Optical Materials

Abstract

To provide a novel high-refractive-index polymer material.SOLUTION: An optical material contains an iodine-containing polymer. The iodine-containing polymer contains: a repeat unit induced from an acrylate monomer (1) containing a 2, 3, 5-triiodine phenyl group or a 2, 4, 6-triiodine phenyl group; and a structure induced from a molecular weight control agent that is at least one selected from the group consisting of a monothiol compound, a dithiol compound, and a RAFT agent.SELECTED DRAWING: None

Description

[Technical field]

[0001] In particular, the present disclosure relates to optical materials that include iodine-containing polymers for use in high refractive index polymeric materials. [Background technology]

[0002] Conventionally, in order to increase the refractive index of a polymer material, it has been considered effective to introduce sulfur atoms into the molecule, and as such a high refractive index polymer material, a sulfur-containing acrylic resin obtained by polymerizing an acrylic compound having a (meth)acryloylthio group and an aromatic ring, a styrene derivative, and a mercapto compound is known (Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 10-130339 Summary of the Invention [Problem to be solved by the invention]

[0004] However, the refractive index of conventional polymer materials is not necessarily sufficient, and from the viewpoint of versatility, the development of new polymer materials with high refractive index is desired. [Means for solving the problem]

[0005] The present disclosure has been made in light of these circumstances. Rather than addressing the problem by simply extending the conventional technology, the present inventors attempted to achieve the above-mentioned objective by addressing the problem in a new direction. As a result, the present inventors discovered that the above-mentioned main objective can be achieved by using a specific raw material, which led to the present disclosure. One embodiment of the present disclosure is as follows: [Section 1] An optical material comprising an iodine-containing polymer which includes a repeating unit derived from a triiodophenyl group-containing acrylate monomer (1). [Section 2] The monomer (1) is represented by the following formula: CH 2 =C(-X 1 )-C(=O)Y 1 -L-TIP [In the formula, TIP is the triiodophenyl group, X 1 is a hydrogen atom, a methyl group or a halogen atom, Y 1 is -O- or -NH-, L is a direct bond or a divalent organic group. Item 3. The optical material according to item 1, represented by: [Section 3] The iodine-containing polymer CH 2 =C(-X 2 )-C(=O)Y 2 -R [In the ceremony 、 X 2 is a hydrogen atom, a methyl group or a halogen atom, Y 2 is -O- or -NH-, R is an organic group having 2 to 30 carbon atoms. Item 3. The optical material according to item 1 or 2, having a repeating unit derived from a triiodophenyl group-free acrylate monomer (2) represented by the following formula: [Section 4] Item 4. The optical material according to item 3, wherein R is an alkylene group or an oxyalkylene group. [Section 5] The R -(R 1 O) q -R 2 [In the formula, R 1 are each independently an alkylene group having 1 to 10 carbon atoms; R 2 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and q is 1 or more and 100 or less.] Item 4. The optical material according to item 3, wherein the oxyalkylene group is represented by the following formula: [Section 6] Item 6. The optical material according to any one of items 3 to 5, wherein the content of the repeating unit derived from the monomer (2) in the iodine-containing polymer is 0.02 parts by mole or more per 1 part by mole of the repeating unit derived from the monomer (1). [Section 7] Item 7. The optical material according to any one of items 1 to 6, wherein the triiodophenyl group is a 2,3,5-triiodophenyl group or a 2,4,6-triiodophenyl group. [Section 8] Item 8. The optical material according to any one of items 1 to 7, wherein the iodine-containing polymer has a structure derived from a molecular weight control agent. [Section 9] Item 9. The optical material according to item 8, wherein the molecular weight control agent is at least one selected from the group consisting of a monothiol compound, a dithiol compound, and a RAFT agent. [Section 10] 10. An optical part formed from the optical material according to claim 1, the optical part being selected from a coating, a film, a sheet, a prism, a lens and a fiber. [Section 11] An optical article comprising the optical component according to claim 10. Effect of the Invention

[0006] According to the present disclosure, there is provided an optical material that is a novel high refractive index polymer material. The optical material of the present disclosure can be excellent not only in refractive index but also in solubility, film-forming property, heat resistance, and the like. [Brief description of the drawings]

[0007] [Figure 1] 1 shows the results of TGA measurement of an iodine-containing polymer in Example 17 of the present disclosure. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] <Optical materials> The optical material in the present disclosure is a material that is a raw material for various optical components, and is particularly used in optical components that utilize its high refractive index. The optical material in the present disclosure includes an iodine-containing polymer that includes a repeating unit derived from a triiodophenyl group-containing acrylate monomer (1).

[0009] [Iodine-containing polymer] The iodine-containing polymer in the present disclosure is a polymer containing a repeating unit derived from a triiodophenyl group-containing acrylate monomer (1). The iodine-containing polymer may be linear or branched, but is preferably linear.

[0010] (Triiodophenyl group-containing acrylate monomer (1)) The acrylate monomer (1) is an acrylate monomer (1) having at least one triiodophenyl group. The triiodophenyl group may be a 2,3,5-triiodophenyl group or a 2,4,6-triiodophenyl group, and is preferably a 2,4,6-triiodophenyl group. Conventionally, there have been problems with molecular weight controllability, solubility, and / or film-forming properties, and the application of iodine-containing monomers has not been considered. The present inventors have unexpectedly found that by selecting a triiodophenyl group-containing acrylate monomer (1) from among iodine-containing monomers, it is possible to solve these problems while having a high refractive index.

[0011] The acrylate monomer (1) in the present disclosure is formula: CH 2 =C(-X 1 )-C(=O)Y 1 -L-TIP [In the formula, TIP is the triiodophenyl group, X 1 is a hydrogen atom, a methyl group or a halogen atom, Y 1 is -O- or -NH- L is a direct bond or a divalent organic group. It may be expressed as:

[0012] X 1 is preferably a hydrogen atom or a methyl group.

[0013] Y 1 is preferably -O-.

[0014] The organic group in L may be an aliphatic or aromatic group, preferably an aliphatic group, and in particular an alkylene group or a (poly)oxyalkylene group.

[0015] When L is an alkylene group, L may have 1 or more, 2 or more, 3 or more, 5 or more, or 10 or more carbon atoms, and may have 30 or less, 25 or less, 20 or less, 15 or less, or 10 or less carbon atoms.

[0016] When L is a (poly)oxyalkylene group, the number of oxygen atoms in L may be 1 or more, 2 or more, or 3 or more, and may be 25 or less, 7 or less, or 5 or less.

