Thermoplastic resin and optical member including same

Abstract

The purpose of the present invention is to provide: a polycarbonate resin that has a high refractive index, low birefringence, and a glass transition temperature that is suited to use in an optical lens; and an optical member that includes the polycarbonate resin.　This thermoplastic resin includes repeating units represented by formula (1), formula (2), and formula (3), the repeating units represented by formula (1) being 70.0–98.0 mass% of all the repeating units, and the repeating units represented by formula (3) being 0.1–3.0 mass% of all the repeating units. (In formula (1), R1–R4 each independently represent a hydrogen atom, a halogen atom, a C1–20 substituent that may include an aromatic group, or a C2–20 substituent that includes a heterocycle, and m1 and m2 each independently represent 0 or 1.) (In formula (2), n1 and n2 each independently represent 0 or 1.) (In formula (3), X represents a C4–14 alkylene group.)

Description

Thermoplastic resins and optical components containing them

[0001] The present invention relates to a thermoplastic resin and an optical component containing the same.

[0002] There is a strong demand for low birefringence and improved aberration correction capabilities in plastic imaging lenses used in devices such as smartphones. Conventionally, aberration correction in such imaging lenses has been achieved by combining multiple lenses with different optical properties (refractive index, Abbe number) and lens shapes.

[0003] Furthermore, when using optical resins as optical lenses, properties other than refractive index and Abbe number are required, such as heat resistance, transparency, low water absorption, chemical resistance, light resistance, low birefringence, and heat and humidity resistance. Therefore, a weakness is that the applications are limited depending on the balance of the resin's physical properties. In particular, in recent years, with the increase in pixel count, there has been a trend towards higher resolution, and there is a demand for camera lenses with higher imaging performance and lower birefringence. Also, in order to display a clear image, it is necessary to maintain high transmittance across all wavelengths in the visible light range.

[0004] Therefore, research has been conducted to develop resins for optical lenses that have a high refractive index, low birefringence, and an excellent balance of physical properties such as heat resistance and transmittance. For example, Patent Document 1 describes that a copolymer resin of a bisphenol compound having a fluorene structure and an aliphatic diol exhibits low birefringence. Patent Document 2 also describes that a copolymer containing the constituent unit represented by the following formula (A) has a high refractive index and exhibits low birefringence.

[0005]

[0006] Furthermore, Patent Documents 3 and 4 describe copolymers containing the constituent unit represented by the following formula (B) exhibiting a high refractive index.

[0007]

[0008] Japanese Patent Publication No. 2007-057916, Japanese Patent Publication No. 2015-086265, Japanese Patent Publication No. 2017-179323, International Publication No. 2018 / 016516

[0009] However, the copolymer resin of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (hereinafter sometimes abbreviated as BPEF) and an aliphatic diol described in Patent Document 1 has a refractive index of approximately 1.639, and a resin with a higher refractive index is required to improve optical lens performance.

[0010] Furthermore, Patent Document 2 describes a copolymer resin having a refractive index of 1.639 to 1.655, consisting of the above formula (A) and one other component. However, a resin with an even higher refractive index is required to improve optical lens performance.

[0011] Patent Document 3 describes a copolymer resin with a refractive index of 1.664 to 1.686 that includes the above formula (B), but its glass transition temperature is high at 169 to 195°C, and its birefringence is 2.9 × 10⁻⁶. ―３ ~6.7 x 10 ―３ Because of its large size, it is difficult to say that it is suitable for use as a resin for optical lenses.

[0012] Patent document 4 describes a copolymer resin consisting of constituent unit (A) and constituent unit (B), but its glass transition temperature is high at 160 to 180°C, making it difficult to say that it is suitable for use as a resin for optical lenses.

[0013] Therefore, the present invention aims to provide a polycarbonate resin having a high refractive index and low birefringence, and a glass transition temperature suitable for use as an optical lens, and an optical component containing the same.

[0014] The inventors have found that the above problems can be solved by the present invention having the following aspects.

[0015] <<Aspect 1>> A thermoplastic resin comprising repeating units represented by the following formulas (1), (2), and (3), wherein the repeating unit represented by formula (1) is 70.0% by mass or more and 98.0% by mass or less based on the total number of repeating units, and the repeating unit represented by formula (3) is 0.1% by mass or more and 3.0% by mass or less based on the total number of repeating units: (In formula (1), R １ ~R ４Each independently represents any one of a hydrogen atom, a halogen atom, a substituent having 1 to 20 carbon atoms which may contain an aromatic group, and a substituent having 2 to 20 carbon atoms containing a heterocyclic ring, and m １ and m ２ each independently represents 0 or 1.) (In formula (2), n １ and n ２ each independently represents 0 or 1.) (In formula (3), X represents an alkylene group having 4 to 14 carbon atoms.) <<Aspect 2>> The thermoplastic resin according to Aspect 1, wherein the repeating unit of the above formula (2) is 2.0% by mass or more and 30.0% by mass or less based on all the repeating units. <<Aspect 3>> In the above formula (1), R １ to R ４ are hydrogen atoms, m １ and m ２ is 1, the thermoplastic resin according to Aspect 1 or 2. <<Aspect 4>> In the above formula (3), X is an alkylene group having 7 to 14 carbon atoms, the thermoplastic resin according to any one of Aspects 1 to 3. <<Aspect 5>> The thermoplastic resin according to any one of Aspects 1 to 4, wherein the repeating unit represented by the above formula (3) is 0.1% by mass or more and 1.5% by mass or less based on all the repeating units. <<Aspect 6>> An optical member containing the thermoplastic resin according to any one of Aspects 1 to 5. <<Aspect 7>> The optical member according to Aspect 6, which is an optical lens.

