Resin and preparation method thereof

Abstract

The present application relates to a resin comprising a unit of Formula 1, a method for manufacturing the same, a resin composition comprising the same, and a molded article comprising the resin composition.

Description

Technology Field

[0001] This specification relates to a resin and a method for manufacturing the same. Background Technology

[0002] 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.

[0003] Generally, as the refractive index of optical materials increases, there is a problem where the Abbe number decreases, and additionally, a certain level of transparency is required for use as an optical material. Prior art literature

[0004] Korean Published Patent Application No. 10-2020-0034523 The problem to be solved

[0005] One embodiment of the present specification aims to provide a resin of a novel structure and a method for manufacturing the same.

[0006] Another embodiment of the present specification aims to provide a composition comprising a resin having a novel structure and a molded article made of said resin composition. means of solving the problem

[0007] One embodiment of the present specification provides a resin comprising a unit of the following chemical formula 1.

[0008] [Chemical Formula 1]

[0009]

[0010] In the above chemical formula 1,

[0011] R1 to R4 are the same or different from each other, and each is an independently substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0012] Y1 and Y2 are the same or different from each other, and each independently is hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0013] L1 and L2 are the same or different from each other, and each is an independently substituted or unsubstituted alkylene group, and

[0014] R11 and R12 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group, and

[0015] a and b are 0 or 1, respectively, and

[0016] R5 is -O-; -S(O2)-; -C(RR')-; -N(R")-; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0017] R, R' and R" are the same or different from each other, and each independently is hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0018] r5 is an integer from 1 to 10, and

[0019] If the above r5 is 2 or more, the above 2 or more R1s are the same or different from each other, and

[0020] * refers to the part connected to the main chain of the resin.

[0021] One embodiment of the present specification provides a compound of the following formula 1a.

[0022] [Chemical Formula 1a]

[0023]

[0024] In the above chemical formula 1a,

[0025] R1 to R4 are the same or different from each other, and each is an independently substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0026] Y1 and Y2 are the same or different from each other, and each independently is hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0027] L1 and L2 are the same or different from each other, and each is an independently substituted or unsubstituted alkylene group, and

[0028] R11 and R12 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group, and

[0029] a and b are 0 or 1, respectively.

[0030] Another embodiment of the present specification provides a method for producing a resin comprising the step of polymerizing a composition for producing a resin comprising a compound of the following formula 1a; and a polyarylenethioether precursor.

[0031] [Chemical Formula 1a]

[0032]

[0033] In the above chemical formula 1a,

[0034] The definitions of R1 to R5, R11, R12, Y1, Y2, L1, L2, a and b are the same as those defined in Chemical Formula 1 above.

[0035] Another embodiment of the present specification provides a resin composition comprising a resin according to the above embodiment.

[0036] Another embodiment of the present specification provides a molded article comprising a composition comprising a resin according to the above embodiment. Effects of the invention

[0037] A resin according to one embodiment of the present specification has a high refractive index and a high Abbe number.

[0038] By using a resin according to one embodiment of the present specification, a thin, excellent optical member, optical lens, optical film, optical thin film, or optical resin can be obtained. Specific details for implementing the invention

[0039] The present specification will be described in more detail below.

[0040] According to one embodiment of the present specification, a resin containing a unit of Formula 1 can be seen from the relationship between molecular structure and refractive index known by Lorentz-Lorenz's formula that the electron density of the molecule is increased and the molecular volume is reduced, thereby increasing the refractive index of the material composed of the molecule.

[0041] In addition, since the core structure of Formula 1 is a derivative of BPA (bisphenol A), it has a small molecular volume and excellent packing ability, which can improve the refractive index of the resin. Furthermore, since R1 to R4 are electron-rich substituents such as substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups, the electron density of the structure of Formula 1 can be increased, thereby further improving the refractive index of the resin. Accordingly, the resin according to one embodiment of the present specification has a high refractive index and high transparency, and an optical lens, optical film, or optical resin using it can have a thin thickness and exhibit excellent optical properties.

[0042] In addition, the refractive index of a polymer can be increased by introducing substituents with high molecular refractive indices and low molar volumes according to the Lorentz-Lorentz equation. Accordingly, cyclic aromatic hydrocarbons, halogen atoms excluding fluorine, and sulfur atoms are factors that can increase the refractive index of a polymer. Therefore, high-refractive index materials can be manufactured by utilizing precursors containing sulfur, which has a high refractive index.

[0043] The above chemical formula 1 contains a derivative of bisphenol A, and since a and b are 0 or 1, a resin with a desired molecular weight and high refractive index can be obtained by appropriately adjusting the alkylene groups of L1 and L2, and when a and b are 1, despite being bulky, the solubility in organic solvents is high, making it suitable for carrying out solution polymerization and advantageous for setting polymerization conditions.

[0044] In one embodiment of the present invention, the unit of Formula 1 may be included in the resin in one or more ways, and if two or more are included, each unit may be the same or different from one another.

[0045] In this specification, the resin is a polyarylenethioether resin.

[0046] Throughout this specification, the term “combination thereof” included in the Markush-type expression means one or more mixtures or combinations selected from the group consisting of the components described in the Markush-type expression, and means including one or more selected from the group consisting of said components.

[0047] Examples of substituents in this specification are described below, but are not limited thereto.

[0048] In this specification, refers to the connected part.

[0049] 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 location is not limited to the location where the hydrogen atom is substituted, that is, any location where a 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.

[0050] 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 group; hydroxyl group; cyano group; alkyl group; cycloalkyl group; alkoxy group; alkenyl group; aryloxy group; arylthio group; alkylthio group; silyl group; aryl group; and heteroaryl group, or is substituted with a substituent in which two or more of the exemplified substituents are connected, or has no substituents.

[0051] In this specification, the connection of two or more substituents means that a hydrogen of one substituent is connected to another substituent. For example, the connection of two substituents means that a phenyl group and a naphthyl group are connected or It can be a substituent. In addition, the connection of three substituents includes not only the consecutive connection of (substituent 1)-(substituent 2)-(substituent 3), but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group are connected, , or It can be a substituent. The aforementioned definition applies equally to the connection of 4 or more substituents.

[0052] In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0053] In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited but is preferably 1 to 30. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, There are, but are not limited to, 2,2-dimethylheptyl groups, 1-ethyl-propyl groups, 1,1-dimethyl-propyl groups, isohexyl groups, 2-methylpentyl groups, 4-methylhexyl groups, 5-methylhexyl groups.

