Thermoplastic resin, molded body, and optical member

Abstract

The present invention provides: a thermoplastic resin which comprises a structural unit that is represented by general formula (P1); a molded body which is obtained by molding this thermoplastic resin; and an optical member which comprises this molded body. In the formula, R represents an aliphatic hydrocarbon group. Two moieties among R1 to R10 each represent a divalent substituent that is represented by general formula (P2), and the remaining eight moieties each represent a hydrogen atom or a monovalent substituent. Formula (P2): *-O-L-O-LP-# In the formula, L represents an alkylene group having 2 to 6 carbon atoms, LP represents a single bond or a carbonyl group, * denotes an atomic bond to the benzene ring in formula (P1), and # denotes an atomic bond.

Description

Thermoplastic resin, molded body, and optical member

[0001] The present invention relates to a thermoplastic resin, a molded article, and an optical member.

[0002] Glass materials have traditionally been used for optical components in imaging modules such as cameras, video cameras, camera-equipped mobile phones, videophones, and camera-equipped door phones. Glass materials have been favorably used because they have a variety of optical properties and excellent environmental resistance, but they have drawbacks such as difficulty in reducing their weight and size, and poor processability and productivity. In contrast, cured resins or molded resins can be mass-produced and have excellent processability, and therefore have recently come to be used for various optical components.

[0003] As imaging modules become smaller, the optical components used in the imaging modules also need to be smaller. However, as optical components become smaller, problems with chromatic aberration arise. Therefore, in optical components using cured resins or molded resins, attempts have been made to correct chromatic aberration by adjusting the dispersion characteristics of the refractive index using monomers or additives that constitute the polymers of the cured resins or molded resins.

[0004] For example, Patent Document 1 describes a polycarbonate resin having structural units derived from a compound containing a polycyclic fused ring containing a nitrogen atom as an atom constituting the fused ring, and describes that this polycarbonate resin has a low Abbe number (νd) as a wavelength dispersion characteristic of refractive index, or a high θg,F value, which is a partial dispersion ratio as an anomalous partial dispersion. Meanwhile, because optical components of imaging modules are used in light-exposed environments such as outdoors, it is also important to suppress coloration (i.e., a decrease in transmittance) of optical components that occurs when used or stored for long periods in light-exposed environments such as outdoors (hereinafter also referred to as "lightfastness"). However, polymers having a polycyclic fused ring structure containing a nitrogen atom as an atom constituting the fused ring are known to be prone to coloration. Therefore, there is a need for the development of new polymers that exhibit both refractive index dispersion characteristics and lightfastness. Meanwhile, 1,3-diphenyl-2-propen-1-one and its hydroxy derivative, a chalcone compound, are known as dyes that exhibit orange-yellow or orange-red colors. As examples of polymers using such chalcone compounds as raw material monomers, Patent Document 2 describes a polyurethane having a diol-derived structural unit in which a cyano group is substituted at the carbonyl α-position of the chalcone skeleton, Patent Document 3 describes a cured product of a liquid crystal composition containing a (meth)acrylic compound in which the carbonyl α-position of the chalcone skeleton is a hydrogen atom, and Patent Document 4 describes a polycarbonate having a diol-derived structural unit in which the carbonyl α-position of the chalcone skeleton is a hydrogen atom.

[0005] International Publication No. 2017 / 146022 Korean Patent Publication No. 2021-0043115 JP 2020-055775 A U.S. Patent No. 3,043,802

[0006] Optical components requiring refractive index dispersion characteristics may also be required to have optical transparency. As a result of studies by the present inventors, the thermoplastic resins having structural units derived from chalcone compounds described in Patent Documents 2 to 4 above exhibit high partial dispersion ratios (θg,F values) and high anomalous partial dispersion of refractive index, but they also exhibit coloration and require improvement in terms of light resistance. An object of the present invention is to provide a thermoplastic resin that exhibits almost no coloration, high anomalous partial dispersion, and excellent light resistance. Another object of the present invention is to provide a molded product obtained by molding this thermoplastic resin, and an optical component including this molded product.

[0007] That is, the above-mentioned object of the present invention has been achieved by the following means: <1> A thermoplastic resin containing a structural unit represented by the following general formula (P1). In the above formula, R represents an aliphatic hydrocarbon group. １ ~R １０ Two of the groups represent a divalent substituent represented by the following general formula (P2), and the remaining eight groups represent a hydrogen atom or a monovalent substituent. In the above formula, L represents an alkylene group having 2 to 6 carbon atoms, and L Ｐ represents a single bond or a carbonyl group. * represents a bond to the benzene ring in formula (P1), and # represents a bond. <2> The thermoplastic resin according to <1>, which contains a structural unit represented by the following general formula (P1-1) or (P1-2): In the above formula, R represents an aliphatic hydrocarbon group, and R １ , R ２ and R ４ ~R １０ represents a hydrogen atom or a monovalent substituent, L １ and L ２ represents an alkylene group having 2 to 6 carbon atoms, and L Ｐ１ and L Ｐ２represents a single bond or a carbonyl group. # represents a bond. <3> The thermoplastic resin according to <1> or <2>, wherein R represents an alkyl group having 1 to 10 carbon atoms. <4> The thermoplastic resin according to any one of <1> to <3>, which is a polyester resin or a polycarbonate resin. <5> A molded product of the thermoplastic resin according to any one of <1> to <4>. <6> An optical member comprising the molded product according to <5>.

[0008] In the present invention, when there are multiple substituents or linking groups, etc., represented by a specific symbol or formula (hereinafter referred to as substituents, etc.), or when multiple substituents, etc. are specified simultaneously, unless otherwise specified, the respective substituents, etc. may be the same or different from each other (regardless of the presence or absence of the expression "independently," the respective substituents, etc. may be the same or different from each other). The same applies to the specification of the number of substituents, etc. Furthermore, in the present invention, when there are multiple structural units represented by a specific general formula, unless otherwise specified, the respective structural units may be the same or different from each other (regardless of the presence or absence of the expression "independently," the respective structural units may be the same or different from each other). Furthermore, when multiple substituents, etc., are adjacent to each other (especially when adjacent), unless otherwise specified, they may be linked to each other to form a ring. Furthermore, unless otherwise specified, rings, such as alicyclic rings, aromatic rings, and heterocyclic rings, may be further condensed to form a condensed ring. In the present invention, unless otherwise specified, with respect to double bonds, when E-type and Z-type double bonds exist in a molecule, either one may be present, or a mixture thereof may be present. For example, in the structural unit represented by general formula (P1) and the structural units represented by any of general formulae (P1-1) to (P1-5), the wavy line in the general formula indicates that the structural unit may be either an E-configuration or a Z-configuration, or may be a mixture thereof. Furthermore, in the present invention, unless otherwise specified, when a compound has one or more asymmetric carbon atoms, the stereochemistry of such asymmetric carbon atoms can each independently be either an (R) or an (S) configuration. As a result, the compound (including oligomers and polymers; the same applies hereinafter) may be a mixture of stereoisomers such as optical isomers or diastereoisomers, or may be a racemate. In the present invention, unless otherwise specified, when a compound has a repeating structure, the repeating number of the repeating structure may all be the same, or may be a mixture of compounds with different repeating numbers. Furthermore, in the present invention, the representation of a compound includes compounds in which the structure has been partially modified, as long as the effects of the present invention are not impaired.Furthermore, for compounds that are not specified as substituted or unsubstituted, it means that they may have any substituent within the scope that does not impair the effects of the present invention. Examples of optional substituents that the compounds may have include alkyl groups, alkoxy groups, fluoro groups, chloro groups, and cyano groups. Here, the alkyl groups and alkoxy groups may have a substituent, and preferred examples of the optional substituents include fluoro groups and chloro groups. For substituents (similar to linking groups and rings) that are not specified as substituted or unsubstituted in the present invention, it means that the group may have any substituent within the scope that does not impair the desired effects. For example, when the term "alkyl group" is used, it includes both unsubstituted alkyl groups and substituted alkyl groups. In the present invention, when the number of carbon atoms of a certain group is specified, this carbon number means the number of carbon atoms of the entire group unless otherwise specified in the present invention or this specification. In other words, if this group further has a substituent, it means the total number of carbon atoms including the substituent. The carbon number may also be expressed using C, for example, C for a carbon number of 6 or more. ６ The above refers to carbon numbers 1 to 4 as C １－４ It is sometimes written as:

[0009] In the present invention, a numerical range expressed using "to" means a range including the numerical values ​​before and after "to" as the lower and upper limits. In the thermoplastic resin of the present invention, each component (the thermoplastic polymer of the present invention and any additives that may be optionally contained) may be used alone or in combination of two or more. This also applies to each component in a molded product of the thermoplastic resin of the present invention and each component in an optical member.

[0010] In the present invention, "(meth)acrylate" refers to either or both of acrylate and methacrylate, and "(meth)acryloyl" refers to either or both of acryloyl and methacryloyl. The term "monomer" in the present invention is distinguished from oligomers and polymers and refers to a compound having a mass average molecular weight of 1,000 or less.

[0011] In the present invention, the term "aliphatic hydrocarbon group" refers to a chain aliphatic hydrocarbon group or an alicyclic hydrocarbon group. The chain aliphatic hydrocarbon group refers to an alkyl group obtained by removing one arbitrary hydrogen atom from a linear or branched alkane, an alkenyl group obtained by removing one arbitrary hydrogen atom from a linear or branched alkene, or an alkynyl group obtained by removing one arbitrary hydrogen atom from a linear or branched alkyne. In the present invention, the chain aliphatic hydrocarbon group is preferably an alkyl group obtained by removing one arbitrary hydrogen atom from a linear or branched alkane. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a 1-methylbutyl group, a 3-methylbutyl group, a hexyl group, a 1-methylpentyl group, a 4-methylpentyl group, a heptyl group, a 1-methylhexyl group, a 5-methylhexyl group, a 2-ethylhexyl group, an octyl group, a 1-methylheptyl group, a nonyl group, a 1-methyloctyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an eicosyl group. In the present invention, the aliphatic hydrocarbon group (unsubstituted) is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably an alkyl group having 1 to 4 carbon atoms, particularly preferably a methyl group or an ethyl group, and most preferably a methyl group.

