Resin and its manufacturing method

Abstract

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

Description

[Technical Field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0113637 filed with the Korean Intellectual Property Office on September 7, 2022, and Korean Patent Application No. 10-2022-0113644 filed with the Korean Intellectual Property Office on September 7, 2022, the entire contents of which are incorporated herein by reference.

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

[0003] The higher the refractive index of an optical material, the thinner the optical lens needed to achieve the same level of correction, which allows for thinner and lighter lenses to be manufactured, allowing for the miniaturization of various devices in which 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 in addition, a certain level of transparency or more is required for use as an optical material. Summary of the Invention [Problem to be solved by the invention]

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

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

[0007] One embodiment of the present disclosure provides a resin comprising units of Formula 1: [ka] In the above Chemical Formula 1, R1 and R2 are different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted silyl group; an aryl group substituted or unsubstituted with deuterium, a halogen group, a hydroxy group, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an aryloxy group, an arylthio group, an alkylthio group, an aryl group, or a heteroaryl group; or a substituted or unsubstituted heteroaryl group, r1 and r2 are each an integer of 1 to 4. When r1 is 2 or more, the two or more R1s are the same as or different from each other. When r2 is 2 or more, the two or more R2s 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, X1 to X4, X9, and X10 are the same as or different from each other and are each independently O; or S, Z1 to Z3 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, La and La’’ are the same as or different from each other and are each independently a direct bond; or -C(=O)-L-, L is a substituted or unsubstituted arylene group, a, b, and p are the same as or different from each other and are each independently an integer of 0 to 6. When a, b, and p are each 2 or more, the structures within each parentheses are the same as or different from each other, q is an integer of 1 to 6. When q is 2 or more, the two or more qs are the same as or different from each other, m is 0 or 1, When m is 0, q, r, and s are 1, and La is -C(=O)-L-, <0000​ * indicates the site connected to the main chain of the resin.

[0008] One embodiment of the present specification provides a method for producing the resin, comprising polymerizing a composition for producing the resin, the composition comprising: a compound represented by the following chemical formula 1a; and 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor:

[0009] [ka] In the above formula 1a, The definitions of R1, R2, r1, r2, L1, L2, X1 to X4, a, b, Z1, and Z2 are the same as those in Chemical Formula 1 above.

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

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

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

[0013] By using a resin according to an embodiment of the present specification, it is possible to obtain an excellent optical lens, optical film, optical thin film, or optical resin with a small thickness. [Brief explanation of the drawings]

[0014] [Figure 1] FIG. 10 is a diagram showing the lens thickness reduction rate depending on the refractive index difference. DETAILED DESCRIPTION OF THE INVENTION

[0015] The present specification will be explained in more detail below.

[0016] The resin containing units of Chemical Formula 1 according to one embodiment of the present specification can be seen to increase the refractive index of a material made up of the molecules by increasing the electron density of the molecule and reducing the molecular volume, based on the Lorentz-Lorenz formula, which shows the relationship between molecular structure and refractive index. Furthermore, the substituents on the benzene rings on both sides of the fluorene structure of Chemical Formula 1 form an asymmetric structure, containing R1 and R2 as substituents, thereby increasing the electron density and improving the refractive index of a molded product containing the resin. Therefore, the resin according to one embodiment of the present specification has a high refractive index and high transparency, and optical lenses, optical films, or optical resins made therefrom can be thin and exhibit excellent optical properties.

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

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

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

[0020] As used herein, 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.

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

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

[0023] As used herein, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

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

[0025] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and an adamantyl group, but are not limited to these.

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

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

[0028] In this specification, the aryl group is not particularly limited, but preferably has 6 to 50 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0029] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably is 6 to 30. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group.

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

[0031] In this specification, the fluorene group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0032] When the fluorene group is substituted, [ka] These include, but are not limited to:

[0033] As used herein, the term "adjacent" groups may refer to a substituent substituted on an atom directly linked to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0034] In this specification, a heteroaryl group includes one or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, an acridine group, a pyridazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, and a phenanthridine group. Examples of such an alkyl group include, but are not limited to, phenanthridine, phenanthroline, isoxazole, thiadiazole, dibenzofuran, dibenzosilole, phenoxathiine, phenoxazine, phenothiazine, dihydroindenocarbazole, spirofluorenexanthene, spirofluorenethioxanthene, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran groups.

[0035] In this specification, the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, etc. The alkyl group in the alkylsilyl group may be the same as the alkyl group exemplified above, the aryl group in the arylsilyl group may be the same as the aryl group exemplified above, the alkyl group and aryl group in the alkylarylsilyl group may be the same as the alkyl group exemplified above, and the heteroaryl group in the heteroarylsilyl group may be the same as the heterocyclic group exemplified above.

[0036] In this specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from the above-mentioned exemplified cycloalkyl groups, aryl groups, and combinations thereof. Examples of the hydrocarbon ring group include, but are not limited to, a phenyl group, a cyclohexyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a tetrahydronaphthalene group, a tetrahydroanthracene group, a 1,2,3,4-tetrahydro-1,4-methanonaphthalene group, a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group, a spirocyclopentanefluorene group, a spiroadamantanefluorene group, and a spirocyclohexanefluorene group.

[0037] In this specification, an aryloxy group may be represented by -ORo, and the above description of the aryl group applies to Ro.

[0038] In this specification, an arylthio group may be represented by -SRs1, and the above description of the aryl group applies to Rs1.

[0039] In this specification, an alkylthio group may be represented by -SRs2, and the above description of the alkyl group applies to Rs2.

[0040] In this specification, the alkylene group refers to an alkyl group having two bonding positions, i.e., a divalent group. The above description of the alkyl group may be applied, except that each of these is a divalent group.

[0041] In this specification, a cycloalkylene group refers to a cycloalkyl group having two bonding positions, i.e., a divalent group. The above description of the cycloalkyl group may be applied, except that each of these is a divalent group.

[0042] In this specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above description of the aryl group may be applied, except that each of these is a divalent group.

[0043] In this specification, a divalent fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring means a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring having two bonding positions, i.e., a divalent group. Except for the fact that these are each divalent groups, the above-mentioned explanation of the fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring may be applied.

[0044] Preferred embodiments of the present invention will be described in detail below. However, the embodiments of the present invention may be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0045] According to one embodiment of the present specification, the resin may contain one or more units of Chemical Formula 1, and when two or more units are contained, the units may be the same or different from each other.

[0046] According to one embodiment of the present specification, the resin may contain one or more units of Chemical Formula 2, and when two or more units are contained, the units may be the same or different from each other.

[0047] That is, the resin according to the present invention includes the unit of Chemical Formula 1, which improves reactivity and simplifies production of the resin, and the refractive index of the resin can be improved by increasing the electron density of each core structure. Therefore, the resin according to one embodiment of the present specification has a high refractive index and high transparency, and an optical lens, optical film, or optical resin using the resin can be thin and exhibit excellent optical properties.

[0048] According to one embodiment of the present specification, the resin is a polyester resin or a polyester-carbonate resin.

[0049] According to one embodiment of the present specification, the resin further includes a unit of the following chemical formula 2:

[0050] [ka] In the above Chemical Formula 2, L11 is a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; or a substituted or unsubstituted arylene group; l11 is an integer of 1 to 5, and when l11 is 2 or more, the two or more L11's may be the same or different from each other; X11 to X16 are the same or different and each independently represent O or S; Z11 to Z13 are the same or different and each independently represent a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; Lb and Lb' are the same or different and each independently represent a direct bond; or -C(=O)-L'-; L' is a substituted or unsubstituted arylene group; a', b', and p' are the same or different and each independently represents an integer of 0 to 6, and when a', b', and p' are each 2 or more, the structures in each parentheses are the same or different, q’ is an integer from 1 to 6, and when the q’ is 2 or more, the q’ values of 2 or more are the same as or different from each other. m’’ is 0 or 1, when m’’ is 0, the q’, r’, and s’ are 1, and the Lb is -C(=O)-L’-, when m’’ is 1, the q’ is an integer from 1 to 6, r’ + s’ = 1, r’ is a real number with 0 < r’ < 1 as the molar fraction, and s is a real number with 0 < s’ < 1 as the molar fraction. * means the site linked to the main chain of the resin.