[0016] <Thermoplastic resin> The thermoplastic resin of the present invention contains repeating units represented by the above formula (1), formula (2) and formula (3), and the repeating unit represented by the above formula (1) is 70.0% by mass or more and 98.0% by mass or less based on all the repeating units, and the repeating unit represented by formula (3) is 0.1% by mass or more and 3.0% by mass or less based on all the repeating units.

[0017] The present inventors have found that the above thermoplastic resin exhibits a refractive index and birefringence useful in the production of optical lenses, and a glass transition temperature useful as a molding material, and have reached the present application.

[0018] <Structure of thermoplastic resin> R in the above formula (1) １ to R ４Each of these independently represents one of the following: a hydrogen atom, a halogen atom, a substituent having 1 to 20 carbon atoms which may contain an aromatic group, or a substituent having 2 to 20 carbon atoms which contains a heterocycle.

[0019] Preferred halogen atoms include fluorine atoms, chlorine atoms, and bromine atoms.

[0020] Examples of substituents having 1 to 20 carbon atoms that may contain an aromatic group include alkyl groups, cycloalkyl groups, and aryl groups.

[0021] Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, and t-butyl groups, with methyl and ethyl groups being preferred.

[0022] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and bicyclo[1.1.1]pentanyl groups.

[0023] Examples of aryl groups include phenyl, tolyl, naphthyl, and xylyl groups, with phenyl being preferred.

[0024] Examples of substituents containing heterocycles with 2 to 20 carbon atoms include furyl groups, thienyl groups, and pyrrolyl groups, with thienyl groups and pyrrolyl groups being preferred.

[0025] R １ ~R ４ Each of these is preferably a hydrogen atom, a methyl group, or a phenyl group, more preferably a hydrogen atom or a phenyl group, and even more preferably a hydrogen atom.

[0026] In the above formula (1), m １ and m ２ Each of these independently represents either 0 or 1, and is preferably 1.

[0027] I understand １ and m ２ It is preferable that the above range is within the range that facilitates synthesis.

[0028] The repeating unit represented by formula (1) above is preferably a repeating unit derived from 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene or 9,9-bis(4-(hydroxyethoxy)-3-phenylphenyl)fluorene, and more preferably a repeating unit derived from 9,9-bis(4-(hydroxyethoxy)-3-phenylphenyl)fluorene.

[0029] The thermoplastic resin of the present invention contains the repeating unit of formula (1) in an amount of 70.0% by mass or more and 98.0% by mass or less, based on the total number of repeating units. The thermoplastic resin of the present invention preferably contains 75.0% by mass or more of the repeating unit of formula (1) based on the total number of repeating units, more preferably 80.0% by mass or more, and even more preferably 84.0% by mass or more. It is also preferably 97.0% by mass or less, more preferably 95.0% by mass or less, even more preferably 93.0% by mass or less, and particularly preferably 90.0% by mass or less.

[0030] When the repeating unit represented by formula (1) above is within the above range, the refractive index is high and birefringence is excellent, thus a thermoplastic resin with an excellent balance between refractive index and birefringence can be obtained.

[0031] n in equation (2) above １ and n ２ Each of these independently represents either 0 or 1, and is preferably 1.

[0032] n １ and n ２ It is preferable that the above range is within the range that facilitates synthesis.

[0033] The repeating unit represented by formula (2) above is preferably a repeating unit derived from 9,9-bis(6-hydroxy-2-naphthyl)fluorene and 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)fluorene, and more preferably a repeating unit derived from 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)fluorene.

[0034] The thermoplastic resin of the present invention preferably contains 2.0% by mass or more of the repeating unit of formula (2) above, more preferably 5.0% by mass or more, and even more preferably 10.0% by mass or more, based on the total number of repeating units. Furthermore, it is preferably 30.0% by mass or less, more preferably 28.0% by mass or less, even more preferably 25.0% by mass or less, and particularly preferably 20.0% by mass or less.

[0035] When the repeating unit represented by formula (2) above is within the above range, the refractive index is high and birefringence is excellent, thus making it possible to obtain a thermoplastic resin with an excellent balance between refractive index and birefringence.

[0036] In formula (3) above, X is preferably an alkylene group having 4 to 14 carbon atoms, more preferably an alkylene group having 7 to 14 carbon atoms or an alkylene group having 4 to 11 carbon atoms, even more preferably an alkylene group having 7 to 10 carbon atoms, and most preferably an alkylene group having 8 to 10 carbon atoms.

[0037] When X is within the above range, the refractive index of the resulting thermoplastic resin is not affected, and the glass transition temperature can be lowered, thus making it possible to obtain a thermoplastic resin with an excellent balance between refractive index and glass transition temperature.

[0038] The repeating unit represented by formula (3) above is preferably 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, or 1,14-tetradecanediol; more preferably 1,6-hexanediol, 1,8-dodecanediol, 1,9-nonanediol, 1,10-decanediol, or 1,12-dodecanediol; even more preferably 1,8-dodecanediol, 1,9-nonanediol, or 1,10-decanediol; and most preferably 1,9-nonanediol.

