JP6759682B2 - Branched aromatic polyketone, method for producing branched aromatic polyketone, branched aromatic polyketone composition, branched aromatic polyketone film, optical element, image display device and substrate with branched aromatic polyketone film - Google Patents

Description

The present invention relates to an aromatic polyketone, a method for producing an aromatic polyketone, an aromatic polyketone composition, an aromatic polyketone film, an optical element, an image display device, and a substrate with an aromatic polyketone film.

Aromatic polyketones having an aromatic ring and a carbonyl group in the main chain have excellent heat resistance and mechanical properties, and are used as engineering plastics. Most of the polymers belonging to the aromatic polyketone are aromatic polyetherketones polymerized by utilizing the nucleophilic aromatic substitution reaction, and also have an ether bond in the main chain. On the other hand, an aromatic polyketone that does not have an ether bond in the main chain can exhibit even better heat resistance and chemical resistance than the aromatic polyetherketone (see, for example, Patent Documents 1 and 2). ).

In recent years, it has been reported that an aromatic polyketone having both high transparency and heat resistance can be obtained by directly polymerizing an alicyclic dicarboxylic acid and a 2,2'-dialkoxybiphenyl compound by Friedel-Crafts acylation. (See, for example, Patent Document 3), and is expected to be applied to optical components.

Japanese Unexamined Patent Publication No. 62-7730 Japanese Unexamined Patent Publication No. 2005-272728 Japanese Unexamined Patent Publication No. 2013-53194

Optical components to which a resin material is applied are expected to have properties that cannot be obtained with an inorganic material. For example, it is lighter and more flexible than inorganic materials. Examples of the application destination of the resin material include a coating material utilizing light weight, a glass substitute material, and a flexible display utilizing flexibility.

Further, the resin material is required to be able to form a layer or film having a desired thickness at the application site. Further, when used as a coating material, the formed layer or film is also required to have a high surface hardness. On the other hand, when a molded product molded from a resin material is used for a flexible display or the like, the molded product is required to have excellent flexibility.

Here, in the aromatic polyketone described in Patent Document 3, if the thickness of the film is increased when the film is formed, cracks may occur on the surface. Further, the molded product using this aromatic polyketone has a problem that the elongation rate is low and the surface hardness and flexibility are low.

The present invention has been made in view of the above situation, has excellent heat resistance and transparency, has an excellent elongation rate when a film is formed, and has cracks on the surface even when a thick film is formed. Provided are a method for producing an aromatic polyketone and an aromatic polyketone whose generation is suppressed, and an aromatic polyketone composition using the aromatic polyketone, an aromatic polyketone film, an optical element, an image display device, and a base material with an aromatic polyketone film. ..

The present invention includes the following embodiments.

<1> At least one structural unit selected from the group consisting of the following general formula (1), the following general formula (2), and the following general formula (4), and the structural unit represented by the following general formula (5). And an aromatic polyketone having a structural unit represented by the following general formula (6).

In the general formula (1), R ¹ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent, and R ² is an independent hydrogen atom or a substituent. Indicates a hydrocarbon group having 1 to 30 carbon atoms which may have.

In the general formula (2), R ¹ independently represents a hydrocarbon atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and X is an oxygen atom or the following general formula (3). The divalent group represented is shown.

In the general formula (3), R ³ and R ⁴ each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent.

In the general formula (4), R ⁵ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent.

In the general formula (5), R ¹ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent, and R ⁶ independently represents a hydrogen atom or a substituent. Represents a hydrocarbon group having 1 to 30 carbon atoms which may have.

In the general formula (6), Y represents a divalent hydrocarbon group having a saturated alicyclic hydrocarbon skeleton.

<2> The aromatic polyketone according to <1>, wherein the saturated alicyclic hydrocarbon skeleton in the general formula (6) has 3 to 30 carbon atoms.

<3> Y of the general formula (6) is a group represented by at least one selected from the group consisting of the following general formula (7) and the following general formula (8) <1> or <2>. Aromatic polyketone described in.

In the general formula (7), the hydrogen atom of the adamantane skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom.

In the general formula (8), the hydrogen atom of the adamantane skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom. Z each independently represents a divalent saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.

<4> The aromatic polyketone according to any one of <1> to <3>, wherein the ratio of the structural unit represented by the general formula (5) is 1 mol% to 10 mol%.

<5> With at least one aromatic monomer selected from the group consisting of the following general formula (1'), the following general formula (2'), and the following general formula (4'), and the following general formula (5'). A method for producing an aromatic polyketone in which an aromatic monomer represented by the above and a dicarboxylic acid represented by the following general formula (6') are condensed and reacted in an acidic medium.

In the general formula (1'), R ¹ independently represents a hydrocarbon atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² is an independent hydrogen atom or a substituent. A hydrocarbon group having 1 to 30 carbon atoms which may have a group is shown.

In the general formula (2'), R ¹ independently represents a hydrocarbon atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and X is an oxygen atom or the following general formula (3'). ) Indicates a divalent group.

In the general formula (3'), R ³ and R ⁴ each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent.

In the general formula (4'), R ⁵ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent.

In the general formula (5'), R ¹ independently represents a hydrocarbon atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ⁶ independently represents a hydrogen atom or a substituent. Represents a hydrocarbon group having 1 to 30 carbon atoms which may have a group.

In the general formula (6'), Y represents a divalent hydrocarbon group having a saturated alicyclic hydrocarbon skeleton.

<6> The method for producing an aromatic polyketone according to <5>, wherein the saturated alicyclic hydrocarbon skeleton in the general formula (6') has 3 to 30 carbon atoms.