[0012] In the present invention, the term "alkyl group" refers to a linear or branched alkyl group. Examples of the alkyl group include those listed above. Similarly, the alkyl group in a group containing an alkyl group (such as an alkoxy group) also refers to a linear or branched alkyl group, and examples of the alkyl group include those listed above. Furthermore, in the present invention, examples of the alkylene group include groups obtained by removing any one hydrogen atom from the above alkyl groups, and may be either linear or branched.

[0013] The thermoplastic resin of the present invention is almost free from coloration, has high anomalous partial dispersion, and is excellent in light resistance. Furthermore, a molded article obtained by molding the thermoplastic resin of the present invention and an optical component including this molded article are almost free from coloration, have high anomalous partial dispersion, and are excellent in light resistance.

[0014] The thermoplastic resin of the present invention is a thermoplastic resin containing a structural unit (structural unit (P1)) represented by the general formula (P1) described below, and exhibits little coloration, high anomalous partial dispersion, and excellent light resistance. Specifically, the thermoplastic resin of the present invention contains a structural unit having two divalent substituents represented by the general formula (P2) on the two benzene rings constituting the chalcone skeleton, and having an aliphatic hydrocarbon group as the substituent R at the carbonyl α-position of the chalcone compound (hence, the thermoplastic resin of the present invention is a thermoplastic resin having an α-substituted chalcone skeleton-containing structural unit). By containing such a unique structural unit, the thermoplastic resin of the present invention can shift the chalcone skeleton-derived light absorption near 430 nm to shorter wavelengths, as exhibited by polyurethanes containing diol-derived structural units having a cyano group at the carbonyl α-position as described in Patent Document 2, and (meth)acrylic polymers or polycarbonates containing diol-derived structural units with an unsubstituted (hydrogen atom) carbonyl α-position as described in Patent Documents 3 and 4, respectively. This thermoplastic resin exhibits little coloration, maintains anomalous partial dispersion, and exhibits excellent light resistance. Therefore, the thermoplastic resin of the present invention can be suitably used as a material for optical components such as optical sheets, optical films, and optical lenses, which require optical transparency, anomalous partial dispersion, and light resistance.

[0015] The present invention will be described in detail below. The following description of the components may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments.

[0016] <Thermoplastic Resin> The thermoplastic resin of the present invention may be composed of a polymer that contains the structural unit (P1) and exhibits thermoplasticity (hereinafter referred to as the "thermoplastic polymer of the present invention"), or may be in the form of a composition in which the thermoplastic polymer of the present invention is blended with the additives described below. The thermoplastic polymer of the present invention will be described in detail below.

[0017] [Thermoplastic Polymer] The thermoplastic polymer of the present invention contains the following structural unit (P1).

[0018] (Structural unit (P1))

[0019] In the above formula, R represents an aliphatic hydrocarbon group. １ ~R １０ Two of these represent a divalent substituent represented by general formula (P2) described below, and the remaining eight represent a hydrogen atom or a monovalent substituent.

[0020] The substituents and the like in formula (P1) will be described in detail below.

[0021] (1) The aliphatic hydrocarbon group represented by R is preferably a chain aliphatic hydrocarbon group, more preferably an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, still more preferably an alkyl group having 1 to 10 carbon atoms, still more preferably an alkyl group having 1 to 4 carbon atoms, still more preferably a methyl group or an ethyl group, and particularly preferably a methyl group.

[0022] (2) R １ ~R １０ R １ ~R １０ Two of the groups represent a divalent substituent represented by the following general formula (P2), and the remaining eight groups represent a hydrogen atom or a monovalent substituent.

[0023]

[0024] In the above formula, L represents an alkylene group having 2 to 6 carbon atoms, and L Ｐ represents a single bond or a carbonyl group (>C=O). * represents a bond to the benzene ring in formula (P1), and # represents a bond.

[0025] L is an alkylene group having 2 to 6 carbon atoms, preferably an alkylene group having 2 to 4 carbon atoms, and more preferably an ethylene group. Ｐ represents a single bond or a carbonyl group. Ｐ As a combination of the above, it is preferable that one is a single bond and the other is a carbonyl group, or that both are single bonds.

[0026] R １ ~R １０ Among these, eight other than the divalent substituent represented by the general formula (P2) (in the present invention, they may also be simply referred to as "the remaining eight") represent a hydrogen atom or a monovalent substituent. １ ~R １０ The remaining eight groups may have monovalent substituents, and any substituent may be used as long as the effects of the present invention are not impaired. Examples include alkyl groups, alkoxy groups, fluoro groups, chloro groups, and cyano groups, with alkyl groups, alkoxy groups, fluoro groups, and chloro groups being preferred. Here, the alkyl groups and alkoxy groups may have a substituent, and preferred examples of the substituents that may be had are fluoro groups and chloro groups. R １ ~R １０ Of the remaining eight groups, the number of groups that are monovalent substituents is preferably four or less, more preferably two or less, and even more preferably one or less. １ ~R １０ It is also preferred that all of the remaining eight are hydrogen atoms.

[0027] From the viewpoint of further enhancing the anomalous partial dispersibility, the structural unit represented by the general formula (P1) is preferably a structural unit represented by any one of the following general formulae (P1-1) to (P1-5), and more preferably a structural unit represented by the following general formula (P1-1) or (P1-2).

[0028]

[0029] In the above formula, R represents an aliphatic hydrocarbon group, and R １ ~R １０ represents a hydrogen atom or a monovalent substituent, L１ and L ２ represents an alkylene group having 2 to 6 carbon atoms, and L Ｐ１ and L Ｐ２ indicates a single bond or a carbonyl group. # indicates a bond.

[0030] R has the same meaning as R in the general formula (P1). １ ~R １０ The monovalent substituent that can be taken by is the same as the above R １ ~R １０ The remaining eight are the same as the possible monovalent substituents. ２ , R ４ , R ５ , R ９ and R １０ is preferably a hydrogen atom. ２ , R ４ ~R ７ , R ９ and R １０ is preferably a hydrogen atom. １ , R ３ ~R ７ , R ９ and R １０ is preferably a hydrogen atom. ２ , R ４ ~R ７ , R ９ and R １０ is preferably a hydrogen atom. １ , R ４ ~R １０ is preferably a hydrogen atom. １ ~R １０ is preferably a hydrogen atom.

[0031] L １ and L ２ represents an alkylene group having 2 to 6 carbon atoms, preferably an alkylene group having 2 to 4 carbon atoms, and more preferably an ethylene group. Ｐ１ and L Ｐ２ represents a single bond or a carbonyl group. Ｐ１ and L Ｐ２As a combination of the above, it is preferable that one is a single bond and the other is a carbonyl group, or that both are single bonds.

[0032] The thermoplastic polymer of the present invention preferably contains a structural unit represented by any one of the above general formulas (P1-1) to (P1-5), and more preferably contains a structural unit represented by the above general formula (P1-1) or (P1-2). In these preferred or more preferred embodiments, the structural unit contained in the thermoplastic polymer of the present invention may be one type or two or more types. For example, "containing a structural unit represented by the above general formula (P1-1) or (P1-2)" means containing only one structural unit or both of the structural unit represented by the above general formula (P1-1) and the structural unit represented by the above general formula (P1-2), and it is preferable to contain only one structural unit.

[0033] Specific examples of the structural unit represented by general formula (P1) of the present invention are listed below, but are not limited to these. In the following table, Me stands for a methyl group, Et stands for an ethyl group, isoPr stands for an isopropyl group, n-Pr stands for an n-propyl group, OMe stands for a methoxy group, and CF ３ is a trifluoromethyl group, H is a hydrogen atom, F is a fluoro group, Cl is a chloro group, C ２ H ４ represents an ethylene group. Ｐ１ and L Ｐ２ is the above-mentioned L Ｐ１ and L Ｐ２ "-" indicates that the corresponding group does not exist.

[0034]

[0035]

[0036] The thermoplastic polymer of the present invention is not limited as long as it is a thermoplastic polymer containing the structural unit (P1), and examples thereof include polyester, polycarbonate, and polyurethane, with polyester and polycarbonate being more preferred. That is, examples of the thermoplastic resin of the present invention include polyester resin, polycarbonate resin, and polyurethane resin, with polyester resin and polycarbonate resin being more preferred. In the present invention, unless otherwise specified, polyester, polycarbonate, and polyurethane refer to thermoplastic polymers, and polyester resin, polycarbonate resin, and polyurethane resin refer to thermoplastic resins.

[0037] The structural unit (P1) in the thermoplastic polymer of the present invention is L in the general formula (P2). Ｐ Specifically, when the thermoplastic polymer of the present invention is a polyester or polyurethane, L in the structural unit (P1) is incorporated into the polymer as a structural unit containing a structure derived from a diol compound in which L is replaced with a hydrogen atom (hereinafter referred to as diol compound (P1)). Ｐ are both single bonds, and this structure is a structural unit derived from the diol compound (P1). On the other hand, when the thermoplastic polymer of the present invention is a polycarbonate, L in the structural unit (P1) Ｐ One of the groups is a single bond and the other is a carbonyl group. This structure is a combination of a structure derived from the diol compound (P1) and a carbonyl group (L) introduced by the phosgene method or transesterification method described later. Ｐ )

[0038] The diol compound (P1), i.e., a diol compound having an α-substituted chalcone skeleton, can be synthesized, for example, by condensing a benzaldehyde compound with an aromatic ketone compound, as shown below, and reference can be made to the synthesis method described in Bing-zhao Ren et al., Medicinal Chemistry Research, 2017, Volume 26, Issue 9, pp. 1871-1883.

