Dibenzo[g,p]chrysene-based diol compound, polyester resin, and method for producing the same

Abstract

To provide a novel dibenzo[g,p]chrysene-based compound which is useful as an optical material.SOLUTION: A dibenzo[g,p]chrysene-based compound is represented by the following formula (1). In the formula, R1 and R2 are each independently a C1-8 alkyl group, and R3 and R4 are each independently a hydroxy C1-4 alkylene group.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a dibenzo[g,p]chrysene diol compound, a polyester resin, and a method for producing the same. [Background technology]

[0002] 2. Description of the Related Art For example, compounds having a dibenzo[g,p]chrysene skeleton and compounds having a fluorene skeleton are known as raw materials for optical resins used in the production of optical products such as optical films and optical lenses.

[0003] Dibenzo[g,p]chrysene having a substituent has attracted attention as a material having organic electroluminescence properties and semiconductor resist properties. Among polycyclic aromatic hydrocarbon compounds, dibenzo[g,p]chrysene is characterized by a helically twisted π-conjugated structure, and by adjusting the structure of the dibenzo[g,p]chrysene skeleton, it is possible to manipulate the photophysical and electronic attributes such as good hole mobility, high quantum yield, and long excited state lifetime. A method for producing dibenzo[g,p]chrysene having a substituent is disclosed in, for example, Patent Document 1.

[0004] In addition, compounds having a fluorene skeleton are known to have excellent functions such as a high refractive index, high heat resistance, etc. A method for producing a compound having a fluorene skeleton is disclosed in, for example, Patent Document 2. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2013-227307 A [Patent Document 2] JP 2011-68624 A Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide a novel dibenzo[g,p]chrysene compound that is useful as an optical material. [Means for solving the problem]

[0007] As a result of extensive investigations, the present inventors have found that dibenzo[g,p]chrysene compounds having a specific structure are useful as optical materials, and have completed the present invention.

[0008] The present invention includes the following embodiments. [1] A dibenzo[g,p]chrysene-based diol compound represented by the following formula (1): [ka] [In the formula, R 1 and R 2 are each independently 1-8 is an alkyl group, R 3 and R 4 each independently represents a hydroxy C 1-4 is an alkylene group. [2] A constitutional unit derived from the dibenzo[g,p]chrysene diol compound according to [1], A structural unit derived from a dicarboxylic acid compound; The polyester resin has the formula: [3] The dicarboxylic acid compound is At least one aromatic dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the following formula (2) and esters thereof; [ka] [wherein Z is a monocyclic or polycyclic aromatic ring] At least one fluorene-based dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the following formula (3) and esters thereof; [ka] [where, X 1 are each independently 1-8 an alkylene group. The polyester resin according to [2], [4] The polyester resin according to [3], wherein Z in the formula (2) is a benzene ring, a naphthalene ring, or a binaphthalene ring. [5] A structural unit derived from the aromatic dicarboxylic acid compound; A structural unit derived from the fluorene-based dicarboxylic acid compound; The polyester resin according to [3] or [4], wherein the molar ratio of [6] A structural unit derived from an aliphatic diol compound represented by the following formula (4): [ka] [where, X 2 is C 2-8 an alkylene group. The polyester resin according to any one of [2] to [5], further comprising: [7] A constitutional unit derived from the dibenzo[g,p]chrysene diol compound; A structural unit derived from the aliphatic diol compound; The polyester resin according to [6], wherein the molar ratio of [8] An optical film comprising the polyester resin according to any one of [2] to [7]. [9] An optical lens comprising the polyester resin according to any one of [2] to [7].

[10] A dibenzo[g,p]chrysene-based raw material represented by the following formula (5) is [ka] [In the formula, R 5 and R 6are each independently 1-8 is an alkyl group. comprising a reaction step of hydroxyalkylating A method for producing a dibenzo[g,p]chrysene-based diol compound represented by the following formula (1) [ka] [In the formula, R 1 and R 2 are each independently 1-8 is an alkyl group, R 3 and R 4 each independently represents a hydroxy C 1-4 is an alkylene group.

