CN111433243A

CN111433243A - Curable resin composition, laminate, optical filter, and compound

Info

Publication number: CN111433243A
Application number: CN201880078115.9A
Authority: CN
Inventors: 牧内直征
Original assignee: JSR Corp
Current assignee: JSR Corp
Priority date: 2017-12-19
Filing date: 2018-12-17
Publication date: 2020-07-17
Anticipated expiration: 2038-12-17
Also published as: KR102577455B1; CN111433243B; JP7192796B2; TWI781263B; JPWO2019124294A1; WO2019124294A1; KR20200090821A; TW201934591A

Abstract

One embodiment of the present invention relates to a curable resin composition containing at least one compound (a) selected from compounds represented by the following formula (a1) and the following formula (a2) and a polymerization initiator (D), a laminate, an optical filter, and a compound. [ R ]¹～R⁶Each independently being a hydrogen atom or a methyl group, X³～X¹⁰Each independently a C6-20 hydrocarbon group having an alicyclic hydrocarbon group, Y¹～Y⁴Each independently an organic group having 6 to 40 carbon atoms and having an alicyclic hydrocarbon group, m is an integer of 0 to 20, and n is an integer of 0 to 20.]

Description

Curable resin composition, laminate, optical filter, and compound

Technical Field

One embodiment of the present invention relates to a curable resin composition, a laminate, an optical filter, and a compound.

Background

In recent years, a laminate in which a resin layer is provided on the surface of a substrate by applying a curable resin composition has been widely used in order to prevent a film from being scratched or to improve the adhesion between the substrate and an upper layer provided thereon. Such a laminate is used as a display device such as a touch panel; surface materials of membrane switch (membrane switch), keypad (keypad), and the like; an electrode substrate of a liquid crystal cell (cell) constituting a liquid crystal display element; optical films such as retardation films, films with transparent electrodes for touch panels, and films for near infrared cut filters (cut filters).

The laminate is required to have a resin layer excellent in various performances such as scratch resistance, adhesion to a substrate or an upper layer, and hardness (for example, patent documents 1 and 2).

Documents of the prior art

Patent document

Patent document 1: japanese patent No. 6041372

Patent document 2: japanese patent laid-open publication No. 2017-47683

Disclosure of Invention

Problems to be solved by the invention

In recent years, development of a laminate having a substrate/resin layer/inorganic film formed thereon has been advanced, and studies have been made on a material for lamination to obtain the laminate. As one of reliability evaluations, a laminate used for an optical member or the like is required to have high adhesion at each layer interface after being held for a long period of time under a high-temperature and high-humidity environment, but there is room for further improvement in order to satisfy the above requirements for a resin layer obtained from a conventional composition. Further, since the resin layer has a low surface hardness, it is desirable that the resin layer has a high hardness because scratches that cause defects are generated, but the adhesion decreases as the hardness increases, and it is difficult to achieve both hardness and adhesion.

One embodiment of the present invention provides a curable resin composition capable of forming a resin layer having high surface hardness and excellent adhesion, particularly adhesion to an inorganic film.

Means for solving the problems

The present inventors have conducted intensive studies to solve the above problems, and as a result, have found that the above problems can be solved by the following configuration examples, and have completed the present invention.

The constitution of the present invention is as follows.

[1] A curable resin composition comprising a compound (A) selected from at least one compound represented by the following formula (A1) and the following formula (A2) and a polymerization initiator (D):

[ solution 1]

In the formula (A1), R¹And R²Each independently being a hydrogen atom or a methyl group, X³～X⁵Each independently a C6-20 hydrocarbon group having an alicyclic hydrocarbon group, Y¹And Y²Each independently an organic group having 6 to 40 carbon atoms and having an alicyclic hydrocarbon group, m is an integer of 0 to 20,when m is 2 or more, plural X' s⁴And Y¹May be the same or different;

[ solution 2]

In the formula (A2), R³～R⁶Each independently being a hydrogen atom or a methyl group, X⁶～X¹⁰Each independently a C6-20 hydrocarbon group having an alicyclic hydrocarbon group, Y³And Y⁴Each independently an organic group having 6 to 40 carbon atoms and having an alicyclic hydrocarbon group, n is an integer of 0 to 20, and when n is 2 or more, a plurality of X' s⁷、X¹⁰、Y⁴And R⁶May be the same or different.

[2]According to [1]The curable resin composition described above, wherein X is³～X⁵At least one of (a) and the X⁶～X¹⁰At least one of the above (A) and (B) is independently a hydrocarbon group having an adamantane ring and having 10 to 20 carbon atoms.

[3]According to [1]Or [ 2]]The curable resin composition, wherein Y is¹～Y²And Y and³～Y⁴at least one of the groups is independently a group represented by any one of the following (y1) to (y 5):

[ solution 3]

In formulae (y1) to (y4), two of the two represent the bonding positions to N constituting the urethane bond in formula (a1) or formula (a2), respectively, and two of E in formula (y5), one represents the bonding position to N constituting the urethane bond in the isocyanurate ring, and the other represents the bonding position to N constituting the urethane bond in formula (a1) or formula (a 2).

[4] The curable resin composition according to any one of [1] to [3], which comprises a compound (B) represented by the following formula (B):

[ solution 4]

In the formula (B), R¹⁰A hydrogen atom or a methyl group, and L is an organic group having an alicyclic hydrocarbon group having 6 to 20 carbon atoms.

[5] The curable resin composition according to [4], wherein the content ratio of the compound (A) to the compound (B) (the mass of the compound (A): the mass of the compound (B)) in the curable resin composition is 1: 99 to 99: 1.

[6] The curable resin composition according to any one of [1] to [5], wherein the compound (A) has a molecular weight of 500 to 5000.

[7] The curable resin composition according to [4] or [5], wherein the molecular weight of the compound (B) is 180 to 600.

[8] A laminate comprising a substrate and a resin layer formed from the curable resin composition according to any one of [1] to [7 ].

[9] The laminate according to [8], wherein at least one of the base material and the resin layer contains a coloring matter.

[10] An optical filter comprising the laminate according to [8] or [9] and a dielectric multilayer film.

