Resin, method for producing the same, resin composition, and molded product

Abstract

The present application relates to resins comprising units of formula 1 and units of formula 2, methods for making the same, resin compositions comprising the same, and molded articles comprising the resin compositions.

Description

TECHNICAL FIELD

[0001] This application claims priority to and the benefit of Korean Patent Application Nos. 10-2021-0106524, 10-2022-0071582, and 10-2022-0071584, filed on August 12, 2021, June 13, 2022, and June 13, 2022, respectively, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

[0002] The present application relates to a resin and a method of preparing the same. BACKGROUND

[0003] The higher the refractive index of an optical material, the thinner the optical lens required to achieve the same level of calibration. Therefore, as the refractive index of the optical material increases, a thinner and lighter lens can be manufactured, making it possible to make various devices in which the lens is used smaller.

[0004] Generally, when the refractive index of an optical material increases, there is a problem that the Abbe number becomes low, and a certain level or higher level of transparency is required for use as an optical material. SUMMARY

[0005] TECHNICAL PROBLEM

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

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

[0008] TECHNICAL SOLUTION

[0009] An exemplary embodiment of the present application provides a resin comprising a unit of the following Chemical Formula 1 and a unit of the following Chemical Formula 2.

[0010] [Chemical Formula 1]

[0011]

[0012] [Chemical Formula 2]

[0013]

[0014] In Chemical Formula 1 and Chemical Formula 2,

[0015] Ar1 and Ar2 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0016] R1is hydrogen; deuterium; a halogen radical; 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; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0017] R2and R3are different from each other, and each independently hydrogen; deuterium; a halogen radical; 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 unsubstituted or substituted with deuterium, a halogen radical, a hydroxyl 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,

[0018] r1is 1 or 2, and when r1is 2, two R1are the same as or different from each other,

[0019] r2and r3are each an integer of 1 to 4, and when r2is 2 or more, two or more R2are the same as or different from each other, and when r3is 2 or more, two or more R3are the same as or different from each other,

[0020] L1and L2are the same as or different from each other, and each independently a substituted or unsubstituted arylene group; or a heteroarylene group,

[0021] X1to X10, X'9, and X'10are the same as or different from each other, and each independently O; or S,

[0022] Z1to Z6are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0023] La, La', La", and La"'are the same as or different from each other, and each independently a direct bond; or -C(=O)-L-,

[0024] L is a substituted or unsubstituted arylene group,

[0025] a, b, c, d, p, and q are the same as or different from each other, and each independently an integer of 0 to 6, and when a, b, c, d, p, and q are each 2 or more, the structures in each bracket are the same as or different from each other,

[0026] t and t' are the same as or different from each other, and each independently an integer of 1 to 6, and when t and t' are each 2 or more, the structures in the brackets are the same as or different from each other,

[0027] m and n are the same as each other, and are 0 or 1,

[0028] when m and n are 0, t, r and s are 1, and La is -C(=0)-L-,

[0029] when m and n are 1, t is an integer of 1 to 6, r+s=l, r is a real number of 0

[0030] m' and n' are the same as each other, and are 0 or 1,

[0031] when m' and n' are 0, t', x and y are 1, and La' is -C(=0)-L-,

[0032] when m' and n' are 1, t' is an integer of 1 to 6, x+y=l, x is a real number of 0

[0033] * means a moiety connected to the main chain of the resin.

[0034] One exemplary embodiment of the present application provides a method for producing a resin, the method comprising polymerization of a composition for producing a resin, the composition for producing a resin comprising: a compound of the following Chemical Formula la; a compound of the following Chemical Formula 2a; and 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor.

[0035] [Chemical Formula la]

[0036]

[0037] [Chemical Formula 2a]

[0038]

[0039] In Chemical Formula la and Chemical Formula 2a,

[0040] Ar1, Ar2, R1 to R3, r1 to r3, X1 to X8, a, b, c, d, L1, L2 and Z1 to Z4 are defined as the same as those defined in Chemical Formula 1 and Chemical Formula 2.

[0041] Another exemplary embodiment of the present application provides a resin composition comprising the resin according to the above exemplary embodiment.

[0042] Still another exemplary embodiment of the present application provides a molded article comprising the resin composition according to the above exemplary embodiment.

[0043] Advantages

[0044] The resin according to the exemplary embodiment of the present application has a high refractive index and high transparency.

[0045] By using the resin according to the exemplary embodiment of the present application, an excellent optical lens can be obtained. BRIEF DESCRIPTION OF DRAWINGS

[0046] Figure 1 is a graph showing a reduction rate of a lens thickness according to a difference in refractive index. DETAILED DESCRIPTION

[0047] Hereinafter, specific exemplary embodiments will be described in more detail.

[0048] In the entire specification of the present application, the term "combination thereof" included in the Markush type expression means a mixture or a combination of one or more selected from the constituent elements described in the Markush type expression, and means to include one or more selected from the above-described constituent elements.

[0049] Examples of substituents in the present specification will be described below, but are not limited thereto.

[0050] In the present specification, means a moiety to be connected.

[0051] In the present specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more are substituted, the two or more substituents can be the same as or different from each other.

[0052] In the present specification, the term "substituted or unsubstituted" means that substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a hydroxyl group; a cyano group; an alkyl group; a cycloalkyl group; an alkoxy group; an alkenyl group; an aryloxy group; an arylthio group; an alkylthio group; a silyl group; an aryl group; a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; and a heterocyclic group, with a substituent bonded to two or more substituents among the exemplified substituents, or not having a substituent.

[0053] In the present specification, the fact that two or more substituents are bonded means that a hydrogen of any one substituent is bonded to another substituent. For example, when two substituents are bonded to each other, a phenyl group and a naphthyl group can be bonded to each other to become a substituent Further, the case where three substituents are bonded to each other includes not only the case where (substituent 1) - (substituent 2) - (substituent 3) are sequentially bonded to each other, but also the case where (substituent 2) and (substituent 3) are bonded to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group can be bonded to each other to form a substituent The above definition also applies to cases where four or more substituents are connected to each other.

[0054] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0055] In this specification, alkyl groups may be straight-chain or branched, and there is no particular limitation on the number of carbon atoms, but it is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0056] In this specification, there is no particular limitation on cycloalkyl groups, but they are preferably composed of 3 to 30 carbon atoms, and specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc.

[0057] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc.

[0058] In this specification, the alkenyl group can be linear or branched, and its number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, etc. Examples of the aryl group include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto.

[0059] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group can be monocyclic or polycyclic.

[0060] When the aryl group is a monocyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 6 to 50. Specific examples of the monocyclic aryl group include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto.

[0061] When the aryl group is a polycyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 10 to 50. Specific examples of the polycyclic aryl group include naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, phenalenyl, phenyl, fluorenyl, and the like, but are not limited thereto.

[0062] In the present specification, the fluorenyl group can be substituted, and adjacent groups can be bonded to each other to form a ring.

[0063] Examples of the case where the fluorenyl group is substituted include

[0064] but are not limited thereto.

[0065] In the present specification, the "adjacent" groups can mean a substituent that substitutes an atom directly connected to an atom substituted by a corresponding substituent, a substituent disposed spatially closest to the corresponding substituent, or another substituent that substitutes an atom substituted by the corresponding substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituting the same carbon in an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0066] In the present specification, the heteroaryl group contains one or more atoms other than carbon (i.e., one or more heteroatoms), and specifically, the heteroatoms can include one or more atoms selected from O, N, Se, S, and the like. The number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30, and the heteroaryl group can be monocyclic or polycyclic. Examples of the heteroaryl group include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phtalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benz oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthridinyl, phenanthrolinyl, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol, phen Phenothiazinyl, dihydroindocarbazolyl, spirofluorenyl succinyl, spirofluorenyl thiopheneyl, tetrahydronaphthothiopheneyl, tetrahydronaphthofuranyl, tetrahydrobenzothiopheneyl, tetrahydrobenzofuranyl, etc., but not limited to these.

[0067] In this specification, silane can be alkylsilane, arylsilane, alkylarylsilane, heteroarylsilane, etc. The above examples of alkyl can be applied to alkyl groups in alkylsilane, the above examples of aryl can be applied to aryl groups in arylsilane, the examples of alkyl and aryl can be applied to alkyl and aryl groups in alkylarylsilane, and the examples of heteroaryl can be applied to heteroaryl groups in heteroarylsilane.

[0068] In this specification, the hydrocarbon cyclogroup can be an aromatic hydrocarbon cyclogroup, an aliphatic hydrocarbon cyclogroup, or a fused cyclogroup of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and can be selected from examples of cycloalkyl, aryl, and combinations thereof. Examples of hydrocarbon cyclogroups include phenyl, cyclohexyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]octyl, tetrahydronaphthyl, tetrahydroanthrayl, 1,2,3,4-tetrahydro-1,4-bridged methylenenaphthyl, 1,2,3,4-tetrahydro-1,4-bridged ethylnaphthyl, spirocyclopentanefluorenyl, spiroadamantanefluorenyl, spirocyclohexanefluorenyl, etc., but are not limited thereto.

[0069] In this specification, a heterocyclic group comprises one or more atoms other than carbon (i.e., one or more heteroatoms), and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The heterocyclic group may be monocyclic or polycyclic, and may be an aromatic heterocyclic group; an aliphatic heterocyclic group; a fused-ring group of aromatic heterocycles and aliphatic heterocycles; a fused-ring group of aliphatic hydrocarbon rings, aromatic hydrocarbon rings and aromatic heterocycles, or a fused-ring group of aliphatic hydrocarbon rings, aromatic hydrocarbon rings and aliphatic heterocycles, and the aromatic heterocyclic group may be selected from examples of heteroaryl groups.

[0070] In this specification, aliphatic heterocyclic group means an aliphatic cyclic group containing one or more heteroatoms. Aliphatic heterocyclic groups include all of the following: aliphatic cyclic groups with single bonds, aliphatic cyclic groups containing multiple bonds, or aliphatic cyclic groups in the form of ring fusion containing both single and multiple bonds. Examples of aliphatic heterocycles include epoxy groups, ethylene oxide groups, tetrahydrofuranyl groups, and 1,4-di(oxygenated) groups. Alkyl, pyrrolidinyl, piperidinyl, morpholinyl, oxetaneheptyl, azirheptanyl, thioheptanyl, tetrahydronaphthothiophene, tetrahydronaphthofuranyl, tetrahydrobenzothiophene, tetrahydrobenzofuranyl, etc., but not limited to these.

[0071] In the present specification, an aryloxy group can be represented by -ORd, and the description about the above-described aryl group is applied to Rd.

[0072] In the present specification, an arylthio group can be represented by -SRs1, and the description about the above-described aryl group is applied to Rs1.

[0073] In the present specification, an alkylthio group can be represented by -SRs2, and the description about the above-described alkyl group is applied to Rs2.

[0074] In the present specification, an alkylene group means a group having two bonding sites in an alkyl group, that is, a divalent group. The above-described description about the alkyl group can be applied to the alkylene group, except that the alkylene group is divalent.

[0075] In the present specification, a cycloalkylene group means a group having two bonding sites in a cycloalkyl group, that is, a divalent group. The above-described description about the cycloalkyl group can be applied to the cycloalkylene group, except that the cycloalkylene group is divalent.

[0076] In the present specification, a fused ring group of a divalent aromatic hydrocarbon ring and aliphatic hydrocarbon ring means a ring group having two bonding sites in a fused ring group of an aromatic hydrocarbon ring and aliphatic hydrocarbon ring, that is, a divalent group. The above-described description about the fused ring group of the aromatic hydrocarbon ring and aliphatic hydrocarbon ring can be applied, except that the groups are each divalent groups.

[0077] In the present specification, an arylene group means a group having two bonding sites in an aryl group, that is, a divalent group. The above-described description about the aryl group can be applied to the arylene group, except that the arylene group is divalent.

[0078] Hereinafter, preferred exemplary embodiments of the present application will be described in detail. However, the exemplary embodiments of the present application can be modified in various other forms, and the scope of the present application is not limited to the exemplary embodiments to be described below.

[0079] According to one exemplary embodiment of the present specification, one or more units of Chemical Formula 1 can be included in the resin, and when two or more are included, the units are the same as or different from each other.

[0080] According to one exemplary embodiment of the present specification, one or more units of Chemical Formula 2 can be included in the resin, and when two or more are included, the units are the same as or different from each other.

[0081] One exemplary embodiment of the present application provides a resin including a unit of Chemical Formula 1 and a unit of Chemical Formula 2.

[0082] It can be seen from the form of the relationship between the molecular structure and the refractive index known according to Lorentz-Lorenz's formula that the refractive index of a material composed of molecules increases by increasing the electron density of the molecules and decreasing the molecular volume.

[0083] Since the core structure of Chemical Formula 1 is a phenylene group, the resin including the unit of Chemical Formula 1 has a small molecular volume and is excellent in packing ability, and thus the refractive index of the resin can be increased. In addition, when Ar1 and Ar2 are electron-rich substituents, such as a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, the refractive index of the resin can be further increased by increasing the electron density of the structure of Chemical Formula 1.

[0084] Since the substituents of the benzene rings on both sides of the fluorene structure of Chemical Formula 2 form an asymmetric structure and R2 and R3 are included as substituents, the refractive index of a molded article including the resin can be increased by increasing the electron density.

[0085] That is, the resin according to the present application includes the unit of Chemical Formula 1 and the unit of Chemical Formula 2 to increase the reactivity so that the resin is easily prepared, and the electron density of each core structure can be increased to increase the refractive index of the resin. Thus, the resin according to one exemplary embodiment of the present specification has a high refractive index and a high transparency, and an optical lens, an optical film, or an optical resin using the same has a small thickness and can exhibit excellent optical properties. According to one exemplary embodiment of the present specification, the resin is a polyester resin, or a polyester-polycarbonate resin.

[0086] According to one exemplary embodiment of the present specification, Chemical Formula 1 is the following Chemical Formula 1-1 or Chemical Formula 1-2.

[0087] [Chemical Formula 1-1]

[0088]

[0089] [Chemical Formula 1-2]

[0090]

[0091] In Chemical Formula 1-1,

[0092] *, Ar1, Ar2, R1, r1, X1 to X4, Z1, Z2, a, and b are the same as those defined in Chemical Formula 1,

[0093] La is -C(=O)-L-,

[0094] L is a substituted or unsubstituted arylene group,

[0095] and in Chemical Formula 1-2,

[0096] *, Ar1, Ar2, R1, r1, X1 to X4, X9, X10, Z1, Z2, Z5, a, b, t, and p are the same as those defined in Chemical Formula 1,

[0097] Laand La' are the same as or different from each other, and each is independently a direct bond; or -C(=O)-L-,

[0098] L is a substituted or unsubstituted arylene group,

[0099] r is a real number of 0 < r < 1 as a mole fraction,

[0100] s is a real number of 0 < s < 1 as a mole fraction, and

[0101] r + s = 1.

