Resin composition and article comprising the same

Abstract

A resin composition according to one embodiment of the present application comprises: a resin comprising a unit represented by the above chemical formula 1; and a resin comprising a unit represented by the above chemical formula 2.

Description

Technology Field

[0001] The present application claims the benefit of the filing dates of Korean Patent Application No. 10-2023-0002967 filed with the Korean Intellectual Property Office on January 9, 2023, and Korean Patent Application No. 10-2023-0135603 filed with the Korean Intellectual Property Office on October 12, 2023, the entire contents of which are incorporated herein by reference.

[0002] The present application relates to a resin composition and an article comprising the same. Background Technology

[0003] High-refractive index materials are materials with excellent photon refractive power and represent a dense medium in terms of photon transmission. Generally, glass has been used as a high-refractive index material, but it has disadvantages such as low safety and high specific gravity. Therefore, there is a need for the development of transparent, soft polymer-based high-refractive index materials.

[0004] The refractive resin, which is an example of the above-mentioned high-refractive index material, can be used in optical components requiring anti-reflection, light scattering, or light extraction effects, and, for example, can be used in optical plastic lenses; high-precision lenses for recording optical discs such as CDs or DVDs; prisms; optical fibers; light guide plates; optical adhesives or sealants; encapsulating materials for opto-semiconductors; or in functional materials applied to PDPs (Plasma Display Panels) or LCDs (Liquid Crystal Displays), such as anti-reflection films, light scattering films, viewing angle enhancement films, brightness enhancement films, or optical filters. Furthermore, the high-refractive index resin can also be used as an additive for preventing plastic degradation, as a cosmetic additive, or in automotive windows.

[0005] In addition, if the refractive index of an optical material is high, the thickness of the optical lens required to achieve the same level of correction becomes thinner. Accordingly, the higher the refractive index of the optical material, the thinner and lighter the lens can be manufactured, which enables the miniaturization of various devices in which the lens is used. High-refractive-index materials provide diversity in lens design, and their applications are gradually increasing.

[0006] Generally, as the refractive index of optical materials increases, there is a problem where the Abbe number decreases, and additionally, a certain level of transmittance is required for use as an optical material.

[0007] Therefore, in this technical field, research on materials capable of achieving high refractive index and high transmittance is necessary. Prior art literature

[0008] Republic of Korea Published Patent Application No. 2016-0067229 The problem to be solved

[0009] The present application aims to provide a resin composition and an article comprising the same. means of solving the problem

[0010] One embodiment of the present application is,

[0011] A resin comprising a unit represented by the following chemical formula 1; and

[0012] A resin comprising a unit represented by the following chemical formula 2.

[0013] A resin composition comprising

[0014] [Chemical Formula 1]

[0015]

[0016] [Chemical Formula 2]

[0017]

[0018] In the above chemical formulas 1 and 2,

[0019] Y1, Y2, Y3 and Y4 are identical or different from each other, and each is independently a hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and

[0020] X1, X2, X7 and X8 are identical or different from one another, and each is independently a directly bonded, O, C=O, or substituted or unsubstituted alkylene group, and

[0021] X3, X4, X5, and X6 are identical or different from each other, and each is independently O, or S, and

[0022] Z1 and Z2 are identical or different from each other, and each is independently a substituted or unsubstituted alkylene group, a substituted or unsubstituted heteroalkylene group, or a substituted or unsubstituted cycloalkylene group, and

[0023] p is an integer from 0 to 8, and when p is 2 or greater, the structures inside the parentheses are identical or different from each other, and

[0024] La is a substituted or unsubstituted divalent or higher alkyl group, a substituted or unsubstituted divalent or higher cycloalkyl group, a substituted or unsubstituted divalent or higher heteroalkyl group, a substituted or unsubstituted divalent or higher aryl group, a substituted or unsubstituted divalent or higher heteroaryl group, O, a divalent ester group, and when p is 0, La is a substituted or unsubstituted divalent alkyl group, a substituted or unsubstituted divalent cycloalkyl group, or a substituted or unsubstituted divalent aryl group, and

[0025] q is an integer from 1 to 12, and when q is 2 or greater, the structures inside the parentheses are identical or different from each other, and

[0026] X9, X10, X11, and X12 are identical or different from one another, and each is independently a directly bonded, divalent amide group, divalent urethane group, divalent urea group, divalent ester group, NR, O, or S, and