[0051] By further including the unit of the chemical formula 2 in the resin, the glass transition temperature (Tg) of the unit of the chemical formula 1 can be complemented or the chain behavior of the unit of the chemical formula 1 can be made flexible, which has an advantageous technical effect on the injection molding of the molded product.

[0052] One embodiment of the present specification provides a resin containing the unit of the chemical formula 1 and the unit of the chemical formula 2.

[0053] According to one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-1 or 1-2. [[ID=​​​​​​​​​​​​​​​​​​L is a substituted or unsubstituted arylene group, r is a real number where 0 < x < 1 as a mole fraction, s is a real number where 0 < y < 1 as a mole fraction, s + r = 1.

[0054] According to one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-1-1.

[0055]

Chemical formula

[0056] According to one embodiment of the present specification, the q is 1.

[0057] According to one embodiment of the present specification, the r1 is 1.

[0058] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 1-1-2 to 1-1-5.

[0059]

Chemical formula

[0060] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 1-2-1 to 1-2-4.

[0061]

Chemical formula

[0062] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 1-2-5 to 1-2-8.

[0063] [ka] In the chemical formulas 1-2-5 to 1-2-8, The definitions of Z1 to Z3, X1 to X4, X9, X10, a, b, r, p, s, q, L1, L2, R1, R2, r1, and r2 are the same as those in Chemical Formula 1. L3 and L4 are the same or different and each independently represent a substituted or unsubstituted arylene group.

[0064] According to one embodiment of the present specification, the chemical formula 2 is the following chemical formula 2-1 or 2-2.

[0065] [ka] In the above Chemical Formula 2-1, *, L11, l11, X11 to X16, Z11 to Z13, a', b', and p' are as defined in Chemical Formula 2 above, Lb is -C(=O)-L'-, L' is a substituted or unsubstituted arylene group; In the above Chemical Formula 2-2, *, L11, l11, X11 to X16, Z11 to Z13, a', b', q'', and p' are as defined in Chemical Formula 2 above, Lb and Lb' are the same or different and each independently represent a direct bond; or -C(=O)-L'-; L’ is a substituted or unsubstituted arylene group, r’ is a real number with 0 < r’ < 1 as a molar fraction, s’ is a real number with 0 < s’ < 1 as a molar fraction, r’ + s’ = 1.

[0066] According to one embodiment of the present specification, the chemical formula 2 is the chemical formula 2-1.

[0067] According to one embodiment of the present specification, the chemical formula 2 is the chemical formula 2-2.

[0068] According to one embodiment of the present specification, the chemical formula 2 is the following chemical formula 2-1-]

[0069]

Chemical formula

[0070] According to one embodiment of the present specification, the chemical formula 2 is any one of the following chemical formulas 2-2-1 to 2-2-4.

[0071]

Chemical formula

[0072] According to one embodiment of the present specification, R1 and R2 are different from each other and each independently represent hydrogen or an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; L1 and L2 are the same as or different from each other and each independently represent a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; X1 to X4, X9, and X10 are O; and Z1 to Z3 are the same as or different from each other and each independently represent a linear or branched alkylene group having 1 to 30 carbon atoms.

[0073] According to one embodiment of the present specification, R1 and R2 are different from each other and each independently represent a hydrogen atom or an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0074] According to one embodiment of the present specification, R1 and R2 are different from each other and each independently represent a hydrogen atom or an unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0075] According to one embodiment of the present specification, R1 and R2 are different from each other and each independently represent hydrogen or an unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.

[0076] According to one embodiment of the present specification, R1 and R2 are different from each other and each independently represent hydrogen or an unsubstituted polycyclic aryl group having 10 to 20 carbon atoms.

[0077] According to one embodiment of the present specification, R1 and R2 are different from each other and each independently represent a hydrogen atom or a naphthyl group.

[0078] According to one embodiment of the present specification, R1 is a naphthyl group.

[0079] According to one embodiment of the present specification, R2 is hydrogen.

[0080] According to one embodiment of the present specification, L1 and L2 are the same or different and each independently represent a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0081] According to one embodiment of the present specification, L1 and L2 are the same or different and each independently represent a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0082] According to one embodiment of the present specification, L1 and L2 are the same or different and each independently represent a polycyclic arylene group having 10 to 30 carbon atoms.

[0083] According to one embodiment of the present specification, L1 and L2 are the same or different and each independently represent a polycyclic arylene group having 10 to 20 carbon atoms.

[0084] According to one embodiment of the present specification, L1 and L2 are divalent naphthalene groups.

[0085] According to one embodiment of the present specification, X1 is O.

[0086] According to one embodiment of the present specification, X2 is O.

[0087] According to one embodiment of the present specification, X3 is O.

[0088] According to one embodiment of the present specification, X4 is O.

[0089] According to one embodiment of the present specification, X9 is O.

[0090] According to one embodiment of the present specification, X10 is O.

[0091] According to one embodiment of the present specification, Z1 to Z3 are the same or different and each independently represent a linear or branched alkylene group having 1 to 30 carbon atoms.

[0092] According to one embodiment of the present specification, Z1 to Z3 are the same or different and each independently represent a linear or branched alkylene group having 1 to 20 carbon atoms.

[0093] According to one embodiment of the present specification, Z1 to Z3 are ethylene groups.

[0094] According to one embodiment of the present specification, La and La'' are the same or different and each independently represent a direct bond; or -C(=O)-L-.

[0095] According to one embodiment of the present specification, La and La″ are different from each other and each independently represent a direct bond; or —C(═O)—L—.

[0096] According to one embodiment of the present specification, La and La'' are direct bonds.

[0097] According to one embodiment of the present specification, La and La'' are -C(=O)-L-.

[0098] According to one embodiment of the present specification, La is a direct bond, and La'' is -C(=O)-L-.

[0099] According to one embodiment of the present specification, La'' is a direct bond, and La is -C(=O)-L-.

[0100] According to one embodiment of the present specification, the L is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0101] According to one embodiment of the present specification, the L is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0102] According to one embodiment of the present specification, L is a phenylene group; or a divalent naphthalene group.

[0103] According to one embodiment of the present specification, L3 and L4 are the same or different and each independently represent a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0104] According to one embodiment of the present specification, L3 and L4 are the same or different and each independently represent a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0105] According to one embodiment of the present specification, L3 and L4 are the same or different and each independently represent a phenylene group or a divalent naphthalene group.

[0106] According to one embodiment of the present specification, a is 1.

[0107] According to one embodiment of the present specification, b is 1.

[0108] According to one embodiment of the present specification, a is 0.

[0109] According to one embodiment of the present specification, b is 0.

[0110] According to one embodiment of the present specification, p is 0.

[0111] According to one embodiment of the present specification, p is 1.

[0112] According to one embodiment of the present specification, X11 to X16 are O, L11 is a monocyclic or polycyclic alkylene group having 1 to 30 carbon atoms; or a monocyclic or polycyclic arylene group having 6 to 50 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, The Z11 to Z13 may be the same or different and each independently represents a linear or branched alkylene group having 1 to 30 carbon atoms.

[0113] According to one embodiment of the present specification, L11 is a monocyclic or polycyclic alkylene group having 1 to 30 carbon atoms; or a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic arylene group having 6 to 50 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0114] According to one embodiment of the present specification, L11 is a monocyclic or polycyclic alkylene group having 1 to 20 carbon atoms; or a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0115] According to one embodiment of the present specification, L11 is a methylene group substituted or unsubstituted with a methyl group; an isopropylene group; a phenylene group substituted or unsubstituted with a methyl group or a phenyl group; a divalent naphthalene group; or a divalent fluorene group.

[0116] According to one embodiment of the present specification, the l11 is 1.

[0117] According to one embodiment of the present specification, the l11 is 2, and the two L11 are the same or different from each other.

