JP2983616B2 - Compound for heat-resistant laminate and method for producing laminate using the compound - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a compound for a heat-resistant laminated material having excellent heat resistance, moisture resistance and storage stability, and a method for producing a heat-resistant laminated material using the same.

[Conventional technology and issues]

2. Description of the Related Art In recent years, the development of electronic devices has been remarkable, and the use of copper-clad laminates used as wiring boards has become diversified. In particular, with the increase in wiring density due to the high-density mounting of electronic components, multilayer wiring boards and smaller through-hole diameters are being promoted. For this reason, a copper-clad laminate having good workability, such as less occurrence of smear during drilling, is required. On the other hand, with the demand for improvement in productivity and cost reduction, increasingly strict processing conditions such as hot air leveler and reflow soldering are added in the wiring board mounting process. Among these requirements, a copper-clad laminate as a substrate has been required to have better heat resistance and moisture resistance than ever before.

In order to satisfy these requirements, an addition-curable polyimide resin has recently been used in place of an epoxy resin which is generally used widely as a laminate for a copper-clad laminate. When this polyimide resin is used as a laminate for a copper-clad laminate, the occurrence of smear during drilling is almost eliminated, and the advantage that the heat resistance in the processing step and long-term test is significantly improved. Are known.

However, conventionally used addition-curable polyimide resins have various problems as described below. That is, the product obtained by reacting the unsaturated dicarboxylic acid N, N'-bisimide with diaminodiphenylmethane is excellent for use as a laminate, but on the other hand, diaminodiphenylmethane has a high reactivity and is suitable for varnish and prepreg. There is a problem that the working time is short. In addition, the toxicity of diaminodiphenylmethane to living organisms can be problematic. Further, those containing N, N'-bisimide of unsaturated dicarboxylic acid and diaminophenol as reaction components show well-balanced properties for laminates and have excellent workability.
However, there is a problem that the moisture resistance is inferior. For example, for the long-term storage of the obtained laminate, special attention must be paid to moisture absorption.

Further, those obtained by reacting an unsaturated dicarboxylic acid with N, N'-bisimidoaminobenzoic acid are suitable for use as laminates, but have poor solubility in low-boiling-point solvents, and the glass used during prepreg production There is a problem in application to cloth etc.
There have been problems such as care must be taken in storage of the resin solution.

[Means for solving the problem]

In view of such circumstances, the present inventors have made intensive studies to solve these technical problems, and as a result, have reached the present invention.

That is, the first aspect of the present invention is that the general formula (1) (Wherein, Ar ₁ and Ar ₃ are divalent organic groups, Ar ₂ is a tetravalent organic group, Ar ₄ is an organic group having thermal crosslinking reactivity, and Ar ₁ and A
r ₂ , Ar ₃ and Ar ₄ may be the same or different. X and Y are copolymerization ratios, X is 1 to 30,
Y represents a positive integer of 0 to 30. A second aspect of the present invention is to prepare a varnish-like resin composition by dissolving the above compound in an organic solvent, and then use a reinforcing material. Is applied and impregnated with the varnish resin composition, and dried so as to have a predetermined residual solvent concentration to prepare a prepreg, and one or more of the prepregs is sandwiched between two copper foils, Each of the methods includes a method for producing a double-sided copper foil laminate characterized by being integrally molded by heating and pressing.

The method for producing the compound for a heat-resistant laminate of the present invention will be described.

The reaction tank is sufficiently dried, and an organic diamine compound represented by the general formula (2): H ₂ N—Ar ₃ —NH ₂ (2) (where Ar ₃ is an inert gas atmosphere such as argon or nitrogen) Divalent organic group) is dissolved in a polar organic solvent, and an ester group-containing organic tetracarboxylic dianhydride represented by the general formula (3) is dissolved in the solution. (Wherein, Ar ₁ is a divalent organic group) or the ester group-containing tetracarboxylic dianhydride and an organic tetracarboxylic dianhydride represented by the general formula (4); (Wherein, Ar ₂ is a tetravalent organic group) is dissolved in the same polar solvent as described above, or is added as a powder while paying attention to heat generation and thickening, and a telechelic oligomer at the terminal of an acid anhydride group is added. obtain. The reaction temperature at this time is
The range of -15 to 120 ° C is suitable, and preferably -15 to 100 ° C.
C, more preferably -5 to 50C. The reaction time is preferably 1 to 5 hours.

