JP3067384B2 - Epoxy resin copper clad laminate - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an epoxy resin copper-clad laminate, and more particularly to an epoxy resin copper-clad laminate excellent in low dielectric properties.

[0002]

2. Description of the Related Art Conventionally, among epoxy resin compositions used for electric and electronic applications, a combination of a bisphenol type epoxy resin and dicyandiamide is mainly used as a material for a printed wiring board. In recent years, with the increase in the number of layers in a printed wiring board, low dielectric properties of a resin have been demanded mainly for the purpose of improving the signal speed. As a means for meeting this demand, addition of a low-dielectric thermoplastic resin to a conventional epoxy resin composition is well known. For example, a method of modifying with a reactive polybutadiene resin, a method of dispersing a powder of a polytetrafluoroethylene resin, a method of using aramid fiber as a base material, and the like. In addition, there has been reported an example in which D-glass or quartz having a lower dielectric constant than conventional E-glass is used as a substrate.

[0003]

However, in these prior arts, the ratio of the thermoplastic resin to be combined is large in order to achieve a desired dielectric constant because the basic epoxy resin has a high dielectric constant. Features such as heat resistance, dimensional stability, and chemical resistance are impaired. Also, when aramid fiber or quartz is used for the base material, there is a drawback that the drill is severely worn at the time of drilling a printed circuit board. When using D-glass, there is no problem of drillability, but the manufacturing cost of the printed circuit board is high. Problem arises. Therefore, a low-dielectric epoxy resin that can obtain a low-dielectric printed board in exactly the same manner as in the past has been desired. An object of the present invention is to solve the above-mentioned problem. That is, the epoxy compound itself is made to have a lower dielectric property, thereby obtaining a low dielectric epoxy resin copper-clad laminate excellent in heat resistance and adhesiveness.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies on the skeletal structure of the epoxy compound, and as a result, have found that the epoxy compound represented by the following formula 2 has excellent low dielectric properties. The invention has been completed. That is, the present invention provides the following

[0005]

Embedded image (In the formula, n represents the average number of repeating units and takes a value of 1 or more and 20 or less. R ₁ , R ₂ , R ₃ , and R ₄ each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. , Carbon number 5
Represents a cycloalkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms.
However, all of R ₁ , R ₂ , R ₃ and R ₄ are not hydrogen atoms. P and Q are each independently a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group and an alkynyl group, a cycloalkyl group having 5 to 12 carbon atoms, and a carbon atom having 6 to 1 carbon atoms.
4, an aryl group having 4 to 6 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyloxy group and an alkynyloxy group, an aryloxy group having 6 to 14 carbon atoms,
Represents either a nitro group or a cyano group, and i takes an integer value of 0 or more and 4 or less only when n = 1, and takes an integer value of 0 or more and 3 or less in other cases. j takes an integer value of 0 or more and 4 or less. When i is 2 or more, P may be the same or different, and when j is 2 or more,
Similarly, Q may be the same or different. Epoxy resin copper clad, characterized in that a prepreg obtained by dissolving an epoxy resin composition comprising an epoxy compound represented by the formula (1) and a curing agent in an organic solvent and impregnating the base material with a copper foil is molded by heating. It relates to a laminate. Further, the present invention provides an epoxy resin composition comprising a curing agent and an adduct obtained by previously reacting an epoxy compound represented by the above formula (2) with a compound having two or more phenolic hydroxyl groups in an organic solvent. A copper prepreg obtained by impregnating a prepreg and a copper foil by heat molding. Preferably, n is 1 or more and 20 or less as the epoxy compound represented by the above formula 2,
R ₁ , R ₂ , R ₃ , and R ₄ are all methyl groups, P is each independently an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 6 to 12 carbon atoms, and i is 2 or more. An epoxy compound in which j is 0 or an integer of 3 or less, or n is 1 or more and 20 or less, and R ₁ , R ₂ ,
R ₃ and R ₄ are all methyl groups, and P has 4 to 8 carbon atoms.
An epoxy compound having the following alkyl group or a cycloalkyl group having 6 to 12 carbon atoms, i is 1 and j is 0 can be used. In the above Chemical Formula 2, as the value of n, a numerical value of 1 or more and 20 or less can be mentioned, and from 1 to 5 or less is preferable on the balance between the heat resistance of the epoxy compound and the low viscosity relating to the operability. .