[0118] According to one embodiment of the present specification, the l11 is 3, and the three L11 are the same as or different from each other.

[0119] According to one embodiment of the present specification, X11 is O.

[0120] According to one embodiment of the present specification, X12 is O.

[0121] According to one embodiment of the present specification, X13 is O.

[0122] According to one embodiment of the present specification, X14 is O.

[0123] According to one embodiment of the present specification, X15 is O.

[0124] According to one embodiment of the present specification, X16 is O.

[0125] According to one embodiment of the present specification, Z11 to Z13 are the same or different and each independently represent a linear or branched alkylene group having 1 to 30 carbon atoms.

[0126] According to one embodiment of the present specification, Z11 to Z13 are the same or different and each independently represent a linear or branched alkylene group having 1 to 20 carbon atoms.

[0127] According to one embodiment of the present specification, Z11 to Z13 are ethylene groups.

[0128] According to one embodiment of the present specification, Lb and Lb' are the same or different and each independently represent a direct bond; or -C(=O)-L'-.

[0129] According to one embodiment of the present specification, Lb and Lb' are different from each other and each independently represent a direct bond; or -C(=O)-L'-.

[0130] According to one embodiment of the present specification, Lb and Lb' are direct bonds.

[0131] According to one embodiment of the present specification, Lb and Lb' are -C(=O)-L'-.

[0132] According to one embodiment of the present specification, Lb' is a direct bond, and Lb is -C(=O)-L'-.

[0133] According to one embodiment of the present specification, Lb is a direct bond, and Lb' is -C(=O)-L'-.

[0134] According to one embodiment of the present specification, L' is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0135] According to one embodiment of the present specification, L' is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0136] According to one embodiment of the present specification, L' is a phenylene group or a divalent naphthalene group.

[0137] According to one embodiment of the present specification, L'1 and L'2 are the same or different and each independently represent a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0138] According to one embodiment of the present specification, L'1 and L'2 are the same or different and each independently represent a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0139] According to one embodiment of the present specification, L'1 and L'2 are the same or different and each independently represent a phenylene group or a divalent naphthalene group.

[0140] According to one embodiment of the present specification, a' is 1.

[0141] According to one embodiment of the present specification, b' is 1.

[0142] According to one embodiment of the present specification, a' is 0.

[0143] According to one embodiment of the present specification, b' is 0.

[0144] According to one embodiment of the present specification, p' is 0.

[0145] According to one embodiment of the present specification, p' is 1.

[0146] According to one embodiment of the present specification, the resin may have terminal groups of -OH; -SH; -CO2CH3; -Cl; or -OC6H5.

[0147] In one embodiment of the present specification, in Chemical Formula 1, r is 0.001 to 0.999 as a molar fraction, and s is 0.001 to 0.999 as a molar fraction, preferably r is 0.01 to 0.99, and s is 0.01 to 0.99, and more preferably r is 0.05 to 0.95, and s is 0.05 to 0.95.

[0148] When r and s in the above formula 1 are within the above ranges, the molar fractions r and s can be appropriately adjusted to obtain a resin with desired physical properties.

[0149] In one embodiment of the present specification, in Chemical Formula 2, r' is 0.001 to 0.999 as a molar fraction, and s' is 0.001 to 0.999 as a molar fraction, preferably r' is 0.01 to 0.99, and s' is 0.01 to 0.99, and more preferably r' is 0.1 to 0.9, and s' is 0.1 to 0.9.

[0150] When r' and s' in the above formula 2 are within the above ranges, the molar fractions r' and s' can be appropriately adjusted to obtain a resin with desired physical properties.

[0151] In one embodiment of the present specification, the weight-average molecular weight of the resin is 3,000 g / mol to 500,000 g / mol, preferably 5,000 g / mol to 300,000 g / mol, 7,000 g / mol to 250,000 g / mol, or 8,000 g / mol to 200,000 g / mol, and more preferably 9,000 g / mol to 150,000 g / mol, 10,000 g / mol to 100,000 g / mol, 12,000 g / mol to 80,000 g / mol, or 13,000 g / mol to 60,000 g / mol.

[0152] In one embodiment of the present invention, the number average molecular weight of the resin is 2,000 g / mol to 300,000 g / mol, 3,000 g / mol to 200,000 g / mol, 4,000 g / mol to 150,000 g / mol, or 4,500 g / mol to 100,000 g / mol, preferably 5,000 g / mol to 80,000 g / mol.

[0153] When the resin satisfies the above-mentioned ranges of weight average molecular weight and number average molecular weight, the resin can have optimal fluidity and processability.

[0154] The weight-average molecular weight (Mw) of resins and oligomers used in their preparation can be measured by gel permeation chromatography (GPC) using a polystyrene standard (PS standard) on an Agilent 1200 series instrument. Specifically, measurements can be performed using a Polymer Laboratories PLgel MIX-B 300 mm column on an Agilent 1200 series instrument at 40°C, tetrahydrofuran (THF) as the solvent, and a flow rate of 1 mL / min. Resin or oligomer samples are prepared to a concentration of 10 mg / 10 mL and then dispensed in 10 μL. The weight-average molecular weight (Mw) values ​​are derived using a calibration curve generated using polystyrene standards. In this case, nine types of polystyrene standards with molecular weights (g / mol) of 2,000 / 10,000 / 30,000 / 70,000 / 200,000 / 700,000 / 2,000,000 / 4,000,000 / 10,000,000 are used.

[0155] In one embodiment of the present specification, the glass transition temperature (Tg) of the resin may be 90°C to 200°C. Preferably, it may be 100°C to 190°C, 120°C to 180°C, 125°C to 170°C, 130°C to 160°C, 152°C to 175°C, or 121°C to 176°C. When the resin satisfies the above-mentioned glass transition temperature range, the resin has excellent heat resistance and injection properties, and when the resin is mixed with a resin having a glass transition temperature different from the above-mentioned range to produce a polycarbonate resin composition, the glass transition temperature can be easily adjusted, and the physical properties targeted in the present specification can be satisfied.

[0156] 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 it, and then heating it for the second time at a heating rate of 10°C / min while scanning.

[0157] In one embodiment of the present specification, the resin has a refractive index of 1.50 to 1.75 measured at a wavelength of 587 nm. The refractive index may be preferably 1.65 to 1.712, or 1.66 to 1.69. When the resin satisfies the above refractive index, it is possible to produce a thin and lightweight optical lens when it is used in a molded product such as an optical lens.

[0158] In one embodiment of the present specification, the Abbe number of the resin measured and calculated at wavelengths of 486, 587, and 656 nm may be 5 to 45. Preferably, it may be 13.5 to 22.5, 16.8 to 20.1, or 16.1 to 20.5. When the resin satisfies the above-mentioned Abbe number range, there is an effect of reducing dispersion and increasing clarity when the resin is applied to a molded product such as an optical lens. Specifically, the Abbe number is determined by the refractive index (n D , n F , n C ) are measured, and the Abbe number can be calculated using the following formula: Abbe number = (n D -1) / (n F -n C )

[0159] The refractive index can be measured by a prism coupler method, for example, SPA-3DR manufactured by SAIRON Technology, but is not limited to this.

[0160] Using a prism coupler, the resin can be placed on a glass slide on a heating plate at 200°C, and the change in the amount of light reflected from the flat sample can be measured to calculate the refractive index. When the sample is placed in contact with the prism and a laser beam is incident on the prism, it undergoes near-total reflection. However, if certain incident angles and conditions are met, an evanescent field is generated at the interface, resulting in light coupling. By measuring the angle at which coupling occurs and the intensity of the light detected by the detector drops sharply, the prism coupler can automatically calculate the refractive index of the film from parameters related to the light polarization mode and the refractive indices of the prism and substrate.

[0161] One embodiment of the present specification provides a method for producing the resin, comprising polymerizing a composition for producing the resin, the composition comprising: a compound represented by the following chemical formula 1a; and 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor:

[0162] [ka] In the above formula 1a, The definitions of R1, R2, r1, r2, L1, L2, X1 to X4, a, b, Z1, and Z2 are the same as those in Chemical Formula 1 above.

