Composition, cured product, optical filter, and method for producing cured product
By using a composition of dyes and specific cationic polymerizable components in an optical filter, especially a polycyclic aliphatic structure and alicyclic epoxy compounds, the problem of insufficient stability over time of light absorption is solved, and an optical filter with high stability and high adhesion is achieved.
Patent Information
- Application Number
- CN202080048137.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-09-04
- Filing Date
- 2020-08-07
- Publication Date
- 2025-07-15
- Estimated Expiration
- 2040-08-07
AI Technical Summary
In the prior art, an optical filter formed by using cationic polymerizable compounds has a problem that the light absorbability is insufficient over time.
The composition containing a dye and a specific cationic polymerizable component is used, and the cationic polymerizable component consists of an epoxy compound having a polycyclic aliphatic structure and an alicyclic epoxy compound. The content of the cationic polymerizable component reaches 50 parts by mass or more in the composition, and the content of the specific epoxy compound is between 20-70 parts by mass and the content of the low molecular weight compound is between 60-99 parts by mass.
It realizes a cured substance with excellent time stability with light absorption, reduces curing shrinkage and dye leakage, improves adhesion and softness with the substrate, and is suitable for image display devices.
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Abstract
Description
Technical Field
[0001] The present invention relates to compositions such as photosensitive resin compositions, cured products thereof, optical filters using the same, and methods for producing the cured products. Background Art
[0002] As a method for forming an optical filter that absorbs light of a specific wavelength, a method of forming a colored pattern by coating a colored composition containing a colorant and a curable compound by various coating methods such as photolithography and inkjet is known. As such a colored composition, for example, a composition in which a radical polymerizable compound is combined with a colorant is known. For example, Patent Document 1 describes a composition containing a dye and a radical polymerizable compound.
[0003] Prior Art Documents
[0004] Patent Documents
[0005] Patent Document 1: US2016216604A1 Summary of the Invention
[0006] Problems to be Solved by the Invention
[0007] However, when a cationic polymerizable compound is used instead of a radical polymerizable compound, a cured product having excellent temporal stability of light absorption is not obtained.
[0008] Therefore, an object of the present invention is to provide a composition capable of forming a cured product having excellent temporal stability of light absorption using a cationic polymerizable compound, a cured product thereof, an optical filter using the same, and a method for producing the cured product.
[0009] Means for Solving the Problems
[0010] The present inventors conducted intensive studies and found that by combining specific two kinds of epoxy compounds, the temporal stability of light absorption is improved.
[0011] Based on the above research findings, the present invention provides a composition containing a dye and a cationic polymerizable component, and the cationic polymerizable component contains an epoxy compound having a polycyclic aliphatic structure and an alicyclic epoxy compound.
[0012] The epoxy compound having a polycyclic aliphatic structure is preferably an aliphatic epoxy compound in terms of easily obtaining a cured product having excellent temporal stability of light absorption.
[0013] The content of the above cationic polymerizable component is preferably 50 parts by mass or more in 100 parts by mass of the solid content of the above composition in terms of easily obtaining a cured product having excellent temporal stability of light absorption.
[0014] The above-mentioned epoxy compound having a polycyclic aliphatic structure and containing a compound having a structure represented by the following formula (I) as the polycyclic aliphatic structure is preferable in terms of the balance between the effect of obtaining a cured product with excellent temporal stability of light absorption and curability.
[0015] [Chemical formula 1]
[0016]
[0017] (In the formula, the polycyclic aliphatic structure means bonding to an adjacent group at the * part.)
[0018] The content of the above-mentioned epoxy compound having a polycyclic aliphatic structure is preferably 20 parts by mass or more and 70 parts by mass or less in 100 parts by mass of the above-mentioned cationic polymerizable component in terms of easily obtaining a cured product with excellent temporal stability of light absorption.
[0019] The above-mentioned alicyclic epoxy compound contains a compound represented by the following formula (1) and is preferable in terms of the balance between the effect of obtaining a cured product with excellent temporal stability of light absorption and curability being excellent.
[0020] [Chemical formula 1A]
[0021]
[0022] (In the formula, X 1 represents a direct bond or a divalent linking group having one or more atoms.)
[0023] The above-mentioned cationic polymerizable component contains an aliphatic epoxy compound not having the above-mentioned polycyclic aliphatic structure and is preferable in terms of obtaining a cured product with excellent temporal stability of light absorption and, in the case of forming a cured product of the cationic polymerizable component on a substrate, obtaining a cured product with good adhesion to the substrate.
[0024] The aliphatic epoxy compound not having the above-mentioned polycyclic aliphatic structure contains a compound represented by the following formula (2) and is preferable in terms of obtaining a cured product with excellent temporal stability of light absorption and good adhesion to the substrate.
[0025] [Chemical formula 1B]
[0026]
[0027] (In the formula, R 1 is a group obtained by removing p hydroxyl groups (-OH) from a p-valent alcohol, and p and q each represent an integer of 1 or more.)
[0028] When p is 2 or more, the p structural units q may be the same or different.
[0029] The above cationic polymerizable component contains a low molecular weight compound having a molecular weight of 1,000 or less.
[0030] The content of the above low molecular weight compound is 60 parts by mass or more and 99 parts by mass or less in 100 parts by mass of the above cationic polymerizable component, and is preferably used because it is easy to form a cured product having excellent light absorption and excellent stability over time.
[0031] The above dye contains at least one of a pyrromethene dye and a tetraazaporphyrin dye, and is preferably used from the viewpoint of being able to effectively exhibit the effect of obtaining a cured product having excellent light absorption and excellent stability over time.
[0032] The above pyrromethene dye is a dipyrromethene complex obtained by coordinating the structure represented by the following formula (11) with a metal atom or a metal compound, and the above tetraazaporphyrin dye is a compound represented by the following formula (12), and is preferably used from the viewpoint of being able to more effectively exhibit the effect of obtaining a cured product having excellent light absorption and excellent stability over time.
[0033] [Chemical formula 2]
[0034]
[0035] (In the formula, R 101 ~R 103 and R 105 ~R 107 each independently represent a linear or branched alkyl group which may have a substituent, and R 104 represents a hydrogen atom, a linear or branched alkyl group which may have a substituent, or an aryl group which may have a substituent.)
[0036] [Chemical formula 3]
[0037]
[0038] (In the formula, R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 and R 308Each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, an alkyl group having 1 to 30 carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 carbon atoms which may have a substituent, or a heteroaryl group having 2 to 30 carbon atoms which may have a substituent.
[0039] R 301 With R 302 、R 303 With R 304 、R 305 With R 306 And R 307 With R 308 They may also be connected to each other to form an alicyclic structure containing the carbon atoms of the pyrrole ring.
[0040] R 301 、R 302 、R 303 、R 304 、R 305 、R 306 、R 307 And R 308 Will not all become hydrogen atoms at the same time.
[0041] M represents a compound of two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, or a trivalent or tetravalent metal.)
[0042] The present invention further provides a cured product of the above composition. The cured product of the present invention can be used as an optical filter having excellent temporal stability of light absorption.
[0043] The present invention also provides an optical filter having a light absorption layer containing the above cured product. By having this light absorption layer, the optical filter becomes an optical filter having excellent temporal stability of light absorption.
[0044] The present invention provides a method for manufacturing a cured product, which includes a step of curing the above composition. Since this manufacturing method is a method of curing the above composition, for example, a cured product that can be used as an optical filter having excellent temporal stability of light absorption can be easily obtained.
[0045] Advantages of the Invention
[0046] The present invention has the effect of being able to provide a composition that can be used to manufacture a cured product having excellent temporal stability of light absorption using a cationically polymerizable component. Detailed Description of the Invention
[0047] First, the composition of the present invention will be described in detail.
[0048] A. Composition
[0049] The composition of the present invention contains a dye and a cationic polymerizable component, and the cationic polymerizable component contains an epoxy compound having a polycyclic aliphatic structure and an alicyclic epoxy compound.
[0050] The inventors of the present invention have found through research that in the case of forming an optical filter using a radical polymerizable coloring composition containing a dye as a colorant, there is sometimes a problem that an optical filter excellent in light absorbency in a desired wavelength region cannot be obtained.
[0051] Moreover, it has been found that by using a cationic polymerizable compound as a curable compound, a cured product excellent in light absorbency in a desired wavelength region can be obtained, and it was filed before the filing of the present application.
[0052] However, as a result of further research by the inventors of the present invention, it has been found that in the case of using a cured product formed by a cationic polymerizable compound, there is sometimes a problem that the light absorbency changes over time. Moreover, as a result of further in-depth research, it has been found that by containing a dye and a cationic polymerizable component containing an epoxy compound having a polycyclic aliphatic structure and an alicyclic epoxy compound, a cured product excellent in the temporal stability of light absorbency can be obtained.
[0053] Regarding the reason why the temporal stability of light absorbency can be obtained by a specific polymerizable component, the inventors of the present invention consider as follows.
[0054] Cationic polymerizable components such as epoxy compounds have a milder curing reaction compared to radical polymerizable compounds such as methacrylates and acrylates, and can suppress the generation of modification in dyes during curing. In particular, the inventors of the present invention have found through research that by using a combination of two specific cationic polymerizable components, the inhibitory effect on the modification of dyes and the like is excellent. As a result, when the composition is cured, the content of the dye, that is, the dye that can absorb light in the desired wavelength region, hardly decreases over time. The reason for this is considered in detail as follows.
[0055] That is, the above two specific cationic polymerizable components can obtain a cured product with less curing shrinkage by containing a ring structure. In particular, an epoxy compound having a polycyclic aliphatic structure can effectively suppress curing shrinkage due to the steric hindrance generated by the polycyclic aliphatic structure. In addition, an epoxy compound having a polycyclic aliphatic structure can effectively block the intrusion of moisture into the cured product through the polycyclic aliphatic structure. In particular, even under high-temperature and high-humidity conditions, it can effectively block the intrusion of moisture into the cured product. As a result, the above composition becomes a composition of a cured product in which the dye is easily stably held, the bleeding of the dye is less, and in addition, the decomposition or modification of the dye caused by the influence of the intruded moisture can be suppressed.
[0056] In addition, the alicyclic epoxy compound has excellent curability, and polymerization can be efficiently carried out between alicyclic epoxy compounds and between an alicyclic epoxy compound and an epoxy compound having a polycyclic aliphatic structure. As a result, the above composition becomes a composition that easily forms a cured product in which the dye is stably held and the bleeding of the dye is small, and it becomes easy to sufficiently carry out polymerization, so that the intrusion of moisture into the cured product can be effectively blocked, and the decomposition or modification of the dye can be suppressed.
[0057] According to the above content, a composition in which two specific cationic polymerizable components are used in combination can obtain a cured product having excellent light absorbency in a desired wavelength region, and the temporal stability of the light absorbency becomes excellent.
[0058] In addition, in the composition of the present invention, by using a cationic polymerizable component containing a specific component, the state in which the dye is stably dispersed can be maintained, which is therefore preferable. A cationic polymerizable component containing two specific epoxy compounds has less curing shrinkage during curing compared to radical polymerizable compounds such as methacrylate and acrylate, and there are fewer adverse conditions such as dye aggregation during curing. As a result, the cured product of the above composition becomes a cured product in which the dye is stably dispersed and held. As a result, the dye in the above cured product can effectively absorb light in a desired wavelength range.
[0059] According to the above content, in addition to obtaining a cured product having excellent temporal stability of light absorbency, the prediction of the light absorbency of the cured product also becomes easy for the composition of the present invention.
[0060] The composition according to the present invention further exhibits the following effects.
[0061] The cationic polymerizable component containing two specific epoxy compounds has less curing shrinkage during polymerization as described above. Therefore, even when the above composition is formed into a cured product after being coated on a member such as a substrate, the generation of curling and further the generation of peeling are reduced.
[0062] In addition, the above composition can be cured by cationic polymerization, and the obtained cured product can be made into a three-dimensionally crosslinked cured product. As a result, the above cured product becomes a cured product having excellent durability such as dye retention performance and strength compared to, for example, a composition obtained by dispersing a dye in a thermoplastic resin.
[0063] Furthermore, the cured product obtained from the above composition becomes a cured product having excellent flexibility compared to radical polymerizable compounds such as acrylate. Therefore, an optical filter manufactured using the above composition can be particularly preferably used for, for example, an image display device that requires flexibility.
[0064] According to the above content, by using a composition containing a specified dye and two specific cationic polymerizable components, the composition can form a cured product with excellent photoabsorbing stability over time, and can obtain a cured product with particularly excellent photoabsorbing properties in the desired wavelength region, less curling and peeling, and excellent adhesion and flexibility.
[0065] Hereinafter, each component contained in the composition of the present invention will be described in detail.
[0066] 1. Cationic polymerizable component
[0067] The cationic polymerizable component refers to a compound that undergoes polymerization or crosslinking reaction by an acid. As this component, in the present invention, an epoxy compound having a polycyclic aliphatic structure and an alicyclic epoxy compound are contained.
[0068] (1) Epoxy compound (A) having a polycyclic aliphatic structure
[0069] The polycyclic aliphatic structure refers to a condensed ring composed only of aliphatic rings. Specifically, it refers to a structure in which two or more aliphatic rings are condensed without including an aromatic ring.
[0070] The polycyclic aliphatic structure can be either a saturated polycyclic aliphatic structure or an unsaturated polycyclic aliphatic structure.
[0071] Examples of the saturated polycyclic aliphatic structure include a camphane ring, an adamantane ring, a norbornane ring, a bicyclo[2.1.0]pentane ring, a bicyclo[2.1.1]hexane ring, a bicyclo[2.2.0]hexane ring, a bicyclo[3.1.0]hexane ring, a norpinane ring, a norcarane ring, a bicyclo[2.2.2]octane ring, a bicyclo[3.2.1]octane ring, a bicyclo[3.3.0]octane ring, a bicyclo[4.2.0]octane ring, a bicyclo[5.1.0]octane ring, a bicyclo[4.3.0]nonane ring, a bicyclo[3.3.1]nonane ring, a bicyclo[4.3.1]decane ring, a tricyclo[5.2.1.0 2,6 decane ring (also called tetrahydrodicyclopentadiene ring).
[0072] Examples of the unsaturated polycyclic aliphatic structure include a norbornene ring, a dicyclopentadiene ring, a bicyclo[2.2.2]oct-2-ene ring.
[0073] As the polycyclic aliphatic structure, from the aspects that the modification inhibition of the dye becomes easier, it is easy to form a cured product with excellent photoabsorbing stability over time, and it is easy to obtain a cured product with excellent photoabsorbing properties in the desired wavelength region, a saturated polycyclic aliphatic structure is preferred.
[0074] The polycyclic aliphatic structure may also contain heteroatoms in the ring-forming atoms, but from the aspect of easily obtaining a cured product with excellent light absorbability in the desired wavelength region, having less reaction with dyes and being easy to suppress modification of dyes, and easily forming a cured product with excellent temporal stability of light absorbability, it is preferably free of heteroatoms.
[0075] The polycyclic aliphatic structure may be any of bicyclic, tricyclic, and tetracyclic or higher, but is particularly preferably tricyclic or bicyclic, and especially preferably tricyclic. This is because the above composition becomes a composition having an excellent balance between the effect of obtaining a cured product with excellent temporal stability of light absorbability and curability.
[0076] It should be noted that the so-called bicyclic refers to a cyclic structure having two rings, and also includes a cyclic structure in which two rings share two or more atoms such as a bicyclo[2.1.0]pentane ring and a norbornane ring, and a structure in which two rings are bonded through one atom such as a spiro ring structure.
[0077] In addition, the so-called tricyclic refers to a cyclic structure having three rings, and examples thereof include a cyclic structure in which two or more atoms are shared between one ring of the bicyclic structure and the third ring.
[0078] The number of carbon atoms constituting the polycyclic aliphatic structure is not particularly limited, but is preferably 7 or more and 12 or less, and more preferably 9 or more and 11 or less. This is because the above composition becomes a composition having an excellent balance between the effect of obtaining a cured product with excellent temporal stability of light absorbability and curability. It should be noted that the number of carbon atoms constituting the polycyclic aliphatic structure represents the number of carbon atoms forming the polycyclic aliphatic ring skeleton, and does not include the number of carbon atoms of substituents.
[0079] As the polycyclic aliphatic structure, a tricyclo[5.2.1.0 2,6 decane ring structure is preferred from the aspect of the balance between the effect of obtaining a cured product with excellent temporal stability of light absorbability and curability, and specifically, the structure represented by the following formula (I) can be cited.
[0080] [Chemical formula 4]
[0081]
[0082] (In the formula, the polycyclic aliphatic structure means bonding to an adjacent group at the * part.)
[0083] The epoxy compound (A) having a polycyclic aliphatic structure may contain only one polycyclic aliphatic structure, or may contain two or more, but is preferably one. This is because the above composition becomes a composition having an excellent balance between the effect of obtaining a cured product with excellent temporal stability of light absorbability and curability.
[0084] In addition, from the aspect of easily obtaining a cured product with more excellent temporal stability of light absorption, the epoxy compound (A) is preferably a compound having a polycyclic aliphatic structure in its main chain.
[0085] It should be noted that the compound having a polycyclic aliphatic structure in its main chain can be set as a compound in which two or more epoxy groups are bonded to the polycyclic aliphatic structure via an ether structure. The so-called ether structure means a structure containing an ether group.
[0086] One or more hydrogen atoms on the ring in the polycyclic aliphatic structure may be substituted by a substituent.
[0087] Examples of the substituent include a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, a group having 2 to 30 carbon atoms containing a heterocycle which may have a substituent, a group obtained by substituting a methylene group in the hydrocarbon group or the group having 2 to 30 carbon atoms with a divalent group selected from the following Group I under the condition that oxygen atoms are not adjacent, an amino group, or a halogen atom.
[0088] Examples of the substituent for substituting one or more hydrogen atoms in the above hydrocarbon group or the group having 2 to 30 carbon atoms or the group obtained by substituting a methylene group in these groups with a divalent group selected from the following Group I include a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, or an isocyanate group.
[0089] Group I: -O-, -CO-, -COO-, -OCO-, -NR 10 -, -NR 10 CO-, -S-, -CS-, -SO2-, -SCO-, -COS-, -OCS-, CSO- or a group formed by combining these groups under the condition that oxygen atoms are not adjacent.
[0090] R 10 represents a hydrogen atom or an unsubstituted hydrocarbon group having 1 to 30 carbon atoms.
[0091] It should be noted that in this specification, when a hydrogen atom in a group having a specified number of carbon atoms is substituted by a substituent containing a carbon atom, it is set to satisfy the specification including the carbon atom of the substituent. Therefore, when a hydrogen atom in a hydrocarbon group having 1 to 30 carbon atoms is substituted by a substituent, the number of carbon atoms of 1 to 30 means the number of carbon atoms after the hydrogen atom is substituted, and does not mean the number of carbon atoms of the group before the hydrogen atom is substituted.
[0092] In addition, the stipulation of the number of carbon atoms for a group obtained by substituting a methylene group in a group having a specified number of carbon atoms with a divalent group is set to be the same as the stipulation of the number of carbon atoms contained in the group before substitution. Therefore, the number of carbon atoms of a group obtained by substituting a methylene group in a hydrocarbon group having 1 to 30 carbon atoms with a divalent group is set to 1 to 30.
[0093] As the hydrocarbon group having 1 to 30 carbon atoms that can substitute a hydrogen atom on the ring of the polycyclic aliphatic structure and R in the above Group I 10 The hydrocarbon group having 1 to 30 carbon atoms represented, as long as it is a hydrocarbon group without a heterocyclic structure, examples thereof include linear or branched chain alkyl groups having 1 to 30 carbon atoms, alkenyl groups having 2 to 30 carbon atoms, cycloalkyl groups having 3 to 30 carbon atoms, and cycloalkylalkyl groups having 4 to 30 carbon atoms, etc., aliphatic hydrocarbon groups, aryl groups having 6 to 30 carbon atoms, and arylalkyl groups having 7 to 30 carbon atoms, etc., aromatic hydrocarbon groups. From the aspect of improving the sensitivity of the curable composition, as the above hydrocarbon group, an alkyl group having 1 to 20, particularly 1 to 10 carbon atoms, an alkenyl group having 2 to 20, particularly 2 to 10 carbon atoms, a cycloalkyl group having 3 to 20, particularly 3 to 10 carbon atoms, a cycloalkylalkyl group having 4 to 20, particularly 4 to 10 carbon atoms, an aryl group having 6 to 20, particularly 6 to 10 carbon atoms, and an arylalkyl group having 7 to 20, particularly 7 to 10 carbon atoms are more preferable.
[0094] As the linear or branched chain alkyl group having 1 to 30 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, tert-pentyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, tert-octyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, and eicosyl can be cited.
