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Adamantane derivative, resin composition containing same, and optoelectronic member and sealing agent for electronic circuit using those

一种树脂组合物、金刚烷的技术，应用在有机化合物的制备、用于光机械设备的光敏材料、光学等方向，能够解决电子电路介电常数高、很难耐热性充分、黄变等问题，达到吸水性优异、透明性优异的效果

Active Publication Date: 2009-02-18
OSAKA ORGANIC CHEM INDS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As the encapsulating resin, adhesive resin or film used in these applications, or resin for lenses, if conventionally used bisphenol A type epoxy resin, etc. are used, the dielectric constant of the electronic circuit is high, and the heat resistance is high. Insufficient, in the packaging of optical waveguide or LED components, there are problems such as decreased transparency or yellowing due to resin deterioration
For example, Patent Document 6 discloses an encapsulating resin composition using a bisphenol A type epoxy resin, but it is difficult to say that the heat resistance is sufficient.
In addition, Patent Documents 7 and 8 disclose resin compositions using alicyclic epoxy resins such as 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, Although the cured product of this resin composition has high heat resistance, it has a problem of high water absorption

Method used

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  • Adamantane derivative, resin composition containing same, and optoelectronic member and sealing agent for electronic circuit using those
  • Adamantane derivative, resin composition containing same, and optoelectronic member and sealing agent for electronic circuit using those
  • Adamantane derivative, resin composition containing same, and optoelectronic member and sealing agent for electronic circuit using those

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0137] Embodiment 1 [1-(2,4-diglycidyloxyphenyl) adamantane [synthesis of formula (I-1)]] (1) 1-(2,4-dihydroxyphenyl) adamantine Synthesis of alkanes

[0138] Add 28.1g (0.18mol) 1-adamantanol, 8.8g (0.05mol) p-toluenesulfonic acid monohydrate and 35mL Ethanol for nitrogen replacement. 39.6 g (0.36 mol) of resorcinol was added thereto. This was added to a 90° C. oil bath, and heated and stirred for 3 hours. The reaction solution was cooled, then 200 mL of pure water was added, stirred for 30 minutes, and then filtered to obtain a solid. The solid was dried under reduced pressure, then recrystallized with methanol / toluene mixed solvent, and the obtained crystal was taken out while washing with toluene, and dried under reduced pressure to a constant weight to obtain the target compound (yield 86%).

[0139] Through nuclear magnetic resonance spectroscopy ( 1 H-NMR, 13 C-NMR) to identify the compound.

[0140] NMR spectroscopy was performed using DMSO-d 6 As a solvent, it...

Embodiment 2

[0149] Example 2 [Synthesis of 1-(2,3,4-trihydroxyphenyl)adamantane [the above formula (II-1)]]

[0150]In Example 1 (1), the resorcinol was changed to 45.3g (0.36mol) pyrogallol, except that the same operation was performed as in Example 1 (1), to obtain the target compound (yield 78%) .

[0151] Through nuclear magnetic resonance spectroscopy ( 1 H-NMR, 13 C-NMR) to identify the compound.

[0152] NMR spectroscopy was performed using DMSO-d 6 As a solvent, it measured with JNM-ECA500 manufactured by JEOL Ltd.

[0153] 1 H-NMR (500MHz): 1.70(s, 6H), 2.02(s, 9H), 6.20(d, IH), 6.36(d, 1H), 7.77(br, 1H), 8.20(br, 1H), 8.84 (br,1H)

[0154] 13 C-NMR (125MHz): 28.46, 35.52, 36.68, 40.30, 105.49, 115.41, 127.27, 132.56, 143.84, 145.36

Embodiment 3

[0155] Example 3 [Synthesis of 1-(2,3,4-triglycidyloxyphenyl)adamantane [the above formula (I-2)]]

[0156] In embodiment 1 (2), change 1-(2,4-dihydroxyphenyl) adamantane into 20.5g (0.08mol) 1-(2,3,4-trihydroxyl) synthesized in embodiment 2 Phenyl) adamantane, the usage-amount of epichlorohydrin is changed into 80g (0.86mol), the usage-amount of sodium hydroxide is changed into 12.2g (0.30mol), carry out similarly with embodiment 1 (2) except this Operation to obtain the target compound (yield 90%). The LC purity of this compound was 92% (92% of the monomer and the rest were oligomers of the target compound).

[0157] Through nuclear magnetic resonance spectroscopy ( 1 H-NMR, 13 C-NMR) to identify the compound.

[0158] NMR spectroscopy was performed using DMSO-d 6 As a solvent, it measured with JNM-ECA500 manufactured by JEOL Ltd.

[0159] 1 H-NMR (500MHz): 1.76(s, 6H), 2.04(s, 9H), 2.68(m, 3H), 2.85(m, 3H), 3.36(m, 3H), 3.84(m, 3H), 4.28 (m, 3H), 6.53(d, 1H), 6.68(d...

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Abstract

Disclosed is an adamantane derivative which enables to obtain a cured product excellent in optical characteristics such as transparency and light resistance, electrical characteristics such as long-term heat resistance and dielectric constant, and low water absorption. Also disclosed are a resin composition containing such an adamantane derivative, a sealing agent for electronic circuits, optoelectronic member, semiconductor device and copper-clad laminate each using such a resin composition, and a radiation-sensitive resin composition which contains such an adamantane derivative as a crosslinking agent. Specifically disclosed are an adamantane derivative represented by the formula (I-1) below, a resin composition containing such an adamantane derivative, a sealing agent for electronic circuits, optoelectronic member, semiconductor device and copper-clad laminate each using such a resin composition, and a radiation-sensitive resin composition which contains such an adamantane derivative as a crosslinking agent.

Description

technical field [0001] The present invention relates to a novel adamantane derivative capable of forming a cured product excellent in optical properties such as transparency and light resistance, long-term heat resistance, electrical properties such as dielectric constant, and low water absorption, and optical and electronic components and electronic devices using the derivative. Encapsulants for circuits, etc. More specifically, the present invention relates to an encapsulant suitable for use as an electronic circuit encapsulant (encapsulant for an optical semiconductor, an encapsulant for an organic electroluminescence (EL) element, etc.), an optical electronic component (optical waveguide, optical communication lens, and Optical films, etc.) and adhesives used for them, or crosslinking agents for radiation-sensitive resin compositions, etc., optical properties such as transparency and light resistance, long-term heat resistance, electrical properties such as dielectric cons...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/30C07C39/14C07D301/28C08G59/20G03F7/004
CPCY10T428/1073C07D303/30C07C2103/74C07D301/28C08G59/24C08G59/4223C07C37/16C07C37/20C08G59/4215Y10T428/31511C07C39/17G03F7/038C08G59/621C07C2603/74C09K2323/055
Inventor 冈田保也伊藤一山根秀树松本信昭
Owner OSAKA ORGANIC CHEM INDS
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