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Polycarboxylic acid and polycarboxylic acid composition containing same, epoxy resin composition, thermosetting resin composition, and cured material of same, and optical semiconductor device

A technology of resin composition and polycarboxylic acid, which is applied in semiconductor devices, semiconductor/solid-state device parts, organic chemistry, etc., can solve problems such as inability to be suitable for mold forming, deviation of cured product properties, high melting point, etc., and achieve full vitrification Transition temperature, excellent resin reactivity, and excellent cured physical properties

Inactive Publication Date: 2017-05-31
NIPPON KAYAKU CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a result, the following problems will occur: environmental pollution caused by harmful substances discharged into the atmosphere, adverse effects on the human body, pollution of the production line, and the absence of a specified amount of carboxylic anhydride (curing agent) in the cured product, resulting in poor curing of the epoxy resin composition. Wait
Variations in curing conditions caused by volatilization of the curing agent will lead to deviations in the physical properties of the cured product, making it difficult to stably obtain a cured product with target properties
[0006] In addition, the problem of volatilization is remarkable when encapsulating LEDs, especially surface mount devices (SMD: Surface Mount Device) with curable resin compositions for optical semiconductor encapsulation composed of conventional acid anhydrides as curing agents. If the amount of resin used is small, there will be a dent, and in severe cases, the lead wire will be exposed
Furthermore, there are problems such as cracks and peeling during reflow soldering, and it is difficult to withstand long-term lighting
[0009] Acid anhydrides used as curing agents for thermosetting resins are volatile and have a low melting point, so there is a problem that they are not suitable for molding
[0010] Tetracarboxylic anhydride has no volatility, but has a high melting point (above 150° C.), so it is difficult to handle as a liquid resin composition and has poor formability. Therefore, considering the ease of use for molding liquid resins, unsuitable for intended use
[0011] It is also known that carboxylic acid is used as a curing agent for epoxy resin, but its melting point is relatively high (150°C or higher), and it has the same problems as above. In addition, it is extremely difficult to ensure high transmission because it is easily colored when heated. rate and therefore not suitable for the intended use
[0012] Similarly, polycarboxylic acid compounds also have problems of high melting point (above 150°C), high crystallinity, difficult resin kneading, and coloring, making them unsuitable for the intended use.
[0013] Therefore, as a conventionally known material, no compound capable of achieving the above-mentioned purpose has been found.

Method used

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  • Polycarboxylic acid and polycarboxylic acid composition containing same, epoxy resin composition, thermosetting resin composition, and cured material of same, and optical semiconductor device
  • Polycarboxylic acid and polycarboxylic acid composition containing same, epoxy resin composition, thermosetting resin composition, and cured material of same, and optical semiconductor device
  • Polycarboxylic acid and polycarboxylic acid composition containing same, epoxy resin composition, thermosetting resin composition, and cured material of same, and optical semiconductor device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0324] Embodiment 1: the manufacture of polyhydric carboxylic acid (A-1)

[0325] 26.1 g of tris(2-hydroxyethyl) isocyanurate, RIKACID MH-T (4-methylhexahydro Phthalic acid) 52.1 g, toluene 70 g, a serpentine double-helix condenser (Dimroth condenser), a stirring device, and a thermometer were installed, and the flask was immersed in an oil bath. The oil bath was heated, and the internal temperature was kept at 115° C., and the reaction was carried out for 7 hours as it was.

[0326] The obtained reaction liquid was concentrated under reduced pressure at 100° C., and toluene was distilled off to obtain 71.5 g of a polyvalent carboxylic acid (A-1) having the following formula (23) as a main component. The GPC purity (GPC area %) of the obtained compound was 92%, the acid value was 203.4 mgKOH / g, and the external appearance was a white solid. In addition, the melting point (peak apex value) using DSC was 57.0°C, and the thermogravimetric reduction was -3.4%. The GPC chart of ...

