JPH06306168A - Cyanate resin composition - Google Patents

Abstract

PURPOSE:To obtain the composition which can provide a cured product having a low permittivity and practical heat resistance. CONSTITUTION:The composition is prepared by using a cyanate compound of the general formula (wherein R1 and R2 are each hydrogen or 1-5 C alkyl; A is 1-3 C alkyl, and i is an integer of 0-3), or its prepolymer and a curing agent or using these components and a brominated epoxy compound or its prepolymer, or a polymaleimide compound or its prepolymer as the essential components.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a cyanate resin composition. INDUSTRIAL APPLICABILITY The cyanate resin composition of the present invention is particularly useful as a resin for laminates in electric / electronic applications that require low dielectric properties, and is also applicable to encapsulation applications and molding resins.

[0002]

2. Description of the Related Art Among thermosetting resin compositions conventionally used for electric and electronic applications, as a material for a printed wiring board, mainly a combination of a bisphenol type epoxy resin and dicyandiamide, or a bismaleimide compound and an amine compound. Is used as an additive. In recent years, with the multilayering of printed wiring boards, low dielectric properties of resins have been demanded mainly for the purpose of improving the signal speed. As a means for meeting this demand, conventional thermosetting resin compositions have It is well known that the addition of dielectric thermoplastic resin is known, but according to this method, the drawback of impairing the heat resistance of thermosetting resin is pointed out, and it is necessary to sufficiently satisfy the requirement of low dielectric resin that can withstand practical use. I couldn't.

From these points, cyanate resin was developed, and German Patent No. 2533122 and International Patent 88/084.
No. 43 etc. have been proposed. A bisphenol A dicyanate is known as a cyanate resin which is generally used at present, but further lowering of dielectric constant has been demanded with the advancement of computer technology. Also,
It is known that the above cyanate compound is generally used as a resin composition, and is commonly used with a bismaleimide or an epoxy compound or the like (Japanese Patent Publication No. 54-30440) depending on its required characteristics. However, in this case, the dielectric constant of the resin composition greatly increased, and it was not at a satisfactory level.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide a cyanate resin composition which has a low dielectric property and gives a cured product having heat resistance that can withstand practical use.

[0005]

Means for Solving the Problems The inventors of the present invention have conducted extensive studies on the skeletal structure of cyanate compounds, and as a result, t
-The increase in the molecular volume due to the bulkiness of the butyl group and the increase in non-polarity due to the large hydrophobic group contribute significantly to the low dielectric property,
It was found that the composition of the specific cyanate having this satisfies the above-mentioned object, and has completed the present invention.
That is, the present invention is as follows. (1) The following general formula (1)

[0006]

[Chemical 10] (In the formula, R ₁ and R ₂ are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. A is an alkyl group having 1 to 3 carbon atoms, and i is 0 to 3 The cyanate resin composition comprises a cyanate compound represented by the following integer) or a prepolymer thereof and a curing agent as essential components.

(2) Cyanate resin composition comprising a cyanate compound represented by the general formula (1) or its prepolymer, a brominated epoxy compound or its prepolymer, and a curing agent as essential components. .

(3) Essentially a cyanate compound represented by the general formula (1) or a prepolymer thereof, a curing agent, and a polymaleimide compound having two or more N-maleimide groups in the molecule or a prepolymer thereof. A cyanate resin composition comprising a component. The cyanate compound which is an essential component of the resin composition of the present invention has the following general formula (1
0)

[0009]

[Chemical 11] (In the formula, R ₁ , R ₂ , A and i are defined in the same manner as in the general formula (1)), and a cyanogen halide represented by chlorocyan or bromcyan is suitable. It can be obtained by carrying out a dehydrohalogenation reaction in the presence of a base in an organic solvent.

The above-mentioned bisphenols may be obtained by any known method. As a general production method, a carbonyl compound is reacted with a phenol in the presence of an acid catalyst. However, this is not the case.

