TW201922717A - Compound, latent ultraviolet light absorber, composition, cured product, and cured product production method - Google Patents

Abstract

A compound shown in general formula (I-1). (In the formula, A represents an atom group having ultraviolet light absorption capacity, B represents a photoelimination group, and k represents an integer from 1 to 10). A composition containing a compound shown in general formula (I-2) and an elimination product derived from the photoelimination group. (In the formula, A represents the atom group having ultraviolet light absorption capacity, and k represents an integer from 1 to 10).

Description

Compound, latent ultraviolet absorber, composition, hardened material and method for manufacturing hardened material

The present invention relates to a compound which has less resistance to hardening and can easily provide a UV-absorbing function to a hardened material.

In order to improve the ultraviolet absorbing function or heat resistance of the curable composition, a method is known in which a UV absorbent or an antioxidant is added to the curable composition and stabilized (Patent Documents 1 to 3).
Prior art literature patent literature

Patent Document 1: Japanese Patent Laid-Open No. 2011-048382 Patent Document 2: US2016016919A1
Patent Document 3: Japanese Patent Laid-Open No. 2015-108649

However, the ultraviolet absorbers described in Patent Documents 1 to 3 have a problem that they may hinder the curing of the curable composition.
In response to such a problem, the present inventors have found that an ultraviolet absorbent has a function of absorbing light irradiated to harden a curable composition; and because of such an effect, there is a case where an ultraviolet absorbent is added to a polymerization system. , There will be a situation of hardening obstacles.

As a solution to the above-mentioned problem, a potential additive capable of deactivating the light absorption function in a polymerization system and activating it after curing is known.
However, the activation of a potential additive that can be activated after hardening may require heating or the like, and as a result, there may be a case where an easier activation is required.

The present invention has been made in view of the above-mentioned problems, and its main object is to provide a compound which has less resistance to hardening and can easily provide a UV-absorbing function to a hardened material.

The present inventors conducted intensive research in order to solve the above-mentioned problems, and as a result, it was found that by using a light-releasing group as a protective group and using the light-releasing group to protect the phenolic hydroxyl group contained in the ultraviolet absorber, it becomes easy to adjust the expression of ultraviolet rays. The above-mentioned problems can be solved at the time of the absorption function, and the present invention has been completed.

That is, the present invention provides a compound represented by the following general formula (I-1).

[Chemical 1]

(In the formula, A represents an atomic group having an ultraviolet absorbing function, B represents a light-releasing group, and k represents an integer of 1 to 10)

The present invention also provides a latent ultraviolet absorber containing a compound represented by the general formula (I-1).

The present invention also provides a composition containing a compound represented by the general formula (I-1).

Moreover, this invention provides the hardened | cured material of the composition containing the compound represented by the said General formula (I-1) and a polymerizable compound.

Moreover, this invention provides the manufacturing method of the hardened | cured material including the process of hardening the composition containing the compound represented by the said General formula (I-1) and a polymerizable compound, and forming a hardened | cured material; and A step of irradiating the hardened material with light to remove light-releasing groups contained in the compound represented by the general formula (I-1).

The present invention also provides a compound (hereinafter sometimes referred to as "compound B") containing a compound represented by the following general formula (I-2) (hereinafter sometimes referred to as "compound I-2") '") (Hereinafter sometimes referred to as" the second composition ").

[Chemical 2]

(In the formula, A is an atomic group having an ultraviolet absorption function, and k represents an integer of 1 to 10)

The present invention relates to a compound, a UV absorber, a composition using the same, a hardened product, a method for producing the hardened product, and a second composition. These will be described in detail below.

A. Compound First, the compound of the present invention will be described.
The compound of the present invention is represented by the following general formula (I-1) (hereinafter, the compound of the present invention is also referred to as compound I-1).

[Chemical 3]

(In the formula, A is an atomic group having an ultraviolet absorbing function, B is a photodissociation group, and k represents an integer of 1 to 10)

The compound I-1 atomic group A of the present invention has a function of absorbing ultraviolet rays. The compound I-1 of the present invention has a low ultraviolet absorption function before the light-release group B is released, and after the light-release group B is released, it exhibits an excellent ultraviolet absorption function based on the atomic group A.
Therefore, in the case where the compound I-1 before addition of the light-releasing group B is added to the polymerization system, for example, the compound I-1 has a low ultraviolet absorption function, and therefore the light absorption function of the light irradiated for polymerization is low, which is not easy. Prevents the hardening of the polymerization system.
On the other hand, the compound I-1 of the present invention exhibits an excellent ultraviolet absorbing function by irradiating light so that the light-releasing group is detached. Therefore, by irradiating the cured product containing the compound I-1 with light, it is possible to easily provide an ultraviolet absorbing function to the cured product. Compound I-1 does not need to be subjected to heat treatment in order to exhibit its ultraviolet absorbing function, and therefore has the advantage that it is difficult to cause damage to peripheral components such as the hardened material and the substrate due to heating.
For the above reasons, the compound I-1 has, for example, less resistance to hardening, and can easily provide an ultraviolet absorbing function to a hardened material.

In addition, the compound I-1 of the present invention has a low absorption function of light irradiated before the light-releasing group B is released in order to exhibit sensitivity. Therefore, when compound I-1 is added to a photosensitive composition whose solubility in an alkaline developing solution changes due to light irradiation, the sensitivity can be stably expressed. Moreover, the said compound I-1 can provide a ultraviolet absorption function etc. easily by irradiating the photosensitive composition with the light-releasable group detachable light.
As described above, the above-mentioned compound I-1 has less hindrance to the performance of the photosensitive composition, and can easily provide an ultraviolet absorbing function to the photosensitive composition.

Furthermore, the compound I-1 of the present invention can easily adjust the dispersion or dissolution stability in the composition by having a photo-release group B, for example.
The compound I-1 can impart excellent dispersibility in the composition by selecting the photo-releasing group B in such a manner as to improve the affinity with other components contained in the composition.
Therefore, the above-mentioned compound I-1 can provide an excellent ultraviolet absorbing function to the composition, and can also provide excellent dispersion stability during storage before use and the like.

Hereinafter, the compound I-1 of the present invention will be described in detail.

1. Light off radical B
The compound I-1 of the present invention has a photo-releasing group B.
The light-releasing group in the present invention may be a group capable of being released from the compound I-1 by irradiating light of a specific wavelength. When the compound I-1 is irradiated with light of a specific wavelength, the light-releasing group B is detached from the compound I-1 to generate a compound represented by the following general formula (I-2) containing a hydroxyl group and an atomic group A having an ultraviolet absorption function.

[Chemical 4]

(In the formula, A represents an atomic group having an ultraviolet absorption function, and k represents an integer of 1 to 10)

The wavelength of the light from which the light-releasing group B is detached from the compound I-1 is, for example, a wavelength region of ultraviolet rays or visible rays. Specifically, it may be set to include a wavelength of 365 nm, more specifically, it may be set to include a wavelength of 250 nm or more and 450 nm or less, and preferably, it may be set to include a wavelength of 280 nm or more and 380 nm or less. Light of wavelength.
The cumulative light amount of light irradiated in order to release the light-releasing group B from the compound I-1 may be, for example, 1,000 mJ / cm ² or more and 10,000 mJ / cm ² or less, and preferably 1000 mJ / cm ² or more and 5000 mJ. / cm ² or less, more preferably 2000 mJ / cm ² or more and 4000 mJ / cm ² or less. The reason for this is that the cumulative light amount of light irradiated to harden a composition containing a polymerizable compound or the like can usually be set to less than 1000 mJ / cm ² . Therefore, when the cumulative light amount is within the above range, application to, for example, a photocurable composition becomes easy.
It should be noted that the so-called light-releasing group B may be detached as long as it can provide a desired ultraviolet absorbing function. For example, the light-releasing group may have a removal rate of 50% or more, and more preferably 80% or more. The reason is that application to a photocurable composition becomes easy.
On the other hand, in the compound I-1, the cumulative amount of light for suppressing light detachment may be as long as the desired hardening inhibitory effect is obtained, and may be set to less than 1000 mJ / cm ² . The reason is that application to a photocurable composition becomes easy.
In addition, the so-called suppression of light detachment is only required to obtain the desired effect of inhibiting hardening. For example, the detachment rate of the light detachment group B may be less than 50%, and preferably 20% or less. The reason is that application to a photocurable composition becomes easy.
About the said cumulative light quantity, the 0.01 mass% acetonitrile solution of the compound I-1 can be prepared and measured using the same method as the measurement method of the detachment rate described in an Example.

Specific examples of the light-releasing group B satisfying the above requirements include the following general formulae (B-1), (B-2), (B-3), (B-4), (B-5), (B-6), (B-7) and (B-8). Among them, the following general formulae (B-1-a), (B-2-a), (B-3-a), (B-4), (B-5), and (B-6) are preferred. The group represented by (B-7-a), (B-7-b), and (B-8-a) is preferably a group represented by the following general formula (B-1-a). The reason is that by using such a light-releasing group, the compound I-1 can be easily detached, and a cured product can be easily provided with an ultraviolet absorbing function. Further, as the light-releasing group B that satisfies the above-mentioned requirements, specifically, groups represented by the following general formulae (B-9) and (B-10) may be mentioned.

[Chemical 5]

[Chemical 6]

(In the formula, R ¹¹ , R ¹³ , R ¹⁶ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²³ , R ²⁶ and R ²⁸ each independently represent a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, and the number of carbon atoms. An alkyl group of 1 to 40, an aryl group of 6 to 20 carbon atoms, an arylalkyl group of 7 to 20 carbon atoms, or a heterocyclic group containing 2 to 20 carbon atoms,
R ¹² , R ¹⁴ , R ¹⁷ , R ²¹ , R ²² , R ²⁴ , R ²⁵ , R ²⁷ , R ^29, and R ³⁰ each independently represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, and a carbon atom. An alkyl group having 1 to 40 atoms, an aryl group having 6 to 20 carbon atoms, an aryl alkyl group having 7 to 20 carbon atoms or a heterocyclic group containing 2 to 20 carbon atoms,
R ¹⁵ represents 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 a heterocyclic group containing 2 to 20 carbon atoms,
R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ The methylene group in the alkyl group and the arylalkyl group represented by R ²⁸ , R ^29, and R ³⁰ is substituted with a carbon-carbon double bond, -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-, -NR'-,> P = O, -SS-, -SO ₂ -or a combination of these,
R 'represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,
There are plural R ¹¹ each other, plural R ¹³ each other, plural R ¹⁶ each other, plural R ¹⁸ each other, plural R ¹⁹ each other, plural R ²⁰ each other, plural R ²³ each other, plural R ²⁶ each other and plural When R ²⁸ are bonded to each other to form a benzene ring or a naphthalene ring,
A plurality of R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²³ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ and R ³⁰ have The same situation, different situations,
b1, b2, b3, b6, b7, b8, and b9 each independently represent an integer from 0 to 4,
b4 and b5 each independently represent an integer from 0 to 5,
** indicates the bonding position with the above AO-)

[化 6A]

(In the formula, R ³¹ and R ⁴⁰ each independently represent 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. Arylalkyl of -20 or heterocyclic group containing 2 to 20 carbon atoms,
R ³² , R ³³ , R ⁴¹ , R ⁴² , R ⁴³ , and R ⁴⁴ each independently represent 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, and a carbon number. An aryl group of 6 to 20, an arylalkyl group of 7 to 20 carbon atoms, or a heterocyclic group containing 2 to 20 carbon atoms,
The methylene group in the alkyl group and the arylalkyl group represented by R ³¹ , R ³² , R ³³ , R ⁴⁰ , R ⁴¹ , R ⁴² , R ⁴³ and R ⁴⁴ is substituted with a carbon-carbon double bond, -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-, -NR'-,> P = O, -SS-, -SO ₂ -or a combination of these,
When the above-mentioned alkyl group, aryl group, arylalkyl group and heterocyclic group have substituents,
c1 represents an integer from 0 to 5,
c2 represents an integer from 0 to 4,
** indicates the bonding position with the above AO-)

R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³² , R ³³ , R ⁴⁰ , R ⁴¹ , R ⁴² , R ^43, and R ⁴⁴ (hereinafter, these functional groups are collectively referred to as R ^11, etc.) Examples of the alkyl group having 1 to 40 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, second butyl, third butyl, isobutyl, pentyl, and iso. Pentyl, third pentyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, Triheptyl, 1-octyl, isooctyl, third octyl and adamantyl, etc.

Examples of the aryl group having 6 to 20 carbon atoms represented by R ¹¹ and the like include a phenyl group, a naphthyl group, and an anthryl group.

Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R ¹¹ and the like include a benzyl group, a fluorenyl group, an indenyl group, a 9-fluorenylmethyl group, and the like.

Examples of the heterocyclic group having 2 to 20 carbon atoms represented by the aforementioned R ¹¹ and the like include a pyridyl group, a pyrimidinyl group, a pyridyl group, a piperidinyl group, a pyranyl group, a pyrazolyl group, a triyl group, and a pyrrolyl group. , Quinolinyl, isoquinolinyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl , Benzothienyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidone-1- Group, 2-piperidone-1-yl, 2,4-dioxyimidazolidin-3-yl, 2,4-dioxyoxazolidin-3-yl, and the like.

Examples of the alkyl group having 1 to 8 carbon atoms represented by the aforementioned R ′ include those having 1 to 8 carbon atoms exemplified as the alkyl group represented by R ¹¹ and the like.

The above-mentioned alkyl group, aryl group, arylalkyl group and heterocyclic group may have a substituent. The compound I-1 of the present invention includes those having no substituent and those having a substituent unless otherwise specified.

Examples of the substituent in the case where a hydrogen atom such as an alkyl group, an aryl group, an arylalkyl group, and a heterocyclic group are substituted include vinyl, allyl, acrylic, and methacrylic groups. Saturated groups; halogen atoms such as fluorine, chlorine, bromine, and iodine; ethyl fluorenyl, 2-chloroethyl fluorenyl, propyl fluorenyl, octyl fluorenyl, propylene fluorenyl, methacryl fluorenyl, phenylcarbonyl (benzyl fluorenyl) Phthalate, 4-trifluoromethylbenzyl, pentamyl, o-hydroxybenzyl, oxalyl, stearyl, methoxycarbonyl, ethoxycarbonyl, Third butoxycarbonyl group, n-octadecyloxycarbonyl group and fluorenyl groups such as carbamoyl group; fluorenyl groups such as ethoxyl and benzyloxy groups; amine, ethylamino, dimethylamino , Diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, aniline, chlorophenylamine, tolylamine, methoxyaniline, N-methyl-aniline, diphenylamino, naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, ethenylamino, benzamidine Amine, methylamino , Pentamylamino, Laurylamino, Aminomethylamino, N, N-Dimethylaminocarbonylamino, N, N-Diethylaminocarbonylamino, Phenylcarbonylamino , Methoxycarbonylamino, ethoxycarbonylamino, tertiary butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxycarbonyl Substituted amino groups such as amine, sulfamoylamino, N, N-dimethylaminosulfoamidoamino, mesulphinomethylamino, butanesulfinoamino and benzenesulfinomethylamino; Amido, sulfoamido, carboxyl, cyano, sulfo, hydroxy, nitro, mercapto, amidoimino, carbamoamido, sulfoamido, phosphonic acid, phosphate or carboxyl, sulfo, Phosphonic acid, phosphate salts, etc.

In the present invention, when the number of carbon atoms of a radical is substituted by a hydrogen atom in the radical by a substituent, the number of carbon atoms of the substituted radical is specified. For example, when a hydrogen atom of an alkyl group having 1 to 40 carbon atoms is replaced, the so-called 1 to 40 carbon atoms refers to the number of carbon atoms after the hydrogen atom is replaced, and does not mean that the hydrogen atom is replaced before the hydrogen atom is replaced. Of carbon atoms.

In the present invention, when the number of carbon atoms of the group is substituted by the above-mentioned divalent group when the methylene group in the group is substituted, the number of carbon atoms of the substituted group is specified. For example, in the present specification, when a methylene group in an alkyl group having 1 to 40 carbon atoms is substituted with the above-mentioned divalent group, the so-called "carbon number 1 to 40" refers to a group after the methylene group is substituted. The number of carbon atoms does not refer to the number of carbon atoms before the methylene group is replaced. Therefore, "-OC ₄₀ H ₈₁ " corresponds to "a terminal methylene group is substituted with -O- alkyl group having 40 carbon atoms (= alkoxy group having 40 carbon atoms)". Similarly, "-CO-OC ₃₉ H ₇₉ " corresponds to "the terminal methylene group is substituted with -CO-O- and a carbon atom having 40 carbon atoms".

The methylene groups in the alkyl and arylalkyl groups used in R ¹¹ and the like are substituted with carbon-carbon double bonds, -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-, -NR'-,> P = O, -SS-, -SO ₂ -or a combination of these.
In addition, the combination replacing the methylene group may be a combination under the condition that oxygen atoms are not adjacent.

When an alkyl group having 1 to 40 carbon atoms represented by R ¹¹ and the like exists, the methylene group at the terminal of the base end side is substituted with -O- to form an alkoxy group. Examples of such an alkoxy group include an alkoxy group having 1 to 10 carbon atoms. Specific examples include methoxy, ethoxy, isopropoxy, butoxy, second butoxy, third butoxy, isobutoxy, pentoxy, isopentoxy, Third pentyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy Group, isoheptyloxy, third heptyloxy, 1-octyloxy, isooctyloxy, third octyloxy and the like.

The aforementioned R ¹¹ , R ¹³ , R ¹⁶ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²³ , R ²⁶ and R ^{28 are} preferably a group other than a hydroxyl group, and are preferably a halogen atom, a cyano group, a nitro group, a carboxyl group, and a carbon group. An alkyl group having 1 to 40 atoms, an aryl group having 6 to 20 carbon atoms, an aryl alkyl group having 7 to 20 carbon atoms or a heterocyclic group containing 2 to 20 carbon atoms, and the like. The reason is that by using a group other than a hydroxyl group, the photo-leaving group B can be easily detached from the compound I-1, and the synthesis of the compound I-1 is easy.
The R ¹¹ and R ^{23 are} particularly preferably an alkoxy group having 1 to 10 carbon atoms such as a nitro group and a methoxy group, an alkyl group having 1 to 40 carbon atoms such as a methyl group, a halogen atom, and the like. The reason is that the photo-leaving group B can be easily detached from the compound I-1, and the synthesis of the compound I-1 is easy.
The aforementioned R ^{11 is} preferably an alkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a halogen atom, more preferably an alkoxy group having 1 to 5 carbon atoms and 1 to 5 carbon atoms. The alkyl group or halogen atom is more preferably an alkoxy group or a halogen atom having 1 to 5 carbon atoms, and particularly preferably an alkoxy group, a chlorine atom, or a bromine atom having 1 to 3 carbon atoms. The reason is that the photo-leaving group B can be easily detached from the compound I-1, and the synthesis of the compound I-1 is easy.
The aforementioned R ¹³ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²⁶ and R ^{28 are} preferably an alkyl group having 1 to 40 carbon atoms. The reason is that the photo-leaving group B can be easily detached from the compound I-1, and the synthesis of the compound I-1 is easy.
The aforementioned R ^{16 is} preferably two adjacent R ¹⁶ bonded to each other to form a benzene ring. The reason is that the photo-leaving group B can be easily detached from the compound I-1, and the synthesis of the compound I-1 is easy.
The R ³¹ and R ^{40 are} preferably a group other than a hydroxyl group, and are preferably a halogen atom, a cyano 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 carbon atoms. An arylalkyl group of 20 or a heterocyclic group containing 2 to 20 carbon atoms, and the like. The reason is that by using a group other than a hydroxyl group, the photo-leaving group B can be easily detached from the compound I-1, and the synthesis of the compound I-1 is easy.
The R ^{31 is} preferably an alkyl group having 1 to 40 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, still more preferably an alkyl group having 1 to 5 carbon atoms, and particularly preferably 1 carbon atom. ~ 3 alkyl.

In the case where the methylene group in the alkyl group and the arylalkyl group represented by R ¹⁸ and R ¹⁹ is substituted with -O-, the alkylene group and the arylalkyl group may be substituted to replace the above-mentioned methylene group. -O- of a methyl group, that is, a methylene group other than the terminal of an alkyl group and an arylalkyl group may be substituted.