[0027] Z3 and Z4 are identical or different from each other and are each independently a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted heteroalkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and

[0028] n1, n2, n3, and n4 are each integers from 0 to 20, and when n1, n2, n3, and n4 are each 2 or greater, the structures inside each parenthesis are identical or different from each other, and

[0029] y1, y2, y3, and y4 are each integers from 1 to 20, and when y1, y2, y3, and y4 are 2 or more, the structures inside each parenthesis are identical or different from each other, and

[0030] R5 to R8 are identical or different from one another, and each is independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and adjacent functional groups can bond with each other to form a hydrocarbon ring, and

[0031] r7 and r8 are each integers from 0 to 4, and when r7 and r8 are each 2 or greater, the structures inside each parenthesis are identical or different from each other, and

[0032] A1 to A4 are identical or different from each other, and each is independently CRR', and

[0033] R and R' are identical or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0034] * refers to the part connected to the main chain of the resin.

[0035] In addition, another embodiment of the present application provides an article comprising the resin composition or a cured product thereof. Effects of the invention

[0036] A resin composition according to one embodiment of the present application has characteristics such as a high refractive index, excellent adhesion, high transmittance, and a high glass transition temperature.

[0037] In addition, the resin composition according to one embodiment of the present application can be applied as a coating material, a curable material, a lens material, an optical substrate material, etc. Specific details for implementing the invention

[0038] The present specification will be described in more detail below.

[0039] In this specification, when it is said that a member is located "on" another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0040] In this specification, when a part is described as "comprising" a certain component, it means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0041] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, the site where the substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0042] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen; nitro(NO2); nitrile(CN); alkyl; cycloalkyl; aryl; aryloxy; arylthio; alkylthio; and heteroaryl, or that it is substituted with two or more of the exemplified substituents connected together, or that it has no substituents.

[0043] In this specification, * indicates a joining site to another structure.

[0044] In this specification, the cycloalkylene group may be a monocyclic or polycyclic cycloalkylene group. Specifically, the cycloalkylene group may be a cycloalkylene group having 3 to 20 carbon atoms; a monocyclic or polycyclic cycloalkylene group having 6 to 18 carbon atoms; or a monocyclic or polycyclic cycloalkylene group having 6 to 12 carbon atoms. More specifically, the cycloalkylene group may be a divalent group derived from alicyclic hydrocarbons, such as a cyclopentylene group, a cyclohepsilene group, or a cycloheptylene group, as a monocyclic cycloalkylene group, and may be an adamantane-diyl group, a norbonane-diyl group, etc., as a polycyclic cycloalkylene group. However, it is not limited thereto. In addition, the cycloalkylene group may be substituted with one or more alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, or halogens, or may not be substituted.

[0045] In this specification, the description of the cycloalkylene group may be applied except that the cycloalkyl group is a monovalent group and not a divalent group.

[0046] In this specification, the alkylene group is a divalent group derived from an aliphatic hydrocarbon having 1 to 30 carbon atoms, 1 to 20 carbon atoms, 1 to 10 carbon atoms, or 1 to 5 carbon atoms, and may be a straight-chain or branched-chain alkylene group. Specific examples of alkylene groups include methylene, ethylene, propylene, n-propylene, isopropylene, butylene, n-butylene, isobutylene, tert-butylene, sec-butylene, 1-methyl-butylene, 1-ethyl-butylene, pentylene, n-pentylene, isopentylene, neopentylene, tert-pentylene, hexylene, n-hexylene, 1-methylpentylene, 2-methylpentylene, 4-methyl-2-pentylene, 3,3-dimethylbutylene, 2-ethylbutylene, heptylene, n-heptylene, 1-methylhexylene, octylene, n-octylene, tert-octylene, 1-methylheptylene. There are, but are not limited to, 2-ethylhexylene groups, 2-propylpentylene groups, n-nonylene groups, 2,2-dimethylheptylene groups, 1-ethyl-propylene groups, 1,1-dimethyl-propylene groups, isohexylene groups, 2-methylpentylene groups, 4-methylhexylene groups, 5-methylhexylene groups.