[11] The reaction step comprises reacting the dibenzo[g,p]chrysene-based raw material with reacting with an alkylene carbonate; reacting with a halogenated alkanol; or reacting with an alkyl halide alkanoate and hydrolyzing the resulting reaction product; The method for producing a semiconductor device according to

[10] , comprising the steps of:

[12] The reacting step is carried out in the presence of a solvent, The method according to

[10] or

[11] , wherein the solvent is selected from the group consisting of aromatic hydrocarbon solvents, halogen-based solvents, amine-based solvents, amide-based solvents, alcohol-based solvents, nitrile-based solvents, ketone-based solvents, and ether-based solvents.

[13] A dibenzo[g,p]chrysene-based diol compound represented by the following formula (1), [ka] [In the formula, R 1 and R 2 are each independently 1-8 is an alkyl group, R 3 and R 4 each independently represents a hydroxy C1-4 an alkylene group. A dicarboxylic acid compound, A method for producing a polyester resin, comprising a polymerization step of reacting

[14] The dicarboxylic acid compound is At least one aromatic dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the following formula (2) and esters thereof; [ka] [wherein Z is a monocyclic or polycyclic aromatic ring] At least one fluorene-based dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the following formula (3) and esters thereof; [ka] [where, X 1 are each independently 1-8 an alkylene group. The method for producing the polyester resin according to

[13] , comprising: Effect of the Invention

[0009] According to the present invention, it is possible to provide a novel dibenzo[g,p]chrysene compound which is useful as an optical material. [Brief description of the drawings]

[0010] [Figure 1] FIG. 1 shows the 1H-NMR spectrum of the dibenzo[g,p]chrysene-based diol compound synthesized in Example 1. [Diagram 2] FIG. 2 shows the 13C-NMR spectrum of the dibenzo[g,p]chrysene-based diol compound synthesized in Example 1. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] Hereinafter, the embodiments of the present invention will be described in detail, however, the present invention is not limited to these and various modifications are possible without departing from the gist of the present invention.

[0012] <Dibenzo[g,p]chrysene-based diol compounds> One embodiment of the present invention relates to a dibenzo[g,p]chrysene diol compound represented by the following formula (1). [ka] [In the formula, R 1 and R 2 are each independently 1-8 is an alkyl group, R 3 and R 4 each independently represents a hydroxy C 1-4 an alkylene group.

[0013] The dibenzo[g,p]chrysene diol compound according to this embodiment has a high refractive index and high heat resistance, and therefore can be suitably used as an optical material.

[0014] In the formula (1), R 1 and R 2 are each independently 1-8 It is an alkyl group. There is no particular limitation. 1 and R 2 are each independently 2-7 Alkyl group, C 3-6 Alkyl group, C 4-5 It may be an alkyl group or a C4 alkyl group.

[0015] In the formula (1), R 3 and R 4 each independently represents a hydroxy C 1-4 An alkylene group. There is no particular limitation. 3 and R 4 each independently represents a hydroxy C 2-3It may be an alkylene group or a hydroxy C2 alkylene group.

[0016] <Method of producing dibenzo[g,p]chrysene diol compound> One embodiment of the present invention relates to a method for producing a dibenzo[g,p]chrysene-based diol compound represented by the formula (1), comprising a reaction step of hydroxyalkylating a dibenzo[g,p]chrysene-based raw material represented by the following formula (5). [ka] [In the formula, R 5 and R 6 is R in the above formula (1). 1 and R 2 is equivalent to

[0017] Examples of the hydroxyalkylation method include the following method. (1) Reaction of the dibenzo[g,p]chrysene-based raw material with an alkylene carbonate. (2) Reaction of the dibenzo[g,p]chrysene-based raw material with a halogenated alkanol. (3) reacting the dibenzo[g,p]chrysene-based raw material with an alkyl halide alkanoate, and hydrolyzing the resulting reaction product.

[0018] The reactions in the above methods (1) to (3) are preferably carried out in the presence of a base, such as potassium carbonate, sodium carbonate, lithium carbonate, triethylamine, diazabicycloundecene, and ethyldiisopropylamine.

[0019] The hydrolysis in the above method (3) may be carried out by a method generally employed in the hydrolysis of esters.

[0020] The dibenzo[g,p]chrysene diol compound represented by the formula (1) (wherein R 3 and R 4is a hydroxy C1 alkylene group. In the case of producing the compound (I), it is preferable to employ the above method (2) and use 1-chloromethanol as the halogenated alkanol, or to employ the above method (3) and use chloromethyl butanoate as the alkyl halide alkanoate.

