Thermoplastic resin and optical lens containing 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 general formula (1), R1 and R11 each independently represent a hydrogen atom, an aryl group having 6-12 carbon atoms, or a linear or branched alkyl group having 1-4 carbon atoms, and X represents one of general formulas (a) to (d).) (In general formulas (a) to (d), R21 to R57 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a linear or branched alkyl group having 1-4 carbon atoms, or a linear or branched alkoxy group having 1-7 carbon atoms.)

Description

[Technical Field]

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

[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] On the other hand, resins with a high aliphatic content are expected to be used in a variety of fields, including optical resins, due to environmental considerations. However, aliphatic resins generally have lower glass transition temperatures than aromatic resins, posing problems in terms of heat resistance. Therefore, there has been a demand for the development of resins with a high aliphatic content that have a higher glass transition temperature and better heat resistance than conventional aliphatic resins, while maintaining excellent optical properties. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Laid-Open No. 2018-2893 [Patent Document 2] Japanese Patent Application Laid-Open No. 2018-2894 [Patent Document 3] Japanese Patent Application Publication No. 2018-2895 [Patent Document 4] Japanese Patent Application Publication No. 2018-59074 [Patent Document 5] WO2017 / 078073 Summary of the Invention [Problem to be solved by the invention]

[0007] An object of the present invention is to provide a resin containing a large amount of aliphatic components that is excellent in optical properties such as refractive index and Abbe number, and also has excellent heat resistance, and an optical lens using the same. [Means for solving the problem]

[0008] As a result of extensive research aimed at solving the problems of the past, the present inventors have discovered that by using an aliphatic monomer having a specific structure as a raw material, it is possible to obtain a resin containing a large amount of aliphatic components that is excellent in optical properties such as refractive index and Abbe number, and also in heat resistance, and have thus completed the present invention.

[0009] That is, the present invention includes the following aspects. <1> The thermoplastic resin contains a structural unit (A) derived from a monomer represented by the following general formula (1). [ka] (In the general formula (1), R and R 11 each independently represents a hydrogen atom, an aryl group having 6 to 12 carbon atoms, or a linear or branched alkyl group having 1 to 4 carbon atoms, and X represents any one of the following general formulae (a) to (d): [ka] (In general formulas (a) to (d), the asterisk indicates a binding site. R 21 ~R57 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 7 carbon atoms. <2> The resin is a polycarbonate resin or a polyester carbonate resin. <1> The thermoplastic resin is as described in <3> R and R in the general formula (1) 11 are each independently a linear or branched alkyl group having 1 to 4 carbon atoms. <1> or <2> The thermoplastic resin is as described in <4> The above, wherein X in the general formula (1) is selected from the group consisting of a phenyl group, a biphenyl group, a 1-naphthyl group, and a 2-naphthyl group. <1> from <3> The thermoplastic resin is any one of the above. <5> The monomer represented by the general formula (1) consists of only the isomer B represented by the following formula, or a mixture of the isomer B and the isomer A represented by the following formula: <1> from <4> The thermoplastic resin is any one of the above. [ka] (In the above formula, R1, R 11 and X have the same meaning as in general formula (1). <6> The above, wherein the isomer ratio of the isomer A to the isomer B is A:B=0:100 to 99:1. <5> The thermoplastic resin is as described in <7> The thermoplastic resin contains a structural unit (B) derived from a monomer represented by the following general formula (2) and / or a structural unit (C) derived from a monomer represented by the following general formula (3): <1> from <6> The thermoplastic resin is any one of the above. [ka] (In general formula (2), R a and R beach 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≡CR 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. [ka] (In general formula (3), 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; Y1 is a single bond, a fluorene group which may have a substituent, or any one of the structural formulae represented by the following formulae (4) to (10): [ka] (In formulas (4) to (10), 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> In the general formula (2) and the general formula (3), A and B each independently represent an alkylene group having 2 or 3 carbon atoms. <7> The thermoplastic resin is as described in <9> The thermoplastic resin contains at least a structural unit derived from any one of BPEF, BNE, BNEF, and DPBHBNA. <7> or <8> The thermoplastic resin is as described in <10> The thermoplastic resin further contains a structural unit derived from at least one monomer selected from the following group of monomers: <1> from <9> The thermoplastic resin is any one of the above. [ka] (In the above formula, R1 and R2 each independently represent a hydrogen atom, a methyl group, or an ethyl group, and R3 and R4 each independently represent a hydrogen atom, a methyl group, an ethyl group, or an alkylene glycol having 2 to 5 carbon atoms.) <11> The thermoplastic resin has a weight average molecular weight (Mw) in terms of polystyrene of 10,000 to 200,000. <1> from <10> The thermoplastic resin is any one of the above. <12> The refractive index (nD) of the thermoplastic resin is 1.599 to 1.750. <1> from <11> The thermoplastic resin is any one of the above. <13> The Abbe number (ν) of the thermoplastic resin is 25.0 to 33.0. <1> from <12> The thermoplastic resin is any one of the above. <14> The glass transition temperature of the thermoplastic resin is 135 to 200°C. <1> from <13> The thermoplastic resin is any one of the above. <15> The thermoplastic resin composition contains a modifier represented by the following general formula (1) and a thermoplastic resin. [ka] (In the general formula (1), R and R 11 each independently represents a hydrogen atom, an aryl group having 6 to 12 carbon atoms, or a linear or branched alkyl group having 1 to 4 carbon atoms, and X represents any one of the following general formulae (a) to (d): [ka] (In general formulas (a) to (d), the asterisk indicates a binding site. R 21 ~R 57 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 7 carbon atoms. <16> the above <1> from <14> or the thermoplastic resin described above. <15> and an optical member comprising the thermoplastic resin composition according to claim 1. <17> the above <1> from <14> or the thermoplastic resin described above. <15> An optical lens comprising the thermoplastic resin composition according to claim 1. <18> the above <1> from <14> or the thermoplastic resin described above. <15> 1. An optical film comprising the thermoplastic resin composition according to claim 1. [Effects of the Invention]

