Diol compound, resin, polycarbonate resin, and optical molded article

Abstract

To provide a diol compound capable of enhancing the refractive index of a resin, and a resin, a polycarbonate resin, and an optical molded article having an enhanced refractive index.SOLUTION: The present invention provides a diol compound represented by the following formula (1). In formula (1), H bonded to C may be substituted with a C1-C10 alkyl group or a C1-C10 heteroatom-containing alkyl group; W represents a group selected from the following formula (W-1) and the like (where * represents a bonding site, and n independently represents an integer of 1 to 4); and Ar1 and Ar2 independently represent a substituted or unsubstituted aromatic group or heteroaromatic group.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a diol compound, a resin, a polycarbonate resin, and an optical molded body.

Background Art

[0002] As a material for an optical lens used in an optical system of various cameras such as a camera, an integrated film camera, and a video camera, optical glass or an optical resin is used. Optical glass is excellent in heat resistance, transparency, dimensional stability, chemical resistance, etc., and there are various types of materials having various refractive indexes and Abbe numbers. However, it has problems such as high material cost, poor moldability, and low productivity.

[0003] On the other hand, an optical lens made of an optical resin has an advantage that it can be mass-produced by injection molding. For example, in a camera lens, a polycarbonate resin or the like is used. However, in recent years, due to the trend of products becoming thinner, lighter, shorter, and smaller, the development of resins with a high refractive index has been demanded. 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, so that the amount of aberration generated on this surface can be reduced. As a result, it becomes possible to reduce the number of lenses, reduce the decentration sensitivity of the lenses, and reduce the lens thickness to make the lens lighter.

[0004] As a technique related to an optical resin, for example, the one described in Patent Document 1 can be mentioned.

[0005] Patent Document 1 describes an optical lens made of a polycarbonate resin obtained by carbonate-bonding 90 to 5 mol% of a dihydroxy compound having a specific structure and 10 to 95 mol% of a dihydroxy compound having a specific structure with a carbonic acid diester, and it is described that an optical lens having a high refractive index and low birefringence that can be industrially produced by injection molding can be provided.

Prior Art Documents

Patent Documents

[0006] Patent Document 1 Japanese Patent Application Laid-Open No. 2005-241962 SUMMARY OF THE INVENTION PROBLEMS TO BE SOLVED BY THE INVENTION

[0007] The present invention provides a diol compound capable of improving the refractive index of a resin, and a resin, a polycarbonate resin, and an optical molded article having an improved refractive index. MEANS FOR SOLVING THE PROBLEMS

[0008] The present inventors have intensively studied to solve the above problems. As a result, they have found that the refractive index can be improved by including a diol compound represented by the following formula (1) as a constituent unit of a resin, and have reached the present invention. According to the present invention, the following diol compound, resin, polycarbonate resin, and optical molded article are provided.

[0009] [1] A diol compound represented by the following formula (1). [Chemical formula] (In the formula (1), the hydrogen atom bonded to the carbon atom may be replaced with an alkyl group having 1 to 10 carbon atoms or a heteroatom-containing alkyl group having 1 to 10 carbon atoms. W represents a group selected from the group consisting of the following formula (W-1) and the following formula (W-2) (where * indicates a bonding point and n is an integer of 1 or more and 4 or less, respectively). [Chemical formula] [Chemical formula] Ar 1 and Ar 2 are each independently an unsubstituted or substituted aromatic group or heteroaromatic group with one or more substituents. [2] In the formula (1), Ar 1 and Ar 2 each independently represent a group selected from the group consisting of the following formula (a) and the following formula (b), and R 1 ~R 3 each independently is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a heteroatom-containing alkyl group having 1 to 10 carbon atoms, a phenyl group, or a fluorine atom. The diol compound according to [1]. [Chemical formula] [Chemical formula] [3] In the formula (a) and the formula (b), the R 1 ~R 3 each independently is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a phenyl group. The diol compound according to [2]. [4] In the formula (W-1) and the formula (W-2), the n is each independently an integer of 1 or more and 3 or less. The diol compound according to any one of [1] to [3]. [5] A resin containing a structural unit derived from the diol compound according to any one of [1] to [4]. [6] A polycarbonate resin containing a structural unit derived from the diol compound according to any one of [1] to [5]. [7] When the total of all the structural units in the polycarbonate resin is 100 mol%, the content of the structural unit derived from the diol compound represented by the formula (1) in the polycarbonate resin is 1 mol% or more and 99 mol% or less. The polycarbonate resin according to [6]. [8] The weight average molecular weight (Mw) in terms of polystyrene is 1.5×10 3 or more and 2.0×10 5 or less. The polycarbonate resin according to [6] or [7]. [9] A polycarbonate resin as described in any one of [6] to [8], having a glass transition temperature measured by a differential scanning calorimeter of 100°C or higher and 190°C or lower.

[10] A polycarbonate resin as described in any one of [6] to [9], having a refractive index nD at a temperature of 23°C and a wavelength of 589 nm of 1.70 or higher and 1.95 or lower.

[11] An optical molded article containing the resin described in [5].

[12] An optical molded article containing a polycarbonate resin as described in any one of [6] to

[10] .

[13] The optical molded article described in

[11] or

[12] , which is an optical lens.

[14] The optical molded article described in

[11] or

[12] , which is an optical film. [Advantages of the Invention]

[0010] According to the present invention, a diol compound capable of improving the refractive index of a resin, as well as a resin, a polycarbonate resin, and an optical molded article with an improved refractive index can be provided. [Embodiments for Carrying Out the Invention]

[0011] Hereinafter, the present invention will be described based on embodiments.

[0012] In the present embodiment, "A to B" indicating a numerical range represents A or more and B or less unless otherwise specified.

[0013] [Diol Compound] The diol compound of the present embodiment is represented by the following formula (1).

[0014] [Chemical Formula]

[0015] In formula (1), the hydrogen atom bonded to the carbon atom may be replaced with an alkyl group having 1 to 10 carbon atoms or a heteroatom-containing alkyl group having 1 to 10 carbon atoms. W represents a group selected from the group consisting of the following formula (W-1) and the following formula (W-2) (wherein * indicates a bonding point and n is an integer of 1 or more and 4 or less independently).

[0016]

Chemical formula

[0017]

Chemical formula

[0018] Ar 1 and Ar 2 are each independently an unsubstituted or substituted aromatic group or heteroaromatic group with one or more substituents.

[0019] The hydrogen atom bonded to the carbon atom in formula (1) may be replaced with an alkyl group having 1 to 10 carbon atoms or a heteroatom-containing alkyl group having 1 to 10 carbon atoms, preferably may be replaced with an alkyl group having 1 to 4 carbon atoms or a heteroatom-containing alkyl group having 1 to 4 carbon atoms, and more preferably may be replaced with a methyl group or a heteroatom-containing alkyl group having 1 carbon atom.

[0020] In formula (1), W represents a group selected from the group consisting of the above formula (W-1) and the above formula (W-2). From the viewpoint of further improving the refractive index, W is preferably a group represented by the above formula (W-1).

[0021] In formula (1), Ar 1 and Ar 2 are preferably selected from the group consisting of aromatic hydrocarbon groups having 6 to 32 carbon atoms and aromatic hetero hydrocarbon groups having 4 to 12 carbon atoms. More preferably, Ar 1 and Ar 2 are each independently the following formula (a) and the following formula (b)

[0022]

Chem.

[0023]

Chem.

[0024] represents a group selected from the group consisting of, and from the viewpoint of further improving the refractive index, it is preferably the group represented by the above (b).

[0025] In formula (a) and formula (b), R 1 ~R 3 are preferably, each independently, a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a heteroatom-containing alkyl group having 1 to 10 carbon atoms, a phenyl group, or a fluorine atom, and from the viewpoint of further improving the refractive index, more preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a phenyl group, still more preferably a hydrogen atom or a phenyl group, and even more preferably a phenyl group.

[0026] In formula (W-1) and formula (W-2), n is each independently an integer of 1 or more and 4 or less, and from the viewpoint of further improving the refractive index, preferably n is an integer of 1 or more and 3 or less, more preferably n is an integer of 1 or 2, and even more preferably n is 2. Further preferably, in formula (W-1) and formula (W-2), n is 2 for both.