R ^{12 is} preferably a hydrogen atom, a carboxyl group, and an alkyl group having 1 to 5 carbon atoms, and particularly preferably a hydrogen atom and a methyl group. The reason is that the photo-leaving group B can be easily detached from the compound I-1, and the synthesis of the compound I-1 is easy.
Regarding the above R ¹⁴ , R ¹⁷ , R ²¹ , R ²⁴ , R ²⁵ , R ²⁷ , R ²⁹ and R ³⁰ , a hydrogen atom and an alkyl group having 1 to 40 carbon atoms are preferred, and a hydrogen atom is particularly preferred. The reason is that the photo-leaving group B can be easily detached from the compound I-1, and the synthesis of the compound I-1 is easy.
The aforementioned R ¹⁵ and R ^{22 are} preferably an alkyl group having 1 to 5 carbon atoms, and particularly preferably a methyl group. The reason therefor is to provide a compound which has less resistance to hardening and can easily provide an ultraviolet absorbing function to a hardened material.
The aforementioned R ³² and R ³³ are each independently, preferably a hydrogen atom, a carboxyl group or an alkyl group having 1 to 5 carbon atoms, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. The reason therefor is to provide a compound which has less resistance to hardening and can easily provide an ultraviolet absorbing function to a hardened material.
The aforementioned R ⁴¹ to R ⁴⁴ are each independently, preferably a hydrogen atom, a carboxyl group or an alkyl group having 1 to 5 carbon atoms, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. The reason therefor is to provide a compound which has less resistance to hardening and can easily provide an ultraviolet absorbing function to a hardened material.

The above b1, b2, b3, b6, b7, b8, and b9 can be independently set to integers of 0 to 4. From the viewpoint of ease of synthesis, the integers of 0 to 3 are preferred, and 0 to 4 are more preferred. An integer of 2 is more preferably 0 to 1, and even more preferably 0. The reason therefor is to provide a compound which has less resistance to hardening and can easily provide an ultraviolet absorbing function to a hardened material.
The above b4 and b5 can be independently set to integers of 0 to 5. In terms of ease of synthesis, an integer of 0 to 3 is preferred, an integer of 0 to 2 is more preferred, and an integer of 0 to 5 is further preferred. 1, particularly preferably 0. The reason therefor is to provide a compound which has less resistance to hardening and can easily provide an ultraviolet absorbing function to a hardened material.
The above c1 can be set to an integer of 0 to 5. In terms of ease of synthesis, an integer of 0 to 3 is preferred, an integer of 0 to 2 is more preferred, and an integer of 0 to 1 is further preferred. Better to be 1. The reason therefor is to provide a compound which has less resistance to hardening and can easily provide an ultraviolet absorbing function to a hardened material.
The above c2 can be set to an integer of 0 to 4. In terms of ease of synthesis, an integer of 0 to 3 is preferred, an integer of 0 to 2 is more preferred, and an integer of 0 to 1 is further preferred. It is preferably 0. The reason therefor is to provide a compound which has less resistance to hardening and can easily provide an ultraviolet absorbing function to a hardened material.

When the kind of the light-releasing group B contained in the compound I-1 of the present invention is k or more, there may be one kind of each compound I-1 and sometimes two or more kinds, so there is less hindering of hardening. From the viewpoint that the ultraviolet-absorbing function and the like can be easily imparted to the cured product and the synthesis of the compound I-1 is facilitated, one type is preferred.

The number k of the light-releasing group is an integer of 1 to 10, from the viewpoints of less resistance to hardening, the ability to easily provide a UV absorbing function to the cured material, and the viewpoint of ease of synthesis, it is preferably 1 to 5 The integer is more preferably an integer of 1 to 4, and even more preferably an integer of 1 to 3.

2.Atomic group A with ultraviolet absorption function
The atomic group A is an atomic group having an ultraviolet absorption function.
The compound I-1 of the present invention survives the compound I-2 having a hydroxyl group by irradiating light of a specific wavelength, and the light-releasing group B is released. In addition, since the atomic group A has an ultraviolet absorption function, the compound I-2 exhibits an ultraviolet absorption function.

The "having an ultraviolet absorbing function" is, for example, a compound I-1 capable of absorbing a compound having an ultraviolet absorbing function, specifically, the light-releasing group B after detachment, that is, the compound I-2 has an absorbable wavelength of 250 nm or more and 450 Light in the range below nm. The atomic group having an ultraviolet absorbing function in the present invention may be a group having an ultraviolet absorbing function or an aggregate containing at least one group having an ultraviolet absorbing group.
More specifically, the so-called compound I-1 having an ultraviolet absorbing function after the light-release group B is detached, that is, the maximum absorption wavelength of the compound I-2 within a range of 250 nm or more and 600 nm or less is 250 nm or more and The light having a maximum absorption wavelength of 400 nm or less is preferably light having a maximum absorption wavelength of 260 nm or more and 390 nm or less, and particularly preferably light having a maximum absorption wavelength of 280 nm or more and 380 nm or less. The reason therefor is to provide a compound which has less resistance to hardening and can easily provide an ultraviolet absorbing function to a hardened material.
The maximum absorption wavelength of the compound I-1, that is, the compound I-2 after the photo-releasing group B is removed, can be measured, for example, by the following measurement method.
As the sample for evaluation, for example, a compound (I-1) obtained by removing the photo-release group B, that is, a compound (I-2) dissolved in a solvent (acetonitrile) at a concentration of 0.01% by mass is used. In addition, it can be obtained by filling a sample for evaluation into a quartz cell (optical path length 10 mm, thickness 1.25 mm) and measuring the absorbance using an absorbance meter (for example, U-3900 (manufactured by Hitachi High-Tech Science)).

In addition, the maximum absorption wavelength of the compound I-1 of the present invention before the light-releasing group B is separated from the maximum absorption wavelength of the compound I-1 (the compound I-2) after the light-releasing group B is removed In this case, it is preferable that the maximum absorption wavelength of the compound I-1 before the light release group B is released is shorter than the maximum absorption wavelength of the compound I-2 in a range of 250 nm or more and 600 nm or less. The reason is that application to a photocurable composition becomes easy.
The difference between the maximum absorption wavelengths of the compound I-1 and the compound I-2 after the photo-dissociating group B is removed is preferably 1 nm or more, more preferably 1 nm or more and 100 nm or less, even more preferably 1 nm or more and Below 50 nm. The reason is that application to a photocurable composition becomes easy.

Such an atomic group A can be the same as the atomic group generally used for the ultraviolet absorber which has a phenolic hydroxyl group. That is, the compound I-2 is generally used as an ultraviolet absorbent having a phenolic hydroxyl group.
Specifically, as the compound I-2, 2-hydroxybenzophenones, 2- (2'-hydroxyphenyl) benzotriazoles, etc. described in Japanese Patent Laid-Open No. 2017-008221 can be used, Benzoates and triaryls, etc., or benzotriazole-based ultraviolet absorbers and benzophenone-based ultraviolet absorbers described in Japanese Patent Laid-Open No. 2002-97224.

Examples of the atomic group A include a phenolic structure in which a phenolic hydroxyl group is protected by a photo-releasing group B, that is, a benzene ring containing a B-O- group directly bonded thereto. Specific examples include: an atomic group containing a BO-directly bonded benzo ring and a benzotriazole ring; an atomic group containing a BO-directly bonded benzophenone ring; and a BO-directly bonded benzene ring With tricyclic radicals. A structure containing at least one type of a benzotriazole group, a benzophenone group, and a triphenyl group directly bonded to a benzene ring contained in the above phenol structure is preferred. Among them, a benzotriazole group, At least one of the benzophenone group and the tri-group has a bond position to the benzene ring relative to the bond position of the BO-. The reason is that it is easy to make a compound that has less resistance to hardening and can easily provide a UV-absorbing function to a cured material.

Examples of the compound I-1 of the present invention include those represented by the following general formulae (A-1), (A-2), and (A-3).

[Chemical 7]

(In the formula, R ¹ and R ² each independently represent 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 a carbon atom. An arylalkyl group having 7 to 20 atoms, a heterocyclic group containing 2 to 20 carbon atoms or the above-OB,
At least one of R ¹ and R ² is the above-OB,
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ each independently represent 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 20 carbon atoms. An aryl group, an arylalkyl group having 7 to 20 carbon atoms, or a heterocyclic group containing 2 to 20 carbon atoms,
The methylene group in the alkyl or arylalkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ^7, and R ⁸ is also substituted with a carbon-carbon double bond,- 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-, -NR'-,> P = O, -SS- , -SO ₂ -or a combination of these,
R 'represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,
There may be cases where a plurality of R ³ each other, a plurality of R ⁴ each other, a plurality of R ⁵ each other, a plurality of R ⁶ each other, and a plurality of R ⁷ are respectively bonded to each other to form a benzene ring or a naphthalene ring,
A plurality of R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 may} be the same as each other, and may be different from each other.
m1 and m2 each independently represent an integer from 1 to 10,
n represents an integer from 1 to 3,
a1 represents an integer from 0 to 4,
a2 represents an integer from 0 to 2,
a3 represents an integer from 0 to 4,
a4 represents an integer from 0 to 3,
a5 represents an integer from 0 to 3,
a6 represents an integer from 0 to 3-n,
(X ¹ and X ² represent the bond groups of valence m1 and m2, respectively)

The above-mentioned R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ represent an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a carbon atom. Examples of the arylalkyl group having 7 to 20 carbon atoms, the heterocyclic group containing 2 to 20 carbon atoms, and the alkyl group having 1 to 8 carbon atoms represented by R ′ may be exemplified as the above-mentioned "1. Photodissociative group B" R ¹¹ and the like described in this item and those exemplified by R '.

At least one of the above R ¹ and R ² is the above-OB.
From the viewpoint of ease of synthesis, R ¹ and R ² are preferably -OB.
R ¹ and R ² above causes the ultraviolet absorbing function of the large variation of the viewpoint, preferably both of R ¹ and R ² above -OB.
When only one of the above-mentioned R ¹ and R ² is the above-OB, the other is preferably a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, and carbon. The arylalkyl group having 7 to 20 atoms or the heterocyclic group containing 2 to 20 carbon atoms is more preferably a hydrogen atom or an alkyl group having 1 to 40 carbon atoms. The reason for this is that, since the other of the R ¹ and R ² is the functional group, the compound I-1 has a large change in the ultraviolet absorption function. The reason is that the above-mentioned compound I-1 becomes one with less hindrance to hardening.
In addition, as the alkyl group, arylalkyl group, and the like, for example, those in which methylene is interrupted by -O-, -CO-, or the like can be preferably used.

The aforementioned R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} preferably a cyano group, a hydroxyl group, an alkyl group having 1 to 40 carbon atoms, and an arylalkyl group having 7 to 20 carbon atoms, and more preferably It is a cyano group, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, and an arylalkyl group having 7 to 10 carbon atoms. Among them, an alkyl group having 3 to 20 carbon atoms is more preferable, and an alkyl group having 3 carbon atoms is more preferable. ~ 10 alkyl. The reason is that the synthesis of the compound I-1 of the present invention becomes easy, and the compound I-1 exhibits an excellent ultraviolet absorbing function after the light-release group B is released.

In addition, from the viewpoint of exhibiting an excellent ultraviolet absorbing function after the light-releasing group B is released, R ^{4 is} preferably an alkyl group having a branched structure having 3 to 15 carbon atoms, and more preferably 5 having carbon atoms. The alkyl group having a branched structure of -12, more preferably an alkyl group having a branched structure of 6 to 11 carbon atoms, and particularly preferably an alkyl group having a branched structure of 7 to 10 carbon atoms.
As the bonding site of R ⁴ in the benzene ring, it can be bonded at any position capable of bonding, and it is preferably para-position relative to the bonding site of -OB. The reason is that the compound I-1 exhibits an excellent ultraviolet absorbing function after the light-release group B is released.

From the standpoint of exhibiting an excellent ultraviolet absorbing function after the photo-leaving group B is detached, R ⁵ and R ^{6 are} preferably those in which the methylene group on the side of the benzene ring side is substituted with -O- with 1 to 20 carbon atoms. The alkyl group, that is, the alkoxy group having 1 to 20 carbon atoms, is preferably an alkoxy group having 3 to 15 carbon atoms, and particularly preferably an alkoxy group having 5 to 12 carbon atoms.
The bonding sites of R ⁵ and R ⁶ in the benzene ring may be bonded at any position capable of bonding, and it is preferred that the bonding site with respect to -OB is meta. The reason is that the compound I-1 exhibits an excellent ultraviolet absorbing function after the light-release group B is released.

From the standpoint that the photo-leaving group B can exhibit an excellent ultraviolet absorbing function after detachment, R ^{7 is} preferably an alkyl group having 1 to 20 carbon atoms in which the methylene group at the benzene ring side end is substituted with -O- That is, an alkoxy group having 1 to 20 carbon atoms. Among them, a methylene chain other than a benzene ring side terminal is preferably substituted with an alkoxy group having 3 to 20 carbon atoms in -O-, -O-CO-. Group, particularly preferably a methylene chain other than the benzene ring side terminal is substituted with -O-, -O-CO- and an alkoxy group having 3 to 15 carbon atoms, particularly preferably a methylene group other than the benzene ring side terminal The base chain is substituted with an alkoxy group having 6 to 15 carbon atoms in -O-, -O-CO-, and particularly preferably a methylene chain other than a benzene ring side end is substituted with -O-, -O- CO- is an alkoxy group having 8 to 13 carbon atoms.
As the bonding site of R ⁷ in the benzene ring, it can be bonded at any position capable of bonding, and it is preferred that the bonding site with respect to -OB is meta. The reason is that the compound I-1 exhibits an excellent ultraviolet absorbing function after the light-release group B is released.
From the standpoint that the light-releasing group B can exhibit an excellent ultraviolet absorption function after detachment, R8 is preferably an aryl group having 6 to 20 carbon atoms, and among them, an aryl group having 6 to 12 carbon atoms is preferred, Particularly preferred is a phenyl group in the presence of a substituent.

Further, as the alkyl group and the arylalkyl group, any of those in which methylene is not interrupted and those in which -O-, -CO-, etc. are interrupted can be preferably used.

The above m1 and m2 represent integers of 1 to 10. From the standpoint of ease of synthesis, the above m1 and m2 are independent of each other, preferably an integer of 1 to 6, more preferably an integer of 1 to 4, particularly preferably an integer of 1 to 3, and particularly preferably 1 to An integer of two. The reason is that the synthesis of the above-mentioned compound I-1 becomes easy, and the compound I-1 exhibits an excellent ultraviolet absorption function after the light-release group B is released.
In addition, from the viewpoint that the compound I-1 exhibits an excellent ultraviolet absorbing function after the light-releasing group B is released, m2 is preferably an integer of 1.

The above-mentioned n represents an integer of 1 to 3. From the viewpoint that the compound I-1 has a large change in the ultraviolet absorbing function, the above-mentioned n is preferably an integer of 2 to 3, particularly preferably 3. From the viewpoint that the compound I-1 exhibits an excellent ultraviolet absorbing function after the light-releasing group B is released, the above-mentioned n is preferably an integer of 1 to 2, and particularly preferably 1.

The above a1 and a3 each independently represent an integer of 0 to 4. From the standpoint of ease of synthesis, the above-mentioned a1 and a3 are independent, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably an integer of 0 to 1. The reason is that the compound I-1 can be made into a compound that exhibits an excellent ultraviolet absorption function after the light-release group B is released.
The a2 is an integer of an integer of 0 to 2. From the viewpoint of solubility, the a2 is preferably an integer of 1 to 2. From the viewpoint that the compound I-1 exhibits an excellent ultraviolet absorbing function after the light-releasing group B is released, the a2 is preferably 1.
The above a4 and a5 each independently represent an integer of 0 to 3. From the viewpoint of ease of synthesis, the above-mentioned a4 and a5 are preferably integers of 0 to 2, particularly preferably integers of 1 to 2, and even more preferably 1. The reason is that the compound I-1 can be made into a compound that exhibits an excellent ultraviolet absorption function after the light-release group B is released.
The above a6 represents an integer of 0 to 3-n. The above-mentioned a6 is preferably an integer of 0 to 1 and more preferably 0 in terms of the viewpoint that the compound I-1 exhibits an excellent ultraviolet absorbing function after detachment of the photo-release group B and the ease of synthesis.

The compound I-1 represented by the above-mentioned general formulae (A-1) and (A-2) has an m1-valence or an m2-valence (hereinafter sometimes referred to as "X") represented by X ¹ and X ² (hereinafter sometimes referred to as "X"). A structure in which a specific atom or group of m is bonded to m1 or m2 (hereinafter sometimes referred to as m). The m specific bases may be the same or different from each other.

The X represents a m-valent bond group.
Specifically, the bonding group X represents a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a group represented by the following (II-a) or (II-b), and> C = O,> NR ⁵³ , -OR ⁵³ , -SR ⁵³ , -NR ⁵³ R ⁵⁴ or an aliphatic hydrocarbon group having 1 to 120 carbon atoms and an aromatic group containing 6 to 35 carbon atoms having the same valence as m A cyclic hydrocarbon group or a heterocyclic group containing 2 to 35 carbon atoms, and R ⁵³ and R ⁵⁴ each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic cyclic hydrocarbon group having 6 to 35 carbon atoms or Heterocyclic group containing 2 to 35 carbon atoms, the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group and heterocyclic group also have -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- , nitrogen atom or a combination of these The above aromatic ring or heterocyclic ring may also be condensed with other rings.
When X is a nitrogen atom, a phosphorus atom, or a bonding group represented by the following (II-a) or (II-b), m is 3, and X is an oxygen atom or a sulfur atom, and> C = In the case of O, -NH-CO-, -CO-NH-, or> NR ⁵³ , m is 2; in the case of X is -OR ⁵³ , -SR ^53, or -NR ⁵³ R ⁵⁴ , m is 1, and There are cases where X forms a ring together with a benzene ring.

[Chemical 8]

(* Means bonded to the adjacent base by * part)

Among the aliphatic hydrocarbon groups having 1 to 120 carbon atoms having the same valence as the value of m represented by the above-mentioned bonding group X, as m being monovalent, for example, methyl, ethyl, propyl, iso Propyl, cyclopropyl, butyl, second butyl, third butyl, isobutyl, pentyl, isopentyl, third pentyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, Cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, third heptyl, n-octyl, isooctyl, third octyl, 2 -Alkyl groups such as ethylhexyl, nonyl, isononyl and decyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, second butoxy, third butoxy , Isobutoxy, pentyloxy, isopentyloxy, third pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, third heptyloxy, n-octyloxy, Isooctyloxy, third octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy and other alkoxy groups; methylthio, ethylthio, propylthio, isopropylthio, butylthio Base, second butylthio, third butylthio, isobutylthio, pentylthio, isopentylthio Third pentylthio, hexylthio, cyclohexylthio, heptylthio, isoheptylthio, third heptylthio, n-octylthio, isooctylthio, third octylthio and 2-ethyl Alkylthio groups such as hexylthio; vinyl, 1-methylvinyl, 2-methylvinyl, 2-propenyl, 1-methyl-3-propenyl, 3-butenyl, 1-methyl -3-butenyl, isobutenyl, 3-pentenyl, 4-hexenyl, cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl Alkenyl groups such as, icosenyl and tescosenyl; and groups in which these groups are substituted with substituents described below.

Among the aliphatic hydrocarbon groups having 1 to 120 carbon atoms having the same valence as the value of m represented by the above-mentioned bonding group X, as m being divalent, examples thereof include methylene, ethylene, and propyl Alkylene such as butylene, butylene and butadiyl; the methylene chain of the above alkylene is replaced with -O-, -S-, -CO-O-, -O-CO-; ethylene glycol, Residues of diol groups such as propylene glycol, butanediol, pentanediol, and hexanediol; dithiol groups such as ethylenedithiol, propylenedithiol, butanedithiol, pentanethiol, and hexanedithiol Residues, and those substituted with substituents described below.

Among the aliphatic hydrocarbon groups having 1 to 120 carbon atoms having the same valence as the value of m represented by the above-mentioned bonding group X, as m is trivalent, for example, propylidene and 1,1,3- An oxyalkylene group such as succinyl propylidene; and a group in which these groups are substituted with a substituent described below.

Among the aromatic ring-containing hydrocarbon groups having 6 to 35 carbon atoms having the same valence as that represented by the above-mentioned bonding group X, as the monovalent valence of m, benzyl, phenethyl, and diphenyl are listed. Arylalkyl groups such as methyl, triphenylmethyl, styryl, and phenallyl; aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; phenylthio and naphthylthio Arylthio, such as radicals: and radicals in which these radicals are substituted with substituents described below.

