TW201221541A - High refractive resin composition and cured resin - Google Patents
High refractive resin composition and cured resin Download PDFInfo
- Publication number
- TW201221541A TW201221541A TW100137678A TW100137678A TW201221541A TW 201221541 A TW201221541 A TW 201221541A TW 100137678 A TW100137678 A TW 100137678A TW 100137678 A TW100137678 A TW 100137678A TW 201221541 A TW201221541 A TW 201221541A
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- Prior art keywords
- group
- compound
- high refractive
- refractive index
- resin composition
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- 239000011342 resin composition Substances 0.000 title claims abstract description 56
- 239000011347 resin Substances 0.000 title claims abstract description 20
- 229920005989 resin Polymers 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- -1 carbazole compound Chemical class 0.000 claims abstract description 93
- 125000000524 functional group Chemical group 0.000 claims abstract description 36
- 239000007788 liquid Substances 0.000 claims abstract description 26
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 18
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000006239 protecting group Chemical group 0.000 claims description 26
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 13
- 239000007822 coupling agent Substances 0.000 claims description 11
- 239000011256 inorganic filler Substances 0.000 claims description 10
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 10
- 238000005401 electroluminescence Methods 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002981 blocking agent Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- WNORZIRJJLYFFF-UHFFFAOYSA-N 2-methylcyclopropan-1-one Chemical group CC1CC1=O WNORZIRJJLYFFF-UHFFFAOYSA-N 0.000 claims 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
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- 229940125904 compound 1 Drugs 0.000 claims 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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- 238000002156 mixing Methods 0.000 description 6
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
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- 238000003786 synthesis reaction Methods 0.000 description 4
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- OJLCQGGSMYKWEK-UHFFFAOYSA-K ruthenium(3+);triacetate Chemical compound [Ru+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OJLCQGGSMYKWEK-UHFFFAOYSA-K 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- AAWSDNAGOTWUPV-UHFFFAOYSA-N sulfanyloxyethene Chemical compound SOC=C AAWSDNAGOTWUPV-UHFFFAOYSA-N 0.000 description 1
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2669—Non-metals or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/269—Mixed catalyst systems, i.e. containing more than one reactive component or catalysts formed in-situ
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
- H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
Abstract
Description
201221541 六、發明說明: 【發明所屬之技術領域】 本發明關於用於有機電致發光裝置(有機EL裝置、 OLED裝置)、LED裝置、顯示器之抗反射膜等需要高折 射率的電子元件之一種高折射率樹脂組成物及其硬化物 ’一種含有南折射率樹脂組成物的封閉劑、密封劑;及 使用該等之有機電致發光裝置、led裝置、顯示器。 【先前技術】 以往有文獻報告出由如苐丙烯酸酯般具有由7個以 上碳原子所構成的共軛構造之化合物,可得到具有高折 射率的硬化物。然而,上述化合物的黏度非常高,會有 在摻合硬化劑時必須加熱’而且在作為封閉劑等使用時 操作性差這些缺點。 在專利文獻1中記載了一種組成物,其係併用第丙烯 酸醋與具有芳香族構造的陽離子聚合性液狀化合物,以 作為塑膠鏡片材料等。然而,在此組成物中,為了要均 勻混合而必須在1 00下加熱或使用溶劑,其操作性不足 ’另外也不適於封閉劑、密封劑等的用途。 另外’在專利文獻2中記載了一種陽離子硬化性組成 物’其含有N-乙烯基咔唑與環氧化物等,而可提供對熱 相對上安定,並且非腐蝕性之硬化後的組成物。此組成 物必須在40〜1 〇(TC左右下製成活性化的膠囊,且使用鍵 結於聚合物的鹼。此外,實際上含有…乙烯基咔唑與環 氧化物等的組成物並未被調製出來,也沒有探討硬化後 組成物的折射率。 -4- [發明所欲解決之課題] 本發明之目的纟於提供—帛高折射精脂組成物 其係可使用作為有機電致發光裝置' LED裝置、顯示 201221541 [先前技術文獻] [專利文獻] [專利文獻1]日本特開2009-235 196號公報 [專利文獻2]日本特表2〇〇7_512414號公報 【發明内容】 之抗反射膜等的要求具有高折射率的電子元件用之封 劑、密封劑、被覆劑等,其在。〜㈣之任一溫度下為 體,並且進一步可賦予具有高折射率的硬化物。 卜本發明其他目的在於提供一種具有高折射 物係使上述高折射率樹脂組成物硬化而得 本發明另一個進一步的目的在於提供一種封閉劑 密封劑,其可时、2 、賦予具有高折射率的硬化物。 種有機電致發光 ,其係藉著上述 ,因此光線取出 [用於解決課題之手段] 本兔明人等為了解決上述課題潛心檢討的結果, 二:H以上含有藉著U V等的放射線或熱而發生反應 s月b基與咔唑骨靼〜 月东的特疋材料與1種以上可藉著尊 放射線或熱而硬化 化而且具有反應性官能基的特定材料 以〉昆合而得的知士 & 、”成物,在聚合開始溫度以下(例如〇 器 閉 液 率 此外本發明其他目的在於提供一 置、LED裝[附抗反射膜的顯示器 閉劑或f封劑將電子元件封閉或密封 裝 封 致 發 的 的 力〇 201221541 9〇°C)為液體,使該組成物硬 (例如1〜),來自電子元件折料高 成本發明。 忐的取出效率高,而完 亦即,本發明提供一種電子 物,其特Μ & ^ + 件用向折射率樹脂組成 观兴W徵為含有:下述式(1)所矣-—μ ” 表不之咔唑化合物(A):201221541 6. TECHNOLOGICAL FIELD OF THE INVENTION The present invention relates to an electronic component requiring high refractive index, such as an organic electroluminescent device (organic EL device, OLED device), an LED device, an antireflection film for a display, and the like. A high refractive index resin composition and a cured product thereof - a blocking agent and a sealant containing a composition of a south refractive index resin; and an organic electroluminescence device, a LED device, and a display using the same. [Prior Art] Conventionally, it has been reported that a compound having a conjugated structure composed of seven or more carbon atoms, such as an oxime acrylate, can provide a cured product having a high refractive index. However, the above-mentioned compound has a very high viscosity, and it must be heated when it is blended with a hardener, and it has a disadvantage that it is inferior in workability when used as a sealant or the like. Patent Document 1 describes a composition in which a acrylic acid vinegar and a cationically polymerizable liquid compound having an aromatic structure are used in combination as a plastic lens material. However, in this composition, in order to be uniformly mixed, it is necessary to heat or use a solvent at 100 Å, which is insufficient in handleability. Further, it is not suitable for use as a sealant, a sealant or the like. Further, Patent Document 2 describes a cationically curable composition which contains N-vinylcarbazole, an epoxide or the like, and which provides a composition which is relatively stable in heat and non-corrosive. This composition must be made into an activated capsule at about 40 to 1 Torr (about TC, and a base bonded to the polymer is used. In addition, the composition of vinyl oxazole and epoxide is actually not contained. It is prepared and does not investigate the refractive index of the composition after hardening. -4- [Problems to be Solved by the Invention] The object of the present invention is to provide a high refractive essential lipid composition which can be used as an organic electroluminescence. DEVICE 'LED DEVICE, DISPLAY 201221541 [PRIOR ART DOCUMENT] [Patent Document 1] [Patent Document 1] Japanese Laid-Open Patent Publication No. 2009-235 196 [Patent Document 2] Japanese Patent Application Publication No. H07-512414 A sealing agent, a sealant, a coating agent, or the like for an electronic component having a high refractive index, such as a reflective film, is required to be a body at any temperature of ~(d), and further capable of imparting a cured product having a high refractive index. Another object of the present invention is to provide a high-refractive-index system for hardening the above-mentioned high-refractive-index resin composition. Another object of the present invention is to provide a sealant sealant which can be provided with time, 2, and A cured product having a high refractive index. Organic electroluminescence, which is obtained by the above-mentioned light, is used as a means for solving the problem. In order to solve the above problems, the results of the review are as follows: Reaction by radiation or heat such as UV s month b-base and carbazole bone 靼 ~ 东 East special material and one or more specific materials which can be hardened by radiation or heat and have reactive functional groups "Knowledge & ", "the product, below the polymerization start temperature (for example, the liquid shutoff rate of the device). Other objects of the present invention are to provide a display, LED package [display with anti-reflection film or The f sealant seals or seals the electronic component to a force of 201221541 9〇°C) as a liquid, making the composition hard (for example, 1~), from the electronic component folding high cost invention. High, and the present invention provides an electronic article, the characteristic of which is used for the composition of the refractive index resin to contain: the following formula (1) 矣--μ" Carbazole compound (A):
(1) 匕3乙烯基、環氧基、氧雜 環丁烷基、丙烯醯基、〗曱基丙烯醯基之群組中之至少 -個反應性官能基之基團⑷;又為鍵結於構成各環的原 子之取代基,其表示齒素原子、烷基、•烷基、芳香基 、可經保護基保護之羥基、可經保護基保護之羥甲基、 可經保護基保護之胺基'可經保護基保護之羧基、可經 保護基保護之續基、側氧基、硝基、氰基、或可經保護 基保護之醯基;m表示〇〜8之整數,爪為2〜8的情況,複 數個X可相同或相異,亦可互相鍵結而與構成式中的環之 碳原子一起形成4員以上的環]; 在1分子中具有1個以上含有選自包含環氧基、氧雜 環丁烷基、乙烯醚基、丙烯醯基、及甲基丙烯醯基之群 組中之至少一個反應性官能基之基團(b)的化合物(B);及 聚合起始劑(C) ’並且在〇〜90 °c之任一溫度下為液體。 本發明之電子元件用高折射率樹脂組成物,係以含 有2種以上相異的複數個前述化合物(B)為佳。 201221541 進一步而言,前述化合物印)或複數個化合物(B)之 至少1種化合物(B),係以含有2個以上上述反應性官能基 與1個以上的芳香族環為佳。 本發月之電子元件用尚折射率樹脂組成物亦可進一 步含無機填料(D)及/或矽烷偶合劑(E)。 ,上述電子元件亦可為有機電致發光裝置、LED裝置 、或顯示器。 · 另外本發明還提供一種硬化物,係使上述電子元件 用南折射率樹脂組成物硬化而成。 本發明進一步提供一種封閉劑、密封劑、及抗反射 用被覆劑’其含有上述電子元件用高折射率樹脂組成物 〇 甚至另外本發明還提供一種有機電致發光裝置、 LED裝置、及顯示器,其含有上述硬化物。 [發明之效果] 與本發明相關之兩折射率樹脂組成物在〇〜9 〇它之 任Τ溫度下為液體,並且操作性優異。另外,與本發明 相關之高折射率樹脂組成物在硬化後的樹脂之折射率高 (例如1.62以上),藉由使用該樹脂可使來自電子元件的Ζ 的取出效率上升《藉由以含有與本發明相關之高折射率 樹脂組成物的封閉劑或渣封劑將電子元件封閉或密封, 可製造出光線取出效率南的有機電致發光裝置、led穿 置、附抗反射膜的顯示器。 ~ 【實施方式】 [用以實施發明之形態] 201221541 [電子元件用高把 折射率樹脂組成物] 本發明之蕾 其特徵 良人古· τ 子元件用高折射率樹脂組成物 為含有·下述 反V 1)所表示之咔唑化合物(A):(1) a group (4) of at least one reactive functional group in the group of a vinyl group, an epoxy group, an oxetanyl group, an acryloyl group, or a fluorenyl fluorenyl group; a substituent of an atom constituting each ring, which represents a dentate atom, an alkyl group, an alkyl group, an aromatic group, a hydroxyl group which can be protected by a protecting group, a methylol group which can be protected by a protecting group, and which can be protected by a protecting group. The amine group can be protected by a protecting group, a protecting group-protected group, a pendant oxy group, a nitro group, a cyano group, or a protecting group capable of protecting a group; m represents an integer of 〇~8, and the claw is In the case of 2 to 8, a plurality of X's may be the same or different, or may be bonded to each other to form a ring of 4 or more members together with a carbon atom of a ring in the structural formula]; a compound (B) comprising a group (b) of at least one reactive functional group of an epoxy group, an oxetanyl group, a vinyl ether group, an acryloyl group, and a methacryl group; and The polymerization initiator (C)' is a liquid at any temperature of 〇~90 °c. The high refractive index resin composition for electronic components of the present invention is preferably a plurality of the above-mentioned compounds (B) having two or more kinds of different components. Further, at least one compound (B) of the above compound (B) or a plurality of compounds (B) preferably contains two or more reactive functional groups and one or more aromatic rings. The composition of the refractive index resin for electronic components of this month may further contain an inorganic filler (D) and/or a decane coupling agent (E). The electronic component may be an organic electroluminescent device, an LED device, or a display. Further, the present invention provides a cured product obtained by hardening the above-mentioned electronic component with a south refractive index resin composition. The present invention further provides a sealant, a sealant, and an antireflection coating agent comprising the above high refractive index resin composition for an electronic component, and even the present invention further provides an organic electroluminescence device, an LED device, and a display. It contains the above hardened material. [Effects of the Invention] The two-refractive-index resin composition according to the present invention is liquid at a temperature of from 〇 to 9 ,, and is excellent in handleability. Further, the high refractive index resin composition according to the present invention has a high refractive index (for example, 1.62 or more) of the cured resin, and the use of the resin can increase the extraction efficiency of the germanium from the electronic component. The sealing agent or the sizing agent of the high refractive index resin composition according to the present invention encloses or seals the electronic component, and can produce an organic electroluminescence device having a light extraction efficiency, a LED through, and a display with an antireflection film. [Embodiment] [Formation for Carrying Out the Invention] 201221541 [High-refractive-index resin composition for electronic components] The bud of the present invention is characterized by a high-refractive-index resin composition for a good τ sub-element. The carbazole compound (A) represented by the inverse V 1):
(1) 在1分子中具有含有丨個以上選自包含環氧基、氧雜 :裒丁烷基、乙烯醚基、丙烯醯基、及甲基丙烯醯基之群 組中之至少—個反應性官能基之基團(b)的化合物⑻;及 聚。起始劑(C),在0〜9〇 〇c之任一溫度下為液體。 [咔唑化合物(A);) 在上述式(1)所表示之咔唑化合物(A)之中式中,尺 表示含有選自包含乙烯基、環氧基、氧雜環丁烷基、丙 烯醯基、及甲基丙烯醯基之群組中之至少一個反應性官 能基之基團(a卜X為鍵結於構成各環的原子之取代基, 表示齒素原子、烧基、齒燒基、芳香基、可經保護基保 護之經基、可經保護基保護之羥甲基、可經保護基保護 之胺基、可經保護基保護之羧基、可經保護基保護之磺 基、側氧基、硝基、氰基、或可經保護基保護之醯基; m表不〇〜8之整數。„!為2〜8的情況’複數個X可相同或 相異’可互相鍵結而與構成式中的環之碳原子一起形成4 員以上的環。 含上述反應性官能基之基團(a)具體而言,可列舉乙 稀基、烯丙基、環氧基(亦即環氧乙烷基)、縮水甘油基 201221541 、氧雜% 丁烷基、(曱基)丙烯醯基、乙基(甲基)丙烯醯基 、乙氧基乙基(甲基)丙烯醯基、(1_曱基乙基)(甲基)丙烯 醯基、(2-甲基乙基)(曱基)丙烯醯基等的烷基(甲基)丙烯 酸酯基等。 上述作為X的齒素原子可列舉例如氟、氣、溴原子等 。烷基可列舉例如曱基、乙基、丙基、異丙基、丁基、 異丁基、第二丁基、第三丁基、己基、辛基、癸基等的 Cido烧基(宜為c]_5烷基)等。鹵烷基可列舉例如氯甲基、 三氟甲基、三氟乙基、五氟乙基等的C110鹵烷基(宜為C15 鹵烷基)。芳香基可列舉例如笨基、萘基等。芳香基之芳 香環亦可具有例如氟原子等的鹵素原子、曱基等的C , 烧基、三I曱基等Ci 5鹵烷基、羥基、甲氧基等的C14烷 氧基、胺基、二烷基胺基、羧基、曱氧基羰基等的烷氧 叛基、墙基、氰基、乙醯基等的醯基等的取代基。 上述作為X的羥基及羥甲基之保護基為有機合成領 域所慣用的保護基,可例示例如烷基(例如甲基、第三丁 基等的Cw燒基等);烯基(例如烯丙基等);環烷基(例如 環己基等);芳香基(例如2,4-二硝基苯基等);芳烷基(例 如节基等);經取代之曱基(例如曱氧基曱基、曱硫基曱 基、苄氧基甲基、第三丁氧基甲基、2_甲氧基乙氧基曱 基等)、經取代之乙基(例如i _乙氧基乙基等)、四氫哌喃 基、四氫呋喃基、1 -羥烷基(例如1 -羥乙基等)等的可形成 經基與縮越或半縮醛基之基團;醯基(例如曱醯基、乙醯 基、丙醯基、丁醯基、異丁醯基、三曱基乙酿基等的ci6 脂肪族醯基;乙醯乙醯基;苯甲醯基等的芳香族醯基等) 201221541 :烧氧羰基(例如甲氧基羰基等的ci·4烷氧基羰基等);芳 烷氧基羰基;取代或無取代之胺甲醯基;取代石夕炫基( 例如二甲基曱石夕烧基等);在分子内存在2個以上經基(包 括經甲基)時,如可具有取代基之2價烴基(例如亞曱基、 亞乙基、亞異丙基、亞環戊基、亞環己基、亞苄基等) 等。 上述作為X的胺基之保護基可列舉例如前述經基之 保護基所例示之院基、芳炫基、酿基、炫氧叛基等。 上述作為X的羧基、績基之保護基可列舉例如烷氧基 (例如甲氧基、乙氧基、丁氧基等的C16烷氧基等)、環烷 氧基、芳香氧基、芳烧氧基、三烷基矽烧氧基、可具有 取代基之胺基、肼基、烷氧羰基肼基 '芳烷基羰基肼基 等。 上述作為X的醯基可列舉例如曱醯基、乙醯基、丙醯 基、丁醯基、異丁醯基、三甲基乙醯基等的C16脂肪族醯 基,乙醯乙醯基,苯甲醯基等的芳香族醯基等。醯基之 保護基可使用有機合成領域所慣用的保護基。醯基受到 保護的形態可列舉例如縮醛(含半縮酿)等。 在X為2個以上的情況,該等互相鍵結而與式(i)中之 構成環之碳原子一起形成4員以上的環,可列舉例如5員 之月s環式碳環(例如ί衣戊烷環)、6員之脂環式碳環(例如環 己烷環)、2以上的脂環式碳環(單環)之縮合環(例如全氫 萘環(十氫萘環))等的脂環式碳環;5員之内醋環(例如γ_ 丁内醋環)、6員之内S旨環(δ•戊内酿環)等的内酷環等。 咔唑化合物(Α)可列舉Ν_乙烯基咔唑;Ν_烯丙基咔唑 -10- 201221541 ;N-縮水甘油基咔唑;N-(甲基)丙烯醢基咔唑;咔唑基 乙基(甲基)丙烯酸醋、咔唑基乙氧基乙基(甲基)丙烯酸酯 、味σ圭基(1-甲基乙基)(曱基)丙稀酸g旨、叶坐基(2_甲基乙 基)(曱基)丙稀酸醋專的咔唑基烧基(甲基)丙烯酸酯等的 Ν -取代味峻衍生物等。 在R為乙烯基、烯丙基、環氧基、或氧雜環丁烷基的 情況’味嗤化合物(Α)具有陽離子硬化性。在尺為丙烯醯 基、或甲基丙烯醯基的情況,咔唑化合物(Α)具有自由基 硬化性。此外,在R為乙烯基或烯丙基的情況,咔唑化合 物(Α)也會有具有自由基硬化性的情形。r為乙烯基或烯 丙基硬化時,會有硬化收縮小的傾向,故為適合。咔唑 化合物(Α)係以Ν_乙烯基咔唑、比烯丙基咔唑為佳。此外 ,咔唑化合物(Α)可單獨使用i種或組合兩種以上使用。 上述咔唑化合物(A)的含量,係以相對於電子元件用 高折射率樹脂組成物中之具有聚合性(硬化性)的化合物( 聚2性化合物)總量的1〇〜8〇重量%為佳較佳為〜 重量%’更佳為40〜60重量%。坐化合物(a)的含量 =适樣的範圍,則樹脂組成物可提供塗布性優異、折射 率南 ' 具有較優異硬度的硬化物。 [化合物 不發明之電子元 --丨τ 1…丁州Λ日組取物所含 δ :(Β)’係在1分子中具有1個以上含有選自包含環氧某 Ζ雜環τ院基、乙稀醚基、丙㈣氧基及f基丙㈣ 土之群組中之至少一個反應性官能基之基團(b)。化入 物W為1種或同時摻合數種皆無妨。且以僅有化合心 -11- 201221541 之組成物在0〜90°C下為液體為佳。藉由這樣的設定,化 合物(B)與化合物(A)之摻合樹脂組成物變得容易在〇〜 90°C下成為液體。此外還設定為在化合物(B)中不含化合 物(A)。 化合物(B)所具有的含有反應性官能基之基團(b)中 ’環氧基、氧雜環丁烷基、乙烯醚基具有陽離子聚合性 ’(甲基)丙烯醯基具有自由基聚合性。乙烯醚基也會有 具有自由基聚合性的情形。 化合物(B)可列舉例如在1分子中具有_上的另 香族環與1個陽離子聚合性官能基的化合物㈣…分 子中具有1個以上的芳香族援命,a , 與1個自由基聚合性官能基 :化合物(Β·2);幻分子中具有!個以上的芳香族環 個以上的陽離子聚合性官 〃 基的化合物(B_3);在1分子 個以上的芳香族環與2個以上的自由基聚合性官 基的化人族環與陽離子聚合性官能 基的化合物(B-5广具有脂肪族 的化合物㈣;具有烧基與陽基聚合性官能基 物具找基與自由基 Μ基的化合 等。 11 s忐基的化合物(Β-8: 方香族環可列舉苯環、蔡 的單環或縮合多環的芳香族環:藉=菲環、剛 使樹脂組成物硬化的情況,可得二=香族環’在 此外’在本說明書之中n個環二硬化物。 環狀骨架的數目定為_。《方式形成的多環之 刀子中具有1個以上的芳香族環與1個陽離子聚 -12- 201221541 合性官能基的化合物(B -1)可列舉例如縮水甘油基苯醚 、苯酚縮水甘油醚、二苯酚二縮水甘油醚、三苯酚縮水 甘油醚等的具有苯環與環氡基的化合物;縮水甘油基曱 基苯醚、縮水甘油基乙苯醚、縮水甘油基丙基苯醚、縮 水甘油基正丁基苯醚、縮水甘油基第三丁基苯醚等的具 有經烧基取代之苯環與環氧基的化合物(例如具有Cl_9烷 基取代苯環與環氧基的化合物);甲基苯酚縮水甘油醚、 乙基苯驗縮水甘油醚、丙基苯酚縮水甘油醚、正丁基苯 酚縮水甘油醚、第三丁基苯酚縮水甘油醚等的經烷基取 代之苯酚縮水甘油醚(例如經c丨_9烷基取代之苯酚縮水甘 油醚);苄基(R)-(-)_縮水甘油醚、苯基苄基縮水甘油醚等 的下基縮水甘油醚化合物;苯基乙烯基醚、苯酚乙烯基 醚、苯氧基曱基乙烯基醚、(苯基苯氧基)甲基乙烯基醚 、(2-苯氧基)乙基乙烯基醚、(2_苯基苯氧基)乙基乙烯基 醚等的具有1或2個笨環的乙烯基醚化合物;苯基氧雜環 丁烷、笨酚氧雜環丁烷、苯氧基甲基氧雜環丁烷、(苯基 苯氧基)甲基氧雜環丁烷' (2_笨氧基)乙基氧雜環丁烷、 (2-苯基笨氧基)乙基氧雜環丁烷等的具有丨或2個苯環的 氧雜環丁烷化合物及該等的鹵化物等。上述Cm烷基取代 基可列舉甲基、乙基、丙基、第三丁基等。 _在1分子中具有1個以上的芳香族環與1個自由基聚 合性官能基之化合物(B - 2)可列舉例如(曱基)丙烯酸苯酯 、(甲基)丙烯酸苯酚酯、(甲基)丙烯酸笨氧基甲酯、(甲 基)&丙烯酸(苯基笨氧基)甲醋、(甲基)丙烯酸(2_笨氧基) 乙酯、(甲基)丙烯酸(2-苯基苯氧基)乙酯等的具有is?個 -13- 201221541 笨環與(曱基)丙烯醯基的化合物;及該等的函化物、或 該等的C1-9烷基取代物等。C,·9烷基取代基可列舉甲基、 乙基、丙基、第三丁基等,鹵素可列舉F、cn、Br等。 在1分子中具有1個以上的芳香族環與2個以上的陽 離子聚合性官能基之化合物(B_3)可列舉例如聯苯鹼二 縮水甘油醚、雙酚A二縮水甘油醚、雙酚F二縮水甘油醚 、雙酚S二縮水甘油醚、四曱基聯苯酚二縮水甘油醚等的 具有苯環與兩個環氧基的化合物;萘二醇二縮水甘油醚 、雙盼第二縮水甘油醚、雙甲酚第二縮水甘油醚、雙苯 氧基乙醇第二縮水甘油醚等的具有縮合環與兩個環氧基 的化合物;雙酚F雙(3-乙基-3-氧雜環丁烷基曱基)醚等的 具有芳香族環與兩個氧雜環丁烷基的化合物;聯苯紛二 乙烯基醚、雙酚A二乙烯基醚、雙酚F二乙烯基醚、雙酚 S二乙烯基醚、四甲基聯苯酚二乙烯基醚等的具有苯環與 兩個乙烯醚基的化合物;萘二醇二乙烯基醚、雙酚第二 乙烯基醚、雙甲酚苐二乙烯基醚、雙苯氧基乙=苐二乙 烯基醚等的具有縮合環與兩個乙烯醚基的化合物、及該 等的il化物、或該等的Cm烷基取代物等。 基可列舉曱基、乙基、丙基、第三丁基等; 、CM、Br等。(1) having at least one reaction selected from the group consisting of an epoxy group, an oxa group: a butane group, a vinyl ether group, a propylene group, and a methacryl group in one molecule a compound (8) of the group of the functional group (b); and poly. The initiator (C) is a liquid at any temperature from 0 to 9 〇 〇c. [Carbazole compound (A);) In the formula of the carbazole compound (A) represented by the above formula (1), the ruler represents a component selected from the group consisting of a vinyl group, an epoxy group, an oxetane group, and an acrylonitrile group. a group of at least one reactive functional group in the group of a group and a methacryl fluorenyl group (a, X is a substituent bonded to an atom constituting each ring, and represents a dentate atom, an alkyl group, a dentate group , an aromatic group, a protecting group which can be protected by a protecting group, a methylol group which can be protected by a protecting group, an amine group which can be protected by a protecting group, a carboxyl group which can be protected by a protecting group, a sulfo group which can be protected by a protecting group, and a side An oxy group, a nitro group, a cyano group, or a thiol group which can be protected by a protecting group; m is not an integer of ~8. „! is a case of 2 to 8 'multiple Xs may be the same or different' may be bonded to each other Further, a ring of 4 or more members is formed together with the carbon atom of the ring in the structural formula. The group (a) containing the above reactive functional group may specifically be an ethyl group, an allyl group or an epoxy group (ie, Ethylene oxide group), glycidyl group 201221541, oxaxanthyl butane, (fluorenyl) propylene sulfhydryl, ethyl (methyl) propyl An alkyl group such as a mercapto group, an ethoxyethyl (meth) acryl fluorenyl group, a (1 fluorenylethyl) (meth) acryl fluorenyl group, or a (2-methylethyl) fluorenyl fluorenyl group The dentate atom of X may, for example, be fluorine, a gas or a bromine atom. Examples of the alkyl group include a mercapto group, an ethyl group, a propyl group, an isopropyl group, a butyl group and a different group. a Cido alkyl group (preferably c)-5 alkyl group or the like of a butyl group, a second butyl group, a tert-butyl group, a hexyl group, an octyl group or a decyl group, etc. The haloalkyl group may, for example, be a chloromethyl group or a trifluoromethyl group. And a C110 haloalkyl group (preferably a C15 haloalkyl group) such as a trifluoroethyl group or a pentafluoroethyl group. Examples of the aryl group include a strepyl group, a naphthyl group, etc. The aromatic ring of the aryl group may have, for example, a fluorine atom or the like. a C14 alkoxy group such as a halogen atom or a fluorenyl group such as a C, a pyridyl group or a triacyl group; a C14 alkoxy group such as a hydroxyl group or a methoxy group; an amine group; a dialkylamino group; a carboxyl group; and a decyloxycarbonyl group; a substituent such as an alkyl group such as an alkoxy group, a wall group, a cyano group or an acetamino group. The above-mentioned protecting group for the hydroxyl group and the methylol group of X is a protecting group conventionally used in the field of organic synthesis. For example, an alkyl group (e.g., a Cw alkyl group such as a methyl group or a tributyl group); an alkenyl group (e.g., allyl group); a cycloalkyl group (e.g., a cyclohexyl group, etc.); an aromatic group (e.g., 2, 4-) can be exemplified. Dinitrophenyl or the like; an aralkyl group (e.g., a benzyl group, etc.); a substituted fluorenyl group (e.g., anthracenyloxy, fluorenylthio, benzyloxymethyl, tert-butoxymethyl) , 2-methoxyethoxymethyl, etc.), substituted