The epoxy compound used in the present invention is represented by the following formula:

Embedded image (However, n, R ₁ , R ₂ , R ₃ , R ₄ , P, Q,
The definitions of i and j are the same as the definitions for the epoxy compound represented by the above formula (2). Can be obtained by a known method in which epihalohydrin is reacted with the compound represented by the formula (1) in a suitable organic solvent in the presence of an alkali such as caustic soda.

The compound represented by the above formula 3 is disclosed in
-121230, 58-121231,
In addition to the method disclosed in JP-A-63-303939 and the like,
Any known method can be used. As a general production method of the compound represented by the above formula 3, diisopropenylbenzene, bis (α-hydroxyisopropyl) benzene, 1-isopropenyl-3-α-
Compounds represented by hydroxyisopropylbenzene, 1-isopropenyl-2-α-hydroxyisopropylbenzene, 1-isopropenyl-4-α-hydroxyisopropylbenzene and their aromatic nucleus-substituted derivatives, and phenols in the presence of an acid catalyst The reaction is exemplified below, but is not limited thereto.

Here, the phenols correspond to compounds having at least one phenolic hydroxyl group, such as phenol, cresol, ethylphenol, and the like.
n-propylphenol, isopropylphenol, n
-Butylphenol, isobutylphenol, t-butylphenol, octylphenol, nonylphenol, xylenol, methylbutylphenol, di-t-
Various o-, m-, and p-isomers of alkylphenols represented by butylphenol, di-t-amylphenol and the like, or alkenyl or alkynylphenol represented by vinylphenol, allylphenol, propenylphenol, ethynylphenol and the like. Various o
-, M-, p-isomer or methoxyphenol,
Various o-, m- and p-isomers of alkoxy, alkenyloxy or alkynyloxyphenol represented by ethoxyphenol, allyloxyphenol, propargyloxyphenol, etc., or cyclopentylphenol, cyclohexylphenol, cyclohexylresole And halogen-substituted phenols such as chlorophenol, dichlorophenol, bromophenol and dibromophenol, and substituted phenols such as nitrophenol, cyanophenol, arylphenol and aralkylphenol.

Among the phenols, 2,6-xylenol, more preferred for lowering the dielectric constant,
2-butyl-5-methylphenol, 2-butyl-4-
Methylphenol, 2,4-dibutylphenol, 2,
4-di (t-amyl) phenol, 2-cyclohexyl-5-methylphenol, 2-t-butylphenol,
Examples thereof include 2- (t-amyl) phenol and 2-cyclohexylphenol.

As the curing agent used in the present invention, known curing agents can be used, for example, polyhydric phenols such as phenol novolak, cresol novolak, 1,1,1-trishydroxyphenylethane, and aromatic compounds. Examples include amine-based curing agents such as amines and aliphatic amines, acid anhydrides, dicyandiamide, and hydrazide compounds. Preferred are dicyandiamide and polyhydric phenols. The amount is preferably 0.3 to 1.2 equivalents to the epoxy group.

As the compound having two or more phenolic hydroxyl groups used in the present invention, known compounds can be used. For example, catechol, resorcin, hydroquinone, bisphenol A, bisphenol F, biphenol, 4,4'-dihydroxy Diphenyl sulfone, 4,
4'-dihydroxydiphenyl ether, tetrabromobisphenol A, polyvinyl phenol and the like.

An epoxy compound and a phenolic hydroxyl group are
The reaction with a compound having two or more compounds may be performed by a known method. For example, the above components can be reacted in the presence of a basic catalyst such as triphenylphosphine or imidazole.

Further, to the extent that the effects of the present invention are not impaired,
It is also possible to use a conventionally known bifunctional epoxy resin, polyfunctional epoxy resin, or a thermoplastic resin having a functional group in combination. Specifically, glycidyl ether of bisphenol A, glycidyl ether of tetrabromobisphenol A, glycidyl ether of phenol novolak, glycidyl ether of cresol novolak, glycidyl ether of brominated phenol novolak, glycidyl-modified polybutadiene, maleic anhydride-modified polyethylene, etc. is there. These resins may be mixed in the epoxy resin composition, or may be used after previously reacting with an epoxy compound or a mixture of an epoxy compound and a compound having two or more phenolic hydroxyl groups.