[0102] According to one exemplary embodiment of the present specification, Chemical Formula 1 is Chemical Formula 1-1.

[0103] According to one exemplary embodiment of the present specification, Chemical Formula 1 is Chemical Formula 1-2.

[0104] According to one exemplary embodiment of the present specification, Chemical Formula 2 is the following Chemical Formula 2-1 or Chemical Formula 2-2.

[0105] [Chemical Formula 2-1]

[0106]

[0107] [Chemical Formula 2-2]

[0108]

[0109] In Chemical Formula 2-1,

[0110] *, R2, R3, r2, r3, L1, L2, X5 to X8, Z3, Z4, c, and d are the same as those defined in Chemical Formula 2,

[0111] La' is -C(=O)-L-,

[0112] L is a substituted or unsubstituted arylene group,

[0113] and in Chemical Formula 2-2,

[0114] *, R2, R3, r2, r3, L1, L2, X5 to X8, X'9, X'10, Z3, Z4, Z6, c, d, t', and q are the same as those defined in Chemical Formula 2,

[0115] La' and La'" are the same as or different from each other, and are each independently a direct bond; or -C(=0)-L-, L being a substituted or unsubstituted arylene group,

[0116] L is a substituted or unsubstituted arylene group,

[0117] x is a real number of 0 < x < 1 as a mole fraction,

[0118] y is a real number of 0 < y < 1 as a mole fraction, and

[0119] x + y = 1.

[0120] According to one exemplary embodiment of the present specification, Chemical Formula 2 is Chemical Formula 2-1.

[0121] According to one exemplary embodiment of the present specification, Chemical Formula 2 is Chemical Formula 2-2.

[0122] According to one exemplary embodiment of the present specification, the resin further comprises a unit of the following Chemical Formula 3.

[0123] [Chemical Formula 3]

[0124]

[0125] In Chemical Formula 3,

[0126] L11 is a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; or a substituted or unsubstituted arylene group,

[0127] l11 is an integer of 1 to 5, and when l11 is 2 or more, two or more L11 are the same as or different from each other,

[0128] X11 to X16 are the same as or different from each other, and are each independently O; or S,

[0129] Z11 to Z13 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,

[0130] Lb and Lb' are the same as or different from each other, and are each independently a direct bond; or -C(=0)-L'-, L' being a substituted or unsubstituted arylene group,

[0131] a', b', and p' are the same as or different from each other, and are each independently an integer of 0 to 6, and when a', b', and p' are each 2 or more, the structures in each bracket are the same as or different from each other,

[0132] t" is an integer of 1 to 6, and when t" is 2 or more, the structures in the brackets are the same as or different from each other,

[0133] m" and n" are the same as each other, and are 0 or 1,

[0134] when m" and n" are 0, t", r' and s' are 1, and Lb is -C(=O)-L'-,

[0135] when m" and n" are 1, t" is an integer of 1 to 6, r'+s'=1, r' is a real number of 0

[0136] * means a moiety bonded to the main chain of the resin.

[0137] According to one exemplary embodiment of the present specification, one or more units of Chemical Formula 3 can be included in the resin, and when two or more are included, the units are the same as or different from each other.

[0138] By further including the unit represented by Chemical Formula 3, the resin can supplement the glass transition temperature (Tg) of the resin including the units of Chemical Formula 1 and Chemical Formula 2 or make the chain behavior of the resin flexible, and has a technical effect of facilitating injection molding processing of a molded article.

[0139] One exemplary embodiment of the present specification provides a resin including a unit of Chemical Formula 1; a unit of Chemical Formula 2; and a unit of Chemical Formula 3.

[0140] According to one exemplary embodiment of the present specification, Chemical Formula 3 is the following Chemical Formula 3-1 or Chemical Formula 3-2.

[0141] [Chemical Formula 3-1]

[0142]

[0143] [Chemical Formula 3-2]

[0144]

[0145] In Chemical Formula 3-1,

[0146] *, L11, l11, X11 to X14, Z11, Z12, a' and b' are the same as those defined in Chemical Formula 3,

[0147] Lb is -C(=O)-L'-,

[0148] L' is a substituted or unsubstituted arylene group,

[0149] and in Chemical Formula 3-2,

[0150] *, the definitions of L11, l11, X11 to X16, Z11, Z12, Z13, a', b', t", and p' are the same as those defined in Chemical Formula 3,

[0151] Lb and Lb' are the same as or different from each other, and each is independently a direct bond; or -C(=O)-L'-,

[0152] L' is a substituted or unsubstituted arylene group,

[0153] r' is a real number of 0 < r' < 1 as a mole fraction,

[0154] s' is a real number of 0 < s' < 1 as a mole fraction, and

[0155] r' + s' = 1.

[0156] According to one exemplary embodiment of the present specification, Chemical Formula 3 is Chemical Formula 3-1.

[0157] According to one exemplary embodiment of the present specification, Chemical Formula 3 is Chemical Formula 3-2.

[0158] According to one exemplary embodiment of the present specification, Chemical Formula 1 is the following Chemical Formula 1-1-1.

[0159] [Chemical Formula 1-1-1]

[0160]

[0161] In Chemical Formula 1-1-1,

[0162] *, the definitions of Ar1, Ar2, R1, r1, X1 to X4, Z1, Z2, a, and b are the same as those defined in Chemical Formula 1, and

[0163] L1 is a substituted or unsubstituted arylene group.

[0164] According to one exemplary embodiment of the present specification, Chemical Formula 2 is the following Chemical Formula 2-1-1.

[0165] [Chemical Formula 2-1-1]

[0166]

[0167] In Chemical Formula 2-1-1,

[0168] *, the definitions of R2, R3, r2, r3, L1, L2, X5 to X8, Z3, Z4, c, and d are the same as those defined in Chemical Formula 2, and

[0169] L3 is a substituted or unsubstituted arylene group.

[0170] According to one exemplary embodiment of the present specification, Chemical Formula 3 is the following Chemical Formula 3-1-1.

[0171] [Chemical Formula 3-1-1]

[0172]

[0173] In Chemical Formula 3-1-1,

[0174] * the definitions of L11, l11, X11 to X14, Z11, Z12, a', and b' are the same as those defined in Chemical Formula 3,

[0175] and L'1 is a substituted or unsubstituted arylene group.

[0176] According to one exemplary embodiment of the present specification, Chemical Formula 1 is any one of the following Chemical Formulae 1-2-1 to 1-2-4.

[0177] [Chemical Formula 1-2-1]

[0178]

[0179] [Chemical Formula 1-2-2]

[0180]

[0181] [Chemical Formula 1-2-3]

[0182]

[0183] [Chemical Formula 1-2-4]

[0184]

[0185] In Chemical Formulae 1-2-1 to 1-2-4,

[0186] * the definitions of Ar1, Ar2, R1, r1, X1 to X4, X9, X10, Z1, Z2, Z5, a, b, p, t, s, and r are the same as those defined in Chemical Formula 1-2, and

[0187] L1 and L2 are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group.

[0188] According to one exemplary embodiment of the present specification, Chemical Formula 2 is any one of the following Chemical Formulae 2-1-2 to 2-1-5.

[0189] [Chemical Formula 2-1-2]

[0190]

[0191] [Chemical Formula 2-1-3]

[0192]

[0193] [Chemical Formula 2-1-4]

[0194]

[0195] [Chemical Formula 2-1-5]

[0196]

[0197] In Chemical Formulae 2-1-2 to 2-1-5,

[0198] *, R2, L1, L2, X5to X8, Z3, Z4, c, and d are the same as those defined in Chemical Formula 2,

[0199] La'is -C(=O)-L-, and

[0200] L is a substituted or unsubstituted arylene group.

[0201] According to one exemplary embodiment of the present specification, Chemical Formula 2 is any one of the following Chemical Formulae 2-2-1 to 2-2-4.

[0202] [Chemical Formula 2-2-1]

[0203]

[0204] [Chemical Formula 2-2-2]

[0205]

[0206] [Chemical Formula 2-2-3]

[0207]

[0208] [Chemical Formula 2-2-4]

[0209]

[0210] In Chemical Formulae 2-2-1 to 2-2-4,

[0211] *, R2, L1, L2, X5to X8, X'9, X'10, Z3, Z4, Z6, c, d, t', and q are the same as those defined in Chemical Formula 2-2,

[0212] La'and La'"are the same as or different from each other, and are each independently a direct bond; or -C(=O)-L-,

[0213] L is a substituted or unsubstituted arylene group,

[0214] x is a real number of 0 < x < 1 as a mole fraction,

[0215] y is a real number of 0 < y < 1 as a mole fraction, and

[0216] x + y = 1.

[0217] According to one exemplary embodiment of the present specification, Chemical Formula 2 is any one of the following Chemical Formulas 2-1-6 to 2-1-9.

[0218] [Chemical Formula 2-1-6]

[0219]

[0220] [Chemical Formula 2-1-7]

[0221]

[0222] [Chemical Formula 2-1-8]

[0223]

[0224] [Chemical Formula 2-1-9]

[0225]

[0226] In Chemical Formulas 2-1-6 to 2-1-9,

[0227] *, R2, L1, L2, X5 to X8, Z3, Z4, c, and d are the same as those defined in Chemical Formula 2, and

[0228] L3 is a substituted or unsubstituted arylene group.

[0229] According to one exemplary embodiment of the present specification, Chemical Formula 2 is any one of the following Chemical Formulas 2-2-6 to 2-2-9.

[0230] [Chemical Formula 2-2-6]

[0231]

[0232] [Chemical Formula 2-2-7]

[0233]

[0234] [Chemical Formula 2-2-8]

[0235]

[0236] [Chemical Formula 2-2-9]

[0237]

[0238] In Chemical Formula 2-2-6 to Chemical Formula 2-2-9,

[0239] Z3, Z4, Z6, X5 to X8, X'9, X'10, c, d, q, t', x, y, L1, L2, R2, R3, r2, and r3 are the same as those defined in Chemical Formula 2-2, and

[0240] L3 and L4 are the same as or different from each other, and each is independently a substituted or unsubstituted arylene.

[0241] According to one exemplary embodiment of the present specification, Chemical Formula 3 is any one of the following Chemical Formula 3-2-1 to Chemical Formula 3-2-4.

[0242] [Chemical Formula 3-2-1]

[0243]

[0244] [Chemical Formula 3-2-2]

[0245]

[0246] [Chemical Formula 3-2-3]

[0247]

[0248] [Chemical Formula 3-2-4]

[0249]

[0250] In Chemical Formula 3-2-1 to Chemical Formula 3-2-4,

[0251] *, L11, l11, X11 to X16, Z11 to Z13, a', b', s', t", r', and p' are the same as those defined in Chemical Formula 3-3, and

[0252] L'1 and L'2 are the same as or different from each other, and each is independently a substituted or unsubstituted arylene.

[0253] According to one exemplary embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, R1is hydrogen, X1to X4, X9, and X10are O, Z1, Z2, and Z5are the same as or different from each other, and each is independently a straight-chain or branched alkylene group having 1 to 30 carbon atoms, and La is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0254] According to one exemplary embodiment of the present specification, R2and R3are different from each other, and each is independently hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is unsubstituted, L1and L2are the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, X5to X8, X'9, and X'10are O, Z3, Z4, and Z6are the same as or different from each other, and each is independently a straight-chain or branched alkylene group having 1 to 30 carbon atoms, and La' is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0255] According to one exemplary embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0256] According to one exemplary embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0257] According to one exemplary embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0258] According to one exemplary embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each is independently a polycyclic aryl group having 10 to 30 carbon atoms.

[0259] According to one exemplary embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each is independently a polycyclic aryl group having 10 to 20 carbon atoms.

[0260] According to one exemplary embodiment of the present specification, Ar1and Ar2are naphthyl groups.

[0261] According to one exemplary embodiment of the present specification, R1is hydrogen.

[0262] According to one exemplary embodiment of the present specification, X1is O.

[0263] According to one exemplary embodiment of the present specification, X2is O.

[0264] According to one exemplary embodiment of the present specification, X3is O.

[0265] According to one exemplary embodiment of the present specification, X4is O.

[0266] According to one exemplary embodiment of the present specification, X9is O.

[0267] According to one exemplary embodiment of the present specification, X10is O.

[0268] According to one exemplary embodiment of the present specification, Z1to Z6are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene having 1 to 10 carbon atoms.

[0269] According to one exemplary embodiment of the present specification, Z1, Z2, and Z5are the same as or different from each other, and each is independently a linear or branched alkylene having 1 to 30 carbon atoms.

[0270] According to one exemplary embodiment of the present specification, Z1, Z2, and Z5are the same as or different from each other, and each is independently a linear or branched alkylene having 1 to 20 carbon atoms.

[0271] According to one exemplary embodiment of the present specification, Z1, Z2, and Z5are the same as or different from each other, and each is independently ethylene; or isopropylene.

[0272] According to one exemplary embodiment of the present specification, Laand La”are the same as or different from each other, and each is independently a direct bond; or -C(=O)-L-.

[0273] According to one exemplary embodiment of the present specification, Laand La”are different from each other, and each is independently a direct bond; or -C(=O)-L-.

[0274] According to one exemplary embodiment of the present specification, Laand La”are a direct bond.

[0275] According to one exemplary embodiment of the present specification, Laand La”are -C(=O)-L-.

[0276] According to one exemplary embodiment of the present specification, La”is a direct bond, and Lais -C(=O)-L-.

[0277] According to one exemplary embodiment of the present specification, La is a direct bond, and La" is -C(=0)-L-.

[0278] According to one exemplary embodiment of the present specification, L is a monocyclic or polycyclic arylene having 6 to 30 carbon atoms.

[0279] According to one exemplary embodiment of the present specification, L is a monocyclic or polycyclic arylene having 6 to 20 carbon atoms.

[0280] According to one exemplary embodiment of the present specification, L is a phenylene; or naphthylene.

[0281] According to one exemplary embodiment of the present specification, L1and L2are the same as or different from each other, and each is independently a monocyclic or polycyclic arylene having 6 to 30 carbon atoms.

[0282] According to one exemplary embodiment of the present specification, L1and L2are the same as or different from each other, and each is independently a monocyclic or polycyclic arylene having 6 to 20 carbon atoms.

[0283] According to one exemplary embodiment of the present specification, L1and L2are the same as or different from each other, and each is independently a phenylene; or naphthylene.

[0284] According to one exemplary embodiment of the present specification, R2and R3are different from each other, and each is independently hydrogen; or an unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms.

[0285] According to one exemplary embodiment of the present specification, R2and R3are different from each other, and each is independently hydrogen; or an unsubstituted monocyclic or polycyclic aryl having 6 to 20 carbon atoms.