[0039] The thermoplastic resin of the present invention contains the repeating unit of formula (3) in an amount of 0.1% by mass or more and 3.0% by mass or less, based on the total number of repeating units. The thermoplastic resin of the present invention preferably contains 0.2% by mass or more of the repeating unit of formula (3) based on the total number of repeating units, more preferably 0.3% by mass or more. It is also preferably 2.5% by mass or less, more preferably 1.8% by mass or less, even more preferably 1.5% by mass or less, particularly preferably 1.3% by mass or less, and most preferably 1.0% by mass or less.

[0040] When the repeating unit represented by formula (3) above is within the above range, it does not affect the refractive index of the thermoplastic resin and can lower the glass transition temperature, thus making it possible to obtain a thermoplastic resin with an excellent balance between refractive index and glass transition temperature.

[0041] The thermoplastic resin of the present invention may contain repeating units other than those represented by formulas (1), (2), and (3) above, to the extent that the advantageous effects of the present invention described above are obtained. Examples of dihydroxy compounds that yield such repeating units include isosorbide, isomannide, isoidide, hydroquinone, resorcinol, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bis(4-hydroxyphenyl)diphenylmethane, 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene, bis(4-hydroxyphenyl)sulfone, bis(4-hydroxyphenyl)sulfide, biphenol, bisphenol fluorene, biscresol fluorene, 9,9-bis(4-(hydroxyethoxy)phenyl)fluorene, and the like. Such repeating units may be present in amounts of 10% by mass or less of the total repeating units.

[0042] <Physical Properties of Thermoplastic Resin> The refractive index of the thermoplastic resin of the present invention is preferably 1.656 or higher, more preferably 1.657 or higher, and even more preferably 1.658 or higher, when measured at a temperature of 20°C and a wavelength of 537.56 nm. It may also be 1.670 or lower, 1.665 or lower, or 1.663 or lower. A refractive index within the above range is preferable because it allows for a thinner lens thickness and thus a thinner optical component.

[0043] The specific viscosity of the thermoplastic resin of the present invention is preferably 0.12 to 0.32, and more preferably 0.18 to 0.30. A specific viscosity of 0.12 to 0.32 provides an excellent balance between moldability and strength.

[0044] The specific viscosity is measured by the specific viscosity (η) of a solution prepared by dissolving 0.7 g of thermoplastic resin in 100 ml of methylene chloride at 20°C. ＳＰ The following is calculated from the following formula a: η ＳＰ = (t １ -t ０ ) / t ０ ...Formula a [t ０ t is the number of seconds the methylene chloride falls. １ [This refers to the number of seconds the sample solution falls.]

[0045] The absolute value of the orientational birefringence (|Δn|) of the thermoplastic resin of the present invention is 1.0 × 10⁻⁶. －３ Preferably, it is 0.6 × 10 －３ It is more preferable that the following conditions are met: 0.4 × 10 －３ It is even more preferable that the following conditions apply: 0.2 × 10 －３ The following is most preferable:

[0046] If the absolute value of the orientational birefringence is below the above value, it does not significantly affect chromatic aberration, and the performance as designed by the optical manufacturer can be maintained. The orientational birefringence is measured at a wavelength of 589 nm after a 100 μm thick cast film obtained from the thermoplastic resin is doubled at Tg + 10°C.

[0047] The thermoplastic resin of the present invention preferably has a total light transmittance of 80% or more at a thickness of 1 mm, more preferably 85% or more, and particularly preferably 88% or more.

[0048] The saturated water absorption rate of the thermoplastic resin of the present invention is preferably 0.10% or more and 0.70% or less, more preferably 0.20% or more and 0.70% or less, and even more preferably 0.30% or more and 0.65% or less.

[0049] The glass transition temperature of the thermoplastic resin of the present invention is preferably 145°C or higher, more preferably 148°C or higher, and even more preferably 150°C or higher. It is also preferably 156°C or lower, more preferably 155°C or lower, and even more preferably 154°C or lower.

[0050] Examples of thermoplastic resins of the present invention include polycarbonates containing carbonate structures represented by formulas (1), (2), and (3) in their repeating units, and polyester carbonates containing repeating units represented by formulas (1), (2), and (3) and other ester structures in their repeating units. Among these, polycarbonates are preferred in terms of heat resistance and moisture heat resistance.

[0051] <Method for Manufacturing Polycarbonate Resin> The polycarbonate resin of the present invention is manufactured by conventional, self-known reaction methods for manufacturing polycarbonate resins, such as reacting a dihydroxy compound with a carbonate precursor such as a diester carbonate. The basic means of these manufacturing methods will be briefly described below.

[0052] The transesterification reaction using diester carbonate as a carbonate precursor is carried out by heating and stirring a predetermined proportion of dihydroxy component with the diester carbonate under an inert gas atmosphere, and distilling off the resulting alcohol or phenol. The reaction temperature varies depending on the boiling point of the resulting alcohol or phenol, but is usually in the range of 120 to 300°C. The reaction is completed under reduced pressure from the beginning, while distilling off the resulting alcohol or phenol. End-terminating agents, antioxidants, etc., may also be added as needed.