[0163] According to one embodiment of the present specification, the method for producing a resin further includes a compound represented by the following Chemical Formula 2a, wherein the compound represented by Chemical Formula 1a and the compound represented by Chemical Formula 2a are contained in an amount of 0.01 mol % to 100 mol %: 99.99 mol % to 0 mol %. Specifically, the amounts are 0.01 mol % to 99.99 mol %: 99.99 mol % to 0.01 mol %. More specifically, the amounts are 0.1 mol % to 99.9 mol %: 99.9 mol % to 0.1 mol %, 1 mol % to 99 mol %: 99 mol % to 1 mol %, or 5 mol % to 90 mol %: 5 mol % to 90 mol %.

[0164] [ka] In the above chemical formula 2a, L11 is a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; a substituted or unsubstituted divalent fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted arylene group; l11 is an integer of 1 to 5, and when l11 is 2 or more, the two or more L11's may be the same or different from each other; X11 to X14 are the same or different and each independently represent O or S; Z11 and Z12 are the same or different and each independently represent 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 0 to 10, and when a' and b' are each 2 or greater, the structures in each parentheses are the same or different.

[0165] One embodiment of the present specification provides a method for producing the resin, comprising polymerizing a composition for producing the resin, the composition including the compound of Formula 1a, a polyester precursor, and a polycarbonate precursor. When the compound of Formula 1a is included, the resin is easily polymerized, has a refractive index in a wide range or a high refractive index depending on the substituent, and has a wide range of glass transition temperatures.

[0166] One embodiment of the present specification provides a method for producing the resin, comprising polymerizing a resin-producing composition containing the compound of Chemical Formula 1a; the compound of Chemical Formula 2a; and 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor. The compound of Chemical Formula 1a and the compound of Chemical Formula 2a are contained in an amount of 0.01 mol% to 100 mol%: 99.99 mol% to 0 mol%. Specifically, the amounts are 0.01 mol% to 99.99 mol%: 99.99 mol% to 0.01 mol%. More specifically, the amounts are 0.1 mol% to 99.9 mol%: 99.9 mol% to 0.1 mol%, 1 mol% to 99 mol%: 99 mol% to 1 mol%, or 5 mol% to 90 mol%: 5 mol% to 90 mol%.

[0167] When the compounds of Formulas 1a and 2a are contained in the above amounts, they are easily polymerized, have a wide range of refractive indexes depending on the substituents, or a high refractive index, and have a wide range of glass transition temperatures. In addition, the glass transition temperature (Tg) and refractive index can be adjusted, and the chain behavior of the resin can be made flexible, which has advantageous technical effects for injection processing of molded products.

[0168] The composition for producing a resin may further contain a solvent.

[0169] 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.

[0170] The solvent may be contained in an amount of 5 to 60 parts by weight relative to 100 parts by weight of the composition for producing a resin.

[0171] The solvent may be contained in an amount of preferably 5 to 50 parts by weight, 7 to 45 parts by weight, or 8 to 40 parts by weight relative to 100 parts by weight of the composition for producing a resin.

[0172] In one embodiment of the present specification, the compound of Formula 1a may be, but is not limited to, the following compound: [ka]

[0173] In one embodiment of the present specification, the compound of Formula 2a may be any one of the following compounds, but is not limited thereto: [ka]

[0174] One embodiment of the present invention preferably provides a method for producing the resin, the method including a step of polymerizing a resin-producing composition containing the polyester precursor, the composition including the compound of Chemical Formula 1a and the compound of Chemical Formula 2a.

[0175] In one embodiment of the present specification, the compound of Chemical Formula 1a may be included in an amount of 1 part by weight to 99 parts by weight based on 100 parts by weight of the composition for producing a resin.

[0176] The compound of 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, 1 to 20 parts by weight, or 1 to 10 parts by weight, based on 100 parts by weight of the composition for producing a resin.

[0177] In one embodiment of the present specification, the compound of Chemical Formula 2a 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.

[0178] The compound of Chemical Formula 2a may be included in an amount of preferably 1 to 60 parts by weight, 1 to 50 parts by weight, 1 to 40 parts by weight, 1 to 30 parts by weight, 1 to 20 parts by weight, or 1 to 10 parts by weight, based on 100 parts by weight of the composition for producing a resin.

[0179] In one embodiment of the present specification, the polyester precursor may be contained in an amount of 1 part by weight to 150 parts by weight based on 100 parts by weight of the composition for producing a resin.

[0180] The polyester precursor may be contained in an amount of preferably 1 to 150 parts by weight, 1 to 140 parts by weight, 1 to 130 parts by weight, 1 to 125 parts by weight, or 1 to 120 parts by weight relative to 100 parts by weight of the composition for producing a resin.

[0181] One embodiment of the present invention preferably provides a method for producing the resin, the method comprising polymerizing a resin-producing composition containing the polyester precursor and the polycarbonate precursor, the composition comprising the compound of Chemical Formula 1a and the compound of Chemical Formula 2a.

[0182] In one embodiment of the present specification, the compound of Chemical Formula 1a may be included in an amount of 1 part by weight to 100 parts by weight, or 1 part by weight to 99 parts by weight, based on 100 parts by weight of the composition for producing a resin.

[0183] The compound of 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, 1 to 20 parts by weight, or 1 to 10 parts by weight, based on 100 parts by weight of the composition for producing a resin.

[0184] In one embodiment of the present specification, the compound of Chemical Formula 2a may be included in an amount of 0 to 99 parts by weight, or 1 to 99 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0185] The compound of Chemical Formula 2a may be included in an amount of preferably 1 to 60 parts by weight, 1 to 50 parts by weight, 1 to 40 parts by weight, 1 to 30 parts by weight, 1 to 20 parts by weight, or 1 to 10 parts by weight, based on 100 parts by weight of the composition for producing a resin.

[0186] In one embodiment of the present specification, the polyester precursor may be contained in an amount of 1 part by weight to 60 parts by weight based on 100 parts by weight of the composition for producing a resin.

[0187] The polyester precursor may be contained in an amount of preferably 1 to 60 parts by weight, 1 to 55 parts by weight, 1 to 50 parts by weight, 1 to 45 parts by weight, or 1 to 40 parts by weight relative to 100 parts by weight of the composition for producing a resin.

[0188] In one embodiment of the present specification, the polycarbonate precursor may be contained in an amount of 1 part by weight to 60 parts by weight based on 100 parts by weight of the composition for producing a resin.

[0189] The polycarbonate precursor may be contained in an amount of preferably 1 to 60 parts by weight, 1 to 55 parts by weight, 1 to 50 parts by weight, 1 to 45 parts by weight, or 1 to 40 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0190] According to one embodiment of the present specification, the polyester precursor is represented by the following chemical formula A, and the polycarbonate precursor is represented by the following chemical formula B.

[0191] [ka] In the above chemical formulas A and B, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a hydrogen atom; a halogen atom; a hydroxyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; Ar1 is a substituted or unsubstituted arylene group; a1 to a4 are each 0 or 1.

[0192] According to one embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a hydrogen atom; a halogen group; a hydroxyl group; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0193] According to one embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a hydrogen atom; a halogen group; a hydroxyl group; a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0194] According to one embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a hydrogen atom; a halogen group; a hydroxy group; a linear or branched alkyl group having 1 to 30 carbon atoms and being unsubstituted or substituted with a hydroxy group; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0195] According to one embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2 are the same or different and each independently represent a hydrogen atom; a halogen group; a hydroxy group; a linear or branched alkyl group having 1 to 20 carbon atoms and being unsubstituted or substituted with a hydroxy group; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0196] According to one embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2 are the same or different from each other and each independently represent hydrogen; -Cl; a hydroxy group; a methyl group; an ethyl group; an n-propyl group; an n-butyl group; an isopropyl group; an isobutyl group; a hydroxyethyl group; or a phenyl group.

