Patent Description:
Optical glass or an optical resin is used as a material for an optical lens used in an optical system of various kinds of cameras such as a camera, a film-integrated camera, and a video camera. The optical glass is excellent in heat resistance, transparency, dimensional stability, and chemical resistance, and there are various kinds of materials having various refractive indices and Abbe numbers. However, there are problems that the material cost is high, the molding processability is poor, and the productivity is low.

An optical lens formed of an optical resin has an advantage that mass production can be achieved by injection molding. For example, a polycarbonate resin is used in camera lenses. However, in recent years, there has been a demand for the development of resins having a high refractive index due to lightness, thinness, shortness, and miniaturization of products. In general, since in a case where the refractive index of an optical material is high, lens elements having the same refractive index can be realized with a surface having a smaller curvature, the aberration amount generated on this surface can be reduced. As a result, it is possible to reduce the number of lenses, reduce the eccentricity sensitivity of a lens, and reduce the thickness and weight of a lens.

Examples of techniques related to the optical resin include those described in <CIT> and <CIT>.

In <CIT>, an optical lens that is formed of a polycarbonate resin having a fluorene structure is described.

In <CIT>, a method for easily improving a refractive index by blending (mixing and adding) a sulfur-containing compound with a fluorene-containing polyester is described.

<CIT> discloses a thermoplastic resin including repeating units of formula (<NUM>)
<CHM>
wherein the rings Z each independently are aromatic hydrocarbon rings, R<NUM> and R<NUM> each independently are H, halogen or a C<NUM>-<NUM>-hydrocarbon group optionally containing an aromatic group, Ar<NUM> and Ar<NUM> are optionally substituted C<NUM>-<NUM>-aromatic groups, L<NUM> and L<NUM> each independently are a divalent linking group, j and k each independently are an integer of ≥ <NUM>, m and n each independently are <NUM> or <NUM>, and W is -C(=O)- or -C(=O)-X-C(=O)- wherein X is a divalent linking group.

<CIT> relates to a polycarbonate resin derived from a diol component containing a specific aromatic diol compound having a fluorene ring structure, and an optical film such as a retardation film formed by molding the polycarbonate resin, and having a small photoelastic coefficient.

However, the polycarbonate resin as described in <CIT> has a low refractive index and is not a sufficiently satisfactory resin.

In addition, as described in <CIT>, in a case where the sulfur-containing compound is blended with the fluorene-containing polyester, the refractive index is improved. However, in a case where the heat stability is lowered due to the addition of a low molecular weight component, and the compatibility of the two components to be blended is poor, the transparency may decrease.

The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a resin and a polycarbonate resin capable of realizing an optical molded article having a high refractive index and excellent transparency.

The present inventors have diligently studied to provide a polycarbonate resin capable of realizing an optical molded article having a high refractive index and excellent transparency. As a result, the present inventors have found that an optical molded article having a high refractive index and excellent transparency can be realized by a resin obtained by polymerization of a compound represented by the following Formula (<NUM>), and have reached the present invention.

Accordingly, the present invention provides a compound of the Formula (<NUM>):
<CHM>
wherein Ar<NUM> and Ar<NUM> each independently are selected from the groups of the following formulae:
<CHM>
<CHM>
<CHM>
wherein.

with the proviso that the following compound is excluded:
<CHM>.

Also, the present invention provides (i) a resin obtained by polymerization of the above compound of the invention, and (ii) an optical molded article containing the resin (i).

Preferred embodiments of the invention are as defined in the appended dependent claims and/or n the following detailed description.

According to the present invention, it is possible to provide the resin and the polycarbonate resin capable of realizing the optical molded article having the high refractive index and excellent transparency.

Unless otherwise specified, the term "to" between the numerical values in the text indicates a range of equal to or more than a numerical value and equal to or less than a numerical value.

A compound according to the present embodiment will be described. The compound according to the present embodiment (also referred to as "the present compound" herein) is a compound of the Formula (<NUM>):
<CHM>
wherein Ar<NUM> and Ar<NUM> each independently are selected from the groups of the following formulae:
<CHM>
<CHM>
<CHM>
wherein.

In Formula (<NUM>), R<NUM>-R<NUM> are preferably each independently H, C<NUM>-<NUM>-alkyl or C<NUM>-<NUM>-aryl, more preferably H, methyl, phenyl, biphenyl, or naphthyl, and even more preferably H.

In Formula (<NUM>), o and p each are an integer of <NUM>-<NUM>, preferably <NUM> or <NUM>, and more preferably <NUM>. By setting o and p to the above range, a polycarbonate resin obtained from the compound of Formula (<NUM>) has excellent heat resistance.

In one embodiment, Ar<NUM> and Ar<NUM> in Formula (<NUM>) independently represent a group selected from the following formulae:
<CHM>.

Examples of preferred aspects of Ar<NUM> and Ar<NUM> in General Formula (<NUM>) each include the following formulae:
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

Examples of the compound of Formula (<NUM>) include.

Among these, preferred examples thereof can include.

Such a compound may be used alone or two or more compounds may be used in combination.

The present compound of Formula (<NUM>) can be synthesized by the following steps (i) and (ii).

Step (i): Dihalogeno-<NUM>-fluorene such as <NUM>,<NUM>-dibromo-<NUM>-fluorene or <NUM>,<NUM>-dibromo-<NUM>-fluorene is treated with a base (for example, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, potassium hydride, methoxy sodium, ethoxy sodium, t-butoxy sodium, t-butoxy potassium, and n-butyllithium) in a solvent (for example, tetrahydrofuran, <NUM>,<NUM>-dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and sulfolane) to extract 9th hydrogen of dihalogeno-<NUM>-fluorene, and thereafter, reacts with hydroxyalkyl having a leaving group (here, examples of a leaving group include halogen such as Cl, Br and I, p-toluenesulfonyloxy, methylsulfonyloxy, and trifluoromethylsulfonyloxy) to produce <NUM>,<NUM>-bis(hydroxyalkyl)-dihalogeno-<NUM>-fluorene such as <NUM>,<NUM>-bis(hydroxyalkyl)-<NUM>,<NUM>-dibromo-<NUM>-fluorene or <NUM>,<NUM>-bis(hydroxyalkyl)-<NUM>,<NUM>-dibromo-<NUM>-fluorene.

Step (ii): <NUM>,<NUM>-bis(hydroxyalkyl)-dihalogeno-<NUM>-fluorene such as <NUM>,<NUM>-bis(hydroxyalkyl)-<NUM>,<NUM>-dibromo-<NUM>-fluorene or <NUM>,<NUM>-bis(hydroxyalkyl)-<NUM>,<NUM>-dibromo-<NUM>-fluorene, which is obtained in Step (i), reacts with naphthyl boric acid in a solvent (for example, toluene and water, tetrahydrofuran and water, and dimethyl sulfoxide and water) in the presence of a base (for example, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, sodium phosphate, and potassium phosphate) and a palladium-based catalyst such as and tetrakis palladium (triphenylphosphine) to produce the compound of Formula (<NUM>) of purpose under a condition of so-called Suzuki-Miyaura Coupling.

Here, the reaction of step (i) can be carried out at any temperature between -<NUM> and the boiling point of the solvent. In addition, as reaction conditions, general alkylation reaction conditions can be applied. As desired, a hydroxy group of hydroxyalkyl having a leaving group is protected with any protecting group (for example, an ester group such as an acetyl group), an ether group such as a tetrahydropyranyl group, a carbonic acid ester group such as a t-butoxycarbonyl group, and then may be deprotected at the end.

