Thermoplastic resin and optical lens including same

Abstract

The present invention makes it possible to provide a thermoplastic resin including a constituent unit (A) derived from a monomer represented by general formula (1). (In the formula, each R1 independently represents a C6-14 aryl group or a C7-17 aralkyl group, each R2 independently represents a hydrogen atom, a C6-14 aryl group, or a C7-17 aralkyl group, each a independently represents an integer of 0 or 1-3, each R3 independently represents -OH or -O-(CH2)n-OH, and n represents an integer of 1-4.)

Description

Thermoplastic resin and optical lens containing same

[0001] The present invention relates to a thermoplastic resin and an optical lens containing the same. More particularly, the present invention relates to a polycarbonate resin, a polyester carbonate resin, or a polyester resin, and an optical lens containing the same.

[0002] Optical glass or optical resin is used as a material for optical lenses used in the optical systems of various cameras, such as cameras with integrated film, video cameras, etc. Optical glass is excellent in heat resistance, transparency, dimensional stability, chemical resistance, etc., but has problems such as high material costs, poor moldability, and low productivity.

[0003] On the other hand, optical lenses made of optical resins have the advantage that they can be mass-produced by injection molding, and polycarbonate, polyester carbonate, polyester resin, etc. are used as high refractive index materials for camera lenses.

[0004] When an optical resin is used as an optical lens, in addition to optical properties such as refractive index and Abbe number, it is required to have heat resistance, transparency, low water absorption, chemical resistance, low birefringence, moist heat resistance, etc. In particular, in recent years, there has been a demand for optical lenses with high refractive index and high heat resistance, and various resins have been developed (Patent Documents 1 to 5).

[0005] JP 2018-2893 A JP 2018-2894 A JP 2018-2895 A JP 2018-59074 A WO2017 / 078073

[0006] An object of the present invention is to provide a thermoplastic resin that has excellent optical properties such as refractive index, Abbe number, and photoelastic coefficient while maintaining heat resistance sufficient for use, and an optical lens using the same.

[0007] As a result of extensive research aimed at solving the problems of the past, the present inventors have found that by using as a raw material a monomer having a specific structure in which a specific aryl group or aralkyl group is introduced into a 1,3-bis(1-methyl-1-phenylethyl)benzene compound, it is possible to obtain a thermoplastic resin that is excellent in optical properties such as refractive index, Abbe number, and photoelastic coefficient, as well as in heat resistance, and have completed the present invention.

[0008] That is, the present invention includes the following aspects: <1> A thermoplastic resin containing a structural unit (A) derived from a monomer represented by the following general formula (1). (In the formula, R １ each independently represents an aryl group having 6 to 14 carbon atoms or an aralkyl group having 7 to 17 carbon atoms; R ２ each independently represents a hydrogen atom, an aryl group having 6 to 14 carbon atoms, or an aralkyl group having 7 to 17 carbon atoms; each a independently represents 0 or an integer of 1 to 3; R ３ are each independently —OH or —O—(CH ２ ) ｎ represents —OH, and n represents an integer of 1 to 4.) <2> The thermoplastic resin according to <1> above, wherein the monomer represented by general formula (1) is a monomer represented by the following formula (1A): (In the formula, R １ , R ２ and a have the same definition as in general formula (1).) <3> The thermoplastic resin according to <1> above, wherein the monomer represented by general formula (1) is a monomer represented by the following formula (5): <4> The thermoplastic resin according to <1> above, wherein the monomer represented by the general formula (1) is a monomer represented by the following formula (1B): (In the formula, R １ , R ２ and a have the same definition as in general formula (1), and n independently represents an integer of 1 to 4.) <5> The thermoplastic resin according to <1> above, wherein the monomer represented by general formula (1) is a monomer represented by the following formula (15): <6> The thermoplastic resin according to any one of <1> to <5> above, wherein the thermoplastic resin is a polycarbonate resin, a polyester carbonate resin, or a polyester resin. <7> The thermoplastic resin according to any one of <1> to <6> above, wherein the thermoplastic resin contains a structural unit (B) derived from a monomer represented by the following general formula (6) and / or a structural unit (C) derived from a monomer represented by the following general formula (7): (In general formula (6), R ａ and R ｂ each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group having 5 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ R is selected from the group consisting of ｈ represents an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N, and S and which may have a substituent; X represents a single bond or an optionally substituted fluorene group; A and B each independently represent an optionally substituted alkylene group having 1 to 5 carbon atoms; m and n each independently represent an integer of 0 to 6; and a and b each independently represent an integer of 0 to 10. (In general formula (7), R ｃ and R ｄ are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group having 5 to 20 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms which may have a substituent; １represents a single bond, a fluorene group which may have a substituent, or any of the structural formulae represented by the following formulae (8) to (14): (In formulas (8) to (14), R ６１ , R ６２ , R ７１ and R ７２ each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent, or R ６１ and R ６２ , or R ７１ and R ７２ represent a carbocyclic or heterocyclic ring having 1 to 20 carbon atoms, which may have a substituent, formed by bonding together, and r and s each independently represent an integer of 0 to 5,000.) A and B each independently represent an alkylene group having 1 to 5 carbon atoms, which may have a substituent, p and q each independently represent an integer of 0 to 4, and a and b each independently represent an integer of 0 to 10.) <8> The thermoplastic resin according to <7> above, wherein in general formula (6) and general formula (7), A and B each independently represent an alkylene group having 2 or 3 carbon atoms. <9> The thermoplastic resin according to <7> or <8> above, which contains at least a structural unit derived from any one of BPEF, BNE, BNEF, and DPBHBNA. <10> The thermoplastic resin according to any one of <1> to <9> above, further comprising a structural unit derived from at least one monomer selected from the following group of monomers: (In the above formula, R １ and R ２ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ３ and R ４each independently represents a hydrogen atom, a methyl group, an ethyl group, or an alkylene glycol having 2 to 5 carbon atoms.) <11> The thermoplastic resin according to any one of <1> to <10> above, wherein the weight average molecular weight (Mw) of the thermoplastic resin in terms of polystyrene is 10,000 to 100,000. <12> The thermoplastic resin according to any one of <1> to <11> above, wherein the refractive index (nD) of the thermoplastic resin is 1.600 to 1.700. <13> The thermoplastic resin according to any one of <1> to <12> above, wherein the Abbe number (ν) of the thermoplastic resin is 22.0 to 26.0. <14> The thermoplastic resin according to any one of <1> to <13> above, wherein the glass transition temperature of the thermoplastic resin is 70 to 200°C. <15> The thermoplastic resin according to any one of <1> to <14> above, wherein the photoelastic coefficient of the thermoplastic resin is 25 to 45. <16> An optical lens containing the thermoplastic resin according to any one of <1> to <15> above.

[0009] According to the present invention, it is possible to provide a thermoplastic resin that has excellent optical properties such as refractive index, Abbe number, and photoelastic coefficient while maintaining heat resistance sufficient for use, and an optical lens containing the same.

[0010] 1 is a chart showing differential scanning calorimetry (DSC) data of the crystals of the compound obtained in Synthesis Example 2. FIG. 2 is a chart showing powder X-ray diffraction (PXRD) measurement of the crystals of the compound obtained in Synthesis Example 2.

[0011] Hereinafter, the present invention will be described in detail by way of examples and synthesis examples. However, the present invention is not limited to the synthesis examples and examples exemplified, and can be carried out by any method as long as it does not significantly deviate from the content of the present invention.

[0012] <Thermoplastic Resin> One embodiment of the present invention is a thermoplastic resin containing a structural unit (A) derived from a monomer represented by the following general formula (1). In the formula, R １ each independently represents an aryl group having 6 to 14 carbon atoms or an aralkyl group having 7 to 17 carbon atoms; R ２each independently represents a hydrogen atom, an aryl group having 6 to 14 carbon atoms, or an aralkyl group having 7 to 17 carbon atoms; each a independently represents 0 or an integer of 1 to 3; R ３ are each independently —OH or —O—(CH ２ ) ｎ represents —OH, and n represents an integer of 1 to 4.

[0013] (R in general formula (1) １ ) R in general formula (1) １ each independently represent an aryl group having 6 to 14 carbon atoms or an aralkyl group having 7 to 17 carbon atoms, of which preferably each independently represent an aryl group having 6 to 14 carbon atoms or an aralkyl group having 7 to 13 carbon atoms, more preferably each independently represent an aryl group having 6 to 14 carbon atoms or an aralkyl group having 7 to 11 carbon atoms, still more preferably each independently represent an aryl group having 6 to 14 carbon atoms, and particularly preferably each independently represent an aryl group having 6 to 10 carbon atoms. Examples of aryl groups having 6 to 14 carbon atoms include a phenyl group, a naphthyl group, an anthryl group, and a phenanthryl group, of which preferably a phenyl group or a naphthyl group, and more preferably a phenyl group. Examples of the aralkyl group having 7 to 17 carbon atoms include a benzyl group, a phenethyl group, a 1-methyl-1-phenylethyl group, a naphthalen-1-yl-methyl group, a naphthalen-2-yl-methyl group, a 1-methyl-1-(1-naphthyl)ethyl group, a 1-methyl-1-(2-naphthyl)ethyl group, an anthracen-9-yl-methyl group, and a phenanthrene-9-yl-methyl group. Among these, a benzyl group, a 1-methyl-1-phenylethyl group, a naphthalen-1-yl-methyl group, and a naphthalen-2-yl-methyl group are preferred, a benzyl group, a naphthalen-1-yl-methyl group, and a naphthalen-2-yl-methyl group are more preferred, and a benzyl group is even more preferred. １ As for the two R １ It is particularly preferable that both are phenyl groups.