<7> Y of the general formula (6') is a group represented by at least one selected from the group consisting of the following general formula (7') and the following general formula (8') <5> or The method for producing an aromatic polyketone according to <6>.

In the general formula (7'), the hydrogen atom of the adamantane skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom.

In the general formula (8'), the hydrogen atom of the adamantane skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom. Z each independently represents a divalent saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.

<8> An aromatic polyketone composition containing the aromatic polyketone according to any one of <1> to <4>, a solvent, and the like.

<9> An aromatic polyketone film containing the aromatic polyketone according to any one of <1> to <4>.

<10> An optical element having the aromatic polyketone film according to <9>.

<11> An image display device having the aromatic polyketone film according to <9>.

<12> A base material with an aromatic polyketone film comprising the aromatic polyketone film according to <9> and a base material.

According to the present invention, an aromatic polyketone having excellent heat resistance and transparency, excellent elongation when a film is formed, and suppressing the occurrence of surface cracks even when a thick film is formed. It is possible to provide a method for producing an aromatic polyketone, an aromatic polyketone composition using the aromatic polyketone, an aromatic polyketone film, an optical element, an image display device, and a base material with an aromatic polyketone film.

Hereinafter, the present invention will be described in detail. However, the present invention is not limited to the following embodiments. In the following embodiments, the components (including element steps and the like) are not essential unless otherwise specified. The same applies to the numerical values and their ranges, and does not limit the present invention.

In the present specification, the numerical range indicated by using "~" indicates a range including the numerical values before and after "~" as the minimum value and the maximum value, respectively.
In the numerical range described stepwise in the present specification, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of another numerical range described stepwise. Good. Further, in the numerical range described in the present specification, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
In the present specification, the content of each component in the composition is the total of the plurality of substances present in the composition unless otherwise specified, when a plurality of substances corresponding to each component are present in the composition. Means the content rate of.
In the present specification, the term "layer" or "membrane" refers to a part of the region in addition to the case where the layer or the membrane is formed in the entire region when the region where the layer or the membrane exists is observed. The case where only is formed is also included.
In the present specification, the term "process" includes not only a process independent of other processes but also the process if the purpose of the process is achieved even if it cannot be clearly distinguished from the other process. Is done.

As used herein, the term "transparency" means that the transparency of visible light (transparency of visible light having a wavelength of at least 400 nm) is 80% or more (converted to a film thickness of 1 μm).
As used herein, the term "heat resistance" means that the decrease in transparency due to heating is suppressed in a member containing an aromatic polyketone.
In the present specification, "excellent in elongation" means that the elongation at break of the formed film is 2% or more.

<Aromatic polyketone>
The aromatic polyketone is represented by at least one structural unit selected from the group consisting of the following general formula (1), the following general formula (2) and the following general formula (4), and the following general formula (5). It has a structural unit and a structural unit represented by the general formula (6). The wavy portion in the chemical formula means a bond. Hereinafter, the same applies to the wavy lines in the chemical formula.

In the general formula (1), R ¹ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent, and from the viewpoint of heat resistance, R ¹ is carbon. A hydrocarbon group having a number of 1 to 10 is preferable, and a hydrocarbon group having 1 to 5 carbon atoms is more preferable from the viewpoint of reaction control.

Examples of the hydrocarbon group represented by R ¹ include a saturated aliphatic hydrocarbon group, an unsaturated aliphatic hydrocarbon group, and an alicyclic hydrocarbon group. Further, a combination of these hydrocarbon groups may be used.

The saturated aliphatic hydrocarbon group represented by R ¹ includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group and an n-pentyl group. , Isopentyl group, sec-pentyl group, neo-pentyl group, t-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-icosanyl group, n -Examples include a triacanthanyl group.

Examples of the unsaturated aliphatic hydrocarbon group represented by R ¹ include an alkenyl group such as a vinyl group and an allyl group, and an alkynyl group such as an ethynyl group.

Examples of the alicyclic hydrocarbon group represented by R ¹ include a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and a norbornyl group, and a cycloalkenyl group such as a cyclohexenyl group. Group etc. can be mentioned.

When the hydrocarbon group represented by R ¹ has a substituent, examples of the substituent include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms. When the hydrocarbon group has a substituent, the carbon number of the hydrocarbon group does not include the carbon number of the substituent. The same applies thereafter.

In the general formula (1), R ² independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent. From the viewpoint of heat resistance, R ² is preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms. Examples of such hydrocarbon groups include the same ones as exemplified for R ¹ of the general formula (1). Examples of the substituent include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

In the general formula (2), R ¹ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent, and details of R ^{1 in} the general formula (2) are described. , The same as R ¹ in the general formula (1).

In the general formula (2), X represents an oxygen atom or a divalent group represented by the following general formula (3).

In the general formula (3), R ³ and R ⁴ each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent. From the viewpoint of heat resistance, hydrocarbon groups having 1 to 5 carbon atoms are preferable as R ³ and R ⁴ , respectively. Examples of such hydrocarbon groups include the same ones as exemplified for R ¹ of the general formula (1). Examples of the substituent include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

In the general formula (4), R ⁵ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent. From the viewpoint of heat resistance, the R ^5, each independently, preferably a hydrocarbon group having 1 to 5 carbon atoms. Examples of such hydrocarbon groups include the same ones as exemplified for R ¹ of the general formula (1). Examples of the substituent include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

In the general formula (5), R ¹ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent. This of more ^{R 1,} is the same as ^{R 1} in general formula (1). Each of R ⁶ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent. From the viewpoint of heat resistance, the R ^6, preferably a hydrocarbon group having 1 to 5 carbon atoms. Examples of such hydrocarbon groups include the same ones as exemplified for R ¹ of the general formula (1). Examples of the substituent include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

The proportion of the structural unit represented by the general formula (5) in the aromatic polyketone is from the viewpoint of achieving both solubility in a solvent and suppression of surface cracks even when a thick film is formed. It is preferably 1 mol% to 10 mol%, more preferably 1 mol% to 7 mol%, and further preferably 1 mol% to 5 mol%.

