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Adamantane derivative, method for producing the same, resin composition containing the adamantane derivative and use thereof

A technology of resin composition and adamantane, which is applied in the photolithographic process of the patterned surface, instruments, electrical components, etc., can solve the problems of low yield, low reactivity, complex reaction path and other problems of cyclic ether compounds, and achieve the goal of sticking Good contact effect

Inactive Publication Date: 2010-03-17
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the low reactivity of adamantanediols, the yield of the cyclic ether compound obtained by the reaction of adamantanediols and cyclic ether group-containing compounds represented by epichlorohydrin is low, and in order to obtain a high yield High-rate cyclic ether compounds must go through complex reaction pathways, so it is hard to say that they are industrially useful

Method used

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  • Adamantane derivative, method for producing the same, resin composition containing the adamantane derivative and use thereof
  • Adamantane derivative, method for producing the same, resin composition containing the adamantane derivative and use thereof
  • Adamantane derivative, method for producing the same, resin composition containing the adamantane derivative and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0115] [Synthesis of 1,3,5-adamantanetricarboxylic acid triglycidyl ester]

[0116] Add 1,3,5-adamantanetricarboxylic acid 30g (0.11mol), epichlorohydrin 124g ( 1.30 mol), 3 g of tetraethylammonium bromide, 90 g of toluene, and 40 g of 50 mass % sodium hydroxide aqueous solution were placed in a 130° C. oil bath for 5 hours and heated to reflux. At this time, a small amount of nitrogen gas was flowed and the mixture was stirred to allow the reaction to proceed while removing water flowing out as the reaction proceeded to the outside of the reaction system. Thereafter, the reaction liquid was cooled to room temperature, and the aqueous layer was washed with water until it became neutral, and then the solvent was distilled off from the organic layer to obtain a yellow viscous liquid.

[0117] Then, this yellow viscous liquid was dissolved in 175 g of toluene, 10.5 g of a 25% by mass aqueous sodium hydroxide solution was added, stirred in a 130° C. oil bath for 2 hours, and heat...

Embodiment 2

[0124] [Synthesis of 1,3-adamantane diacetate diglycidyl ester]

[0125] Add 50 g (0.20 mol) of 1,3-adamantane diacetic acid and 75 g (0.78 mol) of epichlorohydrin into a 500 mL round bottom flask equipped with a Dean-Stark reflux condenser, a stirrer, a thermometer, and a nitrogen inlet tube , 5 g of tetraethylammonium bromide, 225 g of toluene, and 48 g of a 50% by mass sodium hydroxide aqueous solution were placed in a 130° C. oil bath and immersed in a 130° C. oil bath for 3 hours and heated to reflux. At this time, a small amount of nitrogen gas was flowed and the mixture was stirred to allow the reaction to proceed while removing water flowing out as the reaction proceeded to the outside of the reaction system. Thereafter, the reaction liquid was cooled to room temperature, and the aqueous layer was washed with water until it became neutral, and then the solvent was distilled off from the organic layer to obtain a yellow viscous liquid.

[0126] Then, this yellow viscou...

Embodiment 3

[0143] 5 g of 1,3,5-adamantanetricarboxylic acid triglycidyl ester obtained in Example 1, 4.87 g of methyl hexahydrophthalic anhydride (manufactured by Nippon Chemical Co., Ltd., MH700) as an acid anhydride, 0.1 g of 1,8-diazabicyclo[5.4.0]undecene-7 octanoate (manufactured by San-Apro, SA102) as a curing accelerator, 2,6-di-tert-butyl as an antioxidant - 0.03 g of 4-methylphenol (BHT) was mixed at room temperature, defoamed, heated at 110° C. for 2 hours, and then heated at 150° C. for 3 hours to produce a cured product (a sheet with a film thickness of 3 mm).

[0144] Measure the glass transition temperature and light transmittance of the cured product of the resin composition according to the above-mentioned measurement methods (1) and (2), and carry out the light resistance test and long-term heat resistance test according to the above-mentioned evaluation tests (3) and (4). test. The evaluation results are shown in Table 1.

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Abstract

Disclosed is an adamantane derivative represented by the general formula (I) below, which enables to obtain a cured product excellent in transparency, optical characteristics such as light resistance,durabilities such as heat resistance, and electrical characteristics such as dielectric constant. Also disclosed are a method for producing such an adamantane derivative, a resin composition containing such an adamantane derivative and an epoxy resin curing agent, and a sealing agent for optical semiconductors using such a resin composition. (I) (In the formula, Y represents a group selected froma hydrocarbon group, a hydroxy group, a carboxyl group and an =O group wherein two Y's are combined together; Z represents a cyclic ether group; n represents an integer of not less than 0; and p represents an integer of 2-4 and q represents an integer of 0-14, while satisfying 2 = p + q = 16.

Description

technical field [0001] The present invention relates to a novel adamantane derivative, its production method, a resin composition containing the adamantane derivative and its use, and relates in detail to the adamantane derivative, its production method, the adamantane derivative and epoxy resin Resin composition of curing agent and sealing agent for optical semiconductor, optical and electronic parts, and sealing agent for circuit using the same, wherein the adamantane derivative provides a cured product having excellent optical properties such as transparency and light resistance , long-term heat resistance and other durability, electrical properties such as dielectric constant, and the cured product is suitable for optical semiconductor sealants, optical and electronic components (optical waveguides, optical communication lenses, optical films, etc.), circuit sealants and Adhesives etc. Background technique [0002] Optical semiconductor devices widely used in display de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G59/20C07D303/06C07D303/16H01L23/29H01L23/31H01L33/00C07D303/44
CPCC08G59/3218C08G59/42C08G59/24C08L63/00C07D303/16G03F7/038C07D303/06C08G59/20H01L23/29
Inventor 冈田保也大野英俊伊藤克树
Owner IDEMITSU KOSAN CO LTD
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