[0010] According to the present invention, it is possible to provide a resin with a high aliphatic component that is excellent in optical properties such as refractive index and Abbe number, and also excellent in heat resistance, and an optical lens containing the same. DETAILED DESCRIPTION OF THE INVENTION

[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). [ka] In general formula (1), R and R 11 each independently represents a hydrogen atom, an aryl group having 6 to 12 carbon atoms (preferably 6 to 10 carbon atoms, more preferably 6 carbon atoms), or a linear or branched alkyl group having 1 to 4 carbon atoms, and X represents any of the following general formulae (a) to (d): [ka] In the general formulae (a) to (d), the asterisk indicates a binding site. 21 ~R 57 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 7 carbon atoms.

[0013] Among the structures represented by general formula (a), the following structures are preferred. [ka]

[0014] Among the structures represented by general formula (d), the following structures are preferred. [ka]

[0015] In general formula (1), R and R 11 The linear or branched alkyl group having 1 to 4 carbon atoms represented by the formula (I) is not particularly limited, and examples thereof include alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Of these, preferred are a methyl group, an ethyl group, an isobutyl group, and a tert-butyl group, and particularly preferred are an ethyl group and a methyl group. In general formula (1), R and R 11 As the aryl group having 6 to 12 carbon atoms represented by the following formula, a phenyl group is particularly preferred.

[0016] In the general formula (1), X is represented by any one of the general formulas (a) to (d), and R 21 ~R 57 The linear or branched alkyl group having 1 to 4 carbon atoms represented by the formula (I) is not particularly limited, and examples thereof include alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. The linear or branched alkoxy group having 1 to 7 carbon atoms is not particularly limited, and examples thereof include alkoxy groups such as a methoxy group and an ethoxy group.

[0017] In general formulas (a) to (d), R 21 ~R 57 is preferably a hydrogen atom. Specifically, preferred examples of X include a phenyl group (general formula (a)), a biphenyl group (general formula (b)), a 1-naphthyl group (general formula (c)), and a 2-naphthyl group (general formula (d)). Of these, a phenyl group is more preferred.

[0018] Among the cyclic diol compounds represented by the general formula (1), specifically preferred structural formulas include the following. [ka]

[0019] Specific examples of the cyclic diol compound represented by general formula (1) include 5-phenyl-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-ethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3,4-dimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, and 5-(2,4-dimethylphenyl)-1,3-cyclohexanedione. Trimethylolpropane diacetal, 5-(3-fluoro-4-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-isopropylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2,4,6-trimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2,4,5-trimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3-chloro-4-methylphenyl) -1,3-Cyclohexanedione trimethylolpropane diacetal, 5-(4-butylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-tert-butylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-isobutylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(pentamethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-biphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal cyclohexanedione trimethylolpropane diacetal, 5-(3-bromo-4-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-chlorobiphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3,5-dimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-fluoro-3-methylphenyl)-1,3-Cyclohexanedione trimethylolpropane diacetal, 5-(4-methoxy-2,3,6-trimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3-biphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-bromo-5-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3,5-di-tert-butylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-methyl Fluorophenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2,3-dimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2,6-dimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(5-fluoro-2-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-fluoro-2-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3 -fluoro-2-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(5-bromo-2-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(1-naphthalene)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-naphthalene)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-methoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-ethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, nyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3-fluoro-4-methoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-fluoro-4-methoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-isopropoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-propoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2,4-Dimethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3,4-dimethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3-chloro-4-methoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-methoxy-2,3,6-trimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-tert-butoxyphenyl)-1,3-cyclohexanedione Trimethylolpropane diacetal, 5-(2,4-dimethoxy-3-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3-ethoxy-4-methoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-ethoxy-3-methoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-fluoro-4,5-dimethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4- amyloxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2,4-diethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3,4-diethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2,4,5-trimethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3,4,5-trimethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal Diacetal, 5-(2,3,4-trimethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2,4,6-trimethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-chloro-3,4-dimethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-hexyloxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3-bromo-4-methoxyphenyl)-1,3-Cyclohexanedione trimethylolpropane diacetal, 5-(4-heptyloxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-bromo-4,5-dimethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3-bromo-4,5-dimethoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-naphthyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-methoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal -1-naphthyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-methoxy-1-naphthyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-ethoxy-1-naphthyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(6-methoxy-2-naphthyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-phenyl-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-methylphenyl)-1, 3-Cyclohexanedione trimethylolethane diacetal, 5-(4-ethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3,4-dimethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2,4-dimethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3-fluoro-4-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-isopropylphenyl)-1,3-cyclohexanedione Cyclohexanedione trimethylolethane diacetal, 5-(2,4,6-trimethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2,4,5-trimethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3-chloro-4-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-butylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-tert-butylphenyl)-1,3-Cyclohexanedione trimethylolethane diacetal, 5-(4-isobutylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(pentamethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-biphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3-bromo-4-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-chlorobiphenyl)-1,3-cyclohexanedione ethane diacetal, 5-(3-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3,5-dimethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-fluoro-3-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-methoxy-2,3,6-trimethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3-biphenyl)-1,3-cyclohexa 5-(2-bromo-5-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3,5-di-tert-butylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2,3-dimethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2,6-dimethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal Hexanedione trimethylolethane diacetal, 5-(5-fluoro-2-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-fluoro-2-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3-fluoro-2-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(5-bromo-2-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(1-naphthyl)-1,3-Cyclohexanedione trimethylolethane diacetal, 5-(2-naphthyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-methoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-ethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3-fluoro-4-methoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2-fluoro-4-methoxyphenyl)-1, 3-Cyclohexanedione trimethylolethane diacetal, 5-(4-isopropoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-propoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2,4-dimethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3,4-dimethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3-chloro-4-methoxyphenyl)-1 ,3-Cyclohexanedione trimethylolethane diacetal, 5-(4-methoxy-2,3,6-trimethylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-tert-butoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2,4-dimethoxy-3-methylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3-ethoxy-4-methoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal , 5-(4-ethoxy-3-methoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2-fluoro-4,5-dimethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-amyloxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2,4-diethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3,4-diethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal ethane diacetal, 5-(2,4,5-trimethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3,4,5-trimethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2,3,4-trimethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2,4,6-trimethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2-chloro-3,4-dimethoxyphenyl)-1,3-Cyclohexanedione trimethylolethane diacetal, 5-(4-hexyloxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3-bromo-4-methoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-heptyloxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2-bromo-4,5-dimethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(3-bromo-4,5 -dimethoxyphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-methoxy-1-naphthyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2-methoxy-1-naphthyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2-ethoxy-1-naphthyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(6-methoxy-2-naphthyl)-1,3-cyclohexanedione trimethylolethane diacetal, etc.