[0027] The diol compound of this embodiment is preferably one or more selected from the group consisting of 2,2'-(2,7-bis((E)-2-naphthalen-2-yl)vinyl-9H-fluorene-9,9-diyl)bis(ethane-1-ol), 2,2'-(2,7-di((E)-styryl)vinyl-9H-fluorene-9,9-diyl)bis(ethane-1-ol), 2,2'-(2,7-di((E)-4-methoxystyryl)vinyl-9H-fluorene-9,9-diyl)bis(ethane-1-ol), 2,2'-(2,7-di((E)-4-fluorostyryl)vinyl-9H-fluorene-9,9-diyl)bis(ethane-1-ol), 2,2'-(2,7-bis((E)-2-([1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-1-ol), 2,2'-((6,6'-bis((E)-2-naphthalen-2-yl)vinyl)-[1,1'-naphthalene]-2,2'-diyl)bis(oxy))bis(ethane-1-ol), and 2,2'-(6,6'((E)-styryl)-[1,1'-naphthalene]-2,2'-diyl)bis(oxy))bis(ethane-1-ol); more preferably, one or more selected from the group consisting of 2,2'-(2,7-bis((E)-2-naphthalen-2-yl)vinyl-9H-fluorene-9,9-diyl)bis(ethane-1-ol), 2,2'-(2,7-di((E)-styryl)vinyl-9H-fluorene-9,9-diyl)bis(ethane-1-ol), 2,2'-(2,7-bis((E)-2-([1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-1-ol), and 2,2'-((6,6'-bis((E)-2-naphthalen-2-yl)vinyl)-[1,1'-naphthalene]-2,2'-diyl)bis(oxy))bis(ethane-1-ol). These may be used alone or in combination of two or more.

[0028] From the perspective of improving the refractive index of the cured product, the molecular weight of the diol compound of this embodiment is preferably 430 or more, more preferably 450 or more, still more preferably 500 or more, still more preferably 530 or more, still more preferably 550 or more, and preferably 1500 or less, more preferably 1200 or less, still more preferably 900 or less, still more preferably 700 or less.

[0029] The diol compound of this embodiment can be synthesized, for example, according to the methods of Examples 1 to 4 described below.

[0030] [Production method of the diol compound represented by formula (1)] The diol compound of this embodiment can be synthesized, for example, by the following steps (i) and (ii). Step (i): A dihalogeno-9H-fluorene such as 2,2'-(((2,7-dibromo-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(tetrahydro-2H-pyran)) is treated in a solvent (e.g., tetrahydrofuran, 1,4-dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, sulfolane) in the presence of a base (e.g., sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, potassium hydride, sodium methoxide, sodium ethoxide, t-butoxynatrium, t-butoxypotassium, n-butyllithium) and a palladium-based catalyst such as dichloropalladium bis(di-t-butyl(4-dimethylaminophenyl)phosphine) or a nickel-based catalyst such as nickel dichloride bis(triphenylphosphine) to produce a hydroxyl-protected divinylarene such as 2,2'-(((2,7-bis((E)-2-(naphthalen-2-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran).

[0031] Step (ii): The target compound of formula (1) is produced by treating a hydroxyl group-protected divinylarene such as 2,2'-(((2,7-bis((E)-2-(naphthalen-2-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran) obtained in Step (i) with an acid (concentrated hydrochloric acid, concentrated sulfuric acid, concentrated nitric acid, p-toluenesulfonic acid, and pyridinium p-toluenesulfonate) in a solvent (e.g., methyl cellosolve, toluene and water, tetrahydrofuran and water, tetrahydrofuran and methanol, tetrahydrofuran and ethanol, dimethyl sulfoxide and water).

[0032] [Resin] One aspect of this embodiment is a resin containing a structural unit derived from the diol compound represented by formula (1), preferably an optical resin. Here, examples of the resin containing a structural unit derived from the diol compound represented by formula (1) include one or more selected from the group consisting of polyester resins, polyurethane resins, polycarbonate resins, and polyether resins.

[0033] The polyester resin is obtained by reacting the diol compound represented by formula (1) with an aromatic dicarboxylic acid (e.g., terephthalic acid, isophthalic acid, 2,6-naphthalenedicarboxylic acid) or an aliphatic dicarboxylic acid (e.g., oxalic acid, malonic acid, succinic acid).

[0034] The polyurethane resin is obtained by reacting the diol compound represented by formula (1) with an aromatic diisocyanate (e.g., toluylene diisocyanate, xylylene diisocyanate) or an aliphatic diisocyanate (e.g., pentamethylene diisocyanate, hexamethylene diisocyanate, cyclohexane dimethylene diisocyanate).

[0035] As described later, the polycarbonate resin is obtained by reacting a diol compound represented by formula (1) with a carbonate precursor such as a carbonic acid diester.

[0036] The polyether resin is obtained by reacting a diol compound represented by formula (1) with an aliphatic dihalogen compound (for example, dibromoethane, dibromopropane) in the presence of a base.

[0037] In these resins, the reactants other than the diol compound represented by formula (1) may be used alone or in combination of a plurality. It is also possible to polymerize the resin by using in combination a diol compound other than the diol compound represented by formula (1).

[0038] When using in combination a diol compound other than the diol compound represented by formula (1), when the total of the diol compound represented by formula (1) and the diol compound other than the diol compound represented by formula (1) is 100 mol%, from the viewpoint of further improving the refractive index, the proportion of the diol compound represented by formula (1) is preferably 1 mol% or more, more preferably 5 mol% or more, still more preferably 10 mol% or more, still more preferably 15 mol% or more, still more preferably 20 mol% or more, and preferably 99 mol% or less, more preferably 90 mol% or less, still more preferably 80 mol% or less, still more preferably 70 mol% or less.

[0039] Here, examples of diol compounds other than the diol compound represented by the formula (1) include 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-ethylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-n-propylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-n-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-sec-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-tert-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-cyclohexylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-2-phenylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-(3-methylphenyl)phenyl]fluorene, bis[4-(2'-hydroxyethoxy)phenyl]sulfide, bis[4-(2'-hydroxyethoxy)-3-methylphenyl]sulfide, bis[4-(2'-hydroxyethoxy)phenyl]sulfone, bis[4-(2'-hydroxyethoxy)-3-methylphenyl]sulfone, bis[4-(2'-hydroxyethoxy)phenyl]sulfoxide, bis[4-(2'-hydroxyethoxy)phenyl]sulfoxide, bis(4-hydroxyphenyl)methane, 2,2-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)phenyl ethane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxyphenyl)heptane, 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, 4,4-dihydroxyphenyl-1,1-m-diisopropylbenzene and other bis(4-hydroxyaryl)alkanes;Bis(hydroxyaryl)cycloalkanes such as 1,1-bis(4-hydroxyphenyl)cyclopentane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 2,2,2,2-tetrahydro-3,3,3,3-tetramethyl-1,1-spirobis[1H indene]-6,6-diol; Dihydroxyaryl ethers such as bis(4-hydroxyphenyl) ether, bis(4-hydroxy-3,5-dichlorophenyl) ether; 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-tert-butylphenyl)fluorene, 9,9-bis(4-hydroxy-3-isopropylphenyl)fluorene, 9,9-bis(4-hydroxy-3-cyclohexylphenyl)fluorene, 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene; Ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, 2,2-dimethyl-1,3-propanediol, 1,10-decanediol, diethylene glycol, tetraethylene glycol, norbornanedimethanol, decahydronaphthalenedimethanol, tricyclo[5.2.1.0; 2.6 Decanedimethanol, pentacyclopentadecane dimethanol, cyclopentane-1,3-dimethanol, spiroglycol, etc. can be mentioned.

[0040] [Polycarbonate resin] One aspect of this embodiment is a polycarbonate resin containing a structural unit derived from a diol compound represented by formula (1). The polycarbonate resin of this embodiment has a structural unit derived from a diol compound represented by the following formula (1p). In formula (1p), W is represented by a group selected from the group consisting of the following formula (W-1p) and the following formula (W-2p) (where * indicates a bonding point). Such a polycarbonate resin can realize an optical molded body with an improved refractive index. As a result, it can be suitably used as a material for optical lenses.

[0041]

Chemical formula

[0042]

Chemical formula

[0043]

Chemical formula

[0044] In formula (1p), Ar 1 and Ar 2 , R 1 ~R 3 and n have the same meanings as those in formula (1). Also, for the preferred embodiments of formula (1p), they are the same as those of formula (1).

