Hydrolysis-resistant optical thermoplastic resin and preparation method thereof

Abstract

A thermoplastic resin comprises a structural unit derived from a compound represented by a general formula (A), and further comprises a structural unit derived from a compound represented by a general formula (B) and / or (C), and the thermoplastic resin has the advantages of high refractive index, low water absorption, hydrolysis resistance, low temperature impact resistance and the like.

Description

Technical Field

[0001] This invention relates to the field of optical resins, and more specifically to a hydrolysis-resistant optical thermoplastic resin and its manufacturing method. Background Technology

[0002] Compared to traditional glass, resin materials have a lower density, making optical lenses made from resin lighter. This is a significant advantage in applications where weight is a critical factor, such as portable cameras and smartphones. Lighter equipment reduces the burden on the user, making shooting easier and more comfortable. Optical polyester and polycarbonate resins are the preferred choices for manufacturing plastic lenses due to their high refractive index, ease of molding, and high production efficiency. Konica patent JP2001072872 discloses a thermoplastic resin material and its manufacturing method that can be used for optical lenses. It primarily uses 2,2-bis-(2-hydroxyethoxy)-1,1-naphthyl as a polymer monomer and can be used to prepare optical resin materials such as polyester, polycarbonate, polyurethane, and sulfone polymers, with a higher refractive index, reaching approximately 1.66. A foreign journal (Toshihide Hasegawa, Macromolecules (2010), 43, 131–136, Diphenolic 9,9-Diarylfluorene Trimers and Derivatives Possessing Flexible Alkylene Chain Spacers: Synthesis of the Monomers, Their Polymerization, and Properties of the Resulting Polymers) disclosed a method for synthesizing a polycarbonate containing a 9,9-diarylfluorene trimer structure in the main chain via interfacial polycondensation and triphosgene. The resulting highly transparent polymer exhibits high refractive index and low birefringence. However, the glass transition temperature of this polymer is too high (220-250℃), which is difficult to meet the requirements for injection molding in lens processing, thus preventing its application in the field of optical lenses.

[0003] Furthermore, plastic lenses are mainly used in mobile phones, automotive lenses, and security cameras. However, these applications often involve outdoor use, particularly in environments with high humidity in summer or extreme low temperatures in winter. This necessitates materials that not only maintain good refractive index and light transmittance but also possess excellent hydrolysis resistance and low-temperature resistance. Developing a polymer resin with high refractive index, good light transmittance, and excellent hydrolysis and low-temperature resistance is a pressing challenge for the industry. Summary of the Invention

[0004] The purpose of this invention is to provide a hydrolysis-resistant thermoplastic resin, its manufacturing method, and its application in the field of optical resins. This thermoplastic resin has the characteristics of high refractive index and high light transmittance, which can meet the requirements of optical lenses.

[0005] To address the aforementioned problems, the present invention provides a thermoplastic resin comprising structural units derived from compounds of general formula (A), and further comprising structural units derived from compounds of general formula (B) and / or (C).

[0006] In general formula (A), Z1 to Z6 independently represent aryl groups with 6 to 20 carbon atoms, preferably phenyl, naphthyl, or anthracene; X represents an alkylene group with 1 to 4 carbon atoms, and a and b independently represent integers from 1 to 10; R1 to R 12 Each of the following can be independently represented: hydrogen atom, halogen atom, cyano group, alkyl group with 1 to 20 carbon atoms, alkoxy group with 1 to 20 carbon atoms, cycloalkyl group with 5 to 20 carbon atoms, cycloalkoxy group with 5 to 20 carbon atoms, aryl group with 6 to 20 carbon atoms, or aryloxy group with 6 to 20 carbon atoms.

[0007] It also contains structural units derived from compounds represented by general formula (B).

[0008]

[0009] In general formula (B), Y represents an alkylene group having 1 to 4 carbon atoms, and c and d independently represent integers from 1 to 10; R 13 ~R 16 Each of these can be independently represented by a hydrogen atom, a halogen atom, a cyano group, an alkyl group with 1 to 20 carbon atoms, an alkoxy group with 1 to 20 carbon atoms, a cycloalkyl group with 5 to 20 carbon atoms, a cycloalkoxy group with 5 to 20 carbon atoms, an aryl group with 6 to 20 carbon atoms, or an aryloxy group with 6 to 20 carbon atoms; M represents a straight bond, -O-, -S-, or an alkylene group with 1 to 4 carbon atoms.