[11] A compound represented by the following formula (a):

[ solution 5]

In the formula (a), Y ' is an organic group having 6 to 40 carbon atoms and having an alicyclic hydrocarbon group, X ' is independently a hydrocarbon group having 6 to 20 carbon atoms and having an alicyclic hydrocarbon group, R ' is independently a hydrogen atom or a methyl group, p is 2 or 3, and a plurality of X ' and R ' may be the same or different.

[12] The compound according to [11], wherein at least one of X' is adamantanediyl.

[13] The compound according to [11] or [12], wherein the Y' is a group represented by any one of the following (Y1) to (Y5):

[ solution 6]

In the formulae (y1) to (y4), two represent the bonding positions to N constituting the urethane bond in the formula (a), and two of E in the formula (y5), one represents the bonding position to N constituting the urethane bond in the isocyanurate ring, and the other represents the bonding position to N constituting the urethane bond in the formula (a).

ADVANTAGEOUS EFFECTS OF INVENTION

According to one embodiment of the present invention, a curable resin composition capable of forming a resin layer having high surface hardness, excellent adhesion, particularly adhesion to an inorganic film, and a small haze value can be provided. Further, according to one embodiment of the present invention, a laminate and an optical filter having excellent moist heat resistance and few defects can be provided.

Detailed Description

Curable resin composition and compound

The curable resin composition according to an embodiment of the present invention (hereinafter, also referred to as "the present composition") contains at least one compound (a) selected from the compounds represented by the formula (a1) and the formula (a2) and a polymerization initiator (D).

The compound (hereinafter, also referred to as "compound (a)") according to one embodiment of the present invention is represented by the formula (a).

Since the present composition contains the compound (a) and the compound (a) is used, a resin layer having high surface hardness, a small haze value, excellent adhesion to a substrate and an inorganic film, and excellent adhesion to an inorganic film by suppressing moisture absorption and the like even in moist heat can be easily obtained.

Further, since the resin layer is easily elastically restored and easily exhibits toughness, it is expected that the scratch resistance of the film-formed thin film is improved, the yield is improved by suppressing the micro cracks at the time of die stamping, and the like, and further, the adhesion to the substrate or the inorganic film is improved by the interaction between the urethane bond and the inorganic film or by stress relaxation.

Conventional polyfunctional urethane compounds tend to absorb moisture, and the adhesiveness to a substrate or an inorganic film is reduced by moist heat, and further, the polyfunctional compound for realizing high hardness tends to cause curing shrinkage, thereby reducing the adhesiveness to a substrate or an inorganic film. On the other hand, by using the compounds (a) and (a) having a large amount of alicyclic structures, a resin layer which is hydrophobic, hardly undergoes curing shrinkage, and has high hardness can be formed, and adhesion to a substrate or an inorganic film at the time of curing or at the time of moist heat and high hardness can be achieved at the same time.

Further, since the compounds (a) and (a) having a urethane bond are easier to synthesize than the compounds having an ester bond, the present invention relating to the compounds (a) and (a) can be said to have high utility in material development.

The present composition and compound (a) can be preferably used for optical members, particularly optical filters, and further near infrared ray cut filters.

< Compound (A) >

The compound (a) is at least one compound selected from the group consisting of compounds represented by the following formula (a1) and compounds represented by the following formula (a 2). The compound represented by the following formula (a1) is more preferable in that a resin layer having excellent adhesion to a substrate and adhesion to an inorganic film under wet heat and small curing shrinkage can be easily obtained.

[ solution 7]

[ in the formula (A1), R¹And R²Each independently being a hydrogen atom or a methyl group, X³～X⁵Each independently a C6-20 hydrocarbon group having an alicyclic hydrocarbon group, Y¹And Y²Each independently an organic group having 6 to 40 carbon atoms and having an alicyclic hydrocarbon group, m is an integer of 0 to 20, and when m is 2 or more, a plurality of the groupsX⁴And Y¹May be the same or different.]

[ solution 8]

[ in the formula (A2), R³～R⁶Each independently being a hydrogen atom or a methyl group, X⁶～X¹⁰Each independently a C6-20 hydrocarbon group having an alicyclic hydrocarbon group, Y³And Y⁴Each independently an organic group having 6 to 40 carbon atoms and having an alicyclic hydrocarbon group, n is an integer of 0 to 20, and when n is 2 or more, a plurality of X' s⁷、X¹⁰、Y⁴And R⁶May be the same or different.]

X³～X¹⁰Each independently a C6-20 hydrocarbon group having an alicyclic hydrocarbon group, preferably a group including an alicyclic hydrocarbon.

X³～X¹⁰The hydrocarbon group in (2) has a carbon number of 6 or more, preferably 8 or more, more preferably 10 or more, and 20 or less, preferably 17 or less, more preferably 12 or less.

As X³～X¹⁰The alicyclic hydrocarbon group contained in (1) includes: cyclopropanediyl, cyclobutanediyl, cyclopentanediyl, cyclohexanediyl, cycloheptanediyl, cyclooctanediyl, cyclopropylenediyl, cyclobutenediyl, cyclopentenediyl, cyclohexenediyl, cycloheptenediyl, cyclooctenediyl, bicyclo [2.2.1 ] diyl]Heptanediyl, trimethylbicyclo [2.2.1 ]]Heptanediyl, bicyclo [2.2.2]Octanediyl, adamantanediyl, bicyclo [2.2.1 ]]Heptenediyl, bicyclo [2.2.2]Octenediyl, cyclohexanedimethyl, tricyclodecanedimethyl, pentacyclodecandimethyl and the like.

Among these, cyclohexane dimethyl and adamantanediyl are preferable, and adamantanediyl is particularly preferable in that a resin layer having high hardness can be easily obtained even if the crosslinking group concentration is low, and a resin layer having a more excellent balance between high hardness and low curing shrinkage can be easily obtained. That is, X is preferable³～X⁵At least one ofAnd said X⁶～X¹⁰Is preferably X, among them³～X¹⁰Each independently a hydrocarbon group having 10 to 20 carbon atoms and an adamantane ring, and particularly preferably an adamantanediyl group.

Y¹～Y⁴The organic group in (b) has a carbon number of 6 or more, preferably 8 or more, more preferably 10 or more, and 40 or less, preferably 30 or less, more preferably 20 or less.

As Y¹～Y⁴The alicyclic hydrocarbon group contained in (1) includes X³～X¹⁰Examples of the alicyclic hydrocarbon group include the same groups as those listed above.

