Resin and its manufacturing method

Abstract

The present application relates to a resin containing a unit represented by 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. 10-2021-0063570, filed with the Korean Intellectual Property Office on May 17, 2021, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a resin and a method for producing the same. More specifically, the present invention relates to a polyester or polycarbonate having a high refractive index and high transparency 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, which allows for the manufacture of thinner and lighter lenses, thus enabling the miniaturization of various devices in which the lenses are used.

[0004] Generally, when the refractive index of an optical material increases, there is a problem that the Abbe's number decreases, and 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 invention seeks to provide a resin with a novel structure and a method for producing the same.

[0006] Another embodiment of the present invention provides a composition containing a resin of a novel structure and a molded article made from the composition. [Means for solving the problem]

[0007] One embodiment of the present invention provides a resin comprising a unit represented by the following Chemical Formula 1: [ka] In the above Chemical Formula 1, R1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R2 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group; r1 is an integer of 1 to 4, and when r1 is 2 or more, the two or more R1's are the same or different from each other; r2 is an integer of 0 to 4, and when r2 is 2 or more, the two or more R2's are the same or different from each other; L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group; L is a direct bond; or -CO-L'-; L' is a substituted or unsubstituted arylene group; X1 to X4 are the same or different and each independently represents O or S; Z1 and Z2 are the same or different and each independently represents a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; a and b are the same or different and each independently represents an integer of 1 to 10; when a and b are each 2 or greater, the structures in each bracket are the same or different; * indicates a site connected to the main chain of the resin. The term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of a halogen group, a nitro group (NO2), a nitrile group (CN), an alkyl group, a cycloalkyl group, an aryl group, an aryloxy group, an arylthio group, an alkylthio group, and a heteroaryl group, or that the group is substituted with a substituent in which two or more of the substituents exemplified above are linked, or that the group does not have any substituents.

[0008] One embodiment of the present invention provides a compound represented by formula 1a: [ka] In the above formula 1a, R1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R2 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group; r1 is an integer of 1 to 4, and when r1 is 2 or more, the two or more R1's are the same or different from each other; r2 is an integer of 0 to 4, and when r2 is 2 or more, the two or more R2's are the same or different from each other; L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group; X1 to X4 are the same or different and each independently represents O or S; Z1 and Z2 are the same or different and each independently represents a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; a and b are the same or different and each independently represents an integer of 1 to 10; when a and b are each 2 or greater, the structures in each bracket are the same or different; The term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of a halogen group, a nitro group (NO2), a nitrile group (CN), an alkyl group, a cycloalkyl group, an aryl group, an aryloxy group, an arylthio group, an alkylthio group, and a heteroaryl group, or that the group is substituted with a substituent in which two or more of the substituents exemplified above are linked, or that the group does not have any substituents.

[0009] One embodiment of the present invention provides a method for producing a resin, comprising the step of polymerizing a composition for producing a resin, the composition comprising a compound represented by the following chemical formula 1a; and a polyester precursor or a polycarbonate precursor. [ka] In the above Chemical Formula 1a, the definitions of R1, R2, r1, r2, L1, L2, X1 to X4, Z1, Z2, a, and b are the same as those in the above Chemical Formula 1.

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

[0011] Another embodiment of the present invention provides a molded article comprising a composition comprising a resin according to the above-described embodiment. Effect of the Invention

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

[0013] By using a resin according to one embodiment of the present invention, an excellent optical lens can be obtained. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] Specific embodiments will now be described in more detail.

[0015] 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 the 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.

[0016] As used herein, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of a halogen group; a nitro group (NO2); a nitrile group (CN); an alkyl group; a cycloalkyl group; an aryl group; an aryloxy group; an arylthio group; an alkylthio group; and a heteroaryl group, or substituted with a substituent in which two or more of the above-listed substituents are linked, or has no substituents.

[0017] In this specification, * denotes a binding site to another structure.

[0018] In this specification, the cycloalkylene group may be a monocyclic or polycyclic cycloalkylene group. Specifically, the cycloalkylene group may be a cycloalkylene group having 3 to 20 carbon atoms; a monocyclic or polycyclic cycloalkylene group having 6 to 18 carbon atoms; or a monocyclic or polycyclic cycloalkylene group having 6 to 12 carbon atoms. More specifically, the cycloalkylene group may be a divalent group derived from an alicyclic hydrocarbon such as a cyclopentylene group, a cyclohexylene group, or a cycloheptylene group as a monocyclic cycloalkylene group, or a divalent adamantane-diyl group, a divalent norbornane-diyl group as a polycyclic cycloalkylene group. However, the cycloalkylene group is not limited to these. In addition, the cycloalkylene group may be substituted or unsubstituted with one or more alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, or halogen groups.

[0019] In this specification, the explanation of the cycloalkylene group may be applied to the cycloalkyl group, except that the cycloalkyl group is a monovalent group rather than a divalent group.

[0020] In this specification, the alkylene group is a divalent group derived from an aliphatic hydrocarbon having 1 to 30 carbon atoms, 1 to 20 carbon atoms, 1 to 10 carbon atoms, or 1 to 5 carbon atoms, and may be a straight-chain or branched-chain alkylene group. Specific examples of the alkylene group include a methylene group, an ethylene group, a propylene group, an n-propylene group, an isopropylene group, a butylene group, an n-butylene group, an isobutylene group, a tert-butylene group, a sec-butylene group, a 1-methyl-butylene group, a 1-ethyl-butylene group, a pentylene group, an n-pentylene group, an isopentylene group, a neopentylene group, a tert-pentylene group, a hexylene group, an n-hexylene group, a 1-methylpentylene group, a 2-methylpentylene group, a 4-methyl-2-pentylene group, a 3,3-dimethyl- Examples of alkyl groups include, but are not limited to, ethylbutylene, 2-ethylbutylene, heptylene, n-heptylene, 1-methylhexylene, octylene, n-octylene, tert-octylene, 1-methylheptylene, 2-ethylhexylene, 2-propylpentylene, n-nonylene, 2,2-dimethylheptylene, 1-ethyl-propylene, 1,1-dimethyl-propylene, isohexylene, 2-methylpentylene, 4-methylhexylene, and 5-methylhexylene.

