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 the formula, R1s are identical or different from each other and each represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, or a linear or branched alkyl group having 1-4 carbon atoms. Ring A represents a benzene ring which may have 1-4 substituents selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1-6 carbon atoms, and a linear or branched alkyl group having 1-6 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, thermoplastic resins made from diol compounds with a cyclic acetal structure (e.g., spiroglycol) have excellent optical properties and impact resistance, making them useful as various optical resins. However, due to the wide range of molding processes and usage environments, there has been a demand for further improvement in heat resistance without compromising optical properties. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication 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 thermoplastic resin that has excellent 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 found that by using as a raw material a monomer having a specific structure in which an aromatic ring is introduced into a diol compound having a cyclic acetal structure, it is possible to obtain a thermoplastic resin that is excellent in optical properties such as refractive index and Abbe number, as well as in heat resistance, and have 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 formula, R 1 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, or a linear or branched alkyl group having 1 to 4 carbon atoms. Ring A represents a benzene ring optionally substituted with 1 to 4 groups selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, and a linear or branched alkyl group having 1 to 6 carbon atoms. <2> The above resin is a polycarbonate resin or a polyester carbonate resin. <1> The thermoplastic resin is as described in <3> R in the general formula (1) 1 are the same or different and each is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, or a phenyl group. <1> or <2> The thermoplastic resin is as described in <4> In the general formula (1), R 1 are the same or different and each represents a methyl group or an ethyl group. <3> The thermoplastic resin is as described in <5> In the general formula (1), the ring A is a benzene ring optionally substituted with 1 to 4 groups selected from the group consisting of a linear or branched alkoxy group having 1 to 6 carbon atoms and a linear or branched alkyl group having 1 to 6 carbon atoms. <1> from <4> The thermoplastic resin is any one of the above. <6> In the general formula (1), R 1 is a methyl group or an ethyl group, and ring A is a benzene ring optionally substituted with 1 to 4 groups selected from the group consisting of methyl groups and ethyl groups. <1> from <5> The thermoplastic resin is any one of the above. <7> The monomer represented by the general formula (1) is a monomer represented by the following general formula (1a): <1> or <2> The thermoplastic resin is as described in [ka] [In the formula, R 2 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, or a linear or branched alkyl group having 1 to 6 carbon atoms. 1 is the same as above.] <8> The monomer represented by the general formula (1) is a monomer represented by the following general formula (1b): <1> or <2> The thermoplastic resin is as described in [ka] [In the formula, R 2 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, or a linear or branched alkyl group having 1 to 6 carbon atoms. 1 is the same as above.] <9> The monomer represented by the general formula (1) is a monomer represented by the following general formula (1c): <1> or <2> The thermoplastic resin is as described in [ka] [In the formula, R 2 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, or a linear or branched alkyl group having 1 to 6 carbon atoms. 1 is the same as above.] <10> The thermoplastic resin contains a structural unit (B) derived from a monomer represented by the following formula (2) and / or a structural unit (C) derived from a monomer represented by the following formula (3): <1> from <9> The thermoplastic resin is any one of the above. [ka] (In 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≡CR h selected from the group consisting of R hrepresents 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 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. <11> In the formula (2) and the formula (3), A and B each independently represent an alkylene group having 2 or 3 carbon atoms. <10> The thermoplastic resin is as described in <12> The thermoplastic resin contains at least a structural unit derived from any one of BPEF, BNE, BNEF, and DPBHBNA. <10> or <11> The thermoplastic resin is as described in <13> The thermoplastic resin further contains a structural unit derived from at least one monomer selected from the following group of monomers: <1> from <12> 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.) <14> The thermoplastic resin has a weight average molecular weight (Mw) of 10,000 to 200,000 in terms of polystyrene. <1> from <13> The thermoplastic resin is any one of the above. <15> The refractive index (nD) of the thermoplastic resin is 1.599 to 1.750. <1> from <14> The thermoplastic resin is any one of the above. <16> The Abbe number (ν) of the thermoplastic resin is 25.0 to 33.0. <1> from <15> The thermoplastic resin is any one of the above. <17> The glass transition temperature of the thermoplastic resin is 135 to 200°C. <1> from <16> The thermoplastic resin is any one of the above. <18> The thermoplastic resin composition contains a modifier represented by the following general formula (1) and a thermoplastic resin. [ka] [In the formula, R 1 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, or a linear or branched alkyl group having 1 to 4 carbon atoms. Ring A represents a benzene ring optionally substituted with 1 to 4 groups selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, and a linear or branched alkyl group having 1 to 6 carbon atoms. <19> the above <1> from <17> or the thermoplastic resin described above. <20> and an optical member comprising the thermoplastic resin composition according to claim 1. <20> the above <1> from <17> or the thermoplastic resin described above. <18> An optical lens comprising the thermoplastic resin composition according to claim 1. <21> the above <1> from <17> or the thermoplastic resin described above. <18> 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 thermoplastic resin that is excellent in optical properties such as refractive index and Abbe number, and also 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 the formula, R 1are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, or a linear or branched alkyl group having 1 to 4 carbon atoms. Ring A represents a benzene ring optionally substituted with 1 to 4 groups selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, and a linear or branched alkyl group having 1 to 6 carbon atoms.

[0013] In general formula (1), R 1 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, or a linear or branched alkyl group having 1 to 4 carbon atoms, with a linear or branched alkyl group having 1 to 4 carbon atoms being preferred. 1 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. Among these, preferred are a methyl group, an ethyl group, an isobutyl group, and a tert-butyl group, more preferred are a methyl group and an ethyl group, and particularly preferred is a methyl group.

[0014] In general formula (1), ring A means that two acetal groups are bonded to each other at the ortho, meta, or para position on the benzene ring. Specifically, ring A includes the following structures: [ka] [In the formula, ring A is the same as above.]

[0015] In general formula (1), ring A is preferably a benzene ring optionally substituted with 1 to 4 groups selected from the group consisting of linear or branched alkoxy groups having 1 to 6 carbon atoms and linear or branched alkyl groups having 1 to 6 carbon atoms.

[0016] The "straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms" as a substituent is not particularly limited, and examples thereof include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, etc. Among these, a methoxy group, an ethoxy group, an isopropyloxy group, an isobutyloxy group, and a tert-butyloxy group are preferred.

[0017] The "straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms" as a substituent is not particularly limited, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, etc. Among these, a methyl group, an ethyl group, an isopropyl group, an isobutyl group, and a tert-butyl group are preferred.