In the present invention, known additives such as a curing accelerator, a flame retardant and a surface treating agent may be added to the composition depending on the use. Examples of the curing accelerator include imidazoles, tertiary amines and phosphorus compounds, examples of the flame retardant include antimony trioxide and red phosphorus, and examples of the surface treatment agent include a silane coupling agent. Examples of the filler include silica, alumina, talc, clay, and glass fiber.

The preparation of the copper-clad laminate of the present invention can be carried out according to a known method. That is, this is a method in which a resin varnish obtained by dissolving the epoxy resin composition in an organic solvent is impregnated into a base material, heat-treated to form a prepreg, and then a prepreg and a copper foil are laminated and heat-molded to form a copper-clad laminate.

The organic solvent used is not particularly limited.
For example, acetone, methyl ethyl ketone, methyl isobutyl ketone, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, toluene, xylene, N, N-dimethylformamide, dioxane,
It is selected alone or as a mixed solvent of two or more from tetrahydrofuran and the like.

The base material to be impregnated with the resin varnish is made of inorganic fiber such as glass fiber, polyester fiber, polyamide fiber, etc.
Woven or non-woven fabric or mat made of organic fibers,
Paper and the like can be used alone or in combination. The heat treatment conditions for the prepreg are the solvent used,
It is appropriately selected according to the type and amount of the added catalyst and various additives, but is usually performed at a temperature of 80 ° C to 220 ° C for 3 minutes to 30 minutes.

The heat molding conditions 2 at a molding pressure of 10kg / cm ² ~100kg / cm ² at a temperature of 0.99 ° C. to 300 ° C.
Hot press molding for 0 to 300 minutes is exemplified.

[0019]

EXAMPLES Examples of the present invention will be shown below, but the present invention is not limited to these examples. In the examples, the epoxy equivalent is defined as the molecular weight of the epoxy resin per epoxy group. The OH equivalent is defined by the molecular weight of the OH compound per OH group. The hydrolyzable chlorine is obtained by dissolving an epoxy resin in dioxane, adding an alcohol solution of potassium hydroxide, and back-titrating chloride ions released when heated at reflux for 30 minutes with an aqueous silver nitrate solution. It is expressed as a percentage by weight in the table.

Synthesis Example 1 In this example, 4,4 '-[1,3-phenylenebis (1-methylethylidene)] bis [2,6-dimethyl] is used as a raw material of the epoxy compound used in the present invention. It relates to a method for producing phenol. In a 3 liter four-necked round bottom flask equipped with a thermometer, a stirrer, and a reflux condenser,
48-8.0 g (4.0 mol) of 6-xylenol, 51.0 g of bis (α-hydroxyisopropyl) benzene
(0.26 mol), 800 g of concentrated hydrochloric acid,
And hold for 1 hour. 51.0 g (0.26 mol) of bis (α-hydroxyisopropyl) benzene was further charged, and kept at 60 ° C. for 1 hour.
-Hydroxyisopropyl) benzene 53.2 g (0.
28 mol) and kept at 60 ° C. for 7 hours to complete the reaction. After the reaction, the mixture is diluted with toluene to remove the concentrated hydrochloric acid layer, neutralized with warm sodium bicarbonate water, washed with warm water, and then concentrated under reduced pressure to obtain a glassy solid. The crystals were recrystallized from toluene / n-heptane, washed with cold toluene, and dried under reduced pressure to obtain 249.8 g of white crystals (78% yield). Melting point: 129.5-131.5
° C, and as a result of proton nuclear magnetic resonance absorption spectrum measurement, δ7.24-7.00 (4H, m), 6.77 (4
H, s), 4.47 (2H, s), 2.17 (12H,
s) and 1.59 (12H, s). Further, the product was confirmed to be the target product by infrared absorption spectrum, gel permeation chromatography, and mass spectrometry.