[0054] In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms. Specifically, it includes, but is not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, etc.

[0055] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 1 to 30 carbon atoms. Specifically, it may be a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentyloxy group, a neopentyloxy group, an isopentyloxy group, an n-hexyloxy group, a 3,3-dimethylbutyloxy group, a 2-ethylbutyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0056] In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include, butanely, vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0057] In the present specification, the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0058] When the above aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms be 6 to 50. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0059] When the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms be 10 to 50. Specifically, the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc., but is not limited thereto.

[0060] In the present specification, the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.

[0061] When the above fluorene group is substituted, , , , , , , and There are, but are not limited to, the following.

[0062] In this specification, "adjacent" groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the atom on which the substituent is substituted, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0063] In the present specification, the heteroaryl group comprises one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may comprise one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms be 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, pyridine, bipyridine, pyrimidine, triazine, triazole, acridine, pyridazine, pyrazine, quinoline, quinazolin, quinoxaline, phthalazine, pyridopyrimidine, pyridopyrazine, pyrazinopyrazine, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophen, dibenzothiophen, benzofuran, phenanthridine, phenanthroline, isooxazole, and thiadiazole. There are, but are not limited to, dibenzofuran groups, dibenzosilol groups, phenoxanthine groups (phenoxathiine), phenoxazine groups, phenothiazine groups, dihydroindenocarbazole groups, spiroflurenxanthen groups, spiroflurentioxanthen groups, tetrahydronaphthothiophen groups, tetrahydronaphthofuran groups, tetrahydrobenzofuran groups, and tetrahydrobenzofuran groups.

[0064] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group; a heteroarylsilyl group, etc. Among the alkylsilyl groups, the alkyl group may be an example of the alkyl group described above, among the arylsilyl groups, the aryl group may be an example of the aryl group described above, among the alkyl and aryl groups among the alkylarylsilyl groups, the alkyl and aryl groups may be an example of the alkyl and aryl groups described above, and among the heteroarylsilyl groups, the heteroaryl group may be an example of the heteroaryl group described above.

[0065] In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensation ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from examples of the cycloalkyl group, aryl group, and combinations thereof, and the hydrocarbon ring may be a phenyl group, a cyclohexyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a tetrahydronaphthalene group, a tetrahydroanthracene group, a 1,2,3,4-tetrahydro-1,4-methanonaphthalene group, a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group, a spirocyclopentanefluorene group, a spiroadamantanefluorene group, and a spirocyclohexanefluorene group, but is not limited thereto.

[0066] In the present specification, the heterocyclic group comprises one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may comprise one or more atoms selected from the group consisting of O, N, Se, and S. The heterocyclic group may be monocyclic or polycyclic, and may be an aromatic heterocyclic group; an aliphatic heterocyclic group; a condensation group of an aromatic heterocyclic group and an aliphatic heterocyclic group; a condensation group of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aromatic heterocyclic group; or a condensation group of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aliphatic heterocyclic group, and the aromatic heterocyclic group may be selected from the examples of the heteroaryl group.

[0067] In this specification, an aliphatic heterocyclic group refers to an aliphatic ring group comprising one or more heteroatoms. An aliphatic heterocyclic group includes all aliphatic rings with single bonds, aliphatic rings with multiple bonds, or aliphatic rings in the form of condensed rings comprising both single and multiple bonds. Examples of aliphatic heterocyclic groups include, but are not limited to, epoxy groups, oxirane groups, tetrahydrofuran groups, 1,4-dioxane groups, pyrrolidine groups, piperidine groups, morpholine groups, oxephane groups, azocaine groups, thiocane groups, tetrahydronaphthiophen groups, tetrahydronaphthofuran groups, tetrahydrobenzothiophen groups, and tetrahydrobenzofuran groups.

[0068] In this specification, the aryloxy group may be represented as -ORo, and the description of the aryl group described above applies to Ro.

[0069] In this specification, the arylthio group may be represented as -SRs1, and the description of the aryl group described above applies to Rs1.

[0070] In this specification, the alkylthio group may be represented as -SRs2, and the description of the alkyl group described above applies to Rs2.

[0071] In this specification, an alkylene group refers to a group having two bonding positions to an alkyl group, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the alkyl group described above may apply.

[0072] In this specification, a cycloalkylene group refers to a cycloalkyl group having two bonding sites, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the cycloalkyl group described above may apply.

[0073] In this specification, an arylene group refers to a group having two binding sites to an aryl group, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the aryl group described above may apply.

[0074] In this specification, a heteroarylene group refers to a group having two binding sites on an aryl group, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the heteroaryl group described above may apply.

[0075] In this specification, hydrogen is hydrogen, deuterium, or tritium.

[0076] In one embodiment of the present specification, the portion of Formula 1 that is not indicated by a substituent may mean that hydrogen, deuterium, or tritium is substituted.

[0077] Preferred embodiments of the present invention are described in detail below. However, embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

[0078] According to one embodiment of the present specification, the unit of Formula 1 may be included in the resin in one or more ways, and if two or more are included, each unit may be the same or different from one another.

[0079] In this specification, * refers to a part connected to another structure.

[0080] According to one embodiment of the present specification, a is 0.

[0081] According to one embodiment of the present specification, a is 1.

[0082] According to one embodiment of the present specification, b is 0.

[0083] According to one embodiment of the present specification, b is 1.

[0084] According to one embodiment of the present specification, the above chemical formula 1 is the following chemical formula 1-1.

[0085] [Chemical Formula 1-1]

[0086]

[0087] In the above chemical formula 1-1,

[0088] The definitions of R1 to R5, R11, R12, Y1, Y2, and r5 are the same as those defined in Chemical Formula 1 above.

[0089] According to one embodiment of the present specification, the above chemical formula 1 is the following chemical formula 1-2.

[0090] [Chemical Formula 1-2]

[0091]

[0092] In the above chemical formula 1-2,

[0093] The definitions of R1 to R5, R11, R12, Y1, Y2, L1, L2, and r5 are the same as those defined in Chemical Formula 1 above.

[0094] According to one embodiment of the present specification, when r5 is 2 or more, at least one of the 2 or more R5s is a substituted or unsubstituted arylene group.

[0095] According to one embodiment of the present specification, r5 is an integer from 1 to 3.

[0096] According to one embodiment of the present specification, r5 is 1.

[0097] According to one embodiment of the present specification, r5 is 3.

[0098] According to one embodiment of the present specification, when r5 is 1, R5 is a substituted or unsubstituted arylene group.

