TW202325698A - 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, cured product and method for producing the cured product

The present invention relates to a compound that has less hindrance to hardening and can easily impart an ultraviolet absorbing function, etc. to a cured product.

In order to improve the ultraviolet absorbing function or heat resistance of curable compositions, methods of adding ultraviolet absorbers or antioxidants to curable compositions for stabilization are known (Patent Documents 1 to 3). prior art literature patent documents

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 of sometimes hindering the hardening of the curable composition. In view of such a problem, the inventors of the present invention have found that the ultraviolet absorber has the function of absorbing the light irradiated to harden the curable composition; , a situation of hardening obstruction will occur.

As a solution to the above-mentioned problems, there are known latent additives capable of inactivating the above-mentioned light-absorbing effect in the polymerization system and activating it after curing. However, there are cases where heating or the like is necessary for the activation of latent additives that can be activated after hardening, and as a result, there are cases where easier activation is required.

The present invention was made in view of the above-mentioned problems, and a main object of the present invention is to provide a compound that has less hindrance to curing and can easily impart an ultraviolet absorbing function to a cured product.

The inventors of the present invention conducted earnest research in order to solve the above-mentioned problems. As a result, they found that by using a photodetachment group as a protecting group, the photodetachment group is used to protect the phenolic hydroxyl group contained in the ultraviolet absorber, and it becomes easy to adjust the expression of ultraviolet rays. The period of the absorbing function can solve the above-mentioned problems, thereby completing the present invention.

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 with ultraviolet absorption function, B represents a photodetachment group, and k represents an integer from 1 to 10)

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

Moreover, this invention provides the composition containing the compound represented by the said 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 polymeric compound.

Also, the present invention provides a method for producing a cured product, the method for producing a cured product comprising: a step of curing a composition containing a compound represented by the above general formula (I-1) and a polymerizable compound to form a cured product; and A step of irradiating light to the above-mentioned cured product to detach the photodetachable group contained in the compound represented by the above-mentioned general formula (I-1).

Also, the present invention provides a compound (hereinafter sometimes referred to as "compound I-2") represented by the following general formula (I-2) and a detachment product derived from a photodetachment group (hereinafter sometimes referred to as "compound B"). '") composition (hereinafter sometimes referred to as "the second composition").

[Chem 2]

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

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

A. Compound First, the compounds 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).

[Chem 3]

(In the formula, A is an atomic group with ultraviolet absorption function, B is a photodetachment group, and k represents an integer from 1 to 10)

The compound I-1 of the present invention is one whose atomic group A has ultraviolet absorbing function. The compound I-1 of the present invention has a low ultraviolet absorption function before the photo-detachment group B is detached, and exhibits excellent ultraviolet absorption function based on the atomic group A after the photo-detachment group B is detached. Therefore, when the compound I-1 before the photodetachment group B is detached is added to the polymerization system, for example, the compound I-1 has a low ultraviolet absorption function, so the absorption function of the light irradiated for polymerization is low, and it is difficult to Hinder the hardening of the polymer system. On the other hand, the compound I-1 of the present invention exhibits excellent ultraviolet absorption function by detaching the photodegradation group by irradiating light. Therefore, by irradiating a cured product containing compound I-1 with light, it is possible to easily impart an ultraviolet absorbing function to the cured product. Compound I-1 does not require heat treatment in order to express its ultraviolet absorbing function, so it has the advantage that it is less likely to cause damage to surrounding components such as hardened products and substrates due to heating. For the above reasons, the above-mentioned compound I-1 has, for example, little hindrance to curing, and can easily impart an ultraviolet absorbing function to a cured product.

In addition, the compound I-1 of the present invention has a low absorption function of light irradiated in order to express photosensitivity before the photodetachment group B detachment. Therefore, when compound I-1 is added to the photosensitive composition whose solubility with respect to alkaline developing solution changes by light irradiation, photosensitivity can be expressed stably. Moreover, the above-mentioned compound I-1 can easily provide an ultraviolet absorbing function etc. by irradiating a photosensitive composition with light which can detach a photodetachable group. As mentioned above, the said compound I-1 has little hindrance to the expression of photosensitivity with respect to a photosensitive composition, and can easily provide an ultraviolet absorbing function etc. to a photosensitive composition.

Furthermore, by having the photodetachment group B, the compound I-1 of the present invention can easily adjust dispersion or dissolution stability in a composition, for example. Compound I-1 can impart excellent dispersibility in the composition by selecting the photodetachable group B so that the affinity with other components contained in the composition is improved. Therefore, the above-mentioned compound I-1 can impart an excellent ultraviolet absorbing function to the composition, and can also impart 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. Photodetachment group B Compound I-1 of the present invention has a photodetachment group B. The photodetachable group in the present invention may be a group capable of detachment from compound I-1 by irradiation with light of a specific wavelength. When the compound I-1 is irradiated with light of a specific wavelength, the photodetachment group B is detached from the compound I-1 to generate a compound containing a hydroxyl group and an atomic group A having an ultraviolet absorbing function represented by the following general formula (I-2).

[chemical 4]

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

The wavelength of light for the detachment of the photodetachment group B from the compound I-1 is, for example, the wavelength region of ultraviolet light or visible light. Specifically, it can be set to include a wavelength of 365 nm, more specifically, it can be set to include light with a wavelength of 250 nm to 450 nm, preferably 280 nm to 380 nm. Wavelength of Light. The cumulative amount of light irradiated to remove the photodetachable group B from the compound I-1 can be, for example, 1000 mJ/ ^cm2 to 10000 mJ/ ^cm2 , preferably 1000 mJ/ ^cm2 to 5000 mJ /cm ² or less, more preferably 2000 mJ/cm ² or more and 4000 mJ/cm ² or less. This is because the cumulative light intensity of light irradiated to harden the composition containing the polymerizable compound or the like can generally be set to less than 1000 mJ/cm ² . Therefore, application to a photocurable composition becomes easy, for example, by integrating|integrating light quantity being the said range. It should be noted that the detachment of the photodetachable group B is sufficient as long as the desired ultraviolet absorbing function can be imparted. For example, the detachment rate of the photodetachable group can be 50% or more, preferably 80% or more. The reason is that application to photocurable compositions becomes easy. On the other hand, the integrated light amount for suppressing light detachment in the above-mentioned compound I-1 may be less than 1000 mJ/cm ² as long as the desired curing inhibition effect can be obtained. The reason is that application to photocurable compositions becomes easy. In addition, the so-called suppression of photodetachment is sufficient as long as the desired curing inhibition effect can be obtained. For example, the detachment rate of photodetachment group B may be less than 50%, and preferably 20% or less. The reason is that application to photocurable compositions becomes easy. Regarding the above-mentioned cumulative light intensity, a 0.01% by mass acetonitrile solution of Compound I-1 can be prepared and measured using the same method as the method for measuring the detachment rate described in the Examples.

Specific examples of the photodetachable group B satisfying the above requirements include the following general formulas (B-1), (B-2), (B-3), (B-4), (B-5), The groups represented by (B-6), (B-7) and (B-8). Among them, the following general formulas (B-1-a), (B-2-a), (B-3-a), (B-4), (B-5), (B-6) are preferred , (B-7-a), (B-7-b) and (B-8-a) are preferably groups represented by the following general formula (B-1-a). The reason for this is that by using such photodetachable groups, it is possible to easily detach from the compound I-1, and it is easy to impart an ultraviolet absorbing function to the cured product. Moreover, as the photoelimination group B which satisfies the above requirements, specifically, groups represented by the following general formulas (B-9) and (B-10) are also exemplified.

[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 independently represent halogen atom, cyano group, hydroxyl group, nitro group, carboxyl group, number of carbon atoms Alkyl group with 1 to 40 carbon atoms, aryl group with 6 to 20 carbon atoms, arylalkyl group with 7 to 20 carbon atoms or heterocyclic group with 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 with 1 to 40 carbon atoms, An aryl group with 6 to 20 carbon atoms, an arylalkyl group with 7 to 20 carbon atoms, or a heterocyclic group with 2 to 20 carbon atoms, R ¹⁵ represents an alkyl group with 1 to 40 carbon atoms, Aryl group with 6-20 carbon atoms, arylalkyl group with 7-20 carbon atoms or heterocyclic group with 2-20 carbon atoms, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R Alkyl and arylalkyl 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 in it is replaced by 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- In the case of O-, -NR'-, >P=O, -SS-, -SO ₂ - or a combination thereof, R' represents a hydrogen atom or an alkyl group with 1 to 8 carbon atoms, and there are multiple R ¹¹ Each other, multiple ^R13s , multiple ^R16s , multiple ^R18s , multiple ^R19s , multiple ^R20s , multiple ^R23s , multiple ^R26s , and multiple ^R28s When bonding 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 may be the same or different from each other, b1, b2, b3, b6, b7, b8 and b9 independently represent integers from 0 to 4, b4 and b5 Each independently represents an integer of 0 to 5, ** represents the bonding position with the above-mentioned AO-)

[chemical 6A]

(In the formula, R ³¹ and R ⁴⁰ independently represent a halogen atom, cyano group, hydroxyl group, nitro group, carboxyl group, alkyl group with 1 to 40 carbon atoms, aryl group with 6 to 20 carbon atoms, aryl group with 7 carbon atoms An arylalkyl group with ∼20 carbon atoms or a heterocyclic group with 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, Hydroxy, nitro, carboxyl, alkyl with 1 to 40 carbon atoms, aryl with 6 to 20 carbon atoms, arylalkyl with 7 to 20 carbon atoms or heterocyclic group with 2 to 20 carbon atoms , R ³¹ , R ³² , R ³³ , R ⁴⁰ , R ⁴¹ , R ⁴² , R ⁴³ and R ⁴⁴ represented by methylene in the alkyl and arylalkyl groups are 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-CO-O-, -NR'-, >P=O, -SS- , -SO ₂ - or a combination thereof, the above-mentioned alkyl group, aryl group, arylalkyl group and heterocyclic group may have a substituent, 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-)

As the above 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 (these functional groups may be collectively referred to as R ¹¹ etc. below) The alkyl group having 1 to 40 carbon atoms represented includes: methyl, ethyl, propyl, isopropyl, butyl, second butyl, third butyl, isobutyl, pentyl, iso Pentyl, tertiary pentyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, heptyl 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 phenyl, naphthyl and anthracenyl.

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

Examples of the heterocyclic group having 2 to 20 carbon atoms represented by ^R11 and the like above include pyridyl, pyrimidyl, pyridyl, piperidyl, pyranyl, pyrazolyl, triazolyl, Pyrrolyl, quinolinyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl, furyl (furyl), furanyl (furanyl), benzofuryl, thienyl (thienyl), thienyl ( thiophenyl), benzothienyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzooxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidone- 1-yl, 2-piperidinone-1-yl, 2,4-dioxyimidazolidin-3-yl and 2,4-dioxyazolazolidine-3-yl, etc.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R′ include those having 1 to 8 carbon atoms among those 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. Compound I-1 of the present invention includes those without substituents and those with substituents, unless otherwise specified.

Examples of substituents that may substitute hydrogen atoms such as alkyl groups, aryl groups, arylalkyl groups, and heterocyclic groups include: vinyl groups such as vinyl groups, allyl groups, acryl groups, and methacryl groups. Saturated groups; Halogen atoms such as fluorine, chlorine, bromine and iodine; Acetyl, 2-chloroacetyl, propionyl, octyl, acryl, methacryl, phenylcarbonyl (benzoyl) , Phthalyl, 4-trifluoromethylbenzoyl, pivalyl, o-hydroxybenzoyl, oxalyl, stearyl, methoxycarbonyl, ethoxycarbonyl, Acyl groups such as tert-butoxycarbonyl, n-octadecyloxycarbonyl and carbamoyl; acyloxy groups such as acetyloxy and benzoyloxy; amino, ethylamino, dimethylamino , diethylamino, butylamine, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chlorophenylamino, toluidine, methoxyaniline, N-methyl-anilino, diphenylamino, naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzoyl Amino group, formylamino group, pivalylamino group, laurylamino group, aminoformylamino group, N,N-dimethylaminocarbonylamino group, N,N-diethylaminocarbonyl group Amino, 𠰌linylcarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, tert-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxy Carbonylamino, phenoxycarbonylamine, sulfamoylamine, N,N-dimethylaminosulfonylamine, methylsulfonylamine, butanesulfonylamino and benzenesulfonyl Substituted amino group such as amine group; sulfonamide group, sulfonyl group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, imide group, carbamoyl group, sulfonamide group, phosphonic acid group , phosphoric acid group or carboxyl group, sulfo group, phosphonic acid group, salt of phosphoric acid group, etc.

In the present invention, the number of carbon atoms in a group refers to the number of carbon atoms in the substituted group when the hydrogen atom in the group is replaced by a substituent. For example, when the hydrogen atoms of the above-mentioned alkyl group with 1 to 40 carbon atoms are replaced, the so-called carbon number of 1 to 40 refers to the number of carbon atoms after the hydrogen atoms are replaced, not the number of carbon atoms before the hydrogen atoms are replaced. number of carbon atoms.

In the present invention, when the methylene group in the group is substituted with the aforementioned divalent group, the number of carbon atoms in the group specifies the number of carbon atoms in the substituted group. For example, when a methylene group in an alkyl group having 1 to 40 carbon atoms is substituted with the above-mentioned divalent group in this specification, the so-called "1 to 40 carbon atoms" means that the methylene group is substituted The number of carbon atoms, not the number of carbon atoms before the methylene group is substituted. Therefore, "-OC ₄₀ H ₈₁ " corresponds to "an alkyl group having 40 carbon atoms (=alkoxy group having 40 carbon atoms) in which the terminal methylene group is substituted with -O-". Similarly, "-CO-OC ₃₉ H ₇₉ " corresponds to "an alkyl group having 40 carbon atoms in which the terminal methylene group is substituted with -CO-O-".

The presence of methylene in the alkyl and arylalkyl used in R ¹¹ etc. is substituted with 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 thereof. In addition, the combination of substituting the above-mentioned methylene groups may be a combination under the condition that oxygen atoms are not adjacent to each other.

An alkyl group having 1 to 40 carbon atoms represented by R ¹¹ etc. may have an alkoxy group formed by substituting -O- with a methylene group at the end of the base side. As such an alkoxy group, the alkoxy group which has 1-10 carbon atoms is mentioned, for example. Specifically, methoxy, ethoxy, isopropoxy, butoxy, second butoxy, third butoxy, isobutoxy, pentyloxy, isopentyloxy, The third pentyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy Base, isoheptyloxy, third heptyloxy, 1-octyloxy, isooctyloxy and third octyloxy, etc.

The above-mentioned R ¹¹ , R ¹³ , R ¹⁶ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²³ , R ²⁶ and R ²⁸ are preferably groups other than hydroxyl groups, preferably halogen atoms, cyano groups, nitro groups, carboxyl groups, carbon An alkyl group with 1 to 40 atoms, an aryl group with 6 to 20 carbon atoms, an arylalkyl group with 7 to 20 carbon atoms, or a heterocyclic group with 2 to 20 carbon atoms. This is because the photodetachable group B is easily detached from the compound I-1 by making it a group other than a hydroxyl group, and the synthesis of the compound I-1 becomes easy. The aforementioned R ¹¹ and R ²³ are particularly preferably alkoxy groups having 1 to 10 carbon atoms such as nitro and methoxy groups, alkyl groups having 1 to 40 carbon atoms such as methyl groups, halogen atoms, and the like. The reason for this is that the photodetachment group B becomes easy to detach from the compound I-1, and the synthesis of the compound I-1 becomes easy. The above R ¹¹ is preferably an alkoxy group with 1 to 10 carbon atoms, an alkyl group with 1 to 10 carbon atoms, or a halogen atom, more preferably an alkoxy group with 1 to 5 carbon atoms, or an alkoxy group with 1 to 5 carbon atoms. An alkyl group or a halogen atom, more preferably an alkoxy group or a halogen atom having 1 to 5 carbon atoms, especially preferably an alkoxy group having 1 to 3 carbon atoms, a chlorine atom or a bromine atom. The reason for this is that the photodetachment group B becomes easy to detach from the compound I-1, and the synthesis of the compound I-1 becomes 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 for this is that the photodetachment group B becomes easy to detach from the compound I-1, and the synthesis of the compound I-1 becomes easy. The aforementioned R ¹⁶ is preferably such that two adjacent R ¹⁶ are bonded to each other to form a benzene ring. The reason for this is that the photodetachment group B becomes easy to detach from the compound I-1, and the synthesis of the compound I-1 becomes easy. The above-mentioned ^R31 and ^R40 are preferably groups other than hydroxyl groups, preferably halogen atoms, cyano groups, carboxyl groups, alkyl groups with 1 to 40 carbon atoms, aryl groups with 6 to 20 carbon atoms, or aryl groups with 7 to 20 carbon atoms. Arylalkyl group with 20 or heterocyclic group with 2 to 20 carbon atoms. This is because the photodetachable group B is easily detached from the compound I-1 by making it a group other than a hydroxyl group, and the synthesis of the compound I-1 becomes easy. The above-mentioned ^R31 is preferably an alkyl group having 1 to 40 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, further preferably an alkyl group having 1 to 5 carbon atoms, especially preferably 1 carbon atom. ~3 alkyl groups.

When the methylene group in the alkyl group and arylalkyl group represented by ^R18 and ^R19 above is substituted with -O-, the above-mentioned methylene group may be substituted by interrupting the alkyl group and arylalkyl group respectively. -O- of the methyl group sometimes replaces the methylene group other than the terminal of the alkyl group and arylalkyl group.

The aforementioned R ¹² is preferably a hydrogen atom, a carboxyl group, or an alkyl group having 1 to 5 carbon atoms, particularly preferably a hydrogen atom or a methyl group. The reason for this is that the photodetachment group B becomes easy to detach from the compound I-1, and the synthesis of the compound I-1 becomes easy. Regarding the above-mentioned R ¹⁴ , R ¹⁷ , R ²¹ , R ²⁴ , R ²⁵ , R ²⁷ , R ²⁹ and R ³⁰ , among them, a hydrogen atom and an alkyl group having 1 to 40 carbon atoms are preferred, and a hydrogen atom is particularly preferred. The reason for this is that the photodetachment group B becomes easy to detach from the compound I-1, and the synthesis of the compound I-1 becomes easy. The aforementioned R ¹⁵ and R ²² are preferably an alkyl group having 1 to 5 carbon atoms, particularly preferably a methyl group. The reason for this is that it is possible to provide a compound that has less hindrance to hardening and can easily impart an ultraviolet absorbing function to a cured product. The aforementioned R ³² and R ³³ are each independently, preferably a hydrogen atom, a carboxyl group, or an alkyl group with 1 to 5 carbon atoms, more preferably a hydrogen atom or a methyl group, and especially preferably a hydrogen atom. The reason for this is that it is possible to provide a compound that has less hindrance to hardening and can easily impart an ultraviolet absorbing function to a cured product. 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 especially preferably a hydrogen atom. The reason for this is that it is possible to provide a compound that has less hindrance to hardening and can easily impart an ultraviolet absorbing function to a cured product.