[0021] In this specification, the description of a straight-chain or branched-chain alkylene group may be applied, except that the straight-chain or branched-chain alkyl group is a monovalent group, not a divalent group.

[0022] In this specification, unless otherwise specified, alkyl groups include straight chain alkyl groups and branched chain alkyl groups.

[0023] In the present specification, the arylene group may be a monocyclic or polycyclic arylene group, and the number of carbon atoms is not particularly limited, but preferably has 6 to 30 carbon atoms, and may have 6 to 20 carbon atoms. Specific examples of the monocyclic arylene group include, but are not limited to, a phenylene group, a biphenylylene group, and a terphenylylene group. When the arylene group is a polycyclic arylene group, the number of carbon atoms is not particularly limited, but preferably has 10 to 30 carbon atoms, and may have 10 to 20 carbon atoms. Specific examples of the polycyclic arylene group include, but are not limited to, a naphthylene group, a divalent anthracene group, a divalent phenanthrene group, a divalent triphenylene group, a divalent pyrene group, a divalent perylene group, a divalent chrysene group, and a divalent fluorene group.

[0024] In this specification, the explanation of the arylene group may be applied to the aryl group, except that the aryl group is a monovalent group rather than a divalent group.

[0025] In the present specification, a heteroaryl group includes one or more atoms other than carbon, i.e., heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably 1 to 30, and may be 1 to 20. The heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include, but are not limited to, a thiophene group, a furan group, a dibenzofuran group, a dibenzothiophene group, a benzothiophene 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, and a carbazole group.

[0026] In this specification, the explanation of the heteroaryl group may be applied to the heteroarylene group, except that the heteroarylene group is a divalent group rather than a monovalent group.

[0027] In this specification, the divalent aliphatic hydrocarbon group means the above-mentioned alkylene group, cycloalkylene group, etc.

[0028] In this specification, alkoxy may be an alkoxy group having 1 to 10 carbon atoms or 1 to 5 carbon atoms. Specific examples of alkoxy groups include, but are not limited to, 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, a 1-methyl-butoxy group, a 1-ethyl-butoxy group, or a pentoxy group.

[0029] In this specification, a halogen group is a fluoro group, a chloro group, a bromo group, or an iodo group.

[0030] In this specification, the explanation of the cycloalkylene group described above applies to the aliphatic ring, except that it is divalent, and the explanation of the arylene group or heteroarylene group may apply to the aromatic ring, except that it is divalent.

[0031] In this specification, an aryloxy group may be represented by -ORo, where the above description of the aryl group applies to Ro.

[0032] In this specification, an arylthio group may be represented by -SRs1, and the above description of the aryl group applies to Rs1.

[0033] In this specification, an alkylthio group may be represented by -SRs2, and the above description of the alkyl group applies to Rs2.

[0034] One embodiment of the present invention provides a resin comprising a unit represented by the following Chemical Formula 1: [ka] In the above Chemical Formula 1, R1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R2 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group; r1 is an integer of 1 to 4, and when r1 is 2 or more, the two or more R1's are the same or different from each other; r2 is an integer of 0 to 4, and when r2 is 2 or more, the two or more R2's are the same or different from each other; L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group; L is a direct bond; or -CO-L'-; L' is a substituted or unsubstituted arylene group; X1 to X4 are the same or different and each independently represents O or S; Z1 and Z2 are the same or different and each independently represents a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; a and b are the same or different and each independently represents an integer of 1 to 10; when a and b are each 2 or greater, the structures in each bracket are the same or different; * indicates a site connected to the main chain of the resin. The term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of a halogen group, a nitro group (NO2), a nitrile group (CN), an alkyl group, a cycloalkyl group, an aryl group, an aryloxy group, an arylthio group, an alkylthio group, and a heteroaryl group, or that the group is substituted with a substituent in which two or more of the substituents exemplified above are linked, or that the group does not have any substituents.

[0035] In one embodiment of the present invention, the resin may contain one or more units represented by Chemical Formula 1, and when two or more units are contained, the units may be the same or different from each other.

[0036] The relationship between molecular structure and refractive index, known as the Lorentz-Lorenz formula, shows that the refractive index of a substance made of molecules increases by increasing the electron density of the molecule and decreasing the molecular volume.

[0037] In the above Chemical Formula 1, when R1 is an electron-rich substituent such as a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, the electron density of the structure represented by Chemical Formula 1 can be increased, and the refractive index of a molded article containing the resin can be improved.

[0038] In one embodiment of the present invention, the resin may be a polyester or a polycarbonate. The resin may preferably be a polyester.

[0039] In one embodiment of the present invention, the "substituted or unsubstituted" of R1 is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group; a heteroaryl group; an aryloxy group; an arylthio group; and an alkylthio group.

[0040] In one embodiment of the present invention, the "substituted or unsubstituted" of R1 means substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 6 to 30 carbon atoms; a heteroaryl group having 3 to 30 carbon atoms; an aryloxy group having 6 to 30 carbon atoms; an arylthio group having 6 to 30 carbon atoms; and an alkylthio group having 1 to 30 carbon atoms.