[0045] When the total of all structural units in the polycarbonate resin is 100 mol%, the content of the structural unit (1p) derived from the diol compound represented by formula (1) in the polycarbonate resin is preferably 1 mol% or more, more preferably 3 mol% or more, still more preferably 5 mol% or more, still more preferably 10 mol% or more, and preferably 99 mol% or less, more preferably 90 mol% or less, still more preferably 80 mol% or less, still more preferably 70 mol% or less, still more preferably 60 mol% or less.

[0046] When the content of the structural unit (1p) derived from the diol compound represented by the formula (1) in the polycarbonate resin is at least the above lower limit value, the refractive index of the polycarbonate resin of the present embodiment can be further improved. When the content of the structural unit (1p) derived from the diol compound represented by the formula (1) in the polycarbonate resin is at most the above upper limit value, the glass transition temperature (Tg), weight average molecular weight (Mw), etc. of the polycarbonate resin of the present embodiment can be adjusted to a more appropriate range.

[0047] The polycarbonate resin of the present embodiment may further contain a structural unit derived from a diol compound other than the diol compound represented by the formula (1) used in the optical resin of the present embodiment.

[0048] The structural unit derived from a diol compound other than the diol compound represented by the formula (1) in the polycarbonate resin of the present embodiment is preferably a structural unit represented by the formula (2p) derived from the diol compound represented by the following formula (2).

[0049]

Chemical formula

[0050] In formula (2), R 1 ~R 4 each independently represents a hydrogen atom, a halogen atom, an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or a cycloalkyl group having 5 to 20 carbon atoms, A each independently represents an alkylene group having 2 to 8 carbon atoms, and p and q each independently represent an integer of 1 to 8.

[0051] In formula (2), examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. In formula (2), examples of the aryl group having 6 to 20 carbon atoms include a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, etc.

[0052] In formula (2), examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an eicosyl group, and the like.

[0053] In formula (2), examples of the cycloalkyl group having 5 to 20 carbon atoms include a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cycloundecyl group, a cyclododecyl group, a cyclotridecyl group, a cyclotetradecyl group, a cyclopentadecyl group, a cyclohexadecyl group, a cycloheptadecyl group, a cyclooctadecyl group, a cyclononadecyl group, a cycloeicosyl group, and the like.

[0054] In formula (2), R 1 ~R 4 are each independently preferably selected from a hydrogen atom, an aryl group having 6 to 20 carbon atoms, and an alkyl group having 1 to 3 carbon atoms, and R 1 ~R 4 are each independently more preferably selected from a hydrogen atom, an aryl group having 6 to 20 carbon atoms, and a methyl group, and R 1 ~R 4 are more preferably hydrogen atoms.

[0055] In formula (2), A represents an alkylene group having 2 to 8 carbon atoms, and is preferably selected from a 1,2-ethylene group, a 1,2-propylene group, a 1,3-propylene group, a 1,2-butylene group, a 1,3-butylene group, a 1,4-butylene group, a 1,5-pentylene group, a 1,6-hexylene group, a 1,7-heptylene group, and a 1,8-octylene group. More preferably, A is selected from a 1,2-ethylene group, a 1,2-propylene group, and a 1,3-propylene group, and even more preferably, A is a 1,2-ethylene group. In formula (2), A is preferably an alkylene group having 2 to 6 carbon atoms, more preferably an alkylene group having 2 to 4 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms.

[0056] In formula (2), p and q are each independently preferably an integer of 1 to 4, more preferably an integer of 1 to 2, and even more preferably both p and q are 1.

[0057]

Chemical formula

[0058] In formula (2p), R 1 ~R 4 , A, and p and q have the same meanings as those in formula (2). Also, the preferred embodiments of formula (2p) are the same as those of formula (2).

[0059] When the total of all the constitutional units in the polycarbonate of the present embodiment is 100 mol%, the content of the constitutional unit (2p) derived from the diol compound represented by formula (2) in the polycarbonate resin of the present embodiment is preferably 1 mol% or more, more preferably 5 mol% or more, even more preferably 10 mol% or more, even more preferably 15 mol% or more, even more preferably 20 mol% or more, from the viewpoint of making the glass transition temperature (Tg), weight average molecular weight (Mw), etc. fall within a more appropriate range. Also, from the viewpoint of further improving the balance of resin physical properties, it is preferably 99 mol% or less, more preferably 95 mol% or less, even more preferably 85 mol% or less, even more preferably 80 mol% or less.

[0060] When the content of the structural unit (1p) derived from the diol compound represented by the formula (1) in the polycarbonate resin of the present embodiment is 1 mol, the content of the structural unit (2p) derived from the diol compound represented by the formula (2) is preferably 0.10 mol or more, more preferably 0.20 mol or more, still more preferably 0.30 mol or more, still more preferably 0.50 mol or more, still more preferably 0.65 mol or more, still more preferably 1.00 mol or more, still more preferably 1.50 mol or more, still more preferably 2.00 mol or more, and preferably 10.00 mol or less, more preferably 9.50 mol or less, still more preferably 9.00 mol or less, still more preferably 5.00 mol or less.

[0061] The weight average molecular weight (Mw) in terms of polystyrene of the polycarbonate resin of the present embodiment is preferably 1.5×10 3 or more, more preferably 2.0×10 3 or more, still more preferably 5.0×10 3 or more, still more preferably 1.0×10 4 or more, and preferably 2.0×10 5 or less, more preferably 1.2×10 5 or less, still more preferably 1.0×10 5 or less, still more preferably 5.0×10 4 or less, still more preferably 3.0×10 4 or less.

[0062] When Mw is equal to or higher than the above lower limit value, it is possible to more effectively suppress the resulting molded body from becoming brittle. When Mw is equal to or lower than the above upper limit value, the melt viscosity becomes more appropriate, so that the resin can be taken out more easily after production, and furthermore, the fluidity is improved, and it becomes easier to perform injection molding in the molten state.

[0063] The refractive index nD of the polycarbonate resin of the present embodiment at a temperature of 23°C and a wavelength of 589 nm is preferably 1.70 or more, more preferably 1.75 or more, still more preferably 1.77 or more, still more preferably 1.78 or more, still more preferably 1.80 or more, still more preferably 1.82 or more, from the viewpoint of improving the refractive index of the obtained optical molded article, and preferably 1.95 or less, more preferably 1.93 or less, still more preferably 1.90 or less, still more preferably 1.87 or less, from the viewpoint of adjusting the obtained optical molded article.

[0064] The glass transition temperature (Tg) of the polycarbonate resin of the present embodiment measured by a differential scanning calorimeter is preferably 100°C or more, more preferably 110°C or more, still more preferably 120°C or more, still more preferably 130°C or more, still more preferably 140°C or more, and preferably 190°C or less, more preferably 180°C or less, still more preferably 170°C or less, still more preferably 160°C or less. When Tg is at least the above lower limit value, it is preferable because the use temperature range becomes wider. Also, when Tg is at most the above upper limit value, it is preferable because the melting temperature of the resin becomes lower and resin decomposition and coloring are less likely to occur. Also, when Tg is at most the above upper limit value, even with a general-purpose mold temperature controller, the difference between the mold temperature and the glass transition temperature of the resin can be reduced. Therefore, it is preferable and easy to use in applications where strict surface accuracy is required for the product.

[0065] Furthermore, antioxidants, mold release agents, ultraviolet absorbers, fluidity modifiers, crystal nucleating agents, reinforcing agents, dyes, antistatic agents, antibacterial agents, etc. can be added to the polycarbonate resin of the present embodiment.

[0066] [Method for Producing Polycarbonate Resin] The polycarbonate resin of the present embodiment can be produced using the compound represented by formula (1) as a raw material. Specifically, the compound represented by formula (1) and a carbonate precursor such as a diester carbonate can be reacted by a melt polycondensation method in the presence of a basic compound catalyst, a transesterification catalyst, or a mixed catalyst composed of both, or without a catalyst.

[0067] Examples of the diester carbonate used in the production of the polycarbonate resin of the present embodiment include diphenyl carbonate, di-p-tolyl carbonate, di-m-tolyl carbonate, di-o-tolyl carbonate, bis(p-chlorophenyl) carbonate, bis(m-chlorophenyl) carbonate, bis(o-chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, di-n-butyl carbonate, dicyclohexyl carbonate, and the like. Among these, diphenyl carbonate is preferred. Diphenyl carbonate is preferably used in a ratio of preferably 0.90 to 1.20 mol, more preferably 0.95 to 1.10 mol, per 1 mol of the total of the diol compound represented by formula (1) and a diol compound other than the diol compound represented by formula (1) described above.

