TWI798722B - Uv curable composition - Google Patents

Uv curable composition Download PDF

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TWI798722B
TWI798722B TW110122316A TW110122316A TWI798722B TW I798722 B TWI798722 B TW I798722B TW 110122316 A TW110122316 A TW 110122316A TW 110122316 A TW110122316 A TW 110122316A TW I798722 B TWI798722 B TW I798722B
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weight
parts
acrylate
curable composition
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TW110122316A
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TW202300531A (en
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許政偉
尹大中
周德綱
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臺灣永光化學工業股份有限公司
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Abstract

A UV curable composition is disclosed, which comprises: 30 to 60 parts by weight of hydrogenated polybutadiene acrylate; 1 to 10 parts by weight of acid modified polybutadiene acrylate; 30 to 60 parts by weight of alicyclic acrylate monomer; 1 to 10 parts by weight of multi-functional acrylate monomer; 1 to 10 parts by weight of photo-initiator; and 1 to 50 parts by weight of filler.

Description

紫外光固化組成物 UV curable composition

本揭露提供一種紫外光固化組成物，尤指一種可應用於電子產品封裝膠上的紫外光固化組成物。 The disclosure provides an ultraviolet curable composition, especially an ultraviolet curable composition that can be applied to packaging adhesives for electronic products.

於電子產品中多使用封裝膠來進行封裝，以達到阻水或阻氣之特性，來保護電子產品中的元件。其中，以紫外光來固化的高分子組成物為常用的封裝膠之一。 Encapsulation glue is often used for packaging in electronic products to achieve water-blocking or gas-blocking properties to protect components in electronic products. Among them, the polymer composition cured by ultraviolet light is one of the commonly used encapsulants.

為了確保電子產品在使用環境下有良好的耐候度及可靠度，固化後的封裝膠需具有良好的密著度及穩定性。已知目前可使用具極性的小分子酸添加於高分子組成物中來提升固化後的封裝膠的密著度，但這樣的高分子組成物其固化後的穩定性仍不理想。 In order to ensure that electronic products have good weather resistance and reliability in the use environment, the cured encapsulant must have good adhesion and stability. It is known that a polar small molecular acid can be added to the polymer composition to improve the adhesion of the cured encapsulant, but the stability of such a polymer composition after curing is still not ideal.

有鑑於此，目前亟需發展出一種紫外光固化組成物，其固化後仍具有良好的密著度或穩定性，以確保使用其的封裝物(例如，電子產品)具有良好的耐候度及可靠度。 In view of this, there is an urgent need to develop a UV-curable composition, which still has good adhesion or stability after curing, so as to ensure that the package (for example, electronic products) using it has good weather resistance and reliability. Spend.

本揭露的提供一種紫外光固化組成物，可包括：30至60重量份之氫化聚丁二烯丙烯酸酯；1至10重量份之酸基改質的聚丁二烯丙烯酸酯；30至60重量份之脂環式丙烯酸酯單體；1至10重量份之多官能丙烯酸酯單體；1至10重量份之光起始劑；以及1至50重量份之填充物。 The present disclosure provides a UV-curable composition, which may include: 30 to 60 parts by weight of hydrogenated polybutadiene acrylate; 1 to 10 parts by weight of acid-modified polybutadiene acrylate; 30 to 60 parts by weight 1-10 parts by weight of alicyclic acrylate monomer; 1-10 parts by weight of multifunctional acrylate monomer; 1-10 parts by weight of photoinitiator; and 1-50 parts by weight of filler.

本揭露的紫外光固化組成物添加有酸基改質的聚丁二烯丙烯酸酯，其中，酸基改質的聚丁二烯丙烯酸酯中的酸基可提升固化後的組成物與基材間的密著度，且酸基改質的聚丁二烯丙烯酸酯也可與主成分的氫化聚丁二烯丙烯酸酯進行交聯反應，而提升固化後的組成物的穩定性。因此，當將本揭露的紫外光固化組成物塗佈於一基材上時，固化後的組成物與基材間具有良好的密著度，或固化後的組成物具有優良的冷熱衝擊耐受度。特別是，因固化後的組成物與基材間具有良好的密著度，而可做為電子產品(例如：液晶顯示器(LCD)、發光二極體(LED)、有機發光二極體(OLED)、染料敏化太陽能電池(DSSC)、有機太陽能電池(OPV)、鈣鈦礦太陽能電池(PSC)、電子紙等)的封裝膠。 The UV-curable composition of the present disclosure is added with acid group-modified polybutadiene acrylate, wherein the acid group in the acid-group-modified polybutadiene acrylate can improve the bond between the cured composition and the substrate. The degree of adhesion is high, and the polybutadiene acrylate modified by the acid group can also undergo a crosslinking reaction with the hydrogenated polybutadiene acrylate as the main component, so as to improve the stability of the cured composition. Therefore, when the UV-curable composition of the present disclosure is coated on a substrate, the cured composition has good adhesion to the substrate, or the cured composition has excellent cold and heat shock resistance Spend. In particular, due to the good adhesion between the cured composition and the substrate, it can be used as an electronic product (such as: liquid crystal display (LCD), light emitting diode (LED), organic light emitting diode (OLED) ), dye-sensitized solar cells (DSSC), organic solar cells (OPV), perovskite solar cells (PSC), electronic paper, etc.).

本揭露組成物可包括30至60重量份之氫化聚丁二烯丙烯酸酯。於本揭露的一實施例中，氫化聚丁二烯丙烯酸酯的含量可為33至60重量份。於本揭露的另一實施例中，氫化聚丁二烯丙烯酸酯的含量可為34至59重量份。 The composition of the present disclosure may include 30 to 60 parts by weight of hydrogenated polybutadiene acrylate. In an embodiment of the present disclosure, the content of the hydrogenated polybutadiene acrylate may be 33 to 60 parts by weight. In another embodiment of the present disclosure, the hydrogenated polybutadiene acrylate may have a content of 34 to 59 parts by weight.