As the carbonyl compound, a compound having a carbonyl group having 1 to 11 carbon atoms is used. For example, formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, pentyl aldehyde, hexyl aldehyde, octyl aldehyde, etc. Representative aldehyde compounds, ketone compounds represented by acetone, methyl ethyl ketone, methyl propyl ketone, methyl isobutyl ketone, ethyl propyl ketone, diethyl ketone, dipropyl ketone, dibutyl ketone, etc. are mentioned, but in order to achieve the object of the present invention. Of these, formaldehyde, acetaldehyde, propionaldehyde and butyraldehyde are preferable. Further, as the phenols, those having a t-butyl group at the ortho position of the OH group, having no substituent at the para position, and optionally having an alkyl group having 3 or less carbon atoms are used. For example, 2-t-butylphenol, 2-t-butyl-5-
Methylphenol, 2-t-butyl-3-methylphenol, 2-t-butyl-6-methylphenol, 2-t
-Butyl-5-ethylphenol, 2-t-butyl-3
-Ethylphenol, 2-t-butyl-3-propylphenol and the like can be mentioned, but in order to achieve the object of the present invention, 2-t-butylphenol, 2-t-butyl-5.
-Methylphenol is preferred.

As a typical example of the cyanate compound used in the present invention, the following structural formula (9)

[Chemical 12] The compound represented by

The polymaleimide compound used in the present invention is a polymaleimide compound containing two or more N-maleimide groups in the molecule, and any one obtained by any method can be used. Examples of the method for synthesizing the polymaleimide compound include a method in which a raw material phenol is reacted with p-chloronitrobenzene, and then an amine compound obtained by reduction is reacted with maleic anhydride.
It is not limited to this. Examples of polymaleimide compounds preferable for achieving the object of the present invention are as follows. That is, the following general formula (2)

[0014]

[Chemical 13] [In the formula, X represents the following structural formulas (3), (4), (5),
(6), (7) or (8)

[0015]

[Chemical 14]

[0016]

[Chemical 15]

[0017]

[Chemical 16]

[0018]

[Chemical 17] (In the formula, n-Pr represents an n-propyl group.)

[0019]

[Chemical 18]

[0020]

[Chemical 19] Is a group represented by. ) The compound represented by.

Examples of the brominated epoxy compound used in the present invention include glycidyl ether of tetrabromobisphenol A and glycidyl ether of brominated phenol novolac. Flame retardancy can be imparted by adding these compounds to the resin composition of the present invention.

The cyanate compound, brominated epoxy compound and polymaleimide compound used in the present invention may be used as a monomer, or may be used alone or as a prepolymer of a mixture thereof. As the prepolymer, a cyanate compound, a brominated epoxy compound, a polymaleimide compound alone or in a mixture is used together with a curing agent described below.
It can be obtained by heating to about 200 ° C.

When the brominated epoxy compound or its prepolymer is added to the cyanate compound or its prepolymer to impart flame retardancy, the amount of brominated epoxy compound or its prepolymer depends on the bromo content in the composition. The amount is preferably 5 to 50% by weight. The polymaleimide compound or its prepolymer is preferably 1 to 50% by weight, and more preferably 3 to 50% by weight based on the total amount of these and the cyanate compound or its prepolymer.
It is possible to mix in a proportion of 35% by weight.

As the curing agent for the resin composition of the present invention, known ones can be used. For example, protic acid typified by hydrochloric acid and phosphoric acid; aluminum chloride,
Boron trifluoride complex, Lewis acid typified by zinc chloride;
Aromatic hydroxy compounds typified by phenol, pyrocatechol, and dihydroxynaphthalene; organic metal salts such as zinc naphthenate, cobalt naphthenate, tin octylate, and cobalt octylate; tertiary such as triethylamine, tributylamine, quinoline, isoquinoline, etc. Amines; quaternary ammonium salts represented by tetraethylammonium chloride and tetrabutylammonium bromide; imidazoles; sodium hydroxide, sodium methylate, diazabicyclo- (2,2,2) -octane, triphenylphosphine, or these And the like, but more preferably to achieve the purpose,
Organic metal salts such as zinc naphthenate, cobalt octylate and tin octylate, or a mixed system of these organic metal salts and imidazoles is used.