[0099] According to one embodiment of the present specification, when r5 is 1, at least one of R5 is a substituted or unsubstituted arylene group.

[0100] According to one embodiment of the present specification, when r5 is 1, at least two of the R5 are substituted or unsubstituted arylene groups.

[0101] According to one embodiment of the present specification, L1 and L2 are straight-chain or branched-chain alkylene groups having 2 to 30 carbon atoms, and

[0102] The above Y1 and Y2 are the same or different from each other, and each is independently hydrogen; or a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, and

[0103] The above R1 to R4 are the same or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and

[0104] The above R11 and R12 are the same or different from each other, and each is independently a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, and

[0105] The above R5 is -O-; -S(O2)-; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0106] According to one embodiment of the present specification, L1 and L2 are straight-chain or branched-chain alkylene groups having 2 to 30 carbon atoms.

[0107] According to one embodiment of the present specification, L1 and L2 are straight-chain or branched-chain alkylene groups having 2 to 20 carbon atoms.

[0108] According to one embodiment of the present specification, L1 and L2 are straight-chain or branched-chain alkylene groups having 2 to 10 carbon atoms.

[0109] According to one embodiment of the present specification, L1 and L2 are ethylene groups.

[0110] According to one embodiment of the present specification, Y1 and Y2 are the same or different from each other and are each independently hydrogen; or a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

[0111] According to one embodiment of the present specification, Y1 and Y2 are the same or different from each other and are each independently hydrogen; or a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.

[0112] According to one embodiment of the present specification, Y1 and Y2 are the same or different from each other and are each independently hydrogen; or a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms.

[0113] According to one embodiment of the present specification, Y1 and Y2 are the same or different from each other and are each independently hydrogen; or a methyl group.

[0114] According to one embodiment of the present specification, R1 to R4 are the same or different from each other and each independently is any one of the following structures.

[0115]

[0116] In the above structure,

[0117] X1 and X2 are each independently O or S, and

[0118] Any one of G1 to G8 is a site bonded to the above formula 1, and the remainder of G1 to G8 not bonded to the above formula 1 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterogroup, and

[0119] Any one of G9 to G16 is a site bonded to the above formula 1, and the remainder of G9 to G16 not bonded to the above formula 1 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterogroup, and

[0120] Any one of G17 to G26 is a site bonded to the above formula 1, and the remainder of G17 to G26 not bonded to the above formula 1 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterogroup, and

[0121] Any one of G27 to G38 is a site bonded to the above formula 1, and the remainder of G27 to G38 not bonded to the above formula 1 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterogroup, and

[0122] Any one of G39 to G46 is a site bonded to the above formula 1, and the remainder of G39 to G46 not bonded to the above formula 1 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterogroup, and

[0123] Any one of G47 to G52 is a site bonded to the above formula 1, and the remainder of G47 to G52 not bonded to the above formula 1 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterogroup, and

[0124] Any one of G53 to G59 is a site bonded to the above formula 1, and the remainder of G53 to G59 not bonded to the above formula 1 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterogroup, and

[0125] Any one of G60 to G67 is a site bonded to the above formula 1, and the remainder of G60 to G67 not bonded to the above formula 1 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterogroup, and

[0126] Any one of G68 to G76 is a site that is bonded to the above formula 1, and the remainder of G68 to G73 that are not bonded to the above formula 1 are the same or different from one another, and each is independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterogroup.

[0127] According to one embodiment of the present specification, R1 to R4 are the same or different from each other and are each independently a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, a straight-chain or branched-chain alkoxy group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryloxy group having 6 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a polycyclic heteroaryl group having 6 to 30 carbon atoms, and a combination thereof, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more of these; or a polycyclic heteroaryl group having 6 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0128] According to one embodiment of the present specification, R1 to R4 are the same or different from each other and are each independently a phenyl group substituted with one or more of a monocyclic or polycyclic aryloxy group having 6 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a polycyclic heteroaryl group having 6 to 30 carbon atoms, and combinations thereof; a naphthyl group substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, a straight-chain or branched-chain alkoxy group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a carbazole group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a benzofuran group; or a dibenzofuran group.

[0129] According to one embodiment of the present specification, R1 to R4 are the same or different from each other and are each independently a phenyl group substituted with one or more of a phenoxy group, a naphthyl group, a phenyl group, an imidazole group, a carbazole group, and combinations thereof; a naphthyl group substituted or unsubstituted with a methyl group, a methoxy group, or a phenyl group; a carbazole group substituted or unsubstituted with a phenyl group; a benzofuran group; or a dibenzofuran group.

[0130] According to one embodiment of the present specification, R1 to R4 are the same or different from each other and are each independently a phenoxy group, a naphthyl group, an imidazole group substituted with a phenyl group, or a phenyl group substituted with a carbazole group; a naphthyl group substituted or unsubstituted with a methyl group, a methoxy group, or a phenyl group; a carbazole group substituted with a phenyl group; a benzofuran group; or a dibenzofuran group.

[0131] According to one embodiment of the present specification, R1 to R4 are the same as each other.

[0132] According to one embodiment of the present specification, R11 and R12 are the same or different from each other and are each independently straight-chain or branched-chain alkyl groups having 1 to 30 carbon atoms.

[0133] According to one embodiment of the present specification, R11 and R12 are the same or different from each other and are each independently straight-chain or branched-chain alkyl groups having 1 to 10 carbon atoms.

[0134] According to one embodiment of the present specification, R11 and R12 are the same or different from each other and are each independently a methyl group; an ethyl group; or an isopropyl group.

[0135] According to one embodiment of the present specification, R5 is -O-; -S(O2)-; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0136] According to one embodiment of the present specification, R5 is -O-; -S(O2)-; or a single or polycyclic arylene group having 6 to 20 carbon atoms.

[0137] According to one embodiment of the present specification, the R5 is -O-; -S(O2)-; or a monocyclic or polycyclic arylene group having 6 to 10 carbon atoms.

[0138] According to one embodiment of the present specification, R5 is -O-; -S(O2)-; or a phenylene group.

[0139] According to one embodiment of the present specification, the above is one of the following structures.

[0140]

[0141] In the above structure, represents the part connected to the above chemical formula 1.

[0142] According to one embodiment of the present specification, the resin may have -OH; -SH; -CO2CH3; -CO2CH2CH3; or -OC6H5 as terminal groups.