[0010]

[0011] In general formula (C), Z7 and Z8 represent aryl groups having 6 to 14 carbon atoms, preferably phenyl or naphthyl; Z represents alkylene groups having 1 to 4 carbon atoms, preferably methylene or ethylene; R 17 ~R 20 Each of the following can be independently represented: hydrogen atom, halogen atom, cyano group, alkyl group with 1 to 20 carbon atoms, alkoxy group with 1 to 20 carbon atoms, cycloalkyl group with 5 to 20 carbon atoms, cycloalkoxy group with 5 to 20 carbon atoms, aryl group with 6 to 20 carbon atoms, or aryloxy group with 6 to 20 carbon atoms.

[0012] In the thermoplastic resin structural units of the present invention, more than 80% are structural units derived from compounds represented by general formulas (A), (B), and (C); preferably, more than 90% are structural units derived from compounds represented by general formulas (A), (B), and (C), and may also include structural units derived from other diol compounds. Examples of diol compounds include, but are not limited to, those listed below: ethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentanediol, 1,4-cyclohexanediol, 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)-3-methylphenyl)fluorene, and 9,9-bis(6-(2-hydroxyethoxy)naphthyl)fluorene.

[0013] More preferably, all the thermoplastic resin structural units of the present invention are structural units derived from compounds represented by general formula (A), general formula (B) and / or (C).

[0014] Preferably, more than 80% of the thermoplastic resin structural units are structural units derived from compounds represented by general formulas (A) and (B); more preferably, more than 90% of the thermoplastic resin structural units are structural units derived from compounds represented by general formulas (A) and (B).

[0015] Preferably, more than 80% of the thermoplastic resin structural units are structural units derived from compounds represented by general formulas (A) and (C); more preferably, more than 90% of the thermoplastic resin structural units are structural units derived from compounds represented by general formulas (A) and (C).

[0016] In some preferred embodiments of the present invention, the thermoplastic resin structural unit comprises structural units derived from compounds represented by general formulas (A) and (B), wherein the proportion of structural units of the compound represented by general formula (A) is 5 to 90 mol%, and the proportion of structural units of the compound represented by general formula (B) is 10 to 95 mol%; preferably, the proportion of structural units of the compound represented by general formula (A) is 40 to 70 mol%, and the proportion of structural units of the compound represented by general formula (B) is 30 to 60 mol%.

[0017] In some preferred embodiments of the present invention, the thermoplastic resin structural unit comprises structural units derived from compounds represented by general formulas (A) and (C); the proportion of structural units of the compound represented by general formula (A) is 1 to 99 mol%, and the proportion of structural units of the compound represented by general formula (C) is 99 to 1 mol%; preferably, the proportion of structural units of the compound represented by general formula (A) is 30 to 60 mol%, and the proportion of structural units of the compound represented by general formula (C) is 40 to 70 mol%.

[0018] In some preferred embodiments of the present invention, the thermoplastic resin structural units comprise structural units derived from compounds represented by general formulas (A), (B), and (C); the proportion of structural units of the compound represented by general formula (A) is 5–90 mol%, the proportion of structural units of the compound represented by general formula (B) is 5–80 mol%, and the proportion of structural units of the compound represented by general formula (C) is 5–70 mol%; preferably, the proportion of structural units of the compound represented by general formula (A) is 10–80 mol%, the proportion of structural units of the compound represented by general formula (B) is 10–70 mol%, and the proportion of structural units of the compound represented by general formula (C) is 10–60 mol%.

[0019] The thermoplastic resin described in this invention can be one or more of polyester, polycarbonate, and polyester carbonate.

[0020] The form in which the structural units derived from the compounds represented by general formulas (A), (B), and (C) are contained in the resin is not particularly limited. For example, in this invention, the thermoplastic resin may contain a copolymer comprising structural units derived from the compounds represented by general formulas (A), (B), and (C), or it may be a resin composition comprising a homopolymer of each structural unit; or it may be a blend obtained by blending a homopolymer comprising structural units derived from the compounds represented by general formula (A) with a homopolymer comprising structural units derived from the compounds represented by general formulas (B) and (C).

