KR102647609B1 - Triazine ring-containing polymer and composition for forming a film containing the same - Google Patents

Abstract

By using a triazine ring-containing polymer containing a repeating unit structure represented by the following formula (1), a thin film with a high refractive index and excellent weather resistance can be formed.

{Wherein, R and R' independently of each other represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group, and Ar is at least one selected from the group represented by formulas (2) and (3). Indicates the species.

[In the formula, W ¹ and W ² are independently of each other CR ¹ R ² (R ¹ and R ² are independently of each other an alkyl group of 1 to 10 carbon atoms which may be substituted with a hydrogen atom or a halogen atom (however, These may be combined to form a ring.), C=O, O, S, SO, or SO _2. ]

Description

Triazine ring-containing polymer and composition for forming a film containing the same

The present invention relates to a triazine ring-containing polymer and a composition for forming a film containing the same.

Until now, hyperbranched polymers containing a triazine ring as a repeating unit have been able to achieve high heat resistance, high transparency, high refractive index, high solubility, and low volumetric shrinkage by polymer alone, and have been used as films for manufacturing electronic devices and optical members. A suitable material for forming has already been discovered (Patent Document 1).

However, in optical materials having a thin film made from a composition containing the polymer, depending on the framework, deterioration of the thin film due to light (sunlight or ultraviolet light) may be a problem, and improvement in light resistance is difficult. It is being demanded.

A method of adding an ultraviolet absorber and a light stabilizer has been reported as a means of increasing the light resistance of a thin film containing a triazine ring-containing hyperbranched polymer (Patent Document 2), and although this method can prevent deterioration to a certain degree, it is possible to prevent deterioration over time. The effect found to change the refractive index or transmittance depending on the flow cannot be said to be sufficient.

Additionally, it has been reported that it is possible to impart high light resistance to the hyperbranched polymer itself by using a diamine raw material having an alicyclic structure (Patent Document 3), but when an alicyclic structure is used, there is a trade-off relationship with the refractive index, and the refractive index Not only was there a need for improvement in this regard, but there was also room for improvement in terms of heat yellowing resistance to high temperatures such as exceeding 200°C.

International Publication No. 2010/128661 International Publication No. 2015/093508 Japanese Patent Application Publication No. 2014-141596

The present invention has been made in view of the above circumstances, and its purpose is to provide a triazine ring-containing polymer capable of forming a thin film with a high refractive index and excellent weather resistance, and a composition for forming a film containing the same.

The present inventors have conducted extensive studies to achieve the above object and have found that a triazine ring-containing polymer having a diamine-derived skeleton in which two or three benzene rings are bonded through a non-conjugated element can form a thin film with high refractive index and high light resistance. In addition to discovering that a cured film obtained from a composition containing the polymer and various crosslinking agents maintains a high refractive index and is excellent in light resistance and heat yellowing resistance, the present invention was completed.

That is, the present invention:

1. A triazine ring-containing polymer characterized by comprising a repeating unit structure represented by the following formula (1),

{Wherein, R and R' independently of each other represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group, and Ar is at least one selected from the group represented by formulas (2) and (3). Indicates the species.

[In the formula, W ¹ and W ² are independently of each other CR ¹ R ² (R ¹ and R ² are independently of each other an alkyl group of 1 to 10 carbon atoms which may be substituted with a hydrogen atom or a halogen atom (however, These may be combined to form a ring.), C=O, O, S, SO, or SO _2. ]

2. W ¹ and W ² are, independently of each other, CR ¹ R ² (R ¹ and R ² are independently of each other an alkyl group having 1 to 10 carbon atoms which may be substituted with a hydrogen atom or a halogen atom.) , or a triazine ring-containing polymer of 1 representing O,

3. A triazine ring-containing polymer of 1 or 2 wherein Ar is represented by formula (4),

4. A triazine ring-containing polymer of 3 wherein Ar is represented by formula (5),

5. A triazine ring-containing polymer of 1 or 2, wherein Ar is represented by formula (6) or (7),

6. A triazine ring-containing polymer of 5 wherein Ar is represented by formula (8) or (9),

7. A composition for forming a film containing the triazine ring-containing polymer of any one of 1 to 6 and an organic solvent,

8. The film-forming composition of 7 further comprising a crosslinking agent,

9. The film-forming composition of 8, wherein the crosslinking agent is a multifunctional (meth)acrylic compound,

10. A film obtained from the film-forming composition of any one of 7 to 9,

11. An electronic device comprising a substrate and the film of 10 formed on the substrate,

12. An optical member comprising a base material and the film 10 formed on the base material.

provides.

According to the triazine ring-containing polymer of the present invention, a thin film with a high refractive index and excellent light resistance can be formed.

Additionally, by combining this triazine ring-containing polymer with various crosslinking agents, a cured film with excellent light resistance and heat yellowing resistance can be produced while maintaining a high refractive index.

Since the thin film or cured film of the present invention can exhibit the characteristics of high light resistance, high heat resistance, high refractive index, and low volumetric shrinkage, it can be used in liquid crystal displays, organic electroluminescence (EL) displays, touch panels, and optical semiconductor (LED) devices. , electronic devices and optical materials, such as a member for manufacturing solid-state imaging elements, organic thin-film solar cells, dye-sensitized solar cells, organic thin-film transistors (TFTs), lenses, prisms, cameras, binoculars, microscopes, semiconductor exposure devices, etc. It can be used appropriately in the field of

Figure 1 is a ¹ H-NMR spectrum diagram of polymer compound [3] obtained in Example 1-1.
Figure 2 is a ¹ H-NMR spectrum diagram of polymer compound [5] obtained in Example 1-2.
Figure 3 is a ¹ H-NMR spectrum diagram of polymer compound [7] obtained in Example 1-3.
Figure 4 is a diagram showing the change in transmittance of the film produced in Example 2-1 before and after the light resistance test.
Figure 5 is a diagram showing the change in transmittance of the film produced in Example 2-2 before and after the light resistance test.
Figure 6 is a diagram showing the change in transmittance of the film produced in Example 2-3 before and after the light resistance test.
Figure 7 is a diagram showing the change in transmittance of the film produced in Comparative Example 2-1 before and after the light resistance test.
Figure 8 is a diagram showing the change in transmittance of the cured film produced in Example 4-1 before and after the light resistance test.
Figure 9 is a diagram showing the change in transmittance of the cured film produced in Example 4-2 before and after the light resistance test.
Figure 10 is a diagram showing the change in transmittance of the cured film produced in Comparative Example 4-1 before and after the light resistance test.
Figure 11 is a diagram showing the change in transmittance of the cured film produced in Example 4-1 before and after the heat resistance test.
Figure 12 is a diagram showing the change in transmittance of the cured film produced in Example 4-2 before and after the heat resistance test.

(Form for carrying out the invention)

Hereinafter, the present invention will be described in more detail.

The triazine ring-containing polymer according to the present invention contains a repeating unit structure represented by the following formula (1).

In the above formula, R and R' independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group, but it is preferable that both are hydrogen atoms from the viewpoint of further increasing the refractive index.

In the present invention, the number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 20, and considering further improving the heat resistance of the polymer, 1 to 10 carbon atoms is more preferable, and 1 to 3 carbon atoms is even more preferable. Additionally, the structure may be chain-like, branched, or circular.

Specific examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, s-butyl, t-butyl, cyclobutyl, 1-methyl-cyclopropyl, 2-methyl-cyclopropyl, n-pentyl, 1-methyl-n-butyl, 2-methyl-n-butyl, 3-methyl-n-butyl, 1,1-dimethyl-n-propyl, 1,2-dimethyl-n-propyl, 2,2-dimethyl-n-propyl, 1-ethyl-n-propyl, cyclopentyl, 1-methyl-cyclobutyl, 2-methyl-cyclobutyl, 3-methyl-cyclobutyl, 1,2-dimethyl- Cyclopropyl, 2,3-dimethyl-cyclopropyl, 1-ethyl-cyclopropyl, 2-ethyl-cyclopropyl, n-hexyl, 1-methyl-n-pentyl, 2-methyl-n-pentyl, 3-methyl -n-pentyl, 4-methyl-n-pentyl, 1,1-dimethyl-n-butyl, 1,2-dimethyl-n-butyl, 1,3-dimethyl-n-butyl, 2,2- Dimethyl-n-butyl, 2,3-dimethyl-n-butyl, 3,3-dimethyl-n-butyl, 1-ethyl-n-butyl, 2-ethyl-n-butyl, 1,1,2 -trimethyl-n-propyl, 1,2,2-trimethyl-n-propyl, 1-ethyl-1-methyl-n-propyl, 1-ethyl-2-methyl-n-propyl, cyclohexyl, 1- Methyl-cyclopentyl, 2-methyl-cyclopentyl, 3-methyl-cyclopentyl, 1-ethyl-cyclobutyl, 2-ethyl-cyclobutyl, 3-ethyl-cyclobutyl, 1,2-dimethyl-cyclobutyl, 1,3-dimethyl-cyclobutyl, 2,2-dimethyl-cyclobutyl, 2,3-dimethyl-cyclobutyl, 2,4-dimethyl-cyclobutyl, 3,3-dimethyl-cyclobutyl, 1-n-propyl-cyclopropyl, 2-n-propyl-cyclopropyl, 1-isopropyl-cyclopropyl, 2-isopropyl-cyclopropyl, 1,2,2-trimethyl-cyclopropyl, 1,2, 3-Trimethyl-cyclopropyl, 2,2,3-trimethyl-cyclopropyl, 1-ethyl-2-methyl-cyclopropyl, 2-ethyl-1-methyl-cyclopropyl, 2-ethyl-2-methyl- Cyclopropyl, 2-ethyl-3-methyl-cyclopropyl group, etc. can be mentioned.