In the general formula (6), Y represents a divalent hydrocarbon group having a saturated alicyclic hydrocarbon skeleton. The saturated alicyclic hydrocarbon skeleton in Y preferably has 3 to 30 carbon atoms, and more preferably 6 to 30 carbon atoms. When the saturated alicyclic hydrocarbon skeleton has 3 to 30 carbon atoms, a polyketone film having excellent surface hardness or flexibility tends to be obtained.

Saturated alicyclic hydrocarbon skeletons include cyclopropane skeleton, cyclobutane skeleton, cyclopentane skeleton, cyclohexane skeleton, cycloheptane skeleton, cyclooctane skeleton, cubane skeleton, norbornane skeleton, and tricyclo [5.2.1.0] decane skeleton. , Adamantane skeleton, diadamantane skeleton, bicyclo [2.2.2] octane skeleton and the like.

Y in the general formula (6) is preferably a group represented by at least one selected from the group consisting of the following general formula (7) and the following general formula (8). When Y is a group represented by the general formula (7), a film having excellent surface hardness tends to be obtained. Further, when Y is a group represented by the general formula (8), a film having excellent flexibility tends to be obtained.

In the general formula (7), the hydrogen atom of the adamantane skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom.

In the general formula (8), the hydrogen atom of the adamantane skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom. Further, Z independently represents a divalent saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. From the viewpoint of heat resistance, Z is preferably a saturated hydrocarbon group having 1 to 5 carbon atoms.

Examples of the divalent saturated hydrocarbon group represented by Z include a methylene group, an ethylene group, a trimethylene group, a methylethylene group, a tetramethylene group, a 1-methyltrimethylene group, a 2-methyltrimethylene group and an ethylethylene group. 1,1-dimethylethylene group, 1,2-dimethylethylene group, pentylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1-ethyltrimethylene group, 2-ethyltrimethylene group, 1,1 -Dimethyltrimethylene group, 2,2-dimethyltrimethylene group, 1,2-dimethyltrimethylene group, propylethylene group, ethylmethylethylene group, hexylene group, 1-methylpentylene group, 2-methylpentylene group, 3-Methylpentylene group, 1-ethyltetramethylene group, 2-ethyltetramethylene group, 1-propyltrimethylene group, 2-propyltrimethylene group, butylethylene group, 1,1-dimethyltetramethylene group, 2, 2-Dimethyltetramethylene group, 1,2-dimethyltetramethylene group, 1,3-dimethyltetramethylene group, 1,4-dimethyltetramethylene group, 1,2,3-trimethyltrimethylene group, 1,1,2 -Trimethyltrimethylene group, 1,1,3-trimethyltrimethylene group, 1,2,2-trimethyltrimethylene group, 1-ethyl-1-methyltrimethylene group, 2-ethyl-2-methyltrimethylene group, Examples thereof include 1-ethyl-2-methyltrimethylene group, 2-ethyl-1-methyltrimethylene group, heptylene group, octylene group, nonylene group and decylene group.

When the divalent saturated hydrocarbon group represented by Z has a substituent, examples of the substituent include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

<Manufacturing method of aromatic polyketone>
The method for producing the aromatic polyketone of the present embodiment is not particularly limited. For example, at least one aromatic monomer selected from the group consisting of the following general formula (1'), the following general formula (2') and the following general formula (4'), and the following general formula (5') are shown. It can be obtained by subjecting the aromatic monomer to a condensation reaction in an acidic medium with a dicarboxylic acid represented by the following general formula (6'). Hereinafter, the aromatic monomer and the dicarboxylic acid may be referred to as "raw materials".

In the general formula (1'), R ¹ independently represents a hydrocarbon atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² is an independent hydrogen atom or a substituent. A hydrocarbon group having 1 to 30 carbon atoms which may have a group is shown. More general formula (1 ') in ^{R 1} and ^{R 2} each is the same as ^{R 1} and ^{R 2} in the general formula (1).

In the general formula (2'), R ¹ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent. The details of R ¹ in the general formula (2') are the same as those in R ¹ in the general formula (2). X represents an oxygen atom or a divalent group represented by the following general formula (3').

In the general formula (3'), R ³ and R ⁴ each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent. Each of the details of the general formula (3 ') in ^{R 3} and ^{R 4,} are the same respectively as ^{R 3} and ^{R 4} in the general formula (3).

In the general formula (4'), R ⁵ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent. The details of R ⁵ in the general formula (4') are the same as those in R ⁵ in the general formula (4).

In the general formula (5'), R ¹ independently represents a hydrocarbon group having 1 to 30 carbon atoms, and R ⁶ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent. Shows 30 hydrocarbon groups. The general formula (5 ') Details of each of ^{R 1} and ^{R 6} in the same respectively as ^{R 1} and ^{R 6} in the general formula (5).

In the general formula (6'), Y represents a divalent hydrocarbon group having a saturated alicyclic hydrocarbon skeleton. The details of Y in the general formula (6') are the same as those in Y in the general formula (6). Y in the general formula (6') is preferably a group represented by at least one selected from the group consisting of the following general formula (7') and the following general formula (8').

In the general formula (7'), the hydrogen atom of the adamantane skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom.