[0021] The dibenzo[g,p]chrysene diol compound represented by the formula (1) (wherein R 3 and R 4 is a hydroxy C2 alkylene group. When producing the compound (1), it is preferable to employ the above method (1) and use ethylene carbonate as the alkylene carbonate.

[0022] The dibenzo[g,p]chrysene diol compound represented by the formula (1) (wherein R 3 and R 4 is a hydroxy C3 alkylene group. When producing the compound (1), it is preferable to employ the above method (2) and use 1-chloropropanol as the halogenated alkanol.

[0023] The dibenzo[g,p]chrysene diol compound represented by the formula (1) (wherein R 3 and R 4 is a hydroxy C4 alkylene group. When producing the compound (1), it is preferable to employ the above method (2) and use 1-bromobutanol as the halogenated alkanol.

[0024] The molar ratio of the dibenzo[g,p]chrysene-based raw material represented by the formula (5) to the alkylene carbonate, halogenated alkanol, or alkyl halide alkanoate in the methods (1) to (3) is preferably 1.0:2.0-4.0, more preferably 1.0:2.0-3.0, and even more preferably 1.0:2.0-2.5.

[0025] The reaction step is preferably carried out in the presence of a solvent. Examples of the solvent include aromatic hydrocarbon solvents, halogen solvents, amine solvents, amide solvents, alcohol solvents, nitrile solvents, ketone solvents, and ether solvents. The solvent may be used alone or in combination of two or more.

[0026] Aromatic hydrocarbon solvents include, for example, benzene, toluene, and xylene.

[0027] Halogenated solvents include, for example, methylene chloride, chloroform, and carbon tetrachloride.

[0028] Amine solvents include, for example, pyridine, 4-methylpyridine, and 2,6-dimethylpyridine.

[0029] Examples of the amide solvent include dimethylformamide and dimethylacetamide.

[0030] Alcohol-based solvents include, for example, methanol, ethanol, isopropanol, butanol, and hexanol.

[0031] An example of the nitrile solvent is acetonitrile.

[0032] Examples of ketone solvents include acetone, cyclohexanone, cyclopentanone, methyl ethyl ketone, and methyl isopropyl ketone.

[0033] Ether solvents include, for example, diethyl ether, tetrahydrofuran, and dioxane.

[0034] The reaction temperature in the reaction step is not particularly limited, and may be, for example, 20 to 200°C, 50 to 190°C, or 100 to 180°C.

[0035] <Polyester resin> One embodiment of the present invention relates to a polyester resin having a constitutional unit derived from a dibenzo[g,p]chrysene-based diol compound represented by the formula (1) and a constitutional unit derived from a dicarboxylic acid compound. The details of the dibenzo[g,p]chrysene-based diol compound are as described in the <Dibenzo[g,p]chrysene-based diol compound> section.

[0036] The polyester resin according to this embodiment has excellent moldability, a high refractive index, and high heat resistance, and is therefore suitable for producing optical products.

[0037] Generally, 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF) is used as an optical material, but in order to achieve a higher refractive index, it is possible to use 9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]fluorene (BNEF) described in JP 2011-68624 A. However, when BNEF is used, the glass transition temperature increases, resulting in poor moldability. In contrast, the polyester resin according to this embodiment can achieve both a high refractive index and good moldability. In addition, the polyester resin according to this embodiment can have heat resistance equivalent to that of the case where BPEF is used.

[0038] Examples of the dicarboxylic acid compound (including dicarboxylic acid and its ester) constituting the polyester resin according to the present embodiment include: At least one aromatic dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the following formula (2) and esters thereof: [ka] wherein Z is a monocyclic or polycyclic aromatic ring; and At least one fluorene-based dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the following formula (3) and esters thereof: [ka] [where, X 1 are each independently 1-8 an alkylene group. Examples include:

[0039] The polyester resin according to the present embodiment may have only one of the structural units derived from the aromatic dicarboxylic acid compound and the structural units derived from the fluorene-based dicarboxylic acid compound, but preferably has both.

[0040] By containing the structural units derived from the aromatic dicarboxylic acid compound, the refractive index of the polyester resin tends to be increased. By containing the structural unit derived from the fluorene-based dicarboxylic acid compound, the refractive index and heat resistance of the polyester resin tend to be increased.