The reaction of step (ii) can be carried out at any temperature between room temperature and the boiling point of the solvent. As reaction conditions, the reaction conditions generally used in the so-called Suzuki-Miyaura coupling can be applied.

One aspect of the present invention is a resin obtained by polymerization of a compound of Formula (<NUM>).

Here, examples of the resin obtained by polymerization of the compound of Formula (<NUM>) include a polyester resin, a polyurethane resin, a polycarbonate resin, and a polyether resin.

The polyester resin can be obtained by reacting the compound of Formula (<NUM>) with an aromatic dicarboxylic acid (for example, terephthalic acid, isophthalic acid, or <NUM>, <NUM>-naphthalenedicarboxylic acid), or an aliphatic dicarboxylic acid (for example, oxalic acid, malonic acid, or succinic acid).

The polyurethane resin can be obtained by reacting the compound of Formula (<NUM>) with an aromatic diisocyanate (for example, toluene diisocyanate or xylylene diisocyanate) or an aliphatic diisocyanate (for example, pentamethylene diisocyanate, hexamethylene diisocyanate, or cyclohexanedimethylene diisocyanate).

As will be described later, the polycarbonate resin can be obtained by reacting the compound of Formula (<NUM>) with a carbonate precursor such as a carbonic acid diester.

The polyether resin can be obtained by reacting the compound of Formula (<NUM>) with an aliphatic dihalogen compound (for example, dibromoethane or dibromopropane) in presence of a base.

In these resins, a reactant other than the compound of Formula (<NUM>) may be used alone or a plurality of reactants may be used in combination. In addition, it is also possible to polymerize a resin by using a dihydroxy compound other than the compound Formula (<NUM>), in combination.

In a case where the dihydroxy compound other than the compound of Formula (<NUM>) is used in combination, a ratio of the compound of Formula (<NUM>) to the total amount of the compound of Formula (<NUM>) and the dihydroxy compound other than the compound of Formula (<NUM>) is preferably <NUM>-<NUM> mol%, more preferably <NUM>-<NUM> mol%, and even more preferably <NUM>-<NUM> mol%.

Here, examples of the dihydroxy compound other than the compound of Formula (<NUM>) include bis(<NUM>-hydroxyaryl)alkanes such as.

The polycarbonate resin of the present invention ("the present polycarbonate resin") is produced by using the present compound of Formula (<NUM>). The present polycarbonate resin has a structural unit of Formula (1p) and derived from the compound of Formula (<NUM>). Such a polycarbonate resin can realize an optical molded article having a high refractive index and excellent transparency. As a result, the polycarbonate resin can be suitably used as a material for an optical lens. <CHM>
wherein Ar<NUM> and Ar<NUM>, R<NUM> and R<NUM>, and o and p each are synonymous with those in Formula (<NUM>). The same applies to the preferred aspects.

A preferred weight average molecular weight in terms of polystyrene (Mw) of the present polycarbonate resin is preferably <NUM> × <NUM><NUM> to <NUM> × <NUM><NUM>, and more preferably <NUM> × <NUM><NUM> to <NUM> × <NUM><NUM>.

In a case where Mw is equal to or greater than the above lower limit value, it is preferable that the obtained molded article can be suppressed from being fragile. In a case where Mw is equal to or smaller than the above upper limit value, the melt viscosity becomes more appropriate, so that the resin can be easily taken out after production, fluidity further becomes better, and injection molding becomes easier in a molten state, which are preferable.

The refractive index (n633) of the present polycarbonate resin at <NUM> and a wavelength of <NUM> is preferably <NUM>-<NUM>, more preferably <NUM>-<NUM>, even more preferably <NUM>-<NUM>, and particularly preferably <NUM>-<NUM>.

The present polycarbonate resin can be blended with another resin and used for producing a molded article. Examples of other resins include polyamide, polyacetal, polycarbonate, modified polyphenylene ether, polyethylene terephthalate, and polybutylene terephthalate.

Furthermore, e.g. an antioxidant, a mold release agent, an ultraviolet absorber, a fluidity modifier, a crystal nucleating agent, a strengthening agent, a dye, an antistatic agent, and an antibacterial agent can be added to the present polycarbonate resin.

Examples of a molding method include compression molding, casting, roll processing, extrusion molding, and stretching, in addition to injection molding, but the molding method is not limited thereto.

In a case where the present polycarbonate resin is used for injection molding, the glass transition temperature (Tg) is preferably <NUM>-<NUM>, more preferably <NUM>-<NUM>, and even more preferably <NUM>-<NUM>. In a case where Tg is equal to or higher than the above lower limit value, a range of temperature in use is wider, which is preferable. In a case where Tg is equal to or lower than the above upper limit value, the melting temperature of the resin decreases, and decomposition and coloring of the resin are less likely to occur, which is preferable. In addition, in a case where Tg is equal to or lower than the above upper limit value, the difference between the mold temperature and the resin glass transition temperature can be reduced even with a general-purpose mold temperature controller. Therefore, it is easy to use and preferable in applications in which strict surface accuracy is required for a product.

The optical molded article obtained by using the present polycarbonate resin preferably has a total transmittance of ≥ <NUM>%, more preferably ≥ <NUM>%, in which each total transmittance is measured in accordance with JIS K-<NUM>-<NUM> (<NUM>), and is by no means inferior to a bisphenol A-type polycarbonate resin.

The ≥ polycarbonate resin can be produced by using the compound of Formula (<NUM>) as a raw material. Specifically, the compound of Formula (<NUM>) reacts with a carbonate precursor such as a carbonic acid diester by a melt polycondensation method, in presence of a basic compound catalyst, a transesterification catalyst, or a mixed catalyst constituted of both, or in absence of a catalyst, to produce the polycarbonate resin.

Examples of the carbonic acid diester used to produce the ≥ polycarbonate resin 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, and dicyclohexyl carbonate. Among these, diphenyl carbonate is preferred. Diphenyl carbonate is preferably used in a ratio of <NUM>-<NUM> mol and more preferably <NUM>-<NUM> mol, with respect to <NUM> mol of the compound of Formula (<NUM>).

Examples of the basic compound catalyst used in the production of the ≥ polycarbonate resin include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds. As such compounds, e.g. organic acid salts, inorganic salts, oxides, hydroxides, hydrides or alkoxides, or quaternary ammonium hydroxides and salts thereof, amines of alkali metals, or alkaline earth metal compounds, are preferably used, and these compounds can be used alone or in combination.

Examples of the alkali metal compounds include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, and alkoxides of alkali metals. Specific examples thereof for use include sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium hydrogencarbonate, sodium carbonate, potassium hydrogencarbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, cesium acetate, lithium acetate, sodium stearate, potassium stearate, cesium stearate, lithium stearate, sodium borohydride, sodium borophenylate, sodium benzoate, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogenphosphate, dipotassium hydrogenphosphate, dilithium hydrogenphosphate, disodium phenylphosphate, a disodium salt, a dipotassium salt, a dicesium salt, or a dilithium salt of bisphenol A, and a sodium salt, a potassium salt, a cesium salt, or a lithium salt of phenol.

Examples of the alkaline earth metal compounds include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, alkoxides, of alkaline earth metal compounds. Specific examples thereof for use include magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium hydrogencarbonate, calcium hydrogencarbonate, strontium hydrogencarbonate, barium hydrogencarbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, and magnesium phenylphosphate.