To the reaction solution, a primary amine represented by the general formula (5); H ₂ N—Ar ₄ (5) (wherein, Ar ₄ is an organic group having thermal crosslinking reactivity) is added to terminate the terminal. Then, an oligoester amic acid represented by the following general formula (6), which is a precursor of a novel thermosetting oligomer, is obtained.

(Wherein, Ar ₁ and Ar ₃ are divalent organic groups, Ar ₂ is a tetravalent organic group, Ar ₄ is an organic group having thermal crosslinking reactivity, and Ar ₁ and A
r ₂ , Ar ₃ and Ar ₄ may be the same or different. X and Y are copolymerization ratios, X is 1 to 30,
Y represents a positive integer of 0 to 30. The temperature at this time is preferably from 0 to 120 ° C, more preferably from 0 to 100 ° C, and still more preferably from 40 to 100 ° C. The reaction time is preferably about 1 to 5 hours.

Thereafter, a non-solvent is added for thermally closing and dehydrating the oligoester amic acid solution, and the solution is converted into an ester imide oligomer under reflux and azeotropy. As the non-solvent used here, xylene, toluene, and benzene which are aromatic hydrocarbons can be used, but benzene is preferably used. In the reaction, the azeotropically distilled water is refluxed using a Dean-Stark reflux until a stoichiometric amount of water is collected. Further, a chemical ring closing method can be used in combination. Examples of the dehydration ring closing agent used herein include aliphatic acid anhydrides such as acetic anhydride, aromatic acid anhydrides such as phthalic anhydride, and chloroacetic acid. Examples of the dehydration catalyst include aliphatic tertiary amines such as triethylamine, and heterocyclic tertiary amines such as pyridine, picoline and isoquinoline. After the reaction, the esterimide oligomer is precipitated as a powder by pouring the oligoesterimide solution into water or an alcohol-based solvent with vigorous stirring. The powder is collected by filtration and dried at about 80 ° C. under reduced pressure for 48 hours.

As the ester group-containing tetracarboxylic dianhydride used in the present invention, an ester group-containing tetracarboxylic dianhydride of any structure can be used.
P 3182073, Journal of Polymer Science,
Part1,1531pp (1976), JP-A-1-254463, JP-A-2-
As disclosed in 138341, it can also be synthesized by a known technique.

That is, in an atmosphere of an inert gas such as argon or nitrogen, trimellitic acid chloride is dissolved in an organic solvent,
In the solution, a diol represented by the general formula (7) HO-Ar ₁ -OH (7) (wherein, Ar ₁ is a divalent organic group), an amine and an organic solvent are added while paying attention to the state of the reaction system. Added. Tertiary amines such as pyridine and triethylamine can be used as the amine used as a supplement for the reaction by-product hydrogen chloride, but pyridine is preferably used. As the organic solvent, xylene and toluene which are aromatic hydrocarbons can be used, but toluene is preferably used. The reaction temperature at this time is preferably in the range of −15 to 120 ° C., more preferably 0 to 100 ° C., and still more preferably 40 to 100 ° C. The reaction time is preferably 1 to 3 hours.

Thereafter, it is converted into an ester group-containing dianhydride under reflux conditions. After the reaction, the reaction system is sufficiently cooled, the precipitated salt is separated by filtration, the filtrate is collected, and the solvent is distilled off under reduced pressure to obtain an ester group-containing acid dianhydride crystal. This is recrystallized from acetic anhydride, and the crystals are dried at 80 ° C. under reduced pressure for 48 hours.

Ar _{1 in the} general formula (3) is a divalent organic group, and is preferably an aromatic group. Specific examples of this Ar ₁ group include the following, and at least one of them is selected.

More specifically, from the aspect of the balance of various characteristics, It is preferable that at least one of the above is a main component.

Further, in the present invention, as the organic tetracarboxylic dianhydride which can be used in combination with the ester group-containing tetracarboxylic dianhydride, an organic tetracarboxylic dianhydride having any structure can be used, but the general formula (4) Are preferred. The Ar ₄ group in the general formula (4) is a tetravalent organic group, and is preferably an aromatic group. Specific examples of this Ar ₂ include the following, at least one of which is selected.

These organic tetracarboxylic dianhydrides can be used alone or
It may be used in combination of more than one kind. More specifically, from the aspect of the balance of various characteristics, It is preferable that at least one of these is a main component.

