Composition for polymerizing high refractive index resin, high refractive index resin, and product comprising same

Abstract

A composition for polymerizing a high refractive index resin according to one exemplary embodiment of the present specification comprises: a first compound represented by Chemical Formula 1; and one or more types of the following: a second compound represented by Chemical Formula 2 and a third compound represented by Chemical Formula 3, and a high refractive index resin according to another exemplary embodiment of the present specification comprises: a first unit represented by Chemical Formula 11; and one or more of the following: a second unit represented by chemical formula 12 and a third unit represented by chemical formula 13.

Description

TECHNICAL FIELD

[0001] This specification relates to a composition for polymerizing a high refractive index resin, a high refractive index resin, and an article including the same.

[0002] This specification claims the priority and benefits of Korean Patent Applications Nos. 10-2023-0120955 and 10-2024-0124019, filed with the Korean Intellectual Property Office on September 12, 2023, and September 11, 2024, respectively, the entire contents of which are incorporated herein by reference. BACKGROUND ART

[0003] A high refractive index material is a material having excellent refractive ability for photons and means a dense medium in terms of photon transmission. Generally, glass is used as a high refractive index material, but glass has the disadvantages of low safety and high specific gravity. Therefore, it is necessary to develop a material based on a transparent, soft polymer and having a high refractive index.

[0004] A high refractive index resin, which is an example of a high refractive index material, can be used for optical components that require an antireflection effect, a light scattering effect, or a light extraction effect. For example, a high refractive index resin can be used for an optical plastic lens; a high-precision lens for optical disk recording such as a CD or a DVD; a prism; an optical fiber; a light guide plate; an optical adhesive or a pressure-sensitive adhesive; a sealing material for an optical semiconductor; or a functional material applied to a plasma display panel (PDP) or a liquid crystal display (LCD), such as an antireflection film, a light scattering film, a viewing angle improvement film, a brightness improvement film, or an optical filter. In addition, a high refractive index resin can also be used as an additive for preventing the deterioration of plastics, an additive for cosmetics, or a window glass for vehicles.

[0005] In addition, the higher the refractive index of an optical material, the thinner the optical lens required to achieve the same correction level. Therefore, as the refractive index of an optical material increases, thinner and lighter lenses can be manufactured, enabling various devices using lenses to be made smaller. High refractive index materials provide versatility in lens design, and their uses are gradually increasing.

[0006] Therefore, active research has been conducted on high refractive index materials that can be used for small electronic devices and can achieve excellent performance while having a thin thickness.

[0007] [RELATED ART DOCUMENT]

[0008] (Patent Document 1) Korean Patent Application Publication No. 2016-0067229 SUMMARY OF THE INVENTION

[0009] TECHNICAL PROBLEM

[0010] This specification is dedicated to providing a composition for polymerizing a high refractive index resin, a high refractive index resin, and an article containing the same.

[0011] Technical solution

[0012] An exemplary embodiment of this specification provides a composition for polymerizing a high refractive index resin, the composition comprising: a first compound represented by the following Chemical Formula 1; and one or more types of the following: a second compound represented by the following Chemical Formula 2 and a third compound represented by the following Chemical Formula 3.

[0013] [Chemical Formula 1]

[0014]

[0015] [Chemical Formula 2]

[0016]

[0017] [Chemical Formula 3]

[0018]

[0019] In Chemical Formulas 1 to 3,

[0020] R1 is an alkyl group that is unsubstituted or substituted with an aryl or heteroaryl group; a cycloalkyl group that is unsubstituted or substituted with an alkyl group; or an aryl group,

[0021] R2 and R3 are each independently an alkyl group that is unsubstituted or substituted with an aryl or heteroaryl group; a cycloalkyl group that is unsubstituted or substituted with an alkyl group; or an aryl group,

[0022] Z is a direct bond; -O-; or -COO-, and

[0023] X is hydrogen; or an alkyl group.

[0024] Another exemplary embodiment of this specification provides a high refractive index resin, the high refractive index resin comprising: a first unit represented by the following Chemical Formula 11; and one or more of the following: a second unit represented by the following Chemical Formula 12 and a third unit represented by the following Chemical Formula 13.

[0025] [Chemical Formula 11]

[0026]

[0027] [Chemical Formula 12]

[0028]

[0029] [Chemical Formula 13]

[0030]

[0031] In Chemical Formulas 11 to 13,

[0032] * Means the part connected to the main chain of the resin,

[0033] R11 is an unsubstituted or aryl- or heteroaryl-substituted alkyl group; an unsubstituted or alkyl-substituted cycloalkyl group; or an aryl group,

[0034] R21 and R31 are each independently an unsubstituted or aryl- or heteroaryl-substituted alkyl group; an unsubstituted or alkyl-substituted cycloalkyl group; or an aryl group,

[0035] Z1 is a direct bond; -O-; or -COO-, and

[0036] X1 is hydrogen; or an alkyl group.

[0037] Yet another exemplary embodiment of the present specification provides an article including a high refractive index resin.

[0038] Beneficial Effects

[0039] Since the composition for polymerizing a high refractive index resin according to an exemplary embodiment of the present specification is used as a material for polymerizing a high refractive index resin to provide a high refractive index resin having a high refractive index, a small optical material having excellent optical characteristics while having a thin thickness can be provided.

[0040] The resin (polymer) produced using the composition used in the present invention has a non-aromatic main chain and a non-planar three-dimensional amorphous structure (first unit), and therefore, exhibits excellent birefringence characteristics.

[0041] Furthermore, by including a second unit different from the first unit, a high-refractive-index resin having various structures and excellent optical characteristics can be provided. DETAILED DESCRIPTION

[0042] Hereinafter, this specification will be described in more detail.

[0043] In the present specification, when a part “comprises” one constituent element, unless otherwise specifically described, this does not mean excluding another constituent element but means that another constituent element may further be included.

[0044] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom or a nitrogen atom of a compound is changed into another substituent, and the position to be substituted is not limited as long as the position is a position where the hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0045] In this specification, unless otherwise specifically restricted, "substituted by A" means substituted by one or more A, or substituted by one or more types of A. For example, being substituted by an alkyl group includes both the case of being substituted by one alkyl group and the case of being substituted by a plurality of alkyl groups, and specific examples thereof include both the case of being substituted by one or more methyl groups and the case of being substituted by methyl groups and ethyl groups.

[0046] In this specification, the term "unit" means a part of the structure contained in the main chain of a polymer, which can be included in the polymer one or more times and can be used interchangeably with "repeating unit".

