Resin and preparation method thereof

Abstract

The present application relates to a resin including a unit represented by Chemical Formula 1, a method for preparing the same, a resin composition including the same, and a molded article including the resin composition.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2021-0063567, filed on May 17, 2021, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a resin and a method for preparing the same, and more particularly to a resin having a high refractive index and high transparency and a method for preparing the same. Background Art

[0003] The higher the refractive index of an optical material, the thinner the optical lens needs to be to achieve the same level of correction. Therefore, as the refractive index of an optical material increases, thinner and lighter lenses can be made, thereby making various devices using lenses smaller.

[0004] Generally, when the refractive index of an optical material is increased, there is a problem that the Abbe number becomes lower, and in order to be used as an optical material, a certain level or higher of transparency is required. Summary of the Invention

[0005] Technical issues

[0006] An exemplary embodiment of the present invention is directed to providing a resin having a novel structure and a method for preparing the same.

[0007] Another exemplary embodiment of the present invention is directed to providing a composition including a resin having a novel structure and a molded article prepared from the composition.

[0008] Technical Solution

[0009] An exemplary embodiment of the present invention provides a resin including a unit represented by the following Chemical Formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In Chemical Formula 1,

[0013] R1 and R2 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted alkyl; or substituted or unsubstituted cycloalkyl,

[0014] r1 is an integer from 0 to 4, and when r1 is 2 or greater, two or more R1s are the same as or different from each other,

[0015] r2 is an integer from 0 to 4, and when r2 is 2 or greater, two or more R2 are the same as or different from each other,

[0016] L1 and L2 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0017] L is a direct bond or -CO-L'-,

[0018] L' is a substituted or unsubstituted arylene group,

[0019] X1 to X4 are the same as or different from each other and are each independently O or S,

[0020] Z1 and Z2 are the same as or different from each other and are each independently a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group,

[0021] a and b are the same as or different from each other and are each independently an integer from 1 to 10, and when a and b are each 2 or greater, the structures in each bracket are the same as or different from each other, and

[0022] *Indicates the portion connected to the main chain of the resin.

[0023] An exemplary embodiment of the present invention provides a compound represented by the following Chemical Formula 1a.

[0024] [Chemical Formula 1a]

[0025]

[0026] In Chemical Formula 1a,

[0027] R1 and R2 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted alkyl; or substituted or unsubstituted cycloalkyl,

[0028] r1 is an integer from 0 to 4, and when r1 is 2 or greater, two or more R1s are the same as or different from each other,

[0029] r2 is an integer from 0 to 4, and when r2 is 2 or greater, two or more R2 are the same as or different from each other,

[0030] L1 and L2 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0031] X1 to X4 are the same as or different from each other and are each independently O or S,

[0032] Z1 and Z2 are the same as or different from each other and are each independently a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group, and

[0033] a and b are the same as or different from each other and are each independently an integer of 1 to 10, and when a and b are each 2 or greater, the structures in each bracket are the same as or different from each other.

[0034] An exemplary embodiment of the present invention provides a method for preparing the resin, the method including polymerizing a composition for preparing the resin, the composition for preparing the resin including a compound represented by the following Chemical Formula 1a; and a polyester precursor or a polycarbonate precursor.

[0035] [Chemical Formula 1a]

[0036]

[0037] In Chemical Formula 1a, definitions of R1, R2, r1, r2, L1, L2, X1 to X4, Z1, Z2, a, and b are the same as those in Chemical Formula 1.

[0038] Another exemplary embodiment of the present invention provides a resin composition including the resin according to the above exemplary embodiment.

[0039] Yet another exemplary embodiment of the present invention provides a molded article including the resin composition according to the above exemplary embodiment.

[0040] Beneficial effects

[0041] The resin according to the exemplary embodiment of the present invention has a high refractive index and high transparency.

[0042] By using the resin according to the exemplary embodiment of the present invention, an excellent optical lens may be obtained. DETAILED DESCRIPTION

[0043] Hereinafter, specific exemplary embodiments will be described in more detail.

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

[0045] In the present invention, 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; and a heteroaryl group, substituted with a substituent in which two or more substituents among the exemplified substituents are linked, or no substituents.

[0046] In this specification, * means a bonding portion with another structure.

[0047] 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, cyclohexylene, or cycloheptylene group as a monocyclic cycloalkylene group, and may be a divalent adamantanediyl group, a divalent norbornanediyl group, or the like as a polycyclic cycloalkylene group. However, the cycloalkylene group is not limited thereto. In addition, the cycloalkylene group may be unsubstituted or substituted one or more times with an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a halogen group.

[0048] In this specification, the description of the cycloalkylene group can be applied, except that the cycloalkyl group is a monovalent group instead of a divalent group.

[0049] In the present specification, the alkylene group may be a straight chain or branched alkylene group which is a divalent group derived from an aliphatic hydrocarbon having 1 to 30, 1 to 20, 1 to 10, or 1 to 5 carbon atoms. Specific examples of the alkylene group include methylene, ethylene, propylene, n-propylene, isopropylene, butylene, n-butylene, isobutylene, tert-butylene, sec-butylene, 1-methyl-butylene, 1-ethyl-butylene, pentylene, n-pentylene, isopentylene, neopentylene, tert-pentylene, hexylene, n-hexylene, 1-methylpentylene, 2-methylpentylene, 4-methyl-2-pentylene, 3,3-dimethylpentylene, The invention also includes but is not limited to butylene, 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, 5-methylhexylene and the like.

