KR20210006324A - Compound, latent additive, composition, cured product, method for preparing cured product and method for preparing composition - Google Patents

Abstract

An object of the present invention is to provide a compound capable of forming a cured product excellent in light resistance and heat resistance. The present invention is a compound having a structure represented by the following general formula (A) and a polymerizable group-containing group (wherein ring A represents a 5- or 6-membered aromatic ring, or a 5- or 6-membered heterocycle, and R ¹⁰¹ each independently represents an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, etc., and R ¹⁰² is each independently an alkyl group having 1 to 40 carbon atoms, an alkene having 2 to 20 carbon atoms. Represents a nil group, an aryl group having 6 to 20 carbon atoms, etc., a1 represents an integer of 1 or more, and a2 represents an integer of 1 or more.

Description

Compound, latent additive, composition, cured product, method for preparing cured product and method for preparing composition

The present invention relates to a compound capable of forming a cured product excellent in light resistance and heat resistance, and a latent additive.

In order to impart functions such as light resistance and heat resistance to a cured product of a curable composition, a method of adding an additive such as an ultraviolet absorber and an antioxidant is known (Patent Documents 1 to 3).

Japanese Unexamined Patent Application Publication No. 2011-048382 US9518031 Japanese Unexamined Patent Application Publication No. 2015-108649

However, the ultraviolet absorber or the like described in Patent Documents 1 to 3 has a problem in that it may inhibit the curing of the curable composition. This problem is due to the fact that the ultraviolet absorber has an action of absorbing the irradiated light to cure the curable composition, and in order to have such an action, the addition of an ultraviolet absorber to the curable composition may cause curing inhibition. .

As a means of solving the above problems, in the composition before curing, the above-described light-absorbing function is inactivated, and a latent additive capable of being activated after curing has been studied.

However, even when a latent additive is used, functions such as light resistance and heat resistance cannot be sufficiently imparted in some cases.

The present invention has been made in view of the above problems, and its main purpose is to provide a compound and latent additive capable of forming a cured product having excellent light resistance and heat resistance without causing curing inhibition.

The present inventors conducted a careful review to solve the above problems, as a result of simultaneously satisfying both that the latent additive containing a specific compound sufficiently proceeds the curing of the curable composition and that the additive is stably maintained in the cured product, It has found that the effects such as light resistance and heat resistance can be stably exhibited over time.

The inventors of the present invention have come to complete the present invention based on these findings.

That is, the present invention is a compound having a structure represented by the following general formula (A) and a polymerizable group-containing group (hereinafter sometimes referred to as compound A).

(In the formula, ring A represents a 5- or 6-membered aromatic ring, or a 5- or 6-membered heterocycle,

R ¹⁰¹ is each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a carbon atom A heterocyclic-containing group of number 2 to 20,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from the following group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from the following group 2,

R ¹⁰² is each independently an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, and 2 to carbon atoms 20 heterocyclic-containing group, silyl group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from the following group 1,

or

One or two or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represent a group substituted with a divalent group selected from the following group 2,

a1 represents an integer of 1 or more,

a2 represents an integer of 1 or more.)

(Group 1: ethylenic unsaturated group, halogen atom, acyl group, acyloxy group, substituted amino group, sulfonamide group, sulfonyl group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, imide group, car Barmoyl group, sulfonamide group, phosphonic acid group, phosphoric acid group, salt of carboxyl group, salt of sulfo group, salt of phosphonic acid group, salt of phosphoric acid group)

(Group 2: carbon-carbon double bond, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO -S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -O-CO-NH-, -NR '- (R' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.), -SS-, -SO ₂ -, a group combining them under the condition that oxygen atoms are not adjacent to each other)

In the present invention, the compound A is a compound represented by the following general formula (B1), (B2), (B3) or (C) (hereinafter referred to as compound B1, compound B2 and compound B3, compound C, respectively, and compounds B1 to B3 May be collectively referred to as compound B.).

(In the formula, R ³ and R ⁴ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. An arylalkyl group of, a heterocycle-containing group having 2 to 20 carbon atoms, a polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

R ¹¹ and R ¹² are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. An arylalkyl group, a heterocyclic-containing group having 2 to 20 carbon atoms, -OR ¹⁰² , a polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

At least one of R ¹¹ and R ¹² is -OR ¹⁰² ,

R ¹⁰² is the same as R ¹⁰² in the formula (A),

m1 represents the integer of 1-10,

b1 represents an integer of 0-4,

b2 represents the integer of 0-2,

X ¹ represents an m1 valent group or an m1 valent polymerizable group-containing group,

At least one of R ¹¹ , R ¹² , R ³ , R ⁴ and X ¹ is a polymerizable group-containing group.)

(In the formula, R ⁵ and R ⁶ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. An arylalkyl group of, a heterocycle-containing group having 2 to 20 carbon atoms, a polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

R ²¹ and R ²² are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. An arylalkyl group, a heterocyclic-containing group having 2 to 20 carbon atoms, -OR ¹⁰² , a polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

At least one of R ²¹ and R ²² is -OR ¹⁰² ,

R ¹⁰² and R ¹⁰² are as defined in the general formula (A),

m2 represents an integer from 1 to 10,

b3 represents the integer of 0-4,

b4 represents an integer of 0-3,

X ² represents an m2 valent group or an m2 valent polymerizable group-containing group,

At least one of R ²¹ , R ²² , R ⁵ , R ⁶ and X ² is a polymerizable group-containing group.)

(In the formula, R ⁷ , R ⁸ and R ⁹ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and the number of carbon atoms. 7-20 arylalkyl group, C2-C20 heterocyclic-containing group, polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

R ³¹ , R ³² , R ³³ and R ³⁴ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, Arylalkyl group having 7 to 20 carbon atoms, heterocyclic-containing group having 2 to 20 carbon atoms, -OR ¹⁰² , polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

At least one of R ³¹ and R ³² is -OR ¹⁰² ,

At least one of R ³³ and R ³⁴ is -OR ¹⁰² ,

R ¹⁰² and R ¹⁰² are as defined in the general formula (A),

m3 represents an integer from 1 to 10,

m31 is 1,

m32 represents an integer of 0-2,

The sum of m31 and m32 represents an integer of 1 to 3,

b5 represents an integer of 0-2,

b6 represents the integer of 0-3,

b7 represents an integer from 0 to [3-(m31+m32)],

X ³ represents an m3 valent group or an m3 valent polymerizable group-containing group,

At least one of R ³¹ , R ³² , R ³³ , R ³⁴ , R ⁷ , R ⁸ , R ⁹ and X ³ is a polymerizable group-containing group.)

(In the formula, R ⁴² and R ⁴³ each independently represent a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, or a polymerizable group-containing group,

R ⁴⁴ is each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a carbon atom A group containing 2 to 20 heterocyclic rings, a group containing a polymerizable group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

R ¹⁰² and R ¹⁰² are as defined in the general formula (A),

m4 represents an integer from 1 to 10,

c1 represents the integer of 0-2,

X ⁴ represents an m4 valent group or an m4 valent polymerizable group-containing group,

At least one of R ⁴² , R ⁴³ , R ⁴⁴ and X ⁴ is a polymerizable group-containing group.)

In the present invention, at least one of R ³ and R ⁴ in the general formula (B1) is a polymerizable group-containing group, at least one of R ⁵ and R ⁶ in the general formula (B2) is a polymerizable group-containing group, and the general formula It is preferable that at least one of R ⁷ and R ⁸ in (B3) is a polymerizable group-containing group, and at least one of R ⁴⁴ in the general formula (C) is a polymerizable group-containing group.

In the present invention, the compound includes a compound represented by the general formula (B3), and at least one of R ^{7 which is} meta to R ³¹ and R ^{8 which} is meta to R ³³ in the general formula (B3) is the polymerizable group It is preferably a containing group.

In the present invention, R ¹⁰² represents an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 2 It is preferable that the methylene group at the end of the oxygen atom side in the heterocyclic ring-containing group of ~ 20 is substituted with -CO-O-.

The present invention is a latent additive comprising the compound A.

The present invention is a composition comprising the compound A and a resin.

In the present invention, it is preferable that the resin contains a polymerizable compound.

The present invention is a cured product of the above-described composition.

The present invention is a method for producing a cured product having a step of polymerizing the polymerizable compound contained in the above-described composition.

The present invention is a method for preparing a composition having a step of desorbing R ¹⁰² from the compound contained in the above composition.

The present invention relates to a compound, a latent additive, a composition containing the compound, and a method for preparing a cured product and a cured product thereof, and a method for preparing the composition.

Hereinafter, the compound of the present invention, the latent additive, the composition, the cured product, the method of producing the cured product and the method of producing the composition will be described in detail.

A. Compounds and latent additives

First, the compound of the present invention and the latent additive will be described.

The compound of the present invention is a compound (Compound A) having a structure represented by the following general formula (A) and a polymerizable group-containing group.

In addition, the latent additive of the present invention includes the compound A.

(In the formula, ring A represents a 5- or 6-membered aromatic ring, or a 5- or 6-membered heterocycle,

R ¹⁰¹ is each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group or a carbon atom having 7 to 20 carbon atoms Represents a heterocyclic ring-containing group of 2 to 20,

R ¹⁰² is each independently an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, and 2 to carbon atoms Represents a heterocyclic ring-containing group of 20 or a silyl group,

a1 represents an integer of 1 or more,

a2 represents an integer of 1 or more.)

More specifically, in the general formula (A), ring A represents a 5- or 6-membered aromatic ring, or a 5- or 6-membered heterocycle,

R ¹⁰¹ is each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a carbon atom A heterocyclic-containing group of number 2 to 20,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from the following group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from the following group 2,

R ¹⁰² is each independently an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, and 2 to carbon atoms 20 heterocyclic-containing group, silyl group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from the following group 1,

or

One or two or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represent a group substituted with a divalent group selected from the following group 2,

a1 represents an integer of 1 or more,

a2 represents an integer of 1 or more.

(Group 1: ethylenic unsaturated group, halogen atom, acyl group, acyloxy group, substituted amino group, sulfonamide group, sulfonyl group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, imide group, car Barmoyl group, sulfonamide group, phosphonic acid group, phosphoric acid group, salt of carboxyl group, salt of sulfo group, salt of phosphonic acid group, salt of phosphoric acid group)

(Group 2: carbon-carbon double bond, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO -S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -O-CO-NH-, -NR '- (R' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.), -SS-, -SO ₂ -, a group combining them under the condition that oxygen atoms are not adjacent to each other)

When the latent additive of the present invention contains the compound A, a cured product having excellent light resistance and heat resistance can be formed without causing curing inhibition. The reason is inferred as follows.

Since the compound A has a polymerizable group-containing group, copolymerization of the compound A and the polymerizable compound occurs during curing of the curable composition. As a result, the compound A becomes a part of the polymer and can effectively suppress sublimation, precipitation, and the like from the cured product. The suppression of sublimation and precipitation from the cured product is maintained even after R ¹⁰² is desorbed from the compound A to exhibit ultraviolet absorbing ability, antioxidant ability, and the like.

Further, in the compound A, since the phenolic hydroxyl group is protected by R ¹⁰² , the ultraviolet absorbing ability for imparting the function of light resistance and the antioxidant ability for imparting the function of heat resistance are inactivated. As a result, the latent additive containing the compound A can suppress curing inhibition of the curable composition, and a sufficiently cured cured product can be obtained.

Moreover, since the compound A has R ¹⁰² protecting a phenolic hydroxyl group and a polymerizable group-containing group, it is excellent in compatibility with resins such as a polymerizable compound, and it becomes easy to uniformly disperse in the composition. As a result, the compound A can exhibit the like with a tally of R ¹⁰² ease, ultraviolet absorption capability, intelligent room after oxidation of R ¹⁰² desorbed in the total composition or cured product. Further, due to such excellent dispersibility, the precipitation of the compound A and the R ¹⁰² desorbed product from the cured product is less.

From the above, since the compound A contained in the latent additive has the above-described structure and a polymerizable group-containing group, the latent additive has little change over time in ultraviolet absorbing ability and oxidation preventing ability, and has excellent light resistance and heat resistance. It becomes possible to form cargo.

Since the latent additive of the present invention exhibits little change in UV absorbing ability and antioxidant ability over time, it can exhibit the desired UV absorption ability and antioxidant ability over a long period of time by adding a small amount compared to the amount of UV absorber and antioxidant required in the past. I can.

For this reason, the latent additive is used in applications in which it is difficult to increase the amount of additives added, such as thin film members such as optical members, and that a small amount of addition is required to impart a desired ultraviolet absorption ability, and more specifically, displays such as color filters. It is particularly useful for imparting ultraviolet absorption ability, etc. to the use of an optical member used for

In addition, the latent additive has excellent dispersibility as described above, and a composition excellent in uniform dispersibility can be obtained.

The latent additive can express functions such as light resistance at a desired timing. For this reason, for example, when used for a photosensitive resin such as a positive type resin, after decomposition and development of the positive type resin, ultraviolet absorption ability or the like can be expressed in the remaining positive type resin to impart light resistance and the like.

From this point of view, the latent additive is also useful for imparting light resistance to a composition not containing a polymerizable compound.

Hereinafter, each component of the latent additive of the present invention will be described in detail.

1.Compound A

The compound A contained in the latent additive has a structure represented by the general formula (A) (hereinafter sometimes referred to as structure A) and a polymerizable group-containing group.

(1) Polymerizable group-containing group

The compound A has a polymerizable group-containing group.

The polymerizable group of the polymerizable group-containing group can be appropriately set according to the kind and use of the compound A, and examples thereof include a radical polymerizable group, a cationic polymerizable group, an anionic polymerizable group, and the like.

In the present invention, for example, when the latent additive is used together with a radical polymerizable compound, it is preferable that the polymerizable group is a radical polymerizable group. This is because, when the polymerizable group is the group described above, the latent additive can more easily form a cured product excellent in light resistance and heat resistance.

Examples of the radical polymerizable group include an acryloyl group (CH ₂ =CH-CO-), a methacryloyl group (CH ₂ =C(CH ₃ )-CO-), a vinyl group ((CH ₂ =CH-) or (- And ethylenically unsaturated double bond groups such as CH=CH-)).

In the present invention, it is more preferable that the radical polymerizable group is a methacryloyl group. Because the methacryloyl group is excellent in reactivity, the latent additive can more easily form a cured product excellent in light resistance and heat resistance.

Examples of the cationic polymerizable group include cyclic ether groups such as an epoxy group and an oxetane group, and a vinyl ether group.

Examples of the anionic polymerizable group include an epoxy group, a lactone group, an acryloyl group, and a methacryloyl group.

The bonding portion of the polymerizable group-containing group may be an arbitrary portion of the structure A.

The polymerizable group-containing group may be bonded to ring A in the structure A, or bonded as a substituent for substituting one or two or more hydrogen atoms of the substituent R ¹⁰¹ .

The polymerizable group-containing group is not limited as long as it contains a polymerizable group, and the polymerizable group may be directly bonded to the structure A, or the polymerizable group may be bonded through a bonding group.

On the other hand, compounds represented by formulas (B-22), (B-23), (B-24), (B-3), (B-31) and (C-7) to be described later contain a polymerizable group in ring A. A compound to which a group is directly bonded, that is, a compound having a structure in which one of the hydrogen atoms in ring A in the structure represented by the general formula (A) is substituted with the polymerizable group-containing group. In addition, the compound represented by formula (B-32) to be described later is a compound having a structure in which one of the hydrogen atoms of the substituent R ¹⁰¹ is substituted with the polymerizable group-containing group.

The number of the polymerizable group-containing groups may be at least one in the compound A, but is preferably 1 or more and 10 or less, particularly preferably 1 or more and 6 or less, and particularly preferably 1 or more and 3 or less. This is because the compound A is capable of forming a cured product excellent in light resistance and heat resistance, and the compound A is easily synthesized.

As such a polymerizable group-containing group, for example, a group represented by the following general formula (D) (hereinafter, it may be referred to as a polymerizable group-containing group D) can be used.

In the present invention, since the polymerizable group-containing group is the polymerizable group-containing group D, the compound A can form a cured product excellent in light resistance and heat resistance, and the compound A is easily synthesized.

(In the formula, L ₁ represents a direct bond or a d+n-valent bonding group,

D represents a polymerizable group,

d represents the integer of 1-10,

n is the number of bonds to the structure represented by the general formula (A), and represents an integer of 1 to 10,

d+n represents an integer of 2 to 11,

* Represents a bonded portion with the structure represented by the general formula (A).)

D in the polymerizable group-containing group D represents the number of polymerizable groups contained in the polymerizable group-containing group D, and is an integer of 1 to 10, to obtain a latent additive capable of forming a cured product having excellent light resistance and heat resistance. It is preferable that it is 1-3, and it is preferable that it is 1 from a viewpoint of the balance of the effect of being able and the ease of synthesis.

N in the polymerizable group-containing group D is the number of bonds to the structure represented by the general formula (A) and is an integer of 1 to 10. When n is 2 or more, L ₁ is a crosslinking group connecting structures A to each other. Wherein n is appropriately set according to the use of the compound A, for example, m1 to m3 and “(3-2) the second embodiment described in the section “(3-1) First embodiment” to be described later. It can be the same as m4 etc. described in ". In the present invention, it is preferable that n is an integer of 1 to 6, particularly, it is preferably an integer of 1 to 3, and particularly preferably an integer of 1 to 2. This is because the compound A is capable of forming a cured product excellent in light resistance and heat resistance, and the compound A is easily synthesized.