[0197] According to one embodiment of the present specification, the definition of Ar1 may be the same as the definitions of La and Lb described above.

[0198] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0199] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0200] According to one embodiment of the present specification, Ar1 is a phenylene group or a naphthylene group.

[0201] According to one embodiment of the present specification, the compound represented by formula A is any one selected from the following compounds: [ka]

[0202] According to one embodiment of the present specification, the chemical formula B is any one selected from the following compounds: [ka]

[0203] The polycarbonate precursor serves to link additional comonomers as needed, and specific examples 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-cresyl carbonate, dinaphthyl carbonate, bis(diphenyl)carbonate, and bishaloformates, and any one or a mixture of two or more of these may be used.

[0204] In one embodiment of the present specification, the resin is a polyester resin.

[0205] In one embodiment of the present specification, the resin is preferably polymerized from the compound of formula 1a; the compound of formula 2a; and the polyester precursor of formula A.

[0206] The unit of Formula 1 can be formed by polymerizing the compound of Formula 1a and the polyester precursor of Formula A.

[0207] The compound of Chemical Formula 1a may be used in an amount of 1 to 99 parts by mole relative to 100 parts by mole of all monomers constituting the resin containing the unit of Chemical Formula 1.

[0208] The polyester precursor of the chemical formula A may be used in an amount of 1 to 150 parts by mole, or 50 to 150 parts by mole, per 100 parts by mole of all the monomers of the compound of the chemical formula 1a that constitute the resin.

[0209] The compound of Formula 2a and the polyester precursor of Formula A can be polymerized to form the unit of Formula 2.

[0210] The compound of Chemical Formula 2a may be used in an amount of 1 to 99 parts by mole relative to 100 parts by mole of all monomers constituting the resin containing the unit of Chemical Formula 2.

[0211] The polyester precursor of the chemical formula A may be used in an amount of 1 to 150 parts by mole, or 50 to 150 parts by mole, per 100 parts by mole of all the monomers of the compound of the chemical formula 2a that constitute the resin.

[0212] In one embodiment herein, the resin is a polyester-carbonate resin.

[0213] In one embodiment of the present specification, the resin is preferably polymerized from the compound of formula 1a; the polyester precursor of formula A; and the polycarbonate precursor of formula B.

[0214] In one embodiment of the present specification, the resin is preferably polymerized from the compound of formula 1a; the compound of formula 2a; the polyester precursor of formula A; and the polycarbonate precursor of formula B.

[0215] The compound of formula 1a, the polyester precursor of formula A, and the polycarbonate precursor of formula B are polymerized to form the unit of formula 1, and the compound of formula 2a, the polyester precursor of formula A, and the polycarbonate precursor of formula B are polymerized to form the unit of formula 2.

[0216] The compound of Formula 1a, the polyester precursor of Formula A, and the polycarbonate precursor of Formula B can be polymerized to form the unit of Formula 1.

[0217] The compound of Chemical Formula 1a may be used in an amount of 1 to 100 parts by mole, or 1 to 99 parts by mole, relative to 100 parts by mole of all monomers constituting the resin containing the unit of Chemical Formula 1.

[0218] The polyester precursor of the chemical formula A may be used in an amount of 1 to 150 parts by mole, or 25 to 150 parts by mole, per 100 parts by mole of all monomers of the compound of the chemical formula 1a that constitutes the resin.

[0219] The polycarbonate precursor of the chemical formula B may be used in an amount of 1 to 150 parts by mole, or 25 to 150 parts by mole, per 100 parts by mole of all monomers of the compound of the chemical formula 1a that constitutes the resin.

[0220] The compound of Formula 2a, the polyester precursor of Formula A, and the polycarbonate precursor of Formula B can be polymerized to form the unit of Formula 2.

[0221] The compound of Chemical Formula 2a may be used in an amount of 1 to 100 parts by mole, or 1 to 99 parts by mole, relative to 100 parts by mole of all monomers constituting the resin containing the unit of Chemical Formula 2.

[0222] The polyester precursor of the chemical formula A may be used in an amount of 1 to 150 parts by mole, or 25 to 150 parts by mole, per 100 parts by mole of all monomers of the compound of the chemical formula 1a that constitutes the resin.

[0223] The polycarbonate precursor of the chemical formula B may be used in an amount of 1 to 150 parts by mole, or 25 to 150 parts by mole, per 100 parts by mole of all monomers of the compound of the chemical formula 1a that constitutes the resin.

[0224] In one embodiment of the present invention, the molar ratio of the compound of Chemical Formula 1a to the compound of Chemical Formula 2a is 100:0 to 0.01 to 99.99, or 0.01:99.99 to 99.99:0.01, preferably 0.1:99.9 to 99.9:0.1, and more preferably 1:99 to 99:1.

[0225] Preferably, the molar ratio of the compound represented by Chemical Formula 1a to the compound represented by Chemical Formula 2a is 20:80 to 50:50.

[0226] Polymerization of the resins herein may be accomplished using methods well known in the art.

[0227] The polymerization is preferably carried out by a melt polycondensation method.

[0228] The melt polycondensation method may use the resin production composition, and optionally further apply a catalyst, and may perform melt polycondensation under heating and further under atmospheric pressure or reduced pressure while removing by-products through a transesterification reaction. The catalyst may be a substance generally used in the art.

[0229] Specifically, the melt polycondensation method is preferably carried out by melting the compound of Formula 1a and 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor in a reaction vessel, and then allowing by-product compounds to remain.

[0230] More specifically, the melt polycondensation method is preferably carried out by melting the compound of Formula 1a; the compound of Formula 2a; and 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor in a reaction vessel, and then allowing by-product compounds to remain.

[0231] 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.

[0232] The reaction time in 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.

[0233] In this case, if the by-product compounds are distilled off immediately after production, the final resin will have a low content of high molecular weight compounds, 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 high molecular weight compounds.

[0234] 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 stirring blade, a Maxblend stirring blade, a helical ribbon-type stirring blade, or the like, or a horizontal type equipped with a paddle blade, a lattice blade, a spectacle blade, or the like, or an extruder type equipped with a screw. In addition, it is preferable to use a reaction apparatus that is an appropriate combination of these reaction apparatuses, taking into consideration the viscosity of the polymer.

[0235] In the method for producing the resin used in this specification, after the polymerization reaction is completed, the catalyst may be removed or deactivated in order to maintain thermal stability and hydrolytic stability. A method of deactivating the catalyst by adding an acidic substance known in the art is preferably carried out.

[0236] 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; phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid, and dibutylphosphonic acid; phosphonic acid esters such as diethyl phenylphosphonate; phosphines such as triphenylphosphine and bis(diphenylphosphino)ethane; boric acids such as boric acid and phenylboric acid; aromatic sulfonates such as tetrabutylphosphonium dodecylbenzenesulfonate; organic halides such as stearic acid chloride, benzoyl chloride, and p-toluenesulfonic acid chloride; alkyl sulfates such as dimethyl sulfate; and organic halides such as benzyl chloride.

[0237] 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, relative to 100 parts by mol of the catalyst.

[0238] If the amount of the acidic substance is less than 0.1 parts by mole, the deactivation effect will be insufficient, which is undesirable, whereas if it exceeds 5 parts by mole, the heat resistance of the resin will decrease and the molded product will be prone to coloration, which is undesirable.

[0239] After the catalyst is deactivated, a step of devolatilizing low-boiling compounds in the resin at a pressure of 0.1 mmHg to 1 mmHg and a temperature of 200° C. to 350° C. may be further carried out. For this step, a horizontal apparatus equipped with stirring blades with excellent surface renewal ability, such as paddle blades, lattice blades, or spectacle blades, or a thin-film evaporator is preferably used.

[0240] The resin of the present invention preferably has a minimum content of foreign matter, and filtration of the molten raw material, filtration of the catalyst solution, etc. are preferably carried out.

