Resin composition and molded body comprising same

Abstract

One embodiment provides a resin composition containing a compound (A) represented by the provided formula and a resin, wherein the content of the compound (A) in the resin composition is 0.001-50 parts by mass relative to 100 parts by mass of the resin in the resin composition.

Description

Resin composition and molded article containing same

[0001] The present invention relates to a resin composition and a molded article containing the same. The present invention also relates to a method for producing the resin composition, a method for increasing the refractive index of a resin, and a compounding agent added to the resin to increase the refractive index.

[0002] BACKGROUND ART Conventionally, various thermoplastic resins have been used in a wide range of fields. Thermoplastic resins are formed into various molded articles by techniques such as injection molding, and are used in a wide range of industrial fields, such as electrical and electronic equipment, office automation equipment, heavy electrical machinery, precision machinery, and automotive fields.

[0003] Thermoplastic resin components have the advantage of being mass-produced by injection molding, and polycarbonate resins, polyester carbonate resins, polyester resins, and the like are used, for example, as high-refractive-index materials for camera lenses. In recent years, research has also been conducted on aromatic polysiloxane polymers, also known as polyarylenesiloxane compounds (e.g., Patent Documents 1 and 2). The importance of polyarylenesiloxane compounds is increasing, and they are also used, for example, as release layers in photocopying, photoresist materials, plasticizers for resins such as polycarbonate resins, and components of powder surface coating systems.

[0004] When thermoplastic resins are used in optical components, various properties are required depending on the application. For example, when resins are used in optical lenses, they preferably have the desired refractive index and Abbe number, as well as heat resistance, transparency, low water absorption, chemical resistance, low birefringence, and moisture resistance. Much research has been conducted to develop resins with these excellent properties. In recent years, the trend toward lighter, thinner, and smaller products has created a particular demand for optical resins with high refractive indexes. For example, when resins are used in optical lenses, a high refractive index of a resin allows lens elements with the same refractive index to be realized with a smaller surface curvature, thereby reducing the amount of aberration generated by this surface. This results in a reduction in the number of lenses, a reduction in the lens's decentering sensitivity, and a reduction in lens thickness and weight. Thus, resins with various desirable properties have been developed depending on the application, and desired properties can be achieved by adding additives such as antioxidants, release agents, and wavelength dispersion adjusters (see, for example, Patent Document 3).

[0005] Special table No. 08-502537 Publication No. 2015-512999 Patent No. 6717003

[0006] An object of the present invention is to provide a resin composition useful as, for example, an optical material, and a molded article containing the same.

[0007] As a result of extensive research, the present inventors have found that a resin composition obtained by mixing a specific compounding agent with a resin has properties particularly favorable for optical materials. The present invention is, for example, as follows: [1] A resin composition comprising a compound (A) represented by the following formula and a resin, The content of the compound (A) in the resin composition is 0.001 to 50 parts by mass relative to 100 parts by mass of the resin in the resin composition, and the resin contains any one of the following resins (J1) to (J3): Resin (J1) A structural unit represented by the following general formula (1), -OSi(R １ R ２ A thermoplastic resin comprising a structural unit consisting of a silane moiety (S) represented by O— and a diol moiety (M) derived from a dihydroxy compound represented by M: [In general formula (1), R１ and R ２ are each independently selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, which may have a substituent, and an aryl group having 6 to 30 carbon atoms, which may have a substituent.] Resin (J2) A polycarbonate resin, polyester resin, or polyestercarbonate resin containing a structural unit derived from a monomer represented by the following general formula (3) and / or a structural unit derived from a monomer represented by the following general formula (4): [In general formula (3), R ａ and R ｂ each independently represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 20 carbon atoms which may have a substituent, an alkoxyl group of 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group of 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group of 5 to 20 carbon atoms which may have a substituent, an aryl group of 6 to 20 carbon atoms which may have a substituent, a heteroaryl group of 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 of 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 optionally substituted 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; and a and b each independently represent an integer of 0 to 10. [In general formula (4), R ｃ and R ｄare each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group of 1 to 20 carbon atoms which may have a substituent, an alkoxyl group of 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group of 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group of 5 to 20 carbon atoms which may have a substituent, and an aryl group of 6 to 20 carbon atoms which may have a substituent; A and B each independently represent an alkylene group of 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; Y １ represents a single bond, a fluorene group which may have a substituent, or any of the structures represented by the following general formulas (8), (9), (11) to (17): [In general formulas (8), (9), (11) to (14), R ２１ and R ２２ 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 ２１ and R ２２ are bonded to each other to form a carbon ring or hetero ring having 1 to 20 carbon atoms which may have a substituent; r and s each independently represent an integer of 0 to 5000; in the general formulae (15) to (17), R ２３ and R ２４each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, or an alkyl group having 1 to 9 carbon atoms, an alkoxyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms, each of which may have a substituent. Resin (J3) A thermoplastic resin comprising: a dialkoxysilane compound containing at least one of a dialkyldialkoxysilane, a diaryldialkoxysilane, and a monoalkylmonoaryldialkoxysilane; a diaryloxysilane compound containing at least one of a dialkyldiaryloxysilane, a diaryldiaryloxysilane, and a monoalkylmonoaryldiaryloxysilane; and a monoalkoxymonoaryloxysilane compound containing at least one of a dialkylmonoalkoxymonoaryloxysilane, a diarylmonalkoxymonoaryloxysilane, and a monoalkylmonoarylmonalkoxymonoaryloxysilane compound; a fluorene structural unit (F) derived from a fluorene ring-containing dihydroxy compound; and a dinaphthalene structural unit (N) derived from a dinaphthalene-containing dihydroxy compound. [2] The resin composition according to [1], wherein the resin composition comprises the resin (J2), and the weight-average molecular weight (Mw) of the resin (J2) in terms of polystyrene is 10,000 to 300,000. [3] The resin composition according to [1] or [2], wherein the resin composition comprises the resin (J2), and in the general formulas (2) and (3), A and B each independently represent an alkylene group having 2 or 3 carbon atoms. [4] The resin composition according to any one of [1] to [3], wherein the resin composition comprises the resin (J2), and the resin (J2) contains at least a structural unit derived from any one of BPEF, BNE, BNEF, and DPBHBNA. [5] The resin composition according to any one of [1] to [4], wherein any one or more of the resins (J1) to (J3) further contains a structural unit derived from a dicarboxylic acid or an ester-forming derivative thereof. [6] The resin composition according to any one of [1] to [5], having a refractive index (20°C, 589 nm) of 1.640 or more.[7] A molded article comprising the resin composition according to any one of [1] to [6]. [8] The molded article according to [7], which is an optical member. [9] The molded article according to [8], which is an optical member, is an optical lens or an optical film.

[10] A method for producing the resin composition according to any one of [1] to [6], comprising: mixing a monomer constituting the resin with the compound (A) to obtain a mixture; and then subjecting the mixture to polymerization conditions to polymerize the monomer to obtain a resin composition.

[11] A method for improving the refractive index of a resin, comprising: mixing a material containing a monomer constituting the resin with a compound (A) represented by the following formula to obtain a mixture: and then subjecting the mixture to polymerization conditions to polymerize the monomers to obtain a resin composition.

[12] A compounding agent added to a resin to improve the refractive index, comprising a compound (A) represented by the following formula:

[0008] According to the present invention, it is possible to provide a resin composition useful as, for example, an optical material, and a molded article containing the same.

[0009] DETAILED DESCRIPTION OF THE INVENTION In one embodiment, the resin composition of the present invention comprises a compound (A) represented by the following formula (hereinafter also referred to as "H2NTP") and a resin. The content of compound (A) in the resin composition is 0.001 to 50 parts by mass per 100 parts by mass of the resin in the resin composition, and the resin includes any one of the following resins (J1) to (J3).

[0010] Resin (J1) Resin (J1) is a structural unit represented by the following general formula (1): —OSi(R １ R ２ )O— and a diol moiety (M) derived from a dihydroxy compound represented by M: [In general formula (1), R １ and R ２are each independently selected from the group consisting of an alkyl group having 1 to 20 carbon atoms which may have a substituent, and an aryl group having 6 to 30 carbon atoms which may have a substituent.

[0011] Resin (J2) Resin (J2) is a polycarbonate resin, polyester resin, or polyestercarbonate resin containing a structural unit derived from a monomer represented by the following general formula (3) and / or a structural unit derived from a monomer represented by the following general formula (4): [In general formula (3), R ａ and R ｂ each independently represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 20 carbon atoms which may have a substituent, an alkoxyl group of 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group of 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group of 5 to 20 carbon atoms which may have a substituent, an aryl group of 6 to 20 carbon atoms which may have a substituent, a heteroaryl group of 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 of 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 optionally substituted 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; and a and b each independently represent an integer of 0 to 10.

[0012] [In general formula (4), R ｃ and R ｄare each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group of 1 to 20 carbon atoms which may have a substituent, an alkoxyl group of 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group of 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group of 5 to 20 carbon atoms which may have a substituent, and an aryl group of 6 to 20 carbon atoms which may have a substituent; A and B each independently represent an alkylene group of 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; Y １ represents a single bond, an optionally substituted fluorene group, or any of the structures represented by the following general formulae (8), (9), and (11) to (17): (In general formulas (8), (9), (11) to (14), R ２１ and R ２２ 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 ２１ and R ２２ are bonded to each other to form a carbon ring or hetero ring having 1 to 20 carbon atoms which may have a substituent; r and s each independently represent an integer of 0 to 5000; in the general formulae (15) to (17), R ２３ and R ２４ each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, or represents an alkyl group having 1 to 9 carbon atoms, an alkoxyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms, each of which may have a substituent.

[0013] Resin (J3) Resin (J3) is a thermoplastic resin containing: a silane structural unit (S') derived from at least one silane compound selected from: a dialkoxysilane compound containing at least one of dialkyldialkoxysilane, diaryldialkoxysilane, and monoalkylmonoaryldialkoxysilane; a diaryloxysilane compound containing at least one of dialkyldiaryloxysilane, diaryldiaryloxysilane, and monoalkylmonoaryldiaryloxysilane; and a monoalkoxymonoaryloxysilane compound containing at least one of dialkylmonoalkoxymonoaryloxysilane, diarylmonalkoxymonoaryloxysilane, and monoalkylmonoarylmonalkoxymonoaryloxysilane compound; a fluorene structural unit (F) derived from a fluorene ring-containing dihydroxy compound; and a dinaphthalene structural unit (N) derived from a dinaphthalene-containing dihydroxy compound.

[0014] The present inventors have discovered that a resin composition obtained by blending the specific resin described above with compound (A) has physical properties particularly favorable for optical materials. In particular, it has been found that blending compound (A) into a resin improves the refractive index compared to the same resin without compound (A) or a resin using other blending ingredients. That is, blending compound (A) can improve the refractive index, which is a particularly favorable effect when using a resin composition as an optical material. Generally, when the refractive index of an optical material is high, a lens element having the same refractive index can be realized with a surface having a smaller curvature, thereby reducing the amount of aberration generated by this surface. As a result, it is possible to reduce the number of lenses, reduce the decentering sensitivity of the lens, and reduce the lens thickness and weight.

[0015] Possible methods for incorporating compound (A) include (i) polymerizing a monomer to produce a resin and then adding compound (A) to the resin to obtain a resin composition, and (ii) premixing materials containing the monomers constituting the resin and compound (A) and subjecting the resulting mixture to a polymerization process to obtain a resin composition. It has been found that, when method (i) is adopted, the addition of compound (A) particularly improves the melt fluidity of the resin (increasing the MVR value) and lowers the glass transition temperature (Tg). The improved melt fluidity and lowered glass transition temperature of the resin improve the moldability of the resin composition. In recent years, the trend toward lighter, thinner, shorter, and smaller products has created a particular demand for optical resins with high refractive indexes and excellent moldability, making the above-described effects of incorporating compound (A) highly desirable. Furthermore, when method (i) is adopted, a resin composition with particularly excellent moist heat resistance can also be obtained.

[0016] On the other hand, when method (ii) was adopted, it was found that the addition of compound (A) accelerated the polymerization reaction. In other words, compound (A) acted as a polymerization accelerator. By accelerating the polymerization reaction, a resin with a high molecular weight was obtained, and as a result, a resin composition with sufficient strength for molding processing could be obtained. Furthermore, when method (ii) was adopted, the Abbe number was higher relative to the refractive index (i.e., when compared at the same refractive index). This has the advantage of reducing chromatic aberration. Furthermore, when method (ii) was adopted, the effect of lowering the glass transition temperature was also achieved, as in the case of method (i).

[0017] Thus, it can be said that compound (A) has the effect of modifying some of the properties of the resin. The reason why compound (A) exhibits such an effect is unclear, but is speculated as follows. Generally, when a large amount of a resin additive is blended, there is a risk that the resin's inherent optical properties may be reduced. However, compound (A) has a refractive index equal to or higher than that of the resin, and the phosphazene skeleton acts as a wavelength dispersion agent, thereby suppressing wavelength dispersion in the short wavelength region. As a result, compound (A) is thought to be able to improve resin fluidity and lower Tg while modifying the resin's optical properties.

[0018] Hereinafter, each component of the resin composition according to the embodiment, the production method, physical properties, applications, etc. will be described in detail. [1] Compound (A) The resin composition according to the embodiment contains a compound (A) represented by the following formula and a resin. The content of compound (A) in the resin composition is 0.001 to 50 parts by mass, preferably 0.01 to 40 parts by mass, more preferably 0.01 to 30 parts by mass, and particularly preferably 0.01 to 20, 0.01 to 10, or 0.01 to 5 parts by mass, relative to 100 parts by mass of the resin in the resin composition. By including compound (A) in such an amount, the desired effects achieved by adding compound (A) can be more effectively obtained.

[0019] As described above, when compound (A) is blended into a resin, the refractive index is improved compared to the same resin not blended with compound (A) or a resin using other blending agents. Thus, according to one embodiment, an blending agent containing compound (A) is provided that is added to a resin to improve the refractive index. In another embodiment, a method for improving the refractive index of a resin is provided, the method comprising mixing a material containing a monomer constituting the resin and compound (A) to obtain a mixture, and then subjecting the mixture to polymerization conditions to polymerize the monomer to obtain a resin composition.

[0020] [2] Resin The resin contained in the resin composition includes any one of the following resins (J1) to (J3). Resin (J1) Resin (J1) is a structural unit represented by the following general formula (1), -OSi(R １ R ２ )O— and a diol moiety (M) derived from a dihydroxy compound represented by M.

[0021] In general formula (1), R １ and R ２ are each independently selected from the group consisting of an alkyl group having 1 to 20 carbon atoms which may have a substituent, and an aryl group having 6 to 30 carbon atoms which may have a substituent; １ and R ２When R is an alkyl group which may have a substituent, it preferably has a total of 1 to 14 or 1 to 10 carbon atoms, more preferably has a total of 1 to 6 carbon atoms, and particularly preferably has a total of 1 or 2 carbon atoms. １ and R ２ When is an aryl group which may have a substituent, the total number of carbon atoms is preferably 6 to 20, more preferably 6 to 12, and particularly preferably 6 to 8.

[0022] The above-mentioned R １ and R ２ Examples of the substituent in R include a hydroxyl group, a halogen, an amino group, a vinyl group, a carboxyl group, a cyano group, a (meth)acryloxy group, a glycidyloxy group, and a mercapto group. When a substituent is contained, the range of the number of carbon atoms mentioned above means the total number of carbon atoms including the number of carbon atoms of the substituent. １ and R ２ Preferred examples of the group include a methyl group, an ethyl group, a propyl group, a phenyl group, and a benzyl group, and more preferred are a methyl group and a phenyl group.

[0023] Examples of silane compounds for forming the silane portion (S) in general formula (1) include dialkoxysilane compounds, diaryloxysilane compounds, and monoalkoxymonoaryloxysilane compounds. Examples of dialkoxysilane compounds include dialkyldialkoxysilanes, diaryldialkoxysilanes, and monoalkylmonoaryldialkoxysilanes. Examples of diaryloxysilane compounds include dialkyldiaryloxysilanes, diaryldiaryloxysilanes, and monoalkylmonoaryldiaryloxysilanes. Examples of monoalkoxymonoaryloxysilane compounds include dialkylmonoalkoxymonoaryloxysilanes, diarylmonalkoxymonoaryloxysilanes, and monoalkylmonoarylmonalkoxymonoaryloxysilanes.

[0024] The silane compound forming the silane moiety (S) is represented by the general formula Si(R １ R２ ) (OR ３ ) ２ When expressed as １ and R ２ is as described above for formula (1), and OR ３ The two —OR groups each independently represent an alkoxy group or an aryloxy group in the silane compound. ３ The group is not introduced into the polymer chain (main chain) of the thermoplastic resin, but generates by-products such as methanol and phenol. Therefore, the type of alkoxy group or aryloxy group is not particularly limited. However, aryloxy groups and alkoxy groups with a relatively small number of carbon atoms are preferred so that by-products in the polymerization step can be removed from the reaction system as easily as possible. For example, an aryloxy group having 8 or less carbon atoms or an alkoxy group having 3 or less carbon atoms is preferred, and a phenoxy group (-OC ６ H ５ group), benzyloxy group, methoxy group, ethoxy group, etc., and particularly preferred is a phenoxy group or a methoxy group.

[0025] Preferred specific examples of the silane compound include dimethyldiphenoxysilane, dimethyldimethoxysilane, methylethyldimethoxysilane, diethyldimethoxysilane, diphenyldimethoxysilane, and methylphenyldimethoxysilane. More preferred specific examples of the silane compound include diphenyldimethoxysilane, dimethyldiphenoxysilane, and dinaphthyldimethoxysilane (DNDMS). As the silane compound forming the silane moiety (S), a single dialkoxysilane compound may be used, or multiple dialkoxysilane compounds may be used in combination.

