The kneading process can melt-knead the molding composition at 40 to 100 ° C for 10 to 120 minutes using a mixing roll, a kneader, and an extruder. After cooling, the molding material was obtained. According to another embodiment of the present invention, the molding material of the present invention can be used in a transfer molding process to form a cured product having a desired morphology (for example, a white cured product), wherein the cured product has a high light heat Stability, and for a wavelength of light of 450 nm, has a reflectivity greater than 90%. The temperature of the transfer molding process can range from 100 to 200 °C. Since the molding composition has rapid reactivity, the kneaded molding composition may have a fixing time of about 10 to 150 seconds in the transfer molding process.

According to an embodiment of the present invention, the molding composition of the present invention can form a package structure of the photovoltaic device by a kneading process and a transfer molding process. Please refer to According to Fig. 1, a schematic view of a structure of a photovoltaic device 10 according to the present invention is shown. The light emitting device 10 includes a photovoltaic element 12 (eg, a light emitting diode, a laser diode, or a light receiver), and a package structure, such as a reflective cup 14, wherein the photovoltaic element 12 is placed in the reflection Inside the cup 14. Wherein, the reflective cup is a white cured product obtained by the above-mentioned molding composition through a kneading process and a transfer molding process. Since the white cured product has a strong reflectance to the light emitted by the photovoltaic element 12 or the ambient light, it is very suitable as a material of the reflective cup for the purpose of enhancing the efficiency of the photovoltaic device 10.

The above-described and other objects, features, and advantages of the present invention will become more apparent from the claims.

Preparation of a sesquioxane prepolymer having metal oxide clusters Preparation Example 1:

First, 15.7 g of zirconium butoxide, Zr(OBu) ₄ (available from Gelest) and 200 g of butanol were added to a reaction flask and stirring was continued. Next, 0.30 g of terminal sterol-containing polydimethylsiloxane (Silanol terminated polydimethylsiloxanes; DMS-S12 from Gelest), 0.005 g of ammonium hydroxide (Ammonium hydroxide), and 45 g of butanol were stirred and mixed into a homogeneous solution. Thereafter, it was slowly added dropwise to the above reaction bottle. Subsequently, the mixture was stirred at 40 ° C for 64 hours, and the absorption peak at 950 cm ^-1 disappeared by FT-IR observation, indicating that Si-O-Zr bond formation was observed. After the reaction was completed, 390 g of butanol was added to the reaction flask. Next, 0.12 g of ammonium hydroxide, 0.59 g of deionized water, and 108 g of butanol were weighed and stirred to form a homogeneous solution, and then added to the reaction flask, and reacted at 60 ° C for 16 hours. Next, after heating to 100 ° C and heating for 24 hours, 130 g of toluene was added to the reaction flask. After reacting at 125 ° C for 72 hours, 2.57 g of 3-glycidoxypropyltrimethoxysilane (commercial number Z-6040; available from Dow Coring) was added to the reaction flask. After reacting at 125 ° C for 24 hours, the solvent of the obtained solution was completely removed and gradually phase-shifted into toluene, and the obtained sulfonium sesquioxane prepolymer (I) having a metal oxide cluster was dissolved in toluene. (toluene) in solvent. The obtained sesquioxane prepolymer (I) having a metal oxide cluster obtained by gel permeation chromatography (GPC) can be obtained by using a metal oxide cluster. The weight average molecular weight distribution of the alkane prepolymer (I) is between 2,800 and 5,000.

Preparation Example 2:

First, 26.17 g of zirconium butoxide (Zr(OBu) ₄ ; available from Gelest) and 200 g of butanol were added to a reaction flask and stirring was continued. Next, 0.30 g of terminal sterol-containing polydimethylsiloxane (Silanol terminated polydimethylsiloxanes; DMS-S12 from Gelest), 0.005 g of ammonium hydroxide (Ammonium hydroxide), and 72 g of butanol were stirred and mixed into a homogeneous solution. Thereafter, it was slowly added dropwise to the above reaction bottle. Subsequently, the mixture was stirred at 40 ° C for 64 hours, and the absorption peak at 950 cm ^-1 disappeared by FT-IR observation, indicating that Si-O-Zr bond formation was observed. After the reaction was completed, 390 g of butanol was added to the reaction flask. Next, 0.20 g of ammonium hydroxide, 0.98 g of deionized water, and 108 g of butanol were weighed and stirred to form a homogeneous solution, and then added to the reaction flask, and reacted at 60 ° C for 16 hours. Next, after heating to 100 ° C and heating for 24 hours, 130 g of toluene was added to the reaction flask. After reacting at 125 ° C for 72 hours, 4.29 g of 3-glycidoxypropyltrimethoxysilane (commercial number: available from Dow Coring) was added to the reaction flask. After reacting at 125 ° C for 24 hours, the solvent of the obtained solution was completely removed and gradually phase-shifted into toluene, and the obtained sulfonium sesquioxane prepolymer (II) having a metal oxide cluster was dissolved in toluene. (toluene) in solvent. The obtained sesquioxane prepolymer (II) having a metal oxide cluster obtained by gel permeation chromatography (GPC) can be obtained by using a metal oxide cluster. The weight average molecular weight distribution of the alkane prepolymer (II) is between 4,000 and 7800.