Y is preferably Y in terms of easily obtaining a resin layer having more excellent adhesion to the substrate and the inorganic film, particularly to the inorganic film even when it is wet and hot¹～Y²And Y and³～Y⁴is preferably Y, among them¹～Y⁴Each independently a hydrocarbon group having 6 to 20 carbon atoms and having an alicyclic hydrocarbon group or an organic group having 15 to 40 carbon atoms and including an alicyclic hydrocarbon group and an isocyanurate ring, more preferably a group including a cyclohexane ring or a norbornane ring, and still more preferably a group represented by any one of the following (y1) to (y 5).

[ solution 9]

-CH in the formula (y3)₂The position of-is preferably-CH₂-meta or para to Cy (Cy is cyclohexane ring).

m is preferably 0 to 5, and more preferably 0 in view of ease of synthesis of the compound (A), yield during synthesis, and the like.

n is preferably 0 to 5, and more preferably 0 in consideration of the ease of synthesis of the compound (a), the yield during synthesis, and the like.

The compound (a) is particularly preferably a compound represented by the following formula (a) in terms of easily obtaining a resin layer having high surface hardness, a small haze value, and excellent adhesion to a substrate and an inorganic film.

[ solution 10]

In the formula (a), Y' is an organic group having 6 to 40 carbon atoms and having an alicyclic hydrocarbon group, and Y is exemplified¹～Y⁴The same groups and the like, and preferred groups are also the same.

X' is independently a C6-20 hydrocarbon group having an alicyclic hydrocarbon group, and X is exemplified³～X¹⁰The same groups and the like, and preferred groups are also the same.

R' is independently a hydrogen atom or a methyl group, and p is 2 or 3.

The plural X's and R's may be the same or different.

The molecular weight of the compound (a) is preferably 500 to 5000, more preferably 500 to 2000, in terms of easily obtaining a resin layer having high surface hardness, a small haze value, and excellent adhesion to a substrate and an inorganic film.

The method for synthesizing the compound (a) is not particularly limited, and the compound (a) can be synthesized by a conventionally known method, but is preferably a method in which a compound represented by the following formula (a1) is reacted with a compound represented by the following formula (a 2). In addition, a compound represented by the following formula (a3) can also be used in carrying out the reaction.

[ solution 11]

(in the formula (a1), R and X¹Are each independently of the R¹And X³Phase of meaningThe same is true. )

[ solution 12]

(in the formula (a2), Y is the same as Y¹The meaning is the same, q is 2 or 3. )

[ solution 13]

(in the formula (a3), X²And said X³The meaning is the same. )

The reaction is preferably carried out in the presence of a catalyst, a solvent, or the like conventionally used in the reaction of a hydroxyl group and an isocyanate group.

The reaction is preferably carried out under heating, and the reaction temperature is preferably 50 to 90 ℃.

The content of the compound (a) in the present composition is preferably 1% by mass or more, more preferably 10% by mass or more, particularly preferably 30% by mass or more, and preferably 90% by mass or less, more preferably 80% by mass or less, and particularly preferably 70% by mass or less, in terms of easily obtaining a resin layer having high surface hardness, a small haze value, and more excellent adhesion to a substrate and an inorganic film.

< polymerization initiator (D) >

The present composition contains a polymerization initiator (D). The polymerization initiator (D) is not particularly limited as long as it is a compound capable of polymerizing the compound (a) and the following compound (B) or compound (C).

The polymerization initiator (D) contained in the present composition may be one kind, or two or more kinds.

As the polymerization initiator (D), a known photopolymerization initiator can be used, and a heat-polymerization initiator may be used in combination as necessary.

Examples of the polymerization initiator (D) include photopolymerization initiators described in Japanese patent laid-open Nos. 2008-276194 and 2003-241372.

Examples of the polymerization initiator (D) include an alkylphenone compound, an acylphosphine oxide compound, a bisimidazole compound, a triazine compound, an oxime ester compound, a benzoin compound, and a benzophenone compound.

Examples of the alkylphenone compound include α -hydroxyalkylphenone such as 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one and 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl ] phenyl } -2-methyl-propan-1-one, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2- (2-methylbenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (3-methylbenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (4-methylbenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (2-dimethylaminoethyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (2-dimethoxyphenyl) ethyl) -2-morpholinophenyl-1-diethylaminopropyl-2- (2-dimethylamino-1- (4-morpholinophenyl) acetophenone, 2-di-amino-1- (2-morpholinophenyl) acetophenone and the like.

Examples of acylphosphine oxide compounds include: 2, 4, 6-trimethylbenzoyl diphenylphosphine oxide, and bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide.

Examples of the biimidazole compound include: 2, 2 '-bis (2, 4-dichlorophenyl) -4, 5, 4', 5 '-tetraphenyl-1, 2' -biimidazole, 2 '-bis (2-chlorophenyl) -4, 5, 4', 5 '-tetraphenyl-1, 2' -biimidazole, 2 '-bis (2, 4-dimethylphenyl) -4, 5, 4', 5 '-tetraphenyl-1, 2' -biimidazole, 2 '-bis (2-methylphenyl) -4, 5, 4', 5 '-tetraphenyl-1, 2' -biimidazole and 2, 2 '-diphenyl-4, 5, 4', 5 '-tetraphenyl-1, 2' -biimidazole.

Examples of the triazine compound include: 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6-piperonyl-1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxystyryl) -1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (5-methylfuran-2-yl) vinyl ] -1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (furan-2-yl) vinyl ] -1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (4-diethylamino-2-methylphenyl) vinyl ] -1, 3, 5-triazine and 2, 4-bis (trichloromethyl) -6- [ 2- (3, 4-dimethoxyphenyl) vinyl ] -1, 3, 5-triazine.

Examples of the oxime ester compound include: n-benzoyloxy-1- (4-phenylthiophenyl) butane-1-one-2-imine, N-ethoxycarbonyloxy-1-phenylpropan-1-one-2-imine, N-benzoyloxy-1- (4-phenylthiophenyl) octane-1-one-2-imine, N-acetoxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethane-1-imine and N-acetoxy-1- [ 9-ethyl-6- { 2-methyl-4- (3, 3-dimethyl-2, 4-dioxocyclopentylmethyl-oxy) benzoyl } -9H-carbazol-3-yl ] ethane-1-imine.