Examples of the nitrogen-containing compounds include quaternary ammonium hydroxides and salts thereof, and amines. Specific examples thereof for use include quaternary ammonium hydroxides having an alkyl group such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetra n-propylammonium hydroxide, tetra n-butylammonium hydroxide, trimethylbenzylammonium hydroxide, or an aryl group; tertiary amines such as triethylamine, dimethylbenzylamine, triphenylamine; secondary amines such as diethylamine and dibutylamine; primary amines such as n-propylamine and n-butylamine; imidazoles such as <NUM>-methylimidazole, <NUM>-phenylimidazole, and benzoimidazole; or bases such as ammonia, tetramethylammonium borohydride, tetra n-butylammonium borohydride, tetra n-butylammonium tetraphenylborate, tetraphenylammonium tetraphenylborate, or basic salts.

As the transesterification catalyst, salts such as zinc, tin, zirconium, and lead are preferably used, and these salts can be used alone or in combination. Specific examples of the transesterification catalyst for use include zinc acetate, zinc benzoate, zinc <NUM>-ethylhexanoate, tin chloride (II), tin chloride (IV), tin acetate (II), tin acetate (IV), dibutyltin dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead acetate (II), and lead acetate (IV).

Each of these catalysts is used at a ratio of <NUM>-<NUM> to <NUM>-<NUM> mol, preferably <NUM>-<NUM> to <NUM>-<NUM> mol, with respect to a total of <NUM> mol of the compound of Formula (<NUM>).

The melt polycondensation method is a method of performing melt polycondensation using the above described raw material and catalyst under heating and normal pressure or reduced pressure while removing by-products through a transesterification reaction.

In the melt polycondensation method, the reaction is desirably carried out in a state in which the compound of Formula (<NUM>) and the carbonic acid diester are melted in a reaction vessel, and the reaction is then carried out in a state where by-product monohydroxy compounds are kept in the reaction vessel.

In order to keep the by-product monohydroxy compounds, a reacting apparatus can be closed, or can be vacuumed or pressurized for pressure control purposes The reaction time required for this step is preferably <NUM>-<NUM> minutes, more preferably <NUM>-<NUM> minutes, and particularly preferably <NUM>-<NUM> minutes. During this step, in a case where the by-product monohydroxy compounds are distilled off immediately upon the generation of the by-product monohydroxy compounds, the finally obtained polycarbonate resin is low in the content of high molecular weight components. However, in a case where the by-product monohydroxy compounds are kept in the reaction vessel for a certain period of time, the finally obtained polycarbonate resin is high in the content of high molecular weight components.

In general, a melt polycondensation reaction is carried out in a multi-stage step of two or more stages. Specifically, a first-stage reaction is preferably carried out at a temperature of <NUM>-<NUM>, more preferably <NUM>-<NUM>, and is preferably carried out under normal pressure or pressure for <NUM>-<NUM> hours, more preferably under pressure for <NUM>-<NUM> hours. Next, the compound of Formula (<NUM>) reacts with carbonic acid diester with a reaction temperature being increased while increasing the degree of decompression of the reaction system, and finally, the polycondensation reaction is preferably carried out with the degree of decompression of ≤ <NUM> Pa (<NUM> mmHg) at a temperature of <NUM>-<NUM> for <NUM>-<NUM> hours.

The melt polycondensation reaction may be carried out either in a continuous manner or in a batch manner.

Examples of the reacting apparatus for use in this reaction are a vertical reactor equipped with an anchor-type impeller, a Maxblend impeller, or a helical ribbon-type impeller, or a horizontal reactor equipped with a paddle impeller, a grid impeller, or a spectacle impeller, and an extruder-type reacting apparatus equipped with a screw. In addition, it is suitable to use a reacting apparatus constituted of these reactors in combination as appropriate, in consideration of the viscosity of the polymerized product.

In the present polycarbonate resin, after the polycondensation reaction is completed, the catalyst may be removed or deactivated in order to maintain heat stability and hydrolysis stability. In general, known methods for catalyst deactivation which involve addition of an acidic substance can suitably be carried out. Specific examples of an acidic substance suitable for use 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, n-propyl phosphite, n-butyl phosphite, n-hexyl phosphite, n-octyl phosphite, and mono n-octyl phosphite; phosphoric acid esters such as triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, n-butyl phosphate, 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 triphenyl phosphine and bis(diphenylphosphino)ethane; boric acids such as boric acid and phenylboric acid; aromatic sulfonates such as n-dodecylbenzenesulfonic acid tetra n-butylphosphonium salt; 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. Each of these deactivating agents is preferably used in a content of <NUM>-<NUM> times by mole and more preferably <NUM>-<NUM> times by mole with respect to the amount of the catalyst. In a case where the content of the deactivating agent is < <NUM> times by mole with respect to the amount of the catalyst, the deactivating effect is insufficient, which is not preferable. In addition, in a case where the content of the deactivating agent is > <NUM> times by mole with respect to the amount of the catalyst, the heat resistance of the resin is lowered, and the molded article is easily colored, which is not preferable.

After the catalyst is deactivated, a step of devolatilizing and removing compounds having the low boiling point in the polymer at a pressure of <NUM>-<NUM> Pa (<NUM>-<NUM> mmHg) and a temperature of <NUM>-<NUM> may be provided. In this step, a horizontal evaporator equipped with an impeller that is excellent in surface renewal ability, such as a paddle impeller, a grid impeller, and a spectacle impeller, or a thin film evaporator is suitable for use.

The present polycarbonate resin is desired to be extremely low in the content of contaminants, which is suitably accomplished by e.g. filtration of molten raw materials and filtration of the catalyst solution. The mesh size of a filter is preferably ≤ <NUM>, and more preferably ≤ <NUM>. Furthermore, the generated resin is suitably filtered through a polymer filter. The mesh size of the polymer filter is preferably ≤ <NUM>, and more preferably ≤ <NUM>. In addition, a step of collecting resin pellets is, naturally, preferably performed in a low dust environment, and more preferably with cleanness of ≤ class <NUM>.

An optical molded article of the present invention ("the present optical molded article") contains the present polycarbonate resin, and the optical molded article can be produced by using the present polycarbonate resin.

For example, the optical molded article is molded by any method such as an injection molding method, a compression molding method, an injection compression molding method, an extrusion molding method, or a solution casting method.

Since the present polycarbonate resin is excellent in moldability and heat resistance, the polycarbonate resin can be used particularly advantageously in optical lenses that are required to be produced by injection molding. During the molding, the present polycarbonate resin can be mixed with other resins such as other polycarbonate resins and polyester resins, and used.

In addition, it is possible to use various types of additives in order to impart various characteristics in a range that does not impair the object of the present invention. Examples of additives include antioxidants, processing stabilizers, mold release agents, ultraviolet absorbers, bluing agents, polymeric metal deactivators, flame retardants, lubricants, antistatic agents, heat ray shielding agents, fluorescent dyes (including fluorescent whitening agents), pigments, light scattering agents, reinforcing fillers, surfactants, antibacterial agents, plasticizers, compatibilizers, other resins, and elastomers.