[0053] Examples of diester carbonates used in the transesterification reaction include esters such as aryl groups and aralkyl groups having 6 to 12 carbon atoms, which may be substituted. Specifically, diphenyl carbonate, ditrile carbonate, bis(chlorophenyl) carbonate, and m-cresyl carbonate are examples. Among these, diphenyl carbonate is particularly preferred. The amount of diphenyl carbonate used is preferably 0.95 to 1.10 mol, more preferably 0.98 to 1.04 mol, per 1 mol of the total dihydroxy compounds.

[0054] Furthermore, in the melt polymerization method, a polymerization catalyst can be used to accelerate the polymerization rate. Examples of such polymerization catalysts include alkali metal compounds, alkaline earth metal compounds, other metal compounds, nitrogen-containing compounds, and the like.

[0055] Examples of alkali metal compounds include sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, cesium acetate, lithium acetate, sodium stearate, potassium stearate, cesium stearate, lithium stearate, sodium borohydride, sodium benzoate, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, disodium phenyl phosphate, disodium, dipotassium, dicesium, and dilithium salts of bisphenol A, and sodium, potassium, cesium, and lithium salts of phenol.

[0056] Examples of alkaline earth metal compounds include magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium diacetate, calcium diacetate, strontium diacetate, and barium diacetate.

[0057] The amount of these polymerization catalysts used is preferably 0.1 μmol to 500 μmol per 1 mol of dihydroxy component, more preferably 0.5 μmol to 300 μmol, and even more preferably 1 μmol to 100 μmol.

[0058] Other metal compounds include salts of aluminum, zinc, tin, zirconium, lead, titanium, germanium, antimony, and osmium, such as aluminum formate, aluminum acetate, aluminum propionate, aluminum oxalate, aluminum acrylate, aluminum laurate, aluminum stearate, aluminum benzoate, aluminum trichloroacetate, aluminum lactate, aluminum citrate, and aluminum salicylate, aluminum chloride, aluminum hydroxide, aluminum chloride hydroxide, aluminum carbonate, aluminum phosphate, and aluminum phosphonate. Examples include luminium, aluminum acetylacetonate, aluminum acetyl acetate, aluminum ethyl acetate, aluminum ethyl acetate diisopropoxide, zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin(II) chloride, tin(IV) chloride, tin(II) acetate, tin(IV) acetate, dibutyltin dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead(II) acetate, lead(IV) acetate titanium tetrabutoxide(IV), etc. Catalysts used in International Publication No. 2011 / 010741 and Japanese Patent Publication No. 2017-179323 may also be used.

[0059] The amount of these polymerization catalysts used is preferably 50 μmol to 1000 μmol per 1 mol of dihydroxy component, more preferably 60 μmol to 700 μmol, and even more preferably 80 μmol to 400 μmol.

[0060] Furthermore, catalysts consisting of other metal compounds and phosphorus compounds may also be used. Examples of phosphorus compounds include phosphonic acid compounds, phosphinic acid compounds, phosphine oxide compounds, phosphonisulfite compounds, phosphinisulfite compounds, and phosphine compounds. Among these, phosphonic acid compounds, phosphinic acid compounds, and phosphine oxide compounds are particularly noteworthy, with phosphonic acid compounds being especially important.

[0061] In that case, the amount of phosphorus compound used is preferably 50 μmol to 1000 μmol per 1 mol of dihydroxy compound, more preferably 60 μmol to 700 μmol, and even more preferably 80 μmol to 400 μmol.

[0062] Examples of nitrogen-containing compounds include quaternary ammonium hydroxides having alkyl or aryl groups, such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, and trimethylbenzylammonium hydroxide. Examples of bases or basic salts include tetramethylammonium borohydride, tetrabutylammonium borohydride, tetrabutylammonium tetraphenylborate, and tetraphenylammonium tetraphenylborate.

[0063] The amount of these polymerization catalysts used is preferably 50 μmol to 1000 μmol per 1 mol of dihydroxy component, more preferably 60 μmol to 700 μmol, and even more preferably 80 μmol to 400 μmol.

[0064] In the method for producing the polycarbonate resin used in the present invention, the catalyst may be removed or deactivated after the polymerization reaction is complete in order to maintain thermal stability and hydrolysis stability. A method of deactivating the catalyst by adding a known acidic substance can be suitably carried out. Specifically, the acidic substances include esters such as butyl benzoate, aromatic sulfonic acids such as p-toluenesulfonic acid; aromatic sulfonic acid esters such as p-toluenesulfonate butyl and p-toluenesulfonate hexyl; phosphoric acids such as phosphorous acid, phosphoric acid, and phosphonic acid; phosphorous acid esters such as triphenyl phosphate, monophenyl phosphate, diphenyl phosphate, diethyl phosphate, di-n-propyl phosphate, di-n-butyl phosphate, di-n-hexyl phosphate, dioctyl phosphate, and monooctyl phosphate; triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate, and dioctyl phosphate. Phosphate esters such as monooctyl phosphate; phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid, and dibutylphosphonic acid; phosphonic acid esters such as diethyl phenylphosphonate; phosphines such as triphenylphosphine and bis(diphenylphosphino)ethane; boric acids such as boric acid and phenylboric acid; aromatic sulfonates such as tetrabutylphosphonium dodecylbenzenesulfonate; organic halides such as stearate chloride, benzoyl chloride, and p-toluenesulfonic acid chloride; alkyl sulfates such as dimethyl sulfate; and organic halides such as benzyl chloride are preferably used. These deactivators are used in an amount of 0.01 to 50 moles, preferably 0.3 to 20 moles, relative to the amount of catalyst. If the amount is less than 0.01 moles relative to the amount of catalyst, the deactivation effect will be insufficient and undesirable. Also, if the amount is more than 50 moles relative to the amount of catalyst, the heat resistance of the resin will decrease and the molded product will be more prone to discoloration, which is undesirable.