[0018] Particularly preferred as ring A is a benzene ring having no substituent, that is, a divalent phenylene group having the following structure: [ka]

[0019] The compound represented by general formula (1) has a hydroxymethyl group in the two acetal groups and R 1 Depending on the configuration of the carbon atom to which the is bonded, multiple stereoisomers are possible. These isomers may exist alone or in mixture.

[0020] Three compounds included in the compounds represented by general formula (1) are classified based on the substitution positions of the two acetal groups on ring A, that is, the compounds represented by the following general formulas (1a), (1b), and (1c) will be specifically described.

[0021] The compound represented by general formula (1a) is as follows. [ka] [In the formula, R2 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, or a linear or branched alkyl group having 1 to 6 carbon atoms. 1 is the same as above.]

[0022] In general formula (1a), R 1 is preferably a linear or branched alkyl group having 1 to 4 carbon atoms, 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, or a tert-butyl group. Of these, a methyl group, an ethyl group, an isobutyl group, or a tert-butyl group is preferred.

[0023] In general formula (1a), R 2 R is preferably a hydrogen atom, a linear or branched alkoxy group having 1 to 6 carbon atoms, or a linear or branched alkyl group having 1 to 6 carbon atoms. 2 is particularly preferably a hydrogen atom. R 2 The "linear or branched alkoxy group having 1 to 4 carbon atoms" represented by the formula (I) is not particularly limited, and examples thereof include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, etc. Among these, a methoxy group, an ethoxy group, an isopropyloxy group, an isobutyloxy group, and a tert-butyloxy group are preferred.

[0024] R 2 The "linear or branched alkyl group having 1 to 6 carbon atoms" represented by the formula (I) is not particularly limited, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, etc. Among these, a methyl group, an ethyl group, an isopropyl group, an isobutyl group, and a tert-butyl group are preferred.

[0025] The compound represented by general formula (1a) may have isomers such as isomer A, isomer B, or isomer C. These isomers may exist either singly or in mixture. [ka] [In the formula, R 1 and R 2 is the same as above.]

[0026] When the compound represented by general formula (1a) is a mixture of two or more isomers, the isomer ratio can be determined by the area percentage method through gas chromatography (GC) analysis using the method described in the Examples. Each isomer usually has its own unique peak in GC analysis. The content ratio of an isomer can be expressed as the percentage of the peak area of ​​each isomer relative to the total peak area of ​​the cyclic diol compound. The percentage ratio of each isomer can be taken as the isomer ratio. The cyclic diol compound of the present invention can also be subjected to trimethylsilylation of the hydroxyl groups using N,O-bis(trimethylsilyl)trifluoroacetamide or the like, followed by GC analysis.

[0027] The compound represented by general formula (1a) may have isomers such as isomer (1a-A), isomer (1a-B), or isomer (1a-C) as described above. Two or three isomer peaks were detected by GC analysis, which are considered to be isomer (1a-A), isomer (1a-B), or isomer (1a-C). The isomer ratio determined by GC analysis can be in the range of isomer (1a-A):isomer (1a-B):isomer (1a-C) = 10 to 1:10 to 1:1.

[0028] Specific examples of the compound represented by general formula (1a) include isophthalaldehyde trimethylolpropane diacetal, isophthalaldehyde trimethylolethane diacetal, 5-methylisophthalaldehyde trimethylolethane diacetal, 4-methylisophthalaldehyde trimethylolethane diacetal, 4-chloroisophthalaldehyde trimethylolethane diacetal, 5-chloroisophthalaldehyde trimethylolethane diacetal, 5 -Bromoisophthalaldehyde trimethylolethane diacetal, 4-Bromoisophthalaldehyde trimethylolethane diacetal, 2-Bromoisophthalaldehyde trimethylolethane diacetal, 4,6-Dimethylisophthalaldehyde trimethylolethane diacetal, 2,4-Dimethylisophthalaldehyde trimethylolethane diacetal, 2,5-Dichloroisophthalaldehyde trimethylolethane diacetal, 4,6-Dichloroisophthalaldehyde Isophthalaldehyde trimethylolethane diacetal, 4,6-dibromoisophthalaldehyde trimethylolethane diacetal, 2,5-dibromoisophthalaldehyde trimethylolethane diacetal, 5-tert-butylisophthalaldehyde trimethylolethane diacetal, 2,4,5,6-tetrafluoroisophthalaldehyde trimethylolethane diacetal, 5-(bromomethyl)isophthalaldehyde trimethylolethane diacetal, 4-isopropyl Isophthalaldehyde trimethylolethane diacetal, 4,6-diisopropylisophthalaldehyde trimethylolethane diacetal, 2-bromo-5-tert-butylisophthalaldehyde trimethylolethane diacetal, 4-phenylisophthalaldehyde trimethylolethane diacetal, 5-phenylisophthalaldehyde trimethylolethane diacetal, 4-phenyl-6-methylisophthalaldehyde trimethylolethane diacetal, 4,5-Diethyl-6-methylisophthalaldehyde trimethylolethane diacetal, 5-Hexylisophthalaldehyde trimethylolethane diacetal, 4-Hexylisophthalaldehyde trimethylolethane diacetal, 5-Butyloxyisophthalaldehyde trimethylolethane diacetal, 2-Methoxyisophthalaldehyde trimethylolethane diacetal, 4-Methoxyisophthalaldehyde trimethylolethane diacetal, 5-Methoxyisophthalaldehyde trimethylolethane diacetal, 2-Methoxy -4-Methylisophthalaldehyde trimethylolethane diacetal, 2-methyl-4-methoxyisophthalaldehyde trimethylolethane diacetal, 2-methoxy-5-methylisophthalaldehyde trimethylolethane diacetal, 4-methyl-6-methoxyisophthalaldehyde trimethylolethane diacetal, 4,6-dimethoxyisophthalaldehyde trimethylolethane diacetal, 2-methoxy-4-ethylisophthalaldehyde trimethylolethane diacetal, 4,6-dimethyl-2-methoxyisophthalaldehyde aldehyde trimethylolethane diacetal, 2,4-dimethoxy-6-methylisophthalaldehyde trimethylolethane diacetal, 2,4-dimethyl-6-methoxyisophthalaldehyde trimethylolethane diacetal, 4-ethyl-5-methyl-6-methoxyisophthalaldehyde trimethylolethane diacetal, 5-methylisophthalaldehyde trimethylolpropane diacetal, 4-methylisophthalaldehyde trimethylolpropane diacetal, 4-chloroisophthalaldehyde trimethylolpropane diacetal Tar, 5-chloroisophthalaldehyde trimethylolpropane diacetal, 5-bromoisophthalaldehyde trimethylolpropane diacetal, 4-bromoisophthalaldehyde trimethylolpropane diacetal, 2-bromoisophthalaldehyde trimethylolpropane diacetal, 4,6-dimethylisophthalaldehyde trimethylolpropane diacetal, 2,4-dimethylisophthalaldehyde trimethylolpropane diacetal, 2,5-dichloroisophthalaldehyde trimethylolpropane diacetal, 4,6-Dichloroisophthalaldehyde trimethylolpropane diacetal, 4,6-Dibromoisophthalaldehyde trimethylolpropane diacetal, 2,5-Dibromoisophthalaldehyde trimethylolpropane diacetal, 5-tert-butylisophthalaldehyde trimethylolpropane diacetal, 2,4,5,6-Tetrafluoroisophthalaldehyde trimethylolpropane diacetal, Acetal, 4-Isopropylisophthalaldehyde trimethylolpropane diacetal, 4,6-Diisopropylisophthalaldehyde 2-bromo-5-tert-butylisophthalaldehyde trimethylolpropane diacetal, 4-phenylisophthalaldehyde trimethylolpropane diacetal, 5-phenylisophthalaldehyde trimethylolpropane diacetal, 4-phenyl-6-methylisophthalaldehyde trimethylolpropane diacetal, 4,5-diethyl-6-methylisophthalaldehyde trimethylolpropane diacetal, 5-hexylisophthalaldehyde trimethylolpropane diacetal, 4-Hexylisophthalaldehyde trimethylolpropane diacetal, 5-Butyloxyisophthalaldehyde trimethylolpropane diacetal, 2-Methoxyisophthalaldehyde trimethylolpropane diacetal, 4-Methoxyisophthalaldehyde trimethylolpropane diacetal, 5-Methoxyisophthalaldehyde trimethylolpropane diacetal, 2-Methoxy-4-methylisophthalaldehyde trimethylolpropane diacetal, 2-Methyl-4-methoxyisophthalaldehyde trimethylolpropane diacetal Tar, 2-methoxy-5-methylisophthalaldehyde trimethylolpropane diacetal, 4-methyl-6-methoxyisophthalaldehyde trimethylolpropane diacetal, 4,6-dimethoxyisophthalaldehyde trimethylolpropane diacetal, 2-methoxy-4-ethylisophthalaldehyde trimethylolpropane diacetal, 4,6-dimethyl-2-methoxyisophthalaldehyde trimethylolpropane diacetal, 2,4-dimethoxy-6-methylisophthalaldehyde trimethylolpropane diacetal, 2,Examples of suitable compounds include 4-dimethyl-6-methoxyisophthalaldehyde trimethylolpropane diacetal and 4-ethyl-5-methyl-6-methoxyisophthalaldehyde trimethylolpropane diacetal. Among these, preferred compounds include isophthalaldehyde trimethylolpropane diacetal, isophthalaldehyde trimethylolethane diacetal, 5-methylisophthalaldehyde trimethylolethane diacetal, 5-methylisophthalaldehyde trimethylolpropane diacetal, 4-methylisophthalaldehyde trimethylolpropane diacetal, and 4-methylisophthalaldehyde trimethylolethane diacetal. Particularly preferred compounds include isophthalaldehyde trimethylolpropane diacetal and isophthalaldehyde trimethylolethane diacetal.