[0020] Among them, preferred compounds are 5-phenyl-1,3-cyclohexanedione trimethylolpropane diacetal, 5-phenyl-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-tert-butylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2,4,6-trimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2,4-dimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, Sandione trimethylolpropane diacetal, 5-(4-methylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(3,4-dimethylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-methoxyphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-isopropylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-isobutylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal phenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-tert-butylphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(4-biphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(4-biphenyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(1-naphthyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-( 1-naphthyl)-1,3-cyclohexanedione trimethylolethane diacetal, 5-(2-naphthyl)-1,3-cyclohexanedione trimethylolpropane diacetal, 5-(2-naphthyl)-1,3-cyclohexanedione trimethylolethane diacetal, and more preferred compounds are 5-phenyl-1,3-cyclohexanedione trimethylolpropane diacetal and 5-phenyl-1,3-cyclohexanedione trimethylolethane diacetal.

[0021] The cyclic diol compound represented by general formula (1) preferably consists of only isomer B represented by the following formula, or a mixture of isomer B and isomer A represented by the following formula. Another isomer includes isomer C represented by the following formula. [ka] In the above formula, R1, R 11 and X have the same meaning as in general formula (1). In one embodiment of the present invention, the isomer ratio of the isomer A to the isomer B is preferably A:B=0:100 to 99:1, more preferably 0:100 to 50:50, and particularly preferably 20:80 to 50:50. The isomer ratio can be determined by gas chromatography (GC) analysis and the area percentage method.

[0022] The novel cyclic diol compound represented by general formula (1) can be produced, for example, as shown in the following reaction scheme (I). <Reaction formula (I)> [ka] [In the formula, R1, R 11 and X have the same meaning as in the general formula (1).

[0023] As shown in the above reaction formula (I), a method for producing a novel cyclic diol compound represented by general formula (1) is to react a 1,3-cyclohexanedione compound having a substituent X at the 5-position with a substituent R or R at the 2-position. 11 and a 2-hydroxymethyl-1,3-propanediol compound having the formula:

[0024] The above-mentioned 1,3-cyclohexanedione compound having a substituent X at the 5-position (compound of the following formula (3)) can be produced by reacting a compound represented by general formula (5) with a compound represented by general formula (6) in the presence of a base, followed by treatment with an acid, as shown in the following reaction formula (II). <Reaction formula (II)> [ka] [In the formula, R 3 are the same or different and each represents an alkyl group having 1 to 3 carbon atoms. X is the same as above.]

[0025] R 3 Examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, and an isopropyl group.

[0026] This reaction can be carried out according to or in accordance with a known method, for example, the method described in Chemistry - A European Journal (2017), 23(49), 11757-11760, Zhurnal Obshchei Khimii (1957), 27. 3087-92, etc.

[0027] The thermoplastic resin of 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, but is preferably a polycarbonate resin or a polyester carbonate resin, and more preferably contains a structural unit (A) represented by the following formula: [ka] [In the formula, R1, R 11 and X have the same meaning as in the general formula (1).

[0028] In the thermoplastic resin of one embodiment of the present invention, the proportion of the structural unit (A) represented by the above formula in all structural units is not particularly limited, but is preferably 1 to 80 mol % of all structural units, more preferably 1 to 60 mol %, and particularly preferably 5 to 50 mol %. In other words, the thermoplastic resin of one embodiment of the present invention can contain, in addition to the structural unit (A) represented by the above formula, 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. Specifically, various aliphatic dihydroxy compounds can be mentioned, including, in particular, 1,4-cyclohexanedimethanol, tricyclodecanedimethanol, 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, such as 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, and bisphenoxyethanolfluorene.

[0029] 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 (2). [ka] In general formula (2), R a and R b 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≡CR 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. R 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.

[0030] In general formula (2), X represents a single bond or an optionally substituted fluorene group, and is preferably a single bond or an optionally substituted fluorene group having a total of 12 to 20 carbon atoms. In the general formula (2), 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 (2), 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 the general formula (2), 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.

[0031] Specific examples of the structural unit (B) include those derived from 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), DPBHBNA, and the like. [ka]

[0032] Furthermore, the thermoplastic resin according to one embodiment of the present invention preferably has a structural unit (C) derived from a monomer represented by the following general formula (3). [ka] In general formula (3), R c and R d are each independently selected from the group consisting of 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. R 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.