D+n in the polymerizable group-containing group D is an integer of 2 to 11, from the viewpoint of the balance of the effect of obtaining a latent additive capable of forming a cured product excellent in light resistance and heat resistance, and ease of synthesis. It is preferable that it is an integer of 6, it is more preferable that it is an integer of 2-5, and it is especially preferable that it is an integer of 2-4.

The polymerizable group-containing group D is, for example, R ¹¹ , R ¹² , R ²¹ , R ²² in the general formulas (B1) to (B3) described in “(3-1) First Embodiment” to be described later. R ³¹ , R ³² , R ³³ , R ³⁴ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ , and described in the “(3-2) second embodiment” section to be described later In the case of a substituent bonded to the structure A such as R ⁴² , R ⁴³ and R ⁴⁴ in the general formula (C), n=1, and a direct bond or a d+1 valent bonding group can be used as L ₁ .

In addition, the polymerizable group-containing group D is, for example, X when m1 to m3 in the general formulas (B1) to (B3) described in the section "(3-1) First Embodiment" to be described later are each 1 ¹ to X ³ , or in the case of X ⁴ in the general formula (C) described in the section "(3-2) Second Embodiment" to be described later, n=1, and as L ₁ , a direct bond or d+1 valency A coupler can be used.

Moreover, the polymerizable group-containing group D is, for example, m1 to m3 in the general formulas (B1) to (B3) described in the section "(3-1) First Embodiment" to be described later, and "(3- 2) In the case of X ¹ to X ⁴ when m4 in the general formula (C) described in the "Second Embodiment" section is 2 or more, n=m (any one of =m1 to m4), and L ₁ A d+m-valent bonding group can be used.

L ₁ used in the general formula (D) represents a direct bond or a d+n-valent bonding group.

In the present invention, L ₁ is preferably a d+n-valent bonding group from the viewpoint of a balance between the effect of obtaining a latent additive capable of forming a cured product having excellent light resistance and heat resistance, and ease of synthesis.

As L ₁ used as a d+n-valent bonding group, there is no problem as long as it is a divalent or higher group. For example, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, represented by the following (II-a) or (II-b) Group, >C=O, -NH-CO-, -CO-NH-, >NR ⁵³ or an aliphatic hydrocarbon group having 1 to 120 carbon atoms having the same valence as d+n, 6 to 35 carbon atoms An aromatic ring-containing hydrocarbon group or a C2-C35 heterocycle-containing group is mentioned.

R ⁵³ is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 120 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic group having 2 to 35 carbon atoms.

Among the methylene groups of the aliphatic hydrocarbon group having 1 to 120 carbon atoms, the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and the heterocyclic ring-containing group having 2 to 35 carbon atoms used as L ₁ and R ⁵³ One or more than one is -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO-S-,- S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -O-CO-NH-, -NR'-, -SS -, -SO ₂ -, a nitrogen atom, or a combination thereof may be substituted, and the aromatic ring or heterocycle may be condensed with another ring. R'represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. In addition, the combination is conditional on that oxygen atoms are not adjacent to each other.

However, the nitrogen atom, phosphorus atom, or the bonding group represented by the following (II-a) or (II-b) used for L ₁ is used as a trivalent bonding group. In addition, an oxygen atom or a sulfur atom used as L ₁ , a bonding group of >C=O, -NH-CO-, -CO-NH-, or >NR ⁵³ is used as a divalent bonding group.

(* means bonding with adjacent groups as a * part.)

The number of carbon atoms in the case where the methylene group in the aliphatic hydrocarbon group having 1 to 120 carbon atoms is substituted, refers to the number of carbon atoms after the methylene group is substituted, and does not indicate the number of carbon atoms before the methylene group is substituted. The same applies when a methylene group in other groups is substituted.

Examples of the aliphatic hydrocarbon group having 1 to 120 carbon atoms used for R ⁵³ include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, dibutyl, tertiary butyl, isobutyl, amyl, isoamyl, Tertiary amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl , Isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isononyl, and alkyl groups such as decyl; Methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, dibutyloxy, tertiary butyloxy, isobutyloxy, amyloxy, isoamyloxy, tertiary amyloxy, hexyloxy, cyclohexyloxy , Heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, and other alkoxy groups; Methylthio, ethylthio, propylthio, isopropylthio, butylthio, dibutylthio, tertiary butylthio, isobutylthio, amylthio, isoamylthio, tertiary amylthio, hexylthio, cyclohexylthio, heptyl Alkylthio groups such as thio, isoheptylthio, tertiary heptylthio, n-octylthio, isooctylthio, tertiary octylthio, and 2-ethylhexylthio; Vinyl, 1-methylethenyl, 2-methylethenyl, 2-propenyl, 1-methyl-3-propenyl, 3-butenyl, 1-methyl-3-butenyl, isobutenyl, 3-pentenyl, Alkenyl groups such as 4-hexenyl, cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl, eicosenyl, and tricosenyl, and groups in which these groups are substituted by a substituent to be described later. I can.

Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms used for R ⁵³ include arylalkyl groups such as benzyl, phenethyl, diphenylmethyl, triphenylmethyl, styryl and cinnamyl; Aryl groups such as phenyl and naphthyl; Aryloxy groups such as phenoxy and naphthyloxy; And arylthio groups such as phenylthio and naphthylthio, and groups in which one or two or more of the hydrogen atoms of these groups are substituted with a substituent to be described later.

Examples of the heterocyclic-containing group having 2 to 35 carbon atoms used for R ⁵³ include pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, iso Quinolyl, imidazolyl, benzoimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxa Zolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidin-1-yl, 2-piperidon-1-yl, 2,4-dioxyimidazolidin-3-yl, 2,4 -Dioxyoxazolidin-3-yl, benzotriazoyl, and the like, and groups in which one or two or more of the hydrogen atoms of these groups are substituted with a substituent to be described later.

The structure of the aliphatic hydrocarbon group having 1 to 120 carbon atoms used in the bonding group L ₁ can be appropriately set according to the use of the compound A.

The aliphatic hydrocarbon group may be linear, branched, cyclic (alicyclic hydrocarbon), or a combination thereof.

The aliphatic hydrocarbon group having 1 to 120 carbon atoms of a divalent or higher number used for L ₁ is a structure in which one or two or more of the hydrogen atoms are removed from the aliphatic hydrocarbon group having 1 to 120 carbon atoms used for the aforementioned R ⁵³ Can be raised. Specifically, alkylenes such as methylene, ethylene, propylene, butylene and butyldiyl; One or two or more of the methylene groups of the alkylene are substituted with -O-, -S-, -CO-O-, -O-CO-; Residues of diols such as ethanediol, propanediol, butanediol, pentanediol, and hexanediol; Dithiol residues such as ethanedithiol, propanedithiol, butanedithiol, pentanedithiol, and hexanedithiol, and groups in which one or two or more of the hydrogen atoms of these groups are substituted with a substituent to be described later. .

Examples of the trivalent aliphatic hydrocarbon group having 1 to 120 carbon atoms used in L ₁ are, specifically, alkylidines such as propylidine and 1,1,3-butylidine, and one or two or more of the hydrogen atoms of these groups. The group substituted by the substituent mentioned later is mentioned.

The number of carbon atoms in the case where a hydrogen atom in the aliphatic hydrocarbon group having 1 to 120 carbon atoms is substituted with a substituent refers to the number of carbon atoms after the hydrogen atom is substituted with a substituent, and indicates the number of carbon atoms before the hydrogen atom is substituted with a substituent It is not. The same applies when hydrogen atoms in other groups are substituted.

The structure of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms used in L ₁ can be appropriately set according to the use of the compound A.

As the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms of divalent or higher carbon atoms used in the above L ₁ , one or two hydrogen atoms from the monovalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms used for R ⁵³ The group which is the above-removed structure is mentioned. Specifically, arylene groups such as phenylene and naphthylene; Residues of difunctional phenols such as catechol and bisphenol; 2,4,8,10-tetraoxaspiro[5,5]undecane, and the like, and groups in which one or two or more of the hydrogen atoms of these groups are substituted with a substituent to be described later.

As the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms used in L ₁ , one or two or more of phenyl-1,3,5-trimethylene and hydrogen atoms of these groups are substituted by a substituent to be described later. Can be raised.

The structure of the heterocyclic ring-containing group having 2 to 35 carbon atoms used in L ₁ can be appropriately set depending on the use of the compound.

As the heterocyclic-containing group having 2 to 35 carbon atoms of divalent or higher carbon atoms used in L ₁ , for example, one hydrogen atom is formed from the monovalent heterocyclic ring-containing group having 2 to 35 carbon atoms used in R ⁵³ described above. Alternatively, a group having a structure in which two or more are removed may be mentioned. Specifically, groups having a pyridine ring, a pyrimidine ring, a piperidine ring, a piperazine ring, a triazine ring, a furan ring, a thiophene ring, an indole ring, and the like, and one or two or more of the hydrogen atoms of these groups are in the substituents described later. And groups substituted by.

The trivalent heterocycle-containing group having 2 to 35 carbon atoms used in L ₁ is a group having an isocyanuric ring, a group having a triazine ring, and one or two or more of the hydrogen atoms of these groups by a substituent to be described later. And substituted groups.

The aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group, the heterocycle-containing group and the like may have a substituent, and unless otherwise specified, unsubstituted or unsubstituted or substituted with a substituent. Examples of the substituent include the same substituents for substituting a hydrogen atom such as an alkyl group used in R ¹⁰¹ and the like described in the section "(2) Structure A" to be described later.

As for L _{1, when} d+n is 2, 3, 4, 5, 6, general formula (1) that can be used when n is 2 in Japanese Unexamined Patent Application Publication No. 2017-001184, and when n is 3 As general formula (2) that can be used, general formula that can be used when n is 4 (3), general formula that can be used when n is 5 (4), and general formula that can be used when n is 6 (5) The prayers listed are mentioned.

When L ₁ is a divalent bonding group, >C=O, -NH-CO-, -CO-NH-, >NR ⁵³ or a divalent aliphatic hydrocarbon group having 1 to 120 carbon atoms is preferable, and 2 It is preferably an aliphatic hydrocarbon group having 1 to 20 valent carbon atoms, more preferably an aliphatic hydrocarbon group having 1 to 10 divalent carbon atoms, and more preferably a divalent aliphatic hydrocarbon group having 2 to 8 carbon atoms, Among them, it is more preferably a divalent aliphatic hydrocarbon group having 3 to 6 carbon atoms. This is because, when L ₁ has such a structure, the compound A can form a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

When L ₁ is a trivalent to hexavalent bonding group, it is preferably an aliphatic hydrocarbon group having 1 to 30 carbon atoms, and among them, it is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms. When L ₁ is a trivalent bonding group, it is preferably a trivalent aliphatic hydrocarbon group having 2 to 10 carbon atoms, and among them, it is preferably a trivalent aliphatic hydrocarbon group having 3 to 8 carbon atoms. This is because, when L ₁ has such a structure, the compound A can form a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

Wherein L ₁ is an aliphatic hydrocarbon group having 1 to 120 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic-containing group having 2 to 35 carbon atoms, one or two of the methylene groups of these groups This is -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO -S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NH-CO-O-, -NR It is preferably substituted with'-, -SS-, -SO ₂ -or a combination thereof, and among them, it is preferably substituted with -O-, -CO-, -O-CO-, -CO-O- And, in particular, it is preferably substituted with a divalent substituent that is -O- or -O-CO-.

In addition, the group used for L ₁ is one or two or more of the methylene groups in the group is -O-, -S-, -CO-, -O-CO-, -CO-O-, -S-CO-, It is preferably substituted with -CO-S-, and particularly preferably substituted with -O-, -S-, or -O-CO-.

This is because, when L ₁ has such a structure, the compound A can form a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

The number of methylene groups substituted with divalent substituents such as -O- in the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group and heterocycle-containing group in L ₁ is preferably 1 or more and 10 or less, and among them 1 or more and 5 It is preferable that it is below, and it is preferable that it is 1 or more and 3 or less.

In the above L ₁ , it is preferable that the methylene group at the terminal of the structure A side is substituted with -O-, that is, that L ₁ is bonded to the structure A through -O-. This is because, when L ₁ has such a structure, the compound A can form a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

One which is substituted with the L ₁ is a methylene group -S- terminal A side of the structure, that is, it is also preferable that L ₁ is bonded to the structure via A -S-. This is because, when L ₁ has such a structure, the compound A can form a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

Further, the L ₁ group is in the terminal methylene in the side polymerizable group is substituted by -O-, that is, it is preferable that L ₁ is bonded to the polymerizable group with -O-. This is because, when L ₁ has such a structure, the compound A can form a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

As the L ₁ , when d+n is 2, a group represented by the following general formula (1) can be preferably used.

When d+n is 3, L ₁ can preferably use a group represented by the following general formula (2).

When d+n is 4, L ₁ may preferably use a group represented by the following general formula (3).

When d+n is 5, L ₁ may preferably use a group represented by the following general formula (4).

When d+n is 6, L ₁ may preferably use a group represented by the following general formula (5).

(In the general formula (1), Y ¹ is a single bond, -NR ⁵⁷ -, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or 2 to carbon atoms Represents a heterocyclic-containing group of 35, and one or two or more of the methylene groups in the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and the heterocyclic ring-containing group having 2 to 35 carbon atoms are -O-, -S-, -CO-, -COO-, -OCO- or -NH- or a combination of these may be substituted with a bonding group,

Z ¹ and Z ² are each independently a direct bond, -O-, -S-, >CO, -CO-O-, -O-CO-, -SO ₂ -, -SS-, -SO-, >NR ⁵⁸ or >PR ⁵⁸ ,

R ⁵⁷ and R ⁵⁸ represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic-containing group having 2 to 35 carbon atoms,

* Means that the * part is combined with an adjacent group.)

(In the general formula (2), Y ¹¹ represents a trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic-containing group having 2 to 35 carbon atoms,

Z ¹ , Z ² and Z ³ each independently represent a group in the same range as the group represented by Z ¹ to Z ² in the general formula (1),

One or two or more of the methylene groups in the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, and heterocycle-containing group are carbon-carbon double bonds, -O-, -CO-, -O-CO-, -CO-O-, or It may be substituted with -SO ₂ -.)

(In the general formula (3), Y ¹² is a carbon atom or a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic ring having 2 to 35 carbon atoms. Represents a group,

One or two or more of the methylene groups in the aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and a heterocyclic ring-containing group having 2 to 35 carbon atoms are -COO-, -O-, -OCO-, It may be substituted with -NHCO-, -NH- or -CONH-,

Z ¹ to Z ⁴ are each independently a group in the same range as the group represented by Z ¹ to Z ² in the general formula (1).)

(In the general formula (4), Y ¹³ represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 30 carbon atoms, or a heterocyclic-containing group having 2 to 30 carbon atoms,

One or two or more of the methylene groups in the aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and a heterocyclic ring-containing group having 2 to 35 carbon atoms are -COO-, -O-, -OCO-, It may be substituted with -NHCO-, -NH- or -CONH-,

Z ¹ to Z ⁵ are each independently a group in the same range as the group represented by Z ¹ to Z ² in the general formula (1).)

(In the general formula (5), Y ¹⁴ is a single bond, a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic ring having 2 to 35 carbon atoms. Represents a group,

One or more of the methylene groups in the aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic ring-containing group having 2 to 35 carbon atoms is -COO-, -O-, -OCO-, It may be substituted with -NHCO-, -NH- or -CONH-,

Z ¹ to Z ⁶ are each independently a group in the same range as the group represented by Z ¹ to Z ² in the general formula (1).)

In the group represented by the general formula (1), examples of the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms used for Y ¹ include groups having the corresponding number of carbon atoms among the divalent aliphatic hydrocarbon groups used for L ₁ . have.

As the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, more specifically, methane, ethane, propane, iso-propane, butane, sec-butane, tert-butane, iso-butane, hexane, 2-methylhexane, 3-methylhexane, heptane, 2-methylheptane, 3-methylheptane, iso-heptane, tert-heptane, 1-methyloctane, iso-octane, tert-octane, cyclopropane, cyclobutane, cyclopentane, cyclohexane, Divalent groups in which the hydrogen atoms of aliphatic hydrocarbons such as cycloheptane, 2,4-dimethylcyclobutane, and 4-methylcyclohexane are substituted with Z ¹ and Z ² are mentioned.

Further, examples of the aliphatic hydrocarbon group include a divalent group in which the hydrogen atom of an alicyclic hydrocarbon such as cyclooctane, cyclodecane, adamantane, norbornene is substituted with Z ¹ and Z ² .

The methylene group contained in these groups may be substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -NH-, or a combination thereof.

Examples of the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms used for Y ¹ in the group represented by the general formula (1) include a divalent aromatic ring-containing hydrocarbon group used for L ₁ .

Examples of the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms include, more specifically, a divalent group in which the hydrogen atom of an aromatic ring-containing hydrocarbon such as benzene, naphthalene, and biphenyl is substituted with Z ¹ and Z ² . I can.

Examples of the divalent C2-C35 heterocyclic-containing group used for Y ¹ in the group represented by the general formula (1) include a divalent heterocyclic-containing group used for L ₁ .