[0065] After catalyst deactivation, a step may be included to defoliate and remove low-boiling-point compounds in the thermoplastic resin at a pressure of 13.3 to 133 Pa and a temperature of 200 to 320°C.

[0066] <Method for producing polyester carbonate resin> The thermoplastic resin of the present invention may be a polyester carbonate resin. The polyester carbonate resin is produced by conventional, self-known reaction methods for producing polyester carbonate resin, for example, by polycondensation reaction of a dihydroxy compound with a carbonate precursor such as a diester carbonate and a dicarboxylic acid or its ester-forming derivative.

[0067] In the reaction between dihydroxy compounds, dicarboxylic acids, or their acid chlorides and phosgene, the reaction is carried out in a non-aqueous system in the presence of an acid binder and a solvent. Examples of acid binders include pyridine, dimethylaminopyridine, and tertiary amines. Examples of solvents include halogenated hydrocarbons such as methylene chloride and chlorobenzene. It is desirable to use end-terminating agents such as phenol and p-tert-butylphenol as molecular weight modifiers. The reaction temperature is usually 0 to 40°C, and the reaction time is preferably several minutes to 5 hours.

[0068] In the transesterification reaction, a dihydroxy compound is mixed with a dicarboxylic acid or its diester and a bisaryl carbonate under an inert gas atmosphere, and the reaction is carried out under reduced pressure, usually at 120 to 350°C, preferably 150 to 300°C. The degree of reduced pressure is changed in steps, and finally reduced to 133 Pa or less to remove the resulting alcohols from the system by distillation. The reaction time is usually about 1 to 4 hours.

[0069] Furthermore, a polymerization catalyst can be used to accelerate the transesterification reaction. The same catalysts mentioned in the above-mentioned method for producing polycarbonate can be used as polymerization catalysts.

[0070] In the method for producing the polyester carbonate resin used in the present invention, the catalyst may be removed or deactivated after the polymerization reaction is complete in order to maintain thermal stability and hydrolysis stability. A method of deactivating the catalyst by adding a known acidic substance can be suitably carried out, and the substances listed in the above-mentioned method for producing polycarbonate can be used as the acidic substance.

[0071] After catalyst deactivation, a step may be included to defoliate and remove low-boiling-point compounds in the thermoplastic resin at a pressure of 13.3 to 133 Pa and a temperature of 200 to 320°C.

[0072] <Thermoplastic Resin Composition> The thermoplastic resin of the present invention can be used as a resin composition by appropriately adding additives such as mold release agents, heat stabilizers, ultraviolet absorbers, bluing agents, antistatic agents, flame retardants, plasticizers, fillers, antioxidants, light stabilizers, polymerization metal deactivators, lubricants, surfactants, and antibacterial agents as needed. Specific mold release agents and heat stabilizers described in International Publication No. 2011 / 010741 are preferred.

[0073] Particularly preferred release agents include monoglyceride stearate, triglyceride stearate, pentaerythritol tetrastearate, and a mixture of triglyceride stearate and stearyl stearate. The amount of the ester in the release agent is preferably 90% by weight or more, and more preferably 95% by weight or more, when the total release agent is considered to be 100% by weight. Furthermore, the amount of the release agent to be blended with the thermoplastic resin is preferably in the range of 0.005 to 2.0 parts by weight, more preferably in the range of 0.01 to 0.6 parts by weight, and even more preferably in the range of 0.02 to 0.5 parts by weight, per 100 parts by weight of the thermoplastic resin.

[0074] Examples of heat stabilizers include phosphorus-based heat stabilizers, sulfur-based heat stabilizers, and hindered phenol-based heat stabilizers.

[0075] Furthermore, particularly preferred phosphorus-based heat stabilizers include tris(2,4-di-tert-butylphenyl) phosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, and tetrakis(2,4-di-tert-butylphenyl)-4,4'-biphenylenediphosphonite. The content of the phosphorus-based heat stabilizer in the polycarbonate resin is preferably 0.001 to 0.2 parts by weight per 100 parts by weight of the thermoplastic resin.

[0076] Furthermore, a particularly preferred sulfur-based heat stabilizer is pentaerythritol-tetrakis(3-laurylthiopropionate). The preferred content of the sulfur-based heat stabilizer in the thermoplastic resin is 0.001 to 0.2 parts by weight per 100 parts by weight of the thermoplastic resin.

[0077] Furthermore, preferred hindered phenol-based heat stabilizers include octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate].

[0078] The preferred content of the hindered phenol-based heat stabilizer in the thermoplastic resin is 0.001 to 0.3 parts by weight per 100 parts by weight of the thermoplastic resin.

[0079] Phosphorus-based heat stabilizers and hindered phenol-based heat stabilizers can be used in combination.