[0017] When L is a (poly)oxyalkylene group, L is a group of the formula: -(L 1 O) p - [In the formula, L 1 are each independently an alkylene group having 1 to 10 carbon atoms, and p is 1 to 100. It may be expressed as:

[0018] L 1 may have 1 or more, 2 or more, 3 or more, or 5 or more carbon atoms, and may have 10 or less, 7 or less, 5 or less, or 3 or less carbon atoms.

[0019] p may be 1 or more, 3 or more, 5 or more, 10 or more, 25 or more, or 50 or more; and may be 100 or less, 80 or less, 60 or less, 40 or less, 20 or less, or 10 or less.

[0020] -(L 1 O) p -L 1 Specific examples of O- include: -CH 2 CH 2 O- -CH 2 CH(CH 3 )O- -CH 2 CH(C 2 H 5 )O- -CH 2 C(CH 3 ) 2 O- -CH 2 CH 2 CH 2 CH 2 O- etc.

[0021] (Acrylate Monomer Not Containing Triiodophenyl Group (2)) The iodine-containing polymer in the present disclosure may contain a repeating unit derived from a non-triiodophenyl group-containing acrylate monomer (2).

[0022] The triiodophenyl group-free acrylate monomer (2) does not have a triiodophenyl group. The triiodophenyl group-free acrylate monomer (2) may not have an iodophenyl group, and may not have an iodine atom.

[0023] The acrylate monomer (2) in the present disclosure is formula: CH 2 =C(-X 2 )-C(=O)Y 2 -R [In the formula, X 2 is a hydrogen atom, a methyl group or a halogen atom, Y 2 is -O- or -NH- R is a hydrogen atom, a hydroxyl group, or an organic group having 1 to 30 carbon atoms.] It may be expressed as:

[0024] X 2 is preferably a hydrogen atom or a methyl group.

[0025] Y 2 is preferably -O-.

[0026] R may be an aliphatic or aromatic group, preferably an aliphatic group, in particular an alkyl group or a (poly)oxyalkylene group.

[0027] When R is an alkyl group, R may have 1 or more, 2 or more, 3 or more, 5 or more, or 10 or more carbon atoms, and may have 30 or less, 25 or less, 20 or less, 15 or less, or 10 or less carbon atoms.

[0028] When R is a (poly)oxyalkylene group, the number of oxygen atoms in R may be 1 or more, 2 or more, or 3 or more, and may be 25 or less, 7 or less, or 5 or less.

[0029] When R is a (poly)oxyalkylene group, R is a group of the formula: -(R 1 O) q -R 2 [In the formula, R 1 are each independently an alkylene group having 1 to 10 carbon atoms; R 2 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and q is 1 or more and 100 or less.] It may be expressed as:

[0030] R 1 may have 1 or more, 2 or more, 3 or more, or 5 or more carbon atoms, and may have 10 or less, 7 or less, 5 or less, or 3 or less carbon atoms.

[0031] q may be 1 or more, 3 or more, 5 or more, 10 or more, 25 or more, or 50 or more; and may be 100 or less, 80 or less, 60 or less, 40 or less, 20 or less, or 10 or less.

[0032] -(R 1 O) q -R 1 Specific examples of O- include: -CH2 CH 2 O- -CH 2 CH(CH 3 )O- -CH 2 CH(C 2 H 5 )O- -CH 2 C(CH 3 ) 2 O- -CH 2 CH 2 CH 2 CH 2 O- etc.

[0033] R 2 When R is an alkyl group, 2 may have 1 or more, 2 or more, 3 or more, or 5 or more carbon atoms, and may have 10 or less, 7 or less, 5 or less, or 3 or less carbon atoms.

[0034] (Sulfur-containing structure) The iodine-containing polymer in the present disclosure may have a sulfur atom. The refractive index of the iodine-containing polymer may be improved by having a sulfur atom. The sulfur atom may be present in the main chain or in a side chain, and is preferably present in the main chain.

[0035] (Structure derived from molecular weight control agent) The iodine-containing polymer in the present disclosure may have a structure derived from a molecular weight control agent. The molecular weight control agent is an additive that can control the molecular weight range by suppressing polymerization, and is typically a chain transfer agent. The molecular weight control agent is preferably an aromatic compound. By being aromatic, the refractive index of the iodine-containing polymer can be improved. Examples of the molecular weight control agent include various chain transfer agents, RAFT agents, NMP agents, ATRP agents, and TERP agents, and sulfur-containing chain transfer agents such as thiol-type chain transfer agents and RAFT agents are preferred.

[0036] The thiol type chain transfer agent may be a monothiol compound, a dithiol compound, a trithiol compound, or a polythiol compound having tetrathiol or more, but is preferably a monothiol compound or a dithiol compound. The thiol type chain transfer agent may be a thiol compound having a sulfur atom in addition to a thiol group. The thiol compound may be a molecule consisting of only carbon, hydrogen, and sulfur.

[0037] Specific examples of thiol-type chain transfer agents include aliphatic monothiol compounds such as methanethiol, ethanethiol, propanethiol, butanethiol, and cyclohexanethiol;

[0038] Methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6-hexanedithiol, 1,2,3-propanetrithiol, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, 1,1-bis(mercaptomethyl)cyclohexane, thiomalic acid bis(2-mercaptoethyl ester), 2,3-dimercapto-1-propanol(2-mercaptoacetate), 2,3-dimercapto-1-propanol(3-mercaptopropionate), diethylene glycol bis( aliphatic polythiol compounds such as bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), 1,2-dimercaptopropyl methyl ether, 2,3-dimercaptopropyl methyl ether, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, bis(2-mercaptoethyl)ether, ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), trimethylolpropane bis(2-mercaptoacetate), trimethylolpropane bis(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), and tetrakis(mercaptomethyl)methane;