[0029] The compound represented by general formula (1b) is as follows. [ka] [In the formula, R 1 and R 2 is the same as above.]

[0030] Preferred R in general formula (1b) 1 As for R in general formula (1a), 1 In addition, preferred R in general formula (1b) is the same as 2 As for R in general formula (1a), 2 is the same as

[0031] The compound represented by general formula (1b) may have isomers such as isomer (1b-A), isomer (1b-B), or isomer (1b-C) shown below. These isomers may exist alone or in mixture. [ka] [In the formula, R 1 and R 2 is the same as above.]

[0032] When the compound represented by general formula (1b) is a mixture of two or more isomers, the isomer ratio can be determined by the area percentage method through gas chromatography (GC) analysis using the method described in the Examples. Each isomer usually has its own unique peak in GC analysis. The content ratio of an isomer can be expressed as the percentage of the peak area of ​​each isomer relative to the total peak area of ​​the cyclic diol compound. The percentage ratio of each isomer can be taken as the isomer ratio. The cyclic diol compound of the present invention can also be subjected to trimethylsilylation of the hydroxyl groups using N,O-bis(trimethylsilyl)trifluoroacetamide or the like, followed by GC analysis.

[0033] The compound represented by general formula (1b) may have isomers such as isomer (1b-A), isomer (1b-B), or isomer (1b-C) as described above. Two or three isomer peaks were detected by GC analysis, which are considered to be isomer (1b-A), isomer (1b-B), or isomer (1b-C). The isomer ratio determined by GC analysis can be in the range of isomer (1b-A):isomer (1b-B):isomer (1b-C) = 10 to 1:10 to 1:1.

