JPWO2018025673A1 - Polyketone composition containing nitrogen-containing compound, cured product of polyketone, optical element and image display device - Google Patents

Abstract

The polyketone composition contains a polyketone and a nitrogen-containing compound. The polyketone contains the structural unit represented by the general formula (I) in the main chain. The nitrogen-containing compound has a nitrogen atom and at least one group selected from the group consisting of a hydroxymethyl group and an alkoxymethyl group bonded to the nitrogen atom. In the formula (I), X each independently represents a divalent group having 1 to 50 carbon atoms which may have a substituent, and Y may each independently have a substituent A good C1-C30 bivalent hydrocarbon group is shown, n shows the integer of 3-1000.

Description

  The present invention relates to a polyketone composition containing a nitrogen-containing compound, a cured polyketone product, an optical element, and an image display device.

  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 aromatic polyketones are aromatic polyether ketones polymerized using a nucleophilic aromatic substitution reaction, and have ether bonds in the main chain. On the other hand, aromatic polyketones having no ether bond in the main chain are known to be more excellent in heat resistance and chemical resistance than aromatic polyether ketones (for example, Patent Document 1 and Patent Document 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. Application to optical parts is expected (see, for example, Patent Document 3).

  When a resin material such as aromatic polyketone is applied to an optical component, lightness and flexibility are expected as characteristics which can not be obtained with an inorganic material, as compared with, for example, an inorganic material. As the application destination of the resin material, for example, a coating material utilizing its light weight, a glass substitute material, etc., and a flexible display utilizing its flexibility, etc. may be mentioned. In particular, the realization of application to flexible displays has attracted particular attention in recent years.

Japanese Patent Application Laid-Open No. 62-7730 JP, 2005-272728, A JP, 2013-53194, A

  Furthermore, when an aromatic polyketone is used as a film, in addition to transparency, heat resistance and chemical resistance, it may be desired to have a high elongation.

  The present invention was made in view of the above-mentioned present situation, and when it is made a cured film, it is excellent in heat resistance, transparency and chemical resistance, and the polyketone composition and polyketone cured product which show high elongation rate, and polyketone cured product An optical element and an image display device having the

  Means for solving the above problems include the following embodiments.

<1> A polyketone containing a structural unit represented by the following general formula (I) in its main chain, and
A nitrogen-containing compound having a nitrogen atom and at least one group selected from the group consisting of a hydroxymethyl group and an alkoxymethyl group bonded to the nitrogen atom,
Containing polyketone composition.

  In the general formula (I), X each independently represents a divalent group having 1 to 50 carbon atoms which may have a substituent, and Y each independently has a substituent It also has a good hydrocarbon number of 1 to 30 carbon atoms, and n is an integer of 3 to 1000.

<2> The polyketone composition according to <1>, wherein in the general formula (I), each X independently includes an aromatic ring-containing divalent group having 6 to 50 carbon atoms.

<3> In the general formula (I), a divalent group represented by at least one kind of X independently selected from the group consisting of the following general formulas (II-1) to (II-3) The polyketone composition as described in <1> or <2> containing <1> or <2>.

In general formula (II-1), R ¹ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² is independently substituted C1-30 hydrocarbon group which may have a group is shown, and m shows the integer of 0-3 each independently.

In general formula (II-2), R ¹ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² is independently substituted Group each independently represent an integer of 0 to 3, and Z is an oxygen atom or a compound represented by the following formula (III-1): ) To (III-7) are shown.

In general formulas (III-1) to (III-7), R ¹ independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² is And each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ³ and R ⁴ each independently represent a hydrogen atom or carbon which may have a substituent. It represents the number 1 to 30 hydrocarbon group. m independently represents an integer of 0 to 3, n independently represents an integer of 0 to 4, and p independently represents an integer of 0 to 2.

In general formula (II-3), R ⁵ each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n is independently an integer of 0 to 4 Indicates

<4> The polyketone composition according to any one of <1> to <3>, wherein Y in the general formula (I) contains a divalent saturated hydrocarbon group.

<5> The polyketone composition according to <4>, wherein in the general formula (I), Y contains a divalent saturated alicyclic hydrocarbon group.

The polyketone composition as described in any one of <1>-<5> whose carbon number of Y is 6-30 in <6> said General formula (I).

<7> The polyketone composition according to any one of <1> to <6>, wherein the total number of hydroxymethyl groups and alkoxymethyl groups bonded to the nitrogen atom is 2 to 6 in the nitrogen-containing compound. object.

The polyketone composition as described in any one of <1>-<7> which further contains a <8> heat latent acid generator.

The polyketone composition of any one of <1>-<8> which further contains a <9> solvent.

<10> A cured polyketone product, which is a cured product of the polyketone composition according to any one of <1> to <9>.

The optical element which has a polyketone cured material as described in <11> <10>.

The image display apparatus which has a polyketone cured material as described in <12> <10>.

  According to the present invention, a polyketone composition and a cured product of polyketone having excellent heat resistance, transparency and chemical resistance and exhibiting a high elongation when made into a cured film, and an optical element and image display device having the cured polyketone product Can be provided.

  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 constituent elements (including element steps and the like) are not essential unless otherwise specified. The same applies to numerical values and ranges thereof, and does not limit the present invention.

The numerical range shown using "-" in this indication shows the range which includes the numerical value described before and after "-" as minimum value and the maximum value, respectively.
The upper limit value or the lower limit value described in one numerical value range may be replaced with the upper limit value or the lower limit value of the other stepwise description numerical value range in the numerical value range described stepwise in the present disclosure. . In addition, in the numerical range described in the present disclosure, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the example.
In the present disclosure, the content of each component in the composition is the sum of the plurality of substances present in the composition unless a plurality of substances corresponding to each component are present in the composition. It means the content rate.
In the present disclosure, the words “layer” or “film” mean that when the region in which the layer or film is present is observed, in addition to the case where the region is entirely formed, only a part of the region The case where it is formed is also included.