[0033] In general formula (3), Y1 is a single bond, a fluorene group which may have a substituent, or any of the structural formulae represented by the following formulae (4) to (10), and is preferably a single bond or the structural formula represented by the following formula (4). [ka] In formulas (4) to (10), 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 carbon ring or hetero ring having 1 to 20 carbon atoms which may have a substituent. In the formulas (4) to (10), r and s each independently represent an integer of 0 to 5,000.

[0034] In the general formula (3), 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 (3), p and q each independently represent an integer of 0 to 4, and preferably 0 or 1. In the general formula (3), 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.

[0035] 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, 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 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-[ Examples of structural unit (C) include those derived from BPEF or BNEF. [ka]

[0036] A 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. Polymers containing the structural unit (C) but not the structural unit (B) include, for example, those having structural units represented by the following formulae (I-1) to (I-3), and copolymers having the structural unit (B) and the structural unit (C) include, for example, those having structural units represented by the following formulae (II-1) to (II-4). [ka] (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 of 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. [ka] (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 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 the copolymer, the molar ratio of the structural unit (B) to 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. 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.

[0037] 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: [ka] (In the above formula, R1 and R2 each independently represent a hydrogen atom, a methyl group, or an ethyl group, and R3 and R4 each independently represent a hydrogen atom, a methyl group, an ethyl group, or an alkylene glycol having 2 to 5 carbon atoms.)

[0038] The polycarbonate resin of a preferred embodiment of the present invention may contain impurities such as alcohol compounds, such as phenolic compounds, which may be produced as by-products during production, and diol components or carbonate diesters that remain unreacted. Impurities such as alcohol compounds such as phenolic compounds and carbonate diesters can cause a decrease in strength when molded into a product and can also cause odor, so it is preferable that the content of these compounds is as small as possible.

[0039] The content of residual phenolic compounds is preferably 3000 ppm by mass or less, more preferably 1000 ppm by mass or less, and particularly preferably 300 ppm by mass or less, relative to 100% by mass of the polycarbonate resin. The content of the remaining diol component is preferably 1000 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 the remaining carbonate diester is preferably 1000 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 content of compounds such as phenol and t-butylphenol is small, and it is preferable that the content of these compounds is within the above range.

[0040] The content of the phenolic compound remaining in the polycarbonate resin can be measured by a method in which the phenolic compound extracted from the polycarbonate resin is analyzed by gas chromatography. The content of the alcohol-based compound remaining in the polycarbonate resin can also be measured by a method in which the alcohol-based compound extracted from the polycarbonate resin is analyzed by gas chromatography. The contents of the diol component and the carbonate diester remaining in the polycarbonate resin can also be measured by extracting these compounds from the polycarbonate resin and analyzing them by gas chromatography.

[0041] 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.

[0042] The content of each of the remaining phenolic compounds, diol components, or 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 alcohol-based compound 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.

[0043] 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.

[0044] 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.

[0045] 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, and cleavage reactions 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 3000 ppm by mass or less relative to the polycarbonate resin (100% by mass). The content of the remaining alcohol compounds is preferably 3000 ppm by mass or less, more preferably 1000 ppm by mass or less, and particularly preferably 300 ppm by mass or less relative to 100% by mass of the polycarbonate resin.

[0046] <Physical properties of thermoplastic resin> (1) Refractive index (nD) In one embodiment of the present invention, one of the features of the thermoplastic resin is that it has a high refractive index, and the refractive index is preferably 1.500 to 1.750, more preferably 1.599 to 1.750, even more preferably 1.599 to 1.650, and particularly preferably 1.600 to 1.650. In the present invention, the refractive index can be measured by the method described in the examples below.

[0047] (2) Abbe number (ν) In one embodiment of the present invention, the Abbe number of the thermoplastic resin is preferably 20.0 to 55.0, more preferably 25.0 to 33.0, even more preferably 25.5 to 32.0, and particularly preferably 26.0 to 30.0. In the present invention, the Abbe number can be measured by the method described in the examples below.

[0048] (3) Glass transition temperature (Tg) In one embodiment of the present invention, one of the features of the thermoplastic resin is high heat resistance, and the glass transition temperature (Tg) is preferably 135 to 200° C., more preferably 140 to 180° C., and particularly preferably 140 to 170° C. In the present invention, the glass transition temperature can be measured by the method described in the examples below.

[0049] (4) Polystyrene equivalent weight average molecular weight (Mw) In one embodiment of the present invention, the polystyrene-equivalent weight average molecular weight of the thermoplastic resin is preferably 10,000 to 200,000, more preferably 10,000 to 100,000, and particularly preferably 10,000 to 80,000.

[0050] <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.

[0051] [Antioxidants] The thermoplastic resin composition preferably contains an antioxidant as the additive. The antioxidant preferably contains at least one of a phenol-based antioxidant and a phosphite-based antioxidant. 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-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, and phenoxyethanol. 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, and Examples of the phosphite 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.

[0052] The antioxidant is preferably contained in the thermoplastic resin composition in an amount of 1 ppm by weight to 3000 ppm by weight based on the total weight of the resin composition, more preferably 50 ppm by weight to 2500 ppm by weight, even more preferably 100 ppm by weight to 2000 ppm by weight, particularly preferably 150 ppm by weight to 1500 ppm by weight, and even more preferably 200 ppm by weight to 1200 ppm by weight.