Among the aromatic ring-containing hydrocarbon groups having 6 to 35 carbon atoms having the same valence as the value of m represented by the above-mentioned bonding group X, examples of those in which m is divalent include arylene such as phenylene and naphthyl Residues of bifunctional phenol groups such as catechol and bisphenol groups; 2,4,8,10-tetraoxaspiro [5,5] undecyl; and these groups are described below A base substituted with a substituent.

Among the aromatic ring-containing hydrocarbon groups having 6 to 35 carbon atoms having the same valence as that represented by the above-mentioned bonding group X, m is trivalent, and phenyl-1,3,5-trimethylene may be mentioned And a base substituted with a substituent described below.

Among the heterocyclic groups containing 2 to 35 carbon atoms having the same valence as the value of m represented by the above-mentioned bonding group X, those in which m is monovalent include pyridyl, pyrimidinyl, daphthyl, and piperidine. Pyridyl, pyranyl, pyrazolyl, triyl, pyrrolyl, quinolinyl, isoquinolinyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, Benzofuryl, thienyl, thiophenyl, benzothienyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, iso Oxazolyl, indolyl, 2-pyrrolidinone-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazol-3-yl, 2,4-dioxyfluorene Amidazin-3-yl, benzotriazolyl, and the like; and groups in which these groups are substituted with substituents described below.

Among the heterocyclic groups having 2 to 35 carbon atoms having the same valence as the value of m represented by the above-mentioned bonding group X, those in which m is divalent include a pyridine ring, a pyrimidine ring, and a piperidine ring , Piperidine, tricyclic, furan ring, thiophene ring, indole ring and the like; and these groups are substituted with substituents described below.

Among the heterocyclic groups containing 2 to 35 carbon atoms having the same valence as the value of m represented by the above-mentioned bonding group X, those in which m is trivalent include trivalent isocyanuric rings Group, a trivalent group having a tricyclic ring, and a group in which these groups are substituted with a substituent described below.

Examples of the aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by R ⁵³ and R ^{54 include} the carbon atom in the aliphatic hydrocarbon group represented by the above X or the group in which the aliphatic hydrocarbon group is substituted with a substituent described below. The number is 1 to 35.
Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or the heterocyclic group containing 2 to 35 carbon atoms represented by R ⁵³ and R ⁵⁴ include the aromatic ring containing 6 to 35 carbon atoms represented by X described above. A hydrocarbon group or a heterocyclic group containing 2 to 35 carbon atoms, or a group in which these groups are substituted with a substituent described below.

Each of the functional groups such as the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group, and the heterocyclic group may have a substituent. The compound I-1 of the present invention includes those having no substituent and those having a substituent unless otherwise specified.
Examples of such a substituent of an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, a heterocyclic group, and the like include the same substituents as those used to substitute a hydrogen atom of an alkyl group used in R ¹¹ and the like.

In the general formulae (A-1) and (A-2), when m is 2, X may represent a group represented by the following general formula (1).

[Chemical 9]

(In the general formula (1), Y ¹ represents a single bond, -CR ⁵⁵ R ^56- , -NR ^57- , a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, and a divalent carbon atom having 6 to 35. An aromatic ring-containing hydrocarbon group, a divalent heterocyclic group having 2 to 35 carbon atoms, or any of the following groups (1-1) to (1-3), the aliphatic hydrocarbon group, carbon number Aromatic hydrocarbon groups containing 6 to 35 and heterocyclic groups containing 2 to 35 carbon atoms also exist as -O-, -S-, -CO-, -COO-, -OCO- or -NH-, or the like If the basis of the combination is interrupted,
R ⁵⁵ and R ⁵⁶ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms,
Z ¹ and Z ² each independently represent a direct bond, -O-, -S-,> CO, -CO-O-, -O-CO-, -SO _2- , -SS-, -SO-,> NR ⁵⁷ 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 group containing 2 to 35 carbon atoms,
(* Means bonded to the adjacent base by * part)

[Chemical 10]

(In the above formula, R ⁵⁹ represents a hydrogen atom, a phenyl group having a substituent, or a cycloalkyl group having 3 to 10 carbon atoms when a substituent is also present.
R ⁶⁰ represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group or halogen atom having 2 to 10 carbon atoms, and the alkyl group, alkoxy group, and alkenyl group also exist. In the case of substituents,
c1 represents an integer from 0 to 5,
(* Means bonded to the adjacent base by * part)

[Chemical 11]

(* Means bonded to the adjacent base by * part)

[Chemical 12]

(In the above formula, R ⁶¹ and R ⁶² each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, and 6 to 20 carbon atoms. Arylthio group of 20, arylalkenyl group of 6 to 20 carbon atoms, arylalkyl group of 7 to 20 carbon atoms, heterocyclic group or halogen atom containing 2 to 20 carbon atoms, the alkyl group and aromatic group The methylene group in the alkyl group may be substituted with an unsaturated bond, -O- or -S-,
R ^{61 may} also form a ring with adjacent R ⁶¹ ,
c2 represents a number from 0 to 4,
c3 represents a number from 0 to 8,
c4 is a number from 0 to 4,
c5 is a number from 0 to 4,
The total number of c4 and c5 is 2 to 4,
(* Means bonded to the adjacent base by * part)

[Chemical 13]

(In the general formula (2), Y ¹¹ represents a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or Heterocyclic group containing 2 to 35 carbon atoms,
Z ¹ , Z ² and Z ³ each independently represent a direct bond, -O-, -S-,> CO, -CO-O-, -O-CO-, -SO _2- , -SS-, -SO- ,> NR ⁶² , PR ⁶² , aliphatic hydrocarbon group having 1 to 35 carbon atoms, aromatic ring hydrocarbon group having 6 to 35 carbon atoms or heterocyclic group containing 2 to 35 carbon atoms,
R ⁶² represents 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 group containing 2 to 35 carbon atoms,
The aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms and the heterocyclic group containing 2 to 35 carbon atoms have carbon-carbon double bonds, -O-, -CO-, -O-CO-, -CO-O- or -SO ₂ -In case of interruption)

[Chemical 14]

(In the general formula (3), Y ¹² represents a carbon atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms having a tetravalent carbon number, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms having a tetravalent number, or a tetravalent carbon atom. A heterocyclic group containing 2 to 35, the aliphatic hydrocarbon group, an aromatic ring containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic group containing 2 to 35 carbon atoms are present as -COO-, -O-, -OCO In the case of-, -NHCO-, -NH-, or -CONH- interruption, Z ¹ to Z ⁴ each independently represent a base in the same range as the base represented by Z ¹ to Z ³ in the general formula (2))

[Chemical 15]

(In the above general formula (4), Y ¹³ represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a pentavalent carbon atom having 6 to 30 aromatic ring-containing hydrocarbon groups, or a pentavalent carbon atom having 2 to 30 Heterocyclic groups, aliphatic hydrocarbon groups, aromatic ring hydrocarbon groups with 6 to 35 carbon atoms or heterocyclic groups with 2 to 35 carbon atoms also exist -COO-, -O-, -OCO-,- In the case of NHCO-, -NH- or -CONH- interruption, Z ¹ to Z ⁵ each independently represent the same group as the group represented by Z ¹ to Z ³ in the above general formula (2))

[Chemical 16]

(In the above general formula (5), Y ¹⁴ represents a single bond, an aliphatic hydrocarbon group having 2 to 35 carbon atoms in the hexavalent number, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms in the hexavalent group, or a carbon number in the hexavalent group. A heterocyclic group containing 2 to 35, the aliphatic hydrocarbon group, an aromatic ring containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic group containing 2 to 35 carbon atoms are present as -COO-, -O-, -OCO- In the case of interruption of -NHCO-, -NH-, or -CONH-, Z ¹ to Z ⁶ each independently represent the same base as that represented by Z ¹ to Z ³ in the above general formula (7))

Examples of the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y ^{1 in} the group represented by the general formula (1) include methane, ethane, propane, isopropane, butane, and second Butane, third butane, isobutane, hexane, 2-methylhexane, 3-methylhexane, heptane, 2-methylheptane, 3-methylheptane, isoheptane, Third heptane, 1-methyloctane, isooctane, third octane, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, 2,4-dimethylcyclobutane , 4-methylcyclohexane, and other divalent groups substituted with Z ¹ and Z ² . These groups may be interrupted by -O-, -S-, -CO-, -COO-, -OCO-, -NH- or a combination of these groups.

Examples of the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ^{1 in} the group represented by the general formula (1) include a group such as phenylene, naphthyl, and biphenyl via Z Divalent radicals substituted by ¹ and Z ² .

Examples of the divalent heterocyclic group having 2 to 35 carbon atoms represented by Y ^{1 in} the group represented by the general formula (1) include pyridine, pyridine, piperidine, piperidine, pyrimidine, da, tri, Hexahydrotrifuran, tetrahydrofuran, alkane, , Thiophene, thietane, etc. are divalent radicals substituted with Z ¹ and Z ² .

Among the groups represented by the above general formula (1), an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group and a heterocyclic group represented by Y ¹ have a halogen atom, a cyano group, a nitro group, or an alkoxy group having 1 to 8 carbon atoms. The case of radical substitution.
The functional groups such as the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group and the heterocyclic group may have substituents. Unless otherwise specified, they are unsubstituted or substituted without substituents.
Examples of such an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, and a heterocyclic group-containing substituent include the same substituents as those substituted for a hydrogen atom such as an alkyl group used for R ¹¹ and the like.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R ⁵⁵ and R ⁵⁶ among the groups represented by the general formula (1) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, Second butyl, third butyl, isobutyl, pentyl, isopentyl, third pentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2 -Heptyl, 3-heptyl, isoheptyl, third heptyl, 1-octyl, isooctyl, third octyl, etc.

Examples of the aryl group having 6 to 20 carbon atoms represented by R ⁵⁵ and R ⁵⁶ among the groups represented by the general formula (1) include a phenyl group, a naphthyl group, a 2-methylphenyl group, and a 3-methyl group. Phenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4 -Third butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2, 5-Di-third-pentylphenyl, 2,4,5-trimethylphenyl and the like.
Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R ⁵⁵ and R ⁵⁶ in the group represented by the general formula (1) include benzyl, phenethyl, and 2-phenylpropane-2. -Yl, diphenylmethyl, triphenylmethyl, styryl, phenylallyl, and the like.

Among the groups represented by the general formula (1), R ⁵⁷ and R ⁵⁸ represent aliphatic hydrocarbon groups having 1 to 35 carbon atoms, aromatic ring hydrocarbon groups having 6 to 35 carbon atoms, or 2 to 35 carbon atoms. Examples of the heterocyclic group include the same as those exemplified for R ⁵³ and R ⁵⁴ .

Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R ⁵⁹ among the groups represented by the general formula (1-1) include cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, A cyclooctyl group and the like are substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.

Examples of the alkyl group having 1 to 10 carbon atoms represented by R ^{60 in} the group represented by the general formula (1-1) include R ¹¹ and the like in the item of "1. Photodissociative group B". Examples of the alkyl group include those having 1 to 10 carbon atoms.
Examples of the alkoxy group having 1 to 10 carbon atoms represented by R ^{60 in} the group represented by the general formula (1-1) include R ¹¹ and the like in the item of "1. Photodissociation group B". The number of carbon atoms exemplified by the represented alkoxy group is 1 to 10.
Examples of the alkenyl group having 2 to 10 carbon atoms represented by R ^{60 in} the group represented by the general formula (1-1) include vinyl, allyl, 1-propenyl, isopropenyl, 2 -Butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl, and the like.
The alkyl group, alkoxy group, and alkenyl group represented by the above-mentioned R ⁶⁰ may be substituted with a halogen atom, and the substitution position is not limited.

Among the groups represented by the general formula (1-3), R ⁶¹ and R ⁶² represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an alkyl group having 7 to 20 carbon atoms. Examples of the arylalkyl group include those satisfying a specific number of carbon atoms among those exemplified as R ^{11 in} the item "1. Photodissociative group B" described above.

Examples of the aryloxy group having 6 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the group represented by the general formula (1-3) include a phenoxy group, a naphthyloxy group, and 2-methylbenzene. Oxy, 3-methylphenoxy, 4-methylphenoxy, 4-vinylphenyldioxy, 3-isopropylphenoxy, 4-isopropylphenoxy, 4-but Phenoxy, 4-tert-butylphenoxy, 4-hexylphenoxy, 4-cyclohexylphenoxy, 4-octylphenoxy, 4- (2-ethylhexyl) phenoxy , 2,3-dimethylphenoxy, 2,4-dimethylphenoxy, 2,5-dimethylphenoxy, 2,6-dimethylphenoxy, 3,4-dimethyl Methylphenoxy, 3,5-dimethylphenoxy, 2,4-di-tert-butylphenoxy, 2,5-di-tert-butylphenoxy, 2,6-tertiary Butylphenoxy, 2,4-ditripentylphenoxy, 2,5-tertiarypentylphenoxy, 4-cyclohexylphenoxy, 2,4,5-trimethylphenoxy And ferrocenyloxy groups, and these groups are substituted with halogen atoms.

Examples of the arylthio group having 6 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the group represented by the general formula (1-3) include a carbon atom number 6 in the case where the halogen atom is substituted as described above. The aryloxy group of ~ 20 is substituted by a sulfur atom.

Examples of the arylalkenyl group having 8 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the group represented by the above-mentioned general formula (1-3) include the carbon atom in which the halogen atom is substituted as described above. The oxygen atom of the aryloxy group of 6-20 is substituted with vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, Alkenyl groups such as 2-octenyl.

Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R ⁶¹ and R ⁶² among the groups represented by the general formula (1-3) include pyridyl, pyridyl, piperidinyl, and piperidinyl , Pyrimidinyl, daphthyl, triyl, hexahydrotriyl, furyl, tetrahydrofuryl, alkyl, Group, thiophene group, thiofuran group, and the group in which these groups are substituted with a halogen atom, and the like.

When the functional groups such as the aryloxy group, arylthio group, arylalkenyl group, and heterocyclic group-containing group represented by R ⁶¹ and R ⁶² in the group represented by the general formula (1-3) have a substituent, Unless otherwise specified, they are unsubstituted or substituted.
As a substituent that substitutes for a hydrogen atom such as an aryloxy group, an arylthio group, an arylalkenyl group, and a heterocyclic group, it may be the same as a substituent that substitutes for a hydrogen atom such as an alkyl group used in R ¹¹ and the like. content.

Examples of the trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms represented by Y ^{11 in} the group represented by the general formula (2) include the aliphatic exemplified by the description of X in the general formula (1). A trivalent group substituted with a hydrocarbon group by Z ¹ , Z ² and Z ^3. These groups exist in -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -NH- or a combination of these groups.

Examples of the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ¹¹ among the bases represented by the general formula (2) include those exemplified by the description of X in the general formula (1). A trivalent group in which an aromatic cyclic hydrocarbon group is substituted with Z ¹ , Z ² and Z ³ .

Examples of the trivalent heterocyclic group having 2 to 35 carbon atoms represented by Y ^{11 in} the group represented by the general formula (2) include the groups exemplified by the description of X in the general formula (1). A trivalent group in which a heterocyclic group is substituted with Z ¹ , Z ² and Z ³ .

Among the groups represented by the general formula (2), Z ¹ , Z ² and Z ³ and R ⁶² are an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or Examples of the heterocyclic group having 2 to 35 carbon atoms include the same groups as those exemplified as R ⁵³ and R ⁵⁴ described above.

Examples of the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y ^{12 in} the group represented by the general formula (3) include the aliphatic exemplified by the description of X in the general formula (1). A tetravalent group in which a hydrocarbon group is substituted by Z ¹ , Z ² , Z ³ and Z ^4. There are -O-, -S-, -CO-, -COO-, -OCO-, -NH- or the like. When the combined base is broken.

Examples of the tetravalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ¹² among the bases represented by the general formula (3) include those exemplified by the description of X in the general formula (1). A tetravalent group in which the aromatic cyclic hydrocarbon group is substituted with Z ¹ , Z ² , Z ³ and Z ⁴ .

Examples of the tetravalent heterocyclic group having 2 to 35 carbon atoms represented by Y ^{12 in} the group represented by the general formula (3) include the groups exemplified by the description of X in the general formula (1). A tetravalent group in which a heterocyclic group is substituted with Z ¹ , Z ² , Z ³ and Z ⁴ .

Examples of the pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y ^{13 in} the group represented by the general formula (4) include the aliphatic exemplified by the description of X in the general formula (1). A pentavalent group substituted with a hydrocarbon group by Z ¹ , Z ² , Z ³ , Z ⁴ and Z ^5. There are -O-, -S-, -CO-, -CO-O-, -O-CO-, In the case where -SO _2- , -NH- or a combination of these groups is substituted.

Examples of the pentavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ¹³ among the groups represented by the general formula (4) include the groups exemplified by the description of X in the general formula (1). A pentavalent group in which the aromatic cyclic hydrocarbon group is substituted with Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ .

Examples of the pentavalent heterocyclic group having 2 to 35 carbon atoms represented by Y ^{13 in} the group represented by the general formula (4) include the groups exemplified by the description of X in the general formula (1). A pentavalent group in which a heterocyclic group is substituted with Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ .

The general formula Y (5) in the hexavalent of carbon ¹⁴ atoms represented by an aliphatic hydrocarbon group of 2 to 35, include the above described general formula of X (1) in the exemplified by the aliphatic hydrocarbon group Z ^{1 , Z 2, Z 3, Z} 4, Z 5 and Z ⁶ are substituted with hexavalent radical of the group present is -O -, - S -, - CO -, - COO -, - OCO -, - SO 2 -, -NH- or the combination of these groups is broken.

Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms having a hexavalent number represented by Y ¹⁴ in the general formula (5) include the aromatic ring-containing hydrocarbon group exemplified by the description of X in the general formula (1). Hexavalent radicals substituted by Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ .

Examples of the hexavalent heterocyclic group containing 2 to 35 carbon atoms represented by Y ¹⁴ in the above general formula (5) include the heterocyclic group containing exemplified by the description of X in the general formula (1). Hexavalent radicals substituted by Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ .

When the above-mentioned bonding group X is m, it is preferably an aliphatic hydrocarbon group having 1 to 120 carbon atoms, more preferably a residue of an alkylene group or a diol, and more preferably 1 to 10 carbon atoms. An alkylene group or a diol residue having 1 to 10 carbon atoms, of which an alkylene group having 1 to 5 carbon atoms or a diol residue having 1 to 5 carbon atoms is preferred, and a carbon atom number is particularly preferred 1 to 3 alkylene. The reason for this is that it can be made into a compound that has less resistance to hardening and can easily provide a UV-absorbing function to the cured material, and it is easy to produce compound I-1.

The bonding position between the above-mentioned bonding group X and the benzene ring may be any position capable of bonding in the benzene ring, and is preferably ortho or meta with respect to R ² , for example. The reason for this is that it can be made into a compound that has less resistance to hardening and can easily provide a UV-absorbing function to the hardened material.

When X is m = 1, it is preferably a hydrogen atom or the same group as R2.

The atomic group A may be a phenolic hydroxyl group, that is, the compound I-1 may contain a phenolic hydroxyl group that is not protected by a photo-leaving group B. The number of phenolic hydroxyl groups is preferably 2 or less, and more preferably 0. The reason for this is that the above-mentioned compound I-1 becomes one with less hindrance to hardening.

3. Compound The compound of the present invention may be any one represented by the general formula (I-1), and is a compound represented by the general formula (A-1), (A-2), or (A-3). The leaving group B preferably contains one represented by the general formula (B-1-a). The reason is that the synthesis is easier, and further, the light detachment is easier. The reason is that an ultraviolet absorbing function and the like can be easily provided to the cured product. The reason is that the compound I-1 is a compound represented by the general formula (A-1), (A-2), or (A-3). Therefore, the compound I-1 can be stably absorbed by the detachment of the light detaching group B. A compound of light in the ultraviolet region.

Specific examples of the compound I-1 include the compounds shown below.