[0095] As the alkenyl group having 2 to 30 carbon atoms, for example, vinyl, 2-propenyl, 3-butenyl, 2-butenyl, 4-pentenyl, 3-pentenyl, 2-hexenyl, 3-hexenyl, 5-hexenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 3-octenyl, 3-nonenyl, 4-decenyl, 3-undecenyl, 4-dodecenyl, 3-cyclohexenyl, 2,5-cyclohexadien-1-ylmethyl, and 4,8,12-tetradecatrienyl allyl can be cited.
[0096] The cycloalkyl group having 3 to 30 carbon atoms refers to a saturated monocyclic or saturated polycyclic alkyl group having 3 to 30 carbon atoms. For example, as the above cycloalkyl group, a group obtained by removing one hydrogen atom from a cycloalkyl ring such as a monocyclic hydrocarbon ring like a cyclohexyl ring, a crosslinked hydrocarbon ring like a norbornane ring, etc., or a group obtained by substituting one or more hydrogen atoms in the ring obtained by removing one hydrogen atom from a cycloalkyl ring with an aliphatic hydrocarbon group, i.e., a monocyclic hydrocarbon group, a crosslinked hydrocarbon ring group, etc. can be cited.
[0097] As the above monocyclic hydrocarbon group, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, methylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, tetramethylcyclohexyl, pentamethylcyclohexyl, ethylcyclohexyl, methylcycloheptyl, etc. can be cited.
[0098] As the above crosslinked hydrocarbon ring group, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, bicyclo[4.3.1]decyl, bicyclo[3.3.1]nonyl, bornyl, bornenyl, norbornyl, norbornenyl, 6,6-dimethylbicyclo[3.1.1]heptyl, tricyclobutyl, adamantyl can be cited.
[0099] As the cycloalkylalkyl having 4 to 30 carbon atoms, a group formed by combining the above cycloalkyl with the above straight-chain or branched-chain alkyl group can also be used. For example, groups in which one or more hydrogen atoms in the straight-chain or branched-chain alkyl group are substituted by the above cycloalkyl, groups in which one or more methylene groups in the straight-chain or branched-chain alkyl group are substituted by a group obtained by removing one hydrogen atom from the above cycloalkyl, etc. can be mentioned. Specifically, as the group having 4 to 30 carbon atoms in which a hydrogen atom of the straight-chain or branched-chain alkyl group is substituted by a cycloalkyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, cyclononylmethyl, cyclodecylmethyl, 2-cyclobutylethyl, 2-cyclopentylethyl, 2-cyclohexylethyl, 2-cycloheptylethyl, 2-cyclooctylethyl, 2-cyclononylethyl, 2-cyclodecylethyl, 3-cyclobutylpropyl, 3-cyclopentylpropyl, 3-cyclohexylpropyl, 3-cycloheptylpropyl, 3-cyclooctylpropyl, 3-cyclononylpropyl, 3-cyclodecylpropyl, 4-cyclobutylbutyl, 4-cyclopentylbutyl, 4-cyclohexylbutyl, 4-cycloheptylbutyl, 4-cyclooctylbutyl, 4-cyclononylbutyl, 4-cyclodecylbutyl, 3-3-adamantylpropyl, decahydronaphthylpropyl, etc. can be mentioned. As the cycloalkylalkyl having 4 to 10 carbon atoms, for example, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, cyclononylmethyl, 2-cyclobutylethyl, 2-cyclopentylethyl, 2-cyclohexylethyl, 2-cycloheptylethyl, 2-cyclooctylethyl, 3-cyclobutylpropyl, 3-cyclopentylpropyl, 3-cyclohexylpropyl, 3-cycloheptylpropyl, 4-cyclobutylbutyl, 4-cyclopentylbutyl, 4-cyclohexylbutyl, etc. can be mentioned.
[0100] As the aryl having 6 to 30 carbon atoms, a group obtained by removing one hydrogen atom from an aromatic ring or a group in which a hydrogen atom in the aromatic ring contained in the group is substituted by an aliphatic hydrocarbon group can be set. More specifically, a group obtained by removing one hydrogen atom from a monocyclic aromatic ring or a monocyclic aromatic hydrocarbon group in which a hydrogen atom in the aromatic ring contained in the group is substituted by an aliphatic hydrocarbon group can be mentioned; a group obtained by removing one hydrogen atom from a condensed aromatic ring formed by condensing monocyclic aromatic rings or a polycyclic aromatic hydrocarbon group in which a hydrogen atom in the aromatic ring contained in the group is substituted by an aliphatic hydrocarbon group can be mentioned; a group obtained by removing one hydrogen atom from a collective aromatic ring formed by bonding a monocyclic aromatic ring and a condensed aromatic ring via a linking group such as a single bond or a carbonyl group or a ring collective aromatic hydrocarbon group in which a hydrogen atom in the aromatic ring contained in the group is substituted by an aliphatic hydrocarbon group can be mentioned, etc.
[0101] Examples of such aryl groups include phenyl, tolyl, xylyl, ethylphenyl, naphthyl, anthryl, phenanthryl, etc., and phenyl, biphenyl, naphthyl, anthryl, etc. obtained by substituting one or more hydrogen atoms with the above-mentioned alkyl groups, alkenyl groups, etc.
[0102] As the above-mentioned monocyclic aromatic hydrocarbon group, a monocyclic aromatic hydrocarbon group having 6 to 20 carbon atoms is preferred. Specifically, examples include phenyl, o-tolyl, m-tolyl, p-tolyl, 2,4-xylyl, p-cumenyl, mesityl, etc.
[0103] As the above-mentioned polycyclic aromatic hydrocarbon group, a polycyclic aromatic hydrocarbon group having 10 to 20 carbon atoms is preferred. Specifically, examples include 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 5-anthryl, 1-phenanthryl, 9-phenanthryl, 1-acenaphthylenyl, 2-azulenyl, 1-pyrenyl, 2-triphenyl, 1-pyrenyl, 2-pyrenyl, 1-perylenyl, 2-perylenyl, 3-perylenyl, 2-triphenylene, 2-indenyl, 1-acephenanthrylenyl, 2-butaphenyl, 2-pentaphenyl, etc.
[0104] As the above-mentioned ring-aggregated aromatic hydrocarbon group, a ring-aggregated aromatic hydrocarbon group having 12 to 20 carbon atoms is preferred. Specifically, examples include o-biphenyl, m-biphenyl, p-biphenyl, terphenyl, 7-(2-naphthyl)-2-naphthyl, etc.
[0105] The arylalkyl group having 7 to 30 carbon atoms refers to a group having 7 to 30 carbon atoms obtained by substituting a hydrogen atom of an alkyl group with an aryl group. Examples include benzyl, α-methylbenzyl, α,α-dimethylbenzyl, phenylethyl, naphthylpropyl, etc.
[0106] The group having 2 to 30 carbon atoms containing a heterocycle that can replace a hydrogen atom on the ring of the polycyclic aliphatic structure is not particularly limited. For example, pyrrolyl, pyridyl, pyridylethyl, pyrimidinyl, pyridazinyl, piperazinyl, piperidinyl, pyranyl, pyranylethyl, pyrazolyl, triazinyl, triazinylmethyl, pyrrolidinyl, quinolinyl, isoquinolinyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuryl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, morpholinyl, thiomorpholinyl, 2-pyrrolidone-1-yl, 2-piperidone-1-yl, 2,4-dioxoimidazolidin-3-yl, 2,4-dioxooxazolidin-3-yl and the like, which are groups obtained by removing one hydrogen atom from the heterocycle or groups obtained by substituting one or more hydrogen atoms in the groups obtained by removing one hydrogen atom from the heterocycle with a hydrocarbon group, namely heterocyclic groups. As the group containing a heterocycle, there can be mentioned the above-mentioned heterocyclic groups, and groups obtained by substituting one or two or more hydrogen atoms in the hydrocarbon group with the above-mentioned heterocyclic groups. As these hydrocarbon groups, there can be mentioned the hydrocarbon groups listed above as the hydrocarbon groups having 1 to 30 carbon atoms that can replace a hydrogen atom on the ring of the polycyclic aliphatic structure. Specific examples of the group containing a heterocycle include groups having the following structures and the like.
[0107] [Chemical formula 4A]
[0108]
[0109] (In the above formula, each R independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z represents a direct bond or an alkylene group having 1 to 6 carbon atoms. It should be noted that * in the formula means that the group represented by these formulas is bonded to the adjacent group at the * part.)
[0110] As the alkyl group having 1 to 6 carbon atoms represented by R in the above formula, there can be mentioned the alkyl groups having 1 to 6 carbon atoms among the alkyl groups exemplified as the above-mentioned straight-chain or branched-chain alkyl groups having 1 to 30 carbon atoms.
[0111] As the alkylene group having 1 to 6 carbon atoms represented by Z in the above formula, an alkylene group having a specified number of carbon atoms can be exemplified from the straight-chain or branched-chain alkyl groups having 1 to 30 carbon atoms described above by removing one hydrogen atom. Specifically, as the above alkylene group, methylene, ethylene, propylene, methylethylene, butylene, 1-methylpropylene, 2-methylpropylene, 1,2-dimethylpropylene, 1,3-dimethylpropylene, 1-methylbutylene, 2-methylbutylene, 3-methylbutylene, 4-methylbutylene, 2,4-dimethylbutylene, 1,3-dimethylbutylene, pentylene, hexylene, ethane-1,1-diyl, propane-2,2-diyl can be exemplified.
[0112] As the halogen atom that can substitute the hydrogen atom on the ring of the polycyclic aliphatic structure or the hydrogen atom in the substituent of the hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom can be exemplified.
[0113] The amino group that can substitute the hydrogen atom on the ring of the polycyclic aliphatic structure or the hydrogen atom in the substituent of the hydrogen atom can be any of a primary amino group, a secondary amino group, and a tertiary amino group.
[0114] As the secondary amino group and the tertiary amino group, groups obtained by substituting 1 or 2 hydrogen atoms of the primary amino group (-NH2) with a hydrocarbon group having 1 to 30 carbon atoms can be exemplified respectively. As the hydrocarbon group having 1 to 30 carbon atoms, the hydrocarbon groups exemplified above as the group that can substitute the hydrogen atom on the ring of the polycyclic aliphatic structure can be used.
[0115] As the above secondary amino group, for example, N-methylamino, N-ethylamino, N-n-butylamino, etc. can be exemplified.
[0116] As the above tertiary amino group, N,N-dimethylamino, N,N-diethylamino, N,N-di-n-butylamino, N,N-ethylphenyl, etc. can be exemplified.
[0117] From the viewpoints of ease of acquisition and easily obtaining a cured product having excellent temporal stability of light absorption, the polycyclic aliphatic structure preferably has a structure in which the hydrogen atom on the ring is not substituted by a substituent, or a structure in which the substituent is a hydrocarbon group having 1 to 10 carbon atoms or a halogen atom when substituted. From the same viewpoints, it is more preferably that the hydrogen atom on the ring is not substituted by a substituent, or the substituent is a hydrocarbon group having 1 to 5 carbon atoms or a halogen atom when substituted, particularly preferably that the hydrogen atom on the ring is not substituted by a substituent, or the substituent is an alkyl group having 1 to 5 carbon atoms or a halogen atom when substituted, and most preferably that the hydrogen atom on the ring is not substituted by a substituent, or the substituent is a methyl group or a halogen atom when substituted. This is because it is easy to form a cured product having excellent temporal stability of light absorption and the ease of acquisition is excellent.
[0118] The number of polycyclic aliphatic structures or the linking structure between the epoxy group and the polycyclic aliphatic structure in the epoxy compound (A) having a polycyclic aliphatic structure can be any number or linking structure. The epoxy compound (A) having a polycyclic aliphatic structure may also be a monofunctional epoxy compound, but from the aspect of easily obtaining a composition with an excellent balance between the effect of a cured product having excellent light absorptivity over time and curability, a polyfunctional epoxy compound is preferred. Further preferably, it is a compound having 2 or more and 4 or less functional groups, and more preferably a compound having 2 or more and 3 or less functional groups. In particular, the epoxy compound (A) being a compound having a glycidyl ether group is preferred from the aspect of easily obtaining a composition with an excellent balance between the effect of a cured product having excellent light absorptivity over time and curability. Particularly preferably, it is a compound obtained by directly bonding 1 or more glycidyl ether groups to the polycyclic aliphatic structure, and most preferably a compound obtained by directly bonding 2 or more glycidyl ether groups to the polycyclic aliphatic structure. This is because such a compound easily obtains a cured product having excellent light absorptivity over time, and is also easy to obtain.
[0119] As the epoxy compound (A) having a polycyclic aliphatic structure, a compound not having a cycloalkyl epoxy group is preferred from the aspect of easily obtaining a composition with an excellent balance between the effect of a cured product having excellent light absorptivity over time and curability. It should be noted that the cycloalkyl epoxy group can be set in the same manner as described in the item of “(2) Alicyclic epoxy compound (B)” described later.
[0120] The epoxy compound (A) having a polycyclic aliphatic structure is further preferably an aliphatic epoxy compound having a polycyclic aliphatic structure from the viewpoint of the balance between the effect of a cured product having excellent light absorptivity over time and curability. In this specification, an aliphatic epoxy compound refers to an epoxy compound having an aliphatic group but not having an aromatic group and not having a cycloalkyl epoxy group. It should be noted that the reason why a cured product having excellent light absorptivity over time and an excellent balance of curability can be obtained by the epoxy compound (A) being an aliphatic epoxy compound and a cured product having excellent light absorptivity in a desired wavelength region can be more easily obtained is not clear, but it is presumed that because it does not have an aromatic group, stacking between aromatic groups can be effectively suppressed, and curing shrinkage and the like can be more effectively suppressed.
[0121] The preferred constitution of the epoxy compound (A) having a polycyclic aliphatic structure will be described more specifically below.
[0122] From the viewpoint of achieving a composition that provides a cured product with excellent light absorbency and excellent balance between the effects of long-term stability and curability, the epoxy compound (A) having a polycyclic aliphatic structure is preferably represented by the following formula (II) or formula (III), and more preferably by formula (II).
[0123] [Chemical formula 5]
[0124]
[0125] (R 221 and R 222 are a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent or a divalent group containing a heterocycle having 2 to 30 carbon atoms which may have a substituent, or a group obtained by substituting a methylene group in the divalent hydrocarbon group or the divalent group having 2 to 30 carbon atoms with a divalent group selected from the above Group I under the condition that oxygen atoms are not adjacent to each other.)
[0126] R 221 and R 222 may be the same as or different from each other.)
[0127] [Chemical formula 5A]
[0128]
[0129] (R 223 and R 224 are a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent or a group containing a heterocycle having 2 to 30 carbon atoms which may have a substituent, or a group obtained by substituting a methylene group in the hydrocarbon group or the group having 2 to 30 carbon atoms with a divalent group selected from the above Group I under the condition that oxygen atoms are not adjacent to each other.)
[0130] R 223 and R 224 (H) may be the same as or different from each other. R 224 In the case where there are a plurality of them, they may be the same as or different from each other. m1 is an integer of 1 or more.)
[0131] As R 221 , R 222 , R 223 and R 224The hydrocarbon group having 1 to 30 carbon atoms which may sometimes have substituents and the group having 2 to 30 carbon atoms containing a heterocycle which may sometimes have substituents can be respectively exemplified by the hydrocarbon group having 1 to 30 carbon atoms which may sometimes have substituents listed as the group for substituting a hydrogen atom on the ring of a polycyclic aliphatic structure and the group having 2 to 30 carbon atoms containing a heterocycle which may sometimes have substituents obtained by removing a specified number (R 221 ~R 223 is one, R 224 is two) of hydrogen atoms from the groups listed above. For example, as examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R 221 , R 222 , R 223 and R 224 , the straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, the alkenyl group having 2 to 30 carbon atoms, the cycloalkyl group having 3 to 30 carbon atoms, the cycloalkylalkyl group having 4 to 30 carbon atoms and other aliphatic hydrocarbon groups, the aryl group having 6 to 30 carbon atoms, the arylalkyl group having 7 to 30 carbon atoms and other aromatic hydrocarbon groups listed above as the group for substituting a hydrogen atom on the ring of a polycyclic aliphatic structure can be respectively exemplified by the groups obtained by removing a specified number (R 221 ~R 223 is one, R 222 is two) of hydrogen atoms from these groups. In addition, as substituents in these groups, the groups listed above as the substituents of hydrogen atoms in the group for substituting a hydrogen atom on the ring of a polycyclic aliphatic structure can be exemplified.
[0132] R 221 and R 222 The hydrocarbon group having 1 to 30 carbon atoms which may sometimes have substituents is preferably a group having 1 to 20 carbon atoms, and among them, a group having 1 to 10 carbon atoms is preferred.
[0133] In addition, R 221 , R 222 , R 223 and R 224 The hydrocarbon group having 1 to 30 carbon atoms which may sometimes have substituents is preferably an unsubstituted group.
[0134] As a particularly preferred example of the aliphatic epoxide, i.e., the above-mentioned epoxide (A), the epoxide represented by the above formula (II) can be exemplified, in which R 221 and R 222A compound having a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms that may have a substituent, or a group obtained by substituting a methylene group in the divalent aliphatic hydrocarbon group with a divalent group selected from Group I above under the condition that oxygen atoms are not adjacent. More preferably, in the epoxy compound represented by the above formula (II), R 221 and R 222 are a sometimes-substituted alkylene group with 1 to 10 carbon atoms, a sometimes-substituted alkenylene group with 2 to 10 carbon atoms, or a group obtained by substituting a methylene group in the divalent alkylene group or alkenylene group with a divalent group selected from Group I above under the condition that oxygen atoms are not adjacent. More preferably, in the epoxy compound represented by the above formula (II), R 221 and R 222 are a sometimes-substituted alkylene group with 1 to 10 carbon atoms or a group obtained by substituting a methylene group in the alkylene group with a divalent group selected from Group I above under the condition that oxygen atoms are not adjacent. Particularly preferably, in the epoxy compound represented by the above formula (II), R 221 and R 222 are a non-substituted alkylene group with 1 to 10 carbon atoms. Most preferably, in the epoxy compound represented by the above formula (II), R 221 and R 222 are a non-substituted alkylene group with 1 to 6 carbon atoms. By using these compounds, there are the following advantages: a cured product with particularly excellent light absorbency in a desired wavelength region can be manufactured. In addition, a composition with an excellent balance between the effect of obtaining a cured product with excellent light absorbency over time and curability is achieved, and a cured product with less dye bleeding is easily formed.
[0135] As a preferred example of the aromatic epoxy compound, i.e., the above epoxy compound (A), in the epoxy compound represented by the above formula (III), R 223 and R 224 are groups obtained by removing a specified number (R 223 is 1, R 224 is 2) of hydrogen atoms from an aryl group with 6 to 30 (especially 6 to 10) carbon atoms that may have a substituent. The molecular weight of the epoxy compound represented by the above formula (III) is preferably 300 or more and 2,000 or less, more preferably 400 or more and 1,000 or less. There are the following advantages: a cured product with particularly excellent light absorbency in a desired wavelength region can be manufactured. In addition, a composition with an excellent balance between the effect of obtaining a cured product with excellent light absorbency over time and curability is achieved, and a cured product with less dye bleeding is easily formed.
[0136] The epoxy equivalent of the epoxy compound (A) having a polycyclic aliphatic structure is preferably 30 or more and 500 or less, more preferably 50 or more and 300 or less, and still more preferably 70 or more and 250 or less. This is because the above composition becomes a composition having an excellent balance between the effect of obtaining a cured product having excellent temporal stability of light absorption and curability. It should be noted that as a method for measuring the epoxy equivalent, for example, it can be measured by a method based on JIS K 7236:2001 (Method for Determining the Epoxy Equivalent of Epoxy Resins).
[0137] The content of the epoxy compound (A) having a polycyclic aliphatic structure is preferably 20 parts by mass or more and 70 parts by mass or less, more preferably 25 parts by mass or more and 60 parts by mass or less, particularly preferably 30 parts by mass or more and 50 parts by mass or less, and particularly preferably 35 parts by mass or more and 45 parts by mass or less in 100 parts by mass of the cationic polymerizable component. This is because when the content is within the above range, the above composition can easily obtain a cured product having excellent temporal stability of light absorption. In addition, because a cured product having good adhesion to the substrate can be obtained. In addition, because the above composition can obtain a cured product having a steeper absorption peak in the desired wavelength range.
[0138] In addition, in this specification, unless otherwise specified, the content is based on mass.
[0139] The content of the epoxy compound (A) having a polycyclic aliphatic structure is preferably 20 parts by mass or more and 70 parts by mass or less, more preferably 25 parts by mass or more and 60 parts by mass or less, particularly preferably 30 parts by mass or more and 50 parts by mass or less in 100 parts by mass of the total of the epoxy compound (A) having a polycyclic aliphatic structure and the alicyclic epoxy compound (B). This is because when the content is within the above range, the above composition can obtain a cured product having excellent temporal stability of light absorption, and can obtain a cured product having excellent light absorption in the desired wavelength region and good adhesion to the substrate.