Other thermosetting resins can be used in combination with the resin composition of the present invention as long as the purpose is not impaired. Examples include epoxy resins represented by diglycidyl ethers of bisphenol A and bisphenol F, glycidyl ethers of phenol novolac and cresol novolac, bisvinylbenzyl etherification products of bisphenol A and tetrabromobisphenol A, vinylbenzyl ether of diaminodiphenylmethane. Compound represented by alkenyl aryl ether resin,
Bisphenol A and tetrabromobisphenol A
Alkynyl ether resins represented by dipropargyl ether, diaminodiphenylmethane propargyl ether, etc., other, phenol resins, resole resins, allyl ether compounds, allylamine compounds, triallyl cyanurate, triallyl isocyanurate, vinyl group-containing polyolefin Examples thereof include compounds, but are not limited thereto. Thermoplastic resins can also be added and include, but are not limited to, polyphenylene ether, polystyrene, polyethylene, polybutadiene, polyimide, and modified products thereof. These resins may be mixed in the cyanate resin composition, or may be reacted in advance and used.

In the present invention, known additives such as a curing accelerator, a flame retardant, a release agent, a surface treatment agent and a filler may be added to the composition depending on the purpose of use. Imidazoles, tertiary amines, phosphorus compounds, alkylphenols as curing accelerators, antimony trioxide, red phosphorus, etc. as flame retardants, waxes, zinc stearate, etc. as mold release agents, and Examples of the surface treatment agent include silane coupling agents. Examples of the filler include silica, alumina, talc, clay, glass fiber and the like.

The cyanate resin composition of the present invention is used for laminated boards such as printed wiring boards, sealing of electronic parts, and other uses. Using the resin composition of the present invention, as a method for making a laminate, the resin composition is methyl ethyl ketone, methyl isobutyl ketone, ethylene glycol monomethyl ether, propylene glycol dimethyl ether, toluene, xylene, 1,4-dioxane, tetrahydrofuran, Evenly dissolved using an organic solvent such as dimethylformamide, glass fiber, polyester fiber,
Examples include a method in which a prepreg obtained by impregnating a base material made of a woven cloth, a mat, a paper or a combination thereof made of an organic or inorganic fiber such as polyamide fiber or alumina fiber, and dried by heating is hot press molded. The method is not limited to.

[0028]

EXAMPLES Examples of the present invention will be shown below, but the present invention is not limited thereto.

Synthesis Example 1 This synthesis example relates to a process for producing a dicyanate of 1,1-bis (5-t-butyl-2-methyl-4-hydroxyphenyl) butane, which is a cyanate compound.
200 g (1.05 moleq) of 1,1-bis (5-t-butyl-2-methyl-4-hydroxyphenyl) butane (Sumitomo Chemical Co., Ltd., trade name Sumilizer BBM-S) was dissolved in 800 g of acetone. , -5 ° C. Chlorsian
After adding 77.3g (1.26mol), triethylamine 111.3
g (1.10 mol) was added dropwise over 1 hour, taking care not to let the reaction temperature rise above 0 ° C. After completion of the dropping, the mixture is kept warm at 2 to 5 ° C for 1 hour and then diluted with 500 g of chloroform. After removing the salt by filtration, it was washed with water and the solvent was distilled off under reduced pressure to obtain 194.8 g of a yellow resinous material.

The cyanate compound obtained in this way, the results of infrared absorption spectrometry, the absorption 3200-3600Cm ^-1 phenolic OH disappeared and it was confirmed to have an absorption 2270 cm ^-1 of the nitrile of cyanate It was

Synthesis Example 2 This synthesis example relates to a process for producing N, N'-bis (4-aminophenoxyphenyl) menthane bismaleimide, which is the polymaleimide compound used in the present invention. Maleic anhydride 23 in a 5 liter four neck flask
7.3 g and 2373 g of chlorobenzene were charged and stirred under a nitrogen stream to dissolve them. YP-90 (trade name, manufactured by Yasuhara Chemical, reactive compound of dipentene and phenol,
Dimethylacetamide (DMA) of (4-aminophenoxyphenyl) menthane obtained by reacting hydroxyl equivalent of 162 g / eq) with p-chlorobenzene and then reducing
c) Solution (concentration adjusted to 34.3% by weight) 1625.
1 g was added dropwise to the flask at 25 ± 5 ° C. over 2 hours using a dropping funnel. The reaction was continued at 35 ° C. for 2 hours to complete the amidation reaction.