The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Considering the higher heat resistance of the polymer, the number of carbon atoms is more preferably 1 to 10, and even more preferably 1 to 3. Additionally, the structure of the alkyl portion may be linear, branched, or cyclic.

Specific examples of alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentoxy, and 1-methyl-n-. Butoxy, 2-methyl-n-butoxy, 3-methyl-n-butoxy, 1,1-dimethyl-n-propoxy, 1,2-dimethyl-n-propoxy, 2,2-di Methyl-n-propoxy, 1-ethyl-n-propoxy, n-hexyloxy, 1-methyl-n-pentyloxy, 2-methyl-n-pentyloxy, 3-methyl-n-pentyloxy, 4 -methyl-n-pentyloxy, 1,1-dimethyl-n-butoxy, 1,2-dimethyl-n-butoxy, 1,3-dimethyl-n-butoxy, 2,2-dimethyl -n-butoxy, 2,3-dimethyl-n-butoxy, 3,3-dimethyl-n-butoxy, 1-ethyl-n-butoxy, 2-ethyl-n-butoxy, 1, 1,2-trimethyl-n-propoxy, 1,2,2-trimethyl-n-propoxy, 1-ethyl-1-methyl-n-propoxy, 1-ethyl-2-methyl-n-propoxy Examples include explosives.

The number of carbon atoms of the aryl group is not particularly limited, but is preferably 6 to 40. Considering the higher heat resistance of the polymer, the number of carbon atoms is more preferably 6 to 16, and even more preferably 6 to 13.

Specific examples of aryl groups include phenyl, o-chlorophenyl, m-chlorophenyl, p-chlorophenyl, o-fluorophenyl, p-fluorophenyl, o-methoxyphenyl, p-methoxyphenyl, and p-nitro. Phenyl, p-cyanophenyl, α-naphthyl, β-naphthyl, o-biphenylyl, m-biphenylyl, p-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl , 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl groups, etc.

The number of carbon atoms of the aralkyl group is not particularly limited, but preferably has 7 to 20 carbon atoms, and the alkyl portion may be straight-chain, branched, or cyclic.

Specific examples thereof include benzyl, p-methylphenylmethyl, m-methylphenylmethyl, o-ethylphenylmethyl, m-ethylphenylmethyl, p-ethylphenylmethyl, 2-propylphenylmethyl, 4-isopropylphenylmethyl, and 4-isobutyl. Phenylmethyl, α-naphthylmethyl group, etc. can be mentioned.

Said Ar represents at least one type selected from the group represented by formulas (2) and (3).

Said W ¹ and W ² are, independently of each other, CR ¹ R ² (R ¹ and R ² are, independently of each other, an alkyl group having 1 to 10 carbon atoms which may be substituted with a hydrogen atom or a halogen atom (however, these are combined to form It may form a ring.), C=O, O, S, SO, or SO ₂ , but in particular, CR ¹ R ² (R ¹ and R ² are independent of each other and represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom), or O is preferable.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, but a fluorine atom is preferable.

The alkyl group having 1 to 10 carbon atoms may be linear, branched, or cyclic, and includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, straight or branched alkyl groups having 1 to 10 carbon atoms, such as n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl; Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclobutyl, bicyclopentyl, bicyclohexyl, bicycloheptyl, bicyclooctyl, bicyclononyl, bicyclo Cyclic alkyl groups with 3 to 10 carbon atoms, such as decyl groups, are included, but alkyl groups with 1 to 8 carbon atoms are preferable, and alkyl groups with 1 to 5 carbon atoms are more preferable.

Specific examples of the alkyl group substituted with a halogen atom include a group in which at least one hydrogen atom of an alkyl group having 1 to 10 carbon atoms is substituted with a halogen atom.

Specific examples thereof include fluoromethyl group, difluoromethyl group, trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, heptafluoropropyl group, 2,2,3,3,3-penta. Fluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, nonafluorobutyl group, 4,4,4 -Trifluorobutyl group, undecafluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, 2,2,3,3,4,4, 5,5-octafluoropentyl group, tridecafluorohexyl group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl group, 2,2, 3,3,4,4,5,5,6,6-decafluorohexyl group, 3,3,4,4,5,5,6,6,6-nonafluorohexyl group, etc. .

In particular, as Ar, at least one type represented by formulas (4), (6), and (7) is preferable, and at least one type represented by formulas (5), (8), and (9) is more preferable, but is limited to these. It doesn't work.

The weight average molecular weight of the polymer in the present invention is not particularly limited, but is preferably 500 to 500,000, more preferably 500 to 100,000, and 2,000 in terms of improving heat resistance and lowering the shrinkage rate. Above is preferable, and in terms of further improving solubility and lowering the viscosity of the obtained solution, 50,000 or less is preferable, 30,000 or less is more preferable, and 10,000 or less is even more preferable.

In addition, the weight average molecular weight in the present invention is the average molecular weight obtained by conversion to standard polystyrene by gel permeation chromatography (hereinafter referred to as GPC) analysis.

The triazine ring-containing polymer (hyperbranched polymer) of the present invention can be produced according to the method disclosed in Patent Document 1 mentioned above.

For example, as shown in Scheme 1 below, the triazine ring-containing polymer (12) can be obtained by reacting the triazine compound (10) and the aryldiamino compound (11) in an appropriate organic solvent.

(In the formula, X independently represents a halogen atom.)

In the above reaction, the loading ratio of the aryldiamino compound (11) is arbitrary as long as the target polymer is obtained, but 0.01 to 10 equivalents of the diamino compound (11) is preferable relative to 1 equivalent of the triazine compound (10). , 1 to 5 equivalents are more preferable.

The aryldiamino compound (11) may be added without mixing or as a solution dissolved in an organic solvent, but considering ease of operation and ease of reaction control, the latter method is preferable.

The reaction temperature may be appropriately set within the range from the melting point of the solvent used to the boiling point of the solvent, but is particularly preferably about -30 to 150°C, and -10 to 100°C is more preferable.

As the organic solvent, various solvents commonly used in this type of reaction can be used, such as tetrahydrofuran, dioxane, dimethyl sulfoxide; N,N-dimethylformamide, N-methyl-2-pyrrolidone, tetramethylurea, hexamethylphosphoramide, N,N-dimethylacetamide, N-methyl-2-piperidone, N,N -Dimethylethylene urea, N,N,N',N'-tetramethylmalonic acid amide, N-methylcaprolactam, N-acetylpyrrolidine, N,N-diethylacetamide, N-ethyl-2- Amide solvents such as pyrrolidone, N,N-dimethylpropionic acid amide, N,N-dimethylisobutylamide, N-methylformamide, N,N'-dimethylpropylene urea, and mixed solvents thereof. I can hear it.

Among them, N,N-dimethylformamide, dimethylsulfoxide, N-methyl-2-pyrrolidone, N,N-dimethylacetamide and mixtures thereof are preferred, especially N,N-dimethylacetate. Amide, N-methyl-2-pyrrolidone is suitable.

Additionally, in the reaction of Scheme 1 above, various commonly used bases may be added during or after polymerization.

Specific examples of this base include potassium carbonate, potassium hydroxide, sodium carbonate, sodium hydroxide, sodium hydrogen carbonate, sodium ethoxide, sodium acetate, lithium carbonate, lithium hydroxide, lithium oxide, potassium acetate, magnesium oxide, calcium oxide, barium hydroxide, Trilithium phosphate, trisodium phosphate, tripotassium phosphate, cesium fluoride, aluminum oxide, ammonia, n-propylamine, trimethylamine, triethylamine, diisopropylamine, diisopropylethylamine, N-methylpiperidine , 2,2,6,6-tetramethyl-N-methylpiperidine, pyridine, 4-dimethylaminopyridine, N-methylmorpholine, etc.

The amount of base added is preferably 1 to 100 equivalents, more preferably 1 to 10 equivalents, per 1 equivalent of triazine compound (10). Additionally, these bases may be used in an aqueous solution.

It is preferable that no raw material components remain in the obtained polymer, but some raw materials may remain as long as the effect of the present invention is not impaired.

After completion of the reaction, the product can be easily purified by reprecipitation or the like.

In addition, in the present invention, a part of the halogen atom of at least one terminal triazine ring is replaced with alkyl, aralkyl, aryl, alkylamino, alkoxysilyl group-containing alkylamino, aralkylamino, arylamino, alkoxy, aralkyloxy, It may be capped with an aryloxy or ester group.

