JP2017218491A - Photopolymerization sensitizer composition and photopolymerizable composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a photopolymerization sensitizer composition that can reduce the coloring of polymers and cured products, and has high photopolymerization sensitizing effect.SOLUTION: Among anthracene compounds, a 9,10-bis(2-hydroxyalkoxy)anthracene compound having a hydroxyalkoxy group as a substituent is combined with a specific naphthalene compound or a specific benzene compound to give a high photopolymerization sensitizing effect; a photocured product of the combined compounds is a photopolymerization sensitizer composition with less coloring.SELECTED DRAWING: None

Description

The present invention relates to a photopolymerization sensitizer, and more particularly to a photopolymerization sensitizer composition in which a specific anthracene compound and a naphthalene compound or a benzene compound are combined, and a photopolymerizable composition using the same.

Energy ray curable resins are widely used in fields such as coatings, inks, and electronic materials. The energy ray curable resin is obtained by polymerizing and curing the photopolymerizable composition by irradiating the photopolymerizable composition with energy rays such as ultraviolet rays and electron beams. The technology of curing with this energy ray is, for example, wood coating materials, coating materials such as metals, screen printing and offset printing inks, dry film resists used for electronic substrates, hologram materials, sealants, overcoat materials, It is used for various applications such as resin for stereolithography and adhesives.

The photopolymerizable composition mainly comprises a photopolymerizable compound, a photopolymerization initiator that initiates polymerization of the photopolymerizable compound by energy irradiation, and in many cases, a photopolymerization enhancer that activates the photopolymerization initiator. Consists of sensitizers. Industrially, a photopolymerizable composition capable of performing photocationic polymerization, photoradical polymerization, or photohybrid polymerization using a combination thereof is often used.

The photopolymerization sensitizer used in these photopolymerizable compositions is usually used in cases where the polymerization by energy rays is insufficient with only the photopolymerization initiator, or in order to allow the polymerization to proceed more efficiently.

When the photopolymerizable composition contains a filler such as a dye, pigment, stabilizer, etc., and the absorption wavelength of the photopolymerization initiator is shielded, the absorption wavelength of the photopolymerization initiator uses the energy rays (light rays) used for polymerization. In many cases, a photopolymerization sensitizer is used when it does not match the wavelength of). In particular, in photocationic polymerization, many of the photocationic polymerization initiators have a light absorption wavelength of around 365 nm or less. For example, polymerization did not proceed sufficiently by light irradiation in a relatively long wavelength region of about 400 nm.

In such a case, polymerization can be efficiently advanced by using a photopolymerization sensitizer having light absorption on a relatively long wavelength side (in this case, around 400 nm). As such a photopolymerization sensitizer, for example, dialkoxyanthracene and thioxanthone (Patent Documents 1 to 4 and the like) are known.

However, although photopolymerization sensitizers having light absorption around 400 nm, such as dialkoxyanthracene and thioxanthone, exhibit the above sensitizing effect, they often show coloration in the cured product, and therefore, particularly for optical applications and display materials. In some cases it was difficult to use.

Moreover, the photopolymerization sensitizer composition which combined the anthracene compound, the naphthalene compound, or the benzene compound is known as a highly sensitive photopolymerization sensitizer (patent document 6). However, also in this photopolymerization sensitizer composition, when the dialkoxyanthracene used in the examples is used as an anthracene compound, the cured product is often colored, so that it is particularly suitable for optical applications and display materials. It was sometimes difficult to use.

Japanese Patent Laid-Open No. 06-059380 JP 11-279212 A JP-A-11-140110 JP 2001-106648 A JP 2007-99637 A WO2006 / 73021

  Accordingly, an object of the present invention is to provide a photopolymerization sensitizer composition having a high photopolymerization sensitization effect and having no problem of coloring of the polymer or cured product in the photopolymerizable composition.

As a result of intensive studies in view of the above circumstances, the present inventors have found that in addition to the 9,10-bis (2-hydroxyalkoxy) anthracene compound having a hydroxyalkoxy group as a substituent among the anthracene compounds, naphthalene-1,4- Specific naphthalene compounds such as diether compounds, 4-alkoxy-naphthol compounds or naphthalene-1,4-diol compounds, or specific compounds such as hydroquinone (1,4-dihydroxybenzene) and catechol (1,2-dihydroxybenzene) By using a combination of benzene compounds, a high photosensitization effect can be obtained, and a photocured product obtained by polymerizing a photopolymerizable composition containing the photopolymerization sensitizer composition is found to be less colored. Completed the invention.

That is, the gist of the present invention is the gist of the following.

(Invention 1) (A) Anthracene compound represented by general formula (1) and (B) a naphthalene compound represented by general formula (2) or a benzene compound represented by general formula (3) Photopolymerization sensitizer composition.

In the general formula (1), R ¹ is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms, an allyloxymethyl group, or an aryl group having 6 to 10 carbon atoms. And X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.

In the general formula (2), n represents an integer of 1 to 3, R ³ represents either an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted with an oxygen atom, and OR ³ represents When there are a plurality of them, these OR ^{3 s} may be the same or different, and X ² and Y ² may be the same or different, and are a hydrogen atom, a halogen atom, an alkyl having 1 to 8 carbon atoms. Represents any of a group, an aralkyl group, an alkoxy group or an aryloxy group.

In the general formula (3), R ⁴ and R ⁵ may be the same or different and each represents an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted with an oxygen atom, X ³ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aralkyl group, an alkoxy group, or an aryloxy group.

(Invention 2) The photopolymerization sensitizer composition according to Invention 1, wherein the general formula (2) of the component (B) is a naphthalene compound represented by the following general formula (4).

In the general formula (4), R ⁶ and R ⁷ may be the same or different and each represents an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted with an oxygen atom, X ⁴ and Y ³ may be the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aralkyl group, an alkoxy group, or an aryloxy group.

(Invention 3) The photopolymerization sensitizer composition according to Invention 1, wherein the general formula (3) of the component (B) is a benzene compound represented by the following general formula (5).

In the general formula (5), R ⁸ and R ⁹ may be the same or different and each represents an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted with an oxygen atom, X ⁵ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aralkyl group, an alkoxy group or an aryloxy group.

(Invention 4) Photopolymerizability characterized by containing (C) a photopolymerization initiator and (D) a photopolymerizable compound in addition to the photopolymerization sensitizer composition according to any one of Inventions 1 to 3. Composition.

(Invention 5) The photopolymerizable composition according to Invention 4, wherein the photopolymerization initiator (C) is a photocationic polymerization initiator and the photopolymerizable compound (D) is a photocationic polymerizable compound. .

(Invention 6) The photopolymerizable composition according to Invention 4, wherein the photopolymerization initiator (C) is a photoradical polymerization initiator and the photopolymerizable compound (D) is a photoradical polymerizable compound. .

(Invention 7) The photopolymerizable composition according to Invention 4, wherein the photopolymerizable compound (D) contains both a radical photopolymerizable compound and a cationic photopolymerizable compound.

(Invention 8) A method for producing a cured product, wherein a cured product is obtained by irradiating the photopolymerizable composition according to any one of Inventions 4 to 7 with energy rays.

(Invention 9) The method for producing a cured product according to Invention 8, wherein the irradiated energy rays contain light having a wavelength range of 300 nm to 500 nm.

When the photopolymerizable composition using the photopolymerization sensitizer composition of the present invention is cured, the cured product is less colored, and the photopolymerization composition can be cured by light irradiation in a wide wavelength range. In particular, rapid curing is possible by light irradiation on the long wavelength side of 365 nm or more.

((A) component)
First, the anthracene compound represented by the following general formula (1) which is the compound (A) will be described.

In the general formula (1), R ¹ is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms, an allyloxymethyl group, or an aryl group having 6 to 10 carbon atoms. And X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.

In the general formula (1), examples of the alkyl group having 1 to 8 carbon atoms represented by R ¹ include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, Examples include t-butyl group, n-pentyl group, i-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group and the like. Examples of the alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms include a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, a butoxymethyl group, and a pentyloxymethyl group. Examples of the aryloxymethyl group having an aryl group having 6 to 10 carbon atoms include phenoxymethyl group, tolyloxymethyl group, 1-naphthyloxymethyl group, and 2-naphthyloxymethyl group.

In the general formula (1), the alkyl group having 1 to 8 carbon atoms represented by X or Y includes a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, and an i-butyl group. , T-butyl group, n-pentyl group, i-pentyl group, n-hexyl group, n-heptyl group, n-octyl group or 2-ethylhexyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

As specific examples of the anthracene compound represented by the general formula (1) of the present invention, when X and Y are hydrogen atoms, for example, 9,10-bis (2-hydroxyethoxy) anthracene, 9,10 -Bis (2-hydroxypropoxy) anthracene, 9,10-bis (2-hydroxybutoxy) anthracene, 9,10-bis (2-hydroxypentyloxy) anthracene, 9,10-bis (2-hydroxyhexyloxy) anthracene 9,10-bis (2-hydroxyheptyloxy) anthracene, 9,10-bis (2-hydroxyoctyloxy) anthracene, 9,10-bis (2-hydroxy-3-methoxypropoxy) anthracene, 9,10- Bis (2-hydroxy-3-ethoxypropoxy) anthracene, 9,10- Sus (2-hydroxy-3-propoxypropoxy) anthracene, 9,10-bis (2-hydroxy-3-butoxypropoxy) anthracene, 9,10-bis (2-hydroxy-3-pentyloxypropoxy) anthracene, 9, 10-bis (2-hydroxy-3-hexyloxypropoxy) anthracene, 9,10-bis (2-hydroxy-3-heptyloxypropoxy) anthracene, 9,10-bis (2-hydroxy-3-octyloxypropoxy) Anthracene, 9,10-bis (2-hydroxy-3-allyloxypropoxy) anthracene, 9,10-bis (2-hydroxy-3-phenoxypropoxy) anthracene, 9,10-bis [2-hydroxy-3- ( Tolyloxy) propoxy] anthracene, 9,1 - bis (2-hydroxy-3-naphthyloxy propoxy) anthracene, and the like.

When X and Y are other than a hydrogen atom, for example, 2-methyl-9,10-bis (2-hydroxyethoxy) anthracene or 2-methyl-9,10-bis, wherein X and / or Y is an alkyl group (2-hydroxypropoxy) anthracene, 2-methyl-9,10-bis (2-hydroxybutoxy) anthracene, 2-methyl-9,10-bis (2-hydroxypentyloxy) anthracene, 2-methyl-9,10 -Bis (2-hydroxyhexyloxy) anthracene, 2-methyl-9,10-bis (2-hydroxyheptyloxy) anthracene, 2-methyl-9,10-bis (2-hydroxyoctyloxy) anthracene, 2-methyl -9,10-bis (2-hydroxy-3-methoxypropoxy) anthracene, 2-methyl-9,10-bi (2-hydroxy-3-ethoxypropoxy) anthracene, 2-methyl-9,10-bis (2-hydroxy-3-propoxypropoxy) anthracene 2-methyl-, 9,10-bis (2-hydroxy-3-butoxy) Propoxy) anthracene, 2-methyl-9,10-bis (2-hydroxy-3-pentyloxypropoxy) anthracene, 2-methyl-9,10-bis (2-hydroxy-3-hexyloxypropoxy) anthracene, 2- Methyl-9,10-bis (2-hydroxy-3-heptyloxypropoxy) anthracene, 2-methyl-9,10-bis (2-hydroxy-3-octyloxypropoxy) anthracene, 2-methyl-9,10- Bis (2-hydroxy-3-allyloxypropoxy) anthracene, 2- Til-9,10-bis (2-hydroxy-3-phenoxypropoxy) anthracene, 2-methyl-9,10-bis [2-hydroxy-3- (tolyloxy) propoxy] anthracene, 2-methyl-9,10- Bis (2-hydroxy-3-naphthyloxypropoxy) anthracene and the like can be mentioned.

Furthermore, 2-ethyl-9,10-bis (2-hydroxyethoxy) anthracene, 2-ethyl-9,10-bis (2-hydroxypropoxy) anthracene, 2-ethyl-9,10-bis (2-hydroxybutoxy) ) Anthracene, 2-ethyl-9,10-bis (2-hydroxypentyloxy) anthracene, 2-ethyl-9,10-bis (2-hydroxyhexyloxy) anthracene, 2-ethyl-9,10-bis (2 -Hydroxyheptyloxy) anthracene, 2-ethyl-9,10-bis (2-hydroxyoctyloxy) anthracene, 2-ethyl-9,10-bis (2-hydroxy-3-methoxypropoxy) anthracene, 2-ethyl- 9,10-bis (2-hydroxy-3-ethoxypropoxy) anthracene, 2-ethy -9,10-bis (2-hydroxy-3-propoxypropoxy) anthracene 2-ethyl-, 9,10-bis (2-hydroxy-3-butoxypropoxy) anthracene, 2-ethyl-9,10-bis (2 -Hydroxy-3-pentyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2-hydroxy-3-hexyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2-hydroxy-3-heptyl) Oxypropoxy) anthracene, 2-ethyl-9,10-bis (2-hydroxy-3-octyloxypropoxy) anthracene, 2-ethyl-9,10-bis (2-hydroxy-3-allyloxypropoxy) anthracene, 2 -Ethyl-9,10-bis (2-hydroxy-3-phenoxypropoxy) Nthracene, 2-ethyl-9,10-bis [2-hydroxy-3- (tolyloxy) propoxy] anthracene, 2-ethyl-9,10-bis (2-hydroxy-3-naphthyloxypropoxy) anthracene, etc. .

Furthermore, 2,6-dimethyl-9,10-bis (2-hydroxyethoxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxypropoxy) anthracene, 2,6-dimethyl-9,10 -Bis (2-hydroxybutoxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxypentyloxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxyhexyloxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxyheptyloxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxyoctyloxy) anthracene, 2,6-dimethyl-9,10- Bis (2-hydroxy-3-methoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2- Droxy-3-ethoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxy-3-propoxypropoxy) anthracene, 2,6-dimethyl-, 9,10-bis (2-hydroxy-3) -Butoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxy-3-pentyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxy-3-hexyloxy) Propoxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxy-3-heptyloxypropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxy-3-octyloxypropoxy) Anthracene, 2,6-dimethyl-9,10-bis (2-hydroxy-3-allyl) Xylpropoxy) anthracene, 2,6-dimethyl-9,10-bis (2-hydroxy-3-phenoxypropoxy) anthracene, 2,6-dimethyl-9,10-bis [2-hydroxy-3- (tolyloxy) propoxy Anthracene, 2,6-dimethyl-9,10-bis (2-hydroxy-3-naphthyloxypropoxy) anthracene and the like can be mentioned.