  In the present disclosure, "a plurality of aromatic rings are non-conjugated to each other or weakly conjugated to each other" means that two aromatic rings are ether-linked or methylene-linked, or 2,2'-substituted It says that the conjugation of aromatic rings is suppressed by being suitably twisted like biphenyl.

  In the present disclosure, “excellent transparency” means that the transmittance of visible light (transmission of visible light having a wavelength of 400 nm) is 80% or more (film thickness is 1 μm).

  In the present disclosure, “heat resistance” means that the thermal decomposition temperature is 400 ° C. or higher in a member containing a polyketone.

  In the present disclosure, "high elongation" means that the breaking elongation of the formed film is 5% or more.

  In the present disclosure, “chemical resistance of the cured film” means that the polyketone film does not peel from the substrate even when the film-like cured polyketone (polyketone film) formed on the silicon substrate is exposed to a chemical solution, and the polyketone film Means not to dissolve.

<Polyketone composition>
The polyketone composition of the present embodiment is bonded to a polyketone containing a structural unit represented by the following general formula (I) in the main chain (hereinafter also referred to as “specific polyketone”), and a nitrogen atom and the nitrogen atom. It contains a nitrogen-containing compound having a hydroxymethyl group or an alkoxymethyl group (hereinafter also referred to as a "specified nitrogen-containing compound").

  In the general formula (I), X each independently represents a divalent group having 1 to 50 carbon atoms which may have a substituent, and Y each independently has a substituent It also represents a C 1 to C 30 divalent hydrocarbon group, and n represents an integer of 3 to 1000.

The polyketone composition of the present embodiment is excellent in heat resistance, transparency and chemical resistance and exhibits a high elongation when made into a cured film by the above configuration. The reason is not clear but is presumed as follows.
Since the specific polyketone contains a carbonyl group in the main chain, it is excellent in heat resistance and transparency. In addition, since the main chain of the specific polyketone is formed substantially by a C—C bond, the molecular chain itself is stable to a drug solution. Then, it is considered that the nitrogen atom in the specific nitrogen-containing compound acts to strengthen the cohesion of the specific polyketone, and the elongation when the polyketone composition is a cured film becomes large. When the specific nitrogen-containing compound functions as a crosslinking agent, the polyketone main chains crosslink with each other, and as a result, the specific polyketones become more entangled with each other. Conceivable.
Therefore, by using a polyketone composition in which a specific nitrogen-containing compound is combined with a specific polyketone, when it is made a cured film, it is possible to exhibit excellent heat resistance, transparency and chemical resistance, and to show a higher elongation rate. Conceivable.
Each component will be described below.

(A) Polyketone The polyketone composition contains a specific polyketone. The specific polyketone contains a structural unit represented by the following general formula (I) in the main chain.

  In general formula (I), X each independently represents a divalent C1 to C50 group which may have a substituent. Each Y independently represents a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent. n represents an integer of 3 to 1000. In addition, when a bivalent group or a bivalent hydrocarbon group has a substituent, carbon number of a substituent shall not be included in carbon number of bivalent group. The same applies thereafter.

  The carbon number of the divalent group represented by X is 1 to 50, preferably 1 to 30, and more preferably 1 to 24.

  The substituent which X may have is not particularly limited, and specific examples thereof include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

  The divalent group represented by X is preferably a hydrocarbon group, and more preferably an aromatic ring. When X has an aromatic ring, higher heat resistance tends to be realized.

  It is preferable that X contains a C6-C50 bivalent group containing an aromatic ring from a viewpoint of implement | achieving high heat resistance. Examples of the aromatic ring include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, naphthacene ring, chrysene ring, pyrene ring, triphenylene ring, pentacene ring, benzopyrene ring and the like.

  Furthermore, X preferably contains a plurality of aromatic rings, and a plurality of aromatic rings are non-conjugated to each other, or a divalent group having a weak conjugated relationship with each other (hereinafter, also referred to as "specific aromatic ring group" It is more preferred that Thereby, good diacylation can be realized at a low reaction temperature at the time of polyketone synthesis, and a polyketone having high molecular weight and excellent heat resistance can be obtained. The specific aromatic ring group preferably has 12 to 50 carbon atoms.

  Here, "a plurality of aromatic rings are non-conjugated to each other or weakly conjugated to each other" means that a plurality of aromatic rings are bonded via an ether bond or a methylene bond, or 2, Steric hindrance due to substituents like 2'-substituted biphenyl means that conjugation between aromatic rings is suppressed.

  As X, the bivalent group etc. which are represented by the following general formula (II-1)-(II-3), etc. are mentioned.

In general formula (II-1), R ¹ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² is independently substituted C1-30 hydrocarbon group which may have a group is shown, and m shows the integer of 0-3 each independently. The wavy part indicates a bond. The same applies thereafter.

From the viewpoint of heat resistance, the carbon number of the hydrocarbon group represented by R ¹ is 1 to 30, preferably 1 to 10, and more preferably 1 to 6. 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.

Examples of the hydrocarbon group represented by R ^1, a saturated aliphatic hydrocarbon group, an unsaturated aliphatic hydrocarbon group, alicyclic hydrocarbon group and the like.

As a saturated aliphatic hydrocarbon group represented by R ¹ , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group 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-Triacontanyl group etc. are mentioned. In addition, the saturated aliphatic hydrocarbon group may have an alicyclic hydrocarbon group described later at its terminal portion.

Examples of the unsaturated aliphatic hydrocarbon group represented by R ¹ include alkenyl groups such as vinyl group and allyl group, and alkynyl groups such as ethynyl group. In addition, the unsaturated aliphatic hydrocarbon group may have an alicyclic hydrocarbon group described later at its terminal portion.

Examples of the alicyclic hydrocarbon group represented by R ¹ include cycloalkyl groups such as cyclohexyl, cycloheptyl, cyclooctyl and norbornyl, and cycloalkenyl groups such as cyclohexenyl. Further, the alicyclic hydrocarbon group may have at least one selected from the group consisting of saturated aliphatic hydrocarbon groups and unsaturated aliphatic hydrocarbon groups in its alicyclic group.