Preparation of organic-inorganic hybrid resin Preparation Example 3:

First, take 100 parts by weight of a decyl oxide modified epoxy resin (1) (chemical structure is , n>1, weight average molecular weight (Mw) between 800 and 1000, and epoxy resin equivalent weight (EEW) between 400-500) and 1 part by weight of metal oxide clusters The semioxyalkylene prepolymer (I) is fed to a reactor and dissolved in toluene. Then, it stirred for 20 minutes at normal temperature. After homogeneous mixing, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 80 ° C for 120 minutes, and after cooling, an organic-inorganic mixed resin (I) was obtained, showing a colorless, non-flowing state. Finally, the obtained organic-inorganic hybrid resin (I) was measured for melting temperature and viscosity, and the results are shown in Table 1.

Preparation Example 4:

First, take 100 parts by weight of a decyl oxide modified epoxy resin (1) (chemical structure is , n>1, weight average molecular weight (Mw) between 800 and 1000, and epoxy resin equivalent weight (EEW) between 400-500), 1 part by weight of metal oxide clusters The semi-oxyalkylene prepolymer (I), and 3.4 parts by weight of hexahydrophthalic anhydride (HHPA) were charged into a reactor and dissolved in toluene. Subsequently, the mixture was stirred at normal temperature for 20 minutes, and after uniformly mixing, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 90 ° C for 80 minutes, and after cooling, an organic-inorganic mixed resin (II) was obtained, showing a colorless, non-flowing state. Finally, the obtained organic-inorganic hybrid resin (II) was measured for melting temperature and viscosity, and the results are shown in Table 1.

Preparation Example 5:

First, take 100 parts by weight of a decyl oxide modified epoxy resin (1) (chemical structure is , n>1, weight average molecular weight (Mw) between 800 and 1000, and epoxy resin equivalent weight (EEW) between 400-500), and 5 parts by weight of metal oxide clusters The semi-oxyalkylene prepolymer (I), and 3.4 parts by weight of hexahydrophthalic anhydride (HHPA) were charged into a reactor and dissolved in toluene. Next, after uniformly stirring at room temperature for 20 minutes, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 80 ° C for 140 minutes, and after cooling, an organic-inorganic mixed resin (III) was obtained, showing a colorless, non-flowing state. Finally, the obtained organic-inorganic hybrid resin (III) was measured for melting temperature and viscosity, and the results are shown in Table 1.

Preparation Example 6:

First, take 100 parts by weight of a decyl oxide modified epoxy resin (1) (chemical structure is , n>1, weight average molecular weight (Mw) between 800 and 1000, and epoxy resin equivalent weight (EEW) between 400-500), 10 parts by weight of metal oxide clusters The semi-oxyalkylene prepolymer (I), and 3.4 parts by weight of hexahydrophthalic anhydride (HHPA) were charged into a reactor and dissolved in toluene. Next, after uniformly stirring at room temperature for 20 minutes, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 90 ° C for 140 minutes, and after cooling, an organic-inorganic hybrid resin (IV) was obtained, showing a colorless, non-flowing state. Finally, the obtained organic-inorganic hybrid resin (IV) was measured for melting temperature and viscosity, and the results are shown in Table 1.

Preparation Example 7:

First, take 100 parts by weight of a decyl oxide modified epoxy resin (1) (chemical structure is , n>1, weight average molecular weight (Mw) between 800 and 1000, and epoxy equivalent weight (EEW) of between 400 and 500, and 10 parts by weight of metal oxide clusters The sesquioxane prepolymer (I) is fed to a reactor and dissolved in toluene. Next, after uniformly stirring at room temperature for 20 minutes, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 80 ° C for 240 minutes, and after cooling, an organic-inorganic mixed resin (V) was obtained, showing a colorless, non-flowing state. Finally, the obtained organic-inorganic hybrid resin (V) was measured for melting temperature and viscosity, and the results are shown in Table 1.

Preparation Example 8:

First, take 100 parts by weight of a decyl oxide modified epoxy resin (1) (chemical structure is , n>1, weight average molecular weight (Mw) between 800 and 1000, and epoxy resin equivalent weight (EEW) between 400-500), and 5 parts by weight of metal oxide clusters The semi-oxyalkylene prepolymer (II), and 3.4 parts by weight of hexahydrophthalic anhydride (HHPA) were charged into a reactor and dissolved in toluene. Next, after uniformly stirring at room temperature for 20 minutes, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 90 ° C for 110 minutes, and after cooling, an organic-inorganic mixed resin (VI) was obtained, showing a colorless, non-flowing state. Finally, the obtained organic-inorganic hybrid resin (VI) was measured for melting temperature and viscosity, and the results are shown in Table 1.