[0047] In this specification, * means the part connected to the main chain of the resin.

[0048] In this specification, the alkyl group can be a straight-chain or branched alkyl group, and the number of its carbon atoms can be 1 to 60. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, isohexyl, heptyl, n-heptyl, octyl, n-octyl, tert-octyl, n-nonyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, 1-methyl-butyl, 1-ethyl-butyl, 2-ethyl-butyl, 3,3-dimethyl-butyl, 1-methyl-pentyl, 2-methyl-pentyl, 4-methyl-2-pentyl, 2-propyl-pentyl, 1-methyl-hexyl, 4-methyl-hexyl, 5-methyl-hexyl, 2-ethyl-hexyl, 1-methyl-heptyl, 2,2-dimethyl-heptyl, etc., but are not limited thereto.

[0049] In this specification, the cycloalkyl group can be a monocyclic or polycyclic cycloalkyl group, and the number of its carbon atoms can be 3 to 60. Specifically, the cycloalkyl group can be a monocyclic cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cycloheptyl, and polycyclic cycloalkyl groups such as adamantyl and norbornyl, etc., but are not limited thereto.

[0050] In this specification, the aryl group can be a monocyclic or polycyclic aryl group, and the number of its carbon atoms can be 6 to 60. The monocyclic aryl group means an aryl group composed of a single ring aryl group, and the number of its carbon atoms can be 6 to 30. Specific examples of the monocyclic aryl group include phenyl, biphenyl, terphenyl, etc., but are not limited thereto. In the case of the polycyclic aryl group, the number of its carbon atoms can be 10 to 30, and specific examples thereof include naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, phenalenyl, yl, yl, fluorenyl, etc., but are not limited thereto.

[0051] In this specification, a heteroaryl group contains one or more atoms other than carbon, that is, one or more heteroatoms. Specifically, the heteroatoms include one or more atoms selected from O, S, N, Se, etc. The heteroaryl group may have 2 to 60 carbon atoms and may be monocyclic or polycyclic. Examples of the heteroaryl group include thienyl, furyl, dibenzofuryl, dibenzothienyl, benzothienyl, pyrrolyl, imidazolyl, thiazolyl, azolyl, diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, etc., but are not limited thereto.

[0052] A composition for polymerizing a high refractive index resin according to an exemplary embodiment of this specification includes: a first compound represented by the following Chemical Formula 1; and one or more types of the following: a second compound represented by the following Chemical Formula 2 and a third compound represented by the following Chemical Formula 3.

[0053] [Chemical Formula 1]

[0054]

[0055] [Chemical Formula 2]

[0056]

[0057] [Chemical Formula 3]

[0058]

[0059] In Chemical Formulas 1 to 3,

[0060] R1 is an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group,

[0061] R2 and R3 are each independently an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group,

[0062] Z is a direct bond; -O-; or -COO-, and

[0063] X is hydrogen; or an alkyl group.

[0064] When the composition for polymerizing a high refractive index resin is polymerized, the polymerization occurs at the norbornene ring of Chemical Formula 1. That is, the resin produced by polymerizing the composition for polymerizing a high refractive index resin can contain units derived from the compound represented by Chemical Formula 1 in the main chain rather than in the side chain, thereby providing a high refractive index resin having excellent optical properties while having a thin thickness.

[0065] In addition, the resin has a non-aromatic main chain and a non-planar three-dimensional amorphous structure, and thus exhibits excellent birefringence properties.

[0066] In addition, the composition for polymerizing a high refractive index resin further contains a compound represented by Chemical Formula 2 or Chemical Formula 3, so that high refractive index resins having various structures with excellent optical properties while having a thin thickness can be provided.

[0067] When preparing a high refractive index resin by only containing the first compound, there is a problem that polymerization cannot be achieved due to the molecular weight being 1,000 or less.

[0068] In the present specification, the composition for polymerizing a high refractive index resin can be a monomer composition.

[0069] In an exemplary embodiment of the present specification, R1 can be a C1-C10 alkyl group which is unsubstituted or substituted with an aryl or heteroaryl group; a C3-C20 cycloalkyl group which is unsubstituted or substituted with an alkyl group; or a C6-C30 aryl group.

[0070] In an exemplary embodiment of the present specification, R1 can be an unsubstituted or aryl- or heteroaryl-substituted methyl group; an unsubstituted or alkyl-substituted cyclopentyl group; an unsubstituted or alkyl-substituted cyclohexyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0071] In an exemplary embodiment of the present specification, R1 can be a C1-C10 alkyl group which is unsubstituted or substituted with a C6-C30 aryl group or a C2-C30 heteroaryl group; a C3-C20 cycloalkyl group which is unsubstituted or substituted with a C1-C20 alkyl group; or a C6-C30 aryl group.

[0072] In an exemplary embodiment of the present specification, R1 can be a C1-C10 alkyl group which is unsubstituted or substituted with a C6-C20 aryl group or a C2-C20 heteroaryl group; a C3-C20 cycloalkyl group which is unsubstituted or substituted with a C1-C10 alkyl group; or a C6-C30 aryl group.

[0073] When R1 is substituted with a heteroaryl group, the heteroaryl group can contain N and can specifically be a carbazolyl group.

[0074] In an exemplary embodiment of the present specification, R1 may be methyl which is unsubstituted or substituted with a C6-C30 aryl or a C2-C30 heteroaryl; cyclopentyl which is unsubstituted or substituted with a C1-C20 alkyl; cyclohexyl which is unsubstituted or substituted with a C1-C20 alkyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0075] In an exemplary embodiment of the present specification, R1 may be methyl which is unsubstituted or substituted with a C6-C20 aryl or a C2-C20 heteroaryl; cyclopentyl which is unsubstituted or substituted with a C1-C10 alkyl; cyclohexyl which is unsubstituted or substituted with a C1-C10 alkyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0076] In an exemplary embodiment of the present specification, R1 may be methyl which is unsubstituted or substituted with a C6-C20 aryl or a C2-C20 heteroaryl; cyclopentyl which is unsubstituted or substituted with a C1-C5 alkyl; cyclohexyl which is unsubstituted or substituted with a C1-C5 alkyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0077] In an exemplary embodiment of the present specification, R1 may be methyl which is unsubstituted or substituted with phenyl, anthryl or carbazolyl; cyclopentyl which is unsubstituted or substituted with methyl; cyclohexyl which is unsubstituted or substituted with methyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0078] In an exemplary embodiment of the present specification, the first compound may be any one selected from the following compounds.