Among these, alkylamino, alkoxysilyl group-containing alkylamino, aralkylamino, and arylamino groups are preferable, alkylamino and arylamino groups are more preferable, and arylamino groups are still more preferable.

Examples of the alkyl group, alkoxy group, aryl group, and aralkyl group include the same groups as above.

Specific examples of the ester group include methoxy carbon group, ethoxy carbon group, etc.

Specific examples of alkylamino groups include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, s-butylamino, t-butylamino, n-pentylamino, and 1-methyl-n-. Butylamino, 2-methyl-n-butylamino, 3-methyl-n-butylamino, 1,1-dimethyl-n-propylamino, 1,2-dimethyl-n-propylamino, 2,2-di Methyl-n-propylamino, 1-ethyl-n-propylamino, n-hexylamino, 1-methyl-n-pentylamino, 2-methyl-n-pentylamino, 3-methyl-n-pentylamino, 4- Methyl-n-pentylamino, 1,1-dimethyl-n-butylamino, 1,2-dimethyl-n-butylamino, 1,3-dimethyl-n-butylamino, 2,2-dimethyl- n-butylamino, 2,3-dimethyl-n-butylamino, 3,3-dimethyl-n-butylamino, 1-ethyl-n-butylamino, 2-ethyl-n-butylamino, 1,1 ,2-trimethyl-n-propylamino, 1,2,2-trimethyl-n-propylamino, 1-ethyl-1-methyl-n-propylamino, 1-ethyl-2-methyl-n-propylamino group etc. can be mentioned.

Specific examples of aralkylamino groups include benzylamino, methoxycarbonylphenylmethylamino, ethoxycarbonylphenylmethylamino, p-methylphenylmethylamino, m-methylphenylmethylamino, o-ethylphenylmethylamino, and m-ethylphenylmethylamino. , p-ethylphenylmethylamino, 2-propylphenylmethylamino, 4-isopropylphenylmethylamino, 4-isobutylphenylmethylamino, naphthylmethylamino, methoxycarbonylnaphthylmethylamino, ethoxycarbonylnaph. Tylmethylamino group, etc. are mentioned.

Specific examples of arylamino groups include phenylamino, methoxycarbonylphenylamino, ethoxycarbonylphenylamino, naphthylamino, methoxycarbonylnaphthylamino, ethoxycarbonylnaphthylamino, anthranyl amino, and pyrenyl amino. , biphenylamino, terphenylamino, and fluorenylamino groups.

The alkylamino group containing an alkoxysilyl group may be any of an alkylamino group containing a monoalkoxysilyl group, an alkylamino group containing a dialkoxysilyl group, or an alkylamino group containing a trialkoxysilyl group, and specific examples thereof include 3-trimethoxysilylpropylamino, 3- Triethoxysilylpropylamino, 3-dimethylethoxysilylpropylamino, 3-methyldiethoxysilylpropylamino, N-(2-aminoethyl)-3-dimethylmethoxysilylpropylamino, N-(2 -Aminoethyl)-3-methyldimethoxysilylpropylamino, N-(2-aminoethyl)-3-trimethoxysilylpropylamino, etc. are mentioned.

Specific examples of the aryloxy group include phenoxy, naphthoxy, anthranyloxy, pyrenyloxy, biphenyloxy, terphenyloxy, and fluorenyloxy groups.

Specific examples of aralkyloxy groups include benzyloxy, p-methylphenylmethyloxy, m-methylphenylmethyloxy, o-ethylphenylmethyloxy, m-ethylphenylmethyloxy, p-ethylphenylmethyloxy, 2-propylphenylmethyloxy, Examples include 4-isopropylphenylmethyloxy, 4-isobutylphenylmethyloxy, and α-naphthylmethyloxy groups.

These groups can be easily introduced by replacing the halogen atom on the triazine ring with a compound giving a corresponding substituent. For example, as shown in Scheme 2 below, an aniline derivative is added and reacted to form at least one terminal. A highly branched polymer (13) having a phenylamino group is obtained.

(Wherein, X and R have the same meaning as above.)

At this time, the rigidity of the hyperbranched polymer is alleviated by simultaneously charging the organic monoamine, that is, by reacting the cyanuric halide compound and the diaminoaryl compound in the presence of the organic monoamine, making it soft with a low degree of branching. You can obtain Hyper Branched Polymer.

Here, as the organic monoamine, any of alkyl monoamine, aralkyl monoamine, and aryl monoamine can be used.

Alkylmonoamines include methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, s-butylamine, t-butylamine, n-pentylamine, and 1-methyl-n-butyl. Amine, 2-methyl-n-butylamine, 3-methyl-n-butylamine, 1,1-dimethyl-n-propylamine, 1,2-dimethyl-n-propylamine, 2,2-dimethyl -n-propylamine, 1-ethyl-n-propylamine, n-hexylamine, 1-methyl-n-pentylamine, 2-methyl-n-pentylamine, 3-methyl-n-pentylamine, 4-methyl -n-pentylamine, 1,1-dimethyl-n-butylamine, 1,2-dimethyl-n-butylamine, 1,3-dimethyl-n-butylamine, 2,2-dimethyl-n -Butylamine, 2,3-dimethyl-n-butylamine, 3,3-dimethyl-n-butylamine, 1-ethyl-n-butylamine, 2-ethyl-n-butylamine, 1,1, 2-trimethyl-n-propylamine, 1,2,2-trimethyl-n-propylamine, 1-ethyl-1-methyl-n-propylamine, 1-ethyl-2-methyl-n-propylamine, 2-ethylhexylamine, etc. can be mentioned.

Specific examples of aralkyl monoamine include benzylamine, p-methoxycarbonylbenzylamine, p-ethoxycarbonylbenzylamine, p-methylbenzylamine, m-methylbenzylamine, o-methoxybenzylamine, etc. there is.

Specific examples of aryl monoamines include aniline, p-methoxycarbonylaniline, p-ethoxycarbonylaniline, p-methoxyaniline, 1-naphthylamine, 2-naphthylamine, anthranylamine, and 1-amino. Pyrene, 4-biphenylylamine, o-phenylaniline, 4-amino-p-terphenyl, 2-aminofluorene, etc. are mentioned.

In this case, the amount of organic monoamine used is preferably 0.05 to 500 equivalents, more preferably 0.05 to 120 equivalents, and even more preferably 0.05 to 50 equivalents, relative to the cyanuric halide compound.

In addition, since the reaction temperature suppresses linearity and increases the degree of branching, the reaction temperature is preferably 60 to 150°C, more preferably 80 to 150°C, and even more preferably 80 to 120°C.

Additionally, the reaction of reacting the cyanuric halide compound with the diaminoaryl compound in the presence of such an organic monoamine may be performed using the same organic solvent as described above.

The triazine ring-containing polymer of the present invention described above can be suitably used alone or in combination with a crosslinking agent as a composition for forming a film.

The crosslinking agent is not particularly limited as long as it is a compound having a substituent that can react with the above-mentioned triazine ring-containing polymer.

Such compounds include melamine-based compounds having cross-linking substituents such as methylol groups and methoxymethyl groups, substituted urea-based compounds, compounds containing cross-linking substituents such as epoxy groups or oxetane groups, compounds containing blocked isocyanate, Examples include compounds having an acid anhydride, compounds having a (meth)acrylic group, and phenoplast compounds, but compounds containing an epoxy group, a block isocyanate group, and a (meth)acrylic group are preferred from the viewpoint of heat resistance and storage stability. In particular, compounds having a block isocyanate group, multifunctional epoxy compounds and/or multifunctional (meth)acrylic compounds that provide a composition that can be photocured even without using an initiator are preferred.

In addition, when used for end treatment of polymers, these compounds need only have at least one crosslinking substituent, and when used for crosslinking between polymers, they need to have at least two crosslinking substituents.

The multifunctional epoxy compound is not particularly limited as long as it has two or more epoxy groups per molecule.

Specific examples include tris(2,3-epoxypropyl)isocyanurate, 1,4-butanediol diglycidyl ether, 1,2-epoxy-4-(epoxyethyl)cyclohexane, and glycol. Cerol triglycidyl ether, diethylene glycol diglycidyl ether, 2,6-diglycidylphenyl glycidyl ether, 1,1,3-tris[p-(2,3- Epoxypropoxy)phenyl]propane, 1,2-cyclohexanedicarboxylic acid diglycidyl ester, 4,4'-methylenebis(N,N-diglycidylaniline), 3,4-epoxycyclohexyl Examples include methyl-3,4-epoxycyclohexanecarboxylate, trimethylolethane triglycidyl ether, bisphenol-A-diglycidyl ether, and pentaerythritol polyglycidyl ether.

