JPH0234621A - Fluorinated phenol resin, its composition and its use - Google Patents

Abstract

PURPOSE:To make it possible to form a semiconductor device sealing agent which has low permittivity, excellent heat resistance, low water absorptivity and low moisture permeability by using a fluorinated resol phenolic resin having specified structural units. CONSTITUTION:This fluorinated resol phenolic resin has structural units of formula I[wherein Rf is formula II (wherein n is 1-40), formula III (wherein R', R'' and R''' are each F, CF3, C2F5, C3F7 or the like), or the like; X1 is a single bond, -O-, -OCH2-, formula IV, formula V or -N(CH2)2-; R1 is an alkyl, an alkoxy, Cl, Br, F, a phehyl or a fluoroalkyl]. This resin can be used also in combination with a polyepoxy compound, an N-substituted unsaturated imide compound or a poly-p-vinylphonol compound.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention provides a fluorine-containing phenolic resin composition that can have a low dielectric constant, has excellent heat resistance, and has low water absorption and moisture permeability. The present invention relates to a semiconductor device encapsulant made of the same, and a laminate material made of the composition.

[Conventional technology]

Conventionally, epoxy-based materials using a novolac type phenol resin as a curing agent have been the mainstream for resin compositions for encapsulating resin-encapsulated semiconductor devices. However, with the increase in the degree of integration of semiconductor devices and the expansion of applications for resin-encapsulated semiconductor devices, resin compositions for encapsulation are becoming increasingly expensive.

Furthermore, there is a strong desire to develop a resin composition that has excellent heat resistance, moisture resistance, and adhesion, and is also capable of reducing stress (see JP-A-61-9415).

[Problem to be solved by the invention]

However, phenol novolac resin-cured epoxy compositions have a limited ability to improve heat resistance, especially the glass transition point, and have relatively high water absorption and moisture permeability. There was an essential problem in preventing the intrusion. To deal with this problem, attempts have been made to modify the surface treatment by adding siloxane-based or fluoro-based surface treatment agents, but even in this case, there are problems such as mold staining during molding and the appearance of the molded product that needs to be improved. .

The objects of the present invention are a fluorine-containing phenolic resin composition that can have a low dielectric constant, has excellent heat resistance, and has low water absorption and moisture permeability, an encapsulant for semiconductor devices made of this composition, and a sealant for semiconductor devices comprising this composition. An object of the present invention is to provide a material for a laminate consisting of.

[Means to solve the problem]

As a means to achieve the above object, the inventors investigated fluorine modification of resol type phenolic resin and found that the following items were satisfactory. The gist is: (1) - maximum (1) % formula % Ca F 7 or -C-CF s2F11. Further, Xl is either none or -0--〇CH2-. Further, R1 is any one of an alkyl group, an alkoxy group, CQ, Br, F, a phenyl group, and a fluoroalkyl group. ] A fluorine-containing resol type phenolic resin containing a structural unit represented by the following.

(2) - maximum [I) (R', R' and R'' are F, CF3, CzFs+2
F3 C3F? Or it is any zF5 among -C-CFs. Moreover, Xt is either none, -0-, or -0CHz-. Further, R1 is any one of an alkyl group, an alkoxy group, CQ, Br, F, a phenyl group, and a fluoroalkyl group. ] A composition containing a fluorine-containing resol type phenolic resin containing a structural unit represented by the following.

(3) A composition comprising the fluorine-containing resol type phenolic resin of (1) and a polyfunctional epoxy compound.

(4) A semiconductor device coated and/or encapsulated using the composition of (3).

(5) A laminate using the composition of (2).

(6) A prepreg using the composition of (2).

(7) A printed circuit board using the composition of (2).

(8) A semiconductor encapsulation material using the composition of (2).

(9) The fluorine-containing resol type phenolic resin of (1) and N
- A composition characterized by containing an unsaturated imide-based compound.

(to) A composition comprising the fluorine-containing resol type phenolic resin of (1) and a poly-P-vinylphenol compound.