Preparation Example 9:

First, take 100 parts by weight of a decane modified epoxy resin (2) (chemical structure is , n>1, m>1, weight average molecular weight (Mw) between 2400 and 26000, epoxy resin epoxy equivalent weight (EEW) between 250-350), 5 parts by weight of metal oxide cluster The sulfonium sesquioxane prepolymer (I) and 4.56 parts by weight of hexahydrophthalic anhydride (HHPA) were charged into a reactor and dissolved in toluene. Next, after uniformly stirring at room temperature for 20 minutes, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 90 ° C for 100 minutes, and after cooling, an organic-inorganic mixed resin (VII) was obtained, showing a colorless, non-flowing state. Finally, the obtained organic-inorganic hybrid resin (VII) was measured for melting temperature and viscosity, and the results are shown in Table 1.

Preparation Example 10:

First, take 100 parts by weight of a decyl oxide modified epoxy resin (1) (chemical structure is , n>1, weight average molecular weight (Mw) between 800 and 1000, and epoxy resin equivalent weight (EEW) between 400-500), and 5 parts by weight of metal oxide clusters The semi-oxyalkylene prepolymer (I), and 3.69 parts by weight of tetrahydrophthalic anhydride (THPA) were charged into a reactor and dissolved in toluene. Next, after uniformly stirring at room temperature for 20 minutes, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 80 ° C for 150 minutes, and after cooling, an organic-inorganic hybrid resin (VIII) was obtained, showing a colorless, non-flowing state. Finally, the obtained organic-inorganic hybrid resin (VIII) was measured for melting temperature and viscosity, and the results are shown in Table 1.

Preparation 11:

First, take 80 parts by weight of a nonoxyl modified epoxy resin (1) (chemical structure is , n>1, weight average molecular weight (Mw) between 800 and 1000, and epoxy resin equivalent weight (EEW) between 400-500), 20 parts by weight of alicyclic epoxy resin (product number Addition to a reactor for CEL 2021P, available from DAICEL), 5 parts by weight of a sesquioxane prepolymer (I) having a metal oxide cluster, and 6.5 parts by weight of hexahydrophthalic anhydride (HHPA) Medium and soluble in toluene. Next, after uniformly stirring at room temperature for 20 minutes, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 80 ° C for 180 minutes, and after cooling, an organic-inorganic mixed resin (IX) was obtained, showing a colorless, non-flowing state. Finally, the obtained organic-inorganic hybrid resin (IX) was measured for melting temperature and viscosity, and the results are shown in Table 1.

Preparation Example 12:

First, take 100 parts by weight of a decyl oxide modified epoxy resin (1) (chemical structure is , n>1, weight average molecular weight (Mw) between 800 and 1000, and epoxy equivalent weight (EEW) of between 400 and 500, and 15 parts by weight of metal oxide clusters The sesquioxane prepolymer (I) is fed to a reactor and dissolved in toluene. Subsequently, the mixture was stirred at normal temperature for 20 minutes, and after uniformly mixing, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 90 ° C for 140 minutes, and after cooling, an organic-inorganic hybrid resin (X) was obtained, showing a colorless, non-flowing state. Finally, the obtained organic-inorganic hybrid resin (X) was measured for melting temperature and viscosity, and the results are shown in Table 1.

Preparation Example 13:

First, 100 parts by weight of an alicyclic epoxy resin (product number CEL 2021P, available from DAICEL), and 122 parts by weight of methyl hexahydrophthalic anhydride (MHHPA) are added to a reactor and dissolved. In toluene. Next, after uniformly stirring at room temperature for 20 minutes, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 90 ° C for 240 minutes, and after cooling, the resin (I) was obtained to give a colorless liquid. The results are shown in Table 1.

Preparation Example 14:

First, 100 parts by weight of a novolac epoxy resin (product number ECN1273, available from Ciba-Geigy), and 150 parts by weight of a phenolic hardener (product number HRJ1166, available from Schenectady Chemicals) were added to a reactor. Medium and soluble in toluene. Next, it was stirred at normal temperature for 20 minutes to remove a part of toluene. After homogeneous mixing, the resulting product was placed under vacuum for 1 hour to remove residual solvent. Next, the obtained product was heated at 60 ° C for 150 minutes, cooled and aged to obtain a resin (II), which was in a colorless, non-flowing state. Finally, the obtained resin (II) was measured for melting temperature and viscosity, and the results are shown in Table 1.