[0079]

[0080] In an exemplary embodiment of the present specification, with respect to 100 parts by weight of the entire composition for polymerizing the high refractive index resin, the content of the first compound may be 1 part by weight or more, 2 parts by weight or more, 3 parts by weight or more, 4 parts by weight or more, 5 parts by weight or more, 6 parts by weight or more, or 7 parts by weight or more, and 95 parts by weight or less, 90 parts by weight or less, 70 parts by weight or less, 50 parts by weight or less, 40 parts by weight or less, 30 parts by weight or less, 20 parts by weight or less, 10 parts by weight or less, or 8 parts by weight or less.

[0081] In an exemplary embodiment of the present specification, relative to 100 parts by mole of the entire composition for polymerizing a high refractive index resin, the content of the first compound may be 1 part by mole or more, 2 parts by mole or more, 3 parts by mole or more, or 4 parts by mole or more, and 50 parts by mole or less, 40 parts by mole or less, 30 parts by mole or less, 20 parts by mole or less, 10 parts by mole or less, 9 parts by mole or less, 8 parts by mole or less, 7 parts by mole or less, 6 parts by mole or less, or 5 parts by mole or less.

[0082] In parts by weight and parts by mole, 100 parts by weight or 100 parts by mole of the entire composition for polymerizing a high refractive index resin means 100 parts by weight or 100 parts by mole of the entire monomer composition for polymerizing a high refractive index resin. That is, 100 parts by weight or 100 parts by mole of the entire composition for polymerizing a high refractive index resin is based on the case where solvents and catalysts are not included.

[0083] Within the above content range, the effects are that the higher the content of the first compound, the higher the refractive index of the resin becomes, and the better the thermal stability, shrinkage rate, glass transition temperature, and heat resistance become.

[0084] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin contains one or more types of a second compound and a third compound.

[0085] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain a second compound.

[0086] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain one or more types of a second compound.

[0087] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain one type of a second compound.

[0088] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain a third compound.

[0089] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain one or more types of a third compound.

[0090] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain one or two types of a third compound.

[0091] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain two types of third compounds.

[0092] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain a second compound and a third compound.

[0093] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain: a second compound; and one or more types of third compounds.

[0094] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain: one type of second compound; and one or more types of third compounds.

[0095] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain: one type of second compound; and one or two types of third compounds.

[0096] In an exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may contain: one type of second compound; and two types of third compounds.

[0097] In an exemplary embodiment of the present specification, R2 and R3 may each independently be a C1-C10 alkyl group that is unsubstituted or substituted with an aryl or heteroaryl group; a C3-C20 cycloalkyl group that is unsubstituted or substituted with an alkyl group; or a C6-C30 aryl group.

[0098] In an exemplary embodiment of the present specification, R2 and R3 may each independently be an unsubstituted or aryl- or heteroaryl-substituted methyl group; an unsubstituted or alkyl-substituted cyclopentyl group; an unsubstituted or alkyl-substituted cyclohexyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0099] In an exemplary embodiment of the present specification, R2 and R3 may each independently be a C1-C10 alkyl group that is unsubstituted or substituted with a C6-C30 aryl or C2-C30 heteroaryl group; a C3-C20 cycloalkyl group that is unsubstituted or substituted with a C1-C10 alkyl group; or a C6-C30 aryl group.

[0100] In an exemplary embodiment of the present specification, R2 and R3 may each independently be a C1-C10 alkyl group that is unsubstituted or substituted with a C6-C20 aryl or C2-C20 heteroaryl group; a C3-C20 cycloalkyl group that is unsubstituted or substituted with a C1-C10 alkyl group; or a C6-C30 aryl group.

[0101] In an exemplary embodiment of the present specification, R2 and R3 may each independently be methyl that is unsubstituted or substituted with a C6-C30 aryl or a C2-C30 heteroaryl; cyclopentyl that is unsubstituted or substituted with a C1-C10 alkyl; cyclohexyl that is unsubstituted or substituted with a C1-C10 alkyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0102] In an exemplary embodiment of the present specification, R2 and R3 may each independently be methyl that is unsubstituted or substituted with a C6-C20 aryl or a C2-C20 heteroaryl; cyclopentyl that is unsubstituted or substituted with a C1-C10 alkyl; cyclohexyl that is unsubstituted or substituted with a C1-C10 alkyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0103] In an exemplary embodiment of the present specification, R2 and R3 may each independently be methyl that is unsubstituted or substituted with phenyl, anthracenyl or carbazolyl; cyclopentyl that is unsubstituted or substituted with methyl; cyclohexyl that is unsubstituted or substituted with one or more methyl groups; phenyl; biphenyl; naphthyl; or fluorenyl.

[0104] In an exemplary embodiment of the present specification, X may be hydrogen; or a C1-C10 alkyl.

[0105] In an exemplary embodiment of the present specification, X may be hydrogen; or a C1-C5 alkyl.

[0106] In an exemplary embodiment of the present specification, X may be hydrogen; methyl; or ethyl.

[0107] In an exemplary embodiment of the present specification, X may be hydrogen; or methyl.

[0108] In an exemplary embodiment of the present specification, Z may be -O-; or -COO-.

[0109] In an exemplary embodiment of the present specification, Z may be -O-.

[0110] In an exemplary embodiment of the present specification, the second compound may be any one selected from the following compounds.

[0111]

[0112]

[0113] In an exemplary embodiment of the present specification, the third compound may be any one selected from the following compounds.

[0114]

[0115] In an exemplary embodiment of the present specification, relative to 100 parts by weight of the entire composition for polymerizing a high refractive index resin, the content of the second compound may be 1 part by weight or more, 3 parts by weight or more, 5 parts by weight or more, 7 parts by weight or more, 10 parts by weight or more, 12 parts by weight or more, 14 parts by weight or more, or 15 parts by weight or more, and 90 parts by weight or less, 70 parts by weight or less, 50 parts by weight or less, 40 parts by weight or less, 30 parts by weight or less, 20 parts by weight or less, or 16 parts by weight or less.

[0116] In an exemplary embodiment of the present specification, relative to 100 moles of the entire composition for polymerizing a high refractive index resin, the content of the second compound may be 1 mole or more, 5 moles or more, 10 moles or more, 15 moles or more, 18 moles or more, or 19 moles or more, and 60 moles or less, 50 moles or less, 40 moles or less, 30 moles or less, 25 moles or less, 22 moles or less, or 21 moles or less.