於本揭露中，氫化聚丁二烯丙烯酸酯可如下式(I)所示：

Figure 110122316-A0305-02-0004-2
其中，R1及R2可分別獨立為氫或甲基；R3及R4可分別獨立為一二價連接基，該二價連接基包括氧、氮、1至16個碳或其組合；以及m及n的比例(m：n)可為0~100：100~0。 In the present disclosure, the hydrogenated polybutadiene acrylate can be represented by the following formula (I):
Figure 110122316-A0305-02-0004-2
 Wherein, R 1 and R 2 can be independently hydrogen or methyl; R 3 and R 4 can be independently a divalent linking group, the divalent linking group includes oxygen, nitrogen, 1 to 16 carbons or a combination thereof; And the ratio of m and n (m:n) can be 0~100:100~0.

於本揭露的一實施例中，R3及R4可分別為包括一或兩個-NH(CO)O-及C3-10亞環烷基之官能基，其中C3-10亞環烷基可選擇性的被C1-3烷基所取代。 In one embodiment of the present disclosure, R 3 and R 4 can be respectively a functional group including one or two -NH(CO)O- and C 3-10 cycloalkylene, wherein C 3-10 cycloalkylene The group can be optionally substituted by C 1-3 alkyl.

於本揭露的一實施例中，R3及R4可分別如下式(I-1)所示： In an embodiment of the present disclosure, R 3 and R 4 can be represented by the following formula (I-1):

Figure 110122316-A0101-12-0003-6
其中，l及k可分別獨立為0至4的整數；p可為0至6的整數；以及*連接至式(I)中的氧原子，而**連接至式(I)中的碳原子。
Figure 110122316-A0101-12-0003-6
 Wherein, l and k can be independently an integer of 0 to 4; p can be an integer of 0 to 6; and * is connected to the oxygen atom in formula (I), and ** is connected to the carbon atom in formula (I) .

於本揭露的一實施例中，R3及R4可為相同的基團。 In an embodiment of the present disclosure, R 3 and R 4 may be the same group.

於本揭露的一實施例中，式(I-1)中的l可為1、2、3或4。於本揭露的另一實施例中，式(I-1)中的l可為1、2或3。於本揭露的再一實施例中，式(I-1)中的l可為2。 In an embodiment of the present disclosure, l in formula (I-1) can be 1, 2, 3 or 4. In another embodiment of the present disclosure, l in formula (I-1) can be 1, 2 or 3. In yet another embodiment of the present disclosure, l in formula (I-1) may be 2.

於本揭露的一實施例中，式(I-1)中的k可為0、1、2或3。於本揭露的另一實施例中，式(I-1)中的k可為0、1或2。於本揭露的再一實施例中，式(I-1)中的k可為1。 In an embodiment of the present disclosure, k in formula (I-1) can be 0, 1, 2 or 3. In another embodiment of the present disclosure, k in formula (I-1) can be 0, 1 or 2. In yet another embodiment of the present disclosure, k in formula (I-1) may be 1.

於本揭露的一實施例中，式(I-1)中的p可為1至5的整數。於本揭露的另一實施例中，式(I-1)中的p可為2至4的整數。於本揭露的再一實施例中，式(I-1)中的p可為3。 In an embodiment of the present disclosure, p in formula (I-1) may be an integer of 1-5. In another embodiment of the present disclosure, p in formula (I-1) may be an integer of 2-4. In yet another embodiment of the present disclosure, p in formula (I-1) may be 3.

於本揭露中，氫化聚丁二烯丙烯酸酯的重量平均分子量可介於10,000至100,000g/mol之間。於本揭露的一實施例中，氫化聚丁二烯丙烯酸酯的重量平均分子量可介於10,000至50,000g/mol之間。 In the present disclosure, the weight average molecular weight of the hydrogenated polybutadiene acrylate may be between 10,000 and 100,000 g/mol. In an embodiment of the present disclosure, the weight average molecular weight of the hydrogenated polybutadiene acrylate may be between 10,000 and 50,000 g/mol.

於本揭露中，氫化聚丁二烯丙烯酸酯的具體例子可如下式(I-2)所示： In the present disclosure, a specific example of hydrogenated polybutadiene acrylate can be shown in the following formula (I-2):

Figure 110122316-A0101-12-0004-8
Figure 110122316-A0101-12-0004-8

本揭露組成物可包括1至10重量份之酸基改質的聚丁二烯丙烯酸酯。於本揭露的一實施例中，酸基改質的聚丁二烯丙烯酸酯的含量可為1至6重量份。於本揭露的另一實施例中，酸基改質的聚丁二烯丙烯酸酯的含量可為2至5重量份。 The composition of the present disclosure may include 1 to 10 parts by weight of acid-modified polybutadiene acrylate. In an embodiment of the present disclosure, the content of the acid group-modified polybutadiene acrylate may be 1 to 6 parts by weight. In another embodiment of the present disclosure, the content of the acid-modified polybutadiene acrylate may be 2 to 5 parts by weight.

於本揭露中，酸基改質的聚丁二烯丙烯酸酯可如下式(II)所示： In the present disclosure, the acid-modified polybutadiene acrylate can be represented by the following formula (II):

Figure 110122316-A0101-12-0004-7
其中，A可為含有羧酸基且1至6個碳之連接基；x可為小於100的正整數；y可為小於40的正整數；z可為小於10的正整數；以及a可為2、3或4。
Figure 110122316-A0101-12-0004-7
 Wherein, A can be a linking group containing a carboxylic acid group and 1 to 6 carbons; x can be a positive integer less than 100; y can be a positive integer less than 40; z can be a positive integer less than 10; 2, 3 or 4.

於本揭露中，酸基改質的聚丁二烯丙烯酸酯中連接基A的羧酸基可提升固化後的組成物與基材間的密著度。此外，酸基改質的聚丁二烯丙烯酸酯中的丙烯酸酯官能基可與氫化聚丁二烯丙烯酸酯進行交聯反應，而提升固化後的組成物的穩定性。 In the present disclosure, the carboxylic acid group of the linker A in the acid-modified polybutadiene acrylate can improve the adhesion between the cured composition and the substrate. In addition, the acrylate functional group in the acid-modified polybutadiene acrylate can undergo a cross-linking reaction with the hydrogenated polybutadiene acrylate, thereby improving the stability of the cured composition.