[0014] (R in general formula (1) ２ ) R in general formula (1) ２are each independently a hydrogen atom, an aryl group having 6 to 14 carbon atoms, or an aralkyl group having 7 to 17 carbon atoms, and among these, each independently is preferably a hydrogen atom, an aryl group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms, and more preferably each independently is a hydrogen atom, an aryl group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 11 carbon atoms. Examples of aryl groups having 6 to 14 carbon atoms include a phenyl group, a naphthyl group, an anthryl group, and a phenanthryl group, and among these, a phenyl group or a naphthyl group is preferred, and a phenyl group is more preferred. Examples of the aralkyl group having 7 to 17 carbon atoms include a benzyl group, a phenethyl group, a 1-methyl-1-phenylethyl group, a naphthalen-1-yl-methyl group, a naphthalen-2-yl-methyl group, a 1-methyl-1-(1-naphthyl)ethyl group, a 1-methyl-1-(2-naphthyl)ethyl group, an anthracen-9-yl-methyl group, and a phenanthrene-9-yl-methyl group. Among these, a benzyl group, a 1-methyl-1-phenylethyl group, a naphthalen-1-yl-methyl group, and a naphthalen-2-yl-methyl group are preferred, a benzyl group, a naphthalen-1-yl-methyl group, and a naphthalen-2-yl-methyl group are more preferred, and a benzyl group is even more preferred. Each a in general formula (1) independently represents 0 or an integer of 1 to 3, and each a is preferably 0, 1, or 2, more preferably 0 or 1, and even more preferably 0. When a in the general formula (1) represents an integer of 1 to 3, R ３ At least one R in the ortho position of ２ is preferably bonded.

[0015] (R in general formula (1) ３ ) R in general formula (1) ３ are each independently —OH or —O—(CH ２ ) ｎ R in general formula (1) represents —OH. ３ When is —OH, the compound is a compound represented by general formula (1A) (compound 1A). In the formula, R １ , R ２ and a have the same definition as in general formula (1). ３ -O-(CH２ ) ｎ When it is —OH, the compound is a compound represented by general formula (1B) (compound 1B). In the formula, R １ , R ２ , a, and n have the same definitions as in general formula (1). In general formula (1B), n each independently represents an integer of 1 to 4, preferably an integer of 2 to 4, more preferably 2 or 3, and particularly preferably 2.

[0016] Among the 1,3-bis(1-methyl-1-phenylethyl)benzene compounds represented by the general formula (1) in the present invention, specific examples of compound 1A are shown below.

[0017]

[0018]

[0019] <Monomer Production Method-1> There are no particular limitations on the starting materials and production method used in the production of the 1,3-bis(1-methyl-1-phenylethyl)benzene compound represented by general formula (1) in the present invention. Examples of a production method for compound 1A include a production method in which a phenol compound represented by general formula (2) is reacted with α,α,α',α'-tetramethyl-1,3-benzenedimethanol, as exemplified by the following reaction formula: In the formula, R １ , R ２ and a are defined as in general formula (1).

[0020] Specific examples of the phenol compound represented by the general formula (2) include 2-phenylphenol, 2-(1-naphthyl)phenol, 2-(2-naphthyl)phenol, 2-(9-anthracenyl)phenol, 2-(9-phenanthryl)phenol, 2,6-diphenylphenol, 2-benzylphenol, 2-(1-methyl-1-phenylethyl)phenol, 2-(1-naphthylmethyl)phenol, 2-(2-naphthylmethyl)phenol, 2-(9-anthracenylmethyl)phenol, 2-(9-phenanthrylmethyl)phenol, 2-phenyl-6-benzylphenol, 2-phenyl-6-(1-methyl-1-phenylethyl)phenol, 2-phenyl-6-(1-naphthylmethyl)phenol, 2-phenyl-6-(2-naphthylmethyl)phenol, 2-(1-naphthyl)-6-benzylphenol, 2-(1-naphthyl)-6-(1-methyl-1-phenylethyl)phenol, 2-(1-naphthyl)-6-(1-naphthylmethyl)phenol, 2-(1-naphthyl)-6-(2-naphthylmethyl)phenol, 2-(2-naphthyl)-6-benzylphenol, 2-(2-naphthyl)-6-(1-methyl-1-phenylethyl)phenol, 2-(2-naphthyl)-6-(1-naphthylmethyl)phenol, 2-(2-naphthyl)-6-(2-naphthylmethyl)phenol and the like. In the above production method, the amount of the phenol compound represented by general formula (2) used is preferably in the range of 5 to 12 moles, more preferably in the range of 7 to 10 moles, and even more preferably 8 moles, per mole of α,α,α',α'-tetramethyl-1,3-benzenedimethanol.

[0021] The above production method is preferably carried out in the presence of an acid catalyst. Preferred acid catalysts include concentrated hydrochloric acid, sulfuric acid, and hydrochloric acid gas. It is particularly preferred to use hydrochloric acid gas until the reaction solution is saturated. The reaction is usually carried out in the presence of a solvent. There are no particular limitations on the solvent, so long as it does not inhibit the reaction. Compound 1A is readily soluble in a variety of solvents, so various solvents can be used. Among these, alcohols that have good solubility in the phenolic compound represented by general formula (2) are preferred, alcohols having 1 to 10 carbon atoms are more preferred, methanol, ethanol, propanol, and isopropanol are even more preferred, and methanol is particularly preferred. These solvents can be used alone or in combination. The amount of solvent used is not particularly limited as long as it does not interfere with the reaction; however, it is usually preferred to use a solvent in a range of 1 to 5 times by weight, more preferably 1 to 3 times by weight, and even more preferably 1 to 2 times by weight relative to α,α,α',α'-tetramethyl-1,3-benzenedimethanol. The above production method may be carried out under either air or an inert gas atmosphere; however, an inert gas atmosphere such as nitrogen or argon is preferred to suppress coloration of the reaction product. The reaction temperature is typically in the range of 20 to 40°C, preferably 25 to 30°C. The reaction pressure may be normal, elevated, or reduced pressure, but normal pressure is preferred. Compound 1A can be obtained from the resulting reaction mixture by separation and purification according to conventional methods. For example, to neutralize the acid catalyst, an aqueous alkali solution such as aqueous sodium hydroxide or aqueous ammonia is added to the reaction mixture. The neutralized reaction mixture is allowed to stand, and if necessary, a solvent capable of separating from water is added to separate and remove the aqueous layer. If necessary, distilled water is added to the resulting oil layer, followed by stirring and washing with water, and the aqueous layer is separated and removed. This procedure is repeated once or multiple times to remove the neutralized salt. The remaining raw materials and solvent are distilled off from the resulting oil layer to obtain the target compound 1A as a residual liquid.

[0022] Specific examples of the compound 1B of the present invention, which is a 1,3-bis(1-methyl-1-phenylethyl)benzene compound represented by the general formula (1), are shown below.

[0023]

[0024]

[0025] <Monomer Production Method-2> Examples of a method for producing compound 1B include a method of reacting a compound represented by general formula (1A) with an alkylene oxidizing agent. The reaction formula is exemplified below when a carbonate represented by general formula (3) is used as the alkylene oxidizing agent. In the formula, R １ , R ２ , a and n are the same as defined in general formula (1).

[0026] In the above production method, the compound 1A represented by general formula (1A) can be the compound obtained by the above-mentioned production method-1. As the alkylene oxidizing agent, for example, carbonates represented by general formula (3), such as ethylene carbonate, or halogenated alcohols, such as 2-chloroethanol and 3-chloro-1-propanol, can be used depending on the target compound. The use of carbonates represented by general formula (3) as the alkylene oxidizing agent in the above production method is described below. The raw material molar ratio of compound 1A to carbonates, compound 1A / carbonates, is usually in the range of about 1 / 2 to 1 / 5, preferably in the range of about 1 / 2 to 1 / 4, and more preferably in the range of about 1 / 2 to 1 / 3. In the above production method, it is preferable to use a basic catalyst during the reaction, and generally known basic catalysts can be used as the basic catalyst. Specific examples include quaternary ammonium salts such as tetraethylammonium bromide and tetramethylammonium chloride; alkali metal halide salts such as potassium hydroxide, potassium iodide, and sodium bromide; triorganophosphine compounds such as triphenylphosphine and tributylphosphine; amine catalysts such as 1-methylimidazole; and alkali catalysts such as potassium carbonate, calcium carbonate, magnesium carbonate, magnesium hydroxide, calcium hydroxide, sodium hydroxide, sodium bicarbonate, methoxysodium, and phenoxysodium. These basic catalysts may be used alone or in combination of two or more. The amount of this basic catalyst used is 0.001 to 10 wt %, preferably 0.01 to 1 wt %, of compound 1A represented by general formula (1A).