[0034] Specific examples of the compound represented by general formula (1b) include terephthalaldehyde trimethylolpropane diacetal, terephthalaldehyde trimethylolethane diacetal, 2-methylterephthalaldehyde trimethylolethane diacetal, 3-methylterephthalaldehyde trimethylolethane diacetal, 3-chloroterephthalaldehyde trimethylolethane diacetal, 2-chloro ... Trimethylolethane diacetal, 2-bromoterephthalaldehyde trimethylolethane diacetal, 3-bromoterephthalaldehyde trimethylolethane diacetal, 3,6-dimethylterephthalaldehyde trimethylolethane diacetal, 2,3-dimethylterephthalaldehyde trimethylolethane diacetal, 2,5-dichloroterephthalaldehyde trimethylolethane diacetal, 3,6-dichloroterephthalaldehyde Terephthalaldehyde trimethylolethane diacetal, 3,6-dibromoterephthalaldehyde trimethylolethane diacetal, 2,5-dibromoterephthalaldehyde trimethylolethane diacetal, 2-tert-butylterephthalaldehyde trimethylolethane diacetal, 2,3,5,6-tetrafluoroterephthalaldehyde trimethylolethane diacetal, 3-isopropylterephthalaldehyde trimethylol Ethane diacetal, 3,6-diisopropyl terephthalaldehyde trimethylol ethane diacetal, 2-bromo-5-tert-butyl terephthalaldehyde trimethylol ethane diacetal, 3-phenyl terephthalaldehyde trimethylol ethane diacetal, 2-phenyl terephthalaldehyde trimethylol ethane diacetal, 3-phenyl-6-methyl terephthalaldehyde trimethylol ethane diacetal, 3,5-Diethyl-6-methylterephthalaldehyde trimethylolethane diacetal, 2-Hexylterephthalaldehyde trimethylolethane diacetal, 3-Hexylterephthalaldehyde trimethylolethane diacetal, 2-Butyloxyterephthalaldehyde trimethylolethane diacetal, 3-Methoxyterephthalaldehyde trimethylolethane diacetal, 2-Methoxyterephthalaldehyde trimethylolethane diacetal, 2-Methoxy-3-methylterephthalaldehyde trimethylolethane diacetal, 2- Methyl-3-methoxyterephthalaldehyde trimethylolethane diacetal, 2-methoxy-5-methylterephthalaldehyde trimethylolethane diacetal, 3-methyl-6-methoxyterephthalaldehyde trimethylolethane diacetal, 3,6-dimethoxyterephthalaldehyde trimethylolethane diacetal, 2-methoxy-3-ethylterephthalaldehyde trimethylolethane diacetal, 3,6-dimethyl-2-methoxyterephthalaldehyde trimethylolethane diacetal, 2,3-dimethoxy-6-methyl Terephthalaldehyde trimethylolethane diacetal, 2,3-dimethyl-6-methoxyterephthalaldehyde trimethylolethane diacetal, 3-ethyl-5-methyl-6-methoxyterephthalaldehyde trimethylolethane diacetal, 2-methylterephthalaldehyde trimethylolpropane diacetal, 3-methylterephthalaldehyde trimethylolpropane diacetal, 3-chloroterephthalaldehyde trimethylolpropane diacetal, 2-chloroterephthalaldehyde trimethylolpropane diacetal, 2 -Bromoterephthalaldehyde trimethylolpropane diacetal, 3-Bromoterephthalaldehyde trimethylolpropane diacetal, 3,6-Dimethylterephthalaldehyde trimethylolpropane diacetal, 2,3-Dimethylterephthalaldehyde trimethylolpropane diacetal, 2,5-Dichloroterephthalaldehyde trimethylolpropane diacetal, 3,6-Dichloroterephthalaldehyde trimethylolpropane diacetal, 3,6-Dibromoterephthalaldehyde trimethylolpropane diacetal, 2,5-Dibromoterephthalaldehyde trimethylolpropane diacetal, 2-tert-butylterephthalaldehyde trimethylolpropane diacetal, 2,3,5,6-tetrafluoroterephthalaldehyde trimethylolpropane diacetal, 3-isopropylterephthalaldehyde trimethylolpropane diacetal, 3,6-diisopropylterephthalaldehyde trimethylolpropane diacetal, 2-bromo-5-tert-butylterephthalaldehyde trimethylolpropane diacetal olpropane diacetal, 3-phenyl terephthalaldehyde trimethylolpropane diacetal, 2-phenyl terephthalaldehyde trimethylolpropane diacetal, 3-phenyl-6-methyl terephthalaldehyde trimethylolpropane diacetal, 3,5-diethyl-6-methyl terephthalaldehyde trimethylolpropane diacetal, 2-hexyl terephthalaldehyde trimethylolpropane diacetal, 3-hexyl terephthalaldehyde trimethylol Terephthalaldehyde trimethylolpropane diacetal, 2-butyloxyterephthalaldehyde trimethylolpropane diacetal, 3-methoxyterephthalaldehyde trimethylolpropane diacetal, 2-methoxyterephthalaldehyde trimethylolpropane diacetal, 2-methoxy-3-methylterephthalaldehyde trimethylolpropane diacetal, 2-methyl-3-methoxyterephthalaldehyde trimethylolpropane diacetal, 3-methyl-6-methoxyterephthalaldehyde tri Methylolpropane diacetal, 3,6-dimethoxyterephthalaldehyde trimethylolpropane diacetal, 2-methoxy-3-ethylterephthalaldehyde trimethylolpropane diacetal, 2-methoxy-5-methylterephthalaldehyde trimethylolpropane diacetal, 3,6-dimethyl-2-methoxyterephthalaldehyde trimethylolpropane diacetal, 2,3-dimethoxy-6-methylterephthalaldehyde trimethylolpropane diacetal, 2,Examples of suitable compounds include 3-dimethyl-6-methoxyterephthalaldehyde trimethylolpropane diacetal and 3-ethyl-5-methyl-6-methoxyterephthalaldehyde trimethylolpropane diacetal. Among these, preferred compounds include terephthalaldehyde trimethylolpropane diacetal, terephthalaldehyde trimethylolethane diacetal, 2-methylterephthalaldehyde trimethylolethane diacetal, 2-methylterephthalaldehyde trimethylolpropane diacetal, 3-methylterephthalaldehyde trimethylolpropane diacetal, and 3-methylterephthalaldehyde trimethylolethane diacetal. Particularly preferred compounds include terephthalaldehyde trimethylolpropane diacetal and terephthalaldehyde trimethylolethane diacetal.

[0035] The compound represented by general formula (1c) is as follows. [ka] [In the formula, R 1 and R 2 is the same as above.]

[0036] Preferred R in general formula (1c) 1 As for R in general formula (1a), 1 In addition, preferred R in general formula (1c) is the same as 2 As for R in general formula (1a), 2 is the same as

[0037] The compound represented by general formula (1c) may have isomers such as isomer (1c-A), isomer (1c-B), or isomer (1c-C) shown below. These isomers may exist alone or in mixture. [ka] [In the formula, R 1 and R 2 is the same as above.]

[0038] When the compound represented by general formula (1c) is a mixture of two or more isomers, the isomer ratio can be determined by the area percentage method through gas chromatography (GC) analysis using the method described in the Examples. Each isomer usually has its own unique peak in GC analysis. The content ratio of an isomer can be expressed as the percentage of the peak area of ​​each isomer relative to the total peak area of ​​the cyclic diol compound. The percentage ratio of each isomer can be taken as the isomer ratio. The cyclic diol compound of the present invention can also be subjected to trimethylsilylation of the hydroxyl groups using N,O-bis(trimethylsilyl)trifluoroacetamide or the like, followed by GC analysis.

[0039] The compound represented by general formula (1c) may have isomers such as isomer (1c-A), isomer (1c-B), or isomer (1c-C) as described above. Two or three isomer peaks were detected by GC analysis, which are considered to be isomer (1c-A), isomer (1c-B), or isomer (1c-C). The isomer ratio determined by GC analysis can be in the range of isomer (1c-A):isomer (1c-B):isomer (1c-C) = 10 to 1:10 to 1:1.