[0039] Bis(mercaptomethyl)sulfide, bis(mercaptoethyl)sulfide, bis(mercaptopropyl)sulfide, bis(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, bis(3-mercaptopropyl)methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-(2-mercaptoethylthio)ethane, 1,2-(3-mercaptopropyl)ethane, 1,3-bis(mercaptomethylthio)propane, 1,3-bis(2-mercaptoethylthio)propane, 1,3-bis(3-mercaptopropylthio)propane, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 2-mercaptoethylthio-1,3-propanedithiol, 1,2,3-tris(mercaptomethylthio)ethane, 1,2-(2-mercaptoethylthio)ethane, 1,2-(3-mercaptopropylthio)ethane, 1,3-bis(mercaptomethylthio)propane, 1,3-bis(2-mercaptoethylthio)propane, 1,3-bis(3-mercaptopropylthio)propane, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 2-mercaptoethylthio-1,3-propanedithiol, 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3-tris(3-mercaptopropylthio)propane, tetrakis(mercaptomethylthiomethyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthiomethyl)methane, bis(2,3-dimercaptopropyl)sulfide, 2,5-dimercapto-1,4-dithiane, bis(mercaptomethyl)disulfide, bis(mercaptoethyl)disulfide, bis(mercaptopropyl)disulfide, 4-mercaptomethyl-3,6-dithiaoctane-1,8-dithiol, bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, bis(1,3-Dimercapto-2-propyl) sulfide, hydroxymethyl sulfide bis(2-mercaptoacetate), hydroxymethyl sulfide bis(3-mercaptopropionate), hydroxyethyl sulfide bis(2-mercaptoacetate), hydroxyethyl sulfide bis(3-mercaptopropionate), hydroxypropyl sulfide bis(2-mercaptoacetate), hydroxypropyl sulfide bis(3-mercaptopropionate), hydroxymethyl ethyl disulfide bis(2-mercaptoacetate), hydroxymethyl disulfide bis(3-mercaptopropionate), hydroxyethyl disulfide bis(2-mercaptoacetate), hydroxyethyl disulfide bis(3-mercaptopropionate), hydroxypropyl disulfide bis(2-mercaptoacetate), hydroxypropyl disulfide bis(3-mercaptopropionate), 2-mercaptoethyl ether bis(2-mercaptoacetate), 2-Mercaptoethyl ether bis(3-mercaptopropionate), 1,4-dithiane-2,5-diol bis(2-mercaptoacetate), 1,4-dithiane-2,5-diol bis(3-mercaptopropionate), thioglycolic acid bis(2-mercaptoethyl ester), thiodipropionic acid bis(2-mercaptoethyl ester), 4,4'-thiodibutyric acid bis(2-mercaptoethyl ester), dithiodiglycolic acid bis(2-mercaptoethyl ester) Aliphatic thiols containing a sulfur atom in addition to a mercapto group, such as dithiodipropionic acid bis(2-mercaptoethyl ester), 4,4'-dithiodibutyric acid bis(2-mercaptoethyl ester), thiodiglycolic acid bis(2,3-dimercaptopropyl ester), thiodipropionic acid bis(2,3-dimercaptopropyl ester), dithiodiglycolic acid bis(2,3-dimercaptopropyl ester), and dithiodipropionic acid (2,3-dimercaptopropyl ester);

[0040] Aromatic monothiol compounds such as benzenethiol, o-methyl-α-toluenethiol, o-toluenethiol, m-toluenethiol, p-toluenethiol, 1-naphthalenethiol, and 2-naphthalenethiol;

[0041] 1,2-Dimercaptobenzene, 1,3-Dimercaptobenzene, 1,4-Dimercaptobenzene, 1,2-Bis(mercaptomethyl)benzene, 1,3-Bis(mercaptomethyl)benzene, 1,4-Bis(mercaptomethyl)benzene, 1,2-Bis(mercaptoethyl)benzene, 1,3-Bis(mercaptoethyl)benzene, 1,4-Bis(mercaptoethyl)benzene, 1,2,3-Trimercaptobenzene, 1,2,4-Trimercaptobenzene, 1,3,5-Trimercaptobenzene, 1,2,3-Tris(mercaptomethyl)benzene, 1,2, aromatic polythiols such as 4-tris(mercaptomethyl)benzene, 1,3,5-tris(mercaptomethyl)benzene, 1,2,3-tris(mercaptoethyl)benzene, 1,2,4-tris(mercaptoethyl)benzene, 1,3,5-tris(mercaptoethyl)benzene, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,3-di(p-methoxyphenyl)propane-2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, and 2,4-di(p-mercaptophenyl)pentane;

[0042] 1,2-bis(mercaptomethylenethio)benzene, 1,3-bis(mercaptomethylenethio)benzene, 1,4-bis(mercaptomethylenethio)benzene, 1,2-bis(mercaptoethylenethio)benzene, 1,3-bis(mercaptoethylenethio)benzene, 1,4-bis(mercaptoethylenethio)benzene, 1,2-bis(mercaptopropylenethio)benzene, 1,3-bis(mercaptopropylenethio)benzene, 1,4-bis(mercaptopropylenethio)benzene, 1,2-bis(mercaptoethylenethiomethylene)benzene, 1,3 -Bis(mercaptoethylenethiomethylene)benzene, 1,4-bis(mercaptoethylenethiomethylene)benzene, 1,2-bis(mercaptopropylenethiomethylene)benzene, 1,3-bis(mercaptopropylenethiomethylene)benzene, 1,4-bis(mercaptopropylenethiomethylene)benzene, bis(4-mercaptophenyl)sulfide, bis(3-mercaptophenyl)sulfide, 4,4'-oxybisbenzenethiol, 4,4'-biphenyldithiol, 1,2-bis(mercaptomethyleneoxy)benzene, 1,3-bis(methyl) 1,4-bis(mercaptomethyleneoxy)benzene, 1,2-bis(mercaptoethyleneoxy)benzene, 1,3-bis(mercaptoethyleneoxy)benzene, 1,4-bis(mercaptoethyleneoxy)benzene, 1,2-bis(mercaptoethyleneoxymethylene)benzene, 1,3-bis(mercaptoethyleneoxymethylene)benzene, 1,4-bis(mercaptoethyleneoxymethylene)benzene, 1,2-bis(mercaptopropyleneoxymethylene)benzene, 1,3-bis(mercaptopropyleneoxymethylene)benzene, aromatic polythiol compounds containing sulfur atoms in addition to mercapto groups, such as 1,4-bis(mercaptopropyleneoxymethylene)benzene, 1,4-bis(mercaptopropyleneoxymethylene)benzene, 1,3,5-trimercaptobenzene, 1,2,3-tris(mercaptomethylthio)benzene, 1,2,4-tris(mercaptomethylthio)benzene, 1,3,5-tris(mercaptomethylthio)benzene, 1,2,3-tris(mercaptoethylthio)benzene, 1,2,4-tris(mercaptoethylthio)benzene, and 1,3,5-tris(mercaptoethylthio)benzene;

[0043] Heterocyclic compounds containing a sulfur atom in addition to a mercapto group, such as 3,4-thiophenedithiol and 2,5-dimercapto-1,3,4-thiadiazole;

[0044] 2-Mercaptoethanol, 3-Mercapto-1,2-propanediol, Glycerin di(mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 3,4-dimercapto-2-propanol, 1,3-dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, Pentaerythritol tris(3-mercaptopropanediol) Examples of the mercapto group include compounds containing a hydroxy group in addition to a mercapto group, such as pentaerythritol mono(3-mercaptopropionate), pentaerythritol bis(3-mercaptopropionate), pentaerythritol tris(thioglycolate), dipentaerythritol pentakis(3-mercaptopropionate), hydroxymethyl-tris(mercaptoethylthiomethyl)methane, and 1-hydroxyethylthio-3-mercaptoethylthiobenzene, as well as derivatives thereof. These may be used alone or in combination of two or more.

