JP2023124657A - Dibenzoxanthene compound, polymer, composition, cured product, molding and method for producing cured product - Google Patents

Abstract

To provide a compound that gives a polymer having a low melt viscosity and a high refractive index.SOLUTION: Provided herein are a dibenzoxanthene compound represented by formula (I), and a polymer including the dibenzoxanthene compound represented by formula (I) as its constituent monomer (where Ar is a substituted phenyl group or substituted naphthyl group).SELECTED DRAWING: None

Description

TECHNICAL FIELD The present invention relates to a dibenzoxanthene compound and a polymer thereof, a composition containing these and a cured product thereof, a method for producing a cured product using the composition, and a molded product of the polymer.

2. Description of the Related Art Optical glasses or optical transparent resins are used as materials for optical elements and optical paints used in various cameras, such as cameras, film-integrated cameras, and video cameras, and optical systems such as microlenses. Optical glass is excellent in heat resistance, transparency, dimensional stability, chemical resistance, etc., and there are many kinds of materials having various refractive indices (nD) and Abbe numbers (νD). However, optical glass has the problems of high material cost, poor moldability, and low productivity. In particular, the processing of an aspherical lens used for aberration correction requires extremely advanced technology and high cost, which poses a major obstacle for practical use.

On the other hand, optical lenses made from optical transparent resins, especially thermoplastic transparent resins, can be mass-produced by injection molding. used as a purpose. Examples of optical transparent resins include polystyrene, poly-4-methylpentene, and polymethyl methacrylate.

However, when an optical transparent resin is used as an optical material such as an optical lens, heat resistance is required in addition to the refractive index and Abbe number. For example, polystyrene, poly-4-methylpentene, and polymethyl methacrylate all have weak points such as low heat resistance, and are therefore not preferred because they are limited in places where they can be used.

On the other hand, in general, when the refractive index of the optical material is high, a lens element having the same refractive index can be realized with a surface having a smaller curvature, so that the amount of aberration that occurs can be reduced. Increasing the refractive index is useful because it enables a reduction in the number of lenses, a reduction in sensitivity to eccentricity of the lenses, and a reduction in the size and weight of the lens system by reducing the thickness of the lenses.

In Patent Document 1, a polycarbonate resin and a polyester resin having a fluorene skeleton are proposed as resins suitable for use as optical materials. Further, in Patent Document 2, a polycarbonate resin having an indane skeleton is proposed as a resin suitable for use as an optical material.

JP 2017-171827 A JP 2019-108493 A

However, a resin having a dioxy unit of a fluorene skeleton as described in Patent Document 1 has a high melt viscosity and is inferior in moldability (moldability). A resin having an indane skeleton as described in Patent Document 2 has a low melt viscosity, but there is room for improvement in terms of refractive index.
The problem to be solved by the present invention is to provide a compound that gives a polymer having a low melt viscosity and a high refractive index, and the polymer.

The present inventors have made intensive studies and found that the above problems can be solved by using a dibenzoxanthene compound having a specific structure.

That is, the present invention relates to the following items.
[1] A dibenzoxanthene compound represented by the following general formula (I).
(Wherein, Ar is a group represented by the following formula (Ar1), (Ar2) or (Ar3),
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² (hereinafter also referred to as “R ¹ to R ¹² ”) are , each independently, one or more of a hydrogen atom, —O—Y ¹ X ¹ , a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a methylene group in the hydrocarbon group is represents a group substituted with a divalent group selected from <Group A>,
<Group A> is -O-, -CO-, -COO-, -OCO-, -NR ¹³ -, -NR ¹³ CO-, and -S-;
R ¹³ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
Y ¹ is a single bond, a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, or one or more methylene groups in the hydrocarbon group selected from the following <group B> Represents a group substituted by a divalent group represented by
X ¹ represents a hydrogen atom, a hydroxyl group, an acrylic group, a methacrylic group, a vinyl group, an epoxy group, an oxetanyl group, a carboxyl group, an isocyanate group, a mercapto group, an acid anhydride group, or an amino group;
When multiple Y ¹ and X ¹ are present in the molecule, they may be the same or different,
<Group B> is -O-, -CO-, -COO-, -OCO-, -NR ¹⁴ -, -NR ¹⁴ CO-, and -S-;
R ¹⁴ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. )
(In the formula, ^R21 , ^R22 , ^R23 , ^R24 , ^R25 , ^R26 , ^R27 , ^R28 , ^{R29 , R30} , R31, ^R32 , ^R33 , ^R34 , ^R35 , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ (hereinafter also referred to as “R ²¹ to R ³⁹ ”) each independently represent a hydrogen atom, —O—Y ² X ² , substituted or unsubstituted carbon atoms of 1 to 20 hydrocarbon groups or one or more of the methylene groups in the hydrocarbon groups represent a group substituted with a divalent group selected from the following <group C>,
Y ² is a single bond, a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, or one or more methylene groups in the hydrocarbon group selected from <Group C> below. Represents a group substituted by a divalent group represented by
^X2 represents a hydrogen atom, a hydroxyl group, an acrylic group, a methacrylic group, a vinyl group, an epoxy group, an oxetanyl group, a carboxyl group, an isocyanate group, a mercapto group, an acid anhydride group, or an amino group;
When multiple Y ² and X ² are present in the molecule, they may be the same or different,
<Group C> is -O-, -CO-, -COO-, -OCO-, -NR ⁴⁰ -, -NR ⁴⁰ CO-, and -S-;
R ⁴⁰ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
with the proviso that when Ar is Ar1, two or more of R ²¹ , R ²² , R ²³ , R ²⁴ and R ²⁵ are —O—Y ² X ² ;
when Ar is Ar2, one or more of R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ and R ³² is —O—Y ² X ² ;
when Ar is Ar3, one or more of R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ is —O—Y ² X ² ;
* represents a bond. )

[2] when Ar is Ar1, two of R ²¹ , R ²² , R ²³ , R ²⁴ and R ²⁵ are —O—Y ² X ² ;
when Ar is Ar2, two of R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ and R ³² are —O—Y ² X ² ;
The dibenzoxanthene compound according to [1], wherein when Ar is Ar3, two of R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ are —O—Y ² X ² . .

[3] one or more of X ¹ is a hydrogen atom, a hydroxyl group, an acrylic group, or an epoxy group, and one or more of X ² is a hydrogen atom, a hydroxyl group, an acrylic group, or an epoxy group; The dibenzoxanthene compound according to [1] or [2].

[4] Any one of [1] to [3], wherein (Ar1) is represented by the following general formula (Ar4) and (Ar2) is represented by the following general formula (Ar5) or (Ar6) of dibenzoxanthene compounds.
(wherein R ⁴¹ , R ⁴² and R ⁴³ (hereinafter also referred to as “R ⁴¹ to R ⁴³ ”) are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms or one or more of the methylene groups in the hydrocarbon group represents a group substituted with a divalent group selected from <Group D> below,
R ⁴⁴ , R ⁴⁵ , R ⁴⁶ , R ⁴⁷ , R ⁴⁸ , R ⁴⁹ , R ⁵⁰ , R 51 , R ⁵² , R ^{53 ,} R ⁵⁴ and R ⁵⁵ (hereinafter also referred to as “R ⁴⁴ to R ⁵⁵ ”) are , one or more of —O—Y ¹⁵ X ¹⁵ , a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a methylene group in the hydrocarbon group, each independently represents a group substituted with a divalent group selected from <Group D>,
<Group D> is -O-, -CO-, -COO-, -OCO-, -NR ⁶¹ -, -NR ⁶¹ CO-, and -S-;
Y ¹¹ , Y ¹² , Y ¹³ , Y ¹⁴ and Y ¹⁵ (hereinafter also referred to as “Y ¹¹ to Y ¹⁵ ”) are each independently a single bond, substituted or unsubstituted C 1-20 2 one or more of the methylene groups in the valent hydrocarbon group or the hydrocarbon group represents a group substituted with a divalent group selected from the above <group D>,
X ¹¹ , X ¹² , X ¹³ , X ¹⁴ and X ¹⁵ (hereinafter also referred to as “X ¹¹ to X ¹⁵ ”) each independently hydrogen atom, hydroxyl group, acrylic group, methacrylic group, vinyl group, epoxy group, oxetanyl group, carboxyl group, isocyanate group, mercapto group, acid anhydride group, or amino group,
When multiple Y ¹⁵ and X ¹⁵ are present in the molecule, they may be the same or different,
R ⁶¹ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
* represents a bond. )

[5] A polymer comprising the dibenzoxanthene compound according to any one of [1] to [4] as a monomer.

[6] A composition containing the dibenzoxanthene compound according to any one of [1] to [4] or the polymer according to [5].

[7] The composition according to [6], which contains a polymerization initiator.

[8] Cured product obtained from the composition according to [7]

[9] A molded article comprising the polymer according to [5].

[10] A method for producing a cured product, comprising heating or irradiating the composition according to [7].

The dibenzoxanthene compound of the present invention is promising because it gives a polymer having a high refractive index and a low melt viscosity, and is particularly useful as an optical material.

The present invention will now be described in detail with respect to its preferred embodiments.
1. Dibenzoxanthene compound

The dibenzoxanthene compound of the present invention is represented by general formula (I). Hereinafter, the compound represented by general formula (I) is also referred to as the compound of the present invention.