[Effect]

This is essential for achieving the effects of the present invention. The fluorine-containing resol type phenolic resin containing the structural unit of
Examples include:

(R', R' and R'' are F + CF 3r C2F
Either C:2F5 in 5+2F5 C3F T or -C-CFs. Also, Xl is none, -〇-2-〇GHz -
It's either inside. Further, R1 is any one of an alkyl group, an alkoxy group, CQ, Br, F, a phenyl group, and a fluoroalkyl group. ] Table (m; 1-40) CF 3 CF3 etc. These are dehydrated and condensed by themselves to crosslink and harden. Further, a curing accelerator such as a metal oxide, a metal hydroxide, or an amine compound such as hexamethylenetetramine may be used in combination.

In the present invention, general formula (1) % formula % 03F! Alternatively, it is either 2F3 in -C-CFs. Moreover, Xz is either none, -0-, or -0CHz-. In addition, R1 is alkyl L (, alkoxy group,
It is any one of CQ, Br, F, phenyl group, and fluoroalkyl group. ] A fluorine-containing resol type phenolic resin containing a structural unit represented by Rr C1-1zOH (n is 1 to 40) or and/or R' The fluorine-containing compound represented by the formula (same as above) and the general formula (III) may be used.

In the present invention, the perfluoroalkyl ether onogama represented by the formula % is available from Asahi Glass Co., Ltd., where n is up to 40.

Moreover, it is either one of the formula [wherein, Xl is none, -〇-9-〇CH2-]. In addition, Rz is an alkyl group, an alkoxy group, CQ
, Br, F, phenyl group, or fluoroalkyl group. It is obtained by heating and reacting a resol type phenol resin containing a structural unit represented by ] in the presence of a basic catalyst such as a tertiary amine.

A detailed explanation of this reaction can be found in Journal of the Chemical Society of Japan, 1978, 2.
Please refer to the method described on page 53 [In the formula,
R', R'' and R'' are F, CF3.

CzF5. Any of C3F7, and may be the same or different. ] Examples of the fluorine-based compound represented by the formula include hexafluoropyrene or hexafluoropyrene oligomer, and specifically, these compounds are commercially available from ICI Mond Division and the like. Among these compounds, T-2 or the following are preferred in order to exhibit the effects of the present invention.

In addition, examples including the structural unit represented by the general formula [■].

O1+ RI CHxLIH There is.

In the present invention, the fluorine-containing resol type phenol resin represented by the general formula (1) can be used in combination with a polyfunctional epoxy compound. These include, for example, diglycidyl ether of bisphenol A, butadiene diepoxide, 3,4-epoxycyclohexylmethyl-(3,4-
epoxy) cyclohexane carboxylate, vinyl cyclohexane dioxide, 4,4'-di(1,2-epoxyethyl) dibiphenyl ether, 4,4'(1,2
-epoxyethyl)biphenyl, 2,2-bis(3,4
-Epoxycyclohexyl)propane, diglycidyl ether of resorcinol, diglycidyl ether of phloroglucin, diglycidyl ether of methylphloroglucin, bis-(2°3-epoxycyclopentyl)ether, 2-(3,4-epoxy)cyclohexane- 5,5-
Spiro(3,4-epoxy)-cyclohexane-m-dioxane, bis-(3,4-epoxy-6-methylcyclohexyl)adipate, N,N'-m-phenylenebis(4,5-epoxy-1゜2 -Difunctional epoxy compounds such as dicarboximide (cyclohexane).

Triglycidyl ether of para-aminophenol, polyallyl glycidyl ether, 1,3.5-tri(1,2
-epoxyethyl)benzene, 2°2', 4.4'
-Tetraglycidoxybenzophenone, tetraglycidoxytetraphenylethane.

Polyglycidyl ether of phenol formaldehyde novolac, triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane or.

The following formula lower alkyl group, Fluoroal Ru.

) are trifunctional or higher functional epoxy compounds.

Also, The following epoxy compounds are: in molten state Has liquid crystal orientation.

Adding heat resistance to cured products, mechanical strength Every time, Improved adhesion, Very effective in improving electrical characteristics, etc. Hey.

Such compounds include for example, and so on.

Also, The polyfunctional epoxy compound in the present invention includes the following: general formula [] class alkyl group.

Fluoroalkyl group, 10-C-S--S○2 scale tlaCCH3. ] By using an alicyclic epoxy compound having an etherimide bond represented by the formula above, it is possible to provide a cured product with excellent heat resistance, flexibility, moisture resistance, electrical properties, and optical properties.

- Alicyclic epoxy compounds having an etherimide bond represented by maximum (III) are, for example, the compounds shown below. That is, etc.