[0045] Specific examples of RAFT agents include dithioesters such as 2-cyano-2-propyl benzodithioate and 4-cyano-4-(phenylcarbonothioylthio)pentanoic acid; trithiocarbonates such as 2-cyano-2-propyl dodecyl trithiocarbonate, 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid, 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid and cyanomethyl dodecyl trithiocarbonate; dithiocarbamates such as cyanomethyl methyl(phenyl)carbamodithioate; and disulfides such as bis(thiobenzoyl) disulfide and bis(dodecylsulfanylthiocarbonyl) disulfide. These may be used alone or in combination of two or more.

[0046] (Structures derived from other sources) The iodine-containing polymer of the present disclosure may have a structure derived from other raw materials in addition to the above. Specific examples of other raw materials include styrene monomers such as styrene, p-methylstyrene, α-methylstyrene, halogenated styrene, vinylbenzoic acid, 4-vinylbenzenesulfonic acid, 4-vinylbenzenesulfonic acid ester, and 4-vinylbenzenesulfonic acid amide; amide group-containing vinyl monomers such as (meth)acrylamide, N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide, N,N-dimethyl(meth)acrylamide, and N,N-dimethylaminopropyl(meth)acrylamide; methyl(meth)acrylate, ethyl(meth)acrylate, propyl(meth)acrylate, butyl(meth)acrylate, and 2-(meth)acrylic acid; Examples of such monomers include (meth)acrylates such as ethylhexyl, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, glycidyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, Nt-butylaminoethyl (meth)acrylate, and polyethylene glycol (meth)acrylate, (meth)acrylamide monomers, nitrile group-containing vinyl monomers such as (meth)acrylonitrile, and other monomers such as vinyl halides, vinylidene halides, and vinyl acetate. These monomers may be used alone or in combination of two or more.

[0047] (Molecular weight of iodine-containing polymer) The number average molecular weight of the iodine-containing polymer in the present disclosure may be 300 or more, 500 or more, 1000 or more, 1500 or more, 3000 or more, 5000 or more, or 10000 or more, and is preferably 3000 or more. The number average molecular weight of the iodine-containing polymer in the present disclosure may be 100000 or less, 50000 or less, 25000 or less, 15000 or less, 12500 or less, or 10000 or less, and is preferably 50000 or less. By being in the above range, the solubility, film-forming property, heat resistance, and transparency of the iodine-containing polymer can be excellent and moderately well-balanced. The number average molecular weight may be a polystyrene-equivalent molecular weight.

[0048] The dispersion index (Mw / Mn) of the iodine-containing polymer in the present disclosure may be 1.5 or more, 2 or more, 3 or more, or 4 or more. The dispersion index (Mw / Mn) of the iodine-containing polymer in the present disclosure may be 7.5 or less, 5 or less, 4 or less, or 3 or less.

[0049] (Composition of iodine-containing polymer) The content of the repeating unit derived from the monomer (1) in the iodine-containing polymer may be 20% by weight or more, 30% by weight or more, 40% by weight or more, 50% by weight or more, 60% by weight or more, 70% by weight or more, or 80% by weight or more. The content of the repeating unit derived from the monomer (1) in the iodine-containing polymer may be 95% by weight or less, 85% by weight or less, 75% by weight or less, 65% by weight or less, 55% by weight or more, or 45% by weight or less. From the viewpoint of improving the refractive index, the larger the amount of the monomer (1), the more preferable.

[0050] The content of the repeating unit derived from the monomer (2) in the iodine-containing polymer may be 2.0% by weight or more, 4.0% by weight or more, 6.0% by weight or more, 8.0% by weight or more, 10% by weight or more, 15% by weight or more, or 20% by weight or more. The content of the repeating unit derived from the monomer (2) in the iodine-containing polymer may be 50% by weight or less, 40% by weight or less, 30% by weight or less, 20% by weight or less, 10% by weight or less, or 7.5% by weight or less. The presence of the repeating unit derived from the monomer (2) particularly improves the film-forming property.

[0051] The content of the structure derived from the molecular weight control agent in the iodine-containing polymer may be 1.0% by weight or more, 3.0% by weight or more, 5.0% by weight or more, or 10% by weight or more, and preferably 3% by weight or more. The content of the structure derived from the molecular weight control agent in the iodine-containing polymer may be 50% by weight or less, 40% by weight or less, 30% by weight or less, or 25% by weight or less, and preferably 40% by weight or less.

[0052] The content of the structure derived from other raw materials in the iodine-containing polymer may be 1.0% by weight or more, 3.0% by weight or more, 5.0% by weight or more, or 10% by weight or more. The content of the structure derived from other raw materials in the iodine-containing polymer may be 30% by weight or less, 20% by weight or less, or 10% by weight or less.

[0053] The iodine content in the iodine-containing polymer may be 10% by weight or more, 25% by weight or more, 30% by weight or more, 35% by weight or more, 40% by weight or more, or 45% by weight or more, and is preferably 30% by weight or more. The iodine content in the iodine-containing polymer may be 55% by weight or less, 50% by weight or less, or 45% by weight or less.

[0054] The sulfur content in the iodine-containing polymer may be 1.0% by weight or more, 2.0% by weight or more, 3.0% by weight or more, 4.0% by weight or more, 5.0% by weight or more, or 7.5% by weight or more, and is preferably 2.0% by weight or more. The sulfur content in the iodine-containing polymer may be 30% by weight or less, 20% by weight or less, 15% by weight or less, or 10% by weight or less, and is preferably 10% by weight or less.

[0055] The content of the repeating unit derived from the monomer (1) may be 2.0 molar parts or more, 3.0 molar parts or more, 5.0 molar parts or more, 10 molar parts or more, 15 molar parts or more, or 20 molar parts or more, preferably 3 molar parts or more, relative to 1 molar part of the structure derived from the molecular weight regulator in the iodine-containing polymer. The content of the repeating unit derived from the monomer (1) may be 50 molar parts or less, 45 molar parts or less, 40 molar parts or less, 35 molar parts or less, 30 molar parts or less, or 25 molar parts or less, preferably 40 molar parts or less, relative to 1 molar part of the structure derived from the molecular weight regulator.