In addition, commercially available products include YH-434 and YH434L (manufactured by Totokase Co., Ltd.), which are epoxy resins having at least two epoxy groups; Epolid GT-401 and GT-403, which are epoxy resins with a cyclohexene oxide structure; Copper GT-301, Copper GT-302, Celoxide 2021, Copper 3000 (made by Daisel Chemical Co., Ltd.), Bisphenol A type epoxy resin, Epicoat (currently jER) 1001, Copper 1002, Copper 1003, Copper 1004, 1007, 1009, 1010, 828 (manufactured by Japan Epoxy Resin Co., Ltd.), Epicoat (currently jER) 807, a bisphenol F-type epoxy resin (manufactured by Japan Epoxy Resin Co., Ltd.), Phenol novolac type epoxy resins, Epicoat (currently jER) 152, 154 (above, manufactured by Japan Epoxy Resin Co., Ltd.), EPPN201, 202 (above, manufactured by Nippon Kayaku Co., Ltd.), cresol novolac Type epoxy resin, EOCN-102, Copper 103S, Copper 104S, Copper 1020, Copper 1025, Copper 1027 (above, manufactured by Nippon Kayaku Co., Ltd.), Epicoat (currently jER) 180S75 (Japan Epoxy Resin Co., Ltd.) ), alicyclic epoxy resin, Denacol EX-252 (manufactured by Nagase Chemtex Co., Ltd.), CY175, CY177, CY179 (above, manufactured by CIBA-GEIGY A.G.), Araldite CY-182, CY-192 , CY-184 (above, manufactured by CIBA-GEIGY A.G.), Epiclon 200, 400 (above, manufactured by DIC Co., Ltd.), Epicoat (now jER) 871, 872 (above, manufactured by Japan Epoxy Resin Co., Ltd.) ), ED-5661, ED-5662 (above, manufactured by Celanese Coating Co., Ltd.), aliphatic polyglycidyl etherin, Denacol EX-611, EX-612, EX-614, EX-EX -622, EX-411, EX-512, EX-522, EX-421, EX-313, EX-314, EX-321 (manufactured by Nagase Chemtex Co., Ltd.) can also be used. there is.

The polyfunctional (meth)acrylic compound is not particularly limited as long as it has two or more (meth)acrylic groups per molecule.

Specific examples include ethylene glycol diacrylate, ethylene glycol dimethicrylate, polyethylene glycol diacrylate, polyethylene glycol dimethicrylate, ethoxylated bisphenol A diacrylate, and ethoxylated bisphenol A die. Methacrylate, Ethoxylated Trimethylolpropane Triacrylate, Ethoxylated Trimethylolpropane Trimethacrylate, Ethoxylated Glycerine Triacrylate, Ethoxylated Glycerine Trimethacrylate, Ethoxylated Pentaerythate Litol tetraacrylate, ethoxylated pentaerythritol methacrylate, ethoxylated dipentaerythritol hexaacrylate, polyglycerin monoethylene oxide polyacrylate, polyglycerin polyethylene glycol polyacrylate, die Pentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, Trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, tricyclodecane dimethanol diacrylate, tricyclodecane dimethanol dimethacrylate, 1,6-hexanediol diacrylate salt, 1,6-hexanediol dimethacrylate, polybasic acid-modified acrylic oligomer, etc.

In addition, multifunctional (meth)acrylic compounds are available as commercial products, and specific examples thereof include NK Ester A-200, A-400, A-600, A-1000, and A-9300 (isocyanuric acid). Tris (2-acryloyloxyethyl)), A-9300-1CL, A-TMPT, UA-53H, 1G, 2G, 3G, 4G, 9G, 14G, 23G, Copper ABE-300, Copper A-BPE-4, Copper A-BPE-6, Copper A-BPE-10, Copper A-BPE-20, Copper A-BPE-30, Copper BPE-80N, Copper BPE-100N, Bronze BPE-200, Bronze BPE-500, Bronze BPE-900, Bronze BPE-1300N, Bronze A-GLY-3E, Bronze A-GLY-9E, Bronze A-GLY-20E, Bronze A-TMPT-3EO, Bronze A -TMPT-9EO, AT-20E, ATM-4E, ATM-35E, A-DPH, A-TMPT, A-DCP, A-HD-N, TMPT, DCP, NPG, HD-N, A-DPH-48E, A-DPH-96E, NK Oligo U-15HA, NK Polymavana Resin GH-1203 (manufactured by Shinnakamura Kagaku Kogyo Co., Ltd.), KAYARAD (registered) Trademark) DPHA, NPGDA, PET30, DPEA-12, PEG400DA, THE-330, RP-1040, DN-0075 (manufactured by Nippon Kayaku Co., Ltd.), Aronics M-210, M-303, M-305, M-306, M-309, M-306, M-310, M-313, M-315, M-321, M-350, M-310 M-360, M-400, M-402, M-403, M-404, M-405, M-406, M-408, M-450, M-452, M-405. M-460 (above, manufactured by Toagose Co., Ltd.), DPGDA, HDDA, TPGDA, HPNDA, PETIA, PETRA, TMPTA, TMPEOTA, EBECRYL11, Dong 40, Dong 135, Dong 140, Dong 145, Dong 150, Dong 180, Building 1142, Building 204, Building 205, Building 210, Building 215, Building 220, Building 230, Building 244, Building 245, Building 265, Building 270, Building 280/15IB, Building 284, Building 294/25HD, Building 303, Building 436, 438, 446, 450, 524, 525, 600, 605, 645, 648, 767, 770, 800, 810, 811, 812, 846, Building 851, Building 852, Building 853, Building 860, Building 884, Building 885, Building 1259, Building 1290, Building 1606, Building 1830, Building 1870, Building 3500, Building 3603, Building 3608, Building 3700, Building 3701, Building 3702 , Dong 3703, Dong 3708, Dong 4820, Dong 4858, Dong 5129, Dong 6040, Dong 8210, Dong 8454, Dong 8301R, Dong 8307, Dong 8311, Dong 8402, Dong 8405, Dong 8411, Dong 8465, Dong 8701, Dong Dong 8800, Dong 8804, Dong 8807, Dong 9270, Dong 9227EA, Dong 936, KRM8200, Dong 8200AE, Dong 7735, Dong 8296, Dong 08452, Dong 8904, Dong 8528, Dong 8912, OTA480, IRR214-K, Dong 616, Dong 679, 742, 793, PEG400DA-D (ACA)Z200M, Z230AA, Z250, Z251, Z300, Z320, Z254F (Daicel Allnex Co., Ltd.), etc. there is.

The polybasic acid-modified acrylic oligomer is also available as a commercial product, and specific examples thereof include Aronix M-510 and 520 (manufactured by Toagose Co., Ltd.).

The acid anhydride compound is not particularly limited as long as it is a carboxylic acid anhydride obtained by dehydration condensation of two molecules of carboxylic acid. Specific examples include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, Those having one acid anhydride group in the molecule, such as nadic anhydride, methylnadic anhydride, maleic anhydride, succinic anhydride, octylsuccinic anhydride, and dodecenylsuccinic anhydride; 1,2,3,4-cyclobutane tetracarboxylic dianhydride, pyromellitic anhydride, 3,4-dicarboxy-1,2,3,4-tetrahydro-1-naphthalenesuccinic acid dianhydride, bicyclo[ 3.3.0]octane-2,4,6,8-tetracarboxylic dianhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2 -Dicarboxylic acid anhydride, 1,2,3,4-butane tetracarboxylic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, 3,3',4,4'-biphenyl tetra. Carboxylic acid dianhydride, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, 1,3-dimethyl-1,2,3,4-cyclobutane tetracarboxylic acid dianhydride, etc. and those having two acid anhydride groups in the molecule.

Compounds containing blocked isocyanate have two or more blocked isocyanate groups per molecule where the isocyanate group (-NCO) is blocked by an appropriate protecting group, and when exposed to high temperatures during heat curing, the protecting group (Block portion) is thermally dissociated and falls off, and the isocyanate group generated is not particularly limited as long as it causes a crosslinking reaction with the resin. For example, two or more groups in one molecule (also, These groups may be the same or different).

(In the formula, R _b represents an organic group.)

Such compounds can be obtained, for example, by reacting a compound having two or more isocyanate groups per molecule with an appropriate blocking agent.

Examples of compounds having two or more isocyanate groups in one molecule include isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and methylene bis(4-cyclohexyl isocyanate). , polyisocyanates such as trimethylhexamethylene diisocyanate, dimers and trimers thereof, and reactants of these with diols, triols, diamines, or triamines, etc. .

Blocking agents include, for example, alcohols such as methanol, ethanol, isopropanol, n-butanol, 2-ethoxyhexanol, 2-N,N-dimethylaminoethanol, 2-ethoxyethanol, and cyclohexanol. Ryu; Phenols such as phenol, o-nitrophenol, p-chlorophenol, o-, m-, or p-cresol; Lactams such as ε-caprolactam, oximes such as acetone oxime, methyl ethyl ketone oxime, methyl isobutyl ketone oxime, cyclohexanone oxime, acetophenone oxime, and benzophenone oxime; pyrazoles such as pyrazole, 3,5-dimethylpyrazole, and 3-methylpyrazole; Thiols such as dodecanethiol and benzenethiol can be mentioned.