As the divalent C2-C35 heterocycle-containing group, more specifically, pyridine, pyrazine, piperidine, piperazine, pyrimidine, pyridazine, triazine, hexahydrotriazine, furan, tetrahydrofuran , A divalent group in which a hydrogen atom of a heterocycle-containing compound such as chroman, xanthene, thiophene, and thiorane is substituted with Z ¹ and Z ² .

Each functional group, such as an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, and a heterocycle-containing group, used in Y ¹ in the group represented by the above general formula (1) does not have a substituent, and unless otherwise specified, a substituent It may be unsubstituted or have a substituent.

Substituents for substituting hydrogen atoms such as aliphatic hydrocarbon groups, aromatic ring-containing hydrocarbon groups and heterocycle-containing groups are substituted with hydrogen atoms such as alkyl groups used in R ¹⁰¹ and the like described in section "(2) Structure A" to be described later. The same substituents as described above are mentioned, for example, a halogen atom, a cyano group, a nitro group, or an alkoxy group having 1 to 8 carbon atoms.

An aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and a carbon atom number of 2 to 35 used for R ⁵⁷ and R ⁵⁸ in the group represented by the general formula (1) Examples of the heterocyclic-containing group include the same groups as those used for R ⁵³ and R ⁵⁴ described above.

A trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and a compound having 2 to 35 carbon atoms used for Y ¹¹ in the group represented by the general formula (2) Examples of the cyclic-containing group include aliphatic hydrocarbons, aromatic ring-containing hydrocarbons, and heterocycle-containing compounds exemplified in the description of Y ¹ in the above general formula (1) in which hydrogen atoms are substituted with Z ¹ , Z ² and Z ³ . have.

The methylene group contained in these groups may be substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -NH-, or a combination thereof.

In the group represented by the above general formula (3), a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and a compound having 2 to 35 carbon atoms used for Y ¹² As the cyclic-containing group, the aliphatic hydrocarbon, aromatic ring-containing hydrocarbon, and heterocycle-containing compound illustrated in the description of Y ¹ in the general formula (1) have a tetravalent hydrogen atom substituted with Z ¹ , Z ² , Z ³ and Z ⁴ . Can be raised.

The methylene group contained in these groups may be substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -NH-, or a combination thereof.

In the group represented by the general formula (4), a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and a compound having 2 to 35 carbon atoms used for Y ¹³ As the subcyclic-containing group, the hydrogen atoms of the aliphatic hydrocarbon, aromatic ring-containing hydrocarbon, and heterocycle-containing compound illustrated in the description of Y ¹ in the general formula (1) are substituted with Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ . The five-valent flag that was made is mentioned.

The methylene group contained in these groups may be substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -NH-, or a combination thereof.

A hexavalent C2-C35 aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group having 6-35 carbon atoms, and a C2-C35 heterocyclic-containing group used for Y ¹⁴ in the general formula (5) Is substituted with Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ in the aliphatic hydrocarbon, aromatic ring-containing hydrocarbon, and heterocycle-containing compound illustrated in the description of Y ¹ in the above general formula (1). The six-valent flag that was made is mentioned.

The methylene group contained in these groups may be substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -NH-, or a combination thereof.

Y ¹ in the general formula (1) is preferably a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic-containing group having 2 to 35 carbon atoms, , Among them, it is preferably an aliphatic hydrocarbon group having 1 to 35 carbon atoms, particularly preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, and most preferably an aliphatic hydrocarbon group having 1 to 10 carbon atoms, and especially It is preferable that it is a C2-C8 aliphatic hydrocarbon group, and it is especially preferable that it is a C3-C6 aliphatic hydrocarbon group especially. This is because when L ₁ has such a structure, the compound A can form a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

In the general formulas (2) to (5), Y ¹¹ , Y ¹² , Y ¹³ and Y ¹⁴ represent an aliphatic hydrocarbon group having 1 to 35 carbon atoms and an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms of each valency. Or it is preferable that it is a C2-C35 heterocyclic-containing group, Especially it is preferable that it is a C1-C35 aliphatic hydrocarbon group, and it is especially preferable that it is a C1-C30 aliphatic hydrocarbon group, and carbon atom number It is most preferable that it is an aliphatic hydrocarbon group of 1-20. This is because, when L ₁ has such a structure, the compound A can form a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

Among these, in the present invention, Y ¹² in the general formula (3) is preferably an aliphatic hydrocarbon group having 2 to 10 carbon atoms, and most preferably an aliphatic hydrocarbon group having 3 to 8 carbon atoms. This is because, when L ₁ has such a structure, the compound A can form a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

In the general formulas (1) to (5), Y ¹ , Y ¹¹ , Y ¹² , Y ¹³ and Y ¹⁴ are aliphatic hydrocarbon groups having 1 to 35 carbon atoms and aromatic rings having 6 to 35 carbon atoms respectively In the case of a containing hydrocarbon group or a heterocyclic-containing group having 2 to 35 carbon atoms, one or two or more of these methylene groups are -O-, -S-, -CO-, -COO-, -OCO-, -NH- or It is preferable to be substituted with a group combining these, among them, -O-, -CO-, -O-CO-, -CO-O- is preferable, and in particular -O-, -O-CO- It is preferably substituted with. Further, it is also preferable that the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, or heterocycle-containing group used for Y ¹ , Y ¹¹ , Y ¹² , Y ¹³ and Y ¹⁴ is substituted with -O-, -S-. This is because the compound A is capable of forming a cured product excellent in light resistance and heat resistance.

In the general formulas (1) to (5), the number of methylene groups substituted with -O- and the like described above in Y ¹ , Y ¹¹ , Y ¹² , Y ¹³ and Y ¹⁴ is preferably 1 or more and 10 or less. In particular, it is preferably 1 or more and 5 or less, and preferably 1 or more and 3 or less. This is because the compound A is capable of forming a cured product excellent in light resistance and heat resistance.

In the general formulas (1) to (5), Z ¹ to Z ⁶ are preferably -O-. This is because the compound A is capable of forming a cured product excellent in light resistance and heat resistance.

In the present invention, it is preferable that the group bonded to the polymerizable group-containing group in Z ¹ to Z ⁶ is -O-. Further, in the present invention, it is preferable that the groups other than those bonded to the polymerizable group-containing group in Z ¹ to Z ⁶ are -O- and -S-. This is because the compound A is capable of forming a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

On the other hand, as a group other than bonding with a polymerizable group-containing group, specifically, a group bonded to ring A in the above structure A, a group bonded to R ¹⁰¹ as a substituent for substituting one or more of the hydrogen atoms of the substituent R ¹⁰¹ And the like.

The number of the polymerizable group-containing groups is not limited as long as it is 1 or more in Compound A, but is preferably 1 or more and 10 or less, particularly preferably 1 or more and 5 or less, and particularly preferably 1 or more and 3 or less. This is because, when the number is within the above-described range, the latent additive containing the compound A can form a cured product excellent in light resistance and heat resistance. In addition, this is because the compound A is easily synthesized.

When two or more types of the polymerizable group-containing group are contained in Compound A, one type may be used or two or more types may be used.

In the present invention, it is preferable that the type of the polymerizable group-containing group is one. This is because the latent additive containing the compound A is capable of forming an excellent cured product due to light resistance, heat resistance, and the like. In addition, this is because the compound A is easily synthesized.

(2) Structure A

The compound A contains the structure (structure A) represented by the general formula (A) described above.

Ring A in the general formula (A) is a 5- or 6-membered aromatic ring, or a 5- or 6-membered heterocycle.

The 5-membered aromatic ring is a 5-membered ring having aromaticity, and there is no limitation as long as the ring structure of the 5-membered ring contains only carbon atoms, and cyclopentadiene, ferrocene, and the like may be mentioned.

The 5-membered heterocycle is a 5-membered ring having aromaticity, and there is no limitation as long as the ring structure of the 5-membered ring includes atoms other than carbon atoms, furan, thiophene, pyrrole, pyrrolidine, pyrazolidine, and pyra Sol, imidazole, imidazolidine, oxazole, isoxazole, isoxazolidine, thiazole, isothiazole, isothiazolidine, and the like.

The 6-membered aromatic ring is a 6-membered ring having aromaticity, and there is no limitation as long as the ring structure of the 6-membered ring contains only carbon atoms, and benzene, naphthalene, anthracene, fluorene, perylene, pyrene, and the like can be mentioned.

The 6-membered heterocycle is a 6-membered ring having aromaticity, and there is no limitation as long as the ring structure of the 6-membered ring contains atoms other than carbon atoms, piperidine, piperazine, morpholine, thiomorpholine, pyridine, And pyrazine, pyrimidine, pyridazine, and triazine.

Even if these rings are condensed or substituted with other rings, there is no problem, and for example, quinoline, isoquinoline, indole, ulrolidine, benzoxazole, benzotriazole, azulene, and the like may be formed.

In the present invention, the ring A includes both a 5-membered ring and a 6-membered ring to correspond to a 6-membered ring.

In addition, it is assumed that the ring A includes both an aromatic ring and a heterocyclic ring as a heterocyclic ring.

In the present invention, from the viewpoint of obtaining a cured product having excellent functions such as light resistance and heat resistance, it is preferably a 6-membered aromatic ring or a heterocyclic ring, and among them, it is preferable to include only a 6-membered aromatic ring, and in particular benzene , Naphthalene, anthracene, pyrene, etc. are preferable.

R ¹⁰¹ in the general formula (A) is each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 carbon atoms. -20 arylalkyl group or a heterocycle-containing group having 2 to 20 carbon atoms, and R ¹⁰² is each independently an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, and 6 to 20 carbon atoms Aryl group, arylalkyl group having 7 to 20 carbon atoms, heterocyclic-containing group having 2 to 20 carbon atoms, or silyl group.

The halogen atom includes fluorine, chlorine, bromine, and iodine.

Examples of the alkyl group having 1 to 40 carbon atoms include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-octyl, adamantyl And the like.

Examples of the aryl group having 6 to 20 carbon atoms include phenyl, naphthyl, and anthracenyl.

Examples of the arylalkyl group having 7 to 20 carbon atoms include benzyl, fluorenyl, indenyl, and 9-fluorenylmethyl group.

Examples of the heterocyclic-containing group having 2 to 20 carbon atoms include pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzo Imidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzooxazolyl, isothiazolyl, isoxa Zolyl, indolyl, 2-pyrrolidinone-1-yl, 2-piperidon-1-yl, 2,4-dioxyimidazolidin-3-yl, 2,4-dioxyoxazolidine-3 -Work, etc.

Examples of the alkenyl group having 2 to 20 carbon atoms include vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl, and the like. I can.

As the silyl group, a hydrogen atom may be an unsubstituted silyl group or a substituted silyl group in which a hydrogen atom is substituted with another substituent.

As the substituted silyl group, silyl such as a monoalkylsilyl group, monoarylsilyl group, dialkylsilyl group, diarylsilyl group, trialkylsilyl group, triarylsilyl group, monoalkyldiarylsilyl group, dialkylmonoarylsilyl group Can be raised.

Examples of the monoalkylsilyl group include monomethylsilyl group, monoethylsilyl group, monobutylsilyl group, monoisopropylsilyl group, monodecanesilyl, monoicosansilyl group, monotriacontansilyl group, and the like.

Examples of the monoarylsilyl group include a monophenylsilyl group, a monotolylsilyl group, a mononaphthylsilyl group, and a monoanthrylsilyl group.

Examples of the dialkylsilyl group include a dimethylsilyl group, a diethylsilyl group, a dimethylethylsilyl group, a diisopropylsilyl group, a dibutylsilyl group, a dioctylsilyl group, and a didecansilyl group.

Examples of the diarylsilyl group include a diphenylsilyl group and a ditolylsilyl group.

Examples of the trialkylsilyl group include trimethylsilyl group, triethylsilyl group, dimethylethylsilyl group, triisopropylsilyl group, tributylsilyl group, trioctylsilyl group, and the like.

Examples of the triarylsilyl group include a triphenylsilyl group and a tritolylsilyl group.

Examples of the monoalkyldiarylsilyl group include a methyldiphenylsilyl group and an ethyldiphenylsilyl group.

Examples of the dialkyl monoarylsilyl group include a dimethylphenylsilyl group and a methylethylphenyl group.

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, heterocycle-containing group, alkenyl group, and silyl group are carbon-carbon double bonds, -O-, -S-, -CO-, -O-CO -, -CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, A group selected from -NH-CO-, -NH-CO-O-, -O-CO-NH-, -NR'-, -SS- or -SO ₂ -, or a combination of these under the condition that oxygen atoms are not adjacent to each other It can be substituted with one group. R'represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

In some cases, the alkyl group is substituted with an -O- terminal methylene group and is an alkoxy group.

Examples of the alkoxy group include methyloxy, ethyloxy, iso-propyloxy, butyloxy, sec-butyloxy, tert-butyloxy, iso-butyloxy, amyloxy, iso-amyloxy, tert-amyloxy, Hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, iso-heptyloxy, tert-heptyl Oxy, 1-octyloxy, iso-octyloxy, tert-octyloxy, etc. are mentioned.

The alkyl group, aryl group, arylalkyl group, heterocycle-containing group, alkenyl group, silyl group, and the like do not have a problem even if they have a substituent. As a substituent for substituting one or two or more of the hydrogen atoms of these groups, halogen atoms such as fluorine, chlorine, bromine, and iodine; Acetyl, 2-chloroacetyl, propionyl, octanoyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxy Acyl groups such as carbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, and carbamoyl; Acyloxy groups such as acetyloxy and benzoyloxy; Amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chlorophenylamino, toluidino, anicidino, N-methyl-anilino, Diphenylamino, naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzoylamino, formylamino, pivaloylamino, lauroylamino, carbamoylamino , N,N-dimethylaminocarbonylamino, N,N-diethylaminocarbonylamino, morpholinocarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n -Octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino, sulfamoylamino, N,N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, phenyl Substituted amino groups such as sulfonylamino; Sulfonamide group, sulfonyl group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, imide group, carbamoyl group, sulfonamide group, phosphonic acid group, phosphoric acid group or carboxyl group, sulfo group, phosphonic acid group or And salts of phosphoric acid groups.

That is, as a substituent for substituting one or two or more of the hydrogen atoms of an aryl group, arylalkyl group, heterocycle-containing group, alkenyl group and silyl group, ethylenically unsaturated group, halogen atom, acyl group, acyloxy group, substituted amino group, Sulfonamide group, sulfonyl group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, imide group, carbamoyl group, sulfonamide group, phosphonic acid group or phosphoric acid group or carboxyl group, sulfo group, phosphonic acid group or And salts of phosphoric acid groups.

The R ¹⁰¹ may be bonded to a plurality of R ¹⁰¹ to form a ring such as a benzene ring or a naphthalene ring.

R ¹⁰¹ is a latent ultraviolet absorber, preferably an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocyclic-containing group having 2 to 20 carbon atoms from the viewpoint of excellent light resistance, etc. It is more preferable that it is a C7-20 arylalkyl group or a C2-C20 heterocyclic-containing group. In particular, it is preferable that the methylene group at the terminal of the ring A side is an arylalkyl group having 7 to 20 carbon atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms substituted with -CO-. Examples of such a group include a benzoimidazolyl group, a phenylketone group, and a triazine group.

From the viewpoint of excellent heat resistance and the like as a latent antioxidant, R ¹⁰¹ is preferably an alkyl group having 1 to 10 carbon atoms, and more preferably an unsubstituted alkyl group having 1 to 10 carbon atoms not having a substituent. In particular, a group represented by C ₄ H ₉ is preferable, and a tert-butyl group is most preferable.

Although the bonding moiety of R ¹⁰¹ can be an arbitrary moiety of the ring A, it is preferable that the bonding moiety is bonded to a moiety adjacent to R ¹⁰² . This is because it is easy to impart light resistance and heat resistance.

R ¹⁰² is an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or an arylalkyl group having 2 to 20 carbon atoms. In the case of a heterocycle-containing group, it is preferable that the methylene group at the terminal on the oxygen atom side is substituted with -CO-O-, that is, -CO-O- is bonded to the terminal on the oxygen atom side.

Specifically, R ¹⁰² is preferably an alkyl group having 1 to 40 carbon atoms or an alkenyl group having 2 to 20 carbon atoms in which the methylene group at the terminal on the oxygen atom side is substituted with -CO-O-, and among them The methylene group at the end of the oxygen atom is an alkyl group having 1 to 40 carbon atoms substituted with -CO-O-, that is, -CO-O-R''(R'' may have a substituent It is preferably a group represented by an alkyl group having 1 to 40 carbon atoms). R'' is preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an unsubstituted alkyl group having 1 to 8 carbon atoms not having a substituent. In particular, it is preferable that R'' is a group represented by C ₄ H ₉ , and most preferably a tert-butyl group. This is because functions such as light resistance and heat resistance can be efficiently expressed as a latent antioxidant additive.

A1 in the general formula (A) is an integer of 1 or more.

Said a1 represents the number of R ¹⁰¹ bonded to ring A, and can be appropriately set.

The a1 is preferably an integer of 1 to 3, and more preferably an integer of 1 to 2 from the viewpoint of the compound A being capable of forming a cured product excellent in light resistance and heat resistance, and from the viewpoint of ease of synthesis.

A2 in the general formula (A) is an integer of 1 or more.

The a2 represents the number of -OR ¹⁰² bonded to the ring A, and can be appropriately set according to the use of the latent additive.

For example, when ring A is a 5-membered ring, a2 can be an integer of 1 to 4, and when ring A is a 6-membered ring, it can be an integer of 1-5.

