CN-121975100-A - Polyester resin, resin composition, curable resin composition, cured product, prepreg, circuit board, build-up film, semiconductor sealing material, and semiconductor device

Abstract

The invention provides a polyester resin, a resin composition, a curable resin composition, a cured product, a prepreg, a circuit board, a build-up film, a semiconductor sealing material and a semiconductor device. The invention provides a polyester resin, a resin composition, a curable resin composition and a cured product thereof, which can exhibit low dielectric loss tangent and small thermal expansion. As one of the solutions, a polyester resin is one formed of an aromatic polycarboxylic acid or a halide (a) thereof, a monohydroxyaromatic compound (B) and a polyhydroxyaromatic compound (C) containing fluorene in its structure.

Inventors

• KAWASAKI TAKASHI
• Jin Rongcan
• Po Yashu

Assignees

• DIC株式会社

Dates

Publication Date

20260505

Application Date

20250808

Priority Date

20241031

Claims (14)

1. 1. A polyester resin comprising an aromatic polycarboxylic acid or a halide (A) thereof, a monohydroxyaromatic compound (B) and a polyhydroxyaromatic compound (C) containing fluorene in its structure.
2. 2. The polyester resin according to claim 1, wherein the polyvalent hydroxyaromatic compound (C) is a compound formed of a compound represented by the general formula (1), a hydroxyaromatic compound represented by the general formula (2) and fluorene, wherein fluorene has no substituent at the 9-position, [ Chemical 1] In the formula, Ar is an aromatic ring group which may have a substituent, R 1 is independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, X is a leaving group and is a leaving group, R y is each independently a hydrogen atom or an aliphatic hydrocarbon, aryl, arylalkyl, alkoxy or halogen atom, or 2R y may form a ring together with the carbon atoms to which they are bonded, Z is each independently an integer of 0 to 5.
3. 3. The polyester resin according to claim 1, wherein the polyhydroxyaromatic compound (C) is a compound represented by the general formula (3-1), The terminal of the compound represented by the general formula (3-1) is blocked as in the general formula (3-2) by the aromatic polycarboxylic acid or the halide (A) and the monohydroxyaromatic compound (B), [ Chemical 2] In the formula, R 2 is independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, R 3 is each independently an aliphatic hydrocarbon group, an aryl group, an arylalkyl group, an alkoxy group or a halogen atom, Ar 1 is an aromatic ring group which may have a substituent, Ar 2 is an aromatic ring group which may have a substituent, Ar 3 is an aromatic ring group which may have a substituent, P is an integer of 1 or more, p+a is 1 or more, Each m is independently 0,1, 2, 3 or 4.
4. 4. The polyester resin according to claim 3, wherein Ar 1 is any one of, [ Chemical 3] * Indicating the bonding sites to other atoms.
5. 5. The polyester resin according to claim 3, wherein Ar 2 has a structure represented by the general formula (4) or (5), [ Chemical 4] In the formula, R q is each independently a hydrogen atom or an aliphatic hydrocarbon group, aryl group, arylalkyl group, alkoxy group or halogen atom, T is each independently an integer of 0 to 4, U is each independently an integer of 0 to 6, * Indicating the bonding sites to other atoms.
6. 6. The polyester resin according to claim 3, wherein Ar 3 has a structure represented by the general formula (6) or (7), [ Chemical 5] In the formula, R q is each independently a hydrogen atom or an aliphatic hydrocarbon group, aryl group, arylalkyl group, alkoxy group or halogen atom, V is each independently an integer of 0 to 5, W is each independently an integer of 0 to 7, * Indicating the bonding sites to other atoms.
7. 7. A resin composition comprising the polyester resin according to any one of claims 1 to 6.
8. 8. A curable resin composition comprising the polyester resin according to any one of claims 1 to 6 and an epoxy resin.
9. 9. A cured product of the curable resin composition according to claim 8.
10. 10. A prepreg comprising a reinforcing substrate and a prepreg impregnated with the curable resin composition according to claim 8.
11. 11. A circuit board comprising the prepreg according to claim 10 and a copper foil.
12. 12. A build-up film comprising the curable resin composition according to claim 8.
13. 13. A semiconductor sealing material comprising the curable resin composition according to claim 8.
14. 14. A semiconductor device comprising the cured product of the semiconductor sealing material according to claim 13.