Compounds containing blocked isocyanate are also available as commercial products, and specific examples thereof include Takenate (registered trademark) B-830, B-815N, B-842N, B-870N, B-874N, B-882N, B-7005, B-7030, B-7075, B-5010 (manufactured by Mitsui Chemicals Polyurethane Co., Ltd.), Duranate (registered trademark) 17B-60PX, TPA-B80E, MF-B60X, MF-K60X, E402-B80T (above, manufactured by Asahikase Chemical Co., Ltd.), Karenz MOI-BM (registered trademark) (above, manufactured by Showa Denko Co., Ltd.), TRIXENE BI7950, 7951, 7960, Examples include Nos. 7961, No. 7982, No. 7990, No. 7991, and No. 7992 (registered trademark) (above, manufactured by Baxenden Chemical).

The aminoplast compound is not particularly limited as long as it has two or more methoxymethylene groups per molecule, for example, hexamethoxymethylmelamine CYMEL (registered trademark) 303, tetrabutoxymethyl glycoluril 1170 , Cymel series such as tetramethoxymethylbenzoguanamine 1123 (above, manufactured by Allnex Co., Ltd.), methylated melamine resin Nikalac (registered trademark) MW-30HM, MW-390, MW-100LM, Melamine-based compounds such as MX-750LM, methylated urea resins such as MX-270, MX-280, and MX-290 (above, manufactured by Sanwa Chemical Co., Ltd.), and other nickalac series.

The oxetane compound is not particularly limited as long as it has two or more oxetanyl groups per molecule. For example, Aaron Oxetane (registered trademark) OXT-221, OX-SQ-H, which contains an oxetanyl group, Examples include OX-SC (above, manufactured by Toagosei Co., Ltd.).

The phenoplast compound has two or more hydroxymethylene groups per molecule, and when exposed to high temperatures during heat curing, a crosslinking reaction proceeds between the compound and the polymer of the present invention by a dehydration condensation reaction.

As phenoplast compounds, for example, 2,6-dihydroxymethyl-4-methylphenol, 2,4-dihydroxymethyl-6-methylphenol, bis(2-hydroxy-3-hydroxymethyl -5-methylphenyl)methane, bis(4-hydroxy-3-hydroxymethyl-5-methylphenyl)methane, 2,2-bis(4-hydroxy-3,5-dihydroxymethylphenyl)propane , bis(3-formyl-4-hydroxyphenyl)methane, bis(4-hydroxy-2,5-dimethylphenyl)formylmethane, α,α-bis(4-hydroxy-2,5-di) and methylphenyl)-4-formyltoluene.

Penoplast compounds are also available as commercial products, and specific examples include 26DMPC, 46DMOC, DM-BIPC-F, DM-BIOC-F, TM-BIP-A, BISA-F, BI25X-DF, BI25X-TPA (above , Asahi Yuki Zai Kogyo Co., Ltd.), etc. can be mentioned.

Additionally, when a thin film made of the triazine ring-containing polymer of the present invention is laminated on a protective film such as PET or polyolefin film and irradiated with light through the protective film, good curing properties can be obtained even in the thin film laminated film without oxygen interference. In this case, since the protective film needs to be peeled off after curing, it is preferable to use a polybasic acid-modified acrylic oligomer that provides a thin film with good peelability.

The above-mentioned crosslinking agents may be used individually or in combination of two or more types. The amount of the crosslinking agent used is preferably 1 to 100 parts by mass based on 100 parts by mass of the triazine ring-containing polymer. However, considering solvent resistance, the lower limit is preferably 2 parts by mass, more preferably 5 parts by mass, and further. , considering controlling the refractive index, the upper limit is preferably 20 parts by mass, more preferably 15 parts by mass.

The composition of the present invention may also contain an initiator corresponding to each crosslinking agent. In addition, as described above, when a polyfunctional epoxy compound and/or a polyfunctional (meth)acrylic compound is used as a crosslinking agent, photocuring proceeds even without using an initiator to provide a cured film, but in that case, even if an initiator is used, There is no problem.

When using a multifunctional epoxy compound as a crosslinking agent, a photoacid generator or a photobase generator can be used.

The photoacid generator may be appropriately selected from known ones and used, for example, onium salt derivatives such as diazonium salt, sulfonium salt, or iodonium salt can be used.

Specific examples include aryl diazonium salts such as phenyl diazonium hexafluorophosphate, 4-methoxyphenyl diazonium hexafluoroantimonate, and 4-methylphenyl diazonium hexafluorophosphate; Diaryliodonium salts such as diphenyliodonium hexafluoroantimonate, di(4-methylphenyl)iodonium hexafluorophosphate, and di(4-tert-butylphenyl)iodonium hexafluorophosphate; Triphenylsulfonium hexafluoroantimonate, tris(4-methoxyphenyl)sulfonium hexafluorophosphate, diphenyl-4-thiophenoxyphenylsulfonium hexafluoroantimonate, diphenyl-4-thiophenyl Offenoxyphenylsulfonium hexafluorophosphate, 4,4'-bis(diphenylsulfonio)phenyl sulfide-bishexafluoroantimonate, 4,4'-bis(diphenylsulfonio)phenylsulfide- Bishexafluorophosphate, 4,4'-bis[di(β-hydroxyethoxy)phenylsulfonio]phenyl sulfide-bishexafluoroantimonate, 4,4'-bis[di(β-hyde) Roxyethoxy)phenylsulfonio]phenyl sulfide-bis-hexafluorophosphate, 4-[4'-(benzoyl)phenylthio]phenyl-di(4-fluorophenyl)sulfonium hexafluoroantimonate and triarylsulfonium salts such as 4-[4'-(benzoyl)phenylthio]phenyl-di(4-fluorophenyl)sulfonium hexafluorophosphate.

These onium salts may be commercially available, and specific examples include San Aid (registered trademark) SI-60, SI-80, SI-100, SI-60L, SI-80L, SI-100L, SI-L145, and SI-L150. , SI-L160, SI-L110, SI-L147 (above, manufactured by Sanshin Chemical Co., Ltd.), UVI-6950, UVI-6970, UVI-6974, UVI-6990, UVI-6992 (above, manufactured by Union Carbide Co., Ltd.) ), CPI (registered trademark)-100P, CPI-100A, CPI-200K, CPI-200S (above, manufactured by San-Apro Co., Ltd.), Adeka Optomer SP-150, SP-151, SP-170, SP- 171 (above, manufactured by ADEKA Co., Ltd.), Irgacure (registered trademark) 261 (manufactured by BASF Corporation), CI-2481, CI-2624, CI-2639, CI-2064 (above, manufactured by Nihon Soda Co., Ltd.), CD-1010, CD-1011, CD-1012 (manufactured by Sartomer), DS-100, DS-101, DAM-101, DAM-102, DAM-105, DAM-201, DSM-301, NAI-100 , NAI-101, NAI-105, NAI-106, SI-100, SI-101, SI-105, SI-106, PI-105, NDI-105, BENZOIN TOSYLATE, MBZ-101, MBZ-301, PYR- 100, PYR-200, DNB-101, NB-101, NB-201, BBI-101, BBI-102, BBI-103, BBI-109 (above, manufactured by Midorikagaku Co., Ltd.), PCI-061T, PCI -062T, PCI-020T, PCI-022T (above, manufactured by Nippon Kayaku Co., Ltd.), IBPF, IBCF (manufactured by Sanwa Chemical Co., Ltd.), etc.

On the other hand, photobase generators may be appropriately selected and used from known photobase generators. For example, Co-amine complex-based, oxime carboxylic acid ester-based, carbamic acid ester-based, quaternary ammonium salt-based photobase generators, etc. can be used. there is.

Specific examples include 2-nitrobenzylcyclohexylcarbamate, triphenylmethanol, O-carbamoylhydroxylamide, O-carbamoyloxime, [[(2,6-dinitrobenzyl)oxy]carbonyl]cyclohexyl. Amine, bis[[(2-nitrobenzyl)oxy]carbonyl]hexane 1,6-diamine, 4-(methylthiobenzoyl)-1-methyl-1-morpholinoethane, (4-mo Polynobenzoyl)-1-benzyl-1-dimethylaminopropane, N-(2-nitrobenzyloxycarbonyl)pyrrolidine, hexaamminecobalt(III)tris(triphenylmethylborate), 2-benzyl -2-dimethylamino-1-(4-morpholinophenyl)-butanone, 2,6-dimethyl-3,5-diacetyl-4-(2'-nitrophenyl)-1,4- Dihydropyridine, 2,6-dimethyl-3,5-diacetyl-4-(2',4'-dinitrophenyl)-1,4-dihydropyridine, etc. can be mentioned.

Additionally, commercially available photobase generators may be used, and specific examples thereof include TPS-OH, NBC-101, and ANC-101 (all product names, manufactured by Midorikagaku Co., Ltd.).

When using a mineral acid or base generator, it is preferably used in the range of 0.1 to 15 parts by mass, more preferably in the range of 1 to 10 parts by mass, based on 100 parts by mass of the polyfunctional epoxy compound.

Additionally, if necessary, an epoxy resin curing agent may be blended in an amount of 1 to 100 parts by mass based on 100 parts by mass of the multifunctional epoxy compound.