[Chemical 17]

[Chemical 18]

[Chemical 19]

[化 19A]

The molecular weight of the compound I-1 can be set according to the application of the compound I-1 and the like. The molecular weight of the compound I-1 is, for example, preferably from 250 to 5,000, more preferably from 300 to 2500, and even more preferably from 350 to 1500. The reason for this is that it can be made into a compound that has less resistance to hardening and can easily provide a UV-absorbing function to the hardened material.
The molecular weight of the compound I-1 is represented by the weight average molecular weight (Mw) when the compound I-1 is a polymer containing a repeating structure as its structure. The weight average molecular weight (Mw) can be calculated as a standard polystyrene conversion value by gel permeation chromatography (GPC).

The weight average molecular weight Mw can be, for example, HLC-8120GPC manufactured by Tosoh Co., Ltd., the dissolution solvent is set to N-methylpyrrolidone added with 0.01 mol / L lithium bromide, and the calibration curve is set using polystyrene standards Mw377400, 210500, 9600, 50400, 20650, 10850, 5460, 2930, 1300, 580 (the above are Easi PS-2 series manufactured by Polymer Laboratories) and Mw1090000 (manufactured by Tosoh Corporation). TSK-GEL ALPHA-M x 2 (manufactured by Tosoh Co., Ltd.) were measured and obtained. The measurement temperature can be set to 40 ° C, and the flow rate can be set to 1.0 mL / min.

The method for producing the compound I-1 is not particularly limited as long as it can obtain a desired structure. For example, it can be obtained by Japanese Patent Laid-Open No. 57-111375, Japanese Patent Laid-Open No. 3-173843, A phenolic compound produced by a method described in Japanese Patent Laid-Open No. 6-128195, Japanese Patent Laid-Open No. 7-206771, Japanese Patent Laid-Open No. 7-252191, or Japanese Patent Laid-Open No. 2004-501128. An alkyl halide compound is obtained by reaction.

The above-mentioned compound I-1 is inactive before light irradiation, and the light detaches from the gene and is irradiated by light irradiation, thereby generating a compound I-2 having a phenolic hydroxyl group.
Moreover, the said compound I-2 is a person exhibiting a ultraviolet absorption function.
As the application of such a compound I-1, an application requiring an ultraviolet absorbing function by light irradiation is preferred, and examples thereof include an ultraviolet absorber added to the composition.

B. Potential UV Absorbent Next, the potential UV absorber of the present invention will be described.
The potential ultraviolet absorbent of the present invention contains the compound I-1 of the present invention.

By containing the compound I-1 of the present invention, the latent ultraviolet absorbent of the present invention has, for example, less hardening resistance, and can easily provide an ultraviolet absorbing function to a cured product.

The content of the compound I-1 in the latent ultraviolet absorber of the present invention is not particularly limited, and can be appropriately set according to the use of the latent ultraviolet absorber and the like.
The latent ultraviolet absorbent of the present invention may be a compound containing the compound I-1 in 100 parts by mass of the latent ultraviolet absorbent, that is, the latent ultraviolet absorbent may be a compound containing only the compound I-1. .
In addition, the potential ultraviolet absorbent of the present invention may contain other components in addition to Compound I-1. When the latent ultraviolet absorbent of the present invention contains other components, the content of the compound I-1 may be 100 parts by mass of the latent ultraviolet absorber, for example, it may be more than 20 parts by mass and 99 parts by mass or less. 25 mass parts or more and 99 mass parts or less, more preferably 50 mass parts or more and 99 mass parts or less, and even more preferably 80 mass parts or more and 99 mass parts or less. The reason for this is that the above-mentioned latent ultraviolet absorbent can effectively exhibit effects such as less resistance to hardening and easy provision of a UV-absorbing function to a cured product.

The types of the compound I-1 contained in the latent ultraviolet absorber may be only one kind, and may be two or more kinds. When the said latent ultraviolet absorber contains several types of compound I-1, the number of types may be 2 or more and 5 or less, for example.

In addition, since the said compound I-1 can be set as the content described in the item of "A. compound", description is abbreviate | omitted here.

As the other component contained in the latent ultraviolet absorber, for example, the same component as described in the item "2. Other components" of "C. Composition" described below can be used.
It is preferable that the said latent ultraviolet absorber contains resin components, such as a polymer which does not have a polymerizable group, as another component. The reason is that the above-mentioned compound I-1 can be stably maintained.

The shape of the above-mentioned latent ultraviolet absorbent may be powdery or granular.
In the case of pellets, as the method for producing the above-mentioned latent ultraviolet absorber, for example, a method can be used in which the compound I-1 and the resin component are mixed using an extruder or the like, and then molded into pellets.

C. Composition Next, the composition of the present invention will be described.
The composition of the present invention contains compound I-1.

According to the composition of the present invention, for example, it is possible to provide a composition which has less resistance to hardening and can obtain a cured product having excellent ultraviolet absorption function. Hereinafter, each component of the said composition is demonstrated.

1. Compound The content of the compound I-1 in the composition of the present invention is not particularly limited as long as it can provide a desired ultraviolet absorbing function or the like to the composition. The content of the compound I-1 in the composition of the present invention may be, for example, 100 mass parts or more and 20 mass parts or less, preferably 0.005 mass parts or more and 10 mass parts or less, based on 100 mass parts of the solid content of the composition. . The reason for this is that it is easy to make a composition that has less resistance to hardening and can easily provide a UV-absorbing function to the cured material.
The solid component includes all components other than the solvent.
In addition, when there is no special description in this specification, content is a mass basis.
The content of the compound I-1 varies depending on the content of the solvent and the like. For example, it can be 0.001 to 20 parts by mass in 100 parts by mass of the composition. Among them, 0.005 to 10 parts by mass and 10 are preferred. Mass parts or less. The reason for this is that it is easy to make a composition that has less resistance to hardening and can easily provide a UV-absorbing function to the cured material.

The type of the compound I-1 contained in the composition may be only one kind, or two or more kinds. The above-mentioned types may be, for example, two or more and five or less.

In addition, since the said compound I-1 can be set as the content described in the item of "A. compound", description is abbreviate | omitted here.

2. Other components The said composition may contain components other than the said compound I-1 depending on the use etc.
Examples of the other components include a resin component. The reason is that the composition of the present invention contains a resin component in addition to the compound I-1, and for example, it is possible to easily impart hardenability to the composition.
Moreover, it is preferable that the composition of this invention contains the said resin component, and also contains a polymerization initiator as another component. This is because the composition of the present invention contains a resin component and a polymerization initiator as other components, so that hardenability and the like can be easily imparted to the composition.

(1) Resin component As the resin component, those capable of retaining the above-mentioned compound I-1 may be mentioned, and they may be appropriately set according to the use of the composition, and examples thereof include polymerizable compounds having a polymerizable group and those having no polymerizable group. Polymer, etc.
By containing a polymerizable compound as the resin component, the composition can be used, for example, as a photocurable composition or a thermosetting composition.

(a) Polymerizable compound The polymerizable compound varies depending on the type of the polymerizable group, that is, the type of the polymerization reaction, and examples thereof include a radical polymerizable compound, a cation polymerizable compound, and an anionic polymerizable compound.
The polymerizable compound preferably contains a radical polymerizable compound from the viewpoint of effectively exhibiting an effect of reducing hardening resistance.

(i) Radical polymerizable compound The radical polymerizable compound may be one having one or more polymerizable groups capable of radical polymerization, and may include two or more polymerizable groups.
The radical polymerizable compound is usually used together with a radical polymerization initiator.
Examples of the polymerizable group capable of radical polymerization include ethylenically unsaturated double bond groups such as a (meth) acrylic group and a vinyl group.
In addition, (meth) acrylic type is used in the meaning which includes acrylic type and methacrylic type. Moreover, (meth) acrylate is used in the meaning which contains an acrylate and a methacrylate.

The radically polymerizable compound may be a compound having an acid value or a compound having no acid value.
Examples of the compound having an acid value include a compound having a carboxyl group.
The composition described above contains a compound having an acid value as a radical polymerizable compound, and the solubility of the light-irradiated portion in the alkaline developer is reduced. Therefore, the above-mentioned composition can be used, for example, as a photosensitive composition whose solubility in a solvent such as an alkaline developer changes before and after light irradiation. More specifically, the above composition can be used as a negative composition by containing a compound having an acid value.
As the alkaline developer, an aqueous solution of tetramethylammonium hydroxide (TMAH), an aqueous solution of potassium hydroxide, or the like is generally used as the alkaline developer.

Among the above-mentioned radically polymerizable compounds, for example, as the compound having an ethylenically unsaturated double bond group and having an acid value, (meth) acrylic acid, α-chloroacrylic acid, methylene succinic acid, and maleic acid Acid, methyl maleic acid, fumaric acid, dicycloheptenedioic acid, butenoic acid, methacrylic acid, vinyl acetic acid, allyl acetic acid, cinnamic acid, adipic acid, methyl fumaric acid , [2- (meth) acryloxyethyl] succinate, [2- (meth) acryloxyethyl] phthalate, and ω-carboxy polycaprolactone mono (Meth) acrylate is a mono (meth) acrylate of a polymer having a carboxyl group and a hydroxyl group at both ends; hydroxyethyl (meth) acrylate / maleate, hydroxypropyl (meth) acrylate Unsaturation such as esters / maleic acid esters, dicyclopentadiene / maleic acid esters, or polyfunctional (meth) acrylates having one carboxyl group and two or more (meth) acrylfluorenyl groups Monobasic acid; phenol novolac epoxy resin and / or cresol novolac epoxy resin, novolac epoxy resin with biphenyl skeleton, naphthalene skeleton, double A novolac epoxy compounds such as novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds, polyphenylmethane epoxy resins having polyfunctional epoxy groups, and the following general formula (III Epoxy resins such as epoxy compounds represented by) and unsaturated monoacids, and epoxy resins such as epoxy compounds represented by the following general formula (III) Resin obtained by the action of saturated monobasic acid and then with polybasic acid anhydride; as a hydroxyl-containing polyfunctional acrylate such as pentaerythritol triacrylate, dipentaerythritol pentaacrylate, and succinic anhydride, phthalic anhydride, tetrahydrophthalic acid A polyfunctional acrylate having an acid value as a reactant of a dibasic acid anhydride such as formic anhydride.

[Chemical 20]

(In the formula, X ⁴¹ represents a direct bond, an alkylene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, -O-, -S-, -SO _2- , -SS-, -SO-, -CO-, -OCO- or the substituents represented by the above (1-1) to (1-3),
R ⁴¹ , R ⁴² , R ⁴⁴ and R ⁴⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or a halogen atom,
d is an integer from 0 to 10)

Examples of the alkyl group having 1 to 5 carbon atoms, the alkoxy group having 1 to 8 carbon atoms, and the alkenyl group having 2 to 5 carbon atoms represented by R ⁴¹ , R ⁴² , R ⁴⁴ and R ⁴⁴ include the above-mentioned ""A.Compound" among those exemplified as R ¹¹ and the like satisfying a specific number of carbon atoms.
Examples of the alkylene group having 1 to 4 carbon atoms represented by X ⁴¹ include methylene, ethylene, propylene, and butylene.
Examples of the alicyclic hydrocarbon group having 3 to 20 carbon atoms represented by X ⁴¹ include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
The above-mentioned alkyl group, alkoxy group, alkenyl group, alkylene group, and alicyclic hydrocarbon group may have a substituent. Unless otherwise specified, they are unsubstituted or substituted without a substituent. The substituent of the hydrogen atom of the substituted alkyl, alkoxy, alkenyl, alkylene, and alicyclic hydrocarbon group may be the same as the substituent of the hydrogen atom of the alkyl group used in R ¹¹ and the like. Content.

Among the above-mentioned radically polymerizable compounds, for example, as the compound having an ethylenically unsaturated double bond group and not having an acid value, (meth) acrylic acid 2-hydroxyethyl ester and (meth) acrylic acid 2-hydroxy group can be cited. Propyl ester, glycidyl (meth) acrylate, the following compounds No. A1 to No. A4, methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, (formyl) Base) tert-butyl acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, hard (meth) acrylate Fatty ester, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, (meth) Aminopropyl acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxy (meth) acrylate Ethoxyethyl, ethylhexyl (meth) acrylate, phenoxyethyl (meth) acrylate, tetrahydrofuran (meth) acrylate, vinyl (meth) acrylate, (meth) acrylic acid Allyl ester, benzyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol Alcohol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, trihydroxy Methylethane tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, pentaerythritol tetra (methyl) ) Acrylate, pentaerythritol tri (meth) acrylate, tricyclodecane dimethylol di (meth) acrylate, tris [(meth) acrylfluorenylethyl] isocyanurate, polyester ( Unsaturated monobasic acids such as meth) acrylate oligomers and esters of polyhydric alcohols or polyphenols; metal salts of unsaturated polybasic acids such as zinc (meth) acrylate and magnesium (meth) acrylate; maleic anhydride, Methylene succinic anhydride, methyl maleic anhydride, methyl tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5- (2,5 -Dioxo Tetrahydro Furanyl) -3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydrophthalic anhydride-maleic anhydride adduct, dodecenyl succinic acid Acid anhydrides, anhydrides of unsaturated polybasic acids such as methylbicycloheptene dicarboxylic acid anhydride; (meth) acrylamide, methylenebis (meth) acrylamide, diethylene triamine tri (meth) propylene Ammonium amine, xylylene bis (meth) acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide and other unsaturated monoacids and polyamines; ammonium Unsaturated aldehydes such as aldehydes; (meth) acrylonitrile, α-chloroacrylonitrile, dicyanethylene, allyl cyanide, etc .; unsaturated styrene, 4-methylstyrene, 4-ethylstyrene , 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinylphenol, vinylsulfonic acid, 4-vinylbenzenesulfonic acid Unsaturated aromatic compounds such as acids, vinyl benzyl methyl ether and vinyl benzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; vinyl amine, allyl amine, N-vinyl pyrrolidone, Unsaturated amines such as vinylpiperidine Compounds; vinyl ethers such as vinyl methyl ether, vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, allyl glycidyl ether; cis-butylene diimide, N-phenylcis-butyl Unsaturated fluorene imines such as alkene diimide, N-cyclohexyl cis butene difluorene imine; indines such as indene, 1-methylindene; 1,3-butadiene, isoprene, chlorine Aliphatic conjugated diene such as butadiene; polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, polysiloxane is equivalent to a mono (methyl Base) macromonomers of acrylonitrile; (meth) acrylonitrile, ethylene, propylene, butene, vinyl chloride, vinyl acetate and other vinyl compounds, and polymethylmethacrylate macromonomers, polybenzene Macromonomers such as ethylene macromonomers, monomethacrylates with a tricyclodecane skeleton, N-phenylcis-butenedifluorene imine, methacryloxymethyl-3-ethyloxy heterocycle Copolymers of butane and the like with (meth) acrylic acid and reacting these with isocyanate compounds having unsaturated bonds such as Karenz MOI, AOI manufactured by Showa Denko Corporation Copolymer of (meth) acrylic acid obtained, or vinyl chloride, vinylidene chloride, divinyl succinate, diallyl phthalate, triallyl phosphate, triallyl isocyanurate , Vinyl sulfide, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, hydroxyl-containing vinyl monomers, and vinyl carbamates of polyisocyanate compounds Compounds, hydroxyl-containing vinyl monomers and polyepoxy compounds, vinyl epoxy compounds, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, and other polyfunctional acrylates containing toluene and toluene diisocyanate, hexamethylene diisocyanate And other polyfunctional isocyanate reactants.

[Chemical 21]

[Chemical 22]

[Chemical 23]

[Chemical 24]

The said radically polymerizable compound can be used individually or in mixture of 2 or more types. The radical polymerizable compound may be used in combination of a compound having an ethylenically unsaturated double bond group and an acid value and a compound having an ethylenically unsaturated double bond group and an acid value.
When two or more radical polymerizable compounds are used, they can be copolymerized in advance and used as a copolymer.
The content of the radically polymerizable compound can be appropriately set according to the use of the composition and the like. For example, it can be 1 part by mass or more and 99 parts by mass or less, and preferably 10 parts by mass or more in 100 parts by mass of the composition. And 90 mass parts or less, Among these, 40 mass parts or more and 80 mass parts or less are preferable. The reason is that when the content is within the above range, for example, the above composition can be used as a negative composition having excellent sensitivity. The reason therefor is to provide a composition which has less resistance to hardening and can easily provide a UV-absorbing function to a hardened material.
The content of the polymerizable compound may be any composition as long as the composition can be used as a curable composition. The total amount of the compound I-1 and the polymerizable compound may be 1 part by mass or more and 99 parts by mass. Hereinafter, it is preferably 50 parts by mass or more and 99 parts by mass or less, and among them, 80 parts by mass or more and 99 parts by mass or less is preferable, and 90 parts by mass or more and 98 parts by mass or less is preferable. The reason for this is that, when the content is within the above range, the composition can provide a composition that has less resistance to hardening and can easily provide a UV-absorbing function to the hardened material.
The content of the compound I-1 and the radically polymerizable compound can be appropriately set according to the use of the composition and the like. For example, it can be 1 part by mass or more and 99 parts by mass or less in 100 parts by mass of the composition. It is preferably 10 parts by mass or more and 90 parts by mass or less, and among these, 40 parts by mass or more and 80 parts by mass or less is preferable. The reason is that when the content is within the above range, for example, the above composition can be used as a negative composition having excellent sensitivity. The reason therefor is to provide a composition which has less resistance to hardening and can easily provide a UV-absorbing function to a hardened material.

(ii) Cationic polymerizable compound and anionic polymerizable compound The cationic polymerizable compound may have at least one polymerizable group capable of cationic polymerization.
The above-mentioned cationically polymerizable compound is usually used together with a cation polymerization initiator.
Examples of the polymerizable group capable of cation polymerization include a cyclic ether group such as an epoxy group and an oxetanyl group, and a vinyl ether group.
That is, examples of the cationically polymerizable compound include cyclic ether compounds such as epoxy compounds and oxetane compounds, and vinyl ether compounds.

Examples of the epoxy compound include methyl glycidyl ether, 2-ethylhexyl glycidyl ether, butyl glycidyl ether, decyl glycidyl ether, C12 to 13 mixed alkyl glycidyl ether, and phenyl- 2-methyl glycidyl ether, cetyl glycidyl ether, stearyl glycidyl ether, p-second butylphenyl glycidyl ether, p-third butylphenyl glycidyl ether, glycidyl methacrylate Ester, isopropyl glycidyl ether, allyl glycidyl ether, ethyl glycidyl ether, 2-methyloctyl glycidyl ether, phenyl glycidyl ether, 4-n-butylphenyl glycidyl ether, 4 -Phenylphenol glycidyl ether, tolyl glycidyl ether, dibromotolyl glycidyl ether, decyl glycidyl ether, methoxy polyethylene glycol monoglycidyl ether, ethoxy polyethylene glycol monoglycidyl ether Ether, butoxy polyethylene glycol monoglycidyl ether, phenoxy polyethylene glycol monoglycidyl ether, dibromophenyl glycidyl ether, 1,4-butanediol diglycidyl ether, 1,5- Pentylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether Glycidyl etherates such as oleyl ether, 1,1,2,2-tetra (glycidyloxyphenyl) ethane and pentaerythritol tetraglycidyl ether; glycidyl esters such as glycidyl acetate and glycidyl stearate ; 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexane-m-dioxane, methylenebis (3,4-epoxycyclohexane) , Propane-2,2-diyl-bis (3,4-epoxycyclohexane), 2,2-bis (3,4-epoxycyclohexyl) propane, bis (3,4-epoxycyclohexane) Alkanecarboxylic acid) ethylene glycol, bis (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxycyclohexanecarboxylic acid 3,4-epoxycyclohexylmethyl ester, 3, 4-epoxy-1-methylhexanecarboxylic acid 3,4-epoxy-1-methylcyclohexyl ester, 6-methyl-3,4-epoxycyclohexanecarboxylic acid 6-methyl-3 4,4-epoxycyclohexylmethyl ester, 3,4-epoxy-3-methylcyclohexanecarboxylic acid 3,4-epoxy-3-methylcyclohexylmethyl ester, 3,4-epoxy-5 -Methylcyclohexanecarboxylic acid 3,4-epoxy-5-methylcyclohexyl methyl ester, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy-2- Ethylene oxide cyclohexane, dicyclopentadiene diepoxide, carboxylic acid 3,4-epoxy-6-methylcyclohexyl ester, α-pinene oxide, phenylene oxide, epoxy ring Hexane and epoxy cyclopentane Epoxy cycloalkyl compounds and N-glycidylphthalimide.