And furthermore, 2-chloro-9,10-bis (2-hydroxyethoxy) anthracene, 2-chloro-9,10-bis (2-hydroxypropoxy) anthracene, wherein X and / or Y is a halogen atom, 2- Chloro-9,10-bis (2-hydroxybutoxy) anthracene, 2-chloro-9,10-bis (2-hydroxypentyloxy) anthracene, 2-chloro-9,10-bis (2-hydroxyhexyloxy) anthracene 2-chloro-9,10-bis (2-hydroxyheptyloxy) anthracene, 2-chloro-9,10-bis (2-hydroxyoctyloxy) anthracene, 2-chloro-9,10-bis (2-hydroxy) -3-Methoxypropoxy) anthracene, 2-chloro-9,10-bis (2-hydroxy-3) Ethoxypropoxy) anthracene, 2-chloro-9,10-bis (2-hydroxy-3-propoxypropoxy) anthracene 2-chloro-, 9,10-bis (2-hydroxy-3-butoxypropoxy) anthracene, 2-chloro -9,10-bis (2-hydroxy-3-pentyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-hydroxy-3-hexyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-hydroxy-3-heptyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-hydroxy-3-octyloxypropoxy) anthracene, 2-chloro-9,10-bis (2-hydroxy-3) -Allyloxypropoxy) anthracene, 2-chloro-9,10-bis 2-hydroxy-3-phenoxypropoxy) anthracene, 2-chloro-9,10-bis [2-hydroxy-3- (tolyloxy) propoxy] anthracene, 2-chloro-9,10-bis (2-hydroxy-3-) Naphthyloxypropoxy) anthracene and the like.

And also 2-bromo-9,10-bis (2-hydroxyethoxy) anthracene, 2-bromo-9,10-bis (2-hydroxypropoxy) anthracene, 2-bromo-9,10-bis (2-hydroxy) Butoxy) anthracene, 2-bromo-9,10-bis (2-hydroxypentyloxy) anthracene, 2-bromo-9,10-bis (2-hydroxyhexyloxy) anthracene, 2-bromo-9,10-bis ( 2-hydroxyheptyloxy) anthracene, 2-bromo-9,10-bis (2-hydroxyoctyloxy) anthracene, 2-bromo-9,10-bis (2-hydroxy-3-methoxypropoxy) anthracene, 2-bromo -9,10-bis (2-hydroxy-3-ethoxypropoxy) anthracene, 2 Bromo-9,10-bis (2-hydroxy-3-propoxypropoxy) anthracene 2-bromo-, 9,10-bis (2-hydroxy-3-butoxypropoxy) anthracene, 2-bromo-9,10-bis ( 2-hydroxy-3-pentyloxypropoxy) anthracene, 2-bromo-9,10-bis (2-hydroxy-3-hexyloxypropoxy) anthracene, 2-bromo-9,10-bis (2-hydroxy-3-) Heptyloxypropoxy) anthracene, 2-bromo-9,10-bis (2-hydroxy-3-octyloxypropoxy) anthracene, 2-butyl-9,10-bis (2-hydroxy-3-allyloxypropoxy) anthracene, 2-Bromo-9,10-bis (2-hydroxy-3-phenoxypropo C) Anthracene, 2-bromo-9,10-bis [2-hydroxy-3- (tolyloxy) propoxy] anthracene, 2-bromo-9,10-bis (2-hydroxy-3-naphthyloxypropoxy) anthracene, etc. Can be mentioned.

Among these exemplified compounds, 9,10-bis (2-hydroxypropoxy) anthracene (compound A-1) shown below in that the production is easy and the effect as a photopolymerization sensitizer is large. 9,10-bis (2-hydroxy-3-butoxypropoxy) anthracene (Compound A-2) and 9,10-bis (2-hydroxy-3-allyloxypropoxy) anthracene (Compound A-3) are preferred.

The anthracene compound represented by the general formula (1) of the present invention can be synthesized by reducing the corresponding 9,10-anthraquinone compound and then reacting it with a hydroxy etherifying agent.

The anthracene compound represented by the general formula (1) of the present invention has not only a high effect as a photopolymerization sensitizer in a photopolymerization reaction, but also a 9,10-bis (2-hydroxyalkoxy) anthracene compound. When a film is put on a photopolymerizable composition containing a photopolymerization sensitizer as a photopolymerization sensitizer, it is also a useful compound that has extremely low migration property to a coating film. Due to this effect, for example, when using a photopolymerization sensitizer composition containing these photopolymerization sensitizers as a component of a photoadhesive for adhering the films, the photopolymerization sensitizer is placed on top. It has a useful property that it can be prevented from migrating to a thick film (migration) and hardly causes problems of powdering and coloring of the photopolymerization sensitizer on the upper film.

((B) component)
Next, the naphthalene compound represented by the general formula (2) or the benzene compound represented by the general formula (3) which is a compound of the component (B) will be described.

In the general formula (2), n represents an integer of 1 to 3, R ³ represents either an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted with an oxygen atom, and OR ³ represents When there are a plurality of them, these OR ^{3 s} may be the same or different, and X ² and Y ² may be the same or different, and are a hydrogen atom, a halogen atom, an alkyl having 1 to 8 carbon atoms. Represents any of a group, an aralkyl group, an alkoxy group or an aryloxy group.

In the general formula (3), R ⁴ and R ⁵ may be the same or different and each represents an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted with an oxygen atom, X ³ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aralkyl group, an alkoxy group, or an aryloxy group.

First, the naphthalene compound represented by the general formula (2) will be described. In general formula (2), n is 2, and OR ³ is substituted at positions 1 and 4 of the naphthalene ring to obtain a compound of general formula (4).

In the general formula (4), R ⁶ and R ⁷ may be the same or different and each represents an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted with an oxygen atom, X ⁴ and Y ³ may be the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aralkyl group, an alkoxy group, or an aryloxy group.

In the general formulas (2) and (4), examples of the alkyl group having 1 to 9 carbon atoms that may be substituted by oxygen atoms represented by R ³ , R ⁶ , and R ⁷ include, for example, a methyl group , Ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, n -Nonyl group, 2-hydroxyethyl group, 3-hydroxyethyl group, 2-hydroxypropyl group, 2-methoxyethoxy group, 2-ethoxyethoxy group, 2-phenoxyethoxy group and the like can be mentioned. Examples of the glycidyl group include a glycidyl group and a 2-methylglycidyl group.

In the general formulas (2) and (4), examples of the halogen atom represented by X ² , X ^4, Y ² , and Y ³ include a fluorine atom, a chlorine atom, a bromine atom, and the like. Examples of the alkyl group include a methyl group, an ethyl group, and a t-butyl group, examples of the aralkyl group include a benzyl group and a phenethyl group, examples of the alkoxy group include a methoxy group and an ethoxy group, and an aryloxy group. Examples thereof include a phenoxy group.

As typical naphthalene compounds represented by the general formulas (2) and (4), for example, 1,4-dimethoxynaphthalene, 1,4-diethoxynaphthalene, 1,4-bis (n-propoxy) naphthalene, 1,4-bis (n-butoxy) naphthalene, 1,4-bis (i-butoxy) naphthalene, 1,4-bis (n-pentyloxy) naphthalene, 1,4-bis (i-pentyloxy) naphthalene, 1,4-bis (n-hexyloxy) naphthalene, 1,4-bis (n-heptyloxy) naphthalene, 1,4-bis (n-octyloxy) naphthalene, 1,4-bis (2-ethylhexyloxy) Naphthalene, 1,4-bis (n-nonyloxy) naphthalene, 1,4-dibenzyloxynaphthalene, 1,4-diphenethyloxynaphthalene, 1,4-di Glycidyl oxy naphthalene, 1,4-bis (2-methyl-glycidyloxy) naphthalene.

In addition to the above, typical naphthalene compounds represented by the general formula (2) include, for example, 1,2-dimethoxynaphthalene, 1,2-diethoxynaphthalene, 1,2-bis (n-propoxy) naphthalene, 1,2-bis (n-butoxy) naphthalene, 1,2-bis (i-butoxy) naphthalene, 1,2-bis (n-pentyloxy) naphthalene, 1,2-bis (i-pentyloxy) naphthalene, 1,2-bis (n-hexyloxy) naphthalene, 1,2-bis (n-heptyloxy) naphthalene, 1,2-bis (n-octyloxy) naphthalene, 1,2-bis (2-ethylhexyloxy) Naphthalene, 1,2-dibenzyloxynaphthalene, 1,2-diphenethyloxynaphthalene, 1,2-diglycidyloxynaphthalene, 1,2-bis (2 Methylglycidyloxy) naphthalene, 1,6-dimethoxynaphthalene, 1,6-diethoxynaphthalene, 1,6-bis (n-propoxy) naphthalene, 1,6-bis (n-butoxy) naphthalene, 1,6-bis (I-butoxy) naphthalene, 1,6-bis (n-pentyloxy) naphthalene, 1,6-bis (i-pentyloxy) naphthalene, 1,6-bis (n-hexyloxy) naphthalene, 1,6- Bis (n-heptyloxy) naphthalene, 1,6-bis (n-octyloxy) naphthalene, 1,6-bis (2-ethylhexyloxy) naphthalene, 1,6-bis (n-nonyloxy) naphthalene, 1,6 -Dibenzyloxynaphthalene, 1,6-diphenethyloxynaphthalene, 1,6-diglycidyloxynaphthalene, 1,5- Methoxynaphthalene, 1,5-diethoxynaphthalene, 1,5-bis (n-propoxy) naphthalene, 1,5-bis (n-butoxy) naphthalene, 1,5-bis (i-butoxy) naphthalene, 1,5 -Bis (n-pentyloxy) naphthalene, 1,5-bis (i-pentyloxy) naphthalene, 1,5-bis (n-hexyloxy) naphthalene, 1,5-bis (n-heptyloxy) naphthalene, , 5-bis (n-octyloxy) naphthalene, 1,5-bis (2-ethylhexyloxy) naphthalene, 1,5-bis (n-nonyloxy) naphthalene, 1,5-dibenzyloxynaphthalene, 1,5- Examples thereof include diphenethyloxynaphthalene and 1,5-diglycidyloxynaphthalene.

2,7-dimethoxynaphthalene, 2.7-diethoxynaphthalene, 2,7-bis (n-propoxy) naphthalene, 2,7-bis (n-butoxy) naphthalene, 2,7-bis (i-butoxy) ) Naphthalene, 2,7-bis (n-pentyloxy) naphthalene, 2,7-bis (i-pentyloxy) naphthalene, 2,7-bis (n-hexyloxy) naphthalene, 2,7-bis (n- Heptyloxy) naphthalene, 2,7-bis (n-octyloxy) naphthalene, 2,7-bis (2-ethylhexyloxy) naphthalene, 2,7-bis (n-nonyloxy) naphthalene, 2,7-dibenzyloxy Naphthalene, 2,7-diphenethyloxynaphthalene, 2,7-diglycidyloxynaphthalene, 1,8-dimethoxynaphthalene, 1,8-di Toxinaphthalene, 1,8-bis (n-propoxy) naphthalene, 1,8-bis (n-butoxy) naphthalene, 1,8-bis (i-butoxy) naphthalene, 1,8-bis (n-pentyloxy) Naphthalene, 1,8-bis (i-pentyloxy) naphthalene, 1,8-bis (n-hexyloxy) naphthalene, 1,8-bis (n-heptyloxy) naphthalene, 1,8-bis (n-octyl) Oxy) naphthalene, 1,8-bis (2-ethylhexyloxy) naphthalene, 1,8-bis (n-nonyloxy) naphthalene, 1,8-dibenzyloxynaphthalene, 1,8-diphenethyloxynaphthalene, 1,8 -Diglycidyloxynaphthalene, 2,3-dimethoxynaphthalene, 2,3-diethoxynaphthalene, 2,3-bis (n-propoxy ) Naphthalene, 2,3-bis (n-butoxy) naphthalene, 2,3-bis (i-butoxy) naphthalene, 2,3-bis (n-pentyloxy) naphthalene, 2,3-bis (i-pentyloxy) ) Naphthalene, 2,3-bis (n-hexyloxy) naphthalene, 2,3-bis (n-heptyloxy) naphthalene, 2,3-bis (n-octyloxy) naphthalene, 2,3-bis (2- Ethylhexyloxy) naphthalene, 2,3-bis (n-nonyloxy) naphthalene, 2,3-dibenzyloxynaphthalene, 2,3-diphenethyloxynaphthalene, 2,3-diglycidyloxynaphthalene, 2,6-dimethoxynaphthalene 2,6-diethoxynaphthalene, 2,6-bis (n-propoxy) naphthalene, 2,6-bis (n-butoxy) naphth Talene, 2,6-bis (i-butoxy) naphthalene, 2,6-bis (n-pentyloxy) naphthalene, 2,6-bis (i-pentyloxy) naphthalene, 2,6-bis (n-hexyloxy) ) Naphthalene, 2,6-bis (n-heptyloxy) naphthalene, 2,6-bis (n-octyloxy) naphthalene, 2,6-bis (2-ethylhexyloxy) naphthalene, 2,6-bis (n- Nonyloxy) naphthalene, 2,6-dibenzyloxynaphthalene, 2,6-diphenethyloxynaphthalene, 2,6-diglycidyloxynaphthalene and the like.

In the general formulas (2) and (4), examples of the compound in which the naphthalene ring is substituted with an alkyl group include 2-methyl-1,4-dimethoxynaphthalene and 2-methyl-1,4-diethoxynaphthalene. 2-methyl-1,4-bis (n-propoxy) naphthalene, 2-methyl-1,4-bis (n-butoxy) naphthalene, 2-methyl-1,4-bis (i-butoxy) naphthalene, 2, -Methyl-1,4-bis (n-pentyloxy) naphthalene, 2-methyl-1,4-bis (i-pentyloxy) naphthalene, 2-methyl-1,4-bis (n-hexyloxy) naphthalene, 2-methyl-1,4-bis (n-heptyloxy) naphthalene, 2-methyl-1,4-bis (n-octyloxy) naphthalene, 2-methyl-1,4-bis (2-ethyl) Xyloxy) naphthalene, 2-methyl-1,4-bis (n-nonyloxy) naphthalene, 2-methyl-1,4-dibenzyloxynaphthalene, 2-methyl-1,4-diphenethyloxynaphthalene, 2-methyl- Examples include 1,4-diglycidyloxynaphthalene.