[0026] M, which is shown schematically in the above formula (1), is a diol moiety (M) derived from a dihydroxy compound. The diol moiety (M) may contain a unit (B) derived from a diol containing a specific bisphenol, a dinaphthalene unit (N), a fluorene unit (F), or the like. Many of the diol moieties (M) are bonded to a silane moiety (S) at their terminals, and some of the diol moieties (M) may be bonded to each other. The diol moiety (M) will be described in detail below.

[0027] (a) Units (B) Derived from Diols The units (B) derived from diols such as bisphenols are represented by, for example, the following general formula (A-1) or (A-2).

[0028] In general formulas (A-1) and (A-2), R ３ ~R １０ and R ３０ ~R ３３ are each independently hydrogen, halogen, alkoxy, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkenyl group having 2 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent. ３ ~R １０ and R ３０ ~R ３３ When R is an alkyl group which may have a substituent, the total number of carbon atoms in the substituent and the alkyl group is preferably 1 to 10, more preferably 1 to 4, and particularly preferably 1 or 2. ３ ~R １０ and R ３０ ~R ３３ When R is an alkenyl group which may have a substituent, the total number of carbon atoms in the substituent and the alkenyl group is preferably 2 to 10, more preferably 2 to 6, and particularly preferably 2 to 4. ３ ~R １０ and R ３０ ~R ３３When is an aryl group which may have a substituent, the total number of carbon atoms in the substituent and the aryl group is preferably 6 to 20, more preferably 6 to 12, and particularly preferably 6 to 8.

[0029] Z １ and Z ２ are each independently an alkylene group having 1 to 5 carbon atoms which may have a substituent. １ and Z ２ are each preferably an alkylene group having 1 to 3 carbon atoms, more preferably an alkylene group having 1 or 2 carbon atoms. １ and K. １ are each independently an integer of 0 to 5. １ and K. １ are each independently preferably an integer of 0 to 3, more preferably an integer of 1 to 3 or 0 to 2, and particularly preferably 1 or 2, for example.

[0030] Also, J １ and K. １ When each of the —OZ groups in the formulas (A-1) and (A-2) is 1 or more, the diol-derived unit (B) is preferably derived from a dihydroxy compound having an aliphatic hydrocarbon group bonded to a terminal hydroxyl group. １ - and - OZ ２ Each - moiety is independently -CH ２ OH, -CH ２ CH ２ OH, -CH ２ CH ２ CH ２ It is preferably derived from an alkyl group such as OH having 1 to 5 carbon atoms and a terminal hydroxyl group (an alkyl group in which the terminal hydrogen is substituted with a hydroxyl group).

[0031] In addition, the aliphatic dihydroxy compounds having no aromatic ring moiety in the general formulas (A-1) and (A-2) are -CH ２ OH, -CH ２ CH ２ OH, -CH ２ CH ２ CH２ The diol-derived unit (B) may be formed by using an aliphatic dihydroxy compound containing an alkyl group having a terminal hydroxyl group (an alkyl group in which the terminal hydrogen is substituted with a hydroxyl group) having 1 to 5 carbon atoms, such as OH, in combination with the aromatic dihydroxy compound. Alternatively, the diol-derived unit (B) may be formed by using only such an aliphatic dihydroxy compound. The number of carbon atoms in the alkyl group having a terminal hydroxyl group is preferably 1 to 3, and more preferably 1 or 2.

[0032] In the general formulas (A-1) and (A-2), X's each independently represent a single bond or any of the structural formulas represented by the following general formula (2): In general formula (2), R １１ and R １２ each independently represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 30 carbon atoms; or R １１ and R １２ are bonded to each other to form a carbon ring or hetero ring having 1 to 20 carbon atoms, which may have a substituent. a and b each independently represent 0 or an integer of 1 to 5000. R １１ and R １２ are preferably each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an optionally substituted aryl group having 6 to 16 carbon atoms.

[0033] In the general formula (2), a and b each independently represent 0 or an integer of 1 to 5000, preferably an integer of 1000 or less, more preferably an integer of 500 or less, and even more preferably an integer of 100 or less. １１ and R １２ are preferably bonded to each other to form a fluorene ring structure.

[0034] Examples of the substituent in each of the above groups include a hydroxyl group, a halogen, an amino group, a vinyl group, a carboxyl group, a cyano group, a (meth)acryloxy group, a glycidyloxy group, a mercapto group, etc. When a substituent is contained, the above-mentioned preferable range of the number of carbon atoms means the total number of carbon atoms including the number of carbon atoms of the substituent.

[0035] Specific examples of the unit (B) derived from a diol include units derived from bisphenol compounds such as bisphenol A, bisphenol AP, bisphenol AF, bisphenol B, bisphenol C, bisphenol BP, bisphenol E, bisphenol F, bisphenol G, bisphenol M, bisphenol S, bisphenol P, bisphenol PH, bisphenol TMC, and bisphenol Z. The type of resin (J1) is not particularly limited, but is preferably a polycarbonate resin, a polyester resin, or a polyestercarbonate resin.

[0036] (b) Dinaphthalene Unit (N) The dinaphthalene unit (N) is derived from a dinaphthalene-containing dihydroxy compound. The dinaphthalene-containing dihydroxy compound for forming the dinaphthalene unit (N) is represented, for example, by the following general formula (3).

[0037] In general formula (3), R ａ and R ｂ each independently represents a halogen atom, an alkyl group of 1 to 20 carbon atoms which may have a substituent, an alkoxyl group of 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group of 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group of 5 to 20 carbon atoms which may have a substituent, an aryl group of 6 to 20 carbon atoms which may have a substituent, a heteroaryl group of 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 of 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ 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. ａ and R ｂ is preferably a hydrogen atom, an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, more preferably a hydrogen atom or an aryl group having 6 to 20 carbon atoms which may have a substituent, and even more preferably a hydrogen atom or an aryl group having 6 to 12 carbon atoms which may have a substituent.

[0038] In general formula (3), X represents a single bond or an optionally substituted fluorene group. X is preferably a single bond or an optionally substituted fluorene group having a total of 12 to 20 carbon atoms. In general formula (3), A and B each independently represent an optionally substituted alkylene group having 1 to 5 carbon atoms, preferably an alkylene group having 2 or 3 carbon atoms. In general formula (3), m and n each independently represent an integer of 0 to 6, preferably an integer of 0 to 3, more preferably 0 or 1. In general formula (3), a and b each independently represent an integer of 0 to 10, preferably an integer of 1 to 3, more preferably 1 or 2.

[0039] Examples of the substituent in the definition of each group above include a hydroxyl group, a halogen atom, an amino group, a vinyl group, a carboxyl group, a cyano group, a (meth)acryloxy group, a glycidyloxy group, a mercapto group, etc. When a substituent is contained, the above-mentioned preferable range of the number of carbon atoms means the total number of carbon atoms including the number of carbon atoms of the substituent.

[0040] Specific examples of the dinaphthalene unit (N) include those derived from 2,2'-bis(2-hydroxyethoxy)-6,6'-diphenyl-1,1'-binaphthalene (DPBN), 2,2'-bis(2-hydroxyethoxy)-6,6'-di(naphthalen-2-yl)-1,1'-binaphthalene (2NBN), 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), etc., and more preferably, units derived from 2NBN, DPBN, BNE, etc.

[0041] Thermoplastic resins containing dinaphthalene units (N) have the effect of having superior heat resistance compared to thermoplastic resins containing structural units including an alicyclic ring derived from an alicyclic diol, or structural units including a monocyclic aromatic ring derived from bisphenols or the like.

[0042] (c) Fluorene Unit (F) The fluorene unit (F) is derived from a fluorene ring-containing dihydroxy compound. The fluorene ring-containing dihydroxy compound is preferably, for example, one represented by the following general formula (4). In general formula (4), R ｃ and R ｄ are each independently selected from the group consisting of a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkoxyl group having 1 to 20 carbon atoms, an optionally substituted cycloalkyl group having 5 to 20 carbon atoms, an optionally substituted cycloalkoxyl group having 5 to 20 carbon atoms, and an optionally substituted aryl group having 6 to 20 carbon atoms. 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.

[0043] In the general formula (4), Y １is a single bond, a fluorene group which may have a substituent, or any of the structures represented by the following general formulas (8), (9), (11) to (17).

[0044]

[0045] In formulas (8), (9), (11) to (14), R ２１ and R ２２ 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 ２１ and R ２２ are bonded to each other to form a carbon ring or hetero ring having 1 to 20 carbon atoms which may have a substituent. r and s each independently represent an integer of 0 to 5000. In formulas (15) to (17), R ２３ and R ２４ each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, or an alkyl group having 1 to 9 carbon atoms, an alkoxyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms, each of which may have a substituent.

[0046] In the general formula (4), 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 general formula (4), p and q are each independently an integer of 0 to 4, and preferably 0 or 1. In the general formula (4), 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.

[0047] Examples of the substituent in the definition of each group above include a hydroxyl group, a halogen atom, an amino group, a vinyl group, a carboxyl group, a cyano group, a (meth)acryloxy group, a glycidyloxy group, a mercapto group, etc. When a substituent is contained, the above-mentioned preferable range of the number of carbon atoms means the total number of carbon atoms including the number of carbon atoms of the substituent.

[0048] Specific examples of the fluorene unit (F) 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 Nol P-HTG (4,4'-(3,3,5-trimethylcyclohexylidene)bisphenol), bisphenol P-MIBK (4,4'-(1,3-dimethylbutylidene)bisphenol), bisphenol PEO-FL (bisphenoxyethanolfluorene), bisphenol P-3MZ (4-[1-(4-hydroxyphenyl)-3-methylcyclohexyl]phenol), bisphenol OC-FL (4,4'-[1- [4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethylidene]bisphenol), bisphenol Z, BP-2EO (2,2'-[[1,1'-biphenyl]-4,4'-diylbis(oxy)bisethanol), S-BOC (4,4'-(1-methylethylidene)bis(2-methylphenol),) TrisP-HAP (4,4',4''-ethylidene trisphenol), etc. Among these, more preferred specific examples of the fluorene unit (F) include those derived from BNEF, BPEF, or BPPEF.

[0049] When the diol portion (M) contains both the dinaphthalene unit (N) and the fluorene unit (F), a thermoplastic resin with a high refractive index can be obtained. Furthermore, in a thermoplastic resin containing the dinaphthalene unit (N), it is possible to easily incorporate an appropriate amount of additives or low-molecular-weight compounds. Such a thermoplastic resin is thought to have the advantage of improving productivity by improving plasticity during molding, and further reducing energy consumption.

[0050] In the resin (J1), the proportion of the structural units of general formula (1) in all structural units is preferably 70 mol% or more, more preferably 80 mol% or more, even more preferably 90 mol% or more, and particularly preferably 95 mol% or more. Furthermore, the resin (J1) may be composed only of structural units of general formula (1).

[0051] Resin (J2) Resin (J2) is a polycarbonate resin, polyester resin, or polyestercarbonate resin containing a structural unit derived from a monomer represented by the following general formula (3) and / or a structural unit derived from a monomer represented by the following general formula (4):

[0052] In general formula (3), R ａ and R ｂ each independently represents a halogen atom, an alkyl group of 1 to 20 carbon atoms which may have a substituent, an alkoxyl group of 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group of 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group of 5 to 20 carbon atoms which may have a substituent, an aryl group of 6 to 20 carbon atoms which may have a substituent, a heteroaryl group of 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 of 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. ａand R ｂ is preferably a hydrogen atom, an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 6 to 20 carbon atoms which contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, more preferably a hydrogen atom or an aryl group having 6 to 20 carbon atoms which may have a substituent, and even more preferably a hydrogen atom or an aryl group having 6 to 12 carbon atoms which may have a substituent.

[0053] In general formula (3), X represents a single bond or an optionally substituted fluorene group. X is preferably a single bond or an optionally substituted fluorene group having a total of 12 to 20 carbon atoms. In general formula (3), A and B each independently represent an optionally substituted alkylene group having 1 to 5 carbon atoms, preferably an alkylene group having 2 or 3 carbon atoms. In general formula (3), m and n each independently represent an integer of 0 to 6, preferably an integer of 0 to 3, more preferably 0 or 1. In general formula (3), a and b each independently represent an integer of 0 to 10, preferably an integer of 1 to 3, more preferably 1 or 2.

[0054] Examples of the substituent in the definition of each group above include a hydroxyl group, a halogen atom, an amino group, a vinyl group, a carboxyl group, a cyano group, a (meth)acryloxy group, a glycidyloxy group, a mercapto group, etc. When a substituent is contained, the above-mentioned preferable range of the number of carbon atoms means the total number of carbon atoms including the number of carbon atoms of the substituent.

[0055] Specific examples of the monomer represented by general formula (3) include 2,2'-bis(2-hydroxyethoxy)-6,6'-diphenyl-1,1'-binaphthalene (DPBN), 2,2'-bis(2-hydroxyethoxy)-6,6'-di(naphthalen-2-yl)-1,1'-binaphthalene (2NBN), 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), and the like, and more preferably 2NBN, DPBN, and the like.

[0056] Thermoplastic resins containing a structural unit derived from a monomer represented by general formula (3) have the effect of having superior heat resistance compared to thermoplastic resins containing a structural unit containing an alicyclic ring derived from an alicyclic diol, or a structural unit containing a monocyclic aromatic ring derived from a bisphenol or the like.

[0057]

[0058] In general formula (4), R ｃ and R ｄ are each independently selected from the group consisting of a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkoxyl group having 1 to 20 carbon atoms, an optionally substituted cycloalkyl group having 5 to 20 carbon atoms, an optionally substituted cycloalkoxyl group having 5 to 20 carbon atoms, and an optionally substituted aryl group having 6 to 20 carbon atoms. 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.

[0059] In the general formula (4), Y １ is a single bond, a fluorene group which may have a substituent, or any of the structures represented by the following general formulas (8), (9), (11) to (17).

[0060] In formulas (8), (9), (11) to (14), R ２１ and R ２２ 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 ２１ and R ２２are bonded to each other to form a carbon ring or hetero ring having 1 to 20 carbon atoms which may have a substituent. r and s each independently represent an integer of 0 to 5000. In formulas (15) to (17), R ２３ and R ２４ each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, or an alkyl group having 1 to 9 carbon atoms, an alkoxyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms, each of which may have a substituent.

[0061] In the general formula (4), 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 general formula (4), p and q are each independently an integer of 0 to 4, and preferably 0 or 1. In the general formula (4), 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.

[0062] Examples of the substituent in the definition of each group above include a hydroxyl group, a halogen atom, an amino group, a vinyl group, a carboxyl group, a cyano group, a (meth)acryloxy group, a glycidyloxy group, a mercapto group, etc. When a substituent is contained, the above-mentioned preferable range of the number of carbon atoms means the total number of carbon atoms including the number of carbon atoms of the substituent.

[0063] Specific examples of the monomer represented by general formula (4) 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), and bisphenol P-CDE (4,4'-cyclododecylidenebisphenol). 1), bisphenol P-HTG (4,4'-(3,3,5-trimethylcyclohexylidene)bisphenol), bisphenol P-MIBK (4,4'-(1,3-dimethylbutylidene)bisphenol), bisphenol PEO-FL (bisphenoxyethanolfluorene), bisphenol P-3MZ (4-[1-(4-hydroxyphenyl)-3-methylcyclohexyl]phenol), bisphenol OC-FL (4 ,4'-[1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethylidene]bisphenol), bisphenol Z, BP-2EO (2,2'-[[1,1'-biphenyl]-4,4'-diylbis(oxy)bisethanol), S-BOC (4,4'-(1-methylethylidene)bis(2-methylphenol)) TrisP-HAP (4,4',4''-ethylidene trisphenol). Among these, BNEF, BPEF, and BPPEF are preferred.

[0064] In resin (J2), the total proportion of structural units of general formula (3) and structural units of general formula (4) in all structural units is preferably 70 mol% or more, more preferably 80 mol% or more, even more preferably 90 mol% or more, and particularly preferably 95 mol% or more. Furthermore, resin (J2) may be composed solely of structural units of general formula (3) and / or structural units of general formula (4).

[0065] Resin (J3) Resin (J3) is a thermoplastic resin containing: a silane structural unit (S') derived from at least one silane compound selected from: a dialkoxysilane compound containing at least one of dialkyldialkoxysilane, diaryldialkoxysilane, and monoalkylmonoaryldialkoxysilane; a diaryloxysilane compound containing at least one of dialkyldiaryloxysilane, diaryldiaryloxysilane, and monoalkylmonoaryldiaryloxysilane; and a monoalkoxymonoaryloxysilane compound containing at least one of dialkylmonoalkoxymonoaryloxysilane, diarylmonalkoxymonoaryloxysilane, and monoalkylmonoarylmonalkoxymonoaryloxysilane compound; a fluorene structural unit (F) derived from a fluorene ring-containing dihydroxy compound; and a dinaphthalene structural unit (N) derived from a dinaphthalene-containing dihydroxy compound.

[0066] The specific structure of the silane structural unit (S') is as described above for the silane moiety (S) in general formula (1) of resin (J1), and the preferred ranges thereof are also the same. The fluorene structural unit (F) and the dinaphthalene structural unit (N) are as described above for the fluorene unit (F) and the dinaphthalene unit (N) of resin (J1), and the preferred ranges thereof are also the same.

[0067] In resin (J3), the content of fluorene structural units (F) is preferably 30 to 95 mol% based on the total number of moles of the fluorene structural units (F) and the dinaphthalene structural units (N). The content of fluorene structural units (F) based on the total number of moles of the fluorene structural units (F) and the dinaphthalene structural units (N) is more preferably 40 to 92 mol%, even more preferably 50 to 90 mol%, and particularly preferably 50 to 80 mol%. In resin (J3), the content of dinaphthalene structural units (N) is preferably 5 to 70 mol% based on the total number of moles of the fluorene structural units (F) and the dinaphthalene structural units (N). The content of the dinaphthalene structural unit (N) in the total number of moles of the fluorene structural unit (F) and the dinaphthalene structural unit (N) is more preferably 8 to 60 mol%, even more preferably 10 to 50 mol%, and particularly preferably 20 to 50 mol%.