The divalent organic group Ar ₃ in the organic diamine compound represented by the general formula (2) used in the present invention is essentially 2
Any valent organic group can be used, but specifically,
The following are mentioned, and at least one of them is selected.

And the like, but an aromatic group is desirable,
In particular, It is preferable that at least one or more of the above is used as a main component.

Examples of the primary amine Ar ₄ represented by the general formula (5) used in the present invention for terminal termination include the following, and at least one of them is selected.

However, in terms of cost and handling, it is particularly preferable that Is used.

Examples of the aprotic organic solvent used in the reaction for producing the ester imide oligomer solution include, for example, sulphoxide solvents such as dimethylsulfoxide and diethylsulfoxide, and formamides such as N, N'-dimethylformamide and N, N'-diethylformamide. And acetamide solvents such as N, N'-dimethylacetamide and N, N'-diethylacetamide. These can be used alone or as a mixed solvent of two or more. Further, it can be used as a mixed solvent with a non-solvent of a polyamic acid such as methanol, ethanol, isopropanol, benzene and methyl cellosolve together with these polar solvents. Preferably, use of dimethylformamide (hereinafter referred to as DMF) is desirable from the viewpoint of the color tone and the yield of the produced polymer.

The mechanism by which the esterimide oligomer having reactivity according to the present invention gives a cured product having particularly high heat resistance is not clear, but formation of a benzene skeleton by thermal curing (thermal trimerization) of acetylene or biphenylene. This is considered to be the effect of the formation of an aromatic ring due to the formation of a tetrabenzocyclooctadiene skeleton by thermosetting (for example, JK Stille et al., Macromolecules, No.
Vol. 8, No. 1985, p. 1986].

Further, the number average degree of polymerization (DP; PJ Flory, Principle
s of Polymer Chemistry: Cornell University Press: It
haca, NY, page 91, 1953], the copolymerization ratio X is from 1 to 30, and Y is from 0 to 30, preferably from 1 to 30.
15, more preferably 1 to 10. If it exceeds 30, there is a disadvantage that the solubility in organic solvents is reduced. Also,
If it is less than 1, a problem may occur in terms of mechanical strength.

In obtaining a cured product from the ester imide oligomer of the present invention, a known epoxy resin or epoxy resin curing agent, a curing accelerator, a filler, a flame retardant, a reinforcing agent, a surface treatment agent, a pigment, various elastomers and the like are used as necessary. Can be used together.

An epoxy resin is a compound having two or more epoxy (glycidyl) groups in a molecule. Examples thereof include bisphenol A, bisphenol F, hydroquinone, resorcin, furulglycine, tris- (4-hydroxyphenyl) methane, 1,1 Derived from dihydric or trihydric phenols such as 2,2,2-tetrakis (4-hydroxyphenyl) ethane or halogenated polyphenols such as novolak derived from tetrabromobisphenol A or brominated polyphenols. Glycidyl ether compounds, phenols, novolak epoxy resins which are reaction products of phenols such as orthocresol and formaldehyde, aniline, paraaminophenol, metaaminophenol, 4-amino-metacresol, 6-
Amino-metacresol, 4,4'-diaminodiphenylmethane, 8,8'-diaminodiphenylmethane, 4,4'-diaminodiphenylether, 3,4'-diaminodiphenylether, 1,4-bis (4-aminophenoxy) benzene, 1,4-bis (3-aminophenoxy) benzene,
1,3-bis (3-aminophenoxy) benzene, 2,2-bis (4-aminophenoxyphenyl) propane, paraphenylenediamine, metaphenylenediamine, 2,4-toluenediamine, 2,6-toluenediamine, para Xylylenediamine, metaxylylenediamine, 1,4-cyclohexane-bis (methylamine), 1,3-cyclohexane-bis (methylamine), 5-amino-1- (4'-
Aminophenyl) -1,8,8-trimethylindane, 6-
Amine-based epoxy resins derived from amino-1- (4-aminophenyl) -1,8,8-trimethylindane, and the like;
Glycidyl ester compounds derived from aromatic carboxylic acids such as paraoxybenzoic acid, terephthalic acid, and isophthalic acid; hydantoin-based epoxy resins derived from 5,5-dimethylhydantoin; 2,2'-bis (3,4 -Epoxycyclohexyl) propane, 2,2-bis [4- (2,3
-Epoxypropyl) cyclohexyl] propane, vinylcyclohexanedioxide, alicyclic epoxy resins such as 3,4-epoxycyclohexanecarboxylate, and others such as triglycidyl isocyanurate and 2,4,6-triglycidoxy-s-triazine. Species or species or more can be mentioned.