[0039]

[0040] In the above scheme, R and R １ ~R １０ represents R and R in the general formula (P1). １ ~R １０ In the formula (P2), L Ｐ In other words, the diol compound (P1) has the same meaning as the benzaldehyde compound and / or aromatic ketone compound except that R is replaced with a hydrogen atom. １ ~R １０ Two of the substituents are represented by the general formula (P2) (wherein L Ｐ In the above scheme, the benzaldehyde compound and / or aromatic ketone compound can be synthesized by using a compound (raw material) having a group in which R is replaced with a hydrogen atom. １ ~R １０ Two of the substituents are represented by the general formula (P2) (wherein L Ｐ A precursor compound having an α-substituted chalcone skeleton is synthesized using a compound (raw material) having a group that serves as a precursor of the substituent represented by general formula (P2) (where L is replaced with a hydrogen atom), and then subsequent reactions such as deprotection, esterification, and etherification are carried out to obtain a substituent represented by general formula (P2) (where L is replaced with a hydrogen atom). Ｐ is replaced with a hydrogen atom) is a group that serves as a precursor of a substituent represented by general formula (P2) (wherein L Ｐ The diol compound (P1) can be produced by a conventional method, as described above, with reference to the methods described in the Examples below.

[0041] (Structural Unit (PX) Derived from Other Diol Compounds) The thermoplastic polymer of the present invention may contain, in addition to the structural unit (P1) described above, a structural unit derived from a diol compound different from the diol compound (P1) (hereinafter referred to as "structural unit (PX) derived from other diol compounds"). (1) Diol Compound (PX1) Examples of diol compounds used for the structural unit (PX) derived from other diol compounds include diol compounds (PX1) having a fluorene skeleton, such as 9,9-bis(hydroxyaryl)fluorene compounds and 9,9-bis[hydroxy(poly)alkoxyaryl]fluorene compounds.

[0042] In the present invention, unless otherwise specified, the term "(poly)alkoxy" is used to mean both an alkoxy group and a polyalkoxy group (meaning a poly(alkyleneoxy) group).

[0043] Examples of the 9,9-bis(hydroxyaryl)fluorene compound include a 9,9-bis(hydroxyphenyl)fluorene compound, a 9,9-bis(alkyl-hydroxyphenyl)fluorene compound, a 9,9-bis(aryl-hydroxyphenyl)fluorene compound, and a 9,9-bis(hydroxynaphthyl)fluorene compound.

[0044] Examples of the 9,9-bis(hydroxyphenyl)fluorene compound include 9,9-bis(4-hydroxyphenyl)fluorene.

[0045] Examples of the 9,9-bis(alkyl-hydroxyphenyl)fluorene compound include 9,9-bis[(mono- or di-)C]fluorene such as 9,9-bis(4-hydroxy-3-methylphenyl)fluorene and 9,9-bis(4-hydroxy-3,5-dimethylphenyl)fluorene. １－４ alkyl-hydroxyphenyl]fluorene compounds.

[0046] Examples of the 9,9-bis(aryl-hydroxyphenyl)fluorene compound include 9,9-bis(C ６－１０aryl-hydroxyphenyl)fluorene compounds.

[0047] Examples of the 9,9-bis(hydroxynaphthyl)fluorene compound include 9,9-bis(6-hydroxy-2-naphthyl)fluorene and 9,9-bis(5-hydroxy-1-naphthyl)fluorene.

[0048] Examples of the 9,9-bis[hydroxy(poly)alkoxyaryl]fluorene compound include a 9,9-bis[hydroxy(poly)alkoxyphenyl]fluorene compound, a 9,9-bis[alkyl-hydroxy(poly)alkoxyphenyl]fluorene compound, a 9,9-bis[aryl-hydroxy(poly)alkoxyphenyl]fluorene compound, and a 9,9-bis[hydroxy(poly)alkoxynaphthyl]fluorene compound.

[0049] Examples of the 9,9-bis[hydroxy(poly)alkoxyphenyl]fluorene compound include 9,9-bis[hydroxy(mono- to deca)C such as 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene, 9,9-bis[4-(2-hydroxypropoxy)phenyl]fluorene, and 9,9-bis[4-(2-(2-hydroxyethoxy)ethoxy)phenyl]fluorene. ２－４ alkoxy-phenyl]fluorene compounds and the like.

[0050] Examples of the 9,9-bis[alkyl-hydroxy(poly)alkoxyphenyl]fluorene compounds include 9,9-bis[(mono or di)C such as 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxypropoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-(2-hydroxyethoxy)ethoxy)-3-methylphenyl]fluorene, and 9,9-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]fluorene. １－４ Alkyl-hydroxy (mono-deca) C ２－４ alkoxy-phenyl]fluorene compounds and the like.

[0051] Examples of the 9,9-bis[aryl-hydroxy(poly)alkoxyphenyl]fluorene compound include 9,9-bis[C such as 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene, 9,9-bis(4-(2-hydroxypropoxy)-3-phenylphenyl)fluorene, and 9,9-bis[4-(2-(2-hydroxyethoxy)ethoxy)-3-phenylphenyl]fluorene. ６－１０ Aryl-hydroxy (mono-deca) C ２－４ alkoxy-phenyl]fluorene compounds and the like.

[0052] Examples of the 9,9-bis[hydroxy(poly)alkoxynaphthyl]fluorene compound include 9,9-bis[hydroxy(mono- to deca)C such as 9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]fluorene, 9,9-bis[6-(2-hydroxypropoxy)-2-naphthyl]fluorene, 9,9-bis[6-(2-(2-hydroxyethoxy)ethoxy)-2-naphthyl]fluorene, and 9,9-bis[5-(2-hydroxyethoxy)-1-naphthyl]fluorene. ２－４ Alkoxy-naphthyl]fluorene compounds and the like.

[0053] (2) Diol Compound (PX2) The diol compound used for the structural unit (PX) derived from other diol compounds is a diol compound different from the above diol compound (PX1), for example, an aliphatic diol compound (PX2) such as an alkanediol compound (also referred to as an alkylene glycol compound) or a polyalkanediol compound (also referred to as a polyalkylene glycol compound). Note that this diol compound (PX2) does not have a fluorene skeleton.

[0054] Examples of the alkanediol compound include linear or branched C alkanediols such as ethylene glycol, propylene glycol, trimethylene glycol, 1,2-butanediol, 1,3-butanediol, tetramethylene glycol (or 1,4-butanediol), 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,8-octanediol, and 1,10-decanediol. ２－１２ Alkylene glycol compounds are exemplified.

[0055] Examples of the polyalkylene glycol compound include di- to deca-linear or branched C alkylene glycols such as diethylene glycol, dipropylene glycol, and triethylene glycol. ２－１２ Alkylene glycol compounds include di- to hexa-C ２－６ Alkylene glycol compounds are preferred, and di- to tetra-C ２－４ Alkylene glycol compounds are more preferred.

[0056] Among these diol compounds (PX2), alkylene glycols are preferred in terms of their effect on coloration and light resistance, and linear or branched C alkylene glycols such as ethylene glycol and 1,5-pentanediol are preferred. ２－６ Alkylene glycol compounds are more preferred, and C 111 compounds such as ethylene glycol, propylene glycol, and 1,4-butanediol are preferred. ２－４ Alkylene glycol compounds are more preferred, and C alkylene glycol compounds such as ethylene glycol and propylene glycol are preferred. ２－３ Alkylene glycol compounds are particularly preferred, and ethylene glycol is particularly preferred.

[0057] (3) Diol compound (PX3) As the diol compound used for the structural unit (PX) derived from other diol compounds, as the diol compound different from any of the above-mentioned diol compounds (PX1) and (PX2), for example, alicyclic diol compounds, aromatic diol compounds, and the diol compound (PX3) such as alkylene oxide (alkylene carbonate or haloalkanol) adduct of these diol compounds can be enumerated.It should be noted that this diol compound (PX3) does not have a fluorene skeleton.

[0058] The alicyclic diol compound is a diol compound having an alicyclic ring, and examples thereof include cycloalkanediol compounds such as cyclohexanediol; bis(hydroxyalkyl)cycloalkane compounds such as cyclohexanedimethanol; and hydrogenated aromatic diol compounds exemplified below, such as hydrogenated bisphenol A.

[0059] The aromatic diol compound is a diol compound having an aromatic ring, and examples thereof include dihydroxyarene compounds such as hydroquinone and resorcinol; aromatic aliphatic diol compounds such as benzenedimethanol; bisphenol compounds such as bisphenol A, bisphenol F, bisphenol AD, bisphenol C, bisphenol G, and bisphenol S; and biphenol compounds such as p,p'-biphenol.

[0060] Examples of alkylene oxide adducts (corresponding alkylene carbonate adducts or haloalkanol adducts) of these alicyclic diol compounds or aromatic diol compounds include C ２－４ alkylene oxide adducts, such as ethylene oxide adducts and propylene oxide adducts ２－３ Alkylene oxide adducts are preferred. The number of moles added is not particularly limited. Specific examples include adducts in which 2 to 10 moles of ethylene oxide are added to 1 mole of a diol such as bisphenol A.

[0061] (Polycarbonate) The polycarbonate may be a polycarbonate having a carbonate structural unit represented by the structural unit (P1) described above, and may have a carbonate structural unit having a structure different from that of the carbonate structural unit represented by the structural unit (P1) described above. Examples of carbonate structural units having a structure different from that of the carbonate structural unit represented by the structural unit (P1) described above include structural units comprising a structure derived from any of the diol compounds (PX1) to (PX3) described above and a carbonyl group. The proportion of the structural unit (P1) among all the structural units constituting the polycarbonate may be within a range that does not impair the effects of the present invention, and may be, for example, 10 to 100 mol%, preferably 20 to 100 mol%, and more preferably 30 to 100 mol%. The proportion of structural units comprising a structure derived from any one of the diol compounds (PX1) to (PX3) and a carbonyl group in all structural units constituting the polycarbonate may be within a range that does not impair the effects of the present invention, and can be, for example, 90 mol% or less, preferably 80 mol% or less, and more preferably 70 mol% or less.