[0021] The thermoplastic resin described in this invention can contain any structure including random, block, and alternating copolymer structures.

[0022] The thermoplastic resin described in this invention has a refractive index nD of 1.64–1.70 at 20°C and a wavelength of 589 nm, an Abbe number not exceeding 24, and an orientation birefringence Δn of 1.0 × 10⁻⁶. -3 Below this, the average transmittance for wavelengths between 780nm and 1000nm is over 87%.

[0023] The thermoplastic resin, tested according to ASTM D256 standard, has a low-temperature (-30℃) impact resistance of 25-60 J / m, preferably 35-50 J / m.

[0024] The thermoplastic resin was tested according to ASTM D256 standard. A 2mm injection molded specimen was immersed in deionized water at 80°C for 2 weeks, and the impact strength retention rate was ≥98%.

[0025] The thermoplastic resin of the present invention may contain additives such as mold release agents, ultraviolet absorbers, flow improvers, crystal nucleating agents, reinforcing agents, dyes, antistatic agents, or antibacterial agents.

[0026] The thermoplastic resin of the present invention can be prepared by reacting a dihydroxy compound containing the structures represented by general formulas (A), (B) and (C) with a carbonate diester or a dicarboxylic acid and / or a dicarboxylic acid ester.

[0027] Preferably, the dihydroxy compound shown is produced by reacting it with a carbonate diester or a dicarboxylic acid and / or a dicarboxylic acid ester in the presence of a basic compound catalyst, a transesterification catalyst, or a mixed catalyst consisting of both, or in the absence of a catalyst, via melt transesterification polycondensation.

[0028] Preferably, the dihydroxy compound represented by general formula (A) has at least one of the following structures:

[0029]

[0030] Preferably, the dihydroxy compound represented by general formula (B) has at least one of the following structures:

[0031]

[0032] Preferably, the dihydroxy compound represented by general formula (C) has at least one of the following structures:

[0033]

[0034] In this invention, the carbonate diester is one or more of diphenyl carbonate, dimethyl carbonate, diethylphenyl carbonate, diisopropylphenyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, etc., preferably diphenyl carbonate.

[0035] The dicarboxylic acid is selected from any one or a combination of at least two of terephthalic acid, terephthalic acid, 1,4-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,2-biphenyl dicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, and 2,2'-bis(carboxymethoxy)-1,1'-binaphthylene, preferably terephthalic acid and / or 2,6-naphthalenedicarboxylic acid;

[0036] The dicarboxylic acid ester is selected from any one or a combination of at least two of the following: dimethyl terephthalate, diethyl terephthalate, dimethyl terephthalate, dimethyl 1,4-naphthalenedicarboxylate, dimethyl 2,6-naphthalenedicarboxylate, dimethyl 2,2-biphenyl dicarboxylate, dimethyl 1,4-cyclohexanedicarboxylate, and 2,2'-bis(carboxymethyl methoxy)-1,1'-binaphthyl, preferably dimethyl terephthalate and / or dimethyl 2,6-naphthalenedicarboxylate.

[0037] The molar ratio of the carbonate diester or dicarboxylic acid and / or dicarboxylic acid ester to the sum of the added dihydroxy compounds of general formulas (A), (B) and (C) is 0.95 to 1.2:1, preferably 1.01 to 1.1:1.

[0038] The alkaline compound catalyst of this invention is one or more of lithium chloride, sodium chloride, potassium chloride, cesium chloride, lanthanum acetylacetone, cerium acetylacetone, sodium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, lithium bicarbonate, sodium bicarbonate, potassium bicarbonate, magnesium bicarbonate, calcium bicarbonate, strontium bicarbonate, barium bicarbonate, sodium carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenyl phosphate, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide, triethylamine, dimethylbenzylamine, triphenylamine, diethylamine, tetramethylborohydride, tetrabutylammonium borohydride, tetrabutyltetraphenylborate, tetraphenyltetraphenylborate, etc., preferably one or more of sodium hydroxide, sodium bicarbonate, and cesium carbonate.