In addition to the above, in the general formula (2), examples of the compound in which an alkyl group is substituted on the naphthalene ring include 3-methyl-1,2-dimethoxynaphthalene, 3-methyl-1,2-diethoxynaphthalene, 2- Methyl-1,2-bis (n-propoxy) naphthalene, 3-methyl-1,2-bis (n-butoxy) naphthalene, 3-methyl-1,2-bis (i-butoxy) naphthalene, 3-methyl- 1,2-bis (n-pentyloxy) naphthalene, 3-methyl-1,2-bis (i-pentyloxy) naphthalene, 3-methyl-1,2-bis (n-hexyloxy) naphthalene, 3-methyl -1,2-bis (n-heptyloxy) naphthalene, 3-methyl-1,2-bis (n-octyloxy) naphthalene, 3-methyl-1,2-bis (2-ethylhexyl) Xyl) naphthalene, 3-methyl-1,2-bis (n-nonyloxy) naphthalene, 3-methyl-1,2-dibenzyloxynaphthalene, 3-methyl-1,2-diphenethyloxynaphthalene, 3-methyl- 1,2-diglycidyloxynaphthalene, 2-methyl-1,6-dimethoxynaphthalene, 2-methyl-1,6-diethoxynaphthalene, 2-methyl-1,6-bis (n-propoxy) naphthalene, 2- Methyl-1,6-bis (n-butoxy) naphthalene, 2-methyl-1,6-bis (i-butoxy) naphthalene, 2-methyl-1,6-bis (n-pentyloxy) naphthalene, 2-methyl -1,6-bis (i-pentyloxy) naphthalene, 2-methyl-1,6-bis (n-hexyloxy) naphthalene, 2-methyl-1,6-bis ( -Heptyloxy) naphthalene, 2-methyl-1,6-bis (n-octyloxy) naphthalene, 2-methyl-1,6-bis (2-ethylhexyloxy) naphthalene, 2-methyl-1,6-bis ( n-nonyloxy) naphthalene, 2-methyl-1,6-dibenzyloxynaphthalene, 2-methyl-1,6-diphenethyloxynaphthalene, 2-methyl-1,6-diglycidyloxynaphthalene and the like.

Further, 2-methyl-1,5-dimethoxynaphthalene, 2-methyl-1,5-diethoxynaphthalene, 2-methyl-1,5-bis (n-propoxy) naphthalene, 2-methyl-1,5-bis (N-butoxy) naphthalene, 2-methyl-1,5-bis (i-butoxy) naphthalene, 2-methyl-1,5-bis (n-pentyloxy) naphthalene, 2-methyl-1,5-bis ( i-pentyloxy) naphthalene, 2-methyl-1,5-bis (n-hexyloxy) naphthalene, 2-methyl-1,5-bis (n-heptyloxy) naphthalene, 2-methyl-1,5-bis (N-octyloxy) naphthalene, 2-methyl-1,5-bis (2-ethylhexyloxy) naphthalene, 2-methyl-1,5-bis (n-nonyloxy) naphthalene, 2-methyl -1,5-dibenzyloxynaphthalene, 2-methyl-1,5-diphenethyloxynaphthalene, 2-methyl-1,5-diglycidyloxynaphthalene, 3-methyl-2,7-dimethoxynaphthalene, 3-methyl -2,7-diethoxynaphthalene, 3-methyl-2,7-bis (n-propoxy) naphthalene, 3-methyl-2,7-bis (n-butoxy) naphthalene, 3-methyl-2,7-bis (I-butoxy) naphthalene, 3-methyl-2,7-bis (n-pentyloxy) naphthalene, 3-methyl-2,7-bis (i-pentyloxy) naphthalene, 3-methyl-2,7-bis (N-hexyloxy) naphthalene, 3-methyl-2,7-bis (n-heptyloxy) naphthalene, 3-methyl-2,7-bis (n-octyloxy) naphtha 3-methyl-2,7-bis (2-ethylhexyloxy) naphthalene, 3-methyl-2,7-bis (n-nonyloxy) naphthalene, 3-methyl-2,7-dibenzyloxynaphthalene, 3- Methyl-2,7-diphenethyloxynaphthalene, 3-methyl-2,7-diglycidyloxynaphthalene, 2-methyl-1,8-dimethoxynaphthalene, 2-methyl-1,8-diethoxynaphthalene, 2-methyl -1,8-bis (n-propoxy) naphthalene, 2-methyl-1,8-bis (n-butoxy) naphthalene, 2-methyl-1,8-bis (i-butoxy) naphthalene, 2-methyl-1 , 8-bis (n-pentyloxy) naphthalene, 2-methyl-1,8-bis (i-pentyloxy) naphthalene, 2-methyl-1,8-bis (n-hexyl) Ruoxy) naphthalene, 2-methyl-1,8-bis (n-heptyloxy) naphthalene, 2-methyl-1,8-bis (n-octyloxy) naphthalene, 2-methyl-1,8-bis (2- Ethylhexyloxy) naphthalene, 2-methyl-1,8-bis (n-nonyloxy) naphthalene, 2-methyl-1,8-dibenzyloxynaphthalene, 2-methyl-1,8-diphenethyloxynaphthalene, 2-methyl Examples include -1,8-diglycidyloxynaphthalene.

Further, 3-methyl-2,6-dimethoxynaphthalene, 3-methyl-2,6-diethoxynaphthalene, 3-methyl-2,6-bis (n-propoxy) naphthalene, 3-methyl-2,6-bis (N-butoxy) naphthalene, 3-methyl-2,6-bis (i-butoxy) naphthalene, 3-methyl-2,6-bis (n-pentyloxy) naphthalene, 3-methyl-2,6-bis ( i-pentyloxy) naphthalene, 3-methyl-2,6-bis (n-hexyloxy) naphthalene, 3-methyl-2,6-bis (n-heptyloxy) naphthalene, 3-methyl-2,6-bis (N-octyloxy) naphthalene, 3-methyl-2,6-bis (2-ethylhexyloxy) naphthalene, 3-methyl-2,6-bis (n-nonyloxy) naphthalene, 3-methyl -2,6-dibenzyloxynaphthalene, 3-methyl-2,6-diphenethyloxynaphthalene, 3-methyl-2,6-diglycidyloxynaphthalene, 5-methyl-2,3-dimethoxynaphthalene, 5-methyl -2,3-diethoxynaphthalene, 5-methyl-2,3-bis (n-propoxy) naphthalene, 5-methyl-2,3-bis (n-butoxy) naphthalene, 5-methyl-2,3-bis (I-butoxy) naphthalene, 5-methyl-2,3-bis (n-pentyloxy) naphthalene, 5-methyl-2,3-bis (i-pentyloxy) naphthalene, 5-methyl-2,3-bis (N-hexyloxy) naphthalene, 5-methyl-2,3-bis (n-heptyloxy) naphthalene, 5-methyl-2,3-bis (n-octyloxy) naphtha 5-methyl-2,3-bis (2-ethylhexyloxy) naphthalene, 5-methyl-2,3-bis (n-nonyloxy) naphthalene, 5-methyl-2,3-dibenzyloxynaphthalene, 5- Examples include methyl-2,3-diphenethyloxynaphthalene and 5-methyl-2,3-diglycidyloxynaphthalene.

In the general formulas (2) and (4), examples of the compound in which the naphthalene ring is substituted with a halogen atom include 2-chloro-1,4-dimethoxynaphthalene, 2-chloro-1,4-diethoxynaphthalene, 2-chloro-1,4-bis (n-propoxy) naphthalene, 2-chloro-1,4-bis (n-butoxy) naphthalene, 2-chloro-1,4-bis (i-butoxy) naphthalene, 2- Chloro-1,4-bis (n-pentyloxy) naphthalene, 2-chloro-1,4-bis (i-pentyloxy) naphthalene, 2-chloro-1,4-bis (n-hexyloxy) naphthalene, 2 -Chloro-1,4-bis (n-heptyloxy) naphthalene, 2-chloro-1,4-bis (n-octyloxy) naphthalene, 2-chloro-1,4-bis (2-ethyl) Xyloxy) naphthalene, 2-chloro-1,4-bis (n-nonyloxy) naphthalene, 2-chloro-1,4-dibenzyloxynaphthalene, 2-chloro-1,4-diphenethyloxynaphthalene, 2-chloro- Examples include 1,4-diglycidyloxynaphthalene.

In addition to the above, in the general formula (2), examples of the compound in which a halogen atom is substituted on the naphthalene ring include 3-chloro-1,2-dimethoxynaphthalene, 3-chloro-1,2-diethoxynaphthalene, 3- Chloro-1,2-bis (n-propoxy) naphthalene, 3-chloro-1,2-bis (n-butoxy) naphthalene, 3-chloro-1,2-bis (i-butoxy) naphthalene, 3-chloro- 1,2-bis (n-pentyloxy) naphthalene, 3-chloro-1,2-bis (i-pentyloxy) naphthalene, 3-chloro-1,2-bis (n-hexyloxy) naphthalene, 3-chloro -1,2-bis (n-heptyloxy) naphthalene, 3-chloro-1,2-bis (n-octyloxy) naphthalene, 3-chloro-1,2-bis (2-ethylhexyl) Oxy) naphthalene, 3-chloro-1,2-bis (n-nonyloxy) naphthalene, 3-chloro-1,2-dibenzyloxynaphthalene, 3-chloro-1,2-diphenethyloxynaphthalene, 3-chloro- 1,2-diglycidyloxynaphthalene, 2-chloro-1,6-dimethoxynaphthalene, 2-chloro-1,6-diethoxynaphthalene, 2-chloro-1,6-bis (n-propoxy) naphthalene, 2- Chloro-1,6-bis (n-butoxy) naphthalene, 2-chloro-1,6-bis (i-butoxy) naphthalene, 2-chloro-1,6-bis (n-pentyloxy) naphthalene, 2-chloro -1,6-bis (i-pentyloxy) naphthalene, 2-chloro-1,6-bis (n-hexyloxy) naphthalene, 2-chloro-1,6-bis n-heptyloxy) naphthalene, 2-chloro-1,6-bis (n-octyloxy) naphthalene, 2-chloro-1,6-bis (2-ethylhexyloxy) naphthalene, 2-chloro-1,6-bis (N-nonyloxy) naphthalene, 2-chloro-1,6-dibenzyloxynaphthalene, 2-chloro-1,6-diphenethyloxynaphthalene, 2-chloro-1,6-diglycidyloxynaphthalene, 2-chloro- 1,5-dimethoxynaphthalene, 2-chloro-1,5-diethoxynaphthalene, 2-chloro-1,5-bis (n-propoxy) naphthalene, 2-chloro-1,5-bis (n-butoxy) naphthalene 2-chloro-1,5-bis (i-butoxy) naphthalene, 2-chloro-1,5-bis (n-pentyloxy) naphthalene, 2-chloro B-1,5-bis (i-pentyloxy) naphthalene, 2-chloro-1,5-bis (n-hexyloxy) naphthalene, 2-chloro-1,5-bis (n-heptyloxy) naphthalene, 2, -Chloro-1,5-bis (n-octyloxy) naphthalene, 2-chloro-1,5-bis (2-ethylhexyloxy) naphthalene, 2-chloro-1,5-bis (n-nonyloxy) naphthalene, -Chloro-1,5-dibenzyloxynaphthalene, 2-chloro-1,5-diphenethyloxynaphthalene, 2-chloro-1,5-diglycidyloxynaphthalene and the like.

Also, 3-chloro-2,7-dimethoxynaphthalene, 3-chloro-2,7-diethoxynaphthalene, 3-chloro-2,7-bis (n-propoxy) naphthalene, 3-chloro-2,7-bis (N-butoxy) naphthalene, 3-chloro-2,7-bis (i-butoxy) naphthalene, 3-chloro-2,7-bis (n-pentyloxy) naphthalene, 3-chloro-2,7-bis ( i-pentyloxy) naphthalene, 3-chloro-2,7-bis (n-hexyloxy) naphthalene, 3-chloro-2,7-bis (n-heptyloxy) naphthalene, 3-chloro-2,7-bis (N-octyloxy) naphthalene, 3-chloro-2,7-bis (2-ethylhexyloxy) naphthalene, 3-chloro-2,7-bis (n-nonyloxy) naphthalene, 3-chloro -2,7-dibenzyloxynaphthalene, 3-chloro-2,7-diphenethyloxynaphthalene, 3-chloro-2,7-diglycidyloxynaphthalene, 2-chloro-1,8-dimethoxynaphthalene, 2-chloro -1,8-diethoxynaphthalene, 2-chloro-1,8-bis (n-propoxy) naphthalene, 2-chloro-1,8-bis (n-butoxy) naphthalene, 2-chloro-1,8-bis (I-butoxy) naphthalene, 2-chloro-1,8-bis (n-pentyloxy) naphthalene, 2-chloro-1,8-bis (i-pentyloxy) naphthalene, 2-chloro-1,8-bis (N-hexyloxy) naphthalene, 2-chloro-1,8-bis (n-heptyloxy) naphthalene, 2-chloro-1,8-bis (n-octyloxy) naphtha 2-chloro-1,8-bis (2-ethylhexyloxy) naphthalene, 2-chloro-1,8-bis (n-nonyloxy) naphthalene, 2-chloro-1,8-dibenzyloxynaphthalene, 2- Chloro-1,8-diphenethyloxynaphthalene, 2-chloro-1,8-diglycidyloxynaphthalene, 3-chloro-2,6-dimethoxynaphthalene, 3-chloro-2,6-diethoxynaphthalene, 3-chloro -2,6-bis (n-propoxy) naphthalene, 3-chloro-2,6-bis (n-butoxy) naphthalene, 3-chloro-2,6-bis (i-butoxy) naphthalene, 3-chloro-2 , 6-Bis (n-pentyloxy) naphthalene, 3-chloro-2,6-bis (i-pentyloxy) naphthalene, 3-chloro-2,6-bis (n-hexyl) Ruoxy) naphthalene, 3-chloro-2,6-bis (n-heptyloxy) naphthalene, 3-chloro-2,6-bis (n-octyloxy) naphthalene, 3-chloro-2,6-bis (2- Ethylhexyloxy) naphthalene, 3-chloro-2,6-bis (n-nonyloxy) naphthalene, 3-chloro-2,6-dibenzyloxynaphthalene, 3-chloro-2,6-diphenethyloxynaphthalene, 3-chloro Examples include -2,6-diglycidyloxynaphthalene.

In the general formulas (2) and (4), examples of the compound in which the naphthalene ring is substituted with alkoxy include 1,2,4-trimethoxynaphthalene, 2-methoxy-1,4-diethoxynaphthalene, 2- Methoxy-1,4-bis (n-propoxy) naphthalene, 2-methoxy-1,4-bis (n-butoxy) naphthalene, 2-methoxy-1,4-bis (i-butoxy) naphthalene, 2-methoxy- 1,4-bis (n-pentyloxy) naphthalene, 2-methoxy-1,4-bis (i-pentyloxy) naphthalene, 2-methoxy-1,4-bis (n-hexyloxy) naphthalene, 2-methoxy -1,4-bis (n-heptyloxy) naphthalene, 2-methoxy-1,4-bis (n-octyloxy) naphthalene, 2-methoxy-1,4-bis 2-ethylhexyloxy) naphthalene, 2-methoxy-1,4-bis (n-nonyloxy) naphthalene, 2-methoxy-1,4-dibenzyloxynaphthalene, 2-methoxy-1,4-diphenethyloxynaphthalene, 2, -Methoxy-1,4-diglycidyloxynaphthalene and the like.

