Resin and its manufacturing method

Abstract

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

Description

[Technical Field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0082386, filed with the Korean Intellectual Property Office on July 5, 2022, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a resin and a method for producing the same. [Background technology]

[0003] The higher the refractive index of an optical material, the thinner the optical lens required to achieve the same level of correction. This means that the higher the refractive index of an optical material, the thinner and lighter the lenses can be manufactured, allowing for the miniaturization of various devices in which lenses are used.

[0004] Generally, as the refractive index of an optical material increases, the Abbe's number decreases. In addition, a certain level of transparency is required for use as an optical material. Summary of the Invention [Problem to be solved by the invention]

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

[0006] Another embodiment of the present invention seeks to provide compositions containing resins of novel structures and molded articles made from said resin compositions. [Means for solving the problem]

[0007] One embodiment of the present disclosure provides a resin comprising units of Formula 1: [ka] In the above chemical formula 1, X1 to X4 are the same or different and each independently represents O or S; R1 to R4 are the same or different and each independently represent a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R5 and R6 are the same or different and each independently represent a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; R101 and R102 are the same or different and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; r101 is 1 or 2, and when r101 is 2, the two R101 are the same or different from each other; r102 is 1 or 2, and when r102 is 2, the two R102 are the same or different from each other; La is a direct bond; or -C(=O)-L'-; L' is a substituted or unsubstituted arylene group; m and n are each 0 or 1; * indicates the site connected to the main chain of the resin.

[0008] One embodiment of the present disclosure provides a compound of formula 1a: [ka] In the above chemical formula 1a, X1 to X4 are the same or different and each independently represents O or S; R1 to R4 are the same or different and each independently represent a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R5 and R6 are the same or different and each independently represent a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; R101 and R102 are the same or different and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; r101 is 1 or 2, and when r101 is 2, the two R101 are the same or different from each other; r102 is 1 or 2, and when r102 is 2, the two R102 are the same or different from each other; m and n are each 0 or 1.

[0009] Another embodiment of the present disclosure provides a method for producing a resin, comprising polymerizing a resin-producing composition comprising a compound of Formula 1a: and a polyester precursor or a polycarbonate precursor: [ka] In the above chemical formula 1a, X1 to X4 are the same or different and each independently represents O or S; R1 to R4 are the same or different and each independently represent a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R5 and R6 are the same or different and each independently represent a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; R101 and R102 are the same or different and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; r101 is 1 or 2, and when r101 is 2, the two R101 are the same or different from each other; r102 is 1 or 2, and when r102 is 2, the two R102 are the same or different from each other; m and n are each 0 or 1.

[0010] Another embodiment of the present specification provides a resin composition comprising a resin according to the above-described embodiment.

[0011] Another embodiment herein provides a molded article comprising a composition including a resin according to the above-described embodiment. [Effects of the Invention]

[0012] The resin according to one embodiment of the present specification has a high refractive index and high transparency.

[0013] By using a resin according to an embodiment of the present specification, it is possible to obtain an excellent thin optical member, optical lens, optical film, optical thin film, or optical resin. DETAILED DESCRIPTION OF THE INVENTION

[0014] The present specification will be explained in more detail below.

[0015] The resin including the unit of Chemical Formula 1 according to an embodiment of the present specification can be seen to increase the refractive index of a material composed of the molecule by increasing the electron density of the molecule and reducing the molecular volume, based on the relationship between molecular structure and refractive index known from the Lorentz-Lorenz formula. Furthermore, the core structure of Chemical Formula 1 is BPEF(2,2'-(((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(oxy))bis(ethan-1-ol)). By introducing electron-rich substituents into R1 to R4, the electron density of the structure of Chemical Formula 1 can be increased, further improving the refractive index of the resin. Therefore, the polycarbonate resin according to an embodiment of the present specification has a high refractive index and high transparency, and optical lenses, optical films, or optical resins made therefrom can exhibit excellent optical properties despite their thin thickness.

[0016] In one embodiment of the present invention, the resin may contain one or more units of Chemical Formula 1, and when two or more units are contained, the units may be the same or different from each other.

[0017] Throughout this specification, the term "combinations thereof" contained in a Markush expression means a mixture or combination of one or more selected from the group of elements set forth in the Markush expression, and means including one or more selected from the group of elements.

[0018] In this specification, examples of the substituents are described below, but are not limited thereto.

[0019] In this specification, [ka] means the site to be linked.

[0020] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0021] As used herein, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a hydroxy group; a cyano group; an alkyl group; a cycloalkyl group; an alkoxy group; an alkenyl group; an aryloxy group; an arylthio group; an alkylthio group; a silyl group; an aryl group; a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; and a heterocyclic group; or substituted with a substituent in which two or more of the above-exemplified substituents are linked together; or has no substituents.

[0022] In this specification, the term "two or more substituents are linked" means that a hydrogen atom of any one of the substituents is linked to another substituent. For example, the term "two substituents are linked" means that a phenyl group and a naphthyl group are linked to each other. [ka] In addition, the linking of three substituents includes not only the consecutive linking of (substituent 1)-(substituent 2)-(substituent 3), but also the linking of (substituent 1) to (substituent 2) and (substituent 3). For example, the linking of a phenyl group, a naphthyl group, and an isopropyl group results in the following: [ka] The above definitions also apply to the case where four or more substituents are connected.

[0023] In this specification, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0024] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a hexyl ... Examples of alkyl groups include, but are not limited to, butyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0025] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specific examples thereof include 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, and an adamantyl group, but are not limited to these.

[0026] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably 1 to 30. Specific examples of the alkoxy group include, but are not limited to, a methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, and p-methylbenzyloxy group.

[0027] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but preferably is 2 to 30. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0028] In this specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0029] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably is 6 to 50. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group.

[0030] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably is 10 to 50. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, and a fluorene group.

[0031] As used herein, the fluorene group may be substituted, and adjacent groups may be bonded to each other to form a ring. When the fluorene group is substituted, [ka] These include, but are not limited to:

[0032] As used herein, the term "adjacent" refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as "adjacent" groups.