[0286] According to one exemplary embodiment of the present specification, R2and R3are different from each other, and each is independently hydrogen; or an unsubstituted polycyclic aryl having 10 to 30 carbon atoms.

[0287] According to one exemplary embodiment of the present specification, R2and R3are different from each other, and each is independently hydrogen; or an unsubstituted polycyclic aryl having 10 to 20 carbon atoms.

[0288] According to one exemplary embodiment of the present specification, R2and R3are different from each other, and each is independently hydrogen; or a naphthyl.

[0289] According to one exemplary embodiment of the present specification, R2is a naphthyl.

[0290] According to one exemplary embodiment of the present specification, R3is hydrogen.

[0291] According to one exemplary embodiment of the present specification, L1and L2are the same as or different from each other, and each is independently a monocyclic or polycyclic arylene having 6 to 30 carbon atoms.

[0292] According to one exemplary embodiment of the present specification, L1and L2are the same as or different from each other, and each is independently a monocyclic or polycyclic arylene having 6 to 20 carbon atoms.

[0293] According to one exemplary embodiment of the present specification, L1and L2are the same as or different from each other, and each is independently a polycyclic arylene having 10 to 30 carbon atoms.

[0294] According to one exemplary embodiment of the present specification, L1and L2are the same as or different from each other, and each is independently a polycyclic arylene having 10 to 20 carbon atoms.

[0295] According to one exemplary embodiment of the present specification, L1and L2are a divalent naphthyl group.

[0296] According to one exemplary embodiment of the present specification, X5is O.

[0297] According to one exemplary embodiment of the present specification, X6is O.

[0298] According to one exemplary embodiment of the present specification, X7is O.

[0299] According to one exemplary embodiment of the present specification, X8is O.

[0300] According to one exemplary embodiment of the present specification, X'9is O.

[0301] According to one exemplary embodiment of the present specification, X'10is O.

[0302] According to one exemplary embodiment of the present specification, Z3, Z4, and Z6are the same as or different from each other, and each is independently a linear or branched alkylene having 1 to 30 carbon atoms.

[0303] According to one exemplary embodiment of the present specification, Z3, Z4, and Z6are the same as or different from each other, and each is independently a linear or branched alkylene having 1 to 20 carbon atoms.

[0304] According to one exemplary embodiment of the present specification, Z3, Z4, and Z6are ethylene.

[0305] According to one exemplary embodiment of the present specification, La' and La'' are the same as or different from each other, and each is independently a direct bond; or -C(=O)-L-.

[0306] According to an exemplary embodiment of the present specification, La' and La'" are different from each other, and each is independently a direct bond; or -C(=O)-L-.

[0307] According to an exemplary embodiment of the present specification, La' and La'" are a direct bond.

[0308] According to an exemplary embodiment of the present specification, La' and La'" are -C(=O)-L-.

[0309] According to an exemplary embodiment of the present specification, La' is a direct bond, and La'" is -C(=O)-L-.

[0310] According to an exemplary embodiment of the present specification, La' is a direct bond, and La'" is -C(=O)-L-.

[0311] According to an exemplary embodiment of the present specification, L is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0312] According to an exemplary embodiment of the present specification, L is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0313] According to an exemplary embodiment of the present specification, L is a phenylene group; or a naphthylene group.

[0314] According to an exemplary embodiment of the present specification, L3 and L4 are the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0315] According to an exemplary embodiment of the present specification, L3 and L4 are the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0316] According to an exemplary embodiment of the present specification, L3 and L4 are the same as or different from each other, and each is independently a phenylene group; or a naphthylene group.

[0317] According to an exemplary embodiment of the present specification, a is 1.

[0318] According to an exemplary embodiment of the present specification, b is 1.

[0319] According to an exemplary embodiment of the present specification, c is 1.

[0320] According to an exemplary embodiment of the present specification, d is 1.

[0321] According to an exemplary embodiment of the present specification, a is 0.

[0322] According to one exemplary embodiment of the present specification, b is 0.

[0323] According to one exemplary embodiment of the present specification, c is 0.

[0324] According to one exemplary embodiment of the present specification, d is 0.

[0325] According to one exemplary embodiment of the present specification, p is 0.

[0326] According to one exemplary embodiment of the present specification, q is 0.

[0327] According to one exemplary embodiment of the present specification, p is 1.

[0328] According to one exemplary embodiment of the present specification, q is 1.

[0329] According to one exemplary embodiment of the present specification, t is 1.

[0330] According to one exemplary embodiment of the present specification, t' is 1.

[0331] According to one exemplary embodiment of the present specification, L11is a monocyclic or polycyclic alkylene radical having 1 to 30 carbon atoms; a fused ring radical of a bivalent monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic arylene radical having 6 to 50 carbon atoms, which is unsubstituted or substituted by a straight-chain or branched alkyl radical having 1 to 30 carbon atoms or by a monocyclic or polycyclic aryl radical having 6 to 30 carbon atoms.

[0332] According to one exemplary embodiment of the present specification, L11is a monocyclic or polycyclic alkylene radical having 1 to 20 carbon atoms; a fused ring radical of a bivalent monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and an aliphatic hydrocarbon ring having 3 to 20 carbon atoms; or a monocyclic or polycyclic arylene radical having 6 to 30 carbon atoms, which is unsubstituted or substituted by a straight-chain or branched alkyl radical having 1 to 20 carbon atoms or by a monocyclic or polycyclic aryl radical having 6 to 20 carbon atoms.

[0333] According to one exemplary embodiment of the present specification, L11is unsubstituted or methyl-substituted methylene; isopropylidene; unsubstituted or methyl- or phenyl-substituted phenylene; a bivalent naphthyl radical; or a bivalent fluorenyl radical.

[0334] According to one exemplary embodiment of the present specification, l11is 1.

[0335] According to one exemplary embodiment of the present specification, l11is 2, and the two L11are identical to or different from each other.

[0336] According to one exemplary embodiment of the present specification, l11 is 3, and the three L11 are the same or different from each other.

[0337] According to one exemplary embodiment of the present specification, X11 is O.

[0338] According to one exemplary embodiment of the present specification, X12 is O.

[0339] According to one exemplary embodiment of the present specification, X13 is O.

[0340] According to one exemplary embodiment of the present specification, X14 is O.

[0341] According to one exemplary embodiment of the present specification, X15 is O.

[0342] According to one exemplary embodiment of the present specification, X16 is O.

[0343] According to one exemplary embodiment of the present specification, Z11 to Z13 are the same or different from each other, and each is independently a linear or branched alkylene having 1 to 30 carbon atoms.

[0344] According to one exemplary embodiment of the present specification, Z11 to Z13 are the same or different from each other, and each is independently a linear or branched alkylene having 1 to 20 carbon atoms.

[0345] According to one exemplary embodiment of the present specification, Z11 to Z13 are ethylene.

[0346] According to one exemplary embodiment of the present specification, Lb and Lb' are the same or different from each other, and each is independently a direct bond; or -C(=O)-L'-.

[0347] According to one exemplary embodiment of the present specification, Lb and Lb' are different from each other, and each is independently a direct bond; or -C(=O)-L'-.

[0348] According to one exemplary embodiment of the present specification, Lb and Lb' are a direct bond.

[0349] According to one exemplary embodiment of the present specification, Lb and Lb' are -C(=O)-L'-.

[0350] According to one exemplary embodiment of the present specification, Lb' is a direct bond, and Lb is -C(=O)-L'-.

[0351] According to one exemplary embodiment of the present specification, Lb is a direct bond, and Lb' is -C(=O)-L'-.

[0352] According to an exemplary embodiment of the present specification, L' is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0353] According to an exemplary embodiment of the present specification, L' is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0354] According to an exemplary embodiment of the present specification, L' is a phenylene group; or a naphthylene group.

[0355] According to an exemplary embodiment of the present specification, L'1and L'2are the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0356] According to an exemplary embodiment of the present specification, L'1and L'2are the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0357] According to an exemplary embodiment of the present specification, L'1and L'2are the same as or different from each other, and each is independently a phenylene group; or a naphthylene group.

[0358] According to an exemplary embodiment of the present specification, a' is 1.

[0359] According to an exemplary embodiment of the present specification, b' is 1.

[0360] According to an exemplary embodiment of the present specification, a' is 0.

[0361] According to an exemplary embodiment of the present specification, b' is 0.

[0362] According to an exemplary embodiment of the present specification, p' is 0.

[0363] According to an exemplary embodiment of the present specification, p' is 1.

[0364] According to an exemplary embodiment of the present specification, t" is 1.

[0365] In an exemplary embodiment of the present application, Chemical Formula 3 is the following Chemical Formula 3-3. The resin further comprises a unit of the following Chemical Formula 3-3.

[0366] [Chemical Formula 3-3]

[0367]

[0368] In Chemical Formula 3-3,

[0369] R11' and R12' are the same as or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group,

[0370] r11' and r12' are the same as or different from each other, and each is independently an integer of 1 to 4, and when r11' and r12' are each 2 or more, the structures in each bracket are the same as or different from each other,

[0371] L11' and L11" are the same as or different from each other, and each is independently a substituted or unsubstituted arylene; or a substituted or unsubstituted heteroarylene,

[0372] Lb is -C(=O)-L'-,

[0373] L' is a substituted or unsubstituted arylene,

[0374] X11 to X14 are the same as or different from each other, and each is independently O; or S,

[0375] Z11 and Z12 are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene; or a substituted or unsubstituted cycloalkylene,

[0376] a' and b' are the same as or different from each other, and each is independently an integer of 0 to 6, and when a' and b' are each 2 or more, the structures in each bracket are the same as or different from each other, and

[0377] * means a moiety linked to the main chain of the resin.

[0378] By further including the unit of Chemical Formula 3-3 in the resin, there is a technical effect of compensating for the low glass transition temperature (Tg) of the unit of Chemical Formula 1.

[0379] In one exemplary embodiment of the present specification, R11' and R12' are the same as or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl having 1 to 30 carbon atoms.

[0380] In one exemplary embodiment of the present specification, R11' and R12' are the same as or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl having 1 to 20 carbon atoms.

[0381] In one exemplary embodiment of the present specification, R11' and R12' are the same as or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl having 1 to 10 carbon atoms.

[0382] In one exemplary embodiment of the present specification, R11' and R12' are hydrogen.

[0383] In an exemplary embodiment of the present specification, L11and L11are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

[0384] In an exemplary embodiment of the present specification, L11and L11are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

[0385] In an exemplary embodiment of the present specification, L11and L11are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 12 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 10 carbon atoms.

[0386] In an exemplary embodiment of the present specification, L11and L11are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

[0387] In an exemplary embodiment of the present specification, L11and L11are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

[0388] In an exemplary embodiment of the present specification, Lb is -C(=O)-L'-.

[0389] In an exemplary embodiment of the present specification, the definition of L' in Chemical Formula 3-3 is the same as described above.

[0390] In an exemplary embodiment of the present specification, X11to X14are O.

[0391] In an exemplary embodiment of the present specification, X11to X14are S.

[0392] In an exemplary embodiment of the present specification, Z11and Z12are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; or a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms.

[0393] In an exemplary embodiment of the present specification, Z11and Z12are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; or a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms.

[0394] In one exemplary embodiment of the present specification, Z11and Z12are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene having 1 to 10 carbon atoms; or a substituted or unsubstituted cycloalkylene having 3 to 10 carbon atoms.

[0395] In one exemplary embodiment of the present specification, Z11and Z12are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene having 1 to 10 carbon atoms; or a substituted or unsubstituted cycloalkylene having 3 to 10 carbon atoms.

[0396] In one exemplary embodiment of the present specification, Z11and Z12are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene having 1 to 10 carbon atoms; or a substituted or unsubstituted cycloalkylene having 3 to 10 carbon atoms.

[0397] In one exemplary embodiment of the present specification, Z11and Z12are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene having 1 to 10 carbon atoms; or a substituted or unsubstituted cycloalkylene having 3 to 10 carbon atoms.

[0398] [Chemical Formula 3-4]

[0399]

[0400] In Chemical Formula 3-4,

[0401] X13and X14are the same as or different from each other, and each is independently O; or S,

[0402] L11is a substituted or unsubstituted alkylene,

[0403] Lb is -C(=O)-L'-,

[0404] L' is a substituted or unsubstituted arylene, and

[0405] * means a moiety connected to the main chain of the resin.

[0406] By further including the unit of Chemical Formula 3 in the resin, the chain behavior of the resin can be made flexible, and has a technical effect of facilitating injection molding of a molded product.

[0407] In one exemplary embodiment of the present specification, X13and X14are O.

[0408] In one exemplary embodiment of the present specification, X13and X14are S.

[0409] In one exemplary embodiment of the present specification, L11is a substituted or unsubstituted alkylene having 1 to 30 carbon atoms.

[0410] In one exemplary embodiment of the present specification, L11is a substituted or unsubstituted alkylene having 1 to 20 carbon atoms.

[0411] In one exemplary embodiment of the present application, L11is a substituted or unsubstituted alkylene having 1 to 10 carbon atoms.

[0412] In one exemplary embodiment of the present application, L11is a substituted or unsubstituted ethylene.

[0413] In one exemplary embodiment of the present application, L11is ethylene.

[0414] In one exemplary embodiment of the present application, L is -C(=0)-L'-, and the above description applies to L'.

[0415] According to one exemplary embodiment of the present application, the resins can each have -OH; -SH; -C02CH3; -COOH; -Cl; or -COOC6H5as two end groups.

[0416] In one exemplary embodiment of the present application, in Chemical Formula 1, r is 0.001 to 0.999 as a mole fraction, s is 0.001 to 0.999 as a mole 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.

[0417] When r and s of Chemical Formula 1 are within the above range, resins having desired physical properties can be obtained by appropriately adjusting r and s as mole fractions.

[0418] In one exemplary embodiment of the present application, in Chemical Formula 2, x is 0.001 to 0.999 as a mole fraction, y is 0.001 to 0.999 as a mole fraction, preferably, x is 0.01 to 0.99 and y is 0.01 to 0.99, and more preferably, x is 0.1 to 0.9 and y is 0.1 to 0.9.

[0419] When x and y of Chemical Formula 2 are within the above range, resins having desired physical properties can be obtained by appropriately adjusting x and y as mole fractions.

[0420] In one exemplary embodiment of the present application, in Chemical Formula 3, r' is 0.001 to 0.999 as a mole fraction, s' is 0.001 to 0.999 as a mole 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.

[0421] When r' and s' of Chemical Formula 3 are within the above range, resins having desired physical properties can be obtained by appropriately adjusting r' and s' as mole fractions.

[0422] In one exemplary embodiment of the present application, the resin has a weight average molecular weight of 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, 8,000 g / mol to 200,000 g / mol. The resin has a weight average molecular weight more preferably of 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, 13,000 g / mol to 70,000 g / mol.