The above-mentioned b1, b2, b3, b6, b7, b8, and b9 can each independently be an integer of 0 to 4, and from the viewpoint of ease of synthesis, it is preferably an integer of 0 to 3, more preferably 0 to 3 An integer of 2, more preferably 0 to 1, especially preferably 0. The reason for this is that it is possible to provide a compound that has less hindrance to hardening and can easily impart an ultraviolet absorbing function to a cured product. The above-mentioned b4 and b5 can be each independently an integer of 0 to 5, and from the viewpoint of ease of synthesis, it is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and still more preferably 0 to 5. 1, preferably 0. The reason for this is that it is possible to provide a compound that has less hindrance to hardening and can easily impart an ultraviolet absorbing function to a cured product. The above c1 may be an integer of 0 to 5, preferably an integer of 0 to 3 from the viewpoint of ease of synthesis, more preferably an integer of 0 to 2, further preferably an integer of 0 to 1, especially The best is 1. The reason for this is that it is possible to provide a compound that has less hindrance to hardening and can easily impart an ultraviolet absorbing function to a cured product. The above-mentioned c2 may be an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and still more preferably an integer of 0 to 1, especially from the viewpoint of ease of synthesis. Better is 0. The reason for this is that it is possible to provide a compound that has less hindrance to hardening and can easily impart an ultraviolet absorbing function to a cured product.

When the type of the photodetachable group B contained in the compound I-1 of the present invention is in the case where k is 2 or more, sometimes there is one type in each compound I-1, and sometimes there are two or more types, the hardening hindrance is less, One type is preferable from the viewpoint of easily imparting an ultraviolet absorbing function and the like to a cured product and facilitating the synthesis of Compound I-1.

The content number k of the above-mentioned photodetachable group is an integer of 1 to 10, and is preferably 1 to 5 from the viewpoint of less hindrance to hardening and the ability to easily impart an ultraviolet absorbing function to a cured product, etc., and from the viewpoint of ease of synthesis. An integer of 1 to 4 is more preferred, and an integer of 1 to 3 is particularly preferred.

2. Atomic group A with ultraviolet absorption function Atomic group A is an atomic group with ultraviolet absorbing function. The compound I-1 of the present invention is irradiated with light of a specific wavelength, and the photodetachment group B is detached to form the compound I-2 having a hydroxyl group. In addition, the compound I-2 exhibits the ultraviolet absorbing function due to the ultraviolet absorbing function of the atomic group A.

The so-called "having ultraviolet absorbing function" means, for example, that a compound having ultraviolet absorbing function, specifically, compound I-1 after the detachment of photodetachment group B, that is, compound I-2, can absorb wavelengths of 250 nm or more and 450 nm or more. Light in the range below nm. The atomic group having an ultraviolet absorbing function in the present invention can be defined as a group having an ultraviolet absorbing function or an aggregate of atoms containing at least one group having an ultraviolet absorbing function. More specifically, the so-called compound I-1 after the detachment of the photodetachment group B having an ultraviolet absorbing function, that is, the compound I-2 can absorb the maximum absorption wavelength in the range of 250 nm or more and within 600 nm, and the maximum absorption wavelength is 250 nm or more and For light below 400 nm, it is preferable to absorb light with a maximum absorption wavelength of 260 nm to 390 nm, especially preferably to absorb light with a maximum absorption wavelength of 280 nm to 380 nm. The reason for this is that it is possible to provide a compound that has less hindrance to hardening and can easily impart an ultraviolet absorbing function to a cured product. The maximum absorption wavelength of Compound I-1 after detachment of the photodetachment group B, that is, Compound I-2, can be measured, for example, by the following measurement method. As an evaluation sample, for example, a compound I-1 obtained by detaching the photodetachable group B, that is, a compound I-2, was used which was dissolved in a solvent (acetonitrile) so as to have a concentration of 0.01% by mass. Alternatively, it can be obtained by filling a quartz cell (optical path length: 10 mm, thickness: 1.25 mm) with a sample for evaluation, and measuring absorbance using an absorptiometer (for example, U-3900 (manufactured by Hitachi High-Tech Science Co., Ltd.)).

In addition, the maximum absorption wavelength of Compound I-1 of the present invention before the detachment of the photodetachment group B was compared with the maximum absorption wavelength of the compound I-1 (Compound I-2) after the detachment of the photodetachment group B , preferably within the range of 250 nm to 600 nm, the maximum absorption wavelength of Compound I-1 before the detachment of the photodetachable group B is shorter than the maximum absorption wavelength of Compound I-2. The reason is that application to photocurable compositions becomes easy. The difference between the maximum absorption wavelength of Compound I-1 and Compound I-2 after detachment from the photodetachment group B is preferably at least 1 nm, more preferably at least 1 nm and at most 100 nm, particularly preferably at least 1 nm and Below 50nm. The reason is that application to photocurable compositions becomes easy.

As such an atomic group A, it can be set as the same as the atomic group normally used for the ultraviolet absorber which has a phenolic hydroxyl group. That is, the above-mentioned compound I-2 is generally used as an ultraviolet absorber having a phenolic hydroxyl group. Specifically, as the above compound I-2, 2-hydroxybenzophenones, 2-(2'-hydroxyphenyl)benzotriazoles, Benzoic acid esters and triaryltrisalpines, etc., or benzotriazole-based ultraviolet absorbers and benzophenone-based ultraviolet absorbers described in Japanese Patent Application Laid-Open No. 2002-97224.

As the above-mentioned atomic group A, for example, a phenol structure in which a phenolic hydroxyl group is protected by a photodetachable group B, that is, a benzene ring directly bonded to the above-mentioned B—O— can be mentioned. Specifically, there may be mentioned: an atomic group containing a B-O-direct bonded benzene ring and a benzotriazole ring; an atomic group containing a B-O-direct bonded benzophenone ring; and a B-O-direct bonded benzene ring. The atomic group with three 𠯤 rings. It is preferably a structure containing at least one group of benzotriazolyl, benzophenonyl, and trioxoyl directly bonded to the benzene ring contained in the above-mentioned phenol structure, and among them, benzotriazolyl is preferable At least one of the benzophenon group and the trithiol group has a bonding position to the benzene ring that is ortho to the above-mentioned B-O-bonding position. The reason for this is that it is easy to make a compound with less hindrance to hardening, and it is easy to impart an ultraviolet absorbing function to a cured product.

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

[chemical 7]

(wherein, ^R1 and ^R2 independently represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group with 1 to 40 carbon atoms, an aryl group with 6 to 20 carbon atoms, a carbon An arylalkyl group with 7 to 20 atoms, a heterocyclic group with 2 to 20 carbon atoms, or the aforementioned -OB, at least one of R ¹ and R ² is the aforementioned -OB, R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ independently represent a halogen atom, cyano group, hydroxyl group, nitro group, carboxyl group, alkyl group with 1 to 40 carbon atoms, aryl group with 6 to 20 carbon atoms, aryl group with 7 to 20 carbon atoms, Arylalkyl with 20 or heterocyclic group with 2 to 20 carbon atoms, alkyl or aryl represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ The methylene group in the alkyl group also exists and is replaced by 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 In the case of -CO-O-, -NR'-, >P=O, -SS-, -SO ₂ - or a combination thereof, R' represents a hydrogen atom or an alkyl group with 1 to 8 carbon atoms, and there are plural In the case where a plurality of R ³ , a plurality of R ⁴ , a plurality of R ⁵ , a plurality of R ⁶ , and a plurality of R ⁷ are bonded to each other to form a benzene ring or a naphthalene ring, the 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 independently represent an integer of 1 to 10, n represents an integer of 1 to 3, and a1 represents an integer of 0 to 4 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 respectively Represents the bonding group of m1 valence and m2 valence)

An alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to ²⁰ carbon atoms, or a carbon atom represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R 7 and R ⁸ 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' are listed as the above "1. Photodetachment group B" R ¹¹ etc. and R' exemplified in the item.

At least one of the aforementioned R ¹ and R ² is the aforementioned -OB. From the viewpoint of ease of synthesis, one of the above-mentioned R ¹ and R ² is preferably the above-mentioned -OB. It is preferable that both of R ¹ and R ² are the above-mentioned -OB from the viewpoint of greatly changing the ultraviolet absorbing function of the aforementioned R ¹ and R ² . When only one of the above-mentioned ^R1 and ^R2 is the above-mentioned -OB, the other is preferably a hydrogen atom, a hydroxyl group, an alkyl group with 1 to 40 carbon atoms, an aryl group with 6 to 20 carbon atoms, or a carbon An arylalkyl group with 7 to 20 atoms or a heterocyclic group with 2 to 20 carbon atoms, more preferably a hydrogen atom or an alkyl group with 1 to 40 carbon atoms. The reason is that the above-mentioned compound I-1 has a large change in the ultraviolet absorbing function due to the fact that the other one of the above-mentioned R ¹ and R ² is the above-mentioned functional group. Also, the reason is that the above-mentioned compound I-1 is less hindered in hardening. In addition, as the above-mentioned alkyl group and arylalkyl group, for example, those in which the methylene group is interrupted by -O-, -CO-, etc. can also be preferably used.

The above-mentioned R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are preferably cyano, hydroxyl, alkyl with 1 to 40 carbon atoms, arylalkyl with 7 to 20 carbon atoms, more preferably It is a cyano group, a hydroxyl group, an alkyl group with 1 to 20 carbon atoms, and an arylalkyl group with 7 to 10 carbon atoms, among which, an alkyl group with 3 to 20 carbon atoms is more preferred, and 3 carbon atoms is more preferred. ~10 alkyl groups. 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 photodetachment group B is detached.

Also, from the standpoint of being able to exert an excellent ultraviolet absorbing function after the detachment of the photodetachment group B, ^R4 is preferably an alkyl group having a branched chain structure with 3 to 15 carbon atoms, more preferably 5 carbon atoms An alkyl group having a branched chain structure of ∼12, more preferably an alkyl group having a branched chain structure having 6 to 11 carbon atoms, particularly preferably an alkyl group having a branched chain structure having 7 to 10 carbon atoms. As the bonding site of ^R4 in the benzene ring, it can be bonded to any position that can be bonded, and is preferably at the para position relative to the bonding site of -OB. The reason is that compound I-1 exhibits an excellent ultraviolet absorption function after the photodetachment group B is detached.

From the standpoint of being able to exert an excellent ultraviolet absorption function after the detachment of the photodetachment group B, R ⁵ and R ⁶ are preferably 1 to 20 carbon atoms in which the methylene group at the end of the benzene ring is substituted with -O- The alkyl group is an alkoxy group having 1 to 20 carbon atoms, among which, an alkoxy group having 3 to 15 carbon atoms is preferred, and an alkoxy group having 5 to 12 carbon atoms is particularly preferred. As the bonding sites of R ⁵ and R ⁶ in the benzene ring, they can be bonded at any position that can be bonded, and the bonding site relative to -OB is preferably the meta position. The reason is that compound I-1 exhibits an excellent ultraviolet absorption function after the photodetachment group B is detached.

From the standpoint of exhibiting an excellent ultraviolet absorption function after the detachment of the photodetachment group B, ^R7 is preferably an alkyl group with 1 to 20 carbon atoms in which the methylene group at the end of the benzene ring is substituted with -O- , that is, an alkoxy group with 1 to 20 carbon atoms, in which the methylene chain other than the end of the benzene ring is preferably substituted with an alkoxy group with 3 to 20 carbon atoms of -O-, -O-CO- It is especially preferred that the methylene chain other than the end of the benzene ring side is substituted by -O-, -O-CO-alkoxy group with 3 to 15 carbon atoms, especially preferably a methylene group other than the end of the benzene ring side. An alkoxy group with 6 to 15 carbon atoms whose base chain is substituted by -O-, -O-CO-, especially preferably a methylene chain other than the side terminal of the benzene ring is substituted by -O-, -O- CO- is an alkoxy group with 8 to 13 carbon atoms. As the bonding site of R ⁷ in the benzene ring, it can be bonded to any position that can be bonded, preferably the meta position relative to the bonding site of -OB. The reason is that compound I-1 exhibits an excellent ultraviolet absorption function after the photodetachment group B is detached. From the standpoint of being able to exert an excellent ultraviolet absorbing function after the detachment of the photodetachment group B, R8 is preferably an aryl group with 6 to 20 carbon atoms, and among them, an aryl group with 6 to 12 carbon atoms is preferred, Especially preferred is a phenyl group which may have a substituent.

Also, as the above-mentioned alkyl group and the above-mentioned arylalkyl group, either one in which the methylene group is not interrupted or one in which the methylene group is interrupted by -O-, -CO-, etc. can be preferably used.

Said m1 and m2 represent the integer of 1-10. From the viewpoint of ease of synthesis, the aforementioned m1 and m2 are independently independent, preferably an integer of 1 to 6, more preferably an integer of 1 to 4, especially preferably an integer of 1 to 3, especially preferably 1 to 3 Integer of 2. The reason is that the synthesis of the above-mentioned compound I-1 becomes easy, and the compound I-1 exhibits an excellent ultraviolet absorbing function after the photodetachment group B is detached. In addition, m2 is preferably an integer of 1 from the viewpoint that compound I-1 exhibits an excellent ultraviolet absorbing function after detachment of the photodetachment group B.

Said n represents the integer of 1-3. The above-mentioned n is preferably an integer of 2-3, particularly preferably 3, from the viewpoint that Compound I-1 has a large change in ultraviolet absorbing function. The aforementioned n is preferably an integer of 1-2, particularly preferably 1, from the viewpoint that compound I-1 exhibits an excellent ultraviolet absorbing function after the photo-detachment group B is detached.

Said a1 and a3 each independently represent the integer of 0-4. From the viewpoint of ease of synthesis, the aforementioned a1 and a3 are each independently, preferably an integer of 0-3, more preferably an integer of 0-2, and especially preferably an integer of 0-1. The reason is that compound I-1 can be made into a compound that exhibits an excellent ultraviolet absorbing function after the photodetachment group B is detached. The said a2 represents the integer of the integer of 0-2. The above-mentioned a2 is preferably an integer of 1-2 from the viewpoint of solubility. Moreover, the above-mentioned a2 is preferably 1 from the viewpoint of compound I-1 exhibiting an excellent ultraviolet absorbing function after detachment of the photodetachment group B. The said a4 and a5 represent the integer of 0-3 each independently. The aforementioned a4 and a5 are preferably an integer of 0-2, more preferably an integer of 1-2, and especially preferably 1, from the viewpoint of easiness of synthesis. The reason is that compound I-1 can be made into a compound that exhibits an excellent ultraviolet absorbing function after the photodetachment group B is detached. The above-mentioned a6 represents an integer of 0 to 3-n. The above-mentioned a6 is preferably an integer of 0 to 1, preferably 0, from the viewpoint that compound I-1 exhibits an excellent ultraviolet absorbing function after detachment from the photodetachment group B, and from the viewpoint of easiness of synthesis.

Compound I-1 represented by the above-mentioned general formulas (A-1) and (A-2) has m1 valence or m2 valence (hereinafter sometimes referred to as X) represented by ^X1 and ^X2 (hereinafter sometimes referred to as X). A structure in which m1 or m2 (hereinafter sometimes referred to as m) specific groups are bonded to a specific atom or group with a valence of m. The m specific bases may be the same as each other or may be different from each other.

The above-mentioned X represents a bonding group of m valency. As the above-mentioned bonding group X, specifically, 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), >C =O, >NR ⁵³ , -OR ⁵³ , -SR ⁵³ , -NR ⁵³ R ⁵⁴ or an aliphatic hydrocarbon group with 1 to 120 carbon atoms having the same valence as m, or an aromatic group with 6 to 35 carbon atoms Cyclic hydrocarbon group or heterocyclic group with 2 to 35 carbon atoms, R ⁵³ and R ⁵⁴ independently represent hydrogen atom, aliphatic hydrocarbon group with 1 to 35 carbon atoms, aromatic ring hydrocarbon group with 6 to 35 carbon atoms or A heterocyclic group with 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 thereof , the above-mentioned aromatic ring or heterocyclic ring may also condense with other rings. Wherein, 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 when X is an oxygen atom or a sulfur atom, >C= In the case of O, -NH-CO-, -CO-NH- or >NR ⁵³ , m is 2, in the case of X being -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 bonding with the adjacent group through the * moiety)

Among the aliphatic hydrocarbon groups having 1 to 120 carbon atoms having the same valence as m represented by the above-mentioned bonding group X, those in which m is monovalent include, 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, Alkoxy groups such as isooctyloxy, tertiary octyloxy, 2-ethylhexyloxy, nonyloxy and decyloxy; methylthio, ethylthio, propylthio, isopropylthio, butylthio Base, second butylthio, third butylthio, isobutylthio, pentylthio, isopentylthio, third pentylthio, hexylthio, cyclohexylthio, heptylthio, isoheptylthio Alkylthio groups such as the third heptylthio group, n-octylthio group, isooctylthio group, the third octylthio group and 2-ethylhexylthio group; vinyl, 1-methylvinyl, 2-methyl Vinyl, 2-propenyl, 1-methyl-3-propenyl, 3-butenyl, 1-methyl-3-butenyl, isobutenyl, 3-pentenyl, 4-hexenyl, Alkenyl groups such as cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl, eicosenyl and tridecenyl; and A group substituted with a substituent described below, etc.

Among the aliphatic hydrocarbon groups having 1 to 120 carbon atoms represented by the above-mentioned bonding group X having the same valence as m, m is divalent, such as methylene, ethylidene, and propylidene. , butylene, butanediyl and other alkylene groups; the methylene chains of the above-mentioned alkylene groups are substituted with -O-, -S-, -CO-O-, -O-CO-; ethylene glycol, Residues of diol groups such as propylene glycol, butylene glycol, pentanediol, and hexanediol; and the groups substituted by the substituents described below, etc.

Among the aliphatic hydrocarbon groups having 1 to 120 carbon atoms having the same valence as m represented by the above-mentioned bonding group X, those in which m is trivalent include, for example, propylene and 1,1,3- An alkylene group such as a butylidylpropylene group; and a group in which these groups are substituted with the substituents described below.