於本揭露的一實施例中，A可為-(CHR5)qC(=O)-，其中R5為H、C1-3烷基或羧酸基，q為1至6之整數，且至少一R5為羧酸基。此外，左端連接至碳原子，而右端連接至氧原子。 In one embodiment of the present disclosure, A can be -(CHR 5 ) q C(=O)-, wherein R 5 is H, C 1-3 alkyl or carboxylic acid group, q is an integer from 1 to 6, And at least one R 5 is a carboxylic acid group. Also, the left end is attached to a carbon atom, and the right end is attached to an oxygen atom.

於本揭露的一實施例中，R5為H或羧酸基，q為1至3之整數，且其中之一R5為羧酸基。 In an embodiment of the present disclosure, R 5 is H or a carboxylic acid group, q is an integer from 1 to 3, and one of R 5 is a carboxylic acid group.

於本揭露的一實施例中，A可如下式(II-1)所示：

Figure 110122316-A0305-02-0007-3
其中，*連接至碳原子，而**連接至氧原子。 In an embodiment of the present disclosure, A can be represented by the following formula (II-1):
Figure 110122316-A0305-02-0007-3
 Among them, * is attached to a carbon atom, and ** is attached to an oxygen atom.

於本揭露中，酸基改質的聚丁二烯丙烯酸酯的重量平均分子量可介於2,000至8,000g/mol之間。於本揭露的一實施例中，酸基改質的聚丁二烯丙烯酸酯的重量平均分子量可介於4,000至8,000g/mol之間。 In the present disclosure, the weight average molecular weight of the acid-modified polybutadiene acrylate may be between 2,000 and 8,000 g/mol. In an embodiment of the present disclosure, the weight average molecular weight of the acid-modified polybutadiene acrylate may be between 4,000 and 8,000 g/mol.

於本揭露中，酸基改質的聚丁二烯丙烯酸酯的具體例子可如下式(II-2)所示：

Figure 110122316-A0305-02-0007-4
In the present disclosure, a specific example of acid-modified polybutadiene acrylate can be shown in the following formula (II-2):
Figure 110122316-A0305-02-0007-4

本揭露組成物可包括30至60重量份之脂環式丙烯酸酯單體。於本揭露的一實施例中，脂環式丙烯酸酯單體的含量可為33至58重量份。於本揭露的另一實施例中，脂環式丙烯酸酯單體的含量可為35至55重量份。 The disclosed composition may include 30 to 60 parts by weight of alicyclic acrylate monomer. In an embodiment of the present disclosure, the content of the alicyclic acrylate monomer may be 33 to 58 parts by weight. In another embodiment of the present disclosure, the content of the alicyclic acrylate monomer may be 35 to 55 parts by weight.

於本揭露中，脂環式丙烯酸酯單體可為具有橋環徑(脂環烴)骨架的(甲基)丙烯酸化合物。其中，脂環式丙烯酸酯單體的具體例子可包括，但不限於，(甲基)丙烯酸異冰片酯、(甲基)丙烯酸雙環戊烯基酯、(甲基)丙烯酸雙環戊烯基氧乙基酯、(甲基)丙烯酸二環戊基酯、或丙烯酸1-金剛烷基(甲基)酯；且前述單體可單獨使用或兩種以上合併使用。於本揭露的一實施例中，脂環式丙烯酸酯單體可為丙烯酸異冰片酯、丙烯酸雙環戊烯基酯、丙烯酸雙環戊烯基氧乙基酯、丙烯酸二環戊基酯、丙烯酸1-金剛烷基酯或其組合，其與氫化聚丁二烯丙烯酸酯及/或酸基改質的聚丁二烯丙烯酸酯具有較佳的相溶性。 In the present disclosure, the alicyclic acrylate monomer may be a (meth)acrylic compound having a bridging ring (alicyclic hydrocarbon) skeleton. Among them, specific examples of alicyclic acrylate monomers may include, but are not limited to, isobornyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethylene (meth)acrylate base ester, dicyclopentyl (meth)acrylate, or 1-adamantyl (methyl) acrylate; and the aforementioned monomers can be used alone or in combination of two or more. In an embodiment of the present disclosure, the alicyclic acrylate monomer may be isobornyl acrylate, dicyclopentenyl acrylate, dicyclopentenyloxyethyl acrylate, dicyclopentyl acrylate, 1- The adamantyl ester or a combination thereof has better compatibility with hydrogenated polybutadiene acrylate and/or acid-modified polybutadiene acrylate.

本揭露組成物可包括1至10重量份之多官能丙烯酸酯單體。於本揭露的一實施例中，多官能丙烯酸酯單體的含量可為1至6重量份。於本揭露的另一實施例中，多官能丙烯酸酯單體的含量可為2至4重量份。 The composition of the present disclosure may include 1 to 10 parts by weight of a multifunctional acrylate monomer. In an embodiment of the present disclosure, the content of the multifunctional acrylate monomer may be 1 to 6 parts by weight. In another embodiment of the present disclosure, the content of the multifunctional acrylate monomer may be 2 to 4 parts by weight.

於本揭露中，多官能丙烯酸酯單體可為含有3個或3個以上的丙烯酸酯官能基的單體；且前述的丙烯酸酯官能基可與氫化聚丁二烯丙烯酸酯進行交聯反應。其中，多官能丙烯酸酯單體的具體例子可包括，但不限於，三羥甲基丙烷三丙烯酸酯、季戊四醇四丙烯酸酯、二縮三羥甲基丙烷四丙烯酸酯、雙季戊四醇五丙烯酸酯、或雙季戊四醇六丙烯酸酯；且前述單體可單獨使用或兩種以上合併使用。 In the present disclosure, the multifunctional acrylate monomer can be a monomer containing 3 or more acrylate functional groups; and the aforementioned acrylate functional groups can undergo a cross-linking reaction with hydrogenated polybutadiene acrylate. Among them, specific examples of multifunctional acrylate monomers may include, but are not limited to, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, trimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, or dipentaerythritol hexaacrylate; and the aforementioned monomers can be used alone or in combination of two or more.