The substituent which the hydrocarbon group represented by R ¹ may have is not particularly limited, and examples thereof include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

In general formula (II-1), R ² each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent. From the viewpoint of heat resistance, the carbon number of the hydrocarbon group represented by R ² is preferably 1 to 10, and more preferably 1 to 5.

Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R ^2, include the same hydrocarbon group having 1 to 30 carbon atoms exemplified for R ^1. Examples of the substituent may have a hydrocarbon group represented by R ^2, a halogen atom, an alkoxy group having 1 to 5 carbon atoms and an acyl group having 2 to 5 carbon atoms.

  In general formula (II-1), m respectively independently shows the integer of 0-3, It is preferable that it is an integer of 0-2, and it is more preferable that it is 0 or 1.

In general formula (II-2), R ¹ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² is independently substituted Group each independently represent an integer of 0 to 3; and Z is an oxygen atom or a compound represented by the following formula (III-1): It shows a divalent group represented by-(III-7).

In general formulas (III-1) to (III-7), R ¹ independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² is And each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ³ and R ⁴ each independently represent a hydrogen atom or carbon which may have a substituent. It represents the number 1 to 30 hydrocarbon group. m independently represents an integer of 0 to 3, n independently represents an integer of 0 to 4, and p independently represents an integer of 0 to 2.

R ³ and R ⁴ in the general formula (III-1) are preferably a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, from the viewpoint of heat resistance. Examples of the hydrocarbon group R ³ and 1 to 30 carbon atoms represented by ^{R 4,} include those of the general formula (II-1) carbon atoms exemplified by ^{R 1} in 30 similar to the hydrocarbon group Be Examples of the substituent R ³ and R ⁴ may have, a halogen atom, an alkoxy group having 1 to 5 carbon atoms and an acyl group having 2 to 5 carbon atoms.

N in general formulas (III-2) and (III-3) independently represents an integer of 0 to 4, preferably an integer of 0 to 2, and more preferably 0 or 1.
P in the general formulas (III-4), (III-5) and (III-7) each independently represents an integer of 0 to 2, preferably 0 or 1.

Each of the details of the ^R 1, ^{R 2,} and m in formula (II-2), is the same as ^R 1, ^{R 2,} and m in Formula (II-1).

In general formula (II-3), R ⁵ each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n is independently an integer of 0 to 4 Indicates
From the viewpoint of heat resistance, the carbon number of the hydrocarbon group represented by R ⁵ is preferably 1 to 10, and more preferably 1 to 5.
Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R ^5, include the same hydrocarbon groups exemplified C1-30 by formula ^{(II-1) R} 1 in. Examples of the substituent R ⁵ may have, a halogen atom, an alkoxy group having 1 to 5 carbon atoms and an acyl group having 2 to 5 carbon atoms.

  In General Formula (II-3), n independently represents an integer of 0 to 4, preferably 1 to 4, and more preferably 1 to 3, 1 or 2. It is further preferred that

  In General Formula (I), Y each independently represents a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent. The carbon number of the hydrocarbon group represented by Y is 1 to 30, preferably 4 to 30, and more preferably 6 to 30 from the viewpoint of heat resistance.

The hydrocarbon group represented by Y preferably contains a saturated hydrocarbon group from the viewpoint of transparency. The saturated hydrocarbon group may be a saturated aliphatic hydrocarbon group or a saturated alicyclic hydrocarbon group. From the viewpoint of achieving both higher heat resistance and transparency, the hydrocarbon group represented by Y preferably contains a saturated alicyclic hydrocarbon group. Since an alicyclic hydrocarbon group is bulkier than an aliphatic hydrocarbon group having the same carbon number, it tends to be excellent in solubility in nitrogen-containing compounds and solvents while maintaining high heat resistance and transparency.
The hydrocarbon group represented by Y may contain plural types of saturated aliphatic hydrocarbon groups or plural types of saturated alicyclic hydrocarbon groups. In addition, Y may contain a saturated aliphatic hydrocarbon group and a saturated alicyclic hydrocarbon group in combination.

The carbon number of the saturated aliphatic hydrocarbon group represented by Y is 1 to 30, and preferably 3 to 30.
Examples of saturated aliphatic hydrocarbon groups include methylene, ethylene, trimethylene, methylethylene, tetramethylene, 1-methyltrimethylene, 2-methyltrimethylene, ethylethylene and 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-methyl pentylene group, 2-methyl pentylene group, 3-methyl pentylene group 1-ethyltetramethylene group, 2-ethyltetramethylene group, 1-propyltrimethylene group, 2 Propyltrimethylene, butylethylene, 1,1-dimethyltetramethylene, 2,2-dimethyltetramethylene, 1,2-dimethyltetramethylene, 1,3-dimethyltetramethylene, 1,4-dimethyl Tetramethylene, 1,2,3-trimethyltrimethylene, 1,1,2-trimethyltrimethylene, 1,1,3-trimethyltrimethylene, 1,2,2-trimethyltrimethylene, 1- Ethyl-1-methyltrimethylene group, 2-ethyl-2-methyltrimethylene group, 1-ethyl-2-methyltrimethylene group, 2-ethyl-1-methyltrimethylene group, 2,2-ethylmethyltrimethylene group Groups, heptylene groups, octylene groups, nonylene groups, decylene groups, icosanylene groups, triacontanylene groups and the like.

  From the viewpoint of heat resistance, the saturated aliphatic hydrocarbon group is preferably a hexylene group, a methyl pentylene group, an ethyl tetramethylene group, a propyltrimethylene group, a butylethylene group, a dimethyltetramethylene group, a trimethyltrimethylene group, preferably Ethyl methyl trimethylene group, heptylene group, octylene group, nonylene group, decylene group, icosanylene group, triacontanylene group etc. are mentioned.