Moreover, as said epoxy compound, an epoxidized polyolefin can also be used. The so-called epoxidized polyolefin is a polyolefin having an epoxy group modified by an epoxy group-containing monomer. It can be produced by copolymerizing ethylene or an α-olefin having 3 to 20 carbon atoms, an epoxy-group-containing monomer, and other monomers as necessary by using either a copolymerization method or a grafting method. Ethylene or an α-olefin having 3 to 20 carbon atoms, an epoxy-containing monomer, and other monomers may be polymerized individually or in combination with other monomers in a plurality of types. In addition, it can also be obtained by epoxidizing the double bond of a non-conjugated polybutadiene having a hydroxyl group at its terminal by a peracetic acid method, or one having a hydroxyl group in the molecule may be used. Moreover, an epoxy group may be introduce | transduced by hydroxylating a urethane with an isocyanate, and making it react with an epoxy compound containing a primary hydroxyl group.

Examples of the ethylene or the α-olefin having 3 to 20 carbon atoms include ethylene, propylene, butene, isobutylene, 1,3-butadiene, 1,4-butadiene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, pentadiene, 3-butyl-1,3-octadiene, isoprene, etc.

Examples of the epoxy-group-containing monomer include glycidyl esters of α, β-unsaturated acids, vinyl benzyl glycidyl ether, and allyl glycidyl ether. Specific examples of the glycidyl ester of an α, β-unsaturated acid include glycidyl acrylate, glycidyl methacrylate, and glycidyl ethacrylate. Particularly preferred is glycidyl methacrylate.

Examples of the other monomers include unsaturated aliphatic hydrocarbons such as vinyl chloride, vinylidene chloride, vinylidene fluoride, and tetrafluoroethylene; (meth) acrylic acid, α-chloroacrylic acid, methylene succinic acid, Maleic acid, methyl maleic acid, fumaric acid, dicycloheptenedioic acid, butenoic acid, methacrylic acid, vinylacetic acid, allylacetic acid, cinnamic acid, adipic acid, methyl trans Butenedioic acid, succinate mono [2- (meth) acryloxyethyl] ester, phthalate mono [2- (meth) acryloxyethyl] ester, ω-carboxy poly Caprolactone mono (meth) acrylate is equal to mono (meth) acrylate, hydroxyethyl (meth) acrylate / maleate, hydroxypropyl ( (Meth) acrylic acid esters / maleic acid esters, dicyclopentadiene / maleic acid esters, and polyfunctional (meth) acrylic acid having one carboxyl group and two or more (meth) acrylfluorenyl groups Unsaturated polybasic acids such as esters; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, methyl (meth) acrylate, butyl (meth) acrylate, (meth) C) Isobutyl acid, third butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate , Stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethylamino (meth) acrylate Ethyl ester, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, Butoxyethoxyethyl (meth) acrylate, ethylhexyl (meth) acrylate, phenoxyethyl (meth) acrylate, tetrahydrofuran (meth) acrylate, vinyl (meth) acrylate , Allyl (meth) acrylate, benzyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) Acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (methyl) ) Acrylate, Trimethylolethane Tris (methyl) Enoate, trimethylolpropane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (methyl) Acrylate), tricyclodecane dimethylol di (meth) acrylate, tris [(meth) acrylmethylethyl] isocyanurate, and polyester (meth) acrylate oligomers And other unsaturated monobasic acids and esters of polyhydric alcohols or polyphenols; metal salts of unsaturated polybasic acids such as zinc (meth) acrylate and magnesium (meth) acrylate; maleic anhydride, methylene succinic anhydride, formic acid Methyl maleic anhydride, methyl tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuranyl)- 3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydrophthalic anhydride-maleic anhydride adduct, dodecenyl succinic anhydride, and methyl Anhydrides of unsaturated polybasic acids such as dicycloheptene dicarboxylic acid anhydride; (meth) acrylamide, methylene bis (meth) acrylamide, diethylene triamine tri (meth) acrylamide, benzene Dimethylbis (a ) Unsaturated monoacids such as acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide and polyamines; unsaturated aldehydes such as acrolein; (meth) propylene Unsaturated nitriles such as nitrile, α-chloroacrylonitrile, dicyanethylenevinyl, allyl cyanide; styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4- Hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinylphenol, vinylsulfonic acid, 4-vinylbenzenesulfonic acid, vinylbenzyl methyl ether and vinyl Unsaturated aromatic compounds such as naphthalene; Unsaturated ketones such as methyl vinyl ketone; Unsaturated amine compounds such as vinyl amine, allyl amine, N-vinyl pyrrolidone and vinyl piperidine; allyl alcohol and croton Vinyl alcohols such as alcohols; vinyl ethers such as vinyl methyl ether, vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether; maleimide, N-phenylmaleimide Unsaturated fluorene imines such as amines and N-cyclohexyl cis-butene difluorene imine; indines such as indene and 1-methylindene; polystyrene, poly (meth) acrylate, poly (meth) N-butyl enoate and polysiloxane are equivalent to macromonomers with mono (meth) acrylfluorenyl groups at the ends of polymer molecular chains; vinyl chloride, vinylidene chloride, divinyl succinate, phthalate Diallyl formate, triallyl phosphate, triallyl isocyanurate, vinyl sulfide, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine , Vinyl urethane compounds containing hydroxyl-containing vinyl monomers and polyisocyanate compounds, vinyl epoxy compounds containing hydroxyl-containing vinyl monomers and polyepoxides, pentaerythritol triacrylate and dipentaerythritol pentaacrylate Polyfunctional acrylates containing hydroxyl groups such as esters; reactants of polyfunctional isocyanates such as toluene diisocyanate and hexamethylene diisocyanate; as polyfunctional acrylates containing hydroxyl groups such as pentaerythritol triacrylate and dipentaerythritol pentaacrylate and succinic acid Multifunctional acrylates with acid value, reactants of dibasic acid anhydrides such as acid anhydride, phthalic anhydride and tetrahydrophthalic anhydride.

Commercial products can also be used as the epoxidized polyolefin, for example, Epolead PB3600, Epolead PB4700 (manufactured by Daicel); BF-1000, FC-3000 (manufactured by ADEKA); Bondfast 2C, Bondfast E, Bondfast CG5001 , Bondfast CG5004, Bondfast 2B, Bondfast 7B, Bondfast 7L, Bondfast 7M, Bondfast VC40 (manufactured by Sumitomo Chemical Co., Ltd.); JP-100, JP-200 (manufactured by Soda Corporation of Japan); Poly bd R-45HT, Poly bd R-15HT (Manufactured by Idemitsu Kosan Co., Ltd.) and Ricon657 (manufactured by Arkema Co., Ltd.).

In terms of good heat resistance, it is more preferable to use a compound having a Cardo skeleton represented by the general formula (II) as the epoxy compound.

Examples of the oxetane compound include 3,7-bis (3-oxetanyl) -5-oxe-nonane, and 1,4-bis [(3-ethyl-3- Oxetanylmethoxy) methyl] benzene, 1,2-bis [(3-ethyl-3-oxetanylmethoxy) methyl] ethane, 1,3-bis [(3-ethyl -3-oxetanylmethoxy) methyl] propane, ethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, triethylene glycol bis (3-ethyl-3-oxa Cyclobutylmethyl) ether, tetraethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, 1,4-bis (3-ethyl-3-oxetanylmethoxy) butane, 1,6-bis (3-ethyl-3-oxetanylmethoxy) hexane, 3-ethyl-3-[(phenoxy) methyl] oxetane, 3-ethyl- 3- (hexyloxymethyl) oxetane, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- (hydroxymethyl ) Oxetane and 3-ethyl-3- (chloromethyl) oxetane and the like.

Examples of the vinyl ether compound include diethylene glycol monovinyl ether, triethylene glycol divinyl ether, n-dodecyl vinyl ether, cyclohexyl vinyl ether, and 2-ethylhexyl ethylene. Ether, 2-chloroethyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, triethylene glycol vinyl ether, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether 1,6-cyclohexanedimethanol monovinyl ether, ethylene glycol divinyl ether, 1,4-butanediol divinyl ether, 1,6-cyclohexanedimethanol divinyl ether, and the like.

As said anionic polymerizable compound, what is necessary is just to have 1 or more types of polymerizable group which can be anionic polymerized.
The anionic polymerizable compound is usually used together with an anionic polymerization initiator.
Examples of the polymerizable group capable of anionic polymerization include an epoxy group, a lactone group, and a (meth) acrylic group.
That is, examples of the anionic polymerizable compound include an epoxy compound, a lactone compound, and a compound having a (meth) acrylic group.
Examples of the lactone compound include β-propiolactone and ε-caprolactone.
As the epoxy compound, the epoxy compounds exemplified as the cationically polymerizable compound described above can be used. In addition, as the compound having a (meth) acrylic group, those exemplified as the radical polymerizable compound described above can be used.

The cationically polymerizable compound and the anionic polymerizable compound may be used alone or in combination of two or more kinds.

(b) Polymer without polymerizable group As the resin usable in the composition of the present invention, as described above, a polymer without polymerizable group can be used.
The weight-average molecular weight (Mw) of the polymer having no polymerizable group can be appropriately set according to the use of the composition and the like, and can be, for example, 1,500 or more, and 1,500 or more and 300,000 or less.
Examples of such a polymer include those having a repeating structure, and examples thereof include a photosensitive resin having a photosensitive property and a non-photosensitive resin having no photosensitive property.
The composition of the present invention can be used as a photosensitive composition by containing a photosensitive resin as a resin component, for example.

(i) Photosensitive resin The above-mentioned photosensitive resin has photosensitivity. For example, a positive resin may be used. The positive resin is used together with an acid generator, and is bonded to an ester group or an acetal group by the action of an acid. The direction in which the solubility of the developing solution increases, such as cutting, changes.
The composition contains a positive resin as a resin component, and the solubility of the light-irradiated portion in the alkaline developing solution is increased.
Therefore, the above composition can be used, for example, as a photosensitive composition whose solubility in a solvent such as an alkaline developer changes before and after light irradiation, and more specifically, as a positive composition.

As the positive resin, a polymer obtained by partially replacing an acid polymer with an acid-labile group having an alkaline dissolution control function can be used.
Examples of the above-mentioned polymer include polyhydroxystyrene and its derivatives; polyacrylic acid and its derivatives; polymethacrylic acid and its derivatives; derivatives derived from hydroxystyrene, acrylic acid, methacrylic acid, and the like Two or more copolymers formed by selecting materials; two or more copolymers formed by selecting from hydroxystyrene, styrene, and derivatives thereof; selected from cycloolefins and their derivatives, and maleic anhydride And three or more copolymers of acrylic acid and its derivatives; three or more copolymers selected from cycloolefins and their derivatives, maleimide, and acrylic acid and its derivatives; Olefin; one or more types of high molecular polymers selected from the group consisting of metathesis ring-opening polymers.
Examples of the acid-labile group introduced into the above-mentioned polymer include tertiary alkyl, trialkylsilyl, pendant oxyalkyl, aryl-substituted alkyl, and tetrahydropyran-2-yl. Heteroalicyclic, tertiary alkylcarbonyl, tertiary alkylcarbonylalkyl, alkoxycarbonyl and the like.

Specific examples of the above-mentioned positive resin can be described in, for example, Japanese Patent Application Laid-Open No. 2003-192665, Japanese Patent Application Laid-Open No. 2004-323704, Claim 3, Japanese Patent Laid-Open No. 10-10733, and the like. The content is the same.

As the acid generator used together with the positive resin, a known acid generator can be used. Specific examples of the acid generator include a photocationic polymerization initiator and a thermal cationic polymerization initiator described below.

(ii) Non-photosensitive resin The non-photosensitive resin may be any material as long as it does not have photosensitivity, and examples thereof include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, and poly (methyl methacrylate). Base) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS ( acrylonitrile-butadiene-styrene) resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polypropylene Amines, saturated polyesters, phenol-based resins, phenoxy resins, polyamidoamine imine resins, polyamino acid resins, epoxy resins, and the like.
The non-photosensitive resin may be, for example, a polymer of the polymerizable compound.

(c) Resin component The content of the resin component in the composition of the present invention can be appropriately determined according to the use of the composition and the like. For example, it is preferably set to 1 part by mass or more in 100 parts by mass of the solid component of the composition. It is 99 parts by mass or less, more preferably 20 parts by mass or more and 95 parts by mass or less, and even more preferably 30 parts by mass or more and 90 parts by mass or less. The reason is that, when the content is in the above range, the composition can stably maintain the compound I-1, for example.
The content of the resin component can be appropriately set according to the use of the composition and the like. For example, it can be 1 part by mass or more and 99 parts by mass or less, preferably 10 parts by mass or more and 90 parts by mass in 100 parts by mass of the composition. It is preferably 40 parts by mass or more and 80 parts by mass or less. The reason is that when the content is within the above range, for example, the above composition can be used as a negative composition having excellent sensitivity. The reason therefor is to provide a composition which has less resistance to hardening and can easily provide a UV-absorbing function to a hardened material.
The content of the above-mentioned resin component varies depending on the use of the composition and the like, and it can be set to 1 part by mass or more and 99 parts by mass or less, and preferably 50 parts by mass in 100 parts by mass of the total of the compound I-1 and the resin component. The amount is not less than 99 parts by mass, and preferably not less than 80 parts by mass and not more than 99 parts by mass, and more preferably not less than 90 parts by mass and not more than 98 parts by mass. The reason is that when the content is within the above range, the composition can provide a composition that can easily provide an ultraviolet absorbing function and the like to a cured product.
The content of the compound I-1 and the resin component can be appropriately set according to the use of the composition and the like. For example, it can be set to 1 part by mass or more and 99 parts by mass or less in 100 parts by mass of the composition. 10 mass parts or more and 90 mass parts or less, Among these, 40 mass parts or more and 80 mass parts or less are preferable. The reason is that when the content is within the above range, for example, the above composition can be used as a negative composition having excellent sensitivity. The reason therefor is to provide a composition which has less resistance to hardening and can easily provide a UV-absorbing function to a hardened material.

The kind of the resin component contained in the composition of the present invention may be only one kind, or a combination of two or more kinds.
The said resin component can contain only either one of a polymerizable compound and a polymer, or both, for example.
When the resin component contains both a polymerizable compound and a polymer without a polymerizable group, the content of the polymerizable compound may be appropriately set according to the use of the composition, for example, the polymerizable compound and the polymer In 100 parts by mass of the product, the amount can be 1 part by mass or more and 99 parts by mass or less.

(2) Polymerization initiator The polymerization initiator is contained as a curable component, and is usually used together with a polymerizable compound and the like.
The polymerization initiator may be any polymerizable compound, and examples thereof include a photopolymerization initiator capable of polymerizing a polymerizable compound upon irradiation with light, and a polymerizable compound capable of polymerizing upon heating. Thermal polymerization initiators and the like.
The said polymerization initiator is a photoinitiator from a viewpoint of the said compound I-1 exhibiting the effect which functions as an ultraviolet absorber effectively.

(a) Photopolymerization initiator As the photopolymerization initiator, any polymer that can polymerize a polymerizable compound by irradiation with light may be used, and examples thereof include a photoradical polymerization initiator and photocationic polymerization. Initiator, photoanionic polymerization initiator, and the like.

As the photo-radical polymerization initiator, as long as a radical is generated by light irradiation, a previously known compound can be used without particular limitation.
Examples of the photo-radical polymerization initiator include acetophenone-based compounds, benzophenone-based compounds, benzophenone-based compounds, and 9-oxosulfur. As the compound, an oxime ester compound and the like are preferable.

Examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, and 4'-isopropyl-2-hydroxy- 2-methylphenylacetone, 2-hydroxymethyl-2-methylphenylacetone, 2,2-dimethoxy-1,2-diphenylethane-1-one, p-dimethylaminophenethyl Ketone, p-tert-butyldichloroacetophenone, p-tert-butyltrichloroacetophenone, p-azidebenzylidene, 1-hydroxycyclohexylphenylketone, 2-methyl-1 -[4- (methylthio) phenyl] -2-olinylacetone-1, 2-benzyl-2-dimethylamino-1- (4-olinylphenyl) -butanone-1, benzoin , Benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether and 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl- 1-propane-1-one and the like.

Examples of the benzophenazine-based compound include benzophenazine and the like.

Examples of the benzophenone-based compound include benzophenone, methyl orthobenzoylbenzoate, Michelin, 4,4'-bis (diethylamino) benzophenone, 4,4'-dichlorobenzophenone and 4-benzylidene-4'-methyldiphenyl sulfide.

As the above 9-oxysulfur Compounds, 9-oxysulfur 2-methyl-9-oxysulfur , 2-ethyl-9-oxysulfur , 2-chloro-9-oxysulfur , 2-isopropyl-9-oxysulfur , 2,4-diethyl-9-oxysulfur Wait.

Examples of the oxime-based compound include compounds represented by the following general formula (IV).

[Chemical 25]

(In the formula, R ⁷¹ and R ⁷² each independently represent a hydrogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aryl alkyl group having 7 to 30 carbon atoms. Or a heterocyclic group containing 2 to 20 carbon atoms,
R ⁷³ and R ⁷⁴ each independently represent a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, R ⁷⁵ , OR ⁷⁶ , SR ⁷⁷ , NR ⁷⁸ R ⁷⁹ , COR ⁸⁰ , SOR ⁸¹ , SO ₂ R ⁸² or CONR ⁸³ R ⁸⁴ , R ⁷³ and R ^{74 are} also bonded to each other to form a ring,
R ⁷⁵ , R ⁷⁶ , R ⁷⁷ , R ⁷⁸ , R ⁷⁹ , R ⁸⁰ , R ⁸¹ , R ⁸² , R ^83, and R ⁸⁴ each independently represent an alkyl group having 1 to 20 carbon atoms, and an alkyl group having 6 to 30 carbon atoms Aryl, arylalkyl having 7 to 30 carbon atoms or heterocyclic group containing 2 to 20 carbon atoms,
X ³ represents an oxygen atom, a sulfur atom, a selenium atom, CR ⁸⁵ R ⁸⁶ , CO, NR ⁸⁷ or PR ⁸⁸ ,
X ⁴ represents a single bond or CO,
R ⁸⁵ , R ⁸⁶ , R ⁸⁷ and R ⁸⁸ each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms, The methylene group in the alkyl group or the arylalkyl group may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, or a heterocyclic group.
R ⁷³ and R ^{74 may} also form a ring with any adjacent benzene ring independently.
e1 represents an integer from 0 to 4,
e2 represents an integer from 0 to 5)

The number of carbon atoms used as R ⁷¹ , R ⁷² , R ⁷⁵ , R ⁷⁶ , R ⁷⁷ , R ⁷⁸ , R ⁷⁹ , R ⁸⁰ , R ⁸⁵ , R ⁸⁶ , R ^87, and R ⁸⁸ in the general formula (IV) Examples of the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 30 carbon atoms, the aryl alkyl group having 7 to 30 carbon atoms, or the heterocyclic group containing 2 to 20 carbon atoms and the substituents include the above. In the item "1. Photodissociation group B", a specific number of carbon atoms is satisfied among the contents exemplified as R ¹¹ and the like.

Examples of the oxime-based compound include ethyl ketone-1- [9-ethyl-6- (2-methylbenzylidene-9H-carbazol-3-yl] -1- (O-acetamidine) Oxime), 1- [9-ethyl-6-benzylidene-9H-carbazol-3-yl-octane-1-oneoxime-O-acetate, 1- [9-ethyl- 6- (2-methylbenzyl) -9H-carbazol-3-yl] -ethane-1-oneoxime-O-benzoate, 1- [9-n-butyl-6- ( 2-ethylbenzyl) -9H-carbazol-3-yl] -ethane-1-oneoxime-O-benzoate, ethyl ketone-1- [9-ethyl-6- (2 -Methyl-4-tetrahydrofuranylbenzyl) -9H-carbazol-3-yl] -1- (O-ethylamidoxime), ethyl ketone-1- [9-ethyl-6- (2 -Methyl-4-tetrahydropyranylbenzyl) -9H-carbazol-3-yl] -1- (O-ethylfluorenyloxime), ethyl ketone-1- [9-ethyl-6 -(2-methyl-5-tetrahydrofurylbenzyl) -9H-carbazol-3-yl] -1- (O-ethylamidoxime), ethyl ketone-1- [9-ethyl-6 -{2-methyl-4- (2,2-dimethyl-1,3-dioxolyl) methoxybenzyl} -9H-carbazol-3-yl] -1- ( O-acetamidoxime), ethyl ketone-1- [9-ethyl-6- (2-methyl-4-tetrahydrofurylmethoxybenzyl) -9H-carbazol-3-yl]- Carbazole-based oxime ester compounds having a carbazole structure such as 1- (O-acetamidooxime).