In addition to the above, in the general formula (2), examples of the compound in which the naphthalene ring is substituted with alkoxy include, for example, 1,2,3-trimethoxynaphthalene, 3-methoxy-1,2-diethoxynaphthalene, 3-methoxy-1 , 2-bis (n-propoxy) naphthalene, 3-methoxy-1,2-bis (n-butoxy) naphthalene, 3-methoxy-1,2-bis (i-butoxy) naphthalene, 3-methoxy-1,2 -Bis (n-pentyloxy) naphthalene, 3-methoxy-1,2-bis (i-pentyloxy) naphthalene, 3-methoxy-1,2-bis (n-hexyloxy) naphthalene, 3-methoxy-1, 2-bis (n-heptyloxy) naphthalene, 3-methoxy-1,2-bis (n-octyloxy) naphthalene, 3-methoxy-1,2-bis (2-ethyl) Ruhexyloxy) naphthalene, 3-methoxy-1,2-bis (n-nonyloxy) naphthalene, 3-methoxy-1,4-dibenzyloxynaphthalene, 3-methoxy-1,4-diphenethyloxynaphthalene, 3-methoxy -1,2-diglycidyloxynaphthalene, 1,2,6-trimethoxynaphthalene, 2-methoxy-1,6-diethoxynaphthalene, 2-methoxy-1,6-bis (n-propoxy) naphthalene, 2- Methoxy-1,6-bis (n-butoxy) naphthalene, 2-methoxy-1,6-bis (i-butoxy) naphthalene, 2-methoxy-1,6-bis (n-pentyloxy) naphthalene, 2-methoxy -1,6-bis (i-pentyloxy) naphthalene, 2-methoxy-1,6-bis (n-hexyloxy) naphthalene 2-methoxy-1,6-bis (n-heptyloxy) naphthalene, 2-methoxy-1,6-bis (n-octyloxy) naphthalene, 2-methoxy-1,6-bis (2-ethylhexyloxy) naphthalene 2-methoxy-1,6-bis (n-nonyloxy) naphthalene, 2-methoxy-1,6-dibenzyloxynaphthalene, 2-methoxy-1,6-1,4-diphenethyloxynaphthalene, 2-methoxy -1,6-diglycidyloxynaphthalene, 1,2,5-trimethoxynaphthalene, 2-methoxy-1,5-diethoxynaphthalene, 2-methoxy-1,5-bis (n-propoxy) naphthalene, 2- Methoxy-1,5-bis (n-butoxy) naphthalene, 2-methoxy-1,5-bis (i-butoxy) naphthalene, 2-methoxy-1 , 5-bis (n-pentyloxy) naphthalene, 2-methoxy-1,5-bis (i-pentyloxy) naphthalene, 2-methoxy-1,5-bis (n-hexyloxy) naphthalene, 2-methoxy- 1,5-bis (n-heptyloxy) naphthalene, 2-methoxy-1,5-bis (n-octyloxy) naphthalene, 2-methoxy-1,5-bis (2-ethylhexyloxy) naphthalene, 2-methoxy -1,5-bis (n-nonyloxy) naphthalene, 2-methoxy-1,5-dibenzyloxynaphthalene, 2-methoxy-1,5-1,4-diphenethyloxynaphthalene, 2-methoxy-1,5 -Diglycidyl oxynaphthalene etc. are mentioned.

Also, 3-methoxy-2,7-diethoxynaphthalene, 3-methoxy-2,7-bis (n-propoxy) naphthalene, 3-methoxy-2,7-bis (n-butoxy) naphthalene, 3-methoxy- 2,7-bis (i-butoxy) naphthalene, 3-methoxy-2,7-bis (n-pentyloxy) naphthalene, 3-methoxy-2,7-bis (i-pentyloxy) naphthalene, 3-methoxy- 2,7-bis (n-hexyloxy) naphthalene, 3-methoxy-2,7-bis (n-heptyloxy) naphthalene, 3-methoxy-2,7-bis (n-octyloxy) naphthalene, 3-methoxy -2,7-bis (2-ethylhexyloxy) naphthalene, 3-methoxy-2,7-bis (n-nonyloxy) naphthalene, 3-methoxy-2,7-diben Ruoxynaphthalene, 3-methoxy-2,7-diphenethyloxynaphthalene, 3-methoxy-2,7-diglycidyloxynaphthalene, 1,2,8-trimethoxynaphthalene, 2-methoxy-1,8-diethoxy Naphthalene, 2-methoxy-1,8-bis (n-propoxy) naphthalene, 2-methoxy-1,8-bis (n-butoxy) naphthalene, 2-methoxy-1,8-bis (i-butoxy) naphthalene, 2-methoxy-1,8-bis (n-pentyloxy) naphthalene, 2-methoxy-1,8-bis (i-pentyloxy) naphthalene, 2-methoxy-1,8-bis (n-hexyloxy) naphthalene 2-methoxy-1,8-bis (n-heptyloxy) naphthalene, 2-methoxy-1,8-bis (n-octyloxy) naphthalene 2-methoxy-1,8-bis (2-ethylhexyloxy) naphthalene, 2-methoxy-1,8-bis (n-nonyloxy) naphthalene, 2-methoxy-1,8-dibenzyloxynaphthalene, 2-methoxy -1,8-1,4-diphenethyloxynaphthalene, 2-methoxy-1,8-diglycidyloxynaphthalene, 2,3,6-trimethoxynaphthalene, 3-methoxy-2,6-diethoxynaphthalene, 3 -Methoxy-2,6-bis (n-propoxy) naphthalene, 3-methoxy-2,6-bis (n-butoxy) naphthalene, 3-methoxy-2,6-bis (i-butoxy) naphthalene, 3-methoxy -2,6-bis (n-pentyloxy) naphthalene, 3-methoxy-2,6-bis (i-pentyloxy) naphthalene, 3-methoxy- 2,6-bis (n-hexyloxy) naphthalene, 3-methoxy-2,6-bis (n-heptyloxy) naphthalene, 3-methoxy-2,6-bis (n-octyloxy) naphthalene, 3-methoxy -2,6-bis (2-ethylhexyloxy) naphthalene, 3-methoxy-2,6-bis (n-nonyloxy) naphthalene, 3-methoxy-2,6-dibenzyloxynaphthalene, 3-methoxy-2,6 -Diphenethyloxynaphthalene, 3-methoxy-2,6-diglycidyloxynaphthalene, etc. are mentioned.

In the general formulas (2) and (4), examples of the compound in which the naphthalene ring is substituted with aryloxy include, for example, 2-phenoxy-1,4-dimethoxynaphthalene, 2-phenoxy-1,4-diethoxynaphthalene, 2-phenoxy-1,4-bis (n-propoxy) naphthalene, 2-phenoxy-1,4-bis (n-butoxy) naphthalene, 2-phenoxy-1,4-bis (i-butoxy) naphthalene, 2- Phenoxy-1,4-bis (n-pentyloxy) naphthalene, 2-phenoxy-1,4-bis (i-pentyloxy) naphthalene, 2-phenoxy-1,4-bis (n-hexyloxy) naphthalene, 2, -Phenoxy-1,4-bis (n-heptyloxy) naphthalene, 2-phenoxy-1,4-bis (n-octyloxy) naphtha 2-phenoxy-1,4-bis (2-ethylhexyloxy) naphthalene, 2-phenoxy-1,4-bis (n-nonyloxy) naphthalene, 2-phenoxy-1,4-dibenzyloxynaphthalene, 2- Examples include phenoxy-1,4-diphenethyloxynaphthalene and 2-phenoxy-1,4-diglycidyloxynaphthalene.

In addition to the above, in the general formula (2), examples of the compound in which the naphthalene ring is substituted with aryloxy include, for example, 3-phenoxy-1,2-dimethoxynaphthalene, 3-phenoxy-1,2-diethoxynaphthalene, 3- Phenoxy-1,2-bis (n-propoxy) naphthalene, 3-phenoxy-1,2-bis (n-butoxy) naphthalene, 3-phenoxy-1,2-bis (i-butoxy) naphthalene, 3-phenoxy- 1,2-bis (n-pentyloxy) naphthalene, 3-phenoxy-1,2-bis (i-pentyloxy) naphthalene, 3-phenoxy-1,2-bis (n-hexyloxy) naphthalene, 3-phenoxy -1,2-bis (n-heptyloxy) naphthalene, 3-phenoxy-1,2-bis (n-octyloxy) naphthalene, -Phenoxy-1,2-bis (2-ethylhexyloxy) naphthalene, 3-phenoxy-1,2-bis (n-nonyloxy) naphthalene, 3-phenoxy-1,2-dibenzyloxynaphthalene, 3-phenoxy-1 , 2-diphenethyloxynaphthalene, 3-phenoxy-1,2-diglycidyloxynaphthalene, 2-phenoxy-1,6-dimethoxynaphthalene, 2-phenoxy-1,6-diethoxynaphthalene, 2-phenoxy-1, 6-bis (n-propoxy) naphthalene, 2-phenoxy-1,6-bis (n-butoxy) naphthalene, 2-phenoxy-1,6-bis (i-butoxy) naphthalene, 2-phenoxy-1,6- Bis (n-pentyloxy) naphthalene, 2-phenoxy-1,6-bis (i-pentyloxy) naphth Len, 2-phenoxy-1,6-bis (n-hexyloxy) naphthalene, 2-phenoxy-1,6-bis (n-heptyloxy) naphthalene, 2-phenoxy-1,6-bis (n-octyloxy) ) Naphthalene, 2-phenoxy-1,6-bis (2-ethylhexyloxy) naphthalene, 2-phenoxy-1,6-bis (n-nonyloxy) naphthalene, 2-phenoxy-1,6-dibenzyloxynaphthalene, 2, -Phenoxy-1,6-diphenethyloxynaphthalene, 2-phenoxy-1,6-diglycidyloxynaphthalene, 2-phenoxy-1,5-dimethoxynaphthalene, 2-phenoxy-1,5-diethoxynaphthalene, 2- Phenoxy-1,5-bis (n-propoxy) naphthalene, 2-phenoxy-1,5-bis (n-butylene) Toxyl) naphthalene, 2-phenoxy-1,5-bis (i-butoxy) naphthalene, 2-phenoxy-1,5-bis (n-pentyloxy) naphthalene, 2-phenoxy-1,5-bis (i-pentyl) Oxy) naphthalene, 2-phenoxy-1,5-bis (n-hexyloxy) naphthalene, 2-phenoxy-1,5-bis (n-heptyloxy) naphthalene, 2-phenoxy-1,5-bis (n- Octyloxy) naphthalene, 2-phenoxy-1,5-bis (2-ethylhexyloxy) naphthalene, 2-phenoxy-1,5-bis (n-nonyloxy) naphthalene, 2-phenoxy-1,5-dibenzyloxynaphthalene 2-phenoxy-1,5-diphenethyloxynaphthalene, 2-phenoxy-1,5-diglycidyloxynaphth Ren, and the like.

Also, 3-phenoxy-2,7-dimethoxynaphthalene, 3-phenoxy-2,7-diethoxynaphthalene, 3-phenoxy-2,7-bis (n-propoxy) naphthalene, 3-phenoxy-2,7-bis (N-butoxy) naphthalene, 3-phenoxy-2,7-bis (i-butoxy) naphthalene, 3-phenoxy-2,7-bis (n-pentyloxy) naphthalene, 3-phenoxy-2,7-bis ( i-pentyloxy) naphthalene, 3-phenoxy-2,7-bis (n-hexyloxy) naphthalene, 3-phenoxy-2,7-bis (n-heptyloxy) naphthalene, 3-phenoxy-2,7-bis (N-octyloxy) naphthalene, 3-phenoxy-2,7-bis (2-ethylhexyloxy) naphthalene, 3-phenoxy-2, -Bis (n-nonyloxy) naphthalene, 3-phenoxy-2,7-dibenzyloxynaphthalene, 3-phenoxy-2,7-diphenethyloxynaphthalene, 3-phenoxy-2,7-diglycidyloxynaphthalene, 2- Phenoxy-1,8-dimethoxynaphthalene, 2-phenoxy-1,8-diethoxynaphthalene, 2-phenoxy-1,8-bis (n-propoxy) naphthalene, 2-phenoxy-1,8-bis (n-butoxy) ) Naphthalene, 2-phenoxy-1,8-bis (i-butoxy) naphthalene, 2-phenoxy-1,8-bis (n-pentyloxy) naphthalene, 2-phenoxy-1,8-bis (i-pentyloxy) ) Naphthalene, 2-phenoxy-1,8-bis (n-hexyloxy) naphthalene, 2-phenoxy-1 8-bis (n-heptyloxy) naphthalene, 2-phenoxy-1,8-bis (n-octyloxy) naphthalene, 2-phenoxy-1,8-bis (2-ethylhexyloxy) naphthalene, 2-phenoxy-1 , 8-bis (n-nonyloxy) naphthalene, 2-phenoxy-1,8-dibenzyloxynaphthalene, 2-phenoxy-1,8-diphenethyloxynaphthalene, 2-phenoxy-1,8-diglycidyloxynaphthalene, 3-phenoxy-2,6-dimethoxynaphthalene, 3-phenoxy-2,6-diethoxynaphthalene, 3-phenoxy-2,6-bis (n-propoxy) naphthalene, 3-phenoxy-2,6-bis (n -Butoxy) naphthalene, 3-phenoxy-2,6-bis (i-butoxy) naphthalene, 3-phenoxy Cis-2,6-bis (n-pentyloxy) naphthalene, 3-phenoxy-2,6-bis (i-pentyloxy) naphthalene, 3-phenoxy-2,6-bis (n-hexyloxy) naphthalene, 3, -Phenoxy-2,6-bis (n-heptyloxy) naphthalene, 3-phenoxy-2,6-bis (n-octyloxy) naphthalene, 3-phenoxy-2,6-bis (2-ethylhexyloxy) naphthalene, 3-phenoxy-2,6-bis (n-nonyloxy) naphthalene, 3-phenoxy-2,6-dibenzyloxynaphthalene, 3-phenoxy-2,6-diphenethyloxynaphthalene, 3-phenoxy-2,6- And diglycidyloxynaphthalene.

Among these naphthalene compounds, 1,4-dimethoxynaphthalene and 1,4-diethoxynaphthalene are particularly preferable because they are easy to synthesize and have a large effect of enhancing the sensitizing performance of the photopolymerization sensitizer composition.

Next, the benzene compound represented by the general formulas (3) and (5) will be described. In the general formula (3), a compound in which OR ⁴ and OR ⁵ are substituted at positions 1 and 4 of the benzene ring is a compound of the general formula (5).