本揭露組成物可包括1至10重量份之光起始劑。於本揭露的一實施例中，光起始劑的含量可為1至7重量份。於本揭露的另一實施例中，光起始劑的含量可為1至4重量份。 The composition of the present disclosure may include 1 to 10 parts by weight of a photoinitiator. In an embodiment of the present disclosure, the content of the photoinitiator may be 1 to 7 parts by weight. In another embodiment of the present disclosure, the content of the photoinitiator may be 1 to 4 parts by weight.

於本揭露中，光起始劑的具體例子可包括，但不限於，α-羥基酮衍生物、二苯甲酮及其衍生物、醯基磷氧化物或其組合。所述α-羥基酮衍生物 可為2-羥基-2-甲基-1-苯基-1-丙酮、1-羥基-環己基苯甲酮、或2-羥基-2-甲基-對羥乙基醚基苯基丙酮；所述二苯甲酮及其衍生物可為二苯甲酮、4-甲基二苯甲酮、或4,4’-雙(二甲氨基)二苯甲酮；所述醯基磷氧化物可為2,4,6-三甲基苯甲醯基-乙氧基-苯基氧化磷、2,4,6-三甲基苯甲醯基-二苯基氧化磷、或雙(2,4,6-三甲基苯甲醯基)苯基氧化磷。前述光起始劑可單獨使用或兩種以上合併使用。 In the present disclosure, specific examples of photoinitiators may include, but are not limited to, α-hydroxy ketone derivatives, benzophenone and its derivatives, acyl phosphine oxides, or combinations thereof. The α-hydroxy ketone derivative It can be 2-hydroxy-2-methyl-1-phenyl-1-propanone, 1-hydroxy-cyclohexylbenzophenone, or 2-hydroxy-2-methyl-p-hydroxyethyl ether phenylacetone; The benzophenone and its derivatives can be benzophenone, 4-methyl benzophenone, or 4,4'-bis(dimethylamino) benzophenone; the acyl phosphorus oxide It can be 2,4,6-trimethylbenzoyl-ethoxy-phenylphosphine oxide, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, or bis(2, 4,6-Trimethylbenzoyl)phenylphosphine oxide. The aforementioned photoinitiators may be used alone or in combination of two or more.

本揭露組成物可包括1至50重量份之填充物。於本揭露的一實施例中，填充物的含量可為2至50重量份。 The composition of the present disclosure may include 1 to 50 parts by weight of filler. In an embodiment of the present disclosure, the content of the filler may be 2 to 50 parts by weight.

於本揭露中，填充物的具體例子可包括，但不限於，二氧化矽、滑石粉或其組合。藉由添加適量的填充物，可提升固化後的組成物的阻水阻氣能力或耐化性。 In the present disclosure, specific examples of fillers may include, but are not limited to, silicon dioxide, talc or combinations thereof. By adding an appropriate amount of fillers, the water and gas resistance or chemical resistance of the cured composition can be improved.

此外，本揭露更提供前述紫外光固化組成物的用途，係用於一電子裝置的封裝膠上。更詳細而言，本揭露是將前述紫外光固化組成物塗佈於一基材上，而後蓋上另一基材；而後以紫外光照射以固化所塗佈的紫外光固化組成物。其中，基材的種類可為，但不限於，石英、玻璃、矽晶圓、藍寶石、金屬(例如，不鏽鋼)、聚碳酸酯(polycarbonate,PC)、聚醯亞胺(polyimide,PI)、聚丙烯(polypropylene,PP)、聚對苯二甲酸乙二酯(polyethylene terephthalate,PET)、或其他塑膠或高分子材料，或前述之組合。 In addition, the present disclosure further provides the application of the aforementioned ultraviolet curable composition, which is applied to an encapsulant of an electronic device. More specifically, the present disclosure is to coat the aforementioned UV-curable composition on a substrate, and then cover another substrate; and then irradiate with ultraviolet light to cure the coated UV-curable composition. Wherein, the type of substrate can be, but not limited to, quartz, glass, silicon wafer, sapphire, metal (for example, stainless steel), polycarbonate (polycarbonate, PC), polyimide (polyimide, PI), polyimide Propylene (PP), polyethylene terephthalate (PET), or other plastic or polymer materials, or a combination thereof.

以下係藉由具體實施例說明本揭露之實施方式，熟習此技藝之人士可由本說明書所揭示之內容輕易地了解本揭露之其他優點與功效。本揭露亦可藉由其他不同的具體實施例加以施行或應用，本說明書中的各項細節亦可針對不同觀點與應用，在不悖離本創作之精神下進行各種修飾與變更。 The implementation of the present disclosure is described below through specific examples, and those skilled in the art can easily understand other advantages and effects of the present disclosure from the content disclosed in this specification. This disclosure can also be implemented or applied by other different specific embodiments, and various modifications and changes can be made to the details in this specification for different viewpoints and applications without departing from the spirit of this creation.

除非文中另有說明，否則說明書及所附申請專利範圍中所使用之單數形式「一」及「該」包括一或複數個體。 As used in the specification and the appended claims, the singular forms "a" and "the" include one or plural individuals unless the context dictates otherwise.

除非文中另有說明，否則說明書及所附申請專利範圍中所使用之術語「或」通常包括「及/或」之含義。 Unless otherwise stated in the context, the term "or" used in the specification and appended claims generally includes the meaning of "and/or".

此外，在本文中，”約”之用語通常表示在一給定值或範圍的20%內，或10%內，或5%內，或3%之內，或2%之內，或1%之內，或0.5%之內。在此給定的數量為大約的數量，亦即在沒有特定說明”約”的情況下，仍可隱含”約”之含義。 In addition, in this context, the term "about" generally means within 20%, or within 10%, or within 5%, or within 3%, or within 2%, or within 1% of a given value or range within, or within 0.5%. The quantities given here are approximate quantities, that is, the meaning of "approximately" may still be implied if "approximately" is not specifically stated.

本揭露將藉由實施例更具體地說明，但該等實施例並非用於限制本揭露之範疇。除非特別指明，於下列製備例、實施例與比較例中，溫度為攝氏溫度，份數及百分比係以重量計。重量份數和體積份數之關係就如同公斤和公升之關係。 The present disclosure will be described more specifically through examples, but these examples are not intended to limit the scope of the present disclosure. Unless otherwise specified, in the following preparation examples, examples and comparative examples, the temperature is in degrees centigrade, and the parts and percentages are by weight. The relationship between parts by weight and parts by volume is like the relationship between kilograms and liters.

