# US 8,784,682 B2 · Thermosetting composition and printed circuit board using the same

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- Number: US 8,784,682 B2
- Document ID: US8784682B2
- Status: Granted
- Kind: B2
- Application number: 13/048,147
- Filed: 2011-03-15
- Published: 2011-09-29
- Granted: 2014-07-22
- Earliest claimed: 2010-03-29
- Assignees: Samsung Electro-Mechanics Co., Ltd.; Samsung Fine Chemicals Co., Ltd.
- Applicants: Myung-Sup Jung; Jae-Jun Lee
- Inventors: Myung-Sup Jung; Jae-Jun Lee
- Web page: https://patentgrep.com/patent/US8784682B2

## CPC

- C09K 19/3809: {Polyesters; Polyester derivatives, e.g. polyamides}
- C09K 19/322: {Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring}
- C09K 19/3483: {the heterocyclic ring being a non-aromatic ring}
- H05K 1/0353: {consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement}
- H05K 1/0326: {containing O}
- H05K 1/0366: {reinforced, e.g. by fibres, fabrics (H05K1/036 takes precedence)}
- H05K 2201/0141: Liquid crystal polymer [LCP]
- H05K 2201/015: Fluoropolymer, e.g. polytetrafluoroethylene [PTFE]
- H05K 2201/0212: Resin particles
- Y10T 428/24612: Composite web or sheet
- Y10T 428/31678: Of metal
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Disclosed are a thermosetting composition including a liquid crystal oligomer, a bismaleimide-based compound, an epoxy compound, and a fluorinated polymer resin powder. A resin cured product, board, and storage medium each include the thermosetting composition.

## Claims

### Claim 1

A thermosetting composition comprising:
a liquid crystal oligomer; a bismaleimide-based compound; an epoxy compound; and a fluorinated polymer resin powder,
wherein the liquid crystal oligomer comprises a backbone represented by the following Chemical Formula 1:
wherein, in Chemical Formula 1, R1 is represented by the following Chemical Formula 2, R2 is represented by the following Chemical Formula 6, and n and m are independently integers of from 1 to 100:
*—X1—Ar1—Y1—* Chemical Formula 2
wherein, in Chemical Formula 2, X1 and Y1 are independently O, NR″, or C(═O), where R″ is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
Ar1 includes a divalent aromatic organic group or aliphatic cyclic group represented by any of the following Chemical Formula 3-1 to 3-11, where at least one hydrogen in the cycle group is substituted or unsubstituted:
wherein, in Chemical Formula 3-5 and 3-10, A1 is a single bond, a divalent heteroatom group, or a divalent aliphatic organic group, aromatic organic group, or a combination comprising at least one of the foregoing:
*—X2—Ar3—Y2—* Chemical Formula 6
wherein, in Chemical Formula 6, X2 and Y2 are independently O, NR″, or C(═O), where R″ is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination comprising at least one of the foregoing, and
Ar3 includes at least one of a divalent aromatic organic group, aliphatic cyclic group, or a combination comprising at least one of the foregoing represented by any of the following Chemical Formula 7-1 to7-9:
wherein, in Chemical Formula 7-5, A2 is a divalent heteroatom group, aliphatic organic group, aromatic organic group, or a combination comprising at least one of the foregoing, and wherein, in Chemical Formulae 7-6, 7-7, 7-8, and 7-9, Rc and Rd are independently a C1 to C5 alkyl group or a halogen.

### Claim 2 (depends on 1)

The thermosetting composition of claim 1, wherein R1 as a divalent aromatic or aliphatic ring structural unit is linked in an ortho position or a meta position where the aromatic ring is a 6-membered ring, or at the 1,2- or 1,3 position where R1 is an aliphatic ring structural unit.

### Claim 3 (depends on 1)

The thermosetting composition of claim 1, wherein A1 of Chemical Formula 3-5 and 3-10 is selected from O, S, C(═O), S(═O), SO2, a substituted or unsubstituted C2 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkoxylene group, a substituted or unsubstituted C2 to C20 alkoxyleneoxy group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aryleneoxy group, a substituted or unsubstituted C6 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 heteroaryleneoxy group, a linker represented by the following Chemical Formula 3a, a linker represented by the following Chemical Formula 3b, or a combination comprising at least one of the foregoing:
wherein, in Chemical Formula 3b, D1 is O, S, C(═O), S(═O), SO2, a linear or branched C1 to C20 alkylene group, or a combination comprising at least one of the foregoing.