[0027] Although the reaction can be carried out without a solvent by using an excess amount of carbonates, it is usually preferable to carry out the reaction using an organic solvent from the standpoints of economy and operability. When a reaction solvent is used, various known solvents that are inert to the reaction can be used. Examples of such reaction solvents include aromatic hydrocarbons such as toluene and xylene, ether solvents such as tetrahydrofuran, dioxane, and 1,2-dimethoxyethane, ketone solvents such as acetone and methyl isobutyl ketone, halogenated hydrocarbons such as chloroform and 1,2-dichloroethane, aliphatic alcohols such as butanol and ethylene glycol, and polar solvents such as dimethylformamide and dimethyl sulfoxide. The amount of reaction solvent used is not particularly limited, but is preferably in the range of 0.5 to 10 times by weight, and more preferably 0.5 to 5 times by weight, relative to Compound 1A. The above production method may be carried out in either air or an inert gas atmosphere. However, an inert gas atmosphere such as nitrogen or argon is preferred to suppress coloration of the reaction product. The reaction temperature is not particularly limited as long as it is a temperature at which the reaction proceeds, but is usually carried out under heating. For example, the reaction is carried out at 100°C to 250°C, preferably under reflux of the solvent. The reaction time depends on the reaction temperature, the carbonates used, the amount and type of basic catalyst, etc., but is usually about 3 to 24 hours. In this reaction, the time when the generation of carbon dioxide gas subsides can be used as a guideline for the completion of the reaction. The resulting reaction mixture can be separated and purified in accordance with conventional methods to obtain Compound 1B from the reaction mixture. When a basic catalyst is used, it is neutralized by adding acid-containing water (e.g., hydrochloric acid, sulfuric acid), acetic acid, propionic acid, etc. This neutralization step may be carried out after the hydrolysis step described below. In this reaction, an excess amount of carbonates is added, and carbonates remain in the reaction solution even after the reaction is completed. Therefore, if treatment such as heating is carried out in this state, side reactions may proceed, reducing the purity and yield of the target compound, Compound 1B. Therefore, it is preferable to add water to carry out the hydrolysis step of carbonates. The amount of water used is in the range of 1 to 10 moles relative to the amount of carbonate used in the above reaction.The temperature may be below the boiling point of the reaction liquid, but is usually in the range from room temperature to below the boiling point of the reaction liquid. Specifically, the lower limit is 10°C or higher, more preferably 20°C or higher. The upper limit depends on the boiling point of the solvent used, but is preferably 150°C or lower. Thereafter, if necessary, a solvent that separates from water is added, and the oil layer is washed with water multiple times to separate and remove the water layer. Low boiling point substances such as the solvent are distilled and removed from the obtained oil layer under reduced pressure, and post-treatment operations such as water washing, crystallization, filtration, distillation, separation by column chromatography, etc., and drying can be performed. To further increase the purity, further purification by distillation, recrystallization, or column chromatography may be performed in accordance with conventional methods.

[0028] Among the compound 1B in the present invention, crystals of 1,3-bis[1-methyl-1-(4-(2-hydroxyethoxy)-3-phenylphenyl)ethyl]benzene represented by the following formula (15) can be handled as a crystalline solid, and are therefore very useful in industrial production of thermoplastic resins because they have excellent handleability and transportability. The crystals of 1,3-bis[1-methyl-1-(4-(2-hydroxyethoxy)-3-phenylphenyl)ethyl]benzene represented by the above formula (15) have an endothermic peak top temperature in the range of 134 to 140°C, more preferably in the range of 135 to 139°C, and particularly preferably in the range of 136 to 139°C, as measured by differential scanning calorimetry. Furthermore, the crystals of 1,3-bis[1-methyl-1-(4-(2-hydroxyethoxy)-3-phenylphenyl)ethyl]benzene represented by the above formula (15) have diffraction peaks at diffraction angles 2θ of 7.9±0.2°, 10.8±0.2°, 16.3±0.2°, and 18.6±0.2° in a powder X-ray diffraction peak pattern using Cu-Kα radiation. In addition, the crystal may have peaks at diffraction angles 2θ of 12.8±0.2°, 14.9±0.2°, 20.2±0.2°, and 24.1±0.2°. The purity of the crystals of 1,3-bis[1-methyl-1-(4-(2-hydroxyethoxy)-3-phenylphenyl)ethyl]benzene represented by formula (15) is preferably 90% or more, more preferably 93% or more, even more preferably 95% or more, and particularly preferably 98% or more, in terms of area percentage as determined by liquid chromatography analysis.

[0029] Crystals of the compound represented by formula (15) can be obtained by precipitating the compound from a solution in which the compound is dissolved in a chain aliphatic ketone solvent having 5 to 8 carbon atoms. The compound used here can be one obtained by the method described above. Precipitation of the compound represented by formula (15) from a solution in which the compound is dissolved in a chain aliphatic ketone solvent having 5 to 8 carbon atoms can be achieved by cooling the solution or by distilling off the solvent. However, it is preferable to prepare a solution in which a chain or cyclic aliphatic hydrocarbon solvent having 5 to 10 carbon atoms is mixed with a solution in which the compound is dissolved in a chain aliphatic ketone solvent having 5 to 8 carbon atoms, and, if necessary, further cool the solution to further reduce the solubility of the compound in the solution to effect precipitation. Examples of chain aliphatic ketone solvents having 5 to 8 carbon atoms include diethyl ketone (5 carbon atoms), methyl isobutyl ketone (6 carbon atoms), methyl amyl ketone (7 carbon atoms), and methyl hexyl ketone (8 carbon atoms). Among these, methyl isobutyl ketone and methyl amyl ketone are preferred. By using such an organic solvent, the solution can be washed with water before crystallization to remove water-soluble impurities such as salts. The amount of the chain aliphatic ketone solvent used is preferably 1 to 7 times by weight, more preferably 1.5 to 6 times by weight, and even more preferably 2 to 5 times by weight, relative to the weight of the compound represented by formula (15). Examples of chain or cyclic aliphatic hydrocarbon solvents having 5 to 10 carbon atoms include pentane, hexane, heptane, octane, isooctane, cyclopentane, and cyclohexane. Of these, cyclic aliphatic hydrocarbon solvents having 5 to 10 carbon atoms are preferred, and cyclopentane or cyclohexane are more preferred. The amount of the aliphatic hydrocarbon solvent used is preferably 1 to 10 times by weight, more preferably 1 to 7 times by weight, and even more preferably 1 to 5 times by weight, relative to the weight of the compound represented by formula (15).The temperature at which a solution of the compound represented by formula (15) in a chain aliphatic ketone having 5 to 8 carbon atoms is mixed with a chain or cyclic aliphatic hydrocarbon solvent having 5 to 10 carbon atoms varies depending on the chain aliphatic ketone solution used, but is preferably in the range of 60 to 120° C., more preferably in the range of 60 to 100° C., and even more preferably in the range of 60 to 90° C. The temperature at which crystals of the compound represented by formula (15) begin to precipitate is preferably in the range of 10 to 50° C., more preferably in the range of 15 to 40° C.

[0030] The crystals obtained by the above method can be isolated by a conventional method, for example, by centrifugal filtration. It is also preferable to further wash the crystals with a solvent. The solvent used can be removed by drying the obtained crystals.

[0031] The thermoplastic resin according to one embodiment of the present invention is not particularly limited and may be a polyester resin, a polycarbonate resin, a polyester carbonate resin, an epoxy resin, a polyurethane resin, a polyacrylic acid ester resin, a polymethacrylic acid ester resin, or the like. However, it is preferably a polycarbonate resin, a polyester carbonate resin, or a polyester resin, and more preferably contains a structural unit (A) represented by the following formula: In the formula, R １ , R ２ and a are the same as defined in general formula (1).

[0032] In a thermoplastic resin according to one embodiment of the present invention, the proportion of the structural unit (A) represented by the above formula relative to all structural units is not particularly limited, but is preferably 1 to 80 mol %, more preferably 1 to 60 mol %, and particularly preferably 5 to 50 mol % of all structural units. In other words, in addition to the structural unit (A) represented by the above formula, the thermoplastic resin according to one embodiment of the present invention can contain structural units derived from aliphatic dihydroxy compounds and structural units derived from aromatic dihydroxy compounds, which are generally used as structural units in polycarbonate resins and polyester carbonate resins. Specific examples of aliphatic dihydroxy compounds include, but are not limited to, 1,4-cyclohexanedimethanol, tricyclodecane dimethanol, 1,3-adamantanedimethanol, 2,2-bis(4-hydroxycyclohexyl)-propane, 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, 2-(5-ethyl-5-hydroxymethyl-1,3-dioxan-2-yl)-2-methylpropan-1-ol, isosorbide, 1,3-propanediol, 1,4-butanediol, and 1,6-hexanediol. Examples of aromatic dihydroxy compounds include various compounds, particularly 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 4,4'-dihydroxydiphenyl, bis(4-hydroxyphenyl)cycloalkane, bis(4-hydroxyphenyl)oxide, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxyphenyl)sulfone, bis(4-hydroxyphenyl)sulfoxide, bis(4-hydroxyphenyl)ketone, bisphenoxyethanolfluorene, and the like.