[0117] In an exemplary embodiment of the present specification, relative to 100 parts by weight of the entire composition for polymerizing a high refractive index resin, the content of the third compound may be 1 part by weight or more, 10 parts by weight or more, 30 parts by weight or more, 50 parts by weight or more, 60 parts by weight or more, 70 parts by weight or more, 75 parts by weight or more, or 77 parts by weight or more, and 95 parts by weight or less, 90 parts by weight or less, 85 parts by weight or less, 80 parts by weight or less, or 79 parts by weight or less.

[0118] In an exemplary embodiment of the present specification, relative to 100 moles of the entire composition for polymerizing a high refractive index resin, the content of the third compound may be 1 mole or more, 10 moles or more, 30 moles or more, 50 moles or more, 60 moles or more, 70 moles or more, 72 moles or more, 74 moles or more, or 75 moles or more, and 90 moles or less, 85 moles or less, 80 moles or less, 79 moles or less, 78 moles or less, 77 moles or less, or 76 moles or less.

[0119] The above content ranges mean the content of the entire third compound. For example, when two types of third compounds are used, the total content of the two types falls within the above range. That is, when two types are used, the content of each of the two types of third compounds is not particularly limited as long as the above total content is satisfied.

[0120] In terms of parts by weight and parts by mole, 100 parts by weight or 100 parts by mole of the entire composition for polymerizing a high refractive index resin means 100 parts by weight or 100 parts by mole of the entire monomer composition for polymerizing a high refractive index resin. That is, 100 parts by weight or 100 parts by mole of the entire composition for polymerizing a high refractive index resin is based on the case of not containing a solvent and a catalyst.

[0121] The higher the contents of the second compound and the third compound are, the better the processability of the resin is.

[0122] In one exemplary embodiment of the present specification, the composition for polymerizing a high refractive index resin may further contain a fourth compound represented by the following Chemical Formula 4.

[0123] [Chemical Formula 4]

[0124]

[0125] In Chemical Formula 4,

[0126] R4 and R5 are each independently an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group.

[0127] When the composition for polymerizing a high refractive index resin contains the fourth compound, high refractive index resins having various structures with excellent optical properties while having a thin thickness can be provided. In particular, when the composition is used together with the compound of Chemical Formula 1, a resin having excellent birefringence properties can be provided by having a non-aromatic main chain and a non-planar three-dimensional amorphous structure.

[0128] In one exemplary embodiment of the present specification, R4 and R5 may each independently be a C1-C10 alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a C3-C20 cycloalkyl group which is unsubstituted or substituted with an alkyl group; or a C6-C30 aryl group.

[0129] In one exemplary embodiment of the present specification, R4 and R5 may each independently be an unsubstituted or aryl- or heteroaryl-substituted methyl group; an unsubstituted or alkyl-substituted cyclopentyl group; an unsubstituted or alkyl-substituted cyclohexyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0130] In one exemplary embodiment of the present specification, R4 and R5 may each independently be a C1-C10 alkyl group which is unsubstituted or substituted with a C6-C30 aryl group or a C2-C30 heteroaryl group; a C3-C20 cycloalkyl group which is unsubstituted or substituted with a C1-C10 alkyl group; or a C6-C30 aryl group.

[0131] In one exemplary embodiment of the present specification, R4 and R5 may each independently be a C1-C10 alkyl group that is unsubstituted or substituted with a C6-C20 aryl group or a C2-C20 heteroaryl group; a C3-C20 cycloalkyl group that is unsubstituted or substituted with a C1-C10 alkyl group; or a C6-C30 aryl group.

[0132] In one exemplary embodiment of the present specification, R4 and R5 may each independently be a methyl group that is unsubstituted or substituted with a C6-C30 aryl group or a C2-C30 heteroaryl group; a cyclopentyl group that is unsubstituted or substituted with a C1-C10 alkyl group; a cyclohexyl group that is unsubstituted or substituted with a C1-C10 alkyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0133] In one exemplary embodiment of the present specification, R4 and R5 may each independently be a methyl group that is unsubstituted or substituted with a C6-C20 aryl group or a C2-C20 heteroaryl group; a cyclopentyl group that is unsubstituted or substituted with a C1-C10 alkyl group; a cyclohexyl group that is unsubstituted or substituted with a C1-C10 alkyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0134] In one exemplary embodiment of the present specification, R4 and R5 may each independently be a methyl group that is unsubstituted or substituted with a phenyl group, an anthracenyl group, or a carbazolyl group; a cyclopentyl group that is unsubstituted or substituted with a methyl group; a cyclohexyl group that is unsubstituted or substituted with one or more methyl groups; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0135] In one exemplary embodiment of the present specification, the fourth compound may be any one selected from the following compounds.

[0136]

[0137] In one exemplary embodiment of the present specification, relative to 100 parts by weight of the entire composition for polymerizing the high refractive index resin, the content of the fourth compound may be 1 part by weight or more, 2 parts by weight or more, 3 parts by weight or more, 4 parts by weight or more, or 5 parts by weight or more, and 30 parts by weight or less, 20 parts by weight or less, 10 parts by weight or less, 9 parts by weight or less, or 8 parts by weight or less.

[0138] Within the above range, the higher the content of the fourth compound, the better the refractive index and heat resistance of the resin.

[0139] In one exemplary embodiment of the present specification, the composition for polymerizing the high refractive index resin may be a solid at room temperature.

[0140] Another exemplary embodiment of the present invention provides a method for preparing a high refractive index resin, the method comprising polymerizing the above composition for polymerizing the high refractive index resin.

[0141] In an exemplary embodiment of the present specification, the polymerization of the composition for polymerizing a high refractive index resin can be solution polymerization of the composition for polymerizing a high refractive index resin.

[0142] In the solution polymerization of the composition, any solution polymerization method known in the art can be used.

[0143] In an exemplary embodiment of the present specification, the polymerization of the composition for polymerizing a high refractive index resin can include: dissolving the composition for polymerizing a high refractive index resin in a solvent to prepare a solution of the composition for polymerizing a high refractive index resin; dissolving the solution of the composition for polymerizing a high refractive index resin in a nitrogen atmosphere at 80 °C; heating the dissolved solution of the composition for polymerizing a high refractive index resin to 120 °C; dropping a catalyst solution into the dissolved solution of the composition for polymerizing a high refractive index resin; and reacting the resulting mixture for 20 hours.

[0144] The catalyst can be used as a polymerization initiator for the composition for polymerizing a high refractive index resin. The position where polymerization occurs in the first compound can vary depending on the type of catalyst.

[0145] In an exemplary embodiment of the present specification, the catalyst can be a radical polymerization initiator.