### Claim 4 (depends on 1)

The thermosetting composition of claim 1, wherein A2 in Chemical Formula 7-5 is N2, O, S, C(═O), S(═O), SO2, a substituted or unsubstituted C2 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkoxylene group, a substituted or unsubstituted C2 to C20 alkoxyleneoxy group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aryleneoxy group, a substituted or unsubstituted C6 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 heteroaryleneoxy group, a linker represented by Chemical Formulae 8a and 8b, or a combination comprising at least one of the foregoing:
wherein, in Chemical Formulae 8a and 8b, Ra and Rb are independently hydrogen, a halogen, a C1 to C5 alkyl group, or a C1 to C5 haloalkyl group.

### Claim 5 (depends on 1)

The thermosetting composition of claim 1, wherein m/(n+m+2) in Chemical Formula 1 is greater than about 0.05 and less than or equal to about 0.6.

### Claim 6 (depends on 1)

The thermosetting composition of claim 1, wherein the liquid crystal oligomer comprises a hydroxy group, an amine group, a carboxyl group, an acetyl group, or a thiol group at each terminal end, and at least one terminal end includes an organic group including a hydroxy group.

### Claim 7 (depends on 6)

The thermosetting composition of claim 6, wherein the liquid crystal oligomer comprises a liquid crystal oligomer represented by the following Chemical Formulae 11a to 11d:
HO—(R1)m—(R2)n—CO—CH3 Chemical Formula 11a
HO—(R1)m—(R2)n—OH Chemical Formula 11b
HO—(R1)m—(R2)n—COOH Chemical Formula 11c
HO—(R1)m—(R2)n—NH2 Chemical Formula 11d
wherein, in Chemical Formulae 11a to 11d, R1 is a structural unit represented by any of Chemical Formulae 4-1 to 4-3, R2 is a structural unit represented by any of Chemical Formulae 9-1 to 9-6, and m and n are integers of from 1 to 100:
wherein, in Chemical Formula 4-1 to 4-3, Ar2 is selected from a group of the following Chemical Formulae 5-1 to 5-11:
wherein, in Chemical Formulae 9-1 to 9-6, Ar4 is selected from groups represented by the following Chemical Formulae 10-1 to 10-11:
wherein, in Chemical Formulae 10-2, 10-3, 10-4, 10-8, 10-9, and 10-11, Rc and Rd are independently hydrogen, a C1 to C5 alkyl group, or a halogen.

### Claim 8 (depends on 6)

The thermosetting composition of claim 6, wherein the liquid crystal oligomer is selected from the compounds represented by the following Chemical Formulae 13a-13e, 14a-14e, 15a-15e, 16a-16e, or 17a-17e:
wherein, in the above Chemical Formulae, m, n, m1, m2, m3, n1, n2, n3, and n4 are integers of from 1 to 100, in Chemical Formulae 13a, 13b, 13d, 14a, 14b, 14d, 15a, 15b, 15d, 16a, 16b, and 16d, 1≦n1+n2+n3+n4≦100, in Chemical Formulae 13c, 13e, 14c, 14e, 15c, 15e, 16c, and 16e, 1≦n1+n2≦100, in Chemical Formulae 17a, 17c, and 17e, 1≦m1+m2+m3≦100, and in Chemical Formulae 17b and 17d, 1≦m1+m2+m3≦100.

### Claim 9 (depends on 1)

The thermosetting composition of claim 1, wherein the liquid crystal oligomer further independently comprises maleimide, nadimide, citraconimide, tetrahydrophthalimide, acetylene, propargyl ether, benzocyclobutene, cyanate, a substituent thereof, a derivative thereof, or a combination comprising at least one of the foregoing at each terminal end or on a side chain.

### Claim 10 (depends on 9)

The thermosetting composition of claim 9, wherein the liquid crystal oligomer comprises one selected from the compound represented by Chemical Formulae 18a to 18k:
wherein, in Chemical Formulae 18a to 18k, m1, m2, n1, and n2 are independently integers of from 1 to 50.