[0241] The mesh of the filter used for the filtration is preferably 5 μm or less, more preferably 1 μm or less. The produced resin is preferably filtered through a polymer filter. The mesh of the polymer filter is preferably 100 μm or less, more preferably 30 μm or less. The process of collecting resin pellets must be carried out in a low-dust environment, preferably class 6 or less, more preferably class 5 or less.

[0242] Furthermore, methods for molding molded articles containing the resin include, in addition to injection molding, compression molding, casting, roll processing, extrusion molding, stretching, and the like, but are not limited to these.

[0243] Another embodiment of the present invention provides a resin composition comprising a resin according to the above-described embodiment.

[0244] In one embodiment of the present specification, the resin may be contained in an amount of 1 part by weight to 80 parts by weight based on 100 parts by weight of the resin composition.

[0245] In one embodiment of the present specification, the resin composition may further contain a solvent, for example, dimethylacetamide or 1,2-dichlorobenzene.

[0246] The solvent may be included in an amount of 20 to 99 parts by weight based on 100 parts by weight of the resin composition.

[0247] The resin composition may further include an additional monomer in addition to the compound of Chemical Formula 1a. The additional monomer is not particularly limited, and any monomer generally used in the relevant technical field may be appropriately adopted as long as it does not change the main physical properties of the resin composition. The additional monomer may be used in an amount of 1 to 50 parts by mole relative to 100 parts by mole of all monomers constituting the resin containing the unit of Chemical Formula 1.

[0248] In addition to the resin containing the unit of 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.

[0249] The additive may be included in an amount of 1 to 99 parts by weight based on 100 parts by weight of the resin composition.

[0250] The type of the antioxidant, plasticizer, antistatic agent, nucleating agent, flame retardant, lubricant, impact modifier, fluorescent brightener, ultraviolet absorber, pigment, or dye is not particularly limited, and any agent applicable in the relevant technical field may be appropriately adopted.

[0251] Another embodiment of the present specification provides a molded article comprising a resin composition according to the above-described embodiment.

[0252] In one embodiment of the present specification, the molded article may be produced from the resin composition or a cured product thereof.

[0253] An example of a method for producing the molded article may include thoroughly mixing the resin containing the unit of 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 into an injection molding machine.

[0254] In one embodiment of the present specification, the molded article is an optical lens.

[0255] In one embodiment of the present specification, the optical lens has a thickness of 0.1 μm to 30 mm.

[0256] The optical lens has a different focal point where light is focused in a lens of the same thickness depending on the difference in refractive index. This is shown in Figure 1. This changes the focal point between the camera lens and the image sensor, or between the eyeglass lens and the human pupil, and the refractive index increases to achieve the same focal point, thereby reducing the thickness of the lens or film. The optical lens according to one embodiment of this specification has a high refractive index, making it possible to realize a thin optical lens.

[0257] The optical lens is manufactured using the resin, has a small thickness, a high refractive index and high transparency, and is preferably applicable to cameras.

[0258] In one embodiment of the present specification, the molded article is an optical film or an optical thin film, which is manufactured using the resin, has a small thickness, and has excellent light-collecting and light-diffusing effects, and is preferably applicable to backlight modules of liquid crystal displays, flat lenses, metalenses, etc.

[0259] In one embodiment of the present specification, the optical film or optical thin film has a thickness of 0.1 nm to 10 mm.

[0260] In one embodiment of the present specification, the molded article is an optical resin. The optical resin is manufactured using the resin, has a small thickness, a high refractive index, a low birefringence, and a low optical loss.

[0261] An optical resin according to an embodiment of the present specification has a high refractive index, low birefringence, and low optical loss. The optical resin according to an embodiment of the present specification has a glass transition temperature of 90°C to 200°C, which is very high or not low in heat resistance compared to conventional general optical materials, making it easy to process and exhibiting excellent heat resistance. If the glass transition temperature exceeds 200°C, the melt flow index increases, making processing difficult. If the glass transition temperature is less than 90°C, the poor heat resistance results in reduced weather resistance in the external environment. For this reason, there are few optical resins according to an embodiment of the present specification that have suitable thermal properties and achieve a high refractive index. [Example]

[0262] The present invention will now be illustrated in more detail by way of examples.

[0263] [ka]

[0264] Manufacturing Example 1-1. Manufacturing of Resin 1-1 Monomer 1-1 (66.48 g (100 mmol)) and terephthaloyl chloride (TPC) (19.42 g (100 mmol)) were melted and reacted at 250°C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and resin 1-1 was obtained as a polymerized polymer molten resin.

[0265] Manufacturing Example 1-2. Manufacturing of Resin 1-2 Monomer 1-1 (66.48 g (100 mmol)), terephthaloyl chloride (TPC) (9.71 g (50 mmol)), and isophthaloyl chloride (IPC) (9.71 g (50 mmol)) were melted and reacted at 250°C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and resin 1-2 was obtained as a polymerized polymer molten resin.

[0266] Production Example 1-3. Production of Resin 1-3 Monomer 1-1 (36.56 g (55 mmol)), monomer 2-3 (16.84 g (45 mmol)), and terephthaloyl chloride (TPC) (19.42 g (100 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and resin 1-3 was obtained as a polymerized polymer molten resin.

[0267] Manufacturing Example 1-4. Manufacturing of Resin 1-4 Monomer 1-1 (39.89 g (60 mmol)), Monomer 2-3 (14.97 g (40 mmol)), Terephthaloyl chloride (TPC) (9.71 g (50 mmol)), and Isophthaloyl chloride (IPC) (9.71 g (50 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 1-4 was obtained as a polymerized molten polymer.

[0268] Manufacturing Example 1-5. Manufacturing of Resin 1-5 Monomer 1-1 (19.94 g (30 mmol)), Monomer 2-1 (16.16 g (30 mmol)), Monomer 2-3 (14.97 g (40 mmol)), and Terephthaloyl chloride (TPC) (19.42 g (100 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 1-5 was obtained as a polymerized polymer melt resin.

[0269] Production Example 1-6. Production of Resin 1-6 Monomer 1-1 (19.94 g (30 mmol)), Monomer 2-2 (11.81 g (20 mmol)), Monomer 2-3 (18.71 g (50 mmol)), and Terephthaloyl chloride (TPC) (19.42 g (100 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 1-6 was obtained as a polymerized polymer melt resin.

[0270] Manufacturing Example 1-7. Manufacturing of Resin 1-7 Monomer 1-1 (19.94 g (30 mmol)), Monomer 2-3 (18.71 g (50 mmol)), Monomer 2-4 (4.57 g (20 mmol)), and Terephthaloyl chloride (TPC) (19.42 g (100 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 1-7 was obtained as a polymerized polymer melt resin.

[0271] Manufacturing Example 1-8. Manufacturing of Resin 1-8 Monomer 1-1 (19.94 g (30 mmol)), Monomer 2-3 (18.71 g (50 mmol)), Monomer 2-5 (8.77 g (20 mmol)), and Terephthaloyl chloride (TPC) (19.42 g (100 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 1-8 was obtained as a polymerized polymer melt resin.

[0272] Manufacturing Example 1-9. Manufacturing of Resin 1-9 Monomer 1-1 (19.94 g (30 mmol)), Monomer 2-3 (18.71 g (50 mmol)), Monomer 2-6 (3.96 g (20 mmol)), and Terephthaloyl chloride (TPC) (19.42 g (100 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 1-9 was obtained as a polymerized polymer melt resin.

[0273] Manufacturing Example 1-10. Manufacturing of Resin 1-10 Monomer 1-1 (19.94 g (30 mmol)), Monomer 2-3 (22.45 g (60 mmol)), Monomer 2-7 (3.50 g (10 mmol)), and Terephthaloyl chloride (TPC) (19.42 g (100 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 1-10 was obtained as a polymerized polymer melt resin.

[0274] Manufacturing Example 1-11. Manufacturing of Resin 1-11 Monomer 1-1 (19.94 g (30 mmol)), Monomer 2-3 (22.45 g (60 mmol)), Monomer 2-8 (2.86 g (10 mmol)), Terephthaloyl chloride (TPC) (15.54 g (80 mmol)), and Isophthaloyl chloride (IPC) (3.88 g (20 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was adjusted to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 1-11 was obtained as a polymerized molten polymer.