[0056] The content of the repeating unit derived from the monomer (2) may be 0.2 molar parts or more, 0.3 molar parts or more, 0.5 molar parts or more, 1.0 molar parts or more, 1.5 molar parts or more, or 2 molar parts or more, preferably 0.3 molar parts or more, relative to 1 molar part of the structure derived from the molecular weight regulator in the iodine-containing polymer. The content of the repeating unit derived from the monomer (1) may be 5.0 molar parts or less, 4.5 molar parts or less, 4.0 molar parts or less, 3.5 molar parts or less, 3.0 molar parts or less, or 2.5 molar parts or less, preferably 4.0 molar parts or less, relative to 1 molar part of the structure derived from the molecular weight regulator.

[0057] The content of the repeating unit derived from the monomer (2) may be 0.02 molar parts or more, 0.03 molar parts or more, 0.05 molar parts or more, 0.1 molar parts or more, 0.15 molar parts or more, or 0.2 molar parts or more, preferably 0.03 molar parts or more, for example 0.1 molar parts or more, relative to 1 molar part of the repeating unit derived from the monomer (1) in the iodine-containing polymer. The amount of the monomer (2) used may be 0.5 molar parts or less, 0.45 molar parts or less, 0.4 molar parts or less, 0.35 molar parts or less, 0.3 molar parts or less, or 0.25 molar parts or less, preferably 0.4 molar parts or less, relative to 1 molar part of the monomer (1). The presence of the repeating unit derived from the monomer (2) particularly improves the film-forming property.

[0058] By containing each component in the above range, the iodine-containing polymer can have a high refractive index and can also have a suitably well-balanced excellent solubility, film-forming property, heat resistance and transparency.

[0059] (Refractive index of iodine-containing polymer) The refractive index of the iodine-containing polymer in the present disclosure may be 1.65 or more, 1.70 or more, 1.72 or more, 1.76 or more, 1.78 or more, 1.80 or more, or 1.82 or more, preferably 1.72 or more, and more preferably 1.78 or more.

[0060] (Heat resistance of iodine-containing polymers) The heat resistance temperature of the iodine-containing polymer in the present disclosure (the temperature at which a 5% weight loss is observed when the temperature is increased at a rate of 10°C / min in a nitrogen gas atmosphere) may be 250°C or higher, 260°C or higher, 270°C or higher, 280°C or higher, 290°C or higher, 300°C or higher, 310°C or higher, or 320°C or higher, preferably 260°C or higher, and more preferably 280°C or higher.

[0061] (Method for producing iodine-containing polymer) In the method for producing the iodine-containing polymer of the present disclosure, the iodine-containing polymer can be obtained by a step of polymerizing the above-mentioned monomers as raw materials. The method for producing an iodine-containing polymer according to the present disclosure includes the steps of: Polymerizing the monomer in the presence of a molecular weight control agent By polymerizing the monomer in the presence of a molecular weight control agent, it becomes easy to control the molecular weight within the above-mentioned range.

[0062] The amount of the raw material used can be appropriately changed so that the above-mentioned iodine-containing polymer can be obtained. The amount of the monomer (1) used can be 2.0 molar parts or more, 3.0 molar parts or more, 5.0 molar parts or more, 10 molar parts or more, 15 molar parts or more, or 20 molar parts or more, preferably 3 molar parts or more, for example 10 molar parts or more, relative to 1 molar part of the molecular weight control agent. The amount of the monomer (1) used can be 50 molar parts or less, 45 molar parts or less, 40 molar parts or less, 35 molar parts or less, 30 molar parts or less, or 25 molar parts or less, preferably 40 molar parts or less, relative to 1 molar part of the molecular weight control agent. For example, by increasing the amount of the molecular weight control agent, polymerization can be suppressed, and it is possible to suppress the increase in molecular weight.

[0063] The amount of the monomer (2) used may be 0.2 molar parts or more, 0.3 molar parts or more, 0.5 molar parts or more, 1.0 molar parts or more, 1.5 molar parts or more, or 2 molar parts or more, preferably 0.3 molar parts or more, for example 1 molar part or more, relative to 1 molar part of the molecular weight control agent. The amount of the monomer (2) used may be 5.0 molar parts or less, 4.5 molar parts or less, 4.0 molar parts or less, 3.5 molar parts or less, 3.0 molar parts or less, or 2.5 molar parts or less, preferably 4.0 molar parts or less, relative to 1 molar part of the molecular weight control agent. For example, by increasing the amount of the molecular weight control agent, polymerization can be suppressed, and it is possible to suppress the increase in molecular weight.

[0064] The amount of the monomer (2) used may be 0.02 molar parts or more, 0.03 molar parts or more, 0.05 molar parts or more, 0.1 molar parts or more, 0.15 molar parts or more, or 0.2 molar parts or more, preferably 0.03 molar parts or more, for example 0.1 molar parts or more, relative to 1 molar part of the monomer (1). The amount of the monomer (2) used may be 0.5 molar parts or less, 0.45 molar parts or less, 0.4 molar parts or less, 0.35 molar parts or less, 0.3 molar parts or less, or 0.25 molar parts or less, preferably 0.4 molar parts or less, relative to 1 molar part of the monomer (1). The presence of the monomer (2) particularly improves the film-forming property.

[0065] In the present disclosure, the polymerization method is not particularly limited, and can be performed by a known polymerization method such as bulk polymerization, solution polymerization, suspension polymerization, emulsion polymerization, etc., but is preferably solution polymerization. Also, a known polymerization method such as radical polymerization, anionic polymerization, cationic polymerization, etc. can be selected, but is preferably radical polymerization. An appropriate polymerization method can be selected depending on the type of monomer, polymerization temperature, etc.

[0066] In the present disclosure, an appropriate polymerization initiator can be selected and used depending on the type of monomer, polymerization temperature, etc. Examples of polymerization initiators include azo-based initiators such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(2,2-dimethylvaleronitrile), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), and 2,2'-azobis(2-amidinopropane)dihydrochloride; and peroxide-based initiators such as benzoyl peroxide, di-t-butyl hydroperoxide, t-butyl hydroperoxide, cumyl peroxide, cumene hydroperoxide, diisopropylbenzene hydroperoxide, benzoyl peroxide, dicumyl peroxide, ethyl 3,3-di(t-amylperoxy)butyrate, potassium sulfate, and ammonium persulfate. These may be used alone or in combination of two or more kinds.