### Claim 11 (depends on 1)

The thermosetting composition of claim 1, wherein the liquid crystal oligomer has a number average molecular weight of from about 500 to about 9,000.

### Claim 12 (depends on 1)

The thermosetting composition of claim 1, wherein the bismaleimide-based cross-linking agent comprises a bismaleimide-based compound represented by the following Chemical Formula 19:
wherein, in the above Chemical Formula 19, R3 and R4 are independently H or CH3, and
A is at least one of a structural unit selected from a divalent linker including a C2 to C18 alkylene group or an aromatic group, a linker represented by the following Chemical Formula 19a, or a combination comprising at least one of the foregoing:
wherein, in the above Chemical Formula 19a, W is O, S, C(═O), S(═O), SO2, a linear or branched C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkoxylene group, a substituted or unsubstituted C2 to C20 alkoxyleneoxy group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aryleneoxy group, a substituted or unsubstituted C6 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 heteroaryleneoxy group, a linker represented by the following Chemical Formula 19b, or a combination comprising at least one of the foregoing:
*—Z1—Ar5—Z2—* Chemical Formula 19b
wherein, in the above Chemical Formula 19b, Z1 and Z2 are independently, O, S, C(═O), S(═O), SO2, C(═O)NH, or C(═O)O, and Ar5 is selected from linkers represented by any of the following Chemical Formulae 19c-1 19c-6:

### Claim 13 (depends on 1)

The thermosetting composition of claim 1, wherein the bismaleimide-based compound comprises one selected from the compounds represented by the following Chemical Formulae 20a to 20r:

### Claim 14 (depends on 1)

The thermosetting composition of claim 1, wherein the fluorinated polymer resin powder comprises a fluorinated resin or a fluorinated resin copolymer.

### Claim 15 (depends on 1)

The thermosetting composition of claim 1, wherein the fluorinated resin powder has an average particle diameter of from about 0.02 μm to 500 μm.

### Claim 16 (depends on 1)

The thermosetting composition of claim 1, wherein the fluorine-based polymer resin powder comprises poly(tetrafluoroethylene, poly(ethylene-co-tetrafluoroethylene), poly(ethylene-co-chlorotrifluoroethylene), poly(vinylidene fluoride), poly(vinylidene fluoride-co-hexafluoropropylene), poly(tetrafluoroethylene-co-hexafluoropropylene), polychlorotrifluoroethylene, or a combination comprising at least one of the foregoing.

### Claim 17 (depends on 1)

The thermosetting composition of claim 1, wherein the thermosetting composition comprises about 5 parts by weight to about 95 parts by weight of the liquid crystal oligomer, about 5 to about 100 parts by weight of the bismaleimide-based compound, and about 5 to about 100 parts by weight of the epoxy compound based on 100 parts by weight of the organic solvent.

### Claim 18 (depends on 1)

A resin cured product comprising a cross-linked product of the thermosetting composition according to claim 1.

### Claim 19 (depends on 18)

A board comprising a resin cured product according to claim 18.

### Claim 20 (depends on 19)

The board of claim 19, wherein the resin cured product further comprises a reinforcing material, wherein the resin cured product is invaded into the reinforcing material and attached thereto, or disposed on the surface of the reinforcing material surface.

### Claim 21 (depends on 19)

The board of claim 19, wherein the board further comprises a metal foil bonded to at least one side of the resin cured product.

### Claim 22 (depends on 21)

The board of claim 21, wherein the metal foil bonded to at least one side of the resin cured product is patterned.

### Claim 23 (depends on 19)

A storage medium comprising the board according to claim 19; and
a memory chip electrically connected to the board.

### Claim 24 (depends on 1)

The thermosetting composition of claim 1, wherein the epoxy compound includes two or more of a structure represented by Chemical Formula 21:
wherein, in Chemical Formula 21, Q is O, S, P(R)3, or NR, provided that when Q is O or S, n is 1, and when Q is P(R)3 or NR, n is 1 or 2, and wherein R is hydrogen or a C1 to C20 alkyl group.