The a2 is preferably an integer of 1 to 3, and more preferably an integer of 1 to 2 from the viewpoint of the compound A being capable of forming a cured product excellent in light resistance and heat resistance, and from the viewpoint of ease of synthesis.

The sum of a1 and a2 is equal to or less than the number of substituents that ring A may take.

Here, ring A is less than or equal to the number of substituents that ring A may have, meaning that it is less than or equal to the number of substitutable hydrogen atoms of ring A. For example, ring A is a heterocycle of only one 5-membered ring such as pyrrolidine. In the case, the sum of a1 and a2 is 5 or less, and when the ring A is a benzene ring, the sum of a1 and a2 is 6 or less.

The compound A may have at least one structure A, but may have two or more, for example, 1 or more and 10 or less of the structure A.

(3) Compound A

The compound A has a structure (structure A) represented by the general formula (A) and a polymerizable group-containing group.

The specific structure of the compound A may be selected according to the use of the latent additive containing the compound A. For example, a structure suitable for using the latent additive as a latent ultraviolet absorber (first embodiment), a structure suitable for using the latent additive as a latent antioxidant (second embodiment), etc. Can be mentioned.

Hereinafter, a more specific structure of the compound A used in the present invention will be described by dividing into the above embodiments.

(3-1) First embodiment

The first embodiment of the compound A is to have a structure suitable for using the latent additive as a latent ultraviolet absorber.

What has such a structure is, for example, a compound represented by the following general formula (B1), (B2) or (B3) (hereinafter sometimes referred to as compound B1, compound B2, and compound B3, respectively. Compounds B1 to B3 may be collectively referred to as compound B.).

In the latent additive of the present invention, it is preferable to use the compound B1 or the compound B3, and it is particularly preferable to use the compound B3. This is because, by using the above-described compound, the latent additive can form a cured product superior in light resistance.

(In the formula, R ³ and R ⁴ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. Represents an arylalkyl group, a heterocycle-containing group having 2 to 20 carbon atoms, or a polymerizable group-containing group,

R ¹¹ and R ¹² are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. Represents an arylalkyl group of, a heterocycle-containing group having 2 to 20 carbon atoms, -OR ¹⁰² or a polymerizable group-containing group,

At least one of R ¹¹ and R ¹² is -OR ¹⁰² ,

R ¹⁰² is the same as R ¹⁰² in the formula (A),

m1 represents the integer of 1-10,

b1 represents an integer of 0-4,

b2 represents the integer of 0-2,

X ¹ represents an m1 valent group or an m1 valent polymerizable group-containing group,

At least one of R ¹¹ , R ¹² , R ³ , R ⁴ and X ¹ is a polymerizable group-containing group.)

More specifically, in the general formula (B1), R ³ and R ⁴ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, and an aryl having 6 to 20 carbon atoms. Group, arylalkyl group having 7 to 20 carbon atoms, heterocyclic-containing group having 2 to 20 carbon atoms, polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

R ¹¹ and R ¹² are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. An arylalkyl group, a heterocyclic-containing group having 2 to 20 carbon atoms, -OR ¹⁰² , a polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

At least one of R ¹¹ and R ¹² is -OR ¹⁰² ,

R ¹⁰² is the same as R ¹⁰² in the formula (A),

m1 represents the integer of 1-10,

b1 represents an integer of 0-4,

b2 represents the integer of 0-2,

X ¹ represents an m1 valent group or an m1 valent polymerizable group-containing group,

At least one of R ¹¹ , R ¹² , R ³ , R ⁴ and X ¹ is a polymerizable group-containing group.

(In the formula, R ⁵ and R ⁶ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. Represents an arylalkyl group, a heterocycle-containing group having 2 to 20 carbon atoms, or a polymerizable group-containing group,

R ²¹ and R ²² are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. Represents an arylalkyl group of, a heterocycle-containing group having 2 to 20 carbon atoms, -OR ¹⁰² or a polymerizable group-containing group,

At least one of R ²¹ and R ²² is -OR ¹⁰² ,

R ¹⁰² is the same as R ¹⁰² in the formula (A),

m2 represents the integer of 1-10,

b3 represents an integer of 0-4,

b4 represents the integer of 0-3,

X ² represents an m2 valent group or an m2 valent polymerizable group-containing group,

At least one of R ²¹ , R ²² , R ⁵ , R ⁶ and X ² is a polymerizable group-containing group.)

More specifically, in the general formula (B2), R ⁵ and R ⁶ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, and an aryl having 6 to 20 carbon atoms. Group, arylalkyl group having 7 to 20 carbon atoms, heterocyclic-containing group having 2 to 20 carbon atoms, polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

R ²¹ and R ²² are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. An arylalkyl group, a heterocyclic-containing group having 2 to 20 carbon atoms, -OR ¹⁰² , a polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

At least one of R ²¹ and R ²² is -OR ¹⁰² ,

R ¹⁰² is the same as R ¹⁰² in the formula (A),

m2 represents the integer of 1-10,

b3 represents an integer of 0-4,

b4 represents the integer of 0-3,

X ² represents an m2 valent group or an m2 valent polymerizable group-containing group,

At least one of R ²¹ , R ²² , R ⁵ , R ⁶ and X ² is a polymerizable group-containing group.)

(In the formula, R ⁷ , R ⁸ and R ⁹ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and the number of carbon atoms. Represents an arylalkyl group of 7 to 20, a heterocycle-containing group having 2 to 20 carbon atoms, or a polymerizable group-containing group,

R ³¹ , R ³² , R ³³ and R ³⁴ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, Represents an arylalkyl group having 7 to 20 carbon atoms, a heterocyclic-containing group having 2 to 20 carbon atoms, -OR ¹⁰² or a polymerizable group-containing group,

At least one of R ³¹ and R ³² is -OR ¹⁰² ,

At least one of R ³³ and R ³⁴ is -OR ¹⁰² ,

R ¹⁰² and R ¹⁰² are as defined in the general formula (A),

m3 represents an integer from 1 to 10,

m31 is 1,

m32 represents an integer of 0-2,

The sum of m31 and m32 represents an integer of 1 to 3,

b5 represents an integer of 0-2,

b6 represents the integer of 0-3,

b7 represents an integer from 0 to [3-(m31+m32)],

X ³ represents an m3 valent group or an m3 valent polymerizable group-containing group,

At least one of R ³¹ , R ³² , R ³³ , R ³⁴ , R ⁷ , R ⁸ , R ⁹ and X ³ is a polymerizable group-containing group.)

More specifically, in the general formula (B2), R ⁷ , R ⁸ and R ⁹ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, and 6 to carbon atoms. 20 aryl group, arylalkyl group having 7 to 20 carbon atoms, heterocyclic-containing group having 2 to 20 carbon atoms, polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

R ³¹ , R ³² , R ³³ and R ³⁴ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, Arylalkyl group having 7 to 20 carbon atoms, heterocyclic-containing group having 2 to 20 carbon atoms, -OR ¹⁰² , polymerizable group-containing group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,

At least one of R ³¹ and R ³² is -OR ¹⁰² ,

At least one of R ³³ and R ³⁴ is -OR ¹⁰² ,

R ¹⁰² and R ¹⁰² are as defined in the general formula (A),

m3 represents an integer from 1 to 10,

m31 is 1,

m32 represents an integer of 0-2,

The sum of m31 and m32 represents an integer of 1 to 3,

b5 represents an integer of 0-2,

b6 represents the integer of 0-3,

b7 represents an integer from 0 to [3-(m31+m32)],

X ³ represents an m3 valent group or an m3 valent polymerizable group-containing group,

At least one of R ³¹ , R ³² , R ³³ , R ³⁴ , R ⁷ , R ⁸ , R ⁹ and X ³ is a polymerizable group-containing group.

The compound B1 ~ B3 are m1-valent group (m1-valent specific atom or group) represented by X ¹ ~ X ^3, respectively, m2 monovalent group (m2 valent specific atom or group), and m3-valent group (m3-valent specific atom or group) It has a structure in which m1~m3 specific groups are bonded.

These m1-m3 groups may be the same or different.

m1, m2, and m3 are each independently an integer of 1 to 10, and from the viewpoint of the balance of the effect of obtaining a latent additive capable of forming a cured product having excellent light resistance and heat resistance, and the ease of synthesis, it is 1 to 6. It is preferable, it is more preferable that it is 1-5, and it is especially preferable that it is 1-4.

Among these, in the present invention, m1 is preferably 1 to 3, and particularly preferably 1 to 2.

Among these, in the present invention, m2 is preferably 1 to 3, and particularly preferably 1 to 2.

Among these, in the present invention, m3 is preferably 1 to 3, particularly preferably 1 to 2, and 1 is preferable.

This is because, when m1 to m3 are in the above-described range, the effect of obtaining a latent additive capable of forming a cured product having excellent light resistance and heat resistance, and the balance of ease of synthesis are excellent.

In the compound B1, at least one of R ¹¹ , R ¹² , R ³ , R ⁴ and X ¹ is a polymerizable group-containing group. Among these, it is preferable that at least one of R ³ and R ⁴ is a polymerizable group-containing group, and more preferably at least R ⁴ is a polymerizable group-containing group. In particular, it is preferable that only R ⁴ of R ¹¹ , R ¹² , R ³ , R ⁴ and X ¹ is a polymerizable group-containing group.

In addition, when b2 is 2 in the compound B1, it is preferable that only one R ⁴ of two R ⁴ is a polymerizable group-containing group.

In the present invention, it is also preferable that only R ³ of R ¹¹ , R ¹² , R ³ , R ⁴ and X ¹ is a polymerizable group-containing group.

In addition, when b1 in the compound B1 is 2 to 4, it is preferable that only one R ³ of 2 to 4 R ³ is a polymerizable group-containing group.

In the compound B2, at least one of R ²¹ , R ²² , R ⁵ , R ⁶ and X ² is a polymerizable group-containing group. Especially, it is preferable that at least one of said R ⁵ and R ⁶ is a polymerizable group-containing group, and it is more preferable that both R ⁵ and R ⁶ are a polymerizable group-containing group.

In the compound B3, at least one of R ³¹ , R ³² , R ³³ , R ³⁴ , R ⁷ , R ⁸ , R ⁹ and X ³ is a polymerizable group-containing group. In particular, the R ⁷ and R ⁸ preferably have at least one polymerizable group-containing group of, and wherein R ⁷ and R ⁸ are both a polymerizable group-containing group is more preferable.

In the compound B3, it is also preferable that only one of R ⁷ and R ⁸ is a polymerizable group-containing group.

When a polymerizable group-containing group is bonded to a benzene ring bonded to a triazine ring in the compound B3, the number of polymerizable group-containing groups bonded to one benzene ring is preferably 2 or less, and one of them is preferred.

For example, when the benzene ring bonded to the triazine ring in the compound B3 has two or more R ⁷ and contains R ⁷ as a polymerizable group-containing group, it is preferable that only one R ⁷ is a polymerizable group-containing group.

In addition, when m32 is 2 in the compound B3, each of the two benzene rings bonded to the triazine ring has two or more R ⁸ , and contains a polymerizable group-containing group R ⁸ , only one R ⁸ in each benzene ring is It is preferably a polymerizable group-containing group.

Further, it the compound B3 in R ³¹ contains metadata above (triazine ring para above with respect to) the R ⁷ and wherein R is at least one polymerization of the ⁸ groups (p-above with respect to the triazine ring) meth above with respect to R ³³ with respect to the group desirable.

This is because, when the polymerizable group-containing group is included as described above in the compounds B1 to B3, the latent additive containing the compound B can form a cured product excellent in light resistance or the like. In addition, this is because the compound B is easy to synthesize.

At least one of R ¹¹ , R ¹² , R ³ and R ⁴ in the compound B1, at least one of R ²¹ , R ²² , R ⁵ and R ⁶ in the compound B2, R ³¹ , R ³² in the compound B3 When at least one of R ³³ , R ³⁴ , R ⁷ , R ⁸ and R ⁹ is a polymerizable group-containing group, the polymerizable group-containing group is, for example, d+n in the group represented by the general formula (D) is 2 What is an integer of -6 can be used preferably, Especially, what is an integer of 2-4 can be used preferably. This is because the latent additive containing the compound B can form a cured product having more excellent light resistance and the like. In addition, this is because the compound B is easy to synthesize.

In the present invention, the polymerizable group-containing group may be bonded to the entire benzene ring bonded to the triazine ring in the compound B3, or the polymerizable group-containing group may be bonded to only part of the benzene ring bonded to the triazine ring. This is because when the polymerizable group-containing group is bonded to the entire benzene ring, it is easy to set it to have less precipitation or the like. When a polymerizable group-containing group is bonded to only a part of the benzene ring, for example, an alkoxy group is bonded to the benzene ring to which the polymerizable group-containing group is not bonded, and, for example, adhesion to a substrate, etc. is improved. It is because it is easy to impart other functions, such as being easy to do.

On the other hand, the compounds represented by formulas (B-22), (B-23) and (B-24) to be described later are examples of compounds in which a polymerizable group-containing group is bonded to the entire benzene ring bonded to the triazine ring.

In addition, the compound represented by Formula (B-31) described later is an example of a compound in which a polymerizable group-containing group is bonded only to a part of the benzene ring bonded to the triazine ring.

In the present invention, the number of polymerizable group-containing groups of the compound B1 in one molecule may be 1 or more, preferably 1 or more and 2×m1 or less, and among them, 1 or more and m1 or less. That is, when m1 is 2, the compound B1 preferably has 1 or more and 4 or less polymerizable group-containing groups in one molecule, and among them, 1 or more and 2 or less are preferable. Moreover, when m1 is 1, it is preferable that it is 1 or more and 2 or less, and it is preferable that it is 1 among them. This is because the compound B1 is capable of forming a cured product excellent in light resistance and the like. In addition, this is because the compound B1 is easy to synthesize.

Further, the compound B1 has a structure in which m1 groups are bonded by X ¹ as described above, and the number of polymerizable group-containing groups each of m1 groups is preferably 2 or less, and is preferably 1. This is because the compound B1 is capable of forming a cured product excellent in light resistance and heat resistance. In addition, this is because the compound B1 is easy to synthesize.

On the other hand, the compound represented by formula (B-3) to be described later is a compound corresponding to compound B1, and is an example of a compound having one polymerizable group-containing group in one molecule.

In addition, the compound represented by formula (B-3) to be described later is an example of a compound in which m1 is 1 in the compound B1, and the number of polymerizable group-containing groups of m1 groups is 1.

In the present invention, the number of polymerizable group-containing groups in one molecule of the compound B2 may be 1 or more, preferably 1 or more and 2×m2 or less, and among them, 1 or more and m2 or less. That is, when m2 is 2, the compound B2 preferably has 1 or more and 4 or less polymerizable group-containing groups in one molecule, and among them, 1 or more and 2 or less are preferable, and two of them are preferable. In addition, the number of polymerizable group-containing groups that Compound B2 has in one molecule is preferably one or more and two or less, and one of them is preferable when m2 is 1. This is because the compound B2 is capable of forming a cured product excellent in light resistance and heat resistance. In addition, this is because the compound B2 is easy to synthesize.

In addition, the compound B2 has a structure in which m2 groups are bonded by X ² as described above, and the number of polymerizable group-containing groups each of m2 groups is 2 or less, and is preferably 1. This is because the compound B2 is capable of forming a cured product excellent in light resistance and heat resistance. In addition, this is because the compound B2 is easy to synthesize.

In the present invention, the number of polymerizable group-containing groups in one molecule of the compound B3 may be 1 or more, preferably 1 or more and 6×m3 or less, and among them, 1 or more and 3×m3 or less. That is, when m3 is 1, the number of polymerizable group-containing groups of the compound B3 in one molecule is preferably 1 or more and 6 or less, and among them, 1 or more and 3 or less are preferable. This is because the compound A is capable of forming a cured product excellent in light resistance and heat resistance. In addition, this is because the compound B3 is easy to synthesize.

Further, the compound B3 has a structure in which m3 groups are bonded with X ³ as described above, and the number of polymerizable group-containing groups each of m3 groups is 6 or less, and preferably 1 or more and 3 or less. This is because the compound B3 is capable of forming a cured product excellent in light resistance and heat resistance. In addition, this is because the compound B3 is easy to synthesize.

On the other hand, the compounds represented by formulas (B-22), (B-23), and (B-24) to be described later are compounds corresponding to compound B3, and are examples of compounds in which the number of polymerizable group-containing groups in one molecule is 3. .

In addition, the compound represented by formula (B-31) described later is a compound corresponding to compound B3, and is an example of a compound in which the number of polymerizable group-containing groups in one molecule is 1.

Carbon atoms used as R ¹¹ , R ¹² , R ²¹ , R ²² , R ³¹ , R ³² , R ³³ , R ³⁴ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ Alkyl group having 1 to 40, aryl group having 6 to 20 carbon atoms, arylalkyl group having 7 to 20 carbon atoms, heterocycle-containing group having 2 to 20 carbon atoms can be the same as the group used for R ¹⁰¹ above. have.

Wherein R ^3, R ^4, R ^5, R ^6, R ⁷ and R ⁸ are a plurality of R ³ to each other, a plurality of R ⁴ with each other, a plurality of R ⁵ to each other, a plurality of R ⁶ to each other, a plurality of R ⁷ to each other and a plurality R ⁸ of R ⁸ may be bonded to each other to form a benzene ring or a naphthalene ring.

R ¹⁰² in the compound B is the same as R ¹⁰² in the formula (A).