Conventionally known curing agents for epoxy compounds can also be used in combination with the resin composition of the present invention. They are 5 Hiroshi Kakiuchi: Epoxy Resin (published September 1970) pages 109-149, Lee, Neville: EpoxyRes
ins(McGraw-11i11 Book Com
pany Inc: New York.

Published in 1957) pages 63-141, P, E, I'3
Written by runis: Epoxy Re5ins Techn
(Interscience Public
-shers, New York, published 1968)4
Compounds described on pages 5 to 111, for example,
Aliphatic polyamines, aromatic polyamines, amines including secondary and tertiary amines, carboxylic acids, carboxylic acid anhydrides, aliphatic and aromatic polyamide oligomers and polymers, boron trifluoride-amine complexes, phenolic resins , melamine resins, urea resins, urethane resins, and other synthetic resin initial condensates, as well as dicyandiamide, carboxylic acid hydrazide, polyaminomaleimide, and the like.

One or more of these curing agents can be used depending on the use and purpose.

The resin composition of the present invention may contain a catalyst that promotes the curing reaction between the epoxy compound and the fluorine-containing novolak phenol resin.

Such catalysts include, for example, tertiary amines such as triethanolamine, tetramethylbutanediamine, tetramethylpetanediamine, tetramethylhexanediamine, triethylenediamine, dimethylaniline, dimethylaminoethanol, dimethylaminobetanol, etc. Oxyalkylamines and tris(dimethylaminomethyl)
There are amines such as phenol, N-methylmorpholine, and N-ethylmorpholine.

Also, cetyltrimethylammonium bromide, cetyltrimethylammonium chloride, dodecyltrimethylammonium iodide.

There are quaternary ammonium salts such as trimethyldodecyl ammonium chloride, benzyldimethyltetradecylammonium chloride, benzylmethylpalmitylammonium chloride, allyldodecyltrimethylammonium bromide, benzyldimethylstearylammonium bromide, stearyltrimethylammonium chloride syl ammonium acetate.

Also, 2-ethylimidazole, 2-undecylimidazole, 2-heptadecyl imidazole, 2-methyl-
4-ethylimidazole, 1-butylimidazole, 1
-Propyl-2-methylimidazole, 1-benzyl-
2-Methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-azine-2-methylimidazole, 1-azine-2-undecyl Imidazole such as imidazole, triphenylphosphine tetraphenylborate, tetraphenylphosphonium tetraphenylborate, triethylamine tetraphenylborate, N-methylmorpholine tetraphenylborate, 2-ethyl-4-methylimidazole tetraphenylborate, 2-ethyl Examples include tetraphenylborate such as -1,4-dimethylimidazole tetraphenylborate.

Also, 1,5-diaza-bicyclo(4,2,O)octene-5,1,8-diaza-bicyclo(7.

2,0) undecene-8,1,4-diazabicyclo(3
,3,O)octene-4,3-methyl-1,4-diazabicyclo(3,3,O)octene-4,3,6,7.7
-Titramethyl-1,4-diaza-dicyclo(3,3
,O)octene-4,1,5~diaza-bicyclo(3,
4,O) nonene-5,1,8-diaza-bicyclo(7,
3,O) dodecene-8,1,7-diazabicyclo(4,
3.

0) Nonene-6,1,5-diazabicyclo (4.

4,0) Decene-5,1,8-diazabicyclo(7,4
,O) tridecene-8,1,8-diazabicyclo(
5,3,O)decene-7,9-methyl-1,8-diazabicyclo(5,3,O)decene-7,1,8-diazabicyclo(5,4,O)undecene-7,1,6- Diazabicyclo (5,5.

0) Dodecene-6,1,7-diazabicyclo (6.

5,O))-lysocene-7,1,8-diazabicyclo(
7,5,O)tetradecene-8,1.10-diazabicyclo(7,3,O)dodecene-9, ■.

10-diazabicyclo(7,4,O) tridecene-
9,1,14-diazabicyclo(11,3,O)hexadecene-13,1,14-diazabicyclo(1 1,4
, O) diazabicyclo-alkenes such as hebutadecene-13 are also useful. One or more of these compounds can be used in combination depending on the purpose and use.