Examples of benzoin compounds include: benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.

Examples of the benzophenone compound include: benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4 '-methyldiphenyl sulfide, 3', 4, 4 '-bis (diethylamino) benzophenone, 4, 4' -tetrakis (t-butylperoxycarbonyl) benzophenone, and 2, 4, 6-trimethylbenzophenone.

Among these, the acylphosphine oxide compound and the alkylphenone compound are preferable, and the alkylphenone compound is more preferable, in terms of easily obtaining a resin layer having more excellent curability and transparency.

The content of the polymerization initiator (D) in the present composition is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and preferably 15 parts by mass or less, more preferably 8 parts by mass or less, per 100 parts by mass of the total of the compound (a), the compound (B) and the compound (C) described below, in terms of easily obtaining a resin layer having high surface hardness, a small haze value, and more excellent adhesion to a substrate and an inorganic film.

< Compound (B) >

The present composition may contain a compound (B) represented by the following formula (B) in addition to the compound (a) in order to easily obtain a resin layer having more excellent adhesion to a substrate and an inorganic film.

The compound (B) contained in the present composition may be one kind or two or more kinds.

[ solution 14]

In the formula (B), R¹⁰Is a hydrogen atom or a methyl group.

L represents an organic group having an alicyclic hydrocarbon group having 6 to 20 carbon atoms, and may be a group in which a hydrogen atom of the alicyclic structure is substituted with a group other than a (meth) acryloyl group or an atom such as a hydroxyl group, a hydrocarbon group or a halogen atom.

L examples of the alicyclic hydrocarbon group include those mentioned for X³The same groups as those exemplified above, and the like.

L the carbon number of the organic group is preferably 8 or more, more preferably 10 or more, and preferably 15 or less, more preferably 12 or less.

L examples of the alicyclic hydrocarbon group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl and bicyclo [2.2.1 ] ring]Heptylalkyl, bicyclo [2.2.2]Octyl radical, tricyclo [3.3.1.1^3，7]Decyl, bicyclo [2.2.1]Heptenyl, bicyclo [2.2.2]Octenyl and the like. Among these, tricyclo [3.3.1.1 ] is particularly preferable in that a resin layer having a better balance between high hardness and low curing shrinkage can be easily obtained^3，7]A decyl group.

The compound (B) is not particularly limited, and includes: cyclohexyl (meth) acrylate, 1, 4-cyclohexanedimethanol mono (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dimethyloldicyclopentanyl di (meth) acrylate, tricyclodecanedimethanol (meth) acrylate, isobornyl (meth) acrylate, 3-hydroxy-1-adamantyl (meth) acrylate, 2-methyl-2-adamantyl (meth) acrylate, 2-ethyl-2-adamantyl (meth) acrylate, 2-propyl-2-adamantyl (meth) acrylate, 3, 5-dihydroxy-1-adamantyl (meth) acrylate, and mixtures thereof, 3-phenylcarbamoyl-1-adamantyl (meth) acrylate, and the like.

The molecular weight of the compound (B) is preferably 180 or more, more preferably 200 or more, and preferably 600 or less, more preferably 400 or less, from the viewpoint that a resin layer having high surface hardness, a small haze value, and more excellent adhesion to a substrate and an inorganic film can be easily obtained.

When the compound (B) is contained in the present composition, the content of the compound (B) in the present composition is preferably 1 to 50% by mass, more preferably 1 to 30% by mass, from the viewpoint that a resin layer having high surface hardness, a small haze value, and more excellent adhesion to a substrate and an inorganic film can be easily obtained.

The content ratio of the compound (A) to the compound (B) (mass of the compound (A): mass of the compound (B)) in the present composition is preferably 1: 99 to 99: 1, more preferably 80: 20 to 50: 50, for the same reason as described above.

< other ingredients >

The present composition may contain other components known in the art other than the above-mentioned compound (a) and compound (B) and the polymerization initiator (D).

Examples of the other components include: a polyfunctional (meth) acrylic monomer other than the compound (a) and the compound (B) (hereinafter, also referred to as "compound (C)"), a monofunctional (meth) acrylic monomer other than the compound (B), a solvent, an antioxidant, an ultraviolet absorber, a coloring matter, an antireflection agent, a hard coat agent, an antistatic agent, a metal complex compound, a leveling agent, an antifoaming agent, and a coupling agent.

These other components may be one kind or two or more kinds, respectively.

The compound (C) is not particularly limited, and examples thereof include: specific examples of poly (meth) acrylates of trihydric or higher polyhydric alcohols such as glycerin, trimethylolpropane, pentaerythritol, dipentaerythritol include: trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane alkylene oxide-modified tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like. Further, there may be mentioned: tricyclodecane dimethanol di (meth) acrylate, alkanediol di (meth) acrylate, polyalkylene glycol di (meth) acrylate, di-or tri (meth) acrylate having an isocyanurate skeleton, di (meth) acrylate having a bisphenol A skeleton, and the like.

The content of the compound (C) in the present composition is preferably 5% by mass or more, more preferably 15% by mass or more, and preferably 50% by mass or less, more preferably 40% by mass or less, in terms of easily obtaining a resin layer having high surface hardness, a small haze value, and more excellent adhesion to a substrate and an inorganic film.

The proportion of the compound (C) in the present composition with respect to 100% by mass of the total of the compounds (a) to (C) is preferably 10% by mass or more, more preferably 20% by mass or more, and preferably 55% by mass or less, more preferably 45% by mass or less, for the same reason as described above.

The dye is not particularly limited, and may be an inorganic compound or an organic compound, but is preferably an organic compound.

The coloring matter may be appropriately selected from among conventionally known coloring matters according to the intended use of the present composition, but when the present composition is used for a near-infrared cut filter, it is preferable to use a near-infrared absorbing coloring matter.

Examples of such a near-infrared absorbing dye include: squarylium (squarylium) compounds, phthalocyanine compounds, cyanine compounds, dithiol compounds, diimmonium compounds, porphyrin compounds, and crotonium compounds.