[0143] In one embodiment of the present specification, the weight-average molecular weight of the resin is 5,000 g / mol to 200,000 g / mol, preferably 10,000 g / mol to 100,000 g / mol, more preferably 15,000 g / mol to 50,000 g / mol, 20,000 g / mol to 40,000 g / mol.

[0144] When the above resin satisfies the aforementioned weight-average molecular weight range, the resin can have optimal fluidity and processability.

[0145] In one embodiment of the present invention, the number average molecular weight of the resin is 3,000 g / mol to 100,000 g / mol, 5,000 g / mol to 50,000 g / mol, 10,000 g / mol to 30,000 g / mol, 12,000 g / mol to 28,000 g / mol, preferably 14,000 g / mol to 25,000 g / mol.

[0146] In this specification, the weight-average molecular weight (Mw) of the resin and the oligomer used in its manufacture can be measured using gel permeation chromatography (GPC) with a polystyrene standard (PS standard) using an Agilent 1200 series. Specifically, the measurement can be performed using an Agilent 1200 series instrument with a Polymer Laboratories PLgel MIX-B 300 mm long column, at a measurement temperature of 40°C, with tetrahydrofuran (THF) as the solvent and a flow rate of 1 mL / min. Samples of the resin or oligomer are prepared at a concentration of 10 mg / 10 mL, supplied in an amount of 10 μL, and the weight-average molecular weight (Mw) value is derived using a calibration curve formed with a polystyrene standard. At this time, 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.

[0147] In one embodiment of the present specification, the refractive index of the resin measured at a wavelength of 589 nm is 1.65 to 1.80. The refractive index may preferably be 1.680 to 1.750. When the resin 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.

[0148] In one embodiment of the present specification, the Abbe number measured and calculated at wavelengths of 486, 589, and 656 nm of the resin 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 satisfies the above Abbe number range, when the resin is applied to a molded article such as an optical lens, there is an effect of reduced dispersion and increased clarity.

[0149] The above Abbe number is specifically the refractive index (n) at wavelengths D (589 nm), F (486 nm), and C (656 nm) at 20°C. D , n F , n C The Abbe number can be obtained by measuring each of the following formulas.

[0150] Abe number = (n D -1) / (n F - n C )

[0151] The above refractive index and Abbe number measurements can be performed on a film prepared by spin-coating a solution prepared by dissolving the resin in a solvent onto a silicon wafer, and the results according to the wavelength of light can be obtained and measured using an ellipsometer at 20°C. The spin-coating application can be performed at a rotational speed of 150 rpm to 300 rpm, and the thickness of the applied film can be 5 µm to 20 µm. The silicon wafer is not particularly limited and may be appropriately employed as long as it is capable of measuring the refractive index and Abbe number of the resin composition according to the present specification. The solvent may be dimethylacetamide or 1,2-dichlorobenzene, and the solution may be prepared by dissolving the resin sample at 10% by weight based on the total weight of the solution.

[0152] According to one embodiment of the present specification, the chemical formula 1 is any one of the following structures.

[0153]

[0154] .

[0155] One embodiment of the present specification provides the following chemical formula 1a.

[0156] [Chemical Formula 1a]

[0157]

[0158] In the above chemical formula 1a,

[0159] R1 to R4 are the same or different from each other, and each is an independently substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0160] Y1 and Y2 are the same or different from each other, and each independently is hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0161] L1 and L2 are the same or different from each other, and each is an independently substituted or unsubstituted alkylene group, and

[0162] R11 and R12 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group, and

[0163] a and b are 0 or 1, respectively.

[0164] According to one embodiment of the specification, the above chemical formula 1a is the following chemical formula 1a-1.

[0165] [Chemical Formula 1a-1]

[0166]

[0167] In the above chemical formula 1a-1,

[0168] The definitions of R1 to R4, R11, R12, Y1 and Y2 are the same as those defined in Chemical Formula 1a above.

[0169] According to one embodiment of the present specification, the formula 1a is the following formula 1a-2.

[0170] [Chemical Formula 1a-2]

[0171]

[0172] In the above chemical formula 1a-2,

[0173] The definitions of R1 to R4, R11, R12, L1, L2, Y1 and Y2 are the same as those defined in Chemical Formula 1a above.

[0174] One embodiment of the present specification provides a method for producing a resin comprising the step of polymerizing a composition for producing a resin comprising a compound of the following formula 1a; and a polyarylenethioether precursor.

[0175] [Chemical Formula 1a]

[0176]

[0177] In the above chemical formula 1a,

[0178] The definitions of R1 to R5, R11, R12, Y1, Y2, L1 and L2 are the same as those defined in Chemical Formula 1 above.

[0179] According to one embodiment of the present specification, the formula 1a is any one of the following structures.

[0180] .

[0181] When the compound of the above chemical formula 1a is included, polymerization is easy, and depending on the substituent, it has a refractive index of a wide range or a high refractive index and a wide range of glass transition temperatures.

[0182] The above resin manufacturing composition may further include a solvent.

[0183] The above solvent may be, for example, tetrahydrofuran, diphenyl ether, dimethylacetamide, methyl ethyl ketone, ethyl acetate, or methanol, but is not limited thereto, and those applicable in the art may be appropriately employed.

[0184] The above solvent may be included in an amount of 5 to 60 parts by weight per 100 parts by weight of the resin manufacturing composition.

[0185] The above solvent may preferably be included in an amount of 5 to 50 parts by weight, 7 to 45 parts by weight, or 8 to 40 parts by weight per 100 parts by weight of the composition for manufacturing the resin.

[0186] In one embodiment of the present specification, the compound of Formula 1a may be included in an amount of 1 to 100 parts by weight or 1 to 99 parts by weight per 100 parts by weight of the composition for manufacturing the resin.

[0187] More specifically, the compound of formula 1a may be included in an amount of preferably 1 to 60 parts by weight, 1 to 50 parts by weight, 1 to 40 parts by weight, 1 to 30 parts by weight, 1 to 20 parts by weight, or 1 to 10 parts by weight per 100 parts by weight of the composition for manufacturing the resin.

[0188] In one embodiment of the present specification, the polyarylenethioether precursor may be included in an amount of 1 to 60 parts by weight per 100 parts by weight of the composition for manufacturing the resin.

[0189] The above polyarylenethioether precursor may preferably be included in an amount of 1 to 60 parts by weight, 1 to 55 parts by weight, 1 to 50 parts by weight, 1 to 45 parts by weight, or 1 to 40 parts by weight per 100 parts by weight of the composition for manufacturing the resin.

[0190] According to one embodiment of the present specification, the polyarylenethioether precursor is the following chemical formula A.