Examples of antioxidants include triethylene glycol-bis[<NUM>-(<NUM>-tert-butyl-<NUM>-methyl-<NUM>-hydroxyphenyl)propionate], <NUM>,<NUM>-hexanediol-bis[<NUM>-(<NUM>,<NUM>-di-tert-butyl-<NUM>-hydroxyphenyl)propiona te], pentaerythritol-tetrakis[<NUM>-(<NUM>,<NUM>-di-tert-butyl-<NUM>-hydroxyphenyl)pr opionate], octadecyl-<NUM>-(<NUM>,<NUM>-di-tert-butyl-<NUM>-hydroxyphenyl)propionate, <NUM>,<NUM>,<NUM>-trimethyl-<NUM>,<NUM>,<NUM>-tris(<NUM>,<NUM>-di-tert-butyl-<NUM>-hydroxybenzyl)ben zene, N,N-hexamethylene bis(<NUM>,<NUM>-di-tert-butyl-<NUM>-hydroxy-hydrocinnamide), <NUM>,<NUM>-di-tert-butyl-<NUM>-hydroxy-benzyl phosphonate-diethyl ester, tris(<NUM>,<NUM>-di-tert-butyl-<NUM>-hydroxybenzyl) isocyanurate, and <NUM>,<NUM>-bis{<NUM>,<NUM>-dimethyl-<NUM>-[β-(<NUM>-tert-butyl-<NUM>-hydroxy-<NUM>-methylphenyl )propionyloxy]ethyl}-<NUM>,<NUM>,<NUM>,<NUM>-tetraoxaspiro(<NUM>,<NUM>)undecane.

The content of the antioxidant in the polycarbonate resin is preferably <NUM>-<NUM> parts by mass (pbm) with respect to <NUM> pbm of the polycarbonate resin.

Examples of processing stabilizers include phosphorus-based processing heat stabilizers, and sulfur-based processing heat stabilizers.

Examples of phosphorus-based processing heat stabilizers include phosphorous acid, phosphoric acid, phosphonous acid, phosphonic acid, and esters thereof. Specific examples thereof include triphenyl phosphite, tris(nonylphenyl) phosphite, tris(<NUM>,<NUM>-di-tert-butylphenyl) phosphite, tris (<NUM>, <NUM>-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(<NUM>,<NUM>-di-tert-butyl-<NUM>-methylphenyl) pentaerythritol diphosphite, <NUM>,<NUM>-methylene bis(<NUM>,<NUM>-di-tert-butylphenyl) octyl phosphite, bis(n-nonylphenyl) pentaerythritol diphosphite, bis(<NUM>,<NUM>-dicumylphenyl) pentaerythritol diphosphite, bis(<NUM>,<NUM>-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(<NUM>,<NUM>-di-t-butylphenyl)-<NUM>,<NUM>'-biphenylenediphosphonite, tetrakis(<NUM>,<NUM>-di-t-butylphenyl)-<NUM>,<NUM>'-biphenylenediphosphonite, tetrakis(<NUM>,<NUM>-di-t-butylphenyl)-<NUM>,<NUM>'-biphenylenediphosphonite, bis(<NUM>,<NUM>-di-tert-butylphenyl)-<NUM>-phenyl-phenylphosphonite and bis(<NUM>,<NUM>-di-tert-butylphenyl)-<NUM>-phenyl-phenylphosphonite.

The content of the phosphorus-based processing heat stabilizer in the polycarbonate resin is preferably <NUM>-<NUM> pbm with respect to <NUM> pbm of the polycarbonate resin.

Examples of sulfur-based processing heat stabilizers include pentaerythritol-tetrakis(<NUM>-laurylthiopropionate), pentaerythritol-tetrakis(<NUM>-myristylthiopropionate), pentaerythritol-tetrakis(<NUM>-stearylthiopropionate), dilauryl-<NUM>,<NUM>'-thiodipropionate, dimyristyl-<NUM>,<NUM>'-thiodipropionate, and distearyl-<NUM>,<NUM>'-thiodipropionate.

The content of the sulfur-based processing heat stabilizer in the polycarbonate resin is preferably <NUM>-<NUM> pbm with respect to <NUM> pbm of the polycarbonate resin.

As a mold release agent, a mold release agent of which ≥ <NUM> mass% is formed of esters of alcohols and fatty acids is preferable. Specific examples of the esters of alcohols and fatty acids include esters of monohydric alcohol and fatty acid and partial esters or whole esters of polyhydric alcohol and fatty acid. As the ester of a monohydric alcohol and a fatty acid, an ester of a monohydric C<NUM>-<NUM>-alcohol and a saturated C<NUM>-<NUM>-fatty acid is preferable. In addition, as the partial ester or whole ester of a polyhydric alcohol and a fatty acid, a partial ester or whole ester of polyhydric C<NUM>-<NUM>-alcohol and saturated C<NUM>-<NUM>-fatty acid is preferable.

Examples of esters of a monohydric alcohol and a saturated fatty acid include stearyl stearate, palmityl palmitate, n-butyl stearate, methyl laurate, and isopropyl palmitate. Examples of partial esters or whole esters of polyhydric alcohols and saturated fatty acids include whole esters or partial esters of dipentaerythritol such as stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbitate, behenic acid monoglyceride, capric acid monoglyceride, lauric acid monoglyceride, pentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, <NUM>-ethylhexyl stearate, and dipentaerythritol hexastearate.

The content of these mold release agents is preferably <NUM>-<NUM> pbm with respect to <NUM> pbm of the polycarbonate resin, more preferably <NUM>-<NUM> pbm, and even more preferably <NUM>-<NUM> pbm.

As the ultraviolet absorber, it is possible to include at least one type of ultraviolet absorber selected from a benzotriazole-based ultraviolet absorber, a benzophenone-based ultraviolet absorber, a triazine-based ultraviolet absorber, a cyclic imino ester-based ultraviolet absorber, and a cyanoacrylate-based ultraviolet absorber. The ultraviolet absorbers listed below may be used alone or in a combination of two or more types.

Examples of benzotriazole-based ultraviolet absorbers include <NUM>-(<NUM>-hydroxy-<NUM>-methylphenyl) benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>-tert-octylphenyl) benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>,<NUM>-dicumylphenyl) phenylbenzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>-tert-butyl-<NUM>-methylphenyl)-<NUM>-chlorobenzotriazole, <NUM>,<NUM>'-methylenebis[<NUM>-(<NUM>,<NUM>,<NUM>,<NUM>-tetramethylbutyl)-<NUM>-(2N-benzotriazo l-<NUM>-yl) phenol], <NUM>-(<NUM>-hydroxy-<NUM>,<NUM>-di-tert-butylphenyl) benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>,<NUM>-di-tert-butylphenyl)-<NUM>-chlorobenzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>,<NUM>-di-tert-amylphenyl) benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>-tert-octylphenyl) benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>-tert-butylphenyl) benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>-n-octyloxyphenyl) benzotriazole, <NUM>,<NUM>'-methylenebis(<NUM>-cumyl-<NUM>-benzotriazolephenyl), <NUM>,<NUM>'-p-phenylenebis(<NUM>,<NUM>-benzoxazine-<NUM>-one), and <NUM>-[<NUM>-hydroxy-<NUM>-(<NUM>,<NUM>,<NUM>,<NUM>-tetrahydrophthalimidomethyl)-<NUM>-methylphe nyl]benzotriazole.