Subsequently, p-toluenesulfonic acid monohydrate 1
0.46 g was added, and while performing azeotropic dehydration under reduced pressure, 10
The dehydration ring closure reaction was carried out at 0 ° C. for 1 hour, 110 ° C. for 1 hour, and then at 135 ° C. for 4 hours while gradually returning to normal pressure. The produced water was separated from the system using a Dean-Stark azeotropic dehydrator to proceed the reaction. Then, under reduced pressure, a total of 89% of chlorobenzene and subsequently DMAc were recovered.
Then 2200 g of methyl isobutyl ketone (MIBK)
Was added and dissolved. Cool the solution to 60 ° C, then
Baking soda and water 1 so that the pH of the aqueous layer is 5 to 7
After the addition of 000 g for neutralization, washing and liquid separation were performed. After further washing twice with 1000 g of 15% saline at 60 ° C., liquid separation was performed, azeotropic dehydration was performed under reduced pressure, and salts were removed by filtration. The filtrate is concentrated under reduced pressure, finally at 150 ° C / 5To
After reaching the condition of rr, the product was taken out from the flask in a molten state, and a light brown solid was obtained in an amount of 724 g (yield 98.7).
%). According to gel permeation chromatography (GPC), 95% of N, N′-bis (4-aminophenoxyphenyl) menthane bismaleimide and 5% of high molecular weight component were contained.

The physical properties of this product are shown below. Mass spectrum M + = 666-Melting point 96-98 ° C-1H-NMR spectrum δ: 0.6-2.1 ppm (m, aliphatic), 2.8 p
pm (m, methine), 6.8 ppm (s, imide group), 6.9 to 7.4 ppm (m, aromatic) -Infrared absorption spectrum: 1238 cm ^-1 (ether bond), 1712 cm ^-1 (Imide bond)

Synthesis Example 3 This synthesis example relates to a process for producing bis (4-aminophenoxyphenyl) dicyclopentane bismaleimide, which is the polymaleimide compound used in the present invention.
In Synthesis Example 2, YP-90 (trade name, manufactured by Yasuhara Chemical,
Reaction compound of dipentene and phenol, hydroxyl equivalent 1
62 g / eq) instead of bis (4-aminophenoxyphenyl) menthane, DPP-600T
932.9 g of a DMAc solution of bis (4-aminophenoxyphenyl) dicyclopentane similarly derived from (trade name, manufactured by Nippon Oil Co., Ltd.) (concentration: 34.3%)
The same operation as in Synthesis Example 2 is performed using
7.4 g (98% yield) of bis (4-aminophenoxyphenyl) dicyclopentane bismaleimide 191.7
g (yield 97.4%) was obtained as yellow crystals.

The physical properties of this product are shown below. Mass spectrum M + = 662, 1060 1H-NMR spectrum δ: 1.0 to 2.5 ppm (m, aliphatic), 2.7 pp
m (m, methine), 6.8 ppm (s, imide group),
6.6 to 7.3 ppm (m, aromatic) Infrared absorption spectrum: 1222 cm ^-1 (ether bond), 1712 cm ^-1 (imide bond)

Synthesis Example 4 This synthesis example is the polymaleimide compound used in the present invention, N, N'-bis [4- (4-aminophenoxy) -3,5-dimethylphenyl] dicyclopentane bismaleimide. The present invention relates to a method for producing an oligomer. 1
58.8 g of maleic anhydride in a 4-liter four-necked flask
And 137.2 g of acetone were charged, and they were dissolved by stirring under a nitrogen stream. A dicyclopentane oligomer having 4- (4-aminophenoxy) -3,5-dimethylphenyl groups at both ends while maintaining the temperature at room temperature to 35 ° C. [Nippon Oil Co., Ltd. DXP-L-9-1 (2, Reaction product of 6-xylenol and dicyclopentadiene, hydroxyl equivalent 191 g
/ Eq) is reacted with p-chloronitrobenzene and then the nitro group is reduced. 90% of bis [4- (4-aminophenoxy) -3,5-dimethylphenyl] dicyclopentane is contained by GPC measurement. Amine equivalent 275
A solution prepared by dissolving 150.0 g of (g / eq) in 350 g of acetone was added dropwise to the flask over 2 hours. Stirring was continued for another 3 hours. Next, after adding 16.6 g of triethylamine and stirring at room temperature for half an hour, 0.58 g of nickel acetate was added and 4
The temperature was raised to 0 ° C. After 72.4 g of acetic anhydride was added dropwise over 1 hour, the temperature was kept at the same temperature until the reaction was completed. After the reaction was completed, the reaction mixture was added to 1000 g of pure water. The crystals were collected by filtration, washed with water and then with methanol, heated under reduced pressure and dried. Yield 189.
Obtained in 4 g (yield 97.9%).