[0191] [Chemical Formula A]

[0192]

[0193] In the above chemical formula A,

[0194] R5 is -O-; -S(O2)-; -C(RR')-; -N(R")-; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0195] R, R' and R" are the same or different from each other, and each independently is hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0196] r5 is an integer from 1 to 10, and

[0197] If r1 is 2 or more, the above 2 or more R1s are the same or different from each other.

[0198] According to one embodiment of the present specification, the formula A is any one of the following compounds.

[0199]

[0200] It can be formed into the unit of the aforementioned formula 1 by polymerizing the compound of formula 1a and the polyarylenethioether precursor of formula A.

[0201] In one embodiment of the present specification, the resin is preferably polymerized from the compound of Formula 1a and the polyarylenethioether precursor of Formula A.

[0202] The compound of the above chemical formula 1a may be used in an amount of 1 to 100 moles or 1 to 99 moles relative to 100 moles of the total monomer constituting the resin containing the unit of the above chemical formula 1.

[0203] The polyarylenethioether precursor of the above formula A can be used in an amount of 1 to 99 moles relative to 100 moles of the total monomer of the compound of the above formula 1a constituting the resin.

[0204] The polymerization of the resin according to the present specification may utilize methods known in the art.

[0205] It is preferable to perform the above polymerization using a solution polymerization method.

[0206] The above solution polymerization method uses the resin manufacturing composition and base comprising the above solvent, and may additionally use a catalyst as needed. The above solution polymerization method may utilize conventional solution polymerization methods and materials, except that it includes the above formula 1a and the above polyarylentioether precursor.

[0207] The catalyst and base mentioned above may be materials generally applicable in the field of the art. Specifically, for the solution polymerization, it is preferable to dissolve the compound of Formula 1a; the polyarylenethioether precursor and the solvent in a reaction vessel, and then add a base to carry out the reaction.

[0208] The temperature of the above solution polymerization is room temperature to 70°C, preferably room temperature to 60°C, and more preferably room temperature to 50°C.

[0209] The reaction time of the above solution polymerization is 1 hour to 15 hours, preferably 3 hours to 12 hours, and more preferably 12 hours.

[0210] The above solution polymerization may be carried out in a continuous or batch manner, and can be carried out selectively depending on the reaction conditions. The reaction apparatus may be of the vertical type equipped with a soken-type stirring blade, an anchor-type stirring blade, a Max Blend stirring blade, a helical ribbon-type stirring blade, etc., or may be of the horizontal type equipped with a paddle blade, a grid blade, a spectral blade, etc., or may be of the extruder type equipped with a screw. In addition, it is preferable to use a reaction apparatus that appropriately combines these reaction apparatuses, taking into account the viscosity of the polymer.

[0211] The above resin can be obtained by precipitating in a solvent and filtering, and the obtaining process may be repeated one or more times with precipitation and filtration.

[0212] The resin of this specification preferably has the lowest possible foreign matter content, and the removal of unreacted monomers, solvents, by-products, and filtration of the solution is preferably carried out.

[0213] The mesh of the filter used for the above filtration is preferably 5 μm or less, and more preferably 1 μm or less. In addition, filtration of the generated resin by a polymer filter is preferably carried out. The mesh of the polymer filter is preferably 100 μm or less, and more preferably 30 μm or less. In addition, the process of collecting the resin pellets must be in a low-dust environment, preferably Class 6 or less, and more preferably Class 5 or less.

[0214] In addition, molding methods for a molded article containing the above resin include, in addition to injection molding, compression molding, molding, roll processing, extrusion molding, and stretching, but are not limited thereto.

[0215] Another embodiment of the present specification provides a resin composition comprising a resin according to the embodiments described above.

[0216] In one embodiment of the present specification, the resin may be included in an amount of 1 to 80 parts by weight based on 100 parts by weight of the resin composition.

[0217] In one embodiment of the present specification, the resin composition may further include a solvent. The solvent may be, for example, dimethylacetamide or 1,2-dichlorobenzene.

[0218] The above solvent may be included in an amount of 20 to 99 parts by weight based on 100 parts by weight of the resin composition.

[0219] The resin composition may further include additional monomers in addition to the compound of Formula 1a. The additional monomers are not particularly limited, and monomers generally applied in the art related to polyarylenethioethers may be appropriately employed within a range that does not alter the major physical properties of the resin composition. The additional monomers may be used in an amount of 1 to 50 moles relative to 100 moles of total monomers constituting the resin containing the unit of Formula 1.

[0220] In addition to the resin comprising the unit of Formula 1, the resin composition may additionally include, if necessary, one or more additives selected from the group consisting of antioxidants, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, fluorescent whitening agents, ultraviolet absorbers, pigments, and dyes.

[0221] The above additive may be included in an amount of 1 to 99 parts by weight based on 100 parts by weight of the resin composition.

[0222] The types of the above antioxidants, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, fluorescent whitening agents, ultraviolet absorbers, pigments, or dyes are not particularly limited, and those applicable in the field of technology may be appropriately adopted.

[0223] Another embodiment of the present specification provides a molded article comprising a resin composition according to the embodiments described above.

[0224] In one embodiment of the present specification, the molded article may be manufactured from the resin composition or a cured product thereof.

[0225] As an example of a method for manufacturing the above-mentioned molded article, the method may include the step of thoroughly mixing the resin containing the unit of Chemical Formula 1 and the additive using a mixer, then extruding the mixture into pellets using an extruder, drying the pellets, and then injecting them using an injection molding machine.

[0226] In one embodiment of the present specification, the molded article is an optical member.

[0227] In one embodiment of the present specification, the molded article is an optical lens.

[0228] An optical lens according to one embodiment of the present specification has a high refractive index, so a thin optical lens can be implemented.

[0229] The above optical lens is manufactured using the above resin, has a thin thickness, high refractive index and high transparency, and preferably can be applied to a camera.

[0230] The present specification is further illustrated in detail below through examples.