[0068] In resin (J3), the silane structural unit (S') bonds to the end of the fluorene structural unit (F) or the dinaphthalene structural unit (N), and is contained in an amount of approximately equal moles to the total number of moles of the fluorene structural unit (F) and the dinaphthalene structural unit (N) for the following reason. The silane structural unit (S') is formed by elimination of an alkoxy group or a monoaryloxy group in the silane compound during a polymerization reaction between the above-mentioned silane compound and the hydroxyl group of a dinaphthalene-containing dihydroxy compound or a fluorene ring-containing dihydroxy compound. For this reason, in thermoplastic resins, the number of moles of the silane structural unit (S') is usually equal to the total number of moles of the fluorene structural unit (F) and the dinaphthalene structural unit (N). However, when silane structural units (S') are positioned at both ends of structural unit (F) or (N), the number of moles of silane structural units (S') may be slightly in excess of the total number of moles of structural units (F) and (N), and for example, the number of moles of silane structural units (S') may be about 1.01 times the total number of moles of structural units (F) and (N). Thus, the number of moles of silane structural units (S') in resin (J3) is, for example, 1.00 to 1.05 times, preferably 1.00 to 1.03 times, and more preferably 1.00 to 1.01 times the total number of moles of fluorene structural units (F) and dinaphthalene structural units (N).

[0069] In the resin (J3), the total proportion of the silane structural unit (S'), the fluorene structural unit (F), and the dinaphthalene structural unit (N) in all structural units is preferably 70 mol% or more, more preferably 80 mol% or more, even more preferably 90 mol% or more, and particularly preferably 95 mol% or more. Furthermore, the resin (J3) may be a thermoplastic resin composed only of the silane structural unit (S'), the fluorene structural unit (F), and the dinaphthalene structural unit (N). The type of resin (J3) is not particularly limited, but is preferably a polycarbonate resin, a polyester resin, or a polyester carbonate resin.

[0070] Resins (J1) to (J3) may contain other structural units in addition to those described above. That is, for resin (J1), other structural units other than the structural unit of general formula (1); for resin (J2), other structural units other than the structural unit of general formula (3) and the structural unit of general formula (4); and for resin (J3), other structural units other than the silane structural unit (S'), the fluorene structural unit (F), and the dinaphthalene structural unit (N). Such other structural units may be contained in a proportion of preferably 30 mol% or less, more preferably 20 mol% or less, even more preferably 10 mol% or less, and particularly preferably 5 mol% or less, relative to all structural units of resin (J1), (J2), or (J3). By ensuring that the proportion of other structural units is within the above range, the effects of the present invention achieved by incorporating compound (A) can be more effectively exhibited. Furthermore, when resins (J1) to (J3) are composed of multiple types of structural units, they may be random copolymers or block copolymers.

[0071] More specifically, other constituent units include dicarboxylic acids or ester-forming derivatives thereof. Examples of dicarboxylic acids include aliphatic dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, methylmalonic acid, and ethylmalonic acid, monocyclic aromatic dicarboxylic acids such as phthalic acid, isophthalic acid, and terephthalic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, anthracenedicarboxylic acid, phenanthrenedicarboxylic acid, 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl, 9,9-bis(carboxymethyl)fluorene, 9,9-bis(2-carboxyethyl)fluorene, 9,9-bis(1-carboxyethyl)fluorene, and 9,9-bis(1-carboxypropyl)fluorene. Examples of the dicarboxylic acid include polycyclic aromatic dicarboxylic acids such as 9,9-bis(2-carboxypropyl)fluorene, 9,9-bis(2-carboxy-1-methylethyl)fluorene, 9,9-bis(2-carboxy-1-methylpropyl)fluorene, 9,9-bis(2-carboxybutyl)fluorene, 9,9-bis(2-carboxy-1-methylbutyl)fluorene, 9,9-bis(5-carboxypentyl)fluorene, and 9,9-bis(carboxycyclohexyl)fluorene; biphenyl dicarboxylic acids such as 2,2'-biphenyl dicarboxylic acid; 1,4-cyclohexane dicarboxylic acid; and 2,6-decalin dicarboxylic acid; and isophthalic acid, terephthalic acid, 2,6-naphthalenedicarboxylic acid, and 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl are preferred. These may be used alone or in combination of two or more. As the ester-forming derivatives, acid chlorides of the above carboxylic acids, and esters such as methyl esters, ethyl esters, and phenyl esters may also be used.

[0072] As the dicarboxylic acid, for example, a compound represented by the following general formula (C) is also preferably used.

[0073] In the above formula (C), R １ and R ２R each independently represents a hydrocarbon group having 1 to 10 carbon atoms which may contain an aromatic group, and n and m each independently represent an integer of 0 or greater. ３ ~R １０ each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a hydrocarbon group which may contain an aromatic group having 1 to 20 carbon atoms.

[0074] Representative examples of the dicarboxylic acid represented by formula (C) or its ester-forming derivative are shown below, but the invention is not limited thereto: 2,2'-dicarboxy-1,1'-binaphthyl, 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl, 2,2'-bis(2-carboxyethoxy)-1,1'-binaphthyl, 2,2'-bis(3-carboxypropoxy)-1,1'-binaphthyl, 2,2'-dimethoxycarbonyl-1,1'-binaphthyl, 2,2'-bis(methoxycarbonyl) 2,2'-bis(2-methoxycarbonylethoxy)-1,1'-binaphthyl, 2,2'-bis(3-methoxycarbonylpropoxy)-1,1'-binaphthyl, 2,2'-diethoxycarbonyl-1,1'-binaphthyl, 2,2'-bis(ethoxycarbonylmethoxy)-1,1'-binaphthyl, 2,2'-bis(2-ethoxycarbonyl 2,2'-bis(2-phenoxycarbonylethoxy)-1,1'-binaphthyl, 2,2'-bis(3-ethoxycarbonylpropoxy)-1,1'-binaphthyl, 2,2'-diphenoxycarbonyl-1,1'-binaphthyl, 2,2'-bis(2-phenoxycarbonylethoxy)-1,1'-binaphthyl, 2,2'-bis(3-phenoxycarbonylpropoxy)-1,1'-binaphthyl 2,2'-ditert-butoxycarbonyl-1,1'-binaphthyl, 2,2'-bis(tert-butoxycarbonylmethoxy)-1,1'-binaphthyl, 2,2'-bis(2-tert-butoxycarbonylethoxy)-1,1'-binaphthyl, 2,2'-bis(3-tert-butoxycarbonylpropoxy)-1,1'-binaphthyl, and the like. １ and R ２ is a methylene group, o and p are 1, and R ３ ~R１０ is a hydrogen atom, 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl (BINOL-DC) or an ester-forming derivative thereof is preferred, and 2,2'-bis(phenoxycarbonylmethoxy)-1,1'-binaphthyl (BINOL-DP), 2,2'-bis(ethoxycarbonylmethoxy)-1,1'-binaphthyl (BINOL-DE), or 2,2'-bis(methoxycarbonylmethoxy)-1,1'-binaphthyl (BINOL-DM) is also preferred. BINOL-DC is particularly preferred. For example, the resin may contain a structural unit derived from the monomer represented by general formula (4) in resin (J2) and a structural unit derived from the dicarboxylic acid represented by general formula (C) above.

[0075] The resin may contain a structural unit derived from at least one monomer selected from the following group of monomers. (In the above formula, R １ and R ２ each independently represents a hydrogen atom, a methyl group, an ethyl group, or a phenyl group; R ３ and R ４ each independently represents a hydrogen atom, a methyl group, an ethyl group, a phenyl group, or an alkylene glycol having 2 to 5 carbon atoms.

[0076] (4) Optional Structural Unit (Structural Unit (Z)) The resin may contain a structural unit (optional structural unit (Z)) other than those described above. Examples include structural units derived from the following diol compounds.

[0077] The structural unit (Z) may be a unit represented by the following formula (I １ ) ~ (I ６ These diol compounds are each derived from a diol compound represented by the formula (I). １ ) ~ (I ６ ) may be abbreviated as

[0078] Diol compound (I １ ) is represented by the following formula (I １ ) [In the formula, R １ and R ２are independently −(CR ５ R ６ ) ｑ１ - or -(-O-(CR ５ R ６ ) ｑ２ -) ｑ３ - (wherein, R ５ and R ６ are independently H or C １－６ represents an alkyl group; q1 represents an integer of 0 or more and 10 or less; q2 represents an integer of 1 or more and 10 or less; q3 represents an integer of 1 or more and 10 or less; when q1 or q2 is an integer of 2 or more, a plurality of R ５ or R ６ may be the same or different), R ３ and R ４ are independently one or more halogeno groups selected from the group consisting of chloro, bromo and iodo; C １－２０ Aliphatic hydrocarbon group, C １－２０ Alkoxyl group, C ３－２０ Cycloalkyl group, C ６－２０ Aromatic hydrocarbon group, C ７－２０ Aralkyl group, C 6-20 Aromatic hydrocarbon oxy group, or C ３－２０ represents a cycloalkoxyl group; X １ is one of the groups shown below, (In the formula, R ７ and R ８ are independently selected from the group consisting of H, chloro, bromo and iodo, C optionally having a substituent α, １－２０ an aliphatic hydrocarbon group, C optionally having a substituent α １－２０ C optionally having an alkoxyl group or a substituent β ６－２０ represents an aromatic hydrocarbon group, or R ７ and R ８ are bonded to form C ３－２０ may form a carbocyclic ring or a 5- to 12-membered heterocyclic ring, R ９ and R １０ are independently H or C １－６ represents an alkyl group, and when r1 is an integer of 2 or more, a plurality of R ９ or R １０may be the same or different, R １１ ~R １８ C which may have one or more halogeno groups independently selected from the group consisting of chloro, bromo and iodo, １－２０ an aliphatic hydrocarbon group, C optionally having a substituent α １－２０ C optionally having an alkoxyl group or a substituent β ６－１２ represents an aromatic hydrocarbon group, R １９ C optionally having a substituent α １－９ represents an alkylene group, r1 represents an integer of 1 or more and 20 or less, and r2 represents an integer of 1 or more and 500 or less.

[0079] The above formula (I １ In the formula (I), p1 and p2 independently represent an integer of 0 to 4, and the substituent α is C １－６ Alkoxyl group, C １－７ is one or more substituents selected from an acyl group, one or more halogeno groups selected from the group consisting of chloro, bromo, and iodo, an amino group, a nitro group, a cyano group, and a carbamoyl group, and the substituent β is C １－６ Alkyl group, C １－６ Alkoxyl group, C １－７ The substituents are one or more selected from an acyl group, one or more halogeno groups selected from the group consisting of chloro, bromo and iodo, an amino group, a nitro group, a cyano group, and a carbamoyl group.

[0080] The above formula (I １ ) R １ and R ２ - (CR ５ R ６ ) ｑ１ Examples of - include an ethylene group (-CH ２ CH ２ -), and -O-(CR ５ R ６ ) ｑ２ - is, for example, -O-CH ２ CH ２ - and -O-CH(CH ３ ) CH ２ - can be mentioned.１ -(-O-(CR ５ R ６ ) ｑ2 -) ｑ3 -, HO-R from the viewpoint of stability １ -Ph is HO-(-O-(CR ５ R ６ ) ｑ２ -) ｑ３ It does not become -Ph, but HO-(-(CR ５ R ６ ) ｑ２ -O-) ｑ３ -Ph. q2 is preferably 2 or greater. Examples of the "halogeno group" include chloro, bromo, and iodo, with chloro or bromo being preferred, and chloro being more preferred.

[0081] "C １－２０ The term "aliphatic hydrocarbon group" refers to a linear or branched monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, １－２０ Alkyl group, C ２－２０ alkenyl groups, and C ２－２０ Examples of the alkyl group include an alkynyl group. １－２０ Examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, n-hexyl, n-octyl, n-decyl, n-pentadecyl, and n-icosyl. １－１０ Alkyl group or C １－６ alkyl group, more preferably C １－４ Alkyl group or C １－２ C is an alkyl group, and even more preferably methyl. ２－２０ Examples of alkenyl groups include ethenyl (vinyl), 1-propenyl, 2-propenyl (allyl), isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, pentenyl, hexenyl, octenyl, decenyl, pentadecenyl, and icosenyl. ２－１０ Alkenyl group or C ２－６ It is an alkenyl group, more preferably ethenyl (vinyl) or 2-propenyl (allyl). ２－２０Examples of the alkynyl group include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, pentynyl, hexynyl, octynyl, decynyl, pentadecynyl, and icosynyl. ２－１０ Alkynyl group or C ２－６ Alkynyl group, more preferably C ２－４ Alkynyl group or C ２－３ It is an alkynyl group.

[0082] "C １－２０ The term "alkoxyl group" refers to a linear or branched monovalent aliphatic hydrocarbon oxy group having 1 to 20 carbon atoms. Examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, n-pentoxy, and n-hexoxy, and preferably C １－１０ Alkoxyl group or C １－６ is an alkoxyl group, more preferably C １－４ Alkoxyl group or C １－２ It is an alkoxy group, and even more preferably methoxy. ３－２０ The term "cycloalkyl group" refers to a monovalent cyclic saturated aliphatic hydrocarbon group having 3 to 20 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl. Preferably, C ３－１０ It is a cycloalkyl group. ６－２０ The term "aromatic hydrocarbon group" refers to a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms. Examples include phenyl, indenyl, naphthyl, biphenyl, acenaphthenyl, fluorenyl, phenalenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, and perylenyl, and preferably C ６－１２ It is an aromatic hydrocarbon group, and more preferably phenyl. ７－２０ The term "aralkyl group" refers to an alkyl group substituted with one aromatic hydrocarbon group and having 7 to 20 carbon atoms. Examples include benzyl, phenethyl, phenylpropyl, naphthylmethyl, naphthylethyl, and biphenylmethyl, with benzyl being preferred.

[0083] "C６－２０ The term "aromatic hydrocarbon oxy group" refers to a monovalent aromatic hydrocarbon oxy group having 6 to 20 carbon atoms. Examples include phenoxy, indenyloxy, naphthyloxy, biphenyloxy, acenaphthenyloxy, fluorenyloxy, phenalenyloxy, phenanthrenyloxy, anthracenyloxy, triphenylenyloxy, pyrenyloxy, chrysenyloxy, naphthacenyloxy, and perylenyloxy. Preferably, C ６－１２ It is an aromatic hydrocarbon oxy group, more preferably phenoxy. ３－２０ The term "cycloalkoxyl group" refers to a monovalent cyclic saturated aliphatic hydrocarbon oxy group having 3 to 20 carbon atoms. Examples include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, adamantyloxy, and cyclododecanyl. Preferably, C ３－１２ The substituent α is a cycloalkyloxy group. １－６ Alkoxyl group, C １－７ Examples of the substituent β include one or more substituents selected from an acyl group, one or more halogeno groups selected from the group consisting of chloro, bromo, and iodo, an amino group, a nitro group, a cyano group, and a carbamoyl group. １－６ Alkyl group, C １－６ Alkoxyl group, C １－７ Examples of the substituents include an acyl group, one or more halogeno groups selected from the group consisting of chloro, bromo, and iodo, an amino group, a nitro group, a cyano group, and a carbamoyl group. When the diol compound contains a substituent, the range of the carbon number refers to the total number of carbon atoms including the number of carbon atoms of the substituent.

[0084] "Amino group" includes unsubstituted amino groups (-NH ２ ) plus one C １－６ Mono C substituted with alkyl group １－６ Alkylamino group and two C １－６ Alkyl-substituted diC １－６ Alkylamino groups are included. Such amino groups include amino (—NH ２mono-C such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, t-butylamino, n-pentylamino, and n-hexylamino; １－６ Alkylamino groups: di-C groups such as dimethylamino, diethylamino, di(n-propyl)amino, diisopropylamino, di(n-butyl)amino, diisobutylamino, di(n-pentyl)amino, di(n-hexyl)amino, ethylmethylamino, methyl(n-propyl)amino, n-butylmethylamino, ethyl(n-propyl)amino, and n-butylethylamino; １－６ Examples include alkylamino groups, and preferably unsubstituted amino groups.

[0085] "C １－７ The term "acyl group" refers to the remaining atomic group obtained by removing OH from an aliphatic carboxylic acid having 1 to 7 carbon atoms. Examples include formyl, acetyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, t-butylcarbonyl, n-pentylcarbonyl, and n-hexylcarbonyl, and preferably C １－４ It is an acyl group, more preferably acetyl. The number of substituents of the substituent α is not particularly limited as long as it is substitutable, but can be, for example, 1 or more and 20 or less. The number of the substituents is preferably 10 or less, more preferably 5 or less or 3 or less, and even more preferably 2 or less or 1. The number of substituents of the substituent β is not particularly limited as long as it is substitutable, but can be, for example, 1 or more and 10 or less. The number of the substituents is preferably 5 or less, more preferably 3 or less, and even more preferably 2 or less or 1.

[0086] R ７ and R ８ C is formed by bonding ５－２０ The carbocyclic ring is a C ring optionally having a substituent β. ３－２０ Examples of the condensed ring include a cycloalkyl group and a condensed ring of a cycloalkyl group and an aromatic hydrocarbon group. Examples of the condensed ring include acenaphthenyl and fluorenyl. R ７ and R ８Examples of the 5- to 12-membered heterocycle formed by bonding include oxiranyl, aziridinyl, tetrahydrofuranyl, tetrahydrothiophenyl, pyrrolidinyl, oxathiolanyl, piperidinyl, 1(3H)-isobenzofuranonyl, and the like.