The carbon number of the saturated alicyclic hydrocarbon group represented by Y is 3 to 30, preferably 4 to 30, and more preferably 6 to 30.
As a saturated alicyclic hydrocarbon group, cyclopropane skeleton, cyclobutane skeleton, cyclopentane skeleton, cyclohexane skeleton, cycloheptane skeleton, cycloheptane skeleton, cyclooctane skeleton, cubane skeleton, norbornane skeleton, tricyclo [5.2.1.0] decane skeleton And a divalent group having an adamantane skeleton, a diadamantane skeleton, a bicyclo [2.2.2] octane skeleton, a decahydronaphthalene skeleton and the like.

  From the viewpoint of heat resistance, preferred as a saturated alicyclic hydrocarbon group is a cyclohexane skeleton, a cycloheptane skeleton, a cyclooctane skeleton, a cubane skeleton, a norbornane skeleton, a tricyclo [5.2.1.0] decane skeleton, an adamantane skeleton And bivalent groups such as diadamantane skeleton, bicyclo [2.2.2] octane skeleton, decahydronaphthalene skeleton and the like.

  As a substituent which the hydrocarbon group represented by Y may have, an amino group, an oxo group, a hydroxyl group, a halogen atom etc. are mentioned.

  Y preferably contains at least a divalent group represented by at least one selected from the group consisting of the following general formula (IV) and the following general formulas (V-1) to (V-3), It is more preferable to include at least the divalent hydrocarbon group represented by the general formula (IV).

Hydrogen atom of adamantane skeleton in general formula (IV), hydrogen atom of cyclohexane skeleton in general formula (V-1), hydrogen atom of decalin skeleton in general formula (V-2), and norbornane in general formula (V-3) Each hydrogen atom of the skeleton may be substituted by a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom. Moreover, in general formula (IV), Z respectively independently represents a C1-C10 bivalent saturated hydrocarbon group which may have a single bond or a substituent.
From the viewpoint of obtaining a flexible cured film, each Z is preferably independently a C1-C10 divalent saturated hydrocarbon group which may have a substituent, and from the viewpoint of heat resistance Thus, Z is preferably a divalent saturated hydrocarbon group having 1 to 5 carbon atoms.

  The divalent saturated hydrocarbon group represented by Z is a methylene group, an ethylene group, a trimethylene group, a methylethylene group, a tetramethylene group, a 1-methyltrimethylene group, a 2-methyltrimethylene group, 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-methyl pentylene group, 1-ethyl tetramethylene group, 2-ethyl tetramethylene group, 1-propyl trime Lene 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, 1,2,3-trimethyltrimethylene, 1,1,2-trimethyltrimethylene, 1,1,3-trimethyltrimethylene, 1,2,2-trimethyltrile Methylene group, 1-ethyl-1-methyltrimethylene group, 2-ethyl-2-methyltrimethylene group, 1-ethyl-2-methyltrimethylene group, 2-ethyl-1-methyltrimethylene group, heptylene group, Examples include octylene group, nonylene group, decylene group and the like.

  Examples of the substituent that Z may have include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms. When Z has a substituent, the carbon number of the divalent saturated hydrocarbon group of Z does not include the carbon number of the substituent.

  The divalent group represented by Formula (V-3) may be the following Formula (VI-1).

  Y may contain both of the above general formula (IV) and at least one bivalent group selected from the group consisting of the above general formulas (V-1) to (V-3). When Y contains both of the above general formula (IV) and at least one group selected from the group consisting of the above general formulas (V-1) to (V-3), general formula (IV) The mass ratio ((IV): (V-1) to (V-3)) of the content of and the total content of the general formulas (V-1) to (V-3) is not particularly limited. The mass ratio is preferably 5:95 to 95: 5 from the viewpoint of heat resistance and elongation, and more preferably 5:95 to 90:10 from the viewpoint of heat resistance and solubility.

  The specific polyketone may be a commercially available product or one synthesized by a known method.

  From the viewpoint of maintaining heat resistance, the weight average molecular weight (Mw) of the specific polyketone is preferably 500 or more in terms of polystyrene equivalent standard GPC (gel permeation chromatography), and higher heat resistance and It is more preferable that it is 10,000-1,000,000 from a soluble viewpoint to a nitrogen compound and a solvent. When higher heat resistance is required, the weight average molecular weight (Mw) is more preferably 20,000 to 1,000,000. The weight average molecular weight (Mw) of the specific polyketone refers to a value measured by the method described in the examples.

The specific polyketones may be used alone or in combination of two or more.
Also, the polyketone composition may contain other polyketone other than the specific polyketone. Hereinafter, the specific polyketone and the other polyketone may be collectively referred to as "polyketone". From the viewpoint of heat resistance, transparency, and chemical resistance when a cured film is formed, the content of the specific polyketone relative to the total amount of polyketone is preferably 50% by mass or more, and 60% by mass or more More preferably, the content is 70% by mass or more.

  The total content of the polyketone is 50 parts by mass to 99 parts by mass with respect to 100 parts by mass in total of the polyketone and the nitrogen-containing compound from the viewpoints of heat resistance, transparency and chemical resistance when forming a cured film. Is preferable, and 50 parts by mass to 95 parts by mass is more preferable.

<Specific nitrogen-containing compounds>
The polyketone composition of the present embodiment contains a nitrogen-containing compound (specific nitrogen-containing compound) having a nitrogen atom and a hydroxymethyl group or an alkoxymethyl group bonded to the nitrogen atom.
The specific nitrogen-containing compound is preferably a compound having both a hydroxymethyl group and an alkoxymethyl group or a compound having no hydroxymethyl group but having an alkoxymethyl group, and a compound having no hydroxymethyl group and having an alkoxymethyl group is more preferable. preferable.

  The total number of hydroxymethyl groups and alkoxymethyl groups contained in the molecule of the specific nitrogen-containing compound is not particularly limited as long as it is one or more. The total number of hydroxymethyl groups and alkoxymethyl groups contained in the molecule is preferably 2 to 6, and is 4 to 6 from the viewpoint of elongation percentage and chemical resistance when a cured film is formed. Is more preferred.