[0033] Furthermore, the thermoplastic resin according to one embodiment of the present invention preferably contains a structural unit (B) derived from a monomer represented by the following general formula (6). In general formula (6), R ａ and Rｂ each independently represents a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group having 5 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ R ｈ represents an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent. ａ and R ｂ is preferably a hydrogen atom, an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, more preferably a hydrogen atom, or an aryl group having 6 to 20 carbon atoms which may have a substituent, and even more preferably a hydrogen atom, or an aryl group having 6 to 12 carbon atoms which may have a substituent.

[0034] In general formula (6), X represents a single bond or a fluorene group which may have a substituent. X is preferably a single bond or a fluorene group which may have a substituent and has a total of 12 to 20 carbon atoms. In general formula (6), A and B each independently represent an alkylene group having 1 to 5 carbon atoms which may have a substituent, preferably an alkylene group having 2 or 3 carbon atoms. In general formula (6), m and n each independently represent an integer of 0 to 6, preferably an integer of 0 to 3, and more preferably 0 or 1. In general formula (6), a and b each independently represent an integer of 0 to 10, preferably an integer of 1 to 3, and more preferably 1 or 2.

[0035] Specific examples of the structural unit (B) include those derived from 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), DPBHBNA, and the like.

[0036] Furthermore, the thermoplastic resin according to one embodiment of the present invention preferably contains a structural unit (C) derived from a monomer represented by the following general formula (7). In general formula (7), R ｃ and R ｄ are each independently selected from the group consisting of a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group having 5 to 20 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms which may have a substituent. ｃ and R ｄ is preferably a hydrogen atom, an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, more preferably a hydrogen atom, or an aryl group having 6 to 20 carbon atoms which may have a substituent, and even more preferably a hydrogen atom, or an aryl group having 6 to 12 carbon atoms which may have a substituent.

[0037] In the general formula (7), Y １ represents a single bond, a fluorene group which may have a substituent, or any of the structural formulae represented by the following formulas (8) to (14), and is preferably a single bond or the structural formula represented by the following formula (8): In formulas (8) to (14), R ６１ , R ６２ , R ７１ and R ７２ each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent, or R ６１ and R ６２ , or R ７１ and R ７２are bonded to each other to form a carbon ring or hetero ring having 1 to 20 carbon atoms, which may have a substituent. In formulas (8) to (14), r and s each independently represent an integer of 0 to 5,000.

[0038] In the general formula (7), A and B each independently represent an alkylene group having 1 to 5 carbon atoms, which may have a substituent, and preferably an alkylene group having 2 or 3 carbon atoms. In the general formula (7), p and q each independently represent an integer of 0 to 4, and preferably 0 or 1. In the general formula (7), a and b each independently represent an integer of 0 to 10, preferably an integer of 0 to 5, and more preferably an integer of 0 to 2, for example, 0 or 1.

[0039] Specific examples of the structural unit (C) include BPEF (9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene), BPPEF (9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene), 9,9-bis[6-(2-hydroxyethoxy)naphthalen-2-yl]fluorene (BNEF), bisphenol A, bisphenol AP, bisphenol AF, bisphenol B, bisphenol BP, bisphenol C, bis(4-hydroxyphenyl)-2,2-dichloroethylene, bisphenol E, and bisphenol A. Bisphenol F, bisphenol G, bisphenol M, bisphenol S, bisphenol P, bisphenol PH, bisphenol TMC, bisphenol P-AP (4,4'-(1-phenylethylidene)bisphenol), bisphenol P-CDE (4,4'-cyclododecylidenebisphenol), bisphenol P-HTG (4,4'-(3,3,5-trimethylcyclohexylidene)bisphenol), bisphenol P-MIBK (4,4'-(1,3-dimethylbutylidene)bisphenol), bisphenol PEO-FL ( Bisphenoxyethanolfluorene), Bisphenol P-3MZ (4-[1-(4-hydroxyphenyl)-3-methylcyclohexyl]phenol), Bisphenol OC-FL (4,4'-[1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethylidene]bisphenol), Bisphenol Z, BP-2EO (2,2'-[[1,1'-biphenyl]-4,4'-diylbis(oxy)bisethanol), S-BOC (4,4'-(1-methylethylidene)bis(2-methylphenol)), TrisP -HAP (4,4',4''-ethylidene trisphenol), 1,1-bis(4-hydroxyphenyl)-1-phenylethane (BPAP), 1,1-bis(4-hydroxyphenyl)cyclododecane (HPCD), 1,1-bis(4-hydroxyphenyl)cyclohexane (BPZ), 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (BCFL), bis(4-hydroxyphenyl)diphenylmethane (BPBP), 1,3-bis(1-methyl-1-phenylethyl)benzene (BPM), and the like.Among these, preferred examples of the structural unit (C) include those derived from BPEF, BNEF, or BCFL.

[0040] The thermoplastic resin according to one embodiment of the present invention essentially contains the structural unit (A), but may also be a polymer containing the structural unit (B) but not the structural unit (C), a polymer containing the structural unit (C) but not the structural unit (B), a copolymer containing the structural unit (B) and the structural unit (C), a mixture of a polymer containing the structural unit (B) and a polymer containing the structural unit (C), or a combination thereof. Examples of polymers containing the structural unit (C) but not the structural unit (B) include those having structural units represented by the following formulas (I-1) to (I-3), and examples of copolymers having the structural unit (B) and the structural unit (C) include those having structural units represented by the following formulas (II-1) to (II-4). (In formula (I-1), m and n each represent an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1; the number of repeating units in formula (I-3) is an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1.) Furthermore, as the polymer having multiple types of structural units, either a block copolymer in which the values ​​of m and n are large, for example, 100 or more, or a random copolymer can be used, but a random copolymer is preferred, and more preferably a random copolymer in which the values ​​of m and n are 1 is used. (In formulas (II-1) to (II-4), m and n each independently represent an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1.) Furthermore, as the polymer having multiple types of structural units, either a block copolymer in which the values ​​of m and n (or m, n, and l) are large, for example, 100 or greater, or a random copolymer can be used. However, a random copolymer is preferred, and more preferably a random copolymer in which the values ​​of m and n (or m, n, and l) are 1. In the copolymer, the molar ratio of structural unit (B) to structural unit (C) is preferably 1:99 to 99:1, more preferably 10:90 to 90:10, even more preferably 15:85 to 85:15, and particularly preferably 30:70 to 70:30. Furthermore, in the mixture, the mass ratio of the polymer having the structural unit (B) to the polymer having the structural unit (C) is preferably 1:99 to 99:1, more preferably 10:90 to 90:10, even more preferably 15:85 to 85:15, and particularly preferably 30:70 to 70:30.

[0041] The thermoplastic resin according to one embodiment of the present invention preferably further contains a structural unit derived from at least one monomer selected from the following group of monomers: (In the above formula, R １ and R ２ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ３ and R ４ each independently represents a hydrogen atom, a methyl group, an ethyl group, or an alkylene glycol having 2 to 5 carbon atoms.

[0042] Furthermore, the thermoplastic resin of one embodiment of the present invention preferably contains a structural unit (D) derived from a monomer represented by the following general formula (16): In this case, the content of the structural unit (D) derived from the monomer represented by general formula (16) is preferably 1 to 50 mol %, and more preferably 1 to 30 mol %, of all structural units. In the general formula (16), L １ each independently represents a divalent linking group; R ３ and R４ each independently represents a halogen atom or a substituent having 1 to 20 carbon atoms which may contain an aromatic group; j3 and j4 each independently represents an integer of 0 to 4; and t represents an integer of 0 or 1.

[0043] In the above general formula (16), L １ each independently represents a divalent linking group. １ is preferably an alkylene group having 1 to 12 carbon atoms which may have a substituent, more preferably an alkylene group having 1 to 5 carbon atoms, even more preferably an alkylene group having 2 or 3 carbon atoms, and particularly preferably an ethylene group. １ Examples of the substituent on the alkylene group include an alkyl group, a cycloalkyl group, an aryl group, an alkoxyl group, and combinations thereof. Specific examples of these groups include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a phenyl group, a methoxy group, and an ethoxy group.

[0044] R ３ and R ４ When present, each independently represents a halogen atom or a substituent having 1 to 20 carbon atoms which may contain an aromatic group. Examples of halogen atoms include a fluorine atom, a chlorine atom, and a bromine atom. Examples of substituents having 1 to 20 carbon atoms which may contain an aromatic group include a methyl group, a phenyl group, a naphthyl group, a thienyl group, and a benzothienyl group. Examples of naphthyl groups include a 1-naphthyl group and a 2-naphthyl group, and examples of thienyl groups include a 2-thienyl group and a 3-thienyl group. Examples of benzothienyl groups include a 2-benzo[b]thienyl group and a 3-benzo[b]thienyl group. These groups may further have a substituent, and examples of such a substituent include those described above for L. １ Examples of the alkylene group include, but are not limited to, those described above as the substituents of the alkylene group.