[0040] Specific examples of the compound represented by general formula (1c) include orthophthalaldehyde trimethylolpropane diacetal, orthophthalaldehyde trimethylolethane diacetal, 3-methyl orthophthalaldehyde trimethylolethane diacetal, 4-methyl orthophthalaldehyde trimethylolethane diacetal, 3-chloro orthophthalaldehyde trimethylolethane diacetal, 3-bromo orthophthalaldehyde trimethylolethane diacetal, 3,6-dimethyl orthophthalaldehyde trimethylolethane diacetal, Acetal, 3,4-dimethyl orthophthalaldehyde trimethylolethane diacetal, 3,5-dimethyl orthophthalaldehyde trimethylolethane diacetal, 4,5-dimethyl orthophthalaldehyde trimethylolethane diacetal, 3,6-dichloro orthophthalaldehyde trimethylolethane diacetal, 3,6-dibromo orthophthalaldehyde trimethylolethane diacetal, 3,6-diethyl-4-methyl orthophthalaldehyde trimethylolethane diacetal, 3-hexyl orthophthalaldehyde trimethylol Trimethylolethane diacetal, 3-butyloxy orthophthalaldehyde trimethylolethane diacetal, 3-methoxy orthophthalaldehyde trimethylolethane diacetal, 3-methoxy-6-methyl orthophthalaldehyde trimethylolethane diacetal, 3-methyl-6-methoxy orthophthalaldehyde trimethylolethane diacetal, 3,6-dimethoxy orthophthalaldehyde trimethylolethane diacetal, 3-methoxy-6-ethyl orthophthalaldehyde trimethylolethane diacetal, 3,6-dimethyl-4- Methoxy orthophthalaldehyde trimethylolethane diacetal, 3,6-dimethoxy-4-methyl orthophthalaldehyde trimethylolethane diacetal, 3-methyl orthophthalaldehyde trimethylolpropane diacetal, 4-methyl orthophthalaldehyde trimethylolpropane diacetal, 3-chloro orthophthalaldehyde trimethylolpropane diacetal, 3-bromo orthophthalaldehyde trimethylolpropane diacetal, 3,6-dimethyl orthophthalaldehyde trimethylolpropane diacetal, 3,4-Dimethyl orthophthalaldehyde trimethylolpropane diacetal, 3,5-Dimethyl orthophthalaldehyde trimethylolpropane diacetal, 4,5-Dimethyl orthophthalaldehyde trimethylolpropane diacetal, 3,6-Dichloro orthophthalaldehyde trimethylolpropane diacetal, 3,6-Dibromo orthophthalaldehyde trimethylolpropane diacetal, 3,6-Diethyl-4-methyl orthophthalaldehyde trimethylolpropane diacetal, 3-Hexyl orthophthalaldehyde trimethylolpropane diacetal, 3-Butyloxy orthophthalaldehyde trimethylolpropane diacetal Examples of the phthalaldehyde include tar, 3-methoxy orthophthalaldehyde trimethylolpropane diacetal, 3-methoxy-6-methyl orthophthalaldehyde trimethylolpropane diacetal, 3-methyl-6-methoxy orthophthalaldehyde trimethylolpropane diacetal, 3,6-dimethoxy orthophthalaldehyde trimethylolpropane diacetal, 3-methoxy-6-ethyl orthophthalaldehyde trimethylolpropane diacetal, 3,6-dimethyl-4-methoxy orthophthalaldehyde trimethylolpropane diacetal, and 3,6-dimethoxy-4-methyl orthophthalaldehyde trimethylolpropane diacetal. Among these, preferred compounds include orthophthalaldehyde trimethylolpropane diacetal, orthophthalaldehyde trimethylolethane diacetal, 3-methyl orthophthalaldehyde trimethylolethane diacetal, 3-methyl orthophthalaldehyde trimethylolpropane diacetal, 4-methyl orthophthalaldehyde trimethylolpropane diacetal, and 4-methyl orthophthalaldehyde trimethylolethane diacetal, and particularly preferred compounds include orthophthalaldehyde trimethylolpropane diacetal and orthophthalaldehyde trimethylolethane diacetal.

[0041] The method for producing the compound represented by general formula (1) is not particularly limited, and for example, as shown in the following <Reaction Scheme 1>, the compound can be produced via a step of reacting a compound represented by the following general formula (3) with a compound represented by the following general formula (4) (acetalization reaction). [ka] [In the formula, R 1 and ring A is the same as above.] Specifically, the compound represented by general formula (1) can be produced by reacting a compound represented by general formula (3) with a compound represented by general formula (4) in the presence of an acid catalyst (acetalization reaction).

[0042] The reaction can usually be carried out in a solvent (e.g., toluene, etc.). The solvent can be heated to reflux and the reaction can be carried out while removing the generated water azeotropically with the solvent. The acidic catalyst is not particularly limited as long as it has catalytic action, and known acidic catalysts can be used. Examples include mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid; organic acids such as p-toluenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, trifluoroacetic acid, and trifluoromethanesulfonic acid; solid acids such as cation exchange resins, zeolites, silica alumina, and heteropolyacids (e.g., phosphotungstic acid, phosphomolybdic acid, etc.); and various Lewis acids. The amount of the compound represented by formula (4) used is usually about 0.5 to 3 moles, and preferably about 0.8 to 2 moles, per mole of the compound represented by formula (3).

[0043] Compounds represented by general formula (1a), compounds represented by general formula (1b), and compounds represented by general formula (1c), which are included in the compounds represented by general formula (1), can also be produced in the same manner as in <Reaction Scheme 1>. The compound represented by general formula (1a) can be produced by reacting a compound represented by the following general formula (3a) with a compound represented by the following general formula (4) in the presence of an acidic catalyst (acetalization reaction), as shown in the following <Reaction Scheme 2>. [ka] [In the formula, R 1 and R 2 is the same as above.]

[0044] The compound represented by general formula (1b) can be produced by reacting a compound represented by the following general formula (3b) with a compound represented by the following general formula (4) in the presence of an acid catalyst (acetalization reaction), as shown in the following <Reaction Scheme 3>. [ka] [In the formula, R 1 and R 2 is the same as above.]

[0045] The compound represented by general formula (1c) can be produced by reacting a compound represented by the following general formula (3c) with a compound represented by the following general formula (4) in the presence of an acid catalyst (acetalization reaction), as shown in the following <Reaction Scheme 4>. [ka] [In the formula, R 1 and R 2 is the same as above.]