[0039] The transesterification catalyst of the present invention can be one or more of zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin chloride, tin acetate, cerium acetylacetone, zirconium acetylacetone, zirconium acetate, tetrabutoxyzirconium, etc., preferably one or more of lanthanum acetylacetone, zirconium acetate, and zinc acetate.

[0040] The molar ratio of the total amount of the basic compound catalyst and / or transesterification catalyst to the total amount of the dihydroxy compound described in this invention is 5 × 10⁻⁶. -9 ~1×10 -4 The preferred ratio is 1×10 -7 ~1×10 -5 .

[0041] In some preferred embodiments of the present invention, the method for preparing the thermoplastic resin includes adding a dihydroxy compound of optional general formula (A) or optional general formula (B), a diester, a catalyst, and optional additives to a reactor; fully purging the air in the reactor with nitrogen 3 to 5 times; then heating the material in the reactor to melt it at a melting temperature of 180 to 210°C, preferably 190 to 200°C, with a residence time of 40 to 100 minutes, preferably 50 to 80 minutes. After the material has melted, stirring is started, pressure control is activated (either reduced or increased pressure), and the temperature is raised to the transesterification reaction temperature of 210 to 250°C, preferably 220 to 240°C, with a residence time of 60 to 320 minutes, preferably 150 to 240 minutes. Then, the pressure is further reduced and the temperature is increased to initiate the polycondensation reaction. During this stage, the system pressure is 10–500 Pa(A), preferably 50–100 Pa(A), the reaction temperature is 230–270 °C, preferably 230–255 °C, and the residence time is 10–120 min, preferably 20–60 min. During the reaction, the generated small molecule compounds are immediately removed by distillation, ultimately yielding a high molecular weight thermoplastic resin in the reactor.

[0042] The blends described in this invention can be obtained by blending different thermoplastic resins obtained by polymerization in equipment such as extruders, kneaders, and mixers.

[0043] This invention effectively lowers the glass transition temperature of a compound of general formula (A) by copolymerizing it with a flexible compound of general formula (B), thereby meeting the processing and application requirements in the field of optical lenses. Simultaneously, it was unexpectedly discovered that by introducing a compound of general formula (A) with more ether bonds into the comonomer, an optical resin material with high refractive index, high light transmittance, low water absorption, and excellent low-temperature impact resistance and hydrolysis resistance can be prepared. Optical lenses using the thermoplastic resin of this invention can be made thinner and lighter, reducing production costs, and are more suitable for outdoor extreme weather applications, exhibiting better resistance to environmental factors such as light and temperature changes. Detailed Implementation

[0044] The present invention will now be described in conjunction with specific embodiments. It should be noted that the embodiments are only used to further illustrate the present invention and should not be construed as limiting the scope of protection of the present invention. Any non-substantial improvements and adjustments made to the present invention based on its content are within the scope of protection of the present invention.

[0045] 1) Weight-average molecular weight (Mw): Using gel permeation chromatography (GPC), a standard curve was prepared using tetrahydrofuran as the developing solvent and standard polystyrene with a known molecular weight (molecular weight distribution = 1). Based on this standard curve, Mw was calculated from the retention time of GPC.

[0046] 2) Refractive index (nD): For a 1 mm thick film made of the thermoplastic resin prepared in the examples, the refractive index (nD) of the thermoplastic resin of the present invention at 20 °C and wavelength 589 nm was determined using an Abbe refractometer according to the method of JIS-K-7142.

[0047] 3) Abbe number: For the 0.1 mm thick polycarbonate resin film prepared in the examples, the refractive index at wavelengths of 486 nm, 589 nm, and 656 nm at 23 °C was measured using an Abbe refractometer, and the Abbe number ν was calculated using the following formula.

[0048] ν=(nD-1) / (nF-nC).

[0049] 4) Orientation birefringence (Δn): After cutting a 0.1 mm thick cast film into 5.0 cm squares, insert both ends of the film into chucks (3.0 cm apart) and stretch it to 1.5 times its original strength at Tg+5℃ of polycarbonate resin. Use an ellipsometer to measure the phase difference (Re) at 589 nm, and calculate the orientation birefringence (Δn) using the following formula.

[0050] Δn=Re / d

[0051] Δn: Orientation birefringence; Re: Phase difference; d: Thickness.