[0053] [Release agent] The thermoplastic resin composition preferably contains a mold release agent as the additive. Examples of the release agent include ester compounds, for example, 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, full esters or mono-fatty acid esters of aliphatic polyhydric alcohols and aliphatic carboxylic acids, etc. When an ester of aliphatic polyhydric alcohols and aliphatic carboxylic acids is used as the release agent, either monoesters or full esters can be used, but other than full esters, such as monoesters, may also be used. Specific examples of the release agent include the following: namely, sorbitan fatty acid esters such as sorbitan stearate, sorbitan laurate, sorbitan oleate, sorbitan trioleate, sorbitan tribehenate, sorbitan stearate, sorbitan tristearate, sorbitan caprylate, etc.; 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 fatty acid ester monoglycerides, including glycerin monohydroxystearates such as glycerin monostearate and glycerin mono 12-hydroxystearate, glycerin monooleate, glycerin monobehenate, glycerin monocaprylate, glycerin monocaprate, and glycerin monolaurate; and mono- and diglycerides such as glycerin monodistearate, glycerin monodistearate, glycerin monodibehenate, and glycerin monodiolate; Acetylated monoglycerides of glycerin fatty acid esters such as glycerin diacetomonolaurate; Glycerin fatty acid ester organic acid monoglycerides such as citric acid fatty acid monoglyceride, succinic acid fatty acid monoglyceride, and diacetyltartaric acid fatty acid monoglyceride; Examples of the fatty acid ester include polyglycerol fatty acid esters such as diglycerol stearate, diglycerol laurate, diglycerol oleate, diglycerol monostearate, diglycerol monolaurate, diglycerol monomyristate, diglycerol monooleate, tetraglycerol stearate, decaglycerol laurate, decaglycerol oleate, and polyglycerol polyricinoleate.

[0054] The thermoplastic resin composition preferably contains 1 ppm by weight to 5000 ppm by weight of the release agent based on the total weight of the resin composition. The content of the release agent in the thermoplastic resin composition is more preferably 50 ppm by weight to 4000 ppm by weight, even more preferably 100 ppm by weight to 3500 ppm by weight, particularly preferably 500 ppm by weight to 13000 ppm by weight, and even more preferably 1000 ppm by weight to 2500 ppm by weight.

[0055] [Other additives] In addition to the antioxidant and mold release agent, other additives may be added to the thermoplastic resin composition. Examples of additives that may be contained in the thermoplastic resin composition include compounding agents, catalyst deactivators, heat stabilizers, plasticizers, fillers, ultraviolet absorbers, rust inhibitors, dispersants, antifoaming agents, leveling agents, flame retardants, lubricants, dyes, pigments, bluing agents, nucleating agents, and clarifying agents. The content of additives other than the antioxidant and the 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 the transmittance, so it is preferable not to add them in excess, and for example, the total amount added is within the above-mentioned range.

[0056] In the method for producing a thermoplastic resin composition of the present invention, the catalyst may be removed or deactivated after the polymerization reaction to maintain thermal stability and hydrolytic stability, but deactivation is not necessarily required. When deactivating the catalyst, a known method for deactivating the catalyst by adding an acidic substance can be suitably carried out. Specific examples of the acidic substance include esters such as butyl benzoate; aromatic sulfonic acids such as p-toluenesulfonic acid; aromatic sulfonic acid esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate; phosphoric acids such as phosphorous acid, phosphoric acid, and phosphonic acid; phosphite esters such as triphenyl phosphite, monophenyl phosphite, diphenyl phosphite, diethyl phosphite, di-n-propyl phosphite, di-n-butyl phosphite, di-n-hexyl phosphite, dioctyl phosphite, and monooctyl phosphite; triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate, and dioctyl phosphate. Suitable examples of suitable deactivators include phosphate esters such as phenylphosphonic acid and 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 stearic acid chloride, benzoyl chloride, and p-toluenesulfonic acid chloride; alkyl sulfates such as dimethyl sulfate; and organic halides such as benzyl chloride. From the viewpoints of the deactivator effect and stability to the resin, p-toluene or butyl sulfonate is particularly preferred. These deactivators are used in an amount of 0.01 to 50 times, preferably 0.3 to 20 times, the molar amount of the catalyst. Less than 0.01 times the molar amount of the catalyst is undesirable because the deactivation effect is insufficient. Furthermore, if the amount is more than 50 times the amount of the catalyst by mole, the heat resistance of the resin decreases and the molded product tends to be discolored, which is undesirable. The deactivator may be kneaded immediately after the polymerization reaction is completed, or after the polymerized resin is pelletized. In addition to the deactivator, other additives may also be added in the same manner.

[0057] Furthermore, another embodiment of the present invention is a thermoplastic resin composition containing a modifier represented by the following general formula (1) and a thermoplastic resin. [ka] In general formula (1), R1, R 11 and X have the same meanings as in the above-mentioned general formula (1). That is, the novel cyclic diol compound represented by general formula (1) can also be used as a modifier.

[0058] In one embodiment of the present invention, the modifier can be blended so that the mass ratio of the thermoplastic resin to the modifier is 99.9:0.1 to 70:30. The mass ratio is preferably 99:1 to 70:30, and more preferably 98:2 to 70:30, such as 99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 85:15, 80:20, 75:25, or 70:30. In the present invention, when the mass ratio of the thermoplastic resin to the modifier is within the above range, a resin composition with high flowability and good moldability can be provided.

[0059] <Optical components> The thermoplastic resin or thermoplastic resin composition of the present invention (hereinafter simply referred to as "resin composition") can be suitably used for optical components. In one embodiment of the present invention, an optical component comprising the resin composition of the present invention is provided. In one embodiment of the present invention, optical components include, but are not limited to, optical disks, transparent conductive substrates, optical cards, sheets, films, optical fibers, lenses, prisms, optical films, substrates, optical filters, and hard coat films. The resin composition of the present invention can be molded by a casting method with high flow, making it particularly suitable for producing thin optical components. In a preferred embodiment of the present invention, the optical component produced using the resin composition of the present invention may be an optical lens. Among optical lenses, in addition to smartphone lenses, specific examples include lenses for in-vehicle cameras, lenses for goggles for VR (virtual reality) or MR (mixed reality), and lenses for security cameras. In another preferred embodiment of the present invention, the optical component produced using the resin composition of the present invention may be an optical film.

