Adhesive film of quinoline polymer and bismaleimide

Details Adhesive film of quinoline polymer and bismaleimide Adhesive film of quinoline polymer and bismaleimide

1999-10-07

2002-10-08

Sellers, Robert E. L. (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

C524S611000, C525S066000, C525S186000, C525S480000, C525S523000, C525S530000

Reexamination Certificate

active

06462148

ABSTRACT:

TECHNICAL FIELD
This invention relates to a resin composition comprising a polymer containing a quinoline ring and a thermosetting resin, an insulating material constituted by said resin composition and an adhesive film, particularly to a resin composition for an interlayer insulation film excellent in electric characteristics, molding property and adhesiveness with a material to be adhered, and has a low moisture absorption ratio, an insulating material constituted by said resin composition and an adhesive film.
BACKGROUND ART
As an interlayer insulating membrane for electronic parts, a dehydration-condensation type polyimide resin polyimide resin has heretofore been used (Japanese Provisional Patent Publication No. 222444/1988). Whereas the above-mentioned polyimide resin is excellent in heat resistance, mechanical characteristics, etc., a polyamic acid varnish which is a precursor thereof is required to be stored in a refrigerator at −5° C. or less whereby it is insufficient in storage stability. Also, it requires curing at a high temperature of 350° C. or higher and the cured product has the problem that it has a large moisture absorption ratio. Moreover, when copper is used which is a representative conductive material and inferior in adhesiveness with a material to be adhered, it has a problem that it reacts during heating or the like, and has a problem in the point of reliability.
As a measure of the above, an investigation of a polymer containing a quinoline ring has been made in recent years, and synthetic methods thereof have been described in U.S. Pat. No. 4,000,187, U.S. Pat. No. 5,247,050, U.S. Pat. No. 5,247,050, etc. Also, as the other conventional example thereof, there may be mentioned Japanese Provisional Patent Publication No. 25286/1987.
A polymer containing a quinoline ring has low specific permittivity and dielectric dissipation factor, excellent in electric characteristics, low moisture absorption ratio and good stability at high temperatures, but it involves the problems that adhesiveness with a material to be adhered is bad, molding property is poor, and it dissolved in a solvent so that a multi-layered structure can be hardly prepared or the like. In particular, when it is used as an insulating material of a multi-layered wiring board or an interlaminar insulating membrane of LSI, etc., for preparing a multi-layered structure, an insulating layer is formed by using a polymer containing a quinoline ring previously dissolved in a solvent, and then, the next layer is similarly formed by using a polymer containing a quinoline ring dissolved in a solvent whereby an insulating layer is formed. However, the insulating layer previously formed is dissolved in a solvent so that a multi-layered structure can be difficultly formed. Moreover, in order to solve the above-mentioned problems, it can be considered a method in which a semi-cured film removing a solvent is formed, and molding is carried out under heating and pressure. However, the above film does not show flowability even when it is molded under heating and pressure so that, at present, it is difficult to apply the material to an insulating material for a multi-layered structure.
When the polymer containing a quinoline ring as mentioned above is used as an insulating material of a multi-layered wiring board or an interlaminar insulating membrane of LSI, etc., a multi-layered wiring board, etc. can be formed, for example, by forming a varnish previously dissolving in a solvent, coating it and drying to remove the solvent, and forming a conductive material by sputtering or chemical plating, etc., and the procedure is repeated. However, in this method, there are problems that a number of steps is much, an adhesiveness to the conductive material is poor, highly multi-layered structure can be difficultly prepared, and peeling occurs in a soldering step of LSI, etc., whereby reliability is insufficient, or the like.
An object of the present invention is to provide a resin composition and an adhesive film each excellent in molding property and has high adhesive force witha conductive material, resin, ceramics, etc. without impairing electric characteristics, low moisture absorption ratio and thermal stability at high temperatures.
DISCLOSURE OF THE INVENTION
Summary of the present invention which solves the above problems is as follows.
The first invention is a resin composition which comprises, as essential components, (A) a polymer containing a quinoline ring represented by the following formula (1) in the structure, and (B) a bismaleimide compound represented by the following formula (2).
wherein Ar represents a divalent organic group containing at least two carbon atoms.
The second invention is a composition obtained by dissolving a resin composition comprising, as essential components, (A) a polymer containing a quinoline ring represented by the following formula (1) in the structure and (B) a bismaleimide compound represented by the following formula (2), and (C) a polymeric compound selected from an aromatic diamine, an epoxy compound and a polybutadiene compound, etc. in (D) an organic solvent.
wherein Ar has the same meanings as defined above.
The third invention is a resin composition obtained by removing the organic solvent from the composition according to the second invention.
The fourth invention is a cured product obtained by heating and curing the resin composition of the third invention.
The fifth invention is, in either of the first to the third inventions, a resin composition which has a temperature region showing the value of a storage elastic modulus of from 10
7
dyn/cm
2
to 10
2
dyn/cm
2
at the temperature of 250° C. or lower, asaturation moisture absorption ratio of 1% or less, and thermal resistance at the atmosphere of 330° C. for 10 minutes or longer and an adhesive force with a material to be adhered of 0.6 kgf/cm or more.
The sixth invention is, in either of the first to the fifth inventions, a resin composition which comprises using, as the polymer containing a quinoline ring, a polymer containing a quinoline ring represented by the following formula (3) or (4).
Here, in the formula (3) or the formula (4), R′ each represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a formyl group (—COR), an ester group (—COR or —OCOR), an amide group (—NRCOR or —CONRR), a heteroaryl group, a cyano group or a divalent hydrocarbon group which may contain an unsaturated bond formed by binding two groups (wherein R represents a hydrogen atom, an alkyl group or a heteroaryl group.), n is each independently an integer of 0 to 5, x represents a single bond, —O—, —S—, —CO—, —SO—, —SO
2
—, —A—, the following formula (7) or —Q— (wherein q is an integer of 1 to 3, A represents —Ar—O—Ar— (where Ar represents an arylene group), —Hr— (where Hr represents a heteroarylene group), —CO—Ar—, —Ar—S—Ar—, —Ar—SO—Ar—, —Ar— or —Ar—Q—Ar—, Q represents L
1
—C—L
2
, and L
1
and L
2
each represents a methyl group, a trifluoromethyl group, or a divalent hydrocarbon group formed by combining L
1
and L
2
together with a carbon atoms to which they are bound, which may contain an unsaturated bond (s) or may be substituted by an unsaturated group(s).), Z′ represents a single bond or an arylene group, and Y represents —O— or —O—A—O—.
The seventh invention is, in either of the first to the sixth inventions, a resin composition represented by a bismaleimide compound having the formula (5) or the formula (6) in the structure.
wherein R
1
to R
10
represent a hydrogen atom, CH
3
, C
2
H
5
, CF
3
or C
2
F
5
, which may be the same or different from each other, and n is 0 or an integer of 1 to 4, which may be the same or different from each other.
The eighth invention is an adhesive film which comprises using the resin composition in the third, the fifth, the sixth or the seventh invention.
The ninth invention is, in the eighth invention, an adhesive film which comprises using at least one of the organic solvent selected from the group consisting of N-methyl-2-pyrrolidone, quinolin

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