[0068] Examples of the basic compound catalyst used in the production of the polycarbonate resin of the present embodiment include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds. Such compounds are preferably organic acid salts, inorganic salts, oxides, hydroxides, hydrides, or alkoxides of alkali metals and alkaline earth metal compounds, or quaternary ammonium hydroxides and their salts, amines, etc., and these compounds can be used alone or in combination.

[0069] Examples of the alkali metal compound include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, alkoxides, etc. of alkali metals. Specifically, sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium hydrogen carbonate, sodium carbonate, potassium hydrogen carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, cesium acetate, lithium acetate, sodium stearate, potassium stearate, cesium stearate, lithium stearate, sodium borohydride, phenylboron sodium, sodium benzoate, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, disodium phenyl phosphate, disodium salt, dipotassium salt, dicesium salt or dilithium salt of bisphenol A, sodium salt, potassium salt, cesium salt or lithium salt of phenol, etc. are used.

[0070] Examples of the alkaline earth metal compound include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, alkoxides, etc. of alkaline earth metal compounds. Specifically, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium hydrogen carbonate, calcium hydrogen carbonate, strontium hydrogen carbonate, barium hydrogen carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenyl phosphate, etc. are used.

[0071] Examples of the nitrogen-containing compound include quaternary ammonium hydroxides and their salts, amines, etc. Specifically, quaternary ammonium hydroxides having an alkyl group, an aryl group, etc., such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetra-n-propylammonium hydroxide, tetra-n-butylammonium hydroxide, trimethylbenzylammonium hydroxide; tertiary amines such as triethylamine, dimethylbenzylamine, triphenylamine; secondary amines such as diethylamine, dibutylamine; primary amines such as n-propylamine, n-butylamine; imidazoles such as 2-methylimidazole, 2-phenylimidazole, benzimidazole; or bases or basic salts such as ammonia, tetramethylammonium borohydride, tetra-n-butylammonium borohydride, tetra-n-butylammonium tetraphenylborate, tetraphenylammonium tetraphenylborate are used.

[0072] As the transesterification catalyst, salts of zinc, tin, zirconium, lead, etc. are preferably used, and these can be used alone or in combination. Specifically, as the transesterification catalyst, 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, etc. are used. These catalysts are preferably used in a ratio of 10 -9 ~10 -3 moles, more preferably 10 -8 ~10 -4 moles, per 1 mole of the total diol compound.

[0073] The melt polycondensation method is to perform melt polycondensation while removing by-products by a transesterification reaction under heating at normal pressure or reduced pressure using the above raw materials and catalyst. In the melt polycondensation method of this embodiment, it is desirable to melt a diol compound and a carbonic acid diester in a reaction vessel and then carry out the reaction while retaining the monohydroxy compound produced as a by-product.

[0074] In order to retain the monohydroxy compound, the pressure can be controlled by closing the reactor, reducing the pressure, increasing the pressure, etc. The reaction time for this step is preferably 20 minutes or more and 240 minutes or less, more preferably 40 minutes or more and 180 minutes or less, and even more preferably 60 minutes or more and 150 minutes or less. At this time, if the monohydroxy compound produced as a by-product is distilled off immediately after being produced, the finally obtained polycarbonate resin has a low content of high molecular weight substances. However, if the by-produced monohydroxy compound is retained in the reaction vessel for a certain period of time, a polycarbonate resin with a high content of high molecular weight substances can be obtained finally.

[0075] Generally, the melt polycondensation reaction is carried out in a multi-stage process of two or more stages. Specifically, the first-stage reaction is preferably carried out at a temperature of 120 to 270°C, more preferably 180 to 250°C, and preferably for 0.1 to 5 hours, more preferably for 0.5 to 3 hours under normal pressure or pressure. Then, while increasing the degree of vacuum in the reaction system, the reaction temperature is increased to carry out the reaction between the diol compound and the carbonic acid diester. Finally, it is preferable to carry out the polycondensation reaction at a degree of vacuum of 133 Pa (1 mmHg) or less and a temperature of 200 to 350°C for 0.05 to 2 hours.

[0076] The melt polycondensation reaction may be carried out continuously or batchwise. The reaction apparatus used for carrying out the reaction may be a vertical type equipped with an anchor type stirring blade, a max blend stirring blade, a helical ribbon type stirring blade, etc., a horizontal type equipped with a paddle blade, a grid blade, a glasses blade, etc., or an extruder type equipped with a screw. Further, it is preferably implemented to use a reaction apparatus in which these reaction apparatuses are appropriately combined in consideration of the viscosity of the polymer.

[0077] After the polycondensation reaction is completed, in order to maintain the thermal stability and hydrolysis stability, the catalyst may be removed or deactivated. Generally, a method of deactivating the catalyst by adding a known acidic substance can be preferably implemented. Specifically, as the acidic substance, 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, di-n-octyl phosphite, and mono-n-octyl phosphite; phosphoric acid esters such as triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, di-n-butyl phosphate, di-n-octyl phosphate, and mono-n-octyl phosphate; phosphonic acids such as diphenylphosphonic acid, di-n-octylphosphonic acid, and di-n-butylphosphonic acid; phosphonic acid esters such as diethyl phenylphosphonate; phosphines such as triphenylphosphine and bis(diphenylphosphino)ethane; boronic acids such as boric acid and phenylboronic acid; aromatic sulfonates such as tetra-n-butylphosphonium n-dodecylbenzenesulfonate; organic halides such as stearic acid chloride, benzoyl chloride, and p-toluenesulfonic acid chloride; alkyl sulfates such as dimethyl sulfate; and organic halides such as benzyl chloride are preferably used. These deactivators are preferably used in an amount of 0.01 to 50 times the molar amount of the catalyst, more preferably 0.3 to 20 times the molar amount. If the amount is less than 0.01 times the molar amount of the catalyst, the deactivation effect will be insufficient, which is not preferable. Also, if the amount is more than 50 times the molar amount of the catalyst, the heat resistance of the resin will decrease and the molded article will be easily colored, which is not preferable.

[0078] After the catalyst is deactivated, a step of devolatilizing and removing low-boiling compounds in the polymer at a pressure of 13 to 133 Pa (0.1 to 1 mmHg) and a temperature of 200 to 350 °C may be provided. For this step, a horizontal device equipped with a stirring blade with excellent surface renewal ability, such as a paddle blade, a grid blade, or a glasses blade, or a thin-film evaporator is preferably used.

[0079] The polycarbonate resin of this embodiment desirably has as little foreign matter content as possible, and filtration of the molten raw material, filtration of the catalyst solution, etc. are preferably carried out. The mesh of the filter is preferably 5 μm or less, more preferably 1 μm or less. Further, filtration of the resin to be produced by a polymer filter is preferably carried out. The mesh of the polymer filter is preferably 100 μm or less, more preferably 30 μm or less. Also, the step of collecting the resin pellets is preferably a low-dust environment, and more preferably has a cleanliness of class 1000 or less.

[0080] [Optical molded article] The optical molded article of this embodiment contains the resin of this embodiment or a polycarbonate resin, and an optical molded article can be manufactured using the resin of this embodiment or a polycarbonate resin. For example, it is molded by any method such as an injection molding method, a compression molding method, an injection compression molding method, an extrusion molding method, a solution casting method, etc. Since the polycarbonate resin of this embodiment is excellent in moldability and heat resistance, it can be particularly advantageously used in optical lenses that require injection molding. At the time of molding, the polycarbonate resin of this embodiment can be used by mixing it with other resins such as other polycarbonate resins and polyester resins.

[0081] Since the refractive index of the polycarbonate resin of this embodiment is improved, in addition to optical lenses, it can be advantageously used as a structural material or functional material for optical parts such as transparent conductive substrates, optical disks, liquid crystal panels, optical cards, sheets, films, optical fibers, connectors, vapor-deposited plastic mirrors, displays, etc. used in liquid crystal displays, organic EL displays, solar cells, etc.