The maximum absorption wavelength of the near-infrared absorbing dye is preferably 600nm or more, more preferably 620nm or more, particularly preferably 650nm or more, and preferably 800nm or less, more preferably 760nm or less, particularly preferably 740nm or less. If the maximum absorption wavelength is in such a wavelength range, sufficient near infrared absorption characteristics and visible light transmittance can be achieved at the same time. The near-infrared absorbing dye satisfying such absorption characteristics is particularly preferably a squarylium salt compound, phthalocyanine compound, cyanine compound, or ketanium compound.

The content ratio of the pigment in the present composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and preferably 20% by mass or less, more preferably 10% by mass or less, in terms of excellent visible light transmittance, absorption of light of a desired wavelength, and the like.

Laminate

The resin layer formed from the present composition may be used alone as a resin film, for example, but is preferably used in the form of a laminate with a substrate.

The substrate and the resin layer contained in the laminate may be one layer (one sheet) or two or more layers (one sheet). The resin layer may be present on only one side of the substrate or may be present on both sides.

The thickness of the resin layer(s) may be appropriately selected depending on the intended use, but is preferably 0.1 μm or more, more preferably 0.5 μm or more, particularly preferably 0.7 μm or more, and preferably 20 μm or less, more preferably 10 μm or less, and particularly preferably 5 μm or less.

The substrate is preferably a transparent plate-like body having an average transmittance of 85% or more of light in a wavelength region of 400nm to 700nm, and is preferably formed of a material that transmits visible light, and examples thereof include a resin substrate and a glass substrate. Among these, the resin base material is preferable because it is excellent in processability and excellent in adhesion to the resin layer.

Examples of the resin base material include: polycarbonate resins, acrylic resins, polyester resins, polyether resins, polyolefin resins, epoxy resins, alkyd resins, melamine resins, polyurethane resins, polyimide resins, polyamide resins, norbornene resins, and the like.

Examples of the glass substrate include substrates made of soda-lime glass (soda-lime glass), borosilicate glass (borosilicate glass), alkali-free glass (alkali free glass), quartz glass, chemically strengthened glass, physically strengthened glass, phosphate glass containing copper, fluorophosphate glass containing copper, and the like.

At least one of the base material and the resin layer preferably contains a pigment. In particular, when the laminate is used for a near-infrared cut filter, it is preferable to use a near-infrared absorbing dye.

The near-infrared absorbing dye may be the same dye as described above, and the content of the dye in the substrate or the resin layer may be in the same range as the content ratio of the dye in the present composition.

The thickness of these substrates may be appropriately selected depending on the intended use, and is preferably 10 μm or more, more preferably 20 μm or more, and particularly preferably 25 μm or more, and is preferably 100mm or less, more preferably 50mm or less, and particularly preferably 10mm or less.

The method for producing the laminate is not particularly limited, and a laminate can be produced by forming a resin layer (film) from the present composition on a support, peeling off the support, and laminating the obtained resin layer (film) on a substrate.

As the method of the coating, a known method can be appropriately selected. For example, there may be mentioned: wire bar coating method, dip coating method, casting coating method, spray coating method, spinner coating method, bead coating method, blade coating method, roll coating method, curtain coating method, slit film coater method, gravure coater method, slit reverse coater method, micro gravure method, Comma coater method, screen printing method, flexographic printing method.

After the present composition is applied to a substrate, the applied present composition may be dried, for example, before the following hardening.

The curing method is not particularly limited, and there are a method of curing by heating, a method of irradiating light, and the like, and particularly, a method of irradiating light is preferable.

The light to be irradiated is preferably light having a wavelength of 200nm to 500 nm. The curing may be accelerated by heating, for example, after or after irradiation with light.

The temperature condition upon irradiation with light is preferably 0 ℃ or more, more preferably 10 ℃ or more, and preferably 100 ℃ or less, more preferably 60 ℃ or less.

The atmosphere when light is irradiated may be atmospheric air, but an inert gas atmosphere is preferable in terms of reducing the influence of oxygen inhibition and the like. Examples of the inert gas include nitrogen and argon.

The quantity of light (cumulative quantity of light) can be, for example, from 50mJ/cm²～20000mJ/cm²The range of the nitrogen concentration is preferably 100mJ/cm in the nitrogen atmosphere²Above, more preferably 200mJ/cm²Above, and preferably 10000mJ/cm²Hereinafter, more preferably 8000mJ/cm²The following.

The laminate may further have an inorganic film. The inorganic film may be formed on the substrate, but is preferably formed on the resin layer in terms of further exerting the effect of providing the resin layer.

As the inorganic film, there may be mentioned: conductive films such as dielectric multilayer films and Indium Tin Oxide (ITO) films; and films of metals such as gold, platinum, and copper, oxides thereof, and alloys containing these metals.

The laminate can be preferably used for a display device such as a touch panel; surface materials for membrane switches, keypads, and the like; an electrode substrate constituting a liquid crystal cell of a liquid crystal display element; and optical films such as retardation films, transparent electrode-equipped films for touch panels, and films for near-infrared cut filters, and the like, and are particularly preferably used for near-infrared cut filters (films for use).

Optical filter

The optical filter according to an embodiment of the present invention preferably includes the laminate and the dielectric multilayer film. The dielectric multilayer film may be formed directly on the substrate, but is preferably formed on the resin layer in terms of further exerting the effect of providing the resin layer.

The optical filter is not particularly limited, and is preferably a near infrared cut filter.

The dielectric multilayer film is preferably a film having the ability to reflect near infrared rays. The dielectric multilayer film may be provided on one surface or both surfaces of the laminate. When the optical filter is provided on one side, an optical filter excellent in manufacturing cost and manufacturing easiness can be obtained, and when the optical filter is provided on both sides, an optical filter having high strength and being less likely to warp can be obtained.

The dielectric multilayer film may be a film in which high refractive index material layers and low refractive index material layers are alternately stacked.

As a material constituting the high refractive index material layer, a material having a refractive index of 1.7 or more can be used, and a material having a refractive index in a range of usually 1.7 to 2.5 can be selected. Examples of such a material include materials containing titanium oxide, zirconium oxide, tantalum pentoxide, niobium pentoxide, lanthanum oxide, yttrium oxide, zinc sulfide, indium oxide, and the like as a main component, and containing titanium oxide, tin oxide, cerium oxide, and the like in a small amount (for example, 0% to 10% with respect to the main component).