In the general formula (8'), the hydrogen atom of the adamantane skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom. Z each independently represents a divalent saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. The details of Z in the general formula (8') are the same as those in Z in the general formula (8).

The acidic medium used for the condensation reaction is not particularly limited, and for example, an organic solvent solution of aluminum chloride, an organic solvent solution of trifluoroalcan sulfonic acid, polyphosphoric acid, and a mixture of diphosphorus pentoxide and organic sulfonic acid may be used. it can. From the viewpoint of reactivity and ease of handling, it is preferable to use a mixture of diphosphorus pentoxide and organic sulfonic acid as the acidic medium, and methanesulfonic acid is preferable as the organic sulfonic acid.

If the amount of diphosphorus pentoxide is too small in the mixture of diphosphorus pentoxide and organic sulfonic acid, the reactivity tends to be poor. The mixing ratio is preferably diphosphorus pentoxide: organic sulfonic acid = 1: 5 to 1:20, more preferably 1: 5 to 1:10, in terms of mass ratio, from the viewpoint of controlling the mixing ratio and reactivity.

The blending amount of the acidic medium with respect to the raw material is not particularly limited as long as it can dissolve the raw material, and can be used in the range from the catalyst amount to the solvent amount. From the viewpoint of reactivity and ease of handling, the range of 5 parts by mass to 100 parts by mass is preferable with respect to 1 part by mass of the dicarboxylic acid.

The reaction temperature is preferably 10 ° C. to 100 ° C. from the viewpoint of preventing coloring of the reaction product and side reactions, and 20 ° C. to 100 ° C. from the viewpoint of increasing the reaction rate and improving productivity. More preferably.

The atmosphere of the reaction is not particularly limited, and the reaction can be carried out in an open system. However, since the reactivity of the acidic medium decreases due to the presence of water, it is preferable to use dry air, nitrogen, argon or the like. It is more preferable to use nitrogen or argon to prevent unexpected side reactions.

The reaction can be promoted by stirring the reaction solution. The stirring method is not particularly limited, and a stirrer such as a magnetic stirrer or a mechanical stirrer can be used.

The reaction time can vary depending on the reaction temperature, the target molecular weight of the aromatic polyketone, the type of monomer used in the reaction, and the like. In order to obtain a polyketone having a sufficiently high molecular weight, the reaction time is preferably about 1 hour to 120 hours, more preferably 1 hour to 72 hours from the viewpoint of productivity.

The pressure of the reaction is not particularly limited, and the reaction may be carried out under normal pressure, pressurized pressure, or reduced pressure. From the viewpoint of cost, it is preferable to carry out the reaction under normal pressure.

After the reaction is completed, the reaction solution can be brought into contact with a poor solvent to precipitate a resin, impurities can be extracted into the poor solvent layer, and the precipitated resin can be separated from the liquid by a method such as filtration, decantation, or centrifugation. it can. After that, the separated resin is dissolved again in a good solvent, contacted with a poor solvent again to precipitate the resin, impurities are extracted into the poor solvent layer, and the precipitated resin is filtered, decanted, centrifuged, or the like. The step of separating from the liquid may be repeated.

<Aromatic polyketone composition>
The aromatic polyketone composition contains the aromatic polyketone of the present embodiment and a solvent. The aromatic polyketone composition can be obtained by dissolving the aromatic polyketone of the present embodiment in a solvent or the like. The method for dissolving the aromatic polyketone in the solvent is not particularly limited, and a method known in the art can be used. Further, if necessary, the insoluble component may be filtered off after dissolution.

Examples of the solvent include γ-butyrolactone, ethyl lactate, propylene glycol monomethyl ether acetate, butyl acetate, benzyl acetate, ethoxyethyl propionate, 3-methylmethoxypropionate, N-methyl-2-pyrrolidone, and N-cyclohexyl. -2-Pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, hexamethylphosphorylamide, tetramethylenesulfone, diethylketone, diisobutylketone, methylamylketone, cyclohexanone, propylene glycol monomethyl ether, propylene glycol Examples thereof include monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, xylene, mesityrene, ethylbenzene, propylbenzene, cumene, diisopropylbenzene, hexylbenzene, anisole, diglime, dimethyl sulfoxide, chloroform, dichloromethane, dichloroethane, and chlorobenzene. .. These solvents may be used alone or in combination of two or more.

The aromatic polyketone composition may further contain additives and the like in addition to the aromatic polyketone and the solvent. Examples of the additive include an adhesive aid, a surfactant, a leveling agent, an antioxidant, an ultraviolet deterioration inhibitor and the like.

<Aromatic polyketone membrane>
The aromatic polyketone membrane contains the aromatic polyketone of the present embodiment. The aromatic polyketone film can be obtained, for example, by using the above-mentioned aromatic polyketone composition. The aromatic polyketone film of the present embodiment is a conventional aromatic polyketone film (for example, an aromatic polyketone film containing an aromatic polyketone polymerized only from an alicyclic dicarboxylic acid and a 2,2'-dialkoxybiphenyl compound). It can be made thicker than that. The aromatic polyketone film of the present embodiment suppresses the occurrence of surface cracks even when a thick film is formed.

The aromatic polyketone film can be produced, for example, by the following method. First, the aromatic polyketone composition is applied to the surface of at least a part of the base material to form a composition layer. The method for imparting the aromatic polyketone composition to the base material is not particularly limited as long as the composition layer can be formed at any place on the base material in any shape. For example, a dipping method, a spray method, a screen printing method, a rotary coating method and the like are preferably used.