[0041] Examples of Z in the formula (2) include a benzene ring, a naphthalene ring, and a binaphthalene ring.

[0042] Examples of the ester of the dicarboxylic acid represented by the formula (2) include C 1-6 Alkyl esters, C 1-3 Only one or both of the carboxylic acids may be esterified.

[0043] In the formula (3), X 1 are each independently 1-8 An alkylene group. There is no particular limitation. X 1 are each independently 1-6 Alkylene group, C 1-4 Alkylene group, C 1-2 It may be an alkylene group or a C2 alkylene group.

[0044] Examples of the ester of the dicarboxylic acid represented by the formula (3) include C 1-6 Alkyl esters, C 1-3Only one or both of the carboxylic acids may be esterified.

[0045] The molar ratio of the constituent units derived from the aromatic dicarboxylic acid compound to the constituent units derived from the fluorene-based dicarboxylic acid compound is preferably 20:80 to 80:20. The molar ratio can be determined by analysis using a nuclear magnetic resonance apparatus.

[0046] The polyester resin according to this embodiment may further contain a structural unit derived from an aliphatic diol compound represented by the following formula (4). [ka] [where, X 2 is C 2-8 an alkylene group.

[0047] By containing a structural unit derived from the aliphatic diol compound, the flexibility of the polyester resin tends to be increased.

[0048] In the formula (4), X 2 is C 2-8 An alkylene group. There is no particular limitation. X 2 is C 2-6 Alkylene group, C 2-4 Alkylene group, C 2-3 It may be an alkylene group or a C2 alkylene group.

[0049] The molar ratio of the constitutional unit derived from the dibenzo[g,p]chrysene-based diol compound represented by the formula (1) to the constitutional unit derived from the aliphatic diol compound represented by the formula (4) is preferably 99: 1 to 50: 50. The molar ratio can be determined by analysis using a nuclear magnetic resonance apparatus.

[0050] The total of the constituent units derived from the dibenzo[g,p]chrysene diol compound, the constituent units derived from the aromatic dicarboxylic acid compound, the constituent units derived from the fluorene dicarboxylic acid compound, and the constituent units derived from the aliphatic diol compound is preferably 70 to 100 mol %, more preferably 80 to 100 mol %, even more preferably 90 to 100 mol %, and particularly preferably 95 to 100 mol %, based on all the constituent units constituting the polyester resin.

[0051] The polyester resin according to the present embodiment may have additional structural units within a range that does not adversely affect the intended use. The additional structural units are not particularly limited, and any structural units known as structural units of polyester resins may be used.

[0052] The refractive index of the polyester resin according to this embodiment is preferably 1.60 to 1.75, more preferably 1.63 to 1.72, and even more preferably 1.67 to 1.70. A polyester resin exhibiting such a refractive index is particularly suitable for the manufacture of optical products. The refractive index can be adjusted by changing the composition of the structural units constituting the polyester resin. For example, the refractive index of the polyester resin can be increased by increasing the proportion of a monomer compound exhibiting a high refractive index. The refractive index can be measured by the method described in the following examples.

[0053] The Abbe number of the polyester resin according to the present embodiment is preferably 10 to 20, more preferably 12 to 18, and further preferably 14 to 16. Since the Abbe number is usually inversely correlated with the refractive index, the Abbe number can be reduced by increasing the refractive index. The Abbe number can be measured by the method described in the following examples.

[0054] The 5% mass reduction temperature (index of heat resistance) of the polyester resin according to this embodiment is preferably 400 to 440°C, more preferably 405 to 430°C, and even more preferably 410 to 425°C. A polyester resin exhibiting such a 5% mass reduction temperature is particularly suitable for the manufacture of optical products. The 5% mass reduction temperature can be adjusted by changing the composition of the structural units constituting the polyester resin. For example, the 5% mass reduction temperature of the polyester resin can be increased by increasing the proportion of a monomer compound having high heat resistance. The 5% mass reduction temperature can be measured by the method described in the following examples.

[0055] The glass transition temperature (Tg) of the polyester resin according to the present embodiment is preferably 120 to 140°C, more preferably 126 to 134°C, and further preferably 128 to 132°C. The polyester resin exhibiting such a Tg is particularly excellent in moldability. Tg can be adjusted by changing the composition of the structural units constituting the polyester resin. Tg can be measured by the method described in the following examples.