In the general formula (5), R ⁸ and R ⁹ may be the same or different and each represents an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted with an oxygen atom, X ⁵ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aralkyl group, an alkoxy group or an aryloxy group.

In the general formulas (3) and (5), examples of the alkyl group having 1 to 9 carbon atoms that may be substituted by an oxygen atom represented by R ⁴ , R ⁵ , R ⁸ , or R ⁹ include, for example, methyl Group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, Examples include n-nonyl group, 2-hydroxyethyl group, 3-hydroxyethyl group, 2-hydroxypropyl group, 2-methoxyethoxy group, 2-ethoxyethoxy group, 2-phenoxyethoxy group and the like. Examples of the glycidyl group include a glycidyl group and a 2-methylglycidyl group.

In the general formulas (3) and (5), examples of the halogen atom represented by X ³ and X ⁵ include a fluorine atom, a chlorine atom, and a bromine atom, and examples of the alkyl group having 1 to 8 carbon atoms include methyl. Group, ethyl group, t-butyl group, etc., aralkyl group includes benzyl group, phenethyl group, etc., alkoxy group includes methoxy group, ethoxy group, aryloxy group includes phenoxy group, etc. Can be mentioned.

Typical benzene compounds represented by the general formulas (3) and (5) include, for example, 1,4-dimethoxybenzene, 1,4-diethoxybenzene, 1,4-bis (n-propoxy) benzene. 1,4-bis (n-butoxy) benzene, 1,4-bis (i-butoxy) benzene, 1,4-bis (n-pentyloxy) benzene, 1,4-bis (i-pentyloxy) benzene 1,4-bis (n-hexyloxy) benzene, 1,4-bis (n-heptyloxy) benzene, 1,4-bis (n-octyloxy) benzene, 1,4-bis (2-ethylhexyloxy) ) Benzene, 1,4-bis (n-nonyloxy) benzene, 1,4-dibenzyloxybenzene, 1,4-diphenethyloxybenzene, 1,4-diglycidyloxybenzene, etc. It is below.

In addition to the above, typical benzene compounds represented by the general formula (3) include, for example, 1,3-dimethoxybenzene, 1,3-diethoxybenzene, 1,3-bis (n-propoxy) benzene, 1,3-bis (n-butoxy) benzene, 1,3-bis (i-butoxy) benzene, 1,3-bis (n-pentyloxy) benzene, 1,3-bis (i-pentyloxy) benzene, 1,3-bis (n-hexyloxy) benzene, 1,3-bis (n-heptyloxy) benzene, 1,3-bis (n-octyloxy) benzene, 1,5-bis (2-ethylhexyloxy) Benzene, 1,3-bis (n-nonyloxy) benzene, 1,3-dibenzyloxybenzene, 1,3-diphenethyloxybenzene, 1,3-diglycidyloxybenzene, reso Syn, 1,2-dimethoxybenzene, 1,2-diethoxybenzene, 1,2-bis (n-propoxy) benzene, 1,2-bis (n-butoxy) benzene, 1,2-bis (i-butoxy) ) Benzene, 1,2-bis (n-pentyloxy) benzene, 1,2-bis (i-pentyloxy) benzene, 1,2-bis (n-hexyloxy) benzene, 1,2-bis (n- Heptyloxy) benzene, 1,2-bis (n-octyloxy) benzene, 1,2-bis (2-ethylhexyloxy) benzene, 1,2-bis (n-nonyloxy) benzene, 1,2-dibenzyloxy Examples include benzene, 1,2-diphenethyloxybenzene, 1,2-diglycidyloxybenzene and the like.

In the general formulas (3) and (5), examples of the compound in which an alkyl group is substituted on the benzene ring include 2-methyl-1,4-dimethoxybenzene, 2-methyl-1,4-diethoxybenzene, 2-methyl-1,4-bis (n-propoxy) benzene, 2-methyl-1,4-bis (n-butoxy) benzene, 2-methyl-1,4-bis (i-butoxy) benzene, 2- Methyl-1,4-bis (n-pentyloxy) benzene, 2-methyl-1,4-bis (i-pentyloxy) benzene, 2-methyl-1,4-bis (n-hexyloxy) benzene, 2 -Methyl-1,4-bis (n-heptyloxy) benzene, 2-methyl-1,4-bis (n-octyloxy) benzene, 2-methyl-1,4-bis (2-ethylhexyloxy) benzene 2-methyl-1,4-bis (n-nonyloxy) benzene, 2-methyl-1,4-dibenzyloxybenzene, 2-methyl-1,4-diphenethyloxybenzene, 2-methyl-1,4- And diglycidyloxybenzene.

In addition to the above, in the general formula (3), examples of the compound in which an alkyl group is substituted on the benzene ring include 2-methyl-1,3-dimethoxybenzene, 2-methyl-1,3-diethoxybenzene, 2- Methyl-1,3-bis (n-propoxy) benzene, 2-methyl-1,3-bis (n-butoxy) benzene, 2-methyl-1,3-bis (i-butoxy) benzene, 2-methyl- 1,3-bis (n-pentyloxy) benzene, 2-methyl-1,3-bis (i-pentyloxy) benzene, 2-methyl-1,3-bis (n-hexyloxy) benzene, 2-methyl -1,3-bis (n-heptyloxy) benzene, 2-methyl-1,3-bis (n-octyloxy) benzene, 2-methyl-1,3-bis (2-ethylhexyloxy) benzene, 2- Til-1,3-bis (n-nonyloxy) benzene, 2-methyl-1,3-dibenzyloxybenzene, 2-methyl-1,3-diphenethyloxybenzene, 2-methyl-1,3-diglycidyl Oxybenzene, 2-methylresorcin, 3-methyl-1,2-dimethoxybenzene, 3-methyl-1,2-diethoxybenzene, 3-methyl-1,2-bis (n-propoxy) benzene, 3-methyl -1,2-bis (n-butoxy) benzene, 3-methyl-1,2-bis (i-butoxy) benzene, 3-methyl-1,2-bis (n-pentyloxy) benzene, 3-methyl- 1,2-bis (i-pentyloxy) benzene, 3-methyl-1,2-bis (n-hexyloxy) benzene, 3-methyl-1,2-bis (n-heptyloxy) benzene 3-methyl-1,2-bis (n-octyloxy) benzene, 3-methyl-1,2-bis (2-ethylhexyloxy) benzene, 3-methyl-1,2-bis (n-nonyloxy) benzene , 3-methyl-1,2-dibenzyloxybenzene, 3-methyl-1,2-diphenethyloxybenzene, 3-methyl-1,2-diglycidyloxybenzene and the like.

In the general formulas (3) and (5), examples of the compound in which a halogen atom is substituted on the benzene ring include 2-chloro-1,4-dimethoxybenzene, 2-chloro-1,4-diethoxybenzene, 2-chloro-1,4-bis (n-propoxy) benzene, 2-chloro-1,4-bis (n-butoxy) benzene, 2-chloro-1,4-bis (i-butoxy) benzene, 2- Chloro-1,4-bis (n-pentyloxy) benzene, 2-chloro-1,4-bis (i-pentyloxy) benzene, 2-chloro-1,4-bis (n-hexyloxy) benzene, 2 -Chloro-1,4-bis (n-heptyloxy) benzene, 2-chloro-1,4-bis (n-octyloxy) benzene, 2-chloro-1,4-bis (2-ethylhexyloxy) benzene 2-chloro-1,4-bis (n- nonyloxy) benzene, 2-chloro-1,4-benzyloxy benzene, 2-chloro-1,4-phenethyloxycarbonyl benzene.

In addition to the above, in the general formula (3), examples of the compound in which a halogen atom is substituted on the benzene ring include 2-chloro-1,3-dimethoxybenzene, 2-chloro-1,3-diethoxybenzene, 2- Chloro-1,3-bis (n-propoxy) benzene, 2-chloro-1,3-bis (n-butoxy) benzene, 2-chloro-1,3-bis (i-butoxy) benzene, 2-chloro- 1,3-bis (n-pentyloxy) benzene, 2-chloro-1,3-bis (i-pentyloxy) benzene, 2-chloro-1,3-bis (n-hexyloxy) benzene, 2-chloro -1,3-bis (n-heptyloxy) benzene, 2-chloro-1,3-bis (n-octyloxy) benzene, 2-chloro-1,3-bis (2-ethylhexyloxy) benzene, 2 Chloro-1,3-dibenzyloxybenzene, 2-chloro-1,3-diphenethyloxybenzene, 2-chloro-1,3-diglycidyloxybenzene, 3-chloro-1,2-dimethoxybenzene, 3- Chloro-1,2-diethoxybenzene, 3-chloro-1,2-bis (n-propoxy) benzene, 3-chloro-1,2-bis (n-butoxy) benzene, 3-chloro-1,2- Bis (i-butoxy) benzene, 3-chloro-1,2-bis (n-pentyloxy) benzene, 3-chloro-1,2-bis (i-pentyloxy) benzene, 3-chloro-1,2- Bis (n-hexyloxy) benzene, 3-chloro-1,2-bis (n-heptyloxy) benzene, 3-chloro-1,2-bis (n-octyloxy) benzene, 3-chloro-1 2-bis (2-ethylhexyloxy) benzene, 3-chloro-1,2-bis (n-nonyloxy) benzene, 3-chloro-1,2-dibenzyloxybenzene, 3-chloro-1,2-diphenethyl Examples thereof include oxybenzene and 3-chloro-1,2-diglycidyloxybenzene.

In the general formulas (3) and (5), examples of the compound in which alkoxy is substituted on the benzene ring include 1,2,4-trimethoxybenzene, 2-methoxy-1,4-diethoxybenzene, 2- Methoxy-1,4-bis (n-propoxy) benzene, 2-methoxy-1,4-bis (n-butoxy) benzene, 2-methoxy-1,4-bis (i-butoxy) benzene, 2-methoxy- 1,4-bis (n-pentyloxy) benzene, 2-methoxy-1,4-bis (i-pentyloxy) benzene, 2-methoxy-1,4-bis (n-hexyloxy) benzene, 2-methoxy -1,4-bis (n-heptyloxy) benzene, 2-methoxy-1,4-bis (n-octyloxy) benzene, 2-methoxy-1,4-bis (2-ethylhexylo) Ii) benzene, 2-methoxy-1,4-bis (n-nonyloxy) benzene, 2-methoxy-1,4-dibenzyloxybenzene, 2-methoxy-1,4-diphenethyloxybenzene, 2-methoxy- 1,4-diglycidyloxybenzene and the like can be mentioned.

In addition to the above, in the general formula (3), examples of the compound in which the benzene ring is substituted with alkoxy include 1,2,3-trimethoxybenzene, 3-methoxy-1,2-diethoxybenzene, 3-methoxy- 1,2-bis (n-propoxy) benzene, 3-methoxy-1,2-bis (n-butoxy) benzene, 3-methoxy-1,2-bis (i-butoxy) benzene, 3-methoxy-1, 2-bis (n-pentyloxy) benzene, 3-methoxy-1,2-bis (i-pentyloxy) benzene, 3-methoxy-1,2-bis (n-hexyloxy) benzene, 3-methoxy-1 , 2-bis (n-heptyloxy) benzene, 3-methoxy-1,2-bis (n-octyloxy) benzene, 3-methoxy-1,2-bis (2-ethylhexyloxy) , 3-methoxy-1,2-bis (n-nonyloxy) benzene, 3-methoxy-1,2-dibenzyloxybenzene, 3-methoxy-1,2-diphenethyloxybenzene, 3-methoxy-1, 2-diglycidyloxybenzene, 2-methoxy-1,3-diethoxybenzene, 2-methoxy-1,3-bis (n-propoxy) benzene, 2-methoxy-1,3-bis (n-butoxy) benzene 2-methoxy-1,3-bis (i-butoxy) benzene, 2-methoxy-1,3-bis (n-pentyloxy) benzene, 2-methoxy-1,3-bis (i-pentyloxy) benzene 2-methoxy-1,3-bis (n-hexyloxy) benzene, 2-methoxy-1,3-bis (n-heptyloxy) benzene, 2-methoxy-1,3 Bis (n-octyloxy) benzene, 2-methoxy-1,3-bis (2-ethylhexyloxy) benzene, 2-methoxy-1,3-dibenzyloxybenzene, 2-methoxy-1,3-diphenethyloxy Examples thereof include benzene and 2-methoxy-1,3-diglycidyloxybenzene.

In the general formulas (3) and (5), examples of the compound in which aryloxy is substituted on the benzene ring include 2-phenoxy-1,4-dimethoxybenzene, 2-phenoxy-1,4-diethoxybenzene, 2-phenoxy-1,4-bis (n-propoxy) benzene, 2-phenoxy-1,4-bis (n-butoxy) benzene, 2-phenoxy-1,4-bis (i-butoxy) benzene, 2- Phenoxy-1,4-bis (n-pentyloxy) benzene, 2-phenoxy-1,4-bis (i-pentyloxy) benzene, 2-phenoxy-1,4-bis (n-hexyloxy) benzene, 2 -Phenoxy-1,4-bis (n-heptyloxy) benzene, 2-phenoxy-1,4-bis (n-octyloxy) benzene, 2-phenoxy- , 4-bis (2-ethylhexyloxy) benzene, 2-phenoxy-1,4-bis (n-nonyloxy) benzene, 2-phenoxy-1,4-dibenzyloxybenzene, 2-phenoxy-1,4-di Phenethyloxybenzene, 2-phenoxy-1,4-diglycidyloxybenzene, etc. are mentioned.

In addition to the above, in the general formula (3), examples of the compound in which aryloxy is substituted on the benzene ring include 3-phenoxy-1,2-dimethoxybenzene, 3-phenoxy-1,2-diethoxybenzene, 3- Phenoxy-1,2-bis (n-propoxy) benzene, 3-phenoxy-1,2-bis (n-butoxy) benzene, 3-phenoxy-1,2-bis (i-butoxy) benzene, 3-phenoxy- 1,2-bis (n-pentyloxy) benzene, 3-phenoxy-1,2-bis (i-pentyloxy) benzene, 3-phenoxy-1,2-bis (n-hexyloxy) benzene, 3-phenoxy -1,2-bis (n-heptyloxy) benzene, 3-phenoxy-1,2-bis (n-octyloxy) benzene, 3-phenoxy-1,2 Bis (2-ethylhexyloxy) benzene, 3-phenoxy-1,2-bis (n-nonyloxy) benzene, 3-phenoxy-1,2-dibenzyloxybenzene, 3-phenoxy-1,2-diphenethyloxybenzene 3-phenoxy-1,2-diglycidyloxybenzene, 2-phenoxy-1,3-dimethoxybenzene, 2-phenoxy-1,3-diethoxybenzene, 2-phenoxy-1,3-bis (n-propoxy ) Benzene, 2-phenoxy-1,3-bis (n-butoxy) benzene, 2-phenoxy-1,3-bis (i-butoxy) benzene, 2-phenoxy-1,3-bis (n-pentyloxy) Benzene, 2-phenoxy-1,3-bis (i-pentyloxy) benzene, 2-phenoxy-1,3-bis (n-hex) Ruoxy) benzene, 2-phenoxy-1,3-bis (n-heptyloxy) benzene, 2-phenoxy-1,3-bis (n-octyloxy) benzene, 2-phenoxy-1,3-bis (2- Ethylhexyloxy) benzene, 2-phenoxy-1,3-dibenzyloxybenzene, 2-phenoxy-1,3-diphenethyloxybenzene, 2-phenoxy-1,3-diglycidyloxybenzene and the like.