[0087] Diol compound (I １Specific examples of the bis(4-hydroxyphenyl)methane include the following compounds: bis(4-hydroxyphenyl)methane, bis(2-hydroxyphenyl)methane, 2,4'-dihydroxydiphenylmethane, bis(4-hydroxyphenyl)ether, bis(4-hydroxyphenyl)sulfone, 2,4'-dihydroxydiphenylsulfone, bis(2-hydroxyphenyl)sulfone, bis(4-hydroxy-3-methylphenyl)sulfone, bis(4-hydroxyphenyl)sulfoxide, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxyphenyl)ketone, 1,1-bis(4- 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bis(4-hydroxyphenyl)diphenylmethane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 1,1-bis(4-hydroxy-3-methylphenyl)ethane, bis(4-hydroxy-3-methylphenyl)methane, 2,2-bis(4-hydroxy-3-t-butylphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxyphenyl) 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)cycloundecane, 1,1-bis(4-hydroxyphenyl)cyclododecane, 2,2-bis(4-hydroxy-3-allylphenyl)propane, 3,3,5-trimethyl-1,1-bis(4-hydroxyphenyl)cyclohexane, 9,9-bis(4-hydroxy-3-ethylphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxyphenyl)cyclohexane bis(4-hydroxyphenyl)fluorene, α,ω-bis[3-(o-hydroxyphenyl)propyl]polydimethyldiphenyl random copolymer siloxane, α,ω-bis[3-(o-hydroxyphenyl)propyl]polydimethylsiloxane, 4,4'-[1,4-phenylenebis(1-methylethylidene)]bisphenol, 4,4'-[1,3-phenylenebis(1-methylethylidene)]bisphenol, 2,2-bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxyphenyl)-2-ethylhexane, 1,1-bis(4-hydroxyphenyl)-2-methylpropane, 2,2-bis(4-hydroxyphenyl)-4-methylpentane, 1,1-bis(4-hydroxyphenyl)decane, 1,3-bis(4-hydroxyphenyl)-5,7-dimethyladamantane, 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-t-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-t-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-cyclohexylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene, 4-(9-(4-hydroxyethoxy)phenyl)-9H-fluoren-9-yl)phenol, 2,2-bis(4-(2-hydroxyethoxy)phenyl)propane, 4,4-bis(2-hydroxyethoxy)biphenyl, 2,2'(9H-fluorene-9,9'-diyl)bis(ethan-1-ol), 9H- (fluorene-9,9-diyl)dimethanol, 2,2'-(1,4-phenylene)bis(ethan-1-ol), 2,2'-(1,4-phenylene)bis(methane-1-ol), 2,2'-(1,4-phenylenebis(oxy))bis(ethan-1-ol), 1,1-bis(4-hydroxyphenyl)cyclododecane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclododecane, 1,1-bis(4-hydroxy-3-phenylphenyl)cyclododecane, 1,1-bis(4-hydroxy-3-t-butylphenyl)cyclododecane, 1, 1-bis(4-hydroxy-3-sec-butylphenyl)cyclododecane, 1,1-bis(4-hydroxy-3-allylphenyl)cyclododecane, 1,1-bis(4-hydroxy-3,5-dimethylphenyl)cyclododecane, 1,1-bis(4-hydroxy-3-fluorophenyl)cyclododecane, 1,1-bis(4-hydroxy-3-chlorophenyl)cyclododecane, 1,1-bis(4-hydroxy-3-bromophenyl)cyclododecane, 7-ethyl-1,1-bis(4-hydroxyphenyl)cyclododecane, 5,6-dimethyl-1,Examples include 1-bis(4-hydroxyphenyl)cyclododecane.

[0088] Among these, bis(4-hydroxyphenyl)methane, bis(2-hydroxyphenyl)methane, 2,4'-dihydroxydiphenylmethane, bis(4-hydroxyphenyl)ether, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene, 1,1-bis(4-hydroxyphenyl)cyclododecane, and 1,1-bis(4-hydroxy-3-methylphenyl)cyclododecane are particularly preferred. Furthermore, representative diol compounds (I) １ ) are shown below. [In the formula, R １ and R ２ is represented by the above formula (I １ However, in some cases, the diol compound (I １ ) bisphenol A, bisphenol AP, bisphenol B, bisphenol BP, bisphenol E, bisphenol F, bisphenol TMC, and bisphenol Z may be excluded.

[0089] Diol compound (I ２ ) is represented by the following formula (I ２ ) [In the formula, R １ and R ２ is represented by the above formula (I １ ) and X ２ is represented by the above formula (I １ ) in １ The diol compound (I) ２Specific examples of fluorenes include 9,9-bis[6-(1-hydroxymethoxy)naphthalen-2-yl]fluorene, 9,9-bis[6-(2-hydroxyethoxy)naphthalen-2-yl]fluorene, 9,9-bis[6-(3-hydroxypropoxy)naphthalen-2-yl]fluorene, and 9,9-bis[6-(4-hydroxybutoxy)naphthalen-2-yl]fluorene. Of these, 9,9-bis[6-(2-hydroxyethoxy)naphthalen-2-yl]fluorene is preferred.

[0090] Diol compound (I ３ ) is represented by the following formula (I ３ ) is expressed as HO-R １ -X ３ -R ２ -OH (I ３ ) [wherein, R １ and R ２ is represented by the above formula (I １ ) and X ３ is C １５－３２ represents a divalent aromatic hydrocarbon group.] C １５－３２ Examples of the divalent aromatic hydrocarbon group include C groups such as fluoranthenylene, acephenanthrylene, aceanthrylene, triphenylene, pyrenylene, chrysenylene, naphthacenylene, pleiadenylene, picenylene, perylenylene, biphenylene, pentaphenylene, pentacenylene, tetraphenylenylene, hexaphenylene, hexacenylene, rubycenylene, coronenylene, trinaphthylenylene, heptaphenylene, heptacenylene, pyranthrene, and ovalenylene. １５－３２ Divalent condensed polycyclic aromatic hydrocarbon groups such as terphenylene and quaterphenylene. X ３ R above ３ The number of groups is not particularly limited as long as it is substitutable, but can be, for example, 1 or more and 10 or less, preferably 8 or less or 5 or less, and more preferably 1 or 2.

[0091] Diol compound (I ３ Specific examples of the binaphthalenediol compounds include those represented by the following formula: [In the formula, R１ and R ２ is represented by the above formula (I １ ) has the same meaning as in the above.] Examples of such binaphthalene diol compounds include 2,2'-bis(1-hydroxymethoxy)-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene, 2,2'-bis(3-hydroxypropyloxy)-1,1'-binaphthalene, and 2,2'-bis(4-hydroxybutoxy)-1,1'-binaphthalene. Of these, 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene is preferred.

[0092] Diol compound (I ４ ) is represented by the following formula (I ４ ) is expressed as HO-R ２０ -X ４ -R ２１ -OH (I ４ ) [wherein, R ２０ and R ２１ are independently −(CR ５ R ６ ) ｍ１ - or -(-O-(CR ５ R ６ ) ｍ２ -) ｍ３ - (wherein, R ５ and R ６ is represented by the above formula (I １ ) and m １ represents an integer of 1 or more and 10 or less; m ２ represents an integer of 1 or more and 10 or less; m ３ represents an integer of 1 or more and 10 or less; m １ or m ２ is an integer of 2 or more, a plurality of R ５ or R ６ may be the same or different), and X ４ represents a divalent group containing one or more hydrocarbon rings or heterocycles. ２ is preferably 2 or more.

[0093] The above formula (I ４ ) R ２０ and R ２１- (CR ５ R ６ ) ｍ１ Examples of - include an ethylene group (-CH ２ CH ２ -), and -O-(CR ５ R ６ ) ｍ２ - is, for example, -O-CH ２ CH ２ - and -O-CH(CH ３ ) CH ２ - can be mentioned. １ -(-O-(CR ５ R ６ ) ｍ２ -) ｍ３ -, HO-R from the viewpoint of stability １ -X ３ - is HO-(-O-(CR ５ R ６ ) ｍ２ -) ｍ３ -X ３ It does not become -, HO-(-(CR ５ R ６ ) ｍ２ -O-) ｍ３ -X ３ The divalent group containing one or more hydrocarbon rings or heterocycles is a divalent C ６－３２ Aromatic hydrocarbon group, divalent C optionally having a substituent β ３－２０ Cycloalkyl group, divalent C optionally having a substituent β ６－３２ Divalent C optionally having an aromatic hydrocarbon group and a substituent β ３－２０ Divalent groups each having one or more cycloalkyl groups can be mentioned. ６－３２ The aromatic hydrocarbon group may contain a heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom, so long as the aromatic hydrocarbon group as a whole exhibits aromaticity. ６－３２ The aromatic hydrocarbon group is not particularly limited, but examples thereof include the following: Divalent C ３－２０ The cycloalkyl group may also contain a heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. ３－１４The cycloalkyl group is not particularly limited, but examples thereof include the following. Divalent C optionally having a substituent β ６－３２ Divalent C optionally having an aromatic hydrocarbon group and a substituent β ３－２０ The divalent group each having one or more cycloalkyl groups is not particularly limited, but examples thereof include the following.

[0094] Diol compound (I ５ ) is represented by the following formula (I ５ ) is expressed as HO-R １ -X ５ -R ２ -OH (I ５ ) [wherein, R １ and R ２ is represented by the above formula (I １ ) and X ５ represents a divalent saturated heterocyclic group.] The divalent saturated heterocyclic group is not particularly limited, but examples thereof include the following.

[0095] Diol compound (I ６ ) is represented by the following formula (I ６ ) [In the formula, X ６ is C １－１０ represents an alkylene group, and n represents an integer of 13 or more and 50 or less.] C １－１０ The alkylene group refers to a linear or branched divalent saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms. For example, —CH ２ -, -CH ２ CH ２ -, -CH ２ CH ２ CH ２ -, -CH ２ CH (CH ３ ) -, -CH(CH ３ ) CH ２ -, -CH ２ CH ２ CH ２ CH ２ The diol compound (I) ６ ) in X６ may be the same or different, and multiple X ５ When -O-X is present, ６ The arrangement of - may be random or block. １－１０ The alkylene group is ２－１０ An alkylene group is preferred. The diol compound may be used alone or in combination of two or more. For example, by using two or more diol compounds in combination, a copolymer polycarbonate can be produced satisfactorily. However, from the viewpoint of production efficiency, it is preferable to use only one diol compound alone. When two or more diol compounds are used, the number of diol compounds is preferably 5 or less, more preferably 3 or less, and even more preferably 2. By copolymerizing two or more diol compounds using the method of the present invention, the range of physical properties of the resulting polycarbonate is broadened, making it easier to adjust the physical properties.

[0096] C １－４ The amounts of the halogenated hydrocarbon and the diol compound to be used are not particularly limited as long as the reaction proceeds and the desired product is obtained. １－４ The above reaction also proceeds when a diol compound is used in an amount of 1 mole per mole of halogenated hydrocarbon. １－４ The molar ratio of the diol compound to the halogenated hydrocarbon ([diol compound] / [C １－４ It is preferable that the molar ratio [of nucleophilic functional group-containing compounds] is 0.001 or more and 1 or less. The molar ratio is more preferably 0.01 or more, even more preferably 0.1 or more, and more preferably 0.8 or less, and even more preferably 0.5 or less. If the molar ratio is too large, the amount of the nucleophilic functional group-containing compounds increases relatively, and the amount of unreacted nucleophilic functional group-containing compounds increases, while if the molar ratio is too small, the amount of unreacted C １－４ The amount of halogenated hydrocarbons increases, and there is a risk that carbonyl halides may be released outside the reaction system. １－４ When the halogenated hydrocarbon is a liquid at room temperature and pressure and can be used as a solvent, １－４The ratio of the diol compound to the halogenated hydrocarbon may be 1 mg / mL or more and 500 mg / mL or less.

[0097] Among the above-mentioned optional structural units (Z), structural units derived from diols having an aromatic ring are preferred, as they tend to increase the refractive index of the thermoplastic resin. From the viewpoint of the reactivity of the monomer in the polymerization reaction, structural units derived from aliphatic hydroxyl groups (e.g., -CH ２ For the above reasons, a structural unit derived from a diol having an aromatic ring and an aliphatic hydroxyl group, such as a diol having the general formula (I), is preferred. １ ) ~ (I ３ ) １ ) ~ (I ３ It is preferable to provide a structural unit (Z) derived from

[0098] Alternatively, the resin may contain a structural unit (d) represented by the following general formula (2). In formula (2), R ｚ and R ｘ each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; i represents an integer of 2 to 16; and p represents an integer of 1 to 600.

[0099] In a preferred embodiment of the present invention, in formula (2), i is an integer of 2 to 14, 2 to 12, 2 to 10, 2 to 8, 2 to 6, 2 to 4, 4 to 16, 4 to 14, 4 to 12, 4 to 10, 4 to 8, 4 to 6, 6 to 16, 6 to 14, 6 to 12, 6 to 10, or 6 to 8, and p is an integer of 1 to 500, 1 to 400, 1 to 300, 1 to 200, 1 to 100, 1 to 50, 1 to 40, 1 to 30, 1 to 20, 1 to 15, 1 to 10, 1 to 8, 1 to 6, 1 to 4, 1 to 3, or 2 to 3.

[0100] Preferred examples of the aliphatic dihydroxy compound related to the structural unit (d) represented by formula (2) include ethylene glycol, diethylene glycol, triethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, poly-n-propylene glycol, etc. Preferred examples of the poly-n-propylene glycol include polyethylene glycol, polytrimethylene glycol, polytetramethylene glycol, polypentamethylene glycol, polyhexamethylene glycol, etc. Furthermore, a commercially available product of polytrimethylene glycol is "VELVETOL" manufactured by Allessa.

[0101] The structural unit (d) is more preferably a structural unit derived from a compound selected from the group consisting of diethylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,10-decanediol, and 1,12-dodecanediol, and is particularly preferably a structural unit derived from 1,12-dodecanediol.

[0102] [3] Resin Composition The resin composition according to the embodiment contains the above-described compound (A) and resin as main components, and may further contain the following components.

[0103] <Low Molecular Weight Compound (Cyclic Compound)> The thermoplastic resin composition may contain a compound or oligomer having a weight average molecular weight of 1,000 or less. For example, this is a low molecular weight cyclic compound represented by the following general formula (T): The cyclic compound represented by the following general formula (T) is thought to be derived mainly from the dinaphthalene-containing dihydroxy compound that constitutes the resin. (In general formula (T), R １ and R ２R each independently represents 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. １ and R ２ When R is an alkyl group which may have a substituent, it preferably has a total of 1 to 14 or 1 to 10 carbon atoms, more preferably has a total of 1 to 6 carbon atoms, and particularly preferably has a total of 1 or 2 carbon atoms. １ and R ２ When R is an aryl group which may have a substituent, it preferably has a total of 6 to 20 carbon atoms, more preferably has a total of 6 to 12 carbon atoms, and particularly preferably has a total of 6 to 8 carbon atoms. １ and R ２ Preferred examples of the group include a methyl group, an ethyl group, a propyl group, a phenyl group, and a benzyl group, and more preferred are a methyl group and a phenyl group.

[0104] In general formula (T), R ａ and R ｂ each independently represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 20 carbon atoms which may have a substituent, an alkoxyl group of 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group of 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group of 5 to 20 carbon atoms which may have a substituent, an aryl group of 6 to 20 carbon atoms which may have a substituent, a heteroaryl group of 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 of 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ Ra and Rb are 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.

[0105] In general formula (T), X represents a single bond or an optionally substituted fluorene group. X is preferably a single bond or an optionally substituted fluorene group having a total of 12 to 20 carbon atoms. In general formula (T), A and B each independently represent an optionally substituted alkylene group having 1 to 5 carbon atoms, preferably an alkylene group having 2 or 3 carbon atoms. In general formula (T), m and n each independently represent an integer of 0 to 6, preferably an integer of 0 to 3, and more preferably 0 or 1. In general formula (T), 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.

[0106] Examples of the substituent in general formula (T) include a hydroxyl group, a halogen, an amino group, a vinyl group, a carboxyl group, a cyano group, a (meth)acryloxy group, a glycidyloxy group, and a mercapto group. When general formula (T) contains a substituent, the range of the number of carbon atoms mentioned above refers to the total number of carbon atoms including the number of carbon atoms of the substituent. Specific examples of the low-molecular-weight compound represented by general formula (T) include those shown in the following formulae (T-1) to (T-4).

[0107] The low-molecular-weight cyclic compounds that can be contained in the thermoplastic resin composition of the present invention are produced as by-products in the polymerization reaction for producing polyether resins, and their low molecular weight improves the fluidity of the composition and the moldability of the thermoplastic resin. Furthermore, because the cyclic compounds are low-molecular-weight compounds with a molecular structure similar to that of plasticizers, thermoplastic resins containing the cyclic compounds are highly compatible with other resins without the addition of plasticizers, which is believed to reliably prevent problems caused by the bleed-out of plasticizers, which make their addition unnecessary. While it is believed that an appropriate amount of highly plasticizing components is desirable to improve moldability, if too much is present, molds may be contaminated during processing of the thermoplastic resin composition.