Known epoxy curing agents include amine curing agents such as aliphatic amines such as aromatic amines and xylylenediamine,
Examples thereof include polyphenol compounds such as phenol novolak and cresol novolak, and hydrazide compounds.

Benzyldimethylamine, 2,4,6 as curing accelerator
-Tris (dimethylaminomethyl) phenol, 1,8-
Examples thereof include amines such as diazabicycloundecene, imidazole compounds such as 2-ethyl-4-methylimidazole, and boron trifluoride amine complex.

The addition of known elastomers to improve mechanical strength is also effective. As the known elastomer, the following can be specifically exemplified.

The elastomers described above include Silastic (LS-420), S
ylgard (184) is a hiker / ATB from Dow Corning
N (1300x16 etc.), CTB (2000x162), CTBN (1300x13,
1300 x 8,1300 x 31) and VTBN (1300 x 23) can be purchased from Ube Industries, Ltd., and 3F can be purchased from Monsanto.

Further, a flame-retardant material and an inorganic filler can be appropriately blended for imparting flame retardancy.

As the inorganic filler, a water-insoluble and insulating material is used. Examples include silica, alumina, zirconia,
Metal oxides such as titanium dioxide and zinc oxide, metal hydroxides such as magnesium hydroxide and aluminum hydroxide, natural minerals such as talc, kaolin, mica, wollastonite, clay minerals, calcium carbonate, magnesium carbonate, barium sulfate And insoluble salts such as calcium phosphate, and these are used alone or in combination of two or more.

Examples of the reinforcing material include a liquid crystal polyester fiber such as a carbon fiber, a glass fiber, an aramid fiber, and Vectra, a nonwoven fabric made of a polybenzothiazole (PBT) fiber, an alumina fiber, and the like, a mat, a paper (paper), or a combination thereof. It is also effective to use these reinforcing materials together with a silane coupling agent treatment for imparting adhesiveness.

Next, a typical coating process will be described with an example. A uniform varnish-like resin composition is obtained by dissolving and stirring the ester imide oligomer represented by the general formula (I) with a predetermined amount of an organic solvent so as to have a predetermined resin concentration.
After applying and impregnating the thus-prepared resin composition with a reinforcing material such as a glass cloth, a glass nonwoven fabric, and a glass paper, the resin composition is heated to 50 to 250 ° C. in a circulating hot air drying oven, preferably 50 to 250 ° C.
A residence time in a furnace is set and dried at a temperature of 00 ° C., more preferably within a temperature range of 100 ° C. to 200 ° C., to obtain a predetermined residual solvent concentration, thereby producing a prepreg for a heat-resistant laminate.

Examples of the organic solvent used include, for example, dimethyl sulfoxide, sulfoxide solvents such as diethyl sulfoxide, N, N′-dimethylformamide, N, N′-diethylformamide and other formamide solvents, N, N′-dimethylacetamide, Acetamide solvents such as N, N'-diethylacetamide; ether solvents such as dimethyl ether, diethyl ether and dioxane; ketone solvents such as acetone and methyl ethyl ketone; These can be used alone or as a mixed solvent of two or more. Furthermore, with these organic polar solvents,
It can also be used as a mixed solvent with alcohol solvents such as methanol, ethanol and isopropanol, and benzene and methyl cellosolve.

The resin concentration at the time of dissolving and diluting in an organic solvent is 5 to 75% by weight, preferably 15 to 65% by weight, based on the relationship with the resin concentration at the time of prepreg.
%, More preferably 35 to 65% by weight. It is desirable that the residual solvent concentration of the prepreg is adjusted in the range of 1 to 20% by weight, preferably 1 to 10% by weight, and more preferably 1 to 5% by weight, based on the calculation of the residual solvent / resin ratio. If it is larger than the above range, a problem occurs that the mechanical properties of the laminate after prepreg molding are low. Also,
If it is smaller than the above range, the residual solvent is volatilized during prepreg molding, so that there is a disadvantage that voids are generated.

Next, a method for producing a double-sided copper-clad laminate using the heat-resistant prepreg obtained as described above will be described. Adjust the number of copper foils and prepregs to the desired thickness. By inserting a predetermined copper foil and prepreg between two stainless steel plates whose surfaces are mirror-finished, and then heating and pressing under a predetermined time and pressure, a double-sided copper-clad laminate can be produced. It is also effective to use aftercure in combination to improve the mechanical strength.