[0146] In an exemplary embodiment of the present specification, the catalyst can be an azo compound.

[0147] In an exemplary embodiment of the present specification, the catalyst can be 1,1'-azobis(cyclohexanenitrile) (ABCN) or 1,1'-azobisisobutyronitrile (AIBN).

[0148] In an exemplary embodiment of the present specification, the catalyst can be 1,1'-azobis(cyclohexanenitrile) (ABCN).

[0149] In an exemplary embodiment of the present specification, relative to 100 parts by weight of the entire composition for polymerizing a high refractive index resin, the amount of the catalyst used can be 1 part by weight or more, 3 parts by weight or more, 6 parts by weight or more, 8 parts by weight or more, 10 parts by weight or more, 12 parts by weight or more, 13 parts by weight or more, or 14 parts by weight or more, and 20 parts by weight or less, 19 parts by weight or less, 18 parts by weight or less, 17 parts by weight or less, 16 parts by weight or less, or 15 parts by weight or less.

[0150] In one exemplary embodiment of the present specification, relative to 100 parts by mole of the entire composition for polymerizing the high refractive index resin, the amount of the catalyst used may be 1 part by mole or more, 3 parts by mole or more, 5 parts by mole or more, 7 parts by mole or more, 8 parts by mole or more, or 9 parts by mole or more, and 20 parts by mole or less, 15 parts by mole or less, 13 parts by mole or less, 12 parts by mole or less, or 11 parts by mole or less.

[0151] In one exemplary embodiment of the present specification, there is no limitation on the solvent as long as it can dissolve the composition for polymerizing the high refractive index resin.

[0152] In one exemplary embodiment of the present specification, the solvent may be xylene.

[0153] The solvent may be used in an appropriate amount such that the composition for polymerizing the high refractive index resin can be dissolved.

[0154] The high refractive index resin according to one exemplary embodiment of the present specification includes: a first unit represented by the following Chemical Formula 11; and one or more types selected from the following: a second unit represented by the following Chemical Formula 12 and a third unit represented by the following Chemical Formula 13.

[0155] [Chemical Formula 11]

[0156]

[0157] [Chemical Formula 12]

[0158]

[0159] [Chemical Formula 13]

[0160]

[0161] In Chemical Formulas 11 to 13,

[0162] * means a part connected to the main chain of the resin,

[0163] R11 is an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group,

[0164] R21 and R31 are each independently an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group,

[0165] Z1 is a direct bond; -O-; or -COO-, and

[0166] X1 is hydrogen; or an alkyl group.

[0167] In one exemplary embodiment of the present specification, the first unit represented by Chemical Formula 11 is a unit derived from the first compound represented by Chemical Formula 1.

[0168] In one exemplary embodiment of the present specification, the second unit represented by Chemical Formula 12 is a unit derived from the second compound represented by Chemical Formula 2.

[0169] In one exemplary embodiment of the present specification, the third unit represented by Chemical Formula 13 is a unit derived from the third compound represented by Chemical Formula 3.

[0170] In other words, when a high refractive index resin is prepared by polymerizing a composition for polymerizing a high refractive index resin, polymerization occurs at the norbornene ring of Chemical Formula 1, so that a high refractive index resin containing the first unit represented by Chemical Formula 11 in the main chain can be obtained.

[0171] The high refractive index resin containing the unit represented by Chemical Formula 11 has a high refractive index compared to other types of resins, and has excellent optical properties while having a thin thickness. Therefore, the resin can be easily used in products that require small optical materials.

[0172] In one exemplary embodiment of the present specification, R11 may be a C1-C10 alkyl group that is unsubstituted or substituted with an aryl or heteroaryl group; a C3-C20 cycloalkyl group that is unsubstituted or substituted with an alkyl group; or a C6-C30 aryl group.

[0173] In one exemplary embodiment of the present specification, R11 may be an unsubstituted or aryl- or heteroaryl-substituted methyl group; an unsubstituted or alkyl-substituted cyclopentyl group; an unsubstituted or alkyl-substituted cyclohexyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0174] In one exemplary embodiment of the present specification, R11 may be a C1-C10 alkyl group that is unsubstituted or substituted with a C6-C30 aryl or C2-C30 heteroaryl group; a C3-C20 cycloalkyl group that is unsubstituted or substituted with a C1-C10 alkyl group; or a C6-C30 aryl group.

[0175] In one exemplary embodiment of the present specification, R11 may be a C1-C10 alkyl group that is unsubstituted or substituted with a C6-C20 aryl or C2-C20 heteroaryl group; a C3-C20 cycloalkyl group that is unsubstituted or substituted with a C1-C10 alkyl group; or a C6-C30 aryl group.

[0176] In an exemplary embodiment of the present specification, R11 may be methyl that is unsubstituted or substituted with a C6-C30 aryl or a C2-C30 heteroaryl; cyclopentyl that is unsubstituted or substituted with a C1-C10 alkyl; cyclohexyl that is unsubstituted or substituted with a C1-C10 alkyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0177] In an exemplary embodiment of the present specification, R11 may be methyl that is unsubstituted or substituted with a C6-C20 aryl or a C2-C20 heteroaryl; cyclopentyl that is unsubstituted or substituted with a C1-C10 alkyl; cyclohexyl that is unsubstituted or substituted with a C1-C10 alkyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0178] In an exemplary embodiment of the present specification, R11 may be methyl that is unsubstituted or substituted with phenyl, anthryl, or carbazolyl; cyclopentyl that is unsubstituted or substituted with methyl; cyclohexyl that is unsubstituted or substituted with one or more methyl groups; phenyl; biphenyl; naphthyl; or fluorenyl.

[0179] In an exemplary embodiment of the present specification, R21 and R31 may each independently be a C1-C10 alkyl that is unsubstituted or substituted with an aryl or a heteroaryl; a C3-C20 cycloalkyl that is unsubstituted or substituted with an alkyl; or a C6-C30 aryl.

[0180] In an exemplary embodiment of the present specification, R21 and R31 may each independently be methyl that is unsubstituted or substituted with an aryl or a heteroaryl; cyclopentyl that is unsubstituted or substituted with an alkyl; cyclohexyl that is unsubstituted or substituted with an alkyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0181] In an exemplary embodiment of the present specification, R21 and R31 may each independently be a C1-C10 alkyl that is unsubstituted or substituted with a C6-C30 aryl or a C2-C30 heteroaryl; a C3-C20 cycloalkyl that is unsubstituted or substituted with a C1-C10 alkyl; or a C6-C30 aryl.