[0052] 5) Transmittance: The transmittance of a 0.1 mm thick film made of polycarbonate resin prepared in the examples was measured using a turbidimeter according to the method of JIS-K-7361-1.

[0053] 6) Glass transition temperature Tg: Measured using a differential scanning calorimeter (DSC).

[0054] 7) Impact strength: Tested according to ASTM D256 standard.

[0055] 8) Hydrolysis resistance: After immersing the 2mm injection molded specimen in deionized water at 80℃ for 2 weeks, the impact strength was tested according to ASTM D256 standard.

[0056] The sources of some of the reagents used in the embodiments and comparative examples of this invention are as follows; unless otherwise specified, the remaining reagents are commercially available products:

[0057] A-1 and A-2 were prepared according to the method disclosed in Toshihide Hasegawa, Macromolecules (2010), 43, 131–136, Diphenolic 9,9-Diarylfluorene Trimers and Derivatives Possessing Flexible Alkylene Chain Spacers: Synthesis of the Monomers, Their Polymerization, and Properties of the Resulting Polymers. The NMR results for compound A-1 are as follows: 1H-NMR (400MHz, CDCl3) / δ×10⁻⁶ -6 The NMR results for compound A-2 are as follows: 7.87 (m, 6H), 7.55 (m, 6H), 7.68–7.41 (m, 48H), 7.08 (m, 6H), 6.93 (m, 6H), 4.56 (s, 8H), 4.33 (t, 4H), 3.69–3.65 (m, 6H). -6 :7.90-7.87(m,10H),7.68-7.12(m,44H),6.93-6.87(m,6H),4.56(s,8H),4.33(t,4H),3.69-3.65(m,6H).

[0058] B-1 can be prepared by referring to the methods disclosed in Japanese Patent Application Publication Nos. 2014-227387, 2014-227388 and 2015-168658, including (1) a method of reacting 1,1-binaphthol with ethylene glycol monotoluenesulfonate, (2) a method of reacting binaphthol with haloalkanol or alkylene carbonate, and (3) a method of reacting 1,1-binaphthol with ethylene carbonate or propylene carbonate. Compound B-2 can be prepared by referring to the method disclosed in Patent CN112175178A.

[0059] Compound C-1 was prepared according to the method disclosed in patent CN1271025C. The NMR results of compound C-1 are as follows: 1H-NMR (400MHz, CDCl3) / δ×10 -67.87-7.28 (m, 8H), 6.99-6.75 (m, 6H), 4.33 (t, 4H), 3.69-3.65 (m, 6H), 2.15 (s, 6H). C-2 can be prepared according to the method disclosed in Example 3 of patent CN108017521B. The NMR results of compound C-2 are as follows: 1H-NMR (400MHz, CDCl3) / δ×10 -6 :7.90-7.87(m,6H),7.55-7.18(m,14H),4.43(t,4H),3.69-3.65(m,6H).

[0060] Example 1

[0061] 49.40 g (0.03 mol) of Al, 26.19 g (0.07 mol) of B1, 22.28 g (0.104 mol) of diphenyl carbonate, and 260.66 μg (8.0 × 10⁻⁶) of [unclear - possibly a chemical compound or product] were added. -7 Cesium carbonate (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus. The mixture was purged with nitrogen four times and heated to 190 °C under a nitrogen atmosphere of 101 kPa(A). After heating for 60 min to confirm complete dissolution of the raw materials, stirring was started, and the pressure was adjusted to 25 kPa(A). Simultaneously, the temperature was increased to 240 °C at a rate of 30 °C / hr. At this point, phenol, a byproduct, began to distill off. The reaction was maintained at 240 °C for 180 min, then increased to 250 °C at a rate of 60 °C / hr. Once the temperature reached 250 °C, the pressure was gradually reduced to 50 Pa(A) over one hour, and the reaction was continued under stirring for 60 min. The reaction was then terminated. After the reaction, nitrogen was introduced into the four-necked flask to restore atmospheric pressure. The resulting thermoplastic resin was removed, pelletized, molded, and its performance was evaluated. The results are listed in Table 1.