(Wherein, Ar is a group represented by the following formula (Ar1), (Ar2) or (Ar3),
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² are each independently a hydrogen atom, —O—Y ¹ X ¹ , one or more of the substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms or the methylene group in the hydrocarbon group is substituted with a divalent group selected from the following <group A> represents the group
<Group A> is -O-, -CO-, -COO-, -OCO-, -NR ¹³ -, -NR ¹³ CO-, and -S-;
R ¹³ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
Y ¹ is a single bond, a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, or one or more methylene groups in the hydrocarbon group selected from the following <group B> Represents a group substituted by a divalent group represented by
X ¹ represents a hydrogen atom, a hydroxyl group, an acrylic group, a methacrylic group, a vinyl group, an epoxy group, an oxetanyl group, a carboxyl group, an isocyanate group, a mercapto group, an acid anhydride group, or an amino group;
When multiple Y ¹ and X ¹ are present in the molecule, they may be the same or different,
<Group B> is -O-, -CO-, -COO-, -OCO-, -NR ¹⁴ -, -NR ¹⁴ CO-, and -S-;
R ¹⁴ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. )

(In the formula, ^RR21 , ^R22 , ^R23 , ^R24 , ^R25 , R26, ^R27 , ^R28 , ^{R29 , R30} , ^R31 , ^R32 , ^R33 , ^R34 , ^R35 , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ are each independently a hydrogen atom, —O—Y ² X ² , a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or methylene in the hydrocarbon group one or more of the groups represents a group substituted with a divalent group selected from the following <group C>,
Y ² is a single bond, a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, or one or more methylene groups in the hydrocarbon group selected from <Group C> below. Represents a group substituted by a divalent group represented by
^X2 represents a hydrogen atom, a hydroxyl group, an acrylic group, a methacrylic group, a vinyl group, an epoxy group, an oxetanyl group, a carboxyl group, an isocyanate group, a mercapto group, an acid anhydride group, or an amino group;
When multiple Y ² and X ² are present in the molecule, they may be the same or different,
<Group C> is -O-, -CO-, -COO-, -OCO-, -NR ⁴⁰ -, -NR ⁴⁰ CO-, and -S-;
R ⁴⁰ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
with the proviso that when Ar is Ar1, two or more of R ²¹ , R ²² , R ²³ , R ²⁴ and R ²⁵ are —O—Y ² X ² ;
when Ar is Ar2, one or more of R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ and R ³² is —O—Y ² X ² ;
when Ar is Ar3, one or more of R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ is —O—Y ² X ² ;
* represents a bond. )

As shown by the evaluation results of Examples described later, in the present invention, a material having excellent heat resistance, a high refractive index, and a low melting point viscosity can be obtained due to the structure of the compound represented by the formula (I). . Moreover, as shown in the examples described later, the compound of the present invention itself has a high refractive index.

In the present specification, hydrocarbon groups having 1 to 20 carbon atoms include aliphatic hydrocarbon groups having 1 to 20 carbon atoms and aromatic hydrocarbon groups having 6 to 20 carbon atoms. The aliphatic hydrocarbon group having 1 to 20 carbon atoms includes an alkyl group having 1 to 20 carbon atoms and an alkenyl group having 2 to 20 carbon atoms. Aromatic hydrocarbon groups having 6 to 20 carbon atoms include aryl groups having 6 to 20 carbon atoms and arylalkyl groups having 7 to 20 carbon atoms.

Here, the hydrocarbon group having 1 to 20 carbon atoms in the present specification means R ¹ to R ¹² , R ¹³ , R ¹⁴ , R ²¹ to R ³⁹ , R ⁴⁰ , Y ¹ , Y ² as well as the carbons represented by R ⁴¹ to R ⁴³ , R ⁴⁴ to R ⁵⁵ , R ⁶¹ and Y ¹¹ to Y ¹⁵ in (Ar4) to (Ar6) which are preferred forms of formula (I) and will be described later. It also includes hydrocarbon groups with 1 to 20 atoms. The contents of (Ar4) to (Ar6) are as already described in [4] above. Since the contents of the groups used in formula (I) and (Ar4) to (Ar6) have many points in common, hereinafter, as an explanation of examples of the groups used in the present invention, not only the group of formula (I) but also the above [ 4] are also added to the explanation.

In the present specification, an alkyl group having 1 to 20 carbon atoms means a chain alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, and a cycloalkyl group having 4 to 20 carbon atoms. Contains alkyl groups. Among these hydrocarbon groups, when used as an optical material, a chain alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, More preferred are a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkylalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 10 carbon atoms, and the like. .

In the present specification, chain alkyl groups having 1 to 20 carbon atoms include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, amyl, isoamyl, t-amyl and hexyl. , heptyl, octyl, isooctyl, 2-ethylhexyl, t-octyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl and icosyl.

In the present specification, examples of alkenyl groups having 2 to 20 carbon atoms include vinyl, 2-propenyl, 3-butenyl, 2-butenyl, 4-pentenyl, 3-pentenyl, 2-hexenyl, 3-hexenyl, 5 -hexenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 3-octenyl, 3-nonenyl, 4-decenyl, 3-undecenyl, 4-dodecenyl, 3-cyclohexenyl, 2,5-cyclohexadienyl-1- and methyl, and 4,8,12-tetradecatrienyl allyl.

As used herein, a cycloalkyl group having 3 to 20 carbon atoms means a saturated monocyclic or saturated polycyclic alkyl group having 3 to 20 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, adamantyl, decahydronaphthyl, octahydropentalene, bicyclo[1.1.1]pentanyl and tetradecahydroanthracenyl. mentioned. One or two or more hydrogen atoms of these cycloalkyl groups may be substituted with an alkyl group or alkenyl group within the range of 20 or less carbon atoms.

In the present specification, a cycloalkylalkyl group having 4 to 20 carbon atoms means a group having 4 to 20 carbon atoms in which a hydrogen atom of the alkyl group is replaced with a cycloalkyl group. For example, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, cyclononylmethyl, cyclodecylmethyl, 2-cyclobutylethyl, 2-cyclopentylethyl, 2-cyclohexylethyl, 2- cycloheptylethyl, 2-cyclooctylethyl, 2-cyclononylethyl, 2-cyclodecylethyl, 3-cyclobutylpropyl, 3-cyclopentylpropyl, 3-cyclohexylpropyl, 3-cycloheptylpropyl, 3-cyclooctylpropyl, 3-cyclononylpropyl, 3-cyclodecylpropyl, 4-cyclobutylbutyl, 4-cyclopentylbutyl, 4-cyclohexylbutyl, 4-cycloheptylbutyl, 4-cyclooctylbutyl, 4-cyclononylbutyl, 4-cyclodecyl butyl, 3-3-adamantylpropyl and decahydronaphthylpropyl, and the like.

In the present specification, the aryl group having 6 to 20 carbon atoms includes, for example, phenyl, tolyl, xylyl, ethylphenyl, naphthyl, anthryl, phenanthrenyl and the like, the above alkyl groups, the above alkenyl groups and cycloalkyl groups. Phenyl, biphenylyl, naphthyl, anthryl and the like substituted one or more times, such as 4-methylphenyl, 4-vinylphenyl, 2,4,6-trimethylphenyl and the like.

As used herein, an arylalkyl group having 7 to 20 carbon atoms means a group having 7 to 20 carbon atoms in which a hydrogen atom of the alkyl group is replaced with an aryl group. Examples include benzyl, α-methylbenzyl, α,α-dimethylbenzyl, phenylethyl and naphthylpropyl. The above-mentioned arylalkyl group having 7 to 10 carbon atoms means a group having 7 to 10 carbon atoms in which a hydrogen atom of the alkyl group is replaced with an aryl group. Examples include benzyl, α-methylbenzyl, α,α-dimethylbenzyl and phenylethyl.

Since Y ¹ and Y ² in Formula (I) and Y ¹¹ to Y ¹⁵ in (Ar4) to (Ar6) are divalent groups, examples of the above various hydrocarbon groups are Y ¹ and Y ² and Y ¹¹ to Y ¹⁵ , groups obtained by removing one hydrogen atom from the above-mentioned various monovalent hydrocarbon groups are used.

As the group in which one or more methylene groups in the hydrocarbon group having 1 to 20 carbon atoms represented by R ¹ to R ¹² are substituted with a group selected from <Group A>, the above 1 carbon atom group Among the various groups exemplified as hydrocarbon groups of 1 to 20, groups in which one or more of methylene groups in a group having 2 or more carbon atoms are substituted with a group selected from <Group A> can be mentioned. For example, when a methylene group on the bond side of an alkyl group is substituted with an oxygen atom, it becomes an alkoxy group.

Similarly, the group in which the methylene group in the hydrocarbon group having 1 to 20 carbon atoms represented by R ²¹ to R ³⁹ is substituted with a group selected from <Group C> includes Among the various groups exemplified as the hydrocarbon group, groups in which one or more of the methylene groups in the group having 2 or more carbon atoms are substituted with a group selected from <Group C> can be mentioned.

Similarly, the methylene group in the hydrocarbon group having 1 to 20 carbon atoms represented by R ⁴¹ to R ⁴³ and R ⁴⁴ to R ⁵⁵ in (Ar4) to (Ar6), which are preferred embodiments described later, is <group D > as the group substituted with a group selected from >, among the various groups exemplified as the hydrocarbon group having 1 to 20 carbon atoms, one or two or more methylene groups in the group having 2 or more carbon atoms is substituted with a group selected from <Group D>.