[0060] 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.

[0061] <Optical lenses> 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 the case of a smartphone lens, 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 [ka] (In the above formula, R1 and R2 each independently represent a hydrogen atom, a methyl group, or an ethyl group, and R3 and R4 each independently represent 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 and used as a lens unit.

[0062] The optical lens of the present invention is preferably implemented as an aspherical lens, if necessary. Since a single aspherical lens can substantially eliminate spherical aberration, 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.

[0063] Furthermore, the optical lens of the present invention has high molding fluidity and is therefore 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. The lens preferably has a meniscus shape, with one surface convex and the other concave. The optical lens of the present invention can be formed by any method such as mold molding, cutting, polishing, laser processing, electrical discharge processing, etching, etc. Among these, mold molding is more preferred in terms of production costs.

[0064] <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 suitably used for liquid crystal substrate films, optical memory cards, etc. To prevent foreign matter from getting into the optical film as much as possible, the molding environment must naturally be a low-dust environment, preferably class 6 or less, more preferably class 5 or less. [Example]

[0065] Examples of the present invention will be shown below together with comparative examples to explain the details of the invention, but the present invention is not limited to these examples.

[0066] 1) Refractive index (nD) Based on JIS B 7071-2:2018, polycarbonate resin was molded to obtain a V-block as a test piece. Refractometry was performed at 23°C using a refractometer (Shimadzu KPR-3000).

[0067] 2) 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. ν=(nD-1) / (nF-nC) nD: Refractive index at a wavelength of 589 nm nC: Refractive index at a wavelength of 656 nm nF: Refractive index at a wavelength of 486 nm

[0068] 3) Glass transition temperature (Tg) Measurement was carried out using a differential scanning calorimeter (X-DSC7000 manufactured by Hitachi High-Tech Science Corporation) according to JIS K7121-1987, with a temperature increase program of 10°C / min.

[0069] 4) Weight average molecular weight (Mw) The weight average molecular weight of the resin was measured by gel permeation chromatography (GPC) and calculated in terms of standard polystyrene. The apparatus, column, and measurement conditions used are as follows: GPC equipment: Tosoh Corporation, HLC-8420GPC Column: Tosoh Corporation, TSKgel SuperHM-M × 3 Tosoh Corporation, TSKgel guardcolumn SuperH-H x 1 Tosoh Corporation, TSKgel SuperH-RC x 1 Detector: RI detector Standard polystyrene: Tosoh Corporation, Standard Polystyrene Kit PStQuick C Sample solution: 0.2% by mass tetrahydrofuran solution Eluent: tetrahydrofuran ·Eluent flow rate: 0.6mL / min Column temperature: 40℃

[0070] [Synthesis Example 1] A 300 ml recovery flask equipped with a condenser and a Dean-Stark tube was charged with 12.5 g (66.4 mmol) of 5-phenyl-1,3-cyclohexanedione, 625 mg of phosphotungstic acid, 21.3 g (159 mmol) of trimethylolpropane, and 125 ml of toluene, followed by the addition of a stirrer. The temperature was raised while stirring with a magnetic stirrer, and the acetal reaction was carried out for 2 hours under toluene reflux, while the outflowing water was removed with the Dean-Stark tube until the theoretical amount of water produced (132 mmol, 2.3 g) was reached. The reaction mixture was returned to room temperature, neutralized with 125 ml of saturated aqueous sodium bicarbonate, and then 125 ml of toluene was added to separate the aqueous and organic layers. The separated organic layer was washed with 125 ml of warm water at 40 °C. The organic layer was set to 40 °C and 50 mmHg, and the solvent was removed using an evaporator. 125 g of the remaining organic layer was stirred at room temperature, and crystals were isolated. The precipitated crystals were filtered using toluene as a rinse. 16.0 g of the wet crystals were dried at 5 mmHg and 100 °C to obtain 11.8 g (28 mmol) of 5-phenyl-1,3-cyclohexanedione trimethylolpropane diacetal (hereinafter referred to as "Compound 1") with a GC area value of 99.6%. The melting point of the crystals was 135 °C. The obtained 5-phenyl-1,3-cyclohexanedione trimethylolpropane diacetal was analyzed by IR spectrum and 1 The H-NMR spectrum was measured, and it was confirmed to be 5-phenyl-1,3-cyclohexanedione trimethylolpropane diacetal from the following characteristic peaks. IR(cm -1 ):3365,2965,2948,1474,1463,1358,1263,1253,1191,1162,1087,1061,1031,1000,969,820,756,699 1H-NMR(500MHz,ppm):0.80(t,3H),0.87(t,3H),1.24(m,2H),1.33(m,2H),1.39(t,1H),1.49(d,1H),1.67(t, 1H),1.96(d,2H),2.18(d,1H),2.76(d,1H),2.94(m,2H),3.70(m,10H),3.82(m,2H),7.20(m,3H),7.31(m,2H) The peak at around 7.26 ppm is a peak derived from the solvent, deuterated chloroform. Furthermore, as a result of LC analysis of Compound 1, the LC area value of Isomer A represented by the following structural formula was 26.6%, and the LC area value of Isomer B represented by the following structural formula was 73.1%, i.e., the isomer ratio (Isomer A:Isomer B=27:73). [ka]

[0071] [Synthesis Example 2] Using Compound 1 obtained in Synthesis Example 1, recrystallization similar to that in Synthesis Example 1 was repeated until the area value of Isomer A was no longer detected by LC analysis, to obtain Compound 2. As a result of LC analysis of Compound 2, the LC area value of Isomer B was 97.0%, and the LC area value of Isomer A was not detected, i.e., the isomer ratio was (Isomer A:Isomer B=0:100).