[0033] In this specification, a heteroaryl group includes one or more atoms other than carbon, i.e., heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group, a pyridazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, and a phenanthridine group. Examples of the fluorene group include, but are not limited to, a phenanthridine group, a phenanthroline group, an isoxazole group, a thiadiazole group, a dibenzofuran group, a dibenzosilole group, a phenoxathiine group, a phenoxazine group, a phenothiazine group, a dihydroindenocarbazole group, a spirofluorene xanthene group, a spirofluorene oxanthene group, a tetrahydronaphthothiophene group, a tetrahydronaphthofuran group, a tetrahydrobenzothiophene group, and a tetrahydrobenzofuran group.

[0034] In this specification, the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, etc. The alkyl group in the alkylsilyl group may be the same as the alkyl group exemplified above, the aryl group in the arylsilyl group may be the same as the aryl group exemplified above, the alkyl group and aryl group in the alkylarylsilyl group may be the same as the alkyl group exemplified above, and the heteroaryl group in the heteroarylsilyl group may be the same as the heteroaryl group exemplified above.

[0035] In this specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from the above-mentioned exemplified cycloalkyl groups, aryl groups, and combinations thereof. Examples of the hydrocarbon ring group include, but are not limited to, 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.

[0036] In this specification, a heterocyclic group refers to a group containing one or more heteroatoms other than carbon, and specifically, the heteroatoms may contain one or more atoms selected from the group consisting of O, N, Se, S, etc. The heterocyclic group may be monocyclic or polycyclic, and may be an aromatic heterocyclic group; an aliphatic heterocyclic group; a fused ring group of an aromatic heterocycle and an aliphatic heterocycle; a fused ring group of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aromatic heterocycle, or a fused ring group of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aliphatic heterocycle, and the aromatic heterocyclic group may be selected from the examples of the heteroaryl group.

[0037] In this specification, the term "aliphatic heterocyclic group" refers to an aliphatic ring group containing one or more heteroatoms. The aliphatic heterocyclic group includes a single-bond aliphatic ring group, a multiple-bond aliphatic ring group, and an aliphatic ring group in which a ring containing a single bond and a multiple bond is condensed. Examples of aliphatic heterocyclic groups include, but are not limited to, an epoxy group, an oxirane group, a tetrahydrofuran group, a 1,4-dioxane group, a pyrrolidine group, a piperidine group, a morpholine group, an oxepane group, an azocane group, a thiocane group, a tetrahydronaphthothiophene group, a tetrahydronaphthofuran group, a tetrahydrobenzothiophene group, and a tetrahydrobenzofuran group.

[0038] In this specification, an aryloxy group can be represented by -ORo, and the above description of the aryl group applies to Ro.

[0039] In this specification, an arylthio group can be represented by -SRs1, and the above description of the aryl group applies to Rs1.

[0040] In this specification, an alkylthio group can be represented by -SRs2, and the above description of the alkyl group applies to Rs2.

[0041] In this specification, an alkylene group refers to an alkyl group having two bonding positions, i.e., a divalent group. The above description of the alkyl group can be applied to these groups, except that they are both divalent groups.

[0042] In this specification, a cycloalkylene group refers to a cycloalkyl group having two bonding positions, i.e., a divalent group. The above description of the cycloalkyl group can be applied to these groups, except that they are both divalent groups.

[0043] In this specification, a divalent fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring refers to a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring having two bonding positions, i.e., a divalent group. The above description of the fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring can be applied to these groups, except that they are both divalent groups.

[0044] In this specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above description of the aryl group can be applied to these groups, except that they are both divalent groups.

[0045] As used herein, hydrogen is hydrogen, deuterium, or tritium.

[0046] In one embodiment of the present specification, a portion in the above Chemical Formula 1 where no substituent is indicated may mean that hydrogen, deuterium, or tritium is substituted.

[0047] DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Preferred embodiments of the present invention will now be described in detail. However, the present invention may be modified in various ways and the scope of the present invention is not limited to the following embodiments.

[0048] According to one embodiment of the present specification, the resin may contain one or more units of Chemical Formula 1, and when two or more units are contained, the units may be the same or different from each other.

[0049] According to one embodiment of the present specification, R101 is hydrogen.

[0050] According to one embodiment of the present specification, R102 is hydrogen.

[0051] According to one embodiment of the present specification, the above Chemical Formula 1 is the following Chemical Formula 1-1. [ka] In the above chemical formula 1-1, *, La, R1 to R6, m, n, and X1 to X4 are defined as in Chemical Formula 1 above.

[0052] According to one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-2 to 1-5. [ka] In the above chemical formulas 1-2 to 1-5, *, La, R1 to R6, m, n, and X1 to X4 are defined as in Chemical Formula 1 above.

[0053] According to one embodiment of the present specification, X1 to X4 are the same or different and each independently represent O or S, R1 to R4 are the same or different and each independently represent a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched 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, or a combination thereof, which is substituted or unsubstituted with one or more of these; or a polycyclic heteroaryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, R5 and R6 are the same or different and each independently represent a linear or branched alkylene group having 2 to 30 carbon atoms; or a monocyclic or polycyclic cycloalkylene group having 6 to 30 carbon atoms, R101 and R102 are hydrogen atoms; wherein La is a direct bond or —C(═O)—L′—; L' is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0054] According to one embodiment of the present specification, R1 to R4 are the same or different and each independently represent one of the following structures: [ka]

[0055] In the above structure: Y1 and Y2 are each independently O or S; any one of G1 to G8 is a site bonded to the above chemical formula 1, and the remaining ones of G1 to G8 that are not bonded to the above chemical formula 1 are the same as or different from one another and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group; any one of G9 to G16 is a site bonded to the above chemical formula 1, and the remaining ones of G9 to G16 that are not bonded to the above chemical formula 1 are the same as or different from one another and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group; any one of G17 to G26 is a site bonded to the above chemical formula 1, and the remaining ones of G17 to G26 that are not bonded to the above chemical formula 1 are the same as or different from one another and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group; any one of G27 to G38 is a site bonded to the above chemical formula 1, and the remaining ones of G27 to G38 that are not bonded to the above chemical formula 1 are the same as or different from one another and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group; any one of G39 to G46 is a site bonded to the above chemical formula 1, and the remaining ones of G39 to G46 that are not bonded to the above chemical formula 1 are the same as or different from one another and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group; any one of G47 to G52 is a site bonded to the above chemical formula 1, and the remaining ones of G47 to G52 that are not bonded to the above chemical formula 1 are the same as or different from one another and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group; any one of G53 to G59 is a site bonded to the above chemical formula 1, and the remaining ones of G53 to G59 that are not bonded to the above chemical formula 1 are the same or different from one another and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group; any one of G60 to G67 is a site bonded to the above chemical formula 1, and the remaining ones of G60 to G67 that are not bonded to the above chemical formula 1 are the same as or different from one another and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group; Any one of G68 to G76 is a site bonded to the above chemical formula 1, and the remaining ones of G68 to G76 that are not bonded to the above chemical formula 1 are the same as or different from one another and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group.