[0423] In one exemplary embodiment of the present application, the resin has a number average molecular weight of 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, 4,500 g / mol to 100,000 g / mol, preferably 5,000 g / mol to 80,000 g / mol.

[0424] When the resin satisfies the above-mentioned ranges of weight average molecular weight and number average molecular weight, the resin can have optimal flowability and processability.

[0425] The weight average molecular weight and the number average molecular weight of the resin are polystyrene equivalent weight average molecular weight.

[0426] In the present application, the weight average molecular weight and the number average molecular weight of the resin and the oligomer used in the preparation thereof can be measured by gel permeation chromatography (GPC) using polystyrene (PS) standards using an Agilent 1200 series. Specifically, the weight average molecular weight can be measured using an Agilent 1200 series apparatus using a Polymer Laboratories PLgel MIX-B 300 mm length column, and in this case, the measurement temperature is 40°C, the solvent used is tetrahydrofuran (THF), and the flow rate is 1 mL / min. Samples of the resin or the oligomer are each prepared at a concentration of 10 mg / 10 mL, then fed in an amount of 10 μL, and the weight average molecular weight or the number average molecular weight is derived using a calibration curve formed using polystyrene standards. In this case, nine types of polystyrene standard products having a molecular weight (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.

[0427] In one exemplary embodiment of the present application, the resin can have a glass transition temperature (Tg) of 90 to 200°C. The glass transition temperature can preferably be 100 to 190°C, 120 to 170°C, 130 to 160°C, 135 to 191°C. When the resin satisfies the above glass transition temperature range, in the case of preparing a resin composition by mixing with a resin having excellent heat resistance and injection moldability and having a glass transition temperature different from the above range, the glass transition temperature is easily adjusted so that the physical properties desired in the present application can be satisfied.

[0428] The glass transition temperature (Tg) can be measured by a differential scanning calorimeter (DSC). Specifically, the glass transition temperature can be measured from a graph obtained by heating 5.5 to 8.5 mg of a resin sample to 270°C under a nitrogen atmosphere, and then scanning the resin sample while heating the resin sample at a heating rate of 10°C / min during the second heating after cooling.

[0429] In one exemplary embodiment of the present application, the resin can have a refractive index of 1.50 to 1.75 measured at a wavelength of 589 nm. The refractive index can preferably be 1.60 to 1.72, and more preferably 1.632 to 1.696. When the resin satisfies the above refractive index, in the case of applying the resin to a molded article such as an optical lens, an optical lens thin and light can be manufactured.

[0430] In one exemplary embodiment of the present application, the resin can have an Abbe number of 5 to 45 measured and calculated at wavelengths of 589 nm, 486 nm, and 656 nm. The Abbe number can preferably be 10 to 25, and more preferably 15.5 to 23.4.

[0431] When the resin satisfies the above Abbe number range, in the case of applying the resin to a molded article such as an optical lens, there is an effect of reducing dispersion and increasing clarity while maintaining a high refractive index. The Abbe number can be specifically obtained by measuring the refractive indices (nD(589 nm), nF(486 nm), and nC(656 nm)) at wavelengths of D (589 nm), F (486 nm), and C (656 nm), respectively, at 20°C, by the following equation. D , n F , and n C

[0432] Abbe number = (n D -1) / (n F -n C )

[0433] ​The refractive index and Abbe number can be measured from a film prepared by applying a solution prepared by dissolving the resin in a solvent to a silicon wafer by spin coating, and can be measured by obtaining a result value according to the wavelength of light using an ellipsometer at 20°C for the applied film. The solution can be applied by spin coating at a rotation speed of 150 rpm to 300 rpm, and the thickness of the applied film can be 5 μm to 20 μm. The silicon wafer is not particularly limited, and any silicon wafer that can measure the refractive index and Abbe number of the resin composition according to the present application can be appropriately used. The solvent can be dimethylacetamide or 1,2-dichlorobenzene, and the solution can be prepared by dissolving a resin sample in an amount of 10% by weight based on the total weight of the solution.

[0434] One exemplary embodiment of the present application provides a method for producing a resin, the method including polymerizing a composition for producing a resin, the composition for producing a resin including: a compound of the following Chemical Formula 1a; a compound of the following Chemical Formula 2a; and 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor.

[0435] [Chemical Formula 1a]

[0436]

[0437] [Chemical Formula 2a]

[0438]

[0439] In Chemical Formula 1a and Chemical Formula 2a,

[0440] Ar1, Ar2, R1 to R3, r1 to r3, X1 to X8, a, b, c, d, L1, L2, and Z1 to Z4 are defined the same as those defined in Chemical Formula 1 and Chemical Formula 2.

[0441] According to one exemplary embodiment of the present specification, the composition for producing a resin further includes a compound of the following Chemical Formula 3a, and the compound of Chemical Formula 1a, the compound of Chemical Formula 2a, and the compound of Chemical Formula 3a are included in an amount of 0.01 mol% to 99.99 mol%: 0.01 mol% to 99.99 mol%: 0 mol% to 99.98 mol%, specifically 1 mol% to 99 mol%: 1 mol% to 99 mol%: 0 mol% to 98 mol%. More specifically, the compound of Chemical Formula 1a, the compound of Chemical Formula 2a, and the compound of Chemical Formula 3a are included in an amount of 5 mol% to 90 mol%: 5 mol% to 90 mol%: 0 mol% to 90 mol%.

[0442] [Chemical Formula 3a]

[0443]

[0444] in Chemical Formula 3a,

[0445] L11is a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; a fused ring group of a substituted or unsubstituted divalent aromatic hydrocarbon ring and aliphatic hydrocarbon ring; or a substituted or unsubstituted arylene group,

[0446] l11is an integer of 1 to 5, and when l11is 2 or more, two or more L11are the same as or different from each other,

[0447] X11to X14are the same as or different from each other, and each is independently O; or S,

[0448] Z11and Z12are the same as or different from each other, and each is independently a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group,

[0449] a' and b' are the same as or different from each other, and each is independently an integer of 0 to 6, and when a' and b' are each 2 or more, the structures in each bracket are the same as or different from each other.

[0450] One exemplary embodiment of the present application provides a method for preparing a resin, the method including polymerizing a composition for preparing a resin, the composition for preparing a resin including a compound of Chemical Formula 1a; a 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 included in an amount of 0.01 mol% to 99.99 mol% : 99.99 mol% to 0.01 mol%. The compound of Chemical Formula 1a and the compound of Chemical Formula 2a are included in an amount of specifically 0.1 mol% to 99.9 mol% : 99.9 mol% to 0.1 mol%, 1 mol% to 99 mol% : 99 mol% to 1 mol%, 5 mol% to 90 mol% : 5 mol% to 90 mol%.

[0451] When the compound of Chemical Formula 1a and the compound of Chemical Formula 2a are included in the above content, the compound is easily polymerized, has a wide range of refractive index or a high refractive index depending on a substituent, and has a wide range of glass transition temperature.

[0452] One exemplary embodiment of the present application provides a method for preparing a resin, the method including polymerizing a composition for preparing a resin, the composition for preparing a resin including a compound of Chemical Formula 1a; a compound of Chemical Formula 2a; a compound of Chemical Formula 3a; and 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor.

[0453] The compound of Chemical Formula 1a, the compound of Chemical Formula 2a, and the compound of Chemical Formula 3a are included in amounts of 0.01 to 99.99 mole %: 0.01 to 99.99 mole %: 0 to 99.98 mole %. Specifically, the compound of Chemical Formula 1a, the compound of Chemical Formula 2a, and the compound of Chemical Formula 3a are included in amounts of 0.1 to 99.9 mole %: 0.1 to 99.9 mole %: 0 to 99.8 mole %, 1 to 99 mole %: 1 to 99 mole %: 0 to 98 mole %, 5 to 90 mole %: 5 to 90 mole %: 0 to 90 mole %.

[0454] When the compound of Chemical Formula 1a, the compound of Chemical Formula 2a, and the compound of Chemical Formula 3a are included in the above amounts, the glass transition temperature (Tg) and the refractive index can be adjusted, and the chain behavior of the resin can be made flexible, such that a technical effect of facilitating injection molding of a molded article is obtained.

[0455] The composition for preparing a resin can further include a solvent.

[0456] The solvent can be, for example, diphenyl ether, dimethylacetamide, or methanol, but is not limited thereto, and any solvent applied in the art can be appropriately used.

[0457] The solvent can be included in an amount of 5 to 60 parts by weight with respect to 100 parts by weight of the composition for preparing a resin.

[0458] The solvent can be included in an amount of preferably 5 to 50 parts by weight, 7 to 45 parts by weight, or 8 to 40 parts by weight with respect to 100 parts by weight of the composition for preparing a resin.

[0459] According to one exemplary embodiment of the present specification, two or more compounds of Chemical Formula 1a can be included. The two or more compounds of Chemical Formula 1a are the same as or different from each other.

[0460] In one exemplary embodiment of the present application, the compound of Chemical Formula 1a can be any one of the following compounds, but is not limited thereto.

[0461]

[0462] In one exemplary embodiment of the present application, the compound of Chemical Formula 2a can be the following compound, but is not limited thereto.

[0463]

[0464] In one exemplary embodiment of the present application, the compound of Chemical Formula 3a can be the following compound, but is not limited thereto.

[0465]

[0466] In one exemplary embodiment of the present application, Chemical Formula 3a is the following Chemical Formula 3a-1. The composition for preparing a resin can further include a compound of the following Chemical Formula 3a-1.

[0467] [Chemical Formula 3a-1]

[0468]

[0469] In Chemical Formula 3a-1, the limitations of the substituents are the same as those in Chemical Formula 3a, and L11' and L11" are the same as those described above.

[0470] In one exemplary embodiment of the present application, Chemical Formula 3a-1 can be represented by the following chemical formula, but is not limited thereto.

[0471]

[0472] In one exemplary embodiment of the present application, Chemical Formula 3a is the following Chemical Formula 3a-2. The composition for preparing a resin can further include a compound of the following Chemical Formula 3a-2.

[0473] [Chemical Formula 3a-2]

[0474]

[0475] In Chemical Formula 3a-2, the limitations of the substituents are the same as those in Chemical Formula 3a.

[0476] In one exemplary embodiment of the present application, Chemical Formula 3a-2 can be represented by the following chemical formula, but is not limited thereto.

[0477]

[0478] One exemplary embodiment of the present application provides a method for preparing a resin, the method including polymerizing a composition for preparing a resin, the composition for preparing a resin preferably including a compound of Chemical Formula 1a; and a compound of Chemical Formula 2a, and including 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor.

[0479] One exemplary embodiment of the present application preferably provides a method for preparing a resin, the method including polymerizing a composition for preparing a resin, the composition for preparing a resin including a compound of Chemical Formula 1a; a compound of Chemical Formula 2a; and a compound of Chemical Formula 3a, and including 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor.

[0480] One exemplary embodiment of the present application provides a method for producing a resin, the method comprising: polymerizing a composition for producing a resin, the composition for producing a resin preferably comprising a compound of Formula la; and a compound of Formula 2a, and comprising a polyester precursor.

[0481] One exemplary embodiment of the present application preferably provides a method for producing a resin, the method comprising: polymerizing a composition for producing a resin, the composition for producing a resin comprising a compound of Formula la; a compound of Formula 2a; and a compound of Formula 3a, and comprising a polyester precursor.

[0482] In one exemplary embodiment of the present specification, the compound of Formula la can be included in an amount of 1 part by weight to 99 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0483] The compound of Formula la can be included in an amount of preferably 1 part by weight to 60 parts by weight, 1 part by weight to 50 parts by weight, 1 part by weight to 40 parts by weight, 1 part by weight to 30 parts by weight, 1 part by weight to 20 parts by weight, or 1 part by weight to 10 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0484] In one exemplary embodiment of the present specification, the compound of Formula 2a can be included in an amount of 1 part by weight to 99 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0485] The compound of Formula 2a can be included in an amount of preferably 1 part by weight to 60 parts by weight, 1 part by weight to 50 parts by weight, 1 part by weight to 40 parts by weight, 1 part by weight to 30 parts by weight, 1 part by weight to 20 parts by weight, or 1 part by weight to 10 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0486] In one exemplary embodiment of the present specification, the polyester precursor can be included in an amount of 1 part by weight to 150 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0487] The polyester precursor can be included in an amount of preferably 1 part by weight to 150 parts by weight, 1 part by weight to 140 parts by weight, 1 part by weight to 130 parts by weight, 1 part by weight to 125 parts by weight, or 1 part by weight to 120 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0488] In one exemplary embodiment of the present specification, the compound of Formula 3a can be included in an amount of 0 parts by weight to 98 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0489] The compound of Formula 3a can be included in an amount of preferably 0 to 60 parts by weight, 1 to 50 parts by weight, 0 to 40 parts by weight, 0 to 30 parts by weight, 0 to 20 parts by weight, or 0 to 10 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0490] One exemplary embodiment of the present application provides a method for producing a resin, the method including polymerizing a composition for producing a resin, the composition for producing a resin preferably including a compound of Formula 1a; and a compound of Formula 2a, and including a polyester precursor and a polycarbonate precursor.

[0491] One exemplary embodiment of the present application provides a method for producing a resin, the method including polymerizing a composition for producing a resin, the composition for producing a resin preferably including a compound of Formula 1a; a compound of Formula 2a; and a compound of Formula 3a, and including a polyester precursor and a polycarbonate precursor.

[0492] In one exemplary embodiment of the present specification, the compound of Formula 1a can be included in an amount of 1 to 99 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0493] The compound of Formula 1a can 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, relative to 100 parts by weight of the composition for producing a resin.

[0494] In one exemplary embodiment of the present specification, the compound of Formula 2a can be included in an amount of 1 to 99 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0495] The compound of Formula 2a can 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, relative to 100 parts by weight of the composition for producing a resin.

[0496] In one exemplary embodiment of the present specification, the polyester precursor can be included in an amount of 1 to 60 parts by weight, relative to 100 parts by weight of the composition for producing a resin.

[0497] The polyester precursor can be included 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 preparing a resin.

[0498] In one exemplary embodiment of the present specification, the polycarbonate precursor can be included in an amount of 1 to 60 parts by weight, relative to 100 parts by weight of the composition for preparing a resin.

[0499] The polycarbonate precursor can be included 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 preparing a resin.

[0500] In one exemplary embodiment of the present specification, the compound of Chemical Formula 3a can be included in an amount of 0 to 98 parts by weight, relative to 100 parts by weight of the composition for preparing a resin.

[0501] The compound of Chemical Formula 3a can be included in an amount of preferably 0 to 60 parts by weight, 1 to 50 parts by weight, 0 to 40 parts by weight, 0 to 30 parts by weight, 0 to 20 parts by weight, or 0 to 10 parts by weight, relative to 100 parts by weight of the composition for preparing a resin.