ethyl (eg, i-ethoxyethyl, etc.), tetrahydropyranyl, tetrahydrofuranyl, 1-hydroxyalkyl (eg 1-hydroxyl) a group such as an ethyl group or the like which forms a radical and a condensed or hemiacetal group; a fluorenyl group (for example, an anthracenyl group, an ethyl fluorenyl group, a propyl fluorenyl group, a butyl fluorenyl group, an isobutyl fluorenyl group, a tridecyl aryl group, etc.) Ci6 aliphatic fluorenyl group; ethyl acetyl group; aromatic fluorenyl group such as benzamidine group; etc. 201221541 : aerobic carbonyl group (for example, ci. 4 alkoxycarbonyl group such as methoxycarbonyl group); aralkyl An oxycarbonyl group; a substituted or unsubstituted amine carbenyl group; a substituted fluorenyl group (for example, dimethyl fluorene, etc.); when there are more than 2 merid groups (including methyl groups) in the molecule And a divalent hydrocarbon group which may have a substituent (for example, an anthranylene group, an ethylene group, an isopropylidene group, a cyclopentylene group, a cyclohexylene group, a benzylidene group, etc.), or the like. Examples of the protective group of the amine group of X described above include, for example, a hospital base, an aromatic group, a brewing group, and an aerobic group which are exemplified by the protecting group of the above-mentioned group. Examples of the protective group of the carboxyl group and the base group of X include, for example, an alkoxy group (e.g., a C16 alkoxy group such as a methoxy group, an ethoxy group or a butoxy group), a cycloalkoxy group, an aromatic oxy group, and an aromatic group. An oxy group, a trialkyl sulfonium oxy group, an amine group which may have a substituent, a fluorenyl group, an alkoxycarbonyl fluorenyl 'aralkylcarbonyl fluorenyl group, and the like. Examples of the fluorenyl group as X include a C16 aliphatic fluorenyl group such as an anthracenyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group or a trimethylethenyl group, and an ethyl fluorenyl group. Such as aromatic sulfhydryl groups and the like. The protecting group of the thiol group can use a protecting group conventionally used in the field of organic synthesis. Examples of the form in which the thiol group is protected include acetal (including semi-condensed). In the case where X is two or more, these rings are bonded to each other to form a ring of four or more members together with the carbon atom constituting the ring in the formula (i), and for example, a 5-membered s ring carbon ring (for example, ί a pentane ring), a 6-membered alicyclic carbocyclic ring (for example, a cyclohexane ring), a condensed ring of 2 or more alicyclic carbocyclic rings (monocyclic) (for example, a perhydronaphthalene ring (decahydronaphthalene ring)) An alicyclic carbon ring; an internal cigar ring such as a vinegar ring (for example, γ_butane vinegar ring) within 5 members, and a ring inside the 6-membered ring (δ·pentane ring). The carbazole compound (Α) may, for example, be Ν-vinylcarbazole; Ν-allyl carbazole-10-201221541; N-glycidyl carbazole; N-(methyl) propylene fluorenyl oxazole; carbazolyl Ethyl (meth) acrylate, oxazolyl ethoxyethyl (meth) acrylate, sigma quetia (1-methylethyl) (fluorenyl) acrylate acid, leaf-based ( 2-methylethyl)(mercapto)acrylic acid vinegar-specific carbazole-based (meth) acrylate or the like - substituted for the taste derivative. In the case where R is a vinyl group, an allyl group, an epoxy group or an oxetanyl group, the miso compound (Α) has cationic hardenability. In the case where the ruler is an acryloyl group or a methacryloyl group, the carbazole compound (Α) has a radical hardenability. Further, in the case where R is a vinyl group or an allyl group, the carbazole compound (Α) may have a case of having radical curability. When r is a vinyl group or an allylic group, the curing shrinkage tends to be small, which is suitable. The carbazole compound (Α) is preferably Ν-vinylcarbazole or allyl carbazole. Further, the carbazole compound (Α) may be used singly or in combination of two or more. The content of the carbazole compound (A) is 1 〇 to 8 〇% by weight based on the total amount of the polymerizable (curable) compound (poly 2 compound) in the high refractive index resin composition for electronic components. Preferably, it is preferably ~% by weight 'more preferably 40 to 60% by weight. When the content of the compound (a) is in the range of the appropriate amount, the resin composition can provide a cured product having excellent coatability and a high refractive index. [Electrical element not invented by the compound--丨τ 1...The δ:(Β)' contained in the Dingzhou Λ 组 group contains more than one molecule in one molecule and contains a selected one from the epoxy group. a group (b) of at least one reactive functional group in the group of ethylene ether, propyl (tetra)oxy and f-propyl (tetra). It is possible to use one kind of W or one type at the same time. It is preferred that the composition of only the combination of -11-201221541 is liquid at 0 to 90 °C. By such a setting, the blended resin composition of the compound (B) and the compound (A) becomes easy to become a liquid at 〇 to 90 °C. Further, it is also set to contain the compound (A) in the compound (B). In the group (b) containing a reactive functional group of the compound (B), 'epoxy group, oxetanyl group, vinyl ether group having cationically polymerizable' (meth) acrylonitrile group has radical polymerization Sex. The vinyl ether group may also have a case of radical polymerization. The compound (B) may, for example, be a compound having a different aromatic ring and a cationic polymerizable functional group in one molecule, and having one or more aromatic donors, a, and one radical. Polymeric functional group: a compound (Β·2); a compound (B_3) having more than one aromatic ring or more of a cationically polymerizable fluorenyl group in a pseudo molecule; and one or more aromatic rings and two or more The above-mentioned radically polymerizable group-based compound of a human-group ring and a cationically polymerizable functional group (B-5 has an aliphatic compound (IV); and has a base group and a cation-based polymerizable functional group having a radical and a radical Μ Compounds of the group, etc. 11 s fluorenyl compound (Β-8: The scented aromatic ring may be a monocyclic or condensed polycyclic aromatic ring of a benzene ring or a condensed polycyclic ring: a phenanthrene ring, which hardens the resin composition. In the case, it is possible to obtain two ring-hardened materials in the present specification. The number of the ring skeleton is set to _. The multi-ring knife formed by the method has one or more aromatics. a compound (B-1) having a ring and a cationic poly-12-201221541 conjugated functional group Examples thereof include a compound having a benzene ring and a cycloalkyl group, such as glycidyl phenyl ether, phenol glycidyl ether, diphenol diglycidyl ether, and trisphenol glycidyl ether; glycidyl nonylphenyl ether, glycidyl ethylbenzene a compound having an alkyl group substituted with a benzene ring and an epoxy group, such as an ether, glycidyl propyl phenyl ether, glycidyl n-butyl phenyl ether, glycidyl butyl phenyl ether, etc. (for example, having a Cl -9 alkyl group) a compound which substitutes a benzene ring and an epoxy group); methyl phenol glycidyl ether, ethyl benzene glycidyl ether, propyl phenol glycidyl ether, n-butyl phenol glycidyl ether, tert-butyl phenol glycidyl ether, etc. Alkyl-substituted phenol glycidyl ether (for example, phenol glycidyl ether substituted by c丨_9 alkyl); benzyl (R)-(-)-glycidyl ether, phenylbenzyl glycidyl ether, etc. Lower glycidyl ether compound; phenyl vinyl ether, phenol vinyl ether, phenoxymethyl vinyl ether, (phenylphenoxy) methyl vinyl ether, (2-phenoxy) ethyl vinyl Ether, (2-phenylphenoxy)ethylethylene a vinyl ether compound having 1 or 2 acyclic rings, such as a phenyl ether; phenyl oxetane, phenoxy oxetane, phenoxymethyl oxetane, (phenylphenoxy) a methyl oxetane' (2-phenyloxy)ethyloxetane, (2-phenylphenyloxy)ethyloxetane or the like having a hydrazine or two benzene rings An oxetane compound, such a halide, etc. The Cm alkyl substituent may, for example, be a methyl group, an ethyl group, a propyl group or a tert-butyl group. _ One or more aromatic rings in one molecule Examples of the compound (B-2) having one radical polymerizable functional group include phenyl (meth) acrylate, phenol (meth) acrylate, (meth) acrylate, and (meth) &Acrylic (phenyl phenyloxy) methyl vinegar, (meth)acrylic acid (2-phenyloxy) ethyl ester, (meth)acrylic acid (2-phenylphenoxy) ethyl ester, etc. -13- 201221541 A compound of a cyclopentane and (fluorenyl) acrylonitrile; and such a complex, or a C1-9 alkyl substituent, and the like. Examples of the C,·9 alkyl substituents include a methyl group, an ethyl group, a propyl group, and a third butyl group. Examples of the halogen include F, cn, and Br. Examples of the compound (B-3) having one or more aromatic rings and two or more cationically polymerizable functional groups in one molecule include biphenyl diglycidyl ether, bisphenol A diglycidyl ether, and bisphenol F a compound having a benzene ring and two epoxy groups, such as glycidyl ether, bisphenol S diglycidyl ether, tetrakisylbiphenol diglycidyl ether; naphthalenediol diglycidyl ether, double-preferable second glycidyl ether a compound having a condensed ring and two epoxy groups, such as biscresol second glycidyl ether, bisphenoxyethanol second glycidyl ether, etc.; bisphenol F bis(3-ethyl-3-oxetan) a compound having an aromatic ring and two oxetanyl groups, such as an alkyl mercapto) ether; biphenyl divinyl ether, bisphenol A divinyl ether, bisphenol F divinyl ether, bisphenol a compound having a benzene ring and two vinyl ether groups, such as S divinyl ether or tetramethyl biphenol divinyl ether; naphthalenediol divinyl ether, bisphenol second vinyl ether, biscresol bismuth a combination of a condensed ring and two vinyl ether groups, such as vinyl ether or bisphenoxyethylidene divinyl ether And the like il thereof, or such a Cm alkyl substituted like. The base may be an alkyl group, an ethyl group, a propyl group, a third butyl group or the like; or a CM or a Br.