[0082] In addition, in order to impart various characteristics without impairing the object of the present embodiment, various additives can be contained in the optical molded body of the present embodiment. Examples of the additives include antioxidants, processing stabilizers, mold release agents, ultraviolet absorbers, bluing agents, polymerization metal deactivators, flame retardants, lubricants, antistatic agents, heat ray shielding agents, fluorescent dyes (including fluorescent brighteners), pigments, light scattering agents, reinforcing fillers, surfactants, antibacterial agents, plasticizers, compatibilizers, other resins, elastomers, and the like.

[0083] Examples of the antioxidant include triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, N,N-hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamide), 3,5-di-tert-butyl-4-hydroxybenzylphosphonate-diethyl ester, tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, and 3,9-bis{1,1-dimethyl-2-[β-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]ethyl}-2,4,8,10-tetraoxaspiro(5,5)undecane. The content of the antioxidant in the optical molded body of the present embodiment is preferably 0.001 to 0.3 parts by mass with respect to 100 parts by mass of the polycarbonate resin.

[0084] Examples of the processing stabilizer include phosphorus-based processing heat stabilizers and sulfur-based processing heat stabilizers.

[0085] Examples of phosphorus-based processing heat stabilizers include phosphorous acid, phosphoric acid, phosphonous acid, phosphonic acid, and their esters. Specifically, triphenyl phosphite, tris(nonylphenyl) phosphite, tris(2,4-di-tert-butylphenyl) phosphite, tris(2,6-di-tert-butylphenyl) phosphite, tri-n-decyl phosphite, tri-n-octyl phosphite, tri-n-octadecyl phosphite, di-n-decyl monophenyl phosphite, di-n-octyl monophenyl phosphite, diisopropyl monophenyl phosphite, mono-n-butyl diphenyl phosphite, monodecyl diphenyl phosphite, mono-n-octyl diphenyl phosphite, bis(2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, 2,2-methylenebis(4,6-di-tert-butylphenyl) octyl phosphite, bis(n-nonylphenyl) pentaerythritol diphosphite, bis(2,4-dicumylphenyl) pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, tri-n-butyl phosphate, triethyl phosphate, trimethyl phosphate, triphenyl phosphate, diphenyl monoorthoxenyl phosphate, di-n-butyl phosphate, di-n-octyl phosphate, diisopropyl phosphate, dimethyl benzenephosphonate, diethyl benzenephosphonate, dipropyl benzenephosphonate, tetrakis(2,4-di-t-butylphenyl)-4,4′-biphenylenediphosphonite, tetrakis(2,4-di-t-butylphenyl)-4,3′-biphenylenediphosphonite, tetrakis(2,4-di-t-butylphenyl)-3,3′-biphenylenediphosphonite, bis(2,4-di-tert-butylphenyl)-4-phenyl-phenylphosphonite, and bis(2,4-di-tert-butylphenyl)-3-phenyl-phenylphosphonite, etc. The content of the phosphorus-based processing heat stabilizer in the optical molded article of this embodiment is preferably 0.001 to 0.2 parts by mass with respect to 100 parts by mass of the polycarbonate resin.

[0086] Examples of sulfur-based processing heat stabilizers include pentaerythritol-tetrakis(3-laurylthiopropionate), pentaerythritol-tetrakis(3-myristylthiopropionate), pentaerythritol-tetrakis(3-stearylthiopropionate), dilauryl-3,3′-thiodipropionate, dimyristyl-3,3′-thiodipropionate, distearyl-3,3′-thiodipropionate, and the like. The content of the sulfur-based processing heat stabilizer in the optical molded body of the present embodiment is preferably 0.001 to 0.2 parts by mass with respect to 100 parts by mass of the polycarbonate resin.

[0087] As the mold release agent, those in which 90% by mass or more thereof is composed of an ester of an alcohol and a fatty acid are preferable. Specific examples of the ester of an alcohol and a fatty acid include esters of a monohydric alcohol and a fatty acid, partial esters or full esters of a polyhydric alcohol and a fatty acid. As the ester of the monohydric alcohol and the fatty acid, an ester of a monohydric alcohol having 1 to 20 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms is preferable. Further, as the partial ester or full ester of the polyhydric alcohol and the fatty acid, a partial ester or full ester of a polyhydric alcohol having 1 to 25 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms is preferable.

[0088] Examples of esters of monohydric alcohols and saturated fatty acids include stearyl stearate, palmityl palmitate, n-butyl stearate, methyl laurate, isopropyl palmitate, and the like. Examples of partial esters or full esters of polyhydric alcohols and saturated fatty acids include monoglyceride stearate, diglyceride stearate, triglyceride stearate, monosorbitol stearate, monoglyceride behenate, monoglyceride caprate, monoglyceride laurate, pentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetraperargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, 2-ethylhexyl stearate, and full esters or partial esters of dipentaerythritol such as dipentaerythritol hexastearate.

[0089] The content of the mold release agent in the optical molded article of this embodiment is preferably in the range of 0.005 to 2.0 parts by mass, more preferably in the range of 0.01 to 0.6 parts by mass, and even more preferably in the range of 0.02 to 0.5 parts by mass with respect to 100 parts by mass of the polycarbonate resin.

[0090] As the ultraviolet absorber, at least one ultraviolet absorber selected from the group consisting of benzotriazole-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers, triazine-based ultraviolet absorbers, cyclic iminoester-based ultraviolet absorbers, and cyanoacrylate-based ultraviolet absorbers is preferable. Any of the following ultraviolet absorbers may be used alone or in combination of two or more.

[0091] Examples of benzotriazole-based ultraviolet absorbers include 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole, 2-(2-hydroxy-3,5-dicumylphenyl)phenylbenzotriazole, 2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-5-chlorobenzotriazole, 2,2′-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazol-2-yl)phenol], 2-(2-hydroxy-3,5-di-tert-butylphenyl)benzotriazole, 2-(2-hydroxy-3,5-di-tert-butylphenyl)-5-chlorobenzotriazole, 2-(2-hydroxy-3,5-di-tert-amylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-butylphenyl)benzotriazole, 2-(2-hydroxy-4-n-octyloxyphenyl)benzotriazole, 2,2′-methylenebis(4-cumyl-6-benzotriazolylphenyl), 2,2′-p-phenylenebis(1,3-benzoxazin-4-one), 2-[2-hydroxy-3-(3,4,5,6-tetrahydrophthalimidomethyl)-5-methylphenyl]benzotriazole, and the like.

[0092] Examples of benzophenone-based ultraviolet absorbers include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octyloxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone, 2-hydroxy-4-methoxy-5-sulfoxybenzophenone, 2-hydroxy-4-methoxy-5-sulfoxytrihydrate rate benzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy-5-sodium sulfoxybenzophenone, bis(5-benzoyl-4-hydroxy-2-methoxyphenyl)methane, 2-hydroxy-4-n-dodecyloxybenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone, and the like.

[0093] Examples of triazine-based ultraviolet absorbers include 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[(n-hexyl)oxy]-phenol, 2-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)-5-[(n-octyl)oxy]-phenol, and the like.

[0094] Examples of the cyclic imino ester-based ultraviolet absorber include 2,2′-bis(3,1-benzoxazin-4-one), 2,2′-p-phenylene bis(3,1-benzoxazin-4-one), 2,2′-m-phenylene bis(3,1-benzoxazin-4-one), 2,2′-(4,4′-diphenylene) bis(3,1-benzoxazin-4-one), 2,2′-(2,6-naphthalene) bis(3,1-benzoxazin-4-one), 2,2′-(1,5-naphthalene) bis(3,1-benzoxazin-4-one), 2,2′-(2-methyl-p-phenylene) bis(3,1-benzoxazin-4-one), 2,2′-(2-nitro-p-phenylene) bis(3,1-benzoxazin-4-one), and 2,2′-(2-chloro-p-phenylene) bis(3,1-benzoxazin-4-one).

[0095] Examples of the cyanoacrylate-based ultraviolet absorber include 1,3-bis-[(2′-cyano-3′,3′-diphenylacryloyl)oxy]-2,2-bis[(2-cyano-3,3-diphenylacryloyl)oxy]methyl)propane, and 1,3-bis-[(2-cyano-3,3-diphenylacryloyl)oxy]benzene.

[0096] The content of the ultraviolet absorber in the optical molded article of this embodiment is preferably 0.01 to 3.0 parts by mass, more preferably 0.02 to 1.0 parts by mass, and even more preferably 0.05 to 0.8 parts by mass with respect to 100 parts by mass of the polycarbonate resin. Within such a blending amount range, it is possible to impart sufficient weather resistance to the polycarbonate resin according to the application.