It can be seen from Table 1 that when the amount of the sesquioxane prepolymer of the present invention is less than 10 parts by weight and the amount of the siloxane-modified epoxy resin is maintained at 100 parts by weight, the obtained organic-inorganic hybrid resin It is a colorless solid and is suitable for use in a kneading process and therefore can be used as a component of a molding composition. On the other hand, when the amount of the sesquioxane prepolymer of the present invention is more than 10 parts by weight (the amount of the siloxane-modified epoxy resin (1) is 100 parts by weight), the obtained organic Although the inorganic mixed resin (X) is still a colorless solid, the degree of crosslinking is increased due to the excessive addition amount of the sesquisesquioxane prepolymer (I), and the obtained organic-inorganic hybrid resin (X) is heated to 200 ° C or higher. It still cannot be melted and therefore cannot be used in molding compositions. Further, in the preparation of the resin (I) described in Preparation Example 13, the alicyclic epoxy resin was replaced by the addition of the sesquioxane prepolymer having the metal oxide cluster of the present invention, even if A large amount of a hardener (addition amount of more than 100 parts by weight) is added, and the obtained resin cannot maintain a solid state at room temperature, so that a kneading process cannot be performed, and thus it is not suitable for use in a molding composition. On the other hand, in the preparation of the resin (II) described in Preparation Example 14, the phenolic epoxy resin was used instead of the sesquioxane prepolymer having a metal oxide cluster as described in the present invention. The resulting resin is brown. Therefore, when the resin is applied to a molding composition, it is difficult to obtain a white solid.

Molding of molding composition Example 1

The organic-inorganic hybrid resin (III), hexahydrophthalic anhydride (HHPA), and inorganic filler obtained in Preparation Example 5 (fused silica) having an average particle diameter (D50) of 4.9 μm and 19.9 μm, respectively. ), white pigment (titanium dioxide having an average particle diameter (D50) of 0.9 μm), and coupling agent (2-(3,4-epoxycyclohexyl)ethyltrimethyldecane-(2-(3,4-epoxycyclohexyl)- Ethyltrimethoxysilane)), and a fatty acid ester-based release agent (product number Hoechst wax E, available from Clariant) were thoroughly stirred and mixed with an amalgamator according to the ratio of the components shown in Table 2 to obtain a molded composition. (I). Next, the molding composition (I) was melt-kneaded at 80 ° C for 15 minutes using a mixing roll, a kneader, and an extruder. After cooling, the obtained kneaded product was subjected to powder pulverization and tableting to obtain a cake. Next, the obtained rubber cake was subjected to a transfer molding process, and it was found that the flow rate was 175 ° C at the process temperature (it can be completely filled in a predetermined mold), and after cooling, it can be cured in 80 seconds. Finally, the reflectance of the cured product at a wavelength of 450 nm was measured, and the results are shown in Table 2.

Example 2

The organic-inorganic hybrid resin (IV), hexahydrophthalic anhydride (HHPA), and inorganic filler obtained in Preparation Example 6 (fused silica) having an average particle diameter (D50) of 4.9 μm and 19.9 μm, respectively. ), white pigment (titanium dioxide with an average particle diameter (D50) of 0.9 μm), coupling agent (2-(3,4-) 2-(3,4-Epoxycyclohexyl)-ethyltrimethoxysilane), and a fatty acid ester-based release agent (product number Hoechst wax E, available from Clariant) according to Table 2 The composition ratio shown is sufficiently stirred and mixed with an amalgamator to obtain a molded composition (II). Next, the molding composition (II) was melt-kneaded at 60 ° C for 30 minutes using a mixing roll, a kneader, and an extruder. After cooling, the obtained kneaded product was subjected to powder pulverization and tableting to obtain a cake. Next, the obtained rubber cake was subjected to a transfer molding process, and it was found that the flow rate was 175 ° C at the process temperature (it can be completely filled in a predetermined mold), and after cooling, it can be cured in 80 seconds. Finally, the reflectance of the cured product at a wavelength of 450 nm was measured, and the results are shown in Table 2.

Example 3

The organic-inorganic hybrid resin (VI), hexahydrophthalic anhydride (HHPA), and inorganic filler obtained in Preparation Example 8 (fused silica) having an average particle diameter (D50) of 4.9 μm and 19.9 μm, respectively. ), white pigment (titanium dioxide having an average particle diameter (D50) of 0.9 μm), and coupling agent (2-(3,4-epoxycyclohexyl)ethyltrimethyldecane-(2-(3,4-epoxycyclohexyl)- Ethyltrimethoxysilane)), and a fatty acid ester-based release agent (product number Hoechst wax E, available from Clariant) were thoroughly stirred and mixed with an amalgamator according to the ratio of the components shown in Table 2 to obtain a molded composition. (III). Next, the molding composition (III) was melt-kneaded at 60 ° C for 25 minutes using a mixing roll, a kneader, and an extruder. After cooling, the obtained kneaded product was subjected to powder pulverization and tableting to obtain a cake. Next, using the obtained rubber cake for transfer molding It is known that it has fluidity at 175 ° C at the process temperature (can be completely filled into the predetermined mold), and can be cured in 80 seconds after cooling. Finally, the reflectance of the cured product at a wavelength of 450 nm was measured, and the results are shown in Table 2.