Among these benzene compounds, 1,4-dimethoxybenzene and 1,4-diethoxybenzene are particularly preferable because they are easy to synthesize and have a large effect of enhancing the sensitizing performance of the photopolymerization sensitizer composition.

In the photopolymerization sensitizer composition of the present invention, the addition ratio of the 9,10-bis (2-hydroxyalkoxy) anthracene compound to the naphthalene compound and the 9,10-bis (2-hydroxyalkoxy) anthracene compound to the benzene compound The addition ratio is preferably 0.01 or more and less than 10, more preferably 0.02 or more and 5 or less by weight. If it is less than 0.01, the effect as a sensitizer is not sufficient, and if it is 10 or more, the photocurable composition containing the photopolymerization sensitizer composition is cured when cured. Since transparency of an object is impaired, it is not preferable.

In the photopolymerization sensitizer composition of the present invention, a preferred combination of a naphthalene compound and a 9,10-bis (2-hydroxyalkoxy) anthracene compound, or a benzene compound and a 9,10-bis (2-hydroxyalkoxy) anthracene compound 1,4-diethoxynaphthalene and 9,10-bis (2-hydroxypropoxy) anthracene, 1,4-diethoxynaphthalene and 9,10-bis (2-hydroxy-3-butoxypropoxy) anthracene, 1, 4-diethoxynaphthalene and 9,10-bis (2-hydroxy-3-allyloxypropoxy) anthracene, 1,4-dimethoxybenzene and 9,10-bis (2-hydroxypropoxy) anthracene, 1,4-diethoxy Benzene and 9,10-bis (2-hydroxypropoxy) It is anthracene.

Further, as the component (A), one anthracene compound may be used, or two or more compounds may be used. Similarly, one naphthalene compound or benzene compound may be used as the component (B), or two or more naphthalene compounds or benzene compounds may be mixed and used.

Furthermore, these photopolymerization sensitizer compositions can be used as components of the photopolymerizable composition in combination with a photopolymerizable compound and a photopolymerization initiator described later. In that case, although there is no restriction | limiting in the usage-amount with respect to the photopolymerizable composition of the photopolymerization sensitizer composition in this invention, Usually in the range of 0.01 weight%-50 weight% with respect to the whole photopolymerizable composition. Used, preferably in the range of 0.05 wt% to 20 wt%.

The photopolymerization sensitizer composition of the present invention is characterized by giving a cured product with little coloration. In that sense, the amount of component (A) used is 0.05 to the total photopolymerizable composition. It is preferable that the content is from 0.1% by weight to 4.0% by weight, preferably from 0.1% by weight to 2.0% by weight. Even when the addition amount of the component (A) is within the above range, a curing rate having no practical problem can be obtained by using the component (B) in combination.

(Photopolymerizable composition)
The photopolymerizable composition can be obtained by adding a photopolymerization sensitizer composition containing the components (A) and (B) and (C) a photopolymerization initiator to the photopolymerizable compound (D). it can.

(Photopolymerization initiator)
As the photopolymerization initiator, a photocationic polymerization initiator and / or a photoradical polymerization initiator can be used in accordance with the photopolymerizable compound.

(Photocationic polymerization initiator)
As the photocationic polymerization initiator used in the present invention, one that generates a polymerization initiating species for the photocationically polymerizable compound by light irradiation is used. In particular, a photoacid generator that generates Bronsted acid or Lewis acid by light irradiation is preferably used.

Examples of such a cationic photopolymerization initiator include sulfonic acid ester, imide sulfonate, dialkyl-4-hydroxysulfonium salt, arylsulfonic acid-p-nitrobenzyl ester, silanol-aluminum complex, (η6-benzene) (η5-cyclopenta Dienyl) iron (II) and the like, and more specifically, benzoin tosylate, 2,5-dinitrobenzyl tosylate, N-tosicphthalimide and the like.

Furthermore, aromatic iodonium salts, aromatic sulfonium salts, aromatic diazonium salts, aromatic phosphonium salts, triazine compounds, iron arene complexes, and the like can be given. Specifically, chlorides of iodonium such as diphenyliodonium, ditolyliodonium, bis (p-tert-butylphenyl) iodonium, bis (p-chlorophenyl) iodonium, bromide, borofluoride, hexafluorophosphate, hexafluoroantimony Nate salts, triflate salts, iodonium salts such as p-toluenesulfonate, triphenylsulfonium, diphenyl (4-methoxyphenyl) sulfonium, (4-phenoxyphenyl) diphenylsulfonium, diphenyl (4-phenylthiophenyl) sulfonium, Such as tris (4-tert-butylphenyl) sulfonium, tris (4-methylphenyl) sulfonium, triarylsulfonium, S, S-dialkyl-S-phenacylsulfonium, etc. Rufonium chloride, bromide, borofluoride, hexafluorophosphate salt, hexafluoroantimonate salt, triflate salt, sulfonium salt such as perfluoro-1-butanesulfonate, chloride of 5-arylthianthrenium salt, bromide , Borofluoride, hexafluorophosphate salt, hexafluoroantimonate salt, triflate salt, thianthrhenium salt such as perfluoro-1-butanesulfonate, 2,4,6-tris (trichloromethyl) -1, 3,5-triazine, 2-phenyl-4,6-bis (trichloromethyl) -1,3,5-triazine, 2-methyl-4,6-bis (trichloromethyl) -1,3,5-triazine, etc. 2,4,6-substituted-1,3,5-triazine compounds include, but are not limited to, Not intended to be.

Among these photocationic polymerization initiators listed, aromatic sulfonium salts and aromatic iodonium salts are preferred because of their high efficiency and availability.

For example, aromatic sulfonium salts include S, S, S ′, S′-tetraphenyl-S, S ′-(4,4′-thiodiphenyl) disulfonium bishexafluorophosphate, diphenyl-4-phenylthio. Examples thereof include phenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluorophosphate, and the like, for example, manufactured by Dow Chemical Co., Ltd., trade names: UVI6992, manufactured by San Apro, Inc., trade names: CPI-100P, CPI-101A, CPI-200K, CPI-210S, etc. Product name: IRGACURE 270, etc., manufactured by BASF Co., Ltd. can be used ("IRGACURE" is a registered trademark of BASF Corporation). Examples of aromatic iodonium salts include 4-isobutylphenyl-4′-methylphenyliodonium hexafluorophosphate, bis (dodecylphenyl) iodonium hexafluoroantimonate, 4-isopropylphenyl-4′-methylphenyliodonium tetrakispentafluorophenylborate, and the like. For example, trade name: Irgacure 250, manufactured by Rhodes Co., Ltd., trade name: Rhodesill 2074 (“Lordsil” is a registered trademark of Rhodia), and the like.

(Photo radical polymerization initiator)
The photoradical polymerization initiator used in the present invention is a compound that decomposes by light irradiation to generate radicals, or a compound that excites the initiator itself by light irradiation and reacts with other compounds to generate radicals. A compound that generates a radical polymerization initiating species is selected.

Examples of such radical photopolymerization initiators include benzylmethyl such as 2,2-dimethoxy-1,2-diphenylethane-1-one (trade name “Irgacure 651”, manufactured by BASF). Ketals, 1-hydroxycyclohexyl phenyl ketone (trade name “Irgacure 184”, manufactured by BASF), 2-hydroxy-2-methyl-1-phenylpropan-1-one (trade name “Darocur 1173”) ", Manufactured by BASF), 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one (trade name" Irgacure 2959 ") , Manufactured by BASF), 2-hydroxy-1- {4- [4- (2-hydroxy-2-methylpropionyl) -benzyl] Α-hydroxyalkylphenones such as Nil} -2-methyl-1-one (trade name “Irgacure 127” manufactured by BASF), 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one (trade name “Irgacure 907”, manufactured by BASF), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone -1 (trade name “Irgacure 369”, manufactured by BASF), etc., α-aminoacetophenones, acetophenone, 2-hydroxy-2-phenylacetophenone, 2-ethoxy-2-phenylacetophenone, 2- Methoxy-2-phenylacetophenone, 2-isopropoxy-2-phenylacetophenone, 2-isobutoxy-2-phenyla Acetophenones such as tophenone, benzyls such as benzyl and 4,4′-dimethoxybenzyl, anthraquinones such as 2-ethylanthraquinone and 2-t-butylanthraquinone, bis (2,4,6-trimethylbenzoyl) -phenylphosphine Oxides, phosphine oxides such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 1,2-octanedione 1- [4- (phenylthio) -2- (o-benzoyloxime)] and 1- [9-ethyl In addition to (keto) oxime esters such as -6- (2-methylbenzoyl) -9H-carbazol-3-yl] -1- (o-acetyloxime), titanocenes, benzophenones, imidazole derivatives, bisimidazoles Derivatives, N-arylglycine derivatives, organic compounds De compounds, aluminate complexes, organic peroxides, N- alkoxy pyridinium salts, and thioxanthone derivatives. Of course, the present invention is not limited to these examples as long as the gist of the present invention is not exceeded. These may be used alone or in combination of two or more.

Of the exemplified photopolymerization initiators, onium salt photopolymerization initiators are particularly preferable. As an onium salt, not only an iodonium salt but also a sulfonium salt is characterized in that the photopolymerization sensitizer composition of the present invention has a photopolymerization sensitization effect.

The photo radical polymerization initiator and the photo cation polymerization initiator can be used alone, respectively, or both the photo radical polymerization initiator and the photo cation polymerization initiator may be used in combination as required.

The amount of the photopolymerization sensitizer composition of the present invention used with respect to the photopolymerization initiator is not particularly limited, but is usually in the range of 5% by weight to 100% by weight, preferably 10% by weight, based on the photopolymerization initiator. The range is 50% by weight or less. If the amount of the photopolymerization sensitizer composition used is less than 5% by weight, it takes too much time to photopolymerize the photopolymerizable compound. I can't get it.

(Photopolymerization initiator composition)
The photopolymerization sensitizer composition of the present invention can be directly added to the photopolymerizable compound, but after preparing the photopolymerization initiator composition by blending with the photopolymerization initiator in advance, the photopolymerization property It can also be added to the compound.

(Photopolymerizable compound)
The photopolymerizable compound used in the photopolymerizable composition of the present invention may be a photocationically polymerizable compound that undergoes photocationic polymerization, a photoradical polymerizable compound that undergoes photoradical polymerization, and further And a photo-hybrid polymerizable compound containing both of them.

(Photo-cationic polymerizable compound)
The cationic photopolymerizable compound used in the photopolymerizable composition of the present invention is a compound that undergoes cationic polymerization with an acid such as Bronsted acid or Lewis acid. Examples thereof include cyclic ethers including cyclic epoxy ring, oxetane ring, tetrahydrofuran ring, tetrahydropyran ring, dioxolane ring, dithiane ring, trithiane ring, dithiolane ring and the like, cyclic thioethers, thioethers, vinyl ethers, and lactones. .

Examples of the photocationically polymerizable compound include diglycerol diether, phenyl glycidyl ether, p-tert-butylphenyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether, 1,2-butylene oxide, 1,3-butadiene monooxide, 1,2-epoxydodecane, epichlorohydrin, 1,2-epoxydecane, styrene oxide, cyclohexene oxide, 3-methacryloyloxymethylcyclohexene oxide, 3-acryloyloxymethylcyclohexene oxide, 3 -Vinylcyclohexene oxide, glycidyl (meth) acrylate, vinylcyclohexene oxide, 4-vinylepoxycyclohexane, epoxy Compounds having one epoxy ring in the molecule such as dioctyl oxahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, brominated bisphenol A diglycidyl ether, brominated bisphenol F diglycidyl ether, brominated bisphenol S diglycidyl ether, epoxy novolac resin, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol S diglycidyl ether, 3 ', 4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (for example, UVR6105, UVR6110, DAW manufactured by DOW) Celoxide 2021P manufactured by Cell, “Celoxide” is a registered trademark of Daicel Corporation, etc.), 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide 2000 manufactured by Daicel), 2- (3,4-epoxycyclohexyl- 5,5-spiro-3,4-epoxy) cyclohexane metadioxane, bis (3,4-epoxycyclohexylmethyl) adipate, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate, 3,4-epoxy- 6-methylcyclohexyl-3 ′, 4′-epoxy-6′-methylcyclohexanecarboxylate, methylenebis (3,4-epoxycyclohexane), dicyclopentadiene diepoxide, di (3,4-epoxycyclohexylmethyl) of ethylene glycol Ete , Ethylenebis (3,4-epoxycyclohexanecarboxylate), 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, polyethylene glycol diglycidyl Ether, polypropylene glycol diglycidyl ethers, 1,1,3-tetradecadiene dioxide, limonene dioxide, 1,2,7,8-diepoxyoctane, 1,2,5,6-diepoxycyclooctane, etc. A compound having two or more epoxy rings in the molecule, such as 3-ethyl-3-hydroxymethyloxetane (oxetane alcohol), 2-ethylhexyloxetane, xylylenebisoxetane, 3-ethyl-3 {[((3 Compounds having an oxetane ring such as -ethyloxetane-3-yl) methoxy] methyl} oxetane, methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, n-butyl vinyl ether, cyclohexyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether, 2- Vinyl ethers such as hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, cyclohexanemethanol monovinyl ether, diethylene glycol monovinyl ether, 1,4-butanediol divinyl ether, cyclohexanedimethanol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, allyl vinyl ether Etc.

These photocationically polymerizable compounds may be used alone or in combination of two or more. Among these photo-cationic polymerizable compounds, compounds having an epoxy ring or an oxetane ring, and vinyl ethers are preferable from the viewpoint of high cationic polymerization and easy availability. In particular, alicyclic epoxy compounds such as 3 ', 4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate are preferred.

(Photoradical polymerizable compound)
The radical photopolymerizable compound used in the photopolymerizable composition of the present invention is not particularly limited as long as it has a functional group capable of reacting with a radical (radical polymerizable functional group) in the molecule. Such functional groups usually include functional groups containing unsaturated bonds such as (meth) acrylic groups and vinyl groups, and examples of compounds having these include the following. At least one radical polymerizable functional group needs to be contained in the compound, and may be contained in two or more.