[0041] In one embodiment of the present invention, the "substituted or unsubstituted" of R1 means substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 6 to 20 carbon atoms; a heteroaryl group having 3 to 20 carbon atoms; an aryloxy group having 6 to 20 carbon atoms; an arylthio group having 6 to 20 carbon atoms; and an alkylthio group having 1 to 20 carbon atoms.

[0042] In one embodiment of the present invention, the "substituted or unsubstituted" of R1 is substituted or unsubstituted with one or more substituents selected from the group consisting of a carbazole group, a phenoxy group, a naphthyl group, a phenylthio group, a dibenzofuran group, a dibenzothiophene group, a benzothiophene group, and a methylthio group.

[0043] In one embodiment of the present invention, R1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0044] In one embodiment of the present invention, R1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0045] In one embodiment of the present invention, R1 is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 10 carbon atoms.

[0046] In one embodiment of the present invention, R1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted benzothiophene group; or a substituted or unsubstituted thiophene group.

[0047] In one embodiment of the present invention, R1 is a phenyl group substituted or unsubstituted with a carbazole group, a phenoxy group, a naphthyl group, or a phenylthio group; a naphthyl group substituted or unsubstituted with a naphthyl group; a carbazole group substituted or unsubstituted with a phenyl group; a dibenzofuran group; a dibenzothiophene group; a benzothiophene group; or a thiophene group substituted or unsubstituted with a methylthio group.

[0048] In one embodiment of the present invention, R1 is a phenyl group substituted with a carbazole group, a phenoxy group, a naphthyl group, or a phenylthio group; a naphthyl group unsubstituted or substituted with a naphthyl group; a carbazole group substituted with a phenyl group; a dibenzofuran group; a dibenzothiophene group; a benzothiophene group; or a thiophene group substituted with a methylthio group.

[0049] In one embodiment of the present invention, R2 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0050] In one embodiment of the present invention, R2 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0051] In one embodiment of the present invention, R2 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0052] In one embodiment of the present invention, R2 is hydrogen; or deuterium.

[0053] In one embodiment of the invention, R2 is hydrogen.

[0054] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represents an arylene group substituted or unsubstituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0055] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represents an arylene group substituted or unsubstituted with a substituted or unsubstituted alkyl group, or an arylene group substituted or unsubstituted with a substituted or unsubstituted aryl group.

[0056] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0057] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0058] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0059] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represent a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0060] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represents a phenylene group unsubstituted or substituted with a methyl group or a phenyl group; or a naphthylene group.

[0061] In one embodiment of the invention, L is a direct bond.

[0062] In one embodiment of the invention, L is -CO-L'-.

[0063] In one embodiment of the present invention, L' is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0064] In one embodiment of the present invention, L' is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0065] In one embodiment of the present invention, L' is a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0066] In one embodiment of the present invention, L' is a substituted or unsubstituted phenylene group.

[0067] In one embodiment of the invention, L' is a phenylene group.

[0068] In one embodiment of the present invention, X1 to X4 are O.

[0069] In one embodiment of the present invention, X1 to X4 are S.

[0070] In one embodiment of the present invention, Z1 and Z2 are the same or different and each independently represent a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; or a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms.

[0071] In one embodiment of the present invention, Z1 and Z2 are the same or different and each independently represent a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; or a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms.

[0072] In one embodiment of the present invention, Z1 and Z2 are the same or different and each independently represent a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; or a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms.

[0073] In one embodiment of the present invention, Z1 and Z2 are the same or different and each independently represent a substituted or unsubstituted methylene group; a substituted or unsubstituted ethylene group; a substituted or unsubstituted propylene group; or a substituted or unsubstituted hexylene group.

[0074] In one embodiment of the present invention, Z1 and Z2 are the same or different and each independently represents a methylene group; an ethylene group; a propylene group; or a hexylene group.

[0075] In the present invention, the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-4. [ka]

[0076] In the chemical formulas 1-1 to 1-4, the definitions of R1, R2, r2, L1, L2, X1 to X4, Z1, Z2, L, *, a, and b are the same as those in the chemical formula 1.

[0077] Specifically, the formula 1 may be represented by the formula 1-2 or 1-3.

[0078] According to one embodiment of the present invention, the resin may have -OH; -SH; -CO2CH3; or -OC6H5 as end groups.

[0079] In one embodiment of the present invention, 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 or 20,000 g / mol to 50,000 g / mol, and more preferably 25,000 g / mol to 40,000 g / mol.

[0080] When the resin satisfies the above-mentioned weight average molecular weight range, the resin can have optimal fluidity and processability.

[0081] In the present invention, the weight average molecular weight (Mw) of the resin and the oligomer used in its preparation can be measured by gel permeation chromatography (GPC) using a polystyrene standard (PS standard) using an Agilent 1200 series. Specifically, the measurement can be performed using an Agilent 1200 series instrument using a Polymer Laboratories PLgel MIX-B 300 mm long column. In this case, the measurement temperature is 40°C, the solvent used is tetrahydrofuran (THF), and the flow rate is 1 mL / min. The resin or oligomer sample is prepared to a concentration of 10 mg / 10 mL, and then supplied in an amount of 10 μL, and the weight average molecular weight (Mw) value is derived using a calibration curve formed using a polystyrene standard. In this case, nine types of polystyrene standards with molecular weights (g / mol) are used: 2,000 / 10,000 / 30,000 / 70,000 / 200,000 / 700,000 / 2,000,000 / 4,000,000 / 10,000,000.