[0108] From the above, in the thermoplastic resin composition, the total content of the cyclic units represented by the above formula (T) is preferably 15 wt% or less or 13 wt% or less, more preferably 10 wt% or less or 8.0 wt% or less, and even more preferably 6.0 wt% or less or 4.0 wt% or less, based on the total weight of the thermoplastic resin composition. Furthermore, the total content of the cyclic units represented by the above formula (T) contained in the thermoplastic resin composition is preferably 0.1 wt% or more and 15 wt% or less, more preferably 2.0 wt% or more and 13 wt% or less, even more preferably 3.0 wt% or more and 11 wt% or less, based on the total weight of the thermoplastic resin composition, and particularly preferably 4.0 wt% or more or more than 4.0 wt% (higher than 4.0 wt%) and 11 wt% or less. As long as the content of these cyclic units is within the above range, it can be said that there are no problems with the properties of the thermoplastic resin composition, particularly when used for optical applications. However, the thermoplastic resin composition of the present invention does not necessarily contain the above cyclic units.

[0109] <Resins Other Than Resins (J1) to (J3)> The resin composition according to the embodiment may contain a resin other than the above-described resins (J1) to (J3), for example, a polycarbonate resin. The type of polycarbonate resin is not particularly limited as long as it contains an -[O-R-OCO]- unit containing a carbonate bond in the molecular main chain (where R is an aliphatic group, an aromatic group, or both an aliphatic group and an aromatic group, and further has a linear or branched structure). Furthermore, the thermoplastic resin composition may contain a polycarbonate resin such as a polyester carbonate resin or a polyester resin. Similarly, the polyester carbonate resin and polyester resin are not particularly limited as long as they contain an -[O-R-OC]- unit containing a carbonate bond in the molecular main chain (where R is as described above).

[0110] Other resins include various resins such as acrylic resins such as polymethyl methacrylate (PMMA), polyethylene terephthalate (PET), triacetyl cellulose (TAC), polyethylene naphthalate (PEN), polyimide (PI), cycloolefin copolymer (COC), norbornene-containing resins, polyethersulfone, cellophane, and aromatic polyamide.

[0111] Compositions containing thermoplastic resins may contain phenolic compounds that may be produced as by-products of the polymerization reaction, as well as unreacted silane compounds, carbonate compounds, and diol compounds. Because impurities such as phenolic compounds and diphenyl carbonate can reduce the strength of molded articles and cause odors, it is preferable to minimize their content. Therefore, the content of phenolic compounds, silane compounds, carbonate compounds, and diol compounds may be reduced to an undetectable level, but from the perspective of productivity, they may be included in the composition to the extent that the effect is not impaired. Furthermore, by including a predetermined amount of residual monomer, for example, 1 to 1,000 ppm by weight, preferably 10 to 900 ppm, and more preferably 20 to 800 ppm, based on the total weight of the composition, improved fluidity during molding can be achieved, resulting in good plasticity when the resin is molten. The composition of the present invention may also contain, for example, more than 300 ppm by mass or more, more than 500 ppm by mass or more, or more than 700 ppm by mass or more of an aromatic monohydroxy compound, such as aryl alcohols such as phenol.

[0112] <Additives> The resin composition according to the embodiment may further contain an additive. Examples of the additive include an antioxidant. As the antioxidant, a phenol-based antioxidant and a phosphite-based antioxidant are preferred.

[0113] Phenolic antioxidants include 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine e-2,4,6(1H,3H,5H)-trione, 4,4',4''-(1-methylpropanyl-3-ylidene)tris(6-tert-butyl-m-cresol), 6,6'-di-tert-butyl-4,4'-butylidene-m-cresol, ocladecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentyl methyl acrylate ... 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].

[0114] Phosphite antioxidants include 2-ethylhexyl diphenyl phosphite, isodecyl diphenyl phosphite, triisodecyl phosphite, triphenyl phosphite, 3,9-bis(octadecyloxy)-2,4,8,10-tetraoxy-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 2,2'-methylenebis(4,6-di-tert-butylphenyl)2-ethylhexyl phosphite, Examples of the antioxidant include tris(2,4-di-tert-butylphenyl)phosphite, tris(nonylphenyl)phosphite, tetra-C12-15-alkyl(propane-2,2-diylbis(4,1-phenylene))bis(phosphite), and 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, and preferably 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane. As the antioxidant, any one of the above may be used alone, or a mixture of two or more may be used.

[0115] The proportion of the antioxidant in the resin composition is preferably 0.001 parts by mass or more (approximately 10 ppm by mass or more), more preferably 0.01 parts by mass or more (approximately 100 ppm by mass or more), and even more preferably 0.1 parts by mass or more (approximately 1000 ppm by mass or more) relative to the total composition (100 parts by mass). The proportion of the antioxidant in the resin composition is preferably 2.0 parts by mass or less, more preferably 1.0 part by mass or less, even more preferably 0.7 parts by mass or less (approximately 7,000 ppm by mass or less), and particularly preferably 0.5 parts by mass or less (approximately 5,000 ppm by mass or less) relative to the total composition (100 parts by mass). The antioxidant may be used alone or in combination of two or more. When two or more types are used, it is preferable that the total amount thereof is within the above range.

[0116] Examples of further additives include deactivators, stabilizers, flame retardants, UV absorbers, release agents, colorants, compounding agents, plasticizers, fillers, rust inhibitors, dispersants, antifoaming agents, leveling agents, lubricants, dyes, pigments, bluing agents, nucleating agents, and clarifying agents. After the polymerization reaction is complete, the thermoplastic resin of the present invention may have the catalyst removed or deactivated to maintain thermal stability. A known method of deactivating the catalyst by adding an acidic substance can be preferably carried out. Specific examples of acidic substances include esters such as butyl benzoate, aromatic sulfonic acids such as p-toluenesulfonic acid, aromatic sulfonic acid esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate, phosphoric acids such as phosphorous acid, phosphoric acid, and phosphonic acid, phosphorous acid esters such as triphenyl phosphite, monophenyl phosphite, diphenyl phosphite, diethyl phosphite, di-n-propyl phosphite, di-n-butyl phosphite, di-n-hexyl phosphite, dioctyl phosphite, and monooctyl phosphite, and esters such as triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate, and dioctyl phosphate. phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid, dibutylphosphonic acid, etc.; phosphonic acid esters such as diethyl phenylphosphonate, etc.; phosphines such as triphenylphosphine, bis(diphenylphosphino)ethane, etc.; boric acid, phenylboric acid, etc.; aromatic sulfonates such as tetrabutylphosphonium dodecylbenzenesulfonate, etc.; organic halides such as stearic acid chloride, benzoyl chloride, p-toluenesulfonic acid chloride, etc.; alkyl sulfates such as dimethyl sulfate, etc.; organic halides such as benzyl chloride, etc. are preferably used.

[0117] Furthermore, as a deactivator for deactivating the catalyst, alkyl acid phosphate metal salts such as distearyl acid phosphate zinc salt, monostearyl acid phosphate zinc salt, etc. The above-mentioned deactivator may be used in an amount of, for example, 0.001 to 50 times by mole, preferably 0.01 to 30 times by mole, relative to the amount of the catalyst.

[0118] A stabilizer may be added to the thermoplastic resin of the present invention. Examples of stabilizers include heat stabilizers and the above-mentioned antioxidants. When blended, the stabilizer is added in an amount of preferably 0.001 parts by mass or more, more preferably 0.01 parts by mass or more, and even more preferably 0.02 parts by mass or more, per 100 parts by mass of the thermoplastic resin, and preferably 2 parts by mass or less, more preferably 1.4 parts by mass or less, and even more preferably 1.0 part by mass or less. The thermoplastic resin composition may contain only one type of stabilizer, or two or more types. When two or more types are contained, the total amount thereof is preferably within the above range.

[0119] Examples of the heat stabilizer include phenol-based, phosphorus-based, and sulfur-based heat stabilizers. Specific examples include phosphorus oxoacids such as phosphoric acid, phosphonic acid, phosphorous acid, phosphinic acid, and polyphosphoric acid; metal acid pyrophosphates such as sodium acid pyrophosphate, potassium acid pyrophosphate, and calcium acid pyrophosphate; phosphates of Group 1 or Group 10 metals such as potassium phosphate, sodium phosphate, cesium phosphate, and zinc phosphate; organic phosphate compounds, organic phosphite compounds, and organic phosphonite compounds. Also included are at least one compound selected from the group consisting of (a) a phosphite ester compound in which at least one ester in the molecule is esterified with phenol and / or a phenol having at least one alkyl group having 1 to 25 carbon atoms, (b) phosphorous acid, and (c) tetrakis(2,4-di-tert-butylphenyl)-4,4′-biphenylene-di-phosphonite.Specific examples of the phosphite ester compound (a) include trioctyl phosphite, trioctadecyl phosphite, tridecyl phosphite, trilauryl phosphite, tristearyl phosphite, triphenyl phosphite, tris(mononylphenyl)phosphite, tris(mononyl / dinonylphenyl)phosphite, trisnonylphenyl phosphite, tris(octylphenyl)phosphite, tris(2,4-di-tert-butylphenyl)phosphite, trinonyl phosphite, didecyl monophenyl phosphite, dioctyl monophenyl phosphite, diisopropyl monophenyl phosphite, monobutyl diphenyl phosphite, monodecyl diphenyl phosphite, and bis(2,4-di-tert-butylphenyl)pentaerythritol. Examples of suitable diphosphite include bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol phosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol phosphite, monooctyldiphenyl phosphite, distearylpentaerythritol diphosphite, tricyclohexyl phosphite, diphenylpentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, 2,2-methylenebis(4,6-di-tert-butylphenyl)octyl phosphite, bis(nonylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, and bis(2,6-di-tert-butyl-4-ethylphenyl)pentaerythritol diphosphite. These may be used alone or in combination of two or more.

[0120] Examples of organic phosphite compounds include "ADK STAB 1178 (trade name, the same applies hereinafter)," "ADK STAB 2112," and "ADK STAB HP-10" manufactured by Adeka Corporation, "JP-351," "JP-360," and "JP-3CP" manufactured by Johoku Chemical Industry Co., Ltd., and "IRGAFOS 168" manufactured by BASF. Examples of phosphate esters include trimethyl phosphate, triethyl phosphate, tributyl phosphate, trioctyl phosphate, triphenyl phosphate, tricresyl phosphate, tris(nonylphenyl)phosphate, and 2-ethylphenyldiphenyl phosphate.

[0121] When blended, the addition ratio of the heat stabilizer is preferably 0.001 parts by mass or more, more preferably 0.01 parts by mass or more, even more preferably 0.03 parts by mass or more, and preferably 1 part by mass or less, more preferably 0.7 parts by mass or less, even more preferably 0.5 parts by mass or less, relative to 100 parts by mass of the thermoplastic resin. The thermoplastic resin composition may contain only one type of heat stabilizer, or two or more types. When two or more types are contained, it is preferable that the total amount thereof is within the above range.

[0122] The flame retardant may be an organic metal salt-based flame retardant, a phosphorus-based flame retardant, a silicone-based flame retardant, etc. Examples of flame retardants that can be used in the present invention include the flame retardants (flame retardant compositions) described in paragraphs 0085 to 0093 of JP 2016-183422 A, the contents of which are incorporated herein by reference.

[0123] Examples of the ultraviolet absorber include inorganic ultraviolet absorbers such as cerium oxide and zinc oxide, as well as organic ultraviolet absorbers such as benzotriazole compounds, benzophenone compounds, salicylate compounds, cyanoacrylate compounds, triazine compounds, oxanilide compounds, malonic acid ester compounds, hindered amine compounds, and phenyl salicylate compounds. Of these, benzotriazole-based and benzophenone-based organic ultraviolet absorbers are preferred.In particular, specific examples of benzotriazole compounds include 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-[2'-hydroxy-3',5'-bis(α,α-dimethylbenzyl)phenyl]-benzotriazole, 2-(2'-hydroxy-3',5'-di-tert-butyl-phenyl)-benzotriazole, 2-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-3',5'-di-tert-butyl-phenyl)-5-chlorobenzotriazole, and 2-(2'-hydroxy-3',5'-di-tert-butyl-phenyl)-5-chlorobenzotriazole. Chlorobenzotriazole, 2-(2'-hydroxy-3',5'-di-tert-amyl)-benzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole, 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2N-benzotriazol-2-yl)phenol], 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[(hexyl)oxy]-phenol, 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]phenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylmethyl)phenol, 2-[5-chloro(2H)-benzotriazol-2-yl]-4-methyl-6-(tert-butyl)phenol, 2,2'-(1,4-phenylene)bis[4H-3,1-benzoxazin-4-one], [(4-methoxyphenyl)-methylene]-propanediol acid dimethyl ester, 2-(2H-benzotriazol-2-yl)-p-cresol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylmethyl)phenol, 2-[5-chloro(2H)-benzotriazol-2-yl]-4-methyl-6-(tert-butyl)phenol phenol, 2,4-di-tert-butyl-6-(5-chlorobenzotriazol-2-yl)phenol, 2-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetrabutyl)phenol, 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetrabutyl)phenol], [methyl-3-[3-tert-butyl-5-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate-polyethylene glycol] condensate, and the like can be mentioned.Of the above, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole and 2,2'-methylene-bis[4-(1,1,3,3-tetramethylbutyl)-6-(2N-benzotriazol-2-yl)phenol] are preferred. Specific examples of the benzophenone-based ultraviolet absorber include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2-hydroxy-4-octadecyloxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2,2',4,4'-tetrahydroxybenzophenone. Specific examples of phenyl salicylate-based ultraviolet absorbers include phenyl salicylate and 4-tert-butyl-phenyl salicylate. Specific examples of triazine-based ultraviolet absorbers include 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[(hexyl)oxy]phenol and 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol. Specific examples of hindered amine-based ultraviolet absorbers include bis(2,2,6,6-tetramethylpiperidin-4-yl)sebacate.

[0124] When blended, the addition ratio of the ultraviolet absorber is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and preferably 3 parts by mass or less, more preferably 1 part by mass or less, relative to 100 parts by mass of the resin. Only one type of ultraviolet absorber may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is within the above range.

[0125] Examples of the release agent include carboxylic acid esters, polysiloxane compounds, and paraffin wax (polyolefin-based). Other examples of the release agent include ester compounds, such as glycerin fatty acid esters (e.g., mono- and diglycerides of glycerin fatty acid), glycol fatty acid esters (e.g., propylene glycol fatty acid esters, sorbitan fatty acid esters), higher alcohol fatty acid esters, and full esters or mono-fatty acid esters of aliphatic polyhydric alcohols and aliphatic carboxylic acids. When an ester of aliphatic polyhydric alcohols and aliphatic carboxylic acids is used as the release agent, either a monoester or a full ester can be used, but a compound other than a full ester, such as a monoester, may also be used.

[0126] Specific examples include at least one compound selected from the group consisting of aliphatic carboxylic acids, esters of aliphatic carboxylic acids and alcohols, aliphatic hydrocarbon compounds with a number-average molecular weight of 200 to 15,000, and polysiloxane-based silicone oils. Examples of aliphatic carboxylic acids include saturated or unsaturated aliphatic mono-, di-, or tri-carboxylic acids. Here, aliphatic carboxylic acids also include alicyclic carboxylic acids. Among these, preferred aliphatic carboxylic acids are mono- or di-carboxylic acids having 6 to 36 carbon atoms, with saturated aliphatic mono-carboxylic acids having 6 to 36 carbon atoms being more preferred. Specific examples of aliphatic carboxylic acids include palmitic acid, stearic acid, valeric acid, caproic acid, capric acid, lauric acid, arachic acid, behenic acid, lignoceric acid, cerotic acid, melissic acid, tetralinic acid, montanic acid, glutaric acid, adipic acid, and azelaic acid. The aliphatic carboxylic acids in the esters of aliphatic carboxylic acids and alcohols can be the same as those described above.

[0127] On the other hand, examples of alcohols include saturated or unsaturated monohydric or polyhydric alcohols. These alcohols may have a substituent such as a fluorine atom or an aryl group. Among these, monohydric or polyhydric saturated alcohols having 30 or fewer carbon atoms are preferred, and aliphatic saturated monohydric or polyhydric alcohols having 30 or fewer carbon atoms are even more preferred. Here, the term "aliphatic" also encompasses alicyclic compounds. Specific examples of alcohols include octanol, decanol, dodecanol, stearyl alcohol, behenyl alcohol, ethylene glycol, diethylene glycol, glycerin, pentaerythritol, 2,2-dihydroxyperfluoropropanol, neopentylene glycol, ditrimethylolpropane, and dipentaerythritol. The above-mentioned ester compounds may contain aliphatic carboxylic acids and / or alcohols as impurities, or may be a mixture of multiple compounds. Specific examples of esters of aliphatic carboxylic acids and alcohols include beeswax (a mixture primarily composed of myricyl palmitate), stearyl stearate, behenyl behenate, stearyl behenate, glycerin monopalmitate, glycerin monostearate, glycerin distearate, glycerin tristearate, pentaerythritol monopalmitate, pentaerythritol monostearate, pentaerythritol distearate, pentaerythritol tristearate, and pentaerythritol tetrastearate. Aliphatic hydrocarbons having a number-average molecular weight of 200 to 15,000 include liquid paraffin, paraffin wax, microcrystalline wax, polyethylene wax, Fischer-Tropsch wax, and α-olefin oligomers having 3 to 12 carbon atoms. Aliphatic hydrocarbons also include alicyclic hydrocarbons. These hydrocarbon compounds may also be partially oxidized. Among these, paraffin wax, polyethylene wax, or partially oxidized polyethylene wax are preferred, with paraffin wax and polyethylene wax being more preferred. The number average molecular weight is preferably 200 to 5000. These aliphatic hydrocarbons may be a single substance or a mixture of substances with various constituent components and molecular weights, as long as the main component is within the above range.Examples of polysiloxane-based silicone oils include dimethyl silicone oil, phenylmethyl silicone oil, diphenyl silicone oil, fluorinated alkyl silicone, etc. Two or more of these may be used in combination.