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

Among the aromatic ring-containing hydrocarbon groups having 6 to 35 carbon atoms represented by the above-mentioned bonding group X having the same valence as m, those in which m is divalent include: phenylene and naphthylene, etc. group; residues of difunctional phenolic groups such as catechol group and bisphenol group; 2,4,8,10-tetraoxaspiro[5,5]undecyl group; A substituent is substituted with a substituent.

Among the aromatic ring-containing hydrocarbon groups having 6 to 35 carbon atoms represented by the above-mentioned bonding group X having the same valence as m, examples of m being trivalent include phenyl-1,3,5-trimethylene A group and a group obtained by substituting the group with a substituent described below.

Among the heterocyclic groups with 2 to 35 carbon atoms represented by the above-mentioned bonding group X having the same valence as m, those in which m is monovalent include: pyridyl, pyrimidyl, pyridyl, Piperidinyl, pyranyl, pyrazolyl, trioxyl, pyrrolyl, quinolinyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl, furyl (furyl), furanyl (furanyl) ), benzofuryl, thienyl, thiophenyl, benzothienyl, thiadiazolyl, thiazolyl, benzothiazolyl, zozolyl, benzozozolyl, isothiazolyl , Isozazolyl, Indolyl, 2-Pyrrolidinone-1-yl, 2-Piperidinone-1-yl, 2,4-Dioxyimidazolidin-3-yl, 2,4-Dioxy group, oxazolidine-3-yl group, benzotriazolyl group, etc.; and groups in which these groups are substituted with substituents described below, etc.

Among the heterocyclic ring-containing groups having 2 to 35 carbon atoms having the same valence as m represented by the above-mentioned bonding group X, those having a pyridine ring, a pyrimidine ring, and a piperidine ring are examples of m being divalent. , divalent groups such as piperone ring, three-one ring, furan ring, thiophene ring and indole ring; and groups substituted by the substituents described below.

Among the heterocyclic ring-containing groups having 2 to 35 carbon atoms represented by the above-mentioned bonding group X having the same valence as m, examples of m being trivalent include trivalent ones having an isocyanuric acid ring. A group, a trivalent group having a three-ring, and a group obtained by substituting these groups with the substituents described below.

Examples of the aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by ^R53 and ^R54 include carbon atoms in the aliphatic hydrocarbon group represented by the above-mentioned X or a substituent in which the aliphatic hydrocarbon group is substituted with a substituent described below The number is 1-35. Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or the heterocyclic ring-containing group having 2 to 35 carbon atoms represented by R ⁵³ and R ⁵⁴ include the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by X above. A hydrocarbon group or a heterocyclic group having 2 to 35 carbon atoms, or a group in which these groups are substituted with substituents described below.

Each functional group such as the above-mentioned aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, and heterocyclic ring-containing group may have a substituent. Compound I-1 of the present invention includes those without substituents and those with substituents, unless otherwise specified. Examples of substituents for such aliphatic hydrocarbon groups, aromatic ring-containing hydrocarbon groups, and heterocyclic ring-containing groups include the same substituents as substituents for substituting hydrogen atoms of alkyl groups and the like used in R ¹¹ and the like.

In the above general formulas (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 above general formula (1), Y ¹ represents a single bond, -CR ⁵⁵ R ⁵⁶ -, -NR ⁵⁷ -, a divalent aliphatic hydrocarbon group with 1 to 35 carbon atoms, a divalent aliphatic hydrocarbon group with 6 to 35 carbon atoms An aromatic ring-containing hydrocarbon group, a divalent heterocyclic group with 2 to 35 carbon atoms, or any group represented by the following (1-1) to (1-3), the aliphatic hydrocarbon group, the number of carbon atoms Aromatic ring-containing hydrocarbon groups of 6 to 35 and heterocyclic groups with 2 to 35 carbon atoms may also be represented by -O-, -S-, -CO-, -COO-, -OCO- or -NH-, or such When the group of the combination is interrupted, R ⁵⁵ and R ⁵⁶ independently represent a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an aryl group with 6 to 20 carbon atoms, or an aryl alkane with 7 to 20 carbon atoms group, Z ¹ and Z ² 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 hydrogen atom, aliphatic hydrocarbon group with 1 to 35 carbon atoms, aromatic ring hydrocarbon group with 6 to 35 carbon atoms or heterocyclic ring with 2 to 35 carbon atoms group, * means to bond with the adjacent group through the * moiety)

[chemical 10]

(In the above formula, R ⁵⁹ represents a hydrogen atom, a phenyl group that may have a substituent, or a cycloalkyl group with 3 to 10 carbon atoms that may also have a substituent, and R ⁶⁰ represents a cycloalkyl group with 1 to 10 carbon atoms. An alkyl group having 10, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom. The above-mentioned alkyl, alkoxy, and alkenyl groups may also have substituents, and c1 represents 0 Integer of ~5, *means bonding with the adjacent base through * moiety)

[chemical 11]

(*means bonding with the adjacent group through the * moiety)

[chemical 12]

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

[chemical 13]

(In the above general formula (2), ^Y11 represents a trivalent aliphatic hydrocarbon group with 3 to 35 carbon atoms, an alicyclic hydrocarbon group with 3 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group with 6 to 35 carbon atoms, or For a heterocyclic group with 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 with 1 to 35 carbon atoms, aromatic ring hydrocarbon group with 6 to 35 carbon atoms or hydrocarbon group with 2 to 35 carbon atoms A heterocyclic group, ^R62 represents a hydrogen atom, an aliphatic hydrocarbon group with 1 to 35 carbon atoms, an aromatic ring hydrocarbon group with 6 to 35 carbon atoms, or a heterocyclic group with 2 to 35 carbon atoms, the aliphatic hydrocarbon group , Aromatic ring-containing hydrocarbon groups with 6 to 35 carbon atoms and heterocyclic groups with 2 to 35 carbon atoms are surrounded by carbon-carbon double bonds, -O-, -CO-, -O-CO-, -CO-O -or-SO ₂ -in case of interruption)

[chemical 14]

(In the above general formula (3), Y ^represents a carbon atom, a tetravalent aliphatic hydrocarbon group with 1 to 35 carbon atoms, a tetravalent carbon atom with 6 to 35 aromatic ring-containing hydrocarbon groups, or a tetravalent carbon atom A heterocyclic group with a number of 2 to 35, the aliphatic hydrocarbon group, an aromatic ring hydrocarbon group with a carbon number of 6 to 35, or a heterocyclic group with a carbon number of 2 to 35 is replaced by -COO-, -O-, or -OCO When -, -NHCO-, -NH- or -CONH- are interrupted, Z ¹ to Z ⁴ each independently represent a group in the same range as the group represented by Z ¹ to Z ³ in the above general formula (2))

[chemical 15]

(In the above general formula (4), ^Y13 represents an aliphatic hydrocarbon group with 2 to 35 pentavalent carbon atoms, an aromatic ring hydrocarbon group with 6 to 30 pentavalent carbon atoms, or a pentavalent carbon atom with 2 to 30 carbon atoms. The heterocyclic group containing, the aliphatic hydrocarbon group, the aromatic ring hydrocarbon group with 6 to 35 carbon atoms or the heterocyclic group with 2 to 35 carbon atoms may also be replaced by -COO-, -O-, -OCO-, - When NHCO-, -NH- or -CONH- is interrupted, Z ¹ to Z ⁵ each independently represent the same group as that represented by Z ¹ to Z ³ in the above general formula (2))

[chemical 16]

(In the above general formula (5), ^Y14 represents a single bond, an aliphatic hydrocarbon group with a hexavalent carbon number of 2 to 35, an aromatic ring-containing hydrocarbon group with a hexavalent carbon number of 6 to 35, or a hexavalent carbon atom group A heterocyclic group with 2 to 35 carbon atoms, the aliphatic hydrocarbon group, aromatic ring hydrocarbon group with 6 to 35 carbon atoms, or heterocyclic group with 2 to 35 carbon atoms is replaced by -COO-, -O-, -OCO- , -NHCO-, -NH- or -CONH- interrupted, Z ¹ to Z ⁶ each independently represent the same group as that represented by Z ¹ to Z ³ in the above general formula (7))

As the divalent aliphatic hydrocarbon group having ¹ to 35 carbon atoms represented by Y in the group represented by the above general formula (1), methane, ethane, propane, isopropane, butane, second Butane, tertiary butane, isobutane, hexane, 2-methylhexane, 3-methylhexane, heptane, 2-methylheptane, 3-methylheptane, isoheptane, Tertiary heptane, 1-methyloctane, isooctane, tertiary octane, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, 2,4-dimethylcyclobutane , 4-methylcyclohexane, etc. are divalent groups substituted by Z ¹ and Z ² . These groups may be interrupted by -O-, -S-, -CO-, -COO-, -OCO-, -NH- or a combination thereof.

As the divalent aromatic ring-containing hydrocarbon group with 6 to 35 carbon atoms represented by Y in the group represented by the above-mentioned general formula ( ¹ ), phenylene, naphthylene, biphenyl and other groups can be enumerated. ¹ and Z ² substituted divalent groups, etc.

Examples of the divalent heterocyclic group having 2 to 35 carbon atoms represented by Y in the group represented by the above general formula ( ¹ ) include pyridine, pyridine, piperidine, piperidine, pyrimidine, and pyridine. , Three 𠯤, Hexahydrotri 𠯤, Furan, Tetrahydrofuran, 𠳭ane, 𠮿 , thiophene, thiolane, etc. are divalent groups substituted by Z ¹ and Z ² .

The aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, and heterocyclic ring-containing group represented by Y in the group represented by the above general formula ( ¹ ) have a halogen atom, a cyano group, a nitro group, or an alkoxy group with 1 to 8 carbon atoms. The case of group substitution. Each functional group such as the above-mentioned aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, and heterocyclic ring-containing group may have a substituent, unless otherwise specified, it is unsubstituted or has a substituent without a substituent. Examples of the substituents for such aliphatic hydrocarbon groups, aromatic ring-containing hydrocarbon groups, and heterocyclic ring-containing groups include the same substituents as substituents for substituting hydrogen atoms of alkyl groups and the like used in R ¹¹ and the like.

Among the groups represented by the above-mentioned general formula (1), the alkyl groups having 1 to 8 carbon atoms represented by ^R55 and ^R56 include: methyl, ethyl, propyl, isopropyl, butyl, Second butyl, third butyl, isobutyl, pentyl, isopentyl, third pentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2 -heptyl, 3-heptyl, isoheptyl, tertiary heptyl, 1-octyl, isooctyl and tertiary octyl, etc.

Examples of the aryl group having 6 to 20 carbon atoms represented by R ⁵⁵ and R ⁵⁶ in the group represented by the above general formula (1) include: phenyl, naphthyl, 2-methylphenyl, 3-methylphenyl phenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4 - Tertiary 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-tert-pentylphenyl and 2,4,5-trimethylphenyl, etc. Examples of arylalkyl groups having 7 to 20 carbon atoms represented by R ⁵⁵ and R ⁵⁶ in the group represented by the above general formula (1) include: benzyl, phenethyl, 2-phenylpropane-2 -yl, diphenylmethyl, triphenylmethyl, styryl, phenylallyl, etc.

The aliphatic hydrocarbon group with 1 to 35 carbon atoms, the aromatic ring-containing hydrocarbon group with 6 to 35 carbon atoms or the aliphatic hydrocarbon group with 2 to 35 carbon atoms represented by R ⁵⁷ and R ⁵⁸ in the group represented by the above general formula (1) Examples of the heterocyclic group include the same ones as those exemplified for R ⁵³ and R ⁵⁴ .

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

Examples of the alkyl group having 1 to 10 carbon atoms represented by R ⁶⁰ in the group represented by the above general formula (1-1) include those represented by R ¹¹ in the item "1. Photodetachment group B" above. Among the examples of the alkyl group, the number of carbon atoms is 1 to 10. Examples of the alkoxy group having 1 to 10 carbon atoms represented by R ⁶⁰ in the group represented by the above general formula (1-1) include those represented by R ¹¹ in the item "1. Photodetachment group B" above. Among those exemplified by the alkoxy group represented, the number of carbon atoms is 1-10. Examples of the alkenyl group having 2 to 10 carbon atoms represented by ^R60 in the group represented by the above general formula (1-1) include: vinyl group, allyl group, 1-propenyl group, isopropenyl group, 2-propenyl group, -butenyl, 1,3-butadienyl, 2-pentenyl and 2-octenyl, etc. The alkyl group, alkoxy group and alkenyl group represented by R ⁶⁰ above may also be substituted by halogen atoms, and the substitution position is not limited.

As an alkyl group with 1 to 10 carbon atoms, an aryl group with 6 to 20 carbon atoms, and an alkyl group with 7 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the group represented by the above general formula (1-3). The arylalkyl group includes those exemplified as R ¹¹ and the like in the above "1. Photodetachment group B" that satisfy the specified number of carbon atoms.

Examples of the aryloxy group having 6 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the group represented by the above general formula (1-3) include: phenoxy, naphthyloxy, 2-methylbenzene Oxygen, 3-methylphenoxy, 4-methylphenoxy, 4-vinylphenyldioxy, 3-isopropylphenoxy, 4-isopropylphenoxy, 4-butane phenylphenoxy, 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-di Methylphenoxy, 3,5-dimethylphenoxy, 2,4-di-tert-butylphenoxy, 2,5-di-tert-butylphenoxy, 2,6-di-tertiary Butylphenoxy, 2,4-di-tert-pentylphenoxy, 2,5-tri-pentylphenoxy, 4-cyclohexylphenoxy, 2,4,5-trimethylphenoxy group and ferrocenyloxy group and the group formed by substituting these groups 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 above-mentioned general formula (1-3) include the above-mentioned arylthio group having 6 carbon atoms that may be substituted with a halogen atom. ~20 aryloxy groups in which oxygen atoms are substituted with sulfur atoms.

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 above-mentioned carbon atoms that may also be substituted by halogen atoms. The oxygen atom of the aryloxy group with the number 6-20 is replaced by vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl and other alkenyl groups, etc.

As the heterocyclic group having 2 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the group represented by the above general formula (1-3), examples include: pyridyl, pyridyl, piperidyl, piperidine ? group, thiophene group, thiofuran group, and a group obtained by substituting these groups with halogen atoms, etc.

In the group represented by the above general formula (1-3), each functional group represented by ^R61 and ^R62 such as aryloxy group, arylthio group, arylalkenyl group, and heterocyclic ring-containing group may have a substituent, Unless otherwise specified, it is an unsubstituted thing which does not have a substituent, or a thing which has a substituent. As the substituent substituting the hydrogen atom of the aryloxy group, arylthio group, aryl alkenyl group, heterocyclic group, etc., the same substituent as the substituent substituting the hydrogen atom of the alkyl group etc. used in ^R11 etc. can be used. content.

Examples of the trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms represented by Y ¹¹ among the groups represented by the above general formula (2) include the aliphatic hydrocarbon groups exemplified in the description of X in the above general formula (1). Trivalent groups substituted by hydrocarbon groups Z ¹ , Z ² and Z ³ , such groups exist through -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -NH-, or a combination of these substituents.

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

Examples of the trivalent heterocyclic group having 2 to 35 carbon atoms represented by ^Y11 in the group represented by the above general formula (2) include those exemplified in the description of X in the above general formula (1). A trivalent group in which a heterocyclic group is substituted by Z ¹ , Z ² and Z ³ .

As ^an aliphatic hydrocarbon group with ^{1 to 35} carbon atoms, an aromatic ring-containing hydrocarbon group with 6 to 35 carbon atoms, or Examples of the heterocyclic ring-containing group having 2 to 35 carbon atoms are the same as those exemplified above for R ⁵³ and R ⁵⁴ .

Examples of the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by ^Y12 in the group represented by the above general formula (3) include the aliphatic hydrocarbon groups exemplified in the description of X in the above general formula (1). Quaternary groups substituted by hydrocarbon groups Z ¹ , Z ² , Z ³ and Z ⁴ , there are -O-, -S-, -CO-, -COO-, -OCO-, -NH- or the The situation where the basis formed by the combination is interrupted.

As the tetravalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ¹² in the group represented by the above-mentioned general formula (3), there may be mentioned the ones exemplified in the description of X in the above-mentioned general formula (1). Quadrivalent group formed by substituting aromatic ring hydrocarbon group 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 in the group represented by the above general formula (3) include those exemplified in the description of X in the above general formula (1). A tetravalent group formed by substituting a heterocyclic group 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 ^Y13 in the group represented by the above general formula (4) include the aliphatic hydrocarbon groups exemplified in the description of X in the above general formula (1). Pentavalent groups substituted by Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ , there are -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -NH-, or a combination thereof is substituted.

Examples of the pentavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by ^Y13 among the groups represented by the above-mentioned general formula (4) include those exemplified in the description of X in the above-mentioned general formula (1). A pentavalent group formed by substituting an aromatic ring hydrocarbon group 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 ^Y13 in the group represented by the above general formula (4) include those exemplified in the description of X in the above general formula (1). A pentavalent group formed by substituting a heterocyclic group with Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ .

Examples of the hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y ¹⁴ in the above general formula (5) include the aliphatic hydrocarbon groups exemplified in the description of X in the above general formula (1) via Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ are hexavalent groups substituted by -O-, -S-, -CO-, -COO-, -OCO-, -SO ₂ -, -NH-, or a combination of them is interrupted.

Examples of the hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by ^Y14 in the above general formula (5) include the aromatic ring-containing hydrocarbon groups exemplified in the description of X in the above general formula (1). A hexavalent group substituted by Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ .

Examples of the hexavalent heterocyclic group having 2 to 35 carbon atoms represented by ^Y14 in the above general formula (5) include the heterocyclic group exemplified in the description of X in the above general formula (1). A hexavalent group substituted by Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ .

When the above-mentioned bonding group X is 2, it is preferably an aliphatic hydrocarbon group with 1 to 120 carbon atoms, more preferably an alkylene or diol residue, and more preferably an aliphatic hydrocarbon group with 1 to 10 carbon atoms. An alkylene group or a diol residue with 1 to 10 carbon atoms, among them, preferably an alkylene group with 1 to 5 carbon atoms or a diol residue with 1 to 5 carbon atoms, especially preferably a carbon number 1 to 3 alkylene groups. The reason for this is that it can be made into a compound with less hindrance to hardening, and can easily impart an ultraviolet absorbing function to the cured product, and furthermore, compound I-1 can be easily produced.