[0047] In this specification, a heteroalkylene group means a stable straight-chain or branched-chain or cyclic hydrocarbon radical, or a combination thereof, consisting of a carbon atom of the aforementioned alkylene group and one or more heteroatoms selected from the group consisting of O, N, Si, and S. Here, the nitrogen and sulfur atoms may optionally be oxidized, and the nitrogen heteroatom may optionally be quaternized. The heteroatom(s) O, N, S, and Si may be placed at any internal position of the heteroalkyl group or at a position where the alkyl group is attached to the rest of the molecule. Examples include -CH2-CH2-O-CH3, -CH2-CH2-NH-CH3, -CH2-CH2-N(CH3)-CH3, -CH2-S-CH2-CH3, -CH2-CH2-S(O)-CH3, -CH2-CH2-S(O)2-CH3, -CH=CH-O-CH3, -Si(CH3)3, -CH2-CH=N-OCH3, and -CH=CH-N(CH3)-CH3, but are not limited thereto. For example, as in -CH2-NH-OCH3 and -CH2-OSi(CH3)3, two or fewer heteroatoms may be consecutive.

[0048] In this specification, the description of straight-chain or branched-chain alkylenes may apply, except that the straight-chain or branched-chain alkyl is not a divalent group but a monovalent group.

[0049] In this specification, unless otherwise limited, alkyl groups include straight-chain alkyl groups, branched-chain alkyl groups, and cycloalkyl groups.

[0050] In this specification, the arylene group may be a monocyclic or polycyclic arylene, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms, and may be 6 to 20 carbon atoms. Specifically, the monocyclic arylene group may be a phenylene group, a biphenylylene group, a terphenylylene group, etc., but is not limited thereto. When the arylene group is a polycyclic arylene group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30 carbon atoms, and may be 10 to 20 carbon atoms. Specifically, the polycyclic arylene group may be a naphthylene group, anthracenylene group, phenanthrenylene group, triphenylenylene group, pyrenylene group, phenalenylene group, perylenylene group, chrysenylene group, fluorenylene group, etc., but is not limited thereto.

[0051] In this specification, the description of the arylene group may apply except that the aryl group is a monovalent group and not a divalent group.

[0052] In this specification, the heteroaryl group comprises one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms comprise one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms in the heteroaryl group is not particularly limited, but it is preferable that the number of carbon atoms be 1 to 30, and may be 1 to 20. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include, but are not limited to, thiophene, furan, dibenzofuran, dibenzothiophen, benzothiophen, pyrrole, imidazole, thiazole, oxazole, oxadiazole, pyridine, bipyridine, pyrimidine, triazine, triazole, acridine, pyridazine, pyrazine, quinoline, quinazolin, quinoxaline, phthalazine, pyridopyrimidine, pyridopyrazine, pyrazinopyrazine, isoquinoline, indole, and carbazole groups.

[0053] In this specification, the description of a heteroaryl group may apply except that the heteroarylen group is not a monovalent group but a divalent group.

[0054] In this specification, the divalent aliphatic hydrocarbon group refers to the aforementioned alkylene, cycloalkylene, etc.

[0055] In this specification, the alkoxy group may be an alkoxy group having 1 to 10 carbon atoms or 1 to 5 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy groups, ethoxy groups, n-propoxy groups, isopropoxy groups, n-butoxy groups, isobutoxy groups, tert-butoxy groups, sec-butoxy groups, 1-methyl-butoxy groups, 1-ethyl-butoxy groups, or pentoxy groups.

[0056] In this specification, the halogen group is a fluoro group, a chloro group, a bromo group, or an iodo group.

[0057] In this specification, the description of the aliphatic ring as described above for the cycloalkylene group or heterocycloalkylene group may be applied, and the description of the aromatic ring as the arylene group or heteroarylene group may be applied.

[0058] In this specification, the aryloxy group may be represented as -ORo, and the description of the aryl group described above applies to Ro.

[0059] In this specification, the arylthio group may be represented as -SRs1, and the description of the aryl group described above applies to Rs1.

[0060] In this specification, the alkylthio group may be represented as -SRs2, and the description of the alkyl group described above applies to Rs2.

[0061] In this specification, the oxygen of the ester group may be substituted with a straight chain having 1 to 30 carbon atoms, a branched chain having 3 to 30 carbon atoms, a cyclic alkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be any one of the following structural formulas, but is not limited thereto.

