WO2024117252A1

WO2024117252A1 - Polyaryl ether ketone resin material for electronic equipment/devices and electronic equipment/devices using same

Info

Publication number: WO2024117252A1
Application number: PCT/JP2023/043048
Authority: WO
Inventors: 健太萩原; 佑磨芝崎
Original assignee: 本州化学工業株式会社
Priority date: 2022-12-01
Filing date: 2023-12-01
Publication date: 2024-06-06

Abstract

The present invention addresses the problem of providing a polyaryl ether ketone resin material that has excellent dielectric properties, excellent heat resistance, and is suitable as a material for use in electronic equipment/devices, especially electronic equipment/devices in the high-speed communications field that require high-frequency support. Provided as a solution is a polyaryl ether ketone resin material for electronic equipment/devices that contains polyaryl ether ketone having a repeating unit represented by general formula (1), that has a dielectric tangent (Df) measured at a frequency of 10 GHz of 0.004 or less, that has a relative permittivity (Dk) measured at a frequency of 10 GHz of 3.5 or less, that has a glass transition temperature of 150°C or more, and that has a weight average molecular weight (Mw) in the range 2,000-1,000,000. (In the formula, R1 and R2 each independently represent a C1-4 alkyl group, a represents 1 or 2, b each independently represents 0, 1, or 2, and c represents 0 or an integer of 1-4.)

Description

Polyaryl ether ketone resin material for electronic devices and electronic devices using the same

The present invention relates to the use of polyaryl ether ketone (PAEK), and more specifically, to the use of PAEK obtained using bisphenol as a raw material, in particular to a resin material for electronic devices and devices made of PAEK with excellent heat resistance and dielectric properties, and to electronic devices and devices using the same.

Polyaryletherketone (PAEK) resin is known as a thermoplastic that has excellent heat resistance, high strength and rigidity, and chemical resistance. For this reason, PAEK resin is used as a material in fields such as insulating coating agents, insulating films, semiconductors, electrode protective films, flexible printed circuit boards and other electrical and electronic components, aerospace equipment, and transportation equipment. The use of PAEK in these applications tends to become more advanced and specialized, and improved heat resistance is also required.

In recent years, in wireless Internet devices and communication devices, the transmission speed of electric signals flowing therethrough has become extremely high and high frequency, and the insulating parts that insulate the metal wiring of these devices are also required to respond to high frequencies. In particular, higher frequency radio waves such as centimeter waves (SHF: Super High Frequency) and millimeter waves (EHF: Extremely High Frequency) are used to perform even faster data communication. The higher the frequency, the greater the dielectric loss of the insulating parts, and the more the electric signals flow attenuate. Therefore, in response to the increase in frequency, materials with excellent dielectric properties that can reduce dielectric loss are required. At the same time, in the manufacturing and use of electronic devices and electronic devices used therein (hereinafter, in the present invention, they may be collectively referred to as electronic devices and devices), for example, high heat resistance may be required as in power semiconductors when used as devices.
PAEKs are also used as low dielectric materials. For example, PAEKs using 1,1'-bi-2-naphthol (Patent Document 1) and PAEKs copolymerized with hydroquinone, 4,4'-difluorobenzophenone, and 2,6-dichloropyridine (Patent Document 2) are known to be extremely useful as electrical insulating layers in laminates for electronic circuits and as base materials for flexible printed wiring boards.

JP 2005-213393 A JP 2006-002013 A

The objective of the present invention is to provide a PAEK resin material that has excellent dielectric properties and excellent heat resistance and is suitable for use in electronic devices and devices, particularly in electronic devices and devices in the field of high-speed communications that require high frequencies.

As a result of extensive research into solving the above problems, the inventors discovered that polyaryletherketones (PAEKs) with a specific aliphatic ring structure have excellent dielectric properties, excellent heat resistance, and low water absorption, and thus completed the present invention.

The present invention is as follows.
1. A polyaryl ether ketone resin material for electronic devices, comprising a polyaryl ether ketone having a repeating unit represented by general formula (1), having a dielectric loss tangent (Df) measured at a frequency of 10 GHz of 0.004 or less, a relative dielectric constant (Dk) measured at a frequency of 10 GHz of 3.5 or less, a glass transition temperature of 150°C or more, and a weight average molecular weight (Mw) in the range of 2,000 to 1,000,000.
(In the formula, _R1 and _R2 each independently represent an alkyl group having 1 to 4 carbon atoms, a represents 1 or 2, b each independently represents 0, 1, or 2, and c represents 0 or an integer of 1 to 4.)
2. The polyaryl ether ketone resin material for electronic devices and devices according to 1., wherein the repeating unit represented by the general formula (1) is a repeating unit represented by the general formula (1′).
(In the formula, R ₂ , a and c are defined as in general formula (1).)
3. The polyaryl ether ketone resin material for electronic devices and devices according to 2., wherein the repeating unit represented by general formula (1') is a repeating unit represented by general formula (1'').
(In the formula, a is defined as in general formula (1).)
4. An electronic device or device using the polyaryl ether ketone resin material for electronic devices or devices according to 4.1.
5. A method for using a polyaryl ether ketone having a repeating unit represented by general formula (1), which has a dielectric loss tangent (Df) of 0.004 or less measured at a frequency of 10 GHz, a relative dielectric constant (Dk) of 3.5 or less measured at a frequency of 10 GHz, a glass transition temperature of 150°C or more, and a weight average molecular weight (Mw) in the range of 2,000 to 1,000,000, in an electronic device or device.
(In the formula, _R1 and _R2 each independently represent an alkyl group having 1 to 4 carbon atoms, a represents 1 or 2, b each independently represents 0, 1, or 2, and c represents 0 or an integer of 1 to 4.)
6. A method for using the polyaryl ether ketone according to 5. in an electronic device or device, wherein the repeating unit represented by the general formula (1) is a repeating unit represented by the general formula (1').
(In the formula, R ₂ , a and c are defined as in general formula (1).)
7. A method for using the polyaryl ether ketone according to 6. in an electronic device or device, wherein the repeating unit represented by general formula (1') is a repeating unit represented by general formula (1'').
(In the formula, a is defined as in general formula (1).)