[0056] According to one embodiment of the present specification, X1 to X4 are O. According to one embodiment of the present specification, X1 to X4 are S.

[0057] According to one embodiment of the present specification, X1 and X2 are S, and X3 and X4 are O. According to one embodiment of the present specification, X1 and X2 are O, and X3 and X4 are S.

[0058] According to one embodiment of the present specification, X1 is O. According to one embodiment of the present specification, X2 is O. According to one embodiment of the present specification, X3 is O. According to one embodiment of the present specification, X4 is O.

[0059] According to one embodiment of the present specification, X1 is S. According to one embodiment of the present specification, X2 is S. According to one embodiment of the present specification, X3 is S. According to one embodiment of the present specification, X4 is S.

[0060] According to one embodiment of the present specification, R1 to R4 are the same or different and each independently represent a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched 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, or a combination thereof; 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.

[0061] According to one embodiment of the present specification, R1 to R4 are the same or different and each independently represent 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 a combination thereof; a naphthyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched 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.

[0062] According to one embodiment of the present specification, R1 to R4 are the same or different and each independently represent 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.

[0063] According to one embodiment of the present specification, R1 to R4 are the same or different and each independently represent 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 unsubstituted or substituted 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.

[0064] According to one embodiment of the present specification, R1 to R4 are the same as each other.

[0065] According to one embodiment of the present specification, R5 and R6 are the same or different and each independently represent a linear or branched alkylene group having 2 to 30 carbon atoms; or a monocyclic or polycyclic cycloalkylene group having 6 to 30 carbon atoms.

[0066] According to one embodiment of the present specification, R5 and R6 are the same or different and each independently represent a linear or branched alkylene group having 2 to 10 carbon atoms; or a monocyclic or polycyclic cycloalkylene group having 6 to 10 carbon atoms.

[0067] According to one embodiment of the present specification, R5 and R6 are the same or different and each independently represent an ethylene group; an isopropylene group; an isobutylene group; or a cyclohexylene group.

[0068] According to one embodiment of the present specification, R5 and R6 are the same as each other.

[0069] According to one embodiment of the present specification, R101 and R102 are hydrogen.

[0070] According to one embodiment of the present specification, the above-mentioned La is a direct bond; or -C(=O)-L'-. According to one embodiment of the present specification, La is a direct bond. According to one embodiment of the present specification, La is -C(=O)-L'-.

[0071] According to one embodiment of the present specification, the above L' is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms. According to one embodiment of the present specification, the above L' is a monocyclic or polycyclic arylene group having 6 to 10 carbon atoms. According to one embodiment of the present specification, L' is a phenylene group.

[0072] According to one embodiment of the present specification, the resin may have -OH; -SH; -CO2CH3; or -OC6H5 as a terminal group.

[0073] In one embodiment of the present specification, the weight average molecular weight of the resin is 10,000 g / mol to 200,000 g / mol, preferably 15,000 g / mol to 100,000 g / mol, more preferably 20,000 g / mol to 50,000 g / mol, or 25,000 g / mol to 40,000 g / mol.

[0074] When the resin satisfies the above-mentioned range of weight average molecular weight, the resin can have optimal fluidity and processability.

[0075] In one embodiment of the present invention, the number average molecular weight of the resin is 10,000 g / mol to 100,000 g / mol, 10,000 g / mol to 50,000 g / mol, 10,000 g / mol to 30,000 g / mol, or 11,000 g / mol to 28,000 g / mol, preferably 12,000 g / mol to 25,000 g / mol.

[0076] The weight-average molecular weight (Mw) of the resins and oligomers used in their preparation can be measured by gel permeation chromatography (GPC) using an Agilent 1200 series instrument with a polystyrene standard (PS standard). Specifically, measurements can be performed using an Agilent 1200 series instrument with a Polymer Laboratories PLgel MIX-B 300 mm column at a measurement temperature of 40°C, a tetrahydrofuran (THF) solvent, and a flow rate of 1 mL / min. Resin or oligomer samples are prepared to a concentration of 10 mg / 10 mL and then dispensed in 10 μL amounts. The weight-average molecular weight (Mw) values ​​are derived using a calibration curve formed using the polystyrene standard. In this case, nine types of molecular weights (g / mol) of polystyrene standards are used: 2,000 / 10,000 / 30,000 / 70,000 / 200,000 / 700,000 / 2,000,000 / 4,000,000 / 10,000,000.

[0077] In one embodiment of the present specification, the glass transition temperature (Tg) of the resin may be 150°C to 300°C, preferably 160°C to 290°C, 170°C to 280°C, 170°C to 270°C, or 162°C to 235°C.

[0078] When the resin satisfies the above glass transition temperature range, it has excellent heat resistance and injectability, and when it is mixed with a resin having a glass transition temperature different from the above range to produce a resin composition, it is easy to adjust the glass transition temperature, and the physical properties targeted in this specification can be satisfied.

[0079] The glass transition temperature (Tg) can be measured by a differential scanning calorimeter (DSC). Specifically, the glass transition temperature can be measured from a graph obtained by heating 5.5 mg to 8.5 mg of the resin sample to 270°C in a nitrogen atmosphere, cooling it, and then heating it again at a heating rate of 10°C / min.

[0080] In one embodiment of the present specification, the refractive index of the resin measured at a wavelength of 589 nm is 1.68 to 1.76. The refractive index may be preferably 1.685 to 1.755. When the resin satisfies the refractive index, when it is applied to a molded product such as an optical lens, it is possible to produce a thin and lightweight optical lens.

[0081] In one embodiment of the present specification, the Abbe number of the resin measured and calculated at wavelengths of 486, 589, and 656 nm may be 5 to 20, preferably 12.1 to 17.6, and more preferably 10.5 to 15.5. When the resin satisfies the above Abbe number range, when the resin is applied to a molded product such as an optical lens, dispersion is reduced and clarity is improved.