[0062]

[0063] In the above structural formula, R101 and R102 are the same or different from each other and are each independently a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0064] In this specification, a divalent ester group means that R101 or R102 is a divalent group, and there are two connecting portions of the ester group.

[0065] In this specification, hydrogen is hydrogen, deuterium, or tritium.

[0066] A resin composition according to one embodiment of the present application comprises: a resin comprising a unit represented by the following chemical formula 1; and a resin comprising a unit represented by the following chemical formula 2.

[0067] [Chemical Formula 1]

[0068]

[0069] [Chemical Formula 2]

[0070]

[0071] In the above chemical formulas 1 and 2,

[0072] Y1, Y2, Y3 and Y4 are identical or different from each other, and each is independently a hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and

[0073] X1, X2, X7 and X8 are identical or different from one another, and each is independently a directly bonded, O, C=O, or substituted or unsubstituted alkylene group, and

[0074] X3, X4, X5, and X6 are identical or different from each other, and each is independently O, or S, and

[0075] Z1 and Z2 are identical or different from each other, and each is independently a substituted or unsubstituted alkylene group, a substituted or unsubstituted heteroalkylene group, or a substituted or unsubstituted cycloalkylene group, and

[0076] p is an integer from 0 to 8, and when p is 2 or greater, the structures inside the parentheses are identical or different from each other, and

[0077] La is a substituted or unsubstituted divalent or higher alkyl group, a substituted or unsubstituted divalent or higher cycloalkyl group, a substituted or unsubstituted divalent or higher heteroalkyl group, a substituted or unsubstituted divalent or higher aryl group, a substituted or unsubstituted divalent or higher heteroaryl group, O, a divalent ester group, and when p is 0, La is a substituted or unsubstituted divalent alkyl group, a substituted or unsubstituted divalent cycloalkyl group, or a substituted or unsubstituted divalent aryl group, and

[0078] q is an integer from 1 to 12, and when q is 2 or greater, the structures inside the parentheses are identical or different from each other, and

[0079] X9, X10, X11, and X12 are identical or different from one another, and each is independently a directly bonded, divalent amide group, divalent urethane group, divalent urea group, divalent ester group, NR, O, or S, and

[0080] Z3 and Z4 are identical or different from each other and are each independently a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted heteroalkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and

[0081] n1, n2, n3, and n4 are each integers from 0 to 20, and when n1, n2, n3, and n4 are each 2 or greater, the structures inside each parenthesis are identical or different from each other, and

[0082] y1, y2, y3, and y4 are each integers from 1 to 20, and when y1, y2, y3, and y4 are 2 or more, the structures inside each parenthesis are identical or different from each other, and

[0083] R5 to R8 are identical or different from one another, and each is independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and adjacent functional groups can bond with each other to form a hydrocarbon ring, and

[0084] r7 and r8 are each integers from 0 to 4, and when r7 and r8 are each 2 or greater, the structures inside each parenthesis are identical or different from each other, and

[0085] A1 to A4 are identical or different from each other, and each is independently CRR', and

[0086] R and R' are identical or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0087] * refers to the part connected to the main chain of the resin.

[0088] In one embodiment of the present application, R7 and R8 of Formula 1 may be identical or different from each other and may each independently be selected from hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; and the following functional groups.

[0089]

[0090] In the above functional groups, * represents the site connected to Chemical Formula 1.

[0091] In one embodiment of the present application, the formula 1 may be derived from a compound selected from the group consisting of the following compounds.

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140] In the above structural formula, a and b are integers from 0 to 20, respectively.

[0141] In one embodiment of the present application, the formula 2 may be derived from a compound selected from the group consisting of the following compounds.

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] In the above structural formula,

[0153] m, n, and k are integers from 0 to 20, respectively, and

[0154] t and s are integers from 1 to 6, respectively.

[0155] In one embodiment of the present application, the resin composition may further include a resin comprising a unit represented by the following chemical formula 3.