As the bonding position between the above-mentioned bonding group X and the benzene ring, it can be any position in the benzene ring that can be bonded, for example, it is preferably the ortho or meta position relative to R ² . The reason for this is that it can be used as a compound with less hindrance to hardening, and can easily impart an ultraviolet absorbing function to a cured product.

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

The above-mentioned atomic group A may contain phenolic hydroxyl groups, that is, compound I-1 may contain phenolic hydroxyl groups not protected by photodetachment group B, and the number of phenolic hydroxyl groups is preferably 2 or less, more preferably 0. The reason for this is that the above-mentioned compound I-1 has less hardening inhibition.

3. Compounds The compound of the present invention may be represented by the above-mentioned general formula (I-1), and may be a compound represented by the above-mentioned general formula (A-1), (A-2) or (A-3). As the photodetachment group B , preferably those represented by the above general formula (B-1-a). The reason for this is that the synthesis is relatively easy, and furthermore, the light detachment is relatively easy. Moreover, the reason is that an ultraviolet absorbing function and the like can be easily provided to the cured product. Also, the reason is that compound I-1 is a compound represented by general formula (A-1), (A-2) or (A-3), so it can generate stable absorption by detachment of photodetachment group B. Compound of light in the ultraviolet region.

Specific examples of the above compound I-1 include, for example, the compounds shown below.

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The molecular weight of the above compound I-1 can be set according to the use of the compound I-1 and the like. The molecular weight of the compound I-1 is, for example, preferably from 250 to 5000, more preferably from 300 to 2500, and most preferably from 350 to 1500. The reason for this is that it can be used as a compound with less hindrance to hardening, and can easily impart an ultraviolet absorbing function to a cured product. In addition, the molecular weight of the said compound I-1 is represented by weight average molecular weight (Mw) when compound I-1 is a polymer containing a repeating structure as its structure. The weight average molecular weight (Mw) can be calculated|required as a standard polystyrene conversion value by gel permeation chromatography (GPC).

The above-mentioned weight average molecular weight Mw can be used, for example, HLC-8120GPC manufactured by Tosoh Co., Ltd., the dissolution solvent is N-methylpyrrolidone added with 0.01 mol/liter of lithium bromide, and the calibration curve is set using polystyrene standards. For Mw377400, 210500, 96000, 50400, 20650, 10850, 5460, 2930, 1300, 580 (the above are Easi PS-2 series manufactured by Polymer Laboratories) and Mw1090000 (manufactured by Tosoh Co., Ltd.), set the measuring column to TSK-GEL ALPHA-M x 2 tubes (manufactured by Tosoh Co., Ltd.) were measured and obtained. In addition, the measurement temperature may be set to 40° C., and the flow rate may be set to 1.0 mL/min.

The method for producing the above-mentioned compound I-1 is not particularly limited as long as the desired structure can be obtained. Japanese Patent Laid-Open Publication No. 6-128195, Japanese Patent Laid-Open Publication No. 7-206771, Japanese Patent Laid-Open Publication No. 7-252191 or Japanese Patent Laid-Open No. 2004-501128. Alkyl halide compounds are obtained by reacting.

The above compound I-1 is inactive before light irradiation, and the photodetachment gene is detached by light irradiation to generate compound I-2 with phenolic hydroxyl group. Also, the above-mentioned compound I-2 exhibits an ultraviolet absorbing function. The application of such compound I-1 is preferably an application requiring ultraviolet absorbing function by light irradiation, for example, an ultraviolet absorber added to a composition and the like can be mentioned.

B. Potential UV Absorbers Next, the latent ultraviolet absorber of the present invention will be described. The latent ultraviolet absorber 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 absorber of the present invention has, for example, less hindrance to curing, and can easily impart 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 absorber of the present invention can be set as one containing 100 parts by mass of compound I-1 in 100 parts by mass of the latent ultraviolet absorber, that is, the above-mentioned latent ultraviolet absorber can be set as one containing only the above-mentioned compound I-1 . Moreover, the latent ultraviolet absorber of this invention may contain other components besides compound I-1. When the latent ultraviolet absorber of the present invention contains other components, the content of compound I-1 may be, for example, more than 20 parts by mass and not more than 99 parts by mass in 100 parts by mass of the latent ultraviolet absorber, preferably 25 to 99 parts by mass, more preferably 50 to 99 parts by mass, particularly preferably 80 to 99 parts by mass. The reason for this is that the above-mentioned latent ultraviolet absorber can effectively exhibit effects such as less hindrance to hardening and the ability to easily impart an ultraviolet absorbing function to a cured product.

The type of the above-mentioned compound I-1 contained in the above-mentioned latent ultraviolet absorber may be only 1 type, and may be 2 or more types. When the said latent ultraviolet absorber contains several types of compound I-1, the number of types can be made into 2 or more types and 5 or less types, for example.

In addition, the above-mentioned compound I-1 can be assumed to be the same as that described in the item "A. Compound", so the description is omitted here.

As the above-mentioned other components contained in the above-mentioned latent ultraviolet absorber, for example, the same components as those described in "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 polymeric group, as another component. The reason for this is that the above compound I-1 can be stably maintained.

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

C. Composition Next, the composition of this invention is demonstrated. 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 hindrance to curing and can obtain a cured product having an excellent ultraviolet absorbing function. Hereinafter, each component of the said composition is demonstrated.

1. Compound The content of Compound I-1 in the composition of the present invention is not particularly limited as long as it is an amount capable of imparting desired ultraviolet absorbing functions and the like to the composition. The content of Compound I-1 in the composition of the present invention can be, for example, 0.001 to 20 parts by mass, preferably 0.005 to 10 parts by mass, per 100 parts by mass of the solid content of the composition. . This is because it is easy to make a composition with less hindrance to hardening, and it is easy to impart an ultraviolet absorbing function to a cured product. In addition, the so-called solid content includes all components except the solvent. In addition, unless otherwise specified in this specification, the content is based on mass. The content of the above-mentioned compound I-1 varies depending on the content of the solvent and the like. For example, in 100 parts by mass of the composition, it can be set to 0.001 parts by mass to 20 parts by mass, and preferably 0.005 parts by mass to 10 parts by mass. Parts by mass or less. This is because it is easy to make a composition with less hindrance to hardening, and it is easy to impart an ultraviolet absorbing function to a cured product.

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

In addition, the above-mentioned compound I-1 can be assumed to be the same as that described in the item "A. Compound", so the description is omitted here.

2. Other ingredients The above-mentioned composition may contain components other than the above-mentioned compound I-1 depending on its use or the like. As said other component, a resin component is mentioned, for example. This is because the composition of the present invention contains a resin component in addition to the compound I-1, for example, curability can be easily imparted to the above-mentioned composition. Moreover, it is preferable that the composition of this invention contains the said resin component together with a polymerization initiator as another component. This is because curability and the like can be easily imparted to the composition by containing the resin component and the polymerization initiator as other components in the composition of the present invention.

(1) Resin composition As the above-mentioned resin component, those capable of retaining the above-mentioned compound I-1 are mentioned, which can be appropriately set according to the use of the composition, for example, a polymerizable compound having a polymerizable group and a polymer not having a polymerizable group. By containing a polymerizable compound as the resin component, the composition can be used as a photocurable composition or a thermosetting composition, for example.

(a) Polymeric compound The polymerizable compound varies depending on the kind of the polymerizable group, that is, the kind of the polymerization reaction, and examples thereof include radically polymerizable compounds, cationically polymerizable compounds, and anionically polymerizable compounds. The above-mentioned polymerizable compound preferably contains a radical polymerizable compound from the viewpoint of effectively exerting the effect of reducing hardening inhibition.

(i) Radical polymerizable compound The above-mentioned radically polymerizable compound should just have one or more kinds of polymerizable groups capable of radical polymerization, and may contain two or more kinds. The above 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 (meth)acrylic groups and vinyl groups. In addition, (meth)acryl is used in the meaning which includes acryl and methacryl. In addition, (meth)acrylate is used in the meaning including acrylate and methacrylate.

Moreover, as a radically polymerizable compound, the compound which has an acid value may be sufficient, and the compound which does not have an acid value may be sufficient. As a compound which has an acid value, the compound etc. which have a carboxyl group are mentioned, for example. The said composition contains the compound which has an acid value as a radically polymerizable compound, and the solubility of the light-irradiated part in alkaline developing solution falls. Therefore, the said composition can be used as a photosensitive composition whose solubility to solvents, such as an alkaline developing solution, changes before and after light irradiation, for example. More specifically, the above composition can be used as a negative composition by containing a compound having an acid value. As an alkaline developing solution, what is generally used as an alkaline developing solution, such as a tetramethylammonium hydroxide (TMAH) aqueous solution and an aqueous potassium hydroxide solution, can be used.

Among the above-mentioned radically polymerizable compounds, for example, compounds having an ethylenically unsaturated double bond group and an acid value include (meth)acrylic acid, α-chloroacrylic acid, methylene succinic acid, maleic acid, Acid, methylmaleic acid, fumaric acid, bicycloheptenedicarboxylic acid, crotonic acid, methacrylic acid, vinyl acetic acid, allyl acetic acid, cinnamic acid, hexadienoic acid, methyl fumaric acid , succinate mono[2-(meth)acryloxyethyl] ester, phthalate mono[2-(meth)acryloxyethyl] ester and ω-carboxy polycaprolactone mono (Meth)acrylate is equal to the mono(meth)acrylate of a polymer with carboxyl and hydroxyl groups at both ends; hydroxyethyl (meth)acrylate/maleic acid ester, hydroxypropyl (meth)acrylic acid Ester/maleate, dicyclopentadiene/maleate, or polyfunctional (meth)acrylate with 1 carboxyl group and 2 or more (meth)acryl groups, etc. Monobasic acid; phenol novolak epoxy resin and/or cresol novolac epoxy resin, novolac epoxy resin with biphenyl skeleton or naphthalene skeleton, bisphenol A novolak type epoxy compound, dicyclopentadiene novolac Novolak type epoxy compounds such as varnish type epoxy compounds, polyphenylmethane type epoxy resins having polyfunctional epoxy groups, epoxy resins such as epoxy compounds represented by the following general formula (III) A resin obtained by reacting an unsaturated monobasic acid with an unsaturated monobasic acid, and a resin obtained by reacting an epoxy group of an epoxy resin such as an epoxy compound represented by the following general formula (III) with an unsaturated monobasic acid and further reacting with a polybasic acid anhydride ;As the reaction product of pentaerythritol triacrylate, dipentaerythritol pentaacrylate and other hydroxyl-containing polyfunctional acrylates and dibasic anhydrides such as succinic anhydride, phthalic anhydride, and tetrahydrophthalic anhydride, it has an acid value Multi-functional acrylates, etc.

[chemical 20]

(wherein, X ⁴¹ represents a direct bond, an alkylene group with 1 to 4 carbon atoms, an alicyclic hydrocarbon group with 3 to 20 carbon atoms, -O-, -S-, -SO ₂ -, -SS-, -SO-, -CO-, -OCO- or the substituents represented by (1-1) to (1-3) above, R ⁴¹ , R ⁴² , R ⁴⁴ and R ⁴⁴ each independently represent a hydrogen atom or a carbon atom Alkyl group with 1 to 5 carbon atoms, alkoxy group with 1 to 8 carbon atoms, alkenyl group with 2 to 5 carbon atoms or halogen atom, d is an integer of 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 " Among those exemplified as R ¹¹ etc. in the item of "A. Compound", those satisfying the specific number of carbon atoms. Examples of the alkylene group having 1 to 4 carbon atoms represented by ^X41 include methylene group, ethylene group, propylene group, and butylene group. Examples of the alicyclic hydrocarbon group having 3 to 20 carbon atoms represented by ^X41 include cyclopropyl, cyclopentylene, cyclohexylene and cycloheptylene. 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 have a substituent without a substituent. As the substituent for the hydrogen atom of the substituted alkyl group, alkoxy group, alkenyl group, alkylene group, and alicyclic hydrocarbon group, it can be set to be the same as the substituent for the hydrogen atom of the alkyl group used in ^R11 and the like. the content.

Among the above-mentioned radically polymerizable compounds, for example, compounds having an ethylenically unsaturated double bond group and not having an acid value include 2-hydroxyethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, Propyl ester, glycidyl (meth)acrylate, the following compounds No.A1 to No.A4, methyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, (meth)acrylate base) tertiary butyl acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, hard (meth) acrylate Butyl esters, 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 (meth)acrylate, ethylhexyl (meth)acrylate, phenoxyethyl (meth)acrylate, tetrahydrofuryl (meth)acrylate, vinyl (meth)acrylate, vinyl (meth)acrylate Propyl ester, 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(meth)acrylate, Trimethylol Ethyl ethane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, pentaerythritol tetra(meth)acrylate Acrylates, pentaerythritol tri(meth)acrylate, tricyclodecane dimethylol di(meth)acrylate, tris[(meth)acryloylethyl]isocyanurate, polyester(meth)acrylate base) esters of unsaturated monobasic acids such as acrylate oligomers and polyols or polyphenols; metal salts of unsaturated polybasic acids such as zinc (meth)acrylate and magnesium (meth)acrylate; maleic anhydride, Methylsuccinic anhydride, methylmaleic anhydride, methyltetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5-(2,5- Dioxotetrahydrofuranyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydrophthalic anhydride-maleic anhydride adduct, dodecene Anhydrides of unsaturated polybasic acids such as succinic anhydride and methylbicycloheptenedicarboxylic anhydride; (meth)acrylamide, methylenebis(meth)acrylamide, diethylenetriaminetri(form Base) acrylamide, xylylenebis(meth)acrylamide, α-chloroacrylamide, N-2-hydroxyethyl(meth)acrylamide and other unsaturated monobasic acids and polyamines Amines; unsaturated aldehydes such as acrolein; unsaturated nitriles such as (meth)acrylonitrile, α-chloroacrylonitrile, vinylidene dicyanide, and allyl cyanide; styrene, 4-methylstyrene, 4-ethane Styrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinylphenol, vinylsulfonic acid, 4-ethylene Unsaturated aromatic compounds such as benzenesulfonic acid, vinylbenzyl methyl ether, vinylbenzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; vinylamine, allylamine, N-vinylpyrrole Unsaturated amine compounds such as pyridone and vinyl piperidine; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether, and allyl glycidyl ether; butene Unsaturated imides such as diimide, N-phenylmaleimide, N-cyclohexylmaleimide, etc.; indenes such as indene and 1-methylindene; 1,3 - Aliphatic conjugated dienes such as butadiene, isoprene, and chloroprene; polystyrene, polymethyl(meth)acrylate, poly(n-butylmeth)acrylate, polysiloxane Equal to macromonomers with a single (meth)acryl group at the end of the polymer molecular chain; (meth)acrylonitrile, ethylene, propylene, butene, vinyl chloride, vinyl acetate and other vinyl compounds, and poly Methyl methacrylate macromonomer, macromonomers such as polystyrene macromonomer, tricyclodecane skeleton monomethacrylate, N-phenylmaleimide, methacryl oxide Copolymers of methyl-3-ethyloxetane, etc. and (meth)acrylic acid, and reacting these with isocyanate compounds having unsaturated bonds such as Karenz MOI and AOI manufactured by Showa Denko Co., Ltd. The obtained copolymer of (meth)acrylic acid, or vinyl chloride, vinylidene chloride, divinyl succinate, diallyl phthalate, triallyl phosphate, triallyl isocyanurate Vinyl carbamic acid of ester, vinyl sulfide, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, hydroxyl-containing vinyl monomer and polyisocyanate compound Ester compounds, hydroxyl-containing vinyl monomers and vinyl epoxy compounds of polyepoxides, pentaerythritol triacrylate, dipentaerythritol pentaacrylate and other hydroxyl-containing multifunctional acrylates, toluene diisocyanate, hexamethylene diisocyanate Reactants of polyfunctional isocyanates such as isocyanates, etc.

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[chem 23]

[chem 24]

The above-mentioned radically polymerizable compound can be used individually or in mixture of 2 or more types. Moreover, the radically polymerizable compound can use combining the compound which has an ethylenically unsaturated double bond group and has an acid value, and the compound which has an ethylenically unsaturated double bond group and which does not have an acid value. When using a radically polymerizable compound in mixture of 2 or more types, these can be used as a copolymer by copolymerizing these beforehand. The content of the above-mentioned radically polymerizable compound can be appropriately set according to the use of the composition, etc., for example, in 100 parts by mass of the composition, it can be set to 1 mass part or more and 99 mass parts or less, preferably 10 mass parts or more And 90 mass parts or less, Especially, 40 mass parts or more and 80 mass parts or less are preferable. The reason is that, for example, the above-mentioned composition can be used as a negative-type composition excellent in sensitivity when the above-mentioned content is within the above-mentioned range. Moreover, the reason is that it is possible to provide a composition that has less hindrance to curing and can easily impart an ultraviolet absorbing function to a cured product. The content of the above-mentioned polymerizable compound may be 1 part by mass or more and 99 parts by mass in a total of 100 parts by mass of compound I-1 and the polymerizable compound as long as the above-mentioned composition can be used as a curable composition. Below, it is preferably not less than 50 parts by mass and not more than 99 parts by mass, especially, it is preferably not less than 80 parts by mass and not more than 99 parts by mass, and is preferably not less than 90 parts by mass and not more than 98 parts by mass. The reason for this is that the above-mentioned composition can provide a composition that has less hindrance to hardening and can easily impart an ultraviolet absorbing function, etc. to a cured product when the above-mentioned content is within the above-mentioned range. In addition, the content of the above-mentioned compound I-1 and the radically polymerizable compound can be appropriately set according to the use of the composition, etc., for example, in 100 parts by mass of the composition, it can be set to 1 part by mass or more and 99 parts by mass or less, Preferably it is 10 mass parts or more and 90 mass parts or less, Especially, 40 mass parts or more and 80 mass parts or less are preferable. The reason is that, for example, the above-mentioned composition can be used as a negative-type composition excellent in sensitivity when the above-mentioned content is within the above-mentioned range. Moreover, the reason is that it is possible to provide a composition that has less hindrance to curing and can easily impart an ultraviolet absorbing function to a cured product.

(ii) Cationic polymerizable compound and anionic polymerizable compound The above-mentioned cationically polymerizable compound should just have one or more polymerizable groups capable of cationically polymerizing. The above-mentioned cationically polymerizable compound is usually used together with a cationic polymerization initiator. Examples of the polymerizable group capable of cationic polymerization include cyclic ether groups such as epoxy groups and oxetanyl groups, vinyl ether groups, and the like. That is, examples of the cationically polymerizable compound include cyclic ether compounds such as epoxy compounds and oxetane compounds, vinyl ether compounds, and the like.