Synthesis Example 2 In this example, 4,4 ′-[1,3-phenylenebis (1-methylethylidene)] bis [2-t-butyl-, which is a raw material of the epoxy compound used in the present invention, is used. 5-methyl]
It relates to a method for producing phenol. In a 5 liter four-necked round bottom flask equipped with a thermometer, a stirrer, and a reflux condenser, 2-t-butyl-5-methylphenol 123 was added.
1.5 g (7.5 mol), 291.5 g (1.5 mol) of bis (α-hydroxyisopropyl) benzene, 1500 g of concentrated hydrochloric acid, and 1000 g of toluene were charged.
React at 30 ° C. for 30 hours. After the reaction, after removing the concentrated hydrochloric acid layer, the mixture is neutralized with a 10% aqueous sodium hydroxide solution and washed with ion-exchanged water. After removing the solvent by concentration under reduced pressure, the obtained glassy solid is recrystallized with toluene. After filtering off the crystals, the crystals are washed with cold toluene and dried under reduced pressure to obtain 229.3 g of the desired product (yield: 47.1%). The melting point is
180.9-196.5 ° C. The proton nuclear magnetic resonance absorption spectrum, infrared absorption spectrum, gel permeation chromatography, and mass spectrometry confirmed that the product was the desired product in the same manner as in Example 1.

Synthesis Example 3 In this example, an o-cresol having a structure in which o-cresol, which is a raw material of the epoxy compound of the present invention, is bonded with 1,3-α, α, α ′, α′-tetramethylxylylene is used. The present invention relates to a method for producing a cresol oligomer. o-cresol 108.1 g
(1.00 mol), 128.2 g of 1,3-bis (α-hydroxyisopropyl) benzene (0.66 mol)
l), 150 g of toluene and 5.2 g (0.03 mol) of p-toluenesulfonic acid monohydrate were charged into a 1-liter reactor equipped with a separation tube equipped with a reflux condenser, a thermometer, and a stirrer. After dissolving, the temperature is raised to 120 ° C., and the temperature is kept for 8 hours while removing azeotropic water. After the reaction, the mixture was allowed to cool, diluted with toluene, washed with water, and then the solvent was distilled off under reduced pressure.
49.4 g are obtained. In the same manner as in Example 1, it was confirmed that the target compound was obtained by proton nuclear magnetic resonance absorption spectrum, infrared absorption spectrum, gel permeation chromatography, and mass spectrometry. Furthermore, the average n was determined by a calibration curve method using liquid chromatography, and as a result, it was 1.36. The OH equivalent was 245 g / eq.

Synthesis Example 4 This synthesis example relates to a method for producing an epoxy compound from the raw materials obtained in Synthesis Example 1. 4,4 '-[1,3-phenylenebis (1-methylethylidene)] bis [2,6-dimethyl] phenol 10 obtained in Synthesis Example 1
0.7 g (0.25 mol), epichlorohydrin 32
3.8 g (3.5 mol), dimethyl sulfoxide 16
1.9 g was charged into a 1-liter four-necked flat-bottomed flask equipped with a thermometer, a stirrer, and a condenser with a separation tube.
Under a condition of 8 ° C. and 41 torr, 41.2 g (0.5 mol) of a 48.6% aqueous sodium hydroxide solution is added dropwise over 5 hours. During this time, while keeping the temperature at 48 ° C., the azeotropic epichlorohydrin and water were cooled and liquefied, and the reaction was performed while returning the organic layer into the reaction system. After completion of the reaction, unreacted epichlorohydrin was removed by concentration under reduced pressure, an epoxidized product containing by-product salt and dimethyl sulfoxide was dissolved in methyl isobutyl ketone, and the by-product salt and dimethyl sulfoxide were removed by washing with warm water. The solvent was removed under reduced pressure to obtain 125.3 g of an epoxy compound. The epoxy equivalent and hydrolyzable chlorine of the epoxy compound thus obtained were 268.5 g / eq and 100, respectively.
ppm. As a result of infrared absorption spectrum measurement, it was confirmed that the absorption of phenolic OH at 3200 to 3500 cm ^-1 disappeared and the epoxide had absorptions of 1220 and 910 cm ^-1 .

Synthesis Example 5 This synthesis example relates to a method for producing an epoxy compound from the raw materials obtained in Synthesis Example 2. 121.7 g (0.25 mol) of 4,4 ′-[1,3-phenylenebis (1-methylethylidene)] bis [2-t-butyl-5-methyl] phenol obtained in Synthesis Example 2, epichloro 323.8 g (3.5 mol) of hydrin and 161.9 g of dimethylsulfoxide were charged into a 1-liter four-necked flat-bottomed flask equipped with a thermometer, a stirrer, and a condenser equipped with a separation tube. 41.2 g (0.5 mol) of a 6% aqueous sodium hydroxide solution is added dropwise over 5 hours. During this time, while maintaining the temperature at 70 ° C., the azeotropic epichlorohydrin and water were cooled and liquefied, and the reaction was performed while returning the organic layer into the reaction system. After completion of the reaction, Synthesis Example 4
After the same post-treatment as above, 143.2 g of epoxy compound
I got The epoxy equivalent and hydrolyzable chlorine of the epoxy compound thus obtained were each 314 g /
eq was 170 ppm. As a result of infrared absorption spectrum measurement, absorption of phenolic OH 3200-3500c
m ^-1 disappears, epoxide absorption 1260, 900 cm
It was confirmed to have an absorption of ^-1 .