C,_9烷基取代 鹵素可列舉F 在1分子中具有1個以上的芳香族環與2個以上的自 由基聚合性官能基之化合物(B_4)可列舉例如聯苯酚二 甲基)丙烯酸酯、雙酚A二(甲基)丙烯酸酯、雙酚f二 基)丙烯酸酯、雙酚S二(曱基)丙烯酸酯、四^基聯一笨甲 二(甲基)丙稀酸醋等的具有苯環與兩個(甲基^烯酿= -14- 201221541 的化合物;萘二醇二(曱基)丙烯酸酯、聯苯酚第二(曱基) 丙烯酸酯、雙曱酚苐二(曱基)丙烯酸酯、雙苯氧基乙醇 薙二(曱基)丙烯酸酯等的具有縮合環與兩個(甲基)丙烯 醯基的化合物;及該等的鹵化物、或該等的Cw烷基取代 物等。Cw烷基取代基可列舉曱基、乙基、丙基、第三丁 基等,鹵素可列舉F、Cl、Br等。 具有脂肪族環與陽離子聚合性官能基的化合物 (B-5)可列舉例如環己基縮水甘油醚、二環己基縮水甘油 醚、三環己基縮水甘油醚等的C5.20環烷基縮水甘油醚化 合物;環己基氧雜環丁烷基醚、二環己基氧雜環丁烷基 _、三環己基氧雜環丁烷基醚等的C5_2Q環烷基氧雜環丁 烷基醚化合物;環己基乙烯基醚、二環己基乙烯基醚、 三環己基乙烯基醚等的(:5_2〇環烷基乙烯基醚化合物等。 具有脂肪族環與自由基聚合性官能基的化合物 (B-6)可列舉例如(甲基)丙烯酸環己酯、(曱基)丙烯酸二 環己酯、(曱基)丙烯酸三環己酯等的C52〇環烷基之(曱基) 丙烯酸酯化合物等。 具有烷基與陽離子聚合性官能基的化合物(8_7)可 列舉例如縮水甘油基甲醚、縮水甘油基乙醚、丙基縮水 甘油醚、丁基縮水甘油醚' 2·乙基己基縮水甘油醚等的Examples of the C, _9 alkyl-substituted halogen include a compound (B_4) having one or more aromatic rings and two or more radical polymerizable functional groups in one molecule, and examples thereof include biphenol dimethyl acrylate. Bisphenol A di(meth)acrylate, bisphenol f diyl) acrylate, bisphenol S bis(indenyl) acrylate, tetrakis-ethylidene di(methyl) acrylate vinegar, etc. Benzene ring with two (methyl enelate = -14- 201221541 compounds; naphthalenediol bis(indenyl) acrylate, biphenol second (indenyl) acrylate, bisphenol quinone (fluorenyl) a compound having a condensed ring and two (meth) acrylonitrile groups, such as acrylate or bisphenoxyethanol bis(indenyl) acrylate; and such halides or such Cw alkyl substituents Examples of the Cw alkyl substituent include a mercapto group, an ethyl group, a propyl group, a tert-butyl group and the like. Examples of the halogen include F, Cl, Br, etc. Compounds having an aliphatic ring and a cationically polymerizable functional group (B-5) Examples thereof include cyclohexyl glycidyl ether, dicyclohexyl glycidyl ether, tricyclohexyl glycidyl ether, and the like. C5.20 cycloalkyl glycidyl ether compound; C5_2Q cycloalkyl oxalate such as cyclohexyl oxetanyl ether, dicyclohexyl oxetane group, tricyclohexyl oxetane alkyl ether a cyclobutane ether compound; a cyclopentyl vinyl ether, a dicyclohexyl vinyl ether, a tricyclohexyl vinyl ether or the like (: a 5 2 fluorene cycloalkyl vinyl ether compound, etc. having an aliphatic ring and a radical polymerizable property The functional group (B-6) may, for example, be a C52 fluorenylcycloalkyl group such as cyclohexyl (meth) acrylate, dicyclohexyl (meth) acrylate or tricyclohexyl acrylate. The acrylate compound or the like. The compound (8-7) having an alkyl group and a cationically polymerizable functional group may, for example, be glycidyl methyl ether, glycidyl ether, propyl glycidyl ether or butyl glycidyl ether. Hexyl hexyl glycidyl ether
Cm烷基縮水甘油醚化合物;甲基氧雜環丁燒基醚、乙美 氧雜環丁烷基醚、丙基氧雜環丁烷醚、丁基氧雜環丁严 基醚等的Cm烷基氧雜環丁烷基醚化合物;曱基乙烯醚“ 乙基乙烯醚、丙基乙烯醚、丁基乙烯醚等的ci9烷基乙 醚化合物等。 土 -15- 201221541 具有烷基與自由基聚合性官能基的化合物(B_8)可 列舉例如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(曱基) 丙烯酸丙酯、(甲基)丙烯酸丁酯等的Cl_9烷基之(曱基)丙 烯酸酯化合物等。 另外,化合物(B)可列舉例如下述式(2)所表示之化合 物: ΖΗθ-R1),,, (2) [式(2)中,Z1表示由m價之多價羥基化合物經除去功 個OH基之基團;r1表示縮水甘油基、可具有取代基之氧 雜環丁烷基甲基、乙烯基、或(甲基)丙烯醯基;以 上的整數]» 上述Z1係具有1個以上的芳香族環之基團。芳香族環 可列舉前述例示之物質。 上述式(2)中’ m=i之羥基化合物z1〇h可列舉例如紛 、苯酚、二苯酚、三笨酚等具有丨〜3個苯環的酚類;曱 酚、乙酚、丙酚、正丁酚、第三丁酚等的經烷基取代之 酚(例如經Cw烷基取代之酚);甲基苯酚、乙苯酚、丙基 苯酚、正丁基苯酚、第三丁基苯酚等的經烷基取代苯酚( 例如經C!—烷基取代苯酚);曱醇、乙醇、丙醇、丁醇等 的烷基醇(例如Cm烷醇);苄醇、笨基苄醇等的苄醇類; 環己醇、一 j衣己醇、三環己醇等的具有脂肪族環的醇頬 ’及5玄等的南化物等。上述Cm烷基取代基可列舉曱基、 乙基、丙基、第三丁基等,鹵素可列舉F、Cn、Br等。 另外,上述式(2)中,m為2以上的m價之多價羥基化 合物Z (〇H)m可列舉聯苯酚、雙酚A、雙酚f、雙酚s等的 -16 - 201221541 具有2個苯環的化合物、及該等的_化物、或該等的[Η 烷基取代物;萘二醇、雙酚苐、雙甲酚第、雙苯氧基乙 醇苐等的具有縮合環的化合物、及該等的齒化物、或該 等的C"烷基取代4勿;氫化雙酚八、氫化雙酚F'氫化雙 酚S、二環己基等的具有2個環己烷環的化合物;甲酚酚 駿、苯盼紛路等的具有3個以上如苯環等芳香族環的化合 物、及該等的齒化物、或該等的c]9烷基取代物等。c" 院基取代基可列舉甲乙基、丙基、第三丁基等,齒 素可列舉F、CM、Br等。 含有反應性官能基之基團(b)可適合使用纟有陽離子 聚合性之基團,更佳為環氧基’特佳為縮水甘油基。化 合物分子中所含有反應性官能基之基團(b)的數目為 例如2〜30個’宜為2〜10個’更佳為2〜6個,特佳為2〜 3個。所含的複數個反應性官能基之基團⑻可相同或相異 。化合物(B)之分子量沒有受到特別限制,而以重量平均 分子量計係以100〜100000為佳,較佳為1〇〇〜5〇〇〇〇。 上述化合物(B)係以含有相異2種以上的複數個前述 化合物(B)為佳。另外,複數個化合物(B)之至少ι種化合 物(B) ’係以在i分子中具有!個以上的芳香族環與2個以 上的反應性官能基(含有反應性官能基之基團(b))為佳。 ^佳為在i分子甲有2個芳香環。藉由將化合物設定為 k種構成’電子tl件用高折射率樹脂組成物容易成為液 狀在〇〜90 c,宜為〇〜4〇 c,特佳為室溫附近(0〜3〇t 左右)之任一溫度下為液體,在硬化後的情況可得到高 折射率的硬化物。 -17· 201221541 、化。物(B)具體而言可適合使用雙酚ρ二縮水甘油醚 :曱基聯笨酚二縮水甘油醚、雙笨氡基乙醇葬二縮水 >縫等的具有2〜4個笨環的二縮水甘油酸;雙驗?雙 _3_乙基氡雜環丁烷基曱基)醚等的具有2〜4個苯環的 靈氡雜環丁烷基醚;雙酚F二乙烯基醚等的具有2〜*個苯 %的二,乙烯基醚;或雙酚F:(甲基)丙烯酸醋等的具有2 〜4個苯環的(曱基)丙烯酸酷等。化合物⑻,係以具有縮 ^甘油基與笨環各兩個的化合物、具有乙料基與苯環 兩個的化σ物為佳。進—步而言’化合物⑻採用具有 ^稀驗基與苯環各兩個的化合物之樹脂組成物,容易在 較低溫成為液狀,因此特別適合。 上述化合物(Β)的含量並未受到特別限定,而以相對 ;:子兀件用同折射率樹脂組成物中之聚合性化合物之 總置的2 0〜9 0重晉。 置為佳,較佳為30〜7〇重量%,特佳為 4〇〜60重量%。若化合物⑻的含量在這樣的範圍内則 可提供具有優異的硬度、塗布性的硬化物。 另外,化合物(B)的含量並未受到特&限定而以相 對於前述味嗤化合物⑷1〇〇重量份的25〜9〇〇重量份為 佳’較佳為42.9〜233.3重量份,特佳為66 7〜15〇重量份 。藉由使化合物(B)的含量在這樣的範圍内,會有容易使 電子元件用高折射率樹脂組成物在〇〜9〇 _ L 任 〉皿度 y成為液㈣傾向1合物⑻中之在1分子中具有i個以 ^的芳香族環與2個以上的反應性官能基(含有反應性官 成基之基團⑻)的化合物的含量並未受到特別限定, 30〜100重量%為佳,較佳為4〇〜1〇〇重量%。 • 18 - 201221541 [聚合起始劑(c)] 在本發明之電子元件用高折射率樹脂組成物中含有 聚合起始劑(C)。聚合起始劑(C)並未受到特別限定,可 使用周知慣用的聚合起始劑’而可適合使用陽離子型光 或熱聚合起始劑或光或熱自由基聚合起始劑。聚合起始 劑可單獨使用1種或組合兩種以上使用。 <陽離子型光聚合起始劑〉Cm alkyl glycidyl ether compound; methyl oxetane, ethyl acetophene ether, propyl oxetane ether, butyl oxetane ether, etc. An oxetane ether compound; a mercapto vinyl ether ci9 alkyl ether compound such as ethyl vinyl ether, propyl vinyl ether or butyl vinyl ether, etc. Earth-15-201221541 having an alkyl group and a radical polymerization The compound (B_8) having a functional group may, for example, be a Cl_9 alkyl group such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate or butyl (meth)acrylate (曱). Further, the compound (B) may, for example, be a compound represented by the following formula (2): ΖΗ θ - R1),, (2) [In the formula (2), Z1 represents a value of m. The polyvalent hydroxy compound is subjected to removal of a group having an OH group; r1 represents a glycidyl group, an oxetanemethyl group which may have a substituent, a vinyl group, or a (meth) acrylonitrile group; the above integers] » The above Z1 is a group having one or more aromatic rings, and examples of the aromatic ring include the above-exemplified ones. In the above formula (2), the hydroxy compound z1〇h of 'm=i may, for example, be a phenol having 丨~3 benzene rings such as phenol, phenol, diphenol or trisphenol; indophenol, phenol, propofol, An alkyl-substituted phenol such as n-butyl phenol or a third butyl phenol (for example, a phenol substituted with a Cw alkyl group); methyl phenol, ethyl phenol, propyl phenol, n-butyl phenol, or tertiary butyl phenol; Alkyl-substituted phenol (for example, substituted by C?-alkyl); alkyl alcohol of decyl alcohol, ethanol, propanol, butanol, etc. (for example, Cm alkanol); benzyl alcohol, benzyl alcohol, etc. An aliphatic ring-like alcohol oxime of cyclohexanol, a hexylhexanol or tricyclohexanol, and a ruthenium such as 5 ruthenium, etc. The above Cm alkyl substituent may, for example, be an alkyl group, an ethyl group or a propyl group. In the above formula (2), the m-valent polyvalent hydroxy compound Z (〇H)m in which m is 2 or more is exemplified by a phenol, a butyl group, and the like. 1-6 - 201221541 of bisphenol A, bisphenol f, bisphenol s, etc., a compound having two benzene rings, and the like, or such [Η alkyl substituents; naphthalenediol, bisphenol oxime ,double a compound having a condensed ring such as phenol or bisphenoxyethanol oxime, and the like, or a C"alkyl substituted 4; hydrogenated bisphenol VIII, hydrogenated bisphenol F' hydrogenated bisphenol S a compound having two cyclohexane rings such as a dicyclohexyl group; a compound having three or more aromatic rings such as a benzene ring, such as a cresol or a benzophenone, and the like, or The c- 9-alkyl substituent or the like may be mentioned. The c-quot; the substituent of the substituent may, for example, be a methyl group, a propyl group or a third butyl group. Examples of the dentate include F, CM, Br, etc. Groups containing a reactive functional group (b) It is suitable to use a group having a cationic polymerizable property, and more preferably an epoxy group is particularly preferably a glycidyl group. The number of the groups (b) of the reactive functional group contained in the compound molecule is, for example, 2 to 30's preferably 2 to 10's, more preferably 2 to 6, more preferably 2 to 3. The groups (8) of the plurality of reactive functional groups may be the same or different. The molecular weight of the compound (B) is not particularly limited, and is preferably from 100 to 100,000, preferably from 1 to 5 Å, based on the weight average molecular weight. The compound (B) is preferably a plurality of the above-mentioned compounds (B) which are different from each other. Further, at least one compound (B) of the plurality of compounds (B) is present in the i molecule! More than one aromatic ring and two or more reactive functional groups (group (b) containing