[0097] Examples of the bluing agent include Macrolex Violet B and Macrolex Blue RR of Bayer and Polysynthren Blue RLS of Clariant.

[0098] The bluing agent is effective for eliminating the yellowness of polycarbonate resins. Particularly in the case of polycarbonate resins imparted with weather resistance, a certain amount of ultraviolet absorber is compounded, and thus, due to the "action and color of the ultraviolet absorber", polycarbonate resin molded articles tend to become yellowish. In particular, for imparting a natural transparency to sheets and lenses, compounding of the bluing agent is effective. The compounding amount of the bluing agent is, for example, preferably 0.05 to 1.5 ppm, more preferably 0.1 to 1.2 ppm, based on the polycarbonate resin.

[0099] On the surface of the optical molded body, a coat layer such as an antireflection layer or a hard coat layer may be provided as necessary. The antireflection layer may be a single layer or a multilayer, and may be an organic substance or an inorganic substance, but is preferably an inorganic substance. Specifically, oxides or fluorides such as silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, cerium oxide, magnesium oxide, and magnesium fluoride are exemplified.

[0100] [Optical lens] The resin of this embodiment or the optical molded body containing a polycarbonate resin may be used as an optical lens. The optical lens produced using the resin of this embodiment or a polycarbonate resin has an improved refractive index, and thus can be used in fields where expensive high-refractive-index glass lenses have been conventionally used, such as telescopes, binoculars, and television projectors, and is extremely useful. As necessary, it is preferably used in the form of an aspherical lens. Since an aspherical lens can substantially make the spherical aberration zero with a single lens, it is not necessary to remove the spherical aberration by combining a plurality of spherical lenses, and weight reduction and reduction of production costs can be achieved. Therefore, aspherical lenses are particularly useful as camera lenses among optical lenses. The optical lens of this embodiment is molded by an arbitrary method such as an injection molding method, a compression molding method, or an injection compression molding method. According to this embodiment, a high-refractive-index low-birefringence aspherical lens, which is technically difficult to process with a glass lens, can be obtained more easily.

[0101] [Optical film]) The optical molded body containing the resin or polycarbonate resin of this embodiment may be used as an optical film. Since the refractive index of the optical film manufactured using the resin or polycarbonate resin of this embodiment is improved, it is suitably used for films for liquid crystal substrates, optical memory cards, etc.

[0102] As mentioned above, the embodiments of the present invention have been described, but these are examples of the present invention, and various configurations other than the above can also be adopted.

Example

[0103] Hereinafter, this embodiment will be described in detail with reference to Examples and Comparative Examples. Note that this embodiment is not limited to the descriptions of these Examples at all.

[0104] 1. Measurement and evaluation methods In the following Examples and Comparative Examples, the measurement and evaluation of each physical property were performed by the following methods.

[0105] 1) Weight average molecular weight (Mw) in terms of polystyrene: Using a gel permeation chromatograph (GPC: Waters 1515, 2414, and 2489), with chloroform as the eluent, a calibration curve was created using standard polystyrene with a known molecular weight (molecular weight distribution = 1) (product name: EasiCal Type PS-1, manufacturer: Agilent Technologies). Based on this calibration curve, the Mw of the polycarbonate resin in each example was calculated from the retention time of GPC. GPC device: Waters 1515, 2414, and 2489 GPC column: Shodex GPC K-806L Measurement temperature: 40 °C Sample concentration: 0.3 wt%

[0106] 2) Refractive index (nD): A chloroform solution of each example of the polycarbonate resin with a concentration of 4.0 wt% was coated on a silicon wafer using a spin coater at 800 rpm for 40 seconds and 1500 rpm for 10 seconds, baked at 120 °C for 5 minutes to prepare a sample. Using a spectroscopic ellipsometer GES5E (manufactured by SEMILAB), the refractive index nD at a film temperature of 23 °C and a wavelength of 589 nm was calculated by fitting the following optical model to the optical measurement data at 23 °C and a wavelength of 200 - 1000 nm. (Optical model) Laminated structure: Film / SiO 2 (2 nm thick) / Si substrate (500 μm thick) Film dispersion formula: Cauchy + Lorentz oscillator model

[0107] 3) Glass transition temperature (Tg): Measured by a differential scanning calorimeter (DSC: DSC - 60 manufactured by Shimadzu Corporation). Each example of the polycarbonate resin was heated from room temperature to 250 °C at a heating rate of 10 °C / min, held for 5 minutes, then cooled to -20 °C at a cooling rate of 10 °C / min and held for 5 minutes. Then, the glass transition temperature Tg (°C) of each example of the polycarbonate resin was determined from the endothermic curve when heating to 250 °C at a heating rate of 10 °C / min.

[0108] 5) Copolymerization ratio: 1 1H - NMR (Product name: JNM - ECZ400S manufactured by JEOL) was used to measure the NMR of each example of the polycarbonate resin dissolved in chloroform - d 1 and the copolymerization ratio was determined from the integral ratio of the hydrogen bonded to the aromatic carbon.

[0109] <Preparation of the diol compound represented by formula (1)>

[0110] [Example 1] Synthesis of 2,2'-(2,7 - bis((E)-2 - naphthalen - 2 - yl)vinyl - 9H - fluorene - 9,9 - diyl)bis(ethan - 1 - ol) Step (i) A 500 mL three-necked flask equipped with a stirring device, a reflux tube, and a thermometer was charged with 20.0 g (34.5 mmol) of 2,2'-(((2,7-dibromo-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(tetrahydro-2H-pyran)), 12.2 g (79.3 mmol) of 2-vinylnaphthalene, 489 mg (0.69 mmol) of bis(di-t-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium, 44.9 g (137.8 mmol) of cesium carbonate, and 200 mL of DMF, and stirred at 120 °C for 18 hours. Then, it was cooled to room temperature, 200 ml of water and 400 ml of ethyl acetate were added, and the layers were separated. The organic layer was washed with 100 mL of a saturated aqueous sodium chloride solution. Then, the organic layer was separated and concentrated using a rotary evaporator to obtain a viscous solid. The obtained viscous solid was dissolved in methylene chloride and purified by silica gel column chromatography to obtain 15.1 g (20.8 mmol) of 2,2'-(((2,7-bis((E)-2-(naphthalen-2-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran) (the compound represented by the following formula (1-i)) in a yield of 60%.

[0111] [Chemical formula]

[0112] The NMR analysis results of 2,2'-(((2,7-bis((E)-2-(naphthalen-2-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran) are shown below. 1 H-NMR(CDCl 3): δ = 1.20 - 1.69 (m, 12H), 2.51 (t, 4H), 2.80 (q, 2H), 3.19 - 3.28 (m, 4H), 3.50 - 3.57 (m, 2H), 4.15 (t, 2H), 7.33 (d, 4H), 7.42 - 7.56 (m, 6H), 7.30 - 7.35 (m, 4H), 7.43 - 7.52 (m, 4H), 7.52 - 7.75 (d, 2H), 7.63 - 7.70 (m, 4H), 7.76 - 7.88 (m, 8H), 7.90 (s, 2H)

[0113] Step (ii) Into a 500 mL three-necked flask equipped with a stirring device, a reflux tube, and a thermometer, add 15.1 g (20.8 mmol) of 2,2'-(((2,7-bis((E)-2-(naphthalen-2-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran), 125 mL of methyl cellosolve, and 1.5 g of concentrated hydrochloric acid, and stir at 120 °C for 8 hours. Then, cool to room temperature and concentrate using a rotary evaporator to obtain a viscous solid. Add 30 mL of methyl cellosolve to the obtained viscous solid, perform suspension washing at 120 °C, cool to room temperature, and filter to obtain 6.9 g (12.3 mmol) of 2,2'-(2,7-bis((E)-2-naphthalen-2-yl)vinyl-9H-fluorene-9,9-diyl)bis(ethan-1-ol) (the compound represented by the following formula (1-ii)) with a yield of 59%.