[0050] In this specification, the description of the alkylene group may be applied except that the alkyl group is a monovalent group instead of a divalent group.

[0051] In the present specification, unless otherwise limited, an alkyl group includes a linear alkyl group, a branched alkyl group and a cyclic alkyl group.

[0052] In the present specification, the arylene group may be a monocyclic or polycyclic arylene group, and the number of carbon atoms thereof is not particularly limited, but is preferably 6 to 30, and may be 6 to 20. Specific examples of the monocyclic arylene group include phenylene, biphenylene, terphenylene, and the like, but are not limited thereto. When the arylene group is a polycyclic arylene group, the number of carbon atoms thereof is not particularly limited, but is preferably 10 to 30, and may be 10 to 20. Specific examples of the polycyclic arylene group include naphthylene, divalent anthracenyl, divalent phenanthrenyl, divalent triphenylene, divalent pyrenyl, divalent perylene, divalent pyrenyl ... group, divalent fluorenyl group, etc., but are not limited thereto.

[0053] In this specification, the description of the arylene group may be applied, except that the aryl group is a monovalent group instead of a divalent group.

[0054] In the present specification, the heteroaryl group contains one or more atoms other than carbon (i.e., one or more heteroatoms), and specifically, the heteroatoms include one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms of 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 thienyl, furyl, dibenzofuranyl, dibenzothienyl, benzothienyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, The invention also includes, but is not limited to, oxadiazole, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, and carbazolyl.

[0055] In this specification, the description of the heteroaryl group can be applied, except that the heteroarylene group is a divalent group instead of a monovalent group.

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

[0057] In the present specification, the divalent aliphatic hydrocarbon group means the above-mentioned alkylene group, cycloalkylene group, and the like.

[0058] In the present specification, the description of the above-mentioned cycloalkylene group may be applied to an aliphatic ring, and the description of the arylene group or heteroarylene group may be applied to an aromatic ring.

[0059] An exemplary embodiment of the present invention provides a resin including a unit represented by the following Chemical Formula 1.

[0060] [Chemical Formula 1]

[0061]

[0062] In Chemical Formula 1,

[0063] R1 and R2 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted alkyl; or substituted or unsubstituted cycloalkyl,

[0064] r1 is an integer from 0 to 4, and when r1 is 2 or greater, two or more R1s are the same as or different from each other,

[0065] r2 is an integer from 0 to 4, and when r2 is 2 or greater, two or more R2 are the same as or different from each other,

[0066] L1 and L2 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0067] L is a direct bond or -CO-L'-,

[0068] L' is a substituted or unsubstituted arylene group,

[0069] X1 to X4 are the same as or different from each other and are each independently O or S,

[0070] Z1 and Z2 are the same as or different from each other and are each independently a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group,

[0071] a and b are the same as or different from each other and are each independently an integer from 1 to 10, and when a and b are each 2 or greater, the structures in each bracket are the same as or different from each other, and

[0072] *Indicates the portion connected to the main chain of the resin.

[0073] From the relationship between molecular structure and refractive index (which is known from the Lorentz-Lorenz equation), it can be seen that the refractive index of a material composed of molecules is increased by increasing the electron density of the molecules and reducing the molecular volume.

[0074] The resin including the unit represented by Chemical Formula 1 can improve fillability by including spirobifluorene as the core structure of Chemical Formula 1, and L1 and L2 may be a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group to increase the electron density of spirobifluorene as the core structure of Chemical Formula 1, thereby increasing the refractive index of the resin.

[0075] When R1 and R2 are further substituted with an aromatic substituent such as an aryl group or a heteroaryl group in addition to L1 and L2, a thermosetting resin can be prepared instead of a thermoplastic resin which is not preferred as the resin to be provided in the present invention.

[0076] In an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.

[0077] In an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.

[0078] In an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms.

[0079] In an exemplary embodiment of the present invention, R1 and R2 are hydrogen.

[0080] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

[0081] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 4 to 20 carbon atoms.

[0082] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

[0083] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 12 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 10 carbon atoms.

[0084] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted divalent dibenzofuranyl group; a substituted or unsubstituted divalent fluorenyl group; or a substituted or unsubstituted divalent thienyl group.

[0085] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other and are each independently a phenylene group; a biphenylene group; a naphthylene group; a divalent dibenzofuranyl group; a divalent dimethylfluorenyl group; or a divalent thienyl group.

[0086] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a phenylene group; a naphthylene group; or a divalent dibenzofuranyl group.

[0087] In an exemplary embodiment of the present invention, L is a direct bond.

[0088] In an exemplary embodiment of the present invention, L is -CO-L'-.

[0089] In an exemplary embodiment of the present invention, L' is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0090] In an exemplary embodiment of the present invention, L' is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0091] In an exemplary embodiment of the present invention, L' is a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0092] In an exemplary embodiment of the present invention, L' is a substituted or unsubstituted phenylene group.