Examples of benzophenone-based ultraviolet absorbers include <NUM>,<NUM>-dihydroxybenzophenone, <NUM>-hydroxy-<NUM>-methoxybenzophenone, <NUM>-hydroxy-<NUM>-n-octyloxybenzophenone, <NUM>-hydroxy-<NUM>-benzyloxybenzophenone, <NUM>-hydroxy-<NUM>-methoxy-<NUM>-sulfoxybenzophenone, <NUM>-hydroxy-<NUM>-methoxy-<NUM>-sulfoxytrihydratebenzophenone, <NUM>,<NUM>'-dihydroxy-<NUM>-methoxybenzophenone, <NUM>,<NUM>',<NUM>,<NUM>'-tetrahydroxybenzophenone, <NUM>,<NUM>'-dihydroxy-<NUM>,<NUM>'-dimethoxybenzophenone, <NUM>,<NUM>'-dihydroxy-<NUM>,<NUM>'-dimethoxy-<NUM>-sodium sulfoxybenzophenone, bis(<NUM>-benzoyl-<NUM>-hydroxy-<NUM>-methoxyphenyl) methane, <NUM>-hydroxy-<NUM>-n-dodecyloxybenzophenone, and <NUM>-hydroxy-<NUM>-methoxy-<NUM>'-carboxybenzophenone.

Examples of triazine ultraviolet absorbers include <NUM>-(<NUM>,<NUM>-diphenyl-<NUM>,<NUM>,<NUM>-triazin-<NUM>-yl)-<NUM>-[(n-hexyl)oxy]-phenol, and <NUM>-(<NUM>,<NUM>-bis(<NUM>,<NUM>-dimethylphenyl)-<NUM>,<NUM>,<NUM>-triazin-<NUM>-yl)-<NUM>-[(n-octyl)o xy]-phenol.

Examples of cyclic imino ester-based ultraviolet absorbers include <NUM>,<NUM>'-bis(<NUM>,<NUM>-benzoxazine-<NUM>-one), <NUM>,<NUM>'-p-phenylenebis(<NUM>,<NUM>-benzoxazine-<NUM>-one), <NUM>,<NUM>'-m-phenylenebis(<NUM>,<NUM>-benzoxazine-<NUM>-one), <NUM>,<NUM>'-(<NUM>,<NUM>'-diphenylene)bis(<NUM>,<NUM>-benzoxazine-<NUM>-one), <NUM>,<NUM>'-(<NUM>,<NUM>-naphthalene)bis(<NUM>,<NUM>-benzoxazine-<NUM>-one), <NUM>,<NUM> '-(<NUM>,<NUM>-naphthalene)bis(<NUM>,<NUM>-benzoxazine-<NUM>-one), <NUM>,<NUM>'-(<NUM>-methyl-p-phenylene)bis(<NUM>,<NUM>-benzoxazine-<NUM>-one), <NUM>,<NUM> '-(<NUM>-nitro-p-phenylene)bis(<NUM>,<NUM>-benzoxazine-<NUM>-one) and <NUM>,<NUM>'-(<NUM>-chloro-p-phenylene)bis(<NUM>,<NUM>-benzoxazine-<NUM>-one).

Examples of cyanoacrylate-based ultraviolet absorbers include <NUM>,<NUM>-bis-[(<NUM>'-cyano-<NUM>',<NUM>'-diphenylacryloyl)oxy]-<NUM>,<NUM>-bis[[(<NUM>-cyano -<NUM>,<NUM>-diphenylacryloyl)oxy]methyl]propane, and <NUM>,<NUM>-bis-[(<NUM>-cyano-<NUM>,<NUM>-diphenylacryloyl)oxy]benzene.

The content of the ultraviolet absorber is preferably <NUM>-<NUM> pbm with respect to <NUM> pbm of the polycarbonate resin, and more preferably <NUM>-<NUM> pbm, and even more preferably <NUM>-<NUM> pbm. With this blending amount range, it is possible to impart sufficient weather resistance to a polycarbonate resin according to the application thereof.

Examples of bluing agents include Macrolex Violet B and Macrolex Blue RR made by Bayer, and Polysynthren Blue RLS made by Clariant.

The bluing agent is effective to eliminate the yellowness of the polycarbonate resin. In particular, in a case of a polycarbonate resin to which weather resistance is imparted, a certain amount of ultraviolet absorber is blended, thus, the polycarbonate resin molded article tends to be slightly yellow due to the "action and color of the ultraviolet absorber" and blending a bluing agent therein is particularly effective for imparting natural transparency to a sheet or lens.

The blending amount of the bluing agent is, for example, preferably <NUM>-<NUM> ppm with respect to the polycarbonate resin, and more preferably <NUM>-<NUM> ppm.

The present polycarbonate resin exhibits a high refractive index and excellent heat resistance, and has a fluidity suitable for molding. Furthermore, since optical distortion is unlikely to occur due to a low degree of birefringence, the optical molded article can be advantageously used, as an optical molded article, not only for optical lenses, but also as an electrically conductive transparent substrate for use in e.g. liquid crystal displays, organic EL displays, and solar photovoltaic cells, and suitable for use as a structural material or functional material for optical components such as optical disks, liquid crystal panels, optical cards, sheets, films, optical fibers, connectors, evaporated plastic reflecting mirrors, and displays.

A surface of such an optical molded article may be provided with a coating layer such as an antireflection layer or a hard coat layer, as necessary. Such an antireflection layer may be constituted of a single layer or multiple layers, and may be formed of an organic material or an inorganic material, but is preferably formed of an inorganic material. Specific examples include oxides or fluorides such as silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, cerium oxide, magnesium oxide, and magnesium fluoride.

An optical lens produced by using the present polycarbonate resin is very useful since it has a high refractive index and are excellent in heat resistance, and thus can be used in the fields of telescopes, binoculars, television projectors, and others where expensive high refractive index glass lenses have been used in the related art. The optical lens is preferably used in the form of an aspherical lens, as necessary. In the case of the aspherical lens, a single lens achieves substantially zero spherical aberration, which eliminates the need to remove spherical aberration by combining a plurality of spherical lenses, so that light weight and production cost savings can be achieved. Therefore, an aspherical lens is particularly useful as a camera lens among optical lenses.

The present optical lens is molded by any method such as an injection molding method, a compression molding method, or an injection compression molding method. According to the present invention, an aspherical lens with a high refractive index and a low degree of birefringence can be obtained in a simpler manner, which is technically difficult to process in the case of using glass lenses.

An optical film produced by using the present polycarbonate resin is excellent in transparency and heat resistance, and is therefore suitable for use in films for e.g. liquid crystal substrates and optical memory cards.

Hereinafter, the present invention will be described in detail with reference to Examples and Comparative Examples.

In the following Examples and Comparative Examples, the measurement and evaluation of each physical property were performed by the following method.

A <NUM> flask was charged with <NUM> (<NUM> mol) of <NUM>,<NUM>-dibromo-<NUM>-fluorene, <NUM> (<NUM> mol) of potassium hydroxide (powder), <NUM> (<NUM> mol) of potassium iodide, <NUM> of dimethyl sulfoxide, and cooled to <NUM> with ice water. Thereafter, <NUM> (<NUM> mol) of <NUM>-bromoethanol was added dropwise over <NUM> minutes, and the mixture was then stirred overnight at room temperature. Thereafter, the reaction solution was heated to <NUM> and heated and stirred for <NUM> hours. The reaction mixture was discharged into <NUM> liters of distilled water and pH was adjusted to <NUM> with concentrated hydrochloric acid. The obtained solid was filtered and separated, and washed with <NUM> liters of water. The obtained solid was dissolved in <NUM> liter of ethyl acetate, washed with <NUM> of distilled water, and concentrated with an evaporator, and chloroform was added to obtain <NUM> of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-dibromo-<NUM>-fluorene as colorless crystals.