Examples of such compounds include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhydroxy (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, stearyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, isobornyl (meth) ) Acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxy Traethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, nonylphenoxyethyl (meth) acrylate, nonylphenoxytetraethylene glycol (meth) acrylate, methoxydiethylene glycol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, butoxyethyl (Meth) acrylate, butoxytriethylene glycol (meth) acrylate, 2-ethylhexyl polyethylene glycol (meth) acrylate, nonylphenyl polypropylene glycol (meth) acrylate, methoxydipropylene glycol (meth) acrylate, glycidyl (meth) acrylate, glycerol ( (Meth) acrylate, polyethylene glycol (meth) ac Relate, polypropylene glycol (meth) acrylate, epichlorohydrin modified butyl (meth) acrylate, epichlorohydrin modified phenoxy (meth) acrylate, ethylene oxide (EO) modified phthalic acid (meth) acrylate, EO modified succinic acid (meta ) Acrylate, caprolactone-modified 2-hydroxyethyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, morpholino (meth) acrylate, EO-modified phosphoric acid (meth) An acrylate etc. are mentioned. And monofunctional (meth) acrylates such as (meth) acrylate having an imide group such as imide (meth) acrylate (product name: M-140, manufactured by Toagosei Co., Ltd.).

In addition, 2,2-bis (meth) acryloyloxyphenyl) propane, 2,2-bis [4- (3- (meth) acryloyloxy) -2-hydroxypropoxyphenyl] propane, 2,2-bis (4- (Meth) acryloyloxyphenyl) propane, 2,2-bis (4- (meth) acryloyloxypolyethoxyphenyl) propane, 2,2-bis (4- (meth) acryloyloxydiethoxyphenyl) propane, 2,2 -Bis (4- (meth) acryloyloxytetraethoxyphenyl) propane, 2,2-bis (4- (meth) acryloyloxypentaethoxyphenyl) propane, 2,2-bis (4- (meth) acryloyloxydipropoxy) Phenyl) propane, 2 (4- (meth) acryloyloxydiethoxyphenyl) -2 4- (meth) acryloyloxytriethoxyphenyl) propane, 2 (4- (meth) acryloyloxydipropoxyphenyl) -2- (4- (meth) acryloyloxytriethoxyphenyl) propane, 2,2-bis (4 -(Meth) acryloyloxypropoxyphenyl) propane, 2,2-bis (4- (meth) acryloyloxyisopropoxyphenyl) propane, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol di (meth) acrylate, tetraethylene Glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanedi Ruji (meth) acrylate and the corresponding acrylates to these methacrylates, 1,2-bis bifunctional (meth) acrylates such as (3-methacryloyloxy-2-hydroxypropoxy) ethyl.

Further, methacrylates such as trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, trimethylolmethane tri (meth) acrylate, and acrylates corresponding to these methacrylates, pentaerythritol Tetra (meth) acrylate, pentaerythritol tetraacrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, glycerol tri (meth) acrylate, tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate And trifunctional or higher functional (meth) acrylates.

Furthermore, styrene derivatives such as styrene, vinyl toluene, α-methyl styrene, chlorostyrene, styrene sulfonic acid and salts thereof, maleimide, methyl maleimide, ethyl maleimide, propyl maleimide, butyl maleimide, hexyl maleimide, octyl maleimide, dodecyl maleimide, Maleimides such as stearylmaleimide, phenylmaleimide, cyclohexylmaleimide, vinyl esters such as vinyl acetate, vinyl propionate, vinyl pivalate, vinyl benzoate, vinyl cinnamate, allyl (meth) acrylate, divinylbenzene, triallyl (iso ) Aliases such as cyanurate, diallyl iso (tere) phthalate, diallyl isocyanurate, diallyl tris (2-acryloyloxyethylene) isocyanurate maleate Compound compounds having an unsaturated bond such as and the like.

These radical photopolymerizable compounds may be used alone or in combination of two or more. Among these photoradical polymerizable compounds, (meth) acrylates and styrene derivatives are preferred because of their high radical polymerizability and easy availability.

(Other ingredients)
The photopolymerizable composition of the present invention has an alkali-soluble substituent such as a carboxyl group, a phenolic hydroxyl group, or a sulfonic acid group in the molecule of any of the above-mentioned photocationic polymerizable compound and photoradical polymerizable compound. The photopolymerizable compound which has can also be used. In the case of using these alkali-soluble polymerizable compounds, the photopolymerizable composition containing them is irradiated with light through a mask having a pattern, polymerized and cured, and then subjected to alkali development to unpolymerize the masked portion. The photopolymerizable composition is removed, and a pattern can be formed.

Moreover, a solvent can also be added to the photopolymerizable composition of the present invention as necessary. The solvent to be used is not particularly limited, but hydrocarbon compounds such as hexane, heptane, cyclohexane and decalin, halogen-substituted hydrocarbons such as chloroform, carbon tetrachloride and dichloromethane, aromatic compounds such as benzene, toluene and xylene, chlorobenzene Halogen-substituted aromatics such as diethyl ether, tetrahydrofuran, tetrahydropyran, dioxane, propylene glycol monomethoxy acetate, diglyme and other ether compounds, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and other ketone compounds, ethyl acetate, butyl acetate Ester compounds such as are preferably used.

Furthermore, the photopolymerizable composition of the present invention may contain a polymerization inhibitor related to radical polymerization, a chain transfer agent, and the like. As polymerization inhibitors, phenols such as hydroquinone, methoxyhydroquinone, t-butylcatechol and naphthohydroquinone, quinones such as benzoquinone, naphthoquinone, anthraquinone and hydroxynaphthoquinone, 2,2,6,6-tetramethylpiperidinyl-1 -Oxyl (TEMPO), 4-hydroxy-2,2,6,6-tetramethylpiperidinyl-1-oxyl and the like.

Further, a compound containing a sulfur atom in the molecule can also be used for chain transfer or copolymerization component of a photo-radically polymerizable compound, or for reaction control of cationic polymerization or polymerization component polymerization with a photo-cationic polymerizable compound. Examples of these compounds include butanethiol, propanethiol, hexanedithiol, decanedithiol, n-dodecyl mercaptan, dodecyl (4-methylthio) phenyl ether, benzenethiol, 4-dimethylmercaptobenzene, 2-mercaptoethanol, 1-mercapto. Mercapto compounds such as 2-propanol, 3-mercapto-2-butanol, 3-mercapto-1,2-propanediol, mercaptophenol, or disulfides obtained by oxidizing them, butyl thioglycolate, ethylene glycol bisthioglycolate , Ethylene glycol bisthiopropionate, butanediol bis (3-mercaptoisobutyrate), 1,4-butanediol bisthioglycolate, 1,4-butanediol bisthio Lopionate, octyl β-mercaptopropionate, methoxybutyl β-mercaptopropionate, trishydroxyethyl tristhiopropionate, trimethylolpropane tris (3-mercaptoisobutyrate), trimethylolpropane tris (3-mercaptobutyrate) , Trimethylolpropane tris (3-mercaptopropionate), trimethylolpropane tris (β-thiopropionate), trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, pentaerythritol tetrakis (3- Mercaptopropionate), pentaerythritol tetrakisthioglycolate, pentaerythritol tetrakisthiopropionate, thioglycolic acid, thiosalicylic acid Thiomalic acid, mercaptoacetic acid, 2-mercaptoethanesulfonic acid, 2-mercaptonicotinic acid, 2-mercaptopropionic acid, 3-mercaptopropanesulfonic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, 4-mercaptobutanesulfonic acid, 3- [N- (2-mercaptoethyl) amino] propionic acid, 3- [N- (2-mercaptoethyl) carbamoyl] propionic acid, 2-mercapto-3-pyridinol, 2-mercaptoimidazole, 2-mercaptoethylamine, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 6-trimercapto-s-triazine, N- (2-mercaptopropionyl) glycine, N- (3-mercaptopropionyl) alanine, diisopropylthioxanthone, diethyl Thioxanthone, thiophosphites, trimercaptopropionic acid tris (2-hydroxyethyl) isocyanurate and the like are preferably used. Carbon tetrachloride, carbon tetrabromide, trichloroethylene, tribromoethylene, tribromomethane, bromotrichloromethane, 3-chloro-1-propene, iodopropionic acid, iodoacetic acid, 2-iodoethanol, 2-iodoethanesulfone Acids, halogen-containing compounds such as 3-iodopropanesulfonic acid, alcohols and methacrylates, dimethylacetamide, dimethylformamide, triethylamine, α-methylstyrene dimer, and the like can be blended in the photopolymerizable composition of the present invention. it can.

The photopolymerizable composition of the present invention further includes a colorant such as a pigment and a dye, an organic or inorganic filler, a leveling agent, a surfactant, an antifoaming agent, an increase in the range not impairing the effects of the present invention. Various resin additives such as a sticking agent, a flame retardant, an antioxidant, a stabilizer, a lubricant, a plasticizer, and a water repellent can be blended within a normal use range.

Examples of the colorant include black pigments, yellow pigments, red pigments, blue pigments, and white pigments. Examples of the black pigment include carbon black, acetylene black, lamp black, and aniline black. Examples of yellow pigments include yellow lead, zinc yellow, cadmium yellow, yellow iron oxide, mineral fast yellow, nickel titanium yellow, navel yellow, naphthol yellow S, Hansa Yellow G, Hansa Yellow 10G, Benzidine Yellow G, and Benzidine Yellow. GR, quinoline yellow lake, permanent yellow NCG, tartrazine lake and the like. Examples of red pigments include bengara, cadmium red, red lead, mercury cadmium sulfide, permanent red 4R, risor red, lake red D brilliant carmine 6B, eosin lake, rhodamine lake B, alizarin lake, brilliant carmine 3B, and the like. . Examples of blue pigments include bitumen, cobalt blue, alkali blue lake, Victoria blue lake, phthalocyanine blue, metal-free phthalocyanine blue, phthalocyanine blue partial chloride, first sky blue, and indanthrene blue BC. Examples of white pigments include zinc white, titanium oxide, antimony white, and zinc sulfide. Examples of other pigments include barite powder, barium carbonate, clay, silica, white carbon, talc, and alumina white.

(Preparation of photopolymerizable composition)
The photopolymerizable composition of the present invention can be obtained by mixing the photopolymerization sensitizer composition of the present invention, the above-described photopolymerizable compound and a photopolymerization initiator.

As the photopolymerizable compound, the above-mentioned photo radical polymerizable compound or photo cation polymerizable compound is often used. As the photopolymerizable compound, only the photoradical polymerizable compound or the photocationic polymerizable compound may be used, or a mixture of both the photoradical polymerizable compound and the photocationic polymerizable compound may be used.

Since the photopolymerization sensitizer composition of the present invention can act as a sensitizer in both photoradical polymerization and photocationic polymerization, by selecting a suitable photopolymerization initiator, Photopolymerizable compositions containing both photocationically polymerizable compounds can also be polymerized effectively.

The mixing ratio of the photocationically polymerizable compound and the photoradical polymerizable compound is not particularly limited, and is appropriately selected according to the properties of a coating film or a molded product obtained by photopolymerizing and curing the composition. Usually, the composition ratio is determined such that the weight ratio of the photocationically polymerizable compound and the photoradically polymerizable compound is in the range of 1 to 99 to 99 to 1, preferably 20 to 80 to 80:20.

One kind of each of the photocationically polymerizable compound and the radical photopolymerizable compound may be used, or two or more kinds thereof may be used in combination. Even when two or more of these photopolymerizable compounds are used, the mixing ratio of the photocationic polymerizable compound and the photoradical polymerizable compound is considered as a ratio of the total amount of the respective photopolymerizable compounds.

As the photopolymerization initiator used in the photopolymerizable composition of the present invention, the above-mentioned photoradical polymerization initiator or photocationic polymerization initiator can be used. Usually, when a photoradical polymerizable compound is used as the photopolymerizable compound, a photoradical polymerization initiator is often used, and when a photocationic polymerizable compound is used as the photopolymerizable compound, a photocationic polymerization initiator is often used. Furthermore, in the case where a photoradical polymerizable compound and a photocationic polymerizable compound are used in combination as a photopolymerizable compound, a photoradical polymerization initiator or a photocationic polymerization initiator alone may be used as the photopolymerization initiator or both. May be mixed and used.

In particular, some of the cationic photopolymerization initiators generate cationic polymerization initiating active species and radical polymerization initiating active species by light irradiation. When such an initiator is used, only the photo cationic polymerizable compound and It is also possible to initiate photopolymerization of the photoradically polymerizable compound.

In preparing the photopolymerizable composition of the present invention, the above-mentioned compounds can be obtained by measuring each compound in a suitable container such as a beaker, a flask or a reaction vessel, and a reactor, and stirring and mixing them appropriately. Mixing can be performed by stirring using a stirring blade, mixing using a device such as a homogenizer, or mixing while irradiating ultrasonic waves or the like.

Although there is no restriction | limiting in particular in the temperature at the time of mixing, Usually, it is about -10 to 100 degreeC, Preferably it mixes in the temperature range of room temperature to 50 degreeC. If the temperature at the time of mixing is too low, the viscosity of the composition may become too high and sufficient mixing may not be possible. Etc. are likely to occur, which is not preferable.

You may use a solvent as needed in the case of mixing. In addition, preparation can be performed in an environment in which light of the absorption wavelength of the photopolymerization initiator is blocked, such as a yellow room or a dark room equipped with a safety light so that the photoreaction does not start during mixing.

(Polymerization and curing of photopolymerizable composition)
The photopolymerizable composition of the present invention can be polymerized and cured by light irradiation. The photopolymerizable composition according to the present invention can be polymerized and cured by various methods. For example, a coating film, a film, or a sheet can be obtained by irradiating light on a material coated on a suitable substrate or the photopolymerizable composition sandwiched between glass plates or the like provided with spacers. . In addition, a polymerized and cured molded product can be obtained by irradiating light onto a mold in which the photopolymerizable composition is poured into a mold that transmits light. Further, by applying the photopolymerizable composition and then irradiating light through a mask having an appropriate pattern, polymerization and curing according to the pattern can be performed.

Furthermore, photopolymerization of the photopolymerizable compound in the reactor can be carried out by charging the photopolymerizable composition into a suitable reactor such as a flask and irradiating it with stirring as necessary. The polymerization by light irradiation may be performed in an inert atmosphere or may be performed in a normal atmosphere. For example, in the case where the photopolymerizable composition of the present invention contains a photoradical polymerizable compound, the polymerization may proceed efficiently because the generated radicals are less likely to be consumed by oxygen by polymerization under an inert atmosphere. On the other hand, when the photocationic polymerizable composition is included in the photopolymerizable composition of the present invention, it is possible to prevent the generated cationic species from being deactivated by moisture in the atmosphere.