[0156] [Chemical Formula 3]

[0157]

[0158] In the above chemical formula 3,

[0159] Y5 and Y6 are identical or different from each other, and each is independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and

[0160] X13 and X14 are identical or different from each other, and each is independently a C=O, or a substituted or unsubstituted alkylene group, and

[0161] X15, X16, X17, and X19 are identical or different from each other, and each is independently O, or S, and

[0162] X18 is C=O, , or is,

[0163] y5 and y6 are integers from 1 to 20, and if y5 and y6 are 2 or greater, the structures inside each parenthesis are identical or different from each other, and

[0164] r is an integer from 0 to 20, and if r is 2 or greater, the structures inside the parentheses are identical or different from each other, and

[0165] * refers to the part connected to the main chain of the resin,

[0166] Lc and Ld are selected from the following structural formulas, and

[0167]

[0168]

[0169]

[0170] In the above structural formula,

[0171] X are independently O or S, and

[0172] R1 and R2 are identical or different from each other, and each is independently a substituted or unsubstituted alkylene group or a substituted or unsubstituted cycloalkylene group, and

[0173] a and b are each integers from 0 to 50, and when a and b are each 2 or greater, the structures inside each parenthesis are identical or different from each other.

[0174] In one embodiment of the present application, it can be seen from the relationship between molecular structure and refractive index known by Lorentz-Lorenz's formula that a resin comprising a unit represented by Chemical Formula 1 increases the electron density of the molecule and reduces the molecular volume, thereby increasing the refractive index of the material composed of the molecule. Furthermore, since the core structure of Chemical Formula 1 is a derivative of BPA (Bisphenol A), the molecular volume is small and the packing ability is excellent, which can improve the refractive index of the resin. Additionally, since R7 and R8 of Chemical Formula 1 may have electron-rich substituents such as substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups, the electron density of the structure represented by Chemical Formula 1 can be increased, thereby further improving the refractive index of the resin. Accordingly, the resin composition according to one embodiment of the present application has a high refractive index and high transparency, and an optical lens, optical film, or optical resin utilizing it can have a thin thickness and exhibit excellent optical properties.

[0175] In one embodiment of the present application, the resin composition may further include a photoinitiator.

[0176] The above photoinitiator is a compound that generates an active species upon irradiation with an active energy line. The above active energy line can be defined as an energy line capable of generating an active species by decomposing a compound that generates an active species. Examples of such active energy lines include photonic energy lines such as visible light, ultraviolet light, infrared light, X-rays, alpha rays, beta rays, and gamma rays. However, it is preferable to use ultraviolet light as the above active energy line from the perspective that it has a constant energy level and a fast curing speed.

[0177] The above photoinitiator may include benzophenone-based, acetophenone-based, triazine-based, thioxantone-based, benzoin-based, phosphorus-based, oxime-based, or mixtures thereof, but is not limited thereto and may include photoinitiators commonly used in the industry.

[0178] Specific examples of the above-mentioned benzophenone-based photoinitiators may include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, or mixtures thereof, but are not limited thereto and may include conventional benzophenone-based photoinitiators without limitation.

[0179] Specific examples of the above acetophenone-based photoinitiators include acetophenone, 2,2-dimethylpropiophenone, 3-hydroxy-3-methyl-1-phenylbutan-1-one, 2,2-dimethoxy-2-phenylacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexylphenylketone (Irgacure 184), 2,4,6-trimethylbenzoyl diphenylphosphine oxide (Irgacure TPO), 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, (phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide), 2-(dimethylamino)-1-[4-(morpholinyl)phenyl]-2-phenylmethyl-1-butanone, 2-hydroxy-2-methyl-[4-(1-methylvinyl)phenyl]propanol oligomer, 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]-phenyl}-2-methylpropan-1-one (Irgacure 127), a mixture thereof, but not limited thereto, may include any ordinary acetophenone-based photoinitiator without limitation.

[0180] Specific examples of the above triazine-based photoinitiators include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, and bis(trichloromethyl)-6-styryl-s-triazine. It may be 2-(naphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl(piperonyl)-6-triazine, 2,4-(trichloromethyl(4'-methoxystyryl)-6-triazine, or a mixture thereof, but is not limited thereto, and may include any conventional triazine-based photoinitiator without limitation.

[0181] Specific examples of the above thioxantone-based photoinitiators may include thioxantone, 2-methyl thioxantone, isopropyl thioxantone, 2,4-diethyl thioxantone, 2,4-diisopropyl thioxantone, 2-chlorothioxantone, or mixtures thereof, but are not limited thereto and may include conventional thioxantone-based photoinitiators without limitation.

[0182] Specific examples of the above-mentioned benzoin-based photoinitiators may include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, or mixtures thereof, but are not limited thereto, and may include conventional benzoin-based photoinitiators without limitation.