[0182] In an exemplary embodiment of the present specification, R21 and R31 may each independently be a C1-C10 alkyl that is unsubstituted or substituted with a C6-C20 aryl or a C2-C20 heteroaryl; a C3-C20 cycloalkyl that is unsubstituted or substituted with a C1-C10 alkyl; or a C6-C30 aryl.

[0183] In an exemplary embodiment of the present specification, R21 and R31 may each independently be methyl that is unsubstituted or substituted with a C6-C30 aryl or C2-C30 heteroaryl; cyclopentyl that is unsubstituted or substituted with a C1-C10 alkyl; cyclohexyl that is unsubstituted or substituted with a C1-C10 alkyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0184] In an exemplary embodiment of the present specification, R21 and R31 may each independently be methyl that is unsubstituted or substituted with a C6-C20 aryl or C2-C20 heteroaryl; cyclopentyl that is unsubstituted or substituted with a C1-C10 alkyl; cyclohexyl that is unsubstituted or substituted with a C1-C10 alkyl; phenyl; biphenyl; naphthyl; or fluorenyl.

[0185] In an exemplary embodiment of the present specification, R21 and R31 may each independently be methyl that is unsubstituted or substituted with phenyl, anthryl, or carbazolyl; cyclopentyl that is unsubstituted or substituted with methyl; cyclohexyl that is unsubstituted or substituted with one or more methyl groups; phenyl; biphenyl; naphthyl; or fluorenyl.

[0186] In an exemplary embodiment of the present specification, X1 may be hydrogen; or a C1-C10 alkyl.

[0187] In an exemplary embodiment of the present specification, X1 may be hydrogen; or a C1-C5 alkyl.

[0188] In an exemplary embodiment of the present specification, X1 may be hydrogen; methyl; or ethyl.

[0189] In an exemplary embodiment of the present specification, X1 may be hydrogen; or methyl.

[0190] In an exemplary embodiment of the present specification, Z1 may be -O-; or -COO-.

[0191] In an exemplary embodiment of the present specification, Z1 may be -O-.

[0192] In an exemplary embodiment of the present specification, the high refractive index resin may further contain a fourth unit represented by the following Chemical Formula 14.

[0193] [Chemical Formula 14]

[0194]

[0195] In Chemical Formula 14,

[0196] R41 and R51 are each independently an alkyl that is unsubstituted or substituted with an aryl or heteroaryl; a cycloalkyl that is unsubstituted or substituted with an alkyl; or an aryl.

[0197] In an exemplary embodiment of the present specification, the fourth unit represented by Chemical Formula 14 is a unit derived from the fourth compound represented by Chemical Formula 4.

[0198] In an exemplary embodiment of the present specification, R41 and R51 may each independently be a C1-C10 alkyl group that is unsubstituted or substituted with an aryl or heteroaryl group; a C3-C20 cycloalkyl group that is unsubstituted or substituted with an alkyl group; or a C6-C30 aryl group.

[0199] In an exemplary embodiment of the present specification, R41 and R51 may each independently be an unsubstituted or aryl- or heteroaryl-substituted methyl group; an unsubstituted or alkyl-substituted cyclopentyl group; an unsubstituted or alkyl-substituted cyclohexyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0200] In an exemplary embodiment of the present specification, R41 and R51 may each independently be a C1-C10 alkyl group that is unsubstituted or substituted with a C6-C30 aryl group or a C2-C30 heteroaryl group; a C3-C20 cycloalkyl group that is unsubstituted or substituted with a C1-C10 alkyl group; or a C6-C30 aryl group.

[0201] In an exemplary embodiment of the present specification, R41 and R51 may each independently be a C1-C10 alkyl group that is unsubstituted or substituted with a C6-C20 aryl group or a C2-C20 heteroaryl group; a C3-C20 cycloalkyl group that is unsubstituted or substituted with a C1-C10 alkyl group; or a C6-C30 aryl group.

[0202] In an exemplary embodiment of the present specification, R41 and R51 may each independently be an unsubstituted or C6-C30 aryl- or C2-C30 heteroaryl-substituted methyl group; an unsubstituted or C1-C10 alkyl-substituted cyclopentyl group; an unsubstituted or C1-C10 alkyl-substituted cyclohexyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0203] In an exemplary embodiment of the present specification, R41 and R51 may each independently be an unsubstituted or C6-C20 aryl- or C2-C20 heteroaryl-substituted methyl group; an unsubstituted or C1-C10 alkyl-substituted cyclopentyl group; an unsubstituted or C1-C10 alkyl-substituted cyclohexyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0204] In an exemplary embodiment of the present specification, R41 and R51 may each independently be an unsubstituted or phenyl-, anthracenyl- or carbazolyl-substituted methyl group; an unsubstituted or methyl-substituted cyclopentyl group; an unsubstituted or one or more methyl-substituted cyclohexyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

[0205] In an exemplary embodiment of the present specification, the high refractive index resin may be a random copolymer or a block copolymer.

[0206] In an exemplary embodiment of the present specification, the weight average molecular weight (Mw) of the high refractive index resin may be 20,000 g / mol or greater, 22,000 g / mol or greater, 24,000 g / mol or greater, 26,000 g / mol or greater, 28,000 g / mol or greater, 29,000 g / mol or greater, or 30,000 g / mol or greater, and 500,000 g / mol or less, 400,000 g / mol or less, 300,000 g / mol or less, 200,000 g / mol or less, 100,000 g / mol or less, 80,000 g / mol or less, 60,000 g / mol or less, 50,000 g / mol or less, or 40,000 g / mol or less. When the high refractive index resin satisfies the above weight average molecular weight range, the high refractive index resin may have optimal fluidity and processability.

[0207] In an exemplary embodiment of the present specification, the number average molecular weight (Mn) of the high refractive index resin may be 3,000 g / mol or greater, 3,500 g / mol or greater, 4,000 g / mol or greater, 4,100 g / mol or greater, 4,200 g / mol or greater, 4,300 g / mol or greater, or 4,400 g / mol or greater, and 100,000 g / mol or less, 80,000 g / mol or less, 70,000 g / mol or less, 60,000 g / mol or less, 50,000 g / mol or less, 40,000 g / mol or less, 30,000 g / mol or less, 20,000 g / mol or less, 10,000 g / mol or less, 8,000 g / mol or less, or 7,000 g / mol or less.