[0128] Specific examples of the release agent include the following: sorbitan fatty acid esters such as sorbitan stearate, sorbitan laurate, sorbitan oleate, sorbitan trioleate, sorbitan tribehenate, sorbitan stearate, sorbitan tristearate, and sorbitan caprylate; propylene glycol fatty acid esters such as propylene glycol monostearate, propylene glycol monooleate, propylene glycol monobehenate, propylene glycol monolaurate, and propylene glycol monopalmitate; higher alcohol fatty acid esters such as stearyl stearate; glycerin monohydroxystearates such as glycerin monostearate and glycerin mono-12-hydroxystearate, glycerin monooleate, glycerin monobehenate, glycerin monocaprylate, glycerin monocaprate, and glycerin Glycerin fatty acid ester monoglycerides including monoglycerides such as monolaurate: mono- and diglycerides such as glycerin monodistearate, glycerin monodistearate, glycerin monodibehenate, and glycerin monodiolate; acetylated glycerin fatty acid ester monoglycerides 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; polyglycerin fatty acid esters such as diglycerin stearate, diglycerin laurate, diglycerin oleate, diglycerin monostearate, diglycerin monolaurate, diglycerin monomyristate, diglycerin monooleate, tetraglycerin stearate, decaglycerin laurate, decaglycerin oleate, and polyglycerin polyricinoleate. Additionally, the antioxidants listed above can also be used as the mold release agent.

[0129] When a release agent is added, the amount thereof is preferably 0.001 parts by mass or more, more preferably 0.01 parts by mass or more, and preferably 2 parts by mass or less, more preferably 1 part by mass or less, relative to 100 parts by mass of the resin. Only one type of release agent may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is within the above range.

[0130] The colorant may be either a dye or a pigment, and examples thereof include inorganic pigments, organic pigments, organic dyes, etc. Examples of inorganic pigments include sulfide pigments such as carbon black, cadmium red, and cadmium yellow; silicate pigments such as ultramarine; oxide pigments such as titanium oxide, zinc white, red iron oxide, chromium oxide, iron black, titanium yellow, zinc-iron brown, titanium-cobalt green, cobalt green, cobalt blue, copper-chromium black, and copper-iron black; chromate pigments such as yellow lead and molybdate orange; and ferrocyanide pigments such as iron blue. Examples of organic pigments and organic dyes as colorants include phthalocyanine dyes and pigments (dyes and pigments are referred to as dyes and pigments, the same applies hereinafter) such as copper phthalocyanine blue and copper phthalocyanine green; azo dyes and pigments such as nickel azo yellow; condensed polycyclic dyes and pigments such as thioindigo, perinone, perylene, quinacridone, dioxazine, isoindolinone, and quinophthalone; quinoline, anthraquinone, heterocyclic, and methyl dyes and pigments. Among these, titanium oxide, carbon black, cyanine, quinoline, anthraquinone, and phthalocyanine dyes and pigments are preferred from the viewpoint of thermal stability.

[0131] Furthermore, for the purpose of improving handling during extrusion and improving dispersibility in the resin composition, the colorant may be used in the form of a masterbatch with a polystyrene resin, a polycarbonate resin, or an acrylic resin. When blended, the colorant is added in an amount of preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and even more preferably 2 parts by mass or less, and 0.1 parts by mass or more, per 100 parts by mass of the resin. Only one type of colorant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount be within the above range.

[0132] <Physical Properties of Resin Composition> (1) Polystyrene-equivalent Weight Average Molecular Weight (Mw) The polystyrene-equivalent weight average molecular weight (Mw) of the resin is preferably 10,000 to 300,000. More preferably, the polystyrene-equivalent weight average molecular weight (Mw) is 20,000 to 120,000, and even more preferably 20,000 to 60,000. The polystyrene-equivalent weight average molecular weight (Mw) can be measured by the method described in the Examples below.

[0133] By setting the Mw to 10,000 or more, sufficient strength can be obtained when the resin is molded. By setting the Mw to 300,000 or less, the resin has an appropriate melt viscosity during production, allowing the resin to be removed without any problems after production. Furthermore, in the molten state, the resin has a flowability suitable for molding.

[0134] (2) Number Average Molecular Weight (Mn) The number average molecular weight (Mn) of the resin is preferably 1,000 to 30,000. More preferably, the number average molecular weight (Mn) is 2,000 to 10,000, and even more preferably 2,500 to 8,000. The number average molecular weight (Mn) can be measured by the method described in the Examples below.

[0135] By setting Mn to 1,000 or more, sufficient strength can be obtained when the resin is molded. By setting Mn to 30,000 or less, the resin has an appropriate melt viscosity during production, allowing the resin to be removed without problems after production. Furthermore, in the molten state, the resin has a flowability suitable for molding.

[0136] (3) Glass Transition Temperature (Tg) The glass transition temperature (Tg) of the resin composition according to the embodiment is preferably 120 to 170°C, more preferably 125 to 165°C. When the glass transition temperature is in this range, both heat resistance and moldability can be achieved. When compound (A) is blended, Tg is lowered by 1 to 35°C compared to a resin not blended with compound (A). Tg can be measured by the method described in the examples below.

[0137] (4) 5% Thermal Mass Loss Temperature The resin composition according to the embodiment has a 5% thermal mass loss temperature when heated from 30° C. at a rate of 10° C. / min of preferably 300° C. or higher, more preferably 345° C. or higher, and particularly preferably 370° C. or higher. The 5% thermal mass loss temperature is an index of heat resistance (thermal decomposition temperature) and can be measured by the method described in the examples below.

[0138] (5) YI Value The YI value of a solution obtained by dissolving the resin composition according to the embodiment in methylene chloride, measured in accordance with JIS K 7105, is preferably 10.0 or less, more preferably 9.0 or less, and particularly preferably 8.8 or less. When the YI value is in this range, chromatic aberration (mainly chromatic aberration on the short wavelength side) is reduced.

[0139] (6) Refractive Index (nd) The refractive index (nd) of the resin composition according to the embodiment is preferably 1.640 or more (e.g., 1.640 to 1.720), more preferably 1.650 or more (e.g., 1.650 to 1.710), and particularly preferably 1.660 or more (e.g., 1.660 to 1.700). Furthermore, the refractive index may be 1.670 or more, 1.680 or more, or 1.690 or more. When compound (A) is blended, the refractive index is improved by about 0.001 to 0.05 compared to a resin not blended with compound (A). The resin composition according to the embodiment can achieve a high refractive index while exhibiting other desirable effects (e.g., moldability, etc.). Here, the refractive index was measured at 20°C and a wavelength of 589 nm in accordance with JIS B 7071-2:2018. More specifically, the refractive index can be measured by the method described in the examples below.

[0140] (7) Abbe number (ν) The Abbe number of the resin composition according to the embodiment is preferably 24.0 or less, more preferably 21.5 or less, and particularly preferably 21.0 or less, 20.0 or less, or 19.0 or less. The Abbe number can be measured by the method described in the examples below.

[0141] (8) Melt Viscosity (MVR: Melt Volume Flow Rate) The resin composition according to the embodiment preferably has a melt volume flow rate (MVR) of 10 cm at 260°C. ３ / 10 minutes or more, more preferably 20 cm ３ / 10 minutes or more, particularly preferably 30 cm ３ / 10 minutes, 40cm ３ / 10 minutes or more, or 50 cm ３ The melt volume flow rate (MVR) of the resin composition can be measured by the method described in the Examples below. When the MVR is within this range, the plasticity during molding is improved, thereby improving productivity and reducing energy consumption.

[0142] (9) Mw Retention The resin composition according to the embodiment has a weight average molecular weight (Mw) retention rate before and after the melt viscosity measurement [(Mw after melt viscosity measurement / Mw before melt viscosity measurement) x 100] of preferably 90% or more, more preferably 95% or more, and particularly preferably 99% or more or 100%. Furthermore, the resin composition according to the embodiment has a weight average molecular weight (Mw) retention rate before and after a moist heat test [(Mw after moist heat test / Mw before melt viscosity measurement) x 100] of preferably 90% or more, more preferably 95% or more, and particularly preferably 99% or more or 100%. From these findings, it can be said that the resin composition according to the embodiment also has excellent moist heat resistance.

[0143] [4] Method for Producing Resin Composition Possible methods for producing the resin composition according to the embodiment include: (i) a method in which a monomer is polymerized to produce a resin, and then compound (A) is added to the resin to obtain a resin composition; and (ii) a method in which materials containing the monomers constituting the resin and compound (A) are mixed in advance, and the resulting mixture is subjected to a polymerization step to obtain a resin composition.

[0144] Thus, according to one embodiment, a method for producing a resin composition is provided, which includes subjecting a monomer constituting the resin to a polymerization reaction to obtain a resin, and then mixing the resin with compound (A). According to another embodiment, a method for producing a resin composition is provided, which includes mixing a monomer constituting the resin with compound (A) to obtain a mixture, and then subjecting the mixture to polymerization conditions to polymerize the monomer to obtain a resin composition. The advantages and effects of each method are as described above. Furthermore, as described above, components other than the resin and compound (A) can be added, but the timing of their addition is not particularly limited. That is, the other components may be added before the polymerization reaction or after the polymerization reaction is completed.

[0145] In the polymerization step, the use of a catalyst is optional, but when a catalyst is used, it is preferable to use, for example, the following polymerization catalysts. First, specific preferred examples of the polymerization catalyst include metal acetates such as zinc acetate, lead acetate, manganese acetate, cobalt acetate, aluminum acetate, calcium acetate, potassium acetate, lithium acetate, magnesium acetate, sodium acetate, tin acetate, zirconium acetate, and zirconium acetylacetonate (Zr(acac)), as well as other metal salts. Among these metal salts, specific examples of more preferred polymerization catalysts include zinc acetate, lead acetate, manganese acetate, and cobalt acetate.

[0146] As the polymerization catalyst, a phosphonium salt or the like can be used, and a quaternary phosphonium salt is preferred. Specific examples of the phosphonium salt as the polymerization catalyst include alkylphosphonium salts such as tetra-n-butylphosphonium bromide and tetra-n-butylphosphonium chloride; arylphosphonium salts such as tetraphenylphosphonium bromide, tetraphenylphosphonium chloride and tetraphenylphosphonium phenoxide (TPPP); alkylarylphosphonium salts; and the like.

[0147] A catalyst containing a basic compound can also be used as the polymerization catalyst. Examples of the basic compound catalyst include alkali metal compounds, alkaline earth metal compounds, etc., such as organic acid salts of alkali metals and alkaline earth metal compounds, inorganic salts such as carbonates, oxides, hydroxides, hydrides, and alkoxides. Alternatively, quaternary ammonium hydroxides and salts thereof, amines, phosphazenes, etc. can be used. These compounds can be used alone or in combination.

[0148] Of the above-mentioned basic compound catalysts, those containing alkali metal carbonates or alkali metal hydroxides are more preferred. Specific examples of more preferred catalysts include those containing metal carbonates such as cesium carbonate, potassium carbonate, sodium carbonate, and sodium bicarbonate; and metal hydroxides such as cesium hydroxide, potassium hydroxide, and sodium hydroxide. Specific examples of preferred amine catalysts include diazabicycloundecene (DBU: registered trademark), and specific examples of preferred phosphazene catalysts include BTPP (tert-butyliminotripyrrolidinophosphorane).

[0149] Further specific examples of catalysts for the polymerization reaction include the following: Examples of alkali metal compounds include sodium hydroxide, potassium hydroxide, lithium hydroxide, cesium hydroxide, sodium hydrogen carbonate, potassium hydrogen carbonate, lithium hydrogen carbonate, cesium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, sodium acetate, potassium acetate, lithium acetate, cesium acetate, sodium stearate, potassium stearate, lithium stearate, cesium stearate, sodium borohydride, potassium borohydride, lithium borohydride, cesium borohydride, sodium phenylborohydride, and phenylborohydride. Examples of the phenylboronate include potassium boron phenylate, lithium boron phenylate, cesium phenylate, sodium benzoate, potassium benzoate, lithium benzoate, cesium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, disodium hydrogen phosphate, dipotassium phenylphosphate, dilithium phenylphosphate, disodium phenylphosphate, dipotassium phenylphosphate, dilithium phenylphosphate, discesium phenylphosphate; alcoholates and phenolates of sodium, potassium, lithium, and cesium; and disodium salt, dipotassium salt, dilithium salt, and dicesium salt of bisphenol A.

[0150] Examples of alkaline earth metal compounds include calcium hydroxide, barium hydroxide, magnesium hydroxide, strontium hydroxide, calcium hydrogen carbonate, barium hydrogen carbonate, magnesium hydrogen carbonate, strontium hydrogen carbonate, calcium carbonate, barium carbonate, magnesium carbonate, strontium carbonate, calcium acetate, barium acetate, magnesium acetate, strontium acetate, calcium stearate, barium stearate, magnesium stearate, and strontium stearate.

[0151] Specific examples of basic boron compounds that can be used as a catalyst in the polymerization step include sodium salts, potassium salts, lithium salts, calcium salts, barium salts, magnesium salts, and strontium salts of tetramethyl boron, tetraethyl boron, tetrapropyl boron, tetrabutyl boron, trimethylethyl boron, trimethylbenzyl boron, trimethylphenyl boron, triethylmethyl boron, triethylbenzyl boron, triethylphenyl boron, tributylbenzyl boron, tributylphenyl boron, tetraphenyl boron, benzyltriphenyl boron, methyltriphenyl boron, and butyltriphenyl boron.

[0152] Examples of basic phosphorus compounds that can be used as catalysts in the polymerization step include triethylphosphine, tri-n-propylphosphine, triisopropylphosphine, tri-n-butylphosphine, triphenylphosphine, tributylphosphine, and quaternary phosphonium salts.

[0153] Examples of basic ammonium compounds that can be used as a catalyst in the polymerization step include tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylethylammonium hydroxide, trimethylbenzylammonium hydroxide, trimethylphenylammonium hydroxide, triethylmethylammonium hydroxide, triethylbenzylammonium hydroxide, triethylphenylammonium hydroxide, tributylbenzylammonium hydroxide, tributylphenylammonium hydroxide, tetraphenylammonium hydroxide, benzyltriphenylammonium hydroxide, methyltriphenylammonium hydroxide, and butyltriphenylammonium hydroxide.

[0154] Examples of amine compounds that can be used as catalysts in the polymerization step include 4-aminopyridine, 2-aminopyridine, N,N-dimethyl-4-aminopyridine, 4-diethylaminopyridine, 2-hydroxypyridine, 2-methoxypyridine, 4-methoxypyridine, 2-dimethylaminoimidazole, 2-methoxyimidazole, imidazole, 2-mercaptoimidazole, 2-methylimidazole, and aminoquinoline.

[0155] In addition, known polymerization catalysts can also be used, and preferred examples include antimony compounds, titanium compounds, germanium compounds, tin compounds, and aluminum compounds. Examples of such compounds include oxides, acetates, carboxylates, hydrides, alcoholates, halides, carbonates, and sulfates of antimony, titanium, germanium, tin, and aluminum. These compounds can also be used in combination of two or more. Among these, tin, titanium, and germanium compounds are preferred from the viewpoint of the melt stability and color of the thermoplastic resin.

[0156] As described above, known catalysts can be used as catalysts for the polymerization reaction. For example, compounds containing manganese, magnesium, titanium, zinc, aluminum, calcium, cobalt, sodium, lithium, or lead can be used. Specific examples include oxides, acetates, carboxylates, hydrides, alcoholates, halides, carbonates, and sulfates containing these elements. Among these, oxides, acetates, alcoholates, and other compounds of manganese, magnesium, zinc, titanium, and cobalt are preferred from the viewpoints of the melt stability, color, and small amount of insoluble foreign matter in the polymer of the thermoplastic resin. Manganese, magnesium, and titanium compounds are more preferred. These compounds can be used in combination of two or more.

[0157] As catalysts for the polymerization step, zinc, tin, zirconium, and lead salts are preferably used, and these can be used alone or in combination, and can also be used in combination with the above-mentioned alkali metal compounds and alkaline earth metal compounds.

[0158] Specific examples of catalysts that can be used in the polymerization step include zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin(II) chloride, tin(IV) chloride, tin(II) acetate, tin(IV) acetate, dibutyltin dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead(II) acetate, lead(IV) acetate, zirconium acetate, and titanium tetrabutoxide. Of these, zinc acetate, zirconium acetate, and titanium tetrabutoxide are preferred, with titanium tetrabutoxide being more preferred.

[0159] The catalyst can be prepared by a known method, or a commercially available catalyst may be used. In addition, it is preferable to substantially completely remove catalysts, such as alkali metal compound catalysts and alkaline earth metal compound catalysts, from the thermoplastic resin and the thermoplastic resin composition described in detail below.

[0160] In the polymerization reaction for polymerizing the above-mentioned monomer compounds, the mixture of the above-mentioned components is melted, and in the molten state, alcohols derived from the carbonate compounds as by-products, such as aryl alcohols such as phenol, methanol, etc., are removed under reduced pressure. By setting the reaction conditions in this manner, the polymerization reaction can be efficiently carried out.

[0161] In the polymerization step, it is preferable to allow the polymerization reaction to proceed under a pressure of 400 Pa or less. That is, the pressure in the polymerization reaction is preferably within a range of 400 Pa or less. In the polymerization step, it is preferable to maintain a normal pressure state without reducing the pressure or a state where the pressure is not significantly reduced for a certain period of time, and then reduce the pressure in the system to further allow the polymerization reaction to proceed. For example, in the polymerization step, it is preferable to gradually reduce the reaction pressure from the initial atmospheric pressure to 400 Pa or less, such as 40,000 Pa, 27,000 Pa, 24,000 Pa, 20,000 Pa, 16,000 Pa, 8,000 Pa, 4,000 Pa, 2,000 Pa, 400 Pa, 400 Pa or less, or 200 Pa or less. For example, in the polymerization step, the pressure may be reduced stepwise from the initial atmospheric pressure to 40,000 Pa, 20,000 Pa, 10,000 Pa, 5,000 Pa, and 200 Pa or less. This depressurization step in which the pressure in the reaction system is reduced stepwise and the degree of depressurization is increased halfway through is preferred because it allows efficient removal of the by-product alcohol while suppressing distillation of raw materials.

