# US 11,028,059 B2 · Oxazine compound, composition and cured product

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- Number: US 11,028,059 B2
- Document ID: US11028059B2
- Status: Granted
- Kind: B2
- Application number: 15/781,801
- Filed: 2016-11-24
- Published: 2018-12-20
- Granted: 2021-06-08
- Earliest claimed: 2015-12-08
- Assignees: DIC Corporation
- Applicants: DIC Corporation
- Inventors: Tomohiro Shimono; Junji Yamaguchi; Masato Otsu; Kazuo Arita
- Web page: https://patentgrep.com/patent/US11028059B2

## CPC

- C07D 265/16: with only hydrogen or carbon atoms directly attached in positions 2 and 4
- B32B 5/02: characterised by structural features of a {fibrous or filamentary} layer {(layer formed of metallic wires B32B15/02; layer formed of natural mineral fibres B32B19/02; layer formed of wood fibres B32B21/02)}
- B32B 15/08: of synthetic resin
- B32B 15/14: next to a fibrous or filamentary layer
- B32B 15/20: comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)}
- B32B 27/42: comprising condensation resins of aldehydes, e.g. with phenols, ureas or melamines
- C08G 61/122: {derived from five- or six-membered heterocyclic compounds, other than imides}
- C08J 5/243: {using carbon fibres}
- C08J 5/249: {characterised by the additives used in the prepolymer mixture}
- C08K 3/013: Fillers, pigments or reinforcing additives
- H05K 1/0204: {using means for thermal conduction connection in the thickness direction of the substrate (H05K1/0207 takes precedence)}
- H05K 1/03: Use of materials for the substrate
- H05K 1/0373: {containing additives, e.g. fillers (H05K1/036 takes precedence)}
- H10W 40/251: {Organics}
- H10W 70/695: Organic materials
- H10W 74/10: characterised by their shape or disposition
- H10W 74/40: characterised by their materials
- B32B 2260/021: Fibrous or filamentary layer
- B32B 2260/046: Synthetic resin
- B32B 2457/08: PCBs, i.e. printed circuit boards
- C08G 2261/12: Copolymers
- C08G 2261/3245: containing nitrogen and oxygen as heteroatoms
- C08J 2365/00: Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08J2307/00 - C08J2357/00, C08J2361/00 take precedence); Derivatives of such polymers
- H10W 74/473: {containing a filler}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H10W: GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10

## Abstract

The present invention provides an oxazine compound having a specific structure, which contains a group having an aromatic ring structure and a plurality of specified carbon-carbon triple bond structure. The present invention further provides a composition containing the oxazine compound having a specific structure of the present invention, a cured product containing the composition, and a laminate having a layer of the cured product. The present invention further still provides a composition for a heat-resistant material and a composition for an electronic material, which contain the composition containing the oxazine compound of the present invention.

## Claims

### Claim 1

An oxazine compound comprising:
a structure which is represented by General Formula (1-1):
wherein, in General Formula (1-1),
Ar1 represents a substituted or unsubstituted aromatic group,
a ring A represents a substituted or unsubstituted aromatic ring,
each R1 is indenpendtly a functional group represented by General Formula (2)
a1-X1—Y1—X2—≡—R2 (2),
and R3 and R4 each independently represent a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms;
and wherein, in General Formula (2),
X1, X2, and Y1 each independtly represent a single bond or a divalent linking group,
R2 represents a hydrogen atom, a hydrocarbon group, or a hydrocarbon group in which one or more hydrogen atoms contained in the hydrocarbon group are substituted with any one of a hydroxyl group, an alkoxy group, and a halogen atom,
and a1 represents a bonding point to the oxazinc compound (1-1);
and wherein the divalent linking group in each of X1, X2, and Y1 in General Formula (2) is an oxygen atom; a divalent hydrocarbon group; a divalent group in which one or more hydrogen atoms contained in a divalent hydrocarbon group are substituted with a hydroxyl group, an alkoxy group, or a halogen atom; a carbonyl group; an ester group; an amide group; an imino group; an azo group; a sulfide group; a sulfone group; or a divalent linking group formed by combining two or more these groups.

### Claim 2 (depends on 1)

The oxazine compound according to claim 1, wherein the aromatic ring of ring A is a benzene ring or a naphthalene ring.

### Claim 3 (depends on 1)

A composition comprising the oxazine compound according to claim 1.

### Claim 4 (depends on 3)

The composition according to claim 3, further comprising a reactive compound.

### Claim 5 (depends on 3)

The composition according to claim 3, further comprising a filler.

### Claim 6 (depends on 3)

The composition according to claim 3, further comprising a fibrous substrate.

### Claim 7 (depends on 3)

A cured product, which is obtained by curing the composition according to claim 3.

### Claim 8 (depends on 7)

A laminate comprising:
a base material; and
a layer of the cured product according to claim 7.

### Claim 9 (depends on 7)

A heat-resistant member comprising the cured product according to claim 7.

### Claim 10 (depends on 7)

An electronic member comprising the cured product according to claim 7.

### Claim 11 (depends on 3)

A semiconductor sealing material comprising the composition according to claim 3.

### Claim 12 (depends on 6)

A prepreg comprising the composition according to claim 6.

### Claim 13 (depends on 12)

A circuit board comprising the prepreg according to claim 12 and a copper foil layer.

### Claim 14 (depends on 8)

A build-up substrate comprising the laminate of claim 8.