[0208] In this specification, the weight-average molecular weight (Mw) of the high refractive index resin can be measured by gel permeation chromatography (GPC) using polystyrene (PS) standards with an Agilent 1200 series. Specifically, the weight-average molecular weight can be measured using an Agilent 1200 series device with Polymer Laboratories PLgel MIX-B 300 mm length columns. In this case, the measurement temperature is 40 °C, the solvent used is tetrahydrofuran (THF), and the flow rate is 1 mL / min. Each resin sample is prepared at a concentration of 10 mg / 10 mL, then fed in an amount of 10 μL, and the weight-average molecular weight (Mw) value is derived using a calibration curve formed with polystyrene standards. In this case, nine types of polystyrene standard products with molecular weights (g / mol) of 2,000 / 10,000 / 30,000 / 70,000 / 200,000 / 700,000 / 2,000,000 / 4,000,000 / 10,000,000 are used.

[0209] In one exemplary embodiment of this specification, the refractive index of the high refractive index resin measured at a wavelength of 587 nm can be 1.56 or greater, 1.57 or greater, 1.58 or greater, or 1.59 or greater, and 1.90 or less, 1.85 or less, 1.80 or less, 1.75 or less, 1.70 or less, 1.65 or less, or 1.62 or less.

[0210] When the high refractive index resin satisfies the above refractive index, a thin and light optical lens can be manufactured when the resin is applied to a molded article such as an optical lens.

[0211] In one exemplary embodiment of this specification, the Abbe number of the high refractive index resin measured and calculated at wavelengths of 486 nm, 587 nm, and 656 nm can be 10 or greater, 15 or greater, 20 or greater, 22 or greater, 25 or greater, 26 or greater, or 27 or greater, and 40 or less, 35 or less, 33 or less, 32 or less, or 31 or less. When the high refractive index resin satisfies the above Abbe number range, there is an effect of reducing dispersion and increasing clarity when the high refractive index resin is applied to a molded article such as an optical lens.

[0212] The Abbe number can be specifically obtained by measuring the refractive indices (n D , n F and n C ) at wavelengths of D (587 nm), F (486 nm), and C (656 nm) at 25 °C respectively using the following equation.

[0213] Abbe number = (nD -1) / (n F -n C )

[0214] The refractive index can be measured by the prism coupling method, and for example, SPA-3DR manufactured by SAIRON Technology Inc. can be used, but not limited thereto.

[0215] The refractive index of the high refractive index resin can be calculated by measuring the change in the amount of light reflected from a sample prepared by flattening the resin by placing a glass slide on a heating plate at 200 °C using a prism coupler. When the prepared sample is brought into contact with the prism and then a laser is incident on the prism, most of the incident laser is totally reflected, but when specific incident angles and conditions are met, light is coupled due to the generation of an evanescent field at the boundary surface. By measuring the angle at which coupling occurs (and as a result, the intensity of the light detected by the detector decreases sharply), the refractive index of the film can be automatically calculated by the prism coupler from parameters related to the polarization mode of the light and the refractive indices of the prism and the substrate.

[0216] According to an exemplary embodiment of the present specification, the glass transition temperature (Tg) of the high refractive index resin can be 160 °C or higher, 165 °C or higher, 170 °C or higher, 175 °C or higher, 180 °C or higher, 182 °C or higher, 184 °C or higher, or 185 °C or higher, and 200 °C or lower, 198 °C or lower, 196 °C or lower, 195 °C or lower, or 194 °C or lower. When the high refractive index resin satisfies the above glass transition temperature range, the resin has excellent heat resistance and injection molding characteristics.

[0217] In the present specification, the glass transition temperature (Tg) can be measured by a differential scanning calorimeter (DSC). Specifically, the glass transition temperature can be measured from a graph obtained as follows: heating a polycarbonate resin sample of 5.5 mg to 8.5 mg to 270 °C in a nitrogen atmosphere, and then scanning the resin sample while heating the resin sample at a heating rate of 10 °C / min during the second heating after cooling.

[0218] In addition, another exemplary embodiment of the present specification provides an article containing a high refractive index resin. The article can be a coating material, a curable material, a lens material, an optical substrate material, etc., but not limited thereto.

[0219] In an exemplary embodiment of the present specification, the article containing a high refractive index resin can be an optical lens.

[0220] Embodiments of the invention

[0221] Hereinafter, this specification will be described in detail with reference to the embodiments for specifically describing this specification. However, the embodiments according to this specification can be modified in various forms, and it is not to be construed that the scope of this application is limited to the embodiments described in detail below. The embodiments of this application are provided to more fully illustrate this specification to those of ordinary skill in the art.

[0222] <Preparation Example 1> Preparation of a Composition for Polymerizing a High-Refractive-Index Resin

[0223] A composition for polymerizing a high-refractive-index resin was prepared using the monomer composition shown in Table 1 below, and then it was mixed with 30 g of xylene to prepare a solution of the composition for polymerizing a high-refractive-index resin.

[0224] Specifically, the monomers for polymerizing a high-refractive-index resin were mixed in the molar percentages shown in Table 1 below based on 1 mole of all the monomers.

[0225] [Table 1]

[0226]

[0227] The structures of the compounds used as monomers are as follows:

[0228]

[0229] <Preparation Example 2> Preparation of High-Refractive-Index Resin Powder

[0230] The solution of the composition for polymerizing a high-refractive-index resin prepared in Preparation Example 1 was dissolved at 80°C in a nitrogen atmosphere, then heated to 120°C, and then an ABCN solution was dropped into it, and the resulting mixture was reacted for 20 hours.

[0231] As the ABCN solution, an ABCN solution prepared by mixing 0.1 mol% of 1,1'-azobis(cyclohexanenitrile) (ABCN) based on 1 mole of the entire monomers for polymerizing a high-refractive-index resin with 30 g of xylene was used.

[0232] After the reaction was completed, xylene was added to the reactor to dilute the resulting mixture to 10 wt% to 20 wt%, and the mixture was precipitated in methanol and filtered to obtain a high-refractive-index resin.

[0233] The obtained high-refractive-index resin was vacuum-dried in a vacuum oven at 80°C for 24 hours to prepare high-refractive-index resin powder.

[0234] <Experimental Example> Evaluation of High-Refractive-Index Resin Characteristics

[0235] (1) Number-average molecular weight (Mn), weight-average molecular weight (Mw), and molecular weight distribution (PDI)

[0236] The molecular weight and molecular weight distribution of the high refractive index resin sample were determined by gel permeation chromatography (GPC), and a thermogram was obtained using a differential scanning calorimeter (DSC) to study the thermal properties.