[0062] (Polyester) The polyester may be any polyester having a structural unit derived from a diol compound represented by the structural unit (P1) described above and a structural unit derived from a dicarboxylic acid compound, and may have a structural unit derived from a diol compound having a structure different from the structural unit derived from the diol compound represented by the structural unit (P1) described above. Examples of structural units derived from a diol compound having a structure different from the structural unit derived from the diol compound represented by the structural unit (P1) described above include structural units derived from any of the diol compounds (PX1) to (PX3) described above. The proportion of the structural unit (P1) described above among all the structural units constituting the polyester may be within a range that does not impair the effects of the present invention, and may be, for example, 10 to 50 mol%, preferably 20 to 50 mol%, and more preferably 30 to 50 mol%. The proportion of the structural unit derived from any of the diol compounds (PX1) to (PX3) among all the structural units constituting the polyester may be within a range that does not impair the effects of the present invention, and may be, for example, 40 mol% or less, preferably 30 mol% or less, and more preferably 20 mol% or less. The ratio of the structural units derived from dicarboxylic acid compounds to the total structural units derived from diol compounds constituting the polyester is usually 1:1 in molar ratio.

[0063] (1) Dicarboxylic Acid Compound (PY1) Examples of the dicarboxylic acid compound used in the structural unit derived from the dicarboxylic acid compound include aromatic ring-containing dicarboxylic acid compounds (PY1) such as benzenedicarboxylic acid compounds, polycyclic arenedicarboxylic acid compounds (such as condensed polycyclic arenedicarboxylic acid compounds and ring-assembled arenedicarboxylic acid compounds), and aromatic dicarboxylic acid compounds.

[0064] Examples of the benzenedicarboxylic acid compound include benzenedicarboxylic acid and alkylbenzenedicarboxylic acid. Examples of the benzenedicarboxylic acid include phthalic acid, isophthalic acid, and terephthalic acid. Examples of the alkylbenzenedicarboxylic acid include C 16 alkylbenzenedicarboxylic acid such as 5-methylisophthalic acid. １－４Alkyl-benzenedicarboxylic acid compounds and the like.

[0065] Examples of the polycyclic arene dicarboxylic acid compound include condensed polycyclic arene dicarboxylic acid compounds and ring-assembled arene dicarboxylic acid compounds.

[0066] Examples of the condensed polycyclic arene dicarboxylic acid compound include naphthalenedicarboxylic acids such as 1,2-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, and 2,6-naphthalenedicarboxylic acid; anthracene dicarboxylic acid; and condensed polycyclic C compounds such as phenanthrene dicarboxylic acid. １０－２４ Preferred fused polycyclic arene dicarboxylic acids include fused polycyclic C １０－１４ It is an arene-dicarboxylic acid compound.

[0067] Examples of the ring-assembled arene dicarboxylic acid compounds include bi-C compounds such as 2,2'-biphenyldicarboxylic acid, 3,3'-biphenyldicarboxylic acid, and 4,4'-biphenyldicarboxylic acid. ６－１０ Examples include arene-dicarboxylic acid compounds, and biphenyldicarboxylic acid is preferred.

[0068] The aromatic dicarboxylic acid compound means a dicarboxylic acid compound in which two or more aromatic rings are linked by a single bond and a divalent linking group other than an aromatic ring group, and examples thereof include di(C ６－１０ Aryl)C １－６ diarylalkanedicarboxylic acid compounds such as alkane-dicarboxylic acid compounds, di(C ６－１０ Examples of the dicarboxylic acid include diaryl ketone dicarboxylic acid compounds such as diaryl ketone-dicarboxylic acid compounds, and ester-forming derivatives thereof.

[0069] Of these dicarboxylic acid compounds (PY1), preferred are benzenedicarboxylic acid compounds such as isophthalic acid and terephthalic acid, and biphenyldicarboxylic acid compounds such as 2,2'-biphenyldicarboxylic acid.

[0070] (2) Dicarboxylic Acid Compound (PY2) Examples of dicarboxylic acid compounds used in the structural units derived from the dicarboxylic acid compound include dicarboxylic acid compounds different from the dicarboxylic acid compound (PY1), such as aliphatic dicarboxylic acid compounds (PY2) such as aliphatic dicarboxylic acid compounds and alicyclic dicarboxylic acid compounds.

[0071] Examples of the aliphatic dicarboxylic acid compound include C carboxylic acids such as succinic acid, adipic acid, sebacic acid, and decanedicarboxylic acid. ２－１２ C typified by alkanedicarboxylic acids such as alkane-dicarboxylic acid compounds, maleic acid, fumaric acid, and itaconic acid ２－１０ Examples include unsaturated aliphatic dicarboxylic acid compounds such as alkene-dicarboxylic acid compounds, and ester-forming derivatives thereof. The ester-forming derivatives refer to carboxylic acid derivatives capable of forming an ester bond.

[0072] Examples of the alicyclic dicarboxylic acid compound include C cyclohexanedicarboxylic acid, typified by 1,4-cyclohexanedicarboxylic acid. ５－１０ Cycloalkane dicarboxylic acid compounds such as cycloalkane-dicarboxylic acid compounds, bridged cyclic cycloalkane dicarboxylic acid compounds such as di- or tricycloalkane dicarboxylic acid compounds represented by decalin dicarboxylic acid, norbornane dicarboxylic acid, adamantane dicarboxylic acid, and tricyclodecane dicarboxylic acid, C represented by cyclohexene dicarboxylic acid, ５－１０ Examples thereof include cycloalkene dicarboxylic acid compounds such as cycloalkene-dicarboxylic acid compounds, crosslinked cyclic cycloalkene dicarboxylic acids such as di- or tricycloalkene dicarboxylic acid compounds represented by norbornene dicarboxylic acid, and ester-forming derivatives thereof.

[0073] (Polyurethane) The polyurethane may be any polyurethane having a structural unit derived from a diol compound represented by the structural unit (P1) described above and a structural unit derived from a diisocyanate compound, and may also have a structural unit derived from a diol compound or polyol compound having a structure different from the structural unit derived from the diol compound represented by the structural unit (P1) described above. Examples of the structural unit derived from a diol compound having a structure different from the structural unit derived from the diol compound represented by the structural unit (P1) described above include structural units derived from any of the diol compounds (PX1) to (PX3) described above. The proportion of the structural unit (P1) described above among all the structural units constituting the polyurethane may be within a range that does not impair the effects of the present invention, and may be, for example, 10 to 50 mol %, preferably 20 to 50 mol %, and more preferably 30 to 50 mol %. The proportion of structural units derived from any of the diol compounds (PX1) to (PX3) or polyol compounds in all structural units constituting the polyurethane may be within a range that does not impair the effects of the present invention, and can be, for example, 40 mol% or less, preferably 30 mol% or less, and more preferably 20 mol% or less. The proportion of structural units derived from diisocyanate compounds in all structural units constituting the polyurethane is usually 1:1 in molar ratio to the total of structural units derived from diol compounds constituting the polyurethane.

[0074] Examples of diisocyanate compounds used in the structural units derived from the diisocyanate compounds include toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), naphthalene diisocyanate (NDI), tolidine diisocyanate (TODI), hexamethylene diisocyanate (HDI), and isophorone diisocyanate (IPDI). Preferred examples of diol compounds or polyol compounds used in the structural units derived from the diol compounds or polyol compounds include ethylene glycol, propylene glycol, glycerin, and hexanetriol. Diisocyanate compounds, polyol compounds, and chain extension treatments are described in detail, for example, in "Polyurethane Handbook" (edited by Keiji Iwata, published by Nikkan Kogyo Shimbun, 1987). The descriptions of urethane resins and their raw materials in the "Polyurethane Handbook" can be applied to the present invention as appropriate depending on the purpose.

[0075] Specific examples of the thermoplastic polymer of the present invention are listed below, but are not limited to these. In the specific examples of polyesters below, A-1 and B-1 of diol component 1 represent compounds A-1 and B-1 in the examples described below, respectively. Furthermore, the molar ratio in the specific examples of polyesters refers to the proportion of structural units derived from each component in the total of all structural units constituting the polyester, and means the molar ratio when the total of all structural units constituting the polyester is taken as 100.

[0076] (Specific examples of polycarbonate)

[0077] (Specific examples of polyester)

[0078] The weight average molecular weight (Mw) of the thermoplastic polymer of the present invention is a value calculated as a standard polystyrene standard measured by gel permeation chromatography (GPC). The weight average molecular weight (Mw) of the thermoplastic polymer of the present invention can be selected, for example, from a range of about 10,000 to 1,000,000, preferably 20,000 to 100,000, more preferably 30,000 to 80,000, and even more preferably 35,000 to 50,000. (Measurement Conditions) Measuring instrument: TOSOH EcoSEC HLC-8320GPC (trade name, manufactured by Tosoh Corporation) Column: TOSOH TSKgel Super HZM-H (trade name, manufactured by Tosoh Corporation), TOSOH TSKgel Super HZ4000 (trade name, manufactured by Tosoh Corporation), and TOSOH TSKgel Super HZ2000 (trade name, manufactured by Tosoh Corporation) are connected. Carrier: Tetrahydrofuran (containing BHT stabilizer) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) Measurement temperature: 40°C Carrier flow rate: 0.35 ml / min Sample concentration: 0.05 mass% Detector: RI (refractive index) detector, UV detector (254 nm)

[0079] The Abbe number (νd) and partial dispersion ratio (θg, F) ​​of the thermoplastic polymer of the present invention are values ​​measured using an ellipsometer (manufactured by J.A. Woollam, trade name: M-2000XI-210). Specifically, they are measured based on the description in the evaluation of anomalous partial dispersion described in the Examples below. The Abbe number (νd) and partial dispersion ratio (θg, F) ​​of the thermoplastic polymer are calculated by the following formula. In addition, JIS B 7090:1999 Optics and optical instruments - Reference wavelengths (ISO 7944:1998 Optics and optical instruments - Reference wavelengths) can be appropriately referenced. νd=(nd-1) / (nF-nC) θg,F=(ng-nF) / (nF-nC) Here, nd is the refractive index at a wavelength of 589 nm, nF is the refractive index at a wavelength of 486 nm, nC is the refractive index at a wavelength of 656 nm, and ng is the refractive index at a wavelength of 436 nm.