[0140] (2) Alicyclic epoxy compound (B)
[0141] The alicyclic epoxy compound (B) is a compound containing one or more epoxy cycloalkyl groups. From the aspect of easily obtaining a cured product with excellent light absorption stability over time and excellent light absorption in the desired wavelength region, the alicyclic epoxy compound (B) preferably has two or more epoxy cycloalkyl groups. In the present invention, the alicyclic epoxy compound (B) does not have a polycyclic aliphatic structure. It should be noted that an epoxy compound containing an aromatic ring and having an epoxy cycloalkyl group can be defined as an alicyclic epoxy compound. As an example of the alicyclic epoxy compound (B), a compound having an epoxycyclohexane structure or an epoxycyclopentane structure obtained by epoxidizing a compound containing a cyclohexene ring or a cyclopentene ring with an oxidizing agent can be cited. Among alicyclic epoxy compounds, an epoxy resin having an epoxycyclohexane structure cures quickly and is preferred.
[0142] As the above alicyclic epoxy compound (B), a compound having two or more epoxycyclohexane structures such as the compound represented by the following formula (1) can be preferably used. This is because by including such a compound, the composition of the present invention becomes a composition having an excellent balance between the effect of obtaining a cured product with excellent light absorption stability over time and curability. In addition, because a cured product with good adhesion to the substrate can be obtained. In addition, because the above composition can obtain a cured product having a steeper absorption peak in the desired wavelength range.
[0143] [Chemical formula 6]
[0144]
[0145] (In the formula, X 1 represents a direct bond or a divalent linking group having one or more atoms.)
[0146] As the linking group represented by X 1 for example, a divalent hydrocarbon group, a subalkenyl group in which part or all of the carbon-carbon double bonds are epoxidized, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide group, and a group obtained by linking a plurality of them can be cited.
[0147] As the above divalent hydrocarbon group, a straight-chain or branched alkylene group having 1 to 30 carbon atoms, or an alkylene group having a cycloalkyl ring and having 1 to 30 carbon atoms can be cited.
[0148] As the above-mentioned alkylene group having 1 to 30 carbon atoms in the straight chain or branched chain, a group obtained by removing one hydrogen atom from an alkyl group having 1 to 30 carbon atoms in the straight chain or branched chain can be used. As the alkyl group having 1 to 30 carbon atoms in the straight chain or branched chain, the alkyl groups having 1 to 30 carbon atoms that can substitute the hydrogen atoms on the ring of the polycyclic aliphatic structure are the groups exemplified above. For example, if it is an alkylene group having 1 to 6 carbon atoms, as an example of the alkylene group represented by the above Z, the groups exemplified above can be cited.
[0149] As the above-mentioned alkylene group having 1 to 30 carbon atoms having a cycloalkyl ring, a group obtained by removing one hydrogen atom from an alkyl group having 1 to 30 carbon atoms having a cycloalkyl ring can be used. As the above-mentioned alkyl group having a cycloalkyl ring, an alkyl group having no polycyclic aliphatic structure can be cited from the groups obtained by removing one hydrogen atom from a cycloalkyl group having 3 to 30 carbon atoms and a cycloalkylalkyl group having 4 to 30 carbon atoms that can substitute the hydrogen atoms on the ring of the polycyclic aliphatic structure, respectively. For example, cycloalkylene groups (including cycloalkylidene groups) such as 1,2-cyclopentylene, 1,3-cyclopentylene, cyclopentylidene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, cyclohexylidene, etc. can be cited.
[0150] As the alkenylene group in the above-mentioned alkenylene group in which part or all of the carbon-carbon double bonds are epoxidized (hereinafter sometimes referred to as "epoxidized alkenylene group"), a group obtained by removing one hydrogen atom from an alkenyl group having 2 to 30 carbon atoms that can substitute the hydrogen atoms on the ring of the above-mentioned polycyclic aliphatic structure can be cited. For example, straight-chain or branched-chain alkenylene groups having 2 to 8 carbon atoms such as vinylidene, propenylene, 1-butenylene, 2-butenylene, butadienylene, pentenylene, hexenylene, heptenylene, octenylene, etc. can be cited.
[0151] In the present invention, X 1 is preferably a linking group, preferably a divalent hydrocarbon group, an ester bond, or a group obtained by connecting them, and particularly preferably a group obtained by connecting a divalent hydrocarbon group and an ester bond. This is because by using such a compound, a composition having an excellent balance between the effect of obtaining a cured product having excellent temporal stability of light absorption and curability can be obtained.
[0152] In addition, in the present invention, X 1The divalent hydrocarbon group used is preferably an alkylene group obtained by removing one hydrogen atom from a linear or branched alkyl group having 1 to 18 carbon atoms, more preferably an alkylene group obtained by removing one hydrogen atom from a linear or branched alkyl group having 1 to 8 carbon atoms, still more preferably an alkylene group obtained by removing one hydrogen atom from a linear alkyl group having 1 to 5 carbon atoms, and particularly preferably an alkylene group obtained by removing one hydrogen atom from a linear alkyl group having 1 to 3 carbon atoms. This is because when the number of carbon atoms is within the above range, the effect of obtaining a cured product with excellent temporal stability of light absorption can be better exerted. In X 1 In the linking group represented by, the divalent hydrocarbon group may contain one or more, and the ester bond may contain one or more.
[0153] Examples of the alicyclic epoxy compound (B) include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-m-dioxane, bis(3,4-epoxycyclohexylmethyl)adipate, 3,4-epoxy-6-methylcyclohexanecarboxylate, methylenebis(3,4-epoxycyclohexane), dicyclopentadiene diepoxide, ethylenebis(3,4-epoxycyclohexanecarboxylate), dioctyl epoxyhexahydrophthalate, bis(2-ethylhexyl) epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, 3,4-epoxycyclohexylmethyl acrylate, 3,4-epoxycyclohexylmethyl methacrylate, etc.
[0154] The content of the alicyclic epoxy compound (B) is preferably 20 parts by mass or more and 70 parts by mass or less, more preferably 30 parts by mass or more and 60 parts by mass or less, and particularly preferably 35 parts by mass or more and 55 parts by mass or less in 100 parts by mass of the cationic polymerizable component. This is because when the content is within the above range, the above composition becomes a composition having an excellent balance between the effect of obtaining a cured product with excellent temporal stability of light absorption and curability. In addition, because a cured product having excellent light absorption in a desired wavelength region and good adhesion to a substrate can be obtained. In addition, because the above composition can obtain a cured product having a steeper absorption peak in a desired wavelength range.
[0155] (3) Other cationic polymerizable components
[0156] In addition to the components (A) and (B), it is preferable to contain other cationically polymerizable components in the present invention in terms of more easily obtaining a cured product with excellent temporal stability of light absorption and in terms of obtaining a cured product with good adhesion to a substrate when forming a cured product of the cationically polymerizable component on the substrate. As other cationically polymerizable components, for example, epoxy compounds, oxetane compounds, cyclic lactone compounds, cyclic acetal compounds, cyclic thioether compounds, spiro orthoester compounds, vinyl compounds, etc. other than the components (A) and (B) can be used, and one or more selected from them can be used.
[0157] It should be noted that, for example, substances that have a cationically polymerizable group such as an epoxy group but are classified as a dye or an acid generator are respectively set as substances classified as a dye or an acid generator and are not included in the cationically polymerizable components.
[0158] As the epoxy compound other than the components (A) and (B), an aliphatic epoxy compound (C1) without a polycyclic aliphatic structure or an aromatic epoxy compound (C2) without a polycyclic aliphatic structure can be cited.
[0159] In the present invention, as the above-mentioned other cationically polymerizable components, in terms of more easily obtaining a cured product with excellent temporal stability of light absorption and in terms of obtaining a cured product with good adhesion to a substrate when forming a cured product of the cationically polymerizable component on the substrate, it is preferable to contain an aliphatic epoxy compound without a polycyclic aliphatic structure. That is, the above-mentioned cationically polymerizable components preferably further contain an aliphatic epoxy compound without a polycyclic aliphatic structure.
[0160] Specific examples of the aliphatic epoxy compound (C1) without a polycyclic aliphatic structure include polyglycidyl ethers of aliphatic polyols or their alkylene oxide adducts, polyglycidyl esters of aliphatic long-chain polyacids, homopolymers synthesized by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate, copolymers synthesized by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate and other vinyl monomers, etc.
[0161] Among the aliphatic epoxy compounds (C1) without a polycyclic aliphatic structure, it is preferable to use an aliphatic epoxy compound containing a monocyclic aliphatic ring, and it is more preferable to use a compound in which an epoxy group is directly bonded to the monocyclic aliphatic ring, and it is most preferable to use the compound of formula (2). This is because by using the above-mentioned compound, the above-mentioned composition can obtain a cured product with excellent temporal stability of light absorption and good adhesion to the substrate. In addition, because the above-mentioned composition can obtain a cured product having a steeper absorption peak in the desired wavelength range.
[0162] [Chemical Formula 7]
[0163]
[0164] (In the formula, R 1 is a group obtained by removing p hydroxyl groups (-OH) from a p-valent alcohol, and p and q each represent an integer of 1 or more.)
[0165] When p is 2 or more, the p structural units q may be the same or different.)
[0166] In formula (2), the group obtained by removing p hydroxyl groups (-OH) from the p-valent alcohol represented by R 1 is an aliphatic hydrocarbon group. As the group obtained by removing p hydroxyl groups (-OH) from the p-valent alcohol represented by R 1 , from the viewpoints of ease of acquisition and the ability to obtain a cured product with good adhesion to the substrate, an aliphatic hydrocarbon group having 1 to 30 carbon atoms is preferably exemplified. As the aliphatic hydrocarbon group having 1 to 30 carbon atoms, there can be mentioned a group obtained by removing p - 1 hydrogen atoms from each of the alkyl groups having 1 to 30 carbon atoms, alkenyl groups having 2 to 30 carbon atoms, cycloalkyl groups having 3 to 30 carbon atoms, or cycloalkylalkyl groups having 4 to 30 carbon atoms, which are substituents for hydrogen atoms on the ring of a polycyclic aliphatic structure that can be substituted, or groups obtained by substituting methylene groups of these groups with divalent groups selected from the above Group I under the condition that oxygen atoms are not adjacent. From the viewpoints of ease of acquisition and the ability to obtain a cured product with good adhesion to the substrate, the group obtained by removing p hydroxyl groups (-OH) from the p-valent alcohol represented by R 1 is preferably an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and more specifically, preferably a group obtained by removing p - 1 hydrogen atoms from an alkyl group having 2 to 15 carbon atoms, an alkenyl group having 3 to 15 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or a cycloalkylalkyl group having 4 to 15 carbon atoms, or a group obtained by substituting methylene groups of these groups with divalent groups selected from the above Group I. Especially from the viewpoints of ease of acquisition and the ability to obtain a cured product having excellent temporal stability of light absorption and good adhesion to the substrate, an alkyl group having 2 to 10 carbon atoms or a group obtained by substituting methylene groups in the alkyl group with divalent groups selected from the above Group I is preferred, and an alkyl group having 2 to 10 carbon atoms is particularly preferred, and a branched alkyl group having 3 to 8 carbon atoms is most preferred.)
[0167] The compound of formula (2) is obtained from the viewpoints that it can be obtained as an adduct of 1,2-epoxy-4-(2-epoxyethyl)cyclohexane, ease of acquisition, the ability to obtain a cured product having excellent temporal stability of light absorption, and good adhesion to the substrate, and as a means for providing R 1Examples of the p-valent alcohol include dihydric alcohols such as ethylene glycol, propylene glycol, 1,4-butanediol, 1,2-butanediol, neopentyl glycol, 1,6-hexanediol, 1,2-octanediol, 1,8-octanediol, isopentyl glycol, 3-methyl-1,5-pentanediol, 1,4-cyclohexanedimethanol, sorbitol, hydrogenated bisphenol A, hydrogenated bisphenol F, and dimer diol; trihydric alcohols such as glycerol, trihydroxyisobutane, 1,2,3-butanetriol, 1,2,3-pentanetriol, 2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-1,2,3-butanetriol, 2,3,4-pentanetriol, 2,3,4-hexanetriol, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4-pentanetriol, pentamethylglycerol, 1,2,4-butanetriol, 1,2,4-pentanetriol, trimethylolethane, and 2,2-bis(hydroxymethyl)-1-butanol (trimethylolpropane); tetrahydric alcohols such as pentaerythritol, diglycerol, 1,2,3,4-pentanetetrol, 2,3,4,5-hexanetetrol, 1,2,4,5-pentanetetrol, and 1,3,4,5-hexanetetrol; pentahydric alcohols such as triglycerol, adonitol, arabitol, and xylitol; hexahydric alcohols such as dipentaerythritol, sorbitol, mannitol, and iditol; and octahydric alcohols such as sucrose.
[0168] The integer p is preferably 1 or more and 10 or less, more preferably 2 or more and 8 or less, and still more preferably 3 or more and 6 or less, in view of the ease of obtaining the compound. The integer q is preferably 1 or more and 30 or less.
[0169] In particular, from the aspects of the ease of obtaining the compound, the excellent temporal stability of the light absorbency, and the good adhesion to the substrate of the cured product, as the compound of formula (2), preferred examples include the 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol, etc., which have a structure in which an oxiranyl group is directly bonded via a single bond to the cycloalkyl ring derived from the epoxycycloalkyl ring as a structural unit and a structure in which the epoxy groups of the epoxycycloalkyl ring are polymerized with each other as the main chain structure.
[0170] Regarding the molecular weight of the compound represented by the above formula (2), any molecular weight can be used as long as it can form a cured product with excellent light absorption stability over time. Preferably, it is more than 1,000 and 5,000 or less, more preferably 1,500 or more and 4,000 or less, and particularly preferably 2,000 or more and 3,000 or less. This is because when the molecular weight is within the above range, the above composition can obtain a cured product with excellent light absorption stability over time and good adhesion to the substrate. It should be noted that when the compound represented by formula (2) has a part formed by polymerization of monomers or oligomers, the above molecular weight can be set as the weight average molecular weight. In addition, the measurement of such a weight average molecular weight can use the measurement conditions of the weight average molecular weight (Mw) when the compound described later is a polymer.
[0171] Regarding the epoxy equivalent of the compound represented by the above formula (2), any epoxy equivalent can be used as long as it can form a cured product with excellent light absorption stability over time. Preferably, it is 100 or more and 500 or less, and more preferably 150 or more and 200 or less. This is because when the epoxy equivalent is within the above range, the above composition can obtain a cured product with excellent light absorption stability over time and better adhesion to the substrate.
[0172] As the aliphatic epoxy compound containing a monocyclic aliphatic ring, the compound represented by the following formula (3) can also be cited.
[0173] [Chemical formula 8]
[0174]
[0175] (In the formula, Y 1 represents an alkylene group having a cycloalkyl ring and having 6 to 30 carbon atoms.)
[0176] As the alkylene group having a cycloalkyl ring and having 1 to 30 carbon atoms represented by Y 1 , the same groups as those listed above for the alkylene group having a cycloalkyl ring represented by the above X 1 can be used. More specifically, it can be an alkylene group having 2 cycloalkyl rings and having 13 to 20 carbon atoms. For example, the group represented by the following formula (4) can be cited.
[0177] [Chemical formula 9]
[0178]
[0179] (In the formula, R 5a and R 5b represent a hydrogen atom or a methyl group, and * represents the bonding site.)
[0180] In addition, as the aliphatic epoxy compound (C1) that does not have a polycyclic aliphatic structure, as the polyglycidyl ether of an aliphatic polyol or its alkylene oxide adduct, the diglycidyl ether of an aliphatic diol compound can be preferably used, and the compound represented by the following formula (5) can be particularly preferably used. This is because by using the above compound, the above composition easily forms a cured product with excellent temporal stability of light absorption.
[0181] [Chemical Formula 10]
[0182]
[0183] (In the formula, Y 2 represents a linear or branched alkylene group having 1 to 30 carbon atoms or a group obtained by substituting one or more methylene groups in the alkylene group with -O- under the condition that oxygen atoms are not adjacent.)
[0184] As the linear or branched alkylene group having 1 to 30 carbon atoms represented by Y 2 , the same group as the linear or branched alkylene group having 1 to 30 carbon atoms used in the above X 1 can be used. In addition, in the group represented by Y 2 , one or more methylene groups of the alkylene group having 1 to 30 carbon atoms can also be substituted with -O-. That is, the group represented by Y 2 can also be a group obtained by substituting one or more methylene groups in the linear or branched alkylene group having 1 to 30 carbon atoms with -O-.
[0185] It should be noted that when the methylene group in the above alkylene group is substituted with -O-, it is substituted with -O- under the condition that oxygen atoms are not adjacent in the above alkylene group.
[0186] In the present invention, Y 2 is preferably a branched alkylene group or a group obtained by substituting the methylene group in the alkylene group with -O-. This is because by having the above structure, the above composition easily forms a cured product with excellent temporal stability of light absorption and can obtain the above cured product with easy adjustment of light absorption.
[0187] In the present invention, Y 2 is preferably a linear or branched alkylene group having 2 to 30 carbon atoms or a group obtained by substituting the methylene group in the alkylene group with -O-, more preferably a linear or branched alkylene group having 3 to 28 carbon atoms or a group obtained by substituting the methylene group in the alkylene group with -O-, and particularly preferably a linear or branched alkylene group having 4 to 26 carbon atoms or a group obtained by substituting the methylene group in the alkylene group with -O-. In addition, in Y 2When it is an alkylene group in which the methylene group is not substituted with -O-, the number of carbon atoms is preferably 4 to 10, more preferably 4 to 8. The above Y 2 When Y is a group obtained by substituting the methylene group in the alkylene group with -O-, Y 2 is preferably a group having 10 to 26 carbon atoms and having a structure obtained by removing the hydroxyl groups at both ends from a polyalkylene glycol, and among them, preferably a group having 10 to 26 carbon atoms and having a structure obtained by removing the hydroxyl groups at both ends from polyethylene glycol or polypropylene glycol, and more preferably a group having 15 to 24 carbon atoms and having a structure obtained by removing the hydroxyl groups at both ends from polyethylene glycol or polypropylene glycol. This is because the above composition can obtain a cured product that is easily formed and has excellent temporal stability of light absorption.
[0188] Specific examples of the diglycidyl ether compound of the aliphatic diol compound represented by the above formula (3) or formula (5) include diglycidyl ethers of polyalkylene glycols such as diethylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, and tripropylene glycol diglycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, diglycidyl ethers of polyether polyols obtained by adding an alkylene oxide to (poly)alkylene glycols, cyclohexane dimethanol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,9-nonanediol diglycidyl ether, etc.
[0189] In addition, among the aliphatic epoxy compounds (C1) that do not have the above polycyclic aliphatic structure, representative aliphatic epoxy compounds include glycidyl ethers of polyols such as triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane, tetraglycidyl ether of sorbitol, hexaglycidyl ether of dipentaerythritol, polyglycidyl ethers of polyether polyols obtained by adding one or more alkylene oxides to aliphatic polyols such as trimethylolpropane and glycerin, and diglycidyl esters of aliphatic long-chain dibasic acids. Further, monoglycidyl ethers of aliphatic higher alcohols, glycidyl esters of higher fatty acids, epoxidized soybean oil, octyl epoxystearate, butyl epoxystearate, epoxidized polybutadiene, etc. can be cited.
[0190] It should be noted that the aliphatic epoxy resin can be set as an aliphatic epoxy resin that does not contain an epoxy cycloalkyl group and an aromatic ring.
[0191] When the composition of the present invention contains an aliphatic epoxy compound (C1) having no polycyclic aliphatic structure, from the aspect of the cured product which is easily formed into a light absorbent and has excellent temporal stability brought about by the aliphatic epoxy compound (C1) having no polycyclic aliphatic structure, the amount of the aliphatic epoxy compound (C1) having no polycyclic aliphatic structure in the cationic polymerizable component is preferably 1 part by mass or more and 45 parts by mass or less, more preferably 3 parts by mass or more and 40 parts by mass or less, and particularly preferably 5 parts by mass or more and 30 parts by mass or less. The amount of the aliphatic epoxy compound (C1) having no polycyclic aliphatic structure may also be 0 part by mass.
[0192] Furthermore, when the composition of the present invention contains an aliphatic epoxy compound having a monocyclic aliphatic ring as the above (C1), from the aspect of obtaining the above advantages brought about by the aliphatic epoxy compound having a monocyclic aliphatic ring and the aspect of the cured product which is easily formed into a light absorbent and has excellent temporal stability, the amount of the aliphatic epoxy compound having a monocyclic aliphatic ring in the cationic polymerizable component is preferably 0.5 part by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, and particularly preferably 4 part by mass or more and 15 parts by mass or less. The amount of the aliphatic epoxy compound having a monocyclic aliphatic ring may also be 0 part by mass.