The polyaryl ether ketone resin material for electronic devices of the present invention has excellent dielectric properties, excellent heat resistance (high glass transition temperature), and low water absorption. Therefore, it is suitable as a material resin for electronic devices in the field of high-speed communications, which requires high frequencies, and for the electric and electronic components and electronic devices used therein.

(Polyaryl ether ketone resin material for electronic devices according to the present invention)
The PAEK in the polyaryl ether ketone resin material for electronic devices of the present invention has a repeating unit represented by general formula (1).
(In the formula, _R1 and _R2 each independently represent an alkyl group having 1 to 4 carbon atoms, a represents 1 or 2, b each independently represents 0, 1, or 2, and c represents 0 or an integer of 1 to 4.)
_R1 and _R2 each independently represent an alkyl group having 1 to 4 carbon atoms, preferably a t-butyl group or a methyl group, and particularly preferably a methyl group.
The bonding position of _R1 is preferably the ortho position relative to the bonding position of the oxygen atom on the benzene ring.
a represents 1 or 2, and is preferably 1.
Each b independently represents 0, 1 or 2, and from the viewpoint of the heat resistance of the resulting PAEK, it is preferable that each b independently represents 0 or 2, more preferably that both b's represent 0 or 2, and particularly preferably represent 2.
c represents 0 or an integer of 1 to 4, preferably an integer of 1 to 4, more preferably 1, 2 or 3, and particularly preferably 3.
As the PAEK according to the present invention, from the viewpoint of heat resistance and low water absorption, an embodiment having a repeating unit represented by general formula (1') in which R ₁ is a methyl group, b is 2, and R ₁ is bonded at the ortho position relative to the position to which the oxygen atom on each benzene ring is bonded is preferred.
(In the formula, R ₂ , a and c are defined as in general formula (1).)
In the repeating unit represented by formula (1'), it is particularly preferable that the repeating unit further has a repeating unit represented by formula (1'') in which _R2 is a methyl group and c is 3.
(In the formula, a is defined as in general formula (1).)

Specific examples of the repeating unit represented by general formula (1) of the PAEK of the present invention are shown below as chemical formulas (1a) to (1d). As the repeating unit represented by general formula (1), at least one selected from chemical formulas (1a) to (1d) is preferred, at least one selected from chemical formulas (1a) and (1b) is more preferred, chemical formula (1a) or (1b) is even more preferred, and chemical formula (1a) is particularly preferred.

The PAEK according to the present invention may have other repeating units as long as it contains the repeating unit represented by the general formula (1), as long as the effect of the present invention is not impaired. However, it is preferable that the content of the repeating unit represented by the general formula (1) is 100 mol%, that is, it does not have other repeating units. When the PAEK has other repeating units, the lower limit of the range of the content of the repeating unit represented by the general formula (1) is preferably 50 mol% or more of the entire PAEK, more preferably 70 mol% or more, even more preferably 80 mol% or more, and particularly preferably 90 mol% or more. The upper limit is preferably less than 100 mol%, and more preferably 99.9 mol% or less. The above lower limit and upper limit in the range of the content of the repeating unit represented by the general formula (1) may be combined. The repeating unit represented by the general formula (1) and the other repeating units may be regularly arranged or may be randomly present.
PAEK having the repeating unit represented by general formula (1) and other repeating units can be produced by carrying out a polycondensation reaction described later using a biphenol compound represented by general formula (3) described later and other aromatic dihydroxy compounds in combination.

The structures at both ends of the polymer chain of the PAEK according to the present invention are not particularly limited. The end structure may be a halogen atom derived from a dihalogen compound represented by the following general formula (2), a hydroxyl group derived from a bisphenol compound represented by the following general formula (3), or a reactive functional group modified from the hydroxyl group to a group represented by the following general formula (4) (specifically, an acryloyloxy group or a methacryloyloxy group) or a group represented by the following chemical formula (5) (glycidyl ether group).
(In the formula, _R3 represents a hydrogen atom or a methyl group, and * represents a bonding site to the end of a polymer chain.)
When the terminal structures are (i) both halogen atoms, (ii) both hydroxyl groups, or (iii) one halogen atom and the other hydroxyl group, the polyaryletherketone of the present invention can be used as a thermoplastic resin. Conventional molding and processing methods for thermoplastic resins (e.g., melt molding methods such as injection molding, extrusion molding, and compression molding) can be applied. By using such molding and processing methods, molded articles for use in electronic devices and devices can be manufactured, and electronic devices and devices can be manufactured.
In addition, when the terminal structures are (i) both of which are one group selected from the group represented by the general formula (4) or the chemical formula (5), (ii) one of which is one group selected from the group represented by the general formula (4) or the chemical formula (5) and the other is a halogen atom, or (iii) one of which is one group selected from the group represented by the general formula (4) or the chemical formula (5) and the other is a hydroxyl group, at least one of the terminal structures has a reactive functional group, so that it can be used as a curable resin. Conventional molding and processing methods for curable resins (e.g., compression molding and transfer molding) can be applied. By such a molding and processing method, a molded product used in an electronic device or device can be manufactured to manufacture an electronic device or device.

(Dielectric tangent)
The dielectric loss tangent of the PAEK of the polyaryl ether ketone resin material for electronic devices and devices of the present invention measured at a frequency of 10 GHz is 0.004 or less. Since it is 0.004 or less, it can be suitably used as a PAEK material for electronic devices, which will be described later, such as communication devices that require compatibility with high frequencies. The dielectric loss tangent is preferably 0.0038 or less, more preferably 0.0036 or less, and particularly preferably 0.0035 or less. The lower the dielectric loss tangent, the more preferable it is, so there is no particular limit to the lower limit, but it may be 0.0020 or more.

(Dielectric constant)
The dielectric constant of the PAEK of the polyaryl ether ketone resin material for electronic devices and devices of the present invention measured at a frequency of 10 GHz is 3.5 or less. If it is 3.5 or less, it can be suitably used as a PAEK material for electronic devices and devices described later, such as communication devices that are particularly required to support high frequencies. The dielectric constant is preferably 3.0 or less, more preferably 2.9 or less, and particularly preferably 2.8 or less. The lower limit of the dielectric constant is not particularly limited because the lower the dielectric constant, the more preferable it is, but it may be 2.0 or more.

