JP-7855946-B2 - Resin composition, cured product, insulating material, and resist member

Inventors

• 山田 駿介
• 下野 智弘
• キム ヨンチャン

Assignees

• ＤＩＣ株式会社

Dates

Publication Date

20260511

Application Date

20220630

Claims (5)

1. an indane ring-containing compound (A) having a structural unit represented by the following general formula (1a), wherein at least one terminal site bonded to the structural unit is an alkenyl group, A resin (B) having acidic groups and polymerizable unsaturated groups, It contains a photopolymerization initiator and The mass ratio of the solid content of the indan ring-containing compound (A) and the resin (B) having the acid group and polymerizable unsaturated group [(A)/(B)] is in the range of 1/100 to 100/100. Resin composition. (In the above general formula (1a), R 11 , R 12 , and R 13 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n 12 represents the number of repeating units.)
2. The indane ring-containing compound (A) is given by the following general formula (1b): (In the above general formula (1b), R 11 , R 12 , and R 13 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.) Q11 , Q12 , L11 , and L12 each independently represent a single bond or an alkylene group having 1 to 8 carbon atoms, provided that the -CH2- CH2- in the alkylene group may be substituted with -CH=CH-. P11 and P12 each independently represent a hydrogen atom, a polar group, an alkyl group having 1 to 6 carbon atoms which may be substituted with the polar group, an alkenyl group having 2 to 10 carbon atoms, or the following general formula (2), M11 and M12 each independently represent a single bond or the following general formula (3): n 12 represents the average number of repeating units, while n 11 and n 13 independently represent values from 0 to 20. However, at least one of P11 and P12 is an alkenyl group having 2 to 10 carbon atoms. [In the above general formula (2), R 15 independently represents an amino group, a fluoroalkyl group, or an alkyl group having 1 to 3 carbon atoms, and n 2 represents an integer between 0 and 4.] [In the above general formula (3), R 16 independently represents an amino group, a fluoroalkyl group, or an alkyl group having 1 to 3 carbon atoms, and n 3 represents an integer between 0 and 4.] The resin composition according to claim 1, represented by the general formulas (2) and (3), wherein the asterisk (*) in the general formulas (2) and (3) represents bonding with other atoms.
3. A cured product of the resin composition according to claim 1 or 2.
4. An insulating material characterized by using the resin composition described in claim 2 .
5. A resist member characterized by using the resin composition described in claim 2 .

Description

This disclosure relates to resin compositions, and cured products, insulating materials, and resist members obtained from resin compositions. Solder resist is widely used as a material to form a protective film that prevents solder from adhering to areas other than the mounting area when soldering electronic components onto printed circuit boards, and to semi-permanently prevent oxidation or corrosion of the wiring. As a technique for forming patterns on such solder resist, the alkaline-developable liquid photoresist method, which can accurately form fine patterns, is the mainstream method, particularly due to environmental considerations. Furthermore, in order to achieve the high density of electronic components in recent years, printed circuit boards have been steadily becoming smaller, more multilayered, and single-board, and the mounting method has also shifted to surface mount technology (SMT). As a result, there is an increasing demand for solder resist films to be finer, have a higher Tg, higher resolution, higher precision, and higher reliability. Moreover, with the increasing speed of transmitted signals, the solder resist market is also demanding technologies that exhibit low dielectric constant and low dielectric loss tangent to reduce time delay for the use of high frequencies (gigahertz band). Here, since the resist film requires various properties, including low dielectric properties, it is essential to manufacture it using appropriate materials that meet these properties. In this regard, hydrocarbon resins are one type of resin that tends to have excellent low dielectric properties in cured products. For example, Patent Document 1 discloses a hydrocarbon resin made of a polyindane derivative having a predetermined indane skeleton, which has a low dielectric constant even without the introduction of pores and is suitable as an interlayer insulating film material. Japanese Patent Publication No. 2007-311732 Figure 1 shows the GPC chart of the indane ring-containing compound (A-1) obtained in Synthesis Example 1.Figure 2 shows the GPC chart of the indane ring-containing compound (A-2) obtained in synthesis example 2.Figure 3 shows the GPC chart of the indane ring-containing compound (A-3) obtained in synthesis example 3.Figure 4 shows the GPC chart of the indan ring-containing compound (A-4) obtained in synthesis example 4.Figure 5 shows the GPC chart of the indane ring-containing compound (A-5) obtained in synthesis example 5.Figure 6 shows the FD-MS chart of the indane ring-containing compound (A-1) obtained in Synthesis Example 1.Figure 7 shows the 13C -NMR chart of the indan ring-containing compound (A-1) obtained in Synthesis Example 1. The embodiments of this disclosure (hereinafter referred to as "these embodiments") will be described in detail below, but this disclosure is not limited to the following description and can be implemented in various modifications within the scope of its gist. Unless otherwise specified in this specification, the following terms may be applied: "term" In this specification, "developability" refers to the contrast between exposed and unexposed areas. Generally, one of the causes of decreased developability is that when a curable composition (for example, the resin composition of this embodiment) applied to a substrate is exposed after drying, the unexposed areas remain after development (for example, after alkaline development) due to heating during drying, resulting in a decrease in contrast. Therefore, in this invention, as described in the Examples section below, alkaline developability is evaluated using a drying control range (minutes) as one example of an indicator of developability. This drying control range defines a range of drying conditions (drying time, drying temperature, etc.) in which development defects are less likely to occur due to coating drying, etc. The longer the drying time for development, the wider the margin due to drying, and the easier it is to control the manufacturing process. Therefore, if development residue is less likely to occur even if the drying time is extended (i.e., if the drying control range is large), it is considered that excellent developability can be achieved. In this specification, "reaction raw material" refers to a compound used to obtain a target compound by a chemical reaction such as combination or decomposition, and which partially constitutes the chemical structure of the target compound. Substances that act as aids to chemical reactions, such as solvents and catalysts, are excluded. In particular, in this specification, "reaction raw material" refers to a precursor for obtaining an indan ring-containing compound (A) (including a mixture containing one or more indan ring-containing compounds (A)) by a chemical reaction. In this specification, the "aromatic group" preferably has an aromatic ring having 3 to 30 carbon atoms, and more preferably has an aromatic ring having 4 to 26 carbon atoms. Furthermore,