a reactive functional group) are preferred. ^佳为 has two aromatic rings in i molecule A. By setting the compound to k kinds, the composition of the high refractive index resin for the electron tl piece is likely to be liquid in the form of 〇~90 c, preferably 〇~4〇c, particularly preferably near room temperature (0~3〇t) At any temperature of the left and right), it is a liquid, and after hardening, a cured product having a high refractive index can be obtained. -17· 201221541, Hua. Specifically, the substance (B) may be suitably used in the form of bisphenol ρ diglycidyl ether: fluorenyl phenyl diglycidyl diglycidyl ether, bis-mercapto diol condensed water, and the like, having 2 to 4 stupid rings. Glycidic acid; double test? a fluorene-terminated butane-terminated alkyl ether having 2 to 4 benzene rings, such as bis-3_ethyl hydrazinyl fluorenyl) ether; bisphenol F divinyl ether or the like having 2 to * benzene % of the second, vinyl ether; or bisphenol F: (meth)acrylic acid vinegar, etc., having 2 to 4 benzene rings, (mercapto) acrylic, etc. The compound (8) is preferably a compound having two compounds of a condensed glyceryl group and a stupid ring, and a ruthenium having two groups of an ethyl group and a benzene ring. Further, the compound (8) is preferably a resin composition having a compound of two kinds of a test group and a benzene ring, and is easily liquid at a relatively low temperature. The content of the above compound (Β) is not particularly limited, but is reciprocal with respect to the total amount of the polymerizable compound in the composition of the same refractive index resin. Preferably, it is preferably from 30 to 7 % by weight, particularly preferably from 4 to 60% by weight. When the content of the compound (8) is within such a range, a cured product having excellent hardness and coatability can be provided. Further, the content of the compound (B) is not particularly limited to 25 to 9 parts by weight, preferably 42.9 to 233.3 parts by weight, based on 1 part by weight per part by weight of the above-mentioned miso compound (4). It is 66 7~15〇 by weight. When the content of the compound (B) is in such a range, it is easy to make the high refractive index resin composition for electronic components in the range of 〇~9〇_L, and the degree of liquid y becomes liquid (4) in the first compound (8). The content of the compound having i of an aromatic ring and two or more reactive functional groups (containing a reactive group-forming group (8)) in one molecule is not particularly limited, and 30 to 100% by weight is Preferably, it is preferably 4〇~1〇〇% by weight. 18 - 201221541 [Polymerization Initiator (c)] The polymerization initiator (C) is contained in the high refractive index resin composition for electronic components of the present invention. The polymerization initiator (C) is not particularly limited, and a conventional polymerization initiator can be used, and a cationic photo or thermal polymerization initiator or a photo or thermal radical polymerization initiator can be suitably used. The polymerization initiators may be used alone or in combination of two or more. <Cationic photopolymerization initiator>
陽離子型光聚合起始劑可使用例如CYRACURE UVI-6970、CYRACURE UVI-6974、CYRACURE UVI-6990 、CYRACURE UVI-950(以上為美國 Union Carbide公司製 的商品名)、IRGACURE 250、IRGACURE 261、IRGACURE 264(Ciba Specialty Chemicals公司製的商品名)、SP-150 、SP-151、SP-170、OPTOMER SP-171(以上為旭電化工 業股份有限公司製的商品名)、CG-24-61(Ciba Specialty Chemicals公司製的商品名)、DAICATII(DAICEL化學工 業公司製的商品名)、UVAC1 590、UVAC1591(DAICEL CYTEC股份有限公司製的商品名)、CI-2064、CI-2639、 CI-2624、CI-2481、CI-2734、CI-2855、CI-2823、CI-275 8 、CI-1682(以上為曰本曹達公司製品的商品名)、PI-2074 (Rhodia公司製商品名,五氟苯基硼酸鹽異丙苯基錤鏽鹽 )、FFC509(3M公司製品的商品名)、BBI-102、BBI-101 、BBI-103、MPI-103、TPS-103、MDS-103 ' DTS-103、 NAT-103、NDS-103(Midori化學公司製的商品名)、 CD-1010、CD-1011、CD-1012(美國 Sartomer公司製的商 品名)、CPI-100P、CPl-101A(San-Apro公司製的商品名) -19- 201221541 等的市售品所代表的重氮鹽、鏘鑌鹽、錡鹽、鱗鹽、硒 鹽、氧鐵鹽、錢鹽等。 <陽離子型熱聚合起始劑> 陽離子型熱聚合起始劑可使用例如San_Aid δι·45以 及同系列的 SI·47、SI_6〇、SI-60L、SI-8〇、SI_8〇L、SM〇〇 ' SI"1〇〇L' SI-U〇L' SI-145^ SI-150. SI-160 > SMi〇l 、SI-180L(以上為三新化學工業公司製品的商品名 CIm2920、CI_2946、⑴128、叫⑵、ci_⑽ 、CI-2064(以上為日本#達股份有限公司製品的商 ;PP-33、CP_66、cp_77(旭電化工業公司製品的商: 氣I'5:鏽1°:52:3财,司製品的商品名)等所代表的重 孤、"麗、鎳鹽、鐫鹽、硒鹽、正氧鹽、銨 :-步亦可為紹或欽等的金屬與乙醯 :二 合化合物與三苯碎醇等㈣醇之化合物,或螯 金屬與乙醯醋酸戋_醎猫 〆·或鈦專的 類之化合物。戈―酮類之整合化合物與雙盼S等的紛 陽離子型光或熱聚合起始劑之使用 到特別限$,而例如以相對於電子元件用^置)並未受 組成物中所含的含有仆人 门射率樹脂 合物之總量(聚合性化1:()與化合物(Β)的聚合性化 重量份為佳較佳::二總量)1〇。重量份的。 手乂 1主马〇 〇1〜12番县々、@ /土 重量份,最佳為0.Μ。重量份重左量右"佳為〇·。5〜丨。 <硬化促進劑> W ί:明之電子元件用高折射率樹脂組成物中的%-性化合物,在藉由陽 r的眾σ 離子!光或熱聚合起始劑而硬化時 -20- 201221541 ’亦可含有具有促進硬化速度的機能的硬化促進劑。硬 化促進劑可使用周知慣用的硬化促進劑,可列舉例如 1,8-二氮雜雙環[5.4.0]十一烯- 7(DBU)、及其鹽(例如酚鹽 、辛酸鹽、對甲苯續酸鹽 '蟻酸鹽、四苯基硼酸鹽);1,5-二氮雜雙環[4.3.0]壬烯-5(DBN)、及其鹽(例如鱗鹽、銃 鹽、4級銨鹽、鎭鏽鹽);苄基二曱胺、2,4,6_參(二曱基 胺基甲基)酚、Ν,Ν-二甲基環己基胺等的3級胺;2-乙基-4-曱基咪唑、1-氰基乙基-2-乙基-4-曱基咪唑等的咪唑;磷 酸酯、三苯膦等的膦類;四笨基鱗四(對甲苯基)硼酸鹽 等的鐫化合物;辛酸錫、辛酸鋅等的有機金屬鹽;金屬 螯合物等。該等可單獨或混合2種以上使用。As the cationic photopolymerization initiator, for example, CYRACURE UVI-6970, CYRACURE UVI-6974, CYRACURE UVI-6990, CYRACURE UVI-950 (above, trade name of Union Carbide, USA), IRGACURE 250, IRGACURE 261, IRGACURE 264 can be used. (trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.), SP-150, SP-151, SP-170, OPTOMER SP-171 (above, trade name, manufactured by Asahi Kasei Kogyo Co., Ltd.), CG-24-61 (Ciba Specialty) Chemicals company's trade name), DAICATII (trade name by DAICEL Chemical Industry Co., Ltd.), UVAC1 590, UVAC1591 (trade name by DAICEL CYTEC Co., Ltd.), CI-2064, CI-2639, CI-2624, CI- 2481, CI-2734, CI-2855, CI-2823, CI-275 8 , CI-1682 (above is the product name of Sakamoto Saoda Co., Ltd.), PI-2074 (trade name of Rhodia Corporation, pentafluorophenyl boric acid) Salt cumyl sulfonium salt), FFC509 (trade name of 3M company product), BBI-102, BBI-101, BBI-103, MPI-103, TPS-103, MDS-103 'DTS-103, NAT- 103, NDS-103 (trade name by Midori Chemical Co., Ltd.), CD-1010, CD-1011, CD-1012 (US Sar Diazo salt, strontium salt, strontium salt, scale salt represented by a commercial product such as CPI-100P, CPl-101A (trade name, manufactured by San-Apro Co., Ltd.) -19-201221541, etc. Selenium salt, oxynitride salt, money salt, etc. <Cationic thermal polymerization initiator> For the cationic thermal polymerization initiator, for example, San_Aid δι·45 and the same series of SI·47, SI_6〇, SI-60L, SI-8〇, SI_8〇L, SM can be used. 〇〇' SI"1〇〇L' SI-U〇L' SI-145^ SI-150. SI-160 > SMi〇l, SI-180L (The above is the trade name CIm2920 of Sanxin Chemical Industry Co., Ltd. CI_2946, (1)128, called (2), ci_(10), CI-2064 (above is the manufacturer of Japan #达股份有限公司); PP-33, CP_66, cp_77 (the manufacturer of Asahi Chemical Industry Co., Ltd.: Gas I'5: Rust 1°: 52:3, the product name of the company's products, etc., represented by the heavy orphan, " Li, nickel salt, barium salt, selenium salt, oxo salt, ammonium: - step can also be metal and B of Shao or Qin醯: a compound of a di-compound compound such as a diphenyl phenol and a (iv) alcohol, or a compound of a chelate metal and a ruthenium acetate 戋 醎 〆 或 or a titanium compound. The integrated compound of the ketone and the S. The use of cationic photo- or thermal polymerization initiators is particularly limited to $, for example, relative to electronic components, and is not contained in the composition containing the servant gate rate resin composition. The amount (polymerization 1: () and the polymerized weight of the compound (Β) are preferably: two total amounts) 1 part by weight. Handcuffs 1 main horses 1 to 12 Fanxian County , @ /土重量份,优选为0.Μ. Weight by weight left amount right "佳为〇·.5~丨. <hardening accelerator> W ί: Ming electronic components are composed of high refractive index resin The %-supplemented compound can be hardened by a positive sigma ion light or a thermal polymerization initiator which is also a hardening accelerator having a function of promoting the hardening rate. A well-known hardening accelerator can be used, and examples thereof include 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), and salts thereof (for example, phenate, octanoate, p-toluate). 'antate, tetraphenylborate; 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), and salts thereof (eg, scale salts, phosphonium salts, grade 4 ammonium salts, cesium) Rust salt); benzyl diamine, 2,4,6-glycol (didecylaminomethyl) phenol, hydrazine, hydrazine-dimethylcyclohexylamine, etc. - an imidazole such as mercapto imidazole or 1-cyanoethyl-2-ethyl-4-mercaptoimidazole; a phosphine such as an acid ester or a triphenylphosphine; an anthracene compound such as a tetraphenylphosphonium tetra(p-tolyl) borate; an organic metal salt such as tin octylate or zinc octylate; a metal chelate compound or the like. Mix two or more types.