[0056] <Method of producing polyester resin> One embodiment of the present invention relates to a method for producing a polyester resin, comprising a polymerization step of reacting a dibenzo[g,p]chrysene-based diol compound represented by the formula (1) with a dicarboxylic acid compound. Details of the dibenzo[g,p]chrysene-based diol compound are as described in the <Dibenzo[g,p]chrysene-based diol compound> section.

[0057] The dicarboxylic acid compound used in the manufacturing method according to the present embodiment includes, for example, at least one aromatic dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the formula (2) and their esters, and at least one fluorene-based dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the formula (3) and their esters. Either one of the aromatic dicarboxylic acid compound and the fluorene-based dicarboxylic acid compound may be used, but it is preferable to use both. Details of the aromatic dicarboxylic acid compound and the fluorene-based dicarboxylic acid compound are as described in the section of <Polyester Resin>.

[0058] In the production method according to the present embodiment, the aliphatic diol compound represented by the formula (4) may be further polymerized. Details of the aliphatic diol compound are as described in the <Polyester resin> section.

[0059] The polymerization reaction is preferably carried out in the presence of a transesterification catalyst. The transesterification catalyst is not particularly limited, and any catalyst commonly used in the synthesis of polyester resins may be used.

[0060] The temperature of the polymerization reaction is not particularly limited, but may be, for example, 200 to 350°C, 240 to 300°C, or 270 to 280°C.

[0061] <Optical products> One embodiment of the present invention relates to an optical product comprising the polyester resin, such as an optical film and an optical lens. EXAMPLES

[0062] The present invention will be described in more detail below using examples and comparative examples, but the technical scope of the present invention is not limited to these.

[0063] <Example 1> [Synthesis of dibenzo[g,p]chrysene diol compound 1] In an argon atmosphere, dibutyldiol DBC body (2.8 g, 6.0 mmol: synthesized in N. Yoshida et al. Tetrahedron Letters, 61, 2020, 152406), DMF (90 mL), potassium carbonate (1.66 g, 12 mmol), and ethylene carbonate (1.32 g, 15 mmol) were added to a 300 mL wide-mouth flask, and the mixture was immersed in an oil bath set at 175 ° C. in advance and heated and stirred for 1 hour. After the reaction was completed, the mixture was allowed to cool naturally to room temperature and left to stand for 1 hour. After the reaction was stopped with 1 M HCl aqueous solution (72 mL), the mixture was transferred to a separatory funnel and separated into an organic layer and an aqueous layer, and the aqueous layer was extracted with toluene (30 mL × 3). The collected organic layer was washed with Brine (50 mL), magnesium sulfate was added, the water in the organic layer was removed, and the mixture was concentrated using an evaporator. 3.37 g of a brown solid was obtained as a crude product. The crude product was purified using a filtration column (SiO2, 17G3, toluene / ethyl acetate = 2 / 1, h = 5 cm) to obtain 2.75 g (83%) of a whitish yellow solid. After that, recrystallization was performed using methylene chloride / hexane = 2 / 1 v / v, and the solid was collected by filtration under reduced pressure and dried under vacuum (100°C, 1 h) to obtain 2.3 g (70%) of dibenzo[g,p]chrysene-based diol compound 1 as a white solid. The synthesis scheme is shown below. The dibenzo[g,p]chrysene-based diol compound 1 synthesized was 1 H-NMR spectrum and 13 The C-NMR spectra are shown in Figures 1 and 2, respectively. [ka]

[0064] [Synthesis of polyester resin] The dibenzo[g,p]chrysene diol compound 1 (9.3 × 10 -3 moles), ethylene glycol (hereinafter referred to as EG) (23.5 × 10 -3 mol), dimethyl 2,6-naphthalenedicarboxylate (DMN) (3.3 × 10 -3mol), 9,9-di(2-methoxycarbonylethyl)fluorene (hereinafter referred to as FDPM) (7.7 × 10 -3 mol), and manganese acetate tetrahydrate (2.5 × 10 -6 The mixture was gradually heated to melt while stirring under a nitrogen atmosphere, and the temperature was raised to 250°C. The mixture was then stirred for 3 hours to carry out an ester exchange reaction. Then, an aqueous solution of trimethyl phosphate (6.5 × 10 -6 mol) and germanium dioxide aqueous solution (38.6 × 10 -6 The mixture was stirred, and the temperature was gradually increased and the pressure reduced until the temperature reached 275° C. and the pressure reached 0.4 kPa or less, while removing the ethylene glycol. After the predetermined pressure reduction and temperature were reached, the mixture was stirred for 4 hours, and the contents were removed from the reactor to obtain polyester resin pellets. The molar ratio of dibenzo[g,p]chrysene diol compound 1 to EG was 85:15. FDPM was synthesized by using methyl acrylate instead of t-butyl acrylate in Example 1 of JP-A-2005-89422.