In the present specification, a group in which one or more methylene groups in the hydrocarbon group are substituted with a group selected from <group A>, <group C>, or <group D>, <group The groups selected from A>, <Group C> or <Group D> shall not be adjacent to each other.

In addition, as the group in which the methylene group in the hydrocarbon group having 1 to 20 carbon atoms represented by Y ¹ and Y ² is substituted with a group selected from <Group B> or <Group C>, the above-mentioned Y Divalent groups selected from < ^Group B> or <Group C> for 1 or 2 or more methylene groups in the various divalent hydrocarbon groups having 1 to 20 carbon atoms listed as 1 and Y ² A group substituted by is mentioned.

In (Ar4) to (Ar6), which are also suitable forms described later, the methylene group in the hydrocarbon group having 1 to 20 carbon atoms represented by Y ¹¹ to Y ¹⁵ is a group selected from <Group D> As the substituted group, one or more methylene groups in various divalent hydrocarbon groups having 1 to 20 carbon atoms listed as Y ¹¹ to Y ¹⁵ are divalent groups selected from <Group D> A group substituted by a group of

Note that Y ¹ and X ¹ of —O—Y ¹ X ¹ do not have a combination of oxygen atoms adjacent to each other or an oxygen atom and a sulfur atom adjacent to each other. This is the same for Y ² and X ² of —O—Y ² X ² , and Y 11 and X ¹¹ of —O—Y ¹¹ X ¹¹ to Y ¹⁵ and ^X of —O—Y ¹⁵ X ¹⁵ . ¹⁵ is the same.

2 the methylene group in the hydrocarbon group having 1 to 20 carbon atoms or the hydrocarbon group having 1 to 20 carbon atoms is selected from <group A>, <group B>, <group C> or <group D>; one or more of the hydrogen atoms in the group substituted with a valent group is a halogen atom, —O—Y ¹ X ¹ , a tertiary amino group, a nitro group, a cyano group, or a carbon atom number of 2 to It may be substituted with 19 heterocycle-containing groups.
Also, the preferred number of —O—Y ^m X ^m in the compound represented by formula (I) is as described later.

When a hydrocarbon group or a group in which a methylene group in the hydrocarbon group is substituted with a divalent group selected from <group A>, <group B>, <group C> or <group D> has a substituent , The number of carbon atoms of a group in which a hydrocarbon group or a methylene group thereof is substituted with a divalent group selected from <group A>, <group B>, <group C> or <group D> is defined as the above substitution The number includes the number of carbon atoms in the group.

As used herein, a halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.

As used herein, heterocyclic ring-containing groups having 2 to 19 carbon atoms are, for example, pyrrolyl, pyridyl, pyridylethyl, pyrimidyl, pyridazyl, piperazyl, piperidyl, pyranyl, pyranylethyl, pyrazolyl, triazinyl, triazinylmethyl, pyrrolidyl, quinolyl , isoquinolyl, quinoxalyl, quinazolyl, cinnolyl, phthalazyl, pryl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, isoxazolyl, indolyl, benzoxazolyl, benzotriazolyl, isothiazolyl, isoxazolyl, indolyl, morpholinyl, thiomorpholinyl, 2-pyrrolidinon-1-yl, 2-piperidon-1-yl, 2,4-dioxyimidazolidin-3-yl and 2,4 -Dioxyoxazolidin-3-yl, heterocyclic groups such as isocyanur and 1,3-dioxolanyl, and the above hydrocarbon groups in which these heterocyclic groups are selected or the methylene group in the hydrocarbon group is selected from <Group A> It refers to a group etc. bonded to a group substituted with a group. In the heterocyclic group is a hydrocarbon group or a group in which the methylene group in the hydrocarbon group is substituted with a group selected from <group A>, the bond may be present on the heterocyclic ring, and the above hydrocarbon group or A methylene group in the hydrocarbon group may be present in a group substituted with a group selected from <Group A>.

The amino groups represented by X ¹ and X ² in formula (I) and X ¹¹ to X ¹⁵ in [4] include —NH ₂ , primary amino group, secondary amino group and tertiary amino group. is mentioned.

Examples of the acid anhydride groups represented by X ¹ and X ² in formula (I) and X ¹¹ to X ¹⁵ in [4] include a carboxylic anhydride group, a sulfonic anhydride group, a phosphoric anhydride group, and the like. is mentioned.

The compounds of the present invention are represented by —O—Y ^m X ^m (m is 1 or 2. However, when Ar is represented by (Ar4), m is 1, 11, 12 or 15, and Ar is ( When represented by Ar5), m is 1, 13 or 15, and when Ar is represented by (Ar6), m is 1, 14 or 15.) A compound containing a total of two or more From the viewpoint of reactivity, one is preferred, and compounds containing two are most preferred. When the compound of the present invention contains two or more —O—Y ^m X ^m , it is preferred that they have the same functional groups from the viewpoint of polymer production. Examples of similar functional groups include, for example, two or more —O—Y ^m X ^m that are hydroxyl group-containing groups, and two or more —O—Y ^m X ^m in which X ^m is a carboxyl group. Examples include the case where they are of the same type, such as with each other, with each other with acrylic groups, and the like. Further, the compound of the present invention preferably has a high refractive index and a low melt viscosity, and is preferably a compound containing two or more of —O—Y ² X ² as —O—Y ^m X ^m . Compounds containing two —Y ² X ² are more preferred.

Furthermore, when the compound of the present invention has two or more substituents represented by —O—Y ^m X ^m , it is particularly preferable from the viewpoint of polymerizability that each Y ^m and X ^m are the same.

In the formula (I), Ar is preferably (Ar1) because it has a high refractive index and a low melt viscosity, that is, it is excellent in moldability (sometimes referred to as "molding processability").

Ar in the formula (I) is preferably (Ar2) or (Ar3) because it has an excellent refractive index, and (Ar2) is particularly preferable because it is easy to synthesize and has good storage stability.

One of the characteristics of the compound of the present invention is that the group represented by Ar has a substituent represented by —O—Y ² X ² . Thereby, the present invention is excellent in refractive index, polymerizability, and moldability. In addition, there is an effect that negative birefringence can be obtained in the polymer.

Specifically, when Ar is (Ar1), two or more of R ²¹ to R ²⁵ are —O—Y ² X ² , so that the compound of the present invention is excellent in stability and refractive index, Especially excellent in polymerizability and moldability. In particular, it is more preferable that two of R ²¹ to R ²⁵ are —O—Y ² X ² from the viewpoint of excellent stability and refractive index.

When Ar is (Ar2), one or more of R ²⁶ to R ³² are —O—Y ² X ² , so that the compound of the present invention is excellent in stability and refractive index. From the viewpoint of further increasing the stability and refractive index, two or more of R ²⁶ to R ³² are preferably —O—Y ² X ² , and two of R ²⁶ to R ³² are —O—Y ^{2 X2} is most preferred.

In the compound of the present invention, when Ar is (Ar3), one or more of R ³³ to R ³⁹ is —O—Y ² X ² , so that the compound is excellent in stability and refractive index. From the viewpoint of further increasing the stability and refractive index, two or more of R ³³ to R ³⁹ are preferably —O—Y ² X ² , and two of R ³³ to R ³⁹ are —O—Y ² More preferably X ² .

In (Ar1), R ²² , R ²³ or R ²⁴ is preferably —O—Y ² X ² from the standpoints of stability, refractive index and manufacturability.
In (Ar1), it is also preferable that —O—Y ² X ² are adjacent to each other at ortho positions from the viewpoint of moldability and manufacturability.
In terms of moldability and manufacturability, it is particularly preferred that R ²² and R ²³ or R ²³ and R ²⁴ are —O—Y ² X ² .

Furthermore, in terms of ease of manufacture, refractive index, and moldability, at least one of R ²¹ to R ²⁵ in (Ar1) is preferably a hydrogen atom, and more preferably two or more are hydrogen atoms. In terms of ease of manufacture, refractive index, and moldability, the number of carbon atoms in groups other than —O—Y ² X ² among R ²¹ to R ²⁵ is preferably 4 or less, and 1 or less. is more preferred.

In (Ar2), two or more of R ²⁸ to R ³¹ are —O—Y ² X ² , or R ²⁶ , R ²⁷ and R ³² are It is also preferred that one or more are --O--Y ² X ² and one or more of R ²⁸ to R ³¹ are --O--Y ² X ² . Among them, from the viewpoint of ease of production, one or more of R ²⁸ to R ³¹ are —O—Y ² X ² , and one or more of R ²⁶ , R ²⁷ and R ³² are —O—Y ² X ^2. Preferably.

From the viewpoint of ease of production and moldability, when two or more of R ²⁸ to R ³¹ are —O—Y ² X ² , two groups adjacent to each other (that is, R ²⁸ and R ²⁹ , R ²⁹ and R ³⁰ or the two groups R ³⁰ and R ³¹ ) is also --O--Y ² X ² and the two groups in the position of ortho substitution (i.e. R ²⁸ and R ²⁹ or R ³⁰ and R ³¹ ) It is also particularly preferred that is --O--Y ² X ² .