[0093] In an exemplary embodiment of the present invention, L' is a phenylene group.

[0094] In an exemplary embodiment of the present invention, X1 to X4 are O.

[0095] In an exemplary embodiment of the present invention, X1 to X4 are S.

[0096] In an exemplary embodiment of the present invention, Z1 and Z2 are the same as or different from each other, and are each independently 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.

[0097] In an exemplary embodiment of the present invention, Z1 and Z2 are the same as or different from each other, and are each independently 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.

[0098] In an exemplary embodiment of the present invention, Z1 and Z2 are the same as or different from each other, and are each independently 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.

[0099] In an exemplary embodiment of the present invention, Z1 and Z2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

[0100] In an exemplary embodiment of the present invention, Z1 and Z2 are the same as or different from each other, and are each independently 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.

[0101] In an exemplary embodiment of the present invention, Z1 and Z2 are the same as or different from each other, and are each independently a methylene group; an ethylene group; a propylene group; or a hexylene group.

[0102] In an exemplary embodiment of the present invention, Z1 and Z2 are ethylene groups.

[0103] In the present invention, Chemical Formula 1 may be represented by the following Chemical Formula 1-1.

[0104] [Chemical Formula 1-1]

[0105]

[0106] In Chemical Formula 1-1, the definitions of each substituent are the same as those of each substituent in Chemical Formula 1.

[0107] According to an exemplary embodiment of the present invention, the resin may have -OH, -SH, -CO2CH3, or -OC6H5 as a terminal group.

[0108] In an exemplary 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. More preferably, the weight average molecular weight is 25,000 g / mol to 40,000 g / mol or 25,500 g / mol to 27,100 g / mol.

[0109] When the resin satisfies the above weight average molecular weight range, the resin can have optimal fluidity and processability.

[0110] In the present invention, the weight average molecular weight (Mw) of resin and the oligomer for its preparation can be measured by gel permeation chromatography (GPC) using polystyrene (PS) standards using Agilent 1200 series. Specifically, the weight average molecular weight can be measured using an Agilent 1200 series device utilizing a Polymer Laboratories PLgel MIX-B 300 mm length column, and in this case, the measuring temperature is 40 ° C, the solvent used is tetrahydrofuran (THF), and the flow rate is 1 mL / minute. The sample of resin or oligomer is each prepared at a concentration of 10 mg / 10 mL, then fed in an amount of 10 μ L, and the Mw value is derived using a calibration curve formed using polystyrene standards. In this case, nine types of polystyrene standard products having molecular weights (g / mol) of 2,000 / 10,000 / 30,000 / 70,000 / 200,000 / 700,000 / 2,000,000 / 4,000,000 / 10,000,000 were used.

[0111] In an exemplary embodiment of the present invention, the glass transition temperature (Tg) of the resin may be 200° C. to 250° C. The glass transition temperature may preferably be 205° C. to 240° C., more preferably 208° C. to 236° C. When the resin satisfies the above glass transition temperature range, when the resin composition is prepared by mixing with a resin having excellent heat resistance and injectability and having a glass transition temperature different from the above range, the glass transition temperature can be easily adjusted so that the desired physical properties in the present invention can be satisfied.

[0112] 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 a resin sample to 270°C under a nitrogen atmosphere and then scanning the resin sample while heating the resin sample at a heating rate of 10°C / min during the second heating period after cooling.

[0113] In an exemplary embodiment of the present invention, the refractive index of the resin measured at a wavelength of 589 nm is 1.68 to 1.75. The refractive index may preferably be 1.689 to 1.721. When the resin satisfies the above refractive index, when the resin is applied to a molded article such as an optical lens, a thin and light optical lens can be manufactured.

[0114] In an exemplary 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 20. Preferably, the Abbe number may be 12 to 16. More preferably, the Abbe number may be 13.1 to 14.3. When the resin satisfies the above Abbe number range, there is the following effect: while maintaining a high refractive index, when the resin is applied to a molded product such as an optical lens, the dispersion is reduced and the clarity is increased. The Abbe number can be specifically measured by measuring the refractive index (n) at wavelengths of D (589 nm), F (486 nm) and C (656 nm) at 20°C, respectively. D , n F and n C ) is obtained by the following equation.

[0115] Abbe number = (n D -1) / (n F -n C )

[0116] The refractive index and the Abbe number can be measured by applying a solution prepared by dissolving the resin in a solvent to a film prepared by spin coating on a silicon wafer, and for the applied film, the obtained value according to the wavelength of light can be obtained by using an ellipsometer at 20 ° C. The solution can be applied by spin coating at a rotation speed of 150 rpm to 300 rpm, and the thickness of the applied film can be 5 μm to 20 μm. The silicon wafer is not particularly limited, and any silicon wafer that can measure the refractive index and Abbe number of the resin composition according to the present invention can be appropriately adopted. The solvent can be dimethylacetamide or 1,2-dichlorobenzene, and the solution can be prepared by dissolving the resin sample in an amount of 10 weight % based on the total weight of the solution.

[0117] An exemplary embodiment of the present invention provides a compound represented by the following Chemical Formula 1a.