As the oxime-based compound, for example, an indole-based oxime ester compound having an indole structure can be used.
Examples of the indole-based oxime ester compound include an oxime ester compound represented by the following general formula (V) described in International Publication No. 2017/051680.

[Chemical 26]

(In the formula, R ²⁰¹ and R ²⁰² each independently represent R ²¹¹ , OR ²¹¹ , COR ²¹¹ , SR ²¹¹ , CONR ²¹² R ²¹³ or CN,
R ²¹¹ , R ²¹² and R ²¹³ each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or carbon number Heterocyclic group containing 2 to 20,
The hydrogen atom of the base represented by R ²¹¹ , R ²¹² and R ²¹³ also exists and is further substituted with R ²²¹ , OR ²²¹ , COR ²²¹ , SR ²²¹ , NR ²²² R ²²³ , CONR ²²² R ²²³ , NR ²²² OR ²²³ , NCOR ²²² In the case of OCOR ²²³ , NR ²²² COR ²²¹ , OCOR ²²¹ , COOR ²²¹ , SCOR ²²¹ , OCSR ²²¹ , COSR ²²¹ , CSOR ²²¹ , hydroxyl, nitro, CN, halogen atom, or COOR ²²¹ ,
R ²²¹ , R ²²² and R ²²³ each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or carbon number Heterocyclic group containing 2 to 20,
The hydrogen atom of the group represented by R ²²¹ , R ²²² and R ²²³ may be further substituted with a hydroxyl group, a nitro group, a CN, a halogen atom, a hydroxyl group or a carboxyl group.
The methylene group of the alkylene part of the group represented by R ²¹¹ , R ²¹² , R ²¹³ , R ²²¹ , R ²²² and R ²²³ is also substituted with -O-, -S-, -COO-, -OCO- ^{, -OCOO -, - CONR 224 -} , - NR 224 -, - NR 224 CO -, - NR 224 COO -, - OCONR 224 -, - SCO -, - COS -, - OCS- or -SCOO- the case,
R ²²⁴ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group containing 2 to 20 carbon atoms,
R ²¹¹ , R ²¹² , R ²¹³ , R ²²¹ , R ²²² , R ^223, and R ²²⁴ may have a branched side chain in the alkyl portion of the group represented by the alkyl portion, or a cyclic alkyl group.
R ²⁰³ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group containing 2 to 20 carbon atoms, The alkyl portion of the group represented by R ²⁰³ may have branched side chains or a cyclic alkyl group. Also, R ²⁰³ and R ²⁰⁷ and R ²⁰³ and R ²⁰⁸ may form a ring together. situation,
The hydrogen atom of the base represented by R ²⁰³ is also further substituted as R ²²¹ , OR ²²¹ , COR ²²¹ , SR ²²¹ , NR ²²² R ²²³ , CONR ²²² R ²²³ , NR ²²² OR ²²³ , NCOR ²²² OCOR ²²³ , NR ²²² COR ²²¹ , OCOR ²²¹ , COOR ²²¹ , SCOR ²²¹ , OCSR ²²¹ , COSR ²²¹ , CSOR ²²¹ , hydroxyl, nitro, CN, halogen atom, or COOR ²²¹ ,
R ²⁰⁴ , R ²⁰⁵ , R ^206, and R ²⁰⁷ each independently represent R ²¹¹ , OR ²¹¹ , SR ²¹¹ , COR ²¹⁴ , CONR ²¹⁵ R ²¹⁶ , NR ²¹² COR ²¹¹ , OCOR ²¹¹ , COOR ²¹⁴ , SCOR ²¹¹ , OCSR ²¹¹ , COSR ²¹⁴ , CSOR ²¹¹ , hydroxyl, CN, or halogen atom, R ²⁰⁴ and R ²⁰⁵ , R ²⁰⁵ and R ^206, and R ²⁰⁶ and R ^{207 may} also form a ring together,
Hydrogen atoms of the radicals represented by R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ and R ²⁰⁷ also exist and are further substituted with R ²²¹ , OR ²²¹ , COR ²²¹ , SR ²²¹ , NR ²²² R ²²³ , CONR ²²² R ²²³ , NR ²²² OR ²²³ In the case of NCOR ²²² OCOR ²²³ , NR ²²² COR ²²¹ , OCOR ²²¹ , COOR ²²¹ , SCOR ²²¹ , OCSR ²²¹ , COSR ²²¹ , CSOR ²²¹ , hydroxyl, nitro, CN, halogen atom or COOR ²²¹ ,
R ²¹⁴ , R ²¹⁵ and R ²¹⁶ represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,
The alkyl portion of the group represented by R ²¹⁴ , R ^215, and R ²¹⁶ may have a branched side chain or a cyclic alkyl group.
R ²⁰⁸ represents R ²¹¹ , OR ²¹¹ , SR ²¹¹ , COR ²¹¹ , CONR ²¹² R ²¹³ , NR ²¹² COR ²¹¹ , OCOR ²¹¹ , COOR ²¹¹ , SCOR ²¹¹ , OCSR ²¹¹ , COSR ²¹¹ , CSOR ²¹¹ , hydroxyl, CN or halogen atom,
n1 means 0 or 1)

1 to 20 carbon atoms used as R ²⁰³ , R ²¹¹ , R ²¹² , R ²¹³ , R ²¹⁴ , R ²¹⁵ , R ²¹⁶ , R ²²¹ , R ²²² , R ²²³ and R ²²⁴ in the general formula (V) Examples of the alkyl group, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, or heterocyclic group having 2 to 20 carbon atoms include the above-mentioned "1. Photodissociative group B" The item exemplified as R ^{11 in the} item satisfies a specific number of carbon atoms.

Examples of other radical polymerization initiators include phosphine oxide compounds such as 2,4,6-trimethylbenzylidene diphenylphosphine oxide, and bis (cyclopentadienyl) -bis [2,6- Difluorocene compounds such as difluoro-3- (pyrrole-1-yl)] titanium and the like.

Examples of commercially available radical polymerization initiators include: Adeka Optomer N-1414, N-1717, N-1919, Adeka ARKLS NCI-831, NCI-930 (manufactured by ADEKA), IRGACURE184, IRGACURE369, IRGACURE651, IRGACURE907 , IRGACURE OXE 01, IRGACURE OXE 02, OXE 03, OXE 04, IRGACURE784 (made by BASF), TR-PBG-304, TR-PBG-305, TR-PBG-309, and TR-PBG-314 (made by Truly) Wait.

These photo-radical polymerization initiators can be used singly or in combination of two or more according to the required performance.
The content of the photo-radical polymerization initiator is only required to provide the desired curability or photosensitivity. For example, the content of the photo-radical polymerization initiator may be 0.001 to 20 parts by mass based on 100 parts by mass of the polymerizable compound. It is preferably from 0.1 to 30 parts by mass, more preferably from 0.5 to 10 parts by mass. The reason for this is that the composition has excellent curability and the like as well as excellent dispersibility and the like by the content.

The photocationic polymerization initiator is not particularly limited as long as it is a compound capable of releasing a substance that initiates cationic polymerization by light irradiation. Existing compounds can be used, and it is preferably used as irradiation by energy rays. The double salt of the onium salt of Lewis acid, or a derivative thereof is released. As a representative of this compound, the following general formula is mentioned
[A1] ^{r +} [B1] ^r-
The indicated cation and anion salts.

The cation [A1] ^{r + is} preferably an onium, and its structure can be represented by the following general formula, for example.
[(R ¹⁰¹ ) _f1 Q] ^{r +}

Furthermore, here, R ¹⁰¹ is an organic group in which the number of carbon atoms is 1 to 60 and there are atoms other than a few carbon atoms. f1 is any integer from 1 to 5. The e R ⁵⁸ are independent and have the same situation and different situations. In addition, it is preferable that at least one of R ¹⁰¹ is an organic group having an aromatic ring as described above. Examples include alkyl, alkoxy, hydroxyl, hydroxyalkoxy, halogen atoms, benzyl, thiophenoxy, 4-benzylphenylphenylthio, 2-chloro-4-benzyl A phenyl group in the case of a substituted fluorenylphenylthio group. Q is an atom or a group of atoms selected from the group consisting of S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, F, N = N. When the atomic valence of Q in the cation [A1] ^{r +} is set to q, a relationship of r = f1−q must be established (where N = N is treated with an atomic valence of 0).

The anion [B1] ^{r- is} preferably a halide complex, and its structure can be represented, for example, by the following general formula [LX _f2 ] ^r- .

Furthermore, here, L is a metal or semimetal (Metalloid) as the central atom of the halide complex, and is B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn and Co.
X _f2 is a halogen atom or a phenyl group in the case where it is substituted with a halogen atom or an alkoxy group. f2 is an integer from 3 to 7.
When the atomic valence of L in the anion [B1] ^r- is set to p, the relationship of r = f2-p must be established.

Specific examples of the anion [LX _f2 ] ^r- of the general formula include tetrakis (pentafluorophenyl) borate, tetra (3,5-difluoro-4-methoxyphenyl) borate, and tetrakis tetrafluoroborate (BF ₄₎ ^-, hexafluorophosphate (PF ₆₎ ^-, hexafluoroantimonate (SbF ₆₎ ^-, hexafluoroarsenate (AsF ₆₎ ^- and hexachloro antimonate (SbCl ₆₎ ^- and the like.

In addition, the anion [B1] ^r- can also preferably use the following general formula
[LX _{f2 － 1} (OH)] ^r-
The represented structure. L, X, and f2 are the same as described above. Examples of other anions that can be used include perchlorate ion (ClO ₄ ) ^- , trifluoromethylsulfite ion (CF ₃ SO ₃ ) ^- , fluorosulfonate ion (FSO ₃ ) ^- , and tosylate Acid anion, trinitrobenzene sulfonate anion, camphor sulfonate, nonafluorobutane sulfonate, hexafluorooctane sulfonate, tetraaryl borate and tetrakis (pentafluorophenyl) borate.

In the present invention, among such onium salts, it is particularly effective to use the following aromatic onium salts (A) to (C), and therefore it is preferable. Among these, one kind may be used alone, or two or more kinds may be used in combination.

(A) Aryldiazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, and 4-methylphenyldiazonium hexafluorophosphate.

(B) Diphenylphosphonium hexafluoroantimonate, bis (4-methylphenyl) phosphonium hexafluorophosphate, bis (4-thirdbutylphenyl) phosphonium hexafluorophosphate and tolyl cumene Diarylsulfonium salts such as tetrakis (pentafluorophenyl) borate.

(C) A sulfonium salt of a phosphonium cation and a hexafluoroantimony ion, a tetrakis (pentafluorophenyl) borate ion, and the like represented by the following Group I or Group II.

[Chemical 27]
＜ Group I ＞

[Chemical 28]
＜ Group II ＞

As another preferred one, (η5-2,4-cyclopentadien-1-yl) [(1,2,3,4,5,6-η)-(1-methyl Ethyl) benzene] -iron-aromatic hydrocarbon complexes such as iron-hexafluorophosphate; aluminum tris (ethylacetone) aluminum, aluminum tris (ethylacetoneacetate), aluminum (salicylic acid) aluminum complexes ; Mixtures with silanols such as triphenylsilanol: etc.

As the photocationic polymerization initiator, commercially available products can also be used, and examples thereof include IRUGACURE261 (manufactured by BASF), Adeka Optomer SP-150, SP-151, SP-152, SP-170, SP-171, and SP -172 (manufactured by ADEKA), UVE-1014 (manufactured by General Electronics), CD-1012 (manufactured by Sartomer), CI-2064, CI-2481 (manufactured by Soda, Japan), Uvacure1590, 1591 (Daicel UCB), CYRACUREUVI -6990 (manufactured by Union Carbide), BBI-103, MPI-103, TPS-103, MDS-103, DTS-103, NAT-103, and NDS-103 (manufactured by Midori Kagaku).

Among these, in terms of practicality and light sensitivity, it is preferable to use an aromatic sulfonium salt, an aromatic sulfonium salt, and an iron-aromatic hydrocarbon complex.

As the photo-anionic polymerization initiator, one that generates a base by light can be used, and a known one can be used as the photo-anionic polymerization initiator.
Examples of the photoanionic polymerization initiator include acetophenone O-aroyloxime, nifedipine, and the like.

(b) Thermal polymerization initiator The thermal polymerization initiator may be any polymer that can polymerize a polymerizable compound by heating, and examples thereof include a radical polymerization initiator, a cationic polymerization initiator, and anionic polymerization. Starting agent and so on.

As the thermal radical polymerization initiator, those which generate radicals by heating can be used, and those known as thermal radical polymerization initiators can be used.
As said thermal radical polymerization initiator, for example, an azo compound, a peroxide, a persulfate, etc. are mentioned as a preferable thing.

Examples of the azo-based compound include 2,2'-azobisisobutyronitrile, 2,2'-azobis (isobutyric acid methyl ester), and 2,2'-azobis-2,4. -Dimethylvaleronitrile, 1,1'-azobis (1-acetamido-1-phenylethane), and the like.

Examples of the peroxide include benzamidine peroxide, bis (tertiary butyl) benzylidene peroxide, tert-butyl pervalerate and di (4-tert-butyl peroxydicarbonate) Cyclohexyl) ester and the like.

Examples of the persulfate include persulfates such as ammonium persulfate, sodium persulfate, and potassium persulfate.

As the thermal cationic polymerization initiator, one that generates a cationic species or a Lewis acid by heating can be used, and a known one can be used as the thermal cationic polymerization initiator.
Specific examples of the thermal cationic polymerization initiator include salts such as a sulfonium salt, a thienyl salt, a thiolanium salt, a benzyl ammonium, a pyridinium salt, and a salt; Polyalkyl polyamines such as triethylene triamine and tetra ethylene triamine; 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane And alicyclic polyamines such as isophorone diamine; aromatic polyamines such as m-xylylenediamine, diaminodiphenylmethane, and diaminodiphenylphosphonium; the above-mentioned methods are made by conventional methods Polyamines and various epoxy resins such as phenyl glycidyl ether, butyl glycidyl ether, bisphenol A-diglycidyl ether and bisphenol F-diglycidyl ether, or glycidyl esters of carboxylic acids Polyepoxy addition modified product produced by resin reaction; ammonium amine produced by reacting the above organic polyamines with carboxylic acids such as phthalic acid, isophthalic acid and dimer acid by a conventional method Modified product; by using conventional methods, the above polyamines and aldehydes such as formaldehyde and cores such as phenol, cresol, xylenol, third butylphenol, and resorcinol Mannich modification produced by reacting phenols with at least one aldehyde-forming reactive site; polycarboxylic acids (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, heptane Diacid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, 2-methylsuccinic acid, 2-methyladipate, 3-methyladipate, 3-methylpentane Aliphatic dicarboxylic acids such as diacid, 2-methylsuberic acid, 3,8-dimethylsebacic acid, 3,7-dimethylsebacic acid, hydrogenated dimer acid, and dimer acid; o-benzene Aromatic dicarboxylic acids such as dicarboxylic acid, terephthalic acid, isophthalic acid, and naphthalenedicarboxylic acid; alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; trimellitic acid, trimesic acid, and castor oil fatty acids Tricarboxylic acids such as trimer and the like; anhydrides of tetracarboxylic acids such as pyromellitic acid; etc .; dicyandiamide, imidazoles, carboxylic acid esters, sulfonic acid esters, and amine imines.
As the thermal cationic polymerization initiator, commercially available products can also be used, and examples thereof include Adekaopton CP-77, Adekaopton CP-66 (manufactured by ADEKA), CI-2639, CI-2624 (manufactured by Soda Co., Ltd.), San -Aid SI-60L, San-Aid SI-80L, San-Aid SI-100L (manufactured by San Shin Chemical Industry Co., Ltd.), etc.

As the thermal anionic polymerization initiator, one that generates a base by heat can be used, and one known as a thermal anionic polymerization initiator can be used.
As the anionic polymerization initiator, specifically, an aliphatic amine-based compound, an aromatic amine-based compound, a secondary or tertiary amine-based compound, an imidazole-based compound, a polythiol-based compound, and boron trifluoride can be used. -Amine complexes, dicyandiamide, organic hydrazine, etc.

(c) Content of polymerization initiator As the content of the above-mentioned polymerization initiator, it is sufficient as long as it can impart desired hardenability, etc., for example, it can be set to 0.1 parts by mass or more and 30 parts by mass in 100 parts by mass of the solid component. It is preferably 0.5 parts by mass or more and 10 parts by mass or less. The reason for this is that the composition has excellent curability and the like as well as excellent dispersibility and the like by the content.
The content of the polymerization initiator is only required to impart desired curability or light sensitivity. For example, it may be 0.001 to 20 parts by mass, and preferably 0.1 to 100 parts by mass of the polymerizable compound. The mass is not less than 30 parts by mass, and preferably 0.5 part by mass or more and 10 parts by mass or less. The reason for this is that the composition has excellent curability and the like as well as excellent dispersibility and the like by the content.

(3) Others As the above other components, in addition to the resin component and the polymerization initiator, a colorant, a solvent, a chain transfer agent, a sensitizer, a surfactant, a silane coupling agent, a melamine compound, and the like may be included as necessary.
In addition, in addition to the above, the other components described above may optionally include: thermal polymerization inhibitors such as p-anisole, hydroquinone, catechol, third butyl catechol, and phenothion; a plasticizer; Next accelerators; fillers; defoamers; leveling agents; surface modifiers; antioxidants such as phenol-based antioxidants, phosphite-based antioxidants, and thioether-based antioxidants; other than those represented by compound I-1 UV absorber; dispersing aid; anticoagulant; catalyst; effect promoter; crosslinker; tackifier and other additives.

(a) Colorant As the colorant, as long as a desired color can be imparted to, for example, a composition or a cured product thereof, a dye or a pigment can be mentioned.
As the dye, a compound having absorption at 380 to 1200 nm can be used, and examples thereof include an azo compound, an anthraquinone compound, an indigoid compound, a triarylmethane compound, Compounds, alizarin compounds, acridine compounds, amidine compounds, thiazole compounds, naphthol compounds, quinoline compounds, nitro compounds, indamine compounds, amidine compounds, phthalocyanine compounds, cyanine compounds, diimmonium compounds, cyanide Vinyl compounds, dicyanostyrene compounds, rhodamine compounds, fluorene compounds, polyene naphtholactam compounds, coumarin compounds, squarylium compounds, ketonium compounds, spiropyrans Compounds, spironium compounds, merocyanine compounds, oxazonium compounds, styryl compounds, pyranium compounds, rhodanine compounds, oxazolinone compounds, phthalimide compounds, oxazoline compounds, naphthalenes Quinone compounds, azanaphthoquinone compounds, porphyrin compounds, azaporphyrin compounds, pyrrole methylene compounds, quinacridone compounds, pyrrolopyrrole dione compounds, indigo compounds, acridine compounds, acryl compounds , Methylimine compound, aniline compound, quinacridone compound, quinophthalone compound, quinone imine compound, iridium complex Dyes and other complexes can be used in combination.

As the pigment, an inorganic pigment or an organic pigment can be used, and for example, a nitroso compound, a nitro compound, an azo compound, a diazo compound, Compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, isoindolin compounds, quinacridone compounds, anthracene compounds, fluorene compounds, hydrazone compounds, Pyrrolopyrrole dione compound, thioindigo compound, dihydrazone compound, triphenylmethane compound, quinophthalone compound, naphthalene tetracarboxylic acid; metal complex of azo dye and cyanine dye; lake pigment; by Carbon black obtained by furnace method, channel method, thermal method, or carbon black such as acetylene black, Ketjen black, or lamp black; those prepared by adjusting and covering the carbon black with epoxy resin, and previously Carbon black is prepared by dispersing carbon black and adsorbing 20 to 200 mg / g of resin, or by acid or alkaline surface treatment of the carbon black. The average particle diameter is 8 nm or more and DBP (Dibutyl phthalate, Dibutyl phthalate) Oil absorption is 90 ml / 100 g or less, and the total oxygen amount calculated from CO and CO ₂ in volatile components at 950 ° C is 9 mg or more relative to the surface area of carbon black 100 m ² ; Graphite, graphitized carbon black, activated carbon, Carbon fiber, carbon nano tube, spiral carbon fiber, carbon nano angle, carbon aerogel, fullerene; aniline black, pigment black 7, titanium black; hydrophobic resin, chrome oxide green, milori blue, cobalt green, Cobalt Blue, Manganese, Ferrocyanide, Phosphate Ultramarine, Iron Blue, Ultramarine, Sky Blue, Dark Green, Emerald Green, Lead Sulfate, Yellow Dan, Zinc Yellow, Iron Dan (Red Iron (III) Oxide), Cadmium Red , Synthetic iron black, brown earth and other inorganic content or organic pigments. These pigments may be used singly or in combination.

