KR-20260065056-A - A New Curing Agent and A Preparing Method of the Same

Abstract

The present invention relates to a novel curing agent comprising naphthyl ester groups and N-aromatic amide groups, which exhibits excellent low dielectric loss (low Df), desmearability, copper foil adhesion, and solution stability; a method for manufacturing the same; an epoxy composition comprising the same; a cured product; and articles. The curing agent of the present invention not only exhibits excellent solution stability, but also achieves excellent low dielectric loss, desmearability, and copper foil adhesion through an epoxy composition comprising the curing agent and an epoxy resin of the present invention. Therefore, due to these improved characteristics, the epoxy composition comprising the curing agent of the present invention is suitable for use as an insulating film, an epoxy film for semiconductor packaging, an adhesive film, a build-up film, a substrate film, an epoxy sealing material, etc.

Inventors

• 전현애
• 김윤주
• 박숙연

Assignees

• 한국생산기술연구원

Dates

Publication Date

20260508

Application Date

20241031

Claims (8)

1. A curing agent comprising the following components (a), (b), and (c); (a) A diester compound represented by the following chemical formula (1), (b) an amide ester compound of at least one of the following chemical formulas (2-1) and (2-2), and (c) A diamide compound of at least one of the following chemical formulas (3-1) and (3-2).
2. In paragraph 1, A curing agent in which the weight ratio of (a) diester compound: (b) amide ester compound: (c) diamide compound in the above curing agent is 10 to 90:5 to 60:0.1 to 30.
3. A method comprising the step of mixing 0.6 to 1.4 equivalents of at least one amino aromatic alcohol selected from aminophenol and aminonaphthol per 1 equivalent of a diester compound represented by the following chemical formula (1), (a) A diester compound represented by the following chemical formula (1), (b) an amide ester compound of at least one of the following chemical formulas (2-1) and (2-2), and (c) A diamide compound of at least one of the following chemical formulas (3-1) and (3-2). A method for manufacturing a curing agent comprising
4. A method for manufacturing a curing agent according to claim 3, wherein the weight ratio of (a) diester compound: (b) amide ester compound: (c) diamide compound in the curing agent is 10 to 90:5 to 60:0.1 to 30.
5. (A) comprising an epoxy resin and (B) a curing agent, The above (B) curing agent is an epoxy composition comprising the curing agent of claim 1 or 2.
6. Cured product of the epoxy composition of paragraph 5.
7. Article comprising the epoxy composition of paragraph 5.
8. In paragraph 7, the above article is an insulating film, an epoxy film for semiconductor packaging, an adhesive film, a build-up film, a substrate film, or an epoxy sealing material.

Description

A New Curing Agent and A Preparing Method of the Same The present invention relates to a curing agent comprising a naphthyl ester group and an N-aromatic amide group, a method for manufacturing the same, an epoxy composition comprising the same, a cured product, and an article. Specifically, the invention relates to a novel curing agent comprising a naphthyl ester group and an N-aromatic amide group that exhibits excellent low dielectric loss (low Df), desmearability, adhesion, and solution stability, a method for manufacturing the same, an epoxy composition comprising the same, a cured product, and an article. With the advancement of AI, data centers, and HPC technologies, the importance of high-capacity data transmission and reception technologies is increasing. Accordingly, there is a demand for the development of semiconductor packaging material technologies that enable the transmission of large volumes of data as quickly as possible without transmission loss. Since high dielectric loss values in epoxy materials used for semiconductor packaging lead to significant data transmission loss and degraded signal quality, the low dielectric loss (low Df) characteristic of semiconductor materials is a critical feature for high-quality, high-speed data transmission. As disclosed in Patent No. 2051374, the most representative method for lowering the dielectric loss of epoxy materials is to use an active ester compound as a curing agent. Although the dielectric loss characteristics of epoxy insulating materials have been improved by the use of conventional active ester curing agents, there are problems such as insufficient solution dispersibility, desmearability, and adhesion to the copper foil layer. Therefore, in order to manufacture semiconductor components for ultra-high-speed semiconductor data transmission, there is a need to develop an epoxy insulating material that can simultaneously satisfy excellent dielectric loss (i.e., low Df), as well as desmear processability and copper foil adhesion. According to the present invention, a novel curing agent exhibiting excellent low dielectric loss characteristics, solution stability, desmearability, and copper foil adhesion in epoxy materials, a method for manufacturing the same, an epoxy composition comprising the same, a cured product of the epoxy composition, and an article comprising the epoxy composition are provided. These are described below. A. Novel curing agent According to one embodiment of the present invention, as a novel curing agent, (a) A diester compound represented by the following chemical formula (1), (b) an amide ester compound of at least one of the following chemical formulas (2-1) and (2-2) and (c) A novel curing agent is provided comprising a diamide compound which is at least one of the following chemical formulas (3-1) and (3-2). In the novel curing agent above, the weight ratio of (a) diester compound: (b) amide ester compound: (c) diamide compound is 10 to 90: 5 to 60: 0.1 to 30. To ensure dielectric loss characteristics, the diester compound is preferably present in a weight ratio of 10 to 90, more preferably 20 to 90. If the weight ratio exceeds 90, solution stability and adhesion characteristics may deteriorate, and if it is less than 10, it is difficult to ensure low dielectric loss characteristics. To ensure dielectric loss characteristics and processability, the amide ester compound is preferably present in a weight ratio of 5 to 60, more preferably 10 to 60. If the weight ratio exceeds 60, the dielectric loss value may increase, which is undesirable, and if it is less than 5, solution stability and adhesion characteristics may deteriorate. The diamide compound is present in a weight ratio of 0.1 to 30 in terms of dielectric loss and balance of physical properties, and preferably in a weight ratio of 0.1 to 25. If the weight ratio exceeds 30, the dielectric loss value increases, and if it is 0.1 or more in terms of balance of processability, it is desirable. According to another embodiment of the present invention, the curing agent (a) 10 to 90 parts by weight, preferably 20 to 90 parts by weight, of a diester compound represented by the following chemical formula (1), (b) 5 to 60 parts by weight, preferably 10 to 60 parts by weight, of an amide ester compound of at least one of the following chemical formulas (2-1) and (2-2) and (c) It may contain 0.1 to 30 parts by weight, preferably 0.1 to 25 parts by weight, of a diamide compound which is at least one of the following chemical formulas (3-1) and (3-2). The ester and amide groups, which are functional groups of the three compounds constituting the curing agent of the present invention, form a curing structure in which OH groups are not generated during the curing reaction with the epoxy resin, thereby enabling low Df characteristics of the epoxy cured product. In addition, due to the presence of amide groups, not only are the dispersibility and solution stability of the epoxy c