On the other hand, when using a multifunctional (meth)acrylic compound, a radical photopolymerization initiator can be used.

The radical photopolymerization initiator may be appropriately selected and used from known ones, for example, acetophenones, benzophenones, Michler's benzoyl benzoate, amyl oxime ester, oxime ester, tetramethyl thiouram monosulfide, and Thioxanthone types, etc. can be mentioned.

In particular, a photocleavage type photoradical polymerization initiator is preferable. The photocleavage type photoradical polymerization initiator is described in the latest UV curing technology (page 159, publisher: Kazuhiro Takausu, publisher: Technology Information Association Co., Ltd., published in 1991).

Commercially available radical photopolymerization initiators include, for example, Irgacure (registered trademark) 127, 184, 369, 379, 379EG, 651, 500, 754, 819, 903, 907, 784, 1173, 2959, CGI1700, and CGI1750. , CGI1850, CG24-61, OXE01, OXE02, Darocure (registered trademark) 1116, 1173, MBF, Lucirin TPO (manufactured by BASF), Ubecryl (registered trademark) P36 (manufactured by Cytech Surface Specialties), ESACURE ( Registered trademark) KIP150, KIP65LT, KIP100F, KT37, KT55, KTO46, KIP75/B (above, manufactured by Lamberti), etc.

When using a radical photopolymerization initiator, it is preferably used in the range of 0.1 to 200 parts by mass, and more preferably in the range of 1 to 150 parts by mass, based on 100 parts by mass of the polyfunctional (meth)acrylate compound.

It is preferable to use the composition of the present invention by adding various solvents to dissolve the triazine ring-containing polymer.

Solvents include, for example, water, toluene, p-xylene, o-xylene, m-xylene, ethylbenzene, styrene, ethylene glycol dimethyl ether, propylene glycol monomethyl ether, Ethylene glycol monomethyl ether, propylene glycol, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol methyl ether acetate , Propylene Glycol Monomethyl Ether Acetate, Ethylene Glycol Ethyl Ether Acetate, Diethylene Glycol Dimethyl Ether, Propylene Glycol Monobutyl Ether, Ethylene Glycol Monobutyl Ether, Diethylene Glycol diethyl ether, dipropylene glycol monomethyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, diethylene glycol monoethyl ether, triethylene Glycol dimethyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol, 1-octanol, ethylene glycol, hexylene glycol, trimethylene glycol, 1-mer Toxy-2-butanol, cyclohexanol, diacetone alcohol, furfuryl alcohol, tetrahydrofurfuryl alcohol, propylene glycol, benzyl alcohol, 1,3-butanediol, 1,4-butanediol , 2,3-butanediol, γ-butyrolactone, acetone, methyl ethyl ketone, methyl isopropyl ketone, diethyl ketone, methyl isobutyl ketone, methyl n-butyl ketone, cyclopentanone, cyclohexanone, acetic acid. Ethyl, isopropyl acetate, n-propyl acetate, isobutyl acetate, n-butyl acetate, ethyl lactate, methanol, ethanol, isopropanol, tert-butanol, allyl alcohol, n-propanol, 2-methyl-2-butanol, isobutanol. Ethanol, normal butanol, 2-methyl-1-butanol, 1-pentanol, 2-methyl-1-pentanol, 2-ethylhexanol, 1-methoxy-2-propanol, tetrahydrofuran, 1, 4-dioxane, N,N-dimethylformamide, N,N-dimethylacetamide (DMAc), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethylsulfoxide Side, N-cyclohexyl-2-pyrrolidinone, etc. are mentioned, and these may be used individually or in mixture of 2 or more types.

At this time, the solid content concentration in the composition is not particularly limited as long as it is within a range that does not affect storage stability, and may be set appropriately according to the thickness of the target film. Specifically, from the viewpoint of solubility and storage stability, the solid content concentration is preferably 0.1 to 50% by mass, more preferably 0.1 to 40% by mass.

The composition of the present invention contains other components other than the triazine ring-containing polymer, crosslinking agent, and solvent, such as leveling agents, surfactants, silane coupling agents, and antioxidants, as long as the effects of the present invention are not impaired. , rust inhibitors, mold release agents, plasticizers, antifoaming agents, thickeners, dispersants, antistatic agents, anti-settling agents, pigments, dyes, ultraviolet absorbers, light stabilizers, inorganic fine particles, etc. may be included. Examples of the surfactant include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, and polyoxyethylene oleyl ether; Polyoxyethylene alkylaryl ethers such as polyoxyethylene octyl phenol ether and polyoxyethylene nonyl phenol ether; Polyoxyethylene/polyoxypropylene block copolymers; sorbitan fatty acid esters such as sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, and sorbitan tristearate; Polyoxyethylene sorbitan fatty acids such as polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, and polyoxyethylene sorbitan tristearate. Nonionic surfactants such as esters, brand names Ftop EF301, EF303, EF352 (Mitsubishi Materials Denshikase Co., Ltd. (formerly Gemco Co., Ltd.)), Megapak F171, F173, R-08, R-30 , R-40, R-41, F-114, F-410, F-430, F-444, F-477, F-552, F-553, F-554, F-555, F-556, F -557, F-558, F-559, F-561, F-562, RS-75, RS-72-K, RS-76-E, RS-76NS, RS-77 (manufactured by DIC Co., Ltd.), Fluorine-based interfaces such as Florado FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Asahi Guard AG 710, Suplon S-382, SC101, SC102, SC103, SC104, SC105, and SC106 (manufactured by Asahi Glass Co., Ltd.) Activator, organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), BYK-302, BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-370, BYK-375 , BYK-378 (manufactured by Big Chemi Japan Co., Ltd.), etc.

These surfactants may be used individually or in combination of two or more types. The amount of surfactant used is preferably 0.0001 to 5 parts by mass, more preferably 0.001 to 1 part by mass, and even more preferably 0.01 to 0.5 parts by mass, per 100 parts by mass of the triazine ring-containing polymer.

Inorganic fine particles include, for example, Be, Al, Si, Ti, V, Fe, Cu, Zn, Y, Zr, Nb, Mo, In, Sn, Sb, Ta, W, Pb, Bi and Ce. Oxides, sulfides, or nitrides of one or two or more metals selected from In addition, the inorganic fine particles may be used individually or in combination of two or more types.

Specific examples of metal oxides include Al ₂ O ₃ , ZnO, TiO ₂ , ZrO ₂ , Fe ₂ O ₃ , Sb ₂ O ₅ , BeO, ZnO, SnO ₂ , CeO ₂ , SiO ₂ , and WO ₃ .

It is also effective to use multiple metal oxides as a composite oxide. A complex oxide is one in which two or more types of inorganic oxides are mixed in the manufacturing step of fine particles. Examples include complex oxides of TiO ₂ and ZrO ₂ , TiO ₂ , ZrO ₂ and SnO ₂ , and ZrO ₂ and SnO ₂ .

Additionally, it may be a compound of the above metal. For example, ZnSb ₂ O ₆ , BaTiO ₃ , SrTiO ₃ , SrSnO _{3 ,} etc. can be mentioned. These compounds can be used individually or in mixture of two or more types, and may also be used by mixing with the above oxides.

In addition, the above-mentioned other components can be added in any step when preparing the composition of the present invention.

The film-forming composition of the present invention can be applied to a substrate, heated as necessary to evaporate the solvent, and then heated or irradiated with light to form a desired cured film.

The application method of the composition is arbitrary, for example, spin coating method, dipping method, flow coating method, inkjet method, jet dispenser method, spray method, bar coating method, gravure coating method, slit coating method, roll coating method, transfer method. Methods such as printing method, brush coating method, blade coating method, and air knife coating method can be adopted.

In addition, the substrate includes silicon, glass with indium tin oxide (ITO), glass with indium zinc oxide (IZO), polyethylene terephthalate (PET), plastic, glass, quartz, ceramics, etc. Also, a flexible substrate having flexibility may be used.

The calcination temperature is not particularly limited for the purpose of evaporating the solvent, and can be performed at, for example, 110 to 400°C.

The firing method is not particularly limited, and may be evaporated in an appropriate atmosphere such as air, an inert gas such as nitrogen, or vacuum using a hot plate or oven.

As for the firing temperature and firing time, conditions suitable for the process of the target electronic device can be selected, and firing conditions where the physical properties of the resulting film are suitable for the required characteristics of the electronic device can be selected.

Conditions for light irradiation are not particularly limited, and appropriate irradiation energy and time may be adopted depending on the triazine ring-containing polymer and crosslinking agent used.

Since the thin film or cured film of the present invention obtained as described above can achieve high heat resistance, high refractive index, and low volumetric shrinkage, it can be used in liquid crystal displays, organic electroluminescence (EL) displays, touch panels, and optical semiconductors (LEDs). Electronic devices and optical materials, such as a member for manufacturing devices, solid-state imaging devices, organic thin-film solar cells, dye-sensitized solar cells, organic thin-film transistors (TFTs), lenses, prism cameras, binoculars, microscopes, semiconductor exposure devices, etc. It can be used appropriately for the field.