(light source)
As a light source used in the light irradiation in the present invention, it is preferable to use a light source including light having a wavelength of 300 to 500 nm. A light source including a plurality of wavelength components may be used, or a light source that emits so-called monochromatic light using an LED or laser light may be used. Specifically, a high pressure mercury lamp, an ultrahigh pressure mercury metal halide lamp, a gallium doped lamp, a microwave excitation type UV lamp (for example, H bulb, D bulb, V bulb manufactured by Fusion Co., Ltd.), 365 nm, 375 nm, 395 nm, 405 nm, Examples thereof include an LED lamp that emits light having a wavelength of 436 nm or the like, or laser light. It is also possible to use light from lighting fixtures such as sunlight, incandescent lamps and fluorescent lamps.

(Use of photopolymerizable composition)
The photopolymerizable composition of the present invention can be used for coating agents, paints, inks, molding materials and the like that can be reacted, polymerized and cured by light irradiation. Specifically, coating materials and protective film materials such as paints, hard coat agents, antifouling films, antireflection films, impact buffer films, overcoat agents, etc., which are applied onto substrates such as metals, resins, glass, paper, and wood , Photo-curing adhesives, pressure-sensitive adhesives, photo-disintegration / decomposition-type paints, coating films, molded products, optical recording media such as hologram materials or materials for optical recording media, resin for optical modeling, 3D printer ink ( Resins), resists for electronic circuits and semiconductor manufacturing, color filter resists for displays such as liquid crystal displays and organic EL displays, resists for electronic materials such as black matrix resists and dry film resists, interlayer insulation films, protective films, and light extraction Film, sealant, sealant, printing ink for screen printing, offset printing, gravure printing, etc., for inkjet printers Photocurable ink, composition for laser patterning, lens, lens array, optical waveguide, light guide plate, light diffusion plate, diffraction element, optical member such as optical adhesive, nanoimprinting material, etc. Applicable. Since the photopolymerization sensitizer composition and the photopolymerizable composition of the present invention can suppress coloring of the polymerized product and the cured product, in particular, image-related devices such as LCDs and organic EL displays, touch panels, optical lenses, etc. It is suitably used for adhesives such as OCA (Optically Clear Adhesive) and OCR (Optical Clear Resin) used in the device, adhesives, coating agents and the like.

In order to describe the present invention more specifically, some examples will be described below. However, the scope of the present invention is not limited to the scope of these examples. The product was confirmed based on the measurement by the following equipment.

(1) Melting point: Melting point measuring device manufactured by Gelen Camp, model MFB-595 (conforms to JIS K0064)
(2) Infrared (IR) spectrophotometer: Model IR-810 manufactured by JASCO Corporation
(3) Nuclear magnetic resonance apparatus (NMR): manufactured by JEOL Ltd., model ECS-400 FT NMR Spectrometer

The yellowness in this example indicates the degree to which the hue is separated from colorless or white in the yellow direction, and is as described in JIS K7373.

In this example, yellowness was determined as follows. That is, after measuring a transmission spectrum of a cured coating film in a wavelength range of 380 nm to 780 nm using a spectrophotometer UV-2600 manufactured by Shimadzu Corporation, yellowness was calculated using hue analysis software “color measurement” software also manufactured by Shimadzu Corporation. .

(Synthesis Example 1) 9,10-bis (2-hydroxypropoxy) anthracene (Compound A-1)
154 g of a 20 wt% aqueous sodium salt solution of 9,10-dihydroxyanthracene obtained by heating an aqueous sodium salt solution of 9,10-anthraquinone and 1,4,4a, 9a-tetrahydroanthraquinone to 90 ° C. for 2 hours (as anthraquinone) 0.16 mol) was added 46 g (0.78 mol) of propylene oxide under a nitrogen atmosphere. As the reaction proceeds, the reaction solution is weak and exothermic. Within 10 minutes, the internal temperature reaches 40 ° C., and then the liquid temperature gradually decreases, and crystals are deposited with it. After 3 hours, 100 ml of methanol was added and reslurried, and then the precipitated product was filtered to obtain 35.6 g of a yellow powder of 9,10-di (2-hydroxypropoxy) anthracene. The yield based on the starting 9,10-dihydroxyanthracene was 70 mol%.

(Synthesis Example 2) 9,10-bis (2-hydroxy-3-butoxypropoxy) anthracene (Compound A-2)
To a 200 ml four-necked flask equipped with a thermometer, 55.9 g (0.048 mol as anthraquinone) of a sodium salt of 9,10-dihydroxyanthracene sodium salt and 25.0 g of acetone were added under a nitrogen atmosphere. The internal temperature was raised to 50 ° C., and 25.0 g (192 mmol) of butyl glycidyl ether was added dropwise over 20 minutes, followed by stirring for 6.5 hours. The reaction solution was cooled to room temperature, 40 ml of methyl isobutyl ketone was added, and the aqueous layer was removed after stirring. Similarly, after extracting and washing twice with 20 ml of pure water, the reaction solution was suction filtered to remove insoluble matters. The filtrate was concentrated to dryness to give an orange solid. The resulting orange crystals were added with 100 ml of hexane, stirred, slurried, filtered with suction, washed twice with 20 ml of hexane, and dried to give 9,10-bis (2-hydroxy-3-butoxypropoxy) anthracene. 21.3 g (light orange crystals) was obtained. The yield based on the starting 9,10-dihydroxyanthracene was 94 mol%.

(Synthesis Example 3) 9,10-bis (2-hydroxy-3-allyloxypropoxy) anthracene (Compound A-3)
In a 100 ml four-necked flask equipped with a thermometer, 27.9 g (0.024 mol as anthraquinone) aqueous solution of sodium salt of 9,10-dihydroxyanthracene in a nitrogen atmosphere, 20.0 g of methyl isobutyl ketone, tetra 1.2 g of butylammonium bromide was added. The internal temperature was raised to 70 ° C., and 10.9 g (95 mmol) of allyl glycidyl ether was added dropwise over 30 minutes, followed by stirring for 5 hours. The reaction solution was cooled to room temperature and the aqueous layer was removed. Extraction washing was performed by adding 20 ml of pure water to the reaction liquid, stirring and removing the aqueous layer. After performing the same operation once more, the reaction solution was suction filtered to remove insolubles. The filtrate was concentrated to dryness to give a brown solid. To the obtained brown crystals, 60 ml of hexane was added, stirred, slurried, filtered with suction, washed twice with 20 ml of hexane, and dried to give 9,10-bis (2-hydroxy-3-allyloxypropoxy). 10.2 g (light brown) of anthracene was obtained. The yield based on the starting 9,10-dihydroxyanthracene was 97 mol%.

Example 1
As a polymerizable compound, 100 parts of an alicyclic epoxy compound 3 ′, 4′-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (Celoxide 2021P manufactured by Daicel) was used, and isobutylphenyl (4- Methylphenyl) iodonium hexafluorophosphate (Irgacure 250, manufactured by BSF Corporation) 5.0 parts, 9,10-bis (2- A photopolymerization initiator composition obtained by mixing 0.6 part of hydroxypropoxy) anthracene and 0.5 part of 1,4-diethoxynaphthalene was added to prepare a photopolymerizable composition. The composition was applied on a tack film (cellulose triacetate film, thick film 100 μm) using a bar coater (No. 8) so that the film thickness was 12 microns. Thereafter, this coating film was irradiated with light using an ultraviolet LED (manufactured by Phoseon, center wavelength: 395 nm, irradiation intensity: 50 mW / cm ² ) in an air atmosphere, and the coating film was tacky at a certain time. Confirmed by The light irradiation time “tack free time” from the start of light irradiation to the elimination of tackiness on the coated surface of the composition was 5 seconds. Moreover, it was 0.72 when the yellowness of the cured coating film at that time was measured with the spectrophotometer (Shimadzu Corporation UV2600).

(Comparative Example 1)
The 9,10-bis (2-hydroxypropoxy) anthracene used as the photopolymerization sensitizer in Example 1 was replaced with 9,10-dibutoxyanthracene, and the amount used was changed from 0.6 parts to 0.5 parts. A photopolymerizable composition was prepared in the same manner as in Example 1 except for changing, and coating and light irradiation were performed. The light irradiation time “tack free time” from the start of light irradiation to the elimination of tackiness on the coated surface of the composition was 5 seconds. The yellowness of the cured coating film at that time was 1.07.

(Comparative Example 2)
Except that 0.5 part of 1,4-diethoxynaphthalene used as a photopolymerization sensitizer in Example 1 is not used and only 0.6 part of 9,10-bis (2-hydroxypropoxy) anthracene is used. A photopolymerizable composition was prepared in the same manner as in Example 1, and coated and irradiated with light. The light irradiation time “tack free time” from the start of light irradiation until the tackiness of the coated surface of the composition disappeared was 10 seconds. Moreover, it was 0.68 when the yellowness of the cured coating film at that time was measured with the spectrophotometer (Shimadzu Corporation UV2600).

(Comparative Example 3)
A photopolymerizable composition was prepared in the same manner as in Comparative Example 2 except that the amount of 9,10-bis (2-hydroxypropoxy) anthracene used in Comparative Example 2 was changed from 0.6 part to 1.0 part, Application and light irradiation. The light irradiation time “tack free time” from the start of light irradiation to the elimination of tackiness on the coated surface of the composition was 5 seconds. Further, the yellowness of the cured coating film at that time was 1.04.

(Comparative Example 4)
The same as Comparative Example 2 except that 9,10-bis (2-hydroxypropoxy) anthracene in Comparative Example 2 was replaced with 9,10-dibutoxyanthracene and the amount used was changed from 0.6 parts to 0.5 parts. A photopolymerizable composition was prepared, applied and irradiated with light. The light irradiation time “tack free time” from the start of light irradiation until the tackiness of the coated surface of the composition disappeared was 10 seconds. Further, the yellowness of the cured coating film at that time was 0.97.

(Comparative Example 5)
In the same manner as in Comparative Example 2, except that 9,10-bis (2-hydroxypropoxy) anthracene in Comparative Example 2 was replaced with 9,10-dibutoxyanthracene and the amount used was changed from 0.6 part to 1.0 part. A photopolymerizable composition was prepared, applied and irradiated with light. The light irradiation time “tack free time” from the start of light irradiation to the elimination of tackiness on the coated surface of the composition was 5 seconds. The yellowness of the cured coating film at that time was 2.02.

Comparison of Example 1 and Comparative Example 1 reveals the following. That is, a combination of 9,10-dibutoxyanthracene and 1,4-diethoxynaphthalene, which are known photopolymerization sensitizers, and 9,10-bis (2-hydroxypropoxy) anthracene of the present invention and 1,4- When the combination of diethoxynaphthalene is compared, the curing rate when the photopolymerizable composition containing the photopolymerization sensitizer is cured does not change, but the yellowness of the cured product contains 9,10-dibutoxyanthracene. In some cases, it is very high at 1 or more, but in the combination of the present invention, it is 0.72, which is a practically no problem level.

From the comparison between Example 1 and Comparative Example 2, when 9,10-bis (2-hydroxypropoxy) anthracene is used alone, there is no problem with the yellowness of the cured product, but 1,4-diethoxynaphthalene is not used in combination. It can be seen that the curing time is doubled. Further, as is clear from Comparative Example 3, it can be seen that when the amount of 9,10-bis (2-hydroxypropoxy) anthracene added is increased in order to increase the effect speed, the yellowness is deteriorated.

In addition, it can be seen from Comparative Examples 4 and 5 that the cured product is markedly colored when 9,10-dibutoxyanthracene, which is a known photopolymerization sensitizer, is used alone. The problem of coloring of 9,10-dibutoxyanthracene is apparent not only by comparing Example 1 and Comparative Example 1, but also by comparing Comparative Examples 4, 5 and Comparative Examples 2, 3.

From the above results, the following is clear. That is, 9,10-dibutoxyanthracene, which is a conventionally used photopolymerization sensitizer, has a problem of causing coloring of a cured product. This coloring problem and the problem of obtaining a practical effect speed can be solved by using 9,10-bis (2-hydroxypropoxy) anthracene of the present invention and 1,4-diethoxynaphthalene together.

Claims (9)

(A) An anthracene compound represented by the general formula (1) and (B) a naphthalene compound represented by the general formula (2) or a benzene compound represented by the general formula (3). Agent composition.

(In General Formula (1), R ¹ is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxymethyl group having an alkoxy group having 1 to 5 carbon atoms, an allyloxymethyl group, or an aryl having 6 to 10 carbon atoms. Represents any of aryloxymethyl groups having a group, X and Y may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a halogen atom.)

(In General Formula (2), n represents an integer of 1 or more and 3 or less, R ³ represents either an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted by an oxygen atom, OR ³ When there are a plurality of these, OR ³ may be the same or different, X ² and Y ² may be the same or different, a hydrogen atom, a halogen atom, a carbon number of 1 to 8 Represents an alkyl group, an aralkyl group, an alkoxy group or an aryloxy group.)

(In General Formula (3), R ⁴ and R ⁵ may be the same or different and each represents an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted with an oxygen atom. X ³ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aralkyl group, an alkoxy group, or an aryloxy group. The photopolymerization sensitizer composition according to claim 1, wherein the naphthalene compound represented by the general formula (2) of the component (B) is a naphthalene compound represented by the following general formula (4). .

(In General Formula (4), R ⁶ and R ⁷ may be the same or different, and represent either an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted by an oxygen atom. , X ⁴ and Y ³ may be the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aralkyl group, an alkoxy group or an aryloxy group. The photopolymerization sensitizer composition according to claim 1, wherein the benzene compound represented by the general formula (3) of the component (B) is a benzene compound represented by the following general formula (5). .

(In General Formula (5), R ⁸ and R ⁹ may be the same or different, and represent either an alkyl group having 1 to 9 carbon atoms or a glycidyl group which may be substituted by an oxygen atom. X ⁵ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aralkyl group, an alkoxy group or an aryloxy group. In addition to the photopolymerization sensitizer composition as described in any one of Claims 1 thru | or 3, it contains (C) photoinitiator and (D) photopolymerizable compound, The photopolymerizability characterized by the above-mentioned. Composition. The photopolymerizable composition according to claim 4, wherein the photopolymerization initiator (C) is a photocationic polymerization initiator and the photopolymerizable compound (D) is a photocationic polymerizable compound. The photopolymerizable composition according to claim 4, wherein the photopolymerization initiator (C) is a photoradical polymerization initiator, and the photopolymerizable compound (D) is a photoradical polymerizable compound. The photopolymerizable composition (D) according to claim 4, wherein the photopolymerizable compound (D) contains both a radical photopolymerizable compound and a cationic photopolymerizable compound. The manufacturing method of the hardened | cured material which obtains hardened | cured material by irradiating an energy ray to the photopolymerizable composition as described in any one of Claim 4 thru | or 7. The method for producing a cured product according to claim 8, wherein the energy ray to be irradiated contains light in a wavelength range of 300 nm to 500 nm.