另外,硬化促進劑亦可使用U-CAT SA506、U-CAT SA102、U-CAT 5003、U-CAT 18Χ、12XD(開發品)(任一 者皆San-Apro製)、TPP-K、TPP-MK(任一者皆北興化學 工業製)、PX-4ET(曰本化學工業製)等的市售品。 硬化促進劑之使用量(含量)為例如相對於電子元件 用高折射率樹脂組成物中所含的聚合性化合物之總量 1〇〇重量份的0·05〜5重量份,宜為01〜3重量份,特佳為 〇·2〜3重量份,最佳為〇·25〜2·5重量份左右。若硬化促 進劑的使用量低於0_05重量份,則會有硬化促進效果不 足的情況,另一方面,若硬化促進劑的使用量高於5重量 份,則會有硬化物發生著色,色澤惡化的情況。 <光自由基聚合起始劑> 光自由基聚合起始劑可使用例如二苯基酮、苯乙酮 节基、节基二曱基酮、安息香、安息香曱醚、安息香乙 -21 - 201221541 基醚、安息香異丙基醚、二甲氧基苯乙酮、二甲氧基苯 基苯乙酮、二乙氧基苯乙酮、二苯二亞硫酸酯、鄰苯曱 醯基安息香酸曱酯、4-二曱基胺基安息香酸乙酯(日本化 藥股份有限公司製KAYACURE EPA等)、2,4-二乙基噻噸 酮(曰本化藥股份有限公司製KAYACURE DETX等)、2-甲基-1-[4-(曱基)苯基]-2-咮啉基丙酮-1(CIBA-GEIGY股 份有限公司製IRGACURE 907等)、2-二曱基胺基-2·(4-咪 啉基)苯甲醯基-1-苯基丙烷等的2-胺基-2-苯甲醯基-1-苯 基烷化合物、四(第三丁基過氧羰基)二苯基酮、节基、 2-經基-2-甲基-1-苯基丙-1-酮、4,4-雙二乙基胺基二苯基 酮等的胺基苯衍生物、2,2'-雙(2-氣苯基)_4,5,4,,5,-四苯 基-1,2 ’ -聯咪唾(保土谷化學股份有限公司製β _ c〗μ等)等 的咪唑化合物、2,6-雙(三氣曱基)-4-(4-甲氧基萘-1-基 )-1,3,5-三听等的_甲基化三呼化合物、2·三氣甲基·5·(2-苯并呋喃2-基-乙烯基)-1,3,4-嘮二唑等的齒甲基嘮二唑 化合物等,可單獨使用或組合兩種以上(例如混合)使用 ,亦可依需要加入光增感劑。從感度及耐藥品性等的觀 點看來,光自由基聚合起始劑係以咪唑化合物與胺基笨 衍生物之組合、2-胺基-2·苯甲醯基苯基烷化合物、_ 甲基化三畊化合物、産甲基噚二唑化合物等為佳。 <熱自由基聚合起始劑> 熱自由基聚合起始劑可列舉有機過氧化物類。有機 過氧化物類可使用二烧基過氧化物、醯基過氧化物、過 氧化氫、過氧化酮、過氧化酯等。有機過氧化物之具體 例可列舉苯曱醯基過氧化物、過氧化·2_乙基己酸第三丁 -22- 201221541 酯、2,5-二甲基_2,5_二(2·乙基己醯基)過氧化己烷、第三 丁基過氧化笨甲酸醋、第三丁基過氧化物、"素過: 化氫、二異丙苯基過氧化物、二第三丁基過氧化物、2,氕 二甲基-2,5-二丁基過氧己烷、2,4_二氯苯甲醯基過氧化 物一第_ 丁基過氧二異丙苯、^雙(第三丁基過氧 )-3,3,5-三曱基環己烷、過氧化曱基乙基酮等。 甚至於上述熱自由基聚合起始劑還可併用環烷酸鈷 、我⑽、環㈣辞、辛料料的環院酸或辛缔酸 敍、鋅、釩等的金屬鹽。同樣亦可使用二甲 基苯胺#的3級胺。 光或熱自由基聚合起始劑可單獨使用—種,或可將 兩種以上以任意比例組合(例如混合)使用。 子元量)並未受到特別限定,而以相對於電 子X件用间折射率樹脂組成物中所含 總量100重量份的(Μ重量份〜5重量4 化。物之 土 θ 里置伤為佳,較佳Λ 0 5 重量份〜4重量份。 税佳马ϋ.) [無機填料(D)] 本發明之電子开I_ 一古…古射率樹脂組成物亦可進-〆3有,..、機填料(D)。無機 而可使用1 ^ ” π…)並未文到特別限定, 使用一氧化矽、氧化紹、雲母、合成 、 氧化鈣、碳酸鈣、氧化錯、 β石 膨土、矽澡土…μ 乳化鈦、鈦酸鋇、高嶺土、 '、 氮化硼、氮化鋁、碳化矽、襄务拉窗 化鈽、氧化鉋、氧化#、 氧化辞、氧 ^ 玻璃珠、玻璃纖維、石g f 氧化鈣、氫氧化鎂、氫t仆# Μ 乍石墨、埶 。另外,益機填料m 素等之中的1種以上 真科⑼可列舉奈米二氧化石夕、奈米二氧化 -23- 201221541 鈦、奈米鍅、奈米碳管等。無機填料(D)可單獨使用一種 或組合兩種以上使用。 該等的無機填料(D)可藉著例如國際公開第96/ 3 1 5 7 2號所s己載的火焰水解法、或火焰熱分解法、電衆法 等的周知的方法而製造。適合的無機填料(D)可使用經過 安定化的膠體狀無機粒子之奈米分散溶膠類等,市售品 可取得BAYER公司製的二氧化矽溶膠、Goldschmidt公司 製的Sn02溶膠類' MERCK公司製的1^02溶膠類、Nissan Chemicals 公司製的 Si02、Zr02、Al2〇3 及 Sb203 溶膠或 DEGUSSA公司製的Aerosil分散物類等的市售品。 無機填料(D)可藉由表面的改質而使該等的黏度行 為表現發生變化。粒子的表面改質可使用周知的表面改 質劑進行。這種表面改質劑可使用例如可與存在於無機 填料(D)表面的官能基形成共價鍵或錯化等的交互作用 的化合物、或可與聚合物基材發生交互作用的化合物。 這種表面改質劑可採用例如分子内具有叛基、(1級、2級 、3級)胺基、4級銨基羰基、縮水甘油基、乙烯基、(甲 基)丙烯醯氧基、巯基等的官能基的化合物等。這種表面 改質劑通常包含在標準溫度及壓力條件下為液體,分子 内的碳數為例如1 5以下,較佳為1 〇以下,特佳為8以下的 低分子有機化合物。前述低分子有機化合物之分子量並 未受到特別限定,而500以下為佳,較佳為35〇以下,特 佳為2 0 0以下。 適合的表面改質劑可列舉例如曱酸、醋酸、丙酸、 丁酸、戊酸、己酸、丙烯酸、曱基丙烯酸、巴豆酸、檸 -24- 201221541 檬酸、己二酸、琥轴酸、戊二酸、草酸、馬來酸及富馬 酸等之碳數1〜12之飽和或不飽和一元及多元羧酸類%宜 為-元酸類上述飽和或不飽和-元及多元酸類之§旨類 (宜為甲基丙烯酸甲醋等的C〗〜C4烷基酿類);酿胺類· 乙醯基丙酮、2,4_己二g同、3,5_庚二綱、乙醯醋酸及C 〜C4院基乙醢醋酸類等的β_二幾基化合物等。另外,並 未受到特別限定,而亦可使用周知慣偶合 為表面改質劑。 無機Λ料(D)的粒徑並未受到特別限定而通常 O.Olnm〜2〇0叫左右為佳,較佳為〇 Um〜1〇〇㈣特佳 為O.lnm〜50μιη左右。 就無機填料(D)的含量而言,若將化合物(Α)及化入 物之合計含量定為100重量份,則以丨〜加㈧重量份2 佳,更佳為Π)〜1〇〇〇重量份。另外,無機填料(D)相對於 電子元件用高折射率樹脂組成物總量的含量並未受到特 別限定,而以例如5〜95wt%為佳,較佳為i〇〜9〇wt%。’ [矽烷偶合劑(E)] 本發明之電子元件用高折射率樹脂組成物 與基板等被接著體的接著性,.亦可進一 +人 ~ 力J進步含有矽烷偶合 劑(Ε)。矽烷偶合劑(Ε)並未受到特別限定,可使用周知 慣用的矽烷偶合劑。矽烷偶合劑(Ε)係例如選自四甲氧基 矽烷、四乙氧基矽烷、曱基三乙氧基矽烷、二甲基二乙 氧基矽烷、甲基三乙氧基矽烷、乙烯基三乙氧基矽烷、 乙稀基三甲氧基石夕炫、乙稀基參(甲氧基乙氧基石夕烧)、 笨基三甲氧基矽烷、二苯二曱氧基矽烷、乙烯基三乙醯 -25- 201221541 氧基矽烷、γ-(甲基)丙烯醯氧基丙基三乙氧基矽燒、 甲基)丙烯醯氧基丙基三曱氧基矽烷、γ-(甲基)丙缔酿氧 基丙基曱基二甲氧基矽烷、γ_(曱基)丙烯醯氧基丙基甲基 一乙氧基碎烧、^ -縮水甘油謎基丙基三甲氧基秒燒、3 縮水甘油醚基丙基甲基二曱氧基矽烷、3_縮水甘油鱗基 丙基三乙氧基矽烷、3-縮水甘油醚基丙基曱基二乙氧美 石夕烷、2-(3,4-環氧環己基)乙基三甲氧基矽烷、對笨乙稀 基三曱氧基矽烷、3-丙烯醯氧基丙基三甲氧基石夕燒、 Ν-(β-胺乙基)-γ-胺丙基甲基二曱氧基矽烷、Ν_(β_胺乙基 )-γ-胺丙基曱基二乙氧基矽烷、Ν-(β-胺乙基)-γ_胺丙基三 甲氧基矽烷、Ν-(β-胺乙基)-γ_胺丙基三乙氧基矽燒、ν_ 苯基-γ-胺丙基三甲氧基矽烷、γ_胺丙基三曱氧基矽烷、γ· 胺丙基三乙氧基矽烷、3-巯丙基三甲氧基矽烷、3_巯丙 基二乙氧基矽烷、3 -疏丙基甲基二甲氧基矽烷、雙(三乙 氧基甲矽烷基丙基)四硫化物、3-異氰酸酯基丙基三乙氧 基石夕院等在水溶液中較安定的物質。矽烷偶合劑(Ε)可單 獨使用1種或組合兩種以上使用。 石夕烧偶合劑(Ε)之使用量(含量),係以電子元件用高 折射率樹脂組成物中的〇. 1〜20重量%左右的範圍為佳, 較佳為0.3〜8重量%,更佳為〇_5〜5重量%。在未滿〇」 重量%時,缺乏由矽烷偶合劑(E)產生的樹脂的交聯效果 ,因此無法得到緻密的膜,此外還缺乏與金屬基材偶合 =效果,密著性差,而難以得到所希望的耐鹼性與防銹 能力8在高於20重量%的情況,由於水解而造成耐水、 耐鹼性等各性能顯著降低,在造膜性發生問題,此外在 -26- 201221541 經濟方面容易損失利益。 [其他添加劑j 本發明之電子元株 要採用聚合林μ ^ 用呵折射率樹脂組成物可依照需 勻劑、消泡劑、海祖七 先女疋劑、可塑劑、均 吸附體、顏科、螢光體、機溶劑、紫外線吸收劑、離子 本發明之電子-杜脫模劑等的慣用的添加劑。 子元件田古+ 9(TC(較佳為〇〜4〇。 呵射率樹脂組成物在0〜 之任-溫度TMM、/為在室溫附近(G〜抓左右)) 面塗敷時的操作性優異1電子70件之封閉、密封或表 裝置、led裝m V此了使用作為有機電致發光 置4的必需具有高折射率的電子元件用的 封閉劑、密封劑等。另外# “手的電子70件用的 ^ # ® tll .. 卜還可作為顯示器之抗反射膜用 的被覆劑或黏著劑使用。 [電子元件用高折射率樹脂組成物之製造法] 將上之電子元件用高折射率樹脂組成物,係藉由 边t成分均勾混合而得到。為了得到本發明之電子 :二回折射率樹脂組成物,宜使用自轉公轉式攪拌脫 、 自質機、行星式槐拌機、3輥磨機、珠磨機等的 -般所知的混合用機器進行攪袢、溶解、混合、分散等 ,以使各成分盡可能成為均勻。 [硬化物(樹脂硬化物)] 本發明之電子件用高折射率樹脂組成物可藉由光 或熱而使其硬化。藉由光使其硬化的情況,可藉由水銀 燈等以lOOOmJ/cm2以上的照光使其硬化。另外,在藉由 熱使其硬化的情況,可在溫度5〇〜2〇(rc(較佳為5〇〜 -27- 201221541 190 °C,更佳為50〜180 °C),以硬化時間10〜600分鐘(較 佳為10〜480分鐘,更佳為15〜360分鐘)使其硬化。在硬 化溫度與硬化時間低於上述範圍的下限值的情況,硬化 變得不足’相反地在高於上述範圍的上限值的情況,會 有樹脂成分發生分解的情況,故任一者皆會有不佳的情 形。硬化條件依照各種條件而定,而如在硬化溫度高的 情況縮短硬化時間,硬化溫度低的情況延長硬化時間等 方式可適當地作調整。藉由使本發明之電子元件用高折 射率樹脂組成物硬化,可得到折射率高的硬化物。使本 發明之電子兀件用高折射率樹脂組成物硬化而成之硬化 物具有高折射率。硬化物之折射率係以丨62〜175為佳, 更佳為1.64〜1.70。 [有機電致發光裝置、LED裝置、或顯示器] 本發明之電子元件用高折射率樹脂組成物中的電子 疋件,其適合的例子可列棗古M t 夕』舉有機電致發光裝置、:LED裝 置、顯示器等。依據本發明 之電子凡件用高折射率樹脂 組成物,該等電子元件中的朵 们九線之取出效率上升。 [封閉劑、密封劑、或被覆劑] 由於本發明之封閉劑、麥封為丨 、 4封劑、或被覆劑(抗反射用 被覆劑)含有上述電子元件用古 ^ # 阿折射率樹脂組成物,因此 在0〜90 c之任一溫度下為液 的情況具有高折射率。因此 $陡優異’在硬化後 裝置等的必需有高折射率:機電致發光裝置、㈣ 電子元件封閉、密封,以:件方面’可使用在將 。 〃 y、為的抗反射表面塗敷等 -28- 201221541 [實施例] 以下基於實施例對本發明作更詳細的說明,而本發 明並不受該等實施例所限定。 合成例 [雙酚F二乙烯醚之合成] 在設置有附迪安斯塔克冷凝管、攪拌器、及溫度計 的2公升四口燒瓶中,加入碳酸鈉(31 8g,3〇〇 〇mm〇1)、In addition, U-CAT SA506, U-CAT SA102, U-CAT 5003, U-CAT 18Χ, 12XD (developed product) (manufactured by San-Apro), TPP-K, TPP- can also be used as the hardening accelerator. Commercial products such as MK (manufactured by Kitai Chemical Industry Co., Ltd.) and PX-4ET (manufactured by Sakamoto Chemical Industry Co., Ltd.). The amount (content) of the hardening accelerator is, for example, 0. 05 to 5 parts by weight, preferably 01 to 1 part by weight, based on the total amount of the polymerizable compound contained in the high refractive index resin composition for electronic components. 3 parts by weight, particularly preferably 2 to 3 parts by weight, most preferably about 25 to 2. 5 parts by weight. When the amount of use of the curing accelerator is less than 0 to 10 parts by weight, the curing acceleration effect may be insufficient. On the other hand, when the amount of the curing accelerator used is more than 5 parts by weight, the cured product may be colored and the color may be deteriorated. Case. <Photoradical polymerization initiator> The photoradical polymerization initiator may be, for example, diphenyl ketone, acetophenone benzyl, stilbene decyl ketone, benzoin, benzoin ether, benzoin B-21 - 201221541 ether, benzoin isopropyl ether, dimethoxyacetophenone, dimethoxyphenylacetophenone, diethoxyacetophenone, diphenyl disulfite, o-benzoin benzoic acid Ethyl ester, 4-didecylamino benzoic acid ethyl ester (KAYACURE EPA, manufactured by Nippon Kayaku Co., Ltd.), 2,4-diethyl thioxanthone (KAYACURE DETX, manufactured by Sakamoto Chemical Co., Ltd.) 2-methyl-1-[4-(indenyl)phenyl]-2-porphyrinylacetone-1 (IRGACURE 907, manufactured by CIBA-GEIGY Co., Ltd.), 2-didecylamino-2 2-Amino-2-benzylidenyl-1-phenylalkane compound (4-tetraphenyl)benylmercapto-1-phenylpropane, etc., tetrakis(t-butylperoxycarbonyl)diphenyl An aminobenzene derivative such as a ketone, a benzyl group, a 2-phenyl-2-methyl-1-phenylpropan-1-one or a 4,4-bisdiethylaminodiphenyl ketone, 2, 2'-bis(2-phenylphenyl)_4,5,4,,5,-tetraphenyl-1,2'-linked sodium saliva Imidazole compound such as β _ c μ μ, etc. produced by Gu Chemical Co., Ltd., 2,6-bis(trimethylsulfonyl)-4-(4-methoxynaphthalen-1-yl)-1,3,5 - Three-toothed methyl groups such as _methylated three-hook compound, 2·trimethylmethyl·5·(2-benzofuran-2-yl-vinyl)-1,3,4-oxadiazole The oxadiazole compound or the like may be used singly or in combination of two or more kinds (for example, mixed), or a photo sensitizer may be added as needed. From the viewpoints of sensitivity and chemical resistance, the photoradical polymerization initiator is a combination of an imidazole compound and an amine stupid derivative, a 2-amino-2-benzoylphenylene compound, _A It is preferred to use a compounding three-till compound and a methyl oxadiazole compound. <Thermal radical polymerization initiator> The thermal radical polymerization initiator may, for example, be an organic peroxide. As the organic peroxide, a dialkyl peroxide, a mercapto peroxide, a hydrogen peroxide, a ketone peroxide, a peroxyester or the like can be used. Specific examples of the organic peroxide include phenylhydrazine peroxide, peroxy-2-ethylhexanoic acid tert-butyl-22-201221541 ester, and 2,5-dimethyl-2,5-di (2). · Ethylhexyl) peroxyhexane, tert-butyl peroxybenzoic acid vinegar, tert-butyl peroxide, "supply: hydrogen, dicumyl peroxide, second Butyl peroxide, 2, dimethyl dimethyl-2,5-dibutylperoxyhexane, 2,4-dichlorobenzylidene peroxide-tert-butylperoxydiisopropylbenzene, ^Bis(t-butylperoxy)-3,3,5-trimethylcyclohexane, peryl cyanoethyl ketone, and the like. Even the above-mentioned thermal radical polymerization initiator may be used in combination with a metal salt of cobalt naphthenate, I (10), ring (four), ring compound of octyl material or octanoic acid, zinc, vanadium or the like. It is also possible to use a dimethylaniline #3 amine. The photo or thermal radical polymerization initiator may be used singly or in combination of two or more kinds (e.g., mixed) in any ratio. The amount of the sub-element is not particularly limited, and is 100 parts by weight of the total amount of the resin composition in the intermediate refractive index with respect to the electron X. Preferably, Λ 0 5 parts by weight to 4 parts by weight. Tax good horse ϋ.) [Inorganic filler (D)] The electronic opening of the invention I_ An ancient ... ancient rate resin composition can also enter - 〆 3 ,.., machine packing (D). Inorganic and can be used 1 ^ ” π...) is not specifically limited, using cerium oxide, oxidized sulphate, mica, synthetic, calcium oxide, calcium carbonate, oxidized, β stone bentonite, bathing soil...