[0193] Furthermore, when the composition of the present invention contains an aliphatic epoxy compound having no aliphatic ring as the above (C1), from the aspect of obtaining the above advantages brought about by the compound and the aspect of the cured product which is easily formed into a light absorbent and has excellent temporal stability, the amount of the aliphatic epoxy compound having no aliphatic ring in the cationic polymerizable component is preferably 0.5 part by mass or more and 40 parts by mass or less, more preferably 1 part by mass or more and 30 parts by mass or less, and particularly preferably 3 part by mass or more and 25 parts by mass or less. The amount of the aliphatic epoxy compound having no aliphatic ring may also be 0 part by mass.
[0194] As specific examples of the aromatic epoxy compound (C2) not having the above polycyclic aliphatic structure, there can be mentioned monofunctional phenols having at least 1 aromatic ring such as phenol, cresol, tert-butylphenol, polyhydric phenols, or polyglycidyl ethers of their alkylene oxide adducts. As the polyglycidyl ethers of polyhydric phenols or their alkylene oxide adducts, for example, there can be mentioned glycidyl ether compounds of bisphenol A, bisphenol F, or compounds obtained by further adding alkylene oxide thereto, phenol novolak type epoxy compounds; glycidyl ethers of aromatic compounds having 2 or more phenolic hydroxyl groups such as resorcinol, hydroquinone, catechol. As specific examples of other compounds (C2), there can be mentioned polyglycidyl ether compounds of aromatic compounds having 2 or more alcoholic hydroxyl groups such as benzenedimethanol or benzenediethanol, benzenedibutanol; polyglycidyl esters of polybasic acid aromatic compounds having 2 or more carboxylic acids such as phthalic acid, terephthalic acid, trimellitic acid, polyglycidyl esters of benzoic acid such as benzoic acid, toluic acid, naphthoic acid, glycidyl ester of benzoic acid, epoxides of styrene oxide or divinylbenzene, etc.
[0195] Among them, the aromatic epoxy compound (C2) is preferably a monofunctional aromatic epoxy compound having 1 epoxy group such as glycidyl ether of monofunctional phenols, and particularly preferably glycidyl ether of monofunctional phenols. This is because it becomes easy to form a cured product with excellent light absorption and excellent stability over time. In addition, since the viscosity can be easily adjusted, it is easy to prepare a composition with excellent coatability.
[0196] The content of the aromatic epoxy compound not having the above polycyclic aliphatic structure may be an amount that can obtain a cured product with excellent light absorption and excellent stability over time. However, for example, in the case of containing an aromatic epoxy compound, it can be set to 0.5 parts by mass or more and 20 parts by mass or less in 100 parts by mass of the above cationic polymerizable component, and preferably 1 part by mass or more and 20 parts by mass or less. This is because when the content is within the above range, the above composition becomes easy to form a cured product with excellent light absorption and excellent stability over time, and it becomes easy to prepare a composition with excellent coatability. The amount of the aromatic epoxy compound not having the above polycyclic aliphatic structure may also be 0 parts by mass.
[0197] As the above oxetane compound, a compound having an oxetane structure and not containing an epoxy structure can be set.
[0198] As specific examples of such oxetane compounds, for example, the compounds described in Japanese Patent No. 6103653 can be mentioned.
[0199] As the above cationic polymerizable component, other compounds such as episulfide compounds and sulfidocyclopropane compounds can be used.
[0200] Regarding other compounds that can be used as such cationically polymerizable components, cyclic lactone compounds, cyclic acetal compounds, cyclic thioether compounds, spiro orthoester compounds, and vinyl compounds such as vinyl ether compounds and ethylenically unsaturated compounds, they can be set to be the same as those described in Japanese Patent No. 6103653 and the like.
[0201] (4) Others
[0202] In the present invention, the total content of the epoxy compound (A) having a polycyclic aliphatic structure and the alicyclic epoxy compound (B) is preferably 40 parts by mass or more, preferably 50 parts by mass or more, more preferably 60 parts by mass or more, and particularly preferably 70 parts by mass or more in 100 parts by mass of the cationically polymerizable component. This is because a cured product having excellent temporal stability of light absorption and good adhesion to a substrate can be obtained. In addition, a cured product having a steeper absorption peak in a desired wavelength range can be obtained. In the present invention, the total content of the epoxy compound (A) having a polycyclic aliphatic structure and the alicyclic epoxy compound (B) is preferably 99 parts by mass or less, preferably 98 parts by mass or less, and preferably 95 parts by mass or less in 100 parts by mass of the cationically polymerizable component. It is preferable that the content is below these upper limits in terms of facilitating the formation of a cured product having excellent temporal stability of light absorption.
[0203] The cationically polymerizable component in the present invention may be any component that can obtain a cured product having excellent temporal stability of light absorption, and for example, either a low molecular weight compound or a high molecular weight compound can be used.
[0204] From the viewpoints such as the coatability of the composition, the above cationically polymerizable component preferably contains a low molecular weight compound. In addition, since the dispersibility or solubility of the low molecular weight compound in the composition is excellent, a cured product having excellent transparency can be obtained.
[0205] Regarding the molecular weight of the above low molecular weight compound, as long as it is a molecular weight that can obtain a desired coatability or the like, it can be set to 1,000 or less, preferably 50 or more and 500 or less, and preferably 50 or more and 300 or less.
[0206] It should be noted that hereinafter, when the compound is a polymer, the molecular weight represents the weight average molecular weight (Mw).
[0207] In addition, the weight average molecular weight can be determined by gel permeation chromatography (GPC) as a standard polystyrene conversion value.
[0208] The weight-average molecular weight Mw can be obtained, for example, by using GPC (LC-2000plus series) manufactured by JASCO Corporation, setting the elution solvent to tetrahydrofuran, setting the calibration curve with polystyrene standards to Mw 1110000, 707000, 397000, 189000, 98900, 37200, 13700, 9490, 5430, 3120, 1010, 589 (TSKgel standard polystyrene manufactured by Tosoh Corporation), and setting the measurement columns to KF-804, KF-803, KF-802 (manufactured by Showa Denko K.K.) for measurement.
[0209] In addition, the measurement temperature can be set to 40 °C, and the flow rate can be set to 1.0 mL / minute.
[0210] As the sample concentration during measurement, it can be set to 0.1 mass% to 0.2 mass%.
[0211] The content of the above-mentioned low-molecular-weight compound only needs to be the content that can obtain a cured product with excellent temporal stability of light absorbency. For example, in 100 parts by mass of the cationic polymerizable component, it is preferably 10 parts by mass or more, more preferably 30 parts by mass or more, particularly more preferably 50 parts by mass or more, and particularly preferably 60 parts by mass or more and 99 parts by mass or less. This is because when the content is within the above range, the above composition easily forms a cured product with excellent temporal stability of light absorbency.
[0212] The content of the above-mentioned cationic polymerizable component in the composition of the present invention is not a problem as long as it is an amount that can obtain a cured product with excellent temporal stability of light absorbency. For example, in 100 parts by mass of the solid content of the above composition, it can be set to 50 parts by mass or more, preferably 50 parts by mass or more and 99 parts by mass or less, more preferably 70 parts by mass or more and 96 parts by mass or less, and more preferably 85 parts by mass or more and 95 parts by mass or less. This is because when the content is within the above range, the above composition easily forms a cured product with excellent temporal stability of light absorbency.
[0213] It should be noted that the solid content includes all components except the solvent.
[0214] 2. Dye
[0215] The dyes in the present invention are preferably cationic dyes in terms of effectively obtaining the effect of being able to produce a cured product with excellent long-term stability of light absorption, and having excellent light transmittance in wavelength regions other than the specified wavelength region, and being suitable for use in optical filters. As the cationic dye, any dye that can obtain a cured product with excellent long-term stability of light absorption can be used. For example, cyanine dyes, merocyanine dyes, pyrromethene dyes, azo dyes, tetraazaporphyrin dyes, xanthene dyes, triarylmethane dyes, etc. can be cited. As the above dyes, for example, from the viewpoint of an optical filter for reducing the overlap between the visible lights of two colors, etc., a dye that can absorb light in the wavelength range where the emission spectra of two colors overlap is preferably used.
[0216] In the present invention, the above dye preferably contains at least one of a pyrromethene dye and a tetraazaporphyrin dye. This is because these dyes are easily modified in the presence of moisture or the like, and can effectively exhibit the effect of being able to obtain a cured product with excellent long-term stability of light absorption.
[0217] In addition, in the present invention, from the aspect of being easily used for an optical filter for reducing the overlap between blue light and green light and improving color purity, at least one of dyes having a maximum absorption wavelength of 450 nm or more and less than 550 nm is preferably used. In the present invention, as the dye having a maximum absorption wavelength of 450 nm or more and less than 550 nm, a pyrromethene dye is preferably used. In addition, in the present invention, from the viewpoint of being easily used for an optical filter for reducing the overlap between green light and red light and improving color purity, at least one of dyes having a maximum absorption wavelength of 550 nm or more and 610 nm or less is preferably used. As the dye having a maximum absorption wavelength of 550 nm or more and 610 nm or less, a tetraazaporphyrin dye is preferably used. For the above reasons, in the present invention, as the dye, at least one of a pyrromethene dye and a tetraazaporphyrin dye is also preferably contained, and particularly preferably both dyes are contained.
[0218] There is no problem with the method for measuring the above maximum absorption wavelength as long as it can accurately measure the maximum absorption wavelength. For example, the following method can be used.
[0219] (1) Dissolve the dye in a solvent to prepare a dye solution.
[0220] (2) Fill the dye solution into a quartz cell (optical path length: 10 mm, thickness: 1.25 mm), and use a spectrophotometer (for example, visible ultraviolet spectrophotometer V-670 manufactured by JASCO Corporation, etc.) to measure the transmittance.
[0221] It should be noted that the concentration of the dye solution is not a problem as long as it can accurately confirm the maximum absorption wavelength. For example, it can be adjusted so that the transmittance at the wavelength corresponding to the maximum absorption wavelength is about 5% (for example, 3% or more and 7% or less).
[0222] As the above-mentioned solvent, any solvent that can dissolve the dye, has little displacement of the maximum absorption wavelength, and can accurately measure the transmission spectrum of each dye is acceptable. For example, chloroform can be used. In addition, for dyes that are insoluble in chloroform, other solvents can be used.
[0223] The transmission spectrum of the dye solution uses the spectrum corrected by pre-measuring the transmission spectrum of the solvent monomer and subtracting the transmission spectrum of the solvent from the transmission spectrum of the dye solution.
[0224] In addition, the full width at half maximum refers to the distance between two points on both sides of the peak top showing the maximum absorption wavelength (the distance between the wavelengths at which the half value represented by (100 - transmittance at λmax) / 2 is observed).
[0225] Specifically, when the transmittance at the wavelength λmax corresponding to the maximum absorption wavelength is 4%, the distance between the wavelengths when the transmittance becomes 48% is set as the full width at half maximum.
[0226] When the above-mentioned dye contains two or more dyes, dye solutions are prepared using each dye.
[0227] (1) Pyrromethene dyes
[0228] The above-mentioned pyrromethene dyes are compounds that have a pyrromethene skeleton and can absorb light in the desired wavelength range. For example, the compound represented by formula (2) described in JP-A-2013-109105 can be used.
[0229] As the above-mentioned pyrromethene dyes, from the viewpoints of excellent dispersion stability and easy formation of a cured product having excellent light absorbency in the wavelength region of 450 nm or more and less than 550 nm, a dipyrromethene complex compound obtained by coordinating a compound represented by the following formula (11) with a metal atom or a metal compound can be preferably used.
[0230] [Chemical formula 11]
[0231]
[0232] (In formula (11), R 101 , R 102 , R 103 , R 105 , R 106 and R 107Each independently represents a linear or branched chain alkyl group which may sometimes have substituents, R 104 represents a hydrogen atom, a linear or branched chain alkyl group which may sometimes have substituents, or an aryl group which may sometimes have substituents.)
[0233] As the metal atom or metal compound coordinated with the compound represented by the formula (11), any metal atom or metal compound capable of forming a complex may be used.
[0234] The metal atom also includes metalloids such as boron, silicon, germanium, arsenic, antimony, tellurium, selenium, polonium, and astatine.
[0235] As the metal compound, it is a compound containing a metal atom and atoms other than the metal atom. As such a metal compound, metal halides in which a metal atom is bonded to a halogen atom such as a chlorine atom or a fluorine atom, metal hydroxides in which a metal atom is bonded to a hydroxyl group, metal oxides in which a metal atom is bonded to an oxygen atom, etc. can be cited.
[0236] As the metal atom or metal compound, divalent metal atoms, halides, hydroxides, and oxides of trivalent or tetravalent metals, etc. can be cited. As the metal compound, a metal compound having a valence of 2 as a whole can be used.
[0237] As the above metal atom or metal compound, any metal atom or metal compound capable of forming a complex may be used. For example, Zn, Mg, Si, Sn, Rh, Pt, Pd, Mo, Mn, Pb, Cu, Ni, Co, Fe, Al, In, Fe, Ti, Sn, Si, Ge, B, V, AlCl, InCl, FeCl, TiCl2, SnCl2, SiCl2, GeCl2, BCl2, BF2, TiO, VO, Si(OH)2, etc. can be cited.
[0238] More specifically, as a preferred mode of the dipyrromethine complex compound obtained by coordinating the structure represented by the formula (11) with a metal atom or metal compound, the complex compounds represented by the following formula (11-1) or (11-2) can be cited. This is because by using such a complex compound, a cured product excellent in light absorbency in the wavelength region of 450 nm or more and less than 550 nm can be easily obtained.
[0239] In the present invention, from the viewpoints of excellent dissolution rate at the time of preparing the composition and excellent dispersion stability in the composition, and it being easy to form a composition capable of producing a cured product excellent in light absorbency in a desired wavelength region, the above dipyrromethine complex compound is preferably a pyrromethine complex compound having a dimer structure, and particularly preferably the complex compound represented by the above formula (11-2).
[0240] [Chemical Formula 12]
[0241]
[0242] (In Formula (11-1), R 101 , R 102 , R 103 , R 105 , R 106 and R 107 each independently represent the same meaning as in Formula (11),
[0243] X represents a hydroxyl group, a halogen atom, an alkyl group which may sometimes have a substituent, a phenyl group which may sometimes have a substituent, or an alkoxy group which may sometimes have a substituent.)
[0244] [Chemical Formula 13]
[0245]
[0246] (In Formula (11-2), R 101 , R 102 , R 103 , R 105 , R 106 and R 107 each independently represent the same meaning as in Formula (11),
[0247] M a represents Zn, Mg, Si, Sn, Rh, Pt, Pd, Mo, Mn, Pb, Cu, Ni, Co, Fe, Al, In, Fe, Ti, Sn, Si, Ge, B, or V.)
[0248] As the linear or branched chain alkyl group used for R 101 ~R 103 and R 105 ~R 107 and also for R 104 , linear or branched chain alkyl groups having 1 to 30 carbon atoms can be cited. As specific examples of such chain alkyl groups, the same groups as those cited as the hydrocarbon groups which can substitute the hydrogen atoms on the ring of the polycyclic aliphatic structure in the item of "(1) Epoxy compound (A) having a polycyclic aliphatic structure" of the above "1. Cationic polymerizable component" can be cited.
[0249] As the aryl group used for R 104 , groups having 6 to 30 carbon atoms can be cited. As specific examples of such aryl groups, the aryl groups cited as the hydrocarbon groups which can substitute the hydrogen atoms on the ring of the polycyclic aliphatic structure in the item of "(1) Epoxy compound (A) having a polycyclic aliphatic structure" of the above "1. Cationic polymerizable component" can be cited.
[0250] As the alkoxy group used in X, a group having 1 to 30 carbon atoms with -O- bonded to the terminal end on the bonding site side of an aliphatic hydrocarbon group such as a linear or branched chain alkyl group, a cycloalkyl group, or a cycloalkylalkyl group can be used.
[0251] As the linear or branched chain alkyl group, cycloalkyl group, cycloalkylalkyl group, etc. of the aliphatic hydrocarbon group constituting the alkoxy group used in X, the linear or branched chain alkyl group, cycloalkyl group, cycloalkylalkyl group listed as the hydrocarbon group having 1 to 30 carbon atoms capable of substituting the hydrogen atom on the ring of the polycyclic aliphatic structure in the item of "(1) Epoxy compound (A) having a polycyclic aliphatic structure" of the above "1. Cationic polymerizable component" can be respectively cited.
[0252] As the alkyl group used in X, the linear or branched chain alkyl group, cycloalkyl group, cycloalkylalkyl group listed as the hydrocarbon group having 1 to 30 carbon atoms capable of substituting the hydrogen atom on the ring of the polycyclic aliphatic structure in the item of "(1) Epoxy compound (A) having a polycyclic aliphatic structure" of the above "1. Cationic polymerizable component" can be cited.
[0253] As the substituent that substitutes the hydrogen atoms of R 101 ~R 103 and R 105 ~R 107 、R 104 and the groups used in X, it can be set to be the same as the substituent that substitutes the hydrogen atom in the divalent hydrocarbon group represented by R 221 and R 222 described in the item of "(1) Epoxy compound (A) having a polycyclic aliphatic structure" of the above "1. Cationic polymerizable component".
[0254] As the formula (11), formula (11-1) or (11-2), it is preferable to use one or more complex compounds satisfying the following-described constitution because a cured product having excellent light absorption stability over time can be easily obtained. Any of the following-described preferred constitutions can also be arbitrarily combined in multiple. In addition, since a cured product having excellent light absorption in the wavelength region of 450 nm or more and less than 550 nm can be more easily obtained, it is preferable.
[0255] In the formula (11), formula (11-1) or (11-2), as the linear or branched chain alkyl group represented by R 101 、R 103 、R 105 、R 107 , an alkyl group having 1 to 20 carbon atoms is preferable, an alkyl group having 1 to 15 carbon atoms is more preferable, an alkyl group having 1 to 8 carbon atoms is still more preferable, and an alkyl group having 1 to 3 carbon atoms is particularly preferable. In addition, R 101, R 103 , R 105 , R 107 The linear or branched alkyl group represented by is preferably an unsubstituted alkyl group having no substituent substituting a hydrogen atom. This is because the above-mentioned dye becomes a dye with excellent dissolution rate during the preparation of the composition and excellent dispersion stability in the composition.
[0256] In formula (11), formula (11-1) or (11-2), as R 102 and R 106 The linear or branched chain alkyl group represented by is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 15 carbon atoms, particularly preferably an alkyl group having 2 to 10 carbon atoms, among which particularly preferably an alkyl group having 3 to 10 carbon atoms, and most preferably an alkyl group having 3 to 8 carbon atoms.
[0257] R 102 and R 106 The alkyl group represented by is also preferably branched. In addition, R 102 and R 106 The linear or branched chain alkyl group represented by is preferably an unsubstituted alkyl group having no substituent substituting a hydrogen atom. This is because the above-mentioned dye becomes a dye with excellent dissolution rate during the preparation of the composition and excellent dispersion stability in the composition.
[0258] In formula (11), formula (11-1) or (11-2), R 104 is preferably a hydrogen atom or an aryl group which may have a substituent, more preferably a hydrogen atom or a phenyl group which may have a substituent, and most preferably a hydrogen atom or a phenyl group substituted by a substituted amino group. Particularly in formula (11-1), R 104 is preferably a phenyl group substituted by a substituted amino group, and in formula (11-2), R 104 is preferably a hydrogen atom. As the substituted amino group, a tertiary amino group is preferred, and particularly preferably a group in which two hydrogen atoms of the amino group are substituted by a linear or branched chain alkyl group having 1 to 10 carbon atoms, or a group in which two hydrogen atoms of the amino group are substituted by a linear or branched chain alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 10 carbon atoms. This is because the above-mentioned dye becomes a dye with excellent dissolution rate during the preparation of the composition and excellent dispersion stability in the composition.
[0259] As the compound represented by formula (11-1), X is preferably a halogen atom, and particularly further preferably a fluorine atom. This is because the above-mentioned dye becomes a dye with excellent dissolution rate during the preparation of the composition and excellent dispersion stability in the composition.
[0260] As the compound represented by formula (11-2), M aMore preferably, it is Zn, Cu, Ni or Co, and most preferably Co. This is because the above-mentioned dye has excellent dissolution rate during the preparation of the composition and excellent dispersion stability in the composition.
[0261] As the compound represented by the formula (11-1), the following exemplified compounds (1) to (16) etc. can be cited.
[0262] Table A
[0263]
[0264] As the compound represented by the formula (11-2), the following exemplified compounds (17) to (42) etc. can be cited.