Synthesis Example 6 This synthesis example relates to a method for producing an epoxy compound from the raw materials obtained in Synthesis Example 3. O obtained in Synthesis Example 3
Cresol oligomer 100.0 g (0.21 mo
l), 270.0 g of epichlorohydrin (2.94 mo)
l), 134.9 g of dimethyl sulfoxide was added to a liter having a thermometer, a stirrer, and a condenser equipped with a separation tube.
34.6 g (0.4%) of a 48.6% aqueous solution of sodium hydroxide at 48 ° C. and 41 torr.
2 mol) is added dropwise over 5 hours. During this time, the temperature was 4
While maintaining the temperature at 8 ° C., the azeotropic epichlorohydrin and water were cooled and liquefied, and reacted while returning the organic layer into the reaction system. After completion of the reaction, the same post-treatment as in Synthesis Example 4 was performed.
115.5 g of an epoxy compound was obtained. The epoxy equivalent and hydrolyzable chlorine of the epoxy compound thus obtained were 345 g / eq and 240 ppm, respectively. As a result of infrared absorption spectrum measurement, phenolic OH
3200-3500 cm ^-1 disappeared, and it was confirmed to have epoxide absorption of 1240 and 910 cm ^-1 .

Synthesis Example 7 This synthesis example relates to a method for obtaining an epoxy resin terminal by an addition reaction between the epoxy compound obtained in Synthesis Example 5 and tetrabromobisphenol A. 50.0 g (0.0774 mol) of the epoxy compound obtained in Synthesis Example 5
l), diglycidyl ether of tetrabromobisphenol A (trade name: ESB-40, manufactured by Sumitomo Chemical Co., Ltd.)
0, epoxy equivalent 403 g / eq) 20.39 g (0.
0253 mol) was charged into a 300 ml four-necked round-bottomed flask equipped with a thermometer, a condenser and a stirrer.
After heating and melting with tetrabromobisphenol A1
0.25 g (0.0188 mol) is added and dissolved. 11.3 mg of 2-ethyl-4-methylimidazole
(0.1 mmol) in 2.0 g of methyl ethyl ketone was added, the temperature was raised to 140 ° C. while removing the solvent, the temperature was maintained for 53 hours, and the reaction product was cooled and taken out to obtain the desired adduct 82. 0.5 g are obtained. The epoxy equivalent of the obtained adduct was 515.1 g / eq. Met.

Examples 1-4 The epoxy compounds obtained in Synthesis Examples 4-7, dicyandiamide and 2-ethyl-4-methylimidazole are shown in Table 1.
And dissolved in a mixed solvent of methyl ethyl ketone and ethylene glycol monomethyl ether to obtain a uniform resin varnish. Apply the varnish to a glass cloth (trade name:
KS1600S962LP, manufactured by Kanebo Co., Ltd.)
The prepreg was obtained by treating with a hot air drier at 150 ° C. for 5 to 10 minutes. Five prepregs and copper foil (TTAI treatment 35
μm-thick Furukawa Circuit Foil Co., Ltd.) were stacked and hot-pressed at 170 ° C. × 50 kg / cm ² × 120 minutes to obtain a 1 mm-thick copper-clad laminate. Then, in order to further promote curing, the sample was treated in a hot air drier at 180 ° C. for 5 hours to obtain a sample for evaluation. The copper foil peeling strength, solder heat resistance and boiling water absorption of the laminate are JIS-C-64.
81 was measured. The glass transition temperature (Tg) was determined from the inflection point of the thermal expansion curve using a thermal analyzer DT-30 manufactured by Shimadzu Corporation. The dielectric constant and dielectric loss tangent at room temperature are 4275A manufactured by Yokogawa Hewlett-Packard Co., Ltd.
Multi-Frequency LCR mete
Using r, the value of the dielectric constant was calculated from the capacitance of the sample. Table 1 shows the measurement results.