[0275] Manufacturing Example 1-12. Manufacturing of Resin 1-12 Monomer 1-1 (19.94 g (30 mmol)), Monomer 2-3 (22.45 g (60 mmol)), Monomer 2-9 (3.78 g (10 mmol), Terephthaloyl chloride (TPC) (15.54 g (80 mmol)), and Isophthaloyl chloride (IPC) (3.88 g (20 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 1-12 was obtained as a polymerized molten polymer.

[0276] Manufacturing Example 2-1. Manufacturing of Resin 2-1 Monomer 1-1 (66.48 g (100 mmol)), diphenylcarbonate (DPC) 10.711 g (50 mmol), and terephthaloyl chloride (TPC) (9.7095 g (50 mmol)) were melted and reacted at 250°C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and resin 2-1 was obtained as a polymerized molten polymer.

[0277] Manufacturing Example 2-2. Manufacturing of Resin 2-2 Monomer 1-1 (66.48 g (100 mmol)), diphenylcarbonate (DPC) 8.5688 g (40 mmol), terephthaloyl chloride (TPC) (5.8257 g (30 mmol)), and isophthaloyl chloride (IPC) (5.8257 g (30 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and resin 2-2 was obtained as a polymerized molten polymer.

[0278] Manufacturing Example 2-3. Manufacturing of Resin 2-3 Monomer 1-1 (13.296 g (20 mmol)), Monomer 2-1 (16.159 g (30 mmol)), Monomer 2-3 (18.708 g (50 mmol)), Diphenylcarbonate (DPC) 10.711 g (50 mmol), and Terephthaloyl chloride (TPC) 9.7095 g (50 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 2-3 was obtained as a polymerized molten polymer.

[0279] Manufacturing Example 2-4. Manufacturing of Resin 2-4 Monomer 1-1 (13.296 g (20 mmol)), Monomer 2-2 (17.722 g (30 mmol)), Monomer 2-3 (18.708 g (50 mmol)), Diphenylcarbonate (DPC) 10.711 g (50 mmol), and Terephthaloyl chloride (TPC) (9.7095 g (50 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 2-4 was obtained as a polymerized molten polymer.

[0280] Manufacturing Example 2-5. Manufacturing of Resin 2-5 Monomer 1-1 (19.944 g (30 mmol)), Monomer 2-3 (18.708 g (50 mmol)), Monomer 2-4 (4.566 g (20 mmol)), Diphenylcarbonate (DPC) 10.711 g (50 mmol), and Terephthaloyl chloride (TPC) (9.7095 g (50 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 2-5 was obtained as a polymerized molten polymer.

[0281] Manufacturing Example 2-6. Manufacturing of Resin 2-6 Monomer 1-1 (13.296 g (20 mmol)), Monomer 2-3 (18.708 g (50 mmol)), Monomer 2-5 (13.156 g (30 mmol)), Diphenylcarbonate (DPC) 10.711 g (50 mmol), and Terephthaloyl chloride (TPC) 9.7095 g (50 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 2-6 was obtained as a polymerized molten polymer.

[0282] Manufacturing Example 2-7. Manufacturing of Resin 2-7 Monomer 1-1 (13.296 g (20 mmol)), Monomer 2-3 (18.708 g (50 mmol)), Monomer 2-6 (5.947 g (30 mmol)), Diphenylcarbonate (DPC) 10.711 g (50 mmol), and Terephthaloyl chloride (TPC) (9.7095 g (50 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 2-7 was obtained as a polymerized molten polymer.

[0283] Manufacturing Example 2-8. Manufacturing of Resin 2-8 Monomer 1-1 (19.944 g (30 mmol)), Monomer 2-3 (22.449 g (60 mmol)), Monomer 2-7 (3.504 g (10 mmol)), Diphenylcarbonate (DPC) 10.711 g (50 mmol), and Terephthaloyl chloride (TPC) 9.7095 g (50 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 2-8 was obtained as a polymerized molten polymer.

[0284] Manufacturing Example 2-9. Manufacturing of Resin 2-9 Monomer 1-1 (19.944 g (30 mmol)), Monomer 2-3 (22.449 g (60 mmol)), Monomer 2-8 (2.863 g (10 mmol)), Diphenylcarbonate (DPC) 10.711 g (50 mmol), and Terephthaloyl chloride (TPC) (9.7095 g (50 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 2-9 was obtained as a polymerized molten polymer.

[0285] Manufacturing Example 2-10. Manufacturing of Resin 2-10 Monomer 1-1 (19.944 g (30 mmol)), Monomer 2-3 (22.449 g (60 mmol)), Monomer 2-9 (3.7847 g (10 mmol)), Diphenylcarbonate (DPC) 10.711 g (50 mmol), and Terephthaloyl chloride (TPC) 9.7095 g (50 mmol)) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was reduced to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and Resin 2-10 was obtained as a polymerized molten polymer.

[0286] Manufacturing Example 2-11. Manufacturing of Resin 2-11 Monomer 1-1 (13.296 g (20 mmol)), Monomer 2-1 (16.159 g (30 mmol)), Monomer 2-3 (18.708 g (50 mmol)), Diphenylcarbonate (DPC) 8.5688 g (40 mmol), Terephthaloyl chloride (TPC) 5.8257 g (30 mmol), and Isophthaloyl chloride (IPC) 5.8257 g (30 mmol) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was adjusted to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and the polymerized polymer molten resin, Resin 2-11, was obtained.

[0287] Manufacturing Example 2-12. Manufacturing of Resin 2-12 Monomer 1-1 (13.296 g (20 mmol)), Monomer 2-2 (17.722 g (30 mmol)), Monomer 2-3 (18.708 g (50 mmol)), Diphenylcarbonate (DPC) 8.5688 g (40 mmol), Terephthaloyl chloride (TPC) 5.8257 g (30 mmol), and Isophthaloyl chloride (IPC) 5.8257 g (30 mmol) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was adjusted to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and the polymerized polymer molten resin, Resin 2-12, was obtained.

[0288] Manufacturing Example 2-13. Manufacturing of Resin 2-13 Monomer 1-1 (19.944 g (30 mmol)), Monomer 2-3 (18.708 g (50 mmol)), Monomer 2-4 (4.566 g (20 mmol)), Diphenylcarbonate (DPC) 8.5688 g (40 mmol), Terephthaloyl chloride (TPC) 5.8257 g (30 mmol), and Isophthaloyl chloride (IPC) 5.8257 g (30 mmol) were melted and reacted at 250 °C for 5 hours. As the reaction progressed, methanol was generated as a by-product, and the pressure was adjusted to a maximum of 1 Torr to remove it. After the reaction was completed, nitrogen was blown into the reactor to create an atmospheric pressure atmosphere, and the polymerized polymer molten resin, Resin 2-13, was obtained.

[0289] Example: The molecular weight and molecular weight distribution (PDI = Mw / Mn) of the polymerized resin samples were confirmed by 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.

[0290] 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 and filtering the solution through a syringe filter. The solution was then injected and measured at 40°C, and the results are shown in Tables 3 and 4 below. A Waters RI detector was used, and two Agilent PLgel MIXED-B columns were used.

[0291] The glass transition temperature (Tg) of the resin was measured using a differential scanning calorimeter (DSC). 5.5 mg to 8.5 mg of resin sample was heated to 270°C under N2 flow, cooled, and then heated at a heating rate of 10°C / min during the second heating cycle. The glass transition temperature (Tg) was determined from the resulting graph, and is shown in Tables 3 and 4.

[0292] The refractive index can be measured by a prism coupler method, for example, SPA-3DR manufactured by SAIRON Technology, but is not limited to this.