Polymerizable groups used as R ¹¹ , R ¹² , R ²¹ , R ²² , R ³¹ , R ³² , R ³³ , R ³⁴ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ Since the containing group can be the same as that described in the section "(1) Polymerizable group containing group", the description here is omitted.

The R ¹¹ , R ¹² , R ²¹ , R ²² , R ³¹ , R ³² , R ³³ and R ³⁴ are at least one of R ¹¹ and R ¹² , at least one of R ²¹ and R ²² , at least one of R ³¹ and R ³² One and at least one of R ³³ and R ³⁴ is -OR ¹⁰² .

That is, at least one of the combinations of R ¹¹ and R ^12, the combination of R ²¹ and R ^22, the combination of R ³¹ and R ³² , and the combination of R ³³ and R ³⁴ is -OR ^102, respectively.

In the above combination, it is preferable that one of the compounds B is -OR ¹⁰² from the viewpoint of increasing the change in ultraviolet absorption capacity before and after the latent release of the compound B, and from the viewpoint of ease of synthesis of the compound B.

In the above combination, it is preferable that both are -OR ¹⁰² from the viewpoint of making a large change in the ultraviolet absorption capacity before and after the release of the latent.

In the above combination, when only one is -OR ¹⁰² , the other is a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or It is preferable that it is a C2-C20 heterocyclic-containing group, and it is more preferable that it is a hydrogen atom or a C1-C40 alkyl group.

This is because the other side of the combination is the functional group, so that the compound B has a large change in ultraviolet absorption ability. In addition, this is because the compound B has little cure inhibition.

Further, as the alkyl group and the arylalkyl group, for example, those in which a methylene group is substituted with -O-, -CO-, or the like can be preferably used.

When R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are groups other than a polymerizable group-containing group, each independently a cyano group, a hydroxyl group, an alkyl group having 1 to 40 carbon atoms, a carbon atom It is preferably an arylalkyl group having 7 to 20 carbon atoms, more preferably a cyano group, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, an arylalkyl group having 7 to 10 carbon atoms, and an alkyl group having 3 to 10 carbon atoms. It is more preferable.

In addition, R ⁴ is preferably an alkyl group having 1 to 10 carbon atoms, and among them, an alkyl group having 1 to 5 carbon atoms can be more preferably used.

Since R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are the above-described groups, the synthesis of compound B becomes easy, and compound B exhibits excellent ultraviolet absorption ability after desorption of the protecting group R ¹⁰² Because it does.

In addition, it is preferable that the alkyl group and the arylalkyl group used for R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ have a methylene group substituted with -O-, -CO-, etc. Can be used.

In the present invention, it is preferable that R ⁷ and R ⁸ are a group in which the methylene group in the group of an alkyl group having 1 to 10 carbon atoms and an alkyl group having 1 to 20 carbon atoms is substituted by -O-, -CO-, and among them It is preferable that the methylene group in the group of an alkyl group having 1 to 8 carbon atoms or an alkyl group having 2 to 10 carbon atoms is substituted by -O-, -CO-, and in particular, an alkyl group having 1 to 5 carbon atoms, a carbon It is preferable that the methylene group in the group of the alkyl group having 3 to 8 atoms is substituted by -O- and -CO-.

Since R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are the above-described groups, the synthesis of compound B becomes easy, and compound B exhibits excellent ultraviolet absorption ability after desorption of the protecting group R ¹⁰² Because it does.

M31 is 1, m32 represents an integer of 0 to 2, and the sum of m31 and m32 represents an integer of 1 to 3.

The sum of m31 and m32 is preferably an integer of 2 to 3, and particularly preferably 3, from the viewpoint of a large change in the ultraviolet absorption capacity before and after the release of the latent compound B.

B1 represents the integer of 0-4. From the viewpoint of the balance between the effect of obtaining a latent additive capable of forming a cured product excellent in light resistance and heat resistance, and the ease of synthesis, b1 is preferably an integer of 0 to 3, more preferably an integer of 0 to 2. , It is especially preferable that it is an integer of 0-1.

B2 represents the integer of 0-2. From the viewpoint of solubility, b2 is preferably an integer of 1 to 2.

B3 represents the integer of 0-4. From the viewpoint of the balance between the effect of obtaining a latent additive capable of forming a cured product excellent in light resistance, heat resistance, etc., and ease of synthesis, b3 is preferably an integer of 0 to 3, more preferably an integer of 0 to 2. , It is especially preferable that it is an integer of 0-1.

B4 represents the integer of 0-3. From the viewpoint of the balance between the effect of obtaining a latent additive capable of forming a cured product excellent in light resistance and heat resistance, and the ease of synthesis, b4 is preferably an integer of 0-2, and particularly preferably an integer of 1-2. .

B5 represents the integer of 0-2. From the viewpoint of the balance between the effect of obtaining a latent additive capable of forming a cured product excellent in light resistance and heat resistance, and the ease of synthesis, b5 is particularly preferably an integer of 1 to 2.

The b6 represents the integer of 0-3. From the viewpoint of the balance between the effect of obtaining a latent additive capable of forming a cured product excellent in light resistance and heat resistance and the ease of synthesis, b6 is preferably an integer of 0 to 2, and particularly preferably an integer of 1 to 2. .

The b7 represents an integer of 0 to [3-(m31+m32)]. From the viewpoint of ease of synthesis, it is preferable that it is an integer of 0 to 1, and it is preferable that it is 0.

The above X ¹ , X ² and X ³ (hereinafter, X ¹ to X ³ may be collectively referred to as X.) are groups of m1 to m3 (hereinafter, m1 to m3 may be collectively referred to as m). In addition, in some cases, the group of m1 to m3 is collectively referred to as an m-valent group.) Or a group containing an m-valent polymerizable group.

The m-valent polymerizable group-containing group used as X is not particularly limited as long as it has a polymerizable group, and for example, it can be the same as described in the section "(1) Polymerizable group-containing group". Omit it.

The m-valent group used as X is a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a group represented by the following (III-a) or (III-b), >C=O, >NR ¹⁵³ , -OR ¹⁵³ , -SR ¹⁵³ , -NR ¹⁵³ R ¹⁵⁴ or an aliphatic hydrocarbon group of 1 to 120 carbon atoms having the same valence as m, an aromatic ring-containing hydrocarbon group of 6 to 35 carbon atoms, or 2 carbon atoms Is a heterocyclic-containing group of ~35, R ¹⁵³ and R ¹⁵⁴ are a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a compound having 2 to 35 carbon atoms Represents a ring-containing group, and one or two or more of the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group, and the methylene group of the heterocycle-containing group are -O-, -S-, -CO-, -O-CO-, -CO- O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO- NH-, -NH-CO-, -NH-CO-O-, -NH-CO-O-, -NR'-, -SS-, -SO ₂ -, when substituted with a nitrogen atom or a combination thereof In some cases, the aromatic ring or heterocycle may be condensed with another ring. The combination of substituting the methylene group is based on the condition that oxygen atoms are not adjacent to each other.

When X is a nitrogen atom, a phosphorus atom, or a bonding group represented by the following (III-a) or (III-b), m is 3, and X is a direct bond, an oxygen atom, a sulfur atom, >C=O, -NH- When CO-, -CO-NH- or >NR ¹⁵³ , m is 2, and when X is a hydrogen atom, -OR ¹⁵³ , -SR ¹⁵³ or -NR ¹⁵³ R ¹⁵⁴ , m is 1.

(* means bonding with an adjacent group by the * part.)

The structure of an aliphatic hydrocarbon group having 1 to 120 carbon atoms and having the same valence as m as the m-valent group can be appropriately set according to the use of the latent additive.

As the monovalent to trivalent aliphatic hydrocarbon group having 1 to 120 carbon atoms, specifically, an aliphatic hydrocarbon group having 1 to 120 carbon atoms used as R ⁵³ described in the above "(1) polymerizable group-containing group", and A divalent to trivalent aliphatic hydrocarbon group having 1 to 120 carbon atoms used for L ₁ is mentioned.

The structure of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms having the same valence as m and used for the m-valent group can be appropriately set according to the use of the latent additive.

As the monovalent to trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, specifically, an aromatic ring having 6 to 35 carbon atoms used as R ⁵³ described in the above "(1) polymerizable group-containing group" is contained. A hydrocarbon group and an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms of divalent to trivalent used as L ₁ .

The structure of the heterocyclic-containing group having 2 to 35 carbon atoms having the same valence as m and used for the m-valent group can be appropriately set according to the use of the latent additive.

As the monovalent to trivalent heterocyclic group having 2 to 35 carbon atoms, specifically, a heterocyclic group having 2 to 35 carbon atoms used as R ⁵³ described in the above "(1) polymerizable group-containing group" , And a heterocyclic group having 2 to 35 carbon atoms of divalent to trivalent used as L ₁ .

Each of R ¹⁵³ and R ¹⁵⁴ can be the same as the contents of R ⁵³ and R ⁵⁴ described in the section "(1) Polymerizable group-containing group".

When m is 2, 3, 4, 5, and 6, the m-valent group is a general formula (1) that can be used when n is 2 in Japanese Unexamined Patent Application Publication No. 2017-001184, and can be used when n is 3. Described as general formula (2) that can be used when n is 4, general formula (3) that can be used when n is 5, and general formula (5) that can be used when n is 6. You can also use the prayer of becoming.

Specifically, examples of the m-valent group include groups represented by the general formulas (1) to (5) used for L ₁ described in the "(1) polymerizable group-containing group".

When m is 2, the m-valent group is preferably an aliphatic hydrocarbon group having 1 to 120 carbon atoms, more preferably an alkylene group or a diol residue, and an alkylene group having 1 to 10 carbon atoms or 1 to carbon atoms It is preferably a diol residue of 10. This is because the preparation of compound B is easy.

The bonding position of X to the benzene ring may be any position. For example, the bonding position of R ¹⁰² -O- is preferably an ortho or meta position.

The compound B may have a phenolic hydroxyl group, that is, a phenolic hydroxyl group that is not protected by the protecting group R ¹⁰² , but the number of phenolic hydroxyl groups is preferably 2 or less, more preferably 0. Do. This is because the compound B has little cure inhibition.

As a specific example of the said compounds B1-B3, the compound shown below is mentioned, for example.

(3-2) Second embodiment

The second embodiment of the compound A is one having a structure suitable for using a latent additive as a latent antioxidant.

As such compound A, for example, a compound represented by the following general formula (C) (hereinafter sometimes referred to as compound C) can be preferably used.

(In the formula, R ⁴² and R ⁴³ each independently represent a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, or a polymerizable group-containing group,

R ⁴⁴ is each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a carbon atom Represents a heterocycle-containing group or a polymerizable group-containing group of 2 to 20,

R ¹⁰² and R ¹⁰² are as defined in the general formula (A),

m4 represents an integer from 1 to 10,

c1 represents the integer of 0-2,

X ⁴ represents an m4 valent group or an m4 valent polymerizable group-containing group,

At least one of R ⁴² , R ⁴³ , R ⁴⁴ and X ⁴ is a polymerizable group-containing group.)

The compound C has a structure in which m4 specific groups are bonded to an m4 valent group (m4 valent specific atom or group) represented by X ⁴ . These m4 groups may be the same or different from each other.

The value of m4 is an integer of 1 to 10, and it is preferably 1 to 6 from the viewpoint of ease of synthesis, particularly preferably 1 to 5, particularly preferably 1 to 4, and especially 1 to 3 It is preferable and, especially, it is preferable that it is 1-2. This is because the compound C is capable of forming a cured product excellent in light resistance and the like. In addition, this is because the compound C is easy to synthesize.

In the compound C, at least one of R ⁴² , R ⁴³ , R ⁴⁴ and X ⁴ is a polymerizable group-containing group.

Preferred that the compound C is at least one polymerizable group-containing group of R ⁴⁴ in, at least, and the meta above R ⁴⁴ is more preferably a polymerizable group-containing group with respect to the -OR ^102, R ⁴⁴ million meth above with respect to the -OR ¹⁰² It is particularly preferred that it is a polymerizable group-containing group.

This is because, when the polymerizable group-containing group is included as the group described above, the latent additive containing the compound C can form a cured product having more excellent heat resistance and the like. In addition, this is because the compound C is easy to synthesize.

When at least one of R ⁴² , R ^43, and R ⁴⁴ in the compound C is a polymerizable group-containing group, the polymerizable group-containing group is, for example, d+n of the group represented by the general formula (D) is 2 to 6 What is an integer of can be used preferably, Especially, what is an integer of 2-4 can be used preferably. This is because the compound C is capable of forming a cured product excellent in heat resistance and the like. In addition, this is because the compound C is easy to synthesize.

In the present invention, the number of polymerizable group-containing groups in one molecule of the compound C may be 1 or more, preferably 1 or more and 2×m4 or less, and among them, 1 or more and m4 or less. That is, when m4 is 2, the number of polymerizable group-containing groups of the compound C in one molecule is preferably 1 or more and 4 or less, and among them, 1 or more and 2 or less are preferable. Moreover, when m4 is 1, it is preferable that it is 1 or more and 2 or less, and it is preferable that it is 1 among them. This is because the compound C is capable of forming a cured product excellent in heat resistance and the like. In addition, this is because the compound C is easy to synthesize.

In addition, the compound C has a structure in which m4 groups are bonded by X ⁴ as described above, and the number of polymerizable group-containing groups each of m4 groups is preferably 2 or less, and is preferably 1. This is because the compound C is capable of forming a cured product excellent in heat resistance and the like. In addition, this is because the compound C is easy to synthesize.

An alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, and a heterocyclic ring having 2 to 20 carbon atoms used for the R ⁴² , R ⁴³ and R ⁴⁴ About the containing group, it can be made the same as the group used for said R ¹⁰¹ .

The R ⁴⁴ may be a benzene ring or a naphthalene ring by bonding of a plurality of R ⁴⁴ to each other.

R ¹⁰² is the same as R ¹⁰² in General Formula (A).

The polymerizable group-containing group used for R ⁴² , R ⁴³ and R ⁴⁴ can be the same as those described in the section "(1) Polymerizable group-containing group", and the description thereof will be omitted.

When R ⁴² and R ⁴³ are groups other than the polymerizable group-containing group, it is preferably a hydrogen atom and an alkyl group having 1 to 10 carbon atoms, and is an unsubstituted, unsubstituted alkyl group having 1 to 10 carbon atoms without a substituent. It is more preferable. Among these, a group represented by C ₄ H ₉ is preferable, and a tert-butyl group is particularly preferable.

It is preferable that at least one of R ⁴² and R ⁴³ is an alkyl group having 1 to 40 carbon atoms, more preferably both of R ⁴² and R ⁴³ are an alkyl group having 1 to 40 carbon atoms, and among them R ⁴² and R It is preferable that both of ⁴³ are C1-C10 alkyl groups.

It is preferable that both R ⁴² and R ⁴³ are unsubstituted alkyl groups having 1 to 10 carbon atoms that do not have a substituent such as tert-butyl group.

This is because, when R ⁴² and R ⁴³ are the above-described groups, the latent additive containing the compound C can form a cured product having more excellent heat resistance and the like. In addition, this is because the compound C is easy to synthesize.

In the case of a group other than the polymerizable group-containing group, R ⁴⁴ is preferably an alkyl group having 1 to 40 carbon atoms.

This is because, when R ⁴⁴ is the group described above, the latent additive containing the compound C can form a cured product having more excellent heat resistance and the like. In addition, this is because the compound C is easy to synthesize.

The c1 is an integer of 0 to 2, but it is preferably 0 to 1 from the viewpoint of ease of synthesis.

X ⁴ is an m4 valent group or an m4 valent polymerizable group-containing group. Such X ⁴ can be the same as X described in "(3-1) First Embodiment".

The bonding position of the bonding group X ^{4 to} the benzene ring may be any position. For example, it is preferable that the bonding position of R ¹⁰² -O- is para-position.

This is because, when the bonding position is the position described above, the latent additive containing the compound C can form a cured product having more excellent heat resistance and the like. In addition, this is because the compound C is easy to synthesize.

As a specific example of compound C, the compound etc. shown below are mentioned, for example.

(3-3) Other

The method for producing the compound A is not particularly limited as long as it is a method capable of obtaining a desired structure. The above production method is, for example, by introducing a polymerizable group-containing group to the compound having cyclic structure A by the same method as described in International Publication No. WO2000/61685, followed by the same method as described in International Publication No. WO2014/021023. By the method, a method of synthesizing a compound in which the phenolic hydroxyl group is protected by R ¹⁰² can be mentioned.

As for the kind of compound A, among the latent additives, only one type may be sufficient, and even if there are two or more types, there is no problem. The latent additive may contain, for example, 2 or more and 5 or less of Compound A.

For example, as the compound A, compounds B1 to B3 and C may be used in combination. In this case, it becomes easy to obtain a cured product excellent in both ultraviolet absorption ability and oxidation prevention ability.

The content of the compound A is not limited as long as a latent additive capable of forming a cured product having excellent light resistance and heat resistance can be obtained, and is appropriately set according to the type of the latent additive.

The content of the compound A may be, for example, 100 parts by mass per 100 parts by mass of the solid content of the latent additive, that is, the latent additive may be the compound A.

In addition, the content may be less than 100 parts by mass in 100 parts by mass of the solid content of the latent additive, that is, the latent additive may be a composition containing the compound A and other components, for example, more than 10 parts by mass and 99.99 parts by mass. It can be less than a part.