Examples of the epoxy compound include: methyl glycidyl ether, 2-ethylhexyl glycidyl ether, butyl glycidyl ether, decyl glycidyl ether, C12-13 mixed alkyl glycidyl ether, phenyl- 2-Methyl glycidyl ether, cetyl glycidyl ether, stearyl glycidyl ether, p-2-butylphenyl glycidyl ether, p-3-butylphenyl glycidyl ether, glycidyl methacrylate Esters, 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, Cresyl Glycidyl Ether, Dibromocresyl Glycidyl Ether, Decyl Glycidyl Ether, Methoxypolyethylene Glycol Monoglycidyl Ether, Ethoxypolyethylene 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, 1,1,2,2-tetrakis(glycidyloxyphenyl)ethane and pentaerythritol Glycidyl ether compounds such as tetraglycidyl ether; glycidyl esters such as glycidyl acetate and glycidyl stearate; 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-cyclo Oxy)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-epoxycyclohexanecarboxylate) ethylene glycol, adipate bis(3,4-epoxycyclohexylmethyl) Esters, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methyl 3,4-epoxycyclohexanecarboxylate Cyclohexyl ester, 6-methyl-3,4-epoxycyclohexylmethyl 6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexane 3,4-epoxy-3-methylcyclohexylmethyl carboxylate, 3,4-epoxy-5-methylcyclohexylmethyl 3,4-epoxy-5-methylcyclohexanecarboxylate, 1-Oxiranyl-3,4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, dicyclopentadiene diepoxide, carboxylic acid 3,4- Epoxy-6-methylcyclohexyl ester, α-pinene oxide, phenylene oxide, epoxycyclohexane and epoxycyclopentane and other epoxycycloalkyl compounds and N-glycidyl o-phthalate Diformimide, etc.

Moreover, an epoxidized polyolefin can also be used as said epoxy compound. The so-called epoxidized polyolefin refers to the polyolefin introduced with epoxy group by modifying polyolefin with 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 any one of a copolymerization method and a grafting method. Ethylene or α-olefins with 3 to 20 carbons, epoxy group-containing monomers and other monomers can be polymerized individually, or can be polymerized with other monomers in plural. In addition, it can also be obtained by epoxidizing the double bond of non-conjugated polybutadiene having a hydroxyl group at the end by the peracetic acid method, and one having a hydroxyl group in the molecule can also be used. In addition, it is also possible to introduce an epoxy group by urethane-forming a hydroxyl group with an isocyanate to react with an epoxy compound containing a primary hydroxyl group.

Examples of ethylene or α-olefins 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 and isoprene, etc.

Examples of the epoxy group-containing monomer include glycidyl esters of α,β-unsaturated acids, vinylbenzyl glycidyl ether, allyl glycidyl ether, and the like. Specific examples of glycidyl esters of α,β-unsaturated acids include glycidyl acrylate, glycidyl methacrylate, and glycidyl ethacrylate, and glycidyl methacrylate is particularly preferred.

Examples of the above-mentioned 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, methylmaleic acid, fumaric acid, bicycloheptenedicarboxylic acid, crotonic acid, methacrylic acid, vinyl acetic acid, allyl acetic acid, cinnamic acid, hexadienoic acid, methyl trans Butenedioic acid, mono[2-(meth)acryloxyethyl]succinate, mono[2-(meth)acryloxyethyl]phthalate, ω-carboxypoly Caprolactone mono(meth)acrylate is equal to mono(meth)acrylate, hydroxyethyl(meth)acrylate/maleate, hydroxypropyl( Meth)acrylate/maleate, dicyclopentadiene/maleate and multifunctional (meth)acrylic acid with 1 carboxyl group and 2 or more (meth)acryl groups Unsaturated polyacids such as esters; 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, methyl (meth)acrylate, butyl (meth)acrylate, (meth)acrylate ) isobutyl acrylate, tertiary butyl (meth)acrylate, cyclohexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate ester, stearyl (meth)acrylate, lauryl (meth)acrylate, methoxyethyl (meth)acrylate, dimethylaminomethyl (meth)acrylate, dimethylamine (meth)acrylate Ethyl (meth)acrylate, Aminopropyl (meth)acrylate, Dimethylaminopropyl (meth)acrylate, Ethoxyethyl (meth)acrylate, Poly(ethoxy)ethyl (meth)acrylate , Butoxyethoxyethyl (meth)acrylate, ethylhexyl (meth)acrylate, phenoxyethyl (meth)acrylate, tetrahydrofuryl (meth)acrylate, vinyl (meth)acrylate ester, allyl (meth)acrylate, benzyl (meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate ) acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate base) acrylate, trimethylolethane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate ester, pentaerythritol tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, tricyclodecane dimethylol di(meth)acrylate, tris[(meth)acrylethyl isocyanurate Esters of unsaturated monobasic acids and polyols or polyphenols such as esters and polyester (meth)acrylate oligomers; metal salts of unsaturated polybasic acids such as zinc (meth)acrylate and magnesium (meth)acrylate ;Maleic Anhydride, Methylenesuccinic Anhydride, Methylmaleic Anhydride, Methyltetrahydrophthalic Anhydride, Tetrahydrophthalic Anhydride, Trialkyltetrahydrophthalic Anhydride , 5-(2,5-dioxytetrahydrofuranyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydrophthalic anhydride-maleic anhydride Adducts, anhydrides of unsaturated polybasic acids such as dodecenylsuccinic anhydride and methylbicycloheptenedicarboxylic anhydride; (meth)acrylamide, methylene bis(meth)acrylamide, di Ethylenetriaminetri(meth)acrylamide, xylylenebis(meth)acrylamide, α-chloroacrylamide, N-2-hydroxyethyl(meth)acrylamide, etc. Amides of saturated monobasic acids and polyamines; unsaturated aldehydes such as acrolein; unsaturated nitriles such as (meth)acrylonitrile, α-chloroacrylonitrile, vinylidene cyanide, and allyl cyanide; styrene, 4- Methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinylphenol, Unsaturated aromatic compounds such as vinylsulfonic acid, 4-vinylbenzenesulfonic acid, vinylbenzyl methyl ether and vinylnaphthalene; unsaturated ketones such as methyl vinyl ketone; vinylamine, allylamine, N -Unsaturated amine compounds such as vinyl pyrrolidone and vinyl piperidine; vinyl alcohol such as allyl alcohol and crotyl alcohol; vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether and isobutyl vinyl ether, etc. Vinyl ether; unsaturated imides such as maleimide, N-phenylmaleimide and N-cyclohexylmaleimide; indene and 1-methylindene Indenes; polystyrene, polymethyl (meth)acrylate, poly(meth)butyl acrylate and polysiloxane are equal to macromonomers with a single (meth)acryl group at the end of the polymer molecular chain 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 urethane compounds of polyisocyanate compounds, hydroxyl-containing vinyl monomers And polyepoxy compounds such as vinyl epoxy compounds, pentaerythritol triacrylate and dipentaerythritol pentaacrylate and other hydroxyl-containing multifunctional acrylates; reactants of multifunctional isocyanates such as toluene diisocyanate and hexamethylene diisocyanate; as A multifunctional product with an acid value of the reaction product of hydroxyl-containing polyfunctional acrylates such as pentaerythritol triacrylate and dipentaerythritol pentaacrylate and dibasic anhydrides such as succinic anhydride, phthalic anhydride, and tetrahydrophthalic anhydride. Acrylate.

Commercially available items can also be used as the above-mentioned 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); JP-100, JP-200 (manufactured by Nippon Soda); Poly bd R-45HT, Poly bd R-15HT (manufactured by Idemitsu Kosan Co., Ltd.), Ricon657 (manufactured by Arkema Co., Ltd.), and the like.

From the viewpoint of good heat resistance, it is more preferable to use a compound having a Cardo skeleton represented by the above-mentioned general formula (II) as the epoxy compound.

Examples of the oxetane compound include: 3,7-bis(3-oxetanyl)-5-oxa-nonane, 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, 3-ethyl-3-(chloromethyl) oxetane, etc.

Examples of the vinyl ether compound include diethylene glycol monovinyl ether, triethylene glycol divinyl ether, n-dodecyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexylethylene Base 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 and 1,6-cyclohexanedimethanol divinyl ether, etc.

As said anion polymerizable compound, what is necessary is just to have 1 or more polymerizable groups which can perform anionic polymerization. The above-mentioned anionic polymerizable compound is usually used together with an anionic polymerization initiator. As a polymeric group which can carry out said anionic polymerization, an epoxy group, a lactone group, a (meth)acryl group etc. are mentioned, for example. That is, as said anion polymeric compound, the compound which has an epoxy compound, a lactone compound, a (meth)acryl group, etc. are mentioned. As said lactone compound, (beta)-propiolactone, (epsilon)-caprolactone, etc. are mentioned. In addition, as an epoxy compound, the epoxy compound exemplified as the above-mentioned cationically polymerizable compound can be used. Moreover, as a compound which has a (meth)acryl group, what was illustrated as a radical polymerizable compound mentioned above can be used.

The said cationically polymerizable compound and anionically polymerizable compound can be used individually or in mixture of 2 or more types, respectively.

(b) Polymers without polymerizable groups As the resin which can be used for the composition of this invention, the polymer which does not have a polymeric group can be used as mentioned above. The weight average molecular weight (Mw) of the polymer which does not have the said polymeric group can be set suitably according to the use of a composition etc., For example, it can be 1500 or more, and can be 1500 or more and 300000 or less. What is necessary is just to contain a repeating structure as such a polymer, and the photosensitive resin which has photosensitivity, the non-photosensitive resin which does not have photosensitivity, etc. are mentioned. The composition of this 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 type resin is used together with an acid generator, and the chemical bond of the ester group or acetal group is cut off by the action of the acid against the developer. Changes in the direction of increasing solubility. By containing the positive resin as the resin component in the above composition, the solubility of the light-irradiated part in the alkaline developing solution is increased. Therefore, the above-mentioned composition can be used as a photosensitive composition whose solubility in solvents, such as an alkaline developing solution, changes before and after light irradiation, and more specifically, as a positive composition.

As the above-mentioned positive type resin, one in which a polymer is partially replaced by an acid-labile group having a function of controlling alkaline dissolution can be used. Examples of the above polymers include: polyhydroxystyrene and its derivatives; polyacrylic acid and its derivatives; polymethacrylic acid and its derivatives; polyhydroxystyrene, acrylic acid, methacrylic acid and derivatives thereof Two or more kinds of copolymers formed by selection of substances; two or more kinds of copolymers formed by selection from hydroxystyrene, styrene and their derivatives; selected from cycloolefins and their derivatives, maleic anhydride , and copolymers of three or more of acrylic acid and its derivatives; copolymers of three or more selected from cycloolefins and their derivatives, maleimide, and acrylic acid and its derivatives; 𦯉ene; one or more polymers selected from the group consisting of metathesis ring-opening polymers, etc. Examples of the acid-labile group introduced into the above-mentioned high molecular weight polymer include: tertiary alkyl group, trialkylsilyl group, pendant oxyalkyl group, aryl-substituted alkyl group, tetrahydropyran-2-yl group, etc. Heteroalicyclic group, tertiary alkylcarbonyl group, tertiary alkylcarbonylalkyl group, alkoxycarbonyl group and the like.

Detailed specific examples of the above-mentioned positive-type resins can be set, for example, as described in JP-A-2003-192665, claim 3 of JP-A-2004-323704, JP-A-10-10733, etc. The content is the same.

Known acid generators can be used as the acid generator used together with the above-mentioned positive resin. As said acid generator, the photocationic polymerization initiator mentioned below, a thermal cationic polymerization initiator, etc. are mentioned specifically,.

(ii) Non-photosensitive resin As long as the above-mentioned non-photosensitive resin does not have photosensitivity, for example, polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly(meth)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, propylene Nitrile-butadiene-styrene) resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated polyester, phenol Resins, phenoxy resins, polyamideimide resins, polyamide acid resins, epoxy resins, etc. As the above-mentioned non-photosensitive resin, for example, a polymer of the above-mentioned polymerizable compound can also be used.

(c) Resin component The content of the above-mentioned resin component in the composition of the present invention can be appropriately determined according to the use of the composition, etc., for example, in 100 parts by mass of the solid content of the composition, it is preferably not less than 1 part by mass and not more than 99 parts by mass , more preferably at least 20 parts by mass and at most 95 parts by mass, particularly preferably at least 30 parts by mass and at most 90 parts by mass. This is because, for example, the above-mentioned composition can stably maintain the above-mentioned compound I-1 when the above-mentioned content is within the above-mentioned range. The content of the above-mentioned resin component can be appropriately set according to the use of the composition, for example, in 100 parts by mass of the composition, it can be set to 1 mass part or more and 99 mass parts or less, preferably 10 mass parts or more and 90 mass parts Part or less, among them, Preferably it is more than 40 parts by mass and 80 parts by mass or less. The reason is that, for example, the above-mentioned composition can be used as a negative-type composition excellent in sensitivity when the above-mentioned content is within the above-mentioned range. Moreover, the reason is that it is possible to provide a composition that has less hindrance to curing and can easily impart an ultraviolet absorbing function to a cured product. The content of the above-mentioned resin component varies depending on the use of the composition, etc., and may be 1 to 99 parts by mass, preferably 50 parts by mass, in a total of 100 parts by mass of the compound I-1 and the resin component. More than 99 parts by mass, preferably 80 parts by mass to 99 parts by mass, preferably 90 parts by mass to 98 parts by mass. The reason is that the above-mentioned composition can provide a composition capable of easily imparting an ultraviolet absorbing function, etc. to a cured product when the above-mentioned content is within the above-mentioned range. In addition, the content of the above-mentioned compound I-1 and the resin component can be appropriately set according to the use of the composition, for example, in 100 parts by mass of the composition, it can be set to 1 mass part or more and 99 mass parts or less, preferably 10 mass parts or more and 90 mass parts or less, especially preferably 40 mass parts or more and 80 mass parts or less. The reason is that, for example, the above-mentioned composition can be used as a negative-type composition excellent in sensitivity when the above-mentioned content is within the above-mentioned range. Moreover, the reason is that it is possible to provide a composition that has less hindrance to curing and can easily impart an ultraviolet absorbing function to a cured product.

The kind of the said resin component contained in the composition of this invention may be only 1 type, and may be a combination of 2 or more types. For example, the said resin component may contain only any one of a polymeric compound and a polymer, or may contain both. When the above-mentioned resin component contains both a polymerizable compound and a polymer without a polymerizable group, the content of the above-mentioned polymerizable compound can be appropriately set according to the use of the composition, for example, between the polymerizable compound and the polymeric group. In 100 parts by mass of the substance, it may be not less than 1 part by mass and not more than 99 parts by mass.

(2) Polymerization initiator The above-mentioned polymerization initiator is contained as a curable component, and is usually used together with a polymerizable compound or the like. As the above-mentioned polymerization initiator, as long as it can polymerize a polymerizable compound, for example, a photopolymerization initiator that can polymerize a polymerizable compound by being irradiated with light, a photopolymerization initiator that can polymerize a polymerizable compound by heating, etc. thermal polymerization initiator, etc. The above-mentioned polymerization initiator is preferably a photopolymerization initiator from the viewpoint that the above-mentioned compound I-1 effectively exhibits the effect of functioning as an ultraviolet absorber.

(a) Photopolymerization initiator As the above-mentioned photopolymerization initiator, as long as it is capable of polymerizing a polymerizable compound by being irradiated with light, for example, photoradical polymerization initiators, photocationic polymerization initiators, photoanionic polymerization initiators, etc. agent etc.

As the photoradical polymerization initiator, a previously known compound can be used without particular limitation as long as it generates radicals by light irradiation. As the photoradical polymerization initiator, for example, acetophenone-based compounds, benzoyl-based compounds, benzophenone-based compounds, 9-oxothiophene Compounds and oxime ester compounds are preferred.

Examples of the acetophenone-based compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4'-isopropyl-2-hydroxy- 2-methylpropiophenone, 2-hydroxymethyl-2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethan-1-one, p-dimethylaminophenethyl Ketone, p-tert-butyldichloroacetophenone, p-tert-butyltrichloroacetophenone, p-azidobenzylidene acetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1 -[4-(methylthio)phenyl]-2-𠰌linylacetone-1, 2-benzyl-2-dimethylamino-1-(4-𠰌linylphenyl)-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 Base-1-propan-1-one, etc.

Examples of the above-mentioned benzoyl compound include benzoyl and the like.

Examples of the above-mentioned benzophenone-based compounds include benzophenone, methyl o-benzoylbenzoate, michelerone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dichlorobenzophenone and 4-benzoyl-4'-methyl diphenyl sulfide, etc.

As the above-mentioned 9-oxosulfur series compounds, such as: 9-oxosulfur 𠮿 , 2-methyl-9-oxosulfur , 2-Ethyl-9-oxosulfur 𠮿 , 2-Chloro-9-oxosulfur , 2-isopropyl-9-oxothio𠮿 , 2,4-Diethyl-9-oxothio𠮿 wait.

As said oxime type compound, the compound represented by following general formula (IV) is mentioned, for example.

[chem 25]

(In the formula, R ⁷¹ and R ⁷² independently represent a hydrogen atom, a cyano group, an alkyl group with 1 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, an arylalkyl group with 7 to 30 carbon atoms Or a heterocyclic group with 2 to 20 carbon atoms, R ⁷³ and R ⁷⁴ independently represent a halogen atom, nitro, cyano, hydroxyl, carboxyl, 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 bound 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 with 1 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, an arylalkyl group with 7 to 30 carbon atoms, or an alkyl group with 2 carbon atoms. ~20 heterocyclic groups, X ³ represents oxygen atom, sulfur atom, 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 independently represent a hydrogen atom, an alkyl group with 1 to 20 carbon atoms, an aryl group with 6 to 20 carbon atoms, or an arylalkyl group with 7 to 20 carbon atoms. The methylene group may also be substituted by a halogen atom, nitro, cyano, hydroxyl, carboxyl, or a heterocyclic group, and may also be substituted by -O-, and R ⁷³ and R ⁷⁴ may also be independently When forming a ring with any adjacent benzene ring, e1 represents an integer of 0 to 4, and e2 represents an integer of 0 to 5)

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 above general formula (IV) 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 having 2 to 20 carbon atoms, and substituents thereof include the above-mentioned "1. Photodetachable group B" satisfies the specified number of carbon atoms among the contents exemplified as R ¹¹ and the like.