μ emulsified titanium , barium titanate, kaolin, ', boron nitride, aluminum nitride, tantalum carbide, bismuth window, oxidized planer, oxidation #, oxidation word, oxygen ^ glass beads, glass fiber, stone gf calcium oxide, hydrogen Magnesium oxide, hydrogen servant # Μ 乍 graphite, 埶. In addition, one or more of the genus (9) of the yoke filler can be exemplified by nano sulphur dioxide, nano TiO 2 - 201221541 Titanium, Nai Rice bran, carbon nanotubes, etc. The inorganic fillers (D) may be used singly or in combination of two or more. The inorganic fillers (D) may be, for example, International Publication No. 96/3 1 5 7 2 It is produced by a well-known method such as a flame hydrolysis method, a flame thermal decomposition method, or a battery method. A suitable inorganic filler (D) can be a nano-dispersed sol of colloidal inorganic particles which is stabilized. The product can be obtained from cerium oxide sol manufactured by BAYER and manufactured by Goldschmidt. Sn02 sols are commercially available products such as SiO2 manufactured by MERCK Co., Ltd., SiO 2 , ZrO 2 , Al 2 〇 3 and Sb 203 sol manufactured by Nissan Chemicals Co., Ltd., or Aerosil dispersions manufactured by DEGUSSA Co., Ltd. The inorganic filler (D) can be used. The viscosity behavior of the particles is changed by surface modification. Surface modification of the particles can be carried out using well-known surface modifiers. Such surface modifiers can be used, for example, in combination with inorganic fillers (D). The functional group of the surface forms an interaction compound such as a covalent bond or a dislocation, or a compound which can interact with the polymer substrate. Such a surface modifying agent can be, for example, a molecule having a rebel, (level 1, a compound of a functional group such as an amine group, a 4-membered ammonium carbonyl group, a glycidyl group, a vinyl group, a (meth) acryloxy group, or a fluorenyl group, etc., such a surface modifier is usually included in the standard. It is a liquid under temperature and pressure conditions, and the number of carbon atoms in the molecule is, for example, 15 or less, preferably 1 Torr or less, and particularly preferably 8 or less. The molecular weight of the aforementioned low molecular organic compound is not particularly limited. The amount is preferably 500 or less, preferably 35 Å or less, and particularly preferably 200 Å or less. Suitable surface modifiers include, for example, citric acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, and acrylic acid. , thioglycolic acid, crotonic acid, citrus-24- 201221541 citric acid, adipic acid, succinic acid, glutaric acid, oxalic acid, maleic acid and fumaric acid, etc. And the polycarboxylic acid type % is preferably a -acid acid type of the above-mentioned saturated or unsaturated-membered and polybasic acid § (suitably C methacrylate vinegar, etc. - C4 alkyl brewing); A β-diamino compound such as alkoxyacetone, 2,4-dihexamethylene, 3,5-glycolide, acetamidineacetic acid or C~C4 ortho-acetic acid. Further, it is not particularly limited, and a known surface coupling agent can also be used. The particle size of the inorganic material (D) is not particularly limited, and usually O.Olnm~2〇0 is preferably left and right, preferably 〇Um~1〇〇(4) is preferably about 0.1 nm to 50 μmη. In the case of the content of the inorganic filler (D), when the total content of the compound (Α) and the compound is 100 parts by weight, it is preferably 丨 加 加 (eight) parts by weight, more preferably Π) 〜1 〇〇. 〇 by weight. Further, the content of the inorganic filler (D) relative to the total amount of the high refractive index resin composition for electronic components is not particularly limited, and is preferably, for example, 5 to 95% by weight, preferably i 〇 to 9 Å by weight. [The decane coupling agent (E)] The high refractive index resin composition for electronic components of the present invention has adhesion to a substrate such as a substrate, and may further improve the content of a decane coupling agent. The decane coupling agent (Ε) is not particularly limited, and a well-known decane coupling agent can be used. The decane coupling agent (Ε) is, for example, selected from the group consisting of tetramethoxy decane, tetraethoxy decane, decyl triethoxy decane, dimethyl diethoxy decane, methyl triethoxy decane, and vinyl three. Ethoxy decane, ethylene trimethoxy sulphate, ethylene ginseng (methoxy ethoxylate), stupyl trimethoxy decane, diphenyl decyl decane, vinyl triethylene hydrazine - 25- 201221541 oxydecane, γ-(meth) propylene methoxypropyl triethoxy oxime, methyl) propylene methoxy propyl trimethoxy decane, γ-(methyl) propylene Oxypropyl decyl dimethoxy decane, γ-(indenyl) propylene methoxy propyl methyl monoethoxy ketone, ^ - glycidyl propyl propyl trimethoxy sec- ate, 3 glycidyl ether Propyl dimethyl decyloxy decane, 3-glycidyl fluorenyl propyl triethoxy decane, 3-glycidyl ether propyl fluorenyl diethoxy sulphite, 2-(3, 4- Epoxycyclohexyl)ethyltrimethoxydecane, p-ethylethenyltrimethoxy decane, 3-propenyloxypropyltrimethoxy zeoxime, Ν-(β-aminoethyl)-γ-amine Propylmethyldiazine Basear, Ν_(β_aminoethyl)-γ-aminopropyl decyl diethoxy decane, Ν-(β-aminoethyl)-γ-aminopropyltrimethoxy decane, Ν-(β- Amine ethyl)-γ-aminopropyl triethoxy oxime, ν_phenyl-γ-aminopropyltrimethoxydecane, γ-aminopropyltrimethoxy decane, γ·aminopropyltriethoxy Baseline, 3-mercaptopropyltrimethoxydecane, 3-mercaptopropyldiethoxydecane, 3-isopropylpropyldimethoxydecane, bis(triethoxycarbamidopropyl)tetra A substance which is relatively stable in an aqueous solution, such as a sulfide or a 3-isocyanate propyl triethoxy group. The decane coupling agent (Ε) may be used singly or in combination of two or more. The amount (content) of the ceramsite coupling agent (yttrium) is preferably in the range of about 1 to 20% by weight, preferably 0.3 to 8% by weight, based on the composition of the high refractive index resin for electronic components. More preferably 〇5~5 wt%. When the weight % is less than 5% by weight, the crosslinking effect of the resin produced by the decane coupling agent (E) is lacking, so that a dense film cannot be obtained, and the coupling with the metal substrate is not effective, the adhesion is poor, and it is difficult to obtain The desired alkali resistance and rust resistance 8 is higher than 20% by weight, and the water resistance and alkali resistance are remarkably lowered due to hydrolysis, and the film formation property is problematic, and the economical aspect is -26-201221541. It is easy to lose interest. [Other Additives j The electron element of the present invention is to use a polymeric forest. The composition of the refractive index resin can be used according to the need for a homogenizing agent, an antifoaming agent, a sea ancestors, a plasticizer, a absorbing agent, a Yankee. A conventional additive such as a phosphor, an organic solvent, an ultraviolet absorber, or an electron-dual release agent of the present invention. Sub-element Tian Gu + 9 (TC (preferably 〇~4〇. The composition of the resin is 0~-temperature TMM, / is near room temperature (G~ grab left and right)) Excellent operability: a closed, sealed or surface device of 70 electrons, and a packaged device, such as a sealing agent, a sealant, etc., which are necessary for an electronic component having a high refractive index as the organic electroluminescence device 4. ^ # ® tll .. can also be used as a coating or adhesive for anti-reflection film of display. [Manufacturing method of high refractive index resin composition for electronic components] The high refractive index resin composition is obtained by hooking and mixing the t components. In order to obtain the electron: two-refractive index resin composition of the present invention, it is preferable to use a self-rotating agitating agitating, a self-propelled machine, or a planetary crucible. Mixing, dissolving, mixing, dispersing, etc., in a known mixing machine such as a mixer, a 3-roll mill, or a bead mill, so that the components are as uniform as possible. [Cured (resin cured)] The high refractive index resin composition for electronic parts of the present invention can be made by light or It is hardened by heat, and it can be hardened by light of 100 mJJ/cm2 or more by a mercury lamp etc. Moreover, it can harden by heat, and can be the temperature of 5〇2. 