  The carbon number of the alkoxy group in the alkoxymethyl group is preferably 1 to 30, more preferably 1 to 15, still more preferably 1 to 10, and particularly preferably 1 to 3, It is very preferable that it is 1.

  As a specific nitrogen-containing compound, compounds represented by the following general formulas (VII-1) and (VII-2) can be mentioned.

In the general formula (VII-1), A represents an n-valent organic group, and W ¹ and W ² are each independently represented by a hydrogen atom or the following general formula (VIII-1) or (VIII-2) And n represents 2 or 3. However, among the plurality of ^{W 1} and ^{W 2,} at least one is a group represented by the following general formula (VIII-1) or (VIII-2), 2 of the plurality of ^{W 1} and ^{W 2} It is preferable that the above is a group represented by the following general formula (VIII-1) or (VIII-2).

In general formula (VIII-2), R ¹ represents an alkyl group having 1 to 30 carbon atoms which may have a substituent. The carbon number of the alkyl group represented by R ¹ is preferably 1 to 30, more preferably 1 to 15, still more preferably 1 to 10, and particularly preferably 1 to 3. Preferably, 1 is very preferable.

  Examples of the organic group represented by A in the general formula (VII-1) include groups represented by the following general formulas (IX-1) and (IX-2).

In the general formula (VII-2), W ^{3 to} W ⁶ each independently represent a hydrogen atom or a group represented by the above general formula (VIII-1) or (VIII-2). ^However, of W 3 to ^W-6, at least one is a group represented by the following general formula (VIII-1) or ^(VIII-2), 2 or more of W 3 to ^W-6 is the following It is preferable that it is group represented by General formula (VIII-1) or (VIII-2).

  As a specific nitrogen-containing compound, compounds represented by the following general formulas (X-1) to (X-3) can be exemplified.

In formulas (X-1) to (X-3), each R ¹ independently represents an alkyl group having 1 to 30 carbon atoms which may have a substituent. Details of R ^1, is the same as ^{R 1} in the general formula (VIII-2).

  The specific nitrogen-containing compound may be a monomer or an oligomer, or may be a mixture of a monomer and an oligomer. The oligomers include, for example, those formed by the self reaction of monomers.

  The specific nitrogen-containing compounds may be used alone or in combination of two or more. The content of the specific nitrogen-containing compound is 1 part by mass to 50 parts by mass with respect to 100 parts by mass in total of the polyketone and the specific nitrogen-containing compound from the viewpoint of heat resistance, transparency and chemical resistance when forming a cured film. It is preferable that it is a mass part, It is more preferable that it is 5 mass parts-50 mass parts, It is still more preferable that it is 5 mass parts-20 mass parts.

<Thermal latent acid generator>
The polyketone composition may further contain a thermal latent acid generator. The heat latent acid generator is a compound which generates an acid upon heating. When the polyketone composition contains a thermal latent acid generator, the crosslinking reaction by the specific nitrogen-containing compound is accelerated, and a stronger cured product can be obtained, so the chemical resistance of the cured film tends to be improved. .

  Examples of the acid generated from the thermal latent acid generator include arylsulfonic acids such as p-toluenesulfonic acid and benzenesulfonic acid, (±) -10-camphorsulfonic acid, perfluoromethanesulfonic acid, nonafluorobutanesulfonic acid and the like. And fluorosulfonic acid, methanesulfonic acid, ethanesulfonic acid, alkylsulfonic acid such as butanesulfonic acid, and the like.

  The heat latent acid generator may be used alone or in combination of two or more. The content of the thermal latent acid generator is preferably 0.05 parts by mass to 30 parts by mass with respect to 100 parts by mass of the total amount of the polyketone, the nitrogen-containing compound, and the thermal latent acid generator. It is more preferable that it is a mass part-20 mass parts, and it is further more preferable that it is 0.2 mass parts-10 mass parts.

<Solvent>
The polyketone composition may further contain a solvent. The solvent is not particularly limited as long as it dissolves or disperses each component. As the solvent, γ-butyrolactone, ethyl lactate, propylene glycol monomethyl ether acetate, butyl acetate, benzyl acetate, n-butyl acetate, ethoxyethyl propionate, 3-methyl methoxy propionate, N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, hexamethylphosphorylamide, tetramethylene sulfone, diethyl ketone, diisobutyl ketone, methyl amyl ketone, cyclopentanone, cyclohexanone, propylene glycol monomethyl Ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, xylene, mesitylene, ether Rubenzen, propylbenzene, cumene, diisopropylbenzene, hexyl benzene, anisole, diglyme, dimethyl sulfoxide, chloroform, dichloromethane, dichloroethane, chlorobenzene and the like. One of these solvents may be used alone, or two or more thereof may be used in combination.

  When the polyketone composition contains a solvent, the content of the solvent is 5 parts by mass with respect to 100 parts by mass in total of the polyketone, the nitrogen-containing compound, and the latent thermal acid generator optionally contained, and the solvent. It is preferable that it is a part-95 mass parts, and it is more preferable that it is 10 mass parts-90 mass parts.

<Other additives>
The polyketone composition may further contain other additives. Examples of other additives include adhesion assistants, surfactants, leveling agents, antioxidants, and ultraviolet light deterioration inhibitors.

<Polyketone cured product>
The cured polyketone of the present embodiment is a cured product of the polyketone composition of the present embodiment.
The polyketone cured product can be produced, for example, by the following method. First, the polyketone composition is applied to at least a portion of the surface of the substrate to form a composition layer. The method for applying the polyketone composition to the substrate is not particularly limited as long as the composition layer can be formed in an arbitrary shape at any place on the substrate. Examples of the method for applying the polyketone composition to a substrate include an immersion method, a spray method, a screen printing method, a spin coating method, a spin coating method, and a bar coating method.