[0082] The Abbe number is specifically the refractive index (n D ,n F ,n C ) and the Abbe number can be calculated using the following formula: Abbe number = (n D -1) / (n F -n C )

[0083] The refractive index and Abbe number can be measured from a film prepared by spin-coating a solution prepared by dissolving the resin in a solvent onto a silicon wafer. The coated film can be measured at 20°C using an ellipsometer to obtain the resultant value according to the wavelength of light. The spin-coating can be performed at a rotation speed of 150 rpm to 300 rpm, and the coated film can have a thickness of 5 μm to 20 μm. The silicon wafer is not particularly limited, and any suitable silicon wafer can be used as long as it allows the refractive index and Abbe number of the resin composition according to the present specification to be measured. The solvent can be dimethylacetamide or 1,2-dichlorobenzene, and the solution can be prepared by dissolving the resin sample in a concentration of 10 wt % based on the total weight of the solution.

[0084] One embodiment of the present disclosure provides a compound of formula 1a: [ka] In the above chemical formula 1a, X1 to X4 are the same or different and each independently represents O or S; R1 to R4 are the same or different and each independently represent a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R5 and R6 are the same or different and each independently represent a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; R101 and R102 are the same or different and each independently represent hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; r101 is 1 or 2, and when r101 is 2, the two R101 are the same or different from each other; r102 is 1 or 2, and when r102 is 2, the two R102 are the same or different from each other; m and n are each 0 or 1.

[0085] According to one embodiment of the present specification, the above chemical formula 1a is the following chemical formula 1a-1. [ka] In the above chemical formula 1a-1, X1 to X4, R1 to R6, m, and n are defined as in the above chemical formula 1a.

[0086] According to one embodiment of the present specification, the above chemical formula 1a is any one of the following chemical formulas 1a-2 to 1a-5. [ka]

[0087] In the above chemical formulas 1a-2 to 1a-5, X1 to X4, R1 to R6, m, and n are defined as in the above chemical formula 1a.

[0088] One embodiment of the present specification provides a method for producing the resin, comprising polymerizing a composition for producing the resin, the composition comprising a compound of the following formula 1a; and a polyester precursor or a polycarbonate precursor: [ka]

[0089] In the above chemical formula 1a, X1 to X4, R1 to R6, R101, R102, r101, r102, m, and n are defined as in the above chemical formula 1a.

[0090] When the compound of Formula 1a is included, it is easy to polymerize, has a wide range of refractive indexes or a high refractive index depending on the substituent, and has a wide range of glass transition temperatures.

[0091] The composition for producing a resin may further contain a solvent.

[0092] The solvent may be, for example, diphenyl ether, dimethylacetamide, or methanol, but is not limited thereto, and any solvent applicable in the art may be appropriately adopted.

[0093] The solvent may be contained in an amount of 5 to 60 parts by weight relative to 100 parts by weight of the composition for producing a resin.

[0094] The solvent may be contained in an amount of preferably 5 to 50 parts by weight, 7 to 45 parts by weight, or 8 to 40 parts by weight relative to 100 parts by weight of the composition for producing a resin.

[0095] According to one embodiment of the present specification, the compound may contain two or more of the above chemical formula 1a, and the two or more chemical formulas 1a may be the same or different from each other.

[0096] In one embodiment of the present specification, the compound of Formula 1a may be, but is not limited to, any one of the following compounds: [ka]

[0097] In one embodiment of the present specification, the compound of Chemical Formula 1a may be included in an amount of 1 part by weight to 100 parts by weight, or 1 part by weight to 99 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0098] More specifically, the compound of Chemical Formula 1a may be contained 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 relative to 100 parts by weight of the composition for producing a resin.

[0099] In one embodiment of the present specification, the polyester precursor or polycarbonate precursor may be contained in an amount of 1 part by weight to 60 parts by weight relative to 100 parts by weight of the composition for producing a resin.

[0100] The polyester precursor or polycarbonate precursor may be contained in an amount of preferably 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 resin production composition.

[0101] According to one embodiment of the present specification, the polyester precursor is represented by the following chemical formula A, and the polycarbonate precursor is represented by the following chemical formula B. [ka] In the above chemical formulas A and B, Ra1, Ra2, Rb1, and Rb2 are the same or different, and each independently represents a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; Ar1 is a substituted or unsubstituted arylene group; a1 to a4 are each 0 or 1.

[0102] According to one embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a halogen group; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0103] According to one embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a halogen group; a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0104] According to one embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a halogen group; a linear or branched alkyl group having 1 to 30 carbon atoms which is unsubstituted or substituted with a hydroxy group; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0105] According to one embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a halogen group; a linear or branched alkyl group having 1 to 20 carbon atoms which is unsubstituted or substituted with a hydroxy group; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0106] According to one embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2 are the same or different from each other and each independently represent -Cl; a methyl group; an ethyl group unsubstituted or substituted with a hydroxy group; an n-propyl group; an n-butyl group; or a phenyl group.

[0107] In one embodiment of the present specification, Ra1 and Ra2 are the same or different and each independently represent -Cl; or an ethyl group substituted with a hydroxy group.

[0108] In one embodiment herein, Ra1 and Ra2 are -Cl.

[0109] In one embodiment of the present specification, Ra1 and Ra2 are methyl groups.

[0110] In one embodiment of the present specification, Ra1 and Ra2 are ethyl groups substituted with hydroxy groups.

[0111] According to one embodiment of the present specification, Rb1 and Rb2 are the same or different and each independently represent -Cl; a methyl group; an ethyl group; an n-propyl group; an n-butyl group; or a phenyl group.

[0112] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0113] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0114] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0115] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted phenylene group.

[0116] In one embodiment of the present invention, Ar1 is a phenylene group.

[0117] According to one embodiment of the present specification, the above chemical formula A is the following compound: [ka]

[0118] According to one embodiment of the present specification, the above chemical formula B is any one selected from the following compounds: [ka]

[0119] The polycarbonate precursor functions to connect additional comonomers as needed. Specific examples of the polycarbonate precursor that can be used in addition to the compound of Formula B include phosgene, triphosgene, diphosgene, bromophosgene, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, ditolyl carbonate, bis(chlorophenyl) carbonate, m-cresyl carbonate, dinaphthyl carbonate, bis(diphenyl) carbonate, and bishaloformates, and any one or a mixture of two or more of these can be used.

[0120] The compound of Formula 1a can be polymerized with the polyester precursor of Formula A or the polycarbonate precursor of Formula B to form the unit of Formula 1.