As a material constituting the low refractive index material layer, a material having a refractive index of 1.6 or less can be used, and a material having a refractive index in a range of 1.2 to 1.6 can be selected. Examples of such a material include silicon dioxide, aluminum oxide, lanthanum fluoride, magnesium fluoride, and sodium aluminum hexafluoride.

The method of laminating the high refractive index material layer and the low refractive index material layer is not particularly limited as long as a dielectric multilayer film in which these material layers are laminated is formed. For example, a dielectric multilayer film in which high refractive index material layers and low refractive index material layers are alternately stacked may be formed directly on the stacked body by a Chemical Vapor Deposition (CVD) method, a sputtering method, a vacuum evaporation method, an ion-assisted evaporation method, an ion plating method, or the like.

In this case, the surface of the resin layer may be subjected to a surface treatment by corona treatment, plasma treatment, or the like.

When the thickness of each of the high refractive index material layer and the low refractive index material layer is in the above range, the optical film thickness calculated by the product (n × d) of the refractive index (n) and the film thickness (d) becomes substantially the same value as λ/4, and the shielding/transmission of a specific wavelength tends to be easily controlled in relation to the optical characteristics of reflection and refraction.

The value of λ (nm) is, for example, 700nm or more, preferably 750nm or more, and, for example, 1400nm or less, preferably 1300nm or less.

The total number of layers of the high refractive index material layer and the low refractive index material layer in the dielectric multilayer film is preferably 5 layers or more, more preferably 10 layers or more, and preferably 60 layers or less, more preferably 50 layers or less, based on the entire optical filter.

When warpage occurs in the optical filter during formation of the dielectric multilayer film, a method of forming the dielectric multilayer film on both surfaces of the laminate, irradiating the surface of the laminate on which the dielectric multilayer film is formed with electromagnetic waves such as ultraviolet rays, or the like may be performed in order to eliminate the warpage. In the case of irradiating electromagnetic waves, the irradiation may be performed during the formation of the dielectric multilayer film, or may be performed separately after the formation.

In the optical filter, a functional film such as an antireflection film, a hard coat film, or an antistatic film may be appropriately provided on a surface of the laminate opposite to the surface on which the dielectric multilayer film is provided, or on a surface of the dielectric multilayer film opposite to the surface on which the laminate is provided, for the purpose of increasing the surface hardness of the substrate or the dielectric multilayer film, improving chemical resistance, preventing static electricity, and eliminating damage, within a range not to impair the effects of the present invention.

Examples

The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples.

[ measurement of molecular weight ]

The molecular weight of the compound synthesized in the following synthesis example was measured by Gel Permeation Chromatography (GPC) under the following measurement conditions using GPC columns (G2000HX L2, G3000HX L1, G4000HX L1) manufactured by tokoa (Tosoh).

GPC measurement conditions:

dissolution vehicle: tetrahydrofuran (THF)

Flow rate 1.0m L/min

Sample concentration: 1.0% by mass

Sample injection amount 100. mu. L

Column temperature: 40 deg.C

The detector: differential refractometer

Standard substance: monodisperse polystyrene

Synthesis example 1 Synthesis of Compound (A-1)

In a reaction vessel equipped with a stirrer, a thermometer and a condenser, 0.0194g of 2, 6-di-tert-butyl-4-methylphenol, 0.12 g of 3-hydroxy-1-adamantyl acrylate (molecular weight: 222, manufactured by mitsubishi gas chemistry, inc., molecular weight: 222), 27.047g (0.12 mol) and isophorone diisocyanate (molecular weight: 222, manufactured by Evonik corporation, inc., molecular weight: 26.481g (0.12 mol) were dissolved in 19g of Methyl Ethyl Ketone (MEK) at room temperature, and 0.405g of dioctyltin dilaurate was added, followed by heating to 70 ℃ while stirring. After confirming dissolution of the 3-hydroxy-1-adamantyl acrylate and transparentization of the solution, 3-hydroxy-1-adamantylpropyl was additionally added27.047g of alkenoic acid ester, the reaction being continued at 70 ℃. When an absorption spectrum of an isocyanate group was confirmed in the infrared absorption spectrum (2280 cm)^-1) After almost disappeared, the reaction was terminated.

The reaction mixture was purified by column chromatography using silica gel having ethyl acetate/hexane as a dissolution liquid, thereby obtaining an acrylic urethane compound (a-1) molecular weight: 667).

Hydrogen Nuclear Magnetic Resonance (NMR) of Compound (A-1) Using a Nuclear magnetic resonance apparatus (trade name "JNM-ECX 400", manufactured by Nippon electronics Ltd.), (¹H-nuclear magnetic resonance，¹H-NMR) spectrum was measured. As a result, it was confirmed that the structure of the obtained compound (A-1) was represented by the following formula (A-1).

¹H-NMR(DMSO-d₆)；1.04(m，22H)，1.51(m，1H)，2.02(m，20H)，2.26(d，1H)，2.46(d，1H)，3.79(m，1H)，5.86(d，2H)，6.06(t，2H)，6.21(d，2H)，6.82(s，1H)，6.93(s，1H)

[ solution 15]

Synthesis example 2 Synthesis of Compound (A-2)

In a reaction vessel equipped with a stirrer, a thermometer and a condenser, 0.0194g of 2, 6-di-tert-butyl-4-methylphenol, 0.0194g of 3-hydroxy-1-adamantylacrylate (manufactured by mitsubishi gas chemical (kokai), molecular weight: 222)27.047g (0.12 mol), and norbornane diisocyanate (manufactured by mitsui gas chemical (kokai), molecular weight: 206)24.7g (0.12 mol) were dissolved in 19g of MEK, and 0.405g of dioctyltin dilaurate was added, followed by heating to 70 ℃ with stirring at room temperature. After dissolution of 3-hydroxy-1-adamantyl acrylate was confirmed and the solution was made transparent, 27.047g of 3-hydroxy-1-adamantyl acrylate was added thereto and the reaction was continued at 70 ℃. When an absorption spectrum of an isocyanate group was confirmed in the infrared absorption spectrum (2280 cm)^-1) After almost disappeared, the reaction was terminated.

The reaction mixture was purified by column chromatography using silica gel having ethyl acetate/hexane as a dissolution liquid, whereby an acrylic urethane compound (A-2) (molecular weight: 651) was obtained.