Description

Polyester resin, resin composition, curable resin composition, cured product, prepreg, circuit board, build-up film, semiconductor sealing material, and semiconductor device Technical Field The present invention relates to a polyester resin, a resin composition, a curable resin composition, a cured product, a prepreg, a circuit board, a build-up film, a semiconductor sealing material, and a semiconductor device. Background Epoxy resin compositions containing an epoxy resin and a curing agent thereof as essential components are widely used for electronic parts such as semiconductors and multilayer printed boards because cured products thereof exhibit excellent heat resistance and insulation properties. In the field of sealing materials and substrate materials, in recent years, the speed and frequency of signals in various electronic devices have been increased. In view of such a background, with the increase in signal speed and frequency, a material having a low dielectric loss tangent is demanded as a parameter indicating transmission loss. Prior art literature Patent literature Patent document 1 Japanese patent application laid-open No. 2004-169021 Disclosure of Invention Problems to be solved by the invention In response to these demands, as a material capable of realizing a low dielectric constant/low dielectric loss tangent, a technique using an active ester compound as a curing agent for epoxy resins is known (for example, patent document 1), but further realization of a low dielectric loss tangent is desired. In addition, in electronic component applications, small thermal expansion is also desired. The thermal expansion is small, so that warpage during mounting can be suppressed, and connection reliability can be improved. Accordingly, an object of the present disclosure is to provide a polyester resin, a resin composition, a curable resin composition, and a cured product thereof, which can exhibit a low dielectric loss tangent and a small thermal expansion. Means for solving the problems The polyester resin of the present invention is a polyester resin formed from an aromatic polycarboxylic acid or a halide (a) thereof, a monohydroxyaromatic compound (B) and a polyhydroxyaromatic compound (C) containing fluorene in its structure. This can exhibit a low dielectric loss tangent and reduce thermal expansion. In one embodiment of the polyester resin of the present invention, the polyvalent hydroxy aromatic compound (C) is a compound composed of a compound represented by the general formula (1), a hydroxy aromatic compound represented by the general formula (2) and fluorene (wherein, there is no substituent at the 9-position), [ Chemical 1] In the formula, Ar is an aromatic ring group which may have a substituent, R 1 is independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, X is a leaving group and is a leaving group, R y is each independently a hydrogen atom or an aliphatic hydrocarbon, aryl, arylalkyl, alkoxy or halogen atom, or 2R y may form a ring together with the carbon atoms to which they are bonded, Z is each independently an integer of 0 to 5. In one embodiment of the polyester resin of the present invention, the polyhydroxyaromatic compound (C) is a compound represented by the general formula (3-1), the terminal is blocked by an aromatic polycarboxylic acid or a halide (A) thereof, and the monohydroxyaromatic compound (B) is blocked as represented by the general formula (3-2), [ Chemical 2] In the formula, R 2 is independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, R 3 is each independently an aliphatic hydrocarbon group, an aryl group, an arylalkyl group, an alkoxy group or a halogen atom, Ar 1 is an aromatic ring group which may have a substituent, Ar 2 is an aromatic ring group which may have a substituent, Ar 3 is an aromatic ring group which may have a substituent, P is an integer of 1 or more, p+a is 1 or more, Each m is independently 0,1, 2, 3 or 4. In one embodiment of the polyester resin of the present invention, ar 1 is any one of, [ Chemical 3] * Represents a bonding site to bond with another atom of the general formula (3-1). In one embodiment of the polyester resin of the present invention, ar 2 has a structure represented by the general formula (4) or (5), [ Chemical 4] In the formula, R q is each independently a hydrogen atom or an aliphatic hydrocarbon group, aryl group, arylalkyl group, alkoxy group or halogen atom, T is each independently an integer of 0 to 4, U is each independently an integer of 0 to 6, * Represents a bonding site to bond with another atom of the general formula (3-1). In one embodiment of the polyester resin of the present invention, ar 3 has a structure represented by the general formula (6) or (7), [ Chemical 5] In the formula, R q is each independently a hydrogen atom or an aliphatic hydrocarbon group, aryl group, arylalkyl group, alkoxy group or halogen atom, V is each independ