[0502] The compound of Chemical Formula 1a can be prepared by the following Reaction Scheme 1.

[0503] [Reaction Scheme 1]

[0504]

[0505] In Reaction Scheme 1, the description of the substituents is the same as in Chemical Formula 1.

[0506] The compound of Chemical Formula 2a can be prepared by the following Reaction Scheme 2.

[0507] [Reaction Scheme 2]

[0508]

[0509] In Reaction Scheme 2, the description of the substituents is the same as in Chemical Formula 2, and the limitation of R11 is the same as the limitation of R2 in Chemical Formula 2.

[0510] The compound of Chemical Formula 3a-1 can be prepared by the following Reaction Scheme 3-1.

[0511] [Reaction Scheme 3-1]

[0512]

[0513] In Reaction Scheme 3-1, L1and L2are defined identically to L11' and L11" in Chemical Formula 3a-1.

[0514] Reaction Schemes illustrate processes of synthesizing compounds in which specific substituents are bonded to specific positions, but the present application is not limited thereto, and units corresponding to the scope of Chemical Formula 1a, Chemical Formula 2a, or Chemical Formula 3a-1 can be synthesized by appropriately using starting materials, intermediate materials, solvents, additives, etc. known in the art by synthetic methods known in the art.

[0515] According to one exemplary embodiment of the present specification, the polyester precursor is the following Chemical Formula A, and the polycarbonate precursor is the following Chemical Formula B.

[0516] [Chemical Formula A]

[0517]

[0518] [Chemical Formula B]

[0519]

[0520] In Chemical Formula A and Chemical Formula B,

[0521] Ra1, Ra2, Rb1, and Rb2are the same as or different from each other, and each is independently hydrogen; a halogen group; a hydroxyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

[0522] Ar1is a substituted or unsubstituted arylene group, and

[0523] a1to a4are each 0 or 1.

[0524] According to one exemplary embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2are the same as or different from each other, and each is independently hydrogen; a halogen group; a hydroxyl group; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0525] According to an exemplary embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2are the same as or different from each other, and each is independently hydrogen; a halogen group; a hydroxyl group; a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0526] According to an exemplary embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2are the same as or different from each other, and each is independently hydrogen; a halogen group; a hydroxyl group; a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0527] According to an exemplary embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2are the same as or different from each other, and each is independently hydrogen; a halogen group; a hydroxyl group; a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0528] According to an exemplary embodiment of the present specification, Ra1, Ra2, Rb1, and Rb2are the same as or different from each other, and each is independently hydrogen; -Cl; a hydroxyl 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.

[0529] According to an exemplary embodiment of the present specification, the above-described definition of Laand Lbcan be applied to the definition of Ar1.

[0530] According to an exemplary embodiment of the present specification, Ar1is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0531] According to an exemplary embodiment of the present specification, Ar1is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0532] According to an exemplary embodiment of the present specification, Ar1is a phenylene group; or a naphthylene group.

[0533] According to an exemplary embodiment of the present specification, Chemical Formula A is selected from any one of the following compounds.

[0534]

[0535] According to an exemplary embodiment of the present specification, Chemical Formula B is selected from any one of the following compounds.

[0536]

[0537] If necessary, the polycarbonate precursor is used for linking additional comonomers, and other specific examples thereof which can be applied in addition to the compound of Formula B include phosgene, triphosgene, diphosgene, bromo-triphosgene, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, ditolyl carbonate, bis(chlorophenyl) carbonate, m-cresyl carbonate, dinaphthyl carbonate, bis(diphenyl) carbonate, bis-halogenated formate, and the like, and any one of these or a mixture of two or more thereof can be used.

[0538] In one exemplary embodiment of the present specification, the resin is a polyester resin.

[0539] In one exemplary embodiment of the present specification, it is preferable that the resin is polymerized from the compound of Formula la; Formula 2a; and the polyester precursor of Formula A.

[0540] By polymerizing the compound of Formula la and the polyester precursor of Formula A, the above-described unit of Formula 1 can be formed.

[0541] The compound of Formula la can be used in an amount of 1 to 99 mol parts, relative to 100 mol parts of the total monomers constituting the resin containing the unit of Formula 1.

[0542] The polyester precursor of Formula A can be used in an amount of 1 to 150 mol parts, 50 to 150 mol parts, relative to 100 mol parts of the total monomers constituting the resin of the compound of Formula la.

[0543] By polymerizing the compound of Formula 2a and the polyester precursor of Formula A, the above-described unit of Formula 2 can be formed.

[0544] The compound of Formula 2a can be used in an amount of 1 to 99 mol parts, relative to 100 mol parts of the total monomers constituting the resin containing the unit of Formula 2.

[0545] The polyester precursor of Formula A can be used in an amount of 1 to 150 mol parts, 50 to 150 mol parts, relative to 100 mol parts of the total monomers constituting the resin of the compound of Formula 2a.

[0546] In one exemplary embodiment of the present specification, the polyester resin can further contain a unit of Formula 3.

[0547] By polymerizing the compound of Formula 3a and the polyester precursor of Formula A, the above-described unit of Formula 3 can be formed.

[0548] The compound of Formula 3a can be used in an amount of 1 to 100 parts by mole, 1 to 99 parts by mole, relative to 100 parts by mole of the total monomers constituting the resin including the unit of Formula 3.

[0549] The polyester precursor of Formula A can be used in an amount of 1 to 150 parts by mole, 50 to 150 parts by mole, relative to 100 parts by mole of the total monomers constituting the compound of Formula 3a of the resin.

[0550] In one exemplary embodiment of the present specification, the resin is a polyester-polycarbonate resin.

[0551] In one exemplary embodiment of the present specification, it is preferable that the resin is polymerized from the compound of Formula la; the compound of Formula 2a; the compound of Formula 3a; the polyester precursor of Formula A; and the polycarbonate precursor of Formula B.

[0552] In one exemplary embodiment of the present specification, it is preferable that the resin is polymerized from the compound of Formula la; the compound of Formula 2a; the compound of Formula 3a; the polyester precursor of Formula A; and the polycarbonate precursor of Formula B.

[0553] The unit of Formula 1 described above can be formed by polymerizing the compound of Formula la; the polyester precursor of Formula A; and the polycarbonate precursor of Formula B, the unit of Formula 2 described above can be formed by polymerizing the compound of Formula 2a; the polyester precursor of Formula A; and the polycarbonate precursor of Formula B, and the unit of Formula 3 described above can be formed by polymerizing the compound of Formula 3a; the polyester precursor of Formula A; and the polycarbonate precursor of Formula B.

[0554] The unit of Formula 1 described above can be formed by polymerizing the compound of Formula la; the polyester precursor of Formula A; and the polycarbonate precursor of Formula B.

[0555] The compound of Formula la can be used in an amount of 1 to 100 parts by mole, 1 to 99 parts by mole, relative to 100 parts by mole of the total monomers constituting the resin including the unit of Formula 1.

[0556] The polyester precursor of Formula A can be used in an amount of 1 to 150 parts by mole, 50 to 150 parts by mole, relative to 100 parts by mole of the total monomers constituting the compound of Formula la of the resin.

[0557] The polycarbonate precursor of Formula B can be used in an amount of 1 to 150 parts by mole, 50 to 150 parts by mole, relative to 100 parts by mole of the total monomers constituting the compound of Formula la of the resin.

[0558] The unit of the above-described Chemical Formula 2 can be formed by polymerizing a compound of Chemical Formula 2a; a polyester precursor of Chemical Formula A; and a polycarbonate precursor of Chemical Formula B.

[0559] The compound of Chemical Formula 2a can be used in an amount of 1 to 100 parts by mole, 1 to 99 parts by mole, relative to 100 parts by mole of the total monomers constituting the resin including the unit of Chemical Formula 2.

[0560] The polyester precursor of Chemical Formula A can be used in an amount of 1 to 150 parts by mole, 50 to 150 parts by mole, relative to 100 parts by mole of the total monomers constituting the resin of the compound of Chemical Formula 2a.

[0561] The polycarbonate precursor of Chemical Formula B can be used in an amount of 1 to 150 parts by mole, 50 to 150 parts by mole, relative to 100 parts by mole of the total monomers constituting the resin of the compound of Chemical Formula 2a.

[0562] The unit of the above-described Chemical Formula 3 can be formed by polymerizing a compound of Chemical Formula 3a; a polyester precursor of Chemical Formula A; and a polycarbonate precursor of Chemical Formula B.

[0563] The compound of Chemical Formula 3a can be used in an amount of 1 to 100 parts by mole, 1 to 99 parts by mole, relative to 100 parts by mole of the total monomers constituting the resin including the unit of Chemical Formula 3.

[0564] The polyester precursor of Chemical Formula A can be used in an amount of 1 to 150 parts by mole, 50 to 150 parts by mole, relative to 100 parts by mole of the total monomers constituting the resin of the compound of Chemical Formula 3a.

[0565] The polycarbonate precursor of Chemical Formula B can be used in an amount of 1 to 150 parts by mole, 50 to 150 parts by mole, relative to 100 parts by mole of the total monomers constituting the resin of the compound of Chemical Formula 3a.

[0566] In one exemplary embodiment of the present application, the molar ratio of the compound of Chemical Formula 1a: the compound of Chemical Formula 2a is 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.

[0567] Preferably, the molar ratio of the compound of Chemical Formula 1a: the compound of Chemical Formula 2a is 50:50 to 80:20.

[0568] In one exemplary embodiment of the present application, the molar ratio of the compound of Chemical Formula 1a and the compound of Chemical Formula 2a: the compound of Chemical Formula 3a is 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.

[0569] In one exemplary embodiment of the present application, the molar ratio of the compound of Chemical Formula 1a and the compound of Chemical Formula 2a: the compound of Chemical Formula 3a-1 is 1:9 to 9:1.

[0570] In one exemplary embodiment of the present application, the molar ratio of the compound of Chemical Formula 1a and the compound of Chemical Formula 2a: the compound of Chemical Formula 3a-2 is 1:9 to 9:1.

[0571] For polymerization of the resin according to the present application, a method known in the art can be used.

[0572] It is preferable that the polymerization is performed by a melt polycondensation method.

[0573] In the melt polycondensation method, a composition used for preparing the resin is used, a catalyst can be further applied as necessary, and the melt polycondensation can be performed with heating and further under normal pressure or reduced pressure, while removing a by-product compound through an ester exchange reaction. As the catalyst, a material generally applied in the art can be used.

[0574] Specifically, in the melt polycondensation method, it is preferable that the compound of Chemical Formula 1a; the compound of Chemical Formula 2a; and a polyester precursor are melted in a reaction vessel, and then the reaction is performed in a state allowing the by-product compound to remain. The preparation method can further include the compound of Chemical Formula 3a.

[0575] More specifically, in the melt polycondensation method, it is preferable that the compound of Chemical Formula 1a; the compound of Chemical Formula 2a; the compound of Chemical Formula 3a; and a polyester precursor are melted in a reaction vessel, and then the reaction is performed in a state allowing the by-product compound to remain.

[0576] Alternatively, in the melt polycondensation method, it is preferable that the compound of Chemical Formula 1a; the compound of Chemical Formula 2a; a polyester precursor; and a polycarbonate precursor are melted in a reaction vessel, and then the reaction is performed in a state allowing the by-product compound to remain. The preparation method can further include the compound of Chemical Formula 3a.

[0577] Even more specifically, in the melt polycondensation method, it is preferable that the compound of Chemical Formula 1a; the compound of Chemical Formula 2a; the compound of Chemical Formula 3a; a polyester precursor; and a polycarbonate precursor are melted in a reaction vessel, and then the reaction is performed in a state allowing the by-product compound to remain.

[0578] To allow the by-product compound to stay, the pressure can be controlled by shutting down the reaction device, or reducing the pressure or increasing the pressure.

[0579] The reaction time of the process is 20 minutes or more and 600 minutes or less, preferably 40 minutes or more and 450 minutes or less, and more preferably 60 minutes or more and 300 minutes or less.

[0580] In this case, when the by-product compound is distilled out immediately after being produced, the finally obtained resin has a low content of high molecular weight material. However, when the mono-hydroxyl compound of the by-product is allowed to stay in the reaction vessel for a certain period of time, the finally obtained resin has a high content of high molecular weight material.

[0581] The melt polycondensation method can be performed continuously or in a batch manner. The reaction device for performing the reaction can be a vertical type equipped with an anchor-type impeller, a Maxblend impeller, a spiral ribbon-type impeller, or the like, can be a horizontal type equipped with a paddle blade, a lattice blade, a spectacle blade, or the like, and can be an extruder type equipped with a screw. Furthermore, in consideration of the viscosity of the polymer, it is desirable to use a reaction device that appropriately combines these reaction devices.

[0582] In the method for producing the resin used in the present application, the catalyst can be removed or deactivated to maintain thermal stability and hydrolytic stability after completion of the polymerization reaction. A method of deactivating the catalyst by adding an acidic material known in the art can be preferably performed.

[0583] As the acidic material, for example, it is preferable to use an ester such as butyl benzoate; an aromatic sulfonic acid such as p-toluenesulfonic acid; an aromatic sulfonic acid ester such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate; a phosphoric acid such as phosphorous acid, phosphoric acid, and phosphonic acid; a phosphite 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; a phosphate such as triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate, dioctyl phosphate, and monooctyl phosphate; a phosphonic acid such as diphenyl phosphonic acid, dioctyl phosphonic acid, and dibutyl phosphonic acid; a phosphonate such as phenyl diethyl phosphonate; a phosphine such as triphenyl phosphine and bis(diphenyl phosphino)ethane; a boronic acid such as boric acid and phenyl boric acid; an aromatic sulfonate such as dodecylbenzenesulfonic acid tetrabutylammonium salt; an organic halide such as stearic acid chloride, benzoyl chloride, and p-toluenesulfonic acid chloride; an alkyl sulfate such as dimethyl sulfate; an organic halide such as benzyl chloride; and the like. The acidic material can be used in an amount of 0.1 to 5 parts by mole, preferably 0.1 to 1 parts by mole, with respect to 100 parts by mole of the catalyst.

[0584] The acidic material can be used in an amount of 0.1 to 5 parts by mole, preferably 0.1 to 1 parts by mole, with respect to 100 parts by mole of the catalyst.

[0585] When the amount of the acidic material is less than 0.1 molar parts, the deactivation effect becomes insufficient, which is not preferred. In addition, when the amount exceeds 5 molar parts, the heat resistance of the resin deteriorates and the molded article is easily colored, which is not preferred.

[0586] After deactivating the catalyst, a process of devolatilizing the low-boiling-point compound in the resin can also be performed at a pressure of 0.1 mmHg to 1 mmHg and a temperature of 200°C to 350°C. In this process, it is preferable to use a horizontal type apparatus equipped with stirring blades having excellent surface renewal ability, such as paddle blades, lattice blades, and eyeglass blades, or a thin film evaporator.