[0045] j3 and j4 each independently represent an integer of 0 to 4. j3 and j4 are preferably integers of 0 to 2, more preferably 0 or 1, and particularly preferably 0. t represents an integer of 0 or 1, and is preferably 1.

[0046] The monomer represented by the general formula (16) preferably has a structure represented by the following formula (16').

[0047] In a preferred embodiment of the polycarbonate resin of the present invention, impurities such as alcohol compounds such as phenolic compounds that may be generated as by-products during production, and diol components or carbonate diesters that remain unreacted may be present. The impurities, such as alcohol compounds such as phenolic compounds and carbonate diesters, may cause a decrease in strength or the generation of odor when molded into a product, so it is preferable that the content of these impurities is as small as possible.

[0048] The content of residual phenolic compounds is preferably 3,000 ppm by mass or less, more preferably 1,000 ppm by mass or less, and particularly preferably 300 ppm by mass or less, based on 100% by mass of the polycarbonate resin. The content of residual diol components is preferably 1,000 ppm by mass or less, more preferably 100 ppm by mass or less, and particularly preferably 10 ppm by mass or less, based on 100% by mass of the polycarbonate resin. The content of residual carbonate diesters is preferably 1,000 ppm by mass or less, more preferably 100 ppm by mass or less, and particularly preferably 10 ppm by mass or less, based on 100% by mass of the polycarbonate resin. In particular, it is preferable that the contents of compounds such as phenol and t-butylphenol are low, and it is preferable that the contents of these compounds are within the above ranges.

[0049] The content of phenolic compounds remaining in the polycarbonate resin can be measured by a method of analyzing phenolic compounds extracted from the polycarbonate resin using gas chromatography. The content of alcoholic compounds remaining in the polycarbonate resin can also be measured by a method of analyzing alcoholic compounds extracted from the polycarbonate resin using gas chromatography. The content of diol components and carbonate diesters remaining in the polycarbonate resin can also be measured by a method of extracting these compounds from the polycarbonate resin and analyzing them using gas chromatography.

[0050] The contents of by-produced alcohol compounds such as phenolic compounds, diol components, and carbonate diesters may be reduced to an undetectable level, but from the viewpoint of productivity, they may be contained in small amounts within a range that does not impair the effects. Furthermore, small amounts can improve the plasticity of the resin when it is melted.

[0051] The content of each of the remaining phenolic compounds, diol components, and carbonate diesters may be, for example, 0.01 ppm by mass or more, 0.1 ppm by mass or more, or 1 ppm by mass or more, relative to 100% by mass of the polycarbonate resin. The content of the remaining alcoholic compounds may be, for example, 0.01 ppm by mass or more, 0.1 ppm by mass or more, or 1 ppm by mass or more, relative to 100% by mass of the polycarbonate resin.

[0052] The contents of by-produced alcohol compounds such as phenolic compounds, diol components, and carbonate diesters in the polycarbonate resin can be adjusted to fall within the above ranges by appropriately adjusting the polycondensation conditions and apparatus settings, and can also be adjusted by the conditions of the extrusion step after polycondensation.

[0053] For example, the amount of residual by-produced alcohol compounds such as phenolic compounds is related to the type of carbonate diester used in the polymerization of the polycarbonate resin, the polymerization reaction temperature, the polymerization pressure, etc. By adjusting these factors, the amount of residual by-produced alcohol compounds such as phenolic compounds can be reduced.

[0054] For example, when a polycarbonate resin is produced using a dialkyl carbonate such as diethyl carbonate, the molecular weight is difficult to increase, resulting in a low-molecular-weight polycarbonate, and the content of by-product alkyl alcohol compounds tends to be high. Such alkyl alcohols are highly volatile, and if they remain in the polycarbonate resin, the moldability of the resin tends to deteriorate. Furthermore, if a large amount of by-product alcohol compounds such as phenolic compounds remain, odor problems may occur during resin molding, or the cleavage reaction of the resin skeleton may progress during compounding, resulting in a decrease in molecular weight. Therefore, it is preferable that the content of by-product alcohol compounds remaining in the obtained polycarbonate resin be 3,000 ppm by mass or less relative to 100% by mass of the polycarbonate resin. The content of the remaining alcohol compounds is preferably 3,000 ppm by mass or less, more preferably 1,000 ppm by mass or less, and particularly preferably 300 ppm by mass or less, relative to 100% by mass of the polycarbonate resin.

[0055] <Physical Properties of Thermoplastic Resin> (1) Refractive Index (nD) In ​​one embodiment of the present invention, one of the characteristics of the thermoplastic resin is that it has a high refractive index, and the refractive index is preferably 1.600 to 1.700, more preferably 1.626 to 1.700, and particularly preferably 1.630 to 1.650. In the present invention, the refractive index can be measured by the method described in the examples below.

[0056] (2) Abbe number (ν) In one embodiment of the present invention, the Abbe number of the thermoplastic resin is preferably 22.0 to 26.0, more preferably 23.0 to 26.0, and particularly preferably 23.0 to 24.7. In the present invention, the Abbe number can be measured by the method described in the examples below.

[0057] (3) Glass Transition Temperature (Tg) In one embodiment of the present invention, one of the characteristics of the thermoplastic resin is high heat resistance, and the glass transition temperature (Tg) is preferably 70 to 200° C., more preferably 100 to 200° C., even more preferably 100 to 150° C., even more preferably 125 to 150° C., even more preferably 125 to 145° C., and particularly preferably 125 to 140° C. In the present invention, the glass transition temperature can be measured by the method described in the examples below.

[0058] (4) Weight Average Molecular Weight (Mw) in Polystyrene Equivalents In one embodiment of the present invention, the weight average molecular weight of the thermoplastic resin in polystyrene equivalents is preferably 10,000 to 100,000, more preferably 10,000 to 80,000, and particularly preferably 10,000 to 60,000.

[0059] (5) Photoelastic Coefficient In one embodiment of the present invention, one of the characteristics of the thermoplastic resin is that it has a low photoelastic coefficient, and the photoelastic coefficient is preferably 25 to 45, more preferably 25 to 38, and particularly preferably 30 to 38. In the present invention, the photoelastic coefficient can be measured by the method described in the examples below.

[0060] <Thermoplastic Resin Composition> Another embodiment of the present invention is a thermoplastic resin composition containing the above-described thermoplastic resin and an additive. The thermoplastic resin composition of this embodiment can be used in combination with a resin other than the thermoplastic resin of the present invention containing the above-described structural unit (A), as long as the desired effects of this embodiment are not impaired. Examples of such resins include, but are not limited to, at least one resin selected from the group consisting of polycarbonate resins, polyester resins, polyestercarbonate resins, (meth)acrylic resins, polyamide resins, polystyrene resins, cycloolefin resins, acrylonitrile-butadiene-styrene copolymer resins, vinyl chloride resins, polyphenylene ether resins, polysulfone resins, polyacetal resins, and methyl methacrylate-styrene copolymer resins. Various known resins can be used, and one type can be added alone or two or more types can be added in combination to the thermoplastic resin composition.

[0061] [Antioxidant] The thermoplastic resin composition preferably contains an antioxidant as the additive. The antioxidant preferably contains at least one of a phenolic antioxidant and a phosphite-based antioxidant. Examples of phenolic antioxidants include 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine e-2,4,6(1H,3H,5H)-trione, 4,4',4''-(1-methylpropanyl-3-ylidene)tris(6-tert-butyl-m-cresol), 6,6'-di-tert-butyl-4,4'-butylidene-m-cresol, ocladecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentane, methyl ... Examples of the hydroxybenzoate include pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 3,9-bis{2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethyl}-2,4,8,10-tetraoxospiro[5.5]undecane, and pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], and preferably pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate].Phosphite antioxidants include 2-ethylhexyl diphenyl phosphite, isodecyl diphenyl phosphite, triisodecyl phosphite, triphenyl phosphite, 3,9-bis(octadecyloxy)-2,4,8,10-tetraoxy-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 2,2'-methylenebis(4,6-di-tert-butylphenyl)2-ethylhexyl phosphite, Examples of the antioxidant include tris(2,4-di-tert-butylphenyl)phosphite, tris(nonylphenyl)phosphite, tetra-C12-15-alkyl(propane-2,2-diylbis(4,1-phenylene))bis(phosphite), and 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, and preferably 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane. As the antioxidant, any one of the above may be used alone, or a mixture of two or more may be used.

[0062] The antioxidant content in the thermoplastic resin composition is preferably 1 ppm by weight to 3,000 ppm by weight based on the total weight of the resin composition, more preferably 50 ppm by weight to 2,500 ppm by weight, even more preferably 100 ppm by weight to 2,000 ppm by weight, particularly preferably 150 ppm by weight to 1,500 ppm by weight, and even more preferably 200 ppm by weight to 1,200 ppm by weight.