As the inorganic pigment or organic pigment, a commercially available pigment can be used, and examples thereof include pigment red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, and 88. , 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217 , 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62 , 64, 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 109 , 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185; pigments Green 7, 10, 36; Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 22, 24, 56, 60, 61, 62, 64; pigments Purple 1, 19, 23, 27, 29, 30, 32, 37, 40, 50 and so on.

Content of the said coloring agent can be 0.01 mass part or more and 50 mass parts or less with respect to 100 mass parts of solid components of a composition.
The content of the colorant may be 0.01 to 20 parts by mass in 100 parts by mass of the composition.

(b) Solvent The solvent may be any solvent that can dissolve or disperse the above components. Examples include methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, and methyl isopropyl ketone. , Ketones such as methyl isobutyl ketone, cyclohexanone, 2-heptanone; ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, Ether solvents such as dipropylene glycol dimethyl ether; methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, TEXANOL Ester-based solvents; Cellulolytic solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Alcohol solvents such as methanol, ethanol, iso-or-propanol, iso-or-butanol, pentanol, and diacetone alcohol ; Ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate Ester solvents such as esters, ethoxyethyl propionate, 1-third butoxy-2-propanol, 3-methoxybutyl acetate, cyclohexanol acetate; benzene, toluene, xylene Waiting for BTX (Benzene-Toluene -Xylene, benzene-toluene-xylene) series solvents; aliphatic hydrocarbon solvents such as hexane, heptane, octane, cyclohexane; terpene hydrocarbon oils such as turpentine, D-limonene, and pinene; mineral spirits , Swasol # 310 (Cosmo Matsuyama Oil Co., Ltd.), Solvesso # 100 (Exxon Chemical Co., Ltd.) and other paraffin-based solvents; carbon tetrachloride, chloroform, trichloroethylene, dichloromethane, 1,2-dichloroethyl Halogenated aliphatic hydrocarbon solvents such as alkane; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide , N, N-dimethylacetamidamine, N-methylpyrrolidone, dimethylsulfinium, water, etc. These solvents can be used in the form of one or two or more mixed solvents.
The content of the solvent varies depending on the use of the composition, etc., and it can be 1 part by mass or more and 99 parts by mass or less, preferably 10 parts by mass or more and 70 parts by mass in 100 parts by mass of the composition the following. The reason is that it is easy to make it excellent in coating properties and the like.

(c) Chain transfer agent and sensitizer As the above-mentioned chain transfer agent and sensitizer, the sensitivity of the composition can be adjusted, and a compound containing a sulfur atom is usually used. Examples include: thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N- (2-mercaptopropionyl) glycine Acid, 2-mercaptonicotinic acid, 3- [N- (2-mercaptoethyl) aminomethane] propionic acid, 3- [N- (2-mercaptoethyl) amino] propionic acid, N- ( 3-mercaptopropionyl) alanine, 2-mercaptoethanesulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol , 3-mercapto-1,2-propanediol, 1-mercapto-2-propanol, 3-mercapto-2-butanol, mercaptophenol, 2-mercaptoethylamine, 2-mercaptoimidazole, 2-mercaptobenzimidazole Mercapto compounds such as 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, thioglycolic acid, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), etc. Disulfide compounds obtained by oxidation of the mercapto compound, iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2-iodoethanesulfonic acid, 3-iodopropanesulfonic acid and other iodinated alkyl compounds, trimethylolpropanetriol (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, sebacylthiol, 1,4-dimethylmercaptobenzene, butane Alcohol dithiopropionate, butanediol dithioglycolate, ethylene glycol dithioglycolate, trimethylolpropane trithioglycolate, butanediol dithiopropionate, Trimethylolpropane trithiopropionate, trimethylolpropane trithioglycolate, pentaerythritol tetrathiopropionate, pentaerythritol tetrathioglycolate, trihydroxyethyl trithiopropionate And the following compound No. C1, aliphatic polyfunctional thiol compounds such as trimercaptopropionic acid tris (2-hydroxyethyl) isocyanurate, Karenz MT BD1, PE1, NR ¹ and the like manufactured by Showa Denko Corporation.

[Chemical 29]

(d) Surfactants As the surfactants mentioned above, those which can improve the dispersion stability and coating properties of the composition can be used. Fluorine interfacial activities such as perfluoroalkyl phosphate and perfluoroalkyl carboxylate can be used. Agents; anionic surfactants such as higher fatty acid alkali metal salts, alkyl sulfonates, alkyl sulfates; cationic surfactants such as higher amine halide salts, quaternary ammonium salts; polyethylene glycol alkyl ethers , Polyethylene glycol fatty acid esters, sorbitan fatty acid esters, fatty acid monoglycerides and other non-ionic surfactants; amphoteric surfactants; polysiloxane surfactants and other surfactants, these can be used in combination.

(e) Silane coupling agent As the above-mentioned silane coupling agent, a silane compound having a reactive group chemically bonded to an inorganic material such as glass and a reactive group chemically bonded to an organic material such as a synthetic resin can be used to improve the composition or Adhesiveness of hardened materials, etc. As the silane coupling agent, for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be suitably used. Among them, silanes having isocyanate groups, methacryl groups, and epoxy groups such as KBE-9007, KBM-502, and KBE-403 can be suitably used. Coupling agent.

(f) Melamine compound As the melamine compound, those which can improve the hardening property can be used, and examples thereof include (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, A compound in which all or a part (at least 2) of active methylol groups (CH ₂ OH groups) in nitrogen compounds such as (poly) methylol urea are alkylated. Here, as an alkyl group which comprises an alkyl ether, a methyl group, an ethyl group, or a butyl group is mentioned, and may be mutually the same, and may be mutually different. In addition, the methylol group which is not alkyl etherified may be self-condensed in one molecule or may be condensed between two molecules, resulting in the formation of an oligomer component. Specifically, hexamethoxymethylmelamine, hexabutoxymethylmelamine, tetramethoxymethylglycol urea, tetrabutoxymethylglycol urea, and the like can be used. Among these, alkyl melamines such as hexamethoxymethylmelamine and hexabutoxymethylmelamine are preferred.

3. The viscosity of the composition as the composition may be, for example, from the viewpoint of having a coating property, for example, 200 mPa · s or less, and 1 mPa · s or more and 200 mPa · s or less. The reason is that the above-mentioned composition is excellent in coatability.
The above-mentioned viscosity refers to a value measured using a rotary viscometer (for example, manufactured by Anton Paar, Physica MCR ³ 01, etc.) in accordance with JIS Z 8803: 2011. In addition, in this specification, processing and measurement which do not specifically specify temperature can be performed at 25 degreeC.

The method for producing the composition may be a method capable of formulating the above-mentioned components in a desired content, and may be a method of adding the above-mentioned components and mixing them simultaneously, or a method of mixing the components while sequentially adding the components. .

Regarding the use of the above composition, it can be used for: thermosetting coatings, photocuring coatings or varnishes; thermosetting adhesives, photocuring adhesives; printed substrates; or color televisions or PC (Personal Computer) monitoring Filters in liquid crystal display panels for color displays such as cameras, portable information terminals, digital cameras, etc .; color filters for CCD (Charge Coupled Device) image sensors; photosensitive spacers, black columns Spacers; electrode materials for plasma display panels; touch panels; touch sensors; powder coating; printing inks; printing plates; adhesives; dental compositions; photoforming resins; gel coating Photoresist for electronic engineering; electroplating resist; etching resist; both liquid and dry film; solder resist; color filters or plasma display panels for various display applications, electrical Light-emitting display device and LCD (liquid crystal display, liquid crystal display) manufacturing steps for forming a structure resist; a composition for packaging electrical and electronic parts; solder resist Magnetic recording materials; micromechanical parts; waveguides; optical switches; masks for plating; etching masks; color test systems; glass fiber cable coating; stencils for screen printing; Materials for Holographic Recording; Image Recording Materials; Microelectronic Circuits; Decoloring Materials; Decolorizing Materials for Image Recording Materials; Decolorizing Materials for Image Recording Materials Using Microcapsules; Photoresist for Printed Wiring Boards Materials; UV (Ultra Violet, ultraviolet) and visible light laser direct imaging system photoresistive materials; forming a printed circuit board in the successive layers of the dielectric layer used in photoresistive materials; 3D installation of photoresistive materials or protection There are no particular restrictions on the various uses such as films.
In addition, the use described above is not limited to applications requiring durability against ultraviolet rays, such as when used as a product, and may be suitably used for members that are exposed to ultraviolet rays or the like during the manufacturing process, for example.
Examples of members that are exposed to ultraviolet rays during the manufacturing process include members that are exposed to ultraviolet rays and the like in order to improve the surface wettability and improve the adhesion, for example, in order to improve the surface.
Examples of the components that require the improvement of wettability and adhesiveness include components that are laminated with other components. Examples of the components include plasma display panels, organic electroluminescence display devices, and liquid crystal display devices. Color filters, components for various sensors such as touch panels, circuit boards, photosensitive spacers, brightness enhancement boards, light guide plates, thin-film transistor (thin-film transistor) substrates, alignment films, and liquid crystal layers Audio components such as insulating films, speakers, photographic lenses, keyboards, magnetic heads for hard disk drives (hard disk drive), and other components that require surface modification or anti-deterioration during the manufacturing process.
Examples of components that require surface modification or deterioration prevention of the components in the above manufacturing process include components that are laminated with other components through an adhesive, and components that are covered with other components by coatings, for example, automobiles and aircraft. Internal and external components such as transportation equipment, refrigerators, washing machines and other household electrical appliances, residential building materials and other structural components.
In addition, after a pattern-shaped member is formed on the substrate, in order to modify the surface of the exposed substrate, etc., the substrate and the member may be collectively subjected to ultraviolet irradiation or the like. As the above-mentioned application, it can also be preferably used for a component used together with a component that requires surface modification or the like in such a manufacturing process. As the above application, for example, it can be used together with plastic film or glass, silicon wafers, various engineering plastics, optical lenses, metal surfaces, plating, ceramics, molds and other components that require surface cleaning or surface modification. member.

D. Hardened Product Next, the hardened product of the present invention will be described.
The hardened | cured material of this invention is a hardened | cured material containing the composition of the compound I-1 of this invention and a polymerizable compound.

Since the composition of this invention uses the said composition, it has a good ultraviolet absorption function etc.

The hardened | cured material of this invention uses the said composition.
Hereinafter, the hardened | cured material of this invention is demonstrated in detail.

The said composition is a thing containing the said compound I-1 and a polymerizable compound. Moreover, the said composition may contain components other than the said compound I-1 and a polymerizable compound.
The content of each component of such a composition may be the same as that described in the item "2. Other components" of the above-mentioned "C. Composition".

The compound I-1 contained in the composition may be before the photo-release group B is detached in the hardened material, or may be after the detachment, preferably after detachment. The reason for this is that the above-mentioned hardened material has an excellent ultraviolet absorbing function.

The cured product usually contains a polymer of a polymerizable compound.
The remaining amount of the polymerizable compound contained in the hardened material can be appropriately set according to the application of the hardened material, and is, for example, 10 parts by mass or less, and preferably 1 part by mass or less, based on 100 parts by mass of the hardened substance.

As said hardened | cured material, the thing which does not contain a solvent substantially can be used.
The content of the solvent contained in the hardened product may be, for example, 1 part by mass or less and may be 0.5 part by mass or less in 100 parts by mass of the hardened product.

The elastic modulus of the hardened material is usually higher than the composition, and it can be set to, for example, 10 ^-3 M or more and 10 MPa or more. The reason is that, by being the elastic modulus, the cured product can stably hold Compound I-1 and the like.
The upper limit of the above-mentioned elastic modulus can be appropriately set according to the use of the cured product, and can be, for example, 10 ⁶ MPa or less.
In the following, the elastic modulus refers to a compressive elastic modulus, and can be measured at 23 ° C. in accordance with JIS K7181.
As for the measurement sample, for example, a cube test piece with a length of 6 mm on one side can be made or cut out, and measured under the condition of a test speed of 1 ± 0.2 mm / min in accordance with JIS K7181.

The manufacturing method of the said hardened | cured material may just be a method which hardens the said composition, For example, it can be set as the method described in the item of "F. hardened | cured material manufacturing method" mentioned later.

Regarding the use and the like of the cured product, the content described in the item of "C. Composition" may be the same.

E. Composition Next, the second composition of the present invention will be described.
The second composition of the present invention is characterized by comprising a compound represented by the following general formula (I-2) (hereinafter sometimes referred to as "compound I-2") and a release substance derived from a photo-release group (hereinafter sometimes referred to as "compound I-2"). Called "Compound B '").

[Chemical 30]

(In the formula, A is an atomic group having an ultraviolet absorption function, and k represents an integer of 1 to 10)

According to this invention, the said 2nd composition can be easily formed using the said composition, for example. Moreover, the said 2nd composition can provide an ultraviolet absorption function etc. easily.

The second composition of the present invention contains Compound I-2 and Compound B '.
Hereinafter, the second composition of the present invention will be described in detail.

1. Compound I-2
The above-mentioned compound I-2 is a person exhibiting an ultraviolet absorbing function.
The compound I-2 is a compound in which the BO- in the compound I-1 is substituted with an -OH group.
The content of such a compound I-1 may be the same as that described in the above-mentioned "A. Compound", so the description is omitted here.

As the content of the compound I-2 in the composition, it is sufficient as long as it can provide a desired ultraviolet absorption function. For example, the total of the compound I-2 and the compound B 'can be set as the item of the "C. composition" The contents of the solid components of the compound I-1 described above are the same.

2. Compound B '
The above-mentioned compound B 'is a detachment derived from a photo-release group.
The photo-leaving group may be a group capable of binding to a phenolic hydroxyl group as a protective group, and may be the same as described in "1. Photo-Leaving Group B" of the "A. Compound".
As such a compound B ', any one can be used as long as the photo-releasing group is removed from the phenolic hydroxyl group.
In addition, the photo-releasing group B after detachment from a phenolic hydroxyl group is generally highly reactive, and various structures can be adopted.
As the compound B ′, the photo-releasing group B is the general formula (B-1-a), (B-2), (B-3), (B-4), (B-5), (B- 6), (B-7), etc., for example, the following general formulae (B-111-a), (B-112), (B-113), (B-114), Compounds represented by (B-115), (B-116), (B-117), and the like.

[Chemical 31]

Regarding R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ^26, and R ²⁷ and b1, b2, b3, b4, b5, b6, b7, and b8 are the same as those described in the item "A. Compound" above, and therefore descriptions are omitted here.

The kind of the compound B ′ may be only one kind, or a combination of two or more kinds.

3. Other said 2nd composition contains the compound I-2 and the compound B ', and usually contains other components.
Examples of such other ingredients include those described in the item "2. Other ingredients" in the above-mentioned "C. Composition".
Among the other components described above, a resin component is preferable, and a polymer having a polymerizable compound, such as a polymer containing a polymerizable compound, is not particularly preferred. The reason is that the second composition described above can effectively exhibit an effect of easily providing an ultraviolet absorbing function or the like to a cured product or the like.
The type of the resin component may be only one, or two or more kinds may be used in combination.

The second composition may include a solvent, a polymerizable compound, and the like, and may have a coating property, and the viscosity in this case may be the same as that described in the item of "C. Composition" above.
When the second composition is a hardened product of a polymer containing a polymerizable compound, the elastic modulus of the second composition may be the same as that described in the item "D. Hardened product". The content is the same.

The use and the like of the second composition can be the same as those described in the item "D. Hardened product".

F. Manufacturing method of hardened | cured material Next, the manufacturing method of hardened | cured material of this invention is demonstrated.
The method for producing a cured product according to the present invention includes: a step of curing the composition containing Compound I-1 and a polymerizable compound to form a cured product; and irradiating the cured product with light to remove light contained in the compound from the group B. Steps to disengage.

According to the present invention, by using the composition and having the above steps, the production method is easy to harden, and can easily provide an ultraviolet absorbing function.

The manufacturing method of the present invention includes a step of forming a hardened body and a step of detaching.
Hereinafter, each step of the manufacturing method of this invention is demonstrated in detail.

1. Step of Forming a Hardened Body The step of forming a hardened body described above is a step of forming a hardened body of the above composition.

As the method for forming the hardened material of the composition in this step, any method may be used as long as it can form a hardened material having a desired hardness, and it varies depending on the components contained in the composition.
When the composition contains a polymerizable compound and a photopolymerization initiator as a polymerization initiator, for example, a method of polymerizing the polymerizable compounds by irradiating the composition with light may be used.
The light to be irradiated to the composition may be light containing a wavelength of 300 nm to 450 nm.
Examples of the light source for the light irradiation include ultra-high pressure mercury, mercury vapor arc, carbon arc, xenon arc, and the like.
As the above-mentioned irradiated light, laser light can be used. As the laser light, those having a wavelength of 340 to 430 nm can be used.
As a light source of the laser light, an argon ion laser, a helium-neon laser, a YAG (Yttrium Aluminum Garnet) laser, or a semiconductor laser can be used to emit light from the visible light to the infrared region.
Furthermore, in the case where such lasers are used, the above composition may contain a sensitizing pigment that absorbs visible light to the infrared region.

As the total light quantity of the above-mentioned irradiated light, it is preferable to suppress the light from detaching from the radical B. For example, it can be set to less than 1000 mJ / cm ² , 800 mJ / cm ² or less, and 500 mJ / cm ² or less.

The above-mentioned curing method can be used, for example, when the composition contains a polymerizable compound and a thermal polymerization initiator as a polymerization initiator, a method in which the polymerizable compounds are polymerized by subjecting the composition to a heat treatment.
The heating temperature may be any temperature as long as the composition can be stably cured, and may be 60 ° C or higher, and preferably 100 ° C or higher and 300 ° C or lower.
In addition, the heating temperature can be set to the temperature of the coating film surface of the composition.
The heating time may be about 10 seconds to 3 hours.

The types of the above-mentioned hardening methods may include only one type, or may include two or more types.

The composition used in this step is one containing the aforementioned compound I-1 and a polymerizable compound.
The composition may contain components other than the compound I-1 and the polymerizable compound.
The content of each component of such a composition may be the same as that described in the item "2. Other components" of the above-mentioned "C. Composition", and therefore description thereof is omitted here.

2. Step of detachment The step of detachment is a step of detaching the light-release group B contained in the compound I-1.
As a method of removing the light-releasing group B contained in the compound I-1, a method of irradiating the cured product with light may be used.
The light to be irradiated to the hardened object and the total amount of light are not particularly limited as long as the light is released from the radical B, and may be the same as described in the item "1. Light-dissociative group B" of the "A. compound" described above. The content is the same.
The light source to be irradiated may be appropriately selected according to the wavelength of the light to be irradiated. For example, the light source may be the same as that described in the item "1. Step of forming a hardened body".

The temperature of the hardened material in this step can be appropriately set according to the heat resistance of the hardened material or the base material supporting the hardened material. For example, it can be set to 200 ° C or lower, preferably 0 ° C to 150 ° C. It is preferably 0 ° C or higher and 100 ° C or lower. The reason is that when the temperature is in the above-mentioned range, the detachment of the photo-detachment group B becomes easy. The reason for this is that, as a result, for example, damage to peripheral components such as the hardened material and the substrate due to heating can be reduced.
The temperature of the hardened material is the temperature of the surface of the hardened material.

3. Other steps The above manufacturing method includes a step of forming a hardened body and a step of detaching, and other steps may also be included as necessary.
Examples of the other steps include a step of applying the composition to a substrate, and the like.
As a method for applying the composition, a known method such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various printing, and dipping can be used.
The base material can be appropriately set depending on the application of the cured product, and examples thereof include those containing soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, and the like.
Moreover, after the said hardened | cured material is formed on a base material, it can peel and use from a base material, and can also be used by transferring from a base material to another adherend.