Furthermore, when one or more of R ²⁸ to R ³¹ are —O—Y ² X ² and one or more of R ²⁶ , R ²⁷ and R ³² are —O—Y ² X ² , the 1,5-position Alternatively, two groups at positions 4 and 8 (for example, R ²⁷ and R ³¹ , or R ²⁸ and R ³² ) are —O—Y ² X ² to improve stability, ease of manufacture, and moldability. is particularly preferred in terms of

Furthermore, in terms of stability, refractive index, manufacturability, and birefringence, R ³² is —O—Y ² X ² , or one or two selected from R ²⁸ and R ²⁹ are —O—Y ² X ² It is also preferable that

Also in (Ar3), two or more of R ³⁶ to R ³⁹ are —O—Y ² X ² , or one or more of R ³⁶ to R ³⁹ are —O—Y ² X ² and R ³³ to At least one of R ³⁵ is preferably —O—Y ² X ² from the viewpoint of stability, ease of production, and moldability.

Furthermore, from the viewpoints of ease of manufacture, refractive index, and moldability, one or more of each of R ²⁶ to R ³² of (Ar2) and R ³³ to R ³⁹ of (Ar3), more preferably two or more, More preferably, three or more are hydrogen atoms.
In terms of ease of production, refractive index, and molding processability, groups other than —O—Y ² X ² among each of R ²⁶ to R ³² of (Ar2) and R ³³ to R ³⁹ of (Ar3) The number of carbon atoms is preferably 4 or less, more preferably 1 or less.

Preferred configurations of Y ^m and X ^m are described below. Preferred configurations of Y ^m and X ^m described below are all Y ¹ and X 1 , Y ² and X ² , Y ^{11 and X 11 , Y 12 and X 12 , Y 13 and X 13 , Y 14} and X ¹⁴ , Y ¹⁵ and X ¹⁵ respectively. As noted above, it is preferred that Y ^m and X ^m are Y ² and X ² respectively.
^Ym is any one of (y1) to (y3) below.
(y1) a single bond;
(y2) a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms (hereinafter also simply referred to as "(y2)");
(y3) a group in which the methylene group in the hydrocarbon group is substituted with a group selected from the above <group B> (m = 1) or <group C> (m = 2) (hereinafter also simply referred to as "(y3)" ).

When ^Ym is (y2) or (y3), (y2) or (y3) is preferably an unsubstituted group from the viewpoint of ease of production, refractive index, and molding.
Further, when Y ^m is (y2) or (y3), (y2) or (y3) preferably has 1 to 6 carbon atoms in terms of refractive index, and preferably 1 to 2. is particularly preferred.
Furthermore, when ^Ym is (y2) or (y3), the hydrocarbon group of (y2) or (y3) is preferably an alkylene group from the viewpoint of ease of production and moldability. It is preferably a chain alkylene group.

It is preferable in terms of refractive index that ^Ym is a (y1) single bond.
On the other hand, it is preferable that ^Ym is (y2) or (y3) from the viewpoint of polymerizability, moldability after polymerization, and mechanical strength.

Moreover, it is preferable that ^Ym is (y1) or (y2) from the viewpoint of ease of production and heat resistance.

In any case of Ar, in —O—Y ^m X ^m , the oxygen atoms are not adjacent to each other. Therefore, when Y ^m is a single bond, X ^m is a group other than a hydroxyl group. When Y ^m is (y1) a single bond, X ^m is preferably a hydrogen atom, an acrylic group, a methacrylic group, a vinyl group, or an epoxy group, more preferably a hydrogen atom, an acrylic group, or a methacrylic group, and is a hydrogen atom. is particularly preferred. When X ² is the above group, it is preferable from the point of ease of polymer production and the point of refractive index. When Y ^m is (y2) or (y3), X ^m is preferably a group other than a hydrogen atom, preferably an acrylic group, a methacrylic group, a vinyl group, an epoxy group, a hydroxyl group, an acrylic group, or a methacrylic group. A group or a hydroxyl group is more preferred, and a hydroxyl group is most preferred.

When the compound of the present invention has one or two or more —O—Y ^m X ^m , one or more of the one or two or more X ^m in the molecule is a hydrogen atom, a hydroxyl group, an acrylic group, or a methacrylic group. or an epoxy group is preferable because it is excellent in polymerizability, and a hydroxyl group, an acrylic group, and an epoxy group are more preferable. Especially preferred is any one of the following compounds (1) to (3).
(1) The compound of the present invention has two or more —O—Y ^m X ^m , and said X ^m is an acryl group.
(2) The compound of the present invention has two or more —O—Y ^m X ^m , said Y ^m being (y2) or (y3), and said X ^m being an epoxy group.
(3) the compound of the present invention has a total of two or more -O-Y ^mα H and/or -O-Y ^mβ OH, Y ^mα is (y1) a single bond and Y ^mβ is (y2) or (y3).

Among others, (3) the compound of the present invention has a total of two or more —O—Y ^mα H and/or —O—Y ^mβ OH, Y ^mα is (y1) a single bond, and Y ^mβ is The compound (y2) or (y3) is preferable in that the excellent effects of the present invention can be exhibited particularly easily when polymerized as a polycarbonate compound, a polyester compound, or the like.

In formula (I), R ¹ to R ¹² are each independently a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or one or two methylene groups in the hydrocarbon group A group substituted with a divalent group selected from the following <Group A> is preferable in terms of ease of production and refractive index. In particular, those in which R ¹ to R ¹² are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms are preferred because they are easy to produce and have high storage stability. A hydrogen atom is preferred.

Further, among R ¹ to R ¹² , R ¹ and/or R ¹² are preferably hydrogen atoms from the viewpoint of ease of production. From the standpoint of ease of production, R ¹ to R ¹² preferably have 4 or less carbon atoms, more preferably 1 or less.
Furthermore, from the standpoint of ease of production, one or more of R ² to R ⁴ are preferably hydrogen atoms.
Similarly, from the standpoint of ease of production, one or two of R ⁵ to R ⁶ are preferably hydrogen atoms.
Similarly, one or two of R ⁷ to R ⁸ are preferably hydrogen atoms from the viewpoint of ease of production.
Similarly, from the standpoint of ease of production, one or more of R ⁹ to R ¹¹ are preferably hydrogen atoms.
A dibenzoxanthene compound in which R ¹ to R ¹² are the above groups is preferable because it is easy to produce and has high storage stability.

Among R ¹ to R ¹² in general formula (I), it is preferable that R ¹ is the same as R ¹² from the viewpoint of ease of production. Likewise, it is also preferred that R ² is the same as R ¹¹ and it is also preferred that R ³ is the same as R ¹⁰ . It is also preferred that R ⁴ is the same as R ⁹ , it is also preferred that R ⁵ is the same as R ⁸ , and it is also preferred that R ⁶ is the same as R ⁷ .

The dibenzoxanthene compound in which (Ar1) is represented by the following general formula (Ar4) and (Ar2) is represented by the following general formula (Ar5) or (Ar6) has a high refractive index, polymerizability, It is preferable in terms of excellent heat resistance.
(wherein R ⁴¹ , R ⁴² and R ⁴³ are each independently a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or one or two methylene groups in the hydrocarbon group one or more represents a group substituted with a divalent group selected from the following <group D>,
R ⁴⁴ , R ⁴⁵ , R ⁴⁶ , R ⁴⁷ , R ⁴⁸ , R ⁴⁹ , R ⁵⁰ , R 51 , R ⁵² , R ⁵³ , R ⁵⁴ and ^{R 55 are} each independently —O—Y ¹⁵ X ¹⁵ , hydrogen One or more of the atoms, substituted or unsubstituted hydrocarbon groups having 1 to 20 carbon atoms, or methylene groups in the hydrocarbon groups are substituted with a divalent group selected from the following <group D> represents the group
<Group D> is -O-, -CO-, -COO-, -OCO-, -NR ⁶¹ -, -NR ⁶¹ CO-, and -S-;
Y ¹¹ , Y ¹² , Y ¹³ , Y ¹⁴ and Y ¹⁵ are each independently a single bond, a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, or a methylene group in the hydrocarbon group represents a group substituted with a divalent group selected from the above <Group D>,
X ¹¹ , X ¹² , X ¹³ , X ¹⁴ and X ¹⁵ are hydrogen atom, hydroxyl group, acrylic group, methacrylic group, vinyl group, epoxy group, oxetanyl group, carboxyl group, isocyanate group, mercapto group, acid anhydride group, or represents an amino group,
R ⁶¹ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
* represents a bond. )

From the viewpoint of reactivity, any one or more of R ⁴⁴ , R ⁴⁵ , R ⁴⁶ , R ⁴⁷ , R ⁴⁸ and R ⁴⁹ (hereinafter also referred to as “R ⁴⁴ to R ⁴⁹ ”) in (Ar5) is —O —Y ¹⁵ X ¹⁵ , and any one or more of R ⁵⁰ , R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ and R ⁵⁵ (also referred to as “R ⁵⁰ to R ⁵⁵ ”) in (Ar6) is — O—Y ¹⁵ X ¹⁵ is preferred.
More preferably, any one of R ⁴⁴ to R ⁴⁹ in (Ar5) is —O—Y ¹⁵ X ¹⁵ , and any one of R ⁵⁰ to R ⁵⁵ is —O—Y ¹⁵ X ¹⁵ . preferable.

Examples of the groups in the formulas (Ar4), (Ar5) and (Ar6) are as described above, and will be described in more detail below.