[0118] [Chemical Formula 1a]

[0119]

[0120] In Chemical Formula 1a,

[0121] R1 and R2 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted alkyl; or substituted or unsubstituted cycloalkyl,

[0122] r1 is an integer from 0 to 4, and when r1 is 2 or greater, two or more R1s are the same as or different from each other,

[0123] r2 is an integer from 0 to 4, and when r2 is 2 or greater, two or more R2 are the same as or different from each other,

[0124] L1 and L2 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0125] X1 to X4 are the same as or different from each other and are each independently O or S,

[0126] Z1 and Z2 are the same as or different from each other and are each independently a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group, and

[0127] a and b are the same as or different from each other and are each independently an integer of 1 to 10, and when a and b are each 2 or greater, the structures in each bracket are the same as or different from each other.

[0128] An exemplary embodiment of the present invention provides a method for preparing the resin, the method including polymerizing a composition for preparing the resin, the composition for preparing the resin including a compound represented by the following Chemical Formula 1a; and a polyester precursor or a polycarbonate precursor.

[0129] [Chemical Formula 1a]

[0130]

[0131] In Chemical Formula 1a, definitions of R1, R2, r1, r2, L1, L2, X1 to X4, Z1, Z2, a, and b are the same as those in Chemical Formula 1.

[0132] An exemplary embodiment of the present invention preferably provides a method for preparing a resin, the method including polymerizing a composition for preparing a resin, the composition for preparing a resin including a compound represented by Chemical Formula 1a and a polyester precursor.

[0133] An exemplary embodiment of the present invention provides a composition for preparing a resin, the composition for preparing a resin including a compound represented by Chemical Formula 1a; and a polyester precursor or a polycarbonate precursor.

[0134] The composition used to prepare the resin may also contain a solvent.

[0135] The solvent may be, for example, diphenyl ether, dimethylacetamide, or methanol, but is not limited thereto, and any solvent used in the art may be appropriately employed.

[0136] The solvent may be included in an amount of 5 parts by weight to 60 parts by weight relative to 100 parts by weight of the composition for preparing the resin.

[0137] The solvent may be included in an amount of preferably 5 to 50 parts by weight, 10 to 40 parts by weight, or 10 to 30 parts by weight, relative to 100 parts by weight of the composition for preparing the resin.

[0138] In an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1a may be any one of the following compounds, but is not limited thereto.

[0139]

[0140] In an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1a may be included in an amount of 1 to 99 parts by weight relative to 100 parts by weight of the composition for preparing a resin.

[0141] The compound represented by Chemical Formula 1a may be included in an amount of preferably 1 to 60 parts by weight, 1 to 50 parts by weight, 1 to 40 parts by weight, 1 to 30 parts by weight, or 1 to 20 parts by weight relative to 100 parts by weight of the composition for preparing the resin.

[0142] In an exemplary embodiment of the present invention, the polyester precursor or the polycarbonate precursor may be included in an amount of 1 part by weight to 20 parts by weight relative to 100 parts by weight of the composition for preparing the resin.

[0143] The polyester precursor or the polycarbonate precursor may be included 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, relative to 100 parts by weight of the composition for preparing the resin.

[0144] The compound represented by Chemical Formula 1a can be prepared by the following reaction scheme.

[0145] [Reaction scheme]

[0146]

[0147] In the reaction scheme, the definitions of the substituents are the same as those in the above Chemical Formula 1a.

[0148] Although the reaction scheme illustrates the process of synthesizing compounds in which specific substituents are bonded at specific positions, units corresponding to the scope of Chemical Formula 1a can be synthesized by synthetic methods known in the art using starting materials, intermediates, etc. known in the art.

[0149] According to an exemplary 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.

[0150] [Chemical Formula A]

[0151]

[0152] [Chemical Formula B]

[0153]

[0154] In chemical formulas A and B,

[0155] Ra1, Ra2, Rb1 and Rb2 are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

[0156] L' is a substituted or unsubstituted arylene group, and

[0157] a1, a2, b1, and b2 are each 0 or 1.

[0158] In an exemplary embodiment of the present invention, Ra1, Ra2, Rb1 and Rb2 are the same as or different from each other, and are each independently 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.

[0159] In an exemplary embodiment of the present invention, Ra1, Ra2, Rb1 and Rb2 are the same as or different from each other, and are each independently 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.

[0160] In an exemplary embodiment of the present invention, Ra1, Ra2, Rb1 and Rb2 are the same as or different from each other, and are each independently 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.

[0161] In an exemplary embodiment of the present invention, Ra1, Ra2, Rb1, and Rb2 are the same as or different from each other, and are each independently a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted phenyl group.

[0162] In an exemplary embodiment of the present invention, Ra1, Ra2, Rb1, and Rb2 are the same as or different from each other, and are each independently a methyl group; an ethyl group substituted with a hydroxyl group; or a phenyl group.

[0163] In an exemplary embodiment of the present invention, Ra1 and Ra2 are methyl groups.

[0164] In an exemplary embodiment of the present invention, Ra1 and Ra2 are ethyl groups substituted with hydroxyl groups.