高分子-氫化聚丁二烯丙烯酸酯 Polymer-Hydrogenated Polybutadiene Acrylate

於本揭露的下述對照例1及實施例1至14中，所使用的氫化聚丁二烯丙烯酸酯(Hydrogenated polybutadiene acrylate,HPBA)(成祈公司CC-HPBA)，其重量平均分子量介於10,000至50,000g/mol之間。其中，氫化聚丁二烯丙烯酸酯的結構可如下式(I-2)所示。 In the following Comparative Example 1 and Examples 1 to 14 of the present disclosure, the hydrogenated polybutadiene acrylate (Hydrogenated polybutadiene acrylate, HPBA) (Chengqi Company CC-HPBA) used has a weight average molecular weight of 10,000 to 50,000g/mol. Wherein, the structure of the hydrogenated polybutadiene acrylate may be shown in the following formula (I-2).

Figure 110122316-A0305-02-0011-5
Figure 110122316-A0305-02-0011-5

寡聚物-酸基改質的聚丁二烯丙烯酸酯 Oligomer-acid-modified polybutadiene acrylate

於本揭露的下述實施例1至14中，所使用的酸基改質的聚丁二烯丙烯酸酯為馬來酸酐接枝聚丁二烯丙烯酸酯(Maleic anhydride grafted polybutadiene acrylate,MGPA)(克雷威利公司Ricacryl 3500)，其重量平均分子量約為6,000g/mol。其中，馬來酸酐接枝聚丁二烯丙烯酸酯的結構可如下式(II-2)所示。 In the following examples 1 to 14 of the present disclosure, the acid-modified polybutadiene acrylate used is maleic anhydride grafted polybutadiene acrylate (Maleic anhydride grafted polybutadiene acrylate, MGPA) (g Ricacryl 3500 from Lei Weili Company), its weight average molecular weight is about 6,000 g/mol. Wherein, the structure of the maleic anhydride grafted polybutadiene acrylate can be shown in the following formula (II-2).

Figure 110122316-A0305-02-0011-6
Figure 110122316-A0305-02-0011-6

脂環式丙烯酸酯單體 Alicyclic Acrylate Monomer

於本揭露的下述對照例1、實施例1至14及比較例1至2中，所使用的脂環式丙烯酸酯單體為丙烯酸異冰片酯(Acrylic acid isobornyl ester,IBOA)(雙鍵化學股份有限公司DOUBLEMER IBOA)。其中，丙烯酸異冰片酯的結構可如下式(III)所示。 In the following Comparative Example 1, Examples 1 to 14 and Comparative Examples 1 to 2 of the present disclosure, the alicyclic acrylate monomer used is isobornyl acrylate (Acrylic acid isobornyl ester, IBOA) (double bond chemical CO., LTD DOUBLEMER IBOA). Wherein, the structure of isobornyl acrylate can be shown in the following formula (III).

Figure 110122316-A0305-02-0011-7
Figure 110122316-A0305-02-0011-7

多官能丙烯酸酯單體 Multifunctional Acrylate Monomer

於本揭露的下述對照例1及實施例1至14中，所使用的多官能丙烯酸酯單體為雙季戊四醇六丙烯酸酯(Dipentaerythritol hexaacrylate,DPHA)(雙鍵化學股份有限公司DOUBLEMER DPHA)。其中，雙季戊四醇六丙烯酸酯的結構可如下式(IV)所示。 In the following comparative example 1 and examples 1 to 14 of the present disclosure, the multifunctional acrylate monomer used is dipentaerythritol hexaacrylate (DPHA) (DOUBLEMER DPHA, Double Bond Chemical Co., Ltd.). Wherein, the structure of dipentaerythritol hexaacrylate may be shown in the following formula (IV).

Figure 110122316-A0305-02-0012-8
Figure 110122316-A0305-02-0012-8

光起始劑 Photoinitiator

於本揭露的下述對照例1、實施例1至14及比較例1至2中，所使用的光起始劑為雙(2,4,6-三甲基苯甲醯基)苯基氧化磷(Phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide)(安鋒實業股份有限公司Omnirad 819)。其中，雙(2,4,6-三甲基苯甲醯基)苯基氧化磷的結構可如下式(V)所示。 In the following Comparative Example 1, Examples 1 to 14 and Comparative Examples 1 to 2 of the present disclosure, the photoinitiator used is bis(2,4,6-trimethylbenzoyl)phenyl oxide Phosphorus (Phenylbis (2,4,6-trimethylbenzoyl) phosphine oxide) (Omnirad 819 from Anfeng Industrial Co., Ltd.). Wherein, the structure of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide can be shown in the following formula (V).

Figure 110122316-A0305-02-0012-9
Figure 110122316-A0305-02-0012-9

填充物 filler

於本揭露的下述對照例1、實施例1至14及比較例1至2中，所使用的填充物可為二氧化矽(AEROSIL® 380 Evonic(對照例1及實施例1至7)或PF111首立企業股份有限公司(實施例8至10及比較例1至2))或滑石粉(FG-15日本滑石株式會社)。 In the following Comparative Example 1, Examples 1 to 14 and Comparative Examples 1 to 2 of the present disclosure, the filler used may be silicon dioxide (AEROSIL® 380 Evonic (Comparative Example 1 and Examples 1 to 7) or PF111 Shouli Enterprise Co., Ltd. (Examples 8 to 10 and Comparative Examples 1 to 2)) or talcum powder (FG-15 Nippon Talc Co., Ltd.).

寡聚物-末端丙烯酸改性聚丁二烯化合物 Oligomer-terminated acrylic acid modified polybutadiene compound

於本揭露的下述比較例1及2中，所使用的寡聚物為末端丙烯酸改性聚丁二烯化合物(日本曹達株式會社TEAI-1000)，其重量平均分子量約為2,000g/mol。。 In the following comparative examples 1 and 2 of the present disclosure, the oligomer used is acrylic-terminated polybutadiene compound (TEAI-1000 from Nippon Soda Co., Ltd.), with a weight average molecular weight of about 2,000 g/mol. .