[0183] Specific examples of the above phosphorus-based photoinitiator may include bisbenzoylphenyl phosphine oxide, benzoyldiphenyl phosphine oxide, or a mixture thereof, but are not limited thereto, and may include ordinary phosphorus-based photoinitiators without limitation.

[0184] Specific examples of the above-mentioned oxime-based photoinitiators include 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedion and 1-(o-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethanol, (1-hydroxycyclohexyl)(phenyl)methanone, O-acetyloxime, or mixtures thereof, but are not limited thereto and may include conventional oxime-based photoinitiators without limitation.

[0185] According to one embodiment of the present specification, the photoinitiator is the following chemical formula P.

[0186] [Chemical Formula P]

[0187]

[0188] In the above chemical formula P,

[0189] Q1 is O or NG6, and

[0190] G1 to G6 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted ester group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0191] Lb is hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroalkyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0192] lb is an integer from 1 to 10, and

[0193] If the above lb is 2 or more, the above 2 or more Lb are the same or different from each other.

[0194] In particular, in one embodiment of the present application, the photoinitiator may include the following compound.

[0195]

[0196] In one embodiment of the present application, the refractive index of the resin composition measured at a wavelength of 587 nm may be 1.5 or higher, 1.55 to 1.70, or 1.60 to 1.65. When the resin composition satisfies the above refractive index, it is possible to manufacture a thin and light optical lens when applied to a molded article such as an optical lens.

[0197] In one embodiment of the present application, the Abbe number measured and calculated at wavelengths of 486 nm, 587 nm, and 656 nm of the resin composition may be 10 to 40. Preferably, it may be 15 to 38, more preferably 20 to 35, and even more preferably 24.9 to 30.1. When the resin composition satisfies the above Abbe number range, when the resin composition is applied to a molded article such as an optical lens, there is an effect of reduced dispersion and increased clarity.

[0198] The above Abbe number is specifically the refractive index (n) at wavelengths D (587 nm), F (486 nm), and C (656 nm) at 25°C. D , n F , n C By measuring each of the following, the Abbe number can be obtained using the formula below.

[0199] Abbe number = (n D - 1) / (n F - n C )

[0200] The above refractive index can be measured using the prism coupler method; for example, the SPA-3DR from SAIRON Technology can be used, but is not limited to this.

[0201] By using a prism coupler, the refractive index can be calculated by measuring the change in the amount of light reflected from a sample prepared by flattening the resin by placing a slide glass on a 200°C heating plate. When a laser is incident on the prism after the prepared sample is brought into contact with the prism, most of the light undergoes total internal reflection; however, if a specific angle of incidence and conditions are satisfied, an evanescent field is generated at the interface, causing the light to be coupled. By measuring the angle at which the intensity of the light detected by the detector decreases rapidly due to coupling, the prism coupler can automatically calculate the refractive index of the film from parameters related to the polarization mode of light and the refractive indices of the prism and the substrate.

[0202] Additionally, another embodiment of the present application provides an article comprising the resin composition or a cured product thereof. The article may be a coating material, a curable material, a lens material, an optical substrate material, etc., but is not limited thereto.

[0203] Hereinafter, the present application will be described in detail with reference to examples to specifically explain the present application. However, the embodiments according to the present application may be modified in various different forms, and the scope of the present application is not to be interpreted as being limited to the embodiments described below. The embodiments of the present application are provided to more completely explain the present application to those with average knowledge in the art.

[0204] <실시예>

[0205] <실시예 1 ~ 10>

[0206] The mixture was mixed using the composition and content ratios listed in Table 1 below, and 3 parts by weight of a photoinitiator of the following structural formula were added and further stirred.

[0207] [Gwanggaesise]

[0208]

[0209] The completed mixture was coated onto a polycarbonate bare film, and then UV irradiated to form a coating layer with a thickness of 50 μm. At this time, the coating of the mixture was performed using a micrometer film applicator.

[0210] [Table 1]

[0211]

[0212]

[0213] [BPEFA]

[0214]

[0215] [BPEFAEG]

[0216]

[0217] In the above structural formula, m and n are integers from 1 to 20, respectively.

[0218] [TriA]

[0219]

[0220] [BPAAEG3]

[0221]

[0222] In the above structural formula, a + b = 3.