A <NUM>-liter flask was charged with <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-dibromo-<NUM>-fluorene, <NUM> (<NUM> mol) of naphthalene-<NUM>-boronic acid, <NUM> (<NUM> mol) of potassium carbonate, <NUM> of distilled water, and <NUM> of dimethyl sulfoxide. <NUM> of tetrakis(triphenylphosphine) palladium was added to this reaction mixture, the mixture was heated to <NUM>, and heated and stirred for <NUM> hours. After cooling, the produced solid was filtered and separated, washed with <NUM> of water, and vacuum dried at <NUM>. After drying, the solid was suspended and washed with chloroform to obtain <NUM> of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl-<NUM>-fluorene as colorless crystals. The melting point measured by DSC was <NUM>.

A <NUM>-liter round bottomed flask equipped with a stirrer, a thermometer and a dropping funnel was charged with <NUM> (<NUM> mol) of <NUM>-bromoethanol and <NUM> of dichloromethane, and cooled with ice water. Thereafter, when the internal temperature reached <NUM>, <NUM> (<NUM> mol) of <NUM>,<NUM>-dihydro-<NUM>-pyran was added dropwise at equal to or lower than <NUM>. After completion of the dropwise addition, <NUM> (<NUM> mol) of pyridinium p-toluenesulfonate was added, and the mixture was stirred overnight at room temperature. Thereafter, saturated water of sodium hydrogencarbonate was added, and a dichloromethane layer was washed with water. The obtained dichloromethane layer was concentrated by an evaporator to obtain <NUM> of <NUM>-(<NUM>'-bromoethoxy)tetrahydropyran as a pale yellow oil.

A <NUM>-liter round bottomed flask equipped with a stirrer, a thermometer and a reflux tube was charged with <NUM> of <NUM>-(<NUM>'-bromoethoxy)tetrahydropyran, <NUM> of toluene, and <NUM> (<NUM> mol) of <NUM>,<NUM>-dibromo-<NUM>-fluorene, and <NUM> of an aqueous solution of <NUM>% sodium hydroxide were added thereto. Thereafter, <NUM> (<NUM> mmol) of tetrabutylammonium bromide was added, the mixture was heated to <NUM>, and the mixture was heated and stirred for <NUM> hours. Thereafter, the reaction mixture was cooled to room temperature, an aqueous layer was separated, <NUM> of ethyl acetate and <NUM> of distilled water were then added, and the mixture was washed with water. After the washing with water was repeatedly carried out, a layer formed of ethyl acetate and toluene was separated and concentrated by an evaporator. A small amount of seed crystals of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dibromo-<NUM>-fluoren e was added to a viscous liquid obtained after concentration, and methanol was added to carry out crystallization. The obtained crystals was filtered, washed with a small amount of methanol, and then recrystallized by heating from <NUM> of methanol to obtain <NUM> of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyl) ethoxy]-<NUM>,<NUM>-dibromo-<NUM>-fluorene of purpose was obtained as pale yellow crystals.

A <NUM>-liter round bottomed flask equipped with a stirrer, a thermometer and a reflux tube was charged with <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dibromo-<NUM>-fluoren e, <NUM> of toluene, <NUM> (<NUM> mmol) of potassium carbonate, <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid, and <NUM> of distilled water, and <NUM> of tetrakis (triphenylphosphine) palladium were added to this reaction mixture while being stirred, and then the resultant mixture was heated up to <NUM>. The mixture was heated and stirred at <NUM> for <NUM> hours, and then cooled to room temperature. After separating the aqueous layer, a toluene layer was washed with distilled water, and then the toluene layer was concentrated by an evaporator. <NUM> of methanol was added to the concentrated residue, and the resultant solid was filtered and separated, and washed with methanol. Thereafter, purification was carried out by silica gel column chromatography (eluent toluene to toluene/ethyl acetate = <NUM>/<NUM>), and then recrystallization from methyl cellosolve was carried out to obtain <NUM>. <NUM> of a desired product. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (CDCl3) δ1. <NUM>-<NUM> (m, <NUM>), <NUM>, <NUM> (t, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (s, <NUM>).

A <NUM>-liter round bottomed flask equipped with a stirrer, a thermometer and a reflux tube was charged with <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid, the temperature was increased to <NUM> with stirring, and the mixture was heated and stirred at the same temperature for <NUM> hours. Thereafter, the mixture was cooled to room temperature, <NUM> of water was added, and the resulting crystals were filtered and separated. The obtained crystals were washed with distilled water, dried under reduced pressure at <NUM>, and then suspended and washed with hot methyl cellosolve to obtain <NUM> of a desired product. Yield <NUM>%, m. <NUM>,
<NUM>H-NMR (DMSO-d<NUM>) δ2. <NUM> (t, <NUM>), <NUM> (t, <NUM>), <NUM> (t, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (s, <NUM>).

<NUM> of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[dibenzo[b,d]fu ran-<NUM>"-yl]-<NUM>-fluorene was obtained according to the operations described in the step (iii) of Example <NUM>, except that <NUM> (<NUM> mmol) of dibenzo[b,d]furan-<NUM>-yl boronic acid was used instead of using <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid in the step (iii) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (CDCl3) <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM> (<NUM>, dt), <NUM> (<NUM>, q), <NUM> (<NUM>, dt), <NUM> (<NUM>, s), <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM> (<NUM>, d), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m).

<NUM> of a desired product was obtained according to the operations described in the step (iv) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis [<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[dibenzo[b,d]furan-<NUM>"-yl]-<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid were used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid in the step (iv) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (DMSO-d<NUM>) δ2. <NUM> (<NUM>, t), <NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM> (<NUM>, t), <NUM> (<NUM>, dt), <NUM> (<NUM>, dd), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, dd).

<NUM> of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[<NUM>-(naphthalen-<NUM>-yl-)phenyl]-<NUM>-fluorene was obtained according to the operations described in the step (iii) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>-(naphthalen-<NUM>-yl)phenyl boronic acid was used instead of using <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid in the step (iii) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (CDCl3) <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, d), <NUM> (<NUM>, d), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM> (<NUM>, s).

<NUM> of a desired product was obtained according to the operations described in the step (iv) of Example <NUM>, except that <NUM> of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[<NUM>-(naphthalen-<NUM>-yl-)phenyl]-<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid were used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid in the step (iv) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (DMSO-d<NUM>) δ2. <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM> (<NUM>, t), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, d), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, d), <NUM> (<NUM>, s).

<NUM> of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[<NUM>-(naphthalen-<NUM>-yl-)phenyl]-<NUM>-fluorene was obtained according to the operations described in the step (iii) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>-(naphthalen-<NUM>-yl)phenyl boronic acid was used instead of using <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid in the step (iii) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (CDCl3) δ1. <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, d), <NUM> (<NUM>, dd), <NUM> (<NUM>, d), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s).

<NUM> of a desired product was obtained according to the operations described in the step (iv) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[<NUM>-(naphthalen-<NUM>-yl-)phenyl]-<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid were used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid in the step (iv) of Example <NUM>. Yield <NUM>%. The final product was purified by column chromatography (eluent: ethyl acetate/chloroform= <NUM>/<NUM> -> <NUM>/<NUM>). HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (DMSO-d<NUM>) δ: <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, dd), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s).