增塑劑-氫化聚異丁烯 Plasticizer - hydrogenated polyisobutylene

於本揭露的下述比較例1及2中，所使用的增塑劑為氫化聚異丁烯，動黏度為800cSt(98.9℃)(日本油脂株式會社PARLEAM 24)。 In the following comparative examples 1 and 2 of the present disclosure, the plasticizer used is hydrogenated polyisobutylene with a dynamic viscosity of 800 cSt (98.9° C.) (PARLEAM 24 from NOF Corporation).

對照例1 Comparative example 1

分別將55g的IBOA、3g的DPHA與2g的光起始劑置於燒杯中使用機械攪拌機攪拌30分鐘使上述成分均勻混合；而後，加入38g的HPBA與2g的填充物，再使用機械攪拌機攪拌30分鐘，最後使用真空脫泡機脫泡。如此，可得到對照例1的紫外光固化組成物。 Put 55g of IBOA, 3g of DPHA and 2g of photoinitiator in a beaker and stir for 30 minutes with a mechanical stirrer to mix the above ingredients evenly; then, add 38g of HPBA and 2g of filler, and stir with a mechanical stirrer for 30 minutes Minutes, and finally use a vacuum defoamer to defoam. In this way, the UV curable composition of Comparative Example 1 can be obtained.

實施例1 Example 1

分別將2g的MGPA、35g的IBOA、2g的DPHA與2g的光起始劑置於燒杯中使用機械攪拌機攪拌30分鐘使上述成分均勻混合；而後，加入59g的HPBA與2g的填充物，再使用機械攪拌機攪拌30分鐘，最後使用真空脫泡機脫泡。如此，可製得實施例1的紫外光固化組成物。 Put 2g of MGPA, 35g of IBOA, 2g of DPHA and 2g of photoinitiator into a beaker and stir for 30 minutes with a mechanical stirrer to mix the above ingredients evenly; then, add 59g of HPBA and 2g of filler, and then use Stir with a mechanical mixer for 30 minutes, and finally use a vacuum defoamer to defoam. In this way, the UV-curable composition of Example 1 can be prepared.

實施例2至14 Examples 2 to 14

依據下表1及實施例1的製備方法，製備實施例2至14的紫外光固化組成物。 According to the following Table 1 and the preparation method of Example 1, the UV-curable compositions of Examples 2 to 14 were prepared.

比較例1 Comparative example 1

分別將1.5g的光起始劑、17.4g的IBOA置於燒杯中使用機械攪拌機攪拌30分鐘；而後，加入57.9g的TEAI-1000、23.2g的PARLEAM 24與10g的SiO2，再使用機械攪拌機攪拌30分鐘，最後使用真空脫泡機脫泡。如此，可製得比較例1的紫外光固化組成物。 Put 1.5g of photoinitiator and 17.4g of IBOA in a beaker and stir for 30 minutes with a mechanical stirrer; then, add 57.9g of TEAI-1000, 23.2g of PARLEAM 24 and 10g of SiO 2 , and then use a mechanical stirrer to Stir for 30 minutes, and finally use a vacuum defoamer to defoam. In this way, the UV-curable composition of Comparative Example 1 can be prepared.

比較例2 Comparative example 2

依據下表2及比較例1的製備方法，製備比較例2的紫外光固化組成物。 According to the following Table 2 and the preparation method of Comparative Example 1, the UV-curable composition of Comparative Example 2 was prepared.

比較例3 Comparative example 3

比較例3的紫外光固化組成物為市售的紫外光固化組成物(3035B)，其包括32重量份的PU改質寡聚物、8重量份的IBOA、光起始劑及50重量份的SiO2。 The UV curable composition of Comparative Example 3 is a commercially available UV curable composition (3035B), which includes 32 parts by weight of PU modified oligomer, 8 parts by weight of IBOA, photoinitiator and 50 parts by weight of SiO 2 .

冷熱衝擊測試 Thermal Shock Test

將對照例1、實施例1至14及比較例1至3的紫外光固化組成物塗佈於一欲封裝的基材上形成一邊框，而後於上方蓋上另一片有鑽孔的基材。接著，使用365nm波長紫外光將所塗佈的組成物進行固化後(固化條件：LED 365nm燈源、能量9J/cm2)秤重，於孔洞處注入3-甲氧基丙腈(3-Methoxypropionitrile,MPN)溶劑後將此試片進行秤重，扣除前一步驟試片重量得MPN重量。將鑽孔處密封後，再將完成的試片進行秤重。 The UV-curable compositions of Comparative Example 1, Examples 1-14 and Comparative Examples 1-3 were coated on a substrate to be packaged to form a frame, and then another substrate with drilled holes was covered on top. Next, after curing the coated composition with 365nm wavelength ultraviolet light (curing conditions: LED 365nm light source, energy 9J/cm 2 ), weigh it, and inject 3-methoxypropionitrile (3-Methoxypropionitrile) into the hole. , MPN) solvent, weigh the test piece, and subtract the weight of the test piece in the previous step to obtain the MPN weight. After the drilled hole is sealed, the completed test piece is weighed.

將完成封裝之對照例、實施例與比較例試片樣品，置入冷熱衝擊試驗機進行測試後秤重計算MPN的重量損失。冷熱衝擊條件為，-10℃持溫60分鐘與60℃持溫60分鐘間循環，循環次數為50次。MPN重量損失計算方式如下。MPN重量損失=[(冷熱衝擊測試前重量-冷熱衝擊測試後重量)/MPN重量]×100% The samples of the comparative example, the embodiment and the comparative example which have been packaged are put into the thermal shock testing machine for testing, and then weighed to calculate the weight loss of the MPN. The cold and heat shock condition is to cycle between holding the temperature at -10°C for 60 minutes and holding the temperature at 60°C for 60 minutes, and the number of cycles is 50 times. MPN weight loss is calculated as follows. MPN weight loss=[(weight before thermal shock test-weight after thermal shock test)/MPN weight]×100%

結果列於下表1及表2中，其中，◎：無重量損失；X：膠材脫落而造成封裝失效。 The results are listed in Table 1 and Table 2 below, wherein, ◎: no weight loss; X: the adhesive material fell off and the package failed.