[0265] Table B
[0266] No R101 R102 R103 R104 R105 R106 R107 Ma 17 Me Et Me H Me Et Me Cu 18 Me Et Me H Me Et Me Zn 19 Me Et Me H Me Et Me Co 20 Me Et Me H Me Et Me Ni 21 Me n - propyl Me H Me n - propyl Me Zn 22 Et n - propyl Et H Et n - propyl Et Zn 23 Me n - propyl Me H Me n - propyl Me Co 24 Et n - propyl Et H Et n - propyl Et Co 25 Me n - butyl Me H Me n - butyl Me Co 26 Me sec - butyl Me H Me sec - butyl Me Co 27 Me isobutyl Me H Me isobutyl Me Co 28 Me tert - butyl Me H Me tert - butyl Me Co 29 Me pentyl Me H Me n - pentyl Me Zn 30 Me pentyl Me H Me n - pentyl Me Co 31 Me isopentyl Me H Me isopentyl Me Co 32 Me isopentyl Me H Me isopentyl Me Zn 33 Me sec - pentyl Me H Me sec - pentyl Me Zn 34 Me sec - pentyl Me H Me sec - pentyl Me Co 35 Me n - hexyl Me H Me n - hexyl Me Co 36 Me n - hexyl Me H Me n - hexyl Me Zn 37 Me n - octyl Me H Me n - octyl Me Zn 38 Me n - octyl Me H Me n - octyl Me Co 39 Me tert - octyl Me H Me tert - octyl Me Co 40 Me tert - octyl Me H Me tert - octyl Me Zn 41 Me n - dodecyl Me H Me tert - octyl Me Zn 42 Me n - dodecyl Me H Me tert - octyl Me Co
[0267] The manufacturing method of the pyrromethine dye represented by the above formula (11) is not particularly limited. For example, as the synthesis method of the compound having a pyrromethine structure, the method described in Japanese Patent Laid-Open No. 2011-174036 can be used. As the synthesis method of the pyrromethine dye as a dimer, the method described in Japanese Patent Laid-Open No. 2006-189751 can be used.
[0268] The pyrromethine dye preferably has a maximum absorption wavelength of 450 nm or more and less than 550 nm. Having a maximum absorption wavelength of 450 nm or more and less than 550 nm can be defined as meaning that the maximum absorption wavelength in the wavelength range of 380 nm or more and 780 nm or less is included in the range of 450 nm or more and less than 550 nm. The maximum absorption wavelength of the pyrromethine dye is preferably 470 nm or more and 530 nm or less, and preferably 480 nm or more and 510 nm or less among them. This is because it is easy to prepare a composition with excellent color purity of blue light and green light, and further becomes a composition with less reduction in color intensity.
[0269] In addition, because the effect of being able to obtain a cured product with excellent temporal stability of light absorption can be exerted more effectively. Because the effect of being able to obtain a cured product with excellent light absorption in the desired wavelength region can be obtained more effectively.
[0270] As the content of the above pyrromethine dye, it is preferably 10 parts by mass or more in 100 parts by mass of the dye, preferably 20 parts by mass or more and 80 parts by mass or less among them, preferably 30 parts by mass or more and 70 parts by mass or less, and preferably 40 parts by mass or more and 60 parts by mass or less among them. This is because the effect of being able to obtain a cured product with excellent temporal stability of light absorption can be exerted effectively. In addition, because it becomes easy to obtain a cured product with excellent light absorption in the desired wavelength region.
[0271] As the content of the above-mentioned pyrromethene dye, it is preferably 0.01 part by mass or more, more preferably 0.01 part by mass or more and 5 parts by mass or less, and particularly preferably 0.1 part by mass or more and 5 parts by mass or less, based on 100 parts by mass of the solid components of the composition. This is because a cured product with excellent temporal stability of light absorbance can be obtained. Because it becomes easier to obtain a cured product with excellent light absorbance in the desired wavelength region.
[0272] From the viewpoint of obtaining a cured product with more excellent light absorbance in the desired wavelength region, the content of the above-mentioned pyrromethene dye is preferably 0.1 part by mass or more and 2 parts by mass or less, based on 100 parts by mass of the solid components of the composition.
[0273] As the content of the above-mentioned pyrromethene dye, in 100 parts by mass of the composition, it is preferably 0.002 part by mass or more, more preferably 0.002 part by mass or more and 4 parts by mass or less, and particularly preferably 0.02 part by mass or more and 4 parts by mass or less. This is because it becomes easier to obtain a cured product with excellent temporal stability of light absorbance. Because it becomes easier to obtain a cured product with excellent light absorbance in the desired wavelength region.
[0274] This is because a cured product with excellent temporal stability of light absorbance can be obtained by the content of the above-mentioned pyrromethene dye. From the viewpoint of obtaining a cured product with more excellent light absorbance in the desired wavelength region, in 100 parts by mass of the composition, it is preferably 0.002 part by mass or more and 1.8 parts by mass or less.
[0275] (2) Tetraazaporphyrin dye
[0276] The above-mentioned tetraazaporphyrin dye may be any dye having a porphyrin structure and capable of absorbing light in the desired wavelength range.
[0277] As such a tetraazaporphyrin dye, for example, a metal-containing porphyrin compound described in JP-A-2018-081218, an azaporphyrin dye described in WO 2017 / 010076, etc. can be used.
[0278] In the present invention, the above-mentioned tetraazaporphyrin dye is preferably a compound represented by the following formula (12).
[0279] This is because when the above-mentioned tetraazaporphyrin dye is a compound represented by the above formula (12), the effect of being able to obtain a cured product with excellent temporal stability of light absorbance can be effectively exerted. In addition, because the effect of being able to obtain a cured product with excellent light absorbance in the desired wavelength region can be more effectively exerted.
[0280] [Chemical formula 14]
[0281]
[0282] (In the formula, R 301 、R 302 、R 303 、R 304 、R 305 、R 306 、R 307 and R 308 each independently represent a hydrogen atom, a halogen atom, a cyano group, an amino group, an alkyl group having 1 to 30 carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 carbon atoms which may have a substituent, or a heteroaryl group having 2 to 30 carbon atoms which may have a substituent,
[0283] R 301 and R 302 、R 303 and R 304 、R 305 and R 306 and R 307 and R 308 may also be connected to each other to form an alicyclic structure containing the carbon atoms of the pyrrole ring,
[0284] R 301 、R 302 、R 303 、R 304 、R 305 、R 306 、R 307 and R 308 will not simultaneously be hydrogen atoms,
[0285] M represents a compound of two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, or a trivalent or tetravalent metal.)
[0286] The above R 301 ~R 308 may be the same or different.
[0287] For example, R 301 and R 302 、R 303 and R 304 、R 305 and R 306 and R 307 and R 308 may each be the same group or each be different types of groups.
[0288] As R 301 、R 302 、R303 , R 304 , R 305 , R 306 , R 307 and R 308 The halogen atoms and amino groups used in 308 can be the same groups as the halogen atoms and amino groups listed as substituents for one or more hydrogen atoms on the ring of the substituted polycyclic aliphatic structure described in item (1) "Epoxy compound (A) having a polycyclic aliphatic structure" of the above "1. Cationic polymerizable component".
[0289] As the above R 301 -R 308 The alkyl groups having 1 to 30 carbon atoms used in 308 can be the same groups as the linear or branched chain alkyl groups having 1 to 30 carbon atoms listed as substituents for one or more hydrogen atoms on the ring of the substituted polycyclic aliphatic structure described in item (1) "Epoxy compound (A) having a polycyclic aliphatic structure" of the above "1. Cationic polymerizable component".
[0290] The above R 301 -R 308 The alkyl groups having 1 to 30 carbon atoms used in 308 are preferably alkyl groups having 1 to 12 carbon atoms, particularly preferably alkyl groups having 1 to 10 carbon atoms, among which particularly preferably alkyl groups having 1 to 8 carbon atoms, among which particularly preferably alkyl groups having 2 to 6 carbon atoms, among which particularly preferably alkyl groups having 2 to 5 carbon atoms. This is because a cured product having a steeper absorption peak in the desired wavelength range can be obtained.
[0291] As the substituents for the hydrogen atoms in the alkyl groups having 1 to 30 carbon atoms having substituents represented by the above R 301 -R 308 There can be mentioned alkenyl unsaturated groups, halogen atoms, acyl groups, acyloxy groups, substituted amino groups, sulfonamide groups, sulfonyl groups, carboxyl groups, cyano groups, sulfo groups, hydroxyl groups, nitro groups, mercapto groups, imide groups, carbamoyl groups, sulfonamide groups, phosphonic acid groups, phosphoric acid groups or salts of carboxyl groups, sulfo groups, phosphonic acid groups or phosphoric acid groups. The above substituents can also be alkoxy groups, aryl groups, aryloxy groups, heteroaryl groups, etc. described later.
[0292] That is, as the alkyl groups having 1 to 30 carbon atoms having substituents represented by the above R 301 -R 308 For example, there can also be mentioned aralkyl groups, linear, branched or cyclic haloalkyl groups, linear, branched or cyclic alkoxyalkyl groups, linear, branched or cyclic alkoxyalkoxyalkyl groups, aryloxyalkyl groups, aralkyloxyalkyl groups, linear, branched or cyclic haloalkoxyalkyl groups, etc.
[0293] Examples of the above aralkyl groups include benzyl, α-methylbenzyl, α-ethylbenzyl, α,α-dimethylbenzyl, α-phenylbenzyl, α,α-diphenylbenzyl, phenethyl, α-methylphenethyl, and the like.
[0294] Examples of the above linear, branched or cyclic haloalkyl groups include fluoromethyl, 3-fluoropropyl, 6-fluorohexyl, and the like.
[0295] Examples of the above linear, branched or cyclic alkoxyalkyl groups include methoxymethyl, ethoxymethyl, n-butoxymethyl, and the like.
[0296] Examples of the above linear, branched or cyclic alkoxyalkoxyalkyl groups include (2-methoxyethoxy)methyl, (2-ethoxyethoxy)methyl, and the like.
[0297] Examples of the above aryloxyalkyl groups include phenoxymethyl, 4-methylphenoxymethyl, 3-methylphenoxymethyl, and the like.
[0298] Examples of the above aralkyloxyalkyl groups include benzyloxymethyl, phenethyloxymethyl, and the like.
[0299] Examples of the above linear, branched or cyclic haloalkoxyalkyl groups include linear, branched or cyclic haloalkoxyalkyl groups such as fluoromethoxymethyl.
[0300] As for the above R 301 ~R 308 The alkoxy groups having 1 to 30 carbon atoms used in ~ may be groups having 1 to 30 carbon atoms in which -O- is bonded to the terminal side at the bonding site of an alkyl group, a cycloalkyl group or a cycloalkylalkyl group.
[0301] Regarding such alkoxy groups, they can be set to be the same as the alkoxy groups used in X in the above formula (11-1). Specifically, examples of the above alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, and the like.
[0302] As for the above R 301 ~R 308 The alkoxy groups having 1 to 30 carbon atoms with substituents represented by ~ may be alkoxy groups in which one or more hydrogen atoms in the alkoxy group are substituted by substituents.
[0303] Examples of the substituents for substituting the above hydrogen atoms include the groups listed as the substituents for the hydrogen atoms in the alkyl groups represented by the above R 301 ~R 308 represented by ~, and the like.
[0304] More specifically, examples of the alkoxy group having 1 to 30 carbon atoms and having a substituent include an aralkyloxy group and a linear, branched or cyclic halogenoalkoxy group.
[0305] Examples of the aralkyloxy group include a benzyloxy group, an α-methylbenzyloxy group, and an α-ethylbenzyloxy group.
[0306] Examples of the linear, branched or cyclic haloalkoxy group include a fluoromethoxy group and a 3-fluoropropoxy group.
[0307] As R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 and R 308 The aromatic group having 6 to 30 carbon atoms used in the present invention may be the same aromatic group having 6 to 30 carbon atoms as those listed as substituents for replacing 1 or 2 or more hydrogen atoms on the ring of the polycyclic aliphatic structure in the item “(1) Epoxy compound (A) having a polycyclic aliphatic structure” of the above “1. Cationic polymerizable component”.
[0308] As the above R 301 ~R 308 The aryl group having 6 to 30 carbon atoms is preferably an aryl group having 6 to 20 carbon atoms, particularly preferably an aryl group having 6 to 16 carbon atoms, particularly preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. This is because a cured product having a steeper absorption peak in a desired wavelength range can be obtained.
[0309] Examples of the aryl group having 6 to 30 carbon atoms and having a substituent include an aryl group in which one or two or more hydrogen atoms in the aryl group are substituted with a substituent.
[0310] Examples of the substituent group that replaces the hydrogen atom include: 301 ~R 308 The groups exemplified as substituents for hydrogen atoms of the alkyl groups represented by .
[0311] Examples of the aryl group having 6 to 30 carbon atoms, that is, the aryl group having 6 to 30 carbon atoms without a substituent, and the aryl group having 6 to 30 carbon atoms with a substituent include phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 3-ethylphenyl, 2-fluorophenyl, and 3-fluorophenyl.
[0312] As the above R 301 ~R 308The aryloxy group having 6 to 30 carbon atoms represented can include the above R 301 ~R 308 The group obtained by substituting the aryl group for the alkyl group in the alkoxy group used in
[0313] As the above R 301 ~R 308 The aryloxy group having 6 to 30 carbon atoms represented, for example, can include phenoxy group, 2-methylphenoxy group, etc.
[0314] As the above R 301 ~R 308 The aryloxy group represented is preferably an aryloxy group having 6 to 20 carbon atoms, more preferably an aryloxy group having 6 to 16 carbon atoms. This is because a cured product having a steeper absorption peak in the desired wavelength range can be obtained.
[0315] As the above R 301 ~R 308 The aryloxy group having 6 to 30 carbon atoms with substituents represented can include the aryloxy group in which one or more hydrogen atoms are substituted by substituents. As the substituents substituting the above hydrogen atoms, the groups exemplified as the substituents substituting the hydrogen atoms of the alkyl group represented by the above R 301 ~R 308 and the like can be mentioned.
[0316] As the above R 301 ~R 308 The aryloxy group having 6 to 30 carbon atoms with substituents represented can also include 2-methoxyphenoxy group, 4-isopropoxyphenoxy group, etc.
[0317] As the above R 301 ~R 308 The aryloxy group having 6 to 30 carbon atoms with substituents represented can also include 2-fluorophenoxy group, 3-chlorophenoxy group, etc.
[0318] Furthermore, as the above R 301 ~R 308 The aryloxy group having 6 to 30 carbon atoms with substituents represented can also include 3-chloro-4-methylphenoxy group, 2-phenylphenoxy group, etc.
[0319] As the above R 301 ~R 308 The heteroaryl group having 2 to 30 carbon atoms represented, for example, can include the group obtained by removing one hydrogen atom from an aromatic heterocycle containing at least one or more nitrogen atoms, oxygen atoms, or sulfur atoms as heteroatoms.
[0320] As the above R 301 ~R308 The heteroaryl group having 2 to 30 carbon atoms with substituents represented can be exemplified by a heteroaryl group in which one or more hydrogen atoms in the heteroaryl group are substituted with substituents. As the substituents for substituting the above hydrogen atoms, the groups exemplified as the substituents for the hydrogen atoms of the alkyl group represented by R 301 ~R 308 can be mentioned, etc.
[0321] As the above R 301 ~R 308 The heteroaryl group having 2 to 30 carbon atoms, that is, the heteroaryl group having 6 to 30 carbon atoms without substituents and the heteroaryl group having 2 to 30 carbon atoms with substituents can be exemplified by, for example, furyl, pyrrolyl, 3 - pyrrolidinyl, pyrazolyl, imidazolyl, etc.
[0322] As the above R 301 and R 302 、R 303 and R 304 、R 305 and R 306 or R 307 and R 308 connected to each other to form an alicyclic structure, an alicyclic hydrocarbon group having 3 to 20 carbon atoms formed by including the carbon atoms of the pyrrole ring bonded with R 301 etc. can be exemplified, for example, alicyclic structures such as cyclohexane, methylcyclohexane, dimethylcyclohexane, tert - butylcyclohexane, cyanocyclohexane, dichlorocyclohexane, etc.
[0323] In the present invention, the above R 301 ~R 308 are preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms without substituents or with substituents, an alkoxy group having 1 to 30 carbon atoms without substituents or with substituents, or an aryl group having 6 to 30 carbon atoms without substituents or with substituents.
[0324] As the combination of R 301 and R 302 、R 303 and R 304 、R 305 and R 306 and R 307 and R 308 as long as it is a combination capable of absorbing light of a desired wavelength, it can be any combination. Specifically, a combination of (i) a hydrogen atom and an alkyl group, (ii) an alkyl group and an alkoxy group, (iii) an alkyl group and an aryl group, etc. are preferred, and among them, (iii) is most preferred. This is because a cured product having a steep absorption peak in a desired wavelength range can be obtained.
[0325] In addition, R 301 , R 303 , R 305 and R 307 may be the same group or different groups, but are preferably the same group. This is because a cured product having a steeper absorption peak within a desired wavelength range can be obtained.
[0326] Furthermore, R 302 , R 304 , R 306 and R 308 may be the same group or different groups, but are preferably the same group. This is because a cured product having a steeper absorption peak within a desired wavelength range can be obtained.
[0327] As the combination of (iii) above, a combination of an unsubstituted or substituted alkyl group having 1 to 30 carbon atoms and an unsubstituted or substituted aryl group having 6 to 30 carbon atoms is preferred, a combination of an unsubstituted alkyl group having 1 to 10 carbon atoms and a substituted aryl group having 6 to 12 carbon atoms is more preferred, and a combination of an unsubstituted alkyl group having 2 to 5 carbon atoms and a substituted aryl group having 6 carbon atoms is particularly more preferred.
[0328] As a substituent for one or more hydrogen atoms of the substituted aryl group, a halogen atom is preferred, and a fluorine atom is particularly preferred. In addition, it is preferred that one hydrogen atom of the aryl group is substituted with a substituent.
[0329] In the present invention, it is particularly preferred that R 301 , R 303 , R 305 and R 307 are phenyl groups in which one or more hydrogen atoms are substituted with halogen atoms, and R 302 , R 304 , R 306 and R 308 are branched alkyl groups having 3 to 5 carbon atoms without substituents such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, 1,2-dimethylpropyl, 1-methylbutyl, 2-methylbutyl, etc., and most preferably R 301 , R 303 , R 305 and R 307 are phenyl groups in which one hydrogen atom is substituted with a fluorine atom such as 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, etc., and R 302 , R 304 , R 306 and R 308is an alkyl group having 3 to 5 carbon atoms without substituents such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, 1,2-dimethylpropyl, 1-methylbutyl, 2-methylbutyl, etc. This is because a cured product having a steeper absorption peak in the desired wavelength range can be obtained.
[0330] This is because through the above R 301 , R 303 , R 305 and R 307 are the above functional groups, and the above composition can easily obtain a cured product having excellent light absorbency in the desired wavelength region. In addition, when combined with a pyrromethene dye, a cured product having excellent light absorbency in the wavelength region of 450 nm or more and less than 550 nm and excellent light absorbency in the wavelength region of 550 nm or more and less than 610 nm can be easily obtained.
[0331] Examples of the divalent metal atom represented by M above include metal atoms belonging to Groups 3 to 15 of the periodic table. Specifically, Cu, Zn, Fe, Co, Ni, Ru, Pb, Rh, Pd, Pt, Mn, Sn, Pb, etc. can be cited.
[0332] Examples of the monovalent metal atom represented by M include Na, K, Li, etc.
[0333] In addition, examples of the compound of a trivalent or tetravalent metal represented by M include halides, hydroxides, and oxides of trivalent or tetravalent metals belonging to Groups 3 to 15 of the periodic table. As M, divalent M can be cited. Specific examples of the above metal compounds include AlCl, AlOH, InCl, FeCl, MnOH, SiCl2, SnCl2, GeCl2, Si(OH)2, Si(OCH3)2, Si(OPh)2, Si(OSiCH3)2, Sn(OH)2, Ge(OH)2, VO, TiO, etc.
[0334] The above M is preferably Cu, Zn, Co, Ni, Pb, Pd, Pt, Mn, VO, TiO, and particularly preferably Cu, Co, Ni, Pd, VO. This is because a cured product having a steeper absorption peak in the desired wavelength range can be obtained.
[0335] This is because when M is the above-mentioned metal atom or metal compound, the above-mentioned composition can easily obtain a cured product with excellent light absorbability in the desired wavelength region. In addition, when combined with a pyrromethene dye, a cured product with excellent light absorbability in the wavelength region of 450 nm or more and less than 550 nm and excellent light absorbability in the wavelength region of 550 nm or more and 610 nm or less can be easily obtained.
[0336] As the tetraazaporphyrin dye compound represented by the above formula (12), more specifically, compounds similar to the specific examples of the formula (12) described in JP-A-2017-68221 can be cited.
[0337] As a method for producing the above-mentioned tetraazaporphyrin dye compound, a known method can be used. For example, a production method based on the methods described in J.Gen.Chem.USSR vol.47, 1954 - 1958 (1977), JP-A-2012-121821, etc. can be cited.
[0338] As commercially available products of the above-mentioned tetraazaporphyrin dye compound, for example, PD-311S, PD-320, NC-35, SNC-8 (the above are from Yamamoto Chemical Co., Ltd.), FDG-004, FDG-007 (the above are from Yamada Chemical Industry Co., Ltd.), etc. can be cited.