[0046] The thermoplastic resin of one embodiment of the present invention is not particularly limited and may be a polyester resin, polycarbonate resin, polyester carbonate resin, epoxy resin, polyurethane resin, polyacrylic acid ester resin, polymethacrylic acid ester resin, or the like, but is preferably a polycarbonate resin or a polyester carbonate resin, more preferably contains a structural unit (A) represented by the following formula, and particularly preferably contains at least one of structural units (A1), (A2), and (A3) represented by the following formulas: [ka] [In the formula, R 1 and ring A has the same meaning as in the general formula (1). [ka] [In the formula, R 1 and R 2 has the same meaning as in the general formula (1a). [ka] [In the formula, R 1 and R 2 has the same meaning as in the general formula (1b). [ka] [In the formula, R 1 and R 2 has the same meaning as in the general formula (1c).

[0047] 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.

[0048] 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 formula (2). [ka] In equation (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 bis 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.

[0049] In formula (2), X represents a single bond or an optionally substituted fluorene group, preferably a single bond or an optionally substituted fluorene group having a total of 12 to 20 carbon atoms. In 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 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 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.

[0050] 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]

[0051] 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 formula (3). [ka] In equation (3), R c and R dare 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.

[0052] In formula (3), Y1 is a single bond, a fluorene group which may have a substituent, or any of the structural formulae represented by formulas (4) to (10) below, and is preferably a single bond or the structural formula represented by formula (4) below. [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.

[0053] In the above formula (3), A and B are each independently 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 above formula (3), p and q are each independently an integer of 0 to 4, and preferably 0 or 1. In addition, in the above formula (3), a and b are each independently 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.

[0054] 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]

[0055] 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.

[0056] 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.)

[0057] 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 molded article and can also cause odor, so it is preferable that the content of these compounds is as small as possible.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] <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 1.599 to 1.750, 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.

[0066] (2) Abbe number (ν) In one embodiment of the present invention, the Abbe number of the thermoplastic resin is preferably 25.0 to 33.0, 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.

[0067] (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.

[0068] (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.

[0069] <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.

[0070] [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 thereof may be used.

[0071] 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.

[0072] [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.

[0073] 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.

[0074] [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.

[0075] 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), R 1 and ring A 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.

[0076] 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.

[0077] <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, hard coat films, and the like. The resin composition of the present invention can be molded by a casting method with high flow, and is therefore 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. 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.

[0078] 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.

[0079] <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.

[0080] 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.

[0081] 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.

[0082] <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]

[0083] 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.

[0084] <Compound used> Isophthalaldehyde: Tokyo Chemical Industry Co., Ltd. Terephthalaldehyde: Manufactured by Tokyo Chemical Industry Co., Ltd. Ortho-phthalaldehyde: Manufactured by Tokyo Chemical Industry Co., Ltd. p-Toluenesulfonic acid monohydrate: manufactured by Nacalai Tesque, Inc. Trimethylolethane and trimethylolpropane: manufactured by Tokyo Chemical Industry Co., Ltd. Bisphenoxyethanolfluorene (BPEF): manufactured by Tokyo Chemical Industry Co., Ltd. Diphenyl carbonate: manufactured by Tokyo Chemical Industry Co., Ltd.

[0085] <Analysis by gas chromatography (GC)> The purity of the cyclic diol compound was determined by area percentage analysis by gas chromatography (GC) under the following conditions and method. (Sample preparation) 50 ml of methanol was added to 0.5 g of the cyclic diol compound and the mixture was shaken at room temperature to prepare a methanol solution of the cyclic diol compound, which was used as a sample for analysis.

[0086] [Measurement conditions] Equipment: Shimadzu GC-2020 Column: Agilent Technologies DB-1 30m x 0.25mm x 0.25µm Column temperature: 80°C (hold time 5 min) - heating rate 10°C / min - 320°C (hold time 5 min) Injection temperature / detector temperature: 300℃ / 325℃ Split ratio: 30 Column flow rate: 1.17 ml / min Purge flow rate 10.0 ml / min Detector: FID Carrier gas: Helium Gas linear velocity: 30cm / sec Injection volume: 1μl

[0087] <Melting point> The melting points of the cyclic diol compounds were measured using a differential scanning calorimeter (DSC6220) manufactured by SII NanoTechnology. 10.7 mg of the sample was placed in an aluminum pan manufactured by the same company, sealed, and heated from 30 to 200°C at a rate of 10°C / min under a nitrogen gas flow of 50 ml / min, and an endothermic peak was observed. The temperature at the top of the peak was taken as the melting point.

[0088] <Infrared absorption spectrum (IR spectrum)> The IR spectrum of the cyclic diol compound was measured by the ATR (attenuated total reflection) method using an infrared spectrometer (Spectrum 400 manufactured by PerkinElmer Japan Co., Ltd.).

[0089] <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).

[0090] <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

[0091] <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.

[0092] <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 The solution was filtered through a syringe filter (GL Sciences, GL Chromatodisc, pore size 0.45 μm) and then injected into the column. Eluent: tetrahydrofuran ·Eluent flow rate: 0.6mL / min Column temperature: 40℃

[0093] [Synthesis Example 1] A 500 mL four-neck flask equipped with a stirrer, thermometer, and Dean-Stark condenser was charged with 13.4 g (0.1 mol) of isophthalaldehyde, 0.67 g of p-toluenesulfonic acid monohydrate, 26.4 g (0.22 mol) of trimethylolethane, 60 ml of toluene, and 60 ml of N,N-dimethylformamide. The mixture was then heated and stirred under reflux for approximately 6 hours while removing the generated water. The reaction mixture was returned to room temperature and neutralized with 1 g of triethylamine. 59 ml of toluene was then distilled off under reduced pressure. 100 g of ion-exchanged water was then added and the mixture was cooled with ice water. The resulting crystals were filtered and rinsed twice with 50 ml of ion-exchanged water, followed by 100 ml of 60°C warm water. Finally, the mixture was rinsed twice with 50 ml of ion-exchanged water. The wet crystals were dried under reduced pressure at 80°C to obtain 26.7g (0.08mol) of isophthalaldehyde trimethylolethane diacetal with a purity of 99.7GC area%. The melting point of the crystals was 165.9°C.