[0082] In one embodiment of the present invention, the glass transition temperature (Tg) of the resin may be 160° C. to 210° C., preferably 170° C. to 200° C., or 175° C. to 199° C. When the resin satisfies the above glass transition temperature range, the resin has excellent heat resistance and ejection properties, and when a resin composition is produced by mixing the resin with a resin having a glass transition temperature different from the above range, the glass transition temperature can be easily adjusted, so that the physical properties targeted by the present invention can be satisfied.

[0083] The glass transition temperature (Tg) can be measured using 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 the sample, and then heating the sample at a heating rate of 10° C. / min during the second heating step.

[0084] In one embodiment of the present invention, the resin has a refractive index of 1.665 to 1.75 measured at a wavelength of 589 nm. The refractive index may be preferably 1.668 to 1.723. When the resin satisfies the refractive index range, it is possible to manufacture a thin and lightweight optical lens when the resin is applied to a molded product such as an optical lens.

[0085] In one embodiment of the present invention, the Abbe number of the resin measured and calculated at wavelengths of 589 nm, 486 nm, and 656 nm may be 10 to 25. It may be preferably 12 to 22. It may be more preferably 14.2 to 19.5. When the resin satisfies the above Abbe number range, there is an effect that dispersion is small and clarity is high when the resin is applied to a molded product such as an optical lens. Specifically, the Abbe number is 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 )

[0086] The refractive index and Abbe number may be measured from a film prepared by spin-coating a solution prepared by dissolving the resin in a solvent onto a silicon wafer, and the coated film may be measured at 20° C. using an ellipsometer to obtain a result value according to the wavelength of light. The coating by spin-coating may be performed at a rotation speed of 150 rpm to 300 rpm, and the thickness of the coated film may be 5 μm to 20 μm. The silicon wafer is not particularly limited, and may be appropriately adopted as long as it can measure the refractive index and Abbe number of the resin composition according to the present invention. The solvent may be dimethylacetamide or 1,2-dichlorobenzene, and the solution may be prepared by dissolving the resin sample at 10 wt % based on the total weight of the solution.

[0087] One embodiment of the present invention provides a compound represented by formula 1a: [ka] In the above formula 1a, R1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R2 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group; r1 is an integer of 1 to 4, and when r1 is 2 or more, the two or more R1's are the same or different from each other; r2 is an integer of 0 to 4, and when r2 is 2 or more, the two or more R2's are the same or different from each other; L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group; X1 to X4 are the same or different and each independently represents O or S; Z1 and Z2 are the same or different and each independently represents a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; a and b are the same or different and each independently represents an integer of 1 to 10; when a and b are each 2 or greater, the structures in each bracket are the same or different; The term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of a halogen group, a nitro group (NO2), a nitrile group (CN), an alkyl group, a cycloalkyl group, an aryl group, an aryloxy group, an arylthio group, an alkylthio group, and a heteroaryl group, or that the group is substituted with a substituent in which two or more of the substituents exemplified above are linked, or that the group does not have any substituents.

[0088] One embodiment of the present invention provides a method for producing said resin, comprising the step of polymerizing a composition for producing a resin, the composition comprising a compound represented by the following formula 1a; and a polyester precursor or a polycarbonate precursor: [ka] In the above Chemical Formula 1a, the definitions of R1, R2, r1, r2, L1, L2, X1 to X4, Z1, Z2, a, and b are the same as those in the above Chemical Formula 1.

[0089] One embodiment of the present invention preferably provides a method for producing the resin, comprising the step of polymerizing a composition for producing a resin, the composition comprising the compound represented by formula 1a and the polyester precursor.

[0090] One embodiment of the present invention preferably provides a method for producing the resin, comprising the step of polymerizing a composition for producing a resin, the composition comprising the compound represented by formula 1a and the polycarbonate precursor.

[0091] One embodiment of the present invention provides a composition for producing a resin, comprising a compound represented by the above formula 1a; and a polyester precursor or a polycarbonate precursor.

[0092] The composition for producing a resin may further include a solvent.

[0093] 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.

[0094] The solvent may be contained in an amount of 5 parts by weight to 60 parts by weight based on 100 parts by weight of the composition for producing a resin.

[0095] The solvent may be preferably contained in an amount of 5 parts by weight to 50 parts by weight, 10 parts by weight to 40 parts by weight, or 10 parts by weight to 30 parts by weight relative to 100 parts by weight of the composition for producing a resin.

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

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

[0098] The compound represented by the 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 invention, the polyester precursor or the polycarbonate precursor may be contained in an amount of 1 part by weight to 20 parts by weight based on 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 18 parts by weight, 1 to 16 parts by weight, 1 to 14 parts by weight, 1 to 12 parts by weight, or 1 to 10 parts by weight, based on 100 parts by weight of the composition for producing a resin.

[0101] The compound represented by the formula 1a can be prepared according to the following reaction scheme. [ka]

[0102] In the above reaction scheme, Ar is a substituted or unsubstituted aryl group, and the remaining substituents are defined as in Chemical Formula 1 above.

[0103] In the above reaction scheme, the definition of Ar is the same as the definition of L1 and L2 in the above-mentioned Chemical Formula 1, except that Ar has one bonding position.

[0104] The above reaction scheme illustrates a process for synthesizing a compound having a specific substituent bonded to a specific position, but a unit falling within the scope of Chemical Formula 1 can be synthesized by a synthesis method known in the art using starting materials, intermediate materials, etc. known in the art.

[0105] According to one embodiment of the present invention, the polyester precursor may be represented by the following chemical formula A, and the polycarbonate precursor may be 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, a2, b1, and b2 are each 0 or 1.