[0587] It is preferable that the content of foreign matter in the resin of the present application be as small as possible, and filtration of the molten raw material, filtration of the catalyst solution, and the like are preferably performed.

[0588] The mesh of the filter used in the filtration is preferably 5 μm or less, and more preferably 1 μm or less. In addition, it is preferable to perform filtration of the produced resin using a polymer filter. The mesh of the polymer filter is preferably 100 μm or less, and more preferably 30 μm or less. In addition, the process of obtaining the resin pellets needs to be performed in a low-dust environment, and the environment is preferably Class 6 or lower, and more preferably Class 5 or lower.

[0589] In addition, examples of the method of molding a molded article containing the resin other than injection molding include press molding, molding, roll processing, extrusion molding, stretching, and the like, but are not limited thereto.

[0590] Another exemplary embodiment of the present application provides a resin composition containing the resin according to the above-described exemplary embodiment.

[0591] In one exemplary embodiment of the present application, the resin can 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.

[0592] In one exemplary embodiment of the present application, the resin composition can further contain a solvent. The solvent can be, for example, dimethylacetamide or 1,2-dichlorobenzene.

[0593] The solvent can be contained in an amount of 20 parts by weight to 99 parts by weight, based on 100 parts by weight of the resin composition.

[0594] The resin composition can include a resin in which another monomer is polymerized in addition to the compound of Formula 1a and the compound of Formula 2a. The other monomer is not particularly limited, and a monomer generally applied in the field related to a polyester can be appropriately used, as long as the main physical properties of the resin composition are not changed. The other monomer can be used in an amount of 1 to 50 mol parts with respect to 100 mol parts of the total monomers constituting the resin including the unit of Formula 1 and the unit of Formula 2.

[0595] In addition to the resin including the unit of Formula 1 and the unit of Formula 2, the resin composition can further include one or more selected from, for example, an antioxidant, a plasticizer, an antistatic agent, a nucleating agent, a flame retardant, a lubricant, an impact modifier, an optical brightener, a UV absorber, a pigment, and a dye, if necessary.

[0596] The additive can be included in an amount of 1 to 99 parts by weight based on 100 parts by weight of the resin composition.

[0597] The type of the antioxidant, the plasticizer, the antistatic agent, the nucleating agent, the flame retardant, the lubricant, the impact modifier, the optical brightener, the UV absorber, the pigment, or the dye is not particularly limited, and those used in the art can be appropriately used.

[0598] Yet another exemplary embodiment of the present application provides a molded article including the resin composition according to the above-described exemplary embodiments.

[0599] In one exemplary embodiment of the present application, the molded article can be prepared from the resin composition or a cured product thereof.

[0600] As an example of a method of preparing the molded article, it can include: sufficiently mixing the resin including the unit of Formula 1 and the unit of Formula 2 described above with the additive using a mixer, preparing the mixture into a pellet by extrusion molding of the resulting mixture using an extruder, drying the pellet, and then injection molding the pellet using an injection molding machine.

[0601] In one exemplary embodiment of the present application, the molded article is an optical lens.

[0602] In one exemplary embodiment of the present application, the optical lens has a thickness of 0.1 μm to 30 mm.

[0603] According to the difference in refractive index of the optical lens, the position of the focal point of light focusing varies in lenses having the same thickness. This is shown in Figure 1This changes the position of the focus point focused between the camera lens and the image sensor and between the eyeglass lens and the human pupil, and the thickness of the lens and the film decreases as the refractive index increases to adjust the focus point at the same position. The optical lens according to one exemplary embodiment of the present specification has a high refractive index, and thus an optical lens having a small thickness can be implemented.

[0604] The optical lens is manufactured by using the resin, has a high refractive index and high transparency, and can be preferably applied to a camera.

[0605] In one exemplary embodiment of the present specification, the molded product is an optical film or an optical sheet. The optical film or the optical sheet is manufactured using a polyester resin, has a small thickness and excellent light collecting effect and light diffusing effect, and can be preferably applied to a backlight module of a liquid crystal display, a flat lens, a meta lens, and the like.

[0606] In one exemplary embodiment of the present specification, the optical film or the optical sheet has a thickness of 0.1 nm to 10 mm.

[0607] In one exemplary embodiment of the present specification, the molded product is an optical resin. The optical resin is manufactured using a polyester resin, and has a low optical loss due to its small thickness, high refractive index, and low birefringence.

[0608] The optical resin according to one exemplary embodiment of the present specification has a low optical loss due to its high refractive index and low birefringence. The optical resin according to one exemplary embodiment of the present specification has a glass transition temperature of 90℃ to 200℃, which is not very high or very low in terms of heat resistance characteristics compared to general optical materials in the related art, and thus is easily processed and shows excellent heat resistance characteristics. When the glass transition temperature exceeds 200℃, it is difficult to process the optical resin due to an increase in melt flow index, and when the glass transition temperature is lower than 90℃, low heat resistance characteristics result in poor weather resistance caused by external environments. Accordingly, there are few optical resins according to one exemplary embodiment of the present specification that have appropriate heat characteristics and implement a high refractive index.

[0609] Inventive Embodiments

[0610] Hereinafter, the present application will be illustrated in more detail through examples.

[0611] Examples

[0612] 1. Synthesis of monomer 1-1

[0613]

[0614] Monomer 1-1

[0615] 1) Synthesis of Intermediate 1-C

[0616] Dissolve 10.0 g (37 mmol, 1.0 equivalent) of Compound 1-A and 13.16 g (77 mmol, 2.05 equivalents) of Compound 1-B in 90 g of tetrahydrofuran (THF) and stir the resulting solution in an oil bath at 80 °C for 30 minutes. After dissolving 15.48 g (112 mmol, 3.0 equivalents) of K2CO3 in 100 mL of water, add the solution dropwise thereto while maintaining the internal temperature of the solution at 50 °C or higher for 10 minutes. Add 0.76 g (1.5 mmol, 0.04 equivalents) of Pd(t-Bu3P)2 catalyst thereto at an internal temperature of 60 °C. After stirring for 1 hour, wash the mixture with ethyl acetate (EA) / H2O to separate the organic layer, and concentrate the solvent under vacuum. After purifying by column chromatography through n-hexane (n-Hex) and dichloromethane (DCM), precipitate the resulting product in n-hexane (n-Hex) to obtain Intermediate 1-C as a solid.

[0617] 2) Synthesis of Monomer 1-1

[0618] Dissolve 9.0 g (25 mmol, 1.0 equivalent) of Intermediate 1-C, 5.47 g (62 mmol, 2.5 equivalents) of Compound 1-D, and 1.37 g (5 mmol, 0.40 equivalents) of K2CO3 in 45 g of dimethylacetamide (DMAc) and stir the resulting solution in an oil bath at 120 °C for 2 hours. After cooling, precipitate the solid by adding water thereto, and then filter. Purify the obtained solid by column chromatography through ethyl acetate (EA) and dichloromethane (DCM), and then precipitate in n-hexane (n-Hex) to obtain 6.7 g of Monomer 1-1 as a white solid.

[0619] MS: [M+H] + = 450

[0620] 2. Synthesis of Monomer 2-1

[0621]

[0622] 1) Synthesis of Intermediate 2-C

[0623] Dissolve 25.9 g (100 mmol, 1.0 equivalent) of Compound 2-A and 72.1 g (500 mmol, 5.0 equivalents) of Compound 2-B in 80 g of 1,4-dioxane and stir the resulting solution in an oil bath at 120 °C for 2 hours. After cooling, precipitate the solid by adding water thereto, and then filter. Purify the obtained solid by column chromatography through ethyl acetate (EA) and dichloromethane (DCM), and then precipitate in n-hexane (n-Hex) to obtain 23.0 g of Intermediate 2-C as a white solid. In a 2 L round bottom flask, 200 g of compound 1-A was dissolved in 1 L of THF and the resulting solution was stirred in a bath at 60 °C for 30 min. While maintaining the temperature, 29.4 g (300 mmol, 3.0 eq) of H2SO4 was added dropwise to it for 30 min. To it, 0.53 g (5 mmol, 0.05 eq) of 3-mercaptopropionic acid (HSCH2CH2CO2H) was added. After stirring for 6 h, the mixture was neutralized by washing with toluene / 10% NaOH several times and the organic layer was separated and precipitated in n-Hex to obtain intermediate 2-C as an orange solid.

[0624] 2) Synthesis of intermediate 2-D

[0625] In a 2 L round bottom flask, 200 g of compound 1-A was dissolved in 1 L of THF and the resulting solution was stirred in a bath at 60 °C for 30 min. While maintaining the temperature, 29.4 g (300 mmol, 3.0 eq) of H2SO4 was added dropwise to it for 30 min. To it, 0.53 g (5 mmol, 0.05 eq) of 3-mercaptopropionic acid (HSCH2CH2CO2H) was added. After stirring for 6 h, the mixture was neutralized by washing with toluene / 10% NaOH several times and the organic layer was separated and precipitated in n-Hex to obtain intermediate 2-C as an orange solid.

[0626] 3) Synthesis of monomer 2-1

[0627] In a 2 L round bottom flask, 200 g of compound 1-A was dissolved in 1 L of THF and the resulting solution was stirred in a bath at 60 °C for 30 min. While maintaining the temperature, 29.4 g (300 mmol, 3.0 eq) of H2SO4 was added dropwise to it for 30 min. To it, 0.53 g (5 mmol, 0.05 eq) of 3-mercaptopropionic acid (HSCH2CH2CO2H) was added. After stirring for 6 h, the mixture was neutralized by washing with toluene / 10% NaOH several times and the organic layer was separated and precipitated in n-Hex to obtain intermediate 2-C as an orange solid.

[0628] MS: [M+H] + = 664

[0629] 3. Synthesis of monomer 3-6

[0630]

[0631] 1) Synthesis of intermediate 3-C

[0632] 18.1 g (100 mmol, 1.0 eq) of compound 3-A and 47.1 g (500 mmol, 5.0 eq) of compound 3-B were dissolved in 80 g of 1,4-dioxane, and the resulting solution was stirred in a bath at 60°C for 30 minutes. While maintaining the temperature, 29.4 g (300 mmol, 3.0 eq) of H2SO4 was added dropwise thereto for 30 minutes. 0.53 g (5 mmol, 0.05 eq) of 3-mercaptopropionic acid (HSCH2CH2CO2H) was added thereto. After stirring for 6 hours, the mixture was neutralized by washing with toluene / 10% NaOH several times, and the organic layer was separated and precipitated in n-hexane (n-Hex) to obtain intermediate 3-C.

[0633] 2) Synthesis of monomer 3-6

[0634] In the same manner as in the synthesis of monomer 2-1, 28.1 g of monomer 3-6 was obtained, except that intermediate 3-C was used instead of intermediate 2-D in the synthesis of monomer 2-1, 3). In addition, monomer 3-6 can be purchased from TCI or Sigma-Aldrich.

[0635] MS: [M+H] + = 438

[0636] Example 1-1. Preparation of resin 1-1

[0637]

[0638] 36 g (80 mmol) of monomer 1-1, 13.3 g (20 mmol) of monomer 2-1, and 25.4 g (100 mmol) of bis-2-hydroxyethyl terephthalate were melted and reacted at 260°C for 6 hours. As the reaction proceeds, ethylene glycol is produced as a byproduct, and the degree of reduced pressure was adjusted until 1 torr to remove the ethylene glycol. After the completion of the reaction, a molten resin of the polymer polymerized by purging nitrogen into the reactor to generate an atmospheric atmosphere was taken out, thereby obtaining resin 1-1.

[0639] Example 1-2. Preparation of resin 1-2

[0640] Resin 1-2 of Example 1-2 was prepared in the same manner as in the method of preparing the resin of Example 1-1, except that 22 g (50 mmol) of monomer 1-1 in Example 1-1 and 33.2 g (50 mmol) of monomer 2-1 in Example 1-1 were applied.

[0641] ​Example 2-1. Preparation of Resin 2-1

[0642] Melt 40.55 g (90 mmol) of monomer 1-1, 6.65 g (10 mmol) of monomer 2-1, and 19.42 g (100 mmol) of dimethyl terephthalate and react at 250 °C for 5 hours. As the reaction proceeds, methanol is produced as a byproduct, and the degree of reduced pressure is adjusted up to 1 torr to remove the methanol. After the reaction is complete, resin 2-1, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0643] Monomer 1-1:

[0644] Monomer 2-1:

[0645] Example 2-2. Preparation of Resin 2-2

[0646] Melt 4.51 g (10 mmol) of monomer 1-1, 59.83 g (90 mmol) of monomer 2-1, and 19.42 g (100 mmol) of dimethyl terephthalate and react at 250 °C for 5 hours. As the reaction proceeds, methanol is produced as a byproduct, and the degree of reduced pressure is adjusted up to 1 torr to remove the methanol. After the reaction is complete, resin 2-2, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0647] Example 2-3. Preparation of Resin 2-3

[0648] Melt 18.02 g (40 mmol) of monomer 1-1, 3.32 g (5 mmol) of monomer 2-1, 15.75 g (55 mmol) of monomer 3-3, and 19.42 g (100 mmol) of dimethyl terephthalate and react at 250 °C for 5 hours. As the reaction proceeds, methanol is produced as a byproduct, and the degree of reduced pressure is adjusted up to 1 torr to remove the methanol. After the reaction is complete, resin 2-3, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0649]

[0650] Example 2-4. Preparation of Resin 2-4

[0651] 6.76 g (15 mmol) of monomer 1-1, 3.32 g (5 mmol) of monomer 2-1, 29.96 g (80 mmol) of monomer 3-4, and 19.42 g (100 mmol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Methanol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove methanol. After the reaction was complete, resin 2-4 was obtained as a polymer melt resin by purging nitrogen into the reactor to create an atmospheric pressure atmosphere.

[0652] Examples 2-5. Preparation of Resin 2-5

[0653] 0.45 g (1 mmol) of monomer 1-1, 0.66 g (1 mmol) of monomer 2-1, 52.76 g (98 mmol) of monomer 3-1, and 19.42 g (100 mmol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Methanol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove methanol. After the reaction was complete, resin 2-5 was obtained as a polymer melt resin by purging nitrogen into the reactor to create an atmospheric pressure atmosphere.

[0654] Examples 2-6. Preparation of Resin 2-6

[0655] 6.76 g (15 mmol) of monomer 1-1, 3.32 g (5 mmol) of monomer 2-1, 47.26 g (80 mmol) of monomer 3-2, and 19.42 g (100 mmol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Methanol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove methanol. After the reaction was complete, resin 2-6 was obtained as a polymer melt resin by purging nitrogen into the reactor to create an atmospheric pressure atmosphere.