  The substrate to which the polyketone composition is applied is not particularly limited, and glass, semiconductor, metal oxide insulator (titanium oxide, silicon oxide etc.), inorganic material such as silicon nitride, triacetylcellulose, transparent polyimide, polycarbonate, Examples of the transparent substrate include transparent resins such as acrylic polymers and cycloolefin resins. The shape of the substrate is not particularly limited, and may be plate-like or film-like. The polyketone composition of the present embodiment exhibits a high elongation when made into a cured film, and is excellent in chemical resistance, and thus can be suitably used as a coating material of a substrate, a molded article, and the like.

  When the polyketone composition contains a solvent, drying may be performed before and after curing. The drying method is not particularly limited, and examples thereof include a method of heat treatment using an apparatus such as a hot plate or an oven. The drying conditions are not particularly limited as long as the solvent in the polyketone composition is sufficiently volatilized, and the drying conditions are usually 50 ° C. to 150 ° C. for about 1 minute to 90 minutes.

  After forming the composition layer, it is cured to obtain a polyketone cured product. The curing method is not particularly limited, and can be cured by heat treatment or the like. Hardening by heat treatment involves ovens such as a box drier, hot air conveyor drier, quartz tube furnace, hot plate, rapid thermal annealing, vertical diffusion furnace, infrared curing furnace, electron beam curing furnace, microwave curing furnace, etc. It can be done using.

The atmosphere for curing may be any in the air or in an inert atmosphere such as nitrogen, and from the viewpoint of preventing oxidation of the polyketone composition, it is preferable to carry out in a nitrogen atmosphere.
The temperature and time of the heat treatment for curing can be arbitrarily set in view of the composition conditions, work efficiency and the like, and are usually about 30 minutes to 2 hours at 60 ° C to 200 ° C.

The resulting cured polyketone can be used as a substrate bearing a cured polyketone with the substrate attached, and can be peeled off from the substrate and used if necessary.
In the cured polyketone substrate, the cured polyketone may be provided on at least a part of the surface of the substrate, and may be provided only on one side of the substrate or may be provided on both sides. Further, the cured polyketone may have a single-layer structure 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 apparatus of the present embodiment each have the polyketone cured product of the present embodiment. The polyketone cured product applied to the optical element and the image display device may be the above-mentioned polyketone cured substrate. Moreover, if a base material is a transparent base material, it can use suitably for an optical element. As the transparent substrate, those exemplified for the production of a cured polyketone can be mentioned.

  The optical element and the image display device are, for example, affixing the substrate side of the polyketone cured substrate to an application point such as LCD (liquid crystal display) or ELD (electroluminescence display) via an adhesive, an adhesive or the like. Can be obtained.

  The cured polyketone and various optical elements such as a polarizing plate using the same can be preferably used for various image display devices such as liquid crystal display devices. The image display device may have the same configuration as that of the conventional image display device except that the cured polyketone of the present embodiment is used. When the image display device is a liquid crystal display device, the drive circuit may be assembled by appropriately assembling the respective components such as a liquid crystal cell, an optical element such as a polarizing plate, and an illumination system (backlight etc.) as necessary. It can be manufactured. 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 desktop computers, notebook computers, office automation equipment such as copiers, mobile phones, watches, digital cameras, portable information terminals (PDAs), portable devices such as portable game machines, video cameras, televisions, electronic devices Household electric appliances such as ranges, back monitors, monitors for car navigation systems, in-car devices such as car audio, display devices such as information monitors for commercial stores, security devices such as monitoring monitors, nursing care such as nursing care monitors Devices and medical devices such as medical monitors can be mentioned.

The disclosure of Japanese Patent Application 2016-153622 is incorporated by reference in its entirety into the present disclosure.
All documents, patent applications and technical standards in the present disclosure may be incorporated into the present disclosure to the same extent as if each individual document, patent application and technical standard were specifically and individually incorporated by reference. Captured by reference.

  Hereinafter, the present embodiment will be specifically described by way of examples, but the present embodiment is not limited to these examples.

<Polyketone composition>
The components (A) to (D) were blended in the proportions shown in Tables 1 to 4 and filtered with a filter made of PTFE (polytetrafluoroethylene) to obtain the polyketone compositions of Examples and Comparative Examples. The numerical values in the parentheses represent the blending ratio (parts by mass, solid content ratio). "-" Represents that the component is not contained. Each component in Tables 1-4 is shown below.

Component (A) Synthesis Example 1 Synthesis of Polyketone PK-1 In a flask containing 10 mmol of 2,2′-dimethoxybiphenyl and 10 mmol of cis-1,4-cyclohexanedicarboxylic acid as monomers, diphosphorus pentaoxide and methanesulfone 30 ml of a mixture of acids (mass ratio 1:10) was added and stirred at 60.degree. After the reaction, the contents were 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 polyketone PK-1.
The weight average molecular weight of the obtained polyketone PK-1 was 20,000, and the number average molecular weight was 8,000. In addition, a weight average molecular weight and a number average molecular weight are measured by the below-mentioned method, and are computed. The weight average molecular weight (Mw) and the number average molecular weight (Mn) of polyketone PK-2 to polyketone PK-15 described later were also measured by the same method.

Synthesis Example 2 Synthesis of Polyketone PK-2 In the same manner as in Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl and 13 mmol of 1,3-adamantanedicarboxylic acid were used as monomers, polyketone PK-2 was obtained. The The weight average molecular weight of obtained polyketone PK-2 was 280,000, and the number average molecular weight was 44,000.

Synthesis Example 3 Synthesis of Polyketone PK-3 In the same manner as in Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl and 10 mmol of 1,3-adamantanediacetic acid were used as monomers, a polyketone PK-3 was obtained. The The weight average molecular weight of obtained polyketone PK-3 was 42,000, and the number average molecular weight was 12,000.

Synthesis Example 4 Synthesis of Polyketone PK-4 Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanedicarboxylic acid and 5 mmol of cis-1,4-cyclohexanedicarboxylic acid were used as monomers. Polyketone PK-4 was obtained in the same manner as in. The weight average molecular weight of the obtained polyketone PK-4 was 36,000, and the number average molecular weight was 12,000.