Embodiment 2

[0328] Embodiment 2: Manufacture of polyhydric carboxylic acid composition (C-1)

[0329]26.1 g of tris(2-hydroxyethyl) isocyanurate, RIKACID MH-T (4-methylhexahydro Phthalic anhydride) 123.4g, a serpentine double-helix condenser, a stirring device, a thermometer are set, and the flask is soaked in an oil bath. The oil bath was heated, and the internal temperature was kept at 78° C., and the reaction was carried out for 4 hours as it was. It was confirmed by GPC that the peak of tris(2-hydroxyethyl) isocyanurate was 1 area % or less, and 147 g of a polyvalent carboxylic acid composition (C-1) belonging to a mixture of a polyvalent carboxylic acid and a carboxylic anhydride compound was obtained. The resulting mixture is a colorless and transparent liquid, and the purity measured by GPC is 59.5 area % of the polycarboxylic acid (A-1) represented by the aforementioned formula (23), 4-methyl Hexahydrophthalic acid accounted for 1.3 area%, and 4-methylhexahydrophthalic anhydride...

Embodiment 3

[0331] Embodiment 3: the manufacture of polycarboxylic acid composition (C-2)

[0332] In a container made of polypropylene, 20 g of the polyvalent carboxylic acid composition (C-1) obtained in Example 2 and 6.67 g of RIKACIDMH-T (4-methylhexahydrophthalic acid manufactured by Shikoku Chemical Industry Co., Ltd.) were placed. , and mixed with a spatula to obtain 26.6 g of a polycarboxylic acid composition (C-2). The obtained mixture is a colorless and transparent liquid, and the purity measured by GPC is 46.2 area % of the polycarboxylic acid ((A-1) represented by the aforementioned formula (23), 4-methylhexahydrophthalic acid ( The aforementioned formula (24)) was 3.9 area %, and 4-methylhexahydrophthalic anhydride was 49.9 area %. In addition, the functional group equivalent was 187 g / eq, the viscosity was 24678 mPa·s, and the thermogravimetric reduction was -31.7%.

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Abstract

The purpose of the present invention is to provide: a polycarboxylic acid and polycarboxylic acid composition containing the same, an epoxy resin composition, and a thermosetting resin composition having minimal volatility when cured and excellent curing properties, whereby a cured material thereof has excellent transparency and hardness, the glass transition temperature of the cured material can be adequately increased, and excellent moldability and minimal coloring of the cured material are obtained; a cured material of the aforementioned compositions; and a semiconductor device. This polycarboxylic acid is represented by formula (1). (In formula (1), R1 represents a C1-6 alkylene group, and R6 represents a hydrogen atom or a C1-10 organic group containing a carboxyl group. In formula (1), the plurality of R1 and R6 may each be the same or different, but 50 mol% or more of the plurality of R6 are C1-10 organic groups containing a carboxyl group.)

Description

technical field [0001] The present invention relates to parts that are particularly suitable for optical semiconductor packaging applications, optical semiconductor reflective materials, etc. that require high transparency and low coloring, especially when used for optical semiconductor reflective materials or optical semiconductor devices having the optical semiconductor reflective material. Polyhydric carboxylic acid with high glass transition temperature of cured product and excellent moldability, polycarboxylic acid composition containing it, thermosetting resin composition, epoxy resin composition, cured product obtained by curing them, and optical semiconductor device. Background technique [0002] Epoxy resin compositions are used as resins excellent in heat resistance in fields such as construction, civil engineering, automobiles, and aircraft. In recent years, especially in the field of semiconductor-related materials, products with keywords such as light, thin, sh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/34C08G59/42H01L23/29H01L23/31
CPCC07D251/34C08G59/42H01L2924/0002H01L23/29H01L23/31H01L2924/00C08G59/4028C08K5/098
Inventor 宫川直房青木静枪田正人田中荣一川田義浩
Owner NIPPON KAYAKU CO LTD
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