Comparative Example 1 As a epoxy resin, a brominated epoxy resin (trade name: Sumiepoxy ESB-500, manufactured by Sumitomo Chemical Co., Ltd., epoxy equivalent: 472 g / eq) and a cresol novolac type epoxy resin (manufactured by Sumitomo Chemical Co., Ltd.) Name: Sumiepoxy ESCN-220, epoxy equivalent 215 g /
eq) using dicyandiamide and 2-ethyl-4
-Methylimidazole was blended in the ratio shown in Table 1 and dissolved in a mixed solvent of methyl ethyl ketone and ethylene glycol monomethyl ether to obtain a uniform resin varnish. The varnish was impregnated in a glass cloth (KS-1600S962LP, manufactured by Kanebo Co., Ltd.), and dried in a hot air dryer at 150 ° C. for 5 to 1 hour.
The prepreg was obtained by treating for 0 minutes. Five prepregs and a copper foil (35 μm thick with TTAI treatment, manufactured by Furukawa Circuit Foil Co., Ltd.) were superposed, and 170 ° C. × 50 kg / cm ^2.
Hot press molding was performed under the conditions of × 120 minutes to obtain a copper-clad laminate having a thickness of 1 mm. The physical properties of the laminate were measured in the same manner as in Examples 1 to 4, and the results are shown in Table 1.

[0029]

[Table 1]

[0030]

The epoxy resin copper-clad laminate of the present invention has a lower dielectric constant than conventional ones and is excellent in heat resistance and water resistance, so that it is particularly suitable for a multilayer printed wiring board for high-speed arithmetic processing. .

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification code FI C09D 163/00 C09D 163/00 (72) Inventor Yasuhiro Endo 6 Kitahara, Tsukuba, Ibaraki Prefecture Within Sumitomo Chemical Co., Ltd. (58) Survey Field (Int.Cl. ⁷ , DB name) B32B 15/08 C08G 59/62 C08J 5/24 CFC

Claims (4)

(57) [Claims] (1) General formula (1) (In the formula, n represents the average number of repeating units and takes a value of 1 or more and 20 or less. R ₁ , R ₂ , R ₃ , and R ₄ each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. , Carbon number 5
Represents a cycloalkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms.
However, all of R ₁ , R ₂ , R ₃ and R ₄ are not hydrogen atoms. P and Q are each independently a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group and an alkynyl group, a cycloalkyl group having 5 to 12 carbon atoms, and a carbon atom having 6 to 1 carbon atoms.
4, an aryl group having 4 to 6 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyloxy group and an alkynyloxy group, an aryloxy group having 6 to 14 carbon atoms,
Represents either a nitro group or a cyano group, and i takes an integer value of 0 or more and 4 or less only when n = 1, and takes an integer value of 0 or more and 3 or less in other cases. j takes an integer value of 0 or more and 4 or less. When i is 2 or more, P may be the same or different, and when j is 2 or more,
Similarly, Q may be the same or different. Epoxy resin copper clad, characterized in that a prepreg obtained by dissolving an epoxy resin composition comprising an epoxy compound represented by the formula (1) and a curing agent in an organic solvent and impregnating the base material with a copper foil is molded by heating. Laminated board. 2. In the above general formula 1, n is 1 or more and 20 or more.
Wherein R ₁ , R ₂ , R ₃ and R ₄ are all methyl groups, and P is each independently an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 6 to 12 carbon atoms, The epoxy resin copper-clad laminate according to claim 1, wherein an epoxy resin composition comprising an epoxy compound in which i is an integer of 2 to 3 and j is 0 and a curing agent is used. 3. In the general formula 1, n is 1 or more and 20 or more.
Wherein R ₁ , R ₂ , R ₃ , and R ₄ are all methyl groups, P is an alkyl group having 4 to 8 carbon atoms or a cycloalkyl group having 6 to 12 carbon atoms, and i is 1
The epoxy resin copper-clad laminate according to claim 1, wherein an epoxy resin composition comprising an epoxy compound wherein j is 0 and a curing agent is used. 4. An epoxy resin composition comprising a curing agent and an adduct obtained by previously reacting the epoxy compound according to claim 1, 2, or 3 with a compound having two or more phenolic hydroxyl groups, in an organic solvent. An epoxy resin copper-clad laminate obtained by heat-forming a prepreg obtained by melting and impregnating a substrate and a copper foil.