The base material to which the aromatic polyketone composition is applied is not particularly limited, and is glass, semiconductor, metal oxide insulator (titanium oxide, silicon oxide, etc.), silicon nitride, triacetyl cellulose, transparent polyimide, polycarbonate, acrylic type. A transparent base material composed of a transparent resin such as a polymer or a cycloolefin resin can be exemplified. The shape of the base material is not particularly limited, and may be plate-shaped or film-shaped. The aromatic polyketone of the present embodiment, which has excellent surface hardness when formed into a film, can be suitably used as a coating material for a base material.

After applying (coating) the aromatic polyketone composition to the substrate to form the composition layer, the composition layer is dried in the drying step to obtain an aromatic polyketone film. The drying method is not particularly limited, and examples thereof include a method of heating using a device such as a hot plate or an oven.

If necessary, the dried aromatic polyketone membrane may be further heat-treated. The heat treatment method is not particularly limited, and is a box type dryer, a hot air type conveyor type dryer, a quartz tube furnace, a hot plate, a rapid thermal annealing, a vertical diffusion furnace, an infrared curing furnace, an electron beam curing furnace, and a microwave curing furnace. It can be carried out using a device such as. The atmospheric conditions in the heat treatment step may be either in the atmosphere or in an inert atmosphere such as nitrogen.

The aromatic polyketone membrane can also be used by peeling it from the substrate, if necessary.

<Base material with aromatic polyketone film>
The base material with an aromatic polyketone film has the aromatic polyketone film of the present embodiment and the base material. The base material is not particularly limited, and the base material used for producing the above-mentioned aromatic polyketone film may be used as it is without being peeled off. Further, if the base material is a transparent base material, it can be suitably used for the optical element described later. Examples of the transparent substrate include those exemplified in the production of an aromatic polyketone film.

In the base material with an aromatic polyketone film, the aromatic polyketone film may be provided on at least a part of the surface of the base material, and may be provided on only one surface of the base material or on both sides. Good. Further, in the base material with an aromatic polyketone film, the aromatic polyketone film may have one layer or a multi-layer structure in which two or more layers are laminated.

<Optical element and image display device>
The optical element and the image display device each have the aromatic polyketone film of the present embodiment. The aromatic polyketone film in the optical element and the image display device may be the above-mentioned base material with the aromatic polyketone film.

In the optical element and the image display device, for example, the base material side of the base material with an aromatic polyketone film is attached to an application place such as an LCD (liquid crystal display) or an ELD (electroluminescence display) via an adhesive or an adhesive. You can get it with it.

Various optical elements such as an aromatic polyketone film and a polarizing plate using the same can be preferably used in various image display devices such as a liquid crystal display device. The image display device may have the same configuration as the conventional image display device except that the aromatic polyketone film of the present embodiment is used. When the image display device of the present embodiment is a liquid crystal display device, each component such as a liquid crystal cell, an optical element such as a polarizing plate, and a lighting system (backlight or the like) is appropriately assembled to form a drive circuit. It can be manufactured by incorporating it. The liquid crystal cell is not particularly limited, and various types such as TN type, STN type, and π type can be used.

Applications of image display devices include OA devices such as desktop PCs, laptop computers, and copy machines, mobile devices such as mobile phones, clocks, digital cameras, mobile information terminals (PDAs), and portable game machines, video cameras, televisions, and electronic devices. Household electrical equipment such as range, back monitor, car navigation system monitor, in-vehicle equipment such as car audio, exhibition equipment such as information monitor for commercial stores, security equipment such as monitoring monitor, nursing monitor, medical use Examples include nursing care / medical equipment such as monitors.

Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to these examples as long as it does not deviate from the gist thereof.

(Synthesis of 1,3,5-tris (2-methoxyphenyl) benzene)
In a flask, 5.0 mmol of 1,3,5-tribromobenzene, 45.0 mmol of 2-methoxyphenylboronic acid, 30.0 mmol of sodium carbonate, 100 ml of dimethylformamide, and 100 ml of pure water are placed, and acetic acid is placed therein. Palladium was added so as to be 1.5 mol%, and a nitrogen balloon was attached and the mixture was stirred at 60 ° C. for 12 hours. The reaction solution was returned to room temperature (about 25 ° C.), 500 ml of pure water was added, and the mixture was extracted 3 times with 500 ml of ethyl acetate. Then, the organic layer was washed with water and dehydrated with anhydrous sodium sulfate. Then, it was concentrated under reduced pressure to obtain a residue. The residue was purified on a silica gel column to give 1,3,5-tris (2-methoxyphenyl) benzene (yield 43% by mass).

[Synthesis Example 1] Synthesis of polyketone PK1 In a flask, 4.9 mmol of 2,2'-dimethoxybiphenyl, 5.0 mmol of 1,3-adamantandicarboxylic acid, and 1,3,5-tris (2-methoxyphenyl) benzene Add 0.1 mmol, add 15 ml of a mixture of diphosphorus pentoxide and methanesulfonic acid (mass ratio (diphosphorus pentoxide: methanesulfonic acid) = 1:10), attach a nitrogen balloon to 60 ° C. Was stirred for 10 hours. After the reaction, the reaction solution was poured into 500 ml of methanol, and the formed precipitate was collected by filtration. The obtained solid was washed with distilled water and methanol and then dried to obtain a polyketone PK1. The obtained polyketone PK1 had a weight average molecular weight of 21,000 and a number average molecular weight of 2,800.
At this time, when the obtained polyketone PK1 is visually colored, the polyketone PK1 is dissolved in 5 g of N-methyl-2-pyrrolidone (NMP), and the solution is poured into 200 ml of distilled water to produce a precipitate. The steps of filtering, washing and drying the material were repeated until the polyketone PK1 was no longer visible.