[0067] When the polymerization is carried out by solution polymerization, a suitable solvent is selected in consideration of the solubility of the monomer and the radical initiator, the polymerization temperature, etc., and the polymerization can be carried out in the solvent. Examples of the solvent include DMF, N-methyl-2-pyrrolidone, acetone, THF, benzene, toluene, ethylbenzene, xylene, chlorobenzene, methyl ethyl ketone, ethyl lactate, isopropyl alcohol, etc. These may be used alone or in combination of two or more kinds.

[0068] The polymerization temperature may be any temperature at which the polymerization initiator decomposes and polymerization begins, and may be, for example, 0°C or higher, 20°C or higher, 40°C or higher, 60°C or higher, or 70°C or higher, and is preferably 40°C or higher, and may be 100°C or lower, 90°C or lower, 80°C or lower, or 70°C or lower.

[0069] The optimal polymerization time can be determined depending on the selected monomer, polymerization initiator, polymerization temperature, etc., and may be, for example, 1 hour or more, 5 hours or more, 10 hours or more, 15 hours or more, or 20 hours or more, and may be 72 hours or less, 60 hours or less, 48 ​​hours or less, 36 hours or less, or 24 hours or less.

[0070] The amount of the polymerization initiator used may vary depending on the type of monomer and the type of initiator, but may be, for example, 0.1 mol% or more, 1 mol% or more, 3 mol% or more, 5 mol% or more, 10 mol% or more, 15 mol% or more, 20 mol% or more, or 25 mol% or more, and may be 50 mol% or less, 40 mol% or less, 30 mol% or less, 20 mol% or less, or 10 mol% or less, based on the total amount of the monomers used.

[0071] The amount of the polymerization solvent used is not particularly limited, but may be in a range such that the raw material concentration is 5% by weight or more, 10% by weight or more, 15% by weight or more, or 20% by weight or more, and 50% by weight or less, 40% by weight or less, 30% by weight or less, or 20% by weight or less.

[0072] <Optical components> The optical material in the present disclosure may be used as an optical component such as a coating, a film, a sheet, a prism, a lens, or a fiber (hereinafter, referred to as a coating, etc.). When used for these applications, the optical material may be formed by applying the optical material to a substrate. The type of substrate is not particularly limited, and may be a resin, glass, metal, ceramic, or the like.

[0073] When the optical material of the present disclosure is applied to a substrate, the optical material may be a non-solvent type, but may be used as a solution containing the above-mentioned iodine-containing polymer and a solvent that dissolves the iodine-containing polymer. The type of solvent is not particularly limited as long as it dissolves the iodine-containing polymer, but for example, organic solvents such as THF, chloroform, DMF, and DMSO can be used. The concentration of the iodine-containing polymer in the coating liquid may be 0.01 wt% or more, 0.1 wt% or more, 0.5 wt% or more, or 1 wt% or more, and may be 5 wt% or less, 3 wt% or less, 1.5 wt% or less, or 0.5 wt% or less.

[0074] A solution containing an iodine polymer may be applied to a base, and the solvent may be removed as necessary to obtain a coating or the like. As the application method, a commonly used application method such as dipping coating, spray coating, flow coating, shower coating, roll coating, spin coating, gravure coating, microgravure coating, comma roll coating, Mayer bar coating, slot bicoat, air knife coating, lip coating, kiss coating, brush coating, etc. The removal of the solvent is not particularly limited, and may be carried out at, for example, 0 to 200°C.

[0075] The type of the substrate is not particularly limited, and may be resin, glass, metal, ceramic, or the like.

[0076] The coating thickness may be 0.1 μm or more, 1 μm or more, or 3 μm or more, and may be 1 m or less, 500 μm or less, or 200 μm or less.

[0077] <Optical article having optical component> Examples of optical articles having optical components such as the above-mentioned coatings are not particularly limited, but preferred examples include optical devices such as high refractive index light-emitting diodes (LEDs) and image sensors, high refractive index materials such as anti-reflection films, lens materials, and lens coatings, and optical instruments such as telescopes, binoculars, microscopes, cameras, endoscopes (fiberscopes), planetariums, length measuring instruments, comparators, range finders, spectrometers, interferometers, and polarimeters.

Example

[0078] Hereinafter, embodiments of the present disclosure will be described in detail by way of examples, but the present disclosure is not limited to these examples.

[0079] The test method is as follows. <IR measurement> FT / IR 4600 manufactured by JASCO Corporation was used.

[0080] <NMR measurement> 400 MHz-NMR JOEL ECS-400K manufactured by JEOL Ltd. or 400 MHz-NMR JOEL ECZ-400 manufactured by JEOL Ltd. was used.

[0081] <SEC measurement> It was carried out under the following equipment and conditions. HLC-8320GPC manufactured by Tosoh Corporation Column; TSKgel SuperMultipore HZ-M × 2 (4.6 mm I.D. × 15 cm × 2) Standard; Polystyrene SRM706 (NIST) Eluent; THF Detector; RI; Polarity (+), Response (0.5 s) UV; Wavelength (254 nm), Polarity (+), Response (0.5 s)

[0082] <Heat resistance> Using a TGA measuring device (Model TGA-50 / 50H manufactured by Shimadzu Corporation), it was measured in a nitrogen gas atmosphere at a heating rate of 10 °C / min in the temperature range from 25 °C to 450 °C. The temperature T at which a 5% weight loss was observed d is shown in Table 2.

[0083] <Solubility> 2 mg of the obtained iodine-containing polymer was added to 2 ml of various organic solvents and left at 25 °C overnight. The solubility was judged according to the following criteria. The results are shown in Table 2. ○: Dissolved completely without residue △: Some parts remain undissolved ×: Most of the material remains undissolved

[0084] <Refractive index> The refractive index of the iodine-containing polymer was measured by forming a film of the iodine-containing polymer on a silicon wafer, measuring 30 points with a laser having a wavelength of 632 nm using an ellipsometer (SE-101 manufactured by Photonic Lattice Co., Ltd.), and averaging the measurements. The results are shown in Table 2.

[0085] [Synthesis of monomer (TIP-AC)] TIFF0007624704000001.tif4112314.4g (30mmol) of 2,4,6-triiodephenol, 6ml of TEA, and 60ml of THF were placed in a 200ml eggplant flask, and 4.07g (45mmol) of acrylic chloride was added over 10-15 minutes in an ice bath and stirred at room temperature for 24 hours. A yellow solid was obtained. Evaporation was performed and ethyl acetate was added. The salt was removed by filtration, and the solution was separated (1N HCl, sat. NaHCO 3 , sat NaCl) were performed three times. The organic layer was diluted with MgSO 4 The mixture was dehydrated and dried under reduced pressure to obtain 12.58 g of a yellow powdery solid. 1 H-NMR, 13 The physical properties were evaluated by C-NMR and IR measurements. The developing solvent was (chloroform:hexane = 1:1) and column chromatography was performed. After that, it was dried under reduced pressure to obtain a white solid. It was recrystallized using hexane and chloroform, and elemental analysis was performed to confirm that the obtained compound was triiodophenyl acrylate (TIP-AC). The yield was 12.58 g, 87%.