In the present invention, the fluorine-containing resol type phenolic resin represented by -maximum (r) is -maximum (rV) [wherein D is a dicarboxylic acid residue having an ethylenically unsaturated double bond. , x3 is an alkylene group, an arylene group, or
Indicates those substituted divalent organic groups. It can be used in combination with an N,N'-substituted bis-unsaturated imide compound represented by the following formula. For example, N, N'-
Ethylene bismaleimide, N,N'-hexamethylene bismaleimide, N,N'-dodecamethylene bismaleimide, N,N'-m-phenylene bismaleimide,
N, N'-p-phenylene bismaleimide, N, N'
p-phenylenebiscitraconimide, N, N'
-p-phenylene bispiroshiconimide, N, N'
-p-phenylene-endomethylenetetrahydrophthalimide, N, N'-4,4' diphenylmethane bismaleimide, N, N'-4°4' dicyclohexylmethane bismaleimide, N.

N'-m-xylene bismaleimide, N,N'diphenylcyclohexane bismaleimide, 4゜4'bismaleimide cinnamanilide, 6,6'bismaleimide-2,
2'-bipyridine, or ]13C H3 11aCCl1a Cl1a CFa.

It is also one of -maximum (V) Q -CI-40GHzCH=C)Iz)-. ). Also, R6 and R7
are H, CD, Br, F, CHs, C2H5, C3
J-I7゜CF3. CzH5, C51-(7), and may be the same or different from each other. However, if one is I(, R6≠R7.

Also.

R', R', R'' is F, CF3, C2F!1
．． It can also be used in combination with a fluorine-containing unsaturated monoimide compound represented by ], which is any one of C3F71C4FD and may be the same or different from each other. Examples of such things include the following.

etc.

Or, the next H3 2H5 F3 aC FaCCF (CF3)! Either F3C CF(CF3)2. Further, Rδ is any one of H2 lower alkyl group, perfluoroalkyl group, CQ, and Br. It is also effective to use a phenol derivative having a perfluoroalkyl ether substituent represented by the formula [■] or the like.

In addition, the fluorine-containing resol type phenolic resin represented by the general formula (1) of the present invention has the following formula (VD, or
Formula [■] [In the formula, m is 1 to 4o. p is 1-8, q is O-7
And 2 < p + q < 8. Also, X is
H, -c=N, -CH2-CH-CH2-
1 [In the formula, 1 m is 1 to 40. p is 2-200, q is O
~2oO. Also, X1iH, -CEN.

Furthermore, R8 is any one of H2 lower alkyl group, perfluoroalkyl group, CQ, and Br. There is no problem in using together a polyvinylphenol derivative having a perfluoroalkyl ether substituent represented by the following formula.

Specific compounds represented by formula (1) and formula (II) include the following.

CF3 [In the above formula, p, q and R are the same as above. 〕and so on.

Further, the following fluorine-containing phenolic oligomers can also be used in combination. Specific examples include the following.

The composition of the present invention can be exposed to heat, ultraviolet rays, visible light,
The crosslinking reaction progresses due to actinic rays such as electron beams and X-rays.
It becomes a hardened molded product.

That is, when the purpose is to enhance the polymerization effect by actinic rays, conventionally known sensitizers and photopolymerization initiators can be added to the composition of the present invention.

Sensitizers and photoinitiators include Michler's ketone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, 2-te
rt-butylanthraquinone, 1,2-benzo-9,1
0-anthraquinone, 4,4'-bis(diethylamino)benzophenone, acetophenone, benzophenone,
Examples include thioxanthone, 1,5-acenaphthene, and N-acetyl-4-nitro-1-naphthylamine.

The amount added is preferably 0.1 to 50 parts by weight per 100 parts by weight of the fluorine-containing resol type phenolic resin of the acid product of the present invention.

Furthermore, various materials may be blended into the resin composition of the present invention depending on its use. That is, for example, for use as a molding material, zircon oxide, silica, alumina, aluminum hydroxide, titania, subsalt flower, calcium carbonate,
Inorganic fillers such as magnesite, clay kaolin, talc, silica sand, glass, fused silica glass, asbestos, mica, various whiskers, carbon black, graphite, and molybdenum disulfide, higher fatty acids, and waxes. mold release agents, such as epoxy silane, vinyl silane,
Coupling agents such as borane and alkoxy titanate compounds may be incorporated.