(Molecular Weight)
The weight average molecular weight (Mw) of the PAEK in the polyaryl ether ketone resin material for electronic devices of the present invention is in the range of 2,000 to 1,000,000. By being in this range, it can be used as a material with sufficient strength. It is preferably in the range of 10,000 to 500,000, more preferably in the range of 20,000 to 200,000, and particularly preferably in the range of 30,000 to 150,000.
When the end structures of both ends of the polymer chain of the PAEK according to the present invention are (i) both halogen atoms, (ii) both hydroxy groups, or (iii) one halogen atom and the other hydroxy group, in order to provide sufficient mechanical strength when used as a thermoplastic resin, the weight average molecular weight (Mw) is more preferably in the range of 10,000 to 500,000, even more preferably in the range of 20,000 to 200,000, and particularly preferably in the range of 30,000 to 150,000.
In the case where the terminal structures of the PAEK according to the present invention are (i) both of which are a group selected from the group represented by the general formula (4) or the chemical formula (5), (ii) one of which is a group selected from the group represented by the general formula (4) or the chemical formula (5) and the other is a halogen atom, or (iii) one of which is a group selected from the group represented by the general formula (4) or the chemical formula (5) and the other is a hydroxy group, in order to provide good processability when used as a curable resin, the weight average molecular weight (Mw) is preferably in the range of 2,000 to 100,000, more preferably in the range of 2,000 to 50,000, even more preferably in the range of 2,000 to 30,000, and particularly preferably in the range of 2,000 to 10,000.
The ratio of weight average molecular weight (Mw) to number average molecular weight (Mn), Mw/Mn, is preferably in the range of 1.5 or more and 20 or less, more preferably in the range of 2 or more and 15 or less, even more preferably in the range of 2 or more and 10 or less, and particularly preferably in the range of 2 or more and 8 or less.

(Reduced Viscosity)
The reduced viscosity of the PAEK in the polyaryl ether ketone resin material for electronic devices of the present invention is preferably 0.1 dL/g or more, more preferably 0.3 dL/g or more, and even more preferably 0.5 dL/g or more. The reduced viscosity is a measured value of the viscosity of a 1.0 g/dL solution of the PAEK in the present invention using p-chlorophenol as a solvent at 40°C.

(Glass-transition temperature)
The glass transition temperature of the PAEK in the polyaryl ether ketone resin material for electronic devices and devices of the present invention is 150°C or higher. It can be suitably used as a PAEK material for electronic devices and electronic devices that are exposed to high temperatures during the manufacturing process and in use. The glass transition temperature is preferably 170°C or higher, more preferably 200°C or higher, even more preferably 215°C or higher, and particularly preferably 230°C or higher. The higher the glass transition temperature, the better the heat resistance, so the upper limit is not particularly limited, but it may be 300°C or lower.

The water absorption rate of the polyaryl ether ketone resin material for electronic devices and devices of the present invention is preferably 0.35% or less. If the water absorption rate is 0.35% or less, the material can be suitably used as a polyaryl ether ketone resin material for electronic devices, particularly for electronic devices used in high-speed communication using high-frequency radio waves and electronic devices used therein (electronic devices and devices for high-frequency communication). The water absorption rate is more preferably 0.30% or less, even more preferably 0.20% or less, and particularly preferably 0.1% or less. The lower the water absorption rate, the better, so there is no particular restriction on the lower limit, but it may be 0.001% or more.

(Method of producing PAEK according to the present invention)
The method for producing the PAEK of the polyaryl ether ketone resin material for electronic devices of the present invention is not particularly limited, and the PAEK can be produced, for example, by subjecting a dihalogen compound represented by general formula (2) and a bisphenol compound represented by general formula (3) to a desalting polycondensation reaction in the presence of an alkali metal compound.
(In the formula, each X independently represents a halogen atom, and a is defined as in general formula (1).)
(In the formula, R ₁ , R ₂ , b and c are defined as in general formula (1).)

As a specific example, when 4,4'-difluorobenzophenone (2a) is used as the dihalogen compound represented by general formula (2), 1,1-bis(4-hydroxyphenyl)cyclohexane (3a) is used as the bisphenol compound represented by general formula (3), and sodium carbonate is used as the alkali metal compound, a polyaryl ether ketone having a repeating unit represented by chemical formula (1a) can be produced. The reaction formula is shown below.

(Dihalogen compound represented by general formula (2))
Specifically, X in the general formula (2) represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. Among these, a fluorine atom or a chlorine atom is preferable, and a fluorine atom is particularly preferable.
In formula (2), a is preferably 1.
Specific examples of the dihalogen compound represented by the general formula (2) include 4,4'-difluorobenzophenone, 4,4'-dichlorobenzophenone, 4,4'-dibromobenzophenone, 4,4'-diiodobenzophenone, 1,4-bis(4-fluorobenzoyl)benzene, 1,4-bis(4-chlorobenzoyl)benzene, 1,4-bis(4-bromobenzoyl)benzene, and 1,4-bis(4-iodobenzoyl)benzene.
Of these, 4,4'-difluorobenzophenone and 4,4'-dichlorobenzophenone are preferred, with 4,4'-difluorobenzophenone being particularly preferred.