[0231] [Preparation Example 1] Preparation of Compound 1a-1

[0232] 1) Preparation of Compound 1a-a-1

[0233]

[0234] 5.0 g of 2,2'-((propane-2,2-diylbis(2,6-dibromo-4,1-phenylene))bis(oxy))bis(ethan-1-ol) and 5.6 g of naphthalen-2-ylboronic acid were placed in a round-bottom flask, and 95.0 ml of tetrahydrofuran was added. After heating, 6.6 g of K2CO3 dissolved in 10 ml of H2O was added at 50 ℃. 497 mg of BTP (Pd(tBu3P)2) was added at 50 ℃. After heating to 75 ℃, the mixture was stirred for 1 hour. After work-up with ethyl acetate (EA) / H2O, MgSO4 was added to the organic layer, and the mixture was filtered using a Celite filter. The filtrate was vacuum concentrated and adsorbed after adding silica. After purifying the adsorbed substance by MPLC (Medium Pressure Liquid Chromatography) under a 3:7 (n-Hexane: ethyl acetate (EA)) condition, 4.3 g of compound 1a-a-1 (yield, 66%) was obtained through precipitation with methylene chloride (MC) and n-Hexane.

[0235] 1H NMR (500 MHz): δ = 8.10-8.06 (m, 8H), 8.00 (d, 4H), 7.91 (s, 4H), 7.64-7.61 (m, 8H), 7.57 (s, 4H), 7.39 (d, 4H), 4.89 (s, 2H), 4.35 (t, 4H), 3.70 (t, 4H), 1.71 (s, 6H)

[0236] 2) Preparation of Compound 1a-a

[0237]

[0238] 5.0 g of compound 1a-a-1 and 25.0 ml of tetrahydrofuran were placed in a round-bottom flask, and the reaction mixture was placed in an ice bath. 1.9 ml of triethylamine was added, and the mixture was stirred for 30 minutes. Subsequently, 1.2 g of acryloyl chloride was slowly added. After 1 hour, the completion of the reaction was confirmed by monitoring with thin-layer chromatography (TLC). The reaction mixture was filtered to remove the salt byproduct. The filtrate was recovered, and after adding silica, it was vacuum concentrated and adsorbed. The adsorbed substance was purified by medium pressure liquid chromatography (MPLC) under an 8:2 (n-hexane:ethyl acetate (EA)) ratio and dried to obtain 4.8 g of compound 1a-a (yield, 85%).

[0239] 1H NMR (500 MHz): δ = 8.09-8.04 (m, 8H), 8.01 (d, 4H), 7.91 (s, 4H), 7.64-7.62 (m, 8H), 7.55 (s, 4H), 7.37 (d, 4H), 6.43 (dd, 2H), 6.11 (m, 2H), 5.85 (dd, 2H), 4.53 (m, 4H), 4.40 (m, 4H), 1.69 (s, 6H)

[0240] [Preparation Example 2] Preparation of Compounds 1a-b

[0241]

[0242] 1) Preparation of Compound 1a-b-1

[0243] Compound 1a-b-1 was prepared by the same method as the preparation of compound 1a-a-1, except that (9,9-dimethyl-9H-fluoren-2-yl)boronic acid was used instead of naphthalen-2-ylboronic acid.

[0244] 2) Preparation of Compounds 1a-b

[0245] 5.0 g of compound 1a-b-1 and 18.0 ml of tetrahydrofuran were placed in a round-bottom flask, and the reaction mixture was placed in an ice bath. 1.4 ml of triethylamine was added, and the mixture was stirred for 30 minutes. Subsequently, 876 mg of methacryloyl chloride was slowly added. After 1 hour, the completion of the reaction was confirmed via thin-layer chromatography (TLC) monitoring. The reaction mixture was filtered to remove the salt byproduct. The filtrate was recovered, and after adding silica, it was vacuum concentrated and adsorbed. The adsorbed substance was purified by medium pressure liquid chromatography (MPLC) under an 8:2 (n-hexane:ethyl acetate (EA)) ratio and dried to obtain 4.4 g of compound 1a-b (yield, 80%).

[0246] 1H NMR (500 MHz): δ = 8.11 (d, 4H), 7.90-7.88 (m, 12H), 7.79 (d, 4H), 7.57 (d, 4H), 7.40 (t, 4H), 7.31 (t, 4H), 6.43 (dd, 2H), 6.12 (m, 2H), 5.87 (dd, 2H), 4.54 (m, 4H), 4.43 (m, 4H), 1.71 (s, 6H), 1.67 (s, 24H)

[0247] [Preparation Example 3] Preparation of Compounds 1a-c

[0248]

[0249] 1) Preparation of Compound 1a-c-1

[0250] Compound 1a-c-1 was prepared by the same method as the preparation of compound 1a-a-1, except that dibenzo[b,d]thiophen-3-ylboronic acid was used instead of naphthalen-2-ylboronic acid.

[0251] 2) Preparation of compounds 1a-c

[0252] 5.0 g of compound 1a-c-1 and 18.0 ml of tetrahydrofuran were placed in a round-bottom flask, and the mixture was placed in an ice bath. 1.5 ml of triethylamine was added, and the mixture was stirred for 30 minutes. Subsequently, 909 mg of acryloyl chloride was slowly added. After 1 hour, the completion of the reaction was confirmed by monitoring with thin-layer chromatography (TLC). The reaction mixture was filtered to remove the salt byproduct. The filtrate was recovered, and after adding silica, it was vacuum concentrated and adsorbed. The adsorbed substance was purified by medium pressure liquid chromatography (MPLC) under an 8:2 (n-hexane:ethyl acetate (EA)) ratio and dried to obtain 4.5 g of compound 1a-c (yield, 82%).

[0253] 1H NMR (500 MHz): δ = 8.47 (d, 4H), 8.25-8.18 (m, 12H), 7.95 (d, 4H), 7.91 (s, 4H), 7.56-7.45 (m, 8H), 6.41 (dd, 2H), 6.12 (m, 2H), 5.85 (dd, 2H), 4.53 (m, 4H), 4.42 (m, 4H), 1.67 (s, 6H)

[0254] [Preparation Example 4] Preparation of Compound 1-a

[0255] 1) Preparation of Compound 1-a-1

[0256]

[0257] 5.0 g of 4,4'-(propane-2,2-diyl)bis(2,6-dibromophenol) and 6.5 g of naphthalen-2-ylboronic acid were placed in a round-bottom flask, and 100.0 ml of tetrahydrofuran was added. After heating, 7.6 ml of K2CO3 dissolved in 25 ml of H2O was added at 50 ℃. 580 mg of BTP (Pd(tBu3P)2) was added at 50 ℃. The mixture was heated to 75 ℃ and stirred for 1 hour. After work-up with ethyl acetate (EA) / H2O, MgSO4 was added to the organic layer, and the mixture was filtered using a Celite filter. The filtrate was vacuum concentrated and adsorbed after adding silica. After purifying the adsorbed substance by MPLC (Medium Pressure Liquid Chromatography) under a 3:7 (n-Hexane: ethyl acetate (EA)) condition, 5.3 g of compound 1-a-1 (yield, 79%) was obtained through precipitation with methylene chloride (MC) and n-Hexane.