The molecular weight (weight average molecular weight and number average molecular weight) of the polyketone was measured by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as an eluent and determined in terms of standard polystyrene. The details are as follows.

-Device name: Ecosec HLC-8320GPC (Tosoh Corporation)
-Column: TSKgel Supermultipore HZ-M (Tosoh Corporation)
・ Detector: UV detector and RI detector combined ・ Flow velocity: 0.4 ml / min

[Synthesis Example 2] Synthesis of polyketone PK2 The raw materials used were 4.5 mmol of 2,2'-dimethoxybiphenyl, 5.0 mmol of 1,3-adamantandicarboxylic acid, and 1,3,5-tris (2-methoxyphenyl) benzene. Polyketone PK2 was obtained in the same manner as in Synthesis Example 1 except that it was changed to 0.5 mmol. The obtained polyketone PK2 had a weight average molecular weight of 30,000 and a number average molecular weight of 3,400.

[Synthesis Example 3] Synthesis of polyketone PK3 The raw materials used were 2,2'-dimethoxybiphenyl 4.0 mmol, 1,3-adamantane dicarboxylic acid 5.0 mmol, and 1,3,5-tris (2-methoxyphenyl) benzene. Polyketone PK3 was obtained in the same manner as in Synthesis Example 1 except that it was changed to 1.0 mmol. The obtained polyketone PK3 had a weight average molecular weight of 45,000 and a number average molecular weight of 4,900.

[Synthesis Example 4] Synthesis of polyketone PK4 The raw materials used were 4.5 mmol of 2,2'-dimethoxybiphenyl, 5.0 mmol of cyclohexane-1,3-dicarboxylic acid, and 1,3,5-tris (2-methoxyphenyl). Polyketone PK4 was obtained in the same manner as in Synthesis Example 1 except that the benzene was changed to 0.5 mmol. The obtained polyketone PK4 had a weight average molecular weight of 15,000 and a number average molecular weight of 3,000.

[Synthesis Example 5] Synthesis of polyketone PK5 The raw materials used were 4.5 mmol of 2,2'-dimethoxydiphenylmethane, 5.0 mmol of 1,3-adamantane dicarboxylic acid, and 1,3,5-tris (2-methoxyphenyl) benzene. Polyketone PK5 was obtained in the same manner as in Synthesis Example 1 except that it was changed to 0.5 mmol. The obtained polyketone PK5 had a weight average molecular weight of 20,000 and a number average molecular weight of 3,000.

[Synthesis Example 6] Synthesis of polyketone PK6 The raw materials used were 2,2'-dimethoxybiphenyl 4.9 mmol, 1,3-adamantane diacetic acid 5.0 mmol, and 1,3,5-tris (2-methoxyphenyl) benzene. Polyketone PK6 was obtained in the same manner as in Synthesis Example 1 except that it was changed to 0.1 mmol. The obtained polyketone PK6 had a weight average molecular weight of 100,000 and a number average molecular weight of 26,000.

[Synthesis Example 7] Synthesis of polyketone PK7 The raw materials used were 4.5 mmol of 2,2'-dimethoxybiphenyl, 5.0 mmol of 1,3-adamantane diacetic acid, and 1,3,5-tris (2-methoxyphenyl) benzene. Polyketone PK7 was obtained in the same manner as in Synthesis Example 1 except that it was changed to 0.5 mmol. The obtained polyketone PK7 had a weight average molecular weight of 120,000 and a number average molecular weight of 32,000.

[Synthesis Example 8] Synthesis of polyketone PK8 Raw materials used were 2,2'-dimethoxybiphenyl 4.0 mmol, 1,3-adamantane diacetic acid 5.0 mmol, and 1,3,5-tris (2-methoxyphenyl) benzene. Polyketone PK8 was obtained in the same manner as in Synthesis Example 1 except that it was changed to 1.0 mmol. The weight average molecular weight of the obtained polyketone PK8 was 140,000, and the number average molecular weight was 35,000.

[Comparative Synthesis Example 1] Synthesis of polyketone PK9 Polyketone in the same manner as in Synthesis Example 1 except that the raw materials were changed to 2,2'-dimethoxybiphenyl 5.0 mmol and 1,3-adamantane dicarboxylic acid 5.0 mmol. Obtained PK9. The weight average molecular weight of the obtained PK9 was 21,000, and the number average molecular weight was 2,800.

[Comparative Synthesis Example 2] Synthesis of polyketone PK10 The same as in Synthesis Example 1 except that the raw materials were changed to 2,2'-dimethoxybiphenyl 5.0 mmol and cyclohexane-1,3-dicarboxylic acid 5.0 mmol. Polyketone PK10 was obtained. The weight average molecular weight of the obtained PK10 was 11,000, and the number average molecular weight was 2,800.

[Comparative Synthesis Example 3] Synthesis of polyketone PK11 Polyketone in the same manner as in Synthesis Example 1 except that the raw materials were changed to 2,2'-dimethoxybiphenyl 5.0 mmol and 1,3-adamantane diacetic acid 5.0 mmol. Obtained PK11. The weight average molecular weight of the obtained PK11 was 80,000, and the number average molecular weight was 20,000.

[Reference Synthesis Example 4] Synthesis of polyketone PK12 Raw materials were 2,2'-dimethoxybiphenyl 3.8 mmol, 1,3-adamantane dicarboxylic acid 5.0 mmol, and 1,3,5-tris (2-methoxyphenyl). Polyketone PK12 was obtained in the same manner as in Synthesis Example 1 except that the benzene was changed to 1.2 mmol. However, since the obtained polyketone PK12 was insoluble in THF, its molecular weight could not be measured.