[0106] In one embodiment of the present invention, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0107] In one embodiment of the present invention, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0108] In one embodiment of the present invention, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a halogen group; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0109] In one embodiment of the present invention, Ra1, Ra2, Rb1, and Rb2 are the same or different from each other and each independently represent a halogen group; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted phenyl group.

[0110] In one embodiment of the present invention, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represents a chloro group; a methyl group; an ethyl group substituted with a hydroxy group; or a phenyl group.

[0111] In one embodiment of the present invention, Ra1 and Ra2 are chloro groups.

[0112] In one embodiment of the present invention, Ra1 and Ra2 are methyl groups.

[0113] In one embodiment of the present invention, Ra1 and Ra2 are ethyl groups substituted with hydroxy groups.

[0114] In one embodiment of the present invention, Rb1 and Rb2 are chloro groups.

[0115] In one embodiment of the present invention, Rb1 and Rb2 are phenyl groups.

[0116] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0117] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0118] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0119] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted phenylene group.

[0120] In one embodiment of the present invention, Ar1 is a phenylene group.

[0121] In one embodiment of the present invention, a1 is 0.

[0122] In one embodiment of the present invention, a2 is 0.

[0123] In one embodiment of the present invention, b1 is 0.

[0124] In one embodiment of the present invention, b2 is 0.

[0125] In one embodiment of the present invention, a1 is 1.

[0126] In one embodiment of the present invention, a2 is 1.

[0127] In one embodiment of the present invention, b1 is 1.

[0128] In one embodiment of the present invention, b2 is 1.

[0129] The polycarbonate precursor serves to link additional comonomers as necessary, and specific examples that can be used in addition to the compound represented by 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 may be used.

[0130] The compound represented by the formula 1a may be polymerized with the polyester precursor represented by the formula A or the polycarbonate precursor represented by the formula B to form the unit represented by the formula 1.

[0131] In one embodiment of the present invention, the resin is preferably polymerized from the compound represented by the formula 1a and the polyester precursor represented by the formula A.

[0132] The compound represented by the chemical formula 1a may be used in an amount of 1 to 60 parts by mole relative to 100 parts by mole of all monomers constituting the resin containing the unit represented by the chemical formula 1.

[0133] The polyester precursor represented by the chemical formula A or the polycarbonate precursor represented by the chemical formula B may be used in an amount of 50 to 150 parts by mole per 100 parts by mole of the total monomers of the compound represented by the chemical formula 1a constituting the resin.

[0134] Polymerization of the resins according to the present invention may be accomplished using methods well known in the art.

[0135] The polymerization is preferably carried out by a melt polycondensation method.

[0136] The melt polycondensation method may use the composition for producing a resin, and may further apply a catalyst as necessary, and may perform melt polycondensation under heating and additional normal or reduced pressure while removing by-products by transesterification. The catalyst may be a substance generally applied in the technical field.

[0137] Specifically, the melt polycondensation method is preferably carried out by melting the compound represented by the chemical formula 1a and the polyester precursor or the polycarbonate precursor in a reaction vessel, and then carrying out the reaction while retaining by-product compounds.

[0138] In order to retain the by-produced compounds, the reaction apparatus may be blocked or the pressure may be controlled by reducing or increasing the pressure.

[0139] 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.

[0140] In this case, 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.

[0141] The melt polycondensation method may be carried out continuously or batchwise. The reaction apparatus used for the reaction may be a vertical type equipped with an anchor-type impeller, a Max Blend impeller, a helical ribbon-type impeller, or the like, a horizontal type equipped with a paddle impeller, a lattice impeller, a spectacle impeller, or the like, or an extruder type equipped with a screw. In addition, taking into consideration the viscosity of the polymer, it is preferable to use a reaction apparatus that is an appropriate combination of these reaction apparatuses.

[0142] In the method for producing the resin used in the present invention, the catalyst may be removed or deactivated after the polymerization reaction is completed in order to maintain thermal stability and hydrolytic stability. A method for deactivating the catalyst by adding an acidic substance known in the art can be preferably used.

[0143] 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; phosphites 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 the like. Preferred examples of the organic halides that are used include phosphate esters such as monooctyl phosphate; phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid, dibutylphosphonic acid, and the like; phosphonic acid esters such as diethyl phenylphosphonate; phosphines such as triphenylphosphine, bis(diphenylphosphino)ethane, and the like; boric acid, phenylboric acid, and the like; aromatic sulfonates such as tetrabutylphosphonium dodecylbenzenesulfonate, and the like; organic halides such as stearic acid chloride, benzoyl chloride, and p-toluenesulfonic acid chloride, and the like; alkyl sulfates such as dimethyl sulfate, and the like; and organic halides such as benzyl chloride, and the like.

[0144] The acidic substance may be used in an amount of 0.1 to 5 parts by mol, preferably 0.1 to 1 part by mol, based on 100 parts by mol of the catalyst.

[0145] 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 the amount is more than 5 parts by mole, the heat resistance of the resin will decrease and the molded product will tend to be discolored, which is undesirable.

[0146] After the catalyst is deactivated, a volatilization step may be further carried out to remove low boiling point compounds in 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 device equipped with stirring blades with excellent surface renewal ability, such as paddle blades, lattice blades, and spectacle blades, or a thin film evaporator is preferably used.

[0147] The resin of the present invention preferably has a minimum content of foreign matter, and filtration of the molten raw material and the catalyst solution are preferably carried out.

[0148] The mesh of the filter used for the filtration is preferably 5 μm or less, more preferably 1 μm or less. The generated 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 in a low dust environment, preferably class 6 or less, more preferably class 5 or less.