[0162] The time for the polymerization step is determined appropriately taking into consideration the type of the target thermoplastic resin, pressure, temperature, and other conditions, but for example, the total time for the polymerization step is within 5 to 10 hours. More specifically, the reaction time before decompression in the reaction system is 0.5 to 3 hours, preferably 1 to 2 hours, and the reaction time after decompression is 1 to 5 hours, preferably 2 to 4 hours.

[0163] In the polymerization step, the temperature in the polymerization reaction is preferably within a range of 150 to 300° C. More preferably, the temperature in the polymerization reaction is 160 to 280° C., even more preferably 170 to 270° C., and particularly preferably 180 to 260° C. Furthermore, the temperature range in the polymerization reaction may be 190 to 290° C., 210 to 280° C., 230 to 270° C., or 240 to 260° C.

[0164] In the polymerization step, the ratio of the molar amount of the catalyst to the total molar amount of the monomer compounds (molar ratio: i.e., molar amount of the catalyst / molar amount of the monomer compounds) is 1.0×10 －７ ~1.0 x 10－２ (mol / mol: 0.1 to 10,000 μmol / mol, or 1.0 × 10 －４ The molar ratio is preferably 1.0 × 10 to 10 mmol / mol. －７ ~2.0 x 10 －５ mol / mol (or 0.1 to 20 μmol / mol).

[0165] [5] Molded Article According to one embodiment, a molded article containing (or molded by) the resin composition described above is provided. Because the molded article has the effects described above for the resin composition, it can be suitably used, for example, as an optical component. 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 according to the embodiment has high flowability and can be molded by a casting method, making it particularly suitable for producing thin optical components. In a preferred embodiment, the optical component is an optical film or an optical lens.

[0166] The molding method for the molded article is not particularly limited, and examples include injection molding, press molding, blow molding, extrusion molding, vacuum molding, and pressure molding. 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 applied to the mold.

[0167] (Optical Lens) The addition of compound (A) improves the refractive index of the resin composition, and when this is used as an optical lens, it can be used in fields where expensive high-refractive-index glass lenses have traditionally been used, such as telescopes, binoculars, and television projectors, and is extremely useful. The optical lens is preferably used in the form of an aspherical lens, as necessary. Since an aspherical lens can substantially eliminate spherical aberration with a single lens, it is not necessary to eliminate spherical aberration by combining multiple spherical lenses, which enables weight reduction and reduction in production costs. Among optical lenses, aspherical lenses are particularly useful as camera lenses.

[0168] Furthermore, the addition of compound (A) improves the molding fluidity of the resin composition, making it particularly useful as a material for thin, small, and complex-shaped optical lenses. Specifically, the lens size preferably has a central thickness of 0.05 to 3.0 mm, more preferably 0.05 to 2.0 mm, and even more preferably 0.1 to 2.0 mm. The diameter is preferably 1.0 to 20.0 mm, more preferably 1.0 to 10.0 mm, and even more preferably 3.0 to 10.0 mm. Furthermore, the lens preferably has a meniscus shape, with one side convex and the other concave. Optical lenses can be molded by any method, such as mold molding, cutting, polishing, laser machining, electrical discharge machining, or etching. Among these, mold molding is more preferred from the standpoint of production costs.

[0169] (Optical Film) An optical film may be produced using the resin composition according to the embodiment. Such a film has excellent heat resistance, moisture resistance, etc., and is therefore suitable for use as a film for liquid crystal substrates, optical memory cards, etc. In order to prevent foreign matter from being mixed into the optical film as much as possible, the molding environment must naturally be a low-dust environment, preferably class 6 or less, and more preferably class 5 or less.

[0170] The present invention will be described in detail below with reference to examples, but the content of the present invention is not limited thereto. The raw materials used in the examples are as follows. [Polycarbonate Resin] (Synthesis Example 1) As raw materials, 689.762 kg (1.84 kmol) of 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), 1,330 kg (2.25 kmol) of 9,9-bis(3-phenyl-4-(2-hydroxyethoxy)phenyl)fluorene (PG), 903 kg (4.22 kmol) of diphenyl carbonate (DPC), and 104.5 mL of a 0.47 mol / L aqueous sodium hydrogen carbonate solution (12.0 × 10 per mole of the total of the diol compounds) were used. －６ (mol) was placed in a 10 L reactor equipped with a stirrer and a distillation device and heated to 180°C under a nitrogen atmosphere of 760 mmHg. Complete dissolution of the raw materials was confirmed 30 minutes after the start of heating, and stirring was then continued for 120 minutes under the same conditions. The vacuum was then adjusted to 200 mmHg, and the temperature was raised to 200°C at a rate of 60°C / hr. At this time, the start of distillation of by-produced phenol was confirmed. The reaction was then continued at 200°C for 20 minutes. The temperature was then raised to 230°C at a rate of 75°C / hr, and 10 minutes after the temperature increase, the vacuum was reduced to 1 mmHg or less over 2 hours while maintaining the temperature. The temperature was then raised to 245°C at a rate of 60°C / hr, and stirring was continued for an additional 30 minutes. After the reaction was completed, nitrogen was introduced into the reactor to pressurize the reaction system, and the produced polycarbonate resin was pelletized and withdrawn to obtain polycarbonate resin pellets (cylindrical pellets, pellet length: 2 to 5 mm, pellet diameter: 2 to 5 mm). The weight average molecular weight (Mw) of the obtained polycarbonate resin was 38,000.

[0171] Synthesis Examples 2 to 4 Polycarbonate resin pellets were obtained in the same manner as in Synthesis Example 1, except that the raw materials shown in Table 1 below were used.

[0172] Synthesis Example 5 As raw materials, 4.53 kg (12.1 mol) of 9,9-bis[6-(2-hydroxyethoxy)naphthalen-2-yl]fluorene (BNEF), 7.5 kg (20.03 mol) of 2,2′-bis(2-hydroxyethoxy)-1,1′-binaphthalene (BNE), 8.72 kg (14.8 mol) of 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene (BPPEF), 10.25 kg (47.87 mol) of diphenyl carbonate (DPC), and 2.5×10 －２ mol / L sodium bicarbonate (NaHCO ３ ) aqueous solution 16 mL (4.0 x 10 －４ mol, i.e., 8.4 × 10 per 1 mol of the total of dihydroxy compounds －６ mol) was placed in a 50 L reactor equipped with a stirrer and a distillation device and heated from 25°C to 180°C over 30 minutes under a nitrogen atmosphere of 760 mmHg. Complete dissolution of the raw materials was confirmed 30 minutes after the start of heating, and then stirring was continued at 180°C for 120 minutes. The vacuum level was then adjusted to 200 mmHg, and the temperature was raised to 200°C at a rate of 60°C / hr. At this time, the start of distillation of by-produced phenol was confirmed. The reaction was then continued at 200°C for 20 minutes. The temperature was then raised to 230°C at a rate of 75°C / hr, and 10 minutes after the temperature increase, the vacuum level was reduced to 1 mmHg or less over 2 hours while maintaining the temperature. The temperature was then raised to 245°C at a rate of 60°C / hr, and stirring was continued for an additional 40 minutes. After the reaction was completed, nitrogen was introduced into the reactor to return the pressure to normal, and the produced polycarbonate resin was pelletized and taken out (PC5, BNEF / BNE / BPPEF, Mw=31,000).

[0173] The polycarbonate resin (PC5) obtained above was melt-kneaded with 15 ppm by weight of tetrabutylphosphonium dodecylbenzenesulfonate (MGA-614, manufactured by Takemoto Yushi Co., Ltd.) as a deactivator, 300 ppm by weight of 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane (PEP-36, manufactured by ADEKA Corporation) as a mold release agent, and 1,000 ppm by weight of pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] (AO-60, manufactured by ADEKA Corporation) as an antioxidant, and the mixture was pelletized.

[0174] [Monomer] BINOL-DC: 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl BNEF: 9,9-bis[6-(2-hydroxyethoxy)naphthalen-2-yl]fluorene

[0175] [Ingredients] H2NTP: hexa-2-naphthoxycyclotriphosphazene OPTS: octaphenylcyclotetrasiloxane HPTP: hexaphenoxycyclotriphosphazene

[0176] (Example 1-1) 40 g of polycarbonate resin (PC1) and 2 g of H2NTP were placed in a 300 mL four-neck flask equipped with a stirrer, and then the system was replaced with a nitrogen atmosphere. The mixture was heated and melted at 260°C under less than 1 hPa and stirred for 30 minutes to obtain a resin composition. (Examples 1-2 to 1-4, Comparative Examples 1-1 to 1-6) Resin compositions were obtained in the same manner as in Example 1-1 using the raw materials shown in Table 2 below. In these examples and comparative examples, the content of compound (A) was 5 parts by mass per 100 parts by mass of resin in the resin composition. Various physical properties of the resin compositions of the examples and comparative examples were measured as follows. The results are shown in Table 2.

[0177] The various physical properties in Table 2 were measured by the methods described below. <Polystyrene-equivalent weight average molecular weight (Mw)> A calibration curve was prepared using GPC (gel permeation chromatography) with chloroform as the developing solvent and standard polystyrene (Shodex STANDARD, SM-105) of known molecular weight (molecular weight distribution = 1). The elution time and molecular weight value of each peak from the measured standard polystyrene were plotted, and a calibration curve was prepared by approximating using a cubic equation. Then, based on the obtained calibration curve, the weight average molecular weight (Mw) was calculated as a polystyrene-equivalent value using the following formula. [Calculation formula] Mw = Σ(W ｉ ×M ｉ ) / Σ(W ｉ ) (In the above formula, i is the i-th division point when dividing the molecular weight M, W ｉ is the i-th weight, M ｉ represents the i-th molecular weight. The molecular weight M represents the molecular weight in polystyrene equivalent at the same elution time on the calibration curve.)

[0178] [Measurement conditions] Apparatus: Labsolutions manufactured by Shimadzu Corporation Columns: Guard column (Shodex GPC K-G 4A) x 1, analytical column (Shodex GPC K-805L) x 2 Solvent: Chloroform (HPLC grade) Injection volume: 10 μL Sample concentration: 2000 ppm Solvent flow rate: 1 mL / min Measurement temperature: 40° C. Detector: RI

[0179] <Number Average Molecular Weight (Mn)> Using the same method and measurement method as for Mw above, the number average molecular weight (Mn) was calculated as a polystyrene equivalent value from the following formula: [Calculation formula] Mn = Σ(Mi) / Σ(i) (In the above formula, i represents the ith division point when dividing the molecular weight M, and Mi represents the ith molecular weight. Furthermore, the molecular weight M represents the molecular weight in polystyrene equivalent at the same elution time on the calibration curve.) The molecular weights (Mn and Mw) listed in Table 2 are the molecular weights of the polycarbonate resin contained in the resin composition.

[0180] <Glass Transition Temperature (Tg)> Measurement samples were prepared by weighing 5 to 12 mg of test pieces made of the resin compositions of the Examples and Comparative Examples into an AI autosampler sample container (RDC aluminum pan, a cylindrical container with a diameter of 6.8 mm and a height of 2.5 mm). The top of the sample container was sealed with an AI autosampler cover. Measurements were performed using a differential scanning calorimeter (DSC) under a nitrogen atmosphere (nitrogen flow rate: 50 ml / min), and 10.0 mg of sapphire was used as a standard substance in the reference cell. The measurement sample, adjusted to 30°C, was then heated to 280°C at 20°C / min, and then cooled to 30°C at 20°C / min. The sample was then heated to 280°C at 10°C / min and measured. Measurement device: Differential scanning calorimeter (DSC) (product name "DSC-7020", manufactured by Hitachi High-Tech Science Corporation).

[0181] <5% Thermal Mass Reduction Temperature> 10 mg of a measurement sample was precisely weighed in an aluminum pan (Al open-type sample container, φ5.2, H2.5 mm). Measurement was carried out under atmospheric pressure. 0.00519 g of α-alumina was used as a reference material. The sample temperature was adjusted to 30°C and heated to 500°C at a rate of 10°C / min, and the temperature at which the mass had decreased by 5% by mass from the start of the test was defined as the "5% thermal mass reduction temperature." Measurement device: differential thermal / gravimetric simultaneous measurement device (TG / DTA) (TG / DTA7300, manufactured by Hitachi High-Tech Science)

[0182] <YI Value> The YI value is a value indicating the degree to which the hue deviates from colorless or white toward yellow (yellowness). 6 g of a sample of the resin composition was dissolved in 60 ml of methylene chloride to obtain a liquid, and the YI value was measured using a spectrophotometer in accordance with JIS K7105. Spectrophotometer: SE2000 manufactured by Nippon Denshoku Kogyo Co., Ltd.

[0183] <Refractive Index (nd)> A 3 mm thick rectangular piece made of the resin composition produced in each of the examples and comparative examples was measured using an Abbe refractometer according to the method of JIS-K-7142.

[0184] <Abbe Number (νd), θgF, and θhF> Using an Abbe refractometer, the refractive indices of 3 mm thick right-angle pieces made of the resin compositions produced in the Examples and Comparative Examples were measured at wavelengths of 405 nm, 436 nm, 486 nm, 589 nm, and 656 nm at 20°C, and the Abbe number, θgF, and θhF were calculated using the following formulas: νd=(nd-1) / (nF-nC) θgF=(ng-nF) / (nF-nC) θhF=(nh-nF) / (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 ng: refractive index at a wavelength of 436 nm nh: refractive index at a wavelength of 405 nm Here, θgF and θhF represent the wavelength dispersion of the refractive index, and smaller values ​​indicate smaller wavelength dispersion. In particular, when wavelength dispersion increases in the g-line and h-line regions of the short wavelength region, it can become difficult to correct chromatic aberration, so there is a tendency that small values ​​of θgF and θhF are preferable.

[0185] <Melt viscosity (MVR: melt volume flow rate) and Mw retention> Measurements were performed in accordance with ISO 1133 at 260°C and a load of 2.160 kg. A sample for GPC measurement was prepared from the resin after measurement, and the weight average molecular weight was measured. The ratio of the weight average molecular weight after MVR measurement to the weight average molecular weight before MVR measurement (initial) was calculated as the "Mw retention after MVR measurement." Mw retention after MVR measurement (%) = [(weight average molecular weight after MVR measurement) / (weight average molecular weight before MVR measurement)] x 100 Measurement equipment: Melt Indexer F-F01 (manufactured by Toyo Seiki Seisakusho, Ltd.)

[0186] <Damp Heat Test and Mw Retention> 1 g of each resin composition produced in the Examples and Comparative Examples was placed in an aluminum tray, and the aluminum tray was left standing at 85°C and 85% RH (damp heat test). After 72 hours, the resin composition was removed to prepare a sample for GPC measurement, and the weight average molecular weight was measured. The ratio of the weight average molecular weight after the damp heat test to the weight average molecular weight before the damp heat test was calculated as the "Mw retention after damp heat test." Mw retention after damp heat test (%) = [(weight average molecular weight after damp heat test) / (weight average molecular weight before damp heat test)] x 100. Measuring equipment: PR-2J, manufactured by Espec Corporation.

[0187] (Example 2-1) BNEF 16.16g (0.030mol), BINOL-DC 12.07g (0.030mol), and H2NTP 1.36g (0.001mol) were placed in a 300mL four-neck flask equipped with a stirrer, and then the system was replaced with a nitrogen atmosphere. The raw materials were heated and melted at 100hPa and 230 ° C., and reacted for 17 minutes. The reaction was allowed to proceed while condensing and removing water distilled from the reaction system with a cooling tube, and the temperature was raised to 240 ° C., the pressure was reduced to 50hPa, and the reaction was allowed to proceed for 13 minutes. Thereafter, the pressure was gradually reduced to 30hPa, 15hPa, and less than 1hPa over 12 minutes, and the temperature was raised to 250 ° C. Thereafter, the pressure was reduced to less than 1hPa, and the reaction was allowed to proceed for 60 minutes.

[0188] Examples 2-2 to 2-3, Comparative Examples 2-1 to 2-4 Using the raw materials shown in Table 3 below, resin compositions were obtained in the same manner as in Example 1-1.

[0189] (Example 2-1') 16.16 g (0.030 mol) of BNEF and 12.07 g (0.030 mol) of BINOL-DC were placed in a 300 mL four-neck flask equipped with a stirrer, and then the system was replaced with a nitrogen atmosphere. The raw materials were heated and melted at 100 hPa and 230 ° C., and reacted for 17 minutes. The reaction was allowed to proceed while condensing and removing water distilled from the reaction system using a cooling tube, and the temperature was raised to 240 ° C., the pressure was reduced to 50 hPa, and the reaction was allowed to proceed for 13 minutes. Thereafter, the pressure was gradually reduced to 30 hPa, 15 hPa, and less than 1 hPa over 12 minutes, and the temperature was raised to 250 ° C. Thereafter, the pressure was reduced to less than 1 hPa, and the reaction was allowed to proceed for 30 minutes. Stirring was stopped, and N ２After the pressure was restored, 1.36 g (0.001 mol) of H2NTP was added, the pressure was reduced again to less than 1 hPa, and stirring was started. The reaction was continued for 5 minutes. Various physical properties of the resin compositions of the Examples and Comparative Examples were measured in the same manner as above. The results are shown in Table 3. The refractive index and Abbe number of Comparative Examples 2-4 were deemed "impossible to measure" because the resin composition dissolved in the contact liquid used for measuring them, causing the liquid to become cloudy.