[0237] For the molecular weight by gel permeation chromatography (GPC), the results were obtained by injecting a solution produced by dissolving the sample in tetrahydrofuran at a concentration of 1.0 mg / 1 ml using tetrahydrofuran (THF, stabilized without butylated hydroxytoluene (BHT)) as a solvent, filtering the dissolved sample with a syringe filter, and measuring the molecular weight at 40 °C. The results are shown in Table 2 below. A Waters RI detector was used, and two Agilent PLgel MIXED - B columns were used.

[0238] (2) Refractive index (RI) and Abbe number

[0239] The measurement results of the refractive index can be determined from the high refractive index resin sample, and the result values according to the wavelength of light were obtained using a prism - coupler.

[0240] After closely contacting the sample with the prism of the prism - coupler, light at a specific wavelength was incident on the sample through the prism. Thereafter, after measuring the incident angle of light resonance to measure the refractive index therefrom, the Sellmeier coefficients that minimize the error value were obtained and substituted into the Sellmeier equation, and then the refractive index at the wavelength of D(587 nm) was determined.

[0241] Specifically, the refractive index was measured at a wavelength of 587 nm, and the Abbe number was obtained from the following equation by measuring the refractive indices (nD, nF, and nC) at the wavelengths of D(587 nm), F(486 nm), and C(656 nm) respectively, and is shown in Table 2 below.

[0242] Abbe number = (nD - 1) / (nF - nC)

[0243] (3) Glass transition temperature (Tg)

[0244] A differential scanning calorimeter (DSC) was measured to determine the glass transition temperature (Tg) of the resin. The glass transition temperature (Tg) was obtained from the graph obtained by heating a resin sample of 5.5 mg to 8.5 mg to 270 °C under a N2 flow, cooling the resin sample, and then heating the resin sample at a heating rate of 10 °C / min during the second heating while scanning the resin sample, and the glass transition temperature (Tg) is shown in Table 2 below.

[0245] [Table 2]

[0246]

[0247] From the results in Table 2, it can be determined that the refractive index of the high refractive index resin polymerized using the composition for polymerizing a high refractive index resin of the present invention is excellent.

[0248] Specifically, it was determined that the refractive indices of Examples 1 and 2 were 1.56 or greater, which showed higher refractive indices than the comparative example group, and the molecular weights were also within the range providing optimal fluidity and processability. In addition, with an Abbe number and glass transition temperature within an appropriate range, the heat resistance and injection molding characteristics were excellent, and when the composition was applied to a molded article, an effect with small dispersion and high transparency could be exhibited. That is, in the case of the high refractive index resin prepared from the composition for polymerizing a high refractive index resin of the present invention, a small-sized optical material with excellent optical characteristics and a thin thickness could be provided.

[0249] In the case of Comparative Example 1, a resin was prepared by polymerizing only the first compound of Chemical Formula 1, but the molecular weight was 1,000 or less, and polymerization could not be achieved. That is, it was determined that a resin composed only of units derived from the first compound could not be prepared.

[0250] It was determined that Comparative Examples 2 and 3 were resins prepared by polymerizing a composition containing one or two types of the third compound represented by Chemical Formula 3 but not containing the first compound represented by Chemical Formula 1, and the refractive indices were lower than those of the example group. Specifically, it could be seen that Comparative Examples 2 and 3 did not exhibit excellent birefringence characteristics because they did not contain the first unit of the present invention.

Claims

1. A composition for polymerizing a high refractive index resin, comprising: a first compound represented by the following Chemical Formula 1; and one or more types selected from the following: a second compound represented by the following Chemical Formula 2 and a third compound represented by the following Chemical Formula 3: [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] Among them, In Chemical Formulas 1 to 3, R1 is an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group, R2 and R3 are each independently an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group, Z is a direct bond; -O-; or -COO-, and X is hydrogen; or an alkyl group.

2. The composition according to claim 1, wherein R1 is a methyl group substituted with an aryl group or a heteroaryl group; a cyclopentyl group which is unsubstituted or substituted with an alkyl group; a cyclohexyl group which is unsubstituted or substituted with an alkyl group; a phenyl group; a biphenyl group; a naphthyl group; or a fluorenyl group.

3. The composition according to claim 1, wherein, relative to 100 mole parts of the entire composition for polymerizing a high refractive index resin, the content of the first compound is 1 mole part or more and 50 mole parts or less.

4. The composition according to claim 1, wherein the composition comprises: the second compound; and one or more types of the third compound.

5. The composition according to claim 1, wherein the first compound is selected from the following compounds:

6. The composition according to claim 1, wherein the second compound is selected from the following compounds:

7. The composition according to claim 1, wherein the third compound is selected from the following compounds:

8. The composition according to claim 1, further comprising a fourth compound represented by the following Chemical Formula 4: [Chemical Formula 4] Among them, In Chemical Formula 4, R4 and R5 are each independently an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group.

9. A method for preparing a high refractive index resin, the method comprising: Polymerize the composition according to claim 1.

10. The method according to claim 9, wherein the composition for polymerizing a high refractive index resin further comprises a compound represented by the following Chemical Formula 4: [Chemical Formula 4] Among them, In Chemical Formula 4, R4 and R5 are each independently an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group.

11. A high refractive index resin, comprising: a first unit represented by the following Chemical Formula 11; and one or more of the following: a second unit represented by the following Chemical Formula 12 and a third unit represented by the following Chemical Formula 13: [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] Among them, In Chemical Formulas 11 to 13, * means a part connected to the main chain of the resin, R11 is an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group, R21 and R31 are each independently an alkyl group which is unsubstituted or substituted with an aryl group or a heteroaryl group; a cycloalkyl group which is unsubstituted or substituted with an alkyl group; or an aryl group, Z1 is a direct bond; -O-; or -COO-, and X1 is hydrogen; or an alkyl group.

12. The high refractive index resin according to claim 11, further comprising a fourth unit represented by the following Chemical Formula 14: [Chemical Formula 14] Among them, In Chemical Formula 14, R41 and R51 are each independently an alkyl group unsubstituted or substituted with an aryl or heteroaryl group; a cycloalkyl group unsubstituted or substituted with an alkyl group; or an aryl group.

13. The high refractive index resin according to claim 11, wherein the refractive index of the high refractive index resin measured at a wavelength of 587 nm is 1.56 or greater and 1.90 or less.

14. The high refractive index resin according to claim 11, wherein the weight average molecular weight of the high refractive index resin is 20,000 g / mol or greater and 500,000 g / mol or less.

15. An article comprising the high refractive index resin according to any one of claims 11 to 14.

16. The article according to claim 15, wherein the article is an optical lens.

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