As described above, all of the above-mentioned matters regarding -O-Y ^m X ^m are -O-Y ¹¹ X ¹¹ , -O-Y ¹² X ¹² , -O-Y ¹³ X ¹³ and -O-Y ¹⁴ X ¹⁴ and —O—Y ¹⁵ X ¹⁵ , respectively.
That is, the configurations described above as being preferred for Y ^m all apply to Y ¹¹ , Y ¹² , Y ¹³ , Y ¹⁴ and Y ¹⁵ . In particular, Y ¹¹ and Y ¹² are preferably (y1) or (y2) from the standpoint of ease of production and heat resistance, and (y2) is preferred for improving polymerizability and moldability and mechanical strength after polymerization. point is preferable. In terms of refractive index, it is preferable that Y ¹³ , Y ¹⁴ and Y ¹⁵ are (y1) single bonds.

Preferred groups for X ^m correspond to X ¹¹ , X ¹² , X ¹³ , X ¹⁴ and X ¹⁵ , and each of them is preferably a hydrogen atom, a hydroxyl group, an acrylic group, or an epoxy group because of excellent polymerizability.

In -O-Y ¹¹ X ¹¹ , -O-Y ¹² X ¹² , -O-Y ¹³ X ¹³ , -O-Y ¹⁴ X ¹⁴ and -O-Y ¹⁵ X ¹⁵ , the oxygen atoms shall not be adjacent to each other. Therefore, when Y ¹¹ , Y ¹² , Y ¹³ , Y ¹⁴ and Y ¹⁵ are (y1) single bonds, the corresponding X ¹¹ , X ¹² , X ¹³ , X ¹⁴ and X ¹⁵ are groups other than hydroxyl groups. , a hydrogen atom, an acryl group, a methacryl group, a vinyl group and an epoxy group are preferred, a hydrogen atom, an acryl group and a methacryl group are more preferred, and a hydrogen atom is most preferred. This is because the polymer can be easily produced and the refractive index is also excellent. When Y ¹¹ , Y ¹² , Y ¹³ , Y ¹⁴ and Y ¹⁵ are (y2) or (y3), each of X ¹¹ , X ¹² , X ¹³ , X ¹⁴ and X ¹⁵ is a group other than a hydrogen atom. more preferably acrylic group, methacrylic group, vinyl group, epoxy group or hydroxyl group, still more preferably acrylic group, methacrylic group or hydroxyl group, most preferably hydroxyl group.

As —O—Y ¹¹ X ¹¹ and —O—Y ¹² X ¹² , the following aspects (1′) to (3′) are preferred, and (3′) is particularly preferred, from the viewpoint of excellent polymerizability.
(1′) Both X ¹¹ and X ¹² are acrylic groups.
(2') X ¹¹ and X ¹² are epoxy groups, and the Y ¹¹ and Y ¹² are (y2) or (y3).
(3′) —O—Y ¹¹ X ¹¹ and —O—Y ¹² X ¹² are each independently —O—Y ^mα H or —O—Y ^mβ OH, and Y ^mα is (y1) a single bond; , Y ^mβ are (y2) or (y3).

When Ar is (Ar5) and any one of R ⁴⁴ to R ⁴⁹ is —O—Y ¹⁵ X ¹⁵ , from the viewpoint of excellent polymerizability, the following (1″) to (3″) ) is preferred, and (3'') is particularly preferred.
(1'') Both X ¹³ and X ¹⁵ are acrylic groups.
(2'') X ¹³ and X ¹⁵ are epoxy groups, and the Y ¹³ and Y ¹⁵ are (y2) or (y3).
(3″)—O—Y ¹³ X ¹⁵ and —O—Y ¹³ X ¹⁵ are each independently —O—Y ^mα H or —O—Y ^mβ OH, and Y ^mα is (y1) a single bond and Y ^mβ is (y2) or (y3).

When Ar is (Ar6) and one or more of R ⁵⁰ to R ⁵⁵ is —O—Y ¹⁵ X ¹⁵ , the following (1′″) to ( 3''') is preferred, and (3''') is particularly preferred.
(1''') X ¹⁴ and X ¹⁵ are both acryl groups.
(2''') X ¹⁴ and X ¹⁵ are epoxy groups, and said Y ¹⁴ and Y ¹⁵ are (y2) or (y3).
(3''')-O-Y ¹⁴ X ¹⁵ and -O-Y ¹⁴ X ¹⁵ are each independently -O-Y ^mα H or -O-Y ^mβ OH, and Y ^mα is (y1) a single bond and Y ^mβ is (y2) or (y3).

From the viewpoint of excellent stability and refractive index, when Ar is (Ar5), one or more selected from R ⁴⁵ , R ⁴⁶ , R ⁴⁹ and R ⁴⁸ is preferably —O—Y ¹⁵ X ¹⁵ , More preferably, one or more selected from R ⁴⁵ , R ⁴⁶ and R ⁴⁹ is —O—Y ¹⁵ X ¹⁵ , and more preferably R ⁴⁶ or R ⁴⁹ is —O—Y ¹⁵ X ¹⁵ .

From the viewpoint of excellent stability and refractive index, when Ar is (Ar6), one or more selected from R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ and R ⁵⁵ is —O—Y ¹⁵ X ¹⁵ is preferred, one or more selected from R ⁵¹ , R ⁵² and R ⁵³ is more preferably —O—Y ¹⁵ X ¹⁵ , more preferably R ⁵¹ or R ⁵² is —O—Y ¹⁵ X ¹⁵ preferable.

From the viewpoint of excellent stability and refractive index, when Ar is (Ar4), at least one of R ⁴¹ to R ⁴³ is preferably a hydrogen atom, and more preferably two or more are hydrogen atoms. The number of carbon atoms in R ⁴¹ to R ⁴³ is preferably 4 or less, more preferably 1 or less.

when Ar is (Ar5) or (Ar6), one or more of R ⁴⁴ to R ⁴⁹ , one or more of R ⁵⁰ to R ⁵⁵ , more preferably 2 or more, still more preferably 3 or more is also preferably a hydrogen atom. In addition, the number of carbon atoms in groups other than O—Y ¹⁵ X ¹⁵ in R ⁴⁴ to R ⁴⁹ and R ⁵⁰ to R ⁵⁵ is preferably 4 or less, more preferably 1 or less.

As the dibenzoxanthene compound of the present invention, the following compound Nos. A1 to A35 are included. In addition, No. A32 to A35 are compound Nos. to be described later. It is the same compound as 1-4.

A preferred method for producing the compound of the present invention includes a method of reacting a benzaldehyde compound or naphthaldehyde compound with a naphthol compound in the presence of an acid catalyst such as p-toluenesulfonic acid. Benzaldehyde compounds include 3,4-dihydroxybenzaldehyde, 2,4-dihydroxybenzaldehyde, 2,5-dihydroxybenzaldehyde, 2,6-dihydroxybenzaldehyde, 2,4-dihydroxy-3-methylbenzaldehyde, and methyl naphtho having a hydroxyl group. Examples include, but are not limited to, aldehydes and ethylnaphthaldehyde.
Examples of naphthaldehyde compounds include 1,2-dihydroxy-6-naphthaldehyde, 1,5-dihydroxy-2-naphthaldehyde, 2-hydroxy-1-naphthaldehyde, methylnaphthaldehyde and ethylnaphthaldehyde having a hydroxyl group, isopropyl Non-limiting examples include naphthaldehyde, trimethylnaphthaldehyde, methoxynaphthaldehyde.
Hydroxyalkyl groups such as hydroxypropylation and hydroxyethylation; epoxidation; esterification with acrylic acid or methacrylic acid; halogenation, nitration, oxetanyl Various modification reactions such as conversion, vinyl etherification, etherification, thioetherification, acylation, urethanization and carboxylation can be performed.
Another method for producing the compound of the present invention includes a method of reacting a dibenzoxanthone compound with a phenol compound or a naphthol compound in the presence of an acid catalyst such as sulfuric acid.

2. Polymer A polymer comprising a dibenzoxanthene compound represented by the general formula (I) as a monomer exhibits a high refractive index, a low melting point, and high heat resistance, and is particularly useful as a lens-forming material. .

The polymer preferably has a weight average molecular weight (Mw) of 10,000 to 200,000, more preferably 20,000 to 100,000, and particularly preferably 30,000 to 80,000. This is because when the weight-average molecular weight is within the above range, the polymer particularly satisfies a high refractive index, a low melting point and high heat resistance. The weight average molecular weight can be measured by the method described in Examples below.

Examples of the types of polymers include polycarbonate resins, polyester resins, polyvinyl resins, polyurethane resins, and polyamide resins. Polycarbonate resins and polyester resins are preferred because of their excellent moldability, and polycarbonate resins are particularly preferred.

When the polymer of the present invention is a polycarbonate resin or polyester resin, it is formed, for example, from a polymer having a structural unit represented by the following formula (II). A polymer having a structural unit represented by the following formula (II) is a polycarbonate resin when n = 0 and ^M2 is a direct bond, and n = 1 ^{and M2} is a divalent linking group. In some cases, it is a polyester resin.