[0080] In a graph of Abbe number (νd) on the horizontal axis versus wavelength partial dispersion ratio (θg,F) on the vertical axis, the thermoplastic polymer of the present invention has a large deviation (Δθg,F) of the wavelength partial dispersion ratio (θg,F) from the standard line obtained by connecting glass type NSL7 (nd: 1.51, Abbe number (νd): 60.5, wavelength partial dispersion ratio (θg,F): 0.54), which is the standard for normal glass, with glass type PBM2 (nd: 1.62, νd: 36.3, θg,F: 0.58), and is located above the standard line, resulting in a large positive anomalous partial dispersion. The deviation (Δθg,F) of the wavelength partial dispersion ratio (θg,F) of the thermoplastic polymer of the present invention is preferably 0.04 or more, more preferably 0.08 or more. Furthermore, by adjusting the structure of the thermoplastic polymer, it can be made 0.16 or more, or even 0.20 or more. The upper limit of the deviation (Δθg,F) of the wavelength partial dispersion ratio (θg,F) of the thermoplastic polymer of the present invention is not particularly limited, but is usually 0.50 or less.

[0081] The Abbe number (νd) of the thermoplastic polymer of the present invention is not particularly limited, but is preferably 35 or less, more preferably 30 or less, even more preferably 29 or less, and particularly preferably 28 or less. In addition, the Abbe number (νd) of the thermoplastic polymer of the present invention is not particularly limited, but is preferably 1 or more, more preferably 3 or more, even more preferably 5 or more, and particularly preferably 7 or more.

[0082] The partial dispersion ratio (θg,F) of the thermoplastic polymer of the present invention is not particularly limited, but is preferably 0.70 or more, more preferably 0.75 or more, and even more preferably 0.80 or more. The partial dispersion ratio (θg,F) of the thermoplastic polymer of the present invention is not particularly limited, but is preferably 2 or less, more preferably 1.8 or less, and even more preferably 1.7 or less.

[0083] The thermoplastic polymer of the present invention is almost free from coloration and has excellent light transmittance in the visible light region. The thermoplastic polymer of the present invention has substantially no absorption in the long wavelength region of the visible light region, and exhibits a decrease in transmittance toward the short wavelength side. Therefore, the transparency of the thermoplastic polymer of the present invention can be evaluated by measuring the transmittance at a wavelength of 430 nm. The transmittance of the thermoplastic polymer of the present invention at a wavelength of 430 nm is a value measured using an ultraviolet-visible spectrophotometer (e.g., UV-2600 (trade name, manufactured by Shimadzu Corporation)). Specifically, the transmittance at a wavelength of 430 nm is measured, for example, for a THF (tetrahydrofuran) solution in the same manner as the transmittance measurement described in the Examples below. In addition, a light irradiation test for evaluating the light resistance of the thermoplastic polymer is performed based on the xenon light irradiation test described in the Examples below.

[0084] Preferred values ​​for the transmittance of the thermoplastic polymer of the present invention at a wavelength of 430 nm, measured by the above method, are described below. The transmittance of the thermoplastic polymer of the present invention, i.e., the transmittance before the light irradiation test, is not particularly limited, but is preferably 95% or more, and more preferably 97% or more. Furthermore, the transmittance of the thermoplastic polymer of the present invention after the light irradiation test is not particularly limited, but in Evaluation Item 3 (transmittance after 24-hour xenon light irradiation test) described below, it is preferably greater than 87%, more preferably greater than 89%, even more preferably greater than 90%, and particularly preferably greater than 92%. The decrease in transmittance of the thermoplastic polymer of the present invention before and after the light irradiation test is not particularly limited, but in Evaluation Item 3 (transmittance decrease before and after 24-hour xenon light irradiation test) described below, it is preferably less than 8%, more preferably less than 5%. The decrease in transmittance before and after the light irradiation test is calculated by subtracting the transmittance value after the light irradiation test from the transmittance value before the light irradiation test.

[0085] [Method for Producing Thermoplastic Polymer] The method for producing the thermoplastic polymer of the present invention is not particularly limited except for using the diol compound (P1) that derives the structural unit (P1) described above, and the thermoplastic polymer of the present invention can be produced by a conventional method depending on the type of thermoplastic polymer and / or other polymerization components (copolymerization components), etc.

[0086] (Method for Producing Polycarbonate) When the thermoplastic polymer of the present invention is a polycarbonate, a diol compound and a carbonate ester compound are reacted (polymerized or condensed) by a conventional method such as a phosgene method (solvent method) or a transesterification method (melt method). Among these methods, the transesterification method is preferred because it does not require a solvent.

[0087] In the transesterification method, the carbonate compound is used in an amount of, for example, 0.8 to 1.5 mol, preferably 0.9 to 1.2 mol, per mol of the diol component. Examples of the carbonate compound include esters of aryl or aralkyl groups having 6 to 10 carbon atoms, or alkyl groups having 1 to 4 carbon atoms. Specific examples include diphenyl carbonate, ditolyl carbonate, bis(chlorophenyl)carbonate, m-cresyl carbonate, dinaphthyl carbonate, bis(diphenyl)carbonate, dimethyl carbonate, diethyl carbonate, and dibutyl carbonate, with diphenyl carbonate being preferred.

[0088] The transesterification reaction may be carried out in the presence of a catalyst, such as a nitrogen-containing compound or a metal compound, which are commonly used in transesterification reactions.

[0089] Examples of the nitrogen-containing compound include quaternary ammonium hydroxides (e.g., tetraalkylammonium hydroxides such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, and tetrabutylammonium hydroxide; trialkyl-aralkylammonium hydroxides such as trimethylbenzylammonium hydroxide); and tertiary amines (trialkylamines such as trimethylamine and triethylamine; dimethyl-aralkylamines such as dimethylbenzylamine; and triarylamines such as triphenylamine).

[0090] Examples of the metal contained in the metal compound include alkali metals such as sodium, alkaline earth metals such as magnesium, calcium, and barium, transition metals such as manganese, zinc, cadmium, lead, cobalt, and titanium, metals in Group 13 of the periodic table such as aluminum, metals in Group 14 of the periodic table such as germanium, and metals in Group 15 of the periodic table such as antimony.Specific examples of the metal compound include alkoxides, organic acid salts such as acetates and propionates, inorganic acid salts such as borates and carbonates, oxides, and hydroxides of the above metals.

[0091] These catalysts can be used alone or in combination of two or more. Among these catalysts, nitrogen-containing compounds such as quaternary ammonium hydroxides are preferred, and tetraalkylammonium hydroxides such as tetramethylammonium hydroxide are more preferred. The amount of catalyst used is, for example, 0.01 × 10 per mole of the diol compound. －４ ~100 x 10 －４ It is sufficient if the amount is 0.1 × 10 moles, and preferably 0.1 × 10 moles －４ ~40 x 10 －４ It is a molar ratio.

[0092] The reaction may be carried out in the presence of additives (for example, stabilizers such as antioxidants and heat stabilizers) described below, if necessary.

[0093] The reaction can be carried out in an inert gas atmosphere such as nitrogen gas or a rare gas such as helium or argon. The reaction can also be carried out under reduced pressure, for example, at a pressure of 1×10 ２~1 x 10 ４ The reaction temperature can be selected depending on the polymerization method, and for example, the reaction temperature in the transesterification method is, for example, 150 to 320°C, preferably 200 to 310°C, and more preferably 250 to 300°C. In particular, when diphenyl carbonate is used as the carbonate ester, a method of polycondensation while distilling off phenol at high temperature under reduced pressure is effective.

[0094] (Method for producing polyester) When the thermoplastic polymer of the present invention is a polyester, it can be prepared by a conventional method such as a melt polymerization method such as a transesterification method or a direct polymerization method, a solution polymerization method, or an interfacial polymerization method, and the melt polymerization method is preferred. The reaction may be carried out in the presence or absence of a solvent depending on the polymerization method.

[0095] The ratio (or charge ratio) of the diol compound to the dicarboxylic acid compound, in terms of molar ratio, may be, for example, 1 / 1.2 to 1 / 0.8 (diol compound / dicarboxylic acid compound), and preferably 1 / 1.1 to 1 / 0.9. However, this range is not necessarily required, and at least one compound selected from the diol compound and the dicarboxylic acid compound may be used in excess relative to the intended introduction ratio. For example, a diol compound such as ethylene glycol that can be distilled from the reaction system may be used in excess of the ratio (or introduction ratio) that will be introduced into the thermoplastic polymer.