百格測試 Baige test

依ASTM D3359測試規範，使用專用刀具將固化於基材上的UV膠切割成棋盤狀後，使用專用膠帶黏貼於UV膠上方後快速撕開，最後依照規範標準判定密著度。結果列於下表1及表2中，其中，◎：4B~5B，優良；△：2B~3B，尚可；X：0B~1B，不佳。 According to the ASTM D3359 test specification, use a special tool to cut the UV adhesive cured on the substrate into a checkerboard shape, use a special tape to stick it on the top of the UV adhesive and tear it off quickly, and finally judge the adhesion according to the specification standard. The results are listed in Table 1 and Table 2 below, where ◎: 4B~5B, excellent; △: 2B~3B, fair; X: 0B~1B, not good.

冷熱衝擊測試及百格測試結果列於下表1及表2中。 The results of the thermal shock test and the 100-gram test are listed in Table 1 and Table 2 below.

Figure 110122316-A0305-02-0015-10
Figure 110122316-A0305-02-0015-10

在百格測試實驗中，實施例1至14的紫外光固化組成物對玻璃、不鏽鋼、PET的密著等級均為5B，此結果顯示本揭露的紫外光固化組成物對不同基材有良好的密著性。反觀對照例1的紫外光固化組成物，對玻璃、不鏽鋼、PET的密著等級均為1B以下，顯示對照例1的紫外光固化組成物對基材的密著性不佳。 In the Baige test experiment, the adhesion grades of the UV-curable compositions of Examples 1 to 14 to glass, stainless steel, and PET were all 5B. This result shows that the UV-curable compositions of the present disclosure have good adhesion to different substrates. Adhesion. On the other hand, the UV-curable composition of Comparative Example 1 has an adhesion grade of less than 1B to glass, stainless steel, and PET, which shows that the UV-curable composition of Comparative Example 1 has poor adhesion to the substrate.

在冷熱衝擊實驗中，以實施例1至14的紫外光固化組成物製得的試片，在玻璃/玻璃、不鏽鋼/玻璃、PET/PET其MPN重量損失皆為0wt%，此結果亦顯示本揭露的紫外光固化組成物對基材的密着度良好，故在高強度的冷熱收縮情況下，膠體無剝離或從基材上脫落而導致封裝失效，而不會產生溶劑在高溫下有重量損失的情況。反觀對照例1的紫外光固化組成物製得的試片，在玻璃/玻璃、不鏽鋼/玻璃基材雖無明顯的MPN重量損失，但在PET/PET基材的測試中發生封裝膠於PET基材上剝離的封裝失效的情形，顯示對照例1的紫外光固化組成物對基材的密著性不佳。 In the thermal shock test, the weight loss of MPN in glass/glass, stainless steel/glass, PET/PET of the test pieces prepared with the UV-curable composition of Examples 1 to 14 was 0wt%, and this result also shows that the The disclosed UV-curable composition has good adhesion to the substrate, so in the case of high-strength cold and heat shrinkage, the colloid does not peel off or fall off from the substrate, resulting in package failure, and does not cause solvents to lose weight at high temperatures Case. In contrast, the test piece made of the UV-curable composition of Comparative Example 1, although there is no obvious MPN weight loss on the glass/glass and stainless steel/glass substrates, but the encapsulation glue on the PET substrate occurred in the test of the PET/PET substrate. The failure of the package peeled off from the substrate shows that the UV-curable composition of Comparative Example 1 has poor adhesion to the substrate.

Figure 110122316-A0305-02-0017-11
Figure 110122316-A0305-02-0017-11

在百格測試實驗中，比較例1至3的紫外光固化組成物在玻璃、不鏽鋼、PET的密著等級均不佳，顯示它們對基材的密著度差。在冷熱衝擊實驗中，比較例1至3的紫外光固化組成物所製得的試片，在玻璃/玻璃、不鏽鋼/玻璃基材雖無明顯的MPN重量損失，但在PET/PET基材的測試中發生封裝膠於PET基材上剝離而有封裝失效的情形。 In the Baige test, the UV-curable compositions of Comparative Examples 1 to 3 have poor adhesion levels to glass, stainless steel, and PET, indicating that they have poor adhesion to the substrate. In the thermal shock test, although the test pieces made of the UV-curable compositions of Comparative Examples 1 to 3 had no obvious MPN weight loss on glass/glass and stainless steel/glass substrates, they did not show significant MPN weight loss on PET/PET substrates. During the test, the encapsulant was peeled off from the PET substrate and the encapsulation failed.

由前述的實驗結果顯示，於本揭露的紫外光固化組成物中，當以氫化聚丁二烯丙烯酸酯作為封裝膠的主成分時，藉由添加適量的酸基改質的聚丁二烯丙烯酸酯，可提升固化後的組成物對於基材的密著度，並且提升固化後的組成物的穩定性。特別是，在冷熱衝擊測試下，基材與固化後的組成物間的接著在高強度熱脹冷縮的嚴苛環境中，無剝離脫落導致測試溶劑逸散或水氣滲入的情況發生；並且不同基材的百格測試結果皆為密著度最高等級5B，由此可 證明本揭露的紫外光固化組成物可有效確保被封裝物在使用環境下的耐候度與可靠度。 The aforementioned experimental results show that in the UV-curable composition of the present disclosure, when hydrogenated polybutadiene acrylate is used as the main component of the encapsulant, by adding an appropriate amount of acid group-modified polybutadiene acrylate The ester can improve the adhesion of the cured composition to the substrate, and improve the stability of the cured composition. In particular, under the thermal shock test, the bond between the base material and the cured composition is subjected to high-intensity thermal expansion and contraction in a harsh environment, and there is no peeling off that causes the escape of the test solvent or the infiltration of water vapor; and The results of the Baige test for different substrates are all 5B, the highest level of adhesion, so it can be It is proved that the UV curable composition disclosed in the present disclosure can effectively ensure the weather resistance and reliability of the encapsulated object in the use environment.