[0258] 1H NMR (500 MHz): δ = 10.92 (s, 2H), 8.09-7.98 (m, 12H), 7.70 (s, 4H), 7.65-7.56 (m, 12H), 7.37 (d, 4H), 1.71 (s, 6H)

[0259] 2) Preparation of Compound 1-a

[0260]

[0261] 5.0 g of compound 1-a-1 and 23.0 ml of tetrahydrofuran were placed in a round-bottom flask, and the reaction mixture was placed in an ice bath. 2.1 ml of triethylamine was added, and the mixture was stirred for 30 minutes. Subsequently, 1.5 g of acryloyl chloride was slowly added. After 1 hour, the completion of the reaction was confirmed by monitoring with thin-layer chromatography (TLC). The reaction mixture was filtered to remove the salt byproduct. The filtrate was recovered, and after adding silica, it was vacuum concentrated and adsorbed. The adsorbed substance was purified by medium pressure liquid chromatography (MPLC) under an 8:2 (n-hexane:ethyl acetate (EA)) ratio and dried to obtain 5.1 g of compound 1-a (yield, 89%).

[0262] 1H NMR (500 MHz): δ = 8.11-8.08 (m, 8H), 8.00 (d, 4H), 7.88 (s, 4H), 7.64-7.60 (m, 8H), 7.57 (s, 4H), 7.36 (d, 4H), 6.24 (dd, 2H), 6.11 (m, 2H), 5.75 (dd, 2H), 1.70 (s, 6H)

[0263] [Preparation Example 5] Preparation of Compound 1-b

[0264]

[0265] 1) Preparation of Compound 1-b-1

[0266] Compound 1-b-1 was prepared in the same manner as Compound 1-a-1, except that (9,9-dimethyl-9H-fluoren-2-yl)boronic acid was used instead of naphthalen-2-ylboronic acid.

[0267] 2) Preparation of Compound 1-b

[0268] 5.0 g of compound 1-b-1 and 18.0 ml of tetrahydrofuran were placed in a round-bottom flask, and the mixture was placed in an ice bath. 1.5 ml of triethylamine was added, and the mixture was stirred for 30 minutes. Subsequently, 1.1 g of methacryloyl chloride was slowly added. After 1 hour, the completion of the reaction was confirmed by monitoring with thin-layer chromatography (TLC). The reaction mixture was filtered to remove the salt byproduct. The filtrate was recovered, and after adding silica, it was vacuum concentrated and adsorbed. The adsorbed substance was purified by medium pressure liquid chromatography (MPLC) under an 8:2 (n-hexane:ethyl acetate (EA)) ratio and dried to obtain 4.9 g of compound 1-b (yield, 88%).

[0269] 1H NMR (500 MHz): δ = 8.09 (d, 4H), 7.89-7.87 (m, 12H), 7.78 (d, 4H), 7.55 (d, 4H), 7.39 (t, 4H), 7.29 (t, 4H), 6.25 (dd, 2H), 6.11 (m, 2H), 5.74 (dd, 2H), 1.70 (s, 6H), 1.67 (s, 24H)

[0270] [Method for manufacturing resin]

[0271] This is a solution polymerization method in which the compound of formula 1a and the compound of formula A are dissolved in a solvent, and then a base is added to induce an addition reaction and thereby form a polymer.

[0272] Any one of the dithiol monomers of compounds A-1 to A-3 and any one of the diacrylate monomers of compounds 1a-a to 1a-c are dissolved in tetrahydrofuran, and a nitrogen atmosphere is created. Nitrogen bubbling is carried out for at least 30 minutes. Then, triethylamine is slowly added, and stirring is performed at room temperature or 50°C. After reacting for 12 hours, the mixture is precipitated in a methanol solvent and filtered. A white solid is obtained. The precipitation and filtration process is repeated.

[0273] The resins of Examples 1 to 3 below were prepared using the above method.

[0274]

[0275] [Example 1] Preparation of Resin 1

[0276] 3.0 g of compound 1a-a and 459 mg of compound A-1 were dissolved in 13.0 ml of tetrahydrofuran, and a nitrogen atmosphere was created. Nitrogen bubbling was carried out for at least 30 minutes. Subsequently, 0.45 ml of trimethylamine was slowly added, and the mixture was stirred at room temperature. After reacting for 12 hours, the mixture was precipitated in methanol solvent and filtered. A white solid was obtained, and the precipitation and filtration process was repeated to prepare resin 1.

[0277] [Example 2] Preparation of Resin 2

[0278] Resin 2 was prepared in the same manner as in Example 1 above, except that compound A-2 was used instead of compound A-1.

[0279] [Example 3] Preparation of Resin 3

[0280] Resin 3 was prepared in the same manner as in Example 1 above, except that compound 1a-b was used instead of compound 1a-a and compound A-2 was used instead of compound A-1.

[0281] [Example 4] Preparation of Resin 4

[0282] Resin 4 was prepared in the same manner as in Example 1 above, except that compound 1a-c was used instead of compound 1a-a and compound A-2 was used instead of compound A-1.

[0283] [Example 5] Preparation of Resin 5

[0284] Resin 5 was prepared in the same manner as in Example 1 above, except that 1-a was used instead of compound 1a-a and compound A-2 was used instead of compound A-1.

[0285] [Example 6] Preparation of Resin 6

[0286] Resin 6 was prepared in the same manner as in Example 1 above, except that compound 1-b was used instead of compound 1a-a and compound A-2 was used instead of compound A-1.

[0287] [Comparative Example 1] Preparation of Comparative Example Resin 1

[0288] Comparative Example Resin 1 was prepared in the same manner as in Example 1 above, except that the following C-1 was used instead of Compound 1a-1.

[0289]

[0290] [Comparative Example 2] Preparation of Comparative Example Resin 2

[0291] Comparative Example Resin 2 was prepared in the same manner as in Example 1 above, except that Compound 1a-1 was replaced with the following C-2 and Compound A-1 was replaced with Compound A-2.

[0292]

[0293] Experimental Example.

[0294] The molecular weight and molecular weight distribution (PDI(Mw / Mn)) of the polymerized resin samples were confirmed via gel permeation chromatography (GPC), and a thermogram was obtained using differential scanning calorimetry (DSC) to investigate thermal properties. To measure the refractive index and Abbe number, an ellipsometer was used after film formation to obtain results based on the wavelength of light.