[0063] [Release Agent] The thermoplastic resin composition preferably contains a release agent as the additive. Examples of the release agent include ester compounds, such as glycerin fatty acid esters such as mono- and diglycerides of glycerin fatty acid, glycol fatty acid esters such as propylene glycol fatty acid esters and sorbitan fatty acid esters, higher alcohol fatty acid esters, and full esters or mono-fatty acid esters of aliphatic polyhydric alcohols and aliphatic carboxylic acids. When an ester of aliphatic polyhydric alcohols and aliphatic carboxylic acids is used as the release agent, either a monoester or a full ester can be used, but other than a full ester, such as a monoester, may also be used. Specific examples of the release agent include the following.That is, sorbitan fatty acid esters such as sorbitan stearate, sorbitan laurate, sorbitan oleate, sorbitan trioleate, sorbitan tribehenate, sorbitan stearate, sorbitan tristearate, and sorbitan caprylate; propylene glycol fatty acid esters such as propylene glycol monostearate, propylene glycol monooleate, propylene glycol monobehenate, propylene glycol monolaurate, and propylene glycol monopalmitate; higher alcohol fatty acid esters such as stearyl stearate; glycerin monohydroxystearates such as glycerin monostearate and glycerin mono-12-hydroxystearate, glycerin monooleate, glycerin monobehenate, glycerin monocaprylate, glycerin monocaprate, and glycerin Examples of the monoglycerides include monoglycerides such as monolaurate, and mono-diglycerides such as glycerin monodistearate, glycerin monodistearate, glycerin monodibehenate, and glycerin monodiolate; acetylated monoglycerides of glycerin fatty acid esters such as glycerin diacetomonolaurate; organic acid monoglycerides of glycerin fatty acid esters such as citric acid fatty acid monoglyceride, succinic acid fatty acid monoglyceride, and diacetyltartaric acid fatty acid monoglyceride; and polyglycerin fatty acid esters such as diglycerin stearate, diglycerin laurate, diglycerin oleate, diglycerin monostearate, diglycerin monolaurate, diglycerin monomyristate, diglycerin monooleate, tetraglycerin stearate, decaglycerin laurate, decaglycerin oleate, and polyglycerin polyricinoleate.

[0064] The thermoplastic resin composition preferably contains 1 ppm by weight to 5,000 ppm by weight of the release agent based on the total weight of the resin composition, more preferably 50 ppm by weight to 4,000 ppm by weight, even more preferably 100 ppm by weight to 3,500 ppm by weight, particularly preferably 500 ppm by weight to 13,000 ppm by weight, and even more preferably 1,000 ppm by weight to 2,500 ppm by weight.

[0065] [Other Additives] In addition to the antioxidant and mold release agent described above, other additives may be added to the thermoplastic resin composition. For example, additives that may be contained in the thermoplastic resin composition include compounding agents, catalyst deactivators, heat stabilizers, plasticizers, fillers, UV absorbers, rust inhibitors, dispersants, antifoaming agents, leveling agents, flame retardants, lubricants, dyes, pigments, bluing agents, nucleating agents, and clarifying agents. The content of other additives other than the antioxidant and mold release agent in the thermoplastic resin composition is preferably 10 ppm by weight to 5.0% by weight, more preferably 100 ppm by weight to 2.0% by weight, and even more preferably 1000 ppm by weight to 1.0% by weight, but is not limited thereto. The above-mentioned additives may adversely affect transmittance, so it is preferable not to add them in excess; for example, the total amount added is within the above-mentioned range.

[0066] <Optical Members> The thermoplastic resin or thermoplastic resin composition of the present invention (hereinafter simply referred to as "resin composition") can be suitably used for optical members. In one embodiment of the present invention, an optical member comprising the resin composition of the present invention is provided. In one embodiment of the present invention, optical members include, but are not limited to, optical disks, transparent conductive substrates, optical cards, sheets, films, optical fibers, lenses, prisms, optical films, substrates, optical filters, hard coat films, and the like. The resin composition of the present invention can be molded by a casting method with high flowability, and is therefore particularly suitable for producing thin optical members. In a preferred embodiment of the present invention, the optical member produced using the resin composition of the present invention may be an optical lens. In another preferred embodiment of the present invention, the optical member produced using the resin composition of the present invention may be an optical film.

[0067] When an optical element containing the resin composition of the present invention is produced by injection molding, molding is preferably performed under conditions of a cylinder temperature of 260 to 350°C and a mold temperature of 90 to 170°C. More preferably, molding is performed under conditions of a cylinder temperature of 270 to 320°C and a mold temperature of 100 to 160°C. If the cylinder temperature is higher than 350°C, the resin composition will decompose and discolor, and if it is lower than 260°C, the melt viscosity will be high, making molding difficult. Furthermore, if the mold temperature is higher than 170°C, it will be difficult to remove a molded piece made of the resin composition from the mold. On the other hand, if the mold temperature is lower than 90°C, the resin will harden too quickly in the mold during molding, making it difficult to control the shape of the molded piece and making it difficult to sufficiently transfer the shape of the molded piece.

[0068] <Optical Lens> In one embodiment of the present invention, the resin composition can be suitably used for optical lenses. Optical lenses produced using the resin composition of the present invention have a high refractive index and excellent heat resistance, and are therefore extremely useful in fields where expensive high refractive index glass lenses have traditionally been used, such as telescopes, binoculars, and television projectors. For example, in smartphone lenses, a lens molded from a thermoplastic resin containing the structural unit (A) and a resin containing any one of the structural units of formulas (II-1) to (II-4), or (In the above formula, R １ and R ２ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ３ and R ４ each independently represents a hydrogen atom, a methyl group, an ethyl group, or an alkylene glycol having 2 to 5 carbon atoms.) A lens molded from a resin containing a structural unit derived from any one of the monomers of the above formulas can be superimposed on the resin to be used as a lens unit.

[0069] The optical lens of the present invention is preferably implemented as an aspherical lens, if necessary. Since an aspherical lens can substantially eliminate spherical aberration with a single lens, it is not necessary to eliminate spherical aberration by combining multiple spherical lenses, which allows for weight reduction and reduced molding costs. Therefore, aspherical lenses are particularly useful as camera lenses, among other optical lenses.

[0070] Furthermore, because the optical lens of the present invention has high molding fluidity, it is particularly useful as a material for optical lenses that are thin, small, and have complex shapes. Specifically, the lens size preferably has a central thickness of 0.05 to 3.0 mm, more preferably 0.05 to 2.0 mm, and even more preferably 0.1 to 2.0 mm. The diameter is preferably 1.0 to 20.0 mm, more preferably 1.0 to 10.0 mm, and even more preferably 3.0 to 10.0 mm. Furthermore, the lens preferably has a meniscus shape, with one side convex and the other concave. The optical lens of the present invention can be molded by any method, such as mold molding, cutting, polishing, laser machining, electrical discharge machining, or etching. Among these, mold molding is more preferred in terms of production costs.

[0071] <Optical Film> In one embodiment of the present invention, the resin composition can be suitably used for optical films. In particular, optical films produced using the polycarbonate resin of the present invention have excellent transparency and heat resistance, and are therefore suitable for use as films for liquid crystal substrates, optical memory cards, etc. In order to minimize the inclusion of foreign matter in the optical film, the molding environment must naturally be a low-dust environment, preferably class 6 or less, and more preferably class 5 or less.

[0072] Examples of the present invention will be described below together with comparative examples to illustrate the details of the invention, but the present invention is not limited to these examples. The physical properties of the obtained resin were measured using the following methods and devices.

[0073] 1) NMR analysis Measurement device: Fourier transform nuclear magnetic resonance AVANCE III HD 400 (manufactured by BRUKER) Measurement samples were dissolved in deuterated chloroform (CDCl ３) and １３ C-NMR and １ The H-NMR spectrum was measured.

[0074] 2) Refractive index Measuring device: Refractometer (Kyoto Electronics Manufacturing Co., Ltd.: RA-500) Tetrahydrofuran solutions of the measurement sample (solutions with concentrations of 30%, 20%, and 10%) were prepared, and the refractive index was measured with the refractometer. From the obtained results, the relationship between concentration and refractive index was derived, and the value at a concentration of 100% was calculated by extrapolation, and this value was used as the refractive index of the measurement sample.

[0075] 3) Thermal Analysis 3 mg of the crystals obtained in the synthesis example were weighed into an aluminum pan, and thermal analysis of the crystals was performed using a differential scanning calorimeter (DSC7020 manufactured by Hitachi High-Tech Science Corporation) under the following operating conditions, using aluminum oxide as a control. (Operating conditions) Heating rate: 10°C / min. Measurement temperature range: 30 to 400°C. Measurement atmosphere: open, nitrogen 50 mL / min.