[0086] [Example 1] Synthesis of poly(TIP-AC) TIFF0007624704000002.tif45880.52g (1mmol) of TIP-AC, 0.3ml of DMF, and the amount of AIBN shown in Table 1 (3 mol% relative to TIP-AC) were placed in a polymerization tube, degassed and sealed, and stirred for 20 hours in a 60°C oil bath. The mixture was reprecipitated in methanol, filtered through a membrane, and then dried under reduced pressure to obtain an iodine-containing polymer. 1 The composition and molecular weight were determined by H-NMR, IR measurement, and GPC measurement. The obtained iodine-containing polymer was subjected to thermogravimetry, a solubility test, and a refractive index measurement. The results are shown in Tables 1 to 4.

[0087] [Example 2] Synthesis of TBBT-poly(TIP-AC) TIFF0007624704000003.tif361320.52g (1mmol) of TIP-AC, 0.3ml of DMF, 4,4'-Thiobisbenzenethiol (TBBT) (1.5 mol% relative to TIP-AC), and AIBN (3 mol% relative to TIP-AC) were placed in a polymerization tube, degassed and sealed, and stirred in a 60°C oil bath for 20 hours. The mixture was reprecipitated with methanol, filtered through a membrane, and dried under reduced pressure to obtain an iodine-containing polymer. 1 The composition and molecular weight were determined by H-NMR, IR, and GPC measurements. The obtained iodine-containing polymer was subjected to thermogravimetry, a solubility test, and refractive index measurement. The results are shown in Tables 1 to 4. In Table 1, n indicates 1 / 2 the amount (molar parts) of the repeating unit derived from TIP-AC relative to 1 mol part of the structure derived from TBBT in the iodine-containing polymer.

[0088] [Example 3] Synthesis of TBBT-poly(TIP-AC) 0.52g (1mmol) of TIP-AC, 0.3ml of DMF, TBBT (15mol% relative to TIP-AC) and AIBN (30mol% relative to TIP-AC) were placed in a polymerization tube, which was then degassed and sealed, and stirred in a 60°C oil bath for 20h. A yellow liquid and a viscous solid were obtained. The mixture was reprecipitated with methanol, filtered through a membrane, and then dried under reduced pressure. Thermogravimetry, solubility tests, and refractive index measurements were performed on the obtained iodine-containing polymer. The results are shown in Tables 1 to 4. In Table 1, n indicates 1 / 2 of the amount (molar parts) of repeating units derived from TIP-AC relative to 1 mol part of the structure derived from TBBT in the iodine-containing polymer.

[0089] [Example 4] Synthesis of TBBT-poly(TIP-AC) The synthesis and testing were carried out in the same manner as in Example 3, except that the weighing temperature was 65° C. The results are shown in Tables 1 to 4.

[0090] [Example 5] Synthesis of TBBT-poly(TIP-AC) The synthesis and testing were carried out in the same manner as in Example 3, except that the weighing temperature was 70° C. The results are shown in Tables 1 to 4.

[0091] [Example 6] Synthesis of TBBT-poly(TIP-AC) The synthesis and testing were carried out in the same manner as in Example 3, except that the weighing temperature was 75° C. The results are shown in Tables 1 to 4.

[0092] [Example 7] Synthesis of TBBT-poly(TIP-AC) The synthesis and testing were carried out in the same manner as in Example 3, except that the weighing temperature was 80° C. The results are shown in Tables 1 to 4.

[0093] [Example 8] Synthesis of TBBT-poly(TIP-AC-co-EEA) TIFF0007624704000004.tif100141TIP-AC (0.95mmol, 0.50g), 2-(2-Ethoxyethoxy)ethyl Acrylate (EEA) (0.05mmol, 0.009g), 0.3ml DMF, AIBN (30mol% relative to the total amount of TIP-AC and EEA, 0.05g), and TBBT (15mol% relative to the total amount of TIP-AC and EEA, 0.037g) were placed in a polymerization tube, degassed and sealed, and stirred for 20h in a 75°C oil bath. After reprecipitation with methanol and membrane filtration, the mixture was dried under reduced pressure to obtain an iodine-containing polymer. The obtained iodine-containing polymer was subjected to thermogravimetry, solubility test, and refractive index measurement. The results are shown in Tables 1 to 4. In Table 1, n indicates half the amount (by mole) of repeating units derived from TIP-AC relative to 1 molar part of the structure derived from TBBT in the iodine-containing polymer, and m indicates half the amount (by mole) of repeating units derived from EEA relative to 1 molar part of the structure derived from TBBT in the iodine-containing polymer.

[0094] [Example 9] Synthesis of TBBT-poly(TIP-AC-co-EEA) Except for using 0.90 mol of TIP-AC and 0.10 mol of EEA, the synthesis and testing were carried out in the same manner as in Example 8. The results are shown in Tables 1 to 4.

[0095] [Example 10] Synthesis of TBBT-poly(TIP-AC-co-EEA) Except for using 0.80 mol of TIP-AC and 0.20 mol of EEA, the synthesis and testing were carried out in the same manner as in Example 8. The results are shown in Tables 1 to 4.

[0096] [Example 11] Synthesis of BT-poly(TIP-AC-co-EEA) TIFF0007624704000005.tif112138TIP-AC (0.8mmol, 0.42g), 2-(2-Ethoxyethoxy)ethyl Acrylate (EEA) (0.2mmol, 0.037g), 0.3ml DMF, AIBN (7.5 mol% based on the total amount of TIP-AC and EEA), and Benzenethiol (BT) (7.5 mol% based on the total amount of TIP-AC and EEA) were placed in a polymerization tube, degassed and sealed, and stirred for 20h in a 60℃ oil bath. After reprecipitation with methanol and membrane filtration, the iodine-containing polymer was obtained by drying under reduced pressure. 1 The composition and molecular weight obtained by H-NMR, IR, and GPC measurements are shown in Table 1. In Table 1, n indicates the amount (parts by mole) of repeating units derived from TIP-AC relative to 1 part by mole of the structure derived from BT in the iodine-containing polymer, and m indicates the amount (parts by mole) of repeating units derived from EEA relative to 1 part by mole of the structure derived from TBBT in the iodine-containing polymer. The results of thermogravimetry, solubility testing, and refractive index measurement of the obtained iodine-containing polymer are shown in Tables 1 to 4.