In particular, the thin film or cured film produced from the composition of the present invention has high transparency and a high refractive index, so when used as a protective film for a transparent conductive film such as ITO or silver nanowire, the visibility can be improved and the transparent conductive film can be improved. Deterioration of the membrane can be suppressed.

As a transparent conductive film, a transparent conductive film having a conductive nanostructure such as an ITO film, IZO film, metal nanoparticle, metal nanowire, or metal nanomesh is preferable, and a transparent conductive film having a conductive nanostructure is more preferable. The metal constituting the conductive nanostructure is not particularly limited, but includes silver, gold, copper, nickel, platinum, cobalt, iron, zinc, ruthenium, rhodium, palladium, cadmium, osmium, iridium, and alloys thereof. That is, a transparent conductive film having silver nanoparticles, silver nanowires, silver nanomesh, gold nanoparticles, gold nanowires, gold nanomesh, copper nanoparticles, copper nanowires, copper nanomesh, etc. is preferable, especially silver nanowires. A transparent conductive film having is preferred.

Example

Hereinafter, the present invention will be described in more detail through examples and comparative examples, but the present invention is not limited to the following examples. In addition, each measuring device used in the examples is as follows.

[ ^1H -NMR]

Device: BRUKER AVANCEIII HD (500MHz)

Measurement solvent: DMSO-d6

Reference material: tetramethylsilane (TMS) (δ0.0ppm)

[GPC]

Device: HLC-8200 GPC manufactured by Tosoh Corporation

Column: Shodex KF-804L+KF-805L

Column temperature: 40℃

Solvent: N,N-dimethylformamide (hereinafter referred to as DMF)

Detector: UV (254nm)

Calibration curve: standard polystyrene

[Elipsometer]

Apparatus: Multiple incident angle spectroscopic ellipsometer VASE manufactured by J.A. Ulam Japan

[Parallax thermobalance (TG-DTA)]

Device: TG-8120 manufactured by Rigaku Co., Ltd.

Temperature increase rate: 10℃/min

Measurement temperature: 25℃-750℃

[Light fastness tester]

Equipment: Xenon weatherability tester Q-SUN Xe-1-BC manufactured by Q-LAB

Optical Filter: Window Glass-Q

Illuminance: 0.50W/cm ² (λ=340nm)

Black panel temperature: 40℃

[Ultraviolet-Visible Spectrophotometer]

Device: UV-3600 ultraviolet-visible-near-infrared spectrophotometer manufactured by Shimazu Sesakusho Co., Ltd.

[1] Synthesis of hyperbranched polymer containing triazine ring

[Example 1-1] Synthesis of polymer compound [3]

Under nitrogen, m-phenylenediamine [2] (7.35 g, 0.022 mol, manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added to a 100 mL four-neck flask, and 28.26 g of N,N-dimethylacetamide (DMAc, Junsei) was added. It was dissolved with Kagaku Co., Ltd. product. Afterwards, it was cooled to -10°C in an ethanol-dry ice bath, and 2,4,6-trichloro-1,3,5-triazine [1] (3.69 g, 0.02 mol, manufactured by Eponic Degussa) was added. It was added while making sure that the bath temperature did not exceed 0°C. After stirring for 1 hour, the reaction solution was added dropwise to a 200 mL four-neck flask to which 28.16 g of DMAc had been previously added, purged with nitrogen, and set to 85°C in an oil bath. After stirring for 2 hours, aniline (2.79 g, 0.03 mol, manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added dropwise, and the mixture was stirred for 3 hours. After that, the temperature was lowered to room temperature, n-propylamine (2.73 g, manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added dropwise, and after stirring for 1 hour, stirring was stopped. The reaction solution was added dropwise to ion-exchanged water (375 g) and reprecipitated. The precipitate was filtered and redissolved in THF (53.85 g). After stirring for 1 hour, the supernatant was removed, and the solution was added dropwise to ion-exchanged water (431 g) and reprecipitated again. The obtained precipitate was filtered and dried in a reduced pressure dryer at 120°C for 6 hours to obtain 11.0 g of the target polymer compound [3] (hereinafter referred to as HB-TBAFA). The measurement results of the ¹ H-NMR spectrum of HB-TBAFA are shown in Figure 1.

The weight average molecular weight Mw of HB-TBAFA measured in polystyrene conversion by GPC was 23,000, and the polydispersity Mw/Mn was 34.8.

5 mg of the obtained HB-TBAFA was added to a platinum pan and measured by TG-DTA at a temperature increase rate of 10°C/min, and the 5% weight loss was 466.9°C.

[Example 1-2] Synthesis of polymer compound [5]

Under nitrogen, 1,3-bis(3-aminophenoxy)benzene [4] (12.86 g, 0.044 mol, manufactured by Mitsui Chemical Co., Ltd.) was added to a 100 mL four-necked flask, and 51.61 g of DMAc (Jun Sei Chemical Co., Ltd.) was added. It was dissolved in (Co., Ltd.). Afterwards, it was cooled to -10°C in an ethanol-dry ice bath, and 2,4,6-trichloro-1,3,5-triazine [1] (7.38 g, 0.04 mol, manufactured by Eponic Degussa) was added. It was added while making sure that the bath temperature did not exceed 0°C. After stirring for 1 hour, 51.61 g of DMAc was previously added to the reaction solution, purged with nitrogen, and then added dropwise to a 200 mL four-necked flask set at 85°C in an oil bath. After stirring for 2 hours, aniline (11.18 g, 0.12 mol, manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added dropwise, and the mixture was stirred for 3 hours. After that, the temperature was lowered to room temperature, n-propylamine (5.46 g, manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added dropwise, and after stirring for 1 hour, stirring was stopped. The reaction solution was added dropwise to ion-exchanged water (688 g) and reprecipitated. The precipitate was filtered and re-dissolved in THF (94.24 g). After stirring for 1 hour, the supernatant was removed, the concentration of the solution was adjusted with THF, and then it was added dropwise to ion-exchanged water (754 g) and reprecipitated again. The obtained precipitate was filtered and dried in a reduced pressure dryer at 120°C for 6 hours to obtain 13.2 g of the target polymer compound [5] (hereinafter referred to as HB-TAPBA). The measurement results of the ¹ H-NMR spectrum of HB-TAPBA are shown in Figure 2.

The weight average molecular weight Mw of HB-TAPBA measured in polystyrene conversion by GPC was 29,600, and the polydispersity Mw/Mn was 25.3. 5 mg of the obtained HB-TAPBA was added to a platinum pan and measured by TG-DTA at a temperature increase rate of 10°C/min, and the 5% weight loss was 450.9°C.

[Example 1-3] Synthesis of polymer compound [7]

Bisaniline-M [6] (7.58 g, 0.022 mol, manufactured by Mitsui Fine Chemicals Co., Ltd.) was added to a 100 mL four-necked flask under nitrogen, and dissolved in 28.73 g of DMAc (manufactured by Junsei Chemical Co., Ltd.). Afterwards, it was cooled to -10°C in an ethanol-dry ice bath, and 2,4,6-trichloro-1,3,5-triazine [1] (3.69 g, 0.02 mol, manufactured by Eponic Degussa) was added. It was added while making sure that the bath temperature did not exceed 0°C. After stirring for 1 hour, 28.73 g of DMAc was previously added to the reaction solution, purged with nitrogen, and then added dropwise to a 200 mL four-necked flask set at 85°C in an oil bath. After stirring for 2 hours, aniline (5.59 g, 0.06 mol, manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added dropwise, and the mixture was stirred for 3 hours. After that, the temperature was lowered to room temperature, n-propylamine (2.73 g, manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added dropwise, and after stirring for 1 hour, stirring was stopped. The reaction solution was added dropwise to ion-exchanged water (383 g) and reprecipitated. The precipitate was filtered and re-dissolved in THF (50.56 g). After stirring for 1 hour, the supernatant was removed, and the solution was added dropwise to ion-exchanged water (405 g) and reprecipitated again. The obtained precipitate was filtered and dried in a reduced pressure dryer at 120°C for 6 hours to obtain 7.9 g of the target polymer compound [7] (hereinafter referred to as HB-TBAMA).

The measurement results of the ¹ H-NMR spectrum of HB-TBAMA are shown in Figure 3. The weight average molecular weight Mw measured in polystyrene conversion by GPC of HB-TBAMA was 5,700, and the polydispersity Mw/Mn was 4.68. 5 mg of the obtained HB-TBAMA was added to a platinum pan and measured by TG-DTA at a temperature increase rate of 10°C/min, and the 5% weight loss was 435.3°C.

[Comparative Example 1-1] Synthesis of polymer compound [9]

Under nitrogen, 456.02 g of DMAc was added to a 1,000 mL four-necked flask, cooled to -10°C in an acetone-dry ice bath, and 2,4,6-trichloro-1,3,5-triazine [1]( 84.83 g, 0.460 mol, manufactured by Eponic Degussa Co., Ltd.) was added and dissolved. After that, m-phenylenediamine [8] (62.18 g, 0.575 mol) and aniline (14.57 g, 0.156 mol) dissolved in 304.01 g of DMAc were added dropwise. After dropping, stir for 30 minutes, add 621.85 g of DMAc to a 2,000 mL four-neck flask, add dropwise to a tank previously heated to 85°C in an oil bath using a liquid feeding pump over 1 hour, and stir for 1 hour to polymerize. did.