(Bisphenol compound represented by general formula (3))
The definitions and preferred embodiments of R ₁ and n in formula (3) are the same as those in formula (1).
Specific examples of the bisphenol compound represented by the general formula (3) include 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, 4,4'-cyclohexylidenebis(2,6-dimethylphenol), 4-[1-(4-hydroxyphenyl)cyclohexyl]-2-methylphenol, 4-[1-(4-hydroxyphenyl)cyclohexyl]-2,6-dimethylphenol, 4,4'-(3,5-dimethylcyclohexylidene)bisphenol, 4,4'-(2-methylcyclohexylidene)bisphenol, 4,4'-(2-methylcyclohexylidene)bis(2-methylphenol), 4,4'-(2-methylcyclohexylidene)bis(2,6-dimethylphenol), 4, Examples of the cyclohexylidene ester include 4'-(3-methylcyclohexylidene)bisphenol, 4,4'-(3-methylcyclohexylidene)bis(2-methylphenol), 4,4'-(3-methylcyclohexylidene)bis(2,6-dimethylphenol), 4,4'-(4-methylcyclohexylidene)bisphenol, 4,4'-(4-methylcyclohexylidene)bis(2-methylphenol), 4,4'-(4-methylcyclohexylidene)bis(2,6-dimethylphenol), 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane, and 1,1-bis(4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexane.
Among these, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, 4,4'-cyclohexylidenebis(2,6-dimethylphenol), 4,4'-(3-methylcyclohexylidene)bisphenol, 4,4'-(3-methylcyclohexylidene)bis(2-methylphenol), 4,4'-(3-methylcyclohexylidene)bis(2,6-dimethylphenol), 4,4'-(4-methylcyclohexylidene)bisphenol, 4,4'-(4-methylcyclohexylidene)bis(2-methylphenol), 4,4'-(4-methylcyclohexylidene)bisphenol, Preferred are 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, 4,4'-cyclohexylidenebis(2,6-dimethylphenol), 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexane, and more preferred are 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, 4,4'-cyclohexylidenebis(2,6-dimethylphenol), 4,4'-(3-methylcyclohexylidene)bis Phenol, 4,4'-(3-methylcyclohexylidene)bis(2-methylphenol), 4,4'-(3-methylcyclohexylidene)bis(2,6-dimethylphenol), 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane, and 1,1-bis(4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexane are more preferred, and 4,4'-cyclohexylidenebis(2,6-dimethylphenol) and 4,4'-(3-methylcyclohexylidene)bis(2,6 -dimethylphenol), 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane, and 1,1-bis(4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexane are more preferred, and 4,4'-cyclohexylidenebis(2,6-dimethylphenol), 4,4'-(3-methylcyclohexylidene)bis(2,6-dimethylphenol), and 1,1-bis(4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexane are particularly preferred.
In the PAEK according to the present invention, in order to obtain a PAEK having a repeating unit represented by the general formula (1) and another repeating unit, other aromatic dihydroxy compounds can be used in combination with the biphenol compound represented by the general formula (3). The other repeating units have a structure derived from these aromatic dihydroxy compounds and a repeating unit having a structure derived from the dihalogen compound represented by the general formula (2). Specific examples of aromatic dihydroxy compounds that can be used in combination include hydroquinone, resorcin, 2-phenylhydroquinone, 4,4'-biphenol, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,1'-bi-2-naphthol, 2,2'-bi-1-naphthol, 1,3-bis[1-methyl-1-(4-hydroxyphenyl)ethyl]benzene, 1,4-bis[1-methyl-1-(4-hydroxyphenyl)ethyl]benzene, 1,3 -Bis(4-hydroxybenzoyl)benzene, 1,4-bis(4-hydroxybenzoyl)benzene, 1,3-bis(4-hydroxyphenoxy)benzene, 1,4-bis(4-hydroxyphenoxy)benzene, 1,4-bis(4-hydroxyphenyl)benzene, 1,3-bis(4-hydroxyphenyl)benzene, 4,4'-methylenebis(phenol), 4,4'-methylenebis(2,6-dimethylphenol), 4,4'-isopropylidenebiphenol (Bis-A), 2,2-bis(4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 4,4'-dihydroxybenzophenone, 4,4'-bis(hydroxyphenyl)sulfone, 4,4'-dihydroxydiphenyl ether, bis(4-hydroxyphenyl)methane, 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(3-phenyl-4-hydroxyphenyl)fluorene, 9,9-bis(3,5-diphenyl-4- Examples of the fluorene include 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3,5-dimethylphenyl)fluorene, 9,9-bis(4-hydroxy-3-cyclohexylphenyl)fluorene, 2,2-bis(4-hydroxy-3-phenylphenyl)propane, 1,1-bis(4-hydroxyphenyl)cyclododecane, and 1,1-bis(4-hydroxyphenyl)-1-phenylethane. These compounds may be used alone or in combination of two or more.

(alkali metal compounds)
As the alkali metal compound, any compound can be used as long as it can convert the bisphenol compound represented by the general formula (3) into an alkali metal salt, but usually, carbonates, hydrogen carbonates, hydroxides, etc. of alkali metals are preferably used, and carbonates are particularly preferred. Examples of the alkali metal include lithium, sodium, potassium, rubidium, and cesium, and among them, sodium and potassium are preferred, and potassium is particularly preferred.

(solvent)
A solvent can be used in the polycondensation reaction to obtain PAEK, and it is preferable to use the solvent. As the solvent to be used, a neutral polar solvent such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), dimethylimidazolidinone (DMI), dimethylsulfoxide (DMSO), sulfolane, diphenylsulfone, etc. is preferable, but any solvent can be used without any problem as long as the monomer and polymer are soluble in the solvent. The solvent may be used alone or in combination of two or more kinds as a mixed solvent.

(Polycondensation reaction conditions)
The amount of the dihalogen compound represented by the general formula (2) used depends on the target molecular weight relative to the bisphenol compound represented by the general formula (3) (when an aromatic dihydroxy compound other than the general formula (3) is used in combination, the total of the bisphenol compound represented by the general formula (3) and the other aromatic dihydroxy compound). In order to produce a PAEK having a large molecular weight (specifically, preferably in the range of 10,000 to 500,000, more preferably in the range of 20,000 to 200,000, and particularly preferably in the range of 30,000 to 150,000), the amount is usually in the range of 0.9 to 1.1 times by mole, preferably in the range of 0.95 to 1.06 times by mole, and more preferably in the range of 1.0 to 1.04 times by mole.
In order to increase the proportion of halogen atoms in the structures at both ends of the polymer chain of the resulting PAEK, more than 1.00 molar equivalents are used within the above range, and in order to increase the proportion of hydroxyl groups, less than 1.00 molar equivalents are used within the above range.
In the case where the end structures of the polymer chain of the PAEK to be produced are both halogen atoms, the molar ratio is in the range of 1.01 to 1.1 times by mole, preferably in the range of 1.01 to 1.06 times by mole, and more preferably in the range of 1.01 to 1.04 times by mole.
In the case where the terminal structures of the polymer chain of the PAEK to be produced are both hydroxy groups, the molar ratio for a PAEK having a large molecular weight is in the range of 0.9 to 0.99 molar times, and preferably in the range of 0.95 to 0.99 molar times, while the molar ratio for a PAEK having a small molecular weight is usually in the range of 0.6 to 0.95 molar times, preferably in the range of 0.7 to 0.9 molar times, and more preferably in the range of 0.8 to 0.9 molar times.
The amount of the alkali metal compound used is usually in the range of 1.0 to 3.0 moles, preferably 1.01 to 1.3 moles, per mole of the bisphenol compound represented by formula (3).
The reaction temperature is usually in the range of 150 to 350° C., preferably 180 to 250° C., and the reaction time is usually in the range of 1 to 60 hours, preferably 2 to 50 hours.
These reactions are preferably carried out in an atmosphere of an inert gas such as nitrogen, argon, etc. There is no limitation on the reaction pressure, and the reaction may be carried out at reduced pressure, atmospheric pressure, or elevated pressure, but the reaction is usually carried out at atmospheric pressure.