[0065] <Comparative Example 1> Polyester resin pellets were obtained in the same manner as in Example 1, except that the dibenzo[g,p]chrysene-based diol compound 1 in Example 1 was changed to 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF) (manufactured by Osaka Gas Chemicals Co., Ltd.). The molar ratio of BPEF to EG was 85:15.

[0066] <Evaluation method> The monomer compounds and resins of the above-mentioned Examples and Comparative Examples were evaluated as follows.

[0067] [Polymer composition] The sample was dissolved in deuterated chloroform containing tetramethylsilane as an internal standard, and the 1H-NMR spectrum was measured using a nuclear magnetic resonance apparatus ("AVANCE III HD" manufactured by BRUKER). The integral values ​​of the peaks derived from each monomer used in the polymerization were calculated for the obtained spectrum, and the proportion of each monomer component (structural unit) introduced into the polymer was calculated.

[0068] [Refractive index nD] The measurements were performed using a refractometer (Atago Co., Ltd., DR-M2 (circulating thermostatic water bath 60-C3)) at a temperature of 25° C. and a wavelength of 589 nm (D line).

[0069] The refractive index of the monomer compound was calculated by dissolving a sample in chloroform to prepare solutions with concentrations of 7.67% by mass and 16.8% by mass, and extrapolating the concentration to 100% by mass on a calibration curve (approximate straight line) prepared by measuring the refractive index of the obtained solutions.

[0070] The refractive index of the resin sample was measured as follows. The resin sample was heat pressed at 200-240°C to form a film with a thickness of 200-300 μm. This film was cut into a rectangular shape with a length of 20-30 mm and a width of 10 mm to obtain a test piece. The refractive index nD of the obtained test piece at 589 nm (D line) was measured using a multi-wavelength Abbe refractometer (Atago Co., Ltd.'s "DR-M4 (circulating thermostatic bath 60-C3)") at a measurement temperature of 20°C and diiodomethane as a contact liquid.

[0071] [Abbe number] Using the test piece for measuring the refractive index nD at 589 nm (D line), the refractive indexes nF and nC were measured in the same manner as for the refractive index nD, except that the measurement wavelength was changed to 486 nm (F line) or 656 nm (C line). The Abbe number was calculated from the refractive indexes nF, nD, and nC at each wavelength obtained by the following formula. (Abbe number)=(nD-1) / (nF-nC)

[0072] [Glass transition temperature Tg] Measurements were performed using a differential scanning calorimeter (SII NanoTechnology Inc., "EXSTAR6000 DSC6220 ASD-2") in a nitrogen gas atmosphere at a heating rate of 10°C / min.

[0073] [Heat resistance evaluation] Using a thermogravimetry-differential thermal analyzer (TG-DTA) ("TG / DTA6200" manufactured by SII NanoTechnology, Inc.), the temperature at which the mass of the sample decreased by 5% by mass was measured under conditions of a nitrogen atmosphere and a heating rate of 10°C / min.

[0074] <Evaluation Results> [Monomer compounds] [Table 1]

[0075] [Polyester resin compound] [Table 2] [Industrial Applicability]

[0076] The polyester resin of the present embodiment has excellent optical properties such as a high refractive index. In addition, it is also excellent in various properties such as heat resistance and moldability (glass transition temperature). Therefore, the polyester resin of the present embodiment (or a resin composition thereof) can be suitably used for optical lenses, optical films, optical sheets, pickup lenses, holograms, films for liquid crystals, films for organic EL, and the like. In addition, the polyester resin of the present embodiment (or a resin composition thereof) can be suitably used for paints, antistatic agents, inks, adhesives, pressure sensitive adhesives, resin fillers, charging trays, conductive sheets, protective films (protective films for electronic devices, liquid crystal members, and the like), electric and electronic materials (carrier transport agents, light emitters, organic photoconductors, thermal recording materials, hologram recording materials), resins for electric and electronic parts or devices (optical disks, inkjet printers, digital paper, organic semiconductor lasers, dye-sensitized solar cells, EMI shielding films, photochromic materials, organic EL elements, color filters, and the like), resins for mechanical parts or devices (automobiles, aerospace materials, sensors, sliding members, and the like), and the like.