From the results of Synthesis example 1 and the molecular weight, the structure of the obtained compound (A-2) was considered to be a structure represented by the following formula (A-2).

[ solution 16]

Synthesis example 3 Synthesis of Compound (A-3)

In a reaction vessel equipped with a stirrer, a thermometer and a condenser, 0.0194g of 2, 6-di-tert-butyl-4-methylphenol, 0.12 g of 3-hydroxy-1-adamantylacrylate (manufactured by mitsubishi gas chemical (kokai) having a molecular weight of 222)27.047g (0.12 mol) and 23.3g (0.12 mol) of 1, 3-hydrogenated xylylene diisocyanate (manufactured by katsuzai chemical (kokai) having a molecular weight of 194) were dissolved in 19g of MEK at room temperature, and 0.405g of dioctyltin dilaurate was added, followed by heating to 70 ℃ with stirring. After dissolution of 3-hydroxy-1-adamantyl acrylate was confirmed and the solution was made transparent, 27.047g of 3-hydroxy-1-adamantyl acrylate was added thereto and the reaction was continued at 70 ℃. When an absorption spectrum of an isocyanate group was confirmed in the infrared absorption spectrum (2280 cm)^-1) After almost disappeared, the reaction was terminated.

The reaction mixture was purified by column chromatography using silica gel having ethyl acetate/hexane as a dissolution liquid, whereby an acrylic urethane compound (A-3) (molecular weight: 639) was obtained.

From the results of Synthesis example 1 and the molecular weight, the structure of the obtained compound (A-3) was considered to be a structure represented by the following formula (A-3).

[ solution 17]

[ Synthesis example 4] Synthesis of Compound (A-4)

In a reaction vessel equipped with a stirrer, a thermometer and a condenser, 0.0194g of 2, 6-di-tert-butyl-4-methylphenol, 0.0194g of 3-hydroxy-1-adamantyl acrylate (molecular weight: 222, manufactured by mitsubishi gas chemistry, inc., molecular weight: 222), 27.047g (0.12 mol), and 4, 4' -methylenebis (cyclohexyl isocyanate) (manufactured by Evonik corporation, molecular weight: 262), 31.4g (0.12 mol), were dissolved in 19g of MEK, and 0.405g of dioctyltin dilaurate was added thereto, followed by heating to 70 ℃ with stirring at room temperature. After dissolution of 3-hydroxy-1-adamantyl acrylate was confirmed and the solution was made transparent, 27.047g of 3-hydroxy-1-adamantyl acrylate was added thereto and the reaction was continued at 70 ℃. When an absorption spectrum of an isocyanate group was confirmed in the infrared absorption spectrum (2280 cm)^-1) After almost disappeared, the reaction was terminated.

The reaction mixture was purified by column chromatography using silica gel having ethyl acetate/hexane as a dissolution liquid, whereby an acrylic urethane compound (A-4) (molecular weight: 707) was obtained.

From the results of Synthesis example 1 and the molecular weight, the structure of the obtained compound (A-4) was considered to be a structure represented by the following formula (A-4).

[ solution 18]

Synthesis example 5 Synthesis of Compound (A-5)

In a reaction vessel equipped with a stirrer, a thermometer and a condenser, 0.0194g of 2, 6-di-tert-butyl-4-methylphenol, 0.12 g of 3-hydroxy-1-adamantylacrylate (molecular weight: 222, manufactured by mitsubishi gas chemistry, inc., molecular weight: 222), 27.047g (0.12 mol), and isophorone diisocyanate (molecular weight: 222, manufactured by Evonik) corporation, 26.481g (0.12 mol) were dissolved in 19g of MEK, and 0.405g of dioctyltin dilaurate was added thereto, followed by heating to 70 ℃ while stirring at room temperature. After confirming dissolution of 3-hydroxy-1-adamantyl acrylate and transparentization of the solution, 1, 4-cyclohexanedimethanol monoacrylate (Japanese chemical conversion)Strand production, molecular weight: 198)23.8g (0.12 mol), and the reaction was continued at 70 ℃. When an absorption spectrum of an isocyanate group was confirmed in the infrared absorption spectrum (2280 cm)^-1) After almost disappeared, the reaction was terminated.

The reaction mixture was purified by column chromatography using silica gel having ethyl acetate/hexane as a dissolution liquid, whereby an acrylic urethane compound (A-5) (molecular weight: 643) was obtained.

From the results of Synthesis example 1 and the molecular weight, the structure of the obtained compound (A-5) was considered to be a structure represented by the following formula (A-5).

[ solution 19]

[ Synthesis example 6] Synthesis of Compound (A-6)

In a reaction vessel equipped with a stirrer, a thermometer and a condenser, 0.0194g of 2, 6-di-tert-butyl-4-cresol, 0.0194g of 3-hydroxy-1-adamantylacrylate (manufactured by Mitsubishi gas chemistry, molecular weight: 222)27.047g (0.12 mol) and 29.0g of an isocyanurate of isophorone diisocyanate (trade name: Westana (VESTANAT) T1890/100, manufactured by Evonik corporation, NCO value: 17.3 wt%) were dissolved in 19g of MEK at room temperature, and 0.405g of dioctyltin dilaurate was added thereto, followed by stirring and temperature rise to 70 ℃. After confirming that the solution was uniformly transparent, 27.047g of 3-hydroxy-1-adamantyl acrylate and 29.0g of an isocyanurate product of isophorone diisocyanate were added thereto, and the reaction was continued at 70 ℃. When an absorption spectrum of an isocyanate group was confirmed in the infrared absorption spectrum (2280 cm)^-1) After almost disappeared, the reaction was terminated.

The reaction mixture was purified by column chromatography using silica gel with ethyl acetate/hexane as a eluent, whereby an acrylic urethane compound (A-6) (molecular weight: 1334) was obtained.

Of Compound (A-6) determined by the same apparatus as described above¹The results of the H-NMR measurement are as follows,it was confirmed that the structure of the obtained compound (A-6) was represented by the following formula (A-6).