In the present invention, the lower limit of the content is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, and particularly preferably 90 parts by mass or more, because it becomes easy to improve functions such as light resistance and heat resistance by adding to the composition. Do.

In addition, from the fact that particle size control and the like becomes easy, the upper limit of the content is preferably 99 parts by mass or less, particularly preferably 95 parts by mass or less, and particularly preferably 90 parts by mass or less.

On the other hand, the solid content includes all components other than the solvent.

In addition, the content of the compound A represents the total amount of the compound A when two or more types are included.

It is preferable that the compound A is one in which the protecting group R ¹⁰² is removed by heating.

The temperature at which the protecting group R ¹⁰² is desorbed may be, for example, 100°C or more and 300°C or less, preferably 120°C or more and 250°C or less, and more preferably 150°C or more and 230°C or less.

The desorption temperature may be a temperature showing a heat loss of 5% by weight by differential thermal analysis.

As a measurement method, for example, using a STA (differential thermogravimetric simultaneous measuring device), a sample of about 5 mg, nitrogen in an atmosphere of 200 ml/min, a temperature increase start temperature of 30°C under normal pressure, a temperature increase end temperature of 500°C, The heat loss for the sample when the temperature rises at a temperature increase rate of 10°C/min is measured, and the temperature at the time of 5% reduction with respect to the sample weight at 30°C can be set as a 5% weight reduction temperature.

The STA7000 (made by Hitachi Hi-Tech Science Co., Ltd.) can be used as a device for measuring differential thermal weight at the same time.

2. Other ingredients

The latent additive may include other components other than the compound A.

As said other component, the content described in "2. resin" and "3. other component" of "B. composition" mentioned later are mentioned, for example.

It is preferable that the said latent additive contains the non-photosensitive resin of said "2. Resin" as said other component.

The content of the other components can be appropriately set depending on the use of the latent additive, for example, 50 parts by mass or less in 100 parts by mass of the solid content of the latent additive, and preferably 10 parts by mass or less. This is because it becomes easy to make the content ratio of the compound A large in the latent additive, and it becomes easy to improve the functions such as light resistance and heat resistance of the composition.

3. Latent additive

The method for producing the latent additive is not limited as long as it is a method capable of including the compound A and other components in a desired blending amount if necessary.

When the latent additive contains Compound A and other components, a method using a known mixing means is exemplified.

Examples of the use of the latent additive include addition to a composition containing a resin, etc., among others, applications requiring light resistance, heat resistance, etc., and applications requiring uniform dispersion of the latent additive in the composition. desirable.

Applications of the composition to which the latent additive is added include thermosetting paints, photocurable paints or varnishes, thermosetting adhesives, photocurable adhesives, printed circuit boards, or liquid crystals for color displays such as color TVs, PC monitors, portable information terminals, and digital cameras. Color filter for display panel, color filter for CCD image sensor, photo spacer, black column spacer, electrode material for plasma display panel, touch panel, touch sensor, powder coating, printing ink, printing plate, adhesive, dental composition, photolithography Resin, gel coat, photoresist for electronic engineering, electroplating resist, etching resist, both liquid and dry films, solder resist, to manufacture color filters for various display applications, or to manufacture plasma display panels, electroluminescent displays, and LCDs Resist for forming structures in the process, composition for encapsulating electrical and electronic components, solder resist, magnetic recording material, micro mechanical parts, waveguide, optical switch, plating mask, etching mask, color Test systems, fiberglass cable coating, screen printing stencils, materials for manufacturing three-dimensional objects by stereolithography, holographic recording materials, image recording materials, microelectronic circuits, decolorization materials, decolorization materials for image recording materials, and microcapsules. Decolorizing material for image recording materials used, photoresist materials for printed wiring boards, photoresist materials for UV and visible laser direct image systems, photoresist materials used for dielectric layer formation in sequential lamination of printed circuit boards, photoresist for 3D mounting It can be used for various applications such as a material or a protective film, and there is no particular limitation on the use.

In addition, for the above purposes, when the latent additive is used as a latent ultraviolet absorber, it is not limited to a use requiring durability, such as when used as a product, and is suitable for a member subjected to ultraviolet irradiation during the manufacturing process, for example. Can be used.

As a member subjected to ultraviolet irradiation during the manufacturing process, for example, a member that is irradiated with ultraviolet rays or the like in order to improve the surface of the surface such as improving wettability and adhesion may be mentioned.

The above-described members requiring improved wettability and adhesion may be laminated with other members. For example, various image displays such as plasma display panels, organic electroluminescent displays, and liquid crystal displays, As members of various sensors such as touch panels, circuit boards, etc., color filters, photo spacers, luminance enhancing plates, light guide plates, TFT substrates, alignment films, liquid crystal layers, insulating films, acoustic elements such as speakers, imaging lenses, keypads, HDDs A member requiring surface modification or prevention of member deterioration in a manufacturing process such as a magnetic head for use may be mentioned.

As a member requiring surface modification or prevention of member deterioration in the above-described manufacturing process, a member laminated with another member through an adhesive, a member covered by another member with a paint, etc. may be mentioned. For example, a car, Constituent members for various uses, such as conveyance equipment such as interior and exterior members of an aircraft, household appliances such as refrigerators and washing machines, and home building materials, are also mentioned.

In addition, after forming a pattern-shaped member on the substrate, there are cases in which ultraviolet irradiation or the like is applied to the member together with the substrate to modify the surface of the exposed substrate. For the above purposes, it can be preferably used in a member used together with a member requiring surface modification or the like in the manufacturing process. Examples of the above applications include members used with members requiring surface cleaning or surface modification of plastic films, glass, silicon wafers, various engineering plastics, optical lenses, metal surfaces, plating, ceramics, molds, etc. I can.

B. Composition

Next, the composition of the present invention will be described.

The composition of the present invention contains a compound (Compound A) having a structure and a polymerizable group-containing group represented by the following general formula (A), and a resin.

(In the formula, ring A represents a 5- or 6-membered aromatic ring, or a 5- or 6-membered heterocycle,

R ¹⁰¹ is each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group or a carbon atom having 7 to 20 carbon atoms Represents a heterocycle-containing group of 2 to 20 numbers,

R ¹⁰² is each independently an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, and 2 to carbon atoms Represents a heterocyclic ring-containing group of 20 or a silyl group,

a1 represents an integer of 1 or more,

a2 represents an integer of 1 or more.)

More specifically, in the general formula (A), ring A represents a 5- or 6-membered aromatic ring, or a 5- or 6-membered heterocycle,

R ¹⁰¹ is each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a carbon atom A heterocyclic-containing group of number 2 to 20,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from the following group 1,

or

One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from the following group 2,

R ¹⁰² is each independently an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, and 2 to carbon atoms 20 heterocyclic-containing group, silyl group,

A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from the following group 1,

or

One or two or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represent a group substituted with a divalent group selected from the following group 2,

a1 represents an integer of 1 or more,

a2 represents an integer of 1 or more.

(Group 1: ethylenic unsaturated group, halogen atom, acyl group, acyloxy group, substituted amino group, sulfonamide group, sulfonyl group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, imide group, car Barmoyl group, sulfonamide group, phosphonic acid group, phosphoric acid group, salt of carboxyl group, salt of sulfo group, salt of phosphonic acid group, salt of phosphoric acid group)

(Group 2: carbon-carbon double bond, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO -S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -O-CO-NH-, -NR '- (R' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.), -SS-, -SO ₂ -, a group combining them under the condition that oxygen atoms are not adjacent to each other)

The composition of the present invention is excellent in light resistance and heat resistance by including the compound A. In addition, a composition in which the latent additive is uniformly dispersed can be obtained.

Hereinafter, each component of the composition of the present invention will be described in detail.

1.Compound A

The content of the compound A is appropriately set according to the use of the composition. For example, it can be made into 0.01 mass part or more and 20 mass parts or less in 100 mass parts of solid content of a composition, and it is preferable that it is 0.05 mass parts or more and 10 mass parts or less. This is because it becomes possible to stably impart light resistance and heat resistance to the composition.

The compound A may be the same as that described in the section "A. Compound and latent additive", and thus the description thereof will be omitted.

2. Suzy

As the resin, either a polymerizable compound having a polymerizable group or a polymer not having a polymerizable group can be used.

It is preferable that the resin contains a polymerizable compound from the viewpoint of being able to more effectively exhibit the effect of being able to form a cured product excellent in light resistance and heat resistance.

The resin is not limited to a polymerizable compound from the viewpoint of excellent flexibility in timing for imparting light resistance, heat resistance, and the like, and a polymer having no polymerizable group can also be preferably used.

(1) polymerizable compound

The polymerizable compound has a polymerizable group.

The polymerizable compound has different properties depending on the type of polymerizable group, that is, the type of polymerization reaction. For example, a radical polymerizable compound having a radical polymerizable group, a cationic polymerizable compound having a cationic polymerizable group, and an anionic polymerizable group The anionic polymerizable compound etc. of a branch are mentioned.

In the present invention, it is preferable that the polymerizable compound has a polymerizable group of the same type as the polymerizable group of the compound A.

Specifically, when the compound A has a radical polymerizable group as the polymerizable group, it is preferable to use a radical polymerizable compound as the polymerizable compound.

Since the compound A and the polymerizable compound have the same kind of polymerizable group, polymerization easily occurs between them. And it is because it is possible to suppress the precipitation, sublimation, etc. of the compound A and the R ¹⁰² desorbed product from the cured product. In addition, it is because it becomes easy to form a cured product excellent in light resistance and the like as a result.

(1-1) radical polymerizable compound

The radical polymerizable compound has a radical polymerizable group.

The radical polymerizable group is not limited as long as it can be polymerized by a radical, and examples thereof include ethylenically unsaturated groups such as acryloyl group, methacryloyl group, and vinyl group.

The radical polymerizable compound has one or more radical polymerizable groups, and may be a monofunctional compound having one radical polymerizable group or a polyfunctional compound having two or more radical polymerizable groups.

The radical polymerizable compound may be any of a compound having an acid value or a compound not having an acid value.

Examples of the compound having the acid value include acrylate compounds and methacrylate compounds having carboxyl groups such as methacrylic acid and acrylic acid.

Examples of the compound having no acid value include carboxyl groups such as urethane acrylate resin, urethane methacrylate resin, epoxy acrylate resin, epoxy methacrylate resin, acrylate-2-hydroxyethyl, and methacrylate-2-hydroxyethyl. An acrylate compound and a methacrylate compound which do not have a etc. are mentioned.

The radical polymerizable compound may be used alone or in combination of two or more. For example, as a radical polymerizable compound, a compound having an ethylenically unsaturated group and an acid value and a compound having an ethylenic unsaturated group and not having an acid value may be used in combination.

When two or more radical polymerizable compounds are mixed and used, they may be copolymerized in advance and used as a copolymer.

As such a radically polymerizable compound, more specifically, a radically polymerizable compound described in Japanese Unexamined Patent Application Publication No. 2016-176009, and the like can be mentioned.

(1-2) Cationic polymerizable compound

The cationic polymerizable compound has a cationic polymerizable group.

The cationic polymerizable group is not limited as long as it is polymerizable by a cation, and examples thereof include an epoxy group, an oxetane group, and a vinyl ether group.

Examples of the cationic polymerizable compound include compounds having a cyclic ether group such as an epoxy compound having an epoxy group and an oxetane compound having an oxetane group, and a vinyl ether compound having a vinyl ether group.

As such a cationic polymerizable compound, more specifically, a cationic polymerizable compound described in Japanese Unexamined Patent Application Publication No. 2016-176009, etc. are mentioned.

The cationic polymerizable compound may have one or more cationic polymerizable groups, and may be a monofunctional compound having one cationic polymerizable group or a polyfunctional compound having two or more cationic polymerizable groups.

The cationic polymerizable compound may be used alone or in combination of two or more. When two or more types of cationic polymerizable compounds are mixed and used, they may be copolymerized in advance and used as a copolymer.

Cationic polymerizable compounds can be used together with cationic initiators such as photo cationic initiators and thermal cationic initiators.

(1-3) Anionic polymerizable compound

The anionic polymerizable compound has an anionic polymerizable group.

The anionic polymerizable group is not limited as long as it can be polymerized by an anion, and examples thereof include an epoxy group and a lactone group.

Examples of the anionic polymerizable compound include an epoxy compound having an epoxy group, a lactone compound having a lactone group, an acryloyl group, and a compound having a methacryloyl group.

Examples of the lactone compound include β-propiolactone and ε-caprolactone.

Examples of the epoxy compound include an epoxy compound exemplified as the cationic polymerizable compound. Moreover, as a compound which has an acryloyl group, a methacryloyl group, etc., what was illustrated as the said radical polymerizable compound is mentioned.

The anionic polymerizable compound has one or more anionic polymerizable groups, and may be a monofunctional compound having one polymerizable group or a polyfunctional compound having two or more polymerizable groups.

The anionic polymerizable compounds may be used alone or in combination of two or more. When two or more types of anionic polymerizable compounds are mixed and used, they may be copolymerized in advance and used as a copolymer.

(1-4) Other polymerizable compounds

The polymerizable compound is not limited as long as it has a functional group capable of high molecular weight. For example, the phenol resin, unsaturated polyester resin, polyetherimide (PEI), and polyimide (PI) described in Japanese Patent Publication No. 4932070 ), and thermosetting resins such as polyamideimide (PAI).

As said polyimide, what becomes a polyimide by heat hardening and high molecular weight can be used, and specifically, what contains a polyimide precursor is mentioned. Examples of the polyimide precursor include those containing polyamic acid.

As a commercial item of the said polyamide-imide resin, HI406 (made by Hitachi Kasei Corporation, brand name) etc. is mentioned, for example.

Examples of the polyimide include Uimide (made by Unitika, brand name), U-varnish (made by Ubego Corporation, brand name), HCI series (made by Hitachi Kasei, brand name), orum (made by Mitsui Chemical Company, brand name). And the like.

(2) Polymer without a polymerizable group

The polymer does not have a polymerizable group.

There is no restriction|limiting as such a polymer as long as it contains a repeating structure, A photosensitive resin which has photosensitivity, a non-photosensitive resin which does not have photosensitivity, etc. are mentioned.

(2-1) photosensitive resin

The photosensitive resin has photosensitivity, for example, is used with an acid generator, and is positively changed in the direction of increasing solubility in a developer, such as cleavage of chemical bonds such as ester groups or acetal groups by the action of an acid. Mold resin is mentioned.

Examples of such positive resins include resist base resins or compounds described in Japanese Unexamined Patent Application Publication No. 2016-89085.

(2-2) Non-photosensitive resin

The non-photosensitive resin is not limited as long as it does not have photosensitivity. For example, polycarbonate (PC), polyethylene terephthalate (PET), polyethersulfone, polyvinyl butyral, polyphenylene ether, polyamide, poly And thermoplastic resins such as amidimide, polyetherimide, norbornene resin, acrylic resin, methacrylic resin, isobutylene maleic anhydride copolymer resin, and cyclic olefin resin.

As the non-photosensitive resin, in addition to the above-described thermoplastic resin, thermoplastic resins such as polyimide (PI), thermoplastic polyimide resin (TPI), polyamideimide (PAI) and liquid crystal polyester described in International Publication WO2016/159103, and natural rubber And elastomers such as isoprene rubber.

Examples of the non-photosensitive resin include fluororesins such as silicone resins, polyvinyl fluoride, and polyvinylidene fluoride.

As the non-photosensitive resin, a polymer of the polymerizable compound may also be used. That is, the composition may be a cured product of a composition containing a polymerizable compound and compound A.

(2-3) polymer

The weight average molecular weight (Mw) of the polymer is appropriately set depending on the use of the composition, and may be, for example, 1500 or more, and 1500 or more and 300000 or less.

Meanwhile, the weight average molecular weight Mw is, for example, HLC-8120GPC manufactured by Tosoh Corporation, and the elution solvent is N-methylpyrrolidone to which 0.01 mol/liter of lithium bromide is added, and polystyrene for calibration curve Standard Mw 377400, 210500, 96000, 50400, 20650, 10850, 5460, 2930, 1300, 580 (above, Polymer Laboratories Easi PS-2 series) and Mw 1090000 (Tosoh Co., Ltd. product), and the measurement column Can be obtained by measuring with TSK-GEL ALPHA-M x 2 (manufactured by Tosoh Corporation).

In addition, the measurement temperature can be set to 40°C and the flow rate can be set to 1.0 ml/min.

3. Other ingredients

In addition to the compound A and the resin, the composition may include other components as necessary.

The other components include a radical polymerization initiator used with a radical polymerizable compound, a cationic polymerization initiator used with a cationic polymerizable compound or an acid generator used with a photosensitive compound, an anionic polymerization initiator used with an anionic polymerizable compound, etc. And polymerization initiators.

As such a radical polymerization initiator, a cationic polymerization initiator, and the like, more specifically, a radical polymerization initiator and a cationic initiator described in Japanese Unexamined Patent Application Publication No. 2016-176009 can be mentioned.

Further, more specifically, examples of the anionic polymerization initiator and the like include a photoanionic polymerization initiator and a hot anionic polymerization initiator described in Japanese Unexamined Patent Application Publication No. 2017-073389.

In addition to the polymerization initiator, additives such as solvents, coloring agents, inorganic compounds, dispersants, chain transfer agents, sensitizers, surfactants, silane coupling agents, melamine, etc., which disperse or dissolve the above components, etc. Can be lifted.