The physical properties of this product are shown below. -Mass spectrum M + = 718- 1H-NMR spectrum δ: 1.0 to 2.5 ppm (m, aliphatic), 2.7 p
pm (m, methine), 6.8 ppm (s, imide group), 6.5-7.3 ppm (m, aromatic) -infrared absorption spectrum: 1220 cm ^-1 (ether bond), 1714 cm ^-1 (Imide bond)

Synthesis Example 5 In this synthesis example, N, N'-1,1-bis [4- (4-aminophenoxy) -5-t-butyl-2-, which is the polymaleimide compound used in the present invention, is used. The present invention relates to a method for producing methylphenyl] butane bismaleimide. A 2-liter four-necked flask was charged with 97.1 g of maleic anhydride and 226.5 g of acetone, and dissolved by stirring under a nitrogen stream. 1,1-bis [4- (4-aminophenoxy) -5-t-butyl-2 while keeping the temperature at room temperature to 35 ° C.
-Methylphenyl] butane 256.5 g was added to acetone 59
The solution dissolved in 8.5 g was added dropwise over 2 hours. Stirring was continued for another 3 hours. After adding 27.3 g of triethylamine and stirring at room temperature for half an hour, 0.95 g of nickel acetate was added and the temperature was raised to 40 ° C. After adding 119.9 g of acetic anhydride dropwise over 1 hour, the reaction was continued at the same temperature. After completion of the reaction, the reaction mixture was put into 2.5 kg of water, and the crystals were collected by filtration. The crystals were washed with water and then with methanol, heated under reduced pressure and dried. Yield 306.1 g of the desired product as yellow crystals.
(Yield 93.9%). This product can be recrystallized from a mixed solvent of methyl cellosolve / isopropyl alcohol.

The physical properties of this product are shown below. Melting point 127 to 130 ° C., mass spectrum M + = 724 · 1H-NMR δ: 0.97 ppm (t, -CHCH 2 CH 2 C
_{H 3), 1.34 ppm (s} , t- butyl group), 1.
_{92 ppm (q, -CHCH 2 CH} 2 CH 3), 2.
17 ppm (s, methyl group), 4.13 ppm
_{(T, -CHCH 2 CH 2 CH} 3), 6.65 ppm
(S, imide group), 6.8 to 7.2 ppm (m, aromatic) Infrared absorption spectrum: 1219 cm ^-1 (ether bond) 1712 cm ^-1 (imide bond)

Example 1 This example relates to an example of producing a cured product of a resin composition using the cyanate compound obtained in Synthesis Example 1.
0.1% by weight of zinc naphthenate is melt-mixed with the cyanate compound obtained in Synthesis Example 1 and methyl ethyl ketone is added to prepare a 50% by weight solution. After prepolymerization at 180 ° C, press at 200 ° C / 50kg / cm ² for 30 minutes, then 20
By post-curing at 0 ° C. for 2 hours, a cured product having a thickness of about 2 mm was obtained.

Example 2 This example relates to an example of preparing a cured product of the cyanate compound obtained in Synthesis Example 1 and the diglycidyl ether of tetrabromobisphenol A. 80 parts of the cyanate compound obtained in Synthesis Example 1 and diglycidyl ether of tetrabromobisphenol A (Sumitomo Chemical Co., Ltd.,
0.3 part of zinc naphthenate is mixed with 20 parts of trade name Sumiepoxy ESB-400T) and methyl ethyl ketone is added to prepare a 50 wt% solution. After prepolymerization at 180 ° C, press at 200 ° C / 50kg / cm ² for 30 minutes, then 230
By post-curing at 5 ° C. for 5 hours, a cured product having a thickness of about 2 mm was obtained.

Comparative Example 1 This comparative example relates to an example of producing a cured product of a resin composition using dicyanate of bisphenol A. A bisphenol A dicyanate was used to prepare a cured product having a thickness of 2 mm in the same manner as in Example 1.