<NUM> of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-diphenanthrene <NUM>"-yl-<NUM>-fluorene was obtained according to the operations described in the step (iii) of Example <NUM>, except that <NUM> (<NUM> mmol) of phenanthren-<NUM>-yl boronic acid was used instead of using <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid in the step (iii) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, viscous solid,
<NUM>H-NMR (CDCl3) δ1. <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, dt), <NUM> (<NUM>, s), <NUM> (<NUM>, d), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM> (<NUM>, d), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, d), <NUM> (<NUM>, dd).

<NUM> of a desired product was obtained according to the operations described in the step (iv) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-diphenanthren-<NUM>"-y l-<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid were used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid in the step (iv) of Example <NUM>. Yield <NUM>%. The final product was purified by column chromatography (eluent: ethyl acetate/chloroform= <NUM>/<NUM> -> <NUM>/<NUM>). HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (DMSO-d<NUM>) δ2. <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM> (<NUM>, dd), <NUM> (<NUM>, dd).

<NUM> of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[dibenzo[b,d]th iophen-<NUM>"-yl]-<NUM>-fluorene was obtained according to the operations described in the step (iii) of Example <NUM>, except that <NUM> (<NUM> mmol) of dibenzo[b,d]thiophen-<NUM>-yl boronic acid was used instead of using <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid in the step (iii) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, viscous solid,
<NUM>H-NMR (CDCl3) <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM> (<NUM>, dt), <NUM> (<NUM>, q), <NUM> (<NUM>, dt), <NUM> (<NUM>, s), <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM> (<NUM>, d), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m).

<NUM> of a desired product was obtained according to the operations described in the step (iv) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis [<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[dibenzo[b,d]thiophen-<NUM>"-yl]-<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid were used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid in the step (iv) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (DMSO-d<NUM>) δ2. <NUM> (<NUM>, t), <NUM> (<NUM>, dt), <NUM> (<NUM>, t), <NUM> (<NUM>, dd), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, d), <NUM> (<NUM>, s), <NUM> (<NUM>, dd), <NUM> (<NUM>, d), <NUM>-<NUM> (<NUM>, dd).

<NUM> of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[<NUM>-phenoxypheny l]-<NUM>-fluorene was obtained according to the operations described in the step (iii) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>-phenoxyphenyl boronic acid was used instead of using <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid in the step (iii) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, viscous solid,
<NUM>H-NMR (CDCl3) δ1. <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, dt), <NUM> (<NUM>, d), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, d).

<NUM> of a desired product was obtained according to the operations described in the step (iv) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[<NUM>"-phenoxyphen yl]-<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid were used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid in the step (iv) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (DMSO-d<NUM>) δ2. <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM> (<NUM>, t), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM> (<NUM>, dd), <NUM> (<NUM>, t), <NUM> (<NUM>, d).

<NUM> of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[<NUM>"-phenylnapht halen-<NUM>"-yl-]-<NUM>-fluorene was obtained according to the operations described in the step (iii) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>-phenylnaphthalen-<NUM>-yl boronic acid was used instead of using <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid in the step (iii) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (CDCl3) δ1. <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM> (<NUM>, dt), <NUM> (<NUM>, q), <NUM> (<NUM>, dt), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM> (<NUM>), d), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m).

<NUM> of a desired product was obtained according to the operations described in the step (iv) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[<NUM>"-phenylnapht halen-<NUM>"-yl-]-<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid were used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid in the step (iv) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (DMSO-d<NUM>) δ2. <NUM> (<NUM>, t), <NUM> (<NUM>, dt), <NUM> (<NUM>, t), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, d).

<NUM> of <NUM>,<NUM>-bis [<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[<NUM>",<NUM>"-dimethyl-<NUM>"H-fl uoren-<NUM>"-yl]-<NUM>-fluorene was obtained according to the operations described in the step (iii) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>,<NUM>-dimethyl-<NUM>-fluoren-<NUM>-yl boronic acid was used instead of using <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid in the step (iii) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, viscous solid,
<NUM>H-NMR (CDCl3) δ1. <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, s), <NUM> (<NUM>, t), <NUM> (<NUM>, q), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, dd), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m), <NUM>-<NUM> (<NUM>, m).

<NUM> of a desired product was obtained according to the operations described in the step (iv) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis [<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-bis[<NUM>",<NUM>"-dimethyl-<NUM>"H-fl uoren-<NUM>"-yl]-<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid were used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene, <NUM> of methyl cellosolve, <NUM> of distilled water, and <NUM> of concentrated hydrochloric acid in the step (iv) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, m. <NUM>,
<NUM>H-NMR (DMSO-d<NUM>) δ1. <NUM> (<NUM>, s), <NUM> (<NUM>, t), <NUM> (<NUM>, m), <NUM> (<NUM>, t), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, dd), <NUM>-<NUM> (<NUM>, m), <NUM> (<NUM>, d), <NUM> (<NUM>, dd).

<NUM> of <NUM>,<NUM>-bis [<NUM> (<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthyl-<NUM>"-yl-<NUM>-fluorene was obtained according to the operations described in the step (iii) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid was used instead of using <NUM> (<NUM> mmol) of <NUM>-naphthalene boronic acid in the step (iii) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, viscous solid,
<NUM>H-NMR (CDCl<NUM>) δ1. <NUM>-<NUM> (m, <NUM>), <NUM> (t, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM> of a desired product was obtained according to the operations described in the step (iv) of Example <NUM>, except that <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene was used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>-(<NUM>'-tetrahydropyranyloxy)ethyl]-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl -<NUM>-fluorene in the step (iv) of Example <NUM>. Yield <NUM>%, HPLC purity <NUM>%, viscous solid,
<NUM>H-NMR (DMSO-d<NUM>) δ2. <NUM> (t, <NUM>), <NUM> (t, <NUM>), <NUM> (<NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM> of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-diphenyl-<NUM>-fluorene was obtained as colorless crystals according to the operations described in Example <NUM>, except that <NUM> (<NUM> mol) of phenyl boronic acid was used instead of using <NUM> (<NUM> mol) of naphthalene-<NUM>-boronic acid in Example <NUM>.

A reactor equipped with a distiller was charged with <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl-<NUM>-fluorene obtained in Example <NUM>, <NUM> (<NUM> mmol) of diphenylcarbonate (hereinafter, abbreviated as "DPC" in some cases), and <NUM>µL (<NUM> × <NUM>-<NUM> mol) of a <NUM>-sodium hydrogencarbonate aqueous solution, and the mixture reacted at <NUM> and <NUM> kPa for one hour. Thereafter, the degree of decompression was adjusted to <NUM> kPa, and the mixture reacted for <NUM> minutes. Then, the mixture reacted at the same temperature and the same pressure for <NUM> minutes. Next, the degree of decompression was adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes, and the degree of decompression was further adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes. Thereafter, when the degree of decompression was reduced to <NUM> Pa for <NUM> minutes and reached a predetermined torque through the reaction at the same pressure for <NUM> minutes, the vacuum was released with nitrogen gas to extract the polycarbonate resin.

A weight average molecular weight (Mw) of the obtained polycarbonate resin was <NUM>, and a Tg was <NUM>.

A refractive index (n633) of this polycarbonate resin was <NUM>.

A polycarbonate resin was obtained according to the operations in Example <NUM>, except that in Example <NUM>, <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-diphenyl-<NUM>-fluorene was used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl-<NUM>-fluorene obtained in Example <NUM>.