Known materials may be used as the additive, and for example, those described in International Publication No. WO2014/021023 may be used.

The total content of the other components may be 30 parts by mass or less in 100 parts by mass of the solid content of the composition.

C. Hardened product

Next, the cured product of the present invention will be described.

The cured product of the present invention is a cured product of the above-described composition. Curing becomes easy by using the above-described composition.

The cured product of the present invention uses the above-described composition.

Hereinafter, the cured product of the present invention will be described in detail.

1. Composition

The composition contains a polymerizable compound as a resin.

The contents of such a composition can be the same as those described in the section "B. Composition".

2. Cured product

The cured product includes a polymeric product of a polymerizable compound.

The residual ratio of the unreacted polymerizable compound contained in the cured product is appropriately set depending on the use of the cured product, but is preferably 10 parts by mass or less, and preferably 1 part by mass or less, based on 100 parts by mass of the cured product. .

The cured product contains Compound A.

Compound A contained in the cured product is preferably polymerized with a polymerizable compound or the like through a polymerizable group contained in compound A. This is because the cured product is excellent in light resistance and heat resistance.

The cured product is a cured product of the composition, and the compound A contained in the cured product may be in an inactivated state or in an active state, but it is preferably in an active state. This is because the cured product is excellent in light resistance and heat resistance.

Regarding the inactivated state and the active state, when the protecting group R ¹⁰² in the compound A is not desorbed, it can be determined as an inactive state, and when the protecting group R ¹⁰² is desorbed, it can be determined as an active state.

In the inactivated state, more specifically, the ratio (compound F/compound A+compound F) of the compound after the protecting group R ¹⁰² contained in compound A has been desorbed (hereinafter, may be referred to as compound F) is 20/100 It is preferably below, more preferably 10/100 or less, particularly preferably 5/100 or less, and most preferably 0/100. This is because the effect of excellent storage stability of the latent additive can be more effectively exhibited when the ratio is in the above-described range.

When the protecting group R ¹⁰² is desorbed, the cured product includes a compound in which the protecting group R ¹⁰² is desorbed from the compound A, and further includes a desorbed product derived from R ¹⁰² .

The cured product may be made to contain substantially no solvent.

The content of the solvent contained in the cured product may be, for example, 1 part by mass or less, or 0.5 part by mass or less with respect to 100 parts by mass of the cured product.

The planar shape of the cured product can be appropriately set according to the use of the cured product, and may be, for example, a pattern shape such as a dot shape or a line shape.

The use of the cured product and the like can be the same as those described in the section "A. Compound and latent additive".

The method for producing the cured product is not particularly limited as long as it is a method capable of forming the cured product of the composition into a desired shape.

Since such a manufacturing method can be the same as the content described in the section "D. Manufacturing method of a cured product" to be described later, the description here is omitted.

D. Manufacturing method of cured product

Next, a method of manufacturing the cured product of the present invention will be described.

The method for producing a cured product of the present invention includes a step of polymerizing the polymerizable compound contained in the above-described composition.

By having the above-described process, the polymerizable compounds can be polymerized, and the compound A can be polymerized with the compound A and/or the polymerizable compound. As a result, it is possible to obtain a cured product excellent in light resistance and heat resistance.

The production method of the present invention includes a step of polymerization.

Hereinafter, each step of the manufacturing method of the present invention will be described in detail.

On the other hand, since the above-described composition is the same as the content described in the section "B. Composition", the description here is omitted.

1. Polymerization process

The polymerization process is a process of polymerization of the polymerizable compound contained in the above composition.

The polymerization method is different depending on the type of curing agent such as a polymerizable compound and a polymerization initiator contained therein.

For example, when the composition contains a photopolymerization initiator as a polymerization initiator together with a polymerizable compound, a method of subjecting the composition to light irradiation and polymerizing the polymerizable compounds can be used.

The light irradiated to the composition includes, for example, light having a wavelength of 300 nm to 450 nm.

Examples of the light source of the light irradiation include ultra-high pressure mercury, mercury vapor arc, carbon arc, xenon arc, and the like.

Laser light may be used as the irradiated light. Examples of the laser light include those containing light having a wavelength of 340 to 430 nm.

Examples of the laser light source include those that emit light in the visible to infrared region, such as an argon ion laser, a helium neon laser, a YAG laser, and a semiconductor laser.

Meanwhile, when these lasers are used, the composition may contain a sensitizing dye that absorbs the region from visible to infrared.

As the polymerization method, for example, when the composition contains a thermal polymerization initiator as a polymerization initiator together with a polymerizable compound, a method of subjecting the composition to a heat treatment and polymerizing the polymerizable compounds can be used.

The heating temperature is not limited as long as the composition can be stably cured, and may be 60°C or higher, preferably 100°C or higher and 300°C or lower. The heating temperature can be the temperature of the surface of the coating film of the composition.

The heating time can be performed for about 10 seconds to 3 hours.

The kind of the polymerization method may include only one type, or may include two or more types.

2. Other processes

The method for producing the cured product includes the step of polymerization, but may include other steps as necessary.

The other steps include a step of desorbing the R ¹⁰² from the compound A contained in the composition before the polymerization step, the composition after the polymerization step, that is, from the compound A included in the cured product of the above-described composition. A step of removing R ¹⁰² , a step of applying the composition onto a substrate, and the like may be mentioned.

The method of desorbing R ¹⁰² from the compound A in the desorbing step may be the same as that described in the section "E. Manufacturing method of the second composition" to be described later, and thus the description thereof will be omitted.

As a method of applying the composition in the applying step, known methods such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing and dipping may be mentioned.

The substrate may be appropriately set according to the use of the cured product, and examples thereof include soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, and the like.

Further, after the cured product is formed on the substrate, it may be used by peeling from the substrate, or may be used by transferring from the substrate to another adherend.

E. Method for preparing the second composition

Next, a method of manufacturing the second composition will be described.

The method for preparing the second composition of the present invention includes a step of desorbing R ¹⁰² from the compound (Compound A) contained in the above-described composition.

By having the above-described process, the phenolic hydroxyl group protected by R ¹⁰² in the compound A becomes an unprotected phenolic hydroxyl group, and it becomes possible to exhibit ultraviolet ray absorption ability, oxidation preventing ability, and the like. As a result, a composition excellent in light resistance and heat resistance can be obtained.

The method for preparing the second composition of the present invention includes a step of desorbing a protecting group.

Hereinafter, each step of the method for producing the second composition of the present invention will be described in detail.

1. The process of removing the protecting group

This step is a step of desorbing the protecting group R ¹⁰² from the compound A contained in the above composition.

As a method of desorbing the R ¹⁰² from the compound A, there is no problem as long as it is a method capable of stably desorbing the protecting group R ¹⁰² , and for example, a method of performing a heat treatment on the composition may be mentioned.

The heating temperature in the heat treatment is not limited as long as it is a temperature at which the protecting group R ¹⁰² is desorbed, and may be, for example, a temperature equal to or higher than the desorption temperature of the protecting group R ¹⁰² .

In addition, the heating temperature may be less than or equal to the desorption temperature observed in the protecting group R ¹⁰² alone when the composition contains an acid catalyst, a base catalyst, or the like.

The heat treatment temperature can be, for example, 50°C or more and 250°C or less, and among them, it is preferably 60°C or more and 200°C or less, and more preferably 80°C or more and 200°C or less. This is because deterioration of the resin and the like can be suppressed by the heat treatment temperature. The temperature of the composition may be the temperature of the surface of the composition.

By this step, a compound in which the protecting group R ¹⁰² is removed from the compound A is obtained.

The compound from which the protecting group R ¹⁰² has been desorbed is in a state in which the potential is released, and functions as an ultraviolet absorber.

On the other hand, since the above-described composition is the same as the content described in the section "B. Composition", the description here is omitted.

2. Other processes

In addition to the process of removing the protecting group, the manufacturing method may include other processes as necessary.

The other processes include, for example, a step of applying the composition onto a substrate, a step of polymerizing the polymerizable compound when the composition contains a polymerizable compound as a resin, and a photosensitive resin as the composition When containing, the process of developing a photosensitive resin, etc. are mentioned.

The application process and the polymerization process can be the same as those described in the section "D. Manufacturing method of cured product".

As a developing method of the photosensitive resin in the above developing step, a known method may be used, for example, a method of increasing the solubility in a developer by the action of an acid and then developing with a developer.

F. Other

1. A latent additive containing a compound having a structure represented by the general formula (A) and a polymerizable group-containing group.

2. The latent additive according to 1, wherein the compound is a compound represented by the general formula (B1), (B2), (B3) or (C).

3. In 2, at least one of R ³ and R ⁴ in the general formula (B1) is a polymerizable group-containing group, and at least one of R ⁵ and R ⁶ in the general formula (B2) is a polymerizable group-containing group, At least one of R ⁷ and R ⁸ in the general formula (B3) is a polymerizable group-containing group, and at least one of R ⁴⁴ in the general formula (C) is the polymerizable group-containing group.

4. The compound according to 2 or 3, wherein the compound contains a compound represented by the general formula (B3),

In the general formula (B3), at least one of R ⁷ meta-wie to R ³¹ and R ⁸ meta-wiring to R ³³ is a polymerizable group-containing group.

5. In any one of 1 to 4, wherein R ¹⁰² is an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. Is an arylalkyl group or a heterocyclic ring-containing group having 2 to 20 carbon atoms, and the alkyl group, the alkenyl group, the aryl group, the arylalkyl group, and the heterocyclic ring-containing group are the methylene group at the end of the oxygen atom side as -CO-O- A latent additive that is substituted.

6. A composition comprising a resin and a compound having a structure represented by the general formula (A) and a polymerizable group-containing group.

7. The composition according to 6, wherein the resin contains a polymerizable compound.

8. A cured product of the composition according to 7.

9. A method for producing a cured product having a step of polymerizing the polymerizable compound contained in the composition according to 7.

10. A method for producing a composition having a step of desorbing R ¹⁰² from the compound contained in the composition according to 6 or 7.

The present invention is not limited to the above embodiment. The above-described embodiment is an example, and anything that has substantially the same configuration as the technical idea described in the claims, and exhibits the same operating and effects is included in the technical scope of the present invention.

Example

Hereinafter, the present invention will be described in more detail with reference to examples and the like, but the present invention is not limited to these examples.

[Example 1]

4,4',4''-(1,3,5-triazine-2,4,6-tolyl)tris(2-methylbenzene-1,3-diol) (60 mmol), potassium carbonate (180 mmol) ), dimethylacetamide (DMAc) (120 ml) was added to the reaction vessel, and the temperature was raised to 135°C. After temperature rise, 3-chloro-1-propanol (200 mmol) was added dropwise and stirred for 10 hours. After completion of the reaction, toluene (300 ml) and water (300 ml) were added, the oil phase was separated, and water washing was performed 3 times. The oil phase was desolvated under reduced pressure and then crystallized (DMF 800 ml).

The obtained solid (1 equivalent), paratoluenesulfonic acid (PTS)/H ₂ O (0.1 equivalent), paramethoxyphenol (0.05 equivalent), and toluene (800 ml) were added to the reaction vessel, and the temperature was raised to 110°C. . After temperature rise, methacrylic acid (6 equivalents) was added dropwise and stirred for 10 hours. After completion of the reaction, the reaction solution was washed with water and solvent-removed under reduced pressure, followed by crystallization (dimethylformamide (DMF)/butyl acetate = 100/300).

Furthermore, the obtained solid (1 equivalent), di-tert-butyl dioxide (5 equivalents), and pyridine (300 ml) were added to the reaction vessel, and 4-dimethylaminopyridine (0.25 equivalent) was added at room temperature under a nitrogen atmosphere, It stirred at 60 degreeC for 3 hours. After completion of the reaction, toluene (500 ml) and water (500 ml) were added, the oil phase was separated, and water washing was performed three times. After the oil phase was desolvated under reduced pressure, crystallization (300 ml of methanol) was carried out to obtain a latent additive (latent ultraviolet absorber) comprising a compound represented by the following general formula (B-22).

The ¹ H-NMR and IR measurement results of the obtained compound are shown in Tables 1 and 2 below.

[Examples 2 to 3]

In the same manner as in Example 1, except that 6-chloro1-hexanol or 2-(2-chloroethoxy)ethanol was used instead of 3-chloro-1-propanol, the following general formulas (B-23) and ( The compound represented by B-24) was synthesized, and a latent additive (latent ultraviolet absorber) composed of this compound was obtained. The ¹ H-NMR and IR measurement results of the obtained compound are shown in Tables 1 and 2 below.

[Example 4]

2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole (50 mmol), di-tert-butyl itanoate (75 mmol), pyridine (200 ml) ) Was put into a reaction vessel, 4-dimethylaminopyridine (12 mmol) was put at room temperature under a nitrogen atmosphere, and the mixture was stirred at 60°C for 3 hours. After completion of the reaction, toluene (500 ml) and water (500 ml) were added, the oil phase was separated, and water washing was performed three times. After the oil phase was desolvated under reduced pressure, crystallization (300 ml of methanol) was performed to obtain a latent additive (latent ultraviolet absorber) composed of a compound represented by the following general formula (B-3). The ¹ H-NMR and IR of the obtained compound were measured, and the structure was confirmed.

[Example 5]

2-(4-(4,6-bis(4-(hexaoxy)-2-hydroxy-3-methylphenyl)-1,3,5-triazin-2-yl)-3-hydroxy-2- Methylphenoxy)ethyl methacrylate (50 mmol), di-tert-butyl itanoate (200 mmol), and pyridine (200 mL) were added to the reaction vessel, and 4-dimethylaminopyridine (12 mmol) at room temperature under nitrogen atmosphere. ) And stirred at 40°C for 3 hours. After completion of the reaction, ethyl acetate (500 ml) and water (500 ml) were added, the oil phase was separated, and water washing was performed 3 times. After the oil phase was desolvated under reduced pressure, it was purified by silica column, crystallized with methanol, and a latent additive (latent ultraviolet absorber was obtained) composed of a compound represented by the following general formula (B-31). ¹ H-NMR of the obtained compound And IR measurement results are shown in Tables 1 and 2 below.

[Example 6]

2-(tert-butyl)-6-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-methylphenol (60 mmol), potassium carbonate (75 mmol) ), 2-mercaptoethanol (75 mmol), and DMF (60 ml) were added to the reaction vessel, followed by stirring at 110° C. for 4 hours in a nitrogen atmosphere. After completion of the reaction, toluene (500 ml) and water (500 ml) were added, the oil phase was separated, and water washing was performed three times. The oil phase was concentrated to 60 ml, p-toluenesulfonic acid (3 mmol) and methacrylic acid (60 mmol) were added thereto, and a dehydration condensation reaction was performed using a Dean-Stark apparatus. After completion of the reaction, toluene (100 ml) was added, followed by washing with water 3 times. The oil phase was concentrated, di-tert-butyl peatanoate (75 mmol) and pyridine (100 mL) were added to the reaction vessel, and 4-dimethylaminopyridine (12 mmol) was added at room temperature under a nitrogen atmosphere. Stirred for hours. After completion of the reaction, ethyl acetate (500 ml) and water (500 ml) were added, the oil phase was separated, and water washing was performed 3 times. After the oil phase was desolvated under reduced pressure, silica column purification was carried out to obtain a latent additive (latent ultraviolet absorber) comprising a compound represented by the following general formula (B-32). The ¹ H-NMR and IR measurement results of the obtained compound are shown in Tables 1 and 2 below.

[Example 7]

3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid (50 mmol), pentaerythritol (50 mmol), and toluene (300 mL) were added to the reaction vessel, and paratoluenesulfonic acid ( PTS)/H ₂ O (5 mmol) was added and the temperature was increased at 110°C. After making it react for 3 hours after temperature rise, acrylic acid (150 mmol) was added dropwise, and it stirred for 8 hours. After completion of the reaction, the reaction solution was washed with water, and the oil phase was desolvated under reduced pressure to obtain a latent additive (latent antioxidant) comprising a compound represented by the following general formula (C-7). ¹ H-NMR and IR of the obtained compound were measured.

[Examples 2-1 to 2-17 and Comparative Examples 2-1 to 2-12]

According to the formulation shown in Tables 3 to 5 below, the latent additives (latent ultraviolet absorbers and latent antioxidants) obtained in the examples, ultraviolet absorbers and antioxidants, resins (polymerizable compounds having an acid value, polymerization having no acid value) Sex compound), a photoinitiator, an additive (silane coupling agent, leveling agent), a solvent, and a colorant were mixed to obtain a composition.

In addition, each component used the following materials.

In addition, the compounding amount in the table represents the mass part of each component.

[Production Example 1] Preparation of Resin No.1

1,1-bis [4-(2,3-epoxypropyloxy) phenyl] indan 30.0 g, acrylic acid 7.52 g, 2,6-di-t-butyl-p-cresol 0.080 g, tetrabutyl ammonium chloride 0.183 g and 11.0 g of propylene glycol monomethyl ether acetate (PGMEA) was put into a reaction vessel, followed by stirring at 90°C for 1 hour, 105°C for 1 hour, and 120°C for 17 hours. Then, it cooled to room temperature, 8.11g of succinic anhydride, 0.427g of tetrabutylammonium chloride, and 11.1g of PGMEA were added, and it stirred at 100 degreeC for 5 hours. Moreover, 1,1-bis [4-(2,3-epoxypropyloxy) phenyl] indan 12.0 g, 2,6-di-t-butyl-p-cresol 0.080 g and PGMEA 0.600 g were added to After stirring for 90 minutes at 120°C for 5 hours, 24.0 g of PGMEA was added to obtain Resin No. 1 as a PGMEA solution (Mw=4900, Mn=2250, acid value (solid content) 47 mg·KOH/g, solid content 45.0 mass%) .