[0096] The reaction may be carried out in the presence of a catalyst. A commonly used esterification catalyst, such as a metal catalyst, can be used as the catalyst. Examples of the metal catalyst include metal compounds containing alkali metals such as sodium; alkaline earth metals such as magnesium, calcium, and barium; transition metals such as titanium, manganese, and cobalt; metals in Group 12 of the periodic table such as zinc and cadmium; metals in Group 13 of the periodic table such as aluminum; metals in Group 14 of the periodic table such as germanium and lead; and metals in Group 15 of the periodic table such as antimony. Examples of the metal compounds include alkoxides; organic acid salts such as acetates and propionates; inorganic acid salts such as borates and carbonates; oxides, and hydrates thereof. Representative metal compounds include, for example, germanium compounds such as germanium dioxide, germanium hydroxide, germanium oxalate, germanium tetraethoxide, and germanium-n-butoxide; antimony compounds such as antimony trioxide, antimony acetate, and antimony ethylene glycolate; titanium compounds such as tetra-n-propyl titanate, tetraisopropyl titanate, tetra-n-butyl titanate (titanium (IV) tetrabutoxide), titanium oxalate, and titanium potassium oxalate; manganese compounds such as manganese acetate tetrahydrate; and calcium compounds such as calcium acetate monohydrate.

[0097] These catalysts can be used alone or in combination of two or more. When using multiple catalysts, each catalyst can be added depending on the progress of the reaction. Among these catalysts, manganese acetate tetrahydrate, calcium acetate monohydrate, germanium dioxide, titanium (IV) tetrabutoxide, etc. are preferred. The amount of catalyst used is, for example, 0.01 × 10 per mole of the dicarboxylic acid compound. －４ ~100 x 10 －４ mole, preferably 0.1 x 10 －４ ~40 x 10 －４ It is a molar ratio.

[0098] The reaction may be carried out in the presence of a stabilizer such as a heat stabilizer or an antioxidant, if necessary. A heat stabilizer is usually used, and examples thereof include phosphorus compounds such as trimethyl phosphate, triethyl phosphate, triphenyl phosphate, dibutyl phosphate (dibutyl phosphate or dibutyl phosphate), phosphorous acid, trimethyl phosphite, and triethyl phosphite. Among these, dibutyl phosphate is often used. The amount of the heat stabilizer used is, for example, 0.01 × 10 relative to 1 mole of the dicarboxylic acid compound. －４ ~100 x 10 －４ mole, preferably 0.1 x 10 －４ ~40 x 10 －４ It is a molar ratio.

[0099] The reaction is usually carried out in an inert gas atmosphere such as nitrogen gas or a rare gas such as helium or argon. ２ ~1 x 10 ４ The reaction temperature can be selected depending on the polymerization method. For example, the reaction temperature in the melt polymerization method is 150 to 320°C, preferably 180 to 310°C, and more preferably 200 to 300°C.

[0100] (Method for Producing Polyurethane) When the thermoplastic polymer of the present invention is a polyurethane, it can be produced by a conventional method, for example, by referring to the description in "Polyurethane Handbook" (edited by Iwata Keiji, published by Nikkan Kogyo Shimbun, 1987).

[0101] [Additives] The thermoplastic resin of the present invention may contain additives in addition to the thermoplastic polymer of the present invention. Additives commonly used in thermoplastic resins can be used as long as they do not impair the effects of the present invention. For example, the thermoplastic resin may contain fillers or reinforcing agents, conductive agents, flame retardants, plasticizers, lubricants, mold release agents, antistatic agents, dispersants, flow control agents, leveling agents, antifoaming agents, surface modifiers, hydrolysis inhibitors, stabilizers, stress reducers, etc. Examples of stabilizers include antioxidants, ultraviolet absorbers, and heat stabilizers. Examples of stress reducers include silicone oils, silicone rubbers, various plastic powders, and various engineering plastic powders. These additives may be used alone or in combination of two or more.

[0102] When the thermoplastic resin of the present invention is in the form of a composition containing the above-mentioned additives in addition to the thermoplastic polymer of the present invention, the content of the thermoplastic polymer of the present invention in the thermoplastic resin of the present invention is preferably 95% by mass or more, more preferably 97% by mass or more, and even more preferably 99% by mass or more. When two or more types of thermoplastic polymers of the present invention are contained in the thermoplastic resin of the present invention, the total content thereof is preferably within the above range. By setting the content of the thermoplastic polymer of the present invention in the thermoplastic resin of the present invention within the above range, it is possible to achieve the effects of the present invention, such as almost no coloring, high anomalous partial dispersion (i.e., a partial dispersion ratio (θg,F) higher than the predicted partial dispersion ratio (θg,F) is achieved in a thermoplastic resin having a predetermined Abbe number (νd)), and excellent light resistance. Regarding the transmittance, the deviation (Δθg,F) of the wavelength partial dispersion ratio (θg, F), the Abbe number (νd), the partial dispersion ratio (θg, F), the transmittance after the light irradiation test, and the decrease in transmittance before and after the light irradiation test exhibited by the thermoplastic resin of the present invention, the descriptions of the transmittance, the deviation (Δθg,F) of the wavelength partial dispersion ratio (θg, F), the Abbe number (νd), the partial dispersion ratio (θg, F), the transmittance after the light irradiation test, and the decrease in transmittance before and after the light irradiation test exhibited by the thermoplastic polymer of the present invention described above can be applied, respectively.

[0103] As described above, the thermoplastic resin of the present invention is almost free from coloration, has high anomalous partial dispersion, and exhibits excellent light resistance, and therefore can be used in a variety of applications, and is particularly preferably used as a resin material for optical members such as optical films, optical sheets, and optical lenses.

[0104] <Molded article> The molded article of the present invention is a molded article of the thermoplastic resin of the present invention. That is, the molded article of the present invention is obtained by molding the thermoplastic resin of the present invention. As described above, the molded article of the present invention is almost free from coloration, has high anomalous partial dispersion, and can also exhibit excellent light resistance.

[0105] The shape of the molded article of the present invention is not particularly limited, and examples thereof include one-dimensional structures such as linear, fibrous (or fiber-like) and thread-like structures, two-dimensional structures such as film-like, sheet-like and plate-like structures, and three-dimensional structures such as concave or convex lens-like, rod-like and hollow (tubular) structures.

[0106] In particular, the thermoplastic resin of the present invention is useful for forming optical films and optical sheets because it has various excellent optical properties. Therefore, the molded article of the present invention also includes optical films and optical sheets obtained by molding the thermoplastic resin of the present invention (hereinafter referred to as "optical films and optical sheets of the present invention").

[0107] The average thickness of the optical film or optical sheet of the present invention can be selected from the range of about 1 to 1000 μm depending on the application, and is, for example, 1 to 200 μm, preferably 5 to 150 μm, and more preferably 10 to 120 μm.

[0108] The optical film and optical sheet of the present invention can be obtained by forming the thermoplastic resin of the present invention into a film by a conventional method, such as a casting method (solvent casting method), a melt extrusion method, or a calendar method.

[0109] The optical film or optical sheet of the present invention may be a stretched film or sheet. Such a stretched film or sheet may be either a uniaxially stretched film or sheet or a biaxially stretched film or sheet.

[0110] The stretching ratio in each direction in uniaxial or biaxial stretching is, for example, 1.1 to 10 times, preferably 1.2 to 5 times, and more preferably 1.5 to 3 times. In the case of biaxial stretching, equal stretching such as stretching about 1.5 to 5 times in both the longitudinal and transverse directions may be used, or uneven stretching such as stretching about 1.1 to 4 times in the longitudinal direction and about 2 to 6 times in the transverse direction may be used. In the case of uniaxial stretching, longitudinal stretching such as stretching about 2.5 to 8 times in the longitudinal direction may be used, or transverse stretching such as stretching about 1.2 to 5 times in the transverse direction may be used.

[0111] The average thickness of the stretched film or stretched sheet is, for example, 1 to 150 μm, preferably 3 to 120 μm, and more preferably 5 to 100 μm.

[0112] Such a stretched film or sheet can be obtained by stretching a film or sheet (or an unstretched film or sheet) after film formation. The stretching method is not particularly limited, and in the case of uniaxial stretching, either a wet stretching method or a dry stretching method may be used, and in the case of biaxial stretching, either a tenter method (flat method) or a tube method may be used, although the tenter method, which provides excellent uniformity in stretched thickness, is preferred.

[0113] The molded article of the present invention may be joined or adhered to another substrate, and the type and / or material of the substrate is not particularly limited, and may be, for example, a substrate having any one-dimensional, two-dimensional, or three-dimensional shape formed from a resin material, a ceramic material, a metal material, etc. For example, when the molded article of the present invention is in the form of a film or sheet, it may be combined with a substrate having a two-dimensional shape such as a film or sheet to form a laminate, a laminate film, or a laminate sheet.

[0114] Representative examples of the substrate having the two-dimensional shape include ceramic substrates such as glass substrates, resin films, etc., and transparent substrates are preferred.The resin forming the resin film includes, for example, polyolefin resins such as chain olefin resins and cyclic olefin resins (or cycloolefin resins); (meth)acrylic resins; styrene resins; polyester resins such as polyalkylene arylate resins, polyarylate resins, and polycarbonate resins; polyamide resins, etc.For example, the molded article of the present invention may be used by laminating a resin film formed from a cycloolefin resin, a polyamide resin, etc.

[0115] In addition to the above-mentioned casting method (solvent casting method), melt extrusion method, and calendar method, the molded article of the present invention can also be produced by, for example, compression molding methods such as injection molding and injection compression molding, extrusion molding, transfer molding, blow molding, pressure molding, and embossing molding.

[0116] The thermoplastic resin of the present invention may be pelletized before being subjected to hot-press molding. By pelletizing the thermoplastic resin of the present invention, the handleability of the resin during hot-press molding can be improved. When pelletizing the thermoplastic resin of the present invention, for example, a vented single-screw extruder or the like can be used.

[0117] When performing compression molding, a spacer of the desired thickness is used, and the thermoplastic resin of the present invention (preferably a pellet of the thermoplastic resin of the present invention) is sandwiched between resin films such as polyimide films, heated and compressed, and then removed from the resin film along with the spacer, and cooled to room temperature (including standing to cool). The conditions for performing heat compression include a heating temperature of preferably 180 to 450°C, more preferably 180 to 390°C, a pressure of preferably 0.098 MPa to 9.8 MPa, more preferably 0.294 MPa to 9.8 MPa, and even more preferably 1.0 MPa to 9.8 MPa, and a pressure time of preferably 30 to 1000 seconds, more preferably 30 to 500 seconds, and even more preferably 60 to 500 seconds.