<Post-reaction treatment>
The PAEK produced by the polycondensation reaction can be recovered by a commonly used method such as coagulation, solidification, washing, granulation, extraction, or solvent distillation.
The method for treating the PAEK produced by the polycondensation reaction will be described in more detail. The liquid containing the PAEK produced by the polycondensation reaction can be diluted with a solvent as necessary, and mixed with a poor solvent to precipitate the PAEK, thereby obtaining a powdered PAEK. As the solvent used for precipitation of the precipitate, for example, methanol, ethanol, acetone, methyl ethyl ketone, xylene, toluene, etc. are preferable, and acetone and methanol are particularly preferable in view of operability and ease of distillation recovery of the reaction solvent after washing.
The powdered PAEK obtained by precipitation of the precipitate is preferably subjected to a washing step in order to remove alkali metal salts such as potassium chloride produced in the desalting polycondensation reaction, the solvent used in the reaction, and the solvent used in the precipitation of the precipitate.
For washing away alkali metal salts such as potassium chloride produced in the desalting polycondensation reaction, water is preferred, but acidic water containing low concentrations of hydrochloric acid, formic acid, oxalic acid, etc. may also be used.
The conditions for this washing step may be appropriately selected according to the amounts of residual reaction solvent and residual alkali metal salts to be removed, such as the amount of washing solvent used, the number of washings, and the washing temperature.
After washing with water, the powder may be washed with, for example, methanol, ethanol, acetone, methyl ethyl ketone, xylene, or toluene, particularly acetone or methanol.
The washing apparatus may be a combination of a washing tank and a pressure filter or a centrifuge, or a multi-function filter capable of washing, filtering and drying in one apparatus.

A step of drying the powdered PAEK containing moisture and solvent after completion of the washing step obtained by the above washing step can be carried out.
The conditions for this drying step may be any conditions that allow removal of moisture at a temperature equal to or lower than the melting point of the polycondensation reaction product. It is preferable to perform the drying step under an inert gas (nitrogen, argon, etc.) atmosphere, under an inert gas stream, or under reduced pressure so as to minimize contact with air.
The dryer may be a known device such as an evaporator, a tray oven, or a tumbler.

　In the case where the structure of both ends of the polymer chain of the aryl ether ketone (PAEK) of the present invention is a terminal structure modified with reactive functional groups such as a group represented by general formula (4) (acryloyloxy group, methacryloyloxy group) or a group represented by chemical formula (5) (glycidyl ether group), the PAEK can be obtained by modifying the hydroxy group derived from the bisphenol compound represented by general formula (3) to a reactive substituent such as an acryloyloxy group, methacryloyloxy group, or glycidyl ether group.

The PAEK according to the present invention, whose terminal structure is a group represented by general formula (4) (an acryloyl group or a methacryloyl group), can be produced by applying a conventionally known method for (meth)acrylation of a hydroxy compound to a polyaryletherketone having a repeating unit represented by general formula (1) containing a hydroxy group at the end of the polymer chain obtained by the above-mentioned method.
As a method for (meth)acrylation, for example, there is a method of reacting (meth)acrylic acid and its derivatives with the terminal hydroxyl group of polyaryletherketone having a repeating unit represented by general formula (1). When acrylic acid chloride is used as a derivative of (meth)acrylic acid, chloride ions are generated in the form of hydrogen chloride, so it is preferable to use a hydrogen chloride scavenger in combination. As the hydrogen chloride scavenger, inorganic or organic basic substances such as carbonates or hydrogen carbonates of alkali metals, tertiary amines, etc. can be used. Specific examples of (meth)acrylic acid and its derivatives include acrylic acid, methacrylic acid, acrylic acid chloride, methacrylic acid chloride, etc.
In the acrylation reaction, a solvent such as a halogenated hydrocarbon such as methylene chloride, tetrahydrofuran, dioxane, chlorobenzene, or the like may be used.
During the reaction, a polymerization inhibitor such as hydroquinone, hydroquinone monomethyl ether, phenothiazine, or 2,6-di-tert-butyl-4-methylphenol (BHT) may be added.

The PAEK according to the present invention, whose terminal structure is a group represented by chemical formula (5) (glycidyl ether group), can be produced by applying a conventionally known method for glycidyl etherifying a hydroxy compound to a polyaryl ether ketone having a repeating unit represented by general formula (1) containing a hydroxy group at the end of the polymer chain obtained by the above-mentioned method.
As a method for glycidyl etherification, for example, a glycidyl etherified PAEK can be produced by reacting a terminal hydroxy group of a polyaryletherketone having a repeating unit represented by the general formula (1) with epihalohydrin in the presence of an alkali metal hydroxide (e.g., sodium hydroxide or potassium hydroxide) or a quaternary ammonium salt (e.g., tetramethylammonium chloride or tetramethylammonium bromide). Specific examples of the epihalohydrin used include epichlorohydrin and epibromohydrin.