Synthesis Example 5 Synthesis of Polyketone PK-5 Polyketone was prepared in the same manner as Example 1, except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantane dicarboxylic acid and 5 mmol of dodecanedioic acid were used as monomers. Obtained PK-5. The weight average molecular weight of the obtained polyketone PK-5 was 36,000, and the number average molecular weight was 13,000.

Synthesis Example 6 Synthesis of Polyketone PK-6 A polyketone was prepared in the same manner as Example 1, except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid and 5 mmol of dodecanedioic acid were used as monomers. Obtained PK-6. The weight average molecular weight of the obtained polyketone PK-6 was 39,000, and the number average molecular weight was 12,000.

Synthesis Example 7 Synthesis of Polyketone PK-7 A polyketone was prepared in the same manner as in Example 1, except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid and 5 mmol of hexanedioic acid were used as monomers. Obtained PK-7. The weight average molecular weight of the obtained polyketone PK-7 was 39,000, and the number average molecular weight was 12,000.

Synthesis Example 8 Synthesis of Polyketone PK-8 Same as Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid and 5 mmol of cis-1,4-cyclohexanedicarboxylic acid were used. , Polyketone PK-8. The weight average molecular weight of the obtained polyketone PK-8 was 45,000, and the number average molecular weight was 11,000.

Synthesis Example 9 Synthesis of Polyketone PK-9 Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid and 5 mmol of trans-1,4-cyclohexanedicarboxylic acid were used as monomers. Polyketone PK-9 was obtained in the same manner as in. The weight average molecular weight of the obtained polyketone PK-9 was 37,000, and the number average molecular weight was 10,000.

Synthesis Example 10 Synthesis of Polyketone PK-10 As monomers, 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid and 1,4-cyclohexanedicarboxylic acid (a mixture of cis and trans, cis: trans) (Molar ratio) = 7: 3) Polyketone PK-10 was obtained in the same manner as in Example 1 except that 5 mmol was used. The weight average molecular weight of the obtained polyketone PK-10 was 33,000, and the number average molecular weight was 11,000.

Synthesis Example 11 Synthesis of Polyketone PK-11 Example 1 and Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid and 5 mmol of decalin-2,6-dicarboxylic acid were used as monomers. Similarly, polyketone PK-11 was obtained. The weight average molecular weight of the obtained polyketone PK-11 was 33,000, and the number average molecular weight was 10,000.

Synthesis Example 12 Synthesis of Polyketone PK-12 As monomers, 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid and 5 mmol of norbornane dicarboxylic acid (2,4-, 2,5-mixture) A polyketone PK-12 was obtained in the same manner as in Example 1 except that it was used. The weight average molecular weight of the obtained polyketone PK-12 was 27,000, and the number average molecular weight was 9,200.

Synthesis Example 13 Synthesis of Polyketone PK-13 Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid and 5 mmol of trans-2,3-norbornane dicarboxylic acid were used as monomers. Polyketone PK-13 was obtained in the same manner as in. The weight average molecular weight of the obtained polyketone PK-13 was 26,000, and the number average molecular weight was 8,100.

Synthesis Example 14 Synthesis of Polyketone PK-14 As monomers, 10 mmol of 2,2′-bis (2-methoxyphenyl) propane, 5 mmol of 1,3-adamantanediacetic acid and 1,4-cyclohexanedicarboxylic acid (cis and trans A polyketone PK-14 was obtained in the same manner as in Example 1 except that 5 mmol of a mixture of cis: trans (molar ratio) = 7: 3) was used. The weight average molecular weight of the obtained polyketone PK-14 was 28,000, and the number average molecular weight was 8,300.

Synthesis Example 15 Synthesis of Polyketone PK-15 As monomers, 10 mmol of diphenyl ether, 5 mmol of 1,3-adamantanediacetic acid and 1,4-cyclohexanedicarboxylic acid (a mixture of cis and trans, cis: trans (molar ratio) = 7) : 3) In the same manner as in Example 1 except that 5 mmol was used, polyketone PK-15 was obtained. The weight average molecular weight of the obtained polyketone PK-15 was 27,000, and the number average molecular weight was 8,000.

(B) Component B1: a compound represented by the following formula (XII)

B2: a compound represented by the following formula (XIII)

B3: a compound represented by the following formula (XIV)

B4: a compound represented by the following formula (XV)

B5: Compound represented by the following formula (XVI) (epoxy equivalent 188)

B6: Compound represented by the following formula (XVII)

  B7: Triglycidyl-p-aminophenol

(B ') component B'1: compound represented by the following formula (XVIII)

(C) Component C1: a compound represented by the following formula (XVIV)

C2: a compound represented by the following formula (XX)

(D) Component D1: N-methyl-2-pyrrolidone

<Preparation of evaluation sample>
Using the obtained polyketone composition, a cured polyketone product was produced by the following method, and a sample for evaluation described later was prepared.

(1) Chemical resistance test sample A silicon substrate was coated with a polyketone composition by spin coating. The obtained silicon substrate was dried on a hot plate heated to 120 ° C. for 3 minutes. Furthermore, the dried silicon substrate is heat treated at 200 ° C. for 1 hour in a nitrogen stream using an inert gas oven (Koyo Thermo System Co., Ltd.) to obtain a silicon substrate with a cured polyketone, which is chemically resistant It was used as a test sample.

(2) Sample for transmittance measurement A polyketone composition was applied to a glass substrate by spin coating. The obtained glass substrate was dried as in (1) and heat-treated to obtain a glass substrate with a cured polyketone product, which was used as a sample for transmittance measurement.

(3) Thermal decomposition temperature measurement sample The polyketone composition was dropped onto an aluminum cup, dried as in (1), and heat treated to obtain a cured polyketone product (polyketone molded body) formed in the aluminum cup. . The polyketone molded body was peeled off from the aluminum cup and used as a thermal decomposition temperature measurement sample.

