# US 2019/0172768 A1 · Active ester resin and cured product thereof

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- Number: US 2019/0172768 A1
- Document ID: US20190172768A1
- Status: Published application
- Kind: A1
- Application number: 16/313,269
- Filed: 2017-06-22
- Published: 2019-06-06
- Earliest claimed: 2016-07-06
- Assignees: DIC Corporation
- Applicants: DIC Corporation
- Inventors: Yutaka Satou; Tatsuya Okamoto; Akito Kawasaki
- Web page: https://patentgrep.com/patent/US20190172768A1

## CPC

- H10W 74/47: comprising organic materials, e.g. plastics or resins
- C08G 59/02: Polycondensates containing more than one epoxy group per molecule
- C08G 59/4223: {aromatic}
- C08G 63/133: Hydroxy compounds containing aromatic rings
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence)
- H05K 1/03: Use of materials for the substrate
- H10W 74/10: characterised by their shape or disposition
- H10W 74/40: characterised by their materials
- C08L 2203/206: use in coating or encapsulating of electronic parts
- H05K 1/0326: {containing O}
- H10W: GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS

## Abstract

Provided are an active ester resin capable of having low cure shrinkage and forming a cured product having a low dielectric loss tangent, a curable resin composition including the ester resin, a cured product of the resin composition, a printed wiring board, and a semiconductor encapsulating material. The active ester resin includes a product of reaction of essential raw materials including: a phenolic hydroxyl group-containing compound (A); a polynaphthol resin (B) having a molecular structure in which naphthol compound (b) moieties are linked with an aromatic ring- or cyclo ring-containing structural moiety (α); and an aromatic polycarboxylic acid or an acid halide thereof (C). Also provided are a curable resin composition including the ester resin, a cured product of the resin composition, a printed wiring board, and a semiconductor encapsulating material.

## Claims

### Claim 1

An active ester resin comprising a product of reaction of essential raw materials including:
a phenolic hydroxyl group-containing compound (A);
a polynaphthol resin (B) having a molecular structure in which naphthol compound (b) moieties are linked with an aromatic ring- or cyclo ring-containing structural moiety (α); and
an aromatic polycarboxylic acid or an acid halide thereof (C),
wherein the ratio between the number of moles of hydroxyl groups (AOH) in the phenolic hydroxyl group-containing compound (A) and the number of moles of hydroxyl groups (BOH) in the polynaphthol resin (B), [(AOH) (BOH)], is 10/90 to 75/25.

### Claim 2 (depends on 1)

The active ester resin according to claim 1, wherein the polynaphthol resin (B) has a molecular structure represented by the following structural formula (1):
wherein X represents an aromatic ring- or cyclo ring-containing structural moiety (α); R1's each independently represent any one of an aliphatic hydrocarbon group, an alkoxy group, a halogen atom, an aryl group, an aralkyl group, and a structural moiety (β) represented by the following structural formula (2):
wherein X represents an aromatic nucleus- or cyclo ring-containing structural moiety (α); R1's each independently represent any one of an aliphatic hydrocarbon group, an alkoxy group, a halogen atom, an aryl group, an aralkyl group, and a structural moiety (β) represented by structural formula (2), and each of R1's may be bonded to any carbon atom forming the naphthalene ring; m represents 0 or an integer f from 1 to 4; and n represents an integer from 1 to 10;
and each of R1's may be bonded to any carbon atom forming the naphthalene ring; m represents 0 or an integer from 1 to 4; and n represents an integer from 1 to 10.

### Claim 3 (depends on 2)

The active ester resin according to claim 2, wherein X in structural formulas (1) and (2) represents a structural moiety represented by any one of the following structural formulas (X-1) to (X-5):
wherein h represents 0 or 1; R2's each independently represent any one of an aliphatic hydrocarbon group, an alkoxy group, a halogen atom, an aryl group, and an aralkyl group; i represents 0 or an integer from 1 to 4; R3 represents a hydrogen atom or a methyl group; Y represents any one of an alkylene group having 1 to 4 carbon atoms, an oxygen atom, a sulfur atom, and a carbonyl group; and j represents an integer from 1 to 4.

### Claim 4 (depends on 1)

The active ester resin according to claim 1, wherein the polynaphthol resin (B) is a product of reaction of essential raw materials including: a naphthol compound (b) and a compound (x) represented by any one of the following structural formulas (x-1) to (x-5):
wherein h represents 0 or 1; R2's each independently represent any one of an aliphatic hydrocarbon group, an alkoxy group, a halogen atom, an aryl group, and an aralkyl group; i represents 0 or an integer from 1 to 4; Z represents any one of a vinyl group, a halomethyl group, a hydroxymethyl group, and an alkyloxymethyl group; Y represents any one of an alkylene group having 1 to 4 carbon atoms, an oxygen atom, a sulfur atom, and a carbonyl group; and j represents an integer from 1 to 4.

### Claim 5 (depends on 1)

A curable resin composition comprising: the active ester resin according to claim 1; and a curing agent.

### Claim 6 (depends on 5)

A cured product comprising a product obtained by curing the curable resin composition according to claim 5.

### Claim 7 (depends on 5)

A printed wiring board comprising a product produced using the curable resin composition according to claim 5.

### Claim 8 (depends on 5)

A semiconductor encapsulating material comprising the curable resin composition according to claim 5.

### Claim 9 (depends on 1)

The active ester resin according to claim 1, wherein the total of the number of moles of hydroxyl groups in the phenolic hydroxyl group-containing compound (A) and the number of moles of hydroxyl groups in the polynaphthol resin (B) is 0.95 to 1.05 moles based on 1 mole of the total amount of carboxyl groups or acid halide groups in the aromatic polycarboxylic acid or an acid halide thereof (C).

### Claim 10 (depends on 1)

The active ester resin according to claim 1, which comprises an ester compound (AC) of the phenolic hydroxyl group-containing compound (A) and the aromatic polycarboxylic acid or an acid halide thereof (C).

### Claim 11 (depends on 10)

The active ester resin according to claim 10, wherein the content of the ester compound (AC) is in the range of 1% to 30%.

### Claim 12 (depends on 2)

A curable resin composition comprising: the active ester resin according to claim 2; and a curing agent.

### Claim 13 (depends on 3)

A curable resin composition comprising: the active ester resin according to claim 3; and a curing agent.

### Claim 14 (depends on 4)

A curable resin composition comprising: the active ester resin according to claim 4; and a curing agent.

### Claim 15 (depends on 9)

A curable resin composition comprising: the active ester resin according to claim 9; and a curing agent.

### Claim 16 (depends on 10)

A curable resin composition comprising: the active ester resin according to claim 10; and a curing agent.

### Claim 17 (depends on 11)

A curable resin composition comprising: the active ester resin according to claim 11; and a curing agent.

### Claim 18 (depends on 12)

A cured product comprising a product obtained by curing the curable resin composition according to claim 12.

### Claim 19 (depends on 12)

A printed wiring board comprising a product produced using the curable resin composition according to claim 12.

### Claim 20 (depends on 12)

A semiconductor encapsulating material comprising the curable resin composition according to claim 12.