[0165] In an exemplary embodiment of the present invention, Rb1 and Rb2 are phenyl groups.

[0166] In an exemplary embodiment of the present invention, L' is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0167] In an exemplary embodiment of the present invention, L' is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0168] In an exemplary embodiment of the present invention, L' is a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0169] In an exemplary embodiment of the present invention, L' is a substituted or unsubstituted phenylene group.

[0170] In an exemplary embodiment of the present invention, L' is a phenylene group.

[0171] In an exemplary embodiment of the present invention, a1 is 0.

[0172] In an exemplary embodiment of the present invention, a2 is 0.

[0173] In an exemplary embodiment of the present invention, b1 is 0.

[0174] In an exemplary embodiment of the present invention, b2 is 0.

[0175] In an exemplary embodiment of the present invention, a1 is 1.

[0176] In an exemplary embodiment of the present invention, a2 is 1.

[0177] In an exemplary embodiment of the present invention, b1 is 1.

[0178] In an exemplary embodiment of the present invention, b2 is 1.

[0179] If necessary, a polycarbonate precursor is used to link another comonomer, and other specific examples of the polycarbonate precursor that can be used in addition to the compound represented by Chemical Formula B include phosgene, triphosgene, diphosgene, bromophosgene, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, ditolyl carbonate, bis(chlorophenyl) carbonate, m-tolyl carbonate, dinaphthyl carbonate, bis(diphenyl) carbonate, bishaloformates, and the like, and any one of them or a mixture of two or more thereof may be used.

[0180] The unit of the above Chemical Formula 1 may be formed by polymerizing the compound represented by Chemical Formula 1a with the polyester precursor of Chemical Formula A or the polycarbonate precursor of Chemical Formula B.

[0181] In an exemplary embodiment of the present invention, it is preferred that the resin is polymerized from the compound represented by Chemical Formula 1a and the polyester precursor of Chemical Formula A.

[0182] The compound represented by Chemical Formula 1a may be used in an amount of 1 to 60 mol parts relative to 100 mol parts of the entire monomers constituting the resin including the unit represented by Chemical Formula 1.

[0183] The polyester precursor represented by Chemical Formula A or the polycarbonate precursor represented by Chemical Formula B may be used in an amount of 50 to 150 mol parts relative to 100 mol parts of the entire monomers of the compound represented by Chemical Formula 1a constituting the resin.

[0184] For the polymerization of the resin according to the invention, methods known in the art may be used.

[0185] Preferably, the polymerization is carried out by melt polycondensation.

[0186] In the melt polycondensation method, the composition for preparing the resin is used, and a catalyst may be used as needed. The melt polycondensation can be carried out under heating and further under normal pressure or reduced pressure, while removing by-products through an ester exchange reaction. As the catalyst, materials commonly used in the art can be used.

[0187] Specifically, in the melt polycondensation method, it is preferred to melt the compound represented by Chemical Formula 1a and a polyester precursor or a polycarbonate precursor in a reaction vessel and then perform the reaction while allowing by-product compounds to remain.

[0188] To allow the by-product compounds to remain, the pressure can be controlled by shutting down the reaction apparatus or by reducing or increasing the pressure.

[0189] The reaction time of this process is 20 minutes or more and 600 minutes or less, preferably 40 minutes or more and 450 minutes or less, and more preferably 60 minutes or more and 300 minutes or less.

[0190] In this case, when the by-product compounds are distilled out immediately after production, the resin obtained finally has a small content of high molecular weight materials. However, when the by-product monohydroxy compounds are allowed to stay in the reaction vessel for a certain period of time, the resin obtained finally obtains a large content of high molecular weight materials.

[0191] The melt polycondensation method can be carried out continuously or in batches. The reactor used to carry out the reaction can be a vertical type equipped with an anchor-type impeller, a Maxblend impeller, a spiral ribbon impeller, etc., a horizontal type equipped with paddle blades, a grid blade, a spectacled blade, etc., or an extrusion type equipped with a screw. In addition, considering the viscosity of the polymer, it is desirable to use a reaction device that appropriately combines these reaction devices.

[0192] In the method for preparing the resin used in the present invention, the catalyst may be removed or deactivated to maintain thermal stability and hydrolytic stability after the polymerization reaction is completed. A method of deactivating the catalyst by adding an acidic material known in the art may be preferably performed.

[0193] As the acidic material, it is preferable to use, for example, 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; phosphite 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; phosphate esters such as triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate, dioctyl phosphate and monooctyl phosphate; phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid and dibutylphosphonic acid; phosphonic acid esters such as diethylphenylphosphonate; phosphines such as triphenylphosphine and bis(diphenylphosphino)ethane; boric acids such as boric acid and phenylboric acid; aromatic sulfonates such as tetrabutyl dodecylbenzenesulfonate; salts; organic halides such as stearyl chloride, benzoyl chloride and p-toluenesulfonic acid chloride; alkylsulfuric acids such as dimethylsulfuric acid; organic halides such as benzyl chloride; and the like.

[0194] The acidic material may be used in an amount of 0.1 mol part to 5 mol parts, preferably 0.1 mol part to 1 mol part, relative to 100 mol parts of the catalyst.