[0076] 4) Powder X-ray Diffraction Method (PXRD) 0.1 g of the compound obtained in Synthesis Example was filled into the sample filling section of a glass test plate, and measurement was carried out using the following apparatus and conditions. [Measurement apparatus] MiniFlex600-C / Rigaku Corporation [Measurement conditions] X-ray source: CuKα Tube voltage: 40 kV Tube current: 15 mA Scan axis: 2θ / θ Mode: Continuous Measurement range: 2θ = 5° to 90° Step: 0.02° Speed ​​measurement time: 10° / min Entrance slit: 0.25° Receiving slit: 13.00 mm

[0077] 5) Weight-average molecular weight (Mw) The weight-average molecular weight of the obtained resin was measured by gel permeation chromatography (GPC) and calculated in terms of standard polystyrene. The apparatus, column, and measurement conditions used were as follows: GPC apparatus: HLC-8420GPC, manufactured by Tosoh Corporation Columns: TSKgel SuperHM-M x 3, manufactured by Tosoh Corporation TSKgel guard column SuperH-H x 1, manufactured by Tosoh Corporation TSKgel SuperH-RC x 1, manufactured by Tosoh Corporation Detector: RI detector Standard polystyrene: Standard polystyrene kit PStQuick C, manufactured by Tosoh Corporation Sample solution: 0.2% by mass tetrahydrofuran solution Eluent: tetrahydrofuran Eluent flow rate: 0.6 mL / min Column temperature: 40°C

[0078] 6) Glass transition temperature (Tg): Measured according to JIS K7121-1987 using a differential scanning calorimeter with a temperature increase program of 10°C / min. Differential scanning calorimeter: TA Instruments DSC2500

[0079] 7) Refractive index (nD) A test specimen was prepared by molding a polycarbonate resin into a V-shaped block according to JIS B 7071-2:2018. The refractive index was measured at 23°C using a refractometer (Shimadzu KPR-3000).

[0080] 8) Abbe number (ν) Using the same test piece (V-block) as used in the refractive index measurement, the refractive index was measured at wavelengths of 486 nm, 589 nm, and 656 nm at 23°C using a refractometer, and the Abbe number was calculated using the following formula: Refractometer: KPR-3000 manufactured by Shimadzu Corporation ν=(nD-1) / (nF-nC) nD: refractive index at wavelength 589 nm nC: refractive index at wavelength 656 nm nF: refractive index at wavelength 486 nm

[0081] 9) Photoelastic coefficient The obtained resin was dissolved in dichloromethane to obtain a resin solution. This resin solution was spread on a tray, and the solvent was evaporated to obtain a 0.1 mm thick film, which was used as a sample piece. The photoelastic coefficient was measured using an ellipsometer. Measurement method: The photoelastic coefficient was calculated by measuring the change in birefringence with respect to the change in load at a wavelength of 633 nm. Ellipsometer: Ellipsometer M-220 manufactured by JASCO Corporation

[0082] Synthesis Example 1: Production of 1,3-bis[1-methyl-1-(4-hydroxy-3-phenylphenyl)ethyl]benzene A 1000 mL four-neck flask equipped with a reflux condenser was charged with 157.7 g (0.93 mol) of 2-phenylphenol and 21.0 g of methanol. The atmosphere in the flask was completely purged with nitrogen gas, and then the atmosphere in the flask was completely purged with hydrochloric acid gas at an internal temperature of 35°C. Meanwhile, a separate glass vessel was charged with 30.0 g (0.15 mol) of α,α,α',α'-tetramethyl-1,3-benzenedimethanol, 53.0 g (0.31 mol) of 2-phenylphenol, and 37.5 g of methanol, and the vessel was heated to 65°C to prepare Solution A. While maintaining the internal temperature of the four-neck flask at 30°C, hydrochloric acid gas was blown into the vessel, and Solution A was added dropwise over 2 hours using a dropping funnel. After the dropwise addition, the internal temperature was lowered to 25°C, and stirring was continued overnight. After the reaction was completed, the reaction solution was neutralized with aqueous sodium hydroxide, and the separated aqueous layer was removed. 192.5 g of toluene and 45.0 g of water were added, and the mixture was stirred at an internal temperature of 65°C for 30 minutes, then allowed to stand, and the separated aqueous layer was removed. The resulting oil layer was then washed twice with water at an internal temperature of 75°C to remove sodium chloride produced by neutralization. The toluene and 2-phenylphenol in the flask were then distilled off under heating and reduced pressure conditions (internal temperature of the final flask: 270°C, internal pressure: 0.6 kPa). The residue in the flask was then removed. The solid obtained after cooling was colorless and transparent. The above NMR analysis confirmed that the resulting solid was the target product. １ H-NMR (400 MHz, solvent: CDCl ３ ) δ<ppm>: 1.75 (s, 6H), 5.32 (s, 1H), 7.10-7.55 (m, 9H).１３ C-NMR (400 MHz, solvent: CDCl ３ ) δ <ppm>: 31.09, 42.60, 115.43, 123.97, 127.39, 127.69, 127.75, 127.85, 128.48, 129.23, 129.26, 137.73, 148.29, 150.19, 150.37. The yield of the target product was 89 mol% based on the raw material α,α,α',α'-tetramethyl-1,3-benzenedimethanol. The purity measured by high-performance liquid chromatography was 91.9%.

[0083] Synthesis Example 2: Preparation of 1,3-bis[1-methyl-1-(4-(2-hydroxyethoxy)-3-phenylphenyl)ethyl]benzene A 500 mL four-neck flask equipped with a reflux condenser was charged with 52.6 g (0.31 mol) of 3-phenylphenol and 11.8 g of methanol. The atmosphere inside the flask was completely purged with nitrogen gas, and then the atmosphere inside the flask was completely purged with hydrochloric acid gas at an internal temperature of 35°C. Meanwhile, a separate glass vessel was charged with 15.0 g (0.08 mol) of α,α,α',α'-tetramethyl-1,3-benzenedimethanol, 26.0 g (0.15 mol) of 3-phenylphenol, and 18.8 g of methanol, and the vessel was heated to 65°C to prepare Solution A. While maintaining the internal temperature of the four-neck flask at 30°C, hydrochloric acid gas was blown in, and Solution A was added dropwise over 1.5 hours using a dropping funnel. After the dropwise addition, the internal temperature was lowered to 25°C, and stirring was continued overnight. After the reaction was completed, the atmosphere inside the flask was purged with nitrogen gas, and the reaction solution was neutralized with aqueous sodium hydroxide solution, and the separated aqueous layer was removed. 96.2 g of toluene and 22.5 g of water were added and stirred at an internal temperature of 65°C for 30 minutes, then allowed to stand, and the separated aqueous layer was removed. The resulting oil layer was then washed twice with water at an internal temperature of 75°C to remove sodium chloride produced by neutralization. The toluene and 3-phenylphenol in the flask were then distilled off under heated and reduced pressure conditions (internal temperature of the final flask: 220°C, internal pressure: 0.5 kPa). The resulting distillation residue (36.9 g) was confirmed to contain 1,3-bis[1-methyl-1-(4-hydroxy-3-phenylphenyl)ethyl]benzene (hereinafter referred to as "Compound A") synthesized in Synthesis Example 1. The crude yield of Compound A relative to α,α,α',α'-tetramethyl-1,3-benzenedimethanol was 94 mol%. Thereafter, 15.3 g (0.17 mol) of ethylene carbonate, 1.6 g (0.03 mol) of potassium hydroxide, 1.2 g (0.004 mol) of tetrabutylammonium bromide, and 110.7 g of methyl isobutyl ketone were added to the flask, and the atmosphere in the flask was replaced with nitrogen. The liquid temperature in the flask was then heated to 115°C and stirred for 5 hours while maintaining the temperature at 115°C to 116°C. After the reaction, the liquid temperature in the flask was lowered to 85°C, and 22.9 g of pure water was added to the reaction liquid to hydrolyze the remaining ethylene carbonate. Thereafter, 8.8 g of 12% aqueous hydrochloric acid was added to neutralize the liquid, and the aqueous layer was separated.Purified water was added to the resulting oil layer and stirred. The aqueous layer was separated and washed five times to remove potassium chloride produced by neutralization. 73.6 g of cyclohexane was then added, and the liquid in the flask was cooled to 25°C, resulting in the precipitation of crystals. The precipitated crystals were filtered off, yielding 44.6 g of solvent-containing crystals. NMR analysis of the resulting crystals confirmed that they were the target product, 1,3-bis[1-methyl-1-(4-(2-hydroxyethoxy)-3-phenylphenyl)ethyl]benzene (hereinafter referred to as "Compound B"). The yield of Compound B relative to the amount of Compound A used was 77 mol %. Subsequently, 44.3 g of the resulting Compound B crystals (34.0 g as Compound B) and 132.9 g of methyl isobutyl ketone were added to a 500 ml four-neck flask equipped with a reflux condenser. The liquid in the flask was heated to 75°C and stirred to completely dissolve the solids. Thereafter, 88.6 g of cyclohexane was added, and the liquid in the flask was cooled to 25°C, causing crystals to precipitate. The precipitated crystals were filtered out and dried by heating under reduced pressure to obtain white crystals of compound B. １ H-NMR (400 MHz, solvent: CDCl ３ ) δ<ppm>: 1.75 (s, 6H), 2.22 (t, 1H), 3.80-3.83 (q, 2H), 4.03-4.05 (t, 2H), 6.87-6.89 (d, 1H), 7.12-7.55 (m, 10H). １３ C-NMR (400 MHz, solvent: CDCl ３) δ <ppm>: 30.99, 42.59, 61.41, 70.32, 112.94, 123.78, 126.22, 126.97, 127.19, 127.63, 128.12, 129.31, 129.56, 1, 30.47, 138.88, 143.94, 150.30, 153.25. The purity measured by high performance liquid chromatography was 98.8%. The refractive index measured by the above analytical method using the obtained compound as a measurement sample was 1.611. Differential scanning calorimetry analysis of the crystals of the obtained compound showed that the top temperature of the endothermic peak was 137.3 °C. Differential scanning calorimetry (DSC) data is shown in Figure 1. The diffraction angles 2θ (°) of the diffraction peaks that appeared in powder X-ray diffraction (PXRD) measurement of the crystals of the obtained compound and peaks with relative integrated intensities of 30 or more based on the peak with the largest integrated intensity are shown in Table 1. The PXRD measurement chart is shown in Figure 2.