4. Other hardened materials and applications produced by the above-mentioned manufacturing method may be the same as those described in the above item "D. Hardened materials".

The invention is not limited to the embodiments described above. The embodiment described above is an example, and those having substantially the same configuration and exhibiting the same effect as the technical idea described in the present invention are included in the technical scope of the present invention.
Examples

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

[Example 1]
0.005 mol of phenol compound (Compound I-2), 0.005 mol of potassium carbonate, and 12 g of DMF (dimethylformamide, dimethylformamide) in the following Scheme 1 were mixed, and added dropwise at room temperature under a nitrogen atmosphere. O-nitrobenzyl chloride was 0.0075 mol, stirred at 80 ° C. for 2 hours, and a compound I-1-2 corresponding to the compound I-1 was obtained by the following reaction. 50 g of ethyl acetate and 50 g of ion-exchanged water were added to the reaction solution, and oil-water separation was performed. After the organic layer was dried with anhydrous sodium sulfate, the solvent was distilled off, and crystallization was performed with methanol. The obtained white solid was dried under reduced pressure at 45 ° C for 2 hours to obtain the target compound (Compound I-1-2). The obtained white solid was identified as a target by H-NMR (nuclear magnetic resonance) and IR (infrared ray).

[Chemical 32]

[Examples 2 to 7]
The following compounds I-1-3, I-1-40, I-1-32, I-1-35, I-1- were obtained in the same manner as in Example 1 except that o-nitrobenzyl chloride was changed. 28, I-1-34. Specifically, the compounds I-1-3, I-1-40, I-1-32, I-1-35, I-1-28, and 1-1-3 of Examples 2 to 7 were produced by the following method. 34.
In addition, the white solids obtained in Examples 2 to 7 were confirmed by H-NMR as a target substance.
[Example 2]
Relative to 2-ethylnitrobenzene, 1.1 equivalents of N-bromosuccinimide and 0.01 equivalents of AIBN (azobisisobutyronitrile) were used, and the mixture was heated and stirred at 90 ° C in a chlorobenzene solvent. 4 hours. Oil-water separation was performed with ethyl acetate, and after washing with water, it was purified through a silica column to obtain a benzyl bromide compound. Compound I-1-3 was obtained in the same manner as in Example 1 except that the benzyl bromide compound was used instead of o-nitrobenzyl chloride. The obtained white solid was confirmed by H-NMR as a target substance.
[Example 3]
Compound I-1-40 was obtained in the same manner as in Example 2 except that 4-chloro-2-nitrotoluene was used instead of 2-ethylnitrobenzene. The obtained white solid was confirmed by H-NMR as a target substance.
[Example 4]
Compound I-1-32 was obtained in the same manner as in Example 1 except that 4'-methoxybenzyl methyl bromide was used instead of o-nitrobenzyl chloride. The obtained white solid was confirmed by H-NMR as a target substance.
[Example 5]
Compound I-1-35 was obtained in the same manner as in Example 1, except that 2-bromo-2-phenylacetophenone was used instead of o-nitrobenzyl chloride. The obtained white solid was confirmed by H-NMR as a target substance.
[Example 6]
Compound I-1-28 was obtained in the same manner as in Example 1, except that 2-bromo-2'-nitroacetophenone was used instead of o-nitrobenzyl chloride. The obtained white solid was confirmed by H-NMR as a target substance.
[Example 7]
Compound I-1-34 was obtained in the same manner as in Example 1, except that 4-bromomethyl-7-methoxycoumarin was used instead of o-nitrobenzyl chloride. The obtained white solid was confirmed by H-NMR as a target substance.

[Chemical 33]

[Example 8]
With respect to 4-methoxy-2-nitrotoluene, 1.1 equivalents of N-bromosuccinimide and 0.01 equivalents of AIBN were used, and the mixture was heated and stirred at 90 ° C for 4 hours in a chlorobenzene solvent. Oil-water separation was performed with ethyl acetate, and after washing with water, it was purified through a silica column to obtain a corresponding benzyl bromide compound. Compound I-1-4 was obtained in the same manner as in Example 1 except that the benzyl bromide compound was used instead of o-nitrobenzyl chloride. The obtained white solid was confirmed by H-NMR as a target substance.
[Example 9]
Compound I-1-41 was obtained in the same manner as in Example 8 except that 3-chloro-2-nitrotoluene was used instead of 4-methoxy-2-nitrotoluene. The obtained white solid was confirmed by H-NMR as a target substance.
[Example 10]
Compound I-1-42 was obtained in the same manner as in Example 8 except that 3-methoxy-2-nitrotoluene was used instead of 4-methoxy-2-nitrotoluene. The obtained white solid was confirmed by H-NMR as a target substance.
[Example 11]
Compound I-1-43 was obtained in the same manner as in Example 8 except that 3-methoxy-2-nitro-6-bromotoluene was used instead of 4-methoxy-2-nitrotoluene. The obtained white solid was confirmed by H-NMR as a target substance.
[Example 12]
Compound I-1-44 was obtained in the same manner as in Example 1, except that 2-bromo-2'-methylacetophenone was used instead of o-nitrobenzyl chloride. The obtained white solid was confirmed by H-NMR as a target substance.

[Example 13]
An intermediate compound was obtained in the same manner as in Example 1, except that 4- (2-bromoethylfluorenyl) phenyl tert-butyl ester was used instead of o-nitrobenzyl chloride. 0.0035 mol of the intermediate compound was dissolved in 5 ml of ethyl acetate, 5 mL of a 4 M HCl ethyl acetate solution was added, and the mixture was heated and stirred at 50 ° C for 10 hours. The solvent of the reaction solution was distilled off, and the product was isolated through a silica column (ethyl acetate: hexane = 1: 2) to obtain the target compound (Compound I-1-45). The obtained white solid was confirmed to be the target by H-NMR.
[Example 14]
0.004 mol of phenol compound (phenol compound in Scheme 1) was dissolved in 40 mL of pyridine, and 0.006 mol of NPPOC-Cl (2- (2-nitrophenyl) propyl chloroformate) was added dropwise, and stirred at room temperature for 6 hour. 200 g of ethyl acetate and 50 g of ion-exchanged water were added to the reaction solution, and oil-water separation was performed. The organic layer was washed twice with dilute hydrochloric acid, and the organic layer was washed three times with ion-exchanged water, and the solvent was distilled off. Single. The obtained white solid was dispersed with hexane, and then dried under reduced pressure at 45 ° C for 2 hours to obtain the target compound (Compound I-1-46). The obtained white solid was confirmed to be the target by H-NMR.
[Examples 15 to 17]
The following compounds I-1-8, I-1-47, and I-1-48 were obtained in the same manner as in Example 1 except that the compounds of the following formulae (1) to (3) were used as phenol compounds. .

[Chem 34]

[Chemical 35]

[Table 1]

[Table 2]

[Evaluation]
Production Examples 1, 2, 5-9, 12-14, and 16 (Compounds I-1-2, I-1-3, I-1-35, I-1-28, I-1-34, I- 1-4, I-1-41, I-1-44, I-1-45, I-1-46, and I-1-47) 0.01% by mass acetonitrile solution was added to a 1 cm square cristobalite tank. The ultra-high pressure mercury lamp UL750 (manufactured by HOYA) was adjusted to 20 mW / cm ² , and the quartz cell filled with the solution was irradiated with a light amount of 100 mJ / cm ² , 3000 mJ / cm ² , and 10000 mJ / cm ² .
The irradiated liquid was analyzed by high performance liquid chromatography (HPLC), and the removal rate was calculated from the following formula. The results are shown in Table 3 below.
In addition, in the analysis by HPLC, when all the 230 nm peaks from Compound I-1 disappeared, it was calculated assuming 100% detachment.
Release rate (%) = phenol compound (compound I-2) / phenol compound (compound I-2 + compound I-1) × 100

In addition, regarding Examples 1, 2 and 7 (compounds I-1-2, I-1-3 and I-1-34), before light irradiation (0 mJ / cm ² ) and after light irradiation (10000 mJ / cm ² ) Confirm the absorption spectrum of light in a wavelength range of 250 nm to 450 nm. As a result, it was confirmed that the light on the long wavelength side can be widely absorbed after the light irradiation in a range of a wavelength of 250 nm or more and 450 nm or less after the light irradiation. The measurement results of the maximum absorption wavelength (nm) are shown in Tables 3 and 4 below.

[table 3]

[Table 4]

From Tables 3 and 4, it was confirmed that the compound I-1 was irradiated with light and the light-releasing group B was removed.
In addition, it is confirmed from Table 3 that the compound I-1 can efficiently absorb ultraviolet rays having a wide range of wavelengths from 250 nm to 450 nm by irradiation with light. Along with this, it was confirmed that the maximum absorption wavelength shifted toward the long wavelength side.
From the above, it was confirmed that the compound I-1 was protected by the photo-releasing group B before the light irradiation, and that the ultraviolet absorption function was suppressed, the curing resistance was suppressed, and the ultraviolet absorption function was easily imparted by light irradiation.

The components shown in Table 5 were mixed at the ratio shown in the following Table 5, and the compositions of Examples 18 to 20 and Comparative Examples 1 and 2 were obtained. The symbols in Table 5 indicate the following compounds. In addition, the numerical value in a table | surface represents a mass part.

A-1: Polymerizable compound (NK OLIGO EA-1020 (bisphenol A epoxy acrylate) manufactured by Shin Nakamura Chemical Industry Co., Ltd.
A-2: Radical polymerizable compound (Kayarad DPHA (mixture of dipentaerythritol pentaerythritol pentaerythritol and hexaacrylate) manufactured by Nippon Kayaku Co., Ltd.)
B-1: Irgacure 907 (free radical polymerization initiator) manufactured by BASF
C-1: Silane coupling agent KBE-403 manufactured by Shin-Etsu Chemical Industry Co., Ltd.
D-1: 2-butanone
E-1: Compound (ultraviolet absorbent) represented by the following formula (1)
F-1: Compound I-1-3
F-2: Compound I-1-35
F-3: Compound I-1-47

[Chemical 36]

The hardening properties and light resistance of the obtained compositions of Examples 18 to 20 and Comparative Examples 1 and 2 were evaluated by the following methods.

[Sclerosis]
The compositions of Examples 18 to 20 and Comparative Examples 1 and 2 were each applied to a PET (polyethylene terephthalate) film with a thickness of about 3 μm by a bar coater. Next, after pre-baking 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 ). In addition, exposure was performed so that exposure light quantity might become 500 mJ / cm <^2> . In this case, in order to measure the light sensitivity, a negative film (a stepwise exposure meter with an optical density of 0.05 as the first stage and an increase of 0.15 in each stage of optical density) was used in which the light transmittance was gradually decreased. Then, using isopropyl alcohol (IPA), washing and developing at 25 ° C for 10 seconds, and then drying at 80 ° C for 30 minutes. Then, the number of steps of the stepwise exposure meter of the hardened material formed on the PET film was measured to evaluate the light sensitivity. The higher the number of steps of the step-type exposure meter, the higher the light sensitivity and the better the hardenability. The results are shown in Table 5 below.

[Light resistance]
The compositions of Examples 18 to 20 and Comparative Examples 1 and 2 were respectively coated on a glass substrate by a spin coater, pre-baked at 80 ° C for 3 minutes, and then exposed using an ultra-high pressure mercury lamp (UL750) as a light source. (20 mW / cm ² ). The exposure is performed so that the exposure light amount becomes 100 mJ / cm ² . Thereafter, it was further irradiated with 3000 mJ / cm ² to prepare a sample for evaluating light resistance. The Xenon light resistance tester Table Sun XT-1500L manufactured by Suga Test Instruments was used to perform a 24-hour light resistance test on the samples for evaluation. The difference between the transmittance (%) of the sample for evaluation at a wavelength of 470 nm before and after the light resistance test ((transmittance before light resistance test (%)-transmittance (%) after light resistance test)) Lightfastness evaluation was performed on the basis.
〇: The transmittance difference (%) is less than 5% with respect to the transmittance before the light resistance test.
×: The transmittance difference (%) is 5% or more with respect to the transmittance before the light resistance test.
A light resistance evaluation of "0" indicates that the light resistance of the cured product is excellent. The results are shown in Table 5 below.

[table 5]

According to Table 5, the compositions of Examples 18 to 20 containing Compound I-1 had better light resistance than the composition of Comparative Example 1 without a UV absorber. In addition, the compositions of Examples 18 to 20 had better curability than the composition of Comparative Example 2 containing a known ultraviolet absorber. From this, it can be understood that the present invention can obtain a composition with less resistance to curing and excellent light resistance.
Industrial availability

The compound of the present invention can provide a compound which has less resistance to hardening and can easily provide an ultraviolet absorbing function to a cured product.
The latent ultraviolet absorbent of the present invention has less hindrance to curing, and can easily provide an ultraviolet absorbing function to the cured product.
The composition of the present invention can provide a composition which has less resistance to hardening and can obtain a hardened product having excellent ultraviolet absorption function.
By the hardened | cured material of this invention, the hardened | cured material which has the outstanding ultraviolet absorption function can be provided.
By the method for producing a cured product of the present invention, a cured product having excellent ultraviolet absorption function and the like can be produced without causing hardening hindrance.
The second composition of the present invention can provide a composition capable of obtaining a cured product having an excellent ultraviolet absorbing function without causing hardening hindrance.

Claims (9)

A compound represented by the following general formula (I-1), (In the formula, A represents an atomic group having an ultraviolet absorption function, B represents a light-releasing group, and k represents an integer of 1 to 10). The compound according to claim 1, wherein B in the general formula (I-1) contains the following general formulae (B-1), (B-2), (B-3), (B-4), (B -5), (B-6), (B-7), (B-8), (B-9) and (B-10), (In the formula, R ¹¹ , R ¹³ , R ¹⁶ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²³ , R ²⁶ and R ²⁸ each independently represent a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, and the number of carbon atoms. An alkyl group of 1 to 40, an aryl group of 6 to 20 carbon atoms, an arylalkyl group of 7 to 20 carbon atoms, or a heterocyclic group containing 2 to 20 carbon atoms, R ¹² , R ¹⁴ , R ¹⁷ , R ²¹ , R ²² , R ²⁴ , R ²⁵ , R ²⁷ , R ²⁹ and R ³⁰ each independently represent 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, an arylalkyl group having 7 to 20 carbon atoms or a heterocyclic group containing 2 to 20 carbon atoms, R ¹⁵ represents an alkyl group having 1 to 40 carbon atoms and carbon atoms 6 to 20 aryl groups, 7 to 20 carbon atoms arylalkyl groups or 2 to 20 carbon atoms heterocyclic groups, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R Alkyl and arylalkyl groups represented by ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ , R ^29, and R ³⁰ The presence of methylene is replaced by carbon-carbon double bonds, -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 In the case of -CO-O-, -NR'-,> P = O, -SS-, -SO _2- , or a combination thereof, the above alkyl, aryl, arylalkyl, and heterocyclic group-containing In the case of a substituent, R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and there are a plurality of R ¹¹ each other, a plurality of R ¹³ each other, a plurality of R ¹⁶ each other, a plurality of R ¹⁸ each other, and a plurality of R ¹⁹ In the case where each other, a plurality of R ²⁰ each other, a plurality of R ²³ each other, a plurality of R ²⁶ each other and a plurality of R ²⁸ are bonded to each other to form a benzene ring or a naphthalene ring, a plurality of R ¹¹ , R ¹² , R ¹³ , R ^{14, R 16, R 17,} R 18, R 19, R 20, R 23, R 25, R 26, R 27, R 28, R 29 and R ³⁰ respectively have the same case, there is the case of different from each other, b1, b2, b3, b6, b7, b8, and b9 each independently represent an integer of 0 to 4, b4 and b5 each independently represent an integer of 0 to 5, and ** represents the bonding position with the above AO-) (In the formula, R ³¹ and R ⁴⁰ each independently represent 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. An arylalkyl group of -20 or a heterocyclic group containing 2 to 20 carbon atoms, and R ³² , R ³³ , R ⁴¹ , R ⁴² , R ⁴³ and R ⁴⁴ each independently represent a hydrogen atom, a halogen atom, a cyano group, Hydroxyl, nitro, carboxyl, alkyl having 1 to 40 carbon atoms, aryl having 6 to 20 carbon atoms, aryl alkyl having 7 to 20 carbon atoms or heterocyclic group containing 2 to 20 carbon atoms The methylene group in the alkyl group and the arylalkyl group represented by R ³¹ , R ³² , R ³³ , R ⁴⁰ , R ⁴¹ , R ⁴² , R ⁴³ and R ⁴⁴ is substituted with a carbon-carbon double bond,- 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-, -NR'-,> P = O, -SS- In the case of -SO ₂ -or a combination thereof, in the case where the alkyl, aryl, arylalkyl, and heterocyclic group have substituents, c1 represents an integer of 0 to 5, and c2 represents an integer of 0 to 4. Integer, ** indicates the bonding position with the above AO-). The compound according to claim 2, wherein the compound represented by the general formula (I-1) is a compound represented by the following general formula (A-1), (A-2), or (A-3) The photo-releasing group B contains the following general formula (B-1-a), (In the formula, R ¹ and R ² each independently represent 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 a carbon atom. An arylalkyl group having 7 to 20 atoms, a heterocyclic group containing 2 to 20 carbon atoms, or the above-OB, at least one of R ¹ and R ² is the above-OB, R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ each independently represent 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 carbon atoms the alkyl group or an aryl group having 20 carbon atoms, heterocyclic group of 2 to ^{20, R 1, R 2, R} 3, R 4, R 5, R 6, R 7 and R ⁸ represented by the alkyl or aryl group The methylene group in the alkyl group is also substituted with carbon-carbon double bonds, -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 In the case of -CO-O-, -NR'-,> P = O, -SS-, -SO _2- , or a combination thereof, the above alkyl, aryl, arylalkyl, and heterocyclic group-containing In the case of a substituent, R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. In the case where a plurality of R ³ each other, a plurality of R ⁴ each other, a plurality of R ⁵ each other, a plurality of R ⁶ each other, and a plurality of R ⁷ are respectively bonded to each other to form a benzene ring or a naphthalene ring, a plurality of R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 may} be the same or different from each other. M1 and m2 each independently represent an integer of 1 to 10, n represents an integer of 1 to 3, and a1 represents 0 to 4 An integer, a2 represents an integer from 0 to 2, a3 represents an integer from 0 to 4, a4 represents an integer from 0 to 3, a5 represents an integer from 0 to 3, a6 represents an integer from 0 to 3-n, X ¹ and X ² (M1 and m2 valence bond groups, respectively) (In the formula, R ¹² independently represents 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 carbon atoms. Arylalkyl of 20 to 20 or heterocyclic group containing 2 to 20 carbon atoms, R ¹¹ represents halogen atom, cyano, hydroxy, nitro, carboxyl, alkyl of 1 to 40 carbon, 6 carbon Aryl group of 20 to 20, arylalkyl group of 7 to 20 carbon atoms or heterocyclic group containing 2 to 20 carbon atoms, methylene group in the alkyl group or arylalkyl group represented by R ¹¹ and R ¹² Existence of carbon-carbon double bonds, -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-, -NR In the case where '-,> P = O, -SS-, -SO ₂ -or a combination thereof, in the case where the alkyl group, aryl group, arylalkyl group and heterocyclic group have substituents, R' represents A hydrogen atom or an alkyl group having 1 to 8 carbon atoms may have a plurality of R ¹¹ bonded to each other to form a benzene ring or a naphthalene ring. R ¹¹ and R ^{12 may} be the same as each other and may be different from each other. B 1 Represents the integer from 0 to 4 ** represents the bonding position of the AO-). A potential ultraviolet absorbent containing a compound as claimed in claim 1. A composition containing a compound as claimed in claim 1. The composition as claimed in claim 5, further comprising a resin component. A hardened material which is a hardened material containing the composition of the compound of Claim 1 and a polymerizable compound. A method for manufacturing a hardened object, comprising: A step of hardening a composition containing a compound as claimed in claim 1 and a polymerizable compound to form a hardened body; and A step of irradiating the hardened material with light to remove light-releasing groups contained in the compound. A composition comprising a compound represented by the following general formula (I-2) and a release substance derived from a photodissociation group, (In the formula, A represents an atomic group having an ultraviolet absorbing function, and k represents an integer of 1 to 10).