[0094] The IR spectrum of the obtained isophthalaldehyde trimethylolethane diacetal was measured, and it was confirmed that the obtained compound was isophthalaldehyde trimethylolethane diacetal. IR(cm -1 ):653,690,714,803,891,962,982,1007,1024,1043,1100,1164,1378,2866,2955,3349

[0095] [Synthesis Example 2] A 500 mL four-neck flask equipped with a stirrer, thermometer, and Dean-Stark condenser was charged with 13.4 g (0.1 mol) of isophthalaldehyde, 0.67 g of p-toluenesulfonic acid monohydrate, 29.5 g (0.22 mol) of trimethylolpropane, 60 mL of toluene, and 60 mL of N,N-dimethylformamide. The mixture was then heated and stirred under reflux for approximately 8 hours while removing the generated water. The reaction mixture was returned to room temperature and neutralized with 1 g of triethylamine. 60 mL of toluene was then distilled off under reduced pressure. 150 g of ion-exchanged water was then added and the mixture was cooled with ice water. The resulting crystals were filtered and rinsed twice with 50 mL of ion-exchanged water, followed by 100 mL of 60°C warm water. Finally, the mixture was rinsed twice with 50 mL of ion-exchanged water. The wet crystals were dried under reduced pressure at 80°C to obtain isophthalaldehyde trimethylolpropane diacetal with a purity of 92.7 GC area%. The obtained crystals were dissolved by heating with 60 g of isopropyl alcohol, and 40 g of isopropyl alcohol was distilled off, followed by the addition of 100 ml of water. The precipitated crystals were filtered, rinsed twice with 50 ml of ion-exchanged water, and then dried under reduced pressure at 80°C to obtain 27.0 g (0.07 mol) of isophthalaldehyde trimethylolpropane diacetal with a purity of 98.5 GC area%. The melting point of the crystals was 95.5°C.

[0096] The IR spectrum of the obtained isophthalaldehyde trimethylolpropane diacetal was measured, and it was confirmed that the obtained compound was isophthalaldehyde trimethylolpropane diacetal. IR(cm -1):712,803,933,971,1030,1101,1165,1377,2859,2962,3374

[0097] [Synthesis Example 3] A 500 mL four-neck flask equipped with a stirrer, thermometer, and Dean-Stark condenser was charged with 13.4 g (0.1 mol) of terephthalaldehyde, 0.67 g of p-toluenesulfonic acid monohydrate, 26.4 g (0.22 mol) of trimethylolethane, 60 ml of toluene, and 60 ml of N,N-dimethylformamide. The mixture was heated and stirred under reflux conditions for approximately 6 hours while removing the generated water. The reaction mixture was returned to room temperature and neutralized with 1 g of triethylamine. 50 ml of toluene was distilled off under reduced pressure, after which 100 g of ion-exchanged water was added and the mixture was cooled with ice water. The resulting crystals were filtered and rinsed twice with 50 ml of ion-exchanged water, followed by two rinses with 50 ml of 60°C warm water. The wet crystals were dried under reduced pressure at 100°C to obtain 30.4g (0.09mol) of terephthalaldehyde trimethylolethane diacetal with a purity of 99.7GC area%. The melting point of the crystals was 247.3°C.

[0098] The IR spectrum of the obtained terephthalaldehyde trimethylolethane diacetal was measured, and it was confirmed that the obtained compound was terephthalaldehyde trimethylolethane diacetal. IR(cm -1 ):656,778,804,918,964,977,993,1016,1042,1094,1374,2844,2933,2959,3413

[0099] [Synthesis Example 4] A 500mL four-neck flask equipped with a stirrer, thermometer, and Dean-Stark condenser was charged with 13.4g (0.1mol) of terephthalaldehyde, 0.67g of p-toluenesulfonic acid monohydrate, 26.4g (0.2mol) of trimethylolpropane, 60ml of toluene, and 60ml of N,N-dimethylformamide. The mixture was then heated and stirred under reflux for approximately 10 hours while removing the resulting water. The reaction mixture was returned to room temperature and neutralized with 1g of triethylamine. 50ml of toluene was distilled off under reduced pressure, after which 150g of ion-exchanged water was added and the mixture was cooled with ice water. The resulting crystals were filtered and rinsed twice with 50ml of ion-exchanged water, followed by 50ml of 60°C warm water. The wet crystals were dried under reduced pressure at 100°C to obtain terephthalaldehyde trimethylolpropane diacetal with a purity of 96.9GC area%. The obtained crystals were dissolved by heating with 140 g of isopropyl alcohol, and after distilling off the isopropyl alcohol, the precipitated crystals were filtered off, rinsed twice with 50 ml of ion-exchanged water, and then dried under reduced pressure at 100 ° C to obtain 30.0 g (0.08 mol) of terephthalaldehyde trimethylolpropane diacetal with a purity of 97.0 GC area %. The melting point of the crystals was 187.2 ° C.

[0100] The IR spectrum of the obtained terephthalaldehyde trimethylolpropane diacetal was measured, and it was confirmed that the obtained compound was terephthalaldehyde trimethylolpropane diacetal. IR(cm -1 ):801,971,1000,1018,1099,1379,2855,2928,2967,3355

[0101] [Synthesis Example 5] A 1000 mL four-neck flask equipped with a stirrer, thermometer, and Dean-Stark condenser was charged with 40.2 g (0.3 mol) of ortho-phthalaldehyde, 1.0 g of p-toluenesulfonic acid monohydrate, 75.6 g (0.63 mol) of trimethylolethane, 180 mL of xylene, and 180 mL of N-methylpyrrolidone. The mixture was then heated and stirred under reflux conditions for approximately 4 hours while removing the generated water. After distilling off 170 mL of xylene under reduced pressure, the reaction mixture was returned to room temperature, neutralized with 25 mL of saturated sodium bicarbonate, and 400 g of ion-exchanged water was added. 100 mL of ethyl acetate was added, and the organic and aqueous layers were separated using a separatory funnel. This procedure of adding 100 mL of ethyl acetate to the separated aqueous layer and separating the organic and aqueous layers was repeated twice. The obtained organic layer was concentrated using a rotary evaporator to obtain 90.2 g (0.27 mol) of ortho-phthalaldehyde trimethylolethane diacetal with a purity of 99.2% (GC area percentage).