<Polyaryletherketone resin composition>
The PAEK according to the present invention can be blended with various additives such as flame retardants, heat stabilizers, oxidation stabilizers, weathering stabilizers, antistatic agents, lubricants, plasticizers, etc., as desired, by a conventional method of blending additives with raw resins, within a range that does not impair the effects of the present invention. A polyaryl ether ketone resin composition can be obtained, which contains the PAEK according to the present invention and one or more additives selected from the group consisting of flame retardants, heat stabilizers, oxidation stabilizers, weathering stabilizers, antistatic agents, lubricants, and plasticizers.
This polyaryl ether ketone resin composition can be used in the same manner as the PAEK of the present invention described below.

Use of the PAEK according to the present invention
(High-frequency radio waves)
The high-frequency radio waves in the present invention refer to radio waves having a frequency in the range of 1 GHz to 300 GHz, including microwaves, centimeter waves (SHF: Super High Frequency), millimeter waves (EHF: Extremely High Frequency), etc. The range of such high-frequency radio waves is preferably 1 GHz to 100 GHz, more preferably 1 GHz to 80 GHz, and particularly preferably 1 GHz to 30 GHz.

(Polyaryletherketone resin materials for electronic devices)
The PAEK according to the present invention has heat resistance, as well as excellent dielectric properties in the high frequency band and low water absorption. Therefore, a resin material containing the polyaryl ether ketone of the present invention is suitable as a polyaryl ether ketone resin material used in electronic devices and electronic devices used therein (electronic devices and devices), and is particularly suitable as a polyaryl ether ketone resin material used in electronic devices and devices used in high-speed communication using radio waves in the high frequency band (electronic devices and devices for high-frequency communication).
The polyaryletherketone resin material for electronic devices and devices, which contains the PAEK according to the present invention, may be a resin material containing only the polyaryletherketone according to the present invention, depending on the properties required for the electronic device or device to be manufactured, or may be a resin material containing the PAEK according to the present invention and one or more additives selected from the group consisting of a flame retardant, a heat stabilizer, an oxidation stabilizer, a weather resistance stabilizer, an antistatic agent, a lubricant, and a plasticizer.
As described above, the polyaryletherketone resin material for electronic devices can be used as a resin material for electronic devices and devices to produce molded products such as films, sheets, tapes, containers, threads, lenses, tubes, pellets, and chips by applying a conventional molding/processing method for thermoplastic resins (e.g., melt molding methods such as injection molding, extrusion molding, and compression molding) or a conventional molding/processing method for curable resins (e.g., compression molding and transfer molding).Then, the molded products can be used as resin materials for electronic devices and devices to produce electronic devices and devices.

(Electronic equipment and devices)
In the present invention, electronic devices and electronic devices used therein are collectively referred to as electronic devices and devices. In particular, electronic devices and devices used for high-speed communication using radio waves in a high frequency band are collectively referred to as high-frequency communication electronic devices and devices. Since the PAEK of the present invention has excellent dielectric properties in a high frequency band in addition to heat resistance, electronic devices and devices using the PAEK of the present invention are preferred, and high-frequency communication electronic devices and devices are particularly preferred.
Specific examples of the electronic device include mobile phones, smartphones, personal computers, mobile routers, data center communication equipment, base stations, radars, robots, drones, wearable computers, automobiles, aircraft, measuring and measurement equipment used in various industries such as industry, agriculture, logistics, and civil engineering, high-speed wireless communication equipment, electronic organizers, digital still cameras, video cameras, electronic paper, televisions, players, various audio equipment, car navigation devices, in-vehicle displays such as instrument panels, calculators, printers, scanners, copiers, refrigerators, and washing machines.
Among these, electronic devices used for high-speed communication using high-frequency radio waves include mobile phones, smartphones, personal computers, mobile routers, data center communication equipment, base stations, radar, robots, drones, wearable computers, measurement and gaging equipment used in various industries such as the automobile, aircraft, manufacturing, agriculture, logistics, and civil engineering industries, and high-speed wireless communication equipment.
Specific examples of the electronic devices include semiconductors, electronic displays, and electric/electronic components. Examples of the electric/electronic components include capacitors, printed circuits, connectors, various sensors, inductors, switches, and housings. These are also used in electronic devices for high-speed communication using high-frequency radio waves.
More specifically, the polyaryl ether ketone resin material of the present invention can be suitably used for, for example, exterior members, structural members, circuit boards, semiconductor encapsulants, or antenna element members of these electronic devices and devices (preferably, electronic devices and devices for high-frequency communication in the range of 1 GHz to 300 GHz). Among these, the polyaryl ether ketone resin material can be suitably used for the circuit boards, semiconductor encapsulants, or antenna element members of the electronic devices and devices, and can be particularly suitably used for the circuit boards of the electronic devices and devices.