Comparative Example 2 This comparative example relates to an example of preparing a cured product of a resin composition using dicyanate of bis (3,5-dimethyl-4-hydroxyphenyl) methane (bisphenol F). Using the above dicyanate, a thickness of 2 was obtained in the same manner as in Example 1.
A mm cured product was prepared.

Table 1 shows the glass transition temperatures and dielectric constants of the cured products obtained in Examples 1-2 and Comparative Examples 1-2.

[0045]

[Table 1]

Examples 3 to 8 The cyanate compound obtained in Synthesis Example 1 was used at 140 ° C. together with zinc naphthenate which is a curing agent.
Was melt-mixed with and prepolymerized. This cyanate prepolymerized product and the polymaleimide compound obtained in Synthesis Examples 2 to 5, or N, N'-bis (4-aminophenyl) methane bismaleimide (manufactured by KI Kasei Co., Ltd.), N, N '-2,2-bis (4-aminophenoxyphenyl) propane bismaleimide (trade name, MB80
No. 00, manufactured by Mitsubishi Petrochemical Co., Ltd.) was mixed with a curing agent in the proportions shown in Table 2, and hot pressed at 200 ° C./50 Kg / cm ² for 2 hours to prepare a cured product. Table 2 shows these physical property values. The numerical values of the compounding ratios in the table show parts by weight.

Comparative Example 3 Using a bisphenol A dicyanate compound, Table 2
A cured product was prepared in the same manner as in Examples 3 to 8 by using the compounding ratio of. Table 2 shows these physical property values.

[0048]

[Table 2]

In Tables 1 and 2, the physical properties were measured by the following methods. Glass transition temperature: Measured using a thermomechanical analyzer DT-30 manufactured by Shimadzu Corporation.・ Dielectric constant, dielectric loss tangent: Electrostatic capacitance value obtained by using 4275A Multi-Frequency LCR meter manufactured by Yokogawa Hewlett-Packard Co., Ltd. by making electrodes with metallic paint on both sides of a cured product with a thickness of about 2 mm. It was calculated and obtained.

[0050]

EFFECT OF THE INVENTION The cyanate resin composition of the present invention provides a cured product having excellent low dielectric properties and heat resistance (for example, a glass transition temperature of 180 ° C. or higher) that can withstand practical use.

Front page continued (72) Inventor Hisashi Watanabe 6 Kitahara, Tsukuba, Ibaraki Prefecture Sumitomo Chemical Co., Ltd. (72) Inventor Mitsuhiro Shibata 6, Kitahara, Tsukuba, Ibaraki Sumitomo Chemical Co., Ltd. (72) Inventor Shuichi Kanagawa Ibaraki 6 Kitahara, Tsukuba, Japan Sumitomo Chemical Co., Ltd.

Claims (6)

[Claims] 1. The following general formula (1): (In the formula, R ₁ and R ₂ are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. A is an alkyl group having 1 to 3 carbon atoms, and i is 0 to 3 The cyanate resin composition comprises a cyanate compound represented by the following integer) or a prepolymer thereof and a curing agent as essential components. 2. A cyanate compound represented by the general formula (1) according to claim 1 or a prepolymer thereof, a brominated epoxy compound or a prepolymer thereof, and a curing agent as essential components. Cyanate resin composition. 3. A prepolymer obtained by melt-mixing a cyanate compound represented by the general formula (1) according to claim 1 and a brominated epoxy compound with a curing agent alone or as a mixture, and a curing agent. The cyanate resin composition according to claim 2, which comprises as an essential component. 4. A cyanate compound represented by the general formula (1) or a prepolymer thereof according to claim 1, a curing agent, and a polymaleimide compound having two or more N-maleimide groups in the molecule or a compound thereof. A cyanate resin composition comprising a prepolymer as an essential component. 5. A polymaleimide compound has the following structural formula (2): [In the formula, X represents the following structural formulas (3), (4), (5),
(6), (7) or (8) [Chemical 4] [Chemical 5] [Chemical 6] (In the formula, n-Pr represents an n-propyl group.) [Chemical 8] Is a group represented by. The cyanate resin composition according to claim 4, which is a compound represented by the formula (4). 6. A cyanate compound has the following structural formula (9): A cyanate compound represented by:
The cyanate resin composition according to 3, 4, or 5.