[0295] Molecular weights obtained by gel permeation chromatography (GPC) were measured at 40°C using tetrahydrofuran (THF, stabilized with BHT (butylated hydroxytoluene))) as the solvent. The resin sample was dissolved in tetrahydrofuran at a concentration of 1.0 mg / 1 ml, and the resulting solution was filtered through a syringe filter and injected. The results are listed in Table 1 below. A Waters RI detector was used, and two Agilent PLgel MIXED-B columns were used.

[0296] To measure the refractive index and Abbe number of the resin, a polymer solution prepared by dissolving a polymerized resin powder sample in the solvent dimethylacetamide at 10 wt% based on the total weight of the polymer solution was applied to a silicon wafer by spin-coating at a rotation speed of 220 rpm to form a film with a thickness of 20 μm. The results were obtained according to the wavelength of light using an ellipsometer at 20°C and are listed in Table 1 below. Specifically, the refractive index was measured at a wavelength of 589 nm, and the Abbe number was the refractive index (n) at wavelengths D (589 nm), F (486 nm), and C (656 nm). D , n F , n C The Abbe numbers were obtained by measuring each of the following formulas.

[0297] Abe number = (n D -1) / (n F - nC )

[0298] Mw Mn PDI Refractive index (nd) Abesu Example 1 Suzy 1 19270 12150 1.59 1.6840 24.9 Example 2 Suzy 2 21680 14080 1.54 1.6891 27.4 Example 3 Suzy 3 37740 19530 1.93 1.6689 27.7 Example 4 Suzy 4 34460 18390 1.87 1.7122 26.6 Example 5 Suzy 5 29840 19760 1.51 1.7801 30.1 Example 6 Suzy 6 27670 16330 1.69 1.7647 29.8 Comparative Example 1 Comparative Example Suji 1 11020 7760 1.42 1.6003 20 Comparative Example 2 Comparative Example Suji 2 28890 18370 1.57 1.6113 22.1

[0299] In Table 1 above, Mn represents the number-average molecular weight, Mw represents the weight-average molecular weight, and the refractive index is the value measured at a wavelength of 589 nm.

[0300] According to Table 1 above, it was found that the resin according to the embodiment of the present specification contains the unit of Chemical Formula 1 and is a derivative of BPA (Bisphenol A), so it has a small molecular volume and excellent packing ability, and since R1 to R4 are electron-rich substituents, the refractive index and Abbe number of Examples 1 to 6 above are high.

[0301] In addition, it was confirmed that the unit of the above chemical formula 1 contains cyclic aromatic hydrocarbons, halogen atoms excluding fluorine, and sulfur atoms, which are elements that increase the refractive index, and exhibits high refractive index characteristics.

[0302] Comparative Examples 1 and 2 above are resins in which R1 to R4 of Chemical Formula 1 are hydrogen, and since they do not satisfy the conditions of Chemical Formula 1, it was confirmed that they have a low refractive index and a low Abbe number.

Claims

Claim 1 Resin containing units of the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, R1 to R4 are the same or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; Y1 and Y2 are the same or different from each other and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; L1 and L2 are the same or different from each other and are each independently a substituted or unsubstituted alkylene group; R11 and R12 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group; a and b are each 0 or 1; R5 is -O-; -S(O2)-; -C(RR')-; -N(R")-; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R, R' and R" are the same or different from each other and are each independently hydrogen; A substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, where r5 is an integer from 1 to 10, and where r5 is 2 or more, the 2 or more R5s are the same or different from each other, and * means a portion connected to the main chain of the resin. Claim 2 The resin of claim 1, wherein the chemical formula 1 is the following chemical formula 1-1: [Chemical Formula 1-1] In the above chemical formula 1-1, the definitions of R1 to R5, R11, R12, Y1, Y2, and r5 are the same as those defined in the above chemical formula 1. Claim 3 The resin of claim 1, wherein the chemical formula 1 is the following chemical formula 1-2: [Chemical Formula 1-2] In the above chemical formula 1-2, the definitions of R1 to R5, R11, R12, Y1, Y2, L1, L2, and r5 are the same as those defined in the above chemical formula 1. Claim 4 In claim 1, L1 and L2 are the same or different from each other and are each independently a straight-chain or branched-chain alkylene group having 2 to 30 carbon atoms; Y1 and Y2 are the same or different from each other and are each independently hydrogen; or a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; R1 to R4 are the same or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; R11 and R12 are the same or different from each other and are each independently a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; and R5 is -O-; -S(O2)-; Or a resin having a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms. Claim 5 A resin according to claim 1, wherein the weight-average molecular weight (Mw) of the resin is 5,000 g / mol to 200,000 g / mol. Claim 6 A resin according to claim 1, wherein the refractive index of the resin measured at a wavelength of 589 nm is 1.65 to 1.

80. Claim 7 A resin according to claim 1, wherein the Abbe numbers measured at wavelengths of 486, 589, and 656 nm are 10 to 40. Claim 8 A resin according to claim 1, wherein the chemical formula 1 is any one of the following structures: . Claim 9 Compound of the following chemical formula 1a: [Chemical formula 1a] In the above formula 1a, R1 to R4 are the same or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; Y1 and Y2 are the same or different from each other and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; L1 and L2 are the same or different from each other and are each independently a substituted or unsubstituted alkylene group; R11 and R12 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group; and a and b are each 0 or 1. Claim 10 A compound according to claim 9, wherein the formula 1a is selected from the following structures: . Claim 11 A method for producing a resin according to any one of claims 1 to 8, comprising the step of polymerizing a composition for producing a resin comprising a compound of the following chemical formula 1a; and a polyarylenethioether precursor: [Chemical formula 1a] In the above chemical formula 1a, the definitions of R1 to R4, R11, R12, Y1, Y2, L1, L2, a, and b are the same as those defined in the above chemical formula 1. Claim 12 A method for manufacturing a resin according to claim 11, wherein the polyarylenethioether precursor is of the following chemical formula A: [Chemical formula A] In the above chemical formula A, R1 is -O-; -S(O2)-; -C(RR')-; -N(R")-; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and R, R' and R" are the same or different from each other, and each independently is hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and r1 is an integer from 1 to 10, and if r1 is 2 or more, the 2 or more R1s are the same or different from each other. Claim 13 A resin composition comprising a resin according to any one of claims 1 to 8. Claim 14 A molded article comprising a resin composition according to claim 13.

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