(4) Elongation percentage measurement sample The polyketone composition was coated on a polyimide film by a bar coat method, dried as in (1), and heat treated to obtain a polyimide film with a cured polyketone product. The cured polyketone was peeled from the polyimide film to obtain a cured polyketone (polyketone film), which was used as a sample for measurement of elongation.

<Molecular weight measurement of polyketone>
The molecular weight (weight average molecular weight and number average molecular weight) of the polyketone was measured by GPC method using tetrahydrofuran (THF) as an eluent, and determined in terms of standard polystyrene. The details are as follows.

・ Device name: Ecosec HLC-8320GPC (Tosoh Corp.)
・ Column: TSKgel Supermultipore HZ-M (Tosoh Corp.)
・ Detector: UV detector, RI detector combined ・ Flow rate: 0.4 ml / min

<Chemical resistance test>
The silicon substrate with a cured polyketone was singulated to prepare a test piece. The test pieces were immersed in the chemical solution under the following conditions (a) and (b), respectively. During the immersion, it was observed whether the polyketone film which was a cured polyketone dissolved or the polyketone film peeled off from the silicon substrate. The observation results are shown in Tables 5 and 6. In this test, when no dissolution and peeling were observed, it was considered "no change".

Condition (a): A mixture of dimethylsulfoxide (DMSO), 2-ethanolamine (2AE) and (DMSO: 2AE at a volume ratio of 7: 3) was heated to 60 ° C., and the test piece was immersed for 30 minutes.
Condition (b): The test piece was immersed in a 0.5% by mass aqueous solution of hydrofluoric acid (HF) at 23 ° C. for 30 minutes.

<Transmittance measurement>
The transmittance of visible light at 400 nm of the glass substrate with a cured polyketone was measured by UV-visible absorption spectroscopy using a spectrophotometer (V-570, JASCO Corporation). The transmittance of the film converted to a film thickness of 1 μm is shown in Tables 5 and 6 with reference to a glass substrate not having a cured polyketone product.

<Thermal decomposition temperature measurement>
The weight loss of the cured polyketone was measured using a thermogravimetric balance TG-DTA 6300 (Hitachi High-Tech Science (Hitachi High Technologies)). The point of intersection of the tangents of the curve whose weight is greatly reduced by heating is defined as the thermal decomposition temperature. The results are shown in Tables 5 and 6.

<Elongation rate measurement>
Using a tensile tester (AUTOGRAPH EZ-TEST EZ-S, manufactured by Shimadzu Corporation), the cured polyketone product (polyketone film) was subjected to a tensile test at a speed of 5 mm / min to measure the elongation percentage. The results are shown in Tables 5 and 6.

It was found that the cured polyketone product obtained from the polyketone composition of the example is excellent in chemical resistance, transparency and heat resistance, and further has high elongation.
On the other hand, in Comparative Examples 1 to 3 which do not contain the specific nitrogen-containing compound, the chemical resistance was inferior and the elongation was also low. Moreover, in Comparative Examples 4 to 13 containing an epoxy compound instead of the specific nitrogen-containing compound, it was found that although the chemical resistance, the transparency and the heat resistance were equivalent to those of the examples, the elongation was low.

Claims (12)

Polyketone containing a structural unit represented by the following general formula (I) in the main chain, and
A nitrogen-containing compound having a nitrogen atom and at least one group selected from the group consisting of a hydroxymethyl group and an alkoxymethyl group bonded to the nitrogen atom,
Containing polyketone composition.


[In the general formula (I), X each independently represents a divalent group having 1 to 50 carbon atoms which may have a substituent, and Y each independently has a substituent It may be a C 1 to C 30 divalent hydrocarbon group, and n is an integer of 3 to 1000. ]   The polyketone composition according to claim 1, wherein in the general formula (I), each X independently comprises an aromatic ring-containing divalent group having 6 to 50 carbon atoms. In the general formula (I), each X independently includes a divalent group represented by at least one selected from the group consisting of the following general formulas (II-1) to (II-3): A polyketone composition according to claim 1 or claim 2.


[In the general formula (II-1), R ¹ independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² independently represents The hydrocarbon group having 1 to 30 carbon atoms which may have a substituent is shown, and each m independently represents an integer of 0 to 3. ]

[In the general formula (II-2), R ¹ independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² independently represents C1-30 hydrocarbon group which may have a substituent is shown, m shows each independently the integer of 0-3, Z is an oxygen atom or the following general formula General formula (III- 1) shows a divalent group represented by 1 to (III-7). ]

[In the general formulas (III-1) to (III-7), R ¹ independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R ² Each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ³ and R ⁴ may each independently have a hydrogen atom or a substituent It represents a hydrocarbon group having 1 to 30 carbon atoms. m independently represents an integer of 0 to 3, n independently represents an integer of 0 to 4, and p independently represents an integer of 0 to 2. ]

[In general formula (II-3), each R ⁵ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n is each independently 0 to 4 Indicates an integer. ]   The polyketone composition according to any one of claims 1 to 3, wherein in the general formula (I), Y contains a divalent saturated hydrocarbon group.   The polyketone composition according to claim 4, wherein in the general formula (I), Y contains a divalent saturated alicyclic hydrocarbon group.   The polyketone composition according to any one of claims 1 to 5, wherein in the general formula (I), Y has 6 to 30 carbon atoms.   The polyketone composition according to any one of claims 1 to 6, wherein in the nitrogen-containing compound, the total number of hydroxymethyl groups and alkoxymethyl groups bound to a nitrogen atom is 2 to 6.   The polyketone composition according to any one of claims 1 to 7, further comprising a thermal latent acid generator.   The polyketone composition according to any one of claims 1 to 8, further comprising a solvent.   A polyketone cured product which is a cured product of the polyketone composition according to any one of claims 1 to 9.   An optical element comprising the cured polyketone according to claim 10.   The image display apparatus which has a polyketone cured material of Claim 10.