[0118] When injection molding is performed, an injection molding machine (including an injection compression molding machine) is used. In the injection molding machine, the molten thermoplastic resin of the present invention is stored at the tip of a cylinder, and then the molten thermoplastic resin of the present invention is injected into a mold to form the molded product. A commonly used injection molding machine can be used. The cylinder is preferably made of a material that exhibits low adhesion to the thermoplastic resin of the present invention and is corrosion-resistant and abrasion-resistant. An example of an injection molding machine is the Micro-1 manufactured by Meiho Co., Ltd.

[0119] The cylinder temperature during injection molding is preferably 200 to 450° C., more preferably 250 to 390° C. The mold temperature is preferably 50 to 300° C., more preferably 100 to 250° C.

[0120] The molded article of the present invention is a cured product that is almost free of coloration and has high anomalous partial dispersion, and also exhibits excellent light resistance, and therefore can be used in a variety of applications, and is particularly preferably used for optical components such as optical films, optical sheets, and optical lenses.

[0121] <Optical Element> The optical element of the present invention includes the molded article of the present invention. The type of the optical element of the present invention is not particularly limited, but it can be suitably used in particular as long as it is an optical element that transmits light (so-called passive optical element). Examples of optical functional devices equipped with such an optical element include various display devices (liquid crystal displays, plasma displays, etc.), various projector devices (OHPs (overhead projectors), liquid crystal projectors, etc.), optical fiber communication devices (optical waveguides, optical amplifiers, etc.), and photographing devices such as cameras and videos.

[0122] Examples of passive optical components include lenses, prisms, prism sheets, panels (plate-shaped molded products), films, optical waveguides (film-shaped or fiber-shaped, etc.), optical disks, and sealants for LEDs (light-emitting diodes). Passive optical components may be provided with any coating layer or any additional functional layer as needed. For example, passive optical components may be provided with a protective layer that prevents mechanical damage to the coating surface due to friction or wear, a light-absorbing layer that absorbs light of undesirable wavelengths that cause deterioration of inorganic particles or substrates, a transmission-shielding layer that suppresses or prevents the transmission of reactive low molecules such as moisture or oxygen gas, an antiglare layer, an antireflection layer, a low-refractive index layer, etc. Specific examples of coating layers include transparent conductive films or gas barrier films made of inorganic oxide or inorganic nitride coating layers, and gas barrier films or hard coat films made of organic coating layers. The coating layer can be formed by a commonly used coating method such as vacuum deposition, CVD (Chemical Vapor Deposition), sputtering, dip coating, or spin coating.

[0123] The present invention will be described in more detail below with reference to examples. The materials, amounts used, ratios, processing details, processing procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the specific examples shown below. The polymer synthesis process and the storage process before use in evaluation using the polymer were carried out in an environment using yellow light as illumination. The mass average molecular weight of the polymer is a value measured by the method described above.

[0124] Examples Monomer Synthesis Examples Monomer compounds were synthesized as follows: Note that w / v % means mass to volume percentage, and room temperature means 25°C.

[0125] 1. Synthesis of Compound A-1

[0126] (1) Synthesis of Intermediate a-1: 50.0 g of 4-hydroxybenzaldehyde, 63.0 g of 4-hydroxypropiophenone, 170 mL of ethanol, 125 mL of piperidine, and 50 mL of glacial acetic acid were weighed into a 1 L three-neck flask and stirred under reflux for 36 hours to allow the reaction to proceed. After cooling to room temperature, the mixture was diluted with 500 mL of ethyl acetate and washed sequentially with 500 mL of water, 500 mL of dilute hydrochloric acid, and 500 mL of 2% saline. The organic layer was concentrated and purified by silica gel column chromatography to obtain 32.0 g of Intermediate a-1. (2) Synthesis of Compound A-1: ​​22.0 g of Intermediate a-1, 30.0 g of ethylene carbonate, 6.0 g of potassium carbonate, and 60 mL of N,N-dimethylacetamide (DMAc) were weighed into a 500 mL three-neck flask and stirred at 120°C for 1 hour to allow the reaction to proceed. After cooling to 80°C, 15.0 mL of 50 w / v% aqueous sodium hydroxide solution and 60 mL of water were added, followed by stirring for another 1 hour. After cooling to room temperature, the supernatant was decanted to recover the precipitated solid, and the resulting solid was purified by silica gel column chromatography to obtain 18.0 g of Compound A-1. １ H-NMR (400MHz, DMSO-d ６ ): δ2.16ppm (s, 3H), 3.70-3.80ppm (m, 4H), 4.02-4.12ppm (m, 4H), 4.90ppm (m, 2H), 7.00-7.15ppm (m, 5H), 7.46ppm (d, 2H), 7.72ppm (d, 2H)

[0127] 2. Synthesis of Compound B-1

[0128] (1) Synthesis of Intermediate b-1 41.4 g of 2,4-dihydroxybenzaldehyde, 170 mL of N-methylpyrrolidone (DMP), and 100 g of potassium carbonate were weighed into a 1 L three-neck flask and heated to 70°C. 105 g of 2-bromoethyl acetate was added dropwise over 30 minutes, and the mixture was stirred at 80°C for 3 hours to allow the reaction to proceed. After cooling to room temperature, the mixture was diluted with 500 mL of ethyl acetate and washed with 300 mL of water and 300 mL of saturated brine, in that order. The mixture was dehydrated over anhydrous magnesium sulfate and filtered, and then hexane was added to the organic layer to precipitate crystals. The obtained crystals were dried under vacuum, yielding 43.0 g of Intermediate b-1. (2) Synthesis of Compound B-1 27.0 g of intermediate b-1, 12.0 g of propiophenone, 80 mL of ethanol, 20 mL of piperidine, and 10 mL of glacial acetic acid were weighed into a 1 L three-neck flask and stirred at 80°C for 36 hours to allow the reaction to proceed. Subsequently, 15.0 mL of 50 w / v% aqueous sodium hydroxide solution and 10 mL of water were added, and the mixture was further stirred at 80°C for 6 hours. After cooling to room temperature, the mixture was diluted with 300 mL of ethyl acetate and then washed with 300 mL of water, 300 mL of dilute hydrochloric acid, and 300 mL of saturated saline, in that order. The organic layer was concentrated and then purified by silica gel column chromatography to obtain 19.0 g of Compound B-1. １ H-NMR (400MHz, DMSO-d ６ ): δ2.16ppm (s, 3H), 3.65-3.75ppm (m, 4H), 3.96-4.10ppm (m, 4H), 4.78ppm (t, 1H), 4.88ppm (t, 1H), 6.60- 6.64ppm (m, 2H), 7.36-7.46ppm (m, 2H), 7.50-7.56ppm (m, 2H), 7.58-7.64ppm (m, 1H), 7.68-7.74ppm (m, 2H)

[0129] 3. Synthesis of Comparative Compound CM-1

[0130] (1) Synthesis of Intermediate c-1 29.0 g of Intermediate c-1 was obtained in the same manner as in the synthesis of Intermediate a-1, except that 4-hydroxypropiophenone was replaced with 4-hydroxyacetophenone. (2) Synthesis of Comparative Compound CM-1 7.9 g of Comparative Compound CM-1 was obtained in the same manner as in the synthesis of Compound A-1, except that Intermediate a-1 was replaced with Intermediate c-1. This Comparative Compound CM-1 corresponds to the compound used in Example 6 of U.S. Pat. No. 3,043,802.

[0131] 4. Synthesis of Comparative Compound CM-2

[0132] 15.9 g of comparative compound CM-2 was obtained in the same manner as in the synthesis of compound B-1, except that propiophenone was replaced with benzoylacetonitrile. This comparative compound CM-2 corresponds to compound D-3 synthesized in Example 3 of Korean Patent Publication No. 2021-0043115.

[0133] [Polymer Synthesis Example] <Polycarbonate Synthesis Example> (1) Synthesis of Polycarbonate PC-1 15.7 g of Compound A-1, 10.0 g of diphenyl carbonate, and 18 μL of a 0.025 mol / L aqueous sodium bicarbonate solution were placed in a 100 mL three-neck flask equipped with a stirrer and a distillation apparatus, and the mixture was heated to 200°C over 30 minutes under a nitrogen atmosphere of 101 kPa and stirred. The pressure was then reduced to 30 kPa over 30 minutes, the temperature was raised to 240°C at a rate of 60°C / hour, and the mixture was maintained at 240°C and 30 kPa for 10 minutes. The pressure was then reduced from 30 kPa to 0.1 kPa or less over 30 minutes. The mixture was further stirred for 30 minutes at 240°C and 0.1 kPa or less to carry out a polymerization reaction, yielding polycarbonate PC-1. The weight average molecular weight of polycarbonate PC-1 was 42,000. (2) Synthesis of Polycarbonate PC-2, Comparative Polycarbonates PCCM-1 and PCCM-2 Polycarbonate PC-2 and comparative polycarbonates PCCM-1 and PCCM-2 were obtained in the same manner as in the synthesis of polycarbonate PC-1 above, except that an equimolar amount of compound B-1 or comparative compound CM-1 or CM-2 was used instead of compound A-1. The mass average molecular weight of polycarbonate PC-2 was 45,000, the mass average molecular weight of comparative polycarbonate PCCM-1 was 36,000, and the mass average molecular weight of comparative polycarbonate PCCM-2 was 47,000.