[0080] As the ultraviolet absorber, at least one ultraviolet absorber selected from the group consisting of benzotriazole-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers, triazine-based ultraviolet absorbers, cyclic iminoester-based ultraviolet absorbers, and cyanoacrylate-based ultraviolet absorbers is preferred.

[0081] In the benzotriazole-based ultraviolet absorbers, more preferably are 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole and 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol].

[0082] Examples of benzophenone-based UV absorbers include 2-hydroxy-4-n-dodecyloxybenzophenone and 2-hydroxy-4-methoxy-2'-carboxybenzophenone.

[0083] Examples of triazine-based UV absorbers include 2-(4,6-diphenyl-1,3,5-triazine-2-yl)-5-[(hexyl)oxy]-phenol and 2-(4,6-bis(2.4-dimethylphenyl)-1,3,5-triazine-2-yl)-5-[(octyl)oxy]-phenol.

[0084] As a cyclic iminoester-based ultraviolet absorber, 2,2'-p-phenylenebis(3,1-benzoxazine-4-one) is particularly preferred.

[0085] Examples of cyanoacrylate-based ultraviolet absorbers include 1,3-bis-[(2'-cyano-3',3'-diphenylacryloyl)oxy]-2,2-bis[(2-cyano-3,3-diphenylacryloyl)oxy]methyl)propane and 1,3-bis-[(2-cyano-3,3-diphenylacryloyl)oxy]benzene.

[0086] The amount of UV absorber added is preferably 0.01 to 3.0 parts by weight per 100 parts by weight of thermoplastic resin. Within this range of addition, it is possible to impart sufficient weather resistance to the molded article of the thermoplastic resin, depending on the application.

[0087] Antioxidants include triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, and 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert- Examples include butyl-4-hydroxybenzyl)benzene, N,N-hexamethylenebis(3,5-di-tert-butyl-4-hydroxyhydrocinnamide), 3,5-di-tert-butyl-4-hydroxybenzylphosphonate-diethyl ester, tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, and 3,9-bis{1,1-dimethyl-2-[β-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]ethyl}-2,4,8,10-tetraoxaspiro[5.5]undecane. The amount of antioxidant added is preferably 0.50 parts by mass or less, more preferably 0.05 to 0.40 parts by mass, even more preferably 0.05 to 0.20 parts by mass or 0.10 to 0.40 parts by mass, and particularly preferably 0.20 to 0.40 parts by mass, per 100 parts by mass of the thermoplastic resin composition.

[0088] <Optical Components> The optical components of the present invention include the thermoplastic resin described above. Such optical components are not particularly limited as long as they are for optical applications in which the thermoplastic resin is useful, but examples include optical discs, transparent conductive substrates, optical cards, sheets, films, optical fibers, lenses, prisms, optical films, substrates, optical filters, hard coat films, and the like.

[0089] Furthermore, the optical component of the present invention may be composed of a resin composition containing the above-mentioned thermoplastic resin, and the resin composition may optionally contain additives such as heat stabilizers, plasticizers, light stabilizers, polymer metal deactivators, flame retardants, lubricants, antistatic agents, surfactants, antibacterial agents, ultraviolet absorbers, mold release agents, bluing agents, fillers, and antioxidants.

[0090] <Optical Lenses> Optical lenses are particularly noteworthy as optical components of the present invention. Examples of such optical lenses include imaging lenses for mobile phones, smartphones, tablet devices, personal computers, digital cameras, video cameras, in-vehicle cameras, surveillance cameras, etc., as well as sensing cameras such as TOF cameras.

[0091] When manufacturing the optical lens of the present invention by injection molding, it is preferable to mold it under conditions of a cylinder temperature of 230 to 350°C and a mold temperature of 70 to 180°C. More preferably, it is preferable to mold it under conditions of a cylinder temperature of 250 to 300°C and a mold temperature of 80 to 170°C. If the cylinder temperature is higher than 350°C, the thermoplastic resin decomposes and discolors, and if it is lower than 230°C, the melt viscosity is high and molding tends to be difficult. Also, if the mold temperature is higher than 180°C, it tends to be difficult to remove the molded piece made of thermoplastic resin from the mold. On the other hand, if the mold temperature is lower than 70°C, the resin hardens too quickly in the mold during molding, making it difficult to control the shape of the molded piece, and it also tends to be difficult to sufficiently transfer the molded shape applied to the mold.

[0092] The optical lens of the present invention preferably utilizes an aspherical lens shape as needed. Since an aspherical lens can substantially eliminate spherical aberration with a single lens, there is no need to eliminate spherical aberration by combining multiple spherical lenses, which enables weight reduction and a reduction in molding costs. Therefore, aspherical lenses are particularly useful as camera lenses among optical lenses.

[0093] Furthermore, because the thermoplastic resin of the present invention has high moldability, it is particularly useful as a material for thin-walled, small, and complexly shaped optical lenses. Specifically, the lens size is such that the thickness at the center is 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 1.0 mm to 20.0 mm, more preferably 1.0 to 10.0 mm, and even more preferably 3.0 to 10.0 mm. In addition, it is preferable that the shape be a meniscus lens with one side convex and the other side concave.

[0094] The lens made of the thermoplastic resin of the present invention can be formed by any method such as mold molding, cutting, polishing, laser processing, electrical discharge machining, or etching. Among these, mold molding is more preferable from the standpoint of manufacturing cost.