[Reference Synthesis Example 5] Synthesis of polyketone PK13 Raw materials were 2,2'-dimethoxybiphenyl 3.8 mmol, cyclohexane-1,3-dicarboxylic acid 5.0 mmol, and 1,3,5-tris (2-methoxyphenyl). ) Polyketone PK13 was obtained in the same manner as in Synthesis Example 1 except that the benzene was changed to 1.2 mmol. However, since the obtained polyketone PK13 was insoluble in THF, its molecular weight could not be measured.

[Reference Synthesis Example 6] Synthesis of polyketone PK14 Raw materials used were 2,2'-dimethoxybiphenyl 3.8 mmol, 1,3-adamantane diacetic acid 5.0 mmol, and 1,3,5-tris (2-methoxyphenyl). Polyketone PK14 was obtained in the same manner as in Synthesis Example 1 except that the benzene was changed to 1.2 mmol. However, since the obtained polyketone PK14 was insoluble in THF, its molecular weight could not be measured.

[Preparation Example 1] PK1 composition
The polyketone PK1 obtained in Synthesis Example 1 is added to 1-methyl-2-pyrrolidone (NMP) so as to have a concentration of 20% by mass, heated to 50 ° C. to dissolve it, and a membrane filter made of polytetrafluoroethylene (pore size). The mixture was filtered through 5 μm) to obtain a PK1 composition.

[Preparation Examples 2-8] PK2-8 Composition A PK2-8 composition was prepared in the same manner as in Preparation Example 1 except that the polyketone PK2-8 obtained in Synthesis Examples 2-8 was used.

[Comparative Preparation Examples 1 to 3] PK9 to 11 Compositions PK9 to 11 compositions were prepared in the same manner as in Preparation Example 1 except that the polyketones PK9 to 11 obtained in Comparative Synthesis Examples 1 to 3 were used.

[Reference Preparation Examples 4 to 6] PK12 to 14 Composition The polyketones PK12 to 14 obtained in Reference Synthesis Examples 4 to 6 were added to 1-methyl-2-pyrrolidone (NMP) and heated to 50 ° C., but did not dissolve. The composition could not be adjusted.

[Example 1] Base material with PK1 film The PK1 composition obtained in Preparation Example 1 was applied onto a glass base material and a polyimide base material by a bar coating method. Then, after drying for 3 minutes on a hot plate heated to 120 ° C., the mixture is placed in a nitrogen-substituted high-temperature clean oven (Koyo Thermo System Co., Ltd., CLH-21CD (III)) from 25 ° C. to 200 ° C. in 1 hour. The temperature was raised, further heated at 200 ° C. for 1 hour to cure, and then lowered from 200 ° C. to 80 ° C. in 1 hour to obtain two types of PK1 film-coated substrates.
When producing a thick film, the film was dried on a hot plate for 3 minutes, and then the PK1 composition was applied and dried by a bar coating method, and then cured. The obtained base material with a PK1 film was subjected to an evaluation test described later.

[Examples 2 to 8 ] PK2 to 8 film-coated base material PK2 to the same as in Example 1 except that the PK2 to 8 compositions obtained in Preparation Examples 2 to 8 were used instead of the PK1 composition. A substrate with 8 films was obtained and the evaluation test described later was performed.

[Comparative Examples 1 to 3] PK9 to 11 film-coated substrate PK9 in the same manner as in Example 1 except that the PK9 to 11 compositions obtained in Comparative Preparation Examples 1 to 3 were used instead of the PK1 composition. A substrate with a film of ~ 11 was obtained and an evaluation test was conducted.

(Evaluation of transparency)
Among the base materials with PK1 to 11 films obtained in Examples 1 to 8 or Comparative Examples 1 to 3, those using glass as the base material were measured with an ultraviolet-visible spectrophotometer (“U”) for the transmittance of ultraviolet light at 400 nm. It was measured by the ultraviolet-visible absorption spectrum method using -3310 Spectrophotometer (Hitachi High-Tech Co., Ltd.). Table 1 shows the transmittance converted to a film thickness of 1 μm using a glass substrate without a film as a reference.

(Evaluation of heat resistance)
Among the base materials with PK1 to 11 films obtained in Examples 1 to 8 or Comparative Examples 1 to 3, those using glass as the base material were allowed to stand in an oven at 200 ° C. for 24 hours to transmit ultraviolet light at 400 nm. The rate was measured by an ultraviolet-visible absorption spectrum method using an ultraviolet-visible spectrophotometer (“U-3310 Spectrophotometer”, Hitachi High-Technologies Corporation). Table 1 shows the transmittance converted to a film thickness of 1 μm using a glass substrate without a film as a reference.

(Evaluation of cracked film thickness)
The film thickness at which cracks were generated on the surface of the PK1-11 film-coated glass substrate (both the glass substrate and the polyimide substrate) obtained in Examples 1 to 8 or Comparative Examples 1 to 3 was confirmed by the above method. The judgment criteria are as follows. The results are shown in Table 1.
A: No cracks occur on the surface even if the thickness is 50 μm or more.
B: Cracks occur on the surface with a thickness of 40 μm or more and less than 50 μm.
C: Cracks occur on the surface with a thickness of 30 μm or more and less than 40 μm.
D: Cracks occur on the surface with a thickness of 20 μm or more and less than 30 μm.
E: Cracks occur on the surface with a thickness of 10 μm or more and less than 20 μm.
F: Cracks occur on the surface with a thickness of 5 μm or more and less than 10 μm.
G: Cracks occur on the surface with a thickness of less than 5 μm.