[0339] As the maximum absorption wavelength of the above-mentioned tetraazaporphyrin dye, from the viewpoint of use as an optical filter for improving the color purity of green light and red light, it is preferably 550 nm or more and 610 nm or less, more preferably 570 nm or more and 605 nm or less, and particularly preferably 580 nm or more and 600 nm or less.
[0340] As the content of the above-mentioned tetraazaporphyrin dye, in 100 parts by mass of the dye, it is preferably 20 parts by mass or more, preferably 30 parts by mass or more and 90 parts by mass or less, particularly preferably 40 parts by mass or more and 80 parts by mass or less, and particularly preferably 45 parts by mass or more and 70 parts by mass or less. This is because it has the effect of improving the light resistance of pyrromethene.
[0341] As the content of the above-mentioned tetraazaporphyrin dye, in 100 parts by mass of the solid content of the composition, it is preferably 0.01 part by mass or more, preferably 0.01 part by mass or more and 8 parts by mass or less, particularly preferably 0.1 part by mass or more and 5 parts by mass or less, and particularly preferably 0.1 part by mass or more and 3 parts by mass or less. This is because it is necessary to efficiently cut off only specific wavelengths.
[0342] As the content of the above-mentioned tetraazaporphyrin dye, in 100 parts by mass of the composition, it is preferably 0.002 part by mass or more, more preferably 0.02 part by mass or more and 6.4 parts by mass or less, particularly preferably 0.02 part by mass or more and 4 parts by mass or less, and particularly preferably 0.02 part by mass or more and 2.4 parts by mass or less.
[0343] When the above-mentioned tetraazaporphyrin dye and pyrylium dye are used in combination, the total content of the above-mentioned pyrylium dye and tetraazaporphyrin dye is preferably 30 parts by mass or more, more preferably 50 parts by mass or more, particularly preferably 80 parts by mass or more, particularly preferably 90 parts by mass or more, and particularly preferably 95 parts by mass or more, and particularly preferably 100 parts by mass, that is, the dye is a pyrylium dye and a tetraazaporphyrin dye.
[0344] (3) Others
[0345] In the present invention, it is preferred that: the above-mentioned dye is contained in an amount of 0.01 part by mass or more and 10 parts by mass or less in 100 parts by mass of the solid content of the above-mentioned composition, the above-mentioned cationic polymerizable component is contained in an amount of 50 parts by mass or more in 100 parts by mass of the solid content of the above-mentioned composition, and the above-mentioned acid generator is contained in an amount of 0.01 part by mass or more and 10 parts by mass or less in 100 parts by mass of the solid content of the above-mentioned composition.
[0346] This is because when the content is within the above range, it is easy for the above-mentioned composition to obtain a cured product having excellent temporal stability of light absorption.
[0347] In the composition of the present invention, as long as the content of the above-mentioned dye is an amount that can obtain a cured product having excellent temporal stability of light absorption, it is not a problem, and it is appropriately set according to the use of the above-mentioned composition, etc., and can be set to 0.01 part by mass or more and 20 parts by mass or less in 100 parts by mass of the solid content of the composition, more preferably 0.01 part by mass or more and 5 parts by mass or less, and particularly preferably 0.1 part by mass or more and 5 parts by mass or less.
[0348] This is because when the content is within the above range, it is easy for the above-mentioned composition to obtain a cured product having excellent temporal stability of light absorption.
[0349] From the viewpoint of obtaining a cured product having more excellent temporal stability of light absorption, the content of the above-mentioned dye is preferably 0.5 part by mass or more and 4.5 parts by mass or less, preferably 1 part by mass or more and 4 parts by mass or less, and preferably 1.5 part by mass or more and 4 parts by mass or less in 100 parts by mass of the solid content of the composition.
[0350] It should be noted that when the dye contains two or more dyes, the content of the above-mentioned dye refers to the total content of the dyes.
[0351] The content of the above dye is not a problem as long as it is an amount that can obtain a cured product with excellent temporal stability of light absorbency, and it is appropriately set according to the use of the above composition, etc. However, relative to 100 parts by mass of the cationic polymerizable component, it can be set to 0.01 part by mass or more and 10 parts by mass or less, preferably 0.02 part by mass or more and 5 parts by mass or less, particularly preferably 0.05 part by mass or more and 5 parts by mass or less, among which particularly preferably 0.1 part by mass or more and 4.5 parts by mass or less, among which particularly preferably 0.5 part by mass or more and 4.5 parts by mass or less, preferably 0.8 part by mass or more and 4.5 parts by mass or less, preferably 1.0 part by mass or more and 4.5 parts by mass or less, preferably 1.5 part by mass or more and 4.2 parts by mass or less.
[0352] 3. Acid generator
[0353] The composition of the present invention preferably contains an acid generator. This is because by containing an acid generator, the above composition becomes a composition that easily undergoes cationic curing.
[0354] As the above acid generator, any compound is acceptable as long as it is a compound that can generate an acid under specified conditions, and there is no particular limitation.
[0355] As such an acid generator, for example, a photoacid generator that can generate an acid by light irradiation such as ultraviolet irradiation, and a thermal acid generator that can generate an acid by heat can be used.
[0356] The above acid generator can use at least one of the above photoacid generator and thermal acid generator. From the viewpoints of easy curing, reducing thermal damage to surrounding components used adjacent to the composition during curing of the composition, and a higher degree of freedom in the selection of surrounding components, etc., a photoacid generator is preferred. In addition, the above photoacid generator also has the advantage of a fast curing rate.
[0357] In addition, from the viewpoint of making it easier to form a cured product even in a part where light hardly reaches, the above acid generator is preferably a thermal acid generator. In addition, since the curing rate of the above thermal acid generator is relatively slow, after curing treatment (heating treatment) using it, it is possible to easily bond with other components.
[0358] The content of the above acid generator can be set to 0.01 part by mass or more and 10 parts by mass or less, preferably 0.1 part by mass or more and 5 parts by mass or less, in 100 parts by mass of the solid content of the above composition in total for single or multiple types. This is because the above composition can easily obtain a cured product with excellent temporal stability of light absorbency.
[0359] The usage ratio of the acid generator relative to the above cationic polymerizable component is not particularly limited, and it may be used at a generally usual usage ratio as long as it does not hinder the object of the present invention. For example, relative to 100 parts by mass of the cationic polymerizable component, the acid generator is preferably 0.05 parts by mass or more and 10 parts by mass or less, preferably 0.5 parts by mass or more and 8 parts by mass or less, preferably 1 part by mass or more and 7 parts by mass or less, and preferably 1.5 parts by mass or more and 5 parts by mass or less. With the above usage ratio within the above range, it is suitable in terms of sufficiently curing the cationic polymerizable component and having good heat resistance of the cured product of the composition.
[0360] In addition, this is because the above composition can easily obtain a cured product with excellent temporal stability of light absorption.
[0361] (1) Photoacid generator
[0362] As the above photoacid generator, any compound can be used as long as it can generate an acid by light irradiation such as ultraviolet irradiation, and it is preferably an onium salt or a derivative thereof that releases a Lewis acid by ultraviolet irradiation. Representative examples of such compounds include salts of cations and anions represented by the following formula (21).
[0363] [Chemical formula 15]
[0364] [A] m+ [B] m- (21)
[0365] Among them, the cation [A] m+ is preferably onium, and its structure can be represented by the following formula (22), for example.
[0366] [Chemical formula 16]
[0367] [(R 13 ) a Q] m+ (22)
[0368] Among them, R 13 is an organic group having 1 to 60 carbon atoms and may contain several atoms other than carbon atoms. a is an integer of 1 to 5. a R's 13 are each independent and may be the same or different. In addition, at least one is preferably the above organic group having an aromatic ring. Q is an atom or atomic group selected from the group consisting of S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, F, N=N. In addition, when the valence of Q in the cation [A] m+ is set to q, the relationship m = a - q needs to hold (where N=N is treated with a valence of 0).
[0369] In addition, the anion [B] m- is preferably a halide complex, and its structure can be represented, for example, by the following formula (23).
[0370] [Chemical formula 17]
[0371] [LX 2 b m- (23)
[0372] Among them, L is a metal or metalloid that is the central atom of the halide complex, and is B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn, Co, etc. X 2 is a halogen atom. b is an integer from 3 to 7. In addition, when the valence of L in the anion [B] m- is set to p, the relationship of m = b - p needs to hold.
[0373] As the anion [LX 2 b m- in the above formula, specific examples include tetrakis(pentafluorophenyl)borate [(C6F5)4B] - , tetrafluoroborate (BF4) - , hexafluorophosphate (PF6) - , hexafluoroantimonate (SbF6) - , hexafluoroarsenate (AsF6) - , hexachloroantimonate (SbCl6) - , tris(pentafluoromethyl)trifluorophosphate ion (FAP anion), etc.
[0374] In addition, for the anion [B] m- , an anion having the structure represented by the following formula (24) can also be preferably used.
[0375] [Chemical formula 18]
[0376] [LX 2 b-1 (OH)] m- (24)
[0377] Among them, L, X 2 , and b have the same meanings as above. In addition, as other anions that can be used, perchlorate ion (ClO4) - , trifluoromethylsulfite ion (CF3SO3) - , fluorosulfonate ion (FSO3) - , toluenesulfonate anion, trinitrobenzenesulfonate anion, camphorsulfonate, nonafluorobutanesulfonate, hexadecafluorooctanesulfonate, tetraarylborate, tetrakis(pentafluorophenyl)borate, etc.
[0378] In the present invention, among such onium salts, it is particularly effective to use the following aromatic onium salts (1) to (3). One kind can be used alone from them, or two or more kinds can be used in combination.
[0379] (1) Aryldiazonium salts such as phenyl diazonium hexafluorophosphate, 4-methoxyphenyl diazonium hexafluoroantimonate, 4-methylphenyl diazonium hexafluorophosphate
[0380] (2) Diaryliodonium salts such as diphenyliodonium hexafluoroantimonate, bis(4-methylphenyl)iodonium hexafluorophosphate, bis(4-tert-butylphenyl)iodonium hexafluorophosphate, tolyl cumyl iodonium tetrakis(pentafluorophenyl)borate
[0381] (3) Sulfonium salts of sulfonium cations represented by the following Group III or Group IV and hexafluoroantimonate ions, tetrakis(pentafluorophenyl)borate ions, etc.
[0382] [Chemical formula 19]
[0383] [Group III]
[0384]
[0385] [Chemical formula 20]
[0386] [Group IV]
[0387]
[0388] In addition, as other preferred examples, (η 5 -2,4-cyclopentadien-1-yl)[(1,2,3,4,5,6-η)-(1-methylethyl)benzene]-iron-hexafluorophosphate and other iron-arene complexes, mixtures of aluminum complexes such as tris(acetylacetone)aluminum, tris(ethylacetoacetato)aluminum, tris(salicylaldehyde)aluminum and silanol compounds such as triphenylsilanol, etc. can also be cited.
[0389] Among them, from the viewpoints of practicality and photosensitivity, it is preferable to use aromatic iodonium salts, aromatic sulfonium salts, and iron-arene complexes. In particular, aromatic sulfonium salts are further preferred from the viewpoint of sensitivity. Among them, in particular, the triarylsulfonium salt having a triaryl structure represented by the following formula (200) is further preferred from the viewpoint of sensitivity. In addition, this is because when the above photoacid generator is the above aromatic sulfonium salt, the above composition can form a cured product having excellent temporal stability of light absorption.
[0390] In addition, this is because the above-described composition can reduce heat-induced damage to peripheral components such as a substrate during curing, and the degree of freedom in selecting the peripheral components is increased.
[0391] [Chemical Formula 21]
[0392]
[0393] (In the formula, R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, a group obtained by substituting a methylene group other than the terminal on the bonding site side of the above alkyl group with a divalent group selected from the above Group I under the condition that oxygen atoms are not adjacent, an alkoxy group having 1 to 10 carbon atoms which may have a substituent, a group obtained by substituting a methylene group in the above alkoxy group with a divalent group selected from the above Group I under the condition that oxygen atoms are not adjacent, an ester group having 1 to 10 carbon atoms which may have a substituent, or a group obtained by substituting a methylene group in the above ester group with a divalent group selected from the above Group I under the condition that oxygen atoms are not adjacent.
[0394] R 35 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, a group obtained by substituting a methylene group other than the terminal on the bonding site side of the above alkyl group with a divalent group selected from the above Group I under the condition that oxygen atoms are not adjacent, and any substituent selected from the following formulas (A) to (C).
[0395] An1 q1- represents a q1-valent anion.
[0396] q1 represents an integer of 1 or 2.
[0397] p1 represents a coefficient for setting the charge to neutral.)
[0398] [Chemical Formula 22]
[0399]
[0400] (In the formula, R 121 , R 122 , R 123 , R124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 136 , R 137 , R 138 , R 139 , R 140 , R 141 , R 142 , R 143 and R 144 , R 145 , R 146 , R 147 , R 148 and R 149 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, a group obtained by substituting a methylene group other than the terminal at the bonding site side of the above alkyl group with a divalent group selected from the above Group I under the condition that oxygen atoms are not adjacent, an alkoxy group having 1 to 10 carbon atoms which may have a substituent, a group obtained by substituting a methylene group in the above alkoxy group with a divalent group selected from the above Group I under the condition that oxygen atoms are not adjacent, an ester group having 1 to 10 carbon atoms which may have a substituent, or a group obtained by substituting a methylene group in the above ester group with a divalent group selected from the above Group I under the condition that oxygen atoms are not adjacent,
[0401] * represents the bonding position to S in formula (200).)
[0402] In the compound represented by the above formula (200), as R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R127 , R 128 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 136 , R 137 , R 138 , R 139 , R 140 , R 141 , R 142 , R 143 , R144, R 145 , R 146 , R 147 , R 148 and R 149 The halogen atoms represented by R include fluorine, chlorine, bromine, iodine, etc.
[0403] In the compound represented by the above formula (200), as R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 136 , R 137 , R 138 , R 139 , R 140 , R 141 , R 142 , R 143 , R 144 , R 145 , R 146 , R 147 , R148 and R 149 Examples of the alkyl group having 1 to 10 carbon atoms used in 149 include the straight-chain or branched-chain alkyl groups having 1 to 30 carbon atoms, cycloalkyl groups having 3 to 30 carbon atoms, and cycloalkylalkyl groups having 4 to 30 carbon atoms, which are listed as substituents for substituting one or more hydrogen atoms on the ring of the substituted polycyclic aliphatic structure, as described in item (1) "Epoxy compound (A) having a polycyclic aliphatic structure" of "1. Cationic polymerizable component" above.
[0404] In addition, examples of the substituent for substituting the hydrogen atom of the alkyl group having 1 to 10 carbon atoms that may sometimes have a substituent include the groups listed as substituents for substituting the hydrogen atom of the hydrocarbon group, as described in item (1) "Epoxy compound (A) having a polycyclic aliphatic structure" of "1. Cationic polymerizable component" above.
[0405] Examples of the alkyl group having 1 to 10 carbon atoms that may sometimes have a substituent, or the group obtained by substituting the methylene group other than the terminal on the bonding site side of the above alkyl group with a divalent group selected from Group I above under the condition that oxygen atoms are not adjacent, include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, pentyl, isopentyl, tert-pentyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, ethyl octyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-butoxyethyl, methoxyethoxyethyl, methoxyethoxyethoxyethyl, 3-methoxybutyl, 2-methylthioethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, difluoroethyl, trichloroethyl, dichlorodifluoroethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, decafluoropentyl, tridecafluorohexyl, pentadecafluoroheptyl, heptadecafluorooctyl, methoxymethyl, 1,2-epoxyethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl, ethoxyethyl, butoxymethyl, tert-butylthiomethyl, 4-pentenoxymethyl, trichloroethoxymethyl, bis(2-chloroethoxy)methyl, methoxycyclohexyl, 1-(2-chloroethoxy)ethyl, 1-methyl-1-methoxyethyl, ethyldithioethyl, trimethylsilylethyl, tert-butyldimethylsilyloxymethyl, 2-(trimethylsilyl)ethoxymethyl, tert-butoxycarbonylmethyl, ethyloxycarbonylmethyl, ethylcarbonylmethyl, tert-butoxycarbonylmethyl, acryloyloxyethyl, methacryloyloxyethyl, 2-methyl-2-adamantyloxycarbonylmethyl, acetyl ethyl, 2-methoxy-1-propenyl, hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 3-hydroxybutyl, 4-hydroxybutyl, 1,2-dihydroxyethyl, etc.
[0406] In the compound represented by the above formula (200), as R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 、R 34 、R 121 、R 122 、R 123 、R 124 、R 125 、R 126 、R 127 、R 128 、R 129 、R 130 、R 131 、R 132 、R 133 、R 134 、R 136 、R 137 、R 138 、R 139 、R 140 、R 141 、R 142 、R 143 and R 144 、R 145 、R 146 、R 147 、R 148 and R 149 The alkoxy group having 1 to 10 carbon atoms used in R
[0407] Examples of the alkoxy group having 1 to 10 carbon atoms which may sometimes have substituents, or the group obtained by substituting the methylene group in the alkoxy group with a divalent group selected from Group I above under the condition that oxygen atoms are not adjacent to each other include methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy, isobutoxy, pentyloxy, isopentyloxy, tert-pentyloxy, hexyloxy, cyclohexyloxy, cyclohexylmethoxy, tetrahydrofuryloxy, tetrahydropyranyloxy, 2-methoxyethyloxy, 3-methoxypropyloxy, 4-methoxybutyloxy, 2-butoxyethyloxy, methoxyethoxyethyloxy, methoxyethoxyethoxyethyloxy, 3-methoxybutyloxy, 2-methylthioethyloxy, trifluoromethoxy and the like.
[0408] In the compound represented by the above formula (200), as R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 、R 34 、R 121 、R 122 、R 123 、R 124 、R 125 、R 126 、R 127 、R 128 、R 129 、R 130 、R 131 、R 132 、R 133 、R 134 、R 136 、R 137 、R 138 、R 139 、R 140 、R 141 、R 142 、R 143 and R 144 、R 145 、R 146 、R 147 、R 148 and R 149 Examples of the ester group having 1 to 10 carbon atoms used in R
[0409] In addition, as the substituent that replaces one or more hydrogen atoms in the above ester group, it can be set to be the same as the substituent that replaces the hydrogen atom of the group used in X substitution.
[0410] Examples of the ester group having 1 to 10 carbon atoms that may sometimes have a substituent, or the group obtained by substituting the methylene group in the above ester group with a divalent group selected from the above Group I under the condition that oxygen atoms are not adjacent, include methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, phenoxycarbonyl, acetoxy, propionyloxy, butyryloxy, chloroacetoxy, dichloroacetoxy, trichloroacetoxy, trifluoroacetoxy, tert-butylcarbonyloxy, methoxyacetoxy, benzoyloxy, and the like.
[0411] In the present invention, the above R 35 is preferably a group selected from the above chemical formulas (A) to (C), and preferably a group selected from the above formula (A) or (B). This is because when R 35 has the above structure, the composition becomes a composition capable of obtaining a cured product with excellent temporal stability of light absorption.
[0412] In the composition of the present invention, R 35 may also preferably be a group selected from the above formula (A) or (C). This is because the composition becomes a composition with excellent curing speed and adhesion.
[0413] In the composition of the present invention, from the viewpoint of the dispersion stability of the acid generator, R 35 is preferably a compound of chemical formula (C). On the other hand, from the viewpoint of making the composition have more excellent curing speed and adhesion, R 35 is preferably a compound of formula (A).
[0414] In the composition of the present invention, from the viewpoints of being able to obtain a cured product with excellent temporal stability of light absorption and making the composition have excellent curing speed and adhesion, the acid generator preferably contains both R 35 being a compound of formula (A) and being a compound of formula (C).
[0415] When the acid generator contains both R 35 being a compound of formula (A) and being a compound of formula (C), R 35The content of the compound of formula (A) can be set to 10 parts by mass or more and 200 parts by mass or less relative to 100 parts by mass of the compound of formula (C), preferably 50 parts by mass or more and 200 parts by mass or less, preferably 80 parts by mass or more and 120 parts by mass or less. This is because by being the content of the range, a cured product with excellent time stability of light absorption can be obtained, and a composition with excellent curing speed and adhesive strength can be obtained. In addition, because the composition of the present invention becomes a composition also excellent in moisture permeability resistance, etc.
[0416] R 21 , R 22 , R 24 , R 25 , R 26 , R 27 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34 Preferred are hydrogen atoms, halogen atoms, and unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, and particularly preferred are hydrogen atoms. This is because the composition can provide a cured product having excellent light absorption stability over time.
[0417] R 23 and R 28 Preferably, it is a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms in which the hydrogen atom is substituted by a halogen atom or is unsubstituted, and particularly preferably a hydrogen atom or a halogen atom. This is because the composition can be a composition that can obtain a cured product having excellent light absorption stability over time.