A reactor equipped with a distiller was charged with <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl-<NUM>-fluorene obtained in Example <NUM>, <NUM> (<NUM> mmol) of diphenylcarbonate, and <NUM>µL (<NUM> × <NUM>-<NUM> mol) of a <NUM>-sodium hydrogencarbonate aqueous solution, and the mixture reacted at <NUM> and <NUM> kPa for <NUM> minutes and at <NUM> and <NUM> kPa for <NUM> minutes. Thereafter, the degree of decompression was adjusted to <NUM> kPa, and the mixture reacted for <NUM> minutes. Then, the mixture reacted at the same temperature and the same pressure for <NUM> minutes. Next, the degree of decompression was adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes, and the degree of decompression was further adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes. Thereafter, when the degree of decompression was reduced to <NUM> Pa for <NUM> minutes and reached a predetermined torque through the reaction at the same pressure for <NUM> minutes, the vacuum was released with nitrogen gas to extract the polycarbonate resin.

The obtained polycarbonate resin had a weight average molecular weight (Mw) of <NUM>, and was a crystalline polymer having a Tg of <NUM> and a Tm of <NUM> (calorific value: <NUM> J/g).

A reactor equipped with a distiller was charged with <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-bis[dibenzo[b,d]furan-<NUM>"-yl]-<NUM>-flu orene obtained in Example <NUM>, <NUM> (<NUM> mmol) of DPC, and <NUM>µL (<NUM> × <NUM>-<NUM> mol) of a <NUM>-sodium hydrogencarbonate aqueous solution, and the mixture reacted at <NUM> and <NUM> kPa for one hour. Thereafter, the degree of decompression was adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes, and the degree of decompression was further adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes. Thereafter, when the degree of decompression was reduced to <NUM> Pa for <NUM> minutes and reached a predetermined torque through the reaction at the same pressure for <NUM> minutes, vacuum was released with nitrogen gas to extract the polycarbonate resin.

A polycarbonate resin was produced according to the operations in Example <NUM>, except that in Example <NUM>, <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-dihydroxyethyl)-<NUM>,<NUM>-bis[<NUM>-(naphthalen-<NUM>-yl-)phenyl]-<NUM>-fluorene obtained in Example <NUM> was used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-bis[dibenzo[b,d]furan-<NUM>"-yl]-<NUM>-flu orene obtained in Example <NUM>.

A polycarbonate resin was produced according to the operations in Example <NUM>, except that in Example <NUM>, <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis (<NUM>'-dihydroxyethyl) -<NUM>,<NUM>-diphenanthren-<NUM>"-yl-<NUM>-fluorene obtained in Example <NUM> was used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-bis[dibenzo[b,d]furan-<NUM>"-yl]-<NUM>-flu orene obtained in Example <NUM>.

A polycarbonate resin was produced according to the operations in Example <NUM>, except that in Example <NUM>, <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis (<NUM>'-dihydroxyethyl)-<NUM>,<NUM>-bis (<NUM>"-phenoxyphenyl)-<NUM>-fluorene obtained in Example <NUM> was used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-bis[dibenzo[b,d]furan-<NUM>"-yl]-<NUM>-flu orene obtained in Example <NUM>.

A polycarbonate resin was produced according to the operations in Example <NUM>, except that in Example <NUM>, <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-dihydroxyethyl)-<NUM>,<NUM>-bis(<NUM>"-phenylnaphthalen-<NUM>"-yl)-<NUM> -fluorene obtained in Example <NUM> was used instead of using <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-bis[dibenzo[b,d]furan-<NUM>"-yl]-<NUM>-flu orene obtained in Example <NUM>.

A reactor equipped with a distiller was charged with <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl-<NUM>-fluorene obtained in Example <NUM>, <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>'-(<NUM>"-hydroxyethoxy)phenyl]-<NUM>-fluorene, <NUM> (<NUM> mmol) of bisphenol A, <NUM> (<NUM> mmol) of DPC, and <NUM>µL (<NUM> × <NUM>-<NUM> mol) of a <NUM>-sodium hydrogencarbonate aqueous solution, and the mixture reacted at <NUM> and <NUM> kPa for one hour. Thereafter, the degree of decompression was adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes, and the degree of decompression was further adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes. Thereafter, when the degree of decompression was reduced to <NUM> Pa for <NUM> minutes and reached a predetermined torque through the reaction at the same pressure for <NUM> minutes, vacuum was released with nitrogen gas to extract the polycarbonate resin.

In addition, the total transmittance of a sheet that is formed of the polycarbonate resin heat-pressed at <NUM> and has a thickness of <NUM> was <NUM>%.

A reactor equipped with a distiller was charged with <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-bis[<NUM>-(naphthalen-<NUM>-yl-)phenyl]-<NUM>-fluorene obtained in Example <NUM>, <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>'-(<NUM>"-hydroxyethoxy)phenyl]-<NUM>-fluorene, <NUM> (<NUM> mmol) of bisphenol A, <NUM> (<NUM> mmol) of DPC, and <NUM>µL (<NUM> × <NUM>-<NUM> mol) of a <NUM>-sodium hydrogencarbonate aqueous solution, and the mixture reacted at <NUM> and <NUM> kPa for one hour. Thereafter, the degree of decompression was adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes, and the degree of decompression was further adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes. Thereafter, when the degree of decompression was reduced to <NUM> Pa for <NUM> minutes and reached a predetermined torque through the reaction at the same pressure for <NUM> minutes, vacuum was released with nitrogen gas to extract the polycarbonate resin.

A weight average molecular weight (Mw) of the obtained polycarbonate resin was <NUM>, and a Tg was <NUM>. The appearance of the polycarbonate resin was colorless and transparent.

A reactor equipped with a distiller was charged with a mixture formed of <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis(<NUM>'-hydroxyethyl)-<NUM>,<NUM>-dinaphthalen-<NUM>"-yl-<NUM>-fluorene obtained in Example <NUM>, <NUM> (<NUM> mmol) of <NUM>,<NUM>-bis[<NUM>'-(<NUM>"-hydroxyethoxy)phenyl]-<NUM>-fluorene, <NUM> (<NUM> mmol) of <NUM>,<NUM>-naphthalene dicarboxylic acid dimethyl ester, and <NUM>µl (<NUM> ppm as Ti) of titanium tetraisopropoxide, and the mixture reacted at <NUM> and <NUM> kPa for one hour. Thereafter, the degree of decompression was adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes, and the degree of decompression was further adjusted to <NUM> kPa and the mixture reacted for <NUM> minutes. Thereafter, when the degree of decompression was reduced to <NUM> Pa for <NUM> minutes and reached a predetermined torque through the reaction at the same pressure for <NUM> minutes, vacuum was released with nitrogen gas to extract the polyester resin.

A weight average molecular weight (Mw) of the obtained polyester resin was <NUM>, and a Tg was <NUM>.

Claim 1:
A compound of the Formula (<NUM>):
<CHM>
wherein Ar<NUM> and Ar<NUM> each independently are selected from the groups of the following formulae:
<CHM>
<CHM>
<CHM>
wherein
R<NUM>-R<NUM> each are H, a hydrocarbon group, or a heteroatom-containing hydrocarbon group,
A<NUM> is phenyl or phenoxy,
A<NUM> is phenyl, phenoxy, phenylthio or naphthyl,
A<NUM> is phenyl, <NUM>-pyridyl, phenoxy, phenylthio, benzosulfonyl, phenylcarbonyl, diphenylamino or naphthyl, and
o, p each are an integer of <NUM>-<NUM>,
with the proviso that the following compound is excluded:
<CHM>