As the above-mentioned oxime compound, for example, ethanone-1-[9-ethyl-6-(2-methylbenzoyl-9H-carbazol-3-yl]-1-(O-acetyl oxime), 1-[9-ethyl-6-benzoyl-9H-carbazol-3-yl-octane-1-one oxime-O-acetate, 1-[9-ethyl- 6-(2-methylbenzoyl)-9H-carbazol-3-yl]-ethane-1-one oxime-O-benzoate, 1-[9-n-butyl-6-( 2-Ethylbenzoyl)-9H-carbazol-3-yl]-ethane-1-one oxime-O-benzoate, ethyl ketone-1-[9-ethyl-6-(2 -Methyl-4-tetrahydrofurylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyl oxime), ethyl ketone-1-[9-ethyl-6-(2 -Methyl-4-tetrahydropyranylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyl oxime), ethyl ketone-1-[9-ethyl-6 -(2-Methyl-5-tetrahydrofurylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyl oxime), ethyl ketone-1-[9-ethyl-6 -{2-methyl-4-(2,2-dimethyl-1,3-dioxolanyl)methoxybenzoyl}-9H-carbazol-3-yl]-1-( O-acetyl oxime), ethyl ketone-1-[9-ethyl-6-(2-methyl-4-tetrahydrofurylmethoxybenzoyl)-9H-carbazol-3-yl]- Carbazole-based oxime ester compounds having a carbazole structure, such as 1-(O-acetyloxime).

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

[chem 26]

(In the formula, R ²⁰¹ and R ²⁰² independently represent R ²¹¹ , OR ²¹¹ , COR ²¹¹ , SR ²¹¹ , CONR ²¹² R ²¹³ or CN, R ²¹¹ , R ²¹² and R ²¹³ independently represent the number of hydrogen atoms and carbon atoms An alkyl group with 1 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, an arylalkyl group with 7 to 30 carbon atoms, or a heterocyclic group with 2 to 20 carbon atoms, R ²¹¹ , R ²¹² and R ²¹³ The hydrogen atoms of the indicated groups are also substituted by 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 ²²¹ , R ²²² and R ²²³ independently represent a hydrogen atom, a carbon atom An alkyl group with 1 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, an arylalkyl group with 7 to 30 carbon atoms, or a heterocyclic group with 2 to 20 carbon atoms, R ²²¹ , R ²²² and R ²²³ The hydrogen atoms of the groups represented may be further substituted by hydroxyl, nitro, CN, halogen atoms, hydroxyl or carboxyl groups, the groups represented by R ²¹¹ , R ²¹² , R ²¹³ , R ²²¹ , R ²²² and R ²²³ The methylene group of the alkylene part also exists and is substituted by -O-, -S-, -COO-, -OCO-, -OCOO-, -CONR ²²⁴ -, -NR ²²⁴ -, -NR ²²⁴ CO-, In the case of -NR ²²⁴ COO-, -OCONR ²²⁴ -, -SCO-, -COS-, -OCS-, or -SCOO-, R ²²⁴ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 6 to 20 carbon atoms. 30 aryl group, arylalkyl group with 7 to 30 carbon atoms or heterocyclic group with 2 to 20 carbon atoms, represented by R ²¹¹ , R ²¹² , R ²¹³ , R ²²¹ , R ²²² , R ²²³ and R ²²⁴ The alkyl portion of the group represented may also have a branched side chain, or may be a cyclic alkyl group. R ²⁰³ represents a hydrogen atom, an alkyl group with 1 to 20 carbon atoms, or an alkyl group with 6 to 30 carbon atoms. An aryl group, an arylalkyl group with 7 to 30 carbon atoms, or a heterocyclic group with 2 to 20 carbon atoms, the alkyl part of the group represented by ^R203 may also have a branched side chain, and may also be In the case of a cyclic alkyl group, R ²⁰³ and R ²⁰⁷ and R ²⁰³ and R ²⁰⁸ may also form a ring together, and the hydrogen atom of the group represented by R ²⁰³ may be 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 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 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 also exist together to form a ring In the case of R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ and R ²⁰⁷ , the hydrogen atom of the group represented by R ²²¹ , OR ²²¹ , COR ²²¹ , SR ²²¹ , NR ²²² R ²²³ , CONR ²²² R ²²³ , NR In the case of 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 ²¹⁴ , R ²¹⁵ and R ²¹⁶ represent a hydrogen atom or an alkyl group with 1 to 20 carbon atoms, and the alkyl part of the group represented by R ²¹⁴ , R ²¹⁵ and R ²¹⁶ may have a branched side chain or be cyclic In the case of an 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)

The number of carbon atoms used for 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 above general formula (V) is 1 to 20 An alkyl group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms. Among the contents exemplified as R ¹¹ etc. in the item, those satisfying the specific number of carbon atoms.

Examples of other radical polymerization initiators include phosphine oxide compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis(cyclopentadienyl)-bis[2,6- Titanocene-based compounds such as difluoro-3-(pyrrol-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 (manufactured by BASF), TR-PBG-304, TR-PBG-305, TR-PBG-309 and TR-PBG-314 (manufactured by Tronly) wait.

These photoradical polymerization initiators can be used in combination of one type or two or more types according to the required performance. As the content of the photoradical polymerization initiator, as long as the desired curability or photosensitivity can be imparted, for example, with respect to 100 parts by mass of the polymerizable compound, it can be set to 0.001 mass parts or more and 20 mass parts or less. Preferably it is 0.1 mass part or more and 30 mass parts or less, More preferably, it is 0.5 mass parts or more and 10 mass parts or less. The reason for this is that the curability of the composition, etc. are excellent, and the dispersibility, etc. are also excellent by setting it as the said content.

As the above-mentioned photocationic polymerization initiator, there is no particular limitation as long as it is a compound capable of releasing a substance that initiates cationic polymerization by irradiation with light. Existing compounds can be used. And release the double salt of the onium salt of the Lewis acid, or its derivatives. Representative examples of this compound include salts of cations and anions represented by the following general formula [A1] ^r+ [B1] ^r- .

The above-mentioned cation [A1] ^r+ is preferably 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 having 1 to 60 carbon atoms and may contain some atoms other than carbon atoms. f1 is any integer from 1 to 5. The e R ^58s are independent, have the same situation, and have different situations. Also, it is preferable that at least one of R ¹⁰¹ is the above-mentioned organic group having an aromatic ring. For example, there are also alkyl, alkoxy, hydroxyl, hydroxyalkoxy, halogen atoms, benzyl, thiophenoxy, 4-benzoylphenylthio, 2-chloro-4-benzyl Phenyl in case of substitution such as acylphenylthio group. Q is an atom or an atomic group selected from the group consisting of S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, F, N=N. Also, when the atomic valence of Q in the cation [A1] ^r+ is set to q, the relationship of r=f1-q must be established (wherein, N=N is treated as the atomic valence is 0).

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

Furthermore, here, L is a metal or semimetal (Metalloid) as a central atom of a halide complex, and is B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn and Co, etc. X _f2 is a halogen atom, or a phenyl group which may be substituted with a halogen atom or an alkoxy group. f2 is an integer of 3-7. Also, 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 above general formula include tetrakis (pentafluorophenyl) borate, tetrakis (3,5-difluoro-4-methoxyphenyl) borate, tetrakis Fluoroborate (BF ₄ ) ^- , hexafluorophosphate (PF ₆ ) ^- , hexafluoroantimonate (SbF ₆ ) ^- , hexafluoroarsenate (AsF ₆ ) ^- and hexachloroantimonate (SbCl ₆ ) ^- etc.

Also, as the anion _[ B1] ^r-, _a structure represented by the following general formula [LX _f2-1 (OH)] ^r- can also be preferably used. L, X, and f2 are the same as above. In addition, other usable anions include: perchlorate ion (ClO ₄ ) ^- , trifluoromethylsulfite ion (CF ₃ SO ₃ ) ^- , fluorosulfonate ion (FSO ₃ ) ^- , toluenesulfonate Acid anion, trinitrobenzenesulfonate anion, camphorsulfonate, nonafluorobutanesulfonate, hexadecafluorooctylsulfonate, tetraaryl borate and tetrakis(pentafluorophenyl)borate, etc.

In the present invention, among such onium salts, use of the following aromatic onium salts (a) to (c) is particularly effective and therefore preferred. Among these, one type may be used alone, or two or more types may be mixed and used.

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

(B) Diphenyliodonium hexafluoroantimonate, bis(4-methylphenyl)iodonium hexafluorophosphate, bis(4-tert-butylphenyl)iodonium hexafluorophosphate and tolylcumene Diaryl iodonium salts such as base iodonium tetrakis(pentafluorophenyl) borate.

(C) The permeic salts of the permeic cation represented by the following group I or II, hexafluoroantimony ion, tetrakis(pentafluorophenyl)borate ion, etc.

[Chem.27] <Group I>

[Chem.28] <Group II>

Also, as other preferred ones, it is also possible to enumerate: (η5-2,4-cyclopentadien-1-yl)[(1,2,3,4,5,6-η)-(1-methyl Iron-arene complexes such as ethyl)benzene]-iron-hexafluorophosphate; aluminum complexes such as tris(acetylacetone)aluminum, tris(ethylacetone acetate)aluminum, and tris(salicyloxylate)aluminum ; Mixtures with silanols such as triphenylsilanol: etc.

As said photocationic polymerization initiator, you may use a commercial item, For example, IRUGACURE261 (made by BASF company), Adeka Optomer SP-150, SP-151, SP-152, SP-170, SP-171, SP -172 (manufactured by ADEKA), UVE-1014 (manufactured by General Electronics), CD-1012 (manufactured by Sartomer), CI-2064, CI-2481 (manufactured by Nippon Soda), Uvacure1590, 1591 (Daicel UCB), CYRACUREUVI - 6990 (manufactured by Union Carbide), BBI-103, MPI-103, TPS-103, MDS-103, DTS-103, NAT-103, NDS-103 (manufactured by Midori Kagaku), etc.

Among them, it is preferable to use an aromatic iodonium salt, an aromatic cerium salt, and an iron-arene complex from the viewpoint of practicality and photosensitivity.

As said photoanionic polymerization initiator, what generates a base by light can be used, and what is known as a photoanionic polymerization initiator can be used. As said photoanionic polymerization initiator, acetophenone O-aroyl oxime (acetophenone O-aroyloxime), nifedipine (nifedipine), etc. are mentioned, for example.

(b) thermal polymerization initiator As said thermal-polymerization initiator, if it can polymerize a polymerizable compound by heating, a radical polymerization initiator, a cationic polymerization initiator, an anionic polymerization initiator etc. are mentioned.

As said thermal radical polymerization initiator, what generates a radical by heating can be used, and what is known as a thermal radical polymerization initiator can be used. As said thermal radical polymerization initiator, an azo compound, a peroxide, a persulfate, etc. are illustrated as preferable one, for example.

Examples of the above-mentioned azo compounds include: 2,2'-azobisisobutyronitrile, 2,2'-azobis(methyl isobutyrate), 2,2'-azobis-2,4 -Dimethylvaleronitrile, 1,1'-azobis(1-acetyloxy-1-phenylethane) and the like.

Examples of peroxides include: benzoyl peroxide, di(tert-butyl)benzoyl peroxide, tert-butyl peroxypivalate, and di(4-tert-butyl peroxydicarbonate) Cyclohexyl) ester, etc.

As said persulfate, persulfate, such as ammonium persulfate, sodium persulfate, and potassium persulfate, etc. are mentioned.

As said thermal cationic polymerization initiator, what generates a cationic species or a Lewis acid by heating can be used, and what is known as a thermal cationic polymerization initiator can be used. Specific examples of the aforementioned thermal cationic polymerization initiators include: salts such as cerium salts, thiophenium salts, thiolanium salts, benzyl ammonium salts, pyridinium salts, and thiolanium salts; diethylenetriamine , triethylenetriamine and tetraethylenepentamine and other polyalkylene polyamines; 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane alicyclic polyamines such as alkane and isophorone diamine; aromatic polyamines such as m-xylylenediamine, diaminodiphenylmethane and diaminodiphenylmethane; The above-mentioned polyamines and glycidyl ethers such as phenyl glycidyl ether, butyl glycidyl ether, bisphenol A-diglycidyl ether, and bisphenol F-diglycidyl ether, or glycidyl esters of carboxylic acids, etc. Polyepoxy addition modified products produced by reacting epoxy resins; acyl acids produced by reacting the above-mentioned organic polyamines with carboxylic acids such as phthalic acid, isophthalic acid and dimer acid by conventional methods Aminated modified product; by using conventional methods to make the above-mentioned polyamines and formaldehyde and other aldehydes and phenol, cresol, xylenol, tertiary butylphenol and resorcinol have at least one hydroformylation reaction Mannich modified products produced by reacting phenols at the sex position; polycarboxylic acids (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid , azelaic acid, sebacic acid, dodecanedioic acid, 2-methylsuccinic acid, 2-methyladipic acid, 3-methyladipic acid, 3-methylglutaric acid, 2-methyl Aliphatic dicarboxylic acids such as suberic acid, 3,8-dimethylsebacic acid, 3,7-dimethylsebacic acid, hydrogenated dimer acid and dimer acid; phthalic acid, terephthalic acid Aromatic dicarboxylic acids such as formic acid, isophthalic acid, and naphthalene dicarboxylic acid; alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; trimers of trimellitic acid, trimellitic acid, and castor oil fatty acid, etc. Tricarboxylic acids; anhydrides of tetracarboxylic acids such as pyromellitic acid, etc.); dicyandiamide, imidazoles, carboxylates, sulfonates, and amidoimides, etc. As said thermal cationic polymerization initiator, you may use a commercial item, For example, Adekaopton CP-77, Adekaopton CP-66 (made by ADEKA company), CI-2639, CI-2624 (manufactured by Nippon Soda Co., Ltd.), San -Aid SI-60L, San-Aid SI-80L, San-Aid SI-100L (manufactured by Sanshin Chemical Industry Co., Ltd.), etc.

As said thermal anionic polymerization initiator, what generates a base by heat can be used, and what is well-known as a thermal anionic polymerization initiator can be used. As the aforementioned anionic polymerization initiator, specifically, aliphatic amine compounds, aromatic amine compounds, secondary or tertiary amine compounds, imidazole compounds, polythiol compounds, boron trifluoride - Amine complexes, dicyandiamide, organic hydrazines, etc.

(c) Content of polymerization initiator The content of the above-mentioned polymerization initiator is sufficient as long as it can impart desired curability, etc., for example, in 100 parts by mass of solid content, it can be set to 0.1 mass part or more and 30 mass parts or less, preferably 0.5 mass part More than or equal to 10 parts by mass or less. The reason for this is that the curability of the composition, etc. are excellent, and the dispersibility, etc. are also excellent by setting it as the said content. The content of the above-mentioned polymerization initiator is sufficient as long as it can impart desired curability or photosensitivity, for example, it can be set at 0.001 mass parts to 20 mass parts with respect to 100 mass parts of the polymerizable compound, preferably 0.1 It is not less than 30 parts by mass, preferably not less than 0.5 parts by mass and not more than 10 parts by mass. The reason for this is that the curability of the composition, etc. are excellent, and the dispersibility, etc. are also excellent by setting it as the said content.

(3) Others As the above-mentioned other components, in addition to the resin component and the polymerization initiator, colorants, solvents, chain transfer agents, sensitizers, surfactants, silane coupling agents, melamine compounds, and the like may be included as needed. In addition, the above-mentioned other components may also include thermal polymerization inhibitors such as p-anisole, hydroquinone, catechol, tertiary butylcatechol, and phenanthrene; plasticizers. ; Then accelerator; Filler; Defoamer; Leveling agent; Additives other than ultraviolet absorbers; dispersing aids; anticoagulants; catalysts; effect accelerators; crosslinking agents; tackifiers and other additives.

(a) Coloring agent As said coloring agent, if desired coloring can be given to a composition or its hardened|cured material, etc., dyes and pigments are mentioned, for example. As dyes, compounds that absorb at 380-1200 nm can be used, for example, azo compounds, anthraquinone compounds, indigoid compounds, triarylmethane compounds, 𠮿 Compounds, alizarin compounds, acridine compounds, stilbene compounds, thiazole compounds, naphthol compounds, quinoline compounds, nitro compounds, indamine compounds, 㗁𠯤 compounds, phthalocyanine compounds, cyanine compounds, diimonium compounds, Cyanovinyl compounds, dicyanostyrene compounds, rhodamine compounds, perylene compounds, polyene naphtholactam compounds, coumarin compounds, squarylium compounds, crotonium compounds, spiropyridine Pyranium compounds, spiro 㗁𠯤 compounds, merocyanine compounds, oxalanine compounds, styryl compounds, pyrylium compounds, rhodanine compounds, oxazolone compounds, phthalimide compounds, phenoline compounds , naphthoquinone compounds, azanaphthoquinone compounds, porphyrin compounds, azaporphyrin compounds, pyrromethene compounds, quinacridone compounds, diketopyrrolopyrrole compounds, indigo compounds, acridine compounds, Dyes such as acridine compounds, formimine compounds, aniline compounds, quinacridone compounds, quinophthalone compounds, quinoneimine compounds, iridium complexes, europium complexes, and the like may be used in combination.

As pigments, inorganic pigments or organic pigments can be used, for example: nitroso compounds, nitro compounds, azo compounds, diazo compounds, 𠮿 Compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, isoindoline compounds, quinacridone compounds, anthracenthrone compounds, pyrene compounds, perylene compounds, Diketopyrrolopyrrole compounds, thioindigo compounds, dioxane compounds, triphenylmethane compounds, quinophthalone compounds, naphthalene tetracarboxylic acid; metal complexes of azo dyes and cyanine dyes; lake pigments; Carbon black obtained by furnace method, channel method, or thermal method, or carbon black such as acetylene black, Ketjen black, or lamp black; those obtained by adjusting and coating the above-mentioned carbon black with epoxy resin, pre-cured by resin in a solvent The above-mentioned carbon black is dispersed and made to absorb 20 to 200 mg/g of resin, and the above-mentioned carbon black is subjected to acidic or alkaline surface treatment, with an average particle size of 8 nm or more and DBP (Dibutyl phthalate, Dibutyl phthalate) with an oil absorption of 90 ml/100 g or less, and a total oxygen content calculated from CO and CO ₂ in the volatile components at 950°C relative to the surface area of carbon black of 100 m ² is 9 mg or more Graphite, graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, spiral carbon fiber, carbon nanohorn, carbon aerogel, fullerene; aniline black, pigment black 7, titanium black; hydrophobic resin, Chrome oxide green, Milori blue, cobalt green, cobalt blue, manganese series, ferrocyanide, phosphate ultramarine blue, iron blue, ultramarine blue, sky blue, dark green, emerald green, lead sulfate, yellow lead, zinc yellow, iron Dan (red iron oxide (III)), cadmium red, synthetic iron black, umber and other inorganic content or organic pigments. These pigments may be used alone or in combination of plural kinds.