[0062] Example 2

[0063] 72.13g (0.05mol) A2, 20.31g (0.05mol) B2, 24.64g (0.115mol) diphenyl carbonate, and 2.4mg (6.0×10) -5 Sodium hydroxide (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0064] Example 3

[0065] 131.73 g (0.08 mol) A1, 3.74 g (0.01 mol) B1, 4.06 g (0.01 mol) B2, 22.71 g (0.106 mol) diphenyl carbonate, and 550.5 μg (3.0 × 10⁻⁶) were added. -61 mol) of zinc acetate was placed in a 200 ml four-necked flask equipped with a stirrer and a distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0066] Example 4

[0067] 28.85g (0.02mol) A2, 44.02g (0.08mol) C2, 20.35g (0.095mol) diphenyl carbonate, 1.38g (0.008mol) 1,4-cyclohexanedicarboxylic acid, and 2.181mg (5.0×10) -7 Lanthanum acetylacetone (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0068] Example 5

[0069] 7.21g (0.005mol) A2, 16.84g (0.045mol) B1, 23.91g (0.05mol) C1, 21.42g (0.1mol) diphenyl carbonate, and 50.40μg (6.0×10) -7 Sodium bicarbonate (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0070] Example 6

[0071] 129.83 g (0.09 mol) of A2, 4.78 g (0.01 mol) of Cl, 21.21 g (0.099 mol) of diphenyl carbonate, and 3.274 μg (1.0 × 10⁻⁶) of [unclear - likely a chemical compound or similar product] were added. -8 Zirconium acetate (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0072] Comparative Example 1

[0073] 164.67 g (0.1 mol) of Al was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus. Otherwise, the same procedure as in Example 1 was performed, and the results are listed in Table 1.

[0074] Comparative Example 2

[0075] 37.42 g (0.1 mol) B1 was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0076] Comparative Example 3

[0077] 55.02 g (0.1 mol) of C2 was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0078] Comparative Example 4

[0079] 18.71 g (0.05 mol) B1 and 23.91 g (0.05 mol) C1 were placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus. Otherwise, the same procedure as in Example 1 was performed, and the results are listed in Table 1.

[0080] Table 1

[0081]

Claims

1. A thermoplastic resin, characterized by, comprising structural units derived from compounds represented by general formula (A), and further comprising structural units derived from compounds represented by general formula (B) and / or (C): In General Formula (A), Z1to Z6independently represent an aryl group having 6 to 20 carbon atoms, preferably a phenyl group, a naphthyl group, an anthryl group; X represents an alkylene group having 1 to 4 carbon atoms, a and b independently represent an integer of 1 to 10; R1to R 12 independently represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aryloxy group having 6 to 20 carbon atoms; In General Formula (B), Y represents an alkylene group having 1 to 4 carbon atoms, c and d each independently represent an integer of 1 to 10; R 13 ~R 16 each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aryloxy group having 6 to 20 carbon atoms; M represents a direct bond, -O-, -S-, or an alkylene group having 1 to 4 carbon atoms; In General Formula (C), Z7and Z8represent an aryl group having 6 to 14 carbon atoms, preferably a phenyl group or a naphthyl group; Z represents an alkylene group having 1 to 4 carbon atoms, preferably a methylene group or an ethylene group; R 17 ~R 20 each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aryloxy group having 6 to 20 carbon atoms.

2. The thermoplastic resin according to claim 1, wherein more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C); more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C); more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A) and general formula (B); more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A) and general formula (B); 3. The thermoplastic resin according to claim 1 or 2, characterized by, more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A) and general formula (B); more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C).

4. The thermoplastic resin according to any one of claims 1 to 3, characterized by, more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C).

5. The thermoplastic resin according to any one of claims 1 to 4, characterized by, The thermoplastic resin has a refractive index nD of 1.64 to 1.70 at 20°C and a wavelength of 589 nm, an Abbe number of not higher than 24, and an oriented birefringence Δn of 1.0 x 10 -3 Hereinafter, the average transmittance at a wavelength of 780 nm to 1000 nm is 87% or more; more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the thermoplastic resin structural units are derived from compounds represented by general formula (A), general formula (B) and general formula (C). more preferably, 90% or more of the Preferably, the impact strength retention rate of the thermoplastic resin is ≥98% after 2mm injection-molded test pieces are immersed in 80℃ deionized water for 2 weeks according to the standard test of ASTM D256.