[0149] In addition, examples of methods for molding molded articles containing the resin include, in addition to injection molding, compression molding, casting, roll processing, extrusion molding, and stretching, but are not limited to these.

[0150] Another embodiment of the present invention provides a resin composition comprising a resin according to the above-described embodiment.

[0151] In one embodiment of the present invention, the resin may be included in an amount of 1 part by weight to 80 parts by weight based on 100 parts by weight of the resin composition.

[0152] In one embodiment of the present invention, the resin composition may further include a solvent, which may be, for example, dimethylacetamide or 1,2-dichlorobenzene.

[0153] The solvent may be included in an amount of 20 parts by weight to 99 parts by weight based on 100 parts by weight of the resin composition.

[0154] The resin composition may further include an additional monomer in addition to the compound represented by the chemical formula 1a. The additional monomer is not particularly limited, and a monomer generally applied in the technical field related to polyester or polycarbonate may be appropriately adopted within a range that does not change the main physical properties of the resin composition. The additional monomer may be used in an amount of 1 to 50 parts by mole relative to 100 parts by mole of the total monomers constituting the resin containing the unit represented by the chemical formula 1.

[0155] In addition to the resin containing the unit represented by Chemical Formula 1, the resin composition may further contain, as necessary, additives such as one or more selected from the group consisting of antioxidants, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, fluorescent brighteners, ultraviolet absorbers, pigments, and dyes.

[0156] The additive may be included in an amount of 1 part by weight to 99 parts by weight based on 100 parts by weight of the resin composition.

[0157] 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 any agent applicable in the relevant technical field may be appropriately adopted.

[0158] Another embodiment of the present invention provides a molded article comprising a resin composition according to the above-described embodiment.

[0159] In one embodiment of the present invention, the molded article may be produced from the resin composition or a cured product thereof.

[0160] An example of a method for producing the molded product may include a step of thoroughly mixing the resin including the unit represented by Chemical Formula 1 and the additive in a mixer, extruding the mixture in an extruder to prepare pellets, drying the pellets, and then injecting the pellets in an injection molding machine.

[0161] In one embodiment of the present invention, the molded article is an optical lens.

[0162] The optical lens is manufactured using the resin, has a high refractive index and high transparency, and is preferably applicable to cameras.

[0163] In the industry, camera modules use three or more lenses to achieve desired performance. Currently, the primary requirement for optical lenses, especially for mobile camera modules, is to reduce the thickness by molding the lenses or using high refractive index resins, and the present invention focuses on resins with high refractive index that can meet such requirements. Lens combinations that take into account the ideal lens thickness and the degree of difficulty of molding the molded product make it easy to use materials with high refractive index. EXAMPLES

[0164] The present invention will now be illustrated in more detail by way of examples. Examples and Comparative Examples

[0165] 1. Synthesis of Monomer 1 [ka]

[0166] 1) Synthesis of compound 1-C Compound 1-A 25.9g (100mmol, 1.0eq) and compound 1-B 47.1g (500mmol, 5.0eq) were dissolved in 1,4-dioxane 80g and stirred in a 60°C water bath for 30 minutes. While maintaining the temperature, H2SO4 29.4g (300mmol, 3.0eq) was added dropwise for 30 minutes. 3-Mercaptopropionic acid (HSCH2CH2CO2H) 0.53g (5mmol, 0.05eq) was added. After stirring for 6 hours, the mixture was washed several times with toluene / 10% NaOH to neutralize it, and the organic layer was separated and precipitated in n-hexane to obtain compound 1-C as an orange solid.

[0167] 2) Synthesis of compound 1-E Compound 1-C 42.9g (100mmol, 1.0eq) and compound 1-D 18.9g (110mmol, 1.1eq) were dissolved in 200g of tetrahydrofuran (THF) and stirred in an oil bath at 80℃ for 30 minutes. K2CO3 17.9g (130mmol, 1.30eq) was dissolved in 200mL of water, and the solution was added dropwise for 10 minutes while maintaining the internal temperature of the solution above 50℃. Pd(t-Bu3P)2 catalyst 1.53g (3mmol, 0.03eq) was added at an internal temperature of 60℃. After stirring for 1 hour, the organic layer was separated by washing with ethyl acetate (EA) / H2O, and the solvent was concentrated in vacuum. The mixture was purified by column chromatography with n-hexane (n-Hex) and dichloromethane (DCM), and then precipitated with n-hexane (n-Hex) to obtain compound 1-E as a solid.

[0168] 3) Synthesis of Monomer 1 Compound 1-E 47.7g (100mmol, 1.0eq), Compound 1-F 19.39g (220mmol, 2.2eq), and K2CO3 2.77g (20mmol, 0.20eq) were dissolved in dimethylacetamide (DMAc) 240g and stirred in an oil bath at 120℃ for 2 hours. After cooling, water was added and the solid was precipitated and filtered. The obtained solid was purified by column chromatography using ethyl acetate (EA) and dichloromethane (DCM), and then precipitated with n-hexane (n-Hex), and 34g of Monomer 1 was obtained as a white solid. MS: [M+H] + =564

[0169] 2. Synthesis of Monomer 2 [ka] Monomer 2 was obtained in the same manner as in the synthesis of Monomer 1, except that compound 2-A was used instead of compound 1-B. MS: [M+H] + =664

[0170] 3. Synthesis of Monomer 3 [ka] Monomer 3 was obtained in the same manner as in the synthesis of Monomer 1, except that compound 3-A was used instead of compound 1-D. MS: [M+H] + =564