Example 4

The organic-inorganic hybrid resin (VII), hexahydrophthalic anhydride (HHPA), and inorganic filler obtained in Preparation Example 9 (fused silica) having an average particle diameter (D50) of 4.9 μm and 19.9 μm, respectively. ), white pigment (titanium dioxide having an average particle diameter (D50) of 0.9 μm), and coupling agent (2-(3,4-epoxycyclohexyl)ethyltrimethyldecane-(2-(3,4-epoxycyclohexyl)- Ethyltrimethoxysilane)), and a fatty acid ester-based release agent (product number Hoechst wax E, available from Clariant) were thoroughly stirred and mixed with an amalgamator according to the ratio of the components shown in Table 2 to obtain a molded composition. (IV). Next, the molding composition (IV) was melt-kneaded at 80 ° C for 25 minutes using a mixing roll, a kneader, and an extruder. After cooling, the obtained kneaded product was subjected to powder pulverization and tableting to obtain a cake. Next, the obtained rubber cake was subjected to a transfer molding process, and it was found that the flow rate was 175 ° C at the process temperature (it can be completely filled in a predetermined mold), and after cooling, it can be cured in 80 seconds. Finally, the reflectance of the cured product at a wavelength of 450 nm was measured, and the results are shown in Table 2.

Example 5

The organic-inorganic hybrid resin (VIII), hexahydrophthalic anhydride (HHPA), and inorganic filler obtained in Preparation Example 10 (fused silica) having an average particle diameter (D50) of 4.9 μm and 19.9 μm, respectively. ), white pigment (titanium dioxide having an average particle diameter (D50) of 0.9 μm), coupling Agent (2-(3,4-Epoxycyclohexyl)-ethyltrimethoxysilane), and fatty acid ester release agent (product number Hoechst wax E) The product composition (V) was obtained by thoroughly stirring and mixing with an amalgamator according to the ratio of the components shown in Table 2 according to the composition ratio shown in Table 2. Next, the molding composition (V) was melt-kneaded at 50 ° C for 30 minutes using a mixing roll, a kneader, and an extruder. After cooling, the obtained kneaded product was subjected to powder pulverization and tableting to obtain a cake. Next, the obtained rubber cake was subjected to a transfer molding process, and it was found that the flow rate was 175 ° C at the process temperature (it can be completely filled in a predetermined mold), and after cooling, it can be cured in 80 seconds. Finally, the reflectance of the cured product at a wavelength of 450 nm was measured, and the results are shown in Table 2.

Example 6

The organic-inorganic hybrid resin (III) obtained in Preparation Example 5, tetrahydrophthalic anhydride (THPA), and inorganic filler (fused silica) having an average particle diameter (D50) of 4.9 μm and 19.9 μm, respectively. ), white pigment (titanium dioxide having an average particle diameter (D50) of 0.9 μm), and coupling agent (2-(3,4-epoxycyclohexyl)ethyltrimethyldecane-(2-(3,4-epoxycyclohexyl)- Ethyltrimethoxysilane)), and a fatty acid ester-based release agent (product number Hoechst wax E, available from Clariant) were thoroughly stirred and mixed with an amalgamator according to the ratio of the components shown in Table 2 to obtain a molded composition. (VI). Next, the molding composition (VI) was melt-kneaded at 60 ° C for 40 minutes using a mixing roll, a kneader, and an extruder. After cooling, the obtained kneaded product was subjected to powder pulverization and tableting to obtain a cake. Then, using the obtained rubber cake to carry out the transfer molding process, It is known that it has fluidity at 175 ° C at the process temperature (can be completely filled into the predetermined mold) and can be cured in 80 seconds after cooling. Finally, the reflectance of the cured product at a wavelength of 450 nm was measured, and the results are shown in Table 2.

Example 7

The organic-inorganic hybrid resin (VI), hexahydrophthalic anhydride (HHPA), tetrahydrophthalic anhydride (THPA), and inorganic filler obtained in Preparation Example 8 (average particle diameter (D50) were 4.9 μm and 19.9, respectively. Φm fused silica, white pigment (titanium dioxide having an average particle diameter (D50) of 0.9 μm), coupling agent (2-(3,4-epoxycyclohexyl)ethyltrimethylnonane) 2-(3,4-Epoxycyclohexyl)-ethyltrimethoxysilane)), and a fatty acid ester-based release agent (product number Hoechst wax E, available from Clariant) was thoroughly stirred by an amalgamator according to the ratio of the components shown in Table 2. After uniformly mixing, a molding composition (VII) was obtained. Next, the molding composition (VII) was melt-kneaded at 60 ° C for 30 minutes using a mixing roll, a kneader, and an extruder. After cooling, the obtained kneaded product was subjected to powder pulverization and tableting to obtain a cake. Next, the obtained rubber cake was subjected to a transfer molding process, and it was found that the flow rate was 175 ° C at the process temperature (it can be completely filled in a predetermined mold), and after cooling, it can be cured in 80 seconds. Finally, the reflectance of the cured product at a wavelength of 450 nm was measured, and the results are shown in Table 2.