[0121] In one embodiment of the present specification, the resin is preferably polymerized from the compound of formula 1a and the polyester precursor of formula A.

[0122] In one embodiment of the present specification, the resin is preferably polymerized from the compound of formula 1a above and the polycarbonate precursor of formula B above.

[0123] The compound of Formula 1a may be used in an amount of 1 to 100 parts by mole, or 1 to 99 parts by mole, based on 100 parts by mole of the total monomers constituting the resin containing the unit of Formula 1.

[0124] The polyester precursor of Formula A or the polycarbonate precursor of Formula B may be used in an amount of 50 to 150 parts by mole based on 100 parts by mole of the total monomers of the compound of Formula 1a constituting the resin.

[0125] Polymerization of the resins according to the present invention can be carried out by methods known in the art.

[0126] The polymerization is preferably carried out by a melt polycondensation method.

[0127] The melt polycondensation method may involve using the resin-producing composition, optionally with the addition of a catalyst, and performing melt polycondensation under heating, additionally at atmospheric pressure or reduced pressure, while removing by-products through a transesterification reaction. The catalyst may be a substance commonly used in the art.

[0128] Specifically, the melt polycondensation method is preferably carried out by melting the compound of Formula 1a and the polyester precursor or polycarbonate precursor in a reaction vessel, and then allowing the by-product compounds to remain.

[0129] In order to retain the by-produced compounds, the pressure in the reaction apparatus can be controlled by blocking the reaction apparatus or by reducing or increasing the pressure.

[0130] The reaction time for this step is from 20 minutes to 600 minutes, preferably from 40 minutes to 450 minutes, and more preferably from 60 minutes to 300 minutes.

[0131] If the by-product compounds are distilled off immediately after production, the final resin will have a low content of polymers, whereas if the by-product compounds are allowed to remain in the reaction vessel for a certain period of time, the final resin will have a high content of polymers.

[0132] The melt polycondensation method may be carried out continuously or batchwise. The reaction apparatus used to carry out the reaction may be a vertical type equipped with an anchor-type stirring blade, a Maxblend stirring blade, a helical ribbon-type stirring blade, or the like, or a horizontal type equipped with a paddle blade, a lattice blade, a spectacle blade, or the like, or an extruder type equipped with a screw. It is also preferable to use a reaction apparatus that is an appropriate combination of these reaction apparatuses, taking into consideration the viscosity of the polymer.

[0133] In the method for producing the resin used herein, after the polymerization reaction is completed, the catalyst may be removed or deactivated to maintain thermal and hydrolytic stability. A method for deactivating the catalyst by adding an acidic substance, which is known in the art, is preferably carried out.

[0134] Examples of the acidic substance include esters such as butyl benzoate, aromatic sulfonic acids such as p-toluenesulfonic acid, aromatic sulfonic acid esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate, phosphoric acids such as phosphorous acid, phosphoric acid and phosphonic acid, phosphorous acid esters such as triphenyl phosphite, monophenyl phosphite, diphenyl phosphite, diethyl phosphite, di-n-propyl phosphite, di-n-butyl phosphite, di-n-hexyl phosphite, dioctyl phosphite and monooctyl phosphite, and esters of phosphates such as triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate and dioctyl phosphate, Phosphate esters such as monooctyl phosphate; phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid, and dibutylphosphonic acid; phosphonate esters such as diethyl phenylphosphonate; phosphines such as triphenylphosphine and bis(diphenylphosphino)ethane; boric acids such as boric acid and phenylboric acid; aromatic sulfonates such as tetrabutylphosphonium dodecylbenzenesulfonate; organic halides such as stearic acid chloride, benzoyl chloride, and p-toluenesulfonic acid chloride; alkyl sulfates such as dimethyl sulfate; and organic halides such as benzyl chloride are preferably used.

[0135] The acidic substance can be used in an amount of 0.1 to 5 parts by mol, preferably 0.1 to 1 part by mol, relative to 100 parts by mol of the catalyst.

[0136] If the amount of the acidic substance is less than 0.1 parts by mole, the deactivation effect will be insufficient, which is undesirable, whereas if it exceeds 5 parts by mole, the heat resistance of the resin will decrease and the molded product will be prone to coloration, which is undesirable.

[0137] After the catalyst is deactivated, a devolatilization step can be further carried out to remove low-boiling compounds from the resin at a pressure of 0.1 mmHg to 1 mmHg and a temperature of 200° C. to 350° C. For this step, a horizontal apparatus equipped with stirring blades with excellent surface renewal ability, such as paddle blades, lattice blades, or spectacle blades, or a thin-film evaporator is preferably used.

[0138] The resin of the present invention preferably has a minimum content of foreign matter, and filtration of the molten raw material, filtration of the catalyst solution, etc. are preferably carried out.

[0139] The mesh of the filter used for the filtration is preferably 5 μm or less, more preferably 1 μm or less. The produced resin is preferably filtered through a polymer filter. The mesh of the polymer filter is preferably 100 μm or less, more preferably 30 μm or less. The process of collecting the resin pellets must be carried out in a low-dust environment, preferably class 6 or less, more preferably class 5 or less.

[0140] Furthermore, examples of molding methods for molding articles containing the resin include, in addition to injection molding, compression molding, casting, rolling, extrusion molding, and stretching, but are not limited to these.

[0141] Another embodiment of the present specification provides a resin composition comprising a resin according to the above-described embodiment.

[0142] 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.

[0143] In one embodiment of the present specification, the resin composition may further include a solvent, which may be, for example, dimethylacetamide or 1,2-dichlorobenzene.

[0144] The solvent may be included in an amount of 20 to 99 parts by weight based on 100 parts by weight of the resin composition.

[0145] The resin composition may further include an additional monomer in addition to the compound of Formula 1a. The additional monomer is not particularly limited, and any monomer commonly used in the art related to polyesters or polycarbonates may be appropriately used as long as it does not change the main physical properties of the resin composition. The additional monomer may be used in an amount of 1 to 50 moles per 100 moles of the total monomers constituting the resin containing the unit of Formula 1.

[0146] In addition to the resin containing the unit of Chemical Formula 1, the resin composition may further contain, if necessary, additives such as at least one selected from the group consisting of antioxidants, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, fluorescent brighteners, UV absorbers, pigments, and dyes.

[0147] The additive may be included in an amount of 1 to 99 parts by weight based on 100 parts by weight of the resin composition.