[0171] 4. Synthesis of Monomer 4 [ka] Monomer 4 was obtained in the same manner as in the synthesis of Monomer 1, except that compound 4-A was used instead of compound 1-D. MS: [M+H] + =679

[0172] 5. Synthesis of Monomer 5 [ka] Monomer 5 was obtained in the same manner as in the synthesis of Monomer 1, except that compound 5-A was used instead of compound 1-D. MS: [M+H] + =604

[0173] 6. Synthesis of Monomer 6 [ka] Monomer 6 was obtained in the same manner as in the synthesis of Monomer 1, except that compound 6-A was used instead of compound 1-D. MS: [M+H] + =640

[0174] 7. Synthesis of Monomer 7 [ka] Monomer 7 was obtained in the same manner as in the synthesis of Monomer 1, except that compound 7-A was used instead of compound 1-B. MS: [M+H] + =716

[0175] 8. Synthesis of Monomer 8 [ka] Monomer 8 was obtained in the same manner as in the synthesis of Monomer 1, except that compound 8-A was used instead of compound 1-B. MS: [M+H] + =664

[0176] 9. Synthesis of Monomer 9 [ka] Monomer 9 was obtained in the same manner as in the synthesis of Monomer 1, except that compound 9-A was used instead of compound 1-B. MS: [M+H] + =664

[0177] Synthesis of Comparative Example C1 [ka] Comparative Example C1 was obtained in the same manner as in the synthesis of Monomer 1, except that 9-Fluorenone was used instead of Compound 1-A and the reaction with 1-D was omitted. C1 can be obtained from TCI or Sigma-Aldrich. MS: [M+H] + =438

[0178] Production of resin (Polymer) 1 [ka] Monomer 1 (1.77 mmol, 1.0 eq) and terephthaloyl chloride (0.36 g, 1.77 mmol, 1.0 eq) were dissolved in diphenyl ether (DPE) (4.1 g) and reacted in an oil bath at 180°C for 6 hours. As the reaction proceeded, chloric acid (HCl) gas was generated, and in order to remove it, a nitrogen replacement and chloric acid gas collection device were installed. After the reaction, the mixture was cooled to 100°C, and 15 g of dimethylacetamide (DMAc) was added, and the mixture was precipitated with methanol to produce polymer 1.

[0179] Preparation of resins 2 and 4-9 Resins 2 and 4 to 9 were produced in the same manner as Resin 1, except that Monomer 2 and Monomer 4 to 9 were used instead of Monomer 1.

[0180] Preparation of Comparative Resin P1 Comparative resin P1 was prepared in the same manner as resin 1, except that monomer C1 was used instead of monomer 1.

[0181] Preparation of Comparative Resin P2 Comparative resin P2 was prepared in the same manner as resin 1, except that monomer 1 was replaced with the monomer of comparative example C2. [ka]

[0182] Preparation of Comparative Resin P3 Comparative resin P3 was prepared in the same manner as resin 1, except that monomer 1 was replaced with the monomer of comparative example C3. [ka]

[0183] Preparation of Comparative Resin P4 Comparative resin P4 was prepared in the same manner as resin 1, except that monomer 1 was replaced with the monomer of comparative example C4. [ka]

[0184] Manufacture of polymer 10 [ka] 55.3g (98mmol) of Monomer 1 and 21.4g (100mmol) of diphenylcarbonate were melted and reacted at 250℃ for 5 hours. As the reaction proceeded, phenol was generated as a by-product, and the pressure was reduced to a maximum of 1Torr 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 taken out, thereby obtaining polycarbonate resin (Polymer) 10.

[0185] Production of resins 11 to 18 Resins 11 to 18 were produced in the same manner as Resin 10, except that Monomers 2 to 9 were used instead of Monomer 1.

[0186] Preparation of Comparative Resin P5 Comparative resin P5 was prepared in the same manner as resin 10, except that monomer 1 was replaced with the monomer of comparative example C1.

[0187] Preparation of Comparative Resin P6 Comparative resin P6 was prepared in the same manner as resin 10, except that monomer 1 was replaced with the monomer of comparative example C2. [ka]

[0188] Preparation of Comparative Resin P7 Comparative Resin P7 was prepared in the same manner as Resin 10, except that Monomer 1 was replaced with the monomer of Comparative Example C3. [ka]

[0189] Preparation of Comparative Resin P8 Comparative Resin P8 was prepared in the same manner as Resin 10, except that Monomer 1 was replaced with the monomer of Comparative Example C4. [ka]

[0190] Experimental Example The molecular weight and molecular weight distribution of the polymerized resin sample were confirmed through gel permeation chromatography (GPC), and a thermogram was obtained using a differential scanning calorimeter (DSC) to investigate the thermal properties. After film formation, an ellipsometer was used to measure the refractive index and Abbe number, and the results were obtained according to the wavelength of light.

[0191] The molecular weight by gel permeation chromatography (GPC) was measured by dissolving the resin sample in tetrahydrofuran (THF, stabilized with BHT (butylated hydroxytoluene)) as a solvent at a concentration of 1.0 mg / 1 ml, filtering the solution through a syringe filter, injecting the solution, and measuring the results at 40°C, which are shown in Table 1 below. A Waters RI detector was used, and two Agilent PLgel MIXED-B columns were used.

[0192] The glass transition temperature (Tg) of the resin was measured using a differential scanning calorimeter (DSC). 5.5mg to 8.5mg of resin sample was heated to 270℃ under N2 flow, cooled, and then heated at a heating rate of 10℃ / min during the second heating, and the glass transition temperature (Tg) was obtained from the graph obtained and is shown in Table 1 below.