(In the formula, M ¹ represents a divalent linking group obtained by removing two hydroxyl groups from a dibenzoxanthene compound represented by the general formula (I) and having two or more (preferably two) hydroxyl groups,
^M2 represents a direct bond or a divalent linking group,
Multiple M ¹ and M ² present in the structure of the polymer may be the same or different,
n represents 0 or 1; )

As the divalent linking group represented by ^M2 in the above formula (II), a dicarboxylic acid residue is preferably exemplified. However, a dicarboxylic acid residue refers to a residue having a structure obtained by removing two COOH groups from a dicarboxylic acid.
The number of carbon atoms in the divalent linking group represented by M ² is preferably from 1 to 60 from the viewpoint of ease of production and stability of the polymer, and more preferably from 2 to 40. More than or equal to 32 or less is particularly preferable.

The preferred contents of the various structures described above for the dibenzoxanthene compound also apply to the polymer represented by the formula (II).

A polymer in which the mass of the structural unit represented by the above formula (II) is 10 to 100% by mass relative to the polymer is preferable because it has excellent refractive index and heat resistance, and 20 to 100% by mass is more preferable. , 30 to 100% by weight is particularly preferred, 40 to 100% by weight is particularly preferred, and 60 to 100% by weight is most preferred.

The polymer preferably has excellent heat resistance. Specifically, the glass transition temperature (Tg) is preferably 100° C. or higher, more preferably 120° C. or higher, and 150° C. or higher. is most preferred. The glass transition temperature is preferably 250° C. or lower from the viewpoint of ease of production of the polymer. The glass transition temperature can be measured by the method described in Examples below.

The melt viscosity at 300° C. of the polymer is preferably less than 1,000 Pa·s, more preferably less than 800 Pa·s, because of its excellent moldability. The melt viscosity can be measured by the method described in Examples below.

A polymer having n=0 and ^M2 being a direct bond in the above formula (II) is prepared by reacting a diol component and a diester carbonate in the presence of a basic compound catalyst, an ester exchange catalyst, or a mixed catalyst consisting of both. can be produced by the melt polycondensation method (hereinafter referred to as "method for producing a polymer that is a polycarbonate resin").
Further, a polymer in which n=1 and ^M2 is a divalent linking group in the above formula (II) can be produced by reacting a diol component as a starting material with a dicarboxylic acid or a dicarboxylic acid derivative. (Hereafter, it describes as "the manufacturing method of the polymer which is a polyester resin.").
Here, the diol component, the diester carbonate, the dicarboxylic acid and the dicarboxylic acid derivative can be used alone, or can be used in combination of two or more.

First, a method for producing a polymer that is a polycarbonate resin will be described. The compound described in the formula (I) is used as the diol component. Preferable examples of the diol component include a total of two or more of —O—Y ^mα H and/or —O—Y as —O—Y ^m X ^m in the dibenzoxanthene compound represented by formula (I). ^mβ OH, Y ^mα is (y1) a single bond, and Y ^mβ is (y2) or (y3), particularly preferred —O—Y ^mα H and/or —O—Y ^mβ The number of OH is two in total.
Examples of such compounds include Compound No. 1 described above. A1 to A12, A14, A17, A21, A23, A24 to A35.

Examples of the carbonic acid diester include diphenyl carbonate, ditolyl carbonate, bis(chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate and dicyclohexyl carbonate. Among these, diphenyl carbonate is particularly preferable because of its excellent polymerizability. The carbonic acid diester is preferably used in a ratio of 0.97 to 1.20 mol, more preferably 0.98 to 1.10 mol, per 1 mol of the diol component. Only one type of carbonic acid diester can be used, or two or more types can be used.

Examples of the basic compound catalyst include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds.

Examples of the alkali metal compound include organic acid salts, inorganic salts, oxides, hydroxides, hydrides and alkoxides of alkali metals. Specifically, sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium hydrogen carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, cesium acetate, lithium acetate, stearin sodium phosphate, potassium stearate, cesium stearate, lithium stearate, sodium borohydride, sodium borophenylate, sodium benzoate, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, hydrogen phosphate Dipotassium, dilithium hydrogen phosphate, disodium phenylphosphate, disodium salt, dipotassium salt, dicesium salt, dilithium salt of bisphenol A, sodium salt, potassium salt, cesium salt, lithium salt of phenol and the like are used. be done.

Examples of the alkaline earth metal compound include organic acid salts, inorganic salts, oxides, hydroxides, hydrides and alkoxides of alkaline earth metals. Specifically, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium hydrogen carbonate, calcium hydrogen carbonate, strontium hydrogen carbonate, barium hydrogen carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, acetic acid Magnesium, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenylphosphate and the like are used.

Examples of the nitrogen-containing compounds include quaternary ammonium hydroxides, salts thereof, and amines. Specifically, quaternary ammonium hydroxides having alkyl, aryl, groups, etc. such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide, Tertiary amines such as triethylamine, dimethylbenzylamine and triphenylamine, secondary amines such as diethylamine and dibutylamine, primary amines such as propylamine and butylamine, 2-methylimidazole, 2-phenylimidazole, benzimidazole or imidazoles such as ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, tetrabutylammonium tetraphenylborate, tetraphenylammonium tetraphenylborate and the like bases or basic salts.

Salts of zinc, tin, zirconium, and lead are preferably used as transesterification catalysts, and these can be used alone or in combination.
Examples of transesterification catalysts include zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin (II) chloride, tin (IV) chloride, tin (II) acetate, tin (IV) acetate, dibutyltin dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead acetate (II), lead acetate (IV), and the like.

These catalysts are used in a ratio of 10 ^-9 to 10 ^-2 mol, preferably in a ratio of 10 ^-7 to 10 ^-3 mol, per 1 mol of the total diol component.

In the melt polycondensation method, the raw materials and catalysts described above are heated under normal pressure or reduced pressure, and melt polycondensation is performed by transesterification while removing by-products. The reaction is generally carried out in two or more stages.

Specifically, the first stage reaction is carried out at a temperature of 120 to 260° C., preferably 180 to 240° C., for 0.1 to 5 hours, preferably 0.5 to 3 hours, under normal pressure or reduced pressure. Then, the diol component and the diester carbonate are reacted by raising the reaction temperature while increasing the degree of pressure reduction in the reaction system, and finally polycondensing at a temperature of 200 to 350° C. for 0.05 to 2 hours under a reduced pressure of 1 mmHg or less. carry out the reaction. Such a reaction may be carried out continuously or batchwise. The reactor used for the above reaction may be a vertical type equipped with anchor-type stirring blades, Maxblend stirring blades, helical ribbon-type stirring blades, etc., or may be equipped with paddle blades, lattice blades, spectacle blades, etc. It may be a horizontal type or an extruder type equipped with a screw, and it is preferably carried out using a reaction apparatus in which these are appropriately combined in consideration of the viscosity of the polymer.

Next, the method for producing the polyester resin polymer will be described in more detail.
The diol component and its preferred components are the same as those explained in the production method of the polymer that is the polycarbonate resin. Dicarboxylic acids and dicarboxylic acid derivatives include those described above.

The dicarboxylic acid or dicarboxylic acid derivative is preferably used in a ratio of 0.97 to 1.20 mol, more preferably 0.98 to 1.10 mol, per 1 mol of the diol component.

When ^X1 is an epoxy group, the compound of the present invention can be obtained by cationic polymerization, anionic polymerization, or the like. Further, when ^X1 is an acryl group, a polymer can be obtained by, for example, a radical polymerization reaction. Even in these cases, it can be useful as an optical material as described later. In addition, when X ¹ is another reactive group, the polymer can be obtained by reaction corresponding to the reactive group.

3. Molded Article Next, the molded article of the present invention will be described.
The molded article of the present invention is not particularly limited as long as it contains the polymer of the present invention described above. Available. Applications of optical materials using high refractive materials include optical lenses used in various cameras such as cameras, film-integrated cameras, video cameras, and eyeglasses; microlenses used in image sensors; touch panels, displays, etc. Examples include optical paints and the like. Polycarbonate and polyester resins are suitable for the optical lenses of various cameras and eyeglasses, and light/thermosetting products using epoxy resins and acrylic resins are suitable for microlenses and optical paints. many. In the present invention, since a thin film can be formed, it can be preferably used for optical materials, particularly optical lenses.

Since it is desired that the content of foreign matter in the molded article is as low as possible, filtration of the molten raw material and filtration of the catalyst solution are preferably carried out when the polymer is produced. The mesh of the filter used for filtration is preferably 5 μm or less, more preferably 1 μm or less. Furthermore, filtration of the resulting polymer through a polymer filter is preferably carried out. The mesh of the polymer filter is preferably 100 μm or less, more preferably 30 μm or less. The process of collecting the polymer pellets must naturally be in a low dust environment, preferably class 1000 or less, more preferably class 100 or less.

The molded article of the present invention can be obtained by injection molding the polymer of the present invention into a desired shape using an injection molding machine or an injection compression molding machine. Molding conditions for injection molding are not particularly limited, but the molding temperature is preferably 140 to 280°C. Also, the injection pressure is preferably 50 to 1700 kg/cm ² .

In order to avoid contamination of the molded body with foreign matter as much as possible, the molding environment must naturally be a low-dust environment, preferably class 1000 or less, more preferably class 100 or less.

The molded article of the present invention thus obtained has a refractive index of 1.50 or more, preferably 1.55 to 1.8, particularly preferably 1.64, as measured by the method of JIS-K-7142. ~1.75. It is preferable to obtain a compact and lightweight optical lens by using such a molded article with a high refractive index.