[0418] R 121 , R 122 , R 124 , R 125 , R 126 , R 127 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 137 , R 138 , R 139 , R 140 , R 141 , R 142 , R 143 , R 144 , R 145 , R 146 , R147 , R 148 and R 149 is preferably a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with a halogen atom in place of a hydrogen atom, and particularly preferably a hydrogen atom. This is because by being the above functional group, the composition becomes a composition capable of obtaining a cured product having excellent temporal stability of light absorption property.
[0419] R 123 , R 128 and R 136 is preferably a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with a halogen atom in place of a hydrogen atom, and preferably a hydrogen atom or a halogen atom. This is because by being the above functional group, the composition becomes a composition capable of obtaining a cured product having excellent temporal stability of light absorption property.
[0420] In the compound represented by the above formula (200), as the q1-valent anion represented by An1 q1- , for example, tetrakis(pentafluorophenyl)borate [(C6F5)4B] - , tetrafluoroborate (BF4) - , hexafluorophosphate (PF6) - , hexafluoroantimonate (SbF6) - , hexafluoroarsenate (AsF6) - , hexachloroantimonate (SbCl6) - , tris(pentafluoromethyl)trifluorophosphate ion (FAP anion), perchlorate ion (ClO4) - , trifluoromethylsulfite ion (CF3SO3) - , fluorosulfonate ion (FSO3) - , tosylate anion, trinitrobenzenesulfonate anion, camphorsulfonate, nonafluorobutanesulfonate, hexadecafluorooctanesulfonate, tetraarylborate, tetrakis(pentafluorophenyl)borate, etc.
[0421] (2) Thermal acid generator
[0422] Any compound may be used as long as it is a compound capable of generating an acid by heat, and there is no particular limitation. Preferably, an onium salt or a double salt that releases a Lewis acid by heat, or a cured product obtained by curing a resin composition with a derivative thereof has good heat resistance and is suitable.
[0423] As a representative example of such a compound, the salt of the cation and the anion represented by [A] m+ [B] m- described in the above item "(1) Photoacid generator" can be used.
[0424] As the above-mentioned heat acid generator, specifically, the compound represented by formula (2) in International Publication WO2018 / 110297 can be cited. As the above-mentioned heat acid generator, monophenylsulfonium salts are preferred because they are easily available industrially. Examples of such monophenylsulfonium salts include benzyl p-hydroxyphenylmethylsulfonium salt, p-hydroxyphenyldimethylsulfonium salt, p-acetoxyphenyldimethylsulfonium salt, benzyl p-hydroxyphenylmethylsulfonium salt, benzylphenylsulfonium salt, and the like.
[0425] The temperature range at which the above-mentioned heat acid generator can generate acid by heat and cure the composition is not particularly limited. However, from the aspects of obtaining a cured product with appropriate heat resistance and good thermal stability in the process, it is preferably 50°C or higher and 250°C or lower, more preferably 100°C or higher and 220°C or lower, further preferably 130°C or higher and 200°C or lower, and still further preferably 150°C or higher and 180°C or lower. This is because the formation of the cured product of the above composition is easy.
[0426] In addition, as commercially available products that can be suitably used as the heat acid generator in the composition of the present invention, for example, SAN AID SI-B2A, SAN AID SI-B3A, SAN AID SI-B3, SAN AID SI-B4, SAN AID SI-60, SAN AID SI-80, SAN AID SI-100, SAN AID SI-110, SAN AID SI-150 (the above are manufactured by Sanshin Chemical Industry Co., Ltd.), Adeka Opton CP-66, Adeka Opton CP-77 (the above are manufactured by Adeka Corporation), etc. can be cited. They can be used alone or in combination of two or more.
[0427] 4. Other Components
[0428] The above composition contains a dye, a cationic polymerizable component, and may contain an acid generator as needed, but may further contain a solvent and other components.
[0429] As the above-mentioned solvent, an organic solvent (hereinafter sometimes simply referred to as a solvent), water, etc. can be used. The above-mentioned solvent is a substance that is liquid at normal temperature (25°C) and atmospheric pressure. The above-mentioned solvent is a substance that can disperse or dissolve each component in the above composition. Therefore, even if it is liquid at normal temperature (25°C) and atmospheric pressure, the above-mentioned dye and cationic polymerizable component do not conform to the solvent. As the above-mentioned solvent, either water or an organic solvent can be used. In the present invention, the above-mentioned solvent is preferably an organic solvent. This is because the dissolution or dispersion of the above compound A is easy.
[0430] As the above-mentioned other components, various additives can be cited.
[0431] As such solvents and various additives, they can be set to be the same as the solvents and various additives described in International Publication No. 2017 / 098996 etc.
[0432] In addition, as the total content of the above-mentioned other components, it can be set to 30 parts by mass or less per 100 parts by mass of the solid content of the above-mentioned composition. When the above-mentioned composition contains the above-mentioned other components, the content of the above-mentioned other components is preferably 0.05 part by mass or more and 10 parts by mass or less, and preferably 0.1 part by mass or more and 5 parts by mass or less. This is because the above-mentioned composition easily forms a cured product with excellent temporal stability of light absorption.
[0433] As the above-mentioned organic solvent, a substance that is liquid at 25°C and can be dried and removed when forming a cured product using the above-mentioned composition is used.
[0434] Specific examples of the above-mentioned organic solvent include ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone; alcohol solvents such as methanol, ethanol, isopropyl alcohol or n-propanol, isobutanol or n-butanol, pentanol, diacetone alcohol; ether ester solvents such as ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethoxyethyl propionate, 1-tert-butoxy-2-propanol, 3-methoxybutyl acetate, cyclohexyl acetate; BTX solvents such as benzene; aliphatic hydrocarbon solvents such as hexane; terpene hydrocarbon oils such as turpentine; paraffin solvents such as mineral spirits; halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol solvents and the like. These solvents can be used singly or as a mixed solvent of two or more.
[0435] Among them, the organic solvent preferably contains ketones, alcohol solvents, and ether ester solvents, among which alcohol solvents and ether ester solvents are preferably contained, and alcohol solvents are particularly preferably contained. This is because the above-mentioned composition becomes a composition with excellent dispersion stability of dyes.
[0436] The content of the above-mentioned organic solvent is preferably 50 parts by mass or more per 100 parts by mass of the above-mentioned solvent, among which it is preferably 70 parts by mass or more, and particularly preferably 90 parts by mass or more. This is because when the content is within the above-mentioned range, the above-mentioned composition becomes a composition with excellent dispersion stability of dyes.
[0437] In addition, when the above-mentioned organic solvent contains an alcohol-based solvent, the content of the above-mentioned alcohol-based solvent is preferably 20 parts by mass or more and 80 parts by mass or less, more preferably 30 parts by mass or more and 70 parts by mass or less, and still more preferably 40 parts by mass or more and 60 parts by mass or less in 100 parts by mass of the above-mentioned solvent. This is because when the content is within the above range, the above-mentioned composition becomes a composition with excellent dispersion stability of the dye.
[0438] The above-mentioned composition contains the above-mentioned cationic polymerizable component as a resin component, and may contain, if necessary, resin components other than the above-mentioned cationic polymerizable component (hereinafter sometimes referred to as other resin components).
[0439] Examples of the above-mentioned other resin components include condensable compounds and their condensates.
[0440] Examples of the above-mentioned condensable compounds include free-radical polymerizable compounds. In addition, monomer components constituting condensates described later can also be cited.
[0441] The above-mentioned free-radical polymerizable compound is a compound having a free-radical polymerizable group.
[0442] Examples of the above-mentioned free-radical polymerizable group include ethylenically unsaturated groups such as acryloyl group, methacryloyl group, and vinyl group as long as they can be polymerized by free radicals.
[0443] The above-mentioned free-radical polymerizable compound can be set as a compound having one or more free-radical polymerizable groups, and a monofunctional compound having one free-radical polymerizable group or a polyfunctional compound having two or more free-radical polymerizable groups can be used.
[0444] As the above-mentioned free-radical polymerizable compound, a compound having an acid value, a compound not having an acid value, etc. can be used.
[0445] Examples of the above-mentioned compound having an acid value include acrylic acid esters and methacrylic acid esters having a carboxyl group such as methacrylic acid and acrylic acid.
[0446] Examples of the above-mentioned compound not having an acid value include urethane acrylate resin, urethane methacrylate resin, epoxy acrylate resin, epoxy methacrylate resin, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, and other acrylic acid esters and methacrylic acid esters not having a carboxyl group.
[0447] The above-mentioned free-radical polymerizable compound can be used alone or in combination of two or more. For example, the free-radical polymerizable compound can be used in combination of a compound having an ethylenically unsaturated group and an acid value and a compound having an ethylenically unsaturated group and not having an acid value.
[0448] When two or more radical polymerizable compounds are used in combination, they may be pre-copolymerized and used as a copolymer.
[0449] More specifically, examples of such radical polymerizable compounds include those described in JP-A-2016-176009.
[0450] In the present invention, from the viewpoint of forming a cured product having excellent light absorbency in a desired wavelength region and excellent temporal stability of light absorbency, the content of the above radical polymerizable compound is preferably small.
[0451] The content of the above radical polymerizable compound is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, particularly preferably 1 part by mass or less, and most preferably 0.5 part by mass or less, based on 100 parts by mass of the solid content of the above composition. In particular, it is most preferably 0 part by mass, that is, the radical polymerizable compound is not contained.
[0452] As the above polycondensate, oligomers and polymers containing two or more repeating units can be used.
[0453] Examples of the above polycondensate include thermoplastic resins such as polyolefin resins, styrene resins, polyester resins, polyether resins, polycarbonate resins, polyamide resins, and halogen-containing resins.
[0454] As such a polycondensate, for example, it can be set to be the same as the polycondensate described as a thermoplastic resin in WO2017 / 150662.
[0455] Examples of the above other components include sensitizers.
[0456] As such a sensitizer, for example, anthracene compounds, naphthalene compounds, carbazole derivatives, and benzocarbazole derivatives can be preferably used. Among them, carbazole derivatives and benzocarbazole derivatives can be preferably used, and benzocarbazole derivatives can be particularly preferably used. This is because by using the above sensitizer, the effect of obtaining a cured product having excellent temporal stability of light absorbency is not hindered, and the curability and the like can be improved. In addition, since the bleeding of the dye can be effectively suppressed, the effect of obtaining a cured product having excellent temporal stability of light absorbency can be more effectively exhibited. In addition, since the above composition becomes a composition having more excellent moisture permeability resistance and the like.
[0457] As the above anthracene compound, any compound having an anthracene structure may be used. For example, the compound represented by the following formula (IIIa) can be mentioned.
[0458] [Chemical formula 23]
[0459]
[0460] (In the formula, R 201 and R 202 each independently represent an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 12 carbon atoms, and R 203 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.)
[0461] As the alkyl group having 1 to 6 carbon atoms represented by R 201 , R 202 and R 203 , an alkyl group having 1 to 30 carbon atoms that satisfies the specified number of carbon atoms and is used as a substituent for a hydrogen atom on the ring of the above polycyclic aliphatic structure can be used.)
[0462] As the alkoxyalkyl group having 2 to 12 carbon atoms represented by R 201 and R 202 , an alkoxyalkyl group having a specified number of carbon atoms in an alkyl group substituted with an alkoxy group having 1 to 30 carbon atoms represented by R 301 to R 308 can be used.)
[0463] As the above naphthalene-based compound, any compound having a naphthalene structure can be used. For example, a compound represented by the following formula (IIIb) can be cited.)
[0464] [Chemical formula 24]
[0465]
[0466] (In the formula, R 204 and R 205 each independently represent an alkyl group having 1 to 6 carbon atoms.)
[0467] As the alkyl group having 1 to 6 carbon atoms represented by R 204 and R 205 , an alkyl group having 1 to 30 carbon atoms that satisfies the specified number of carbon atoms and is used as a substituent for a hydrogen atom on the ring of the polycyclic aliphatic structure listed above can be used.)
[0468] As the above carbazole derivative, any compound having a carbazole structure can be used. For example, a compound represented by the following formula (VI) can be cited.)
[0469] [Chemical formula 25]
[0470]
[0471] (In the formula, R 226arepresents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group, or an aryl group having 6 to 20 carbon atoms, R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a , and R 234a each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group, a hydroxyl group, or a carboxyl group.)
[0472] As examples of the alkyl group having 1 to 10 carbon atoms and the aryl group having 6 to 20 carbon atoms represented by R 226a , R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a , and R 234a , groups satisfying the specified number of carbon atoms in the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 30 carbon atoms used as substituents for the hydrogen atoms on the ring of the above polycyclic aliphatic structure can be used. As the halogen atoms represented by R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a , and R 234a , the same halogen atoms as those listed above for the substituents of the hydrogen atoms on the ring of the polycyclic aliphatic structure can be cited.
[0473] As the above benzocarbazole derivative, any compound having a benzocarbazole structure can be used. For example, the compounds represented by the following formulas (VII-1) to (VII-3) can be cited.
[0474] In the present invention, the above benzocarbazole derivative is preferably the compound represented by the above formula (VII-1). This is because the above composition becomes a composition having excellent curability.
[0475] [Chemical formula 26]
[0476]
[0477] (In the formula, R 235 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group, or an aryl group having 6 to 20 carbon atoms, R 236 , R 237 , R238 , R 239 , R 240 , R 241 , R 242 , R 243 , R 244 and R 245 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group, a hydroxyl group, or a carboxyl group.)
[0478] [Chemical formula 27]
[0479]
[0480] (In the formula, R 246 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group, or an aryl group having 6 to 20 carbon atoms, R 247 , R 248 , R 249 , R 250 , R 251 , R 252 , R 253 , R 254 , R 255 and R 256 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group, a hydroxyl group, or a carboxyl group.)
[0481] [Chemical formula 28]
[0482]
[0483] (In the formula, R 257 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group, or an aryl group having 6 to 20 carbon atoms, R 258 , R 259 , R 260 , R 261 , R 262 , R 263 , R 264 , R 265 , R 266 and R 267 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group, a hydroxyl group, or a carboxyl group.)
[0484] As R 235 , R 236 , R 237 , R 238 , R 239 , R 240 , R241 , R 242 , R 243 , R 244 , R 245 , R 246 , R 247 , R 248 , R 249 , R 250 , R 251 , R 252 , R 253 , R 254 , R 255 , R 256 , R 257 , R 258 , R 259 , R 260 , R 261 , R 262 , R 263 , R 264 , R 265 , R 266 and R 267 The halogen atoms, alkyl groups having 1 to 10 carbon atoms, and aryl groups having 6 to 20 carbon atoms represented by R can use groups satisfying the specified number of carbon atoms among the halogen atoms, alkyl groups having 1 to 30 carbon atoms, and aryl groups having 6 to 30 carbon atoms that can be used as substituents for the hydrogen atoms on the ring of the above polycyclic aliphatic structure.
[0485] In the present invention, in the benzocarbazole derivatives represented by formulas (VII-1) to (VII-3), the groups bonded to the nitrogen atom of the benzocarbazole ring, namely R 235 , R 246 and R 257 are preferably alkyl groups having 1 to 10 carbon atoms, and among them, branched alkyl groups having 3 to 10 carbon atoms are preferred. This is because the above composition becomes a composition having excellent curability.
[0486] In the present invention, the above R 236 , R 237 , R 238 , R 239 , R 240 , R 241 , R 242 , R 243 , R 244 , R 245 , R 247 , R 248 , R 249 , R 250 , R 251 , R 252 , R 253 , R 254 , R255 , R 256 , R 258 , R 259 , R 260 , R 261 , R 262 , R 263 , R 264 , R 265 , R 266 and R 267 Preferably, they are a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and preferably a hydrogen atom. This is because when the above-mentioned groups are the above-mentioned groups or atoms, the above-mentioned composition becomes a composition having excellent curability.
[0487] As the content of the above-mentioned sensitizer, any content that can promote the polymerization of cationic polymerizable components may be used. For example, when counted alone or in combination of multiple ones, it can be set to 0.01 parts by mass or more and 6 parts by mass or less in 100 parts by mass of the solid content of the above-mentioned composition, preferably 0.1 parts by mass or more and 3 parts by mass or less, and particularly preferably 0.5 parts by mass or more and 2 parts by mass or less. This is because the above-mentioned composition becomes a composition having excellent curability.
[0488] The use ratio of the above-mentioned sensitizer to the cationic polymerizable compound is not particularly limited, and it may be used at a generally usual use ratio as long as it does not hinder the object of the present invention.
[0489] For example, the content of the above-mentioned sensitizer is preferably 1 part by mass or more and 200 parts by mass or less, preferably 5 parts by mass or more and 100 parts by mass or less, preferably 10 parts by mass or more and 60 parts by mass or less, preferably 15 parts by mass or more and 50 parts by mass or less, relative to 100 parts by mass of the acid generator. This is because when the above-mentioned use ratio is within the above-mentioned range, a composition having excellent curability is obtained.
[0490] 5. Composition
[0491] The content of each of the above-mentioned components can be combined with the content described for each component.
[0492] For example, when the above-mentioned composition contains a cationic polymerizable component, a dye, and an acid generator, the content of each component can be combined with the content described in the items of "1. Cationic polymerizable component", "2. Dye", and "3. Acid generator", respectively.
[0493] When the above composition contains a cationic polymerizable component, a dye, and an acid generator, for example, the content of the above dye is 0.01 part by mass or more and 10 parts by mass or less in 100 parts by mass of the solid components of the above composition, the content of the above cationic polymerizable component is 50 parts by mass or more in 100 parts by mass of the solid components of the above composition, and the content of the above acid generator can be set to 0.01 part by mass or more and 10 parts by mass or less in 100 parts by mass of the solid components of the above composition. With the content of each of the above components being the above combination, a cured product with excellent temporal stability of light absorption can be easily obtained from the above composition.
[0494] As a method for manufacturing the above composition, any method can be used as long as it can form a composition containing the above components in desired amounts, and examples thereof include methods using known mixing means.
[0495] The composition of the present invention is used for various applications as a composition for photo- or thermo-curing. As specific applications, there can be mentioned optical filters, coatings, coating agents, lining agents, adhesives, printing plates, insulating varnishes, insulating sheets, laminated boards, printed circuit boards, sealants for semiconductor devices / LED packages / liquid crystal injection ports / organic electroluminescence (EL) / optical elements / electrical insulation / electronic components / separation membranes, molding materials, putties, glass fiber impregnating agents, caulking agents, passivation films for semiconductors / solar cells, interlayer insulating films, protective films, printed circuit boards, or color filters for color television sets, PC monitors, portable information terminals, CCD image sensors, electrode materials for plasma display panels, printing inks, dental compositions, resins for stereolithography, both liquid and dry films, micro mechanical components, glass fiber cable coatings, and various applications of materials for holographic recording.
[0496] As the above optical filter, a filter that requires a change in the spectral shape of the light passing through the optical filter can be set, and for example, it can be used for image display devices such as liquid crystal display devices (LCDs), plasma display panels (PDPs), electroluminescent displays (ELDs), cathode ray tube display devices (CRTs), CCD image sensors, CMOS sensors, fluorescent display tubes, field emission displays, for analytical devices, for manufacturing semiconductor devices, for astronomical observations, for optical communications, for spectacle lenses, windows, and the like.
[0497] In the present invention, the above composition is preferably for forming an optical filter, more preferably for forming an optical filter for an image display device, and particularly preferably for forming a color adjustment filter for an image display device.
[0498] Among them, the color adjustment filter may include filters that adjust light of each color. More specifically, as the color adjustment filter, there may be mentioned a filter that is arranged so as to overlap with a color filter in a plan view for further adjusting the color of light passing through the color filter configured with pixels of R (red), G (green), B (blue) and other colors used as an optical filter; a filter that is arranged so as to overlap with each color light-emitting body in a plan view for further adjusting the color of light emitted from each color light-emitting body such as an electroluminescent element of each color, etc.
[0499] This is because by using it for the above-mentioned purposes, the effect of being able to produce a cured product with excellent temporal stability of light absorption can be more effectively exerted.
[0500] Among them, when the above-mentioned dye contains a dye having a maximum absorption wavelength at 450 nm or more and less than 550 nm, the above-mentioned use is preferably for forming a color adjustment filter of an image display device having light-emitting light of blue light and green light. In addition, when the above-mentioned dye contains a dye having a maximum absorption wavelength at 550 nm or more and 610 nm or less, it is also preferably for forming a color adjustment filter of an image display device arranged so as to overlap with a green pixel or a red pixel.
[0501] In addition, as the use of the above-mentioned composition, there may also be mentioned the use for forming a member that requires flexibility.
[0502] Specifically, the above-mentioned composition can be preferably used for forming an optical filter of a flexible image display device, etc.
[0503] B. Cured Product
[0504] Next, the cured product of the present invention will be described.
[0505] The cured product of the present invention is characterized in that it is a cured product of the above-mentioned composition.
[0506] According to the present invention, the above-mentioned cured product, which is a cured product obtained by curing the above-mentioned composition, can be used, for example, as an optical filter having excellent temporal stability of light absorption.
[0507] The cured product of the present invention is a cured product using the above-mentioned composition.
[0508] Hereinafter, the cured product of the present invention will be described in detail.