[0148] The types of the antioxidant, plasticizer, antistatic agent, nucleating agent, flame retardant, lubricant, impact modifier, fluorescent brightener, ultraviolet absorber, pigment, or dye are not particularly limited, and those used in the art can be appropriately adopted.

[0149] Another embodiment of the present specification provides a molded article comprising the resin composition according to the above-described embodiment.

[0150] In one embodiment of the present specification, the molded article can be produced from the resin composition or a cured product thereof.

[0151] An example of a method for producing the molded product may include the steps of thoroughly mixing a resin containing the unit of Chemical Formula 1 and the additive using a mixer, extruding the mixture using an extruder to prepare pellets, drying the pellets, and then injecting them into an injection molding machine.

[0152] In one embodiment of the present specification, the molded article is an optical member.

[0153] In one embodiment of the present specification, the molded article is an optical lens.

[0154] An optical lens according to an embodiment of the present specification can realize an optical lens with a high refractive index and a small thickness.

[0155] The optical lens is manufactured using the resin, has a small thickness, a high refractive index and high transparency, and can be preferably applied to cameras. [Example]

[0156] The present invention will now be illustrated in more detail through the following examples.

[0157] 1. Synthesis of Monomer 1 [ka]

[0158] 1) Synthesis of compound 1-C 24.1 g (68.9 mmol, 1.0 eq) of compound 1-A and 51.51 g (289.4 mmol, 4.2 eq) of compound 1-B were dissolved in 200 g of tetrahydrofuran (THF) and stirred at room temperature for 25 hours. The mixture was then concentrated under vacuum to completely remove the solvent. The organic layer was separated by washing with dichloromethane (DCM) / HO, and the solvent was concentrated under vacuum. The resulting solid was purified by column chromatography using ethyl acetate (EA) and dichloromethane (DCM), and then precipitated with n-hexane (n-Hex) to obtain 27 g of compound 1-C as a white solid.

[0159] 2) Synthesis of Compound 1-E Compound 1-C (67.5 g, 79 mmol, 1.0 eq) and compound 1-D (56.06 g, 326 mmol, 4.12 eq) were dissolved in 510 g of tetrahydrofuran (THF) and stirred in an 80 °C oil bath for 30 minutes. KCO (56.86 g, 411 mmol, 5.20 eq) was dissolved in 489 mL of water and added dropwise over 10 minutes while maintaining the internal temperature above 50 °C. Pd(t-BuP) catalyst (0.20 g, 0.4 mmol, 0.005 eq) was added at an internal temperature of 60 °C. After stirring for 1 hour, the mixture was washed with ethyl acetate (EA) / HO, the organic layer was separated, and the solvent was concentrated in vacuo. After purification by column chromatography using n-hexane (n-Hex) and dichloromethane (DCM), the product was precipitated with n-hexane (n-Hex) to obtain 45 g of compound 1-E as a white solid.

[0160] 3) Synthesis of Monomer 1 156.5 g (183 mmol, 1.0 eq) of compound 1-E, 48.57 g (552 mmol, 3.0 eq) of compound 1-F, and 0.33 g (147 mmol, 0.80 eq) of KCO were dissolved in 400 g of dimethylacetamide (DMAc) and stirred in a 120°C oil bath for 2 hours. After cooling, water was added to precipitate a solid, which was then filtered. The resulting solid was purified by column chromatography using ethyl acetate (EA) and dichloromethane (DCM), and then precipitated with n-hexane (n-Hex) to obtain 104 g of a white solid, compound Monomer 1. MS: [M+H] + =942

[0161] 2. Synthesis of Monomer 2 [ka] Monomer 2 was obtained through the same synthesis method as for Monomer 1, except that compound 2-A was used instead of compound 1-D. MS: [M+H] + =942

[0162] 3. Synthesis of Monomer 3 [ka] Monomer 3 was obtained through the same synthesis method as for Monomer 1, except that compound 3-A was used instead of compound 1-D. MS: [M+H] + =1247

[0163] 4. Synthesis of Monomer 4 [ka] Monomer 4 was obtained through the same synthesis method as for Monomer 1, except that compound 4-A was used instead of compound 1-D. MS: [M+H] + =1062

[0164] 5. Synthesis of Monomer 5 [ka] Monomer 5 was obtained through the same synthesis method as for Monomer 1, except that compound 5-A was used instead of compound 1-D. MS: [M+H] + =998

[0165] 6. Synthesis of Monomer 6 [ka] Monomer 6 was obtained through the same synthesis method as for Monomer 1, except that compound 6-A was used instead of compound 1-D. MS: [M+H] + =998

[0166] 7. Synthesis of Monomer 7 [ka] Monomer 7 was obtained through the same synthesis method as for Monomer 1, except that compound 7-A was used instead of compound 1-D. MS: [M+H] + =1246

[0167] 8. Synthesis of Monomer 8 [ka] Monomer 8 was obtained through the same synthesis method as for Monomer 1, except that compound 8-A was used instead of compound 1-D. MS: [M+H] + =1110

[0168] 9. Synthesis of Monomer 9 [ka] Monomer 9 was obtained through the same synthesis method as for Monomer 1, except that compound 9-A was used instead of compound 1-D. MS: [M+H] + =1246

[0169] 10. Synthesis of Monomer 10 [ka] Monomer 10 was obtained through the same synthesis method as for Monomer 1, except that compound 10-A was used instead of compound 1-D. MS: [M+H] + =1246

[0170] 11. Synthesis of Monomer 11 [ka] Monomer 11 was obtained through the same synthesis method as for Monomer 1, except that compound 11-A was used instead of compound 1-D. MS: [M+H] + =1510

[0171] 12. Synthesis of Monomer 12 [ka] Monomer 12 was obtained through the same synthesis method as for Monomer 1, except that compound 12-A was used instead of compound 1-D. MS: [M+H] + =1402

[0172] 13. Synthesis of Monomer 13 [ka] Monomer 13 was obtained through the same synthesis method as for Monomer 1, except that compound 13-A was used instead of compound 1-D. MS: [M+H] + =1402

[0173] 14. Synthesis of Monomer 14 [ka] Monomer 14 was obtained through the same synthesis method as for Monomer 1, except that compound 14-A was used instead of compound 1-D. MS: [M+H] + =902

[0174] 15. Synthesis of Monomer 15 [ka] Monomer 15 was obtained through the same synthesis method as for Monomer 1, except that compound 15-A was used instead of compound 1-D. MS: [M+H] + =1102