6. The thermoplastic resin according to any one of claims 1 to 5, characterized by, The thermoplastic resin further comprises one or more of a release agent, an ultraviolet absorber, a flowability improver, a crystallization nucleating agent, a reinforcing agent, a dye, an antistatic agent, or an antibacterial agent.

7. The thermoplastic resin according to any one of claims 1 to 6, characterized by, The thermoplastic resin is prepared by reacting dihydroxy compounds represented by structural general formula (A), general formula (B), and general formula (C) with a carbonic acid diester or a dicarboxylic acid and / or a dicarboxylic acid ester. Preferably, the dihydroxy compounds and the carbonic acid diester or the dicarboxylic acid and / or the dicarboxylic acid ester are reacted by melt transesterification polycondensation in the presence of a basic compound catalyst and / or an ester exchange catalyst, or without a catalyst.

8. The thermoplastic resin according to claim 7, characterized by The dihydroxy compounds represented by general formula (A) are at least one of the following structures: Preferably, the dihydroxy compounds represented by general formula (B) are at least one of the following structures: Preferably, the dihydroxy compounds represented by general formula (C) are at least one of the following structures: Preferably, the carbonic acid diester is one or more of diphenyl carbonate, ditolyl carbonate, diethylphenyl carbonate, diisopropylphenyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, preferably diphenyl carbonate; Preferably, the dicarboxylic acid is selected from any one or a combination of at least two of terephthalic acid, p-phenylenediacetic acid, 1,4-naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, 2,2-biphenyl dicarboxylic acid, 1,4-cyclohexane dicarboxylic acid, 2,2'-bis(carboxymethyloxy)-1,1'-binaphthalene, preferably terephthalic acid and / or 2,6-naphthalene dicarboxylic acid; Preferably, the dicarboxylic acid ester is selected from any one or a combination of at least two of dimethyl terephthalate, diethyl terephthalate, dimethyl p-phenylenediacetate, 1,4-naphthalene dicarboxylic acid dimethyl ester, 2,6-naphthalene dicarboxylic acid dimethyl ester, 2,2-biphenyl dicarboxylic acid dimethyl ester, 1,4-cyclohexane dicarboxylic acid dimethyl ester, 2,2'-bis(carboxylic acid methyl ester methyloxy)-1,1'-binaphthalene, preferably dimethyl terephthalate and / or 2,6-naphthalene dicarboxylic acid dimethyl ester; Preferably, the molar ratio of the carbonic acid diester or the dicarboxylic acid and / or the dicarboxylic acid ester to the total amount of the dihydroxy compounds represented by general formula (A), (B), and (C) is 0.95-1.2:1, preferably 1.01-1.1:

1. Preferably, the basic compound catalyst is one or more of lithium chloride, sodium chloride, potassium chloride, cesium chloride, lanthanum acetylacetonate, cerium acetylacetonate, sodium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, lithium bicarbonate, sodium bicarbonate, potassium bicarbonate, magnesium bicarbonate, calcium bicarbonate, strontium bicarbonate, barium bicarbonate, sodium carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenylphosphate, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide, triethylamine, dimethylbenzylamine, triphenylamine, diethylamine, tetramethylammonium borohydride, tetrabutylammonium borohydride, tetrabutylammonium tetraphenylborate, tetraphenylammonium tetraphenylborate, preferably one or more of sodium hydroxide, sodium bicarbonate, cesium carbonate; Preferably, the transesterification catalyst is one or more of zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin chloride, tin acetate, cerium acetylacetonate, zirconium acetylacetonate, zirconium acetate, tetrabutoxyzirconium, preferably one or more of lanthanum acetylacetonate, zirconium acetate, zinc acetate; Preferably, the molar ratio of the sum of the added basic compound catalyst and / or transesterification catalyst to the sum of the dihydroxy compounds is 5 x 10 -9 ~ 1 x 10 -4 , preferably the ratio is 1 x 10 -7 ~ 1 x 10 -5 .

9. The use of the thermoplastic resin according to any one of claims 1 to 8 for an optical molding, an optical lens, and an optical film.

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