[0509] It should be noted that regarding the above-mentioned composition, it can be set to be the same as the content described in the above item "A. Composition".
[0510] The above-mentioned cured product is usually a cured product of a polymer containing a cationically polymerizable component.
[0511] Regarding the top view shape, thickness, etc. of the above-mentioned cured product, they can be appropriately set according to the use of the above-mentioned cured product, etc.
[0512] As the above-mentioned thickness, for example, it can be set to 0.05 μm or more and 300 μm or less, etc.
[0513] As the manufacturing method of the above-mentioned cured product, as long as it is a method capable of forming the cured product of the above-mentioned composition in a manner that becomes the desired shape, there is no particular limitation.
[0514] As such a manufacturing method, for example, it can be set to be the same as the content described in the item "D. Manufacturing method of cured product" described later, so the description is omitted here.
[0515] Regarding the use, etc. of the above-mentioned cured product, it can be set to be the same as the content described in the item "A. Composition" above.
[0516] C. Optical filter
[0517] Next, the optical filter of the present invention will be described.
[0518] The optical filter of the present invention is characterized in that it has a light absorption layer containing the above-mentioned cured product.
[0519] According to the present invention, by the above-mentioned light absorption layer containing the above-mentioned cured product, an optical filter with excellent temporal stability of light absorption property is obtained.
[0520] The optical filter of the present invention has the above-mentioned light absorption layer.
[0521] Hereinafter, the light absorption layer contained in the optical filter of the present invention will be described in detail.
[0522] 1. Light absorption layer
[0523] The above-mentioned light absorption layer contains the above-mentioned cured product.
[0524] The content of the above-mentioned cured product contained in the above-mentioned light absorption layer is usually 100 parts by mass in 100 parts by mass of the light absorption layer. That is, the above-mentioned light absorption layer can be formed into a layer composed of the above-mentioned cured product.
[0525] Regarding the above-mentioned cured product, it can be set to be the same as the content described in the item "B. Cured product" above.
[0526] Regarding the top view shape, area, thickness and other shapes of the above-mentioned light absorption layer, they can be appropriately set according to the use of the optical filter, etc.
[0527] As the method for forming the above light absorption layer, any method capable of forming a light absorption layer with a desired shape and thickness can be used, and a known method for forming a coating film can be employed. As the above forming method, for example, it can be set to be the same as the content described in the item "D. Method for manufacturing a cured product" described later.
[0528] 2. Optical filter
[0529] The above optical filter may contain only the above light absorption layer, or may contain other layers in addition to the above light absorption layer.
[0530] Examples of the above other layers include a transparent support, a primer layer, an antireflection layer, a hard coat layer, a lubricating layer, an adhesive layer, and the like.
[0531] Regarding the content of each such layer and its forming method, etc., it can be set to the content and forming method commonly used in optical filters. For example, it can be set to be the same as the content described in Japanese Patent Application Laid-Open No. 2011-144280, International Publication No. 2016 / 158639, etc.
[0532] The above light absorption layer can also be used, for example, as an adhesive layer that bonds the above transparent support and any of the respective layers.
[0533] In addition, at this time, the above optical filter can also be provided with a known separator such as a polyethylene terephthalate film that is easily sealable on the surface of the light absorption layer that serves as an adhesive layer.
[0534] When the above optical filter is used for an image display device, it can usually be disposed in front of the display. For example, it is also acceptable to directly attach the optical filter to the surface of the display. When there is a front panel or electromagnetic wave shielding in front of the display, the optical filter can also be attached to the front side (outer side) or the back side (display side) of the front panel or electromagnetic wave shielding.
[0535] The above optical filter can also be used, for example, as various components included in an image display device, such as optical components such as color filters and polarizers.
[0536] In addition, the above optical filter can also be a filter directly laminated on various components included in the above image display device.
[0537] D. Method for manufacturing a cured product
[0538] Next, the method for manufacturing a cured product of the present invention will be described.
[0539] The method for manufacturing a cured product of the present invention is characterized in that it includes a step of curing the above composition.
[0540] According to the present invention, since the method for manufacturing the cured product is a method for curing the above composition, for example, a cured product that can be used as an optical filter with excellent temporal stability of light absorption can be obtained.
[0541] The method for manufacturing the cured product of the present invention includes the above curing step.
[0542] Hereinafter, each step of the method for manufacturing the cured product of the present invention will be described in detail.
[0543] It should be noted that the above composition can be set to be the same as that described in the item of "A. Composition" above, so the description is omitted here.
[0544] 1. Curing step
[0545] The above curing step is a step of curing the above composition.
[0546] As the method for curing the above composition, any method that can polymerize the above cationically polymerizable components with each other can be used.
[0547] Examples include a method of irradiating an energy ray to a coating film of the composition, a method of heating a coating film of the composition, etc. When the above composition contains an acid generator, such a polymerization method is preferably determined according to the type of the acid generator. Specifically, when the composition contains a photoacid generator as the acid generator, a method of irradiating an energy ray can be preferably used, and when the composition contains a thermal acid generator as the acid generator, a method of heating can be preferably used. This is because the polymerization of the above cationically polymerizable components is easy.
[0548] In this step, as the light source of the energy ray used in the polymerization of the cationically polymerizable component, electromagnetic wave energy having a wavelength of 2,000 Å to 7,000 Å or high energy rays such as electron rays, X-rays, and radiation obtained from a super high pressure mercury lamp, high pressure mercury lamp, medium pressure mercury lamp, low pressure mercury lamp, mercury vapor arc lamp, xenon arc lamp, carbon arc lamp, metal halide lamp, fluorescent lamp, tungsten lamp, excimer lamp, germicidal lamp, light emitting diode, CRT light source, etc. can be used. It is preferable to use a super high pressure mercury lamp, mercury vapor arc lamp, carbon arc lamp, xenon arc lamp, light emitting diode, etc. that emit light having a wavelength of 300 to 450 nm. This is because the polymerization of the cationically polymerizable component is easy.
[0549] There is no particular limitation on the irradiation amount of the energy ray, and it can be appropriately determined according to the composition of the composition. From the viewpoint of preventing the deterioration of the components in the composition, the irradiation amount is preferably 100 mJ / cm 2 ~2,000 mJ / cm 2 .
[0550] As a method of heating the coating film of the composition in this step, methods such as using a hot plate such as a heating plate, an air oven, an inert gas oven, a vacuum oven, a hot air circulation oven, etc. can be cited.
[0551] The heating temperature when heating the coating film is not particularly limited, but from the viewpoint of easy polymerization of the cationically polymerizable component, it is preferably 70°C or higher and 200°C or lower, more preferably 90°C or higher and 150°C or lower.
[0552] The heating time when heating the coating film is not particularly limited, but from the aspect of improving productivity, it is preferably 1 to 60 minutes, more preferably 1 to 30 minutes.
[0553] In this step, the above-mentioned curing method is preferably a method in which the method of irradiating energy rays and the method of heating are used in combination. More specifically, it is preferably to sequentially perform the method of irradiating energy rays and the method of heating. This is because the polymerization of the cationically polymerizable component can be effectively carried out.
[0554] 2. Other steps
[0555] The above-mentioned manufacturing method may also have other steps as required.
[0556] As such a step, a step of coating the above-mentioned composition before the step of curing the composition, etc. can be cited.
[0557] As a method of coating the composition, known methods such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various printing methods, dipping, etc. can be used.
[0558] The above-mentioned substrate can be appropriately set according to the use of the cured product, etc., and substrates including soda glass, quartz glass, semiconductor substrates, metals, papers, plastics, etc. can be cited.
[0559] In addition, the above-mentioned cured product can be used after being peeled off from the substrate after being formed on the substrate, or can be used after being transferred from the substrate to other adherends.
[0560] 3. Cured product
[0561] Regarding the cured product manufactured by the manufacturing method of the present invention and its uses, etc., it can be set to be the same as the content described in the above item "B. Cured product".
[0562] The present invention is not limited to the above-mentioned embodiments. The above-mentioned embodiments are for illustration, and any mode having a configuration substantially the same as the technical idea described in the claims of the present invention and exhibiting the same effects is included in the technical scope of the present invention.
[0563] Examples
[0564] Hereinafter, examples and comparative examples will be listed to describe the present invention in more detail, but the present invention is not limited to these examples and the like.
[0565] [Production Example 1]
[0566] In a reaction flask, 3,3’,5,5’-tetramethyl-4,4’-bis(3-methylbutoxycarbonyl) dipyrromethane obtained by reacting 2,4-dimethyl-3-(3-methylbutoxycarbonyl) pyrrole, ethyl orthoformate, and trifluoroacetic acid in dichloromethane was reacted with cobalt(II) acetate tetrahydrate and triethylamine in methanol to obtain a pyrromethane dye having a dimer structure represented by the following formula (H-1). The molecular weight of the target product was confirmed by mass spectrometry.
[0567] [Production Example 2]
[0568] A compound (tetraaza porphyrin dye) represented by the following formula (H-2) was obtained by the production method of azaporphyrin-based compounds described in JP-A-2012-121821.
[0569] [Examples 1 to 15 and Comparative Examples 1 to 5]
[0570] According to the formulations described in Tables 1 and 2 below, a cationic polymerizable component, an acid generator, a dye, a solvent, and an additive were blended, and the blend was passed through a 5-μm membrane filter to remove insoluble components to obtain a composition.
[0571] In addition, the following materials were used for each component.
[0572] It should be noted that the blending amounts in the tables represent parts by mass of each component.
[0573] Table 1
[0574]
[0575] Table 2
[0576]
[0577] The following shows each component such as the cationic polymerizable component, the acid generator, the sensitizer, the antioxidant, and the dye described in Tables 1 and 2.
[0578] A-1: A compound represented by the following formula (A-1) (an epoxy compound having a polycyclic aliphatic structure, a low molecular weight compound) was used.
[0579] A-2: A compound represented by the following formula (A-2) (HP-7200 of DIC Corporation, an epoxy compound having a polycyclic aliphatic structure) was used.
[0580] B-1: A compound represented by the following formula (B-1) (alicyclic epoxy compound, low molecular weight compound) is used.
[0581] C-1: A compound represented by the following formula (C-1) (epoxy compound having no polycyclic aliphatic structure, aliphatic epoxy compound, low molecular weight compound) is used.
[0582] C-2: A compound represented by the following formula (C-2) (epoxy compound having no polycyclic aliphatic structure, aliphatic epoxy compound, low molecular weight compound) is used.
[0583] C-3: EHPE-3150 of Daicel Corporation (adduct of 1,2-epoxy-4-(2-oxiranyl)cyclohexane with 2,2-bis(hydroxymethyl)-1-butanol, high molecular weight compound with a weight average molecular weight exceeding 1,000, epoxy compound having no polycyclic aliphatic structure, aliphatic epoxy compound) is used.
[0584] D-1: A compound represented by the following formula (D-1) (epoxy compound having no polycyclic aliphatic structure, aromatic epoxy compound, low molecular weight compound) is used.
[0585] E-1: A 50 mass% solution of PC (propylene carbonate) using the compound shown in the following formula (E-1) is used.
[0586] E-2: A 50 mass% solution of PC (propylene carbonate) using the compound shown in the following formula (E-2) is used.
[0587] E-3: A 50 mass% solution of PC (propylene carbonate) using the compound shown in the following formula (E-3) is used.
[0588] F-1: A compound represented by the following formula (F-1) (benzocarbazole derivative, sensitizer) is used.
[0589] G-1: A compound shown in the following formula (G-1) (antioxidant) is used.
[0590] H-1: A compound represented by the following formula (H-1) (pyrromethine dye produced in Production Example 1, maximum absorption wavelength: 493 nm (in chloroform)) is used.
[0591] H-2: A compound represented by the following formula (H-2) (tetraazaporphyrin dye produced in Production Example 2, maximum absorption wavelength: 594 nm (in chloroform)) is used.
[0592] I-1: SH-29PA manufactured by Dow Corning Toray Co., Ltd. is used.
[0593] J-1: Diacetone alcohol (DAA, solvent) was used.
[0594] J-2: Propylene glycol monomethyl ether (PGMEA, solvent) was used.
[0595] J-3: Dipropylene glycol monomethyl ether acetate (DPMA, solvent) was used.
[0596] [Chemical formula 29]
[0597]
[0598] R101 = Me, R102 = isoamyl, R103 = Me, R104 = H,
[0599] R105 = Me, R106 = isoamyl, R107 = Me, Ma = Co
[0600] [Evaluation]
[0601] For various measurements, the following methods were used.
[0602] Evaluation 1 and Evaluation 2. Changes in transmittance before and after damp heat for the two maximum absorption wavelengths
[0603] Using the compositions of the examples and comparative examples, the measurements were carried out by the following method.
[0604] (Method for measuring changes in transmittance before and after damp heat)
[0605] (1) The above composition was coated on glass (EAGLE XG, 0.7 mm) by the bar coating method.
[0606] The thickness of the coating film was adjusted so that the transmittance at the maximum absorption wavelength of the sample for evaluation was about 4% - 7%.
[0607] (2) Then, the coating film was dried in an oven at 80 °C for 5 minutes to remove the solvent. Using a high-pressure mercury lamp, ultraviolet rays of 1500 mJ / cm 2 were irradiated for curing treatment to obtain a sample for evaluation. The obtained sample for evaluation was left standing in a constant temperature and humidity chamber at 60 °C and 90% for 5 days, and the changes in transmittance at 496.0 nm (λmax1, from the compound represented by formula (H-1)) before and after the damp heat test (Evaluation 1), and the changes in transmittance at 596.0 nm (λmax2, from the compound represented by formula (H-2)) (Evaluation 2) were investigated respectively, and evaluated according to the following criteria. The results are shown in Table 1 and Table 2 above.
[0608] It should be noted that the change in transmittance is a value expressed as "(transmittance before the test - transmittance after the damp heat test) (%)".
[0609] The smaller the change in transmittance, the better the temporal stability of the light absorption property can be judged.
[0610] (Evaluation criteria for Evaluation 1)
[0611] Change in transmittance is 1% or less: +++
[0612] Change in transmittance exceeds 1% and is 3% or less: ++
[0613] Change in transmittance exceeds 3% and is 5% or less: +
[0614] Change in transmittance exceeds 5%: -
[0615] (Evaluation criteria for Evaluation 2)
[0616] Change in transmittance is 1% or less: +++
[0617] Change in transmittance exceeds 1% and is 3% or less: ++
[0618] Change in transmittance exceeds 3% and is 5% or less: +
[0619] Change in transmittance exceeds 5%: -
[0620] It was confirmed from Table 1 and Table 2 that the compositions of each example formed by combining specific two kinds of epoxy compounds have less change in transmittance before and after damp heat at any wavelength above 450 nm and below 550 nm and above 550 nm and below 610 nm compared with the compositions of each comparative example not having this combination, and a cured product with excellent temporal stability of light absorption property can be obtained.
[0621] According to the formulation described in Table 3 below, a dye, a radically polymerizable component, a radical polymerization initiator, a solvent, and an additive were combined, and the mixture was passed through a 5-μm membrane filter to remove insoluble components to obtain a composition (Comparative Examples 6 and 7).
[0622] It should be noted that the following materials were used as the radically polymerizable component and the radical polymerization initiator. In addition, the same components as those used in the above Examples 1 to 15 and Comparative Examples 1 to 5 were used for other components.
[0623] It should be noted that the compounding amounts in the table represent parts by mass of each component.
[0624] Table 3
[0625]
[0626] K-1: Dipentaerythritol hexaacrylate (A-DPH manufactured by Shin-Nakamura Chemical Co., Ltd.) was used.
[0627] K-2: Polyethylene glycol diacrylate (A-200 manufactured by Shin-Nakamura Chemical Co., Ltd.) was used.
[0628] L-1: Irgacure OXE-01 was used.
[0629] Evaluation 3. Minimum transmittance and maximum absorption wavelength of the composition and its cured product
[0630] Using the compositions of Example 1, Comparative Example 1, and Comparative Examples 6 and 7, samples for evaluation before curing and samples for evaluation after curing were prepared by the following method. Using a visible ultraviolet spectrophotometer V-670 manufactured by JASCO Corporation, the transmittance spectrum at 496.0 nm of the compound (pyrromethene dye) represented by formula (H-1) was measured. The results are shown in Table 4 below.
[0631] (Method for preparing samples for evaluation before curing)
[0632] (1) The above composition was coated on a substrate (PET film A9300, 100 μm manufactured by Toyobo Co., Ltd.) by the bar coating method.
[0633] The thickness of the coating film was adjusted so that the transmittance at the maximum absorption wavelength of the sample for evaluation before curing became about 4 to 7%.
[0634] (2) Then, the coating film was dried at 80°C for 5 minutes using an oven to remove the solvent, and a sample for evaluation before curing was obtained.
[0635] (Method for preparing samples for evaluation after curing)
[0636] For the sample for evaluation before curing, a high-pressure mercury lamp was used to irradiate ultraviolet rays of 1500 mJ / cm 2 for curing treatment, and a sample for evaluation after curing was obtained.
[0637] Table 4
[0638]
[0639] From the results in Table 4, it was confirmed that the compositions containing cationic polymerizable components in Example 1 and Comparative Example 1 had less change in transmittance before and after curing compared to the compositions containing radical polymerizable components in Comparative Examples 6 to 7, and cured products with excellent light absorbability in the wavelength region of 450 nm or more and less than 550 nm could be obtained.
Claims
1. A composition comprising: a dye; and a cationic polymerizable component, wherein the dye comprises a pyrromethene dye, and the cationic polymerizable component comprises an epoxide having a polycyclic aliphatic structure and an alicyclic epoxide.
2. The composition according to claim 1, wherein, The epoxide having a polycyclic aliphatic structure is an aliphatic epoxide.
3. The composition according to claim 1 or claim 2, wherein, The content of the cationic polymerizable component is 50 parts by mass or more per 100 parts by mass of the solid content of the composition.
4. The composition according to claim 1 or claim 2, wherein The epoxide having a polycyclic aliphatic structure comprises a compound having a structure represented by the following formula (I) as the polycyclic aliphatic structure, wherein the polycyclic aliphatic structure in the formula means bonding to an adjacent group at the * part.
5. The composition according to claim 1 or claim 2, wherein The content of the epoxide having a polycyclic aliphatic structure is 20 parts by mass or more and 70 parts by mass or less per 100 parts by mass of the cationic polymerizable component.
6. The composition according to claim 1 or claim 2, wherein, The alicyclic epoxide comprises a compound represented by the following formula (1), In the formula, X 1 represents a divalent linking group that is directly bonded or has more than 1 atom.
7. The composition according to claim 1 or claim 2, wherein The cationic polymerizable component further comprises an aliphatic epoxide not having a polycyclic aliphatic structure.
8. The composition according to claim 7, wherein, The aliphatic epoxide not having a polycyclic aliphatic structure comprises a compound represented by the following formula (2), In the formula, R 1 is a group obtained by removing p hydroxyl groups, i.e., -OH, from a p-valent alcohol, and p and q each represent an integer of 1 or more; When p is 2 or more, p structural units q may be the same or different.
9. The composition according to claim 1 or claim 2, wherein the cationic polymerizable component comprises a low molecular weight compound having a molecular weight of 1,000 or less, and the content of the low molecular weight compound is 60 parts by mass or more and 99 parts by mass or less per 100 parts by mass of the cationic polymerizable component.
10. The composition according to claim 1 or claim 2, wherein the pyrromethene dye is a dipyrromethene complex compound formed by coordination of a structure represented by the following formula (11) with a metal atom or a metal compound, In the formula, R 101 , R 102 , R 103 , R 105 , R 106 , and R 107 each independently represent a linear or branched alkyl group, R 104 represents a hydrogen atom, a linear or branched alkyl group, or an aryl group, and the alkyl group and the aryl group may have substituents.
11. The composition according to claim 1 or claim 2, wherein the dye comprises a tetraazaporphyrin dye, and the tetraazaporphyrin dye is a compound represented by the following formula (12), In the formula, R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 , and R 308 each independently represent a hydrogen atom, a halogen atom, a cyano group, an amino group, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms, and the alkyl group, the alkoxy group, the aryl group, the aryloxy group, and the heteroaryl group may have substituents. R 301 With R 302 、R 303 With R 304 、R 305 With R 306 And R 307 With R 308 They can also be connected to each other to form an alicyclic structure containing the carbon atoms of the pyrrole ring. R 301 、R 302 、R 303 、R 304 、R 305 、R 306 、R 307 and R 308 will not simultaneously become hydrogen atoms. where M represents two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, or a compound of a trivalent or tetravalent metal.
12. A cured product which is a cured product of the composition according to any one of claims 1 to 11.
13. An optical filter having a light absorption layer comprising a cured product of the composition according to any one of claims 1 to 11.
14. A method for producing a cured product, comprising a step of curing the composition according to any one of claims 1 to 11.
Citation Information
Patent Citations
Sliding nozzle device having sealing mechanism
JP1986003653A
Optical filter for display
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JP2012121821A