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.
The analytical method in the present invention is as follows.
<Analysis method>
1. Measurement of Glass Transition Temperature (Tg) The glass transition temperatures of the PAEKs obtained in the Examples and Comparative Examples were measured using the following apparatus and conditions.
Measuring device: DSC7020 (manufactured by Hitachi, Ltd.)
Pan: Aluminum Atmosphere: _N2
Heating rate: 10° C./min.
Analysis method: Glass transition point of ^2nd heating (intersection of baseline and tangent line)
2. Measurement of dielectric constant and dielectric loss tangent The PAEK powder obtained in the examples and comparative examples described below was molded into test pieces by the following molding method. The dielectric constant and dielectric loss tangent of the obtained test pieces were measured using the following device and conditions.
(Molding method)
The PAEK powder was molded into a test piece using a Mini Test Press MP-2FH (Toyo Seiki Co., Ltd.). The molding was performed by melting and degassing the powder several times at a temperature of 350°C and a pressure of 1 to 5 MPa, and then pressing the powder at a temperature of 350°C and a pressure of 12 MPa for 5 minutes. (Measurement device and conditions)
Measurement device: Synthesized Sweeper 8340B (YHP)
Network analyzer 8510B (YHP)
Cylindrical cavity resonator (material: copper, internal mirror finish)
Semi-rigid cable for signal transmission Sample size: Cut into approximately 50 mm square Measurement frequency: Around 10 GHz Measurement environment: Room temperature (23±2°C/50±5% RH)
3. Molecular Weight Measurement The molecular weights of the PAEKs obtained in the Examples and Comparative Examples described below were measured by gel permeation chromatography (GPC) using the following apparatus and conditions.
Equipment: 515 HPLC pump, 717plus automatic insertion device, 2487 UV-Vis detector (Waters)
Column/temperature: 2x PLgel 5μ MIXED-D, 7.5x300mm (Agilent Technologies)/40°C
Mobile phase: chloroform for HPLC Flow rate: 1.0 mL/min.
Injection volume: 2.5uL
Detection: UV-visible detector 254 nm
Column calibration: monodisperse PS; EasiCal Type PS-1 polystyrene (Agilent Technologies)
Molecular weight calibration: PS conversion 4. Measurement of reduced viscosity The PAEK powder obtained in the examples and comparative examples described later was prepared into a solution having a concentration of 1.0 g/dL using p-chlorophenol as a solvent, and the viscosity at 40° C. was measured.
5. Measurement of Water Absorption Rate Test pieces were prepared from the PAEK powders obtained in the Examples and Comparative Examples described below by the following molding method. The water absorption rate was measured using the obtained test pieces with the following device and under the following conditions.
(Molding method)
The PAEK powder was molded into a test piece using a Mini Test Press MP-2FH (Toyo Seiki Co., Ltd.). The molding was performed by melting and degassing several times at a temperature of 350°C and a pressure of 1 to 5 MPa, and then pressing at a temperature of 350°C and a pressure of 12 MPa for 5 minutes. The obtained PAEK sheet was cut into a size of 10 cm x 10 cm.
(Water absorption measurement and calculation method)
The prepared PAEK sheet was dried in a vacuum dryer at 120° C. and 1.0 kPa for 2 hours, and then the weight (weight before immersion) was measured. The PAEK sheet was then completely immersed in a container filled with distilled water and allowed to absorb water for 24 hours at a water temperature of 25° C. After 24 hours, the PAEK sheet was removed, the surface moisture was wiped off, and the weight (weight after immersion) was measured again, and the water absorption rate was calculated using the following calculation formula.
[a formula]
Water absorption rate (%) = (weight after immersion - weight before immersion) ÷ weight before immersion × 100

Example 1
In a 500 mL four-necked reaction vessel equipped with a Dean-Stark tube filled with toluene, a stirrer, and a nitrogen inlet tube, 25.4 g of 4,4'-difluorobenzophenone, 30.0 g of 1,1-bis(4-hydroxyphenyl)cyclohexane, 14.2 g of sodium carbonate, and 145 g of N-methylpyrrolidone (NMP) were charged and dissolved at room temperature while passing nitrogen through. The reaction vessel was then heated to 200°C over 1 hour, after which a small amount of toluene was added and refluxed, followed by polymerization at 200°C for 10 hours.
After the reaction was completed, the reaction solution was cooled to room temperature, and the solution diluted with 150 g of NMP was added to 2400 g of methanol to precipitate. The precipitate was filtered off, and the resulting powder was suspended and washed with 700 g of 1.4% oxalic acid aqueous solution, and then repeatedly washed with hot water until the water after washing became neutral, and then washed with methanol. The washed powder was dried at 150° C. for 12 hours to obtain 40 g of PAEK powder in a yield of 90%.
The resulting PAEK had a reduced viscosity of 1.1 dL/g.
The glass transition temperature (Tg) of the resulting PAEK was 173° C. as measured by differential scanning calorimetry.
The water absorption rate of the obtained PAEK was measured to be 0.38%. In addition, it was revealed that the PAEK sheet produced by this measurement can be bent into an arc shape, and is a resin material having excellent flexibility.

Example 2
In a 1000 mL four-necked reaction vessel equipped with a Dean-Stark tube filled with toluene, a stirrer, and a nitrogen inlet tube, 31 g of 4,4'-difluorobenzophenone, 50 g of 4,4'-(3,3,5-trimethylcyclohexylidene)bis(2,6-dimethylphenol), 17 g of sodium carbonate, and 240 g of NMP were charged and dissolved at room temperature while passing nitrogen through. The reaction vessel was then heated to 200°C over 1 hour, after which a small amount of toluene was added and refluxed, followed by polymerization at 200°C for 50 hours.
After the reaction was completed, the reaction solution was cooled to room temperature, and the solution diluted with 180 g of NMP was added to 3200 g of methanol to precipitate. The precipitate was filtered off, and the resulting powder was suspended and washed in 1000 g of a 1.4% aqueous oxalic acid solution, and then repeatedly washed with hot water until the water after washing became neutral, and then washed with methanol. The washed powder was dried at 150° C. for 12 hours to obtain 65 g of PAEK powder in a yield of 85%.
The resulting PAEK had a reduced viscosity of 0.45 dL/g.
The glass transition temperature (Tg) of the resulting PAEK was 243° C. as measured by differential scanning calorimetry.
The water absorption of the resulting PAEK was measured and found to be 0.06%.

<Comparative Example 1>
Commercially available PEEK450G (manufactured by Victrex) was used to measure the molecular weight, glass transition temperature, relative dielectric constant, dielectric loss tangent, and water absorption rate by the above-mentioned analytical methods.

<Comparative Example 2>
In a 500 mL four-necked reaction vessel equipped with a Dean-Stark tube filled with toluene, a stirrer, and a nitrogen inlet tube, 27 g of 4,4'-difluorobenzophenone, 50 g of 4,4'-(9-fluorenylidene)bis(2,6-dimethylphenol), 20 g of potassium carbonate, and 200 g of NMP were charged and dissolved at room temperature while passing nitrogen through. The reaction vessel was then heated to 200°C over 1 hour, after which a small amount of toluene was added and refluxed, followed by polymerization at 200°C for 10 hours.
After the reaction was completed, the reaction solution was cooled to room temperature, and the solution diluted with 156 g of NMP was added to 2850 g of methanol to precipitate. The precipitate was filtered off, and the resulting powder was suspended and washed in 1000 g of a 1.4% aqueous oxalic acid solution, and then repeatedly washed with hot water until the water after washing became neutral, and then washed with methanol. The washed powder was dried under reduced pressure at 150° C. for 12 hours, and 65 g of PAEK powder was obtained in a yield of 87%.
The resulting PAEK had a reduced viscosity of 0.63 dL/g.
The glass transition temperature (Tg) of the resulting PAEK was 285° C. as measured by differential scanning calorimetry.
The water absorption of the resulting PAEK was measured and found to be 0.53%.

