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Siloxane compound and cured product thereof

A technology of siloxane compounds and cured products, which is applied in the direction of silicon organic compounds, electrical solid devices, semiconductor/solid device components, etc., can solve the problems of heat resistance degradation and not yet obtained, and achieve excellent heat resistance.

Inactive Publication Date: 2014-01-01
CENT GLASS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, materials that do not deteriorate even after thousands of hours of heating at high temperatures above 250°C have not yet been obtained
When encapsulating semiconductors, etc., the hydrosilylation reaction is often used in the synthesis of silsesquioxanes that are liquid at around room temperature and can be potted. An alkylene chain at the terminal, such as a propylene chain, causes heat resistance to deteriorate (see Non-Patent Document 5 and Non-Patent Document 6)

Method used

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  • Siloxane compound and cured product thereof
  • Siloxane compound and cured product thereof
  • Siloxane compound and cured product thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0079] Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to these Examples. In addition, the quality evaluation of the siloxane compound obtained in this Example and a comparative example, and its hardened|cured material was performed by the method shown below.

[0080] [Evaluation method]

[0081]

[0082] The viscosity of the sample at 25° C. was measured using a rotational viscometer (produced by Brookfield Engineering Inc., product name “DV-II+PRO”) and a temperature control unit (Brookfield Engineering Inc., product name THERMOSEL).

[0083]

[0084] Using a thermogravimetric differential thermal analyzer (manufactured by Rigaku Corporation, product name TG8120), under the air flow of 50ml / min, the cured product of each siloxane compound was heated from 30°C at a heating rate of 5°C / min to measure Based on the previous mass, the temperature at the moment of 5 mass% reduction was measured.

[0085] 1. Synthesis of ...

Synthetic example 1

[0087] [Synthesis Example 1: Synthesis of Precursor Compound (A) Containing a Crosslinking Group Represented by Structural Formula (7)]

[0088] 14.6 g (80.0 mmol) of 4-bromobenzocyclobutene and 50 g of diethyl ether were added to a 1 L three-necked flask equipped with a thermometer and a reflux cooler, and cooled to -78° C. while stirring. After the internal temperature reached -78°C, 56 ml (90 mmol) of a 1.6 mol / L butyllithium hexane solution was added dropwise over 30 minutes. After stirring for 30 minutes after completion of the dropwise addition, 6.89 g (26.7 mmol) of trimethyltrivinylcyclotrisiloxane was added. The temperature was raised to room temperature while stirring, and the mixture was stirred at room temperature for 12 hours to obtain a diethyl ether solution of the compound represented by the structural formula (14) in the following reaction scheme.

[0089]

Synthetic example 2

[0090] [Synthesis Example 2: Synthesis of Precursor Compound (B) Containing a Crosslinking Group Represented by Structural Formula (10)]

[0091] 20.6 g (80.0 mmol) of 4-bromodiphenylacetylene and 50 g of diethyl ether were added to a 1 L three-necked flask equipped with a thermometer and a reflux cooler, and cooled to -78° C. while stirring. After the internal temperature reached -78°C, 56 ml (90 mmol) of a 1.6 mol / L butyllithium hexane solution was added dropwise over 30 minutes. After stirring for 30 minutes after completion of the dropwise addition, 5.94 g (26.7 mmol) of hexamethylcyclotrisiloxane was added. The temperature was raised to room temperature while stirring, and the mixture was stirred at room temperature for 12 hours to obtain a diethyl ether solution of precursor compound B represented by structural formula (15) in the following reaction scheme.

[0092]

[0093] 2. Synthesis of siloxane compound (1)

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Abstract

This siloxane compound is represented by general formula (1). (In formula (1): X is X1 or X2; at least on X is X1; R1-R5 are a hydrogen atom, an alkyl group, alkenyl group, or alkynyl group having 1-8 carbon atoms, a phenyl group or a pyridyl group; the carbon atoms may be substituted with an oxygen atom; the structure may contain an ether bond, a carbonyl group, or an ester bond; m is an integer from 3 to 8; n is an integer from 0 to 9; p is 0 or 1; and Y is a cross-linking group.) The siloxane compound can be easily molded and has fluidity at low temperatures and high heat resistance compared to conventional silsesquioxanes.

Description

technical field [0001] The present invention relates to heat-resistant resins, especially siloxane-based compounds and cured products thereof. The cured product obtained by curing the siloxane compound of the present invention can be used for various packaging materials and adhesives that require heat resistance, such as semiconductor applications, and can also be used for packaging for optical components when it is colorless and transparent. materials, lens materials or optical films, etc. Background technique [0002] Encapsulation materials for semiconductors such as Light Emitting Diodes (LEDs) are required to have heat resistance against heat generated by semiconductors during operation. [0003] Conventionally, epoxy resins and silicones, which are heat-resistant resins, have been used as sealing materials for semiconductors. However, when used in high-performance semiconductors represented by high-performance semiconductors using silicon carbide (SiC) that have a hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/21C08F30/08C08F38/00C08G77/04
CPCC08F30/08C09J183/08C08F38/00C08G77/04H01L23/296C08G77/26C09J183/04C08G77/20C07F7/21H01L2924/0002H01L2924/00
Inventor 本城启司江口弘山中一广
Owner CENT GLASS CO LTD
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