Figure 110122316-A0305-02-0002-1
Figure 110122316-A0305-02-0002-1

Claims (9)

一種紫外光固化組成物，包括：30至60重量份之氫化聚丁二烯丙烯酸酯；1至10重量份之酸基改質的聚丁二烯丙烯酸酯；30至60重量份之脂環式丙烯酸酯單體；1至10重量份之多官能丙烯酸酯單體；1至10重量份之光起始劑；以及1至50重量份之填充物；該氫化聚丁二烯丙烯酸酯如下式(I)所示：
Figure 110122316-A0305-02-0019-12
 其中，R1及R2分別獨立為氫或甲基；R3及R4分別為包括一或兩個-NH(CO)O-及C3-10亞環烷基之官能基，其中C3-10亞環烷基可選擇性的被C1-3烷基所取代；以及m及n的比例(m：n)為0~100：100~0；其中該酸基改質的聚丁二烯丙烯酸酯如下式(II)所示：
Figure 110122316-A0305-02-0019-13
 其中，A為含有羧酸基且1至6個碳之連接基；x為小於100的正整數； y為小於40的正整數；z為小於10的正整數；以及a為2、3或4。 An ultraviolet light curing composition, comprising: 30 to 60 parts by weight of hydrogenated polybutadiene acrylate; 1 to 10 parts by weight of polybutadiene acrylate modified by acid groups; 30 to 60 parts by weight of alicyclic Acrylate monomer; 1 to 10 parts by weight of multifunctional acrylate monomer; 1 to 10 parts by weight of photoinitiator; and 1 to 50 parts by weight of filler; the hydrogenated polybutadiene acrylate is as follows ( I) Shown:
Figure 110122316-A0305-02-0019-12
 Wherein, R 1 and R 2 are independently hydrogen or methyl; R 3 and R 4 are respectively functional groups including one or two -NH(CO)O- and C 3-10 cycloalkylene, wherein C 3 The -10 cycloalkylene can be optionally substituted by C 1-3 alkyl; and the ratio of m and n (m:n) is 0~100:100~0; wherein the polybutylene modified by the acid group Acrylic acid ester is shown in the following formula (II):
Figure 110122316-A0305-02-0019-13
 Wherein, A is a linking group containing a carboxylic acid group and 1 to 6 carbons; x is a positive integer less than 100; y is a positive integer less than 40; z is a positive integer less than 10; and a is 2, 3 or 4 . 如請求項1所述的紫外光固化組成物，其中R3及R4分別如下式(I-1)所示：
Figure 110122316-A0305-02-0020-14
 其中，l及k分別獨立為0至4的整數；p為0至6的整數；以及*連接至氧原子，而**連接至碳原子。 The UV-curable composition as described in Claim 1, wherein R 3 and R 4 are shown in the following formula (I-1):
Figure 110122316-A0305-02-0020-14
 Wherein, l and k are independently an integer from 0 to 4; p is an integer from 0 to 6; and * is connected to an oxygen atom, and ** is connected to a carbon atom. 如請求項1所述的紫外光固化組成物，其中該氫化聚丁二烯丙烯酸酯的重量平均分子量介於10,000至100,000g/mol之間。 The ultraviolet curable composition according to claim 1, wherein the weight average molecular weight of the hydrogenated polybutadiene acrylate is between 10,000 and 100,000 g/mol. 如請求項1所述的紫外光固化組成物，其中A如下式(II-1)所示：
Figure 110122316-A0305-02-0020-15
 其中，*連接至碳原子，而**連接至氧原子。 The ultraviolet light curing composition as described in claim item 1, wherein A is shown in the following formula (II-1):
Figure 110122316-A0305-02-0020-15
 Among them, * is attached to a carbon atom, and ** is attached to an oxygen atom. 如請求項1所述的紫外光固化組成物，其中該酸基改質的聚丁二烯丙烯酸酯的重量平均分子量介於2,000至8,000g/mol之間。 The ultraviolet curable composition according to claim 1, wherein the weight average molecular weight of the acid-modified polybutadiene acrylate is between 2,000 and 8,000 g/mol. 如請求項1所述的紫外光固化組成物，其中該脂環式丙烯酸酯單體為具有橋環烴骨架的(甲基)丙烯酸化合物。 The UV-curable composition according to claim 1, wherein the alicyclic acrylate monomer is a (meth)acrylic compound having a bridged ring hydrocarbon skeleton. 如請求項1所述的紫外光固化組成物，其中該多官能丙烯酸酯單體為含有3個或3個以上的丙烯酸酯官能基的單體。 The ultraviolet curable composition according to claim 1, wherein the multifunctional acrylate monomer is a monomer containing 3 or more acrylate functional groups. 如請求項1所述的紫外光固化組成物，其中該光起始劑為α-羥基酮衍生物、二苯甲酮及其衍生物、醯基磷氧化物或其組合。 The UV-curable composition according to claim 1, wherein the photoinitiator is an α-hydroxy ketone derivative, benzophenone and its derivatives, acyl phosphine oxide or a combination thereof. 如請求項1所述的紫外光固化組成物，其中該填充物為二氧化矽、滑石粉或其組合。 The ultraviolet curable composition according to claim 1, wherein the filler is silicon dioxide, talc or a combination thereof.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1516723A (en) * 2001-01-18 2004-07-28 通用电气公司 Electrically conductive thermoset composition, method for preparation thereof and articles derived therefrom
WO2007047513A1 (en) * 2005-10-19 2007-04-26 Henkel Corporation Adhesive useful for film laminating applications
JP2013539489A (en) * 2010-08-18 2013-10-24 ヘンケル コーポレイション Radiation curable temporary adhesive for use in high temperature applications

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1516723A (en) * 2001-01-18 2004-07-28 通用电气公司 Electrically conductive thermoset composition, method for preparation thereof and articles derived therefrom
WO2007047513A1 (en) * 2005-10-19 2007-04-26 Henkel Corporation Adhesive useful for film laminating applications
JP2013539489A (en) * 2010-08-18 2013-10-24 ヘンケル コーポレイション Radiation curable temporary adhesive for use in high temperature applications

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