[0114] [Chemical formula]

[0115] The NMR analysis results of 2,2'-(2,7-bis((E)-2-naphthalen-2-yl)vinyl-9H-fluorene-9,9-diyl)bis(ethan-1-ol) are shown below. 1 H-NMR (DMSO-d6): δ = 1.50 (t, 4H), 1.88 - 1.96 (m, 4H), 3.39 (t, 2H), 6.62 - 6.73 (m, 8H), 6.79 (d, 2H), 6.99 (d, 2H), 7.04 - 7.11 (m, 10H), 7.24 (s, 2H)

[0116] [Example 2] Synthesis of 2,2'-(2,7-di((E)-styryl)vinyl-9H-fluorene-9,9-diyl)bis(ethane-1-ol) Step (i) Synthesis was carried out in the same manner as in Step (i) of Example 1, except that 8.99 g (86.2 mmol) of styrene was used instead of 2-vinylnaphthalene as the starting material, to obtain 11.7 g (18.6 mmol) of 2,2'-(((2,7-di((E)-styryl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran) (compound represented by the following formula (2-i)) in a yield of 54%.

[0117] [Chemical formula]

[0118] The NMR analysis results of 2,2'-(((2,7-di((E)-styryl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran) are shown below. 1 H-NMR(CDCl 3 ): δ = 1.20 - 1.69 (m, 12H), 2.48 (t, 4H), 2.77 (q, 2H), 3.12 - 3.28 (m, 4H), 3.46 - 3.58 (m, 2H) 4.13 (t, 2H), 7.15 - 7.19 (m, 4H), 7.27 (t, 2H), 7.38 (t, 4H), 7.48 (t, 2H), 7.52 - 7.61 (m, 6H), 7.64 (d, 2H)

[0119] Step (ii) Instead of 2,2'-(((2,7-bis((E)-2-(naphthalen-2-yl)vinyl)-9H-fluoren-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran), the synthesis was carried out in the same manner as in step (ii) of Example 1, except that 2,2'-(((2,7-di((E)-styryl)-9H-fluoren-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran) obtained in the above step (i) was used, and 2,2'-(2,7-di((E)-styryl)vinyl-9H-fluoren-9,9-diyl)bis(ethan-1-ol) (compound represented by the following formula (2-ii)) was obtained in a yield of 77% (6.5 g, 14.1 mmol).

[0120] [Chemical formula]

[0121] The NMR analysis results of 2,2'-(2,7-di((E)-styryl)vinyl-9H-fluoren-9,9-diyl)bis(ethan-1-ol) are shown below. 1 H-NMR (DMSO-d6): δ = 1.47 (t, 4H), 1.85 - 1.92 (m, 4H), 3.35 (t, 2H), 6.43 (t, 2H), 6.51 - 6.58 (m, 8H), 6.73 (d, 2H), 6.80 (d, 4H), 6.75 (d, 2H), 6.98 (s, 2H)

[0122] [Example 3] Synthesis of 2,2'-(2,7-bis((E)-2-([1,1'-biphenyl]-4-yl)vinyl)-9H-fluoren-9,9-diyl)bis(ethan-1-ol) Step (i) As the starting material, 13.0 g (72.4 mmol) of 4-vinylbiphenyl was used instead of 2-vinylnaphthalene, and the synthesis was carried out in the same manner as in step (i) of Example 1 to obtain 18.1 g (23.2 mmol) of 2,2'-(((2,7-bis((E)-2-[1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran) (the compound represented by the following formula (3-i)) in a yield of 67%.

[0123] [Chemical formula]

[0124] The NMR analysis results of 2,2'-(((2,7-bis((E)-2-[1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran) are shown below. 1 H-NMR(CDCl 3 ): δ = 1.28 - 1.68 (m, 12H), 2.50 (t, 4H), 2.79 (q, 2H), 3.18 - 3.27 (m, 4H), 3.50 - 3.57 (m, 2H), 4.15 (t, 2H), 7.21 (q, 4H), 7.36 (t, 2H), 7.42 - 7.53 (m, 6H), 7.60 - 7.67 (m, 16H)

[0125] Step (ii) Instead of 2,2'-(((2,7-bis((E)-2-(naphthalen-2-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran), 2,2'-(((2,7-bis((E)-2-[1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(tetrahydro-2H-pyran) obtained in the above step (ii) was used, and the synthesis was carried out in the same manner as in step (ii) of Example 1. 2,2'-(2,7-bis((E)-2-([1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethan-1-ol) (compound represented by the following formula (3-ii)) was obtained in a yield of 91% (12.9 g, 21.1 mmol).

[0126] [Chemical formula]

[0127] The NMR analysis results of 2,2'-(2,7-bis((E)-2-([1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethan-1-ol) are shown below. 1 H-NMR (DMSO-d6): δ = 1.50 (t, 4H), 1.86 - 1.95 (m, 4H), 3.38 (t, 2H), 6.55 (t, 2H), 6.60 (s, 4H), 6.56 (t, 4H), 6.78 (d, 4H), 6.87 - 6.95 (m, 12H), 6.98 (d, 2H), 7.03 (s, 2H)

[0128] [Example 4] Synthesis of 2,2'-((6,6'-bis((E)-2-naphthalen-2-yl)vinyl)-[1,1'-naphthalene]-2,2'-diyl)bis(oxy))bis(ethan-1-ol) Step (i) As the starting material, instead of 2,2'-(((2,7-dibromo-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl))bis(tetrahydro-2H-pyran)), 21.1 g (47.4 mmol) of 6,6'-dibromo[1,1'-binaphthalene]-2,2'-diol was used, and the synthesis was carried out in the same manner as in step (i) of Example 1 to obtain 19.2 g (32.5 mmol) of 6,6'-bis((E)-2-(naphthalen-2-yl)vinyl)-[1,1'-binaphthalene]-2,2'-diol (the compound represented by the following formula (4-i)) in a yield of 69%.

[0129]

Chemical formula

[0130] The NMR analysis results of 6,6'-bis((E)-2-(naphthalen-2-yl)vinyl)-[1,1'-binaphthalene]-2,2'-diol are shown below. 1 1H-NMR (DMSO-d6): δ = 7.01 (d, 2H), 7.33 - 7.64 (m, 12H), 7.85 - 7.95 (m, 10H), 7.98 - 8.05 (m, 4H), 9.42 (br, 2H)

[0131] Step (ii) A 200 mL three-necked flask equipped with a stirring device, a reflux tube, and a thermometer was charged with 17.0 g (28.8 mmol) of 6,6'-bis((E)-2-(naphthalen-2-yl)vinyl)-[1,1'-binaphthalene]-2,2'-diol, 15.2 g (63.3 mmol) of (2-bromoethoxy)(t-butyl)dimethylsilane, 28.1 g (86.3 mmol) of cesium carbonate, and DMF, and stirred at 100 °C for 2 hours. Then, it was cooled to room temperature, 200 ml of ethyl acetate and 200 ml of water were added, and liquid separation was performed. The organic layer was washed with 200 ml of a saturated aqueous sodium chloride solution and separated, and the organic layer was concentrated using a rotary evaporator to obtain a solid. The obtained solid was dissolved in toluene, purified by a silica gel column, and concentrated to obtain a solid. The obtained solid was dissolved by heating in toluene and cooled for crystallization to obtain 13.3 g (14.6 mmol) of ((((6,6'-bis((E)-2-(naphthalen-2-yl)vinyl)-[1,1'-binaphthalene]-2,2'-diyl)bis(oxy))bis(ethane-2,1-diyl))bis(t-butyldimethylsilane) (the compound represented by the following formula (4-ii)) in a yield of 51%.

[0132]

Chemical formula

[0133] The NMR analysis results of ((((6,6'-bis((E)-2-(naphthalen-2-yl)vinyl)-[1,1'-binaphthalene]-2,2'-diyl)bis(oxy))bis(ethane-2,1-diyl))bis(t-butyldimethylsilane) are shown below. 1 H-NMR(CDCl 3 ): δ = -0.25 (s, 6H), -0.22 (s, 6H), 0.74 (s, 18H), 3.60 (t, 4H), 4.03 (t, 4H), 7.16 (d, 2H), 7.27 (d, 2H), 7.37 (d, 2H), 7.40 - 7.49 (m, 6H), 7.52 (d, 2H), 7.75 - 7.96 (m, 14H)

[0134] Step (iii) Into a 200 mL three-necked flask equipped with a stirring device, a reflux tube and a thermometer, 13.6 g (14.6 mmol) of ((6,6'-bis((E)-2-(naphthalen-2-yl)vinyl)-[1,1'-binaphthalene]-2,2'-diyl)bis(oxy))bis(ethane-2,1-diyl))bis(t-butyldimethylsilane), 130 ml of THF and 1.3 g of concentrated hydrochloric acid were added, and the mixture was stirred at 60 °C for 24 hours. Then, it was cooled to room temperature and the slurry was filtered. 60 ml of DMF was added to the solid obtained by filtration, and the mixture was stirred at 110 °C for 1 hour. Then, it was cooled to room temperature, filtered and washed with acetone to obtain 7.8 g (11.4 mmol) of 2,2'-((6,6'-bis((E)-2-naphthalen-2-yl)vinyl)-[1,1'-naphthalene]-2,2'-diyl)bis(oxy))bis(ethan-1-ol) (the compound represented by the following formula (4-iii)) with a yield of 78%.