[0223] [BPAMAEG3]

[0224]

[0225] In the above structural formula, a + b = 3.

[0226] [BPAMAEG20]

[0227]

[0228] In the above structural formula, a + b = 20.

[0229] [COA]

[0230]

[0231] [TriAU]

[0232]

[0233] In the above structural formula, m, n, and k are integers from 1 to 20, respectively.

[0234] [DiAU]

[0235]

[0236] In the above structural formula, n is an integer from 1 to 20.

[0237] [IPAU]

[0238]

[0239] In the above structural formula, t and s are integers from 1 to 6, respectively.

[0240] [HMAU]

[0241]

[0242] In the above structural formula, t and s are integers from 1 to 6, respectively.

[0243] <실험예 1>

[0244] The characteristics of the resin composition prepared in the above example were evaluated and are shown in Table 2 below.

[0245] [Table 2]

[0246]

[0247] As shown in the above results, the resin composition according to one embodiment of the present application has characteristics such as a high refractive index and a high glass transition temperature.

[0248] Accordingly, the resin composition according to one embodiment of the present application can be applied as a coating material, a curable material, a lens material, an optical substrate material, etc.

Claims

Claim 1 A unit represented by the following chemical formula 1; and a resin composition comprising a unit represented by the following chemical formula 2: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formulas 1 and 2, Y1, Y2, Y3, and Y4 are identical or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; X1, X2, X7, and X8 are identical or different from each other and are each independently a direct bond, O, C=O, or a substituted or unsubstituted alkylene group; X3, X4, X5, and X6 are identical or different from each other and are each independently O or S; Z1 and Z2 are identical or different from each other and are each independently a substituted or unsubstituted alkylene group, a substituted or unsubstituted heteroalkylene group, or a substituted or unsubstituted cycloalkylene group; p is an integer from 0 to 8, and when p is 2 or more, the structures in parentheses are identical or different from each other; La is a substituted or unsubstituted divalent or higher alkyl group, a substituted or unsubstituted divalent or higher cycloalkyl group, or a substituted or unsubstituted divalent or higher A heteroalkyl group, a substituted or unsubstituted divalent or higher aryl group, a substituted or unsubstituted divalent or higher heteroaryl group, O, or a substituted or unsubstituted divalent ester group; where p is 0, La is a substituted or unsubstituted divalent alkyl group, a substituted or unsubstituted divalent cycloalkyl group, or a substituted or unsubstituted divalent aryl group; q is an integer from 1 to 12; where q is 2 or more, the structures in parentheses are identical or different from each other; X9, X10, X11, and X12 are identical or different from each other, and each is independently a direct bond, a divalent amide group, a divalent urethane group, a divalent urea group, a divalent ester group, NR, O, or S; and one or more of X11 and X12 are a divalent amide group, a divalent urethane group, or a divalent It is a urea group, and Z3 and Z4 are identical or different from each other, and each is independently a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted heteroalkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and n1, n2, n3 and n4 are each integers from 0 to 20, and n1, n2,If n3 and n4 are each 2 or more, the structures within each parenthesis are identical or different from each other, n3+n4 is 1 or more, y1, y2, y3, and y4 are each integers from 1 to 20, and if y1, y2, y3, and y4 are each 2 or more, the structures within each parenthesis are identical or different from each other, R5 to R8 are identical or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; a substituted or unsubstituted aryl group; or is a substituted or unsubstituted heteroaryl group, and adjacent functional groups can bond to each other to form a hydrocarbon ring, r7 and r8 are each integers from 0 to 4, and if r7 and r8 are each 2 or more, the structures in each parenthesis are identical or different from each other, A1 to A4 are identical or different from each other and are each independently CRR', R and R' are identical or different from each other and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, * indicates a site connected to the main chain of the resin. Claim 2 A resin composition according to claim 1, wherein the resin composition further comprises a photoinitiator. Claim 3 A resin composition according to claim 1, wherein R7 and R8 of Formula 1 are identical or different from each other and each independently select from hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; and the following functional groups: In the above functional groups, * represents the site connected to Chemical Formula 1. Claim 4 A resin composition according to claim 1, wherein the formula 1 is derived from a compound selected from the group consisting of the following compounds: In the above structural formula, a and b are integers from 0 to 20, respectively. Claim 5 A resin composition according to claim 1, wherein the formula 2 is derived from a compound selected from the group consisting of the following compounds: In the above structural formula, m, n, and k are integers from 0 to 20, respectively, and