<Comparative Example 3>
In a 500 mL four-necked reaction vessel equipped with a Dean-Stark tube filled with toluene, a stirrer and a nitrogen inlet tube, 34 g of 4,4'-difluorobenzophenone, 19 g of 1,3-dihydro-3,3-bis(4-hydroxyphenyl)-1-phenyl-2H-indol-2-one, 11 g of sodium carbonate and 161 g of NMP were charged and dissolved at room temperature while passing nitrogen. Next, the reaction vessel was heated to 200°C over 1 hour, after which a small amount of toluene was added and refluxed, and polymerization was carried out at 200°C for 7 hours. After the reaction was completed, the product was cooled to room temperature, and a solution diluted with 107 g of NMP was added to 2150 g of methanol to precipitate a precipitate. The precipitate was filtered, suspended and washed with 800 g of a 1.4% aqueous oxalic acid solution, washed with hot water until neutral, and then washed with methanol. After drying under reduced pressure at 150°C for 12 hours, 44 g of PAEK powder was obtained in a yield of 87%.
The resulting PAEK had a reduced viscosity of 0.56 dL/g.
The glass transition temperature (Tg) of the resulting PAEK was 243° C. as measured by differential scanning calorimetry.
The water absorption of the resulting PAEK was measured and found to be 0.32%.

The results of the measurements of the weight average molecular weight (Mw), number average molecular weight (Mn), dispersity (Mw/Mn), glass transition temperature (Tg), relative dielectric constant (Dk) and dielectric loss tangent (Df), and water absorption rate (%) for the PAEK obtained in Examples 1 and 2, the PEEK resin used in Comparative Example 1, and the PAEK obtained in Comparative Examples 2 and 3, measured by the above analytical methods, are summarized in Table 1.

The PAEK obtained in Examples 1 and 2 of the present invention is compared with the PEEK resin of Comparative Example 1. It was revealed that the glass transition temperature (Tg) is 24°C or 94°C higher, and has excellent heat resistance. It was revealed that the relative dielectric constant (Dk) is 0.3 or 0.5 lower, and the dielectric loss tangent (Df) is 0.0003 higher in Example 2 but is the same as in Example 1, and thus the PAEK has equally low and excellent dielectric properties.
The PAEK resins obtained in Comparative Examples 2 and 3 are compared with the PEEK resin in Comparative Example 1. The glass transition temperature (Tg) is high and excellent in heat resistance, and the dielectric constant (Dk) among the dielectric properties is low, but the dielectric loss tangent (Df) is about twice as large, and it can be seen that the resin is generally significantly inferior in dielectric properties. Therefore, it can be seen that the resin is not suitable as a resin material for electronic devices and devices, particularly electronic devices and devices in the high-speed communication field that require high frequency compatibility.
In this regard, the PAEK resins obtained in Examples 1 and 2 of the present invention are compared with the PAEK resins of Comparative Examples 2 and 3. Although the heat resistance of Example 2 and Comparative Example 3 is equivalent, Example 1 is lower than Comparative Examples 2 and 3. However, in terms of the dielectric properties, the relative dielectric constant (Dk) of Example 1 is equivalent to Comparative Example 2, but is lower than Comparative Example 3, and in particular, Example 2 is lower than Comparative Examples 2 and 3. In terms of the dielectric loss tangent (Df), Examples 1 and 2 are significantly lower, about half that of Comparative Examples 2 and 3. From these facts, it has become clear that the resins have both good heat resistance and excellent dielectric properties.
Furthermore, the water absorption rates of the PAEK resins obtained in Examples 1 and 2 of the present invention were 0.38% and 0.06%, respectively, and it was also revealed that they also had low water absorption.
From the above, it has become clear that the polyaryl ether ketone according to the present invention is a resin material that combines good heat resistance, excellent dielectric properties, and low water absorption, and can be suitably used as a resin material for electronic devices and devices.

Claims

A polyaryl ether ketone resin material for use in an electronic device or device, comprising a polyaryl ether ketone having a repeating unit represented by general formula (1), having a dielectric loss tangent (Df) measured at a frequency of 10 GHz of 0.004 or less, a relative dielectric constant (Dk) measured at a frequency of 10 GHz of 3.5 or less, a glass transition temperature of 150°C or more, and a weight average molecular weight (Mw) in the range of 2,000 or more and 1,000,000 or less.
(In the formula, R1 and R2 each independently represent an alkyl group having 1 to 4 carbon atoms, a represents 1 or 2, b each independently represents 0, 1, or 2, and c represents 0 or an integer of 1 to 4.)
2. The polyaryl ether ketone resin material for electronic devices according to claim 1, wherein the repeating unit represented by general formula (1) is a repeating unit represented by general formula (1').
(In the formula, R 2 , a and c are defined as in general formula (1).)
The polyaryl ether ketone resin material for electronic devices and devices according to claim 2, wherein the repeating unit represented by general formula (1') is a repeating unit represented by general formula (1'').
(In the formula, a is defined as in general formula (1).)
Electronic devices and devices using the polyaryl ether ketone resin material for electronic devices and devices described in claim 1.
A method for using a polyaryl ether ketone having a repeating unit represented by general formula (1), which has a dielectric loss tangent (Df) of 0.004 or less measured at a frequency of 10 GHz, a relative dielectric constant (Dk) of 3.5 or less measured at a frequency of 10 GHz, a glass transition temperature of 150°C or more, and a weight average molecular weight (Mw) in the range of 2,000 or more and 1,000,000 or less, in an electronic device or device.
(In the formula, R1 and R2 each independently represent an alkyl group having 1 to 4 carbon atoms, a represents 1 or 2, b each independently represents 0, 1, or 2, and c represents 0 or an integer of 1 to 4.)
A method for using the polyaryl ether ketone according to claim 5 in an electronic device or device, wherein the repeating unit represented by the general formula (1) is a repeating unit represented by the general formula (1').
(In the formula, R 2 , a and c are defined as in general formula (1).)
A method for using the polyaryletherketone according to claim 6 in an electronic device or device, wherein the repeating unit represented by the general formula (1') is a repeating unit represented by the general formula (1'').
(In the formula, a is defined as in general formula (1).)