[0190] Tables 2 and 3 show that resin compositions containing compound (A) (H2NTP) have properties particularly favorable for optical materials. That is, when compound (A) was added to a resin, the refractive index was improved compared to the same resin without compound (A) or resins containing other additives. Furthermore, when resin compositions were produced using the methods of Examples 1-1 to 1-4, the addition of compound (A) improved the melt fluidity of the resin (increased MVR value) and lowered the glass transition temperature (Tg). On the other hand, when the methods of Examples 2-1 to 2-3 were used, the addition of compound (A) promoted the polymerization reaction, resulting in a higher Abbe number and a lower glass transition temperature when compared at equivalent refractive indices.

[0191] Comparing Example 2-1 and Example 2-1', the amounts of polymer raw materials (BINOL-DC and BNEF) and H2NTP added were the same, but the timing of adding the H2NTP was different. That is, in Example 2-1, H2NTP was added before the polymerization reaction, whereas in Example 2-1', H2NTP was added after the polymerization reaction. As can be seen from Table 3, Example 2-1, in which H2NTP was added before the polymerization reaction, had a higher molecular weight and appropriate fluidity (MVR) was obtained. A high molecular weight is advantageous in terms of strength, and appropriate fluidity is advantageous in terms of moldability during molding. When the resin compositions obtained in Example 2-1 and Example 2-1' were subjected to cast film formation by a solvent (dichloromethane) evaporation method, the resin composition of Example 2-1, in which H2NTP was added before the polymerization reaction, was easier to form into a film and obtained a high pencil hardness (H). For these reasons, when adding H2NTP, it is preferable to add H2NTP before the polymerization reaction rather than adding it after the polymerization reaction. Other advantages of adding H2NTP before the polymerization reaction include a reduction in the number of steps, a reduction in thermal history, and an improvement in color tone.

[0192] (Example 3-1) 21.55g (0.0400mol) of BNEF, 9.97g (0.0408mol) of diphenyldimethoxysilane (hereinafter also referred to as "DPDMS"), 1.576g of H2NTP, and 3μmol / mol of lithium acetylacetonate as a catalyst (the amount of catalyst is the relative molar amount to BNEF) were added and placed in a 300mL four-necked flask equipped with a stirrer, and the system was replaced with a nitrogen atmosphere. The raw materials were heated and melted at 200hPa and 230°C, and reacted for 20 minutes. The reaction was allowed to proceed while the methanol distilled from the reaction system was condensed and removed using a cooling tube, and the temperature was raised to 245°C, the pressure was reduced to 100hPa, and the reaction was allowed to proceed for 20 minutes. Thereafter, the pressure was reduced to 50hPa and the reaction was allowed to proceed for 10 minutes, and the pressure was reduced to less than 1hPa and the temperature was raised to 260°C. Then, the mixture was reacted for 120 minutes under reduced pressure of less than 1 hPa.

[0193] (Example 3-2) BNEF 15.08g (0.0280mol), DPBN 6.32g (0.0120mol), DPDMS 9.97g (0.0408mol), H2NTP 1.569g, and lithium acetylacetonate as a catalyst 3μmol / mol (catalyst amount is the relative molar amount to BNEF and DPBN) were added, and placed in a 300mL four-necked flask equipped with a stirrer, and the system was replaced with a nitrogen atmosphere. The raw materials were heated and melted at 200hPa and 230 ° C, and reacted for 20 minutes. While removing the methanol distilled from the reaction system by condensation with a cooling tube, the reaction was allowed to proceed, heated to 245 ° C, reduced pressure to 100hPa, and reacted for 20 minutes. Thereafter, the pressure was reduced to 50hPa and the reaction was allowed to proceed for 10 minutes, and the pressure was reduced to less than 1hPa and the temperature was increased to 260 ° C. Then, the mixture was reacted for 150 minutes under reduced pressure of less than 1 hPa.

[0194] (Example 3-3) BNEF 21.55g (0.0400mol), DPDMS 4.98g (0.0204mol), dinaphthyldimethoxysilane (hereinafter also referred to as "DNDMS") 7.03g (0.0204mol), H2NTP 1.613g, and lithium acetylacetonate as a catalyst 10μmol / mol (catalyst amount is the relative molar amount with respect to BNEF) was added, placed in a 300mL four-necked flask equipped with a stirrer, and the system was replaced with a nitrogen atmosphere. The raw materials were heated and melted at 200hPa and 230 ° C, and reacted for 20 minutes. The reaction was allowed to proceed while condensing and removing the methanol distilled from the reaction system with a cooling tube, and the temperature was raised to 245 ° C, the pressure was reduced to 100hPa, and the reaction was allowed to proceed for 20 minutes. Thereafter, the pressure was reduced to 50 hPa and the mixture was reacted for 10 minutes, and the pressure was reduced to less than 1 hPa and the temperature was raised to 260° C. Then, the mixture was reacted for 120 minutes under reduced pressure of less than 1 hPa.

[0195] (Example 3-4) BPEF 17.56 g (0.0400 mol), DNDMS 14.05 g (0.0408 mol), H2NTP 1.450 g, and lithium acetylacetonate as a catalyst 20 μmol / mol (catalyst amount is the relative molar amount to BNEF) were added and placed in a 300 mL four-necked flask equipped with a stirrer, and the system was replaced with a nitrogen atmosphere. The raw materials were heated and melted at 200 hPa and 230 ° C., and reacted for 20 minutes. While the methanol distilled from the reaction system was condensed and removed with a cooling tube, the reaction was allowed to proceed and the temperature was raised to 245 ° C., the pressure was reduced to 100 hPa, and the reaction was allowed to proceed for 20 minutes. Thereafter, the pressure was reduced to 50 hPa and the reaction was allowed to proceed for 10 minutes, and the pressure was reduced to less than 1 hPa and the temperature was raised to 260 ° C. Then, the reaction was allowed to proceed for 120 minutes under a reduced pressure of less than 1 hPa.

[0196] (Comparative Example 3-1) 21.55 g (0.0400 mol) of BNEF, 9.97 g (0.0408 mol) of DPDMS, and 3 μmol / mol of lithium acetylacetonate as a catalyst (catalyst amount is the relative molar amount to BNEF) were added and placed in a 300 mL four-necked flask equipped with a stirrer, and the system was replaced with a nitrogen atmosphere. The raw materials were heated and melted at 200 hPa and 230 ° C., and reacted for 20 minutes. While removing the methanol distilled from the reaction system by condensation with a cooling tube, the reaction was allowed to proceed and the temperature was raised to 245 ° C., the pressure was reduced to 100 hPa, and the reaction was allowed to proceed for 20 minutes. Thereafter, the pressure was reduced to 50 hPa and the reaction was allowed to proceed for 10 minutes, and the pressure was reduced to less than 1 hPa and the temperature was raised to 260 ° C. Then, the reaction was allowed to proceed for 100 minutes under a reduced pressure of less than 1 hPa.

[0197] (Comparative Example 3-2) BNEF 15.08 g (0.0280 mol), DPBN 6.32 g (0.0120 mol), DPDMS 9.97 g (0.0408 mol), and lithium acetylacetonate as a catalyst 3 μmol / mol (catalyst amount is the relative molar amount to BNEF and DPBN) were added, and placed in a 300 mL four-necked flask equipped with a stirrer, and the system was replaced with a nitrogen atmosphere. The raw materials were heated and melted at 200 hPa and 230 ° C., and reacted for 20 minutes. While removing the methanol distilled from the reaction system by condensation with a cooling tube, the reaction was allowed to proceed and the temperature was raised to 245 ° C., the pressure was reduced to 100 hPa, and the reaction was allowed to proceed for 20 minutes. Thereafter, the pressure was reduced to 50 hPa and the reaction was allowed to proceed for 10 minutes, and the pressure was reduced to less than 1 hPa and the temperature was raised to 260 ° C. The mixture was then reacted for 120 minutes under reduced pressure of less than 1 hPa.

[0198] (Comparative Example 3-3) BNEF 21.55g (0.0400mol), DPDMS 4.98g (0.0204mol), DNDMS 7.03g (0.0204mol), and lithium acetylacetonate as a catalyst 10μmol / mol (catalyst amount is the relative molar amount to BNEF) were added, and placed in a 300mL four-necked flask equipped with a stirrer, and the system was replaced with a nitrogen atmosphere. The raw materials were heated and melted at 200hPa and 230 ° C, and reacted for 20 minutes. While removing the methanol distilled from the reaction system by condensation with a cooling tube, the reaction was allowed to proceed and the temperature was raised to 245 ° C, the pressure was reduced to 100hPa, and the reaction was allowed to proceed for 20 minutes. Thereafter, the pressure was reduced to 50hPa and the reaction was allowed to proceed for 10 minutes, and the pressure was reduced to less than 1hPa and the temperature was raised to 260 ° C. Then, the reaction was allowed to proceed for 90 minutes under a reduced pressure of less than 1hPa.

[0199] (Comparative Example 3-4) 17.56 g (0.0400 mol) of BPEF, 14.05 g (0.0408 mol) of DNDMS, and 20 μmol / mol of lithium acetylacetonate as a catalyst (the amount of catalyst is the relative molar amount to BNEF) were added and placed in a 300 mL four-necked flask equipped with a stirrer, and the system was replaced with a nitrogen atmosphere. The raw materials were heated and melted at 200 hPa and 230 ° C., and reacted for 20 minutes. While the methanol distilled from the reaction system was removed by condensation using a cooling tube, the reaction was allowed to proceed, the temperature was raised to 245 ° C., the pressure was reduced to 100 hPa, and the reaction was allowed to continue for 20 minutes. Thereafter, the pressure was reduced to 50 hPa, the reaction was allowed to continue for 10 minutes, the pressure was reduced to less than 1 hPa, and the temperature was raised to 260 ° C. Then, the reaction was allowed to continue for 100 minutes under a reduced pressure of less than 1 hPa. Various physical properties of the resin compositions of the examples and comparative examples were measured in the same manner as described above. The results are shown in Table 4.

[0200] Table 4 shows that even when a resin containing Si is used, the resin composition containing compound (A) (HNTP) has properties particularly favorable for optical materials. In particular, it has been found to be particularly effective in improving the melt flowability of the resin (increasing the MVR value).

[0201] Example 4-1 0.5 wt% of H2NTP was added to the polycarbonate resin (PC5) produced in Synthesis Example 5 above, and the mixture was kneaded and extruded at 260 ° C using a TEM-18SS kneading extruder (Shibaura Machine Co., Ltd.). The Mw, Tg, and MVR of the resulting composition were measured. The composition was then vacuum dried in a dryer at 110 ° C for 12 hours, and then molded into 3 mm square plate test pieces and 2 mm disc test pieces using an SE50EV fully automatic small injection molding machine (Sumitomo Heavy Industries, Ltd.) (resin temperature 274 ° C, mold temperature 124 ° C). The refractive index and Abbe number were measured using the resulting square plate test pieces, and the water absorption and dimensional change rate were measured using the disc test pieces.

[0202] (Example 4-2, Example 4-3 and Comparative Example 4-1) Compositions and test pieces were produced in the same manner as in Example 4-1, except that the amount of H2NTP added was changed to the amount shown in Table 5 below, and various physical properties were measured. The results of measuring various physical properties for the resin compositions of the examples and comparative examples are shown in Table 5 below. The measurement methods were the same as those for the other examples described above. The water absorption rate and dimensional change rate were measured as follows.

[0203] <Water Absorption Rate> The weight of the 2 mmt disk test pieces produced in the Examples and Comparative Examples was measured in an environment with a temperature of 23°C and humidity of 50%. In the same environment, the test pieces were immersed in water at a temperature of 23°C, and after a predetermined time had passed (24 hours, 336 hours), the test pieces were removed and the weight was measured. The "water absorption rate (%)" was calculated from the difference between the weight before immersion in water (before the test) and the weight after the predetermined time had passed (after the test). Water absorption rate (%) = [(weight after the test - weight before the test) ÷ (weight before the test)] × 100

[0204] <Water absorption rate and dimensional change rate by accelerated test> The weight and dimensions of the 2 mmt disk test pieces produced in the examples and comparative examples were measured before the test. Then, the test pieces were placed in an apparatus with an environment of 85°C and 85% RH and left to stand. After 94 hours, the test pieces were removed and the weight and dimensions were measured again. The "water absorption rate (%)" and "dimensional change rate (%)" were calculated from the difference in weight and dimensions before and after the test. Water absorption rate (%) = [(weight after test - weight before test) ÷ (weight before test)] × 100 Dimensional change rate (%) = [(dimension after test - dimension before test) ÷ (dimension before test) × 100] Apparatus used: PR-2J manufactured by Espec Corporation Measuring equipment: LM-1100 manufactured by Keyence Corporation

[0205] From Table 5, it can be seen that the resin composition containing compound (A) (H2NTP) has properties particularly suitable for optical materials. In particular, it has excellent effects in terms of small water absorption and dimensional change.

[0206] Although several embodiments of the present invention have been described, these embodiments are presented as examples and are not intended to limit the scope of the invention. These novel embodiments can be embodied in various other forms, and various omissions, substitutions, and modifications can be made without departing from the spirit of the invention. These embodiments and their modifications are included within the scope and spirit of the invention, and are also included in the scope of the invention and its equivalents as defined in the claims.

Claims

1. A resin composition comprising a compound (A) represented by the following formula and a resin: The content of the compound (A) in the resin composition is 0.001 to 50 parts by mass relative to 100 parts by mass of the resin in the resin composition, and the resin contains any one of the following resins (J1) to (J3): Resin (J1) A structural unit represented by the following general formula (1), -OSi(R １ R ２ A thermoplastic resin comprising a structural unit consisting of a silane moiety (S) represented by O— and a diol moiety (M) derived from a dihydroxy compound represented by M: [In general formula (1), R １ and R ２ are each independently selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, which may have a substituent, and an aryl group having 6 to 30 carbon atoms, which may have a substituent.] Resin (J2) A polycarbonate resin, polyester resin, or polyestercarbonate resin containing a structural unit derived from a monomer represented by the following general formula (3) and / or a structural unit derived from a monomer represented by the following general formula (4): [In general formula (3), R ａ and R ｂ each independently represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 20 carbon atoms which may have a substituent, an alkoxyl group of 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group of 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group of 5 to 20 carbon atoms which may have a substituent, an aryl group of 6 to 20 carbon atoms which may have a substituent, a heteroaryl group of 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 of 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 optionally substituted 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; and a and b each independently represent an integer of 0 to 10. [In general formula (4), R ｃ and R ｄ are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group of 1 to 20 carbon atoms which may have a substituent, an alkoxyl group of 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group of 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group of 5 to 20 carbon atoms which may have a substituent, and an aryl group of 6 to 20 carbon atoms which may have a substituent; A and B each independently represent an alkylene group of 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; Y １ represents a single bond, a fluorene group which may have a substituent, or any of the structures represented by the following general formulas (8), (9), (11) to (17): [In general formulas (8), (9), (11) to (14), R ２１ and R ２２ 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 ２１ and R ２２ are bonded to each other to form a carbon ring or hetero ring having 1 to 20 carbon atoms which may have a substituent; r and s each independently represent an integer of 0 to 5000; in the general formulae (15) to (17), R ２３ and R ２４ each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, or an alkyl group having 1 to 9 carbon atoms, an alkoxyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms, each of which may have a substituent. Resin (J3) A thermoplastic resin comprising: a dialkoxysilane compound containing at least one of a dialkyldialkoxysilane, a diaryldialkoxysilane, and a monoalkylmonoaryldialkoxysilane; a diaryloxysilane compound containing at least one of a dialkyldiaryloxysilane, a diaryldiaryloxysilane, and a monoalkylmonoaryldiaryloxysilane; and a monoalkoxymonoaryloxysilane compound containing at least one of a dialkylmonoalkoxymonoaryloxysilane, a diarylmonalkoxymonoaryloxysilane, and a monoalkylmonoarylmonalkoxymonoaryloxysilane compound; a fluorene structural unit (F) derived from a fluorene ring-containing dihydroxy compound; and a dinaphthalene structural unit (N) derived from a dinaphthalene-containing dihydroxy compound.

2. The resin composition according to claim 1, wherein the resin composition contains the resin (J2), and the weight average molecular weight (Mw) of the resin (J2) in terms of polystyrene is 10,000 to 300,000.

3. The resin composition according to claim 1 or 2, wherein the resin composition contains the resin (J2), and in the general formula (3) and the general formula (4), A and B each independently represent an alkylene group having 2 or 3 carbon atoms.

4. The resin composition according to any one of claims 1 to 3, wherein the resin composition contains resin (J2), and resin (J2) contains at least a structural unit derived from any one of BPEF, BNE, BNEF, and DPBHBNA.

5. The resin composition according to any one of claims 1 to 4, wherein one or more of the resins (J1) to (J3) further contain a structural unit derived from a dicarboxylic acid or an ester-forming derivative thereof.

6. A resin composition according to any one of claims 1 to 5, having a refractive index (20°C, 589 nm) of 1.640 or more.

7. A molded article comprising the resin composition according to any one of claims 1 to 6.

8. The molded article according to claim 7, which is an optical component.

9. The molded article according to claim 8, wherein the optical component is an optical lens or an optical film.

10. A method for producing a resin composition according to any one of claims 1 to 6, comprising: mixing a monomer constituting said resin with said compound (A) to obtain a mixture; and then subjecting said mixture to polymerization conditions to polymerize said monomer to obtain a resin composition.

11. A method for improving the refractive index of a resin, comprising: mixing a material containing a monomer constituting the resin and a compound (A) represented by the following formula to obtain a mixture; then subjecting the mixture to polymerization conditions to polymerize the monomers to obtain a resin composition.

12. A compounding agent added to a resin to improve the refractive index, comprising a compound (A) represented by the following formula:

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