[0175] 16. Synthesis of Monomer 16 [ka] Monomer 16 was obtained through the same synthesis method as for Monomer 1, except that compound 16-A was used instead of compound 1-F. MS: [M+H] + =970

[0176] 17. Synthesis of Monomer 17 [ka] The synthesis of the compound 1-E is the same as the production method of the monomer 1. 78.2 g (91.5 mmol, 1.0 eq) of compound 1-E, 17.32 g (192 mmol, 2.1 eq) of compound 17-A, and 350.36 g (192 mmol, 2.1 eq) of PPh were dissolved in 2,000 g of tetrahydrofuran (THF), and 38.82 g (192 mmol, 2.1 eq) of diisopropyl azodicarboxylate was added over 70 minutes. After addition, the mixture was stirred at room temperature for 12 hours. The solvent was removed by vacuum concentration, and the organic layer was separated by washing with dichloromethane (DCM) / HO. The solvent was then vacuum concentrated. The resulting product was purified by column chromatography using ethyl acetate (EA) and dichloromethane (DCM) and precipitated with n-hexane (n-Hex), yielding 55 g of monomer 17 as a white solid. MS: [M+H] + =998

[0177] 18. Synthesis of Monomer 18 [ka] The synthesis of the compound 1-E is the same as the production method of the monomer 1. 78.2 g (91.5 mmol, 1.0 eq) of compound 1-E was dissolved in 500 g of tetrahydrofuran (THF) and 500 g of t-BuOH, and 21.56 g (192 mmol, 2.1 eq) of KOTBu was added. After the addition, 18.84 g (192 mmol, 2.0 eq) of compound 18-A was slowly added. The mixture was then heated and stirred at reflux for 72 hours. After cooling, the mixture was concentrated and purified by column chromatography using ethyl acetate (EA) and dichloromethane (DCM). The resulting mixture was then precipitated with n-hexane (n-Hex) to obtain 48 g of monomer 18 as a white solid. MS: [M+H] + =1050

[0178] 19. Synthesis of Monomer 19 [ka] Monomer 19 was obtained through the same synthesis method as for Monomer 17, except that compound 19-A was used instead of compound 17-A. MS: [M+H] + =1050

[0179] 20. Synthesis of Monomer 20 [ka] Monomer 20 was obtained through the same synthesis method as for Monomer 17, except that compound 20-A was used instead of compound 17-A. MS: [M+H] + =1050

[0180] 21. Synthesis of Monomer 21 [ka] Monomer 21 was obtained through the same synthesis method as for Monomer 1, except that compound 21-A was used instead of compound 1-A. MS: [M+H] + =974

[0181] 22. Synthesis of Monomer C1 [ka] Comparative Example C1 was obtained through the same synthesis method as Monomer 1. MS: [M+H] + =438

[0182] 23. Synthesis of Monomer C2 [ka] Comparative Example C2 was obtained in the same manner as in the synthesis of Monomer 1, except that 1-C2 was used instead of Compound 1-A and phenylboronic acid was used instead of Compound 1-D. MS: [M+H] + =590

[0183] 24. Synthesis of Monomer C3 [ka] Comparative Example C3 was obtained through the same synthesis method as Monomer 1, except that Compound 1-C2 was used instead of Compound 1-A. MS: [M+H] + =690

[0184] 25. Synthesis of Monomer C4 [ka] Comparative Example C4 was obtained in the same manner as in the synthesis of Monomer 1, except that compound 1-C3 was used instead of compound 1-A and compound 1-G was used instead of compound 1-D. MS: [M+H] + =590

[0185] Manufacture of polyester resin 1 [ka] 1.67g (1.77mmol, 1.0eq) of Monomer 1 and 0.36g (1.77mmol, 1.0eq) of Terephthaloyl Chloride were dissolved in 4.1g of Diphenyl Ether (DPE) and reacted for 6 hours in an oil bath at 180°C. As the reaction progressed, hydrochloric acid (HCl) gas was generated, and to remove this, a nitrogen purge and hydrochloric acid gas collection device were installed. After the reaction, the mixture was cooled to 100°C, and 15g of dimethylacetamide (DMAc) was added, followed by precipitation with methanol to produce Resin 1.

[0186] Manufacture of polyester resins 2-21 Polyester Resins 2 to 21 were produced in the same manner as Polyester Resin 1, except that Monomers 2 to 21 were used instead of Monomer 1, respectively.

[0187] Preparation of comparative resins PE1 to PE4 Comparative resins PE1 to PE4 were produced in the same manner as the production method for polyester resin 1, except that monomers C1 to C4 were used instead of monomer 1, respectively.

[0188] Manufacture of polycarbonate resin 1 [ka] The raw materials were 282.9 g (0.3 mol, 1 eq) of monomer 1, 67.5 g (0.315 mol, 1.05 eq) of diphenyl carbonate (hereinafter sometimes abbreviated as "DPC"), and 0.37 mg (4.4 × 10 -6 mol, 0.000015 eq) was placed in a reactor and melted, followed by a reaction at 250°C for 5 hours. As the reaction proceeded, phenol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create a normal pressure atmosphere, and the polymerized polymer molten resin was removed, yielding polycarbonate resin 1.

[0189] Manufacture of polycarbonate resins 2-21 Polycarbonate resins 2 to 21 were produced in the same manner as the production method for polycarbonate resin 1, except that monomers 2 to 21 were used instead of monomer 1, respectively.

[0190] Manufacture of comparative resins PC1 to PC4 Comparative resins PC1 to PC4 were produced in the same manner as the production method for polycarbonate resin 1, except that monomers C1 to C4 were used instead of monomer 1, respectively.

[0191] Experimental Example The molecular weight and molecular weight distribution of the polymerized resin sample were confirmed by gel permeation chromatography (GPC), and a thermogram was obtained using a differential scanning calorimeter (DSC) to examine the thermal properties. After film formation, an ellipsometer was used to measure the refractive index and Abbe number, and the results were obtained depending on the wavelength of light.

[0192] The molecular weight was measured by gel permeation chromatography (GPC) using tetrahydrofuran (THF, stabilized with BHT (butylhydroxytoluene))) as a solvent. The resin sample was dissolved in tetrahydrofuran at a concentration of 1.0 mg / 1 ml and filtered through a syringe filter. The solution was then injected and measured at 40°C, and the results are shown in Tables 1 and 2 below. A Waters RI detector was used, and two Agilent PLgel MIXED-B columns were used.