t and s are integers from 1 to 6, respectively. Claim 6 A resin composition according to claim 1, wherein the refractive index of the resin composition measured at 587 nm is 1.5 or higher. Claim 7 A resin composition comprising: a first unit represented by the following chemical formula 1; a second unit represented by the following chemical formula 2; and a third unit represented by the following chemical formula 3, wherein the third unit is in an amount of 55 parts by weight or more per 100 parts by weight of the total weight of the first to third units: [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 1 and 2, Y1, Y2, Y3, and Y4 are identical or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; X1, X2, X7, and X8 are identical or different from each other and are each independently a direct bond, O, C=O, or a substituted or unsubstituted alkylene group; X3, X4, X5, and X6 are identical or different from each other and are each independently O or S; Z1 and Z2 are identical or different from each other and are each independently a substituted or unsubstituted alkylene group, a substituted or unsubstituted heteroalkylene group, or a substituted or unsubstituted cycloalkylene group; p is an integer from 0 to 8, and when p is 2 or more, the structures in parentheses are identical or different from each other; La is a substituted or unsubstituted divalent or higher alkyl group, a substituted or unsubstituted divalent or higher cycloalkyl group, or a substituted or unsubstituted divalent or higher A heteroalkyl group, a substituted or unsubstituted divalent or higher aryl group, a substituted or unsubstituted divalent or higher heteroaryl group, O, or a substituted or unsubstituted divalent ester group; where p is 0, La is a substituted or unsubstituted divalent alkyl group, a substituted or unsubstituted divalent cycloalkyl group, or a substituted or unsubstituted divalent aryl group; q is an integer from 1 to 12; where q is 2 or more, the structures in parentheses are identical or different from each other; X9, X10, X11, and X12 are identical or different from each other, and each is independently a direct bond, a divalent amide group, a divalent urethane group, a divalent urea group, a divalent ester group, NR, O, or S; Z3 and Z4 are identical or different from each other, and each is independently a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted A heteroalkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, where n1, n2, n3, and n4 are each integers from 0 to 20, and where n1, n2, n3, and n4 are each 2 or more, the structures within each parenthesis are identical or different from each other, y1, y2,y3 and y4 are each integers from 1 to 20, and when y1, y2, y3, and y4 are 2 or more, the structures within each parenthesis are identical or different from each other, R5 and R6 are identical or different from each other and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or R5 and R6 can be combined to form an aliphatic hydrocarbon ring, and R7 and R8 are identical or different from each other and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; a substituted or unsubstituted aryl group; or are substituted or unsubstituted heteroaryl groups, or adjacent functional groups may bond to each other to form a hydrocarbon ring, r7 and r8 are each integers from 0 to 4, and when r7 and r8 are each 2 or more, the structures in each parenthesis are identical or different from each other, A1 to A4 are identical or different from each other and are each independently CRR', R and R' are identical or different from each other and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted heteroalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, * denotes a site connected to the main chain of the resin, and in the above chemical formula 3, Y5 and Y6 are identical or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, X13 and X14 are identical or different from each other and are each independently C=O, or a substituted or unsubstituted alkylene group, X15, X16, X17 and X19 are identical or different from each other and are each independently O, or S, and X18 is C=O, , or , and y5 and y6 are integers from 1 to 20, and if y5 and y6 are 2 or greater, the structures within each parenthesis are identical or different from each other, r is an integer from 0 to 20, and if r is 2 or greater, the structures within the parentheses are identical or different from each other, * indicates a region connected to the main chain of the resin, Lc and Ld are selected from the following structural formulas, and In the above structural formula, X is independently O or S, R1 and R2 are identical or different from each other, and are independently a substituted or unsubstituted alkylene group or a substituted or unsubstituted cycloalkylene group, a and b are each integers from 0 to 50, and when a and b are each 2 or more, the structures in each parenthesis are identical or different from each other. Claim 8 An article comprising a resin composition of any one of claims 1 to 7 or a cured product thereof. Claim 9 A resin composition according to claim 7, wherein the formula 2 is derived from a compound selected from the group consisting of the following compounds: In the above structural formula, m, n, and k are integers from 0 to 20, respectively, and t and s are integers from 1 to 6, respectively.

Images