[0095] The present invention will be described in more detail by the following examples, but the present invention is not limited thereto.

[0096] The evaluation was performed using the following method.

[0097] <Thermoplastic resin composition> JEOL JNM-ECZ400S １ The copolymerization ratio of each thermoplastic resin was calculated by measuring 1H NMR.

[0098] <Refractive Index> After preparing and polishing 3 mm thick test specimens of each thermoplastic resin, the refractive index nd (587.56 nm) was measured using a Shimadzu KPR-2000 precision refractometer.

[0099] <Absolute Value of Orientational Birefringence> A thermoplastic resin was dissolved in methylene chloride, cast onto a glass petri dish, and thoroughly dried to produce a 100 μm thick cast film. The film was stretched twice at Tg + 10°C, and the phase difference (Re) at 589 nm was measured using an ellipsometer M-220 manufactured by JASCO Corporation. The absolute value of orientational birefringence (|Δn|) was calculated from the following equation b: |Δn| = |Re / d| …Equation b Δn: Orientational birefringence Re: Phase difference (nm) d: Thickness (nm)

[0100] <Glass Transition Temperature (Tg)> The obtained thermoplastic resin was measured using a Discovery DSC 25Auto model manufactured by TA Instrument Japan Co., Ltd. at a heating rate of 20°C / min. Samples of 5 to 10 mg were used for measurement.

[0101] <Example 1> 101.7 g of 9,9-bis(4-(hydroxyethoxy)-3-phenylphenyl)fluorene (hereinafter sometimes abbreviated as OPBPEF), 14.0 g of 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)fluorene (hereinafter sometimes abbreviated as BNEF), 0.3 g of 1,9-nonanediol (hereinafter sometimes abbreviated as NOD), 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ 1 g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and distillation apparatus. After purging with nitrogen three times, the jacket was heated to 200°C to melt the raw materials. After complete melting, the pressure was reduced to 20 kPa over 20 minutes, and the jacket was heated to 260°C at a rate of 60°C / hr to carry out the transesterification reaction. Thereafter, the jacket was maintained at 260°C, and when the phenol efflux reached 70%, the pressure was reduced to 60 kPa / hr, and the polymerization reaction was carried out until the predetermined power was reached. After the reaction was complete, the resin was removed from the flask.

[0102] The copolymerization ratio of the obtained polycarbonate resin is １ The refractive index, absolute value of orientational birefringence, and Tg of the polycarbonate resin were measured by HMR.

[0103] <Example 2> 100.5 g of OPBPEF, 14.0 g of BNEF, 0.6 g of NOD, 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0104] <Example 3> 100.5 g of OPBPEF, 11.9 g of BNEF, 1.3 g of NOD, 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0105] <Example 4> 94.6 g of OPBPEF, 14.0 g of BNEF, 2.2 g of NOD, 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0106] <Example 5> 85.1 g of OPBPEF, 23.7 g of BNEF, 1.9 g of NOD, 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0107] <Example 6> 94.6 g of OPBPEF, 19.4 g of BNEF, 0.6 g of NOD, 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0108] <Example 7> 104.0 g of OPBPEF, 10.8 g of BNEF, 0.6 g of NOD, 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0109] <Example 8> 112.3 g of OPBPEF, 3.2 g of BNEF, 0.6 g of NOD, 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0110] <Example 9> 100.5 g of OPBPEF, 14.0 g of BNEF, 0.6 g of 1,6-hexanediol (hereinafter sometimes abbreviated as HD), 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0111] <Example 10> 100.5 g of OPBPEF, 14.0 g of BNEF, 0.6 g of 1,12-dodecanediol (hereinafter sometimes abbreviated as DDD), 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0112] <Comparative Example 1> 100.5 g of OPBPEF, 16.2 g of BNEF, 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0113] <Comparative Example 2> 53.2 g of OPBPEF, 59.3 g of BNEF, 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0114] <Comparative Example 3> 82.7 g of OPBPEF, 20.5 g of BNEF, 3.5 g of NOD, 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0115] <Comparative Example 4> 100.5 g of OPBPEF, 14.0 g of BNEF, 0.6 g of 1,2-ethanediol (hereinafter sometimes abbreviated as EG), 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0116] <Comparative Example 5> 100.5 g of OPBPEF, 14.0 g of BNEF, 0.6 g of 1,3-propanediol (hereinafter sometimes abbreviated as PD), 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0117] <Comparative Example 6> 100.5 g of OPBPEF, 14.0 g of BNEF, 0.6 g of cyclohexane-1,4-dimethanol (hereinafter sometimes abbreviated as CHDM), 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0118] <Comparative Example 7> 100.5 g of OPBPEF, 14.0 g of BNEF, 0.6 g of tricyclo[5.2.1.0 ２，６ Decandimethanol (hereinafter sometimes abbreviated as TCDDM), 43.7 g of diphenyl carbonate, and 6.5 × 10 as a catalyst －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide was placed in a reaction vessel equipped with a stirrer and a distillation device, and polycarbonate resin was produced in the same manner as in Example 1. The obtained polycarbonate resin was then evaluated.

