IP Library Granted Patent US 12674019
Granted Patent B2
US 12674019 · App. 18/296,042 · Granted Jul 7, 2026

Ester compound and resin composition

Inventor: Ichiro Ogura (Kawasaki, JP)
Assignee: AJINOMOTO CO., INC.
C08G59/4276C08G59/06C08G63/197C08G63/916H10W70/685H10W74/473
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Quick Facts
Patent No.
US 12674019
App. No.
18/296,042
Granted
Jul 7, 2026
Kind
B2
Abstract

Compounds containing, in one molecule thereof, a structure represented by formula (1), a structure represented by formula (2), and a structure represented by formula (3) (all the symbols are those described in the specification). are useful as epoxy resin curing agents.

Claims (93)

1 . A compound comprising, in one molecule thereof,

a structure represented by formula (1):

wherein

a ring A 1 and a ring A 2 each independently represent an aromatic ring optionally having a substituent group;

X represents a single bond or a divalent organic group;

a represents 0 or 1; and

*1 indicates a bonding site to a carbonyl carbon atom to form an ester structure by bonding to the carbonyl carbon atom;

a structure represented by formula (2):

wherein

a ring B represents an aromatic ring substituted with one or more fluorine atoms; and

*2 indicates a bonding site with a carbonyl carbon atom to form an ester structure by bonding to the carbonyl carbon atom; and

a structure represented by formula (3):

wherein

Y represents a divalent organic group; and

*3 indicates a bonding site with an oxygen atom to form an ester structure by bonding to the oxygen atom.

2 . The compound according to claim 1 , wherein the ring B is an aromatic ring substituted with two or more fluorine atoms.

3 . The compound according to claim 1 , wherein the structure represented by the formula (1) comprises 3 or more fluorine atoms in one unit of the structure.

4 . The compound according to claim 1 , wherein the compound is represented by formula (A1):

wherein

the ring A 1 and the ring A 2 each independently represent an aromatic ring optionally having a substituent group;

each of the ring B independently represents an aromatic ring substituted with one or more fluorine atoms;

each X independently represents a single bond or a divalent organic group;

each Y independently represents a divalent organic group;

each a independently represents 0 or 1; and

n represents an integer of 1 or more.

5 . The compound according to claim 4 , wherein the compound is represented by formula (A2):

wherein

the ring A 1 and the ring A 2 each independently represent an aromatic ring optionally having a substituent group;

each of the ring B independently represents an aromatic ring substituted with one or more fluorine atoms;

each X 1 independently represents a single bond, —C(R x ) 2 —, —O—, —CO—, —S—, —SO—, —SO 2 —, —CONH—, or —NHCO—;

each R x independently represents a hydrogen atom, an alkyl group optionally having a substituent group, or an aryl group optionally having a substituent group;

each of the ring X 2 independently represents an aromatic ring optionally having a substituent group or a non-aromatic ring optionally having a substituent group;

each of the ring Y 1 independently represents an aromatic carbon ring optionally having a substituent group;

each a independently represents 0 or 1;

each b independently represents an integer of 0 to 3; and

n represents an integer of 1 or more.

6 . The compound according to claim 1 , wherein a content of the fluorine atom is 28% or more by mass.

7 . An epoxy resin curing agent comprising the compound according to claim 1 .

8 . A method for producing a compound comprising, in one molecule thereof,

a structure represented by formula (1):

wherein

a ring A 1 and a ring A 2 each independently represent an aromatic ring optionally having a substituent group;

X represents a single bond or a divalent organic group;

a represents 0 or 1; and

*1 indicates a bonding site to a carbonyl carbon atom to form an ester structure by bonding to the carbonyl carbon atom;

a structure represented by formula (2):

wherein

a ring B represents an aromatic ring substituted with one or more fluorine atoms; and

*2 indicates a bonding site with a carbonyl carbon atom to form an ester structure by bonding to the carbonyl carbon atom; and

a structure represented by formula (3):

wherein

Y represents a divalent organic group; and

*3 indicates a bonding site with an oxygen atom to form an ester structure by bonding to the oxygen atom,

the method comprising reacting a mixture comprising a compound represented by formula (B1):

wherein all the symbols are the same as those described above,

a compound represented by formula (C1):

wherein all the symbols are the same as those described above, and

a compound represented by formula (D1-1) or (D1-2):

wherein Hal represents a halogen atom; other symbols are the same as those described above, or a salt thereof.

9 . A product obtained by reacting a mixture comprising

a compound represented by formula (B1):

wherein a ring A 1 and a ring A 2 each independently represent an aromatic ring optionally having a substituent group; X represents a single bond or a divalent organic group; and a represents 0 or 1;

a compound represented by formula (C1):

wherein a ring B represents an aromatic ring substituted with one or more fluorine atoms; and

a compound represented by formula (D1-1) or (D1-2):

wherein Hal represents a halogen atom; Y represents a divalent organic group, or a salt thereof.

10 . A resin composition comprising an epoxy resin and a compound comprising, in one molecule thereof,

a structure represented by formula (1):

wherein

a ring A 1 and a ring A 2 each independently represent an aromatic ring optionally having a substituent group;

X represents a single bond or a divalent organic group;

a represents 0 or 1; and

*1 indicates a bonding site to a carbonyl carbon atom to form an ester structure by bonding to the carbonyl carbon atom;

a structure represented by formula (2):

wherein

a ring B represents an aromatic ring substituted with one or more fluorine atoms; and

*2 indicates a bonding site with a carbonyl carbon atom to form an ester structure by bonding to the carbonyl carbon atom; and

a structure represented by formula (3):

wherein

Y represents a divalent organic group; and

*3 indicates a bonding site with an oxygen atom to form an ester structure by bonding to the oxygen atom.

11 . The resin composition according to claim 10 , further comprising an inorganic filler.

12 . The resin composition according to claim 11 , wherein a content of the inorganic filler is 60% or more by mass relative to 100% by mass of nonvolatile components in the resin composition.

13 . The resin composition according to claim 10 , wherein the resin composition is to form an insulating layer of a printed wiring board.

14 . The resin composition according to claim 10 , wherein the resin composition is to encapsulate a semiconductor chip.

15 . A cured product of a resin composition according to claim 10 .

16 . A sheet-like laminate material comprising a resin composition according to claim 10 .

17 . A resin sheet comprising:

a support; and

a resin composition layer formed on the support, the resin composition layer being formed of a resin composition according to claim 10 .

18 . A printed wiring board comprising an insulating layer formed of a cured product of a resin composition according to claim 10 .

19 . A semiconductor device comprising a printed wiring board according to claim 18 .

20 . The semiconductor device according to claim 19 , wherein the semiconductor device is a Fan-Out semiconductor device.