[0134] <Polyester Synthesis Example> (1) Synthesis of Polyester PE-3 0.04 mol of Compound A-1, 0.11 mol of ethylene glycol, and 0.05 mol of dimethyl isophthalate were added to a 100 mL three-neck flask equipped with a stirrer and a distillation device, and the mixture was gradually heated and melted with stirring to carry out an ester exchange reaction. －４mol of ethylene glycol was added, and the temperature was gradually increased until the temperature reached 320°C and the pressure was reduced to 0.1 kPa or less, and ethylene glycol was removed while the pressure was reduced, thereby obtaining polyester PE-3. The weight average molecular weight of polyester PE-3 was 39,000. (2) Synthesis of comparative polyesters PECM-1 and PECM-2 Comparative polyesters PECM-1 and PECM-2 were obtained in the same manner as in the synthesis of polyester PE-3 above, except that an equimolar amount of comparative compound CM-1 or CM-2 was used instead of compound A-1. The weight average molecular weight of comparative polyester PECM-1 was 41,000, and the weight average molecular weight of comparative polyester PECM-2 was 35,000.

[0135] The transmittance, anomalous partial dispersion, and light resistance of each of the polymers prepared above were evaluated as follows. The results are shown in Table 1. Note that polycarbonates PC-1 and PC-2 and polyester PE-3 are thermoplastic resins of the present invention, and comparative polycarbonates PCCM-1 and PCCM-2 and comparative polyesters PECM-1 and PECM-2 are comparative thermoplastic resins.

[0136] <Evaluation Item 1: Transmittance> Using a Shimadzu ultraviolet-visible spectrophotometer (UV-2550), the transmittance of the diluted solution at a wavelength of 430 nm was measured under the following conditions, and evaluated according to the following criteria. A higher transmittance at a wavelength of 430 nm indicates less yellow coloration. (Measurement Conditions) Cell: Square quartz cell (optical path length: 1 cm) Sample: The thermoplastic resin of the present invention, the comparative thermoplastic resin, or polycarbonate (manufactured by Teijin Limited, trade name: Panlite L-1225Y) was dissolved in tetrahydrofuran (THF) to prepare a concentration of 50.0 mg / 5 mL. Blank: THF - Evaluation Criteria - A: 97% or more B: 95% or more and less than 97% C: 90% or more and less than 95% D: 80% or more and less than 90% E: Less than 80%

[0137] <Evaluation Item 2: Anomalous Partial Dispersion> (1) Sample Preparation 1.0 g of the thermoplastic resin of the present invention, the comparative thermoplastic resin, or polycarbonate (manufactured by Teijin Limited, trade name: Panlite L-1225Y) was dissolved in 20 mL of cyclohexanone to prepare a coating solution. Each coating solution was spin-coated onto a quartz substrate to prepare a polymer spin-coated film, which was used as a sample for refractive index measurement. (2) Evaluation of Anomalous Partial Dispersion The refractive index of the refractive index measurement sample prepared above was measured at wavelengths of 436 nm, 486 nm, 589 nm, and 656 nm using an ellipsometer (manufactured by J.A. Woollam Co., Ltd., trade name: M-2000XI-210). The wavelength partial dispersion ratio (θg, F) ​​of the refractive index and the Abbe number (νd) were calculated using the following equations. νd=(nd-1) / (nF-nC) θg,F=(ng-nF) / (nF-nC) In the above formulas, nd is the refractive index at a wavelength of 589 nm, nF is the refractive index at a wavelength of 486 nm, nC is the refractive index at a wavelength of 656 nm, and ng is the refractive index at a wavelength of 436 nm. Next, in a graph of Abbe number (νd) on the horizontal axis versus wavelength partial dispersion ratio (θg,F) on the vertical axis, the standard line obtained by connecting glass type NSL7 (refractive index at d-line (nd): 1.51, Abbe number (νd): 60.5, wavelength partial dispersion ratio (θg,F): 0.54) serving as a standard for normal glass with glass type PBM2 (nd: 1.62, νd: 36.3, θg,F: 0.58) was used to obtain the deviation (Δθg,F) of the wavelength partial dispersion ratio (θg,F) from the standard line (i.e., the distance from the standard line). The deviation (Δθg,F) was determined for each of the thermoplastic resin of the present invention, the comparative thermoplastic resin, and polycarbonate (manufactured by Teijin Limited, trade name: Panlite L-1225Y), and evaluated according to the following criteria. Note that both NSL7 and PBM2 are optical glasses manufactured by Ohara Inc. The definitions of nd, νd, and θg,F are the same as those in the above formula. - Evaluation criteria - A: 0.20 or more B: 0.16 or more and less than 0.20 C: 0.08 or more and less than 0.16 D: 0.04 or more and less than 0.08 E: Less than 0.04

[0138] <Evaluation Item 3: Lightfastness> (1) Preparation of Lightfastness Evaluation Sample 1.0 g of the thermoplastic resin of the present invention, the comparative thermoplastic resin, or polycarbonate (manufactured by Teijin Limited, product name: Panlite L-1225Y) was dissolved in 5.0 mL of methylene chloride. 1.5 g of this was weighed out and placed in an aluminum dish with a diameter of 4 cm, and dried at room temperature for 3 days to prepare a film-like sample for lightfastness evaluation with a thickness of approximately 0.1 mm. (2) Evaluation of Lightfastness A xenon light irradiation test was conducted on the lightfastness evaluation sample prepared above under the following conditions, and the decrease in transmittance at a wavelength of 450 nm before and after irradiation with xenon light was determined, and the lightfastness was evaluated according to the following criteria. This irradiation test corresponds to an accelerated lightfastness test under a sunlight environment. The decrease in transmittance at a wavelength of 430 nm for all of the thermoplastic resins PC-1, PC-2, and PE-3 of the present invention was less than 5%. (Xenon Light Irradiation Conditions) Apparatus: Xenon accelerated weather resistance tester Q-SUN Xe-1 (trade name, manufactured by Q-Lab Corporation) Light source: Xenon arc lamp Optical filter: Extended UV Q / B (trade name, manufactured by Q-Lab Corporation) Illuminance: 0.43 W / m ２ (340 nm illuminance meter) Black panel temperature: 63°C Test time: 24 hours - Evaluation criteria - A: The decrease in transmittance is less than 5% B: The decrease in transmittance is 5% or more and less than 8% C: The decrease in transmittance is 8% or more and less than 10% D: The decrease in transmittance is 10% or more

[0139]

[0140] PC-1, PC-2, and PE-3: Polycarbonate PC-1, PC-2, and polyester PE-3, respectively. PCCM-1, PCCM-2, PECM-1, and PECM-2: Comparative polycarbonate PCCM-1, PCCM-2, and comparative polyester PECM-1, PECM-2, respectively. Panlite L-1225Y: Trade name, manufactured by Teijin Limited, polycarbonate

[0141] The results in Table 1 reveal the following: Comparative polycarbonates PCCM-1 and PCCM-2, and comparative polyesters PECM-1 and PECM-2 are not thermoplastic resins containing the structural units defined in the present invention, in that R in general formula (P1) of the present invention is not an aliphatic hydrocarbon group but a hydrogen atom or a cyano group. These comparative thermoplastic resins exhibited coloration derived from the chalcone skeleton and were poor in lightfastness. That is, the transmittance at a wavelength of 430 nm, at which absorption derived from the chalcone skeleton is observed, was low, less than 90% for comparative polycarbonate PCCM-1 and comparative polyester PECM-1, and less than 80% for comparative polycarbonate PCCM-2 and comparative polyester PECM-2, while the decrease in transmittance at a wavelength of 450 nm due to xenon light irradiation was high, being 10% or more for comparative polycarbonate PCCM-1 and comparative polyester PECM-1, and 8% or more for comparative polycarbonate PCCM-2 and comparative polyester PECM-2. Furthermore, commercially available polycarbonate (manufactured by Teijin Limited, trade name: Panlite L-1225Y) had a small anomalous partial dispersion of refractive index of less than 0.04, indicating poor anomalous partial dispersion. In contrast, the thermoplastic resins of the present invention, polycarbonates PC-1 and PC-2, and polyester PE-3, all have a high transmittance of 95% or more at a wavelength of 430 nm, and also a high anomalous partial dispersion of 0.08 or more. The decrease in transmittance at wavelengths of 430 nm or 450 nm due to xenon light irradiation was low at less than 5%, with almost no coloring, excellent anomalous partial dispersion, and excellent light resistance. Thus, the thermoplastic resin of the present invention has almost no coloring, excellent anomalous partial dispersion, and excellent light resistance. Therefore, it can be seen that even in molded articles of the thermoplastic resin of the present invention, there is almost no coloring derived from the thermoplastic resin of the present invention, and the articles have excellent anomalous partial dispersion and light resistance.

[0142] This application claims priority based on Japanese Patent Application No. 2023-107393, filed in Japan on June 29, 2023, the contents of which are incorporated herein by reference.

Claims

1. A thermoplastic resin containing a structural unit represented by the following general formula (P1): In the above formula, R represents an aliphatic hydrocarbon group. １ ~R １０ Two of the groups represent a divalent substituent represented by the following general formula (P2), and the remaining eight groups represent a hydrogen atom or a monovalent substituent. In the above formula, L represents an alkylene group having 2 to 6 carbon atoms; Ｐ represents a single bond or a carbonyl group. * represents a bond to the benzene ring in formula (P1), and # represents a bond.

2. The thermoplastic resin according to claim 1, which contains a structural unit represented by the following general formula (P1-1) or (P1-2). In the above formula, R represents an aliphatic hydrocarbon group, R １ , R ２ and R ４ ~R １０ represents a hydrogen atom or a monovalent substituent; L １ and L ２ represents an alkylene group having 2 to 6 carbon atoms; L Ｐ１ and L Ｐ２ indicates a single bond or a carbonyl group. # indicates a bond.

3. The thermoplastic resin according to claim 1, wherein R is an alkyl group having 1 to 10 carbon atoms.

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

5. A molded article of the thermoplastic resin according to any one of claims 1 to 4.

6. An optical member comprising the molded article according to claim 5.