A coat layer such as an antireflection layer or a hard coat layer may be provided on the surface of the optical lens made of the molded article, if necessary. The antireflection layer may be a single layer or multiple layers, and may be organic or inorganic, but is preferably inorganic. Specifically, oxides or fluorides such as silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, cerium oxide, magnesium oxide and magnesium fluoride are exemplified. Among these, more preferred are silicon oxide and zirconium oxide, and more preferred is a combination of silicon oxide and zirconium oxide.
As for the antireflection layer, although there are no particular limitations on the combination of single layer/multilayer, the combination of their components and thickness, etc., a two-layer structure or a three-layer structure is preferred, and a three-layer structure is particularly preferred. In addition, the antireflection layer as a whole is preferably formed with a thickness of 0.00017 to 3.3%, specifically 0.05 to 3 μm, particularly preferably 1 to 2 μm, of the thickness of the optical lens. .

4. Composition The composition of the invention contains the dibenzoxanthene compound of the invention or the polymer of the invention described above. The composition of the present invention may contain optional ingredients in addition to the dibenzoxanthene compound of the present invention or the polymer of the present invention. For example, when producing a cured product using the dibenzoxanthene compound of the present invention or the polymer of the present invention, the composition of the present invention contains a curable component such as a radically polymerizable compound, a cationic polymerizable compound, an anionically polymerizable compound, or the like. can contain The curable component may contain a radically polymerizable compound, a cationic polymerizable compound, an anionically polymerizable compound, and the like.

The radically polymerizable compound has a radically polymerizable reactive group. Examples of radically polymerizable reactive groups include ethylenically unsaturated double bond groups such as acrylic groups, methacrylic groups, and vinyl groups.
The cationically polymerizable compound has a cationically polymerizable reactive group. Examples of cationic polymerizable reactive groups include cyclic ether groups such as epoxy groups and oxetane groups, and vinyl ether groups.
The anionically polymerizable compound has an anionically polymerizable reactive group. Examples of the anionically polymerizable reactive group include an epoxy group, a lactone group, an acrylic group, and a methacrylic group.
In the composition of the present invention, the dibenzoxanthene compound of the present invention or the polymer of the present invention may have the above-described various reactive groups, or the dibenzoxanthene compound of the present invention or a compound other than the polymer of the present invention may be It may have the various reactive groups described above.

The compositions of the invention may contain polymerization initiators tailored to the reactive groups in the curable component contained in the compositions of the invention. Examples of polymerization initiators include radical photopolymerization initiators, cationic photopolymerization initiators, anionic photopolymerization initiators, thermal radical polymerization initiators, thermal cationic polymerization initiators, and thermal anionic polymerization initiators. The amount of polymerization initiator includes an amount suitable for polymerizing the curable components.
Specific examples of the curable component and various polymerization initiators include those described in Retable 2019/069961.

5. Cured Product and Production Method Thereof The composition of the present invention can be produced into a cured product by a method for producing a cured product including a heating step or a light (energy ray) irradiation step. Suitable conditions such as heating temperature and light (energy ray) irradiation amount can be appropriately adopted depending on the types of the curable component and the polymerization initiator.

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

[Example 1] Compound No. Synthesis of 1 Nitrogen was flowed into a 5 L four-necked flask, and 93.94 g (0.652 mol) of 2-naphthol, 40.00 g (0.290 mol) of 3,4-dihydroxybenzaldehyde, p-toluenesulfonic acid monohydrate2. 75 g (0.014 mol) and 2000 g of EDC were added and stirring was started. After stirring for 10 hours while refluxing, 1000 g of ion-exchanged water and 650 g of ethyl acetate were added to separate oil and water. The organic layer was washed twice with ion-exchanged water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 150 g of chloroform was added to the residue, dissolved at 60° C., and air-cooled to precipitate crystals, which were collected by filtration and dried. Compound no. 56.2 g of 1 was obtained in a yield of 49.7%. HPLC purity (254 nm): ≧99.9%, ¹ H NMR (DMSO): 6.50 ppm (s, 1H), 6.52 ppm (d, 1H), 6.78 ppm (s, 1H), 7.04 ppm ( d, 1H), 7.46-7.95 ppm (m, 10H), 8.63 ppm (m, 4H). MALDI-TOF-MS confirmed the formation of the desired product with a molecular weight of 413.2 [Na adduct]. The resulting compound no. The refractive index of 1 was measured to be 1.71.

[Example 2] Compound no. Synthesis of Compound No. 2 A 2 L flask was flushed with nitrogen. 1 50.00 g (0.13 mol), 24.81 g (0.28 mol) of ethylene carbonate, 0.35 g (0.0030 mol) of potassium carbonate, and 183.35 g of DMAc were added, and stirring was started. After stirring at 125° C. for 3 hours, 600 g of ethyl acetate and 550 g of ion-exchanged water were added to separate oil and water. The organic layer was washed twice with ion-exchanged water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 798 g of MIBK was added to the residue and dissolved by stirring at 100° C., and 570 g of IPE was added while air-cooling to precipitate crystals, which were collected by filtration and dried. Compound no. 54.5 g of 2 was obtained in a yield of 88.9%. HPLC purity (254 nm): 99.5%, ¹ H NMR (DMSO): 3.60 ppm (t, 4H), 3.82 ppm (t, 4H), 4.71 ppm (s, 2H), 6.63 ppm (s , 1H), 6.73 ppm (d, 1H), 6.96 ppm (s, 1H), 7.46-7.57 ppm (m, 7H), 7.92 ppm (m, 4H), 8.70 ppm (d, 2H). MALDI-TOF-MS confirmed the formation of the desired product with a molecular weight of 501.25 [Na adduct]. The resulting compound no. The refractive index of 2 was measured to be 1.67.

[Example 3] Compound No. Synthesis of 3 Nitrogen flow into a 5 L four-necked flask, 86.19 g (0.598 mol) of 2-naphthol, 50.00 g (0.266 mol) of 1,5-dihydroxy-2-naphthaldehyde, p-toluenesulfonic acid monohydrate 2.53 g (0.013 mol) of hydrate and 2000 g of EDC were added and stirring was started. After stirring for 12 hours while refluxing, 1000 g of ion-exchanged water and 800 g of ethyl acetate were added to separate oil and water. The organic layer was washed twice with ion-exchanged water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 200 g of 1,2-dichloroethane was added to the residue, dissolved at 70° C., and air-cooled to precipitate crystals, which were collected by filtration and dried. Compound no. 51.0 g of 3 was obtained in a yield of 43.6%. HPLC purity (254 nm): 99.8%, ¹ H NMR (DMSO): 6.19 ppm (d, 1H), 6.50 ppm (s, 1H), 6.90 ppm (d, 1H), 7.33-7 .95 ppm (m, 13H), 8.41 ppm (s, 1H), 8.63 ppm (m, 2H), 9.01 ppm (s, 1H). MALDI-TOF-MS confirmed the formation of the desired product with a molecular weight of 463.43 [Na adduct]. The resulting compound no. The refractive index of 3 was measured to be 1.77.

[Example 4] Compound No. Synthesis of 4 Nitrogen flow to a 3L four-necked flask, 2-naphthol 86.19g (0.598mol), 1,2-dihydroxy-6-naphthaldehyde 50.00g (0.266mol), p-toluenesulfonic acid monohydrate 2.53 g (0.013 mol) of hydrate and 2000 g of EDC were added and stirring was started. After stirring for 11 hours while refluxing, 800 g of ion-exchanged water and 600 g of ethyl acetate were added to separate oil and water. The organic layer was washed twice with ion-exchanged water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 170 g of 1,2-dichloroethane was added to the residue, dissolved at 80° C., and air-cooled to precipitate crystals, which were collected by filtration and dried. Compound no. 4 was obtained in 43.0 g, 36.8% yield. HPLC purity (254 nm): 99.6%, ¹ H NMR (DMSO): 6.50 ppm (s, 1H), 6.72 ppm (d, 1H), 6.96 ppm (d, 1H), 7.33-7 .95 ppm (m, 12H), 8.20 ppm (d, 1H), 8.63 ppm (m, 2H), 9.50 ppm (s, 1H), 9.88 ppm (s, 1H). MALDI-TOF-MS confirmed the formation of the desired product with a molecular weight of 463.51 [Na adduct]. The resulting compound no. The refractive index of 4 was measured to be 1.74.

[Example 5] Polycarbonate polymer no. Preparation of compound no. 1.00 mol of 1, 1.05 mol of diphenyl carbonate, and 1.00×10 ⁻⁶ mol of sodium hydrogen carbonate were placed in a 1 L reactor equipped with a stirrer and a distiller and stirred under a nitrogen atmosphere of 760 torr. while heating to 180°C.
Thereafter, the degree of pressure reduction was adjusted to 200 torr and the temperature to 200° C. over 15 minutes, and the same conditions were maintained for 20 minutes to carry out transesterification. Further, the temperature was raised to 240° C. at a rate of 30° C./hr and held at 240° C. and 150 torr for 10 minutes. After that, it was adjusted to 120 torr over 10 minutes, and held at 240° C. and 120 torr for 70 minutes. After that, it was adjusted to 100 torr over 10 minutes, and held at 240° C. and 100 torr for 10 minutes. Further, the temperature was lowered to 1 torr or less over 40 minutes, and the polymerization reaction was carried out for 10 minutes under the conditions of 240° C. and 1 torr or less. After completion of the reaction, nitrogen was blown into the reactor to return to normal pressure, and polymer no. got 1.