(Evaluation of pencil hardness)
Among the PK1 to 11 film-attached substrates obtained in Examples 1 to 8 or Comparative Examples 1 to 3, those using glass as the substrate were evaluated by a pencil hardness test. The test was performed according to JIS K5600-5-4: 1999. The test results are shown in Table 1.

(Evaluation of bending resistance)
Among the base materials with PK1 to 11 films obtained in Examples 1 to 8 or Comparative Examples 1 to 3, those using polyimide as the base material were evaluated by a mandrel test (cylindrical mandrel method). The test was carried out according to JIS K5600-5-1: 1999. The diameter of the mandrel was changed from 25 mm to 2 mm, and the presence or absence of cracks was visually confirmed. Table 1 shows the minimum diameter of the mandrel without cracks.

(Measurement of elongation rate)
The aromatic polyketone film was peeled off from the base material with the PK1-11 film obtained in Examples 1 to 8 or Comparative Examples 1 to 3 using polyimide as the base material. Then, the peeled aromatic polyketone film was subjected to a tensile test at a speed of 5 mm / min using AUTOGRAPH EZ-TEST EZ-S (manufactured by Shimadzu Corporation), and the elongation rate was measured. The results are shown in Table 1.

As can be seen by comparing Examples 1 to 8 and Comparative Examples 1 to 3, the aromatic polyketone of the example has a higher elongation rate when a film is formed and thickens the film as compared with the polyketone of the comparative example. Can be done. Further, in Examples 1 to 5, by using 1,3-adamantane dicarboxylic acid or cyclohexane-1,3-dicarboxylic acid as a raw material, a film having transparency, heat resistance and high hardness is obtained. On the other hand, in Examples 6 to 8, a film having excellent transparency, heat resistance and flexibility was obtained by using 1,3-adamantane diacetic acid as a raw material. In this way, a polyketone film having a high pencil hardness and a polyketone having excellent flexibility can be produced according to the purpose.

Claims (12)

At least one structural unit selected from the group consisting of the following general formula (1), the following general formula (2), and the following general formula (4), the structural unit represented by the following general formula (5), and the following An aromatic polyketone having a structural unit represented by the general formula (6).

(In the general formula (1), R ¹ independently represents a hydrocarbon atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² is an independent hydrogen atom or a substituent. Indicates a hydrocarbon group having 1 to 30 carbon atoms which may have a group.)

(In the general formula (2), R ¹ independently represents a hydrocarbon atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and X is an oxygen atom or the following general formula (3). Indicates a divalent group represented by.)

(In the general formula (3), R ³ and R ⁴ each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent.)

(In the general formula (4), R ⁵ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent.)

(In the general formula (5), R ¹ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent, and R ⁶ independently represents a hydrogen atom or a substituent. It represents a hydrocarbon group having 1 to 30 carbon atoms which may have a group.)

(In the general formula (6), Y represents a divalent hydrocarbon group having a saturated alicyclic hydrocarbon skeleton.) The aromatic polyketone according to claim 1, wherein the saturated alicyclic hydrocarbon skeleton in the general formula (6) has 3 to 30 carbon atoms. The invention according to claim 1 or 2, wherein Y of the general formula (6) is a group represented by at least one selected from the group consisting of the following general formula (7) and the following general formula (8). Aromatic polyketone.

(In the general formula (7), the hydrogen atom of the adamantane skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom.)

(In the general formula (8), the hydrogen atom of the adamantan skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom. Z has a substituent independently. It shows a divalent saturated hydrocarbon group having 1 to 10 carbon atoms.) The aromatic polyketone according to any one of claims 1 to 3, wherein the ratio of the structural unit represented by the general formula (5) is 1 mol% to 10 mol%. It is represented by at least one aromatic monomer selected from the group consisting of the following general formula (1'), the following general formula (2') and the following general formula (4'), and the following general formula (5'). A method for producing an aromatic polyketone in which an aromatic monomer and a dicarboxylic acid represented by the following general formula (6') are condensed in an acidic medium.

(In the general formula (1'), R ¹ independently represents a hydrocarbon atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² independently represents a hydrogen atom or a hydrocarbon group. Indicates a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent.)

(In the general formula (2'), R ¹ independently represents a hydrocarbon atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and X is an oxygen atom or the following general formula (3). Indicates a divalent group represented by').)

(In the general formula (3'), R ³ and R ⁴ each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent.)

(In the general formula (4'), R ⁵ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a hydrogen atom or a substituent.)

(In the general formula (5'), R ¹ independently represents a hydrocarbon atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ⁶ independently represents a hydrogen atom or a hydrocarbon group. It represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent.)

(In the general formula (6'), Y represents a divalent hydrocarbon group having a saturated alicyclic hydrocarbon skeleton.) The method for producing an aromatic polyketone according to claim 5, wherein the saturated alicyclic hydrocarbon skeleton according to the general formula (6') has 3 to 30 carbon atoms. Claim 5 or claim 6 in which Y of the general formula (6') is a group represented by at least one selected from the group consisting of the following general formula (7') and the following general formula (8'). The method for producing an aromatic polyketone according to.

(In the general formula (7'), the hydrogen atom of the adamantane skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom.)

(In the general formula (8'), the hydrogen atom of the adamantan skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom. Each Z independently has a substituent. Indicates a divalent saturated hydrocarbon group having 1 to 10 carbon atoms which may be used.) The aromatic polyketone composition containing the aromatic polyketone according to any one of claims 1 to 4 and a solvent. An aromatic polyketone film containing the aromatic polyketone according to any one of claims 1 to 4. The optical element having the aromatic polyketone film according to claim 9. An image display device having the aromatic polyketone film according to claim 9. A base material with an aromatic polyketone film, which comprises the aromatic polyketone film according to claim 9 and a base material.