〔Example〕

Next, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to these examples, and the present invention is not limited to those skilled in the art without departing from the scope of the present invention. Various modifications, improvements, and changes can be made based on the knowledge of the above.

Reference Example 1 A 1-liter three-necked flask was equipped with a three-way cock, a Dimroth reflux condenser, and a dropping funnel. After the reaction system was sufficiently dried and purged with nitrogen, 42.1 g (200 mmol) of trimellitic acid chloride and 250 ml of dry toluene (dried on a sodium wire) were placed in a flask, and the oil bath was used.
The mixture was heated to 100 ° C. to dissolve trimellitic chloride. 22.8 g (100 mmol) of bisphenol A in the dropping funnel
And 20 ml of dry toluene were added thereto, and the mixture was added dropwise over 15 minutes while paying attention to the state of the reaction system, and then reacted as it was for 30 minutes.
Thereafter, the reaction was carried out under reflux for 3 hours. After the reaction was completed, the reaction system was sufficiently cooled, and the white precipitate of the precipitated pyridinium salt was filtered by suction. When the filtrate was collected and the solvent was distilled off under reduced pressure by an evaporator, 57.2 g (yield: 99%) of white crystals was precipitated. This was recrystallized from acetic anhydride to obtain 16.3 g of the target compound represented by the following structural formula.

The following formula Example 1 A three-way cock, a Din Stark still, a Dimroth reflux condenser, a dropping funnel, and a seam cap were attached to a 1-liter four-port frust. After drying the reactor under reduced pressure and sufficiently purging with nitrogen, the following formula The reaction system was charged with 3.54 g (10.0 mmol) of the diamine represented by the formula and 30 ml of dry dimethylformamide (hereinafter referred to as DMF), and cooled with ice.

Next, the following formula obtained in Reference Example 1 Was dissolved in 11.53 g (20.0 mmol) of DMF in a dropping funnel and added to the reaction system while paying attention to heat generation. After reacting at 0 ° C for 1 hour and at 60 ° C for 0.5 hour, the following formula Was dissolved in DMF and added to the reaction system. After the reaction at 60 ° C. for 0.5 hour, 200 ml of toluene was added.

Reaction under reflux for 45 hours, 0.6 ml under azeotropic toluene
(Theoretical value: 0.72 ml) was distilled off. After the reaction, the reaction solution was poured into 500 ml of methanol to precipitate an imide oligomer. The precipitated oligomer was filtered under reduced pressure and dried in vacuum at 80 ° C. for 48 hours to give 14.88 g (yield: 89.1
%) As a pale yellow powder.

165 g of the obtained ester imide oligomer, 200 g of DMF
(Resin concentration; 45% by weight / DMF). Sixteen 20 × 20 cm glass cloths (WEA-18K105F117; manufactured by Nitto Boseki) were impregnated. In a hot air circulating drying oven, dry at 120 ° C for 90 minutes,
A prepreg having a resin concentration of 38.9% by weight (per glass cloth) and a residual solvent concentration of 4.2% was prepared.

Eight pieces of prepreg thus prepared were subjected to electrolytic copper foil (35μ).
m, 3EC; manufactured by Mitsui Kinzoku Kogyo Co., Ltd.)
Heat and pressure were integrally molded under the conditions of 2 hours and 25 kg / cm ² to obtain a 13 mm thick double-sided copper-clad laminate.

Example 2 11.53 g (20 mmol) of aromatic acid dianhydride 2.92 g (10 mmol) of aromatic diamine 2.34 g (20 mmol) of aromatic primary amine Was used to carry out a reaction under the same conditions as in Example 1 to obtain 14.50 g of an esterimide oligomer (yield: 90.2%).

Example 1 using 165 g of the above esterimide oligomer
Under the same conditions as above, a double-sided copper-clad laminate having a thickness of 9 mm was obtained.

Example 3 Aromatic acid dianhydride (A) 5.77 g (10 mmol) 4.44 g (10 mmol) of aromatic dianhydride (B) 2.92 g (10 mmol) of aromatic diamine 2.34 g (20 mmol) of aromatic primary amine Was used to carry out a reaction under the same conditions as in Example 1 to obtain 13.16 g (yield: 89.2%) of an ester imide oligomer.