[0293] Using a prism coupler, the resin is placed on a slide glass on a heating plate at 200°C, and the change in the amount of light reflected from the flat sample is measured to calculate the refractive index. When the prepared sample is brought into contact with the prism and a laser is incident on the prism, almost total reflection occurs. However, if a specific incident angle and conditions are met, an evanescent field is generated at the interface, and light is coupled. By measuring the angle at which coupling occurs and the intensity of the light detected by the detector drops sharply, the prism coupler can automatically calculate the refractive index of the film from parameters related to the light polarization mode and the refractive index of the prism and substrate. The refractive index and Abbe number are listed in Tables 3 and 4 below. Specifically, the refractive index was measured at a wavelength of 587 nm, and the Abbe number is 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 )

[0294] [Table 1]

[0295] [Table 2]

[0296] The mole percentage (mol%) of each monomer contained in Resins 1-1 to 1-12 of Examples 1-1 to 1-12 is shown in Table 1. Furthermore, TPC is terephthaloyl chloride, and IPC is isophthaloyl chloride.

[0297] Table 2 lists the mol % (mol %) of each monomer contained in Resins 2-1 to 2-13 of Examples 2-1 to 2-13. DPC is diphenyl carbonate, TPC is terephthaloyl chloride, and IPC is isophthaloyl chloride.

[0298] [Table 3]

[0299] [Table 4]

[0300] In Tables 3 and 4, Mn means number average molecular weight, Mw means weight average molecular weight, PDI means polydispersity index, RI means refractive index, and Tg means glass transition temperature, and the refractive index is a value measured at a wavelength of 587 nm.

[0301] According to Tables 3 and 4, the resin according to the embodiment of the present invention comprises a unit of Chemical Formula 1, and in particular, the benzene ring of the fluorene core structure of Chemical Formula 1 is substituted with an electron-rich R2 substituent, which increases the electron density of the fluorene core structure and improves the refractive index of the resin containing it.

[0302] In addition, by further including the unit of Chemical Formula 2 in addition to the unit of Chemical Formula 1, the glass transition temperature (Tg) and refractive index can be adjusted and the chain behavior of the resin can be made flexible, which has advantageous technical effects for injection processing of molded products.

[0303] According to Table 4, by appropriately adjusting the molar ratio and isomers of the polyester precursor and polycarbonate precursor, it is possible to produce a resin with desired physical properties by combining the characteristics of polyester resin and polycarbonate resin.

[0304] Therefore, in order to appropriately apply the resin according to the embodiment of the present invention to molded products such as optical lenses, a high refractive index is a high refractive index performance that is preferentially required, and therefore it can be confirmed that the resins of the examples are even more excellent as optical materials.

Claims

1. A resin comprising units of the following formula 1: 【Chemical 1】 In the above Chemical Formula 1, R1 is an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, R2 is hydrogen; r1 is 1, r2 is 4, L1 and L2 are the same or different and each independently represent a substituted or unsubstituted arylene group; X1 to X4, X9, and X10 are the same or different and each independently represent O or S; Z1 to Z3 are the same or different and each independently represent a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; L a and L a″ are the same or different and each independently represent a direct bond; or —C(═O)—L—; L is a substituted or unsubstituted arylene group; a, b, and p are the same or different and each independently represents an integer of 0 to 6, and when a, b, and p are each 2 or more, the structures in each parentheses are the same or different, q is an integer of 1 to 6, and when q is 2 or more, the two or more q's may be the same or different from each other; m is 0 or 1; When m is 0, q, r, and s are 1, and La is —C(═O)-L—; When m is 1, q is an integer of 1 to 6, r+s=1, r is a molar fraction and is a real number in the range of 0<r<1, and s is a molar fraction and is a real number in the range of 0<s<1; * indicates the site connected to the main chain of the resin.

2. The resin of claim 1 , wherein the resin further comprises a unit of the following formula 2: 【Chemistry 2】 In the above Chemical Formula 2, L11 is a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; or a substituted or unsubstituted arylene group; l11 is an integer of 1 to 5, and when l11 is 2 or more, the two or more L11's are the same or different from each other; X11 to X16 are the same or different and each independently represent O or S; Z11 to Z13 are the same or different and each independently represent a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group; Lb and Lb' are the same or different and each independently represent a direct bond; or -C(=O)-L'-; L' is a substituted or unsubstituted arylene group; a', b', and p' are the same or different and each independently represents an integer of 0 to 6, and when a', b', and p' are each 2 or more, the structures in each parentheses are the same or different, q' is an integer of 1 to 6, and when q' is 2 or more, the two or more q's may be the same or different from each other; m″ is 0 or 1; when m″ is 0, q′, r′, and s′ are 1, and Lb is —C(═O)-L′—; When m″ is 1, q′ is an integer of 1 to 6, r′+s′=1, r′ is a molar fraction and is a real number of 0<r′<1, and s is a molar fraction and is a real number of 0<s′<1; * indicates the site connected to the main chain of the resin.

3. The resin according to claim 1, wherein the chemical formula 1 is the following chemical formula 1-1 or 1-2: 【Chemistry 3】 In the above Chemical Formula 1-1, *, R1, R2, r1, r2, L1, L2, X1 to X4, X9, X10, Z1 to Z3, a, b, and p are defined as in Chemical Formula 1. La' is -C(=O)-L-; L is a substituted or unsubstituted arylene group; In the above Chemical Formula 1-2, *, R1, R2, r1, r2, L1, L2, X1 to X4, X9, X10, Z1 to Z3, a, b, p, and q are defined as in Chemical Formula 1. L a and L a″ are the same or different and each independently represent a direct bond; or —C(═O)—L—; L is a substituted or unsubstituted arylene group; r is a real number, 0<x<1, as a mole fraction; s is a real number, 0<y<1, as a mole fraction; s+r=1.

4. L1 and L2 are the same or different and each independently represent a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, X1 to X4, X9, and X10 are O; 2. The resin according to claim 1, wherein Z1 to Z3 are the same or different and each independently represents a linear or branched alkylene group having 1 to 30 carbon atoms.

5. The resin according to claim 1, wherein r is a molar fraction of 0.001 to 0.999, and s is a molar fraction of 0.001 to 0.

999.

6. The resin of claim 1, wherein the weight average molecular weight (Mw) is from 3,000 g / mol to 500,000 g / mol.

7. 2. The resin according to claim 1, wherein the refractive index measured at a wavelength of 587 nm is 1.50 to 1.

75.

8. The resin of claim 1, wherein the glass transition temperature (Tg) is from 90°C to 200°C.

9. 2. The resin of claim 1, wherein the Abbe number measured at wavelengths of 486, 587, and 656 nm is between 5 and 45.

10. A method for producing the resin according to any one of claims 1 to 9, comprising polymerizing a resin-producing composition comprising a compound of the following chemical formula 1a; and 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor: 【Chemistry 4】 In the above formula 1a, The definitions of R1, R2, r1, r2, L1, L2, X1 to X4, a, b, Z1, and Z2 are the same as those in Chemical Formula 1 above.

11. The method for producing a resin according to claim 10, further comprising a compound of the following formula 2a, wherein the compound of formula 1a and the compound of formula 2a are contained in an amount of 0.01 mol % to 100 mol %: 99.99 mol % to 0 mol %: 【Chemistry 5】 In the above Chemical Formula 2a, L11 is a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; a substituted or unsubstituted divalent fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted arylene group, l11 is an integer of 1 to 5, and when l11 is 2 or more, the two or more L11's are the same or different from each other; X11 to X14 are the same or different and each independently represent O or S; Z11 and Z12 are the same or different and each independently represent 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 0 to 10, and when a' and b' are each 2 or more, the structures in the parentheses are the same or different.

12. The method for producing a resin according to claim 10, wherein the polyester precursor is represented by the following chemical formula A, and the polycarbonate precursor is represented by the following chemical formula B: 【Chemistry 6】 In the above chemical formulas A and B, R a1 , R a2 , R b1 , and R b2 are the same or different and each independently represent a hydrogen atom; a halogen atom; a hydroxyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; Ar1 is a substituted or unsubstituted arylene group; a1 to a4 each represent 0 or 1.

13. A resin composition comprising the resin according to any one of claims 1 to 9.

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

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