[Example 6] Polycarbonate polymer no. Preparation of compound no. 1 as compound no. Polymer No. 2 was used in the same manner except that Polymer No. 2 was used. got 2.

[Example 7] Polycarbonate polymer no. Preparation of compound no. 1 as compound no. The same procedure was repeated except that polymer No. 3 was used. got 3.

[Example 8] Polycarbonate polymer no. Preparation of compound no. 1 as compound no. Polymer No. 4 was prepared in the same manner except that Polymer No. 4 was used. Got 4.

[Comparative Example 1] Polycarbonate comparative polymer No. Preparation of Compound No. 1 In Example 5, compound no. Comparative Polymer No. 1 was prepared in the same manner except that bisphenol A (refractive index: 1.61) was used instead of Polymer No. 1. got 1.

[Comparative Example 2] Polycarbonate comparative polymer No. Preparation of compound no. Comparative Polymer No. 1 was prepared in the same manner except that 9,9-bis(4-hydroxyphenyl)fluorene [FL-BP] (refractive index: 1.68) was used instead of Polymer No. 1. got 2.

[Comparative Example 3] Polycarbonate comparative polymer No. Preparation of compound no. Comparative Polymer No. 1 was prepared in the same manner, except that phenylindane-bisphenol [PI-BP] (refractive index: 1.65) was used for Comparative Polymer No. 1. got 3.

(Evaluation example)
<Polystyrene equivalent weight average molecular weight (Mw)>
Using gel permeation chromatography (GPC: ChromNAV manufactured by JASCO Corporation, column: KF-805, 804, 803 linked), tetrahydrofuran as a developing solvent, calibration using standard polystyrene of known molecular weight (molecular weight distribution = 1) created a line. Based on this calibration curve, it was calculated from the retention time of GPC.

<Glass transition temperature (Tg)>
Measurement was performed using a differential scanning calorimeter (DSC: manufactured by Hitachi, model number: DSC7000X), and the temperature at the intersection of the baseline of the obtained DSC curve and the tangent line at the inflection point was taken as Tg.
A polymer having a glass transition temperature of 150° C. or higher is preferable from the viewpoint of high heat resistance, and a polymer having a glass transition temperature of 150° C. or higher and 250° C. or lower is particularly preferable in consideration of moldability.

<Refractive index>
The obtained polymer was press-molded into a rectangular parallelepiped of 3 mm thick×8 mm×8 mm, and measured by JIS-K-7142 A method using a refractometer (manufactured by ATAGO, model number: DR-M2).
A cured product having a refractive index of 1.63 or more can be preferably used for optical lenses, and a higher refractive index is preferable because the lens can be made thinner.
The refractive index of the compound before being polymerized was measured using a refractometer (Abbemat refractometer manufactured by Anton Paar). The sample sample was prepared as a 10 wt% NMP (N-methylpyrrolidone) solution of the compound. .

<Melt viscosity>
Using a capillary flow rheometer (manufactured by Toyo Seiki Seisakusho Co., Ltd., model number: F-F01), the following operations were performed to measure the melt viscosity.
After the obtained polymer was heated to 300° C. to melt, the injection speed was set to 0.01 to 150 mm/s, and the length (L) to diameter (D) ratio (L/D) was 40. Measurement was performed using six types of capillaries for melt viscosity measurement: /2, 20/1, 10/0.5, 15/1, 10/1, and 5/1.
In the above evaluation, A is given when the melt viscosity is less than 800 Pa·s, B is given when 800 Pa·s or more and less than 1000 Pa·s, and C is given when 1000 Pa·s or more.

As shown in Table 1, the compounds of the present invention are useful because they can provide high-quality optical materials. Specifically, the compounds of the present invention can form polymers with high refractive indices and low melting point viscosities. Due to this, the polymer can have a low film thickness and is excellent in moldability. Furthermore, as shown in each example, the polymer of the present invention has a high glass transition temperature and high heat resistance. Taking advantage of these properties, the polymer of the present invention is suitable for optical materials.

Claims (10)

A dibenzoxanthene compound represented by the following general formula (I).
(Wherein, Ar is a group represented by the following formula (Ar1), (Ar2) or (Ar3),
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² are each independently a hydrogen atom, —O—Y ¹ X ¹ , one or more of the substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms or the methylene group in the hydrocarbon group is substituted with a divalent group selected from the following <group A> represents the group
<Group A> is -O-, -CO-, -COO-, -OCO-, -NR ¹³ -, -NR ¹³ CO-, and -S-;
R ¹³ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
Y ¹ is a single bond, a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, or one or more methylene groups in the hydrocarbon group selected from the following <group B> Represents a group substituted by a divalent group represented by
X ¹ represents a hydrogen atom, a hydroxyl group, an acrylic group, a methacrylic group, a vinyl group, an epoxy group, an oxetanyl group, a carboxyl group, an isocyanate group, a mercapto group, an acid anhydride group, or an amino group;
When multiple Y ¹ and X ¹ are present in the molecule, they may be the same or different,
<Group B> is -O-, -CO-, -COO-, -OCO-, -NR ¹⁴ -, -NR ¹⁴ CO-, and -S-;
R ¹⁴ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. )
(In the formula, ^R21 , ^R22 , ^R23 , ^R24 , ^R25 , ^R26 , ^R27 , ^R28 , ^{R29 , R30} , R31, ^R32 , ^R33 , ^R34 , ^R35 , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ are each independently a hydrogen atom, —O—Y ² X ² , a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or methylene in the hydrocarbon group one or more of the groups represents a group substituted with a divalent group selected from the following <group C>,
Y ² is a single bond, a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, or one or more methylene groups in the hydrocarbon group selected from <Group C> below. Represents a group substituted by a divalent group represented by
^X2 represents a hydrogen atom, a hydroxyl group, an acrylic group, a methacrylic group, a vinyl group, an epoxy group, an oxetanyl group, a carboxyl group, an isocyanate group, a mercapto group, an acid anhydride group, or an amino group;
When multiple Y ² and X ² are present in the molecule, they may be the same or different,
<Group C> is -O-, -CO-, -COO-, -OCO-, -NR ⁴⁰ -, -NR ⁴⁰ CO-, and -S-;
R ⁴⁰ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
with the proviso that when Ar is Ar1, two or more of R ²¹ , R ²² , R ²³ , R ²⁴ and R ²⁵ are —O—Y ² X ² ;
when Ar is Ar2, one or more of R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ and R ³² is —O—Y ² X ² ;
when Ar is Ar3, one or more of R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ is —O—Y ² X ² ;
* represents a bond. ) when Ar is Ar1, two of R ²¹ , R ²² , R ²³ , R ²⁴ and R ²⁵ are —O—Y ² X ² ;
when Ar is Ar2, two of R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ and R ³² are —O—Y ² X ² ;
The dibenzoxanthene compound of claim 1, wherein when Ar is Ar3, two of R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ are —O—Y ² X ² . . one or more of X ¹ is a hydrogen atom, a hydroxyl group, an acrylic group, or an epoxy group, and one or more of X ² is a hydrogen atom, a hydroxyl group, an acrylic group, or an epoxy group; The dibenzoxanthene compound according to claim 1 or 2. The dibenzoxanthene according to any one of claims 1 to 3, wherein (Ar1) is represented by the following general formula (Ar4), and (Ar2) is represented by the following general formula (Ar5) or the following general formula (Ar6). Compound.
(wherein R ⁴¹ , R ⁴² and R ⁴³ are each independently a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or one or two methylene groups in the hydrocarbon group one or more represents a group substituted with a divalent group selected from the following <group D>,
R ⁴⁴ , R ⁴⁵ , R ⁴⁶ , R ⁴⁷ , R ⁴⁸ , R ⁴⁹ , R ⁵⁰ , R 51 , R ⁵² , R ⁵³ , R ⁵⁴ and ^{R 55 are} each independently —O—Y ¹⁵ X ¹⁵ , hydrogen One or more of the atoms, substituted or unsubstituted hydrocarbon groups having 1 to 20 carbon atoms, or methylene groups in the hydrocarbon groups are substituted with a divalent group selected from the following <group D> represents the group
<Group D> is -O-, -CO-, -COO-, -OCO-, -NR ⁶¹ -, -NR ⁶¹ CO-, and -S-;
Y ¹¹ , Y ¹² , Y ¹³ , Y ¹⁴ and Y ¹⁵ are each independently a single bond, a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms, or a methylene group in the hydrocarbon group represents a group substituted with a divalent group selected from the above <Group D>,
X ¹¹ , X ¹² , X ¹³ , X ¹⁴ and X ¹⁵ each independently represent a hydrogen atom, a hydroxyl group, an acrylic group, a methacrylic group, a vinyl group, an epoxy group, an oxetanyl group, a carboxyl group, an isocyanate group, a mercapto group, an acid represents an anhydride group or an amino group,
When multiple Y ¹⁵ and X ¹⁵ are present in the molecule, they may be the same or different,
R ⁶¹ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
* represents a bond. ) A polymer comprising the dibenzoxanthene compound according to any one of claims 1 to 4 as a monomer. A composition containing the dibenzoxanthene compound according to any one of claims 1 to 4 or the polymer according to claim 5. 7. The composition according to claim 6, containing a polymerization initiator. A cured product of the composition according to claim 7 . A molded article comprising the polymer according to claim 5 . A method for producing a cured product comprising a heating step or a light irradiation step for the composition according to claim 7 .