[0119] <Comparative Example 8> 76.8 g of OPBP EF, 35.6 g of BNEF, 0.6 g of NOD, 43.7 g of diphenyl carbonate, and as a catalyst, 6.5 × 10 －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide were placed in a reaction kettle equipped with a stirrer and a distillation device, and a polycarbonate resin was produced in the same manner as in Example 1, and the obtained polycarbonate resin was evaluated.

[0120] <Comparative Example 9> 74.6 g of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (hereinafter sometimes abbreviated as BP EF), 14.0 g of BNEF, 0.6 g of NOD, 43.7 g of diphenyl carbonate, and as a catalyst, 6.5 × 10 －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide were placed in a reaction kettle equipped with a stirrer and a distillation device, and a polycarbonate resin was produced in the same manner as in Example 1, and the obtained polycarbonate resin was evaluated.

[0121] <Comparative Example 10> 114.7 g of OPBP EF, 1.0 g of NOD, 43.7 g of diphenyl carbonate, and as a catalyst, 6.5 × 10 －３ g of aluminum acetylacetonate, 14.2 × 10 －３ g of diethyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate, 3.6 × 10 －３ g of tetramethylammonium hydroxide were placed in a reaction kettle equipped with a stirrer and a distillation device, and a polycarbonate resin was produced in the same manner as in Example 1, and the obtained polycarbonate resin was evaluated.

[0122] <Results> The compositions and evaluation results of each example and comparative example are summarized in Table 1 below.

[0123]

[0124] OPBPEF: 9,9-bis(4-(hydroxyethoxy)-3-phenylphenyl)fluorene BPEF: 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene BNEF: 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)fluorene NOD: 1,9-nonanediol HD: 1,6-hexanediol DDD: 1,12-dodecanediol ED: 1,2-ethanediol PD: 1,3-propanediol CHDM: cyclohexane-1,4-dimethanol TCDDM: tricyclo[5.2.1.0 ２，６ Decandimethanol

[0125] Examples 1 to 10 have a refractive index of 1.657 to 1.670 and an absolute value of orientational birefringence (|Δn|) of 1.0 × 10⁻⁶. －３ As described below, and because the glass transition temperature is between 145°C and 156°C, it can be suitably used as a thermoplastic resin for optical lens applications.

[0126] Comparative Examples 1 and 2 both illustrate copolymer resins consisting only of OPBPEF and BNEF, but because they do not contain NOD, their glass transition temperature is higher than that of the Examples, making them unsuitable as thermoplastic resins for optical lens applications.

[0127] Furthermore, Comparative Example 3 illustrates a thermoplastic resin containing 3.3% by mass of NOD, but its refractive index is lower than that of the Examples due to its high NOD content.

[0128] Furthermore, Comparative Examples 4 and 5 illustrate thermoplastic resins containing EG and PD, but their refractive indices are lower than those in the Examples.

[0129] Furthermore, Comparative Examples 6 and 7 illustrate thermoplastic resins containing CHDM and TCDDM, but their glass transition temperatures are higher than those of the Examples.

[0130] Furthermore, Comparative Example 8 illustrates a thermoplastic resin containing 31.5% by mass of BNEF, which has a higher absolute value of orientational birefringence and a higher glass transition temperature compared to the Examples.

[0131] Furthermore, Comparative Example 9 illustrates a thermoplastic resin containing BPEF, but its refractive index is lower than that of the Examples.

[0132] Furthermore, Comparative Example 10 illustrates a thermoplastic resin that does not contain BNEF, but it has a lower refractive index and a higher absolute value of orientational birefringence compared to the examples.

[0133] The thermoplastic resin of the present invention is used in optical materials and can be used in optical components such as optical lenses, prisms, optical discs, transparent conductive substrates, optical cards, sheets, films, optical fibers, optical films, optical filters, and hard coat films, and is particularly useful for optical lenses.

Claims

1. A thermoplastic resin containing repeating units represented by the following formulas (1), (2), and (3), wherein the repeating unit represented by formula (1) is 70.0% by mass or more and 98.0% by mass or less based on the total number of repeating units, and the repeating unit represented by formula (3) is 0.1% by mass or more and 3.0% by mass or less based on the total number of repeating units: (In formula (1), R １ ~R ４ Each of these independently represents one of the following: a hydrogen atom, a halogen atom, a substituent having 1 to 20 carbon atoms which may contain an aromatic group, or a substituent having 2 to 20 carbon atoms which contains a heterocycle. １ and m ２ Each of these independently represents either 0 or 1. (In formula (2), n １ and n ２ Each of these independently represents either 0 or 1. (In formula (3), X represents an alkylene group having 4 to 14 carbon atoms.) 2. The thermoplastic resin according to claim 1, wherein the repeating unit of formula (2) above is 2.0% by mass or more and 30.0% by mass or less, based on the total number of repeating units.

3. In the above formula (1), R １ ~R ４ is a hydrogen atom, m １ and m ２ are 1, the thermoplastic resin according to claim 1 or 2.

4. The thermoplastic resin according to claim 1 or 2, wherein in formula (3) above, X is an alkylene group having 7 to 14 carbon atoms.

5. The thermoplastic resin according to claim 1 or 2, wherein the repeating unit represented by formula (3) above is 0.1% by mass or more and 1.5% by mass or less based on the total number of repeating units.

6. An optical component comprising the thermoplastic resin described in claim 1 or 2.

7. The optical component according to claim 6, which is an optical lens.

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