Example 8

The organic-inorganic hybrid resin (V), hexahydrophthalic anhydride (HHPA), and inorganic filler obtained in Preparation Example 7 (having an average particle diameter (D50) of 0.7 μm, 4.9 μm, and 19.9 μm, respectively. (fused Silica)), white pigment (titanium dioxide with an average particle diameter (D50) of 0.9 μm), coupling agent (2-(3,4-epoxycyclohexyl)ethyltrimethylnonane) (2-(3,4-epoxycyclohexyl) )-ethyltrimethoxysilane)), and a fatty acid ester-based release agent (product number Hoechst wax E, available from Clariant) was thoroughly stirred and mixed with an amalgamator according to the ratio of the components shown in Table 2, and then molded. Composition (VIII). Next, the molding composition (VIII) was melt-kneaded at 60 ° C for 15 minutes using a mixing roll, a kneader, and an extruder. After cooling, the obtained kneaded product was subjected to powder pulverization and tableting to obtain a cake. Next, the obtained rubber cake was subjected to a transfer molding process, and it was found that the flow rate was 175 ° C at the process temperature (it can be completely filled in a predetermined mold), and after cooling, it can be cured in 80 seconds. Finally, the reflectance of the cured product at a wavelength of 450 nm was measured, and the results are shown in Table 2.

Comparative Example 1

The organic-inorganic hybrid resin (III) obtained in Preparation Example 5, methyl hexahydrophthalic anhydride (MHHPA) (liquid acid anhydride), and inorganic filler (average particle diameter (D50) were 0.7 μm, 4.9 μm, and 19.9 μm fused silica, white pigment (titanium dioxide having an average particle diameter (D50) of 0.9 μm), coupling agent (2-(3,4-epoxycyclohexyl)ethyltrimethyldecane (2-(3,4-Epoxycyclohexyl)-ethyltrimethoxysilane)), and a fatty acid ester-based release agent (product number Hoechst wax E, available from Clariant) according to the composition ratio shown in Table 2 with an amalgamator After stirring and mixing uniformly, the molded composition (IX) was obtained. Next, the molding composition (IX) was melt-kneaded at 50 ° C for 20 minutes using a mixing roll, a kneader, and an extruder. After cooling, the resulting kneaded product remained in a liquid state.

Comparative Example 2

The resin (I), tetrahydrophthalic anhydride (THPA), and inorganic filler (average particle diameter (D50)) obtained in Preparation Example 13 were 0.7 μm, 4.9 μm, and 19.9 μm, respectively, of fused silica. )), white pigment (titanium dioxide with an average particle diameter (D50) of 0.9 μm), coupling agent (2-(3,4-epoxycyclohexyl)ethyltrimethylnonane (2-(3,4-epoxycyclohexyl)) -ethyltrimethoxysilane)), and a fatty acid ester-based release agent (product number Hoechst wax E, available from Clariant) according to the composition ratio shown in Table 2, fully stirred and mixed with an amalgamator to obtain a molded composition. (X). Next, the molding composition (X) was melt-kneaded at 80 ° C for 120 minutes using a mixing roll, a kneader, and an extruder. After cooling, the resulting kneaded product remained in a liquid state.

Comparative Example 3

The resin (II), the hexahydrophthalic anhydride (HHPA), and the inorganic filler (average particle diameter (D50)) obtained in Preparation Example 14 were 0.7 μm, 4.9 μm, and 19.9 μm, respectively, of fused silica. )), white pigment (titanium dioxide with an average particle diameter (D50) of 0.9 μm), coupling agent (2-(3,4-epoxycyclohexyl)ethyltrimethylnonane (2-(3,4-epoxycyclohexyl)) -ethyltrimethoxysilane)), and a fatty acid ester-based release agent (product number Hoechst wax E, available from Clariant) according to the composition ratio shown in Table 2, fully stirred and mixed with an amalgamator to obtain a molded composition. (XI). Next, the molding composition (XI) was melt-kneaded at 80 ° C for 15 minutes using a mixing roll, a kneader, and an extruder. After cooling, the obtained kneaded product is powdered and pulverized. Ingots are made to obtain a cake. Next, the obtained rubber cake was subjected to a transfer molding process, and it was found that fluidity at 175 ° C at the process temperature (which can be completely filled in a predetermined mold) was cured in 175 ° C / 180 seconds. Finally, the reflectance of the cured product at a wavelength of 450 nm was measured, and the results are shown in Table 2.

As is clear from Table 2, the molded composition having the organic-inorganic hybrid resin of the present invention was still solid after kneading. Further, when the products obtained by the kneading of Examples 1-8 were subjected to a transfer molding process, it was found that the kneaded products have high fluidity, rapid reactivity, and good processability, and the reflectance of the cured product at a wavelength of 450 nm was More than 90% (presenting white), very suitable as a package structure for optoelectronic devices (such as reflective cups). Further, as is clear from Table 2, when the hardening agent of the molding composition was changed to a liquid acid anhydride (Comparative Example 1), the product obtained by the kneading was liquid and could not be processed by a transfer molding process. Still refer to Table 2, when molding When the resin of the composition was changed to the liquid resin obtained in Preparation Example 13 (Comparative Example 2), the product obtained by the kneading was also in a liquid state and could not be processed by a transfer molding process. On the other hand, when the resin of the molding composition was changed to the brown resin obtained in Preparation Example 14 (Comparative Example 3), even if a white pigment was added, the product obtained by the kneading was still yellowish, resulting in a cured product at a wavelength of 450 nm. The reflectivity is only 73%.