[0072] [Synthesis Example 3] 42.8 g (264 mmol) of 4-t-butylbenzaldehyde and 396 ml of acetone were placed in a 1 L beaker, and while stirring at room temperature, 264 g of a 10 wt % aqueous sodium hydroxide solution was added dropwise at a temperature of 30° C. or less. The mixture was then stirred at room temperature for 2.5 hours, neutralized with 44 g of acetic acid, and the acetone was then distilled off. 264 ml of ethyl acetate was added, and the organic phase was separated. The obtained organic phase was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, and concentrated under reduced pressure to obtain 65.1 g of a pale yellow liquid with a purity of 90.7 GC area %. The obtained crude reaction product was subjected to simple distillation under reduced pressure at 141-145°C and 0.1-0.2 kPa to obtain 35.4 g of a pale yellow liquid with a purity of 98.8 GC area %. A 500 ml four-neck flask equipped with a thermometer, nitrogen inlet tube, and condenser was charged with 30 ml of ethanol, 17.4 g (110 mmol) of diethyl malonate, and 37.4 g (110 mmol) of a 20 wt% sodium ethoxide ethanol solution, and stirred at room temperature for 30 minutes. The temperature was then raised to 70°C, and a solution of 20.2 g (100 mmol) of 4-t-butylbenzylideneacetone dissolved in 30 ml of ethanol was added dropwise over 25 minutes at the same temperature. 80 ml of ethanol was then added, and the temperature was raised, followed by stirring under reflux for 2 hours. Next, hydrolysis was carried out under reflux with 10 wt% aqueous sodium hydroxide for 2 hours, and then 150 ml of ethanol was distilled off under reduced pressure. After cooling to room temperature, 80 g of 20 wt% aqueous hydrogen chloride was added, and decarboxylation reaction was carried out under reflux for 4 hours. The precipitated crystals were rinsed with 50 ml of water four times and dried under reduced pressure to obtain 25.6 g of crude crystals with a GC purity of 91.3%. Subsequently, 200 ml of ethyl acetate was added, and the mixture was stirred at 70 ° C for 1 hour. The precipitated crystals were filtered and rinsed with 50 ml of ethyl acetate, and then dried under reduced pressure at 100 ° C for 2 hours to obtain 19.7 g of a pale dark solid with a purity of 98.9 GC area%. A 500 ml four-neck flask equipped with a thermometer, nitrogen inlet tube, and condenser with a water separator was charged with 12.4 g (50 mmol) of 5-(4-t-butylphenyl)-1,3-cyclohexanedione, 16.8 g (125 mmol) of trimethylolpropane, 625 mmg of phosphotungstic acid, and 120 ml of toluene, and the mixture was heated and stirred at reflux temperature for 2.5 hours. After the reaction was completed, the mixture was cooled to room temperature, 50 ml of saturated aqueous sodium bicarbonate solution was added, and the mixture was stirred for 0.5 hours. Then, 50 ml of ethyl acetate was added, and the resulting organic phase was washed with warm water and concentrated under reduced pressure to obtain 23.5 g of crude diacetal. The obtained crude product was purified by recrystallization from 90 g of toluene, filtered, the cake washed (40 ml of cold toluene), and dried under reduced pressure at 100°C for 2 hours, yielding 14.8 g of 5-(4-t-butylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal (hereinafter referred to as "compound 3") with a purity of 98.5 GC area %. [ka]

[0073] Example 1 As raw materials, 23.5810 g (0.0538 mol) of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF) represented by the following structural formula, 9.6899 g (0.0230 mol) of 5-phenyl-1,3-cyclohexanedione trimethylolpropane diacetal obtained in Synthesis Example 1, 16.9474 g (0.0791 mol) of diphenyl carbonate (DPC), and 1.29071 × 10 sodium hydrogen carbonate were used. -4 g(1.53638×10 -6 (mol) was placed in a 300 mL reactor equipped with a stirrer and distillation device, and the system was set to a nitrogen atmosphere of 101.3 kPa. The reactor was immersed in an oil bath heated to 200°C to initiate the transesterification reaction. Stirring began 5 minutes after the start of the reaction, and 20 minutes later, the pressure was reduced from 101.3 kPa to 26.66 kPa over 10 minutes. The temperature was heated to 210°C while reducing the pressure, and 70 minutes after the start of the reaction, the temperature was raised to 220°C. From 80 minutes later, the pressure was reduced to 20.00 kPa over 30 minutes. The temperature was raised to 240°C, and the pressure was reduced to 0.133 kPa and maintained for 10 minutes. After that, nitrogen gas was introduced into the reaction system, and the pressure was returned to 101.3 kPa, yielding a polycarbonate resin. The refractive index of the obtained polycarbonate resin was 1.6076, the Abbe number was 27.46, the Tg was 144°C, and the weight average molecular weight (Mw) in terms of polystyrene was 37,000. The content of the diol compound as a raw material and the physical properties of the obtained resin are shown in Table 1 below.

[0074] Example 2 As raw materials, 25.4506 g (0.0580 mol) of BPEF, 6.0881 g (0.0145 mol) of 5-phenyl-1,3-cyclohexanedione trimethylolpropane diacetal obtained in Synthesis Example 2, 16.0044 g (0.0747 mol) of DPC, and 4.25154 × 10 sodium hydrogen carbonate were used. -7 g(3.65573×10 -5 A polycarbonate resin was obtained in the same manner as in Example 1, except that a hydroxybenzoate (100%) was used. The resulting polycarbonate resin had a refractive index of 1.6125, an Abbe number of 26.02, a Tg of 148°C, and a polystyrene-equivalent weight average molecular weight (Mw) of 40,000. The contents of the diol compounds used as raw materials and the physical properties of the resulting resin are shown in Table 1 below.