〇 (rc (preferably 5〇~ -27- 201221541 190 °C, more preferably 50~180 °C), with a hardening time of 10 to 600 minutes (preferably 10 to 480 minutes, more preferably 15 to 360) In the case where the hardening temperature and the hardening time are less than the lower limit of the above range, the hardening becomes insufficient. In contrast, when the upper limit is higher than the above range, the resin component may be decomposed. Therefore, there is a case where neither of them may be inferior. The hardening conditions are determined according to various conditions, and the hardening time may be shortened in the case where the hardening temperature is high, and the hardening time may be appropriately adjusted in the case where the hardening temperature is low. When the high refractive index resin composition for an electronic component of the present invention is cured, a cured product having a high refractive index can be obtained. The cured product obtained by curing the high refractive index resin composition for an electronic component of the present invention has a high refractive index. Refractive index丨62 to 175 is preferable, and more preferably 1.64 to 1.70. [Organic electroluminescent device, LED device, or display] An electronic component of the high refractive index resin composition for electronic components of the present invention is a suitable example. An organic electroluminescent device, an LED device, a display, etc. according to the present invention, a high refractive index resin composition for an electronic component, the extraction efficiency of the nine lines of the electronic components is increased [Blocking agent, sealant, or coating agent] The sealing agent, the wheat seal, the sealant, or the coating agent (antireflective coating agent) of the present invention contain the above-mentioned electronic component The composition thus has a high refractive index in the case of a liquid at any temperature of 0 to 90 c. Therefore, it is necessary to have a high refractive index after hardening of the device or the like: an electroluminescent device, (4) electronic components are sealed, sealed, and the parts can be used. 〃 y, the anti-reflective surface coating, etc. -28-201221541 [Examples] Hereinafter, the present invention will be described in more detail based on the examples, and the present invention is not limited by the examples. Synthesis Example [Synthesis of bisphenol F divinyl ether] Sodium carbonate (31 8 g, 3 〇〇〇 mm 加入) was placed in a 2 liter four-necked flask equipped with a Dean Stark condenser, a stirrer, and a thermometer. 1),
甲笨(537.2g)、丙酸乙稀酯(2〇〇g,2〇〇〇mmol)、雙酴F (51.6g,257.7mm〇l)、及氣化銥環辛二烯錯合物[IrC1 (c〇d)]2(5.04g,7.50mmol),浸於 130°C的油浴,並加熱回 流。將由反應進行所產生的水移除至反應統系外,同時 授拌4小時。然後’將反應液放涼至室溫,加水並移至分 液漏斗。以醋酸乙酯萃取水層,在有機層中加入飽和食 鹽水,並且洗淨。然後分出有機層,以無水硫酸鎂脫水 之後,將溶劑餾除’而得到液狀之粗產物。以減壓蒸餾 將其精製(142°C,30Pa) ’得到下述無色透明液體的目標產 物(雙酚F二乙烯基醚)(63.0g,97%)。 'H-NMR (500MHz, CDC13)63.90(s,0.58H), 3.95(s, 1·〇4Η), 4.01(s, 0.30H), 4.36-4.40(m, 2H), 4.63-4.74(m, 2H),6.57-6.63(m, 2H), 6.93-7.00(m, 4H),7.10-7.21(m, 4H). ’ 實施例1 將N-乙烯基咔唑(商品名P0656 ;東京化成製)4〇重量 份、雙酚F二縮水甘油醚(商品名re-303 S;日本化藥製)3〇 重量份、鄰苯酚縮水甘油醚(商品名G0098 ;東京化成製 -29- 201221541 )30重量份、及光陽離子起始劑Ρΐ·2〇74 1重量份,投入自 公轉式擾拌脫泡裝置(型式AR-25〇;Thinky製)内,進行 攪拌、溶解、混合、分散,調製出樹脂組成物液體。所 得到的樹脂組成物在室溫(20°C )呈均勻的液態(亦即軟化 點未滿20°C)。 實施例2〜3 除了以表1所示的量使用表1所示的咔唑化合物 、及化合物(B)以外,係以與實施例1同樣之方式調製出 樹脂組成物液體。在實施例2中’所得到的樹脂組成物在 室溫(20°C )呈均勻的液態(亦即軟化點未滿2〇°c ),在實施 例3中,軟化點為46°C。 實施例4 將N -乙稀基叶嗤(商品名p〇656 ;東京化成製)4〇重量 份、雙紛F二縮水甘油醚60重量份、及熱陽離子起始劑 SI-60L 1重量份’投入自公轉式攪拌脫泡裝置(型式 AR-250 ; Thinky製)内,進行攪拌、溶解、混合、分散, 調製出樹脂組成物液體。所得到的樹脂組成物在室溫 (20°C)呈均勻的液態(亦即軟化點未滿2〇〇c)。 實施例5〜7 除了以表1所示的量使用表1所示的咔唑化合物(A) 、及化合物(B)以外,係以與實施例4同樣的方式調製出 樹脂組成物液體。所得到的樹脂組成物任一者皆在室^ (20°C )呈均勻的液態(亦即軟化點未滿2〇。匚)。 <樹脂組成物之硬化> 以水銀燈對於實施例1〜3所得到的樹脂組成物進行 1000mJ/cm2的照光’而製作出硬化物。 -30- 201221541 在1 〇 0 C對於實施例4〜7所得到的樹脂組成物進行工 小時加熱,而製作出硬化物。 <折射率之測定> 針對所得到的硬化物,使用Metdcon公司製Model 2〇10稜鏡耦合儀測定在589nm的折射率。將結果揭示於 表1。 <軟化點之測定> 針對所得到的樹脂組成物之中在室溫下為固態者 使用Yanaco製微量熔點測定裝置Mp_5〇〇D測定軟化點。 [表 1] ”A stupid (537.2g), ethyl propionate (2〇〇g, 2〇〇〇mmol), biguanide F (51.6g, 257.7mm〇l), and gasified anthracycline octane complex [ IrC1 (c〇d)] 2 (5.04 g, 7.50 mmol) was immersed in an oil bath at 130 ° C and heated to reflux. The water produced by the reaction was removed to the outside of the reaction system while mixing for 4 hours. Then the reaction solution was allowed to cool to room temperature, water was added and transferred to a sep. funnel. The aqueous layer was extracted with ethyl acetate, saturated brine was added to the organic layer, and washed. Then, the organic layer was separated and dried over anhydrous magnesium sulfate, and then the solvent was evaporated to give a crude product. This was purified by vacuum distillation (142 ° C, 30 Pa) to give the desired product ( bisphenol F divinyl ether) (63.0 g, 97%). 'H-NMR (500MHz, CDC13) 63.90 (s, 0.58H), 3.95 (s, 1·〇4Η), 4.01 (s, 0.30H), 4.36-4.40 (m, 2H), 4.63-4.74 (m, 2H), 6.57-6.63 (m, 2H), 6.93-7.00 (m, 4H), 7.10-7.21 (m, 4H). 'Example 1 N-vinylcarbazole (trade name P0656; manufactured by Tokyo Chemical Industry Co., Ltd.) 4 parts by weight, bisphenol F diglycidyl ether (trade name re-303 S; manufactured by Nippon Kasei Co., Ltd.) 3 parts by weight, o-phenol glycidyl ether (trade name G0098; Tokyo Chemical Co., Ltd. -29-201221541) 30 weight And a photocationic initiator Ρΐ·2〇74 1 part by weight, put into a revolving scavenging defoaming device (type AR-25〇; manufactured by Thinky), stir, dissolve, mix, disperse, and prepare a resin Composition liquid. The obtained resin composition was uniformly liquid at room temperature (20 ° C) (i.e., the softening point was less than 20 ° C). (Examples 2 to 3) A resin composition liquid was prepared in the same manner as in Example 1 except that the carbazole compound shown in Table 1 and the compound (B) were used in the amounts shown in Table 1. In the Example 2, the obtained resin composition exhibited a uniform liquid state at room temperature (20 ° C) (i.e., the softening point was less than 2 ° C), and in Example 3, the softening point was 46 °C. Example 4 4 parts by weight of N-ethylene sulfanthine (trade name p〇656; manufactured by Tokyo Chemical Industry Co., Ltd.), 60 parts by weight of F diglycidyl ether, and 1 part by weight of thermal cationic initiator SI-60L 'Into a revolutionary stirring and defoaming device (type AR-250; manufactured by Thinky), stirring, dissolving, mixing, and dispersing were carried out to prepare a resin composition liquid. The obtained resin composition exhibited a uniform liquid state at room temperature (20 ° C) (i.e., the softening point was less than 2 〇〇 c). (Examples 5 to 7) A resin composition liquid was prepared in the same manner as in Example 4 except that the carbazole compound (A) and the compound (B) shown in Table 1 were used in the amounts shown in Table 1. Either of the obtained resin compositions exhibited a uniform liquid state (i.e., a softening point of less than 2 Å) at room temperature (20 ° C). <Curing of Resin Composition> The resin composition obtained in Examples 1 to 3 was irradiated with light at 1000 mJ/cm 2 by a mercury lamp to produce a cured product. -30-201221541 The resin composition obtained in each of Examples 4 to 7 was heated at 1 〇 0 C to produce a cured product. <Measurement of Refractive Index> The refractive index at 589 nm of the obtained cured product was measured using a Model 2〇10稜鏡 coupler manufactured by Metdcon. The results are disclosed in Table 1. <Measurement of softening point> The softening point was measured using a Yanaco micro melting point measuring apparatus Mp_5〇〇D for the solid resin at room temperature among the obtained resin compositions. [Table 1] "
^化物之折料(589nm) [產業上之可利用性 本發明之電子元件用高折射率樹脂組成物對於電子 元件而έ ,在封閉、密封或表面塗敷時的操作性優異。 因此,可使用作為有機電致發光裝置、led裝置等必需 具有高折射率的電子零件用的封閉劑、密封劑等。另外 還可使用作為顯示器的抗反射膜用的表面塗敷劑或接着 劑。 【圖式簡單說明】 無。 【主要元件符號說明】 M. 〇 -31-(Fabricity of the compound (589 nm) [Industrial Applicability The high refractive index resin composition for electronic components of the present invention is excellent in handleability at the time of sealing, sealing or surface coating. Therefore, a blocking agent, a sealant, or the like for an electronic component having a high refractive index, such as an organic electroluminescence device or a led device, can be used. Further, a surface coating agent or an adhesive for an antireflection film of a display can also be used. [Simple description of the diagram] None. [Main component symbol description] M. 〇 -31-
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