[0084]

[0085] Example 1 As raw materials, 16.694 g (0.0381 mol) of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF), 8.1361 g (0.0163 mol) of 4-(1-{3-[1-(4-hydroxy-3-phenylphenyl)-isopropyl]phenyl}-isopropyl)-2-phenylphenol (also known as 1,3-bis[1-methyl-1-(4-hydroxy-3-phenylphenyl)ethyl]benzene, abbreviated as BisOPP-M) obtained in Synthesis Example 1, 12.000 g (0.0560 mol) of diphenyl carbonate (DPC), and 2.5 × 10 －２ 20 μl (5.0 × 10 －７ mole, i.e., 9.2 × 10 per mole of the total of dihydroxy compounds －６ (mol) was placed in a 300 mL reactor equipped with a stirrer and a distillation device, and the system was placed under nitrogen flow conditions. The reactor was immersed in an oil bath heated to 200°C to initiate the transesterification reaction. The temperature was raised to 240°C over 140 minutes, and the pressure was reduced to 0 kPa. After maintaining this temperature for 30 minutes, nitrogen gas was introduced into the reaction system, and the pressure was returned to 101.3 kPa, yielding a polycarbonate resin. The physical properties of the resulting resin are shown in Table 1.

[0086] Example 2 A polycarbonate resin was obtained in the same manner as in Example 1, except that the amounts of raw materials charged were as shown in Table 2. The physical properties of the obtained resin are shown in Table 1.

[0087] Comparative Example 1 A polycarbonate resin was obtained in the same manner as in Example 1, except that 5.6527 g (0.0163 mol) of 1,3-bis(1-methyl-1-phenylethyl)benzene (abbreviation: BPM) was used instead of 8.1361 g (0.0163 mol) of 1,3-bis[1-methyl-1-(4-hydroxy-3-phenylphenyl)ethyl]benzene (abbreviation: BisOPP-M) obtained in Synthesis Example 1. The physical properties of the obtained resin are shown in Table 1.

[0088]

[0089]

[0090] Examples 3 and 4, Comparative Example 2 Polycarbonate resins were obtained in the same manner as in Example 1, except that the amounts of raw materials charged were as shown in Table 4. Table 3 shows the physical properties of the obtained resins.

[0091] Example 5 (Step 1) 36.1 g of BisOPP-M obtained in Synthesis Example 1 and 63.9 g of 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (abbreviation, BCFL), i.e., BisOPP-M:BCFL = 30:70 (mol %), were added to 500 ml of a 9 wt % aqueous sodium hydroxide solution, and 0.5 g of hydrosulfite was further added and dissolved. To this solution, 300 ml of dichloromethane and 0.1 g of triethylbenzylammonium chloride (TEBAC: manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added, and the solution temperature was set to 20°C with stirring, and 47.8 g of phosgene was further blown in over 30 minutes. (Step 2) After the phosgene injection was completed, 1.45 g of p-tert-butylphenol (PTBP) dissolved in 50 ml of dichloromethane was added and emulsified by vigorously stirring for 7 minutes. Then, 0.5 ml of triethylamine was added as a polymerization catalyst and polymerization was allowed to proceed for 30 minutes. (Post-Step) The polymerization solution was separated into an aqueous layer and an organic layer. The organic layer was neutralized with phosphoric acid and repeatedly washed with pure water until the pH of the washings reached pH 7.0. The organic solvent was evaporated and distilled off from this purified polycarbonate resin, yielding a polycarbonate resin powder. This polycarbonate resin powder was dried at 120°C for 24 hours to completely distill off the solvent. The physical properties of the resulting resin are shown in Table 5.

[0092] Comparative Example 3 A polycarbonate resin was obtained in the same manner as in Example 5, except that BisOPP-M was replaced with 28.2 g of BPM and 71.8 g of BCFL, i.e., BPM:BCFL=30:70 (mol %), and the phosgene and PTBT were replaced with 37.6 g and 2.04 g, respectively. The physical properties of the obtained resin are shown in Table 5.

[0093]

Claims

1. A thermoplastic resin containing a structural unit (A) derived from a monomer represented by the following general formula (1): 【Chemistry 1】 (In the formula, R １ each independently represents an aryl group having 6 to 14 carbon atoms or an aralkyl group having 7 to 17 carbon atoms; R ２ each independently represents a hydrogen atom, an aryl group having 6 to 14 carbon atoms, or an aralkyl group having 7 to 17 carbon atoms; each a independently represents 0 or an integer of 1 to 3; R ３ are each independently —OH or —O—(CH ２ ) ｎ -OH, and n is an integer of 1 to 4.

2. The thermoplastic resin according to claim 1, wherein the monomer represented by the general formula (1) is a monomer represented by the following formula (1A): 【Chemistry 2】 (In the formula, R １ , R ２ and a have the same definition as in general formula (1).

3. The thermoplastic resin according to claim 1, wherein the monomer represented by the general formula (1) is a monomer represented by the following formula (5): 【Transformation 3】

4. The thermoplastic resin according to claim 1, wherein the monomer represented by the general formula (1) is a monomer represented by the following formula (1B): 【Chemistry 4】 (In the formula, R １ , R ２ and a have the same definition as in general formula (1), and n independently represents an integer of 1 to 4.

5. The thermoplastic resin according to claim 1, wherein the monomer represented by the general formula (1) is a monomer represented by the following formula (15): 【Transformation 5】

6. The thermoplastic resin according to claim 1 , wherein the thermoplastic resin is a polycarbonate resin, a polyester carbonate resin, or a polyester resin.

7. The thermoplastic resin according to claim 1, wherein the thermoplastic resin comprises a structural unit (B) derived from a monomer represented by the following general formula (6) and / or a structural unit (C) derived from a monomer represented by the following general formula (7): 【Transformation 6】 (In general formula (6), R ａ and R ｂ each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group having 5 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ selected from the group consisting of R ｈ represents an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, X represents a single bond or an optionally substituted fluorene group; A and B each independently represent an alkylene group having 1 to 5 carbon atoms which may have a substituent; m and n each independently represent an integer of 0 to 6; a and b each independently represent an integer of 0 to 10. 【Transformation 7】 (In general formula (7), R ｃ and R ｄ are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkoxyl group having 1 to 20 carbon atoms, an optionally substituted cycloalkyl group having 5 to 20 carbon atoms, an optionally substituted cycloalkoxyl group having 5 to 20 carbon atoms, and an optionally substituted aryl group having 6 to 20 carbon atoms; Y １ represents a single bond, a fluorene group which may have a substituent, or any of the structural formulae represented by the following formulae (8) to (14): 【Transformation 8】 (In formulas (8) to (14), R ６１ , R ６２ , R ７１ and R ７２ each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent, or R ６１ and R ６２ , or R ７１ and R ７２ are bonded to each other to form a carbocyclic or heterocyclic ring having 1 to 20 carbon atoms, which may have a substituent; r and s each independently represent an integer of 0 to 5000. A and B each independently represent an alkylene group having 1 to 5 carbon atoms which may have a substituent; p and q each independently represent an integer of 0 to 4; a and b each independently represent an integer of 0 to 10.

8. The thermoplastic resin according to claim 7, wherein in the general formula (6) and the general formula (7), A and B each independently represent an alkylene group having 2 or 3 carbon atoms.

9. The thermoplastic resin according to claim 7, wherein the thermoplastic resin contains at least a structural unit derived from any one of BPEF, BNE, BNEF, and DPBHBNA.

10. The thermoplastic resin according to claim 1, further comprising a structural unit derived from at least one monomer selected from the following group of monomers: 【Chemistry 9】 (In the above formula, R １ and R ２ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ３ and R ４ each independently represents a hydrogen atom, a methyl group, an ethyl group, or an alkylene glycol having 2 to 5 carbon atoms.

11. The thermoplastic resin according to claim 1, wherein the weight average molecular weight (Mw) of the thermoplastic resin in terms of polystyrene is 10,000 to 100,000.

12. The thermoplastic resin according to claim 1, wherein the refractive index (nD) of the thermoplastic resin is 1.600 to 1.

700.

13. 2. The thermoplastic resin according to claim 1, wherein the Abbe number (ν) of the thermoplastic resin is 22.0 to 26.

0.

14. The thermoplastic resin according to claim 1, wherein the glass transition temperature of the thermoplastic resin is 70 to 200°C.

15. 2. The thermoplastic resin according to claim 1, wherein the thermoplastic resin has a photoelastic coefficient of 25 to 45.

16. An optical lens comprising the thermoplastic resin according to any one of claims 1 to 15.

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