Claims

1. A dibenzo[g,p]chrysene-based diol compound represented by the following formula (1): 【Chemistry 1】 [In the formula, R 1 and R 2 are each independently 1-8 is an alkyl group, R 3 and R 4 are each independently a hydroxy C 1-4 is an alkylene group.

2. A structural unit derived from the dibenzo[g,p]chrysene diol compound according to claim 1; A structural unit derived from a dicarboxylic acid compound; The polyester resin has the formula:

3. The dicarboxylic acid compound is At least one aromatic dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the following formula (2) and esters thereof; 【Chemistry 2】 wherein Z is a monocyclic or polycyclic aromatic ring. At least one fluorene-based dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the following formula (3) and esters thereof; 【Chemistry 3】 [In the formula, X 1 are each independently 1-8 an alkylene group. The polyester resin of claim 2 , comprising:

4. The polyester resin according to claim 3 , wherein Z in the formula (2) is a benzene ring, a naphthalene ring, or a binaphthalene ring.

5. A structural unit derived from the aromatic dicarboxylic acid compound; A structural unit derived from the fluorene-based dicarboxylic acid compound; The polyester resin according to claim 3 or 4, wherein the molar ratio of

6. A structural unit derived from an aliphatic diol compound represented by the following formula (4): 【Chemistry 4】 [In the formula, X 2 is C 2-8 an alkylene group. The polyester resin according to any one of claims 2 to 5, further comprising:

7. A constitutional unit derived from the dibenzo[g,p]chrysene diol compound; A structural unit derived from the aliphatic diol compound; The polyester resin according to claim 6, wherein the molar ratio of

8. An optical film comprising the polyester resin according to any one of claims 2 to 7.

9. An optical lens comprising the polyester resin according to any one of claims 2 to 7.

10. A dibenzo[g,p]chrysene-based raw material represented by the following formula (5), 【Chemistry 5】 [In the formula, R 5 and R 6 are each independently 1-8 is an alkyl group. comprising a reaction step of hydroxyalkylating A method for producing a dibenzo[g,p]chrysene-based diol compound represented by the following formula (1): 【Chemistry 6】 [In the formula, R 1 and R 2 are each independently 1-8 is an alkyl group, R 3 and R 4 are each independently a hydroxy C 1-4 is an alkylene group.

11. The reaction step comprises reacting the dibenzo[g,p]chrysene-based raw material with reacting with an alkylene carbonate; reacting with a halogenated alkanol; or reacting with an alkyl halide alkanoate and hydrolyzing the resulting reaction product; The method of claim 10, comprising:

12. The reacting step is carried out in the presence of a solvent, The method according to claim 10 or 11, wherein the solvent is selected from the group consisting of aromatic hydrocarbon solvents, halogen-based solvents, amine-based solvents, amide-based solvents, alcohol-based solvents, nitrile-based solvents, ketone-based solvents, and ether-based solvents.

13. A dibenzo[g,p]chrysene-based diol compound represented by the following formula (1), 【Chemistry 7】 [In the formula, R 1 and R 2 are each independently 1-8 is an alkyl group, R 3 and R 4 are each independently a hydroxy C 1-4 an alkylene group. A dicarboxylic acid compound, A method for producing a polyester resin, comprising a polymerization step of reacting

14. The dicarboxylic acid compound is At least one aromatic dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the following formula (2) and esters thereof; 【Chemistry 8】 wherein Z is a monocyclic or polycyclic aromatic ring. At least one fluorene-based dicarboxylic acid compound selected from the group consisting of dicarboxylic acids represented by the following formula (3) and esters thereof; 【Chemistry 9】 [In the formula, X 1 are each independently 1-8 an alkylene group. The method for producing the polyester resin according to claim 13, comprising:

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