[0097] [Example 12] Synthesis of BT-poly(TIP-AC-co-EEA) The synthesis and testing were carried out in the same manner as in Example 10, except that the amount of AIBN was 15 mol% based on the total amount of TIP-AC and EEA, and the amount of BT was 15 mol% based on the total amount of TIP-AC and EEA. The results are shown in Tables 1 to 4.

[0098] [Example 13] Synthesis of BT-poly(TIP-AC-co-EEA) AIBN amount relative to the total amount of TIP-AC and EEA 30 mol%, amount of BT relative to the total amount of TIP-AC and EEA 30 Except for using mol %, the synthesis and testing were carried out in the same manner as in Example 10. The results are shown in Tables 1 to 4.

[0099] Example 14 ] p Synthesis of oly(TIP-AC-co-EEA) TIFF0007624704000006.tif53133TIP-AC (0.95mmol, 0.50g), 2-(2-Ethoxyethoxy)ethyl Acrylate (EEA) (0.05mmol, 0.009g), 0.3ml of DMF, and AIBN (3mol%, 0.005g) were placed in a polymerization tube, which was then degassed and sealed, and stirred in a 60℃ oil bath for 20h. The mixture was reprecipitated with methanol, filtered through a membrane, and dried under reduced pressure to obtain an iodine-containing polymer. 1 The composition and molecular weight determined by H-NMR, IR, and GPC measurements are shown in Table 1. The obtained iodine-containing polymer was subjected to thermogravimetry, a solubility test, and refractive index measurement. The results are shown in Tables 1 to 4. In Table 1, n and m indicate the ratio of the amount (parts by mole) of repeating units derived from TIP-AC to the amount (parts by mole) of repeating units derived from EEA in the iodine-containing polymer.

[0100] Example 15 ] p Synthesis of oly(TIP-AC-co-EEA) The amount of TIP-AC was 0.9 mmol. EEA The synthesis and testing were carried out in the same manner as in Example 14, except that the amount of was 0.1 mmol. The results are shown in Tables 1 to 4.

[0101] [Example 16] ] p Synthesis of oly(TIP-AC-co-EEA) The amount of TIP-AC was 0.9 mmol. EEA The synthesis and testing were carried out in the same manner as in Example 14, except that the amount of was 0.15 mmol. The results are shown in Tables 1 to 4.

[0102] Example 17 ] p Synthesis of oly(TIP-AC-co-EEA) The amount of TIP-AC was 0.9 mmol. EEAThe synthesis and testing were carried out in the same manner as in Example 14, except that the amount of was 0.2 mmol. The results are shown in Tables 1 to 4. [Table 1] [Table 2] [Table 3] [Table 4] [Industrial Applicability]

[0103] The iodine-containing polymer of the present disclosure can be used in optical devices such as high refractive index light-emitting diodes (LEDs) and image sensors, high refractive index materials such as high refractive index polymer materials for antireflection films, lens materials, lens coating films, etc., and optical instruments such as telescopes, binoculars, microscopes, cameras, endoscopes (fiberscopes), planetariums, length measuring instruments, comparators, range finders, spectrometers, interferometers, polarimeters, etc. In particular, the iodine-containing polymer of the present disclosure can be preferably used in applications requiring solubility, film-forming ability, heat resistance, transparency, etc. in addition to a high refractive index.

Claims

1. An optical material comprising an iodine-containing polymer including a repeating unit derived from a triiodophenyl group-containing acrylate monomer (1), The number average molecular weight of the iodine-containing polymer is 50,000 or less, and the iodine-containing polymer satisfies at least one of the following (I) and (II): (I) The iodine-containing polymer is formula: CH 2 =C(-X 2 )-C(=O)Y 2 -R [In the formula, X 2 is a hydrogen atom, a methyl group or a halogen atom; Y 2 is —O— or —NH—; R is an organic group having 2 to 30 carbon atoms. The repeating unit is derived from a triiodophenyl group-free acrylate monomer (2) represented by the formula: The R is an alkyl group, or -(R 1 O) q -R 2 [In the formula, R 1 is independently an alkylene group having 1 to 10 carbon atoms, R 2 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and q is 1 to 100.] It is a (poly)oxyalkylene group represented by the following formula: (II) The iodine-containing polymer has a structure derived from a molecular weight control agent.

2. The monomer (1) is formula: CH 2 =C(-X １ )-C(=O)Y １ -L-TIP [In the formula, TIP is the triiodophenyl group; X １ is a hydrogen atom, a methyl group or a halogen atom, Y １ is —O— or —NH—, L is a direct bond or a divalent aliphatic or aromatic group. The optical material according to claim 1 ,

3. The iodine-containing polymer is formula: CH 2 =C(-X ２ )-C(=O)Y ２ -R [In the formula, X ２ is a hydrogen atom, a methyl group or a halogen atom, Y ２ is —O— or —NH—, R is an organic group having 2 to 30 carbon atoms. The repeating unit is derived from a triiodophenyl group-free acrylate monomer (2) represented by the formula: The R is an alkyl group, or -(R 1 O) q -R 2 [In the formula, R 1 is independently an alkylene group having 1 to 10 carbon atoms, R 2 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and q is 1 to 100.] The optical material according to claim 1 or 2, wherein the (poly)oxyalkylene group is represented by the following formula:

4. The optical material according to claim 3 , wherein R is an alkyl group.

5. The optical material according to claim 3 , wherein R is the (poly)oxyalkylene group.

6. The optical material according to any one of claims 3 to 5, wherein in the iodine-containing polymer, a content of the repeating unit derived from the monomer (2) is 0.02 parts by mole or more per 1 part by mole of the repeating unit derived from the monomer (1).

7. The optical material according to any one of claims 1 to 6, wherein the triiodophenyl group is a 2,3,5-triiodophenyl group or a 2,4,6-triiodophenyl group.

8. The optical material according to any one of claims 1 to 7, wherein the iodine-containing polymer has a structure derived from a molecular weight control agent.

9. The optical material according to claim 8 , wherein the molecular weight control agent is at least one selected from the group consisting of a monothiol compound, a dithiol compound, and a RAFT agent.

10. An optical component formed from the optical material according to any one of claims 1 to 9, and selected from a coating, a film, a sheet, a prism, a lens and a fiber.

11. An optical article comprising the optical component according to claim 10.

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