Further, flame retardant imparting agents such as halogen-containing compounds, antimony oxide, and phosphorus compounds can be used as necessary.

In addition, various polymers such as polystyrene, polyethylene, polybutadiene, polymethyl methacrylate, polyacrylic ester, acrylic ester-methacrylic ester copolymer, phenolic resin, phenoxy resin,
Known resin modifiers such as melamine resin, urea resin, polyvinyl butyral, etc. can be used.

〔Example〕

<Example 1> Method for producing monofluorine-containing resol type resin - The following three types were used as resol type phenolic resins.

a) Phenol and formalin were subjected to a dehydration condensation reaction in the presence of a loading soda catalyst to obtain a resol type phenolic resin RF-(A) having methylene bonds. The number average molecular weight of this resin is 1375.

b) Phenol and formalin were subjected to a dehydration condensation reaction in the presence of an ammonia catalyst to obtain a resol type phenol resin RF-(B) having a methyleneimine bond. The number average molecular weight of the resin is 480.

C) Performing a dehydration condensation reaction of orthocresol and formalin in the presence of a dicyandiamide catalyst.

A resol type phenolic resin RF-(C) was obtained.

The number average molecular weight of this resin is 420.

The following two types of perfluoroalkyl ether oligomers were used.

The fluorine-containing resol type resin of the present invention is prepared by blending the above-mentioned resol type phenol resin and perfluoroalkyl ether oligomer in the predetermined amounts (parts by weight) shown in Table 1. 2-pyrrolidone (NMP
) A reaction was carried out in an equal amount mixed solution in a nitrogen atmosphere in the coexistence of a triethylamine catalyst, followed by repeated washing with water and drying under reduced pressure to obtain a fluorine-containing resol resin of the chemical type.

<Examples 2 to 9> FRF-(A) and FRF-(B) obtained in Example 1 as fluorine-containing resol type phenolic resins.

Five types were selected: FRF-(C), FRF-CD), and FRF-(E). In addition to these, bisphenol A type epoxy DER332 (manufactured by Dow Chemical Company), orthodiallyl bisphenol F, 2°2-bis(4-(4-
Alechmidophenoxy)phenyl]hexafluoropropane (abbreviated).

DAPP-FMI) and triallyl isocyanurate (TAIC) were separately blended in the predetermined amounts (parts by weight) shown in Table 2 to make the following formulations. To these formulations were added dicyandiamide, benzoguanamine, and dicumyl peroxide (DCPO) as curing accelerators, and predetermined amounts of epoxysilane KBM403 (manufactured by Shin-Etsu Chemical Co., Ltd.) as a coupling agent.

These formulations were then dissolved in an isostatic mixture of N-methyl-2-pyrrolidone (NMP) and methyl ethyl ketone (MEK) to form a varnish containing 45-48% solids by weight.

Using this varnish solution, apply a glass cloth (WE-made by Nittobo Co., Ltd.)
116P, BY-54), coated with resin and heated at 160°C.
The coated cloth was dried for 13 minutes to prepare a coated cloth having a resin content of 45 to 48% by weight.

Next, apply a sheet to this coated cloth, and apply a layer of 35 μm above and below it.
Thick TAI-treated copper foil (Furukawa type knee CFC Co., Ltd. v5) was stacked and heated at 170 to 185°C and 40 kg-f/d.
A double-sided copper-clad laminate with a thickness of about 1.6 nwn was produced by laminating and bonding for 0 minutes.

This copper-clad laminate was further post-cured at 200° C. for 4 hours. The various properties of the resulting copper-clad laminates were
Shown in the table.

The method for measuring each characteristic is as follows.

(a) Copper foil peeling strength After cutting a test piece into a size of 25+m x 100m from the tensile laminate, leave a copper foil with a width of 101m in the center.
Other copper foils were removed by etching.

Next, the copper foil in the center was peeled off in the vertical direction at a rate of 5 mm/min, and its strength was measured.

(b) A test piece was cut into a 25 mm square piece from a solder heat resistant copper clad laminate. This test piece was floated in a solder bath heated to 300°C, and the time required for abnormalities such as blistering to occur was measured.

(c) Anti-inflammatory properties were measured according to the UL-94 vertical method. A test piece was cut from the above copper-clad laminate to a width of 12 mm and a length of 125 m, and a copper foil was etched thereon. Ten test pieces were each measured and expressed as an average flame-out time.