[0656] Examples 2-7. Preparation of Resin 2-7

[0657] 6.76 g (15 mmol) of monomer 1-1, 3.32 g (5 mmol) of monomer 2-1, 6.85 g (30 mmol) of monomer 3-5, 18.72 g (50 mmol) of monomer 3-4, and 19.42 g (100 mmol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Methanol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove methanol. After the reaction was complete, resin 2-7 was obtained as a polymer melt resin by purging nitrogen into the reactor to create an atmospheric pressure atmosphere.

[0658] Examples 2-8. Preparation of Resin 2-8

[0659] Melt 2.25 g (5 mmol) of monomer 1-1, 3.32 g (5 mmol) of monomer 2-1, 10.9 g (55 mmol) of monomer 3-8, 13.11 g (35 mmol) of monomer 3-4, and 19.42 g (100 mmol) of dimethyl terephthalate and react at 250 °C for 5 hours. As the reaction proceeds, methanol is produced as a byproduct and the degree of reduced pressure is adjusted up to 1 torr to remove the methanol. After the reaction is complete, resin 2-8, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0660] Example 2-9. Preparation of Resin 2-9

[0661] Melt 0.45 g (1 mmol) of monomer 1-1, 0.66 g (1 mmol) of monomer 2-1, 52.22 g (97 mmol) of monomer 3-1, 0.44 g (1 mmol) of monomer 3-6, and 19.42 g (100 mmol) of dimethyl terephthalate and react at 250 °C for 5 hours. As the reaction proceeds, methanol is produced as a byproduct and the degree of reduced pressure is adjusted up to 1 torr to remove the methanol. After the reaction is complete, resin 2-10, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0662] Example 2-10. Preparation of Resin 2-10

[0663] Melt 0.45 g (1 mmol) of monomer 1-1, 0.66 g (1 mmol) of monomer 2-1, 52.22 g (97 mmol) of monomer 3-1, 0.44 g (1 mmol) of monomer 3-6, and 19.42 g (100 mmol) of dimethyl terephthalate and react at 250 °C for 5 hours. As the reaction proceeds, methanol is produced as a byproduct and the degree of reduced pressure is adjusted up to 1 torr to remove the methanol. After the reaction is complete, resin 2-10, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0664] Example 2-11. Preparation of Resin 2-11

[0665] Melt 0.45 g (1 mmol) of monomer 1-1, 0.66 g (1 mmol) of monomer 2-1, 52.22 g (97 mmol) of monomer 3-1, 0.44 g (1 mmol) of monomer 3-6, and 19.42 g (100 mmol) of dimethyl terephthalate and react at 250 °C for 5 hours. As the reaction proceeds, methanol is produced as a byproduct and the degree of reduced pressure is adjusted up to 1 torr to remove the methanol. After the reaction is complete, resin 2-10, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0666] Example 2-12. Preparation of Resin 2-12

[0667] 15.77 g (35 mmol) of monomer 1-1, 3.32 g (5 mmol) of monomer 2-1, 10.51 g (30 mmol) of monomer 3-7, 8.59 g (30 mmol) of monomer 3-3, and 19.42 g (100 mmol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Methanol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove methanol. After the reaction was complete, resin 2-12 was obtained as a polymer melt resin by purging nitrogen into the reactor to create an atmospheric pressure atmosphere.

[0668] Example 2-13. Preparation of Resin 2-13

[0669] 0.45 g (1 mmol) of monomer 1-1, 0.66 g (1 mmol) of monomer 2-1, 10.6 g (28 mmol) of monomer 3-9, 26.21 g (70 mmol) of monomer 3-4, and 19.42 g (100 mmol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Methanol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove methanol. After the reaction was complete, resin 2-13 was obtained as a polymer melt resin by purging nitrogen into the reactor to create an atmospheric pressure atmosphere.

[0670] Example 2-14. Preparation of Resin 2-14

[0671] 18.02 g (40 mmol) of monomer 1-1, 0.66 g (1 mmol) of monomer 2-1, 2.29 g (8 mmol) of monomer 3-3, 19.3 g (51 mmol) of monomer 3-9, and 19.42 g (100 mmol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Methanol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove methanol. After the reaction was complete, resin 2-14 was obtained as a polymer melt resin by purging nitrogen into the reactor to create an atmospheric pressure atmosphere.

[0672] Example 2-15. Preparation of Resin 2-15

[0673] 2.25 g (5 mmol) of monomer 1-1, 9.97 g (15 mmol) of monomer 2-1, 14.98 g (40 mmol) of monomer 3-4, 21.54 g (40 mmol) of monomer 3-1, and 19.42 g (100 mmol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Methanol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove methanol. After the reaction was complete, resin 2-15 was obtained as a polymer melt resin by purging nitrogen into the reactor to create an atmospheric pressure atmosphere.

[0674] Example 2-16. Preparation of Resin 2-16

[0675] 0.45 g (1 mmol) of monomer 1-1, 0.66 g (1 mmol) of monomer 2-1, 11.81 g (20 mmol) of monomer 3-2, 29.21 g (78 mmol) of monomer 3-4, and 19.42 g (100 mmol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Methanol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove methanol. After the reaction was complete, resin 2-16 was obtained as a polymer melt resin by purging nitrogen into the reactor to create an atmospheric pressure atmosphere.

[0676] Example 2-17. Preparation of Resin 2-17

[0677] 2.25 g (5 mmol) of monomer 1-1, 3.32 g (5 mmol) of monomer 2-1, 1.98 g (10 mmol) of monomer 3-8, 18.26 g (80 mmol) of monomer 3-5, and 19.42 g (100 mmol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Methanol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove methanol. After the reaction was complete, the reactor was purged with nitrogen to create an atmospheric pressure atmosphere to obtain resin 2-17, the polymer melt resin to be polymerized.

[0678] Example 2-18. Preparation of Resin 2-18

[0679] melt 2.25 g (5 mmol) of monomer 1-1, 9.97 g (15 mmol) of monomer 2-1, 14.98 g (40 mmol) of monomer 3-4, 21.54 g (40 mmol) of monomer 3-1, 9.71 g (50 mmol) of dimethyl terephthalate, and 9.71 g (50 mmol) of dimethyl isophthalate, and react at 250°C for 5 hours. As the reaction proceeds, methanol is produced as a byproduct, and the degree of reduced pressure is adjusted up to 1 torr to remove the methanol. After completion of the reaction, resin 2-18, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0680] Example 2-19. Preparation of Resin 2-19

[0681] melt 2.25 g (5 mmol) of monomer 1-1, 9.97 g (15 mmol) of monomer 2-1, 14.98 g (40 mmol) of monomer 3-4, 21.54 g (40 mmol) of monomer 3-1, 9.71 g (50 mmol) of dimethyl terephthalate, and 9.71 g (50 mmol) of dimethyl isophthalate, and react at 250°C for 5 hours. As the reaction proceeds, methanol is produced as a byproduct, and the degree of reduced pressure is adjusted up to 1 torr to remove the methanol. After completion of the reaction, resin 2-19, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0682] Example 2-20. Preparation of Resin 2-20

[0683] melt 2.25 g (5 mmol) of monomer 1-1, 9.97 g (15 mmol) of monomer 2-1, 14.98 g (40 mmol) of monomer 3-4, 21.54 g (40 mmol) of monomer 3-1, 9.71 g (50 mmol) of dimethyl terephthalate, and 9.71 g (50 mmol) of dimethyl isophthalate, and react at 250°C for 5 hours. As the reaction proceeds, methanol is produced as a byproduct, and the degree of reduced pressure is adjusted up to 1 torr to remove the methanol. After completion of the reaction, resin 2-20, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0684] [Table 1]

[0685]

[0686]

[0687] Table 1 shows the mole fraction of each monomer contained in the resins 2-1 to 2-20 of Examples 2-1 to 2-20. In addition, para means the mole fraction of dimethyl terephthalate as a polyester precursor, and meta means the mole fraction of dimethyl isophthalate as a polyester precursor.

[0688] Example 3-1. Preparation of Resin 3-1

[0689] melt 31.5371 g (0.07 mol) of monomer 1-1, 19.9440 g (0.03 mol) of monomer 2-1, 10.7110 g (0.05 mol) of diphenyl carbonate, and 9.7095 g (0.05 mol) of dimethyl terephthalate, and react at 250°C for 5 hours. As the reaction proceeds, phenol is produced as a by-product, and the degree of reduced pressure is adjusted up to 1 torr to remove the phenol. After the completion of the reaction, resin 3-2 is obtained as a polymerized polymer melt resin by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0690] Monomer 1-1:

[0691] Monomer 2-1:

[0692] Example 3-2. Preparation of Resin 3-2

[0693] melt 31.5371 g (0.07 mol) of monomer 1-1, 19.9440 g (0.03 mol) of monomer 2-1, 10.7110 g (0.05 mol) of diphenyl carbonate, and 9.7095 g (0.05 mol) of dimethyl terephthalate, and react at 250°C for 5 hours. As the reaction proceeds, phenol is produced as a by-product, and the degree of reduced pressure is adjusted up to 1 torr to remove the phenol. After the completion of the reaction, resin 3-2 is obtained as a polymerized polymer melt resin by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0694] Example 3-3. Preparation of Resin 3-3

[0695] melt 31.5371 g (0.07 mol) of monomer 1-1, 19.9440 g (0.03 mol) of monomer 2-1, 10.7110 g (0.05 mol) of diphenyl carbonate, and 9.7095 g (0.05 mol) of dimethyl terephthalate, and react at 250°C for 5 hours. As the reaction proceeds, phenol is produced as a by-product, and the degree of reduced pressure is adjusted up to 1 torr to remove the phenol. After the completion of the reaction, resin 3-2 is obtained as a polymerized polymer melt resin by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0696] Example 3-4. Preparation of Resin 3-4

[0697] Melt 13.5159 g (0.03 mol) of monomer 1-1, 19.7440 g (0.03 mol) of monomer 2-1, 19.1436 g (0.04 mol) of monomer 1-2, 10.7110 g (0.05 mol) of diphenyl carbonate, and 9.7095 g (0.05 mol) of dimethyl terephthalate, and react at 250°C for 5 hours. As the reaction proceeds, phenol is produced as a by-product, and the degree of reduced pressure is adjusted up to 1 torr to remove the phenol. After the completion of the reaction, resin 3-4, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0698] Monomer 1-2:

[0699] Example 3-5. Preparation of resin 3-5

[0700] Melt 4.5053 g (0.01 mol) of monomer 1-1, 6.6480 g (0.01 mol) of monomer 2-1, 21.5456 g (0.04 mol) of monomer 3-1, 14.9660 g (0.04 mol) of monomer 3-4, 10.7110 g (0.05 mol) of diphenyl carbonate, and 9.7095 g (0.05 mol) of dimethyl terephthalate, and react at 250°C for 5 hours. As the reaction proceeds, phenol is produced as a by-product, and the degree of reduced pressure is adjusted up to 1 torr to remove the phenol. After the completion of the reaction, resin 3-5, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0701]

[0702] Example 3-6. Preparation of resin 3-6

[0703] Melt 4.5053 g (0.01 mol) of monomer 1-1, 6.6480 g (0.01 mol) of monomer 2-1, 23.6288 g (0.04 mol) of monomer 3-2, 14.9660 g (0.04 mol) of monomer 3-4, 10.7110 g (0.05 mol) of diphenyl carbonate, and 9.7095 g (0.05 mol) of dimethyl terephthalate, and react at 250°C for 5 hours. As the reaction proceeds, phenol is produced as a by-product, and the degree of reduced pressure is adjusted up to 1 torr to remove the phenol. After the completion of the reaction, resin 3-6, which is a polymerized polymer melt resin, is obtained by purging nitrogen into the reactor to create an atmosphere of normal pressure.

[0704] Example 3-7. Preparation of resin 3-7

[0705] 4.5053 g (0.01 mol) of monomer 1-1, 6.6480 g (0.01 mol) of monomer 2-1, 21.5456 g (0.04 mol) of monomer 3-1, 23.6288 g (0.04 mol) of monomer 3-2, 10.7110 g (0.05 mol) of diphenyl carbonate and 9.7095 g (0.05 mol) of dimethyl terephthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, nitrogen was purged into the reactor to create an atmospheric pressure atmosphere to obtain resin 3-7, the polymer melt resin for polymerization.

[0706] Examples 3-8. Preparation of Resin 3-8

[0707] 4.5053 g (0.01 mol) of monomer 1-1, 6.6480 g (0.01 mol) of monomer 2-1, 19.4558 g (0.052 mmol) of monomer 3-4, 6.3921 g (0.028 mmol) of monomer 3-5, 6.4266 g (0.030 mol) of diphenyl carbonate, 9.7095 g (0.050 mol) of dimethyl terephthalate, and 3.8838 g (0.020 mol) of dimethyl isophthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, resin 3-8 was obtained by purging the reactor with nitrogen to create an atmospheric pressure atmosphere, yielding the polymer melt resin for polymerization.

[0708] Examples 3-9. Preparation of Resin 3-9

[0709] 2.2527 g (0.005 mol) of monomer 1-1, 3.3240 g (0.005 mol) of monomer 2-1, 18.7075 g (0.050 mol) of monomer 3-4, 17.5408 g (0.040 mol) of monomer 3-6, 6.4266 g (0.030 mol) of diphenyl carbonate, 9.7095 g (0.050 mol) of dimethyl terephthalate, and 3.8838 g (0.020 mol) of dimethyl isophthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, resin 3-9 was obtained by purging the reactor with nitrogen to create an atmospheric pressure atmosphere, yielding the polymer melt resin for polymerization.

[0710] Examples 3-10. Preparation of Resin 3-10

[0711] 2.2527 g (0.005 mol) of monomer 1-1, 3.3240 g (0.005 mol) of monomer 2-1, 24.2388 g (0.045 mol) of monomer 3-1, 16.8368 g (0.045 mol) of monomer 3-4, 6.4266 g (0.030 mol) of diphenyl carbonate, 9.7095 g (0.050 mol) of dimethyl terephthalate, and 3.8838 g (0.020 mol) of dimethyl isophthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, resin 3-10 was obtained by purging the reactor with nitrogen to create an atmospheric pressure atmosphere, yielding the polymer melt resin.

[0712] Example 3-11. Preparation of Resin 3-11

[0713] 2.2527 g (0.005 mol) of monomer 1-1, 3.3240 g (0.005 mol) of monomer 2-1, 20.6752 g (0.035 mol) of monomer 3-2, 20.5783 g (0.055 mol) of monomer 3-4, 6.4266 g (0.030 mol) of diphenyl carbonate, 9.7095 g (0.050 mol) of dimethyl terephthalate, and 3.8838 g (0.020 mol) of dimethyl isophthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, resin 3-11, the polymer melt resin, was obtained by purging the reactor with nitrogen to create an atmospheric pressure atmosphere.