In summary, the organic-inorganic hybrid resin of the present invention can ensure that the obtained organic-inorganic hybrid resin can be less than 50 ° C by using a specific ratio of the sesquisesquioxane prepolymer having a metal oxide cluster to the epoxy resin. The following is a non-flowing solid, and has a melt flowability (having a melt viscosity ranging from 100 to 10,000 mPa.s) when heated to a temperature range of 80 to 150 °C. Further, the molding composition having the organic-inorganic hybrid resin of the present invention can be formed into a molding material by kneading, and has high fluidity, rapid reactivity, and good processability in the transfer molding process. Furthermore, the cured product obtained by the kneading process and the transfer molding process of the molding composition of the present invention has high light reflectivity and photothermal stability, and thus can be widely applied to package structures of various types of photovoltaic devices.

Although the present invention has been disclosed in the above embodiments, it is not intended to limit the present invention, and any one of ordinary skill in the art can make some changes and refinements without departing from the spirit and scope of the present invention. The scope of the invention is defined by the scope of the appended claims.

10‧‧‧Optoelectronic devices

12‧‧‧Optoelectronic components

14‧‧‧Reflection Cup

Claims (31)

An organic-inorganic hybrid resin is a reaction product of a first composition, wherein the first composition comprises: 0.1-10 parts by weight of the starting material (a), wherein the starting material (a) is one having a metal oxide cluster of a silsesquioxane prepolymer, wherein the metal is titanium (Ti), zirconium (Zr), zinc (Zn), or a combination thereof; 100 parts by weight of the starting material (b), wherein the starting material (b) is an epoxy resin. The organic-inorganic hybrid resin as described in claim 1, wherein the starting material (a) has a weight molecular weight distribution of between 2,500 and 7,800. The organic-inorganic hybrid resin as described in claim 1, wherein the first composition further comprises: 1-35 parts by weight of the starting material (c), wherein the starting material (c) is a monoanhydride. The organic-inorganic hybrid resin as described in claim 3, wherein the starting material (c) comprises succinic anhydride, maleic anhydride, phthalic anhydride, PA), tetrahydrophthalic anhydride (THPA), hexahydrophthalic anhydride (HHPA), methyltetrahydrophthalic anhydride (MTHPA), methyl hexahydrophthalic anhydride (MHHPA), or The combination. The organic-inorganic hybrid resin as described in claim 3, wherein an equivalent ratio of the acid anhydride group of the starting material (c) to the epoxy group of the starting material (b) is between 0.001 and 0.5. The organic-inorganic hybrid resin as described in claim 1, wherein the starting material (a) is a reaction product of a second composition, wherein the second composition comprises: 1-10 parts by weight of the starting material (d) wherein the starting material (d) has the structure represented by the formula (I): Wherein R ¹ is independently C _{1 -10} alkyl, and n is a positive integer selected from 4-31; 100 parts by weight of the starting material (e), wherein the starting material (e) is a titanium alkoxide, a zirconium alkoxide, a zinc alkoxide, or a combination thereof; and 5 to 20 parts by weight of the starting material (f), wherein the starting material (f) has the structure represented by the formula (II): Wherein, R ² is independently a C _1-3 alkoxy-based group, and R ³ C _3-12 based epoxy group (epoxy group), C _3-12 acrylate group (acrylate group), C _4-12 alkyl acrylate, An alkylacryloxy group or a C _3-12 alkenyl group. The organic-inorganic hybrid resin as described in claim 6, wherein the starting material (e) comprises zirconium ethoxide, zirconium isopropoxide, zirconium n-propoxide, zirconium n-butoxide, zirconium tert-butoxide, zinc ethoxide , zinc isopropoxide, zinc n-propoxide, zinc n-butoxide, third Zinc butoxide, titanium ethoxide, titanium isopropoxide, titanium n-propoxide, titanium n-butoxide, titanium tributoxide, or a combination thereof. The organic-inorganic hybrid resin as described in claim 6, wherein the starting material (f) comprises 2-(3,4-epoxycyclohexyl)ethyltrimethylnonane (2-(3,4-) Epoxycyclohexyl)-ethyltrimethoxysilane, 3-Glycidoxypropyltrimethoxysilane, 3-Glycidoxypropyl methoxydiethoxysilane, 3-glycerylpropyl 3-Glycidoxypropyl triethoxysilane, 3-methacryloxypropyl trimethoxysilane, 3-Methacryloxypropyl triethoxysilane, Or 3-acryloxypropyl trimethoxysilane. The organic-inorganic hybrid resin as described in claim 6, wherein the second composition further comprises: 3-10 parts by weight of the starting material (g), wherein the starting material (g) is water, hydrogen hydroxide Ammonium, or a combination of the above. The organic-inorganic hybrid resin as described in claim 1, wherein the starting material (a) has the structure represented by the