As the above-mentioned inorganic pigments or organic pigments, commercially available pigments can be used, for example, pigment red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 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; pigment 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; Pigment Purple 1, 19, 23, 27, 29, 30, 32, 37, 40, 50, etc.

As content of the said coloring agent, it can be made into 0.01 mass part or more and 50 mass parts or less with respect to 100 mass parts of solid content of a composition. As content of the said coloring agent, it can be made into 0.01 mass part or more and 20 mass parts or less in 100 mass parts of compositions.

(b) solvent As the above-mentioned solvent, as long as it can dissolve or disperse the above-mentioned components, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isopropyl ketone, Butyl ketone, cyclohexanone, 2-heptanone and other ketones; ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl Ether solvents such as ether; ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, TEXANOL, etc. ; Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether and other cellosolve solvents; methanol, ethanol, iso-or n-propanol, iso-or n-butanol, amyl alcohol, diacetone alcohol and other alcohol-based solvents; ethylene glycol Monomethyl acetate, Ethylene glycol monoethyl acetate, Propylene glycol-1-monomethyl ether-2-acetate (PGMEA), Dipropylene glycol monomethyl ether acetate, 3-Methoxybutyl acetate, Propionic acid Ethoxyethyl ester, 1-tert-butoxy-2-propanol, 3-methoxybutyl acetate, cyclohexanol acetate and other ether ester solvents; benzene, toluene, xylene and other BTX (Benzene -Toluene-Xylene, benzene-toluene-xylene) solvents; aliphatic hydrocarbon solvents such as hexane, heptane, octane, cyclohexane, etc.; terpene hydrocarbon oils such as turpentine, D-limonene, pinene, etc.; Paraffinic solvents such as olein, Swasol#310 (Cosmo Matsuyama Oil Co., Ltd.), Solvesso#100 (Exxon Chemical Co., Ltd.); carbon tetrachloride, chloroform, trichloroethylene, dichloromethane, 1,2-bis Halogenated aliphatic hydrocarbon solvents such as ethyl chloride; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformaldehyde Amide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, water, etc. These solvents can be used in the form of one or more mixed solvents. The content of the above-mentioned solvent varies depending on the use of the above-mentioned composition, etc., and may be 1 to 99 parts by mass in 100 parts by mass of the composition, preferably 10 to 70 parts by mass the following. The reason for this is that it is easy to make one excellent in applicability and the like.

(c) Chain transfer agent and sensitizer As the above-mentioned chain transfer agent and sensitizer, which can adjust the sensitivity of the composition, etc., a sulfur atom-containing compound 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)aminoformyl]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 , 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, mercaptoacetic acid, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate) and other mercapto compounds, will Disulfide compounds obtained by oxidation of the mercapto compound, iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2-iodoethanesulfonic acid, 3-iodopropanesulfonic acid and other iodide alkyl compounds, trimethylolpropane (3-mercaptoisobutyrate), butanediol bis(3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4-dimethylmercaptobenzene, butanediol dithio Propionate, Butylene Glycol Dithioglycolate, Ethylene Glycol Bisthioglycolate, Trimethylolpropane Trithioglycolate, Butylene Glycol Dithiopropionate, Trimethylol Propane trithiopropionate, trimethylolpropane trithioglycolate, pentaerythritol tetrathiopropionate, pentaerythritol tetrathioglycolate, trihydroxyethyl trithiopropionate, the following compounds No. C1, aliphatic polyfunctional thiol compounds such as trimercaptopropionic acid tris(2-hydroxyethyl)isocyanurate, Karenz MT BD1, PE1, NR ¹ manufactured by Showa Denko Co., Ltd., etc.

[chem 29]

(d) Surfactant As the above-mentioned surfactants, those that can improve the dispersion stability and coating properties of the composition can be used, and can be used: fluorosurfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates; higher fatty acid bases Anionic surfactants such as metal salts, alkyl sulfonates, and alkyl sulfates; cationic surfactants such as advanced amine halide salts and quaternary ammonium salts; polyethylene glycol alkyl ethers, polyethylene glycol fats Non-ionic surfactants such as acid esters, sorbitan fatty acid esters, and fatty acid monoglycerides; amphoteric surfactants; and polysiloxane-based surfactants, etc. can be used in combination.

(e) Silane coupling agent As the above-mentioned silane coupling agent, it is a silane compound that has a reactive group that chemically bonds with inorganic materials such as glass and a reactive group that chemically bonds with organic materials such as synthetic resins, and can be used to improve the adhesion of the composition or its cured product, etc. By. As the silane coupling agent, for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, silanes having isocyanate groups, methacryl groups, and epoxy groups such as KBE-9007, KBM-502, and KBE-403 can be used suitably. Coupler.

(f) Melamine compound As the above-mentioned melamine compound, those capable of improving curability can be used, for example, (poly)methylolmelamine, (poly)methylol glycoluril, (poly)methylolbenzoguanamine, Compounds in which all or part (at least 2) of active methylol groups (CH ₂ OH groups) in nitrogen compounds such as (poly)methylol urea are etherified with alkyl groups. Here, examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, or a butyl group, and may be the same as or different from each other. In addition, the methylol group without alkyl etherification can undergo self-condensation in one molecule, and can also condense between two molecules, resulting in the formation of oligomer components. Specifically, hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril, etc. can be used. Among them, alkyl-etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferred.

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

The method for producing the above-mentioned composition may be any method as long as the above-mentioned components can be prepared in a desired content, and may be a method of adding and mixing the above-mentioned components at the same time, or a method of mixing the components while sequentially adding them. .

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, PC (Personal Computer, personal computer) monitors Color filters in liquid crystal display panels for color displays such as devices, portable information terminals, digital cameras, etc.; color filters in CCD (Charge Coupled Device, Charge Coupled Device) image sensors; photosensitive spacers, black columns Shape spacer; Electrode material for plasma display panel; Touch panel; Touch sensor; Powder coating; Printing ink; Printing plate; Adhesive agent; Dental composition; Optical shaping resin; Gel coating ; photoresists for electronic engineering; electroplating resists; etching resists; both liquid and dry films; soldering resists; used in the manufacture of color filters or plasma display panels for various display purposes, electrical Resists used to form structures in the manufacturing steps of light-emitting display devices and LCDs (liquid crystal displays); compositions used to encapsulate electrical and electronic parts; solder resists; magnetic recording materials; micromechanical parts; Waveguides; Optical switches; Masks for plating; Etching masks; Color testing systems; Coating of glass fiber cables; Stencils for screen printing; Materials for the manufacture of three-dimensional objects by stereolithography; Materials for holographic recording; Image recording materials; microelectronic circuits; decolorizing materials; decolorizing materials for image recording materials; decolorizing materials for image recording materials using microcapsules; photoresist materials for printed wiring boards; UV (Ultra Violet, ultraviolet rays) and photoresist materials for visible laser direct imaging systems; photoresist materials used to form dielectric layers in layer-by-layer build-up of printed circuit boards; photoresist materials or protective films for 3D mounting, etc. special restrictions. In addition, the above-mentioned use is not limited to the use requiring durability against ultraviolet rays, such as when used as a product, and can also be suitably used for members that are exposed to ultraviolet rays during the manufacturing process, for example. Examples of members that are irradiated with ultraviolet rays during the production process include members that are irradiated with ultraviolet rays or the like in order to improve surface wettability, improve adhesion, or the like. Examples of members requiring improved wettability, improved adhesion, etc., include members laminated with other members, for example, various image displays, Color filter, photosensitive spacer, brightness enhancement plate, light guide plate, TFT (thin-film transistor, thin film transistor) substrate, alignment film, liquid crystal layer, etc. Components that require surface modification or anti-deterioration of components during the manufacturing process, such as audio components such as insulating films and speakers, lenses for photography, keyboards, and magnetic heads for HDD (hard disk drive). As members requiring surface modification or deterioration prevention of members in the above-mentioned manufacturing process, members laminated with other members through an adhesive, members covered with other members by paint, etc., for example, automobiles and aircrafts Components for various purposes such as transportation machines such as interior and exterior components, home appliances such as refrigerators and washing machines, and housing building materials. In addition, after forming a pattern-shaped member on the base material, in order to modify the surface of the exposed base material, etc., the base material and the above-mentioned member may be irradiated with ultraviolet light or the like. As the above-mentioned use, it can also be preferably used in a member used together with a member requiring surface modification or the like in such a manufacturing process. As the above-mentioned uses, for example, it can be used together with plastic film or glass, silicon wafer, various engineering plastics, optical lenses, metal surfaces, plating, ceramics, molds and other components that require surface cleaning or surface modification. member.

D. hardening Next, the cured product of the present invention will be described. The cured product of the present invention is a cured product of a composition containing the compound I-1 of the present invention and a polymerizable compound.

The composition of the present invention has a good ultraviolet absorbing function and the like due to the use of the above-mentioned composition.

The cured product of the present invention uses the above-mentioned composition. Hereinafter, the cured product of the present invention will be described in detail.

The above-mentioned composition contains the above-mentioned compound I-1 and a polymerizable compound. In addition, the above-mentioned composition may contain components other than the above-mentioned compound I-1 and the polymerizable compound. The content of each component of such a composition can be set to be the same as the content described in the item "2. Other components" of the above-mentioned "C. Composition".

The above compound I-1 contained in the above composition may be before or after detachment of the photodetachment group B in the cured product, preferably after detachment. The reason for this is that the cured product has an excellent ultraviolet absorbing function.

The above cured product usually contains a polymer of a polymerizable compound. The remaining amount of the polymerizable compound contained in the cured product can be appropriately set according to the use of the cured product, for example, 10 parts by mass or less, preferably 1 part by mass or less, per 100 parts by mass of the cured product.

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

The modulus of elasticity of the above-mentioned cured product is usually higher than that of the above-mentioned composition, for example, it may be set to 10 ^-3 M or more, and may be set to 10 MPa or more. The reason for this is that the cured product can stably hold Compound I-1 and the like by having the above elastic modulus. The upper limit of the elastic modulus can be appropriately set according to the application of the cured product, for example, it can be set to 10 ⁶ MPa or less. In addition, below, an elastic modulus means a compression elastic modulus, It can measure at 23 degreeC in accordance with JISK7181. As for the measurement sample, for example, a cube test piece with a side length of 6 mm can be made or cut out, and it can be measured at a test speed of 1±0.2 mm/min in accordance with JIS K7181.

The method for producing the cured product may be any method as long as it can cure the above-mentioned composition. For example, it may be the same as the method described in "F. Method for producing a cured product" described below.

Regarding the application and the like of the above-mentioned cured product, it can be set to be the same as that described in the item "C. Composition" above.

E. Composition Next, the second composition of the present invention will be described. The second composition of the present invention is characterized in that it contains a compound represented by the following general formula (I-2) (hereinafter sometimes referred to as "compound I-2") and a detachment product derived from a photodetachment group (hereinafter sometimes referred to as "Compound B'").

[chem 30]

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

According to the present invention, the above-mentioned second composition can be easily formed using the above-mentioned composition, for example. In addition, the above-mentioned second composition can easily impart an ultraviolet absorbing function and the like.

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 one exhibiting an ultraviolet absorbing function. The above-mentioned compound I-2 is one in which the above-mentioned B-O- in the above-mentioned compound I-1 is substituted with an -OH group. The content of this compound I-1 can be assumed to be the same as the content described in the above-mentioned item "A. Compound", so the description is omitted here.

As the content of the above-mentioned compound I-2 in the composition, as long as it can impart the desired ultraviolet absorbing function, etc., for example, the total of compound I-2 and compound B' can be set as the item of the above-mentioned "C. Composition" The content in the solid content of the above-mentioned compound I-1 is the same.

2. Compound B' The above-mentioned compound B' is a detachment product derived from a photodetachment group. Also, the photodetachable group may be the same as that described in "1. Photodetachable group B" of the above "A. Compound" as long as it is a group that can be bonded to a phenolic hydroxyl group as a protecting group. As such a compound B', what is necessary is just to use after detaching|eliminating the said photodegradation group from a phenolic hydroxyl group. Furthermore, the photodetachable group B detached from the phenolic hydroxyl group generally has high reactivity, and various structures can be adopted. As the above-mentioned compound B', the photodetachment group B is the above-mentioned general formula (B-1-a), (B-2), (B-3), (B-4), (B-5), (B- 6), (B-7), etc., may contain the following general formulas (B-111-a), (B-112), (B-113), (B-114), Compounds represented by (B-115), (B-116), (B-117), etc.

[chem 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. Compounds" above, so descriptions are omitted here.

The type of the above-mentioned compound B' may be only one type, or may be a combination of two or more types.

3. Other The above-mentioned second composition contains compound I-2 and compound B', and usually contains other components. Examples of such other components include those described in the item "2. Other components" of the above-mentioned "C. Composition", and the like. Among the above-mentioned other components, it is preferable to contain a resin component, and it is particularly preferable to be a polymer without a polymerizable group, such as a polymer containing a polymerizable compound. This is because, for example, the second composition can effectively exhibit the effect of easily imparting an ultraviolet absorbing function to a cured product or the like. In addition, only 1 type may be sufficient as the kind of resin component, and 2 or more types may be used in combination.

The above-mentioned second composition contains a solvent, a polymerizable compound, etc., and may have coating properties. In this case, the viscosity may be the same as that described in the above "C. Composition". In addition, when the above-mentioned second composition is a cured product of a polymer containing a polymerizable compound, the modulus of elasticity of the above-mentioned second composition can be the same as that described in the item "D. Cured product" above. The content is the same.

Regarding the application and the like of the above-mentioned second composition, it can be set to be the same as the content described in the item "D. Hardened product" above.

F. Manufacturing method of hardened product Next, the manufacturing method of the cured product of this invention is demonstrated. The method for producing a cured product of the present invention includes: curing the above-mentioned composition comprising compound I-1 and a polymerizable compound to form a cured product; Steps to escape.

According to the present invention, the above-mentioned production method can be easily cured by using the above-mentioned composition and having the above-mentioned steps, and can also easily impart an ultraviolet absorbing function and the like.

The manufacturing method of the present invention includes a step of forming a cured product and a step of detaching. Hereinafter, each step of the production method of the present invention will be described in detail.

1. The step of forming a hardened product The above step of forming a cured product is a step of forming a cured product of the above composition.

The method for forming the cured product of the composition in this step may be any method as long as it can form a cured product with a desired hardness, and it varies depending on the components contained in the composition. As the curing method, for example, when the composition contains a photopolymerization initiator as a polymerization initiator together with a polymerizable compound, a method of irradiating the composition with light to polymerize the polymerizable compounds can be used. As the light to irradiate the composition, it can be set to include light with a wavelength of 300 nm to 450 nm. Examples of the light source for the above-mentioned light irradiation include ultrahigh pressure mercury, mercury vapor arc, carbon arc, xenon arc, and the like. As the light to be irradiated, laser light can be used. As the laser light, those including light with a wavelength of 340 to 430 nm can be used. As the light source of laser light, argon ion laser, helium-neon laser, YAG (Yttrium Aluminum Garnet, yttrium aluminum garnet) laser, semiconductor laser, etc. that emit light from visible light to infrared region can also be used. Furthermore, when such lasers are used, the composition may contain a sensitizing pigment that absorbs the region from visible light to infrared light.

The total light quantity of the above-mentioned irradiated light is preferably one that can suppress the detachment of the photodetachment group B, for example, it may be set to less than 1000 mJ/cm ² , may be set to 800 mJ/cm ² or less, may be set to 500 mJ/cm 2 ^cm2 or less.

As the curing method, for example, when the composition contains a polymerizable compound together with a thermal polymerization initiator as a polymerization initiator, a method of heat-treating the composition to polymerize the polymerizable compounds can be used. As a heating temperature, what is necessary is just to make the said composition harden|cure stably, It can be 60 degreeC or more, Preferably it can be 100 degreeC or more and 300 degreeC or less. Furthermore, the heating temperature may be set to the temperature of the coating film surface of the composition. As heating time, about 10 seconds to 3 hours can be performed.

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

The composition used in this step contains the above-mentioned compound I-1 and a polymerizable compound. In addition, the above-mentioned composition may contain other components other than the above-mentioned compound I-1 and the polymerizable compound. The content of each component of this composition can be set to be the same as the content described in the item "2. Other components" of the above-mentioned "C. Composition", so the description is omitted here.

2. Steps to escape The above-mentioned detachment step is a step of detachment of the photo-detachment group B contained in the above-mentioned compound I-1. As a method for detaching the photo-detachable group B contained in the compound I-1, a method of irradiating the above-mentioned cured product with light may be used. The light to be irradiated on the cured product and the total amount of light are not particularly limited as long as the photodetachable group B can be desorbed, and it can be used as described in the item "1. Photodetachable group B" of the above "A. Compound". The content is the same. In addition, as a light source for light irradiation, it can select suitably according to the wavelength of the light irradiated, For example, it can be set as the content described in the said item "1. Step of forming hardened|cured material".

The temperature of the cured product in this step can be appropriately set according to the heat resistance of the cured product or the substrate supporting the cured product. For example, it can be set to 200°C or lower, preferably 0°C or higher and 150°C or lower. Among them, Preferably, it is 0°C or more and 100°C or less. The reason is that detachment of the photodetachable group B becomes easy when the said temperature is the said range. The reason for this is that, as a result, for example, damage to surrounding members such as the cured product and the base material due to heating can be reduced. Furthermore, the above-mentioned temperature of the cured product is the temperature of the surface of the cured product.

3. Other steps The above-mentioned manufacturing method includes the steps of forming a cured product and the step of detaching, and may also include other steps as necessary. As said other process, the process of apply|coating the said composition to a base material etc. are mentioned, for example. As a method for coating the composition, known methods such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, and dipping can be used. As the above-mentioned base material, it can be appropriately set according to the use of the cured product, etc., and examples include those containing soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, and the like. In addition, after the above-mentioned cured product is formed on the base material, it can be peeled from the base material and used, and can also be used by transferring from the base material to another adherend.

4. Other Regarding the cured product produced by the above-mentioned production method, its application, etc., it can be set to be the same as that described in the item "D. Hardened product" above.