¹H-NMR(DMSO-d₆)；1.04-2.02(m，87H)，2.26(m，3H)，2.46(m，3H)，3.79(m，3H).5.86(m，3H)，6.06(m，3H)，6.21(m，3H)，6.99(m，3H)

[ solution 20]

Example 1 preparation of curable resin composition solution

A curable resin composition was prepared by adding 3.0g of compound (A-1) and 0.09g of compound (D-1) to a 20m L sample tube and diluting the mixture with 10g of MEK.

[ examples 2 to 11 and comparative examples 1 to 4] preparation of curable resin compositions

Compositions were prepared in the same manner as in example 1, except that the compounds described in table 1 were used in such proportions as described in table 1. The numerical values in the columns of the compositions in table 1 are the proportions (parts by mass) of the compounds used when the total of the compounds (a) to (C) is 100 parts by mass.

The details of the compounds (B-1) to (B-4), the compounds (C-1) to (C-3) and the compounds (D-1) to (D-3) described in Table 1 are shown in Table 2.

[ measurement of haze ]

The curable resin compositions obtained in the examples and comparative examples were applied to a substrate (norbornane resin film [ 100 a thick in arton (arm) FEKE100, manufactured by JSR corporation ]) so that the thickness of the obtained resin layer became 3 μm, and then cured by ultraviolet irradiation in a nitrogen atmosphere, thereby obtaining a substrate with a resin layer. The haze value of the resin layer-provided substrate obtained was measured using the substrate obtained by the method according to Japanese Industrial Standard (JIS) K7136 using a haze meter (trade name: haiz gard (yard-gard) II) manufactured by tokyo seiki. The haze value was judged to be good when it was 0.1 or less. The results are shown in Table 1.

[ Pencil hardness test ]

The hardness of the resin layer in the obtained substrate with a resin layer was measured by the pencil hardness test in the same manner as the haze measurement according to the method described in JIS K5600-5-4.

Specifically, after the substrate with the resin layer was subjected to humidity adjustment at a temperature of 25 ℃ and a humidity of 60% RH for 2 hours, the surface of the resin layer was scratched with a test pencil at a load of 4.9N, and the highest pencil hardness without damage among three or more of the five test materials was set as an evaluation value. The case where the pencil hardness was B or more was judged to be good. The results are shown in Table 1.

[ test for resistance to moist Heat (adhesion) ]

In the same manner as the haze measurement, a substrate with a resin layer was obtained. On the resin layer of the obtained substrate with a resin layer, the following inorganic film (dielectric multilayer film, ITO sputtering film or gold vapor deposition film) was formed. The obtained substrate with the inorganic film was placed in a constant temperature and humidity chamber at 85 ℃ and 85% RH for 1000 hours. After that, the adhesiveness between the inorganic film and the resin layer was evaluated as follows. The results are shown in Table 1.

Dielectric multilayer film: SiO is alternately laminated by a conventionally known vapor deposition method₂(film thickness: 10 nm-100 nm) layer and TiO₂(film thickness: 10 nm-120 nm) layer (number of layers 28, total thickness 3 μm)

ITO sputtering film: ITO was deposited by a known method to form a film (thickness: 500nm)

Gold vapor deposition film: a film (thickness: 500nm) obtained by vapor deposition of gold by a conventionally known method

Using a cutter, 11 cuts reaching the resin layer were drawn at 1mm intervals in a checkered pattern in the longitudinal direction and in the transverse direction on the inorganic film surface, and a total of 100 square squares were drawn. An adhesive tape (cellophane tape (registered trademark), available under the trade name CT24 from Nichiban (stock) was attached to the surface of the notch, and the number of inorganic films remaining on the substrate was evaluated by peeling off the adhesive tape. The number of inorganic films remaining on the substrate side even after the tape was peeled off in 100 squares was 90 or more, and the adhesion was judged to be good.

[ Table 2]

Claims

1. A curable resin composition comprising a compound (A) selected from at least one compound represented by the following formula (A1) and the following formula (A2) and a polymerization initiator (D):

[ solution 1]

In the formula (A1), R¹And R²Each independently being a hydrogen atom or a methyl group, X³～X⁵Each independently a C6-20 hydrocarbon group having an alicyclic hydrocarbon group, Y¹And Y²Each independently an organic group having 6 to 40 carbon atoms and having an alicyclic hydrocarbon group, m is an integer of 0 to 20, and when m is 2 or more, a plurality of X' s⁴And Y¹May be the same or different;

[ solution 2]

In the formula (A2), R³～R⁶Each independently being a hydrogen atom or a methyl group, X⁶～X¹⁰Each independently a C6-20 hydrocarbon group having an alicyclic hydrocarbon group, Y³And Y⁴Each independently an organic group having an alicyclic hydrocarbon group and having 6 to 40 carbon atoms, and n is an integer of 0 to 20A plurality of X's in the case where n is 2 or more⁷、X¹⁰、Y⁴And R⁶May be the same or different.

2. The curable resin composition according to claim 1, wherein X is³～X⁵At least one of (a) and the X⁶～X¹⁰At least one of the above (A) and (B) is independently a hydrocarbon group having an adamantane ring and having 10 to 20 carbon atoms.

3. The curable resin composition according to claim 1 or 2, wherein Y is¹～Y²And Y and³～Y⁴at least one of the groups is independently a group represented by any one of the following (y1) to (y 5):

[ solution 3]

4. The curable resin composition according to any one of claims 1 to 3, comprising a compound (B) represented by the following formula (B):

[ solution 4]

5. The curable resin composition according to claim 4, wherein the content ratio of the compound (A) to the compound (B) (mass of compound (A): mass of compound (B)) in the curable resin composition is 1: 99 to 99: 1.

6. The curable resin composition according to any one of claims 1 to 5, wherein the compound (A) has a molecular weight of 500 to 5000.

7. The curable resin composition according to claim 4 or 5, wherein the molecular weight of the compound (B) is 180 to 600.

8. A laminate comprising a substrate and a resin layer formed from the curable resin composition according to any one of claims 1 to 7.

9. The laminate according to claim 8, wherein at least one of the base material and the resin layer comprises a pigment.

10. An optical filter comprising the laminate according to claim 8 or 9 and a dielectric multilayer film.

11. A compound represented by the following formula (a):

[ solution 5]

12. The compound of claim 11, wherein at least one of said X "is adamantanediyl.

13. The compound according to claim 11 or 12, wherein the Y "is a group represented by any one of the following (Y1) to (Y5):

[ solution 6]