[0195] When the amount of the acidic material is less than 0.1 mol parts, the deactivation effect becomes insufficient, which is not preferred. In addition, when the amount exceeds 5 mol parts, the heat resistance of the resin deteriorates and the molded article is easily colored, which is not preferred.

[0196] After the catalyst is deactivated, a process of devolatilizing low-boiling-point compounds in the resin may be further performed at a pressure of 0.1 to 1 mmHg and a temperature of 200° C. to 350° C. In this process, a horizontal type apparatus equipped with a stirring blade having excellent surface recovery ability, such as a paddle blade, a grid blade, and a spectacled blade; or a thin film evaporator is preferably used.

[0197] It is preferred that the content of foreign matter in the resin of the present invention be as small as possible, and filtration of the molten raw material, filtration of the catalyst solution, etc. are preferably performed.

[0198] The mesh size of the filter used for filtration is preferably 5 μm or less, and more preferably 1 μm or less. Furthermore, it is preferred to filter the produced resin using a polymer filter. The mesh size of the polymer filter is preferably 100 μm or less, and more preferably 30 μm or less. Furthermore, the process of obtaining the resin pellets needs to be performed in a low-dust environment, and the environment is preferably Class 6 or less, and more preferably Class 5 or less.

[0199] Furthermore, examples of the method of molding a molded article including a resin include, in addition to injection molding, press molding, roll processing, extrusion molding, stretching, and the like, but are not limited thereto.

[0200] Another exemplary embodiment of the present invention provides a resin composition including the resin according to the above exemplary embodiment.

[0201] In an exemplary 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.

[0202] In an exemplary embodiment of the present invention, the resin composition may further include a solvent, and the solvent may be, for example, dimethylacetamide or 1,2-dichlorobenzene.

[0203] 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.

[0204] The resin composition may further comprise an additional monomer in addition to the compound represented by Chemical Formula 1a. The additional monomer is not particularly limited and may be suitably a monomer commonly used in the field related to polyester or polycarbonate, as long as the main physical properties of the resin composition are not changed. The additional monomer may be used in an amount of 1 to 50 mol parts relative to 100 mol parts of the total monomers constituting the resin comprising the unit represented by Chemical Formula 1.

[0205] If necessary, in addition to the resin containing the unit represented by Chemical Formula 1, the resin composition may further contain one or more additives selected from the group consisting of, for example, antioxidants, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, fluorescent brighteners, UV absorbers, pigments, and dyes.

[0206] 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.

[0207] The types of antioxidants, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, fluorescent brighteners, UV absorbers, pigments or dyes are not particularly limited, and those used in the art may be appropriately employed.

[0208] Yet another exemplary embodiment of the present invention provides a molded article including the resin composition according to the above exemplary embodiment.

[0209] In an exemplary embodiment of the present invention, a molded article may be prepared from the resin composition or a cured product thereof.

[0210] As an example of a method for preparing a molded article, it may include well mixing a resin and an additive using a mixer, preparing the resulting mixture into pellets by extrusion-molding the mixture using an extruder, drying the pellets, and then injection-molding the pellets using an injection molding machine.

[0211] In an exemplary embodiment of the present invention, the molded article is an optical lens.

[0212] The optical lens is manufactured by using a resin having a high refractive index and high transparency, and may be preferably applied to a camera.

[0213] In the case of camera modules in the prior art, desired performance is achieved by using three or more, or four or more, lenses. Currently, in the case of optical lenses, particularly mobile camera modules, the primary requirement is to reduce thickness by molding the lenses or using high-refractive-index resins. The present invention focuses on high-refractive-index resins that can meet such requirements. Considering the ideal lens thickness and the difficulty of molding the molded product, lens combinations promote the use of high-refractive-index materials.

[0214] Embodiments of the invention

[0215] Hereinafter, the present invention will be illustrated in more detail by way of examples.

[0216] Examples and Comparative Examples.

[0217] 1. Synthesis of Monomer 1

[0218]

[0219] 1) Synthesis of Compound 1-C

[0220] 47.4 g (100 mmol, 1.0 equivalent) of compound 1-A and 34.5 g (250 mmol, 2.5 equivalent) of compound 1-B were dissolved in 280 g of tetrahydrofuran (THF), and the resulting solution was stirred in an oil bath at 80° C. for 30 minutes. After 55.2 g (400 mmol, 4.0 equivalent) of K CO was dissolved in 300 mL of water, the solution was added dropwise thereto for 10 minutes while the internal temperature of the solution was maintained at 50° C. or higher. 1.53 g (3 mmol, 0.03 equivalent) of Pd(t-Bu P) catalyst was added thereto at an internal temperature of 60° C. After stirring for 1 hour, the mixture was washed with ethyl acetate (EA) / H O to separate the organic layer, and the solvent was concentrated in vacuo. After purification by column chromatography using n-hexane (n-Hex) and dichloromethane (DCM), the resulting product was precipitated in n-hexane (n-Hex) to obtain Compound 1-C as a solid.