[0075] Example 3 As raw materials, 23.3726 g (0.0533 mol) of BPEF, 6.5309 g (0.0129 mol) of 5-(4-t-butyl)-phenyl-1,3-cyclohexanedione trimethylolpropane diacetal obtained in Synthesis Example 3, 14.6156 g (0.0682 mol) of DPC, and 4.25154 × 10 sodium hydrogen carbonate were used. -7 g(3.65573×10 -5 A polycarbonate resin was obtained in the same manner as in Example 1, except that a hydroxybenzoate (100%) was used. The refractive index of the obtained polycarbonate resin was 1.6119, the Abbe number was 26.35, the Tg was 146°C, and the weight average molecular weight (Mw) in terms of polystyrene was 37,000. The content of the diol compound as a raw material and the physical properties of the obtained resin are shown in Table 1 below.

[0076] (Comparative Example 1) The raw materials used were 42.5953 g (0.0971 mol) of BPEF, 12.6658 g (0.0416 mol) of spiro glycol (3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane) (SPG) represented by the following structural formula, 30.6188 g (0.1429 mol) of DPC, and 1.1656 × 10 sodium bicarbonate. -4 g(1.3874×10 -6 A polycarbonate resin was obtained in the same manner as in Example 1 except that a hydroxybenzoate (100%) was used. The resulting polycarbonate resin had a refractive index of 1.5998, an Abbe number of 26.53, a Tg of 134°C, and a polystyrene-equivalent weight average molecular weight (Mw) of 39,000. The contents of the diol compounds used as raw materials and the physical properties of the resulting resin are shown in Table 1 below. [ka] [Table 1] The results in Table 1 show that Examples 1 to 3, which used the novel cyclic diol compound represented by general formula (1), have higher refractive index (nD) and glass transition temperature than Comparative Example 1, which used spiroglycol, a conventional cyclic diol compound, and can provide resins with a high aliphatic component content that are excellent not only in optical properties but also in heat resistance.

Claims

1. A thermoplastic resin comprising a structural unit (A) derived from a monomer represented by the following general formula (1), wherein the thermoplastic resin is a polycarbonate resin or a polyester carbonate resin: 【Chemical 1】 (In general formula (1), R １ and R １１ each independently represents a hydrogen atom, an aryl group having 6 to 12 carbon atoms, or a linear or branched alkyl group having 1 to 4 carbon atoms, and X represents any one of the following general formulas (a) to (d): 【Chemistry 2】 (In general formulas (a) to (d), the asterisk indicates the binding site. R ２１ ~R ５７ each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 7 carbon atoms.

2. R in the general formula (1) １ and R １１ and each independently represent a linear or branched alkyl group having 1 to 4 carbon atoms.

3. 3. The thermoplastic resin according to claim 1, wherein X in the general formula (1) is selected from the group consisting of a phenyl group, a biphenyl group, a 1-naphthyl group, and a 2-naphthyl group.

4. The thermoplastic resin according to any one of claims 1 to 3, wherein the monomer represented by general formula (1) consists of only isomer B represented by the following formula, or a mixture of isomer B and isomer A represented by the following formula: 【Chemistry 3】 (In the above formula, R １ , R １１ and X have the same meaning as in general formula (1).

5. 5. The thermoplastic resin according to claim 4, wherein the isomer ratio of the isomer A to the isomer B is A:B=0:100 to 99:

1.

6. The thermoplastic resin according to any one of claims 1 to 5, wherein the thermoplastic resin comprises a structural unit (B) derived from a monomer represented by the following general formula (2) and / or a structural unit (C) derived from a monomer represented by the following general formula (3): 【Chemistry 4】 (In general formula (2), 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. 【Chemistry 5】 (In general formula (3), 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 (4) to (10): 【Chemistry 6】 (In formulas (4) to (10), 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.

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

8. The thermoplastic resin comprises at least 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (BPEF), 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), 9,9-bis[6-(2-hydroxyethoxy)naphthalen-2-yl]fluorene (BNEF), and the following structural formula: DPBHBNA. The thermoplastic resin according to claim 6 or 7, which contains a structural unit derived from any one of them. 【Chemistry 7】

9. The thermoplastic resin according to any one of claims 1 to 8, further comprising a structural unit derived from at least one monomer selected from the following group of monomers: 【Chemistry 8】 (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.

10. The thermoplastic resin according to any one of claims 1 to 9, wherein the weight average molecular weight (Mw) of the thermoplastic resin in terms of polystyrene is 10,000 to 200,000.

11. The thermoplastic resin according to any one of claims 1 to 10, wherein the refractive index (nD) of the thermoplastic resin is 1.599 to 1.

750.

12. The thermoplastic resin according to any one of claims 1 to 11, wherein the Abbe number (ν) of the thermoplastic resin is 25.0 to 33.

0.

13. The thermoplastic resin according to any one of claims 1 to 12, wherein the glass transition temperature of the thermoplastic resin is 135 to 200°C.

14. A thermoplastic resin composition comprising a modifier represented by the following general formula (1) and a thermoplastic resin, wherein the thermoplastic resin is a polycarbonate resin or a polyester carbonate resin. 【Chemistry 9】 (In general formula (1), R １ and R １１ each independently represents a hydrogen atom, an aryl group having 6 to 12 carbon atoms, or a linear or branched alkyl group having 1 to 4 carbon atoms, and X represents any one of the following general formulas (a) to (d): 【Chemistry 10】 (In general formulas (a) to (d), R ２１ ~R ５７ each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 7 carbon atoms.

15. An optical member comprising the thermoplastic resin according to any one of claims 1 to 13 or the thermoplastic resin composition according to claim 14.

16. An optical lens comprising the thermoplastic resin according to any one of claims 1 to 13 or the thermoplastic resin composition according to claim 14.

17. An optical film comprising the thermoplastic resin according to any one of claims 1 to 13 or the thermoplastic resin composition according to claim 14.

Images