formula (III): Wherein R ¹ is independently C _{1 -10} alkyl; n is a positive integer selected from 4-31; and, Y is (MO _4/2 ) _l [(MO) _(4-a)/2 M(OH _a/2 ] _m [MO _(4-b)/2 M(OZ) _b/2 ] _p , wherein M is a metal; l is a positive integer from 5-20; m is selected from 2-8 a positive integer; p is a positive integer selected from 2-5; a is a positive integer selected from 1-2; b is a positive integer selected from 1-2; and, Z-SiR ³ (R ⁴ ) ₂ , wherein R ³ is independently a C _3-12 epoxy group, a C _3-12 acrylate group, a C _4-12 alkylacryloxy group, or a C _3-12 alkenyl group ( Alkenyl group); and, R ⁴ is independently a hydroxyl group or a C _1-8 alkoxy group. The organic-inorganic hybrid resin according to claim 1, wherein the starting material (b) comprises a triglycidyl isocyanurate epoxy resin, a hydrogenated epoxy resin, an alicyclic epoxy resin, A siloxane-modified epoxy resin, or a combination thereof. The organic-inorganic hybrid resin as described in claim 1, wherein the starting material (b) comprises a decane-modified epoxy resin. The organic-inorganic hybrid resin as described in claim 12, wherein the starting material (b) has the structure represented by the formula (IV): Wherein R ¹ is independently C _{1 -10} alkyl; R ⁵ is independently C _{1 -10} alkyl, or phenyl; R ⁶ is epoxycyclohexylethyl, or epoxycyclohexyl Epoxycyclohexylpropyl; R ⁷ is independently C _{1 -10} alkyl, epoxycyclohexylethyl, or epoxycyclohexylpropyl; and, 1≦c≦150, and 0 ≦ d ≦ 15, wherein, when d> 0, c / d-based ranging between 1 and 10; when d = 0, at least one R ⁷ group is an epoxy-based cyclohexylethyl (epoxycyclohexylethyl), or cyclic Epoxycyclohexylpropyl. The organic-inorganic hybrid resin according to claim 12, wherein the siloxane-modified epoxy resin has a weight average molecular weight of between 400 and 10,000. The organic-inorganic hybrid resin according to claim 12, wherein the starting material (b) further comprises a triglycidyl isocyanurate epoxy resin, a hydrogenated epoxy resin, an alicyclic epoxy resin. Or a combination of the above. The organic-inorganic hybrid resin according to claim 1, wherein the organic-inorganic hybrid resin has a melting point of more than 50 ° C, and the organic-inorganic hybrid resin has a melt viscosity of from 100 to 10,000 at 80 to 120 ° C. mPa.s. A molding composition comprising: the organic-inorganic hybrid resin described in claim 1; an inorganic filler; a hardener; and a white pigment. The molding composition according to claim 17, wherein the inorganic filler comprises cerium oxide, aluminum hydroxide, magnesium hydroxide, magnesium carbonate, cerium carbonate, or a combination thereof. The molding composition of claim 17, wherein the white pigment comprises titanium oxide, aluminum oxide, magnesium oxide, zirconium oxide, calcium carbonate, zinc sulfide, zinc oxide, or a combination thereof. The molding composition of claim 17, wherein the hardener is a solid non-aromatic anhydride. The molding composition of claim 17, wherein the hardening agent comprises tetrahydrophthalic anhydride (THPA), hexahydrophthalic anhydride (HHPA), maleic anhydride, or Combination of the above. The molding composition according to claim 17, wherein the inorganic filler and the white pigment have a total weight of from 30 to 84% by weight based on the total weight of the molding composition. The molding composition of claim 17, wherein the weight ratio of the white pigment to the inorganic filler is between 0.1 and 0.5. The molding composition according to claim 17, wherein the organic-inorganic hybrid resin has a weight percentage of from 11 to 55 wt% based on the total weight of the molding composition. The molding composition of claim 17, wherein the hardener has a weight percentage of from 3 to 15% by weight based on the total weight of the molding composition. The molding composition according to claim 17, further comprising: an additive, wherein the additive comprises a coupling agent, a releasing agent, or a combination thereof. The molding composition of claim 26, wherein the additive has a weight percentage of from 0.5 to 1.5% by weight based on the total weight of the molding composition. The molding composition according to claim 17, wherein the molding composition is subjected to a kneading process and a cured product obtained by a transfer molding process for a wavelength of 450 nm. Light, with a reflectivity greater than 90%. The molding composition of claim 28, wherein the temperature of the transfer molding process is between 100 and 200 ° C, and the molding composition has a bonding time in the transfer molding process. Between 10 and 150 seconds. An optoelectronic device comprising: a reflective cup; and a photovoltaic element disposed in the reflective cup, wherein the reflective cup is kneading by a molding composition according to claim 17 The process and the cured product obtained after a transfer molding process. The photovoltaic device of claim 30, wherein the photovoltaic element comprises a light emitting diode, a laser diode, or a light receiver.