[0221] 3) Synthesis of Monomer 1

[0222] 50.0 g (100 mmol, 1.0 equivalent) of compound 1-C, 22.0 g (250 mmol, 2.5 equivalents) of compound 1-D and 2.77 g (20 mmol, 0.20 equivalents) of K CO were dissolved in 250 g of dimethylacetamide (DMAc), and the resulting solution was stirred in an oil bath at 120° C. for 2 hours. After cooling, a solid was precipitated by adding water thereto, and then filtered. The obtained solid was purified by column chromatography using ethyl acetate (EA) and dichloromethane (DCM), and then precipitated in n-hexane (n-Hex) to obtain 46.3 g of monomer 1 as a white solid.

[0223] MS: [M+H] + =588

[0224] 2. Synthesis of Monomer 2

[0225]

[0226] 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.

[0227] MS: [M+H] + =588

[0228] 3. Synthesis of Monomer 3

[0229]

[0230] 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-B.

[0231] MS: [M+H] + =688

[0232] 4. Synthesis of Monomer 4

[0233]

[0234] 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-B.

[0235] MS: [M+H] + =768

[0236] 5. Synthesis of Monomer 5

[0237]

[0238] 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-B.

[0239] MS: [M+H] + =768

[0240] Synthesis of Comparative Example Monomer C1

[0241]

[0242] Comparative Example Monomer 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. C1 can also be purchased from TCI or Sigma-Aldrich.

[0243] MS: [M+H] + =438

[0244] Preparation of resin (polymer) 1

[0245]

[0246] 1 g (1.70 mmol, 1.0 equivalent) of monomer 1 and 0.35 g (1.77 mmol, 1.0 equivalent) of terephthaloyl chloride were dissolved in 4.1 g of diphenyl ether (DPE), and the reaction solution was reacted in an oil bath at 180°C for 6 hours. As the reaction proceeded, hydrochloric acid (HCl) gas was generated, and a nitrogen replacement device and a hydrochloric acid gas capture device were installed to remove the gas. After the reaction, the resulting product was cooled to 100°C, 15 g of dimethylacetamide (DMAc) was added thereto, and the resulting mixture was precipitated with methanol (methyl alcohol) to prepare Resin (Polymer) 1.

[0247] Preparation of resins 2 to 5

[0248] Resins 2 to 5 were prepared in the same manner as in the method for preparing Resin 1, except that Monomers 2 to 5 were used instead of Monomer 1.

[0249] Preparation of Comparative Example Resin P1

[0250] Comparative Example Resin P1 was prepared in the same manner as in the method for preparing Resin 1, except that Monomer C1 of the Comparative Example was used instead of Monomer 1.

[0251] Preparation of Resin (Polymer) 6

[0252]

[0253] 57.7 g (98 mmol) of monomer 1 and 21.4 g (100 mmol) of diphenyl carbonate were melted and reacted at 250° C. for 5 hours. As the reaction proceeded, phenol was produced as a by-product, and the degree of reduced pressure was adjusted to as high as 1 torr to remove the phenol. After the reaction was completed, a molten resin of a polymer polymerized by flowing nitrogen into the reactor to create a normal pressure atmosphere was taken out, thereby obtaining resin (polymer) 6.

[0254] Preparation of resins 7 to 10

[0255] Resins 7 to 10 were prepared in the same manner as in the method for preparing Resin 6, except that Monomers 2 to 5 were used instead of Monomer 1.

[0256] Preparation of Comparative Example Resin P2

[0257] Comparative Example Resin P2 was prepared in the same manner as in the method for preparing Resin 6, except that Monomer C1 of the Comparative Example was used instead of Monomer 1.

[0258] Experimental example.

[0259] The molecular weight and molecular weight distribution of the polymerized resin samples were determined by gel permeation chromatography (GPC), and a differential scanning calorimeter (DSC) was used to obtain thermograms to study thermal properties. After forming a film, the refractive index and Abbe number were measured, and the resulting values ​​according to the wavelength of light were obtained using an ellipsometer.

[0260] For the molecular weight by gel permeation chromatography (GPC), the results were obtained by injecting a solution produced using tetrahydrofuran (THF, stabilized with butylated hydroxytoluene (BHT)) as a solvent, dissolving the resin sample in tetrahydrofuran at a concentration of 1.0 mg / 1 ml, filtering the dissolved resin sample with a syringe filter, and measuring the molecular weight at 40° C. The results are shown in the following Table 1. A Waters RI detector was used, and two Agilent PLgel MIXED-B columns were used.

[0261] Differential Scanning Calorimetry (DSC) was used to measure the glass transition temperature (Tg) of the resin. The glass transition temperature (Tg) was obtained on a graph obtained by heating 5.5 mg to 8.5 mg of a resin sample to 270°C under a N2 stream, cooling the resin sample, and then scanning the resin sample while heating the resin sample at a heating rate of 10°C / min during the second heating period. The glass transition temperature (Tg) is shown in Table 1 below.

[0262] In order to measure the refractive index and Abbe number of the resin, a polymer solution prepared by dissolving a resin powder sample obtained by polymerization in a solvent dimethylacetamide in an amount of 10% by weight based on the total weight of the polymer solution was applied to a silicon wafer by spin coating at a rotation speed of 220 rpm to form a film having a thickness of 20 μm, and then the resulting values ​​according to the wavelength of light were obtained at 20° C. using an ellipsometer and are shown in the following Table 1. Specifically, the refractive index was measured at a wavelength of 589 nm, and for the Abbe number, the refractive index (n) at wavelengths D (589 nm), F (486 nm), and C (656 nm) was measured, respectively. D 、n F and n C ), the Abbe number is obtained by the following equation.