(Potential UV absorber)

B-1: Compound represented by the general formula (B-22) (latent additive obtained in Example 1)

B-2: Compound represented by the general formula (B-23) (latent additive obtained in Example 2)

B-3: Compound represented by the general formula (B-24) (latent additive obtained in Example 3)

B-4: Compound represented by the general formula (B-3) (latent additive obtained in Example 4)

B-5: Compound represented by the general formula (B-31) (latent additive obtained in Example 5)

B-6: Compound represented by the general formula (B-32) (latent additive obtained in Example 6)

(Ultraviolet absorber)

B'-1: compound represented by the following general formula (B'-1)

B'-2: compound represented by the following general formula (B'-2)

B'-3: compound represented by the following general formula (B'-3)

B'-4: compound represented by the following general formula (B'-4)

(Latent antioxidant)

C-1: Compound represented by the general formula (C-7) (latent additive obtained in Example 7)

(Antioxidant)

C'-1: compound represented by the following general formula (C'-1)

C'-2: compound represented by the following general formula (C'-2)

(Polymerizable compound having an acid value)

D-1: Radical polymerizable compound (Showa Denko Corporation Lipoxy SPC-1000 solid content 29% by mass PGMEA solution)

D-2: Resin No. 1 prepared in Preparation Example 1

(Polymerizable compound with no acid value)

E-1: Radical polymerizable compound (Aronix M-450 manufactured by Doagosei (a mixture of pentaerythritol tri and tetraacrylate 3-4))

E-2: Radical polymerizable compound (Kayarad DPHA manufactured by Nippon Kayaku Corporation (mixture of dipentaerythritol penta and hexaacrylate))

E-3: Radical polymerizable compound (Shin-Nakamura Chemical Co., Ltd. NK Oligo EA-1020 (bisphenol A type epoxy acrylate))

E-4: Radical polymerizable compound (Atresin UN-3320 (urethane acrylate) manufactured by Negami Kogyo)

(Photopolymerization initiator)

F-1: Compound represented by the following formula (F1) (oxime ester-based photoradical polymerization initiator)

F-2: Compound represented by the following formula (F2) (oxime ester-based photoradical polymerization initiator)

F-3: Irgacure TPO (phosphine oxide radical polymerization initiator) manufactured by BASF

F-4: Compound represented by the following formula (F3) (aminoacetophenone radical polymerization initiator)

(additive)

G-1: Shin-Etsu Chemical Co., Ltd. silane coupling agent KBE-403 (silane coupling agent)

G-2: FZ-2122 (Toray Dow Corning, PGMEA solution leveling agent with 1% solid content)

(solvent)

H-1: PGMEA

H-2: methyl ethyl ketone (MEK)

H-3: dimethylacetamide (DMAc)

(coloring agent)

I-1: Acid Red52

I-2: pentamethine cyanine represented by the following formula (I-2)

[evaluation]

The following evaluation was performed on the compositions of Examples and Comparative Examples.

1. Sensitivity evaluation 1

Evaluation of the composition sensitivity of Examples 2-1 to 2-9, 2-13 to 2-17 and Comparative Examples 2-1 to 2-12 containing a polymerizable compound having an acid value among the compositions prepared in each Example and Comparative Example As, the following line width sensitivity evaluation was performed.

First, each of the compositions of Examples and Comparative Examples was spin-coated on a glass substrate (500 rpm, 2 seconds, 900 rpm, 5 seconds), and a coating film having a thickness of 10 μm after drying (after prebaking) was formed.

Subsequently, the coating film was prebaked at 90°C for 90 seconds using a hot plate, and exposed (40mJ/cm2) through a mask (line width of the opening part 20㎛) using a high-pressure mercury lamp as a light source. Got it.

Subsequently, it was developed using a 2.5% by mass aqueous sodium carbonate solution as a developer, washed well, and then post-baked at 230°C for 30 minutes using an oven, and the pattern was fixed.

The line width of the obtained pattern was measured with an electron microscope, and the line width sensitivity was evaluated based on the following criteria. The results are shown in Tables 3 to 5 below.

In addition, the film thickness of the obtained pattern was measured using a stylus type surface shape measuring device, and residual film sensitivity was evaluated based on the following criteria. The results are shown in Tables 3 to 5 below.

(Line width sensitivity)

(Circle): The line width/20 micrometers of hardened|cured material is 1.0 or more.

X: The line width/20 µm of the cured product is less than 1.0.

On the other hand, if the line width sensitivity is "○", the composition is suppressed from occurring and sufficiently cured.

(Remaining film sensitivity)

○: The film thickness of the cured product/10 µm is 0.75 or more.

×: The film thickness of the cured product/10 µm is less than 0.75.

On the other hand, when the residual film sensitivity is "o", it indicates that the curing inhibition of the composition is suppressed and sufficiently cured.

2. Sensitivity evaluation 2

As the sensitivity evaluation of the compositions of Examples 18-20 and Comparative Examples 17-19 which do not contain a polymerizable compound having an acid value among the compositions prepared in Examples and Comparative Examples, evaluation was performed using a step tablet.

Specifically, the composition was applied to a PET film to a thickness of about 3 μm with a bar coater.

Next, after prebaking at 80°C for 3 minutes, exposure was performed using an ultra-high pressure mercury lamp (UL750) as a light source (20 mW/cm 2 ). On the other hand, exposure was performed so that the exposure light amount became 400 mJ.

At this time, a negative film (a step tablet with an optical density of 0.05 as the first step and an optical density of 0.15 increments for each step) was used so that the light transmittance was gradually decreased in order to measure the light sensitivity.

Subsequently, it was developed by washing over 10 seconds in an environment of 25°C using PGMEA.

Then, it dried at 80 degreeC for 30 minutes.

Next, the light sensitivity was evaluated by measuring the number of steps of the step tablet of the cured product formed on the PET film. The results are shown in Tables 3 to 5 below.

On the other hand, the higher the number of steps of the step tablet, the higher the light sensitivity.

In addition, when the number of steps of the step tablet is 10 or more, the composition is suppressed from occurrence of curing inhibition, indicating that the composition is sufficiently cured.

3. Heat resistance

A sample for evaluation was obtained in the same manner as in "1. Sensitivity evaluation 1" except that development treatment and water washing were not performed.

Next, a heat resistance test was performed in which the sample for evaluation was heat-treated at 200°C for 2 hours using an oven.

The difference in transmittance (%) at a wavelength of 430 nm before and after the heat resistance test of the sample for evaluation (transmittance before heat resistance test (%)-transmittance before heat resistance test (%)) was measured, and heat resistance evaluation was performed according to the following criteria.

○: The difference in transmittance (%) is less than 1% with respect to the transmittance before the heat resistance test.

?: The difference in transmittance (%) is 1% or more and less than 3% with respect to the transmittance before the heat resistance test.

×: The difference in transmittance (%) is 3% or more with respect to the transmittance before the heat resistance test.

On the other hand, if the heat resistance evaluation is "○", the cured product exhibits excellent heat resistance, followed by "Δ" and "X" in the order of excellent heat resistance.

4. Light fastness

A sample for evaluation was obtained in the same manner as in "1. Sensitivity evaluation 1" except that development treatment and water washing were not performed.

Next, the sample for evaluation was subjected to a light resistance test for 96 hours using a xenon light resistance tester table ray XT-1500L manufactured by Sugashi Kenki.

The difference in transmittance (%) at a wavelength of 430 nm before and after the light resistance test of the evaluation sample (transmittance (%) before the light resistance test-transmittance (%) after the light resistance test) was measured, and light resistance evaluation was performed according to the following criteria.

○: The difference in transmittance (%) is less than 3% with respect to the transmittance before the light resistance test.

?: The difference in transmittance (%) is 3% or more and less than 5% with respect to the transmittance before the light resistance test.

×: The difference in transmittance (%) is 5% or more with respect to the transmittance before the light resistance test.

On the other hand, if the light resistance evaluation is "○", the cured product is excellent in light resistance, and then, in the order of "Δ" and "x", the cured product shows excellent light resistance.

5. HAZE evaluation

A sample for evaluation was obtained in the same manner as in "1. Sensitivity evaluation 1" except that development treatment and water washing were not performed.

Next, haze measurement was performed about the sample for evaluation using a haze meter. For the measurement, a haze meter NDH5000 manufactured by Nippon Denshoku was used, and the criteria for determination were as follows.

○: HAZE is less than 2

×: HAZE is 2 or more

On the other hand, the larger the HAZE, the more precipitates of additives such as antioxidants and ultraviolet absorbers. Therefore, the more the evaluation is ○, the less precipitation of additives and the like and the better.

6. Sublimation test

As a sublimation test of the composition obtained in Example 2-5, Comparative Example 2-2, and Comparative Example 2-3, the following evaluation was performed.

First, the composition was spin-coated on a glass substrate (500 rpm, for 7 seconds), and prebaked at 90°C for 90 seconds using a hot plate.

Subsequently, exposure (100 mJ/cm 2) was performed using a high-pressure mercury lamp as a light source to obtain a cured film. A 0.7 mm spacer and a glass substrate were provided on this cured film, and it heated at 230 degreeC for 2 hours using a hot plate.

After heating, the absorption spectrum of the glass substrate provided on the cured film was measured. The results are shown in Table 6 below.

On the other hand, the lower the absorbance at 365 nm is, the less sublimation of the additive is.

[theorem]

From Tables 3 to 5, it was confirmed that, by including the latent additive of the present invention, the composition of the example could obtain a cured product having excellent light resistance or heat resistance without causing curing inhibition.

In particular, from the results of Example 2-1 and Comparative Example 2-1, the latent additive of the present invention is capable of obtaining a sufficiently cured cured product, polymerized with a resin through a polymerizable group, and precipitated from the cured product, It is speculated that a cured product with little change over time in ultraviolet absorbing ability and oxidation preventing ability is obtained by becoming less sublimation.

When comparing the HAZE evaluation result of Example 2-2 with the results of Comparative Example 2-2 and Comparative Example 2-3, it was confirmed that the latent additive of the present invention had a polymerizable group, so that precipitation into a cured product was suppressed. Could

Comparing the results of the sensitivity evaluation of Example 2-2 with the results of Comparative Examples 2-2 to 2-4, the latent additive of the present invention has excellent sensitivity because the phenolic hydroxyl group is protected by R ¹⁰² . It was confirmed that the composition was obtained.

From the results of Table 6, it was confirmed that the latent additive of the present invention has low sublimation properties from the cured product. Further, from the results of Comparative Example 2-2 and Comparative Example 2-3, it was confirmed that the sublimation of the additive was suppressed as a result of obtaining a sufficiently cured cured product by protecting the phenolic hydroxyl group by R ¹⁰² .

According to the present invention, it is possible to provide a latent additive and composition capable of forming a cured product excellent in light resistance and heat resistance.

Claims (11)

The structure represented by the following general formula (A), and
A compound having a polymerizable group-containing group.

(In the formula, ring A represents a 5- or 6-membered aromatic ring, or a 5- or 6-membered heterocycle,
R ¹⁰¹ is each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a carbon atom A heterocyclic-containing group of number 2 to 20,
A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from the following group 1,
or
One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from the following group 2,
R ¹⁰² is each independently an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, and 2 to carbon atoms 20 heterocyclic-containing group, silyl group,
A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from the following group 1,
or
One or two or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represent a group substituted with a divalent group selected from the following group 2,
a1 represents an integer of 1 or more,
a2 represents an integer of 1 or more.)
(Group 1: ethylenically unsaturated group, halogen atom, acyl group, acyloxy group, substituted amino group, sulfonamide group, sulfonyl group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, imide group, car Barmoyl group, sulfonamide group, phosphonic acid group, phosphoric acid group, salt of carboxyl group, salt of sulfo group, salt of phosphonic acid group, salt of phosphoric acid group)
(Group 2: carbon-carbon double bond, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO -S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -O-CO-NH-, -NR '- (R' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.), -SS-, -SO ₂ -, a group combining them under the condition that oxygen atoms are not adjacent to each other) The method of claim 1,
The compound is represented by the following general formula (B1), (B2), (B3) or (C).

(In the formula, R ³ and R ⁴ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. An arylalkyl group of, a heterocycle-containing group having 2 to 20 carbon atoms, a polymerizable group-containing group,
A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,
or
One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,
R ¹¹ and R ¹² are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. An arylalkyl group, a heterocyclic-containing group having 2 to 20 carbon atoms, -OR ¹⁰² , a polymerizable group-containing group,
A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,
or
One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,
At least one of R ¹¹ and R ¹² is -OR ¹⁰² ,
R ¹⁰² is the same as R ¹⁰² in the formula (A),
m1 represents the integer of 1-10,
b1 represents an integer of 0-4,
b2 represents the integer of 0-2,
X ¹ represents an m1 valent group or an m1 valent polymerizable group-containing group,
At least one of R ¹¹ , R ¹² , R ³ , R ⁴ and X ¹ is a polymerizable group-containing group.)

(In the formula, R ⁵ and R ⁶ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. An arylalkyl group of, a heterocycle-containing group having 2 to 20 carbon atoms, a polymerizable group-containing group,
A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,
or
One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,
R ²¹ and R ²² are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms. An arylalkyl group, a heterocyclic-containing group having 2 to 20 carbon atoms, -OR ¹⁰² , a polymerizable group-containing group,
A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,
or
One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,
At least one of R ²¹ and R ²² is -OR ¹⁰² ,
R ¹⁰² is the same as R ¹⁰² in the formula (A),
m2 represents the integer of 1-10,
b3 represents an integer of 0-4,
b4 represents the integer of 0-3,
X ² represents an m2 valent group or an m2 valent polymerizable group-containing group,
At least one of R ²¹ , R ²² , R ⁵ , R ⁶ and X ² is a polymerizable group-containing group.)

(In the formula, R ⁷ , R ⁸ and R ⁹ are each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and the number of carbon atoms. 7-20 arylalkyl group, C2-C20 heterocyclic-containing group, polymerizable group-containing group,
A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,
or
One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,
R ³¹ , R ³² , R ³³ and R ³⁴ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, Arylalkyl group having 7 to 20 carbon atoms, heterocyclic-containing group having 2 to 20 carbon atoms, -OR ¹⁰² , polymerizable group-containing group,
A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,
or
One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,
At least one of R ³¹ and R ³² is -OR ¹⁰² ,
At least one of R ³³ and R ³⁴ is -OR ¹⁰² ,
R ¹⁰² and R ¹⁰² are as defined in the general formula (A),
m3 represents an integer from 1 to 10,
m31 is 1,
m32 represents an integer of 0-2,
The sum of m31 and m32 represents an integer of 1 to 3,
b5 represents an integer of 0-2,
b6 represents the integer of 0-3,
b7 represents an integer from 0 to [3-(m31+m32)],
X ³ represents an m3 valent group or an m3 valent polymerizable group-containing group,
At least one of R ³¹ , R ³² , R ³³ , R ³⁴ , R ⁷ , R ⁸ , R ⁹ and X ³ is a polymerizable group-containing group.)

(In the formula, R ⁴² and R ⁴³ each independently represent a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, or a polymerizable group-containing group,
R ⁴⁴ is each independently a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a carbon atom A group containing 2 to 20 heterocyclic rings, a group containing a polymerizable group,
A group in which one or two or more of the hydrogen atoms of the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group are substituted with a group selected from group 1,
or
One or more of the methylene groups in the alkyl group, aryl group, arylalkyl group, or heterocycle-containing group represents a group substituted with a divalent group selected from group 2,
R ¹⁰² and R ¹⁰² are as defined in the general formula (A),
m4 represents an integer from 1 to 10,
c1 represents the integer of 0-2,
X ⁴ represents an m4 valent group or an m4 valent polymerizable group-containing group,
At least one of R ⁴² , R ⁴³ , R ⁴⁴ and X ⁴ is a polymerizable group-containing group.) The method of claim 2,
At least one of R ³ and R ⁴ in the general formula (B1) is a polymerizable group-containing group,
At least one of R ⁵ and R ⁶ in the general formula (B2) is a polymerizable group-containing group,
At least one of R ⁷ and R ⁸ in the general formula (B3) is a polymerizable group-containing group,
The compound in which at least one of R ⁴⁴ in the general formula (C) is the polymerizable group-containing group. The method according to claim 2 or 3,
The compound contains a compound represented by the general formula (B3),
The compound in which at least one of R ⁷ meta-wie to R ³¹ in General Formula (B3) and R ⁸ meta-wiring to R ³³ is a polymerizable group-containing group. The method according to any one of claims 1 to 4,
R ¹⁰² is an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or an arylalkyl group having 2 to 20 carbon atoms A compound wherein the methylene group at the terminal on the side of the oxygen atom in the heterocycle-containing group is substituted with -CO-O-. A latent additive containing the compound according to any one of claims 1 to 5. The compound according to any one of claims 1 to 5, and
A composition comprising a resin. The method of claim 7,
The composition, wherein the resin comprises a polymerizable compound. A cured product of the composition according to claim 8. A method for producing a cured product having a step of polymerizing the polymerizable compound contained in the composition according to claim 8. A method for producing a composition having a step of desorbing R ¹⁰² from the compound contained in the composition according to claim 7 or 8.