[0714] Example 3-12. Preparation of Resin 3-12

[0715] 2.2527 g (0.005 mol) of monomer 1-1, 3.3240 g (0.005 mol) of monomer 2-1, 4.9555 g (0.025 mol) of monomer 3-8, 18.6108 g (0.065 mol) of monomer 3-3, 6.4266 g (0.030 mol) of diphenyl carbonate, 9.7095 g (0.050 mol) of dimethyl terephthalate, and 3.8838 g (0.020 mol) of dimethyl isophthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, resin 3-12 was obtained by purging the reactor with nitrogen to create an atmospheric pressure atmosphere, yielding the polymer melt resin.

[0716] Example 3-13. Preparation of Resin 3-13

[0717] 2.2527 g (0.005 mol) of monomer 1-1, 3.3240 g (0.005 mol) of monomer 2-1, 6.9377 g (0.035 mol) of monomer 3-8, 20.8159 g (0.055 mol) of monomer 3-9, 6.4266 g (0.030 mol) of diphenyl carbonate, 9.7095 g (0.050 mol) of dimethyl terephthalate, and 3.8838 g (0.020 mol) of dimethyl isophthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, nitrogen was purged into the reactor to create an atmospheric pressure atmosphere to obtain resin 3-13, the polymer melt resin for polymerization.

[0718] Example 3-14. Preparation of Resin 3-14

[0719] 2.2527 g (0.005 mol) of monomer 1-1, 3.3240 g (0.005 mol) of monomer 2-1, 3.9644 g (0.020 mol) of monomer 3-8, 24.5287 g (0.070 mol) of monomer 3-7, 6.4266 g (0.030 mol) of diphenyl carbonate, 9.7095 g (0.050 mol) of dimethyl terephthalate, and 3.8838 g (0.020 mol) of dimethyl isophthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, resin 3-14 was obtained as a polymer melt resin by purging nitrogen into the reactor to create an atmospheric pressure atmosphere.

[0720] Example 3-15. Preparation of Resin 3-15

[0721] 2.2527 g (0.005 mol) of monomer 1-1, 3.3240 g (0.005 mol) of monomer 2-1, 18.7075 g (0.050 mol) of monomer 3-4, 17.5408 g (0.040 mol) of monomer 3-6, 6.4266 g (0.030 mol) of diphenyl carbonate, 9.7095 g (0.050 mol) of dimethyl terephthalate, and 3.8838 g (0.020 mol) of dimethyl isophthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, resin 3-15 was obtained by purging the reactor with nitrogen to create an atmospheric pressure atmosphere, yielding the polymer melt resin.

[0722] Example 3-16. Preparation of Resin 3-16

[0723] Example 3-16. Preparation of resin 3-16

[0724] Example 3-17. Preparation of resin 3-17

[0725] Example 3-18. Preparation of resin 3-18

[0726] Example 3-17. Preparation of resin 3-17

[0727] Example 3-18. Preparation of resin 3-18

[0728] Example 3-19. Preparation of Resin 3-19

[0729] 2.2527 g (0.005 mol) of monomer 1-1, 3.3240 g (0.005 mol) of monomer 2-1, 18.7075 g (0.050 mol) of monomer 3-4, 17.5408 g (0.040 mol) of monomer 3-6, 10.7110 g (0.050 mol) of diphenyl carbonate, 6.7967 g (0.035 mol) of dimethyl terephthalate, and 2.9129 g (0.015 mol) of dimethyl isophthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, nitrogen was purged into the reactor to create an atmospheric pressure atmosphere to obtain resin 3-19, the polymer melt resin for polymerization.

[0730] Example 3-20. Preparation of Resin 3-20

[0731] 2.2527 g (0.005 mol) of monomer 1-1, 3.3240 g (0.005 mol) of monomer 2-1, 16.8368 g (0.045 mol) of monomer 3-4, 10.2731 g (0.045 mol) of monomer 3-5, 12.8532 g (0.060 mol) of diphenyl carbonate, 5.8257 g (0.030 mol) of dimethyl terephthalate, and 1.9419 g (0.010 mol) of dimethyl isophthalate were melted and reacted at 250 °C for 5 hours. Phenol was produced as a byproduct during the reaction, and the pressure was adjusted to 1 Torr to remove phenol. After the reaction was complete, resin 3-20 was obtained by purging the reactor with nitrogen to create an atmospheric pressure atmosphere, yielding the polymer melt resin.

[0732] [Table 2]

[0733]

[0734]

[0735]

[0736] Table 2 shows the molar amounts of each monomer contained in resins 3-1 to 3-20 of Examples 3-1 to 3-20. Furthermore, PE precursor (para) refers to the molar amount of dimethyl terephthalate as a polyester precursor, and PE precursor (meta) refers to the molar amount of dimethyl isophthalate as a polyester precursor.

[0737] Experimental example.

[0738] The molecular weight and molecular weight distribution of the polymeric resin sample were determined by gel permeation chromatography (GPC), and the thermogram was obtained using a differential scanning calorimeter (DSC) to investigate thermal properties. After forming a film to measure the refractive index and Abbe number, the result values according to the wavelength of light were obtained using an ellipsometer.

[0739] For the molecular weight by gel permeation chromatography (GPC), the result was obtained by injecting a solution prepared by dissolving a resin sample in tetrahydrofuran at a concentration of 1.0 mg / 1 ml using tetrahydrofuran (THF, stabilized with butylated hydroxytoluene (BHT)) as a solvent, and filtering the dissolved resin sample with a syringe filter, and measuring the molecular weight at 40℃, and the results are shown in Tables 3 to 5 below, respectively. A Waters RI detector was used, and two Agilent PLgel MIXED-B columns were used.

[0740] A differential scanning calorimeter (DSC) was measured to determine the glass transition temperature (Tg) of the resin. The glass transition temperature (Tg) was obtained on a graph obtained by heating 5.5 mg to 8.5 mg of a resin sample to 270℃ under N2 flow, cooling the resin sample, and then scanning the resin sample while heating the resin sample at a heating rate of 10℃ / minute during the second heating, and the glass transition temperature (Tg) is shown in Tables 3 to 5 below, respectively.

[0741] To measure the refractive index and Abbe number of the resin, a polymer solution prepared by dissolving a resin powder sample obtained by polymerization in a solvent dimethylacetamide at an amount of 10 wt% based on the total weight of the polymer solution was applied to a silicon wafer by spin coating at a rotation speed of 220 rpm to form a film having a thickness of 20 μm, and then the result values according to the wavelength of light were obtained at 20℃ using an ellipsometer, and are shown in Tables 3 to 5 below, respectively. Specifically, the refractive index was measured at a wavelength of 589 nm, and the Abbe number was obtained by measuring the refractive index (n D , n F , and n C ) at wavelengths of D (589 nm), F (486 nm), and C (656 nm), respectively, by the following equation.

[0742] Abbe number = (n D -1) / (n F -n C )

[0743] [Table 3]

[0744]

[0745] [Table 4]

[0746]

[0747] [Table 5]

[0748]

[0749]

[0750] In Tables 3 to 5, Mn means number average molecular weight, Mw means weight average molecular weight, PDI means polydispersity index, RI means refractive index, Tg means glass transition temperature, the refractive index of Table 3 is a value measured at a wavelength of 589 nm, and the refractive index of Tables 4 and 5 is a value measured at a wavelength of 587 nm.

[0751] According to Tables 3 to 5, the resin according to one exemplary embodiment of the present application includes the unit of Chemical Formula 1 and the unit of Chemical Formula 2, and in particular, the core structure of Chemical Formula 1 is phenylene, so that it can be determined that the refractive index of the resin is improved due to small molecular volume and excellent packing ability. In addition, Ar1 and Ar2 have electron-rich substituents, and thus have high electron density, and the benzene ring of the fluorene core structure of Chemical Formula 2 is also substituted with an electron-rich R2 substituent, so that the refractive index of the resin including the same is improved due to the high electron density of the fluorene core structure.

[0752] In addition, since the unit of Chemical Formula 3 is also included in the unit of Chemical Formula 1 and the unit of Chemical Formula 2, the glass transition temperature (Tg) and the refractive index can be adjusted, and the chain behavior of the resin can be made flexible, so that there is a technical effect that is advantageous for injection molding of a molded article.

[0753] According to Table 5, it can be seen that for the resin, a resin having desired physical properties can be prepared by appropriately adjusting the molar ratio of the polyester precursor to the polycarbonate precursor and the isomer to combine the properties of the polyester resin and the polycarbonate resin.

[0754] Therefore, since high refractive index is a high refractive property that is required in priority for appropriately applying the resin according to the exemplary embodiment of the present application to a molded article such as an optical lens, it can be determined that the resin of the example is excellent as an optical material.

Claims

1. A resin comprising units of the following Chemical Formula 1 and units of the following Chemical Formula 2: [Chemical Formula 1] [Chemical Formula 2] in, In Chemical Formula 1 and Chemical Formula 2, Ar1 and Ar2 are each independently an unsubstituted aryl group, R1 is hydrogen, R2 is an unsubstituted aryl group, R3 is hydrogen, r1 is 2, r2 is an integer from 1 to 4, and when r2 is 2 or greater, two or more R2s are the same as or different from each other, r3 is 4, L1 and L2 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group; or a heteroarylene group, X1 to X10, X'9 and X'10 are the same as or different from each other and are each independently O; or S, Z1 to Z6 are the same as or different from each other and are each independently a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, La, La', 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, c, d, p and q are the same as or different from each other and are each independently an integer from 0 to 6, and when a, b, c, d, p and q are each 2 or greater, the structures in each bracket are the same as or different from each other, t and t' are the same as or different from each other and are each independently an integer from 1 to 6, and when t and t' are each 2 or greater, the structures in the brackets are the same as or different from each other, m and n are the same and are either 0 or 1, When m and n are 0, t, r and s are 1, and La is -C(=O)-L-, When m and n are 1, t is an integer from 1 to 6, r + s = 1, r is a real number with a mole fraction of 0 < r < 1, and s is a real number with a mole fraction of 0 < s < 1, m' and n' are the same and are either 0 or 1, When m' and n' are 0, t', x and y are 1, and La' is -C(=O)-L-, When m' and n' are 1, t' is an integer from 1 to 6, x + y = 1, x is a real number with a mole fraction of 0 < x < 1, and y is a real number with a mole fraction of 0 < y < 1, and * means the part connected to the main chain of the resin.

2. The resin according to claim 1, further comprising units of the following Chemical Formula 3: [Chemical Formula 3] In Chemical Formula 3, 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 from 1 to 5, and when l11 is 2 or greater, two or more L11s are the same as or different from each other, X11 to X16 are the same as or different from each other and are each independently O; or S, Z11 to Z13 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, Lb and Lb' 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 each independently is an integer from 0 to 6, and when a', b', and p' are each 2 or greater, the structures in each parentheses are the same as or different from each other, t" is an integer from 1 to 6, and when t" is 2 or greater, the structures in the parentheses are the same as or different from each other, m" and n" are the same as each other and are 0 or 1, when m" and n" are 0, t", r', and s' are 1, and Lb is -C(=O)-L'- when m" and n" are 1, t" is an integer from 1 to 6, r' + s' = 1, r' is a real number with a molar fraction of 0 < r' < 1, and s' is a real number with a molar fraction of 0 < s' < 1, and * means the part connected to the main chain of the resin.

3. The resin according to claim 1, wherein Chemical Formula 1 is the following Chemical Formula 1-1 or Chemical Formula 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In Chemical Formula 1-1, the definitions of *, Ar1, Ar2, R1, r1, X1 to X4, Z1, Z2, a, and b are the same as those defined in Chemical Formula 1, La is -C(=O)-L-, L is a substituted or unsubstituted arylene group, In Chemical Formula 1-2, the definitions of *, Ar1, Ar2, R1, r1, X1 to X4, X9, X10, Z1, Z2, Z5, a, b, t, and p are the same as those defined in Chemical Formula 1, La and La" are the same as or different from each other, and each independently is a direct bond; or -C(=O)-L-, L is a substituted or unsubstituted arylene group, r is a real number with a molar fraction of 0 < r < 1, s is a real number with a molar fraction of 0 < s < 1, and r+s＝1。 4. The resin according to claim 1, wherein Chemical Formula 2 is the following Chemical Formula 2-1 or Chemical Formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] In Chemical Formula 2-1, the definitions of *, R2, R3, r2, r3, L1, L2, X5 to X8, Z3, Z4, c, and d are the same as those defined in Chemical Formula 2, La' is -C(=O)-L-, L is a substituted or unsubstituted arylene group, In Chemical Formula 2-2, the definitions of *, R2, R3, r2, r3, L1, L2, X5 to X8, X'9, X'10, Z3, Z4, Z6, c, d, t', and q are the same as those defined in Chemical Formula 2, La' and La"' are the same as or different from each other, and each independently is a direct bond; or -C(=O)-L-, L is a substituted or unsubstituted arylene group, x is a real number with a molar fraction of 0 < x < 1, y is a real number with a molar fraction of 0 < y < 1, and x + y = 1.

5. The resin according to claim 1, wherein Ar1 and Ar2 are the same as each other and each independently is an unsubstituted aryl group having 6 to 30 carbon atoms.

6. The resin according to claim 1, wherein Z1 to Z6 are the same as or different from each other, and each independently is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

7. The resin according to claim 1, wherein the weight-average molecular weight of the resin is from 3,000 g / mol to 500,000 g / mol.

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

9. The resin according to claim 1, wherein the refractive index of the resin, measured at a wavelength of 589 nm, is from 1.50 to 1.

75.

10. A method for preparing a resin according to any one of claims 1 to 9, the method comprising polymerizing a composition for preparing the resin, the composition comprising: a compound of the following chemical formula 1a; a compound of the following chemical formula 2a; and 1) a polyester precursor, or 2) a polyester precursor and a polycarbonate precursor: [Chemical Formula 1a] [Chemical Formula 2a] in, In chemical formulas 1a and 2a, The definitions of Ar1, Ar2, R1 to R3, r1 to r3, X1 to X8, a, b, c, d, L1, L2, and Z1 to Z4 are the same as those defined in Chemical Formula 1 and Chemical Formula 2.

11. The method of claim 10, wherein the polyester precursor is of chemical formula A, and the polycarbonate precursor is of chemical formula B: [Chemical Formula A] [Chemical Formula B] In chemical formula A and chemical formula B, Ra1, Ra2, Rb1, and Rb2 may be the same as or different from each other, and each is independently hydrogen; a halogen group; a hydroxyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Ar1 is a substituted or unsubstituted aryl group, and a1 to a4 are each 0 or 1.

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

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

14. The molding article according to claim 13, wherein the molding article is an optical lens.

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