[0263] Abbe number = (n D -1) / (n F -n C )

[0264] [Table 1]

[0265]

[0266] In Table 1, Mn means number average molecular weight, Mw means weight average molecular weight, and refractive index is the value measured at a wavelength of 589nm. According to Table 1, the resin according to the exemplary embodiment of the present invention includes a unit represented by Chemical Formula 1, and in particular, when L1 and L2 of the spirobifluorene core structure are substituted with an electron-rich aromatic substituent such as an arylene or a sub-heteroaryl group, the refractive index can be increased by increasing the electron density of the spirobifluorene core structure. In addition, it can be determined that the resin of the embodiment has a higher glass transition temperature (Tg) than the resin of the comparative example and therefore has excellent heat resistance. On the contrary, it can be determined that the resin according to Comparative Examples 1 and 2 does not have an electron-rich substituent in the phenyl ring of the fluorene core structure, and therefore has a very low refractive index compared to the embodiments of the present invention.

[0267] Currently, in the case of optical lenses, especially mobile camera modules, the primary requirement is to reduce the thickness by molding the lens or using a high-refractive-index resin. It can be determined that the resin according to an exemplary embodiment of the present specification is a highly useful resin as an optical material because Examples 1 to 10 have a refractive index that can meet the above requirements, rather than Comparative Examples 1 to 2.

Claims

1. A polycarbonate resin or polyester resin comprising a unit represented by the following Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R1 and R2 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted alkyl; or substituted or unsubstituted cycloalkyl, r1 is an integer from 0 to 4, and when r1 is 2 or greater, two or more R1s are the same as or different from each other, r2 is an integer from 0 to 4, and when r2 is 2 or greater, two or more R2 are the same as or different from each other, L1 and L2 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, L is a direct bond or -CO-L'-, L' is a substituted or unsubstituted arylene group, X1 to X4 are the same as or different from each other and are each independently O or S, Z1 and Z2 are the same as or different from each other and are each independently a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group, a and b are the same as or different from each other and are each independently an integer from 1 to 10, and when a and b are each 2 or greater, the structures in each bracket are the same as or different from each other, and * means the portion connected to the main chain of the resin.

2. The polycarbonate resin or polyester resin according to claim 1, wherein R1 and R2 are hydrogen.

3. The polycarbonate resin or polyester resin according to claim 1, wherein L1 and L2 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 4 to 20 carbon atoms. 4 . The polycarbonate resin or polyester resin according to claim 1 , wherein Z 1 and Z 2 are the same as or different from each other and are each independently a substituted or unsubstituted ethylene group. The polycarbonate resin or polyester resin according to claim 1 , wherein X 1 to X 4 are O. 6 . The polycarbonate resin or polyester resin according to claim 1 , wherein the weight average molecular weight of the resin is 10,000 g / mol to 200,000 g / mol. 7 . The polycarbonate resin or polyester resin according to claim 1 , wherein the resin has a glass transition temperature (Tg) of 200° C. to 250° C. 8 . The polycarbonate resin or polyester resin according to claim 1 , wherein the resin has a refractive index measured at a wavelength of 589 nm of 1.68 to 1.

75.

9. A compound represented by the following Chemical Formula 1a: [Chemical Formula 1a] In Chemical Formula 1a, R1 and R2 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted alkyl; or substituted or unsubstituted cycloalkyl, r1 is an integer from 0 to 4, and when r1 is 2 or greater, two or more R1s are the same as or different from each other, r2 is an integer from 0 to 4, and when r2 is 2 or greater, two or more R2 are the same as or different from each other, L1 and L2 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, X1 to X4 are the same as or different from each other and are each independently O or S, Z1 and Z2 are the same as or different from each other and are each independently a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group, and a and b are the same as or different from each other and are each independently an integer of 1 to 10, and when a and b are each 2 or greater, the structures in each bracket are the same as or different from each other.

10. The compound according to claim 9, wherein Chemical Formula 1a is any one selected from the following compounds:

11. A method for preparing a polycarbonate resin or a polyester resin according to any one of claims 1 to 8, the method comprising polymerizing a composition for preparing a resin, the composition for preparing a resin comprising a compound represented by the following Chemical Formula 1a; and a polyester precursor or a polycarbonate precursor: [Chemical Formula 1a] In Chemical Formula 1a, definitions of 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 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: [Chemical Formula A] [Chemical Formula B] In chemical formulas A and B, Ra1, Ra2, Rb1 and Rb2 are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, L' is a substituted or unsubstituted arylene group, and a1, a2, b1, and b2 are each 0 or 1. 13 . A polycarbonate resin or polyester resin composition comprising the polycarbonate resin or polyester resin according to claim 1 . 14 . A molded article comprising the polycarbonate resin or polyester resin composition according to claim 13 .

15. The molded article according to claim 14, wherein the molded article is an optical lens.

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