After that, aniline (113.95 g, 1.224 mol) was added, and after stirring for 1 hour, the reaction was terminated. After cooling to room temperature in an ice bath, triethylamine (116.36 g, 1.15 mol) was added dropwise, stirred for 30 minutes, and hydrochloric acid was added. After that, the precipitated hydrochloride was filtered off. The filtered reaction solution was reprecipitated in a mixed solution of 28% aqueous ammonia solution (279.29 g) and ion-exchanged water (8,820 g). The precipitate was filtered, dried in a reduced pressure dryer at 150°C for 8 hours, re-dissolved in THF (833.1 g), and reprecipitated in ion-exchanged water (6,665 g). The obtained precipitate was filtered and dried in a reduced pressure dryer at 150°C for 25 hours to obtain 118.0 g of the target polymer compound [9] (hereinafter referred to as HB-TmDA 40).

The obtained HB-TmDA 40 is a compound having a structural unit represented by formula (1). The weight average molecular weight Mw of HB-TmDA 40 measured in terms of polystyrene by GPC was 4,300, and the polydispersity Mw/Mn was 3.44. 405 mg of the obtained HB-TmDA was added to a platinum pan and measured by TG-DTA at a temperature increase rate of 10°C/min, and the 5% weight loss was 419°C.

[2] Production of film-forming composition and film

[Example 2-1]

0.5 g of HB-TBAFA obtained in Example 1-1 was dissolved in 4.5 g of cyclopentanone, and a light yellow transparent solution was obtained. The obtained polymer varnish was spin coated on a glass substrate using a spin coater at 200 rpm for 5 seconds and at 1000 rpm for 30 seconds, heated at 120°C for 3 minutes to remove the solvent, and a film was obtained. The refractive index of the obtained film was measured and found to be 1.648.

[Example 2-2]

A film was produced in the same manner as in Example 2-1 except that HB-TAPBA synthesized in Example 1-2 was used, and its refractive index was measured and found to be 1.718.

[Example 2-3]

A film was obtained in the same manner as in Example 2-1, except that HB-TBAMA synthesized in Example 1-3 was used. The refractive index was measured and was 1.684.

[Comparative Example 2-1]

A film was obtained in the same manner as in Example 2-1, except that HB-TmDA 40 obtained in Comparative Example 1-1 was used. The refractive index was measured to be 1.803.

For the films produced in Examples 2-1 to 2-3 and Comparative Example 2-1, each film was placed in a light resistance tester (0.50 W/m ² (λ=340 nm), black panel temperature 40°C), and subjected to 24 Changes in each film thickness, refractive index, and transmittance over time were measured. Their results are shown in Table 1. Additionally, graphs of transmittance are shown in FIGS. 4 to 7.

As shown in Table 1 and Figures 4 to 7, the film of the triazine polymer produced in Examples 2-1 to 2-3 and Comparative Example 2-1 has a small refractive index change rate after 24 hours, but Comparative Example 2-1 Since the film prepared from the varnish has a large change in transmittance, it can be seen that Examples 2-1 to 2-3 have excellent light resistance.

In particular, regarding Example 2-2, it can be seen that a high refractive index film of 1.7 or more was obtained. On the other hand, with respect to Examples 2-1 and 2-3, no change was observed in the transmittance, showing that they had very good light resistance.

[3] Production of composition for forming a cured film

[Example 3-1]

0.4 g of HB-TAPBA synthesized in Example 1-2 was dissolved in 1.6 g of cyclopentanone, and 0.2 g of urethane acrylate (KRM8452, manufactured by Dicell Allnex Co., Ltd.) in a 20 mass% cyclopentanone solution was used as a crosslinking agent. As a surfactant, 0.02 g of Megapak R-40 (manufactured by DIC Co., Ltd.) of a 1% by mass cyclopentanone solution, 0.04 g of ion-exchanged water, and 0.89 g of cyclohexanone were added, and the dissolution was confirmed with the naked eye, and the total solid content was A varnish with a concentration of 14% by mass (hereinafter referred to as HB-TAPBAV1) was prepared.

[Example 3-2]

0.4 g of HB-TBAMA synthesized in Example 1-3 was dissolved in 1.6 g of cyclopentanone, and 0.4 g of urethane acrylate (KRM8452, manufactured by Dicell Allnex Co., Ltd.) in a 20 mass% cyclopentanone solution was used as a crosslinking agent. As a surfactant, 0.02 g of Megapak R-40 (manufactured by DIC Co., Ltd.) of a 1% by mass cyclopentanone solution, 0.04 g of ion-exchanged water, and 0.97 g of cyclohexanone were added, and the dissolution was confirmed visually, and the total solid content was A varnish with a concentration of 14% by mass (hereinafter referred to as HB-TBAMAV1) was prepared.

[Comparative Example 3-1]

0.8 g of HB-TmDA 40 synthesized in Comparative Example 1-1 was dissolved in 3.2 g of cyclopentanone, and ethoxylated glycerol triacrylate (A-GLY-20-E, 200 mPa·s, Shin-Nakamura Kagaku Kogyo Co., Ltd.) 0.8 g and ethoxylated pentaerythritol tetraacrylate in 10 mass% cyclopentanone solution (ATM-35E, 350 mPa·s, Shin-Nakamura Kagaku Kogyo Co., Ltd.) Article) 0.24 g, 1.28 g of Irgacure 184 (manufactured by BASF) in a 5 mass% cyclopentanone solution as a photoradical polymerization initiator, and Megapak R-40 (DIC Co., Ltd.) in a 1 mass% cyclopentanone solution as a surfactant. 0.04 g, 0.09 g of ion-exchanged water, and 0.09 g of cyclopentanone were added, and the dissolution was confirmed visually to prepare a varnish with a total solid concentration of 15% by mass (hereinafter referred to as HB-TmDA40V1).

[4] Production of cured film

[Example 4-1]

HB-TAPBAV1 prepared in Example 3-1 was spin-coated on an alkali-free glass substrate at 200 rpm for 5 seconds and 1500 rpm for 30 seconds using a spin coater, and plasticized at 120°C for 1 minute using a hot plate, then heated to 230°C. Cured film 1 was obtained by heating for 10 minutes. The refractive index of the obtained cured film 1 was measured and found to be 1.714.

[Example 4-2]

Cured film 2 was produced in the same manner as in Example 4-1 except that HB-TBAMAV1 prepared in Example 3-2 was used, and its refractive index was measured and found to be 1.656.

[Comparative Example 4-1]

HB-TmDA40VF1 prepared in Comparative Example 3-1 was spin-coated at 200 rpm for 5 seconds and 2000 rpm for 30 seconds with a spin coater on an alkali-free glass substrate, and baked at 120°C for 3 minutes using an oven. After that, it was irradiated with a high-pressure mercury lamp at an integrated exposure amount of 200 mJ/cm ² to obtain cured film 3. The refractive index of the obtained cured film 3 was measured and found to be 1.766.

For the cured films 1 to 3 produced in Examples 4-1, 4-2 and Comparative Example 4-1, each was cured in a light resistance tester (0.50 W/m ² (λ = 365 nm), black panel temperature 50° C.) The membrane was placed, and 24 hours later, each membrane thickness, refractive index change, and transmittance change were measured. The results are shown in Table 2 and Figures 8 to 10.

As shown in Table 2 and Figures 8 to 10, the polymers synthesized in Examples 1-2 and 1-3 were found to have small changes in film thickness, refractive index, and transmittance before and after the light resistance test.

For the films produced in Examples 4-1 and 4-2, each film was placed on a hot plate previously heated to 230°C, and after heating for 20 minutes, the film thickness, refractive index change, and transmittance change were measured. The results are shown together in Table 3. The results are shown in Table 3 and Figures 11 and 12.

As shown in Table 3 and Figures 11 and 12, the polymers synthesized in Examples 1-2 and 1-3 show little change in film thickness and refractive index even when heated on a hot plate at 230°C for 20 minutes, and there is no change in transmittance. , it can be seen that it is a high refractive index cured film with excellent heat resistance and light resistance.

Claims (12)

A triazine ring-containing polymer characterized by comprising a repeating unit structure represented by the following formula (1).

{wherein R and R' represent hydrogen atoms,
Ar represents at least one type selected from the group represented by formulas (5) and (8).}
A composition for forming a film comprising the triazine ring-containing polymer according to claim 1 and an organic solvent. According to claim 2,
A composition for forming a film, characterized in that it further comprises a cross-linking agent. According to claim 3,
A composition for forming a film, characterized in that the crosslinking agent is a multifunctional (meth)acrylic compound. A film obtained from the film-forming composition according to any one of claims 2 to 4. An electronic device comprising a substrate and the film according to claim 5 formed on the substrate. An optical member comprising a base material and the film according to claim 5 formed on the base material.
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