[0193] To measure the refractive index and Abbe number of the resin, the polymerized resin powder sample was dissolved in dimethylacetamide solvent at 10% by weight based on the total weight of the polymer solution to prepare a polymer solution, which was then spin-coated onto a silicon wafer at a rotation speed of 220 rpm to form a film with a thickness of 20 μm. Then, using an ellipsometer at 20° C., the results according to the wavelength of light were obtained and are listed in Table 1 below. Specifically, the refractive index was measured at a wavelength of 589 nm, and the Abbe number was measured at 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 )

[0194] [Table 1]

[0195] In Table 1, 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.

[0196] According to Table 1, the resin according to the embodiment of the present invention includes a unit represented by Chemical Formula 1, and in particular, when the benzene ring of the fluorene core structure is substituted with an electron-rich R1 substituent 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.

[0197] In contrast, the resins according to Comparative Examples 1, 3, 5, and 7 do not have an electron-rich substituent on the benzene ring of the fluorene core structure, and therefore it can be confirmed that they have a refractive index much lower than that of the examples of the present invention.

[0198] In addition, it can be seen that the resins according to Comparative Examples 2 and 6 have a much lower refractive index than the examples of the present invention because they contain alkyl groups, which are electron-poor substituents, on both sides of the benzene ring of the fluorene core.

[0199] It can be seen that the resins of Comparative Examples 4 and 10 are substituted with an alkynyl group (triple bond) substituted with an aryl group at the R1 position of the fluorene core, and thus the electron density is higher on the R1 side that is not the fluorene core, and the refractive index is lower than that of the Examples.

[0200] Currently, the primary requirement for optical lenses, particularly for mobile camera modules, is to reduce the thickness by molding the lens or by using a high refractive index resin. It has been confirmed that the resin according to one embodiment of the present specification, in Examples 1 to 17, has a refractive index that satisfies the above requirement, compared to Comparative Examples 1 and 8, and is therefore a resin that is highly usable as an optical material.

Claims

1. A resin including a unit represented by the following chemical formula 1: 【Chemistry 1】 In the above Chemical Formula 1, R1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R2 is hydrogen; r1 is an integer of 1 to 4, and when r1 is 2 or more, the two or more R1's are the same or different from each other; r2 is 4; L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group; L is a direct bond; or -CO-L'-; L' is a substituted or unsubstituted arylene group; X1 to X4 are the same or different and each independently represents O; or S; Z1 and Z2 are the same or different and each independently represents a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; a and b are the same or different and each independently represents an integer from 1 to 10; when a and b are each 2 or more, the structures in each bracket are the same or different; * indicates a site connected to the main chain of the resin. The term "substituted or unsubstituted" includes a halogen group; a nitro group (NO ２ ), a nitrile group (CN); an alkyl group; a cycloalkyl group; an aryl group; an aryloxy group; an arylthio group; an alkylthio group; and a heteroaryl group, or is substituted with a substituent in which two or more of the substituents exemplified above are linked, or does not have any substituents.

2. The resin according to claim 1, wherein the "substituted or unsubstituted" of R1 is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group; a heteroaryl group; an aryloxy group; an arylthio group; and an alkylthio group.

3. The resin according to claim 1 , wherein L1 and L2 are the same or different and each independently represents an arylene group substituted or unsubstituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

4. 2. The resin of claim 1, wherein Z1 and Z2 are the same or different and each independently represents a substituted or unsubstituted ethylene group.

5. The resin according to claim 1, wherein X1 to X4 are O.

6. The resin of claim 1, wherein the weight average molecular weight is from 10,000 g / mol to 200,000 g / mol.

7. The resin of claim 1, having a glass transition temperature (Tg) of 160°C to 210°C.

8. The resin according to claim 1, having a refractive index of 1.665 to 1.75 measured at a wavelength of 589 nm.

9. A compound represented by the following chemical formula 1a: 【Chemistry 2】 In the above formula 1a, R1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R2 is hydrogen; r1 is an integer of 1 to 4, and when r1 is 2 or more, the two or more R1's are the same or different from each other; r2 is 4; L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group; X1 to X4 are the same or different and each independently represents O; or S; Z1 and Z2 are the same or different and each independently represents a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; a and b are the same or different and each independently represents an integer from 1 to 10; when a and b are each 2 or more, the structures in each bracket are the same or different; The term "substituted or unsubstituted" includes a halogen group; a nitro group (NO ２ ), a nitrile group (CN); an alkyl group; a cycloalkyl group; an aryl group; an aryloxy group; an arylthio group; an alkylthio group; and a heteroaryl group, or is substituted with a substituent in which two or more of the substituents exemplified above are linked, or does not have any substituents.

10. The compound according to claim 9, wherein the compound represented by formula 1a is any one selected from the following compounds: 【Chemistry 3-1】 【Chemistry 3-2】 【Chemistry 3-3】

11. A compound represented by the following formula 1a: A method for producing the resin according to any one of claims 1 to 8, comprising the step of polymerizing a composition for producing a resin comprising a polyester precursor or a polycarbonate precursor: 【Chemistry 4】 In Chemical Formula 1a, R1, R2, r1, r2, L1, L2, X1 to X4, Z1, Z2, a, and b are the same as those in Chemical Formula 1.

12. The method for producing a resin according to claim 11, 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 5】 In the above chemical formulas A and B, R, R, R, and R 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, a2, b1, and b2 are each 0 or 1.

13. A resin composition comprising the resin according to any one of claims 1 to 8.

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

15. 15. The molded article of claim 14 which is an optical lens.

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