The present invention is not limited to the above-mentioned embodiments. The above-mentioned embodiments are examples, and those having substantially the same configuration as the technical idea described in the present invention and exerting the same effects are included in the technical scope of the present invention. Example

Hereinafter, although an Example etc. are given and this invention is demonstrated in detail, this invention is not limited to these Examples.

[Example 1] Mix 0.005 mol of the phenolic compound (compound I-2) in the following scheme 1, 0.005 mol of potassium carbonate and 12 g of DMF (dimethylformamide, dimethylformamide), and add dropwise at room temperature under a nitrogen atmosphere 0.0075 mol of o-nitrobenzyl chloride was stirred at 80° C. for 2 hours, and Compound I-1-2 corresponding to 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 for oil-water separation. 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 confirmed as the target substance by H-NMR (nuclear magnetic resonance, nuclear magnetic resonance) and IR (infrared ray, infrared).

[chem 32]

[Embodiments 2-7] Except for changing o-nitrobenzyl chloride, the following compounds I-1-3, I-1-40, I-1-32, I-1-35, I-1- 28. I-1-34. Specifically, compounds I-1-3, I-1-40, I-1-32, I-1-35, I-1-28, and 1- 34. In addition, it was confirmed by H-NMR that the white solid obtained in Examples 2 to 7 was the target substance. [Example 2] Use 1.1 equivalent of N-bromobutanediimide and 0.01 equivalent of AIBN (azobisisobutyronitrile, azobisisobutyronitrile) relative to 2-ethylnitrobenzene, heat and stir at 90°C in chlorobenzene solvent 4 hours. Separation of oil and water with ethyl acetate, washing with water, and refining with 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 this benzyl bromide compound was used instead of o-nitrobenzyl chloride. The obtained white solid was confirmed as the target substance by H-NMR. [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 as the target substance by H-NMR. [Example 4] Compound I-1-32 was obtained in the same manner as in Example 1 except that 4′-methoxyphenacyl bromide was used instead of o-nitrobenzyl chloride. The obtained white solid was confirmed as the target substance by H-NMR. [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 as the target substance by H-NMR. [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 as the target substance by H-NMR. [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 as the target substance by H-NMR.

[chem 33]

[Example 8] Using 1.1 equivalent of N-bromobutanediimide and 0.01 equivalent of AIBN with respect to 4-methoxy-2-nitrotoluene, heated and stirred at 90° C. for 4 hours in a chlorobenzene solvent. Separation of oil and water by ethyl acetate, washing with water and purification by a silica column to obtain the corresponding benzyl bromide compound. Compound I-1-4 was obtained in the same manner as in Example 1 except that this benzyl bromide compound was used instead of o-nitrobenzyl chloride. The obtained white solid was confirmed as the target substance by H-NMR. [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 as the target substance by H-NMR. [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 as the target substance by H-NMR. [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 as the target substance by H-NMR. [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 as the target substance by H-NMR.

[Example 13] An intermediate compound was obtained in the same manner as in Example 1 except that 4-(2-bromoacetyl)phenyl carbonate tert-butyl 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 4 M HCl ethyl acetate solution was added, and heated and stirred at 50° C. for 10 hours. The solvent of the reaction solution was distilled off, and the target compound (compound I-1-45) was obtained by isolation through a silica column (ethyl acetate:hexane=1:2). It was confirmed by H-NMR that the obtained white solid was the target object. [Example 14] Dissolve 0.004 mol of the phenolic compound (the phenolic compound in Scheme 1) in 40 mL of pyridine, add dropwise 0.006 mol of NPPOC-Cl (2-(2-nitrophenyl)propyl chloroformate), and stir at room temperature for 6 Hour. 200 g of ethyl acetate and 50 g of ion-exchanged water were added to the reaction solution for oil-water separation. 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 by silica column (ethyl acetate: hexane = 1:4). Separated. After dispersing the obtained white solid with hexane, it dried under reduced pressure at 45 degreeC for 2 hours, and obtained the target object (compound I-1-46). It was confirmed by H-NMR that the obtained white solid was the target object. [Examples 15-17] 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 formulas (1) to (3) were used as the phenolic compound .

[chem 34]

[chem 35]

[Table 1] H-NMR Chemical shift ppm (multiplicity, number of protons) Embodiment 1 (compound 1-1-2) 8.14 (d, 1H), 8.06 (d, 1H), 8.00 (d, 1H), 7.78 (d, 1H), 7.76 (s, 1H), 7.52-7.45 (m, 4H), 7.40 (t, 1H) , 7.17 (d, 1H), 5.58 (s, 2H), 1.78 (s, 2H), 1.42 (s, 6H), 0.77 (s, 9H) Embodiment 2 (compound 1-1-3) 8.01-7.95 (m, 2H), 7.93 (d, 1H), 7.67 (d, 1H), 7.60 (s, 1H), 7.49-7.45 (m, 3H), 7.37-7.33 (m, 2H), 6.85 ( d, 1H), 6.07 (dd, 1H), 1.70 (s, 2H), 1.58 (s, 3H), 1.34 (s, 6H), 0.70 (s, 9H) Embodiment 3 (compound 1-1-40) 8.11 (d, 1H), 8.05-8.03 (m, 2H), 7.86 (s, 1H), 7.45 (dd, 1H), 7.25 (m, 1H), 7.37 (dd, 1H), 5.56 (s, 2H) , 1.79 (s, 2H), 1.44 (s, 6H), 0.78 (s, 9H) Embodiment 4 (compound 1-1-32) 7.95 (dd, 2H), 7.83 (d, 2H), 7.66 (s, 1H), 7.46-7.41 (m, 3H), 7.03 (d, 1H), 6.73 (d, 2H), 5.19 (s, 2H) , 3.80 (s, 3H), 1.74 (s, 2H), 1.38 (s, 6H), 0.76 (s, 9H) Embodiment 5 (compound 1-1-35) 7.88-7.84 (m, 4H), 7.70 (d, 1H), 7.48 (d, 2H), 7.40 (m, 2H), 7.37-7.32 (m, 2H), 7.28-7.22 (m, 3H), 7.13 ( t, 2H), 6.96 (d, 1H), 1.74 (s, 2H), 1.36 (s, 6H), 0.72 (s, 9H) Embodiment 6 (compound 1-1-28) 7.86-7.83 (m, 2H), 7.71-7.08 (m, 6H), 7.21-7.08 (m, 2H), 6.98 (d, 1H), 4.94 (s, 2H), 1.71 (s, 2H), 1.35 ( s, 6H), 0.73 (s, 9H) Embodiment 7 (compound 1-1-34) 7.96 (dd, 2H), 7.52 (s, 1H), 7.50 (dd, 1H), 7.44 (dd, 2H), 7.35 (d, 1H), 7.14 (d, 1H), 6.78 (d, 1H), 6.69 (dd, 1H), 6.45 (s, 1H), 5.23 (s, 2H), 3.84 (s, 3H), 1.78 (s, 2H), 1.42 (s, 6H), 0.77 (s, 9H)

[Table 2] H-NMR Chemical shift ppm (multiplicity, number of protons) Embodiment 8 (compound 1-1-4) 8.16 (d, 1H), 7.98 (dd, 2H), 7.71 (s, 1H), 7.55 (dd, 2H), 7.24 (d, 1H), 7.14 (s, 1H), 6.80 (d, 1H), 5.59 (s, 2H), 3.42 (s, 3H), 1.78 (s, 2H), 1.42 (s, 6H), 0.79 (s, 9H) Embodiment 9 (compound 1-1-41) 8.00 (dd, 2H), 7.74 (d, 1H), 7.53-7.41 (m, 5H), 7.34 (t, 1H), 7.06 (d, 1H), 5.16 (s, 2H), 1.76 (s, 2H) , 1.40 (s, 6H), 0.76 (s, 9H) Embodiment 10 (Compound I-1-42) 8.00 (dd, 2H), 7.71 (d, 1H), 7.48-7.44 (m, 3H), 7.30 (t, 1H), 7.11 (d, 1H), 7.04 (d, 1H), 6.93 (d, 1H) , 5.16 (s, 2H), 3.88 (s, 3H), 1.75 (s, 2H), 1.39 (s, 6H), 0.76 (s, 9H) Embodiment 11 (compound 1-1-43) 7.98 (dd, 2H), 7.68 (d, 1H), 7.53-7.48 (m, 2H), 7.41 (dd, 2H), 7.22 (d, 1H), 6.84 (d, 1H), 5.21 (s, 2H) , 3.82 (s, 3H), 1.76 (s, 2H), 1.40 (s, 6H), 0.77 (s, 9H) Embodiment 12 (compound 1-1-44) 7.93 (dd, 2H), 7.66 (d, 1H), 7.47-7.41 (m, 4H), 7.21 (t, 1H), 7.10 (d, 1H), 7.08-6.98 (m, 2H), 5.13 (s, 2H), 2.38 (s, 3H), 1.74 (s, 2H), 1.38, 6H), 0.75 (s, 9H) Embodiment 13 (compound 1-1-45) 7.96 (dd, 2H), 7.73 (d, 2H), 7.67 (s, 1H), 7.64-7.43 (m, 3H), 7.01 (d, 1H), 6.66 (d, 2H), 5.16 (s, 2H) , 1.74 (s, 2H), 1.37 (s, 6H), 0.75 (s, 9H) Embodiment 14 (Compound I-1-46) 8.14 (s, 1H), 7.88 (dd, 2H), 7.77 (d, 1H), 7.53-7.41 (m, 5H), 7.35 (t, 1H), 7.27 (d, 1H), 4.45-4.40 (m, 2H), 3.76 (q, 1H), 1.82 (s, 2H), 1.46 (s, 6H), 1.40 (d, 3H), 0.78 (s, 9H) Embodiment 15 (compound 1-1-8) 7.94 (d, 2H), 7.79 (dd, 4H), 7.67 (s, 2H), 7.57 (d, 2H), 7.41-7.33 (m, 8H), 7.25 (t, 2H), 5.14 (s, 4H) , 4.33 (s, 2H), 1.75 (s, 4H), 1.37 (s, 12H), 0.78 (s, 18H) Embodiment 16 (compound 1-1-47) 8.69 (d, 4H), 8.28 (d, 1H), 8.26 (d, 1H), 8.14 (d, 1H), 7.60 (t, 2H), 7.51 (t, 4H), 7.34 (t, 1H), 7.08 (t, 1H), 6.80 (s, 1H), 6.75 (d, 1H), 5.63 (s, 2H), 4.52 (t, 2H), 4.30 (t, 2H), 2.39-2.34 (m, 1H), 1.68-1.48 (m, 4H), 1.32-1.26 (m, 4H), 0.92 (t, 3H), 0.88 (t, 3H)

[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) in 0.01 mass % acetonitrile solution, added to 1 cm cristobalite in the slot. An ultra-high pressure mercury lamp UL750 (manufactured by HOYA) was adjusted to 20 mW/cm ² , and 100 mJ/cm ² , 3000 mJ/cm ² , and 10000 mJ/cm ² were irradiated to the quartz cell filled with the solution. The solution after irradiation was analyzed by high-performance liquid chromatography (HPLC), and the release rate was calculated from the following formula. The results are shown in Table 3 below. In addition, in the analysis by HPLC, when the 230 nm peak originating in compound I-1 disappeared completely, it calculated assuming that it was 100% detached. Detachment rate (%) = phenolic compound (compound I-2) / phenolic compound (compound I-2 + compound I-1) × 100

Also, 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 cm ² ) Confirm the absorption spectrum of light having a wavelength of 250 nm to 450 nm. As a result, it was confirmed that light on the longer wavelength side was widely absorbed in the wavelength range of 250 nm to 450 nm after light irradiation compared with before light irradiation. In addition, the measurement results of the maximum absorption wavelength (nm) are shown in Tables 3 and 4 below.

[table 3] Embodiment 1 (compound 1-1-2) Embodiment 2 (compound 1-1-3) Embodiment 7 (compound 1-1-34) Disengagement rate (%) 100 mJ/ ^cm2 10.3 13.9 1.2 3000 mJ/ ^cm2 87.9 92.6 58.1 10000 mJ/ ^cm2 99.7 100.0 100.0 Maximum absorption wavelength (nm) Before light irradiation (0 mJ/cm ² ) 286 286 289 After light irradiation (10000 mJ/cm ² ) 338 338 338

[Table 4] Embodiment 5 (compound 1-1-35) Embodiment 6 (compound 1-1-28) Embodiment 8 (compound 1-1-4) Embodiment 9 (compound 1-1-41) Disengagement rate (%) 100 mJ/ ^cm2 0.6 0.8 1.2 11.1 3000 mJ/ ^cm2 12.8 9.3 39.2 85.6 10000 mJ/ ^cm2 64.0 30.9 76.3 98.4 Embodiment 12 (compound 1-1-44) Embodiment 13 (compound 1-1-45) Embodiment 14 (Compound I-1-46) Embodiment 16 (compound 1-1-47) Disengagement rate (%) 100 mJ/ ^cm2 0.1 0.3 17.2 14.7 3000 mJ/ ^cm2 3.4 3.7 97.6 97.6 10000 mJ/ ^cm2 16.3 8.0 100 100

From Tables 3 and 4, it was confirmed that the photodetachment group B desorbed from the compound I-1 by light irradiation. Also, from Table 3, it was confirmed that the above-mentioned compound I-1 can efficiently absorb ultraviolet rays having wavelengths ranging from 250 nm to 450 nm in a wide range when irradiated with light. Also, along with this, a shift of the maximum absorption wavelength to the longer wavelength side was confirmed. From the above, it was confirmed that the phenolic hydroxyl group of compound I-1 was protected by the photodetachable group B before light irradiation, and the ultraviolet absorption function was inhibited, and the inhibition of hardening was suppressed, and the ultraviolet absorption function could be easily imparted by light irradiation.

The components shown in Table 5 were mixed at the ratio shown in Table 5 below to obtain the compositions of Examples 18-20 and Comparative Examples 1 and 2. The symbols in Table 5 represent the following compounds. In addition, the numerical value in a table shows a mass part.

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

[chem 36]

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

[Hardness] The compositions of Examples 18-20 and Comparative Examples 1 and 2 were coated on PET (polyethylene terephthalate, polyethylene terephthalate) with a thickness of about 3 μm by a bar coater membrane. Then, after prebaking at 80° C. for 3 minutes, exposure (20 mW/cm ² ) was performed using an ultra-high pressure mercury lamp (UL750) as a light source. In addition, exposure was performed so that the exposure light quantity might become 500 mJ/cm ^<2> . At this time, in order to measure the light sensitivity, a film made in such a way that the light transmittance decreases step by step (a stepped exposure meter with an optical density of 0.05 as the first step and an optical density increase of 0.15 per step) was used. Then, using isopropyl alcohol (IPA), after cleaning and developing for 10 seconds at 25° C., it was dried at 80° C. for 30 minutes. Then, the number of stages of the step exposure meter of the cured product formed on the PET film was measured to evaluate the photosensitivity. The higher the number of stages of the stage exposure meter, the higher the light sensitivity and the better the hardening property. The results are shown in Table 5 below.

[Light resistance] The compositions of Examples 18-20 and Comparative Examples 1 and 2 were respectively coated on glass substrates by a spin coater, pre-baked at 80°C for 3 minutes, and then used an ultra-high pressure mercury lamp (UL750) Exposure was performed as a light source (20 mW/cm ² ). Exposure was performed so that the amount of exposure light became 100 mJ/cm ² . Thereafter, 3000 mJ/cm ² was further irradiated to prepare a sample for light resistance evaluation. A 24-hour light resistance test was implemented on the sample for evaluation using a xenon light resistance tester Table Sun XT-1500L manufactured by Suga Test Instruments. Measure the difference in transmittance (%) at a wavelength of 470 nm of the sample for evaluation before and after the light resistance test ((transmittance before the light resistance test (%) - transmittance after the light resistance test (%)), according to the following The light resistance was evaluated based on the standard. 〇: Transmittance difference (%) is less than 5% relative to the transmittance before the light resistance test. ×: The transmittance difference (%) is more than 5% relative to the transmittance before the light resistance test. When the light resistance evaluation is "O", it means that the light resistance of the cured product is excellent. The results are shown in Table 5 below.

[table 5] Example 18 Example 19 Example 20 Comparative example 1 Comparative example 2 A-1 50 50 50 50 50 A-2 50 50 50 50 50 B-1 5 5 5 5 5 C-1 1 1 1 1 1 D-1 50 50 50 50 50 E-1 5 F-1 5 F-2 5 F-3 5 sclerosis 16 17 16 17 12 Lightfastness 〇 〇 〇 x 〇

According to Table 5, the composition of Examples 18 to 20 containing Compound I-1 has better light resistance than the composition of Comparative Example 1 containing no ultraviolet absorber. Also, 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 seen that according to the present invention, a composition having less hindrance to hardening and excellent light resistance can be obtained. Industrial availability

According to the compound of the present invention, it is possible to provide a compound that has less hindrance to curing and can easily impart an ultraviolet absorbing function to a cured product. The latent ultraviolet absorber of the present invention has less hindrance to hardening, and can easily impart ultraviolet absorbing functions to cured products. According to the composition of the present invention, it is possible to provide a composition that has less hindrance to curing and can obtain a cured product having an excellent ultraviolet absorbing function. According to the cured product of the present invention, a cured product having an excellent ultraviolet absorbing function can be provided. By the method for producing a cured product of the present invention, a cured product having an excellent ultraviolet absorbing function and the like can be produced without causing hindrance to curing. According to the second composition of the present invention, it is possible to provide a composition capable of obtaining a cured product having an excellent ultraviolet absorbing function without causing inhibition of curing.

Claims (6)

A kind of compound, it is following formula (I-1-6), (I-1-7), (I-1-9), (I-1-10), (I-1-11), (I -1-12), (I-1-14), (I-1-15), (I-1-16), (I-1-18), (I-1-19), (I-1 -20), (I-1-21), (I-1-22), (I-1-23), (I-1-24), (I-1-26), (I-1-27 ), (I-1-36), (I-1-37), (I-1-38), (I-1-39) or (I-1-47), . A latent ultraviolet absorber, which contains the compound as claimed in claim 1. A composition containing the compound according to claim 1. The composition according to claim 3, further comprising a resin component. A cured product comprising a compound according to claim 1 and a polymerizable compound. A method of manufacturing a cured product, comprising: A step of hardening the composition containing the compound according to claim 1 and the polymerizable compound to form a hardened product; and A step of irradiating light to the above-mentioned cured product to detach the photo-detachable group contained in the above-mentioned compound.