[0135] [Chemical formula]

[0136] The NMR analysis results of 2,2'-((6,6'-bis((E)-2-naphthalen-2-yl)vinyl)-[1,1'-naphthalene]-2,2'-diyl)bis(oxy))bis(ethan-1-ol) are shown below. 1 1H-NMR (DMSO-d6): δ = 2.56 (d, 4H), 3.23 (t, 4H), 3.77 (t, 2H), 6.15 (d, 2H), 6.57 - 6.75 (m, 8H), 6.79 - 6.85 (m, 4H), 7.05 - 7.12 (m, 8H), 7.18 (s, 2H), 7.24 (d, 2H), 7.28 (s, 2H)

[0137] [Production of polycarbonate resin] [Example 5] 4.00 g (8.72 mmol) of 2,2'-(2,7-di((E)-styryl)vinyl-9H-fluorene-9,9-diyl)bis(ethane-1-ol) obtained in Example 2, 1.92 g (8.99 mmol) of diphenyl carbonate (hereinafter sometimes abbreviated as "DPC"), and 3 μL (6 × 10 -8 mol) of 0.02 M aqueous sodium hydrogen carbonate solution were charged into a reactor equipped with a distillation apparatus and reacted at 240 °C and 100 kPa for 1 hour. Then, the degree of vacuum was adjusted to 19 kPa and the reaction was carried out for 20 minutes, followed by reaction at the same temperature and pressure for 70 minutes. Next, the degree of vacuum was adjusted to 16 kPa and the reaction was carried out for 20 minutes, and further the degree of vacuum was adjusted to 13 kPa and the reaction was carried out for 20 minutes. Then, the degree of vacuum was set to 130 Pa over 40 minutes and the reaction was carried out at the same pressure for 30 minutes. When the torque became constant, the vacuum was released with nitrogen gas and the polycarbonate resin was taken out. The weight average molecular weight (Mw) of the obtained polycarbonate resin was 6580, and the Tg was 126.7 °C. The refractive index nD of this polycarbonate resin was 1.8005.

[0138] [Example 6-1] Instead of 2,2'-(2,7-di((E)-styryl)vinyl-9H-fluorene-9,9-diyl)bis(ethane-1-ol), 1.22 g (2.00 mmol) of 2,2'-(2,7-bis((E)-2-([1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-1-ol) obtained in Example 3 was used, and also 7.89 g (18.0 mmol) of 2,2'-(((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(oxy))bis(ethane-1-ol) (hereinafter sometimes abbreviated as "BPEF"; the compound represented by the following formula (2a)), 4.41 g (20.6 mmol) of DPC, and 8 μL (2 × 10 -7 mol) of 0.02 M aqueous sodium hydrogen carbonate solution were used, and a polycarbonate resin was produced according to the procedure described in Example 5. The weight average molecular weight (Mw) of the obtained polycarbonate resin was 23200, and the Tg was 149.7 °C. The refractive index nD of this polycarbonate resin was 1.7880.

[0139] [Chemical Formula]

[0140] [Example 6-2] A polycarbonate resin was produced according to the procedure described in Example 6-1, except that 2.44 g (4.00 mmol) of 2,2'-(2,7-bis((E)-2-([1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-1-ol) obtained in Example 3 and 7.02 g (16.0 mmol) of BPEF were used. The weight average molecular weight (Mw) of the obtained polycarbonate resin was 19,700, and the Tg was 152.7 °C. The refractive index nD of this polycarbonate resin was 1.8162.

[0141] [Example 6-3] A polycarbonate resin was produced according to the procedure described in Example 6-1, except that 3.66 g (6.00 mmol) of 2,2'-(2,7-bis((E)-2-([1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-1-ol) obtained in Example 3 and 6.14 g (14.0 mmol) of BPEF were used. The weight average molecular weight (Mw) of the obtained polycarbonate resin was 7,440, and the Tg was 151.6 °C. The refractive index nD of this polycarbonate resin was 1.8387.

[0142] Approximation formulas for the refractive indices of Example 6-1, 6-2, and Example 6-3 were calculated. The refractive index nD of the polycarbonate resin composed of 2,2'-(2,7-bis((E)-2-([1,1'-biphenyl]-4-yl)vinyl)-9H-fluorene-9,9-diyl)bis(ethane-1-ol) (20.0 mmol) and DPC (20.6 mmol) was 1.8921 as an extrapolated approximate value.

[0143] [Comparative Example 1] Instead of 2,2'-(2,7-di((E)-styryl)vinyl-9H-fluorene-9,9-diyl)bis(ethane-1-ol), 2,2'-(2,7-di(naphthalen-2-yl)-9H-fluorene-9,9-diyl)bis(ethane-1-ol) (compound represented by the following formula (X)) 20.26 g (40 mmol), DPC 8.56 g (40 mmol) and 15 μL of 0.02 M aqueous sodium hydrogen carbonate solution (3×10 -6 mol) were used, and a polycarbonate resin was produced according to the procedure described in Example 5. The weight average molecular weight (Mw) of the obtained polycarbonate resin was 32300, and the Tg was 135°C. The refractive index nD of this polycarbonate resin was 1.7608.

[0144] [Chemical Formula]

Claims

1. A diol compound represented by the following formula (1). 【Chemical 1】 (In the formula (1), the hydrogen atom bonded to the carbon atom may be replaced by an alkyl group having 1 to 10 carbon atoms or a heteroatom-containing alkyl group having 1 to 10 carbon atoms, W represents a group selected from the group consisting of the following formula (W-1) and the following formula (W-2) (where * indicates a bonding point in the formula, and n is an integer of 1 or more and 4 or less independently for each).), [Chemical Formula 2] 【Chemical 3】 Ar １ and Ar ２ is each independently an unsubstituted or substituted aromatic or heteroaromatic group with one or more substituents.

2. In the formula (1), Ar １ and Ar ２ each independently represents a group selected from the group consisting of the following formula (a) and the following formula (b), and R １ to R ３ each independently is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a heteroatom-containing alkyl group having 1 to 10 carbon atoms, a phenyl group, or a fluorine atom, The diol compound according to claim 1. 【Chemical Formula 4】 【Chemical 5】

3. In the formula (a) and the formula (b), the R １ to R ３ are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a phenyl group, and the diol compound according to claim 2.

4. The diol compound according to any one of Claims 1 to 3, wherein in the formula (W-1) and the formula (W-2), n is an integer of 1 or more and 3 or less independently for each.

5. A resin containing a structural unit derived from the diol compound according to any one of Claims 1 to 4.

6. A polycarbonate resin containing a structural unit derived from the diol compound according to any one of Claims 1 to 4.

7. The polycarbonate resin according to Claim 6, wherein when the total of all the structural units in the polycarbonate resin is 100 mol%, the content of the structural unit derived from the diol compound represented by the formula (1) in the polycarbonate resin is 1 mol% or more and 99 mol% or less.

8. The weight average molecular weight (Mw) in terms of polystyrene is 1.5×10 ３ or more and 2.0×10 ５ or less. The polycarbonate resin according to claim 6 or 7.

9. The polycarbonate resin according to any one of Claims 6 to 8, having a glass transition temperature measured by a differential scanning calorimeter of 100°C or higher and 190°C or lower.

10. The polycarbonate resin according to any one of Claims 6 to 9, having a refractive index nD of 1.70 or higher and 1.95 or lower at a temperature of 23°C and a wavelength of 589 nm.

11. An optical molded article containing the resin according to Claim 5.

12. An optical molded article containing the polycarbonate resin according to any one of Claims 6 to 10.

13. The optical molded article according to Claim 11 or 12, which is an optical lens.

14. The optical molded article according to Claim 11 or 12, which is an optical film.

Images