In addition, the average flame-out time is within 5 seconds, the longest flame-out time is within 10 seconds, and V-0 is UL-94, and the average flame-out time is within 25 seconds, and the longest flame-out time is within 30 seconds, which is UL-94 and V-1.

<Examples 10-20. Comparative Example> As a polyfunctional epoxy compound, a fluorine-containing resol type phenol resin was used for 100 parts by weight of an orthocresol novolac type epoxy resin EOCN-12O3 (manufactured by Hitachi Chemical Co., Ltd., epoxy equivalent weight 211, softening point 66.4°C).
The two types of FRF-(F) and FRF-(G) obtained in Example 1 were also combined with novolac type phenolic resin HP-607.
N (manufactured by Hitachi Chemical Co., Ltd., softening point 78-82°C), poly P-hydroxystyrene M resin (manufactured by Marukubi Sekiyu Co., Ltd., number average molecular weight 4800), N,N'-bismaleimide-4,4'
- Picked up diphenylmethane.

The prescribed amounts shown in Table 1 were blended.

To these formulations, 2.0 parts by weight of triphenylphosphine was added as a curing accelerator, and 2.0 parts by weight of epoxysilane KBM303 (manufactured by iM Chemical Co., Ltd.) was added as a coupling agent.
parts by weight and 0.0 parts by weight of the Acylay type I titanate compound.
8 parts by weight, 1 part calcium stearate as a template agent
．． 0 parts by weight, Hoechst Wax E (Hoechst Japan Co., Ltd. 12) 1.0 parts by weight, 5 parts by weight of addition-type imide coated red phosphorus as a flame retardant, and an average particle size of 1 μm as a filler.
50 weight percent of spherical alumina (based on the entire composition), 30 weight percent of fused silica glass powder of 10 to 44 μm, and 2.0 parts of carbon blank (manufactured by Cabot) as a coloring agent were separately added. did.

Next, the above-mentioned mixture was heated and mixed for 8 minutes using two 8-inch diameter rolls at 75 to 85°C, and then cooled.

The mixture was coarsely ground to obtain a molding material composition for semiconductor encapsulation.

Cured product obtained from this composition and 1M bit D-RAM
Table 3 shows the results of the moisture resistance reliability of the LSI encapsulation molded products made from the above compositions.

〔Effect of the invention〕

The composition containing the fluorine-containing resol type phenolic resin of the present invention has great effects in terms of heat resistance, flexibility, adhesiveness, anti-inflammatory properties, and lower dielectric constant.

Claims (10)

[Claims] 1. General formula [ I ] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [ I ] [In the formula, R_f is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (n is 1 to 40), ▲ Numerical formulas, chemical formulas , tables, etc.▼ (R', R'' and R''' are F, CF_3, C_2F_5
, C_3F_7 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. Also, there is no X_1, -O-, -OCH_2-, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, -N -(CH_2)_2-. Also, R
_1 is any one of an alkyl group, an alkoxy group, Cl, Br, F, a phenyl group, and a fluoroalkyl group. ] A fluorine-containing resol type phenolic resin containing a structural unit represented by the following. 2. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] [In the formula, R_f is ▲There are mathematical formulas, chemical formulas, tables, etc.▼
, (n is 1 to 40), ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (R', R'' and R''' are F, CF_3, C_2F_5
, C_3F_7 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. Also, there is no X_1, -O-, -OCH_2-, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, -N -(CH_2)_2-. Also, R
_1 is any one of an alkyl group, an alkoxy group, Cl, Br, F, a phenyl group, and a fluoroalkyl group. ] A composition containing a fluorine-containing resol type phenolic resin containing a structural unit represented by the following. 3. A composition comprising the fluorine-containing resol type phenol resin according to claim 1 and a polyfunctional epoxy compound. 4. A semiconductor device coated and/or encapsulated using the composition according to claim 3. 5. A laminate using the composition according to claim 2. 6. A prepreg using the composition according to claim 2. 7. A printed circuit board using the composition according to claim 2. 8. A semiconductor encapsulation material using the composition according to claim 2. 9. A composition comprising the fluorine-containing resol type phenolic resin according to claim 7 and an N-substituted unsaturated imide compound. 10. A composition comprising the fluorine-containing resol type phenolic resin according to claim 1 and a poly-P-vinylphenol compound.