[0102] The IR spectrum of the obtained ortho-phthalaldehyde trimethylolethane diacetal was measured, and the obtained compound was confirmed to be ortho-phthalaldehyde trimethylolethane diacetal. IR(cm -1 ):663,698,760,920,948,969,1003,1021,1042,1082,1099,1203,1386,1455,2850,2955,3414

[0103] Example 1 As raw materials, 22.6470 g (0.0516 mol) of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF) represented by the following structural formula, 7.4982 g (0.0222 mol) of isophthalaldehyde trimethylolethane diacetal (hereinafter referred to as Compound 1) obtained in Synthesis Example 1, 16.2833 g (0.0760 mol) of diphenyl carbonate (DPC), and 0.6201 × 10 sodium hydrogen carbonate were used. -4 g(0.7381×10 -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 was started 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 60 minutes after the start of the reaction, the temperature was raised to 220°C. After 80 minutes, the pressure was reduced to 20.00 kPa over 10 minutes. The temperature was raised to 240°C, and the pressure was reduced to 0 kPa and maintained for 30 minutes. After that, nitrogen gas was introduced into the reaction system, and the pressure was returned to 101.3 kPa, and a polycarbonate resin was obtained. The resulting polycarbonate resin had a refractive index of 1.6125, an Abbe number of 25.98, a Tg of 142°C, and a polystyrene-equivalent weight average molecular weight (Mw) of 34459. The contents of the diol compounds used as raw materials and the physical properties of the resulting resin are shown in Table 1 below.

[0104] Example 2 As raw materials, 24.9709 g (0.0738 mol) of compound 1, 16.2833 g (0.0760 mol) of diphenyl carbonate (DPC), and 0.6201 × 10 sodium bicarbonate were used. -4 g(0.7381×10 -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 1.536, an Abbe number of 38.01, a Tg of 134°C, and a polystyrene-equivalent weight average molecular weight (Mw) of 34425. The contents of the diol compounds used as raw materials and the physical properties of the resulting resin are shown in Table 1 below.

[0105] Example 3 As raw materials, 20.9233 g (0.0477 mol) of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF) represented by the following structural formula, 6.9132 g (0.0204 mol) of terephthalaldehyde trimethylolethane diacetal (hereinafter referred to as Compound 2) obtained in Synthesis Example 3, 15.0581 g (0.0703 mol) of diphenyl carbonate (DPC), and 0.5725 × 10 sodium hydrogen carbonate were used.-4 g(0.6814×10 -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 was started 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. After 90 minutes, the pressure was reduced to 20.00 kPa over 10 minutes. The temperature was raised to 240°C, and the pressure was reduced to 0 kPa and maintained for 30 minutes. After that, nitrogen gas was introduced into the reaction system, and the pressure was returned to 101.3 kPa, and a polycarbonate resin was obtained. The refractive index of the obtained polycarbonate resin was 1.6095, the Abbe number was 26.09, the Tg was 153°C, and the weight average molecular weight (Mw) in terms of polystyrene was 16844. The contents of the diol compounds used as raw materials and the physical properties of the obtained resin are shown in Table 1 below.

[0106] Example 4 A polycarbonate resin was obtained in the same manner as in Example 3, except that the amounts were changed as shown in Table 1 below. The physical properties of the obtained resin are shown in Table 1 below.

[0107] (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.

[0108] (Comparative Example 2) As raw materials, 42.2300 g (0.0416 mol) of spiroglycol (3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane) (SPG), 30.6188 g (0.1429 mol) of DPC, and 1.1656 × 10 sodium bicarbonate were used. -4 g(1.3874×10 -6 A reaction was attempted in the same manner as in Example 1 except that 1,000 mol of methyl methyl ether was used instead, but crystallization occurred during the reaction, and no polycarbonate resin was obtained.

[0109] [ka]

[0110] [Table 1] *After preparing the sample solution, the presence of insoluble matter was confirmed visually. The sample was filtered through a syringe filter (GL Sciences, GL Chromatodisc, pore size 0.45 μm) before being injected into the column, so the data only covers the dissolved portion.

Claims

1. A thermoplastic resin containing a structural unit (A) derived from a monomer represented by the following general formula (1): 【Chemistry 1】 [In the formula, R １ are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, or a linear or branched alkyl group having 1 to 4 carbon atoms. Ring A represents a benzene ring optionally substituted with 1 to 4 groups selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, and a linear or branched alkyl group having 1 to 6 carbon atoms.] The monomer represented by the general formula (1) is a monomer represented by the following general formula (1a) or (1b): 【Chemistry 2】 [In the formula, R 2 s may be the same or different and each represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, or a linear or branched alkyl group having 1 to 6 carbon atoms; and R 1 is the same as defined above.] 【Transformation 3】 [In the formula, R 2 s may be the same or different and each represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a phenyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, or a linear or branched alkyl group having 1 to 6 carbon atoms; and R 1 is the same as defined above.] The thermoplastic resin comprises a structural unit (B) derived from a monomer represented by the following formula (2) and / or a structural unit (C) derived from a monomer represented by the following formula (3): 【Chemistry 4】 (In formula (2), R a and R b 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, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R h ; R h represents an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent; X represents a single bond or an optionally substituted fluorene group; A and B each independently represent an alkylene group having 1 to 5 carbon atoms which may have a substituent; m and n each independently represent an integer of 0 to 6; a and b each independently represent an integer of 0 to 10. 【Transformation 5】 (In 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; Y 1 represents 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): 【Transformation 6】 (In formulas (4) to (10), R 61 , R 62 , R 71 and R 72 each independently represent 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 bond together 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.

2. The thermoplastic resin according to claim 1 , which is a polycarbonate resin or a polyester carbonate resin.

3. R in the general formula (1) １ are the same or different and each represents a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, or a phenyl group. The thermoplastic resin according to claim 1 or 2.

4. In the general formula (1), R １ and are the same or different and each is a methyl group or an ethyl group.

5. The thermoplastic resin according to any one of claims 1 to 4, wherein in the general formula (1), ring A is a benzene ring optionally substituted with 1 to 4 groups selected from the group consisting of linear or branched alkoxy groups having 1 to 6 carbon atoms and linear or branched alkyl groups having 1 to 6 carbon atoms.

6. In the general formula (1), R １ is a methyl group or an ethyl group, and ring A is a benzene ring optionally substituted with 1 to 4 groups selected from the group consisting of methyl groups and ethyl groups. The thermoplastic resin according to any one of claims 1 to 5.

7. The thermoplastic resin according to any one of claims 1 to 6, wherein in the formulas (2) and (3), A and B each independently represent an alkylene group having 2 or 3 carbon atoms.

8. The thermoplastic resin according to any one of claims 1 to 7, wherein the thermoplastic resin contains at least a structural unit derived from any one of BPEF, BNE, BNEF, and DPBHBNA.

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: 【Transformation 7】 (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. An optical member comprising the thermoplastic resin according to claim 1 .

15. An optical lens comprising the thermoplastic resin of any one of claims 1 to 13.

16. An optical film comprising the thermoplastic resin according to claim 1 .

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