[0193] The glass transition temperature (Tg) of the resin was measured using a differential scanning calorimeter (DSC). 5.5 mg to 8.5 mg of resin sample was heated to 270°C under N2 flow, then cooled, and heated a second time at a heating rate of 10°C / min. The glass transition temperature (Tg) was determined from the graph obtained, and is shown in Tables 1 and 2 below.

[0194] To measure the refractive index and Abbe number of the resin, a polymerized resin powder sample was dissolved in dimethylacetamide solvent at 10 wt % based on the total weight of the polymer solution to prepare a polymer solution. The polymer solution was spin-coated onto a silicon wafer at a rotation speed of 220 rpm to form a film with a thickness of 20 μm. The results were obtained using an ellipsometer at 20°C according to the wavelength of light, and are listed in Tables 1 and 2 below. Specifically, the refractive index was measured at a wavelength of 589 nm, and the Abbe number was measured by measuring the refractive index (n D ,n F ,n C ) were measured, and the Abbe number was calculated using the following formula. Abbe number = (n D -1) / (n F -n C )

[0195] [Table 1]

[0196] [Table 2]

[0197] In Tables 1 and 2 above, Mn means number average molecular weight, Mw means weight average molecular weight, and the refractive index is a value measured at a wavelength of 589 nm.

[0198] According to Tables 1 and 2 above, the resins of Examples 1-1 to 1-21 and 2-1 to 2-21 contain units of Chemical Formula 1 according to one embodiment of the present specification, and in particular, when the fluorene core structure is substituted with electron-rich substituents R1 to R4 such as an aryl group or a heteroaryl group, the refractive index can be improved by increasing the electron density of the fluorene core structure.

[0199] In contrast, the resins of Comparative Examples 1-1 to 1-4 and 2-1 to 2-4 lack electron-rich substituents on the benzene ring of the fluorene core structure, and therefore have lower refractive indices than the resins of Examples 1-1 to 1-21 and 2-1 to 2-21 of this specification.

[0200] In order to appropriately apply the resin according to the embodiment of the present invention to molded articles such as optical lenses, a high refractive index is a priority. In the case of Comparative Examples 1-1 to 1-4 and 2-1 to 2-4, although the Abbe number is higher than that of Examples 1-1 to 1-21 and 2-1 to 2-21, the refractive index is very low. Therefore, it was confirmed that Examples 1-1 to 1-21 and 2-1 to 2-21 are superior as optical materials to Comparative Examples 1-1 to 1-4 and 2-1 to 2-4.

Claims

1. A resin comprising units of the following formula 1: 【Chemical 1】 In the above Chemical Formula 1, X1 to X4 are the same or different and each independently represents O or S; R1 to R4 are the same or different and each independently represent a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched 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, or a combination thereof, which is substituted or unsubstituted with one or more of these; or a polycyclic heteroaryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, R5 and R6 are the same or different and each independently represent a linear or branched alkylene group having 2 to 30 carbon atoms; or a monocyclic or polycyclic cycloalkylene group having 6 to 30 carbon atoms, R101 and R102 are hydrogen; r101 is 2, r102 is 2, L a is a direct bond; or —C(═O)-L′—; L' is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; m and n are each 0 or 1; * indicates the site connected to the main chain of the resin.

2. The resin according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1: 【Chemistry 2】 In the above Chemical Formula 1-1, *, La, R1 to R6, m, n, and X1 to X4 are defined as in Formula 1 above.

3. The resin according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 1-2 to 1-5: 【Chemistry 3】 In the chemical formulas 1-2 to 1-5, *, La, R1 to R6, and X1 to X4 are defined as in Formula 1 above.

4. 2. The resin of claim 1, wherein the weight average molecular weight (Mw) is from 10,000 g / mol to 200,000 g / mol.

5. 2. The resin according to claim 1, wherein the refractive index measured at a wavelength of 589 nm is 1.68 to 1.

76.

6. 2. The resin of claim 1, wherein the resin has a glass transition temperature (Tg) of 150°C to 300°C.

7. 2. The resin according to claim 1, which has an Abbe number of 5 to 20 measured at wavelengths of 589 nm, 486 nm, and 656 nm.

8. A compound of formula 1a: 【Chemistry 4】 In the above formula 1a, X1 to X4 are the same or different and each independently represents O or S; R1 to R4 are the same or different and each independently represent a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched 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, or a combination thereof, which is substituted or unsubstituted with one or more of these; or a polycyclic heteroaryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, R5 and R6 are the same or different and each independently represent a linear or branched alkylene group having 2 to 30 carbon atoms; or a monocyclic or polycyclic cycloalkylene group having 6 to 30 carbon atoms, R101 and R102 are hydrogen; r101 is 2, r102 is 2, m and n are each 0 or 1;

9. The compound according to claim 8, wherein the chemical formula 1a is any one selected from the following compounds: 【Chemistry 5】

10. A compound of formula 1a: A method for producing the resin according to any one of claims 1 to 7, comprising the step of polymerizing a resin-producing composition comprising a polyester precursor or a polycarbonate precursor: 【Chemistry 6】 In the above formula 1a, X1 to X4 are the same or different and each independently represents O or S; R1 to R4 are the same or different and each independently represent a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched 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, or a combination thereof, which is substituted or unsubstituted with one or more of these; or a polycyclic heteroaryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, R5 and R6 are the same or different and each independently represent a linear or branched alkylene group having 2 to 30 carbon atoms; or a monocyclic or polycyclic cycloalkylene group having 6 to 30 carbon atoms, R101 and R102 are hydrogen; r101 is 2, r102 is 2, m and n are each 0 or 1;

11. The method for producing a resin according to claim 10, wherein the polyester precursor is represented by the following chemical formula A, and the polycarbonate precursor is represented by the following chemical formula B: 【Chemistry 7】 In the above chemical formulas A and B, R a1 , R 2 , R b1 , and R b2 are the same or different, and each independently represents a halogen group or an aryl group; Ar1 is an arylene group; a1 to a4 each represent 0 or 1.

12. A resin composition comprising the resin according to any one of claims 1 to 7.

13. A molded article comprising the resin composition according to claim 12.

14. The molded article according to claim 13, wherein the molded article is an optical element.

15. The molded article according to claim 13, wherein the molded article is an optical lens.

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