Using 165 g of the esterimide oligomer, a 9 mm-thick double-sided copper-clad laminate was obtained under the same conditions as in Example 1.

Example 4 11.53 g (20 mmol) of aromatic dianhydride 4.32 g (10 mmol) of aromatic diamine Aromatic primary amine 3.34g (20mmol) Was performed under the same reaction conditions as in Example 1 to obtain 16.93 g of an esterimide oligomer (yield: 91.6%).

Example 1 using 165 g of the above esterimide oligomer
Under the same conditions as above, a double-sided copper-clad laminate having a thickness of 9 mm was obtained.

Example 5 Aromatic acid dianhydride (A) 5.77 g (10 mmol) 3.52 g (10 mmol) of aromatic dianhydride (B) 4.32 g (10 mmol) of aromatic diamine Aromatic primary amine 3.34g (20mmol) Was used to carry out a reaction under the same conditions as in Example 1 to obtain 15.05 g of an esterimide oligomer (yield: 92.7%).

Example 1 using 165 g of the above esterimide oligomer
Under the same conditions as above, a double-sided copper-clad laminate having a thickness of 9 mm was obtained.

Comparative Example 1 165 g of a commercially available imide oligomer was dissolved in 200 g of DMF (resin concentration; 45% by weight / DMF). 20 × 20cm glass cloth (WEA
−18K105F117; Nittobo Co., Ltd.). It was dried in a hot air drying oven at 120 ° C. for 80 minutes to prepare a prepreg having a resin concentration of 38.9% by weight (per glass cloth) and a residual solvent concentration of 4.1%.

Eight pieces of prepreg thus prepared were subjected to electrolytic copper foil (35μ).
m, 3EC; manufactured by Mitsui Kinzoku Kogyo Co., Ltd.)
Heat and pressure were integrally molded under the conditions of 2 hours and 25 kg / cm ² to obtain a 13 mm thick double-sided copper-clad laminate.

Table 1 shows the physical properties of the copper-clad laminates obtained in Examples 1 to 5 and Comparative Example 1.

[Effect of the Invention] The compound for heat-resistant laminates of the present invention enables the production of prepregs for heat-resistant laminates having high moisture resistance and excellent storage stability. It is capable of producing a laminate such as a double-sided copper-clad laminate having excellent heat resistance, and its usefulness is extremely large.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI C09D 179/08 C09D 179/08 Z // C07D 209/48 H05K 1/03 630C H05K 1/03 630 630H C07D 209/48 Z B29K 101: 10 105: 06 C08L 79:08 (56) Reference US Pat. No. 4,649,189 (US, A). Macromol. Sci. -C hem. , A28 (7) (1991), pp. 633-640 Acta Polymerica, 42 (2-3) (1991), pp. 125-128 Revue Roumaine de Chimie, 34 (7) (1989), pp. 1467-1472 (58) Field surveyed (Int.Cl. ⁶ , DB name) C08G 73/06-73/22 C08L 79/04-79/08

Claims (8)

(57) [Claims] 1. The general formula (1) (Wherein, Ar ₁ and Ar ₃ are divalent organic groups, Ar ₂ is a tetravalent organic group, Ar ₄ is an organic group having thermal crosslinking reactivity, and Ar ₁ and A
r ₂ , Ar ₃ and Ar ₄ may be the same or different. X and Y are copolymerization ratios, X is 1 to 30,
Y represents a positive integer of 0 to 30. A compound for heat-resistant lamination, comprising the compound represented by the formula (1) as a main component. 2. The compound according to claim 1, wherein Ar ₁ is at least one selected from the following groups. 3. The compound according to claim 1, wherein Ar ₂ is at least one selected from the following groups. 4. The compound according to claim 1, wherein Ar ₃ is at least one selected from the following groups. 5. The compound according to claim 1, wherein Ar ₄ is at least one selected from the following groups. 6. A varnish-like resin composition is prepared by dissolving the compound according to claim 1 in an organic solvent, and then a reinforcing material is applied and impregnated with the varnish resin composition, and then a predetermined residual solvent is prepared. A double-sided copper foil laminate, wherein one or more of the prepregs are sandwiched between two copper foils, and heated and pressed to be integrally formed. Manufacturing method. 7. A varnish-like resin composition having a concentration of 5 to 75% by weight.
7. The method according to claim 6, wherein 8. A prepreg having a residual solvent concentration of 1 to resin.
The method according to claim 6 or 7, wherein the amount is from 20 to 20% by weight.