Phenanthrene-based compound having high refractive index and method for preparing the same

Abstract

The present invention relates to a phenanthrene-based compound having a high refractive index and a method for manufacturing the same. More specifically, the present invention relates to a high refractive index monomer that can be used in optical resins requiring a refractive index of 1.7 or higher, and a method for manufacturing the same, wherein the compound is a phenanthrene-based composite cardo structure. By using the phenanthrene-based composite cardo structure of the present invention, the fluidity of the molecular chain is suppressed to the maximum extent, and it can be utilized in the manufacture of resins with excellent thermal stability having a high glass transition temperature.

Description

Technology Field

[0001] The present invention relates to a phenanthrene-based compound having a high refractive index and a method for manufacturing the same. More specifically, the present invention relates to a high refractive index monomer that can be used in an optical resin requiring a refractive index of 1.7 or higher, wherein the compound is a phenanthrene-based composite cardo structure. Background Technology

[0003] Conventionally, monomers with improved refractive index, such as compounds represented by the following chemical formulas A to C, have been used to manufacture optical resins having a high refractive index. However, the following compounds also had limitations in that they could not be applied to high refractive index applications where a refractive index of 1.7 or higher is required.

[0004] [Chemical Formula A]

[0005]

[0006] [Chemical Formula B]

[0007]

[0008] [Chemical Formula C]

[0009]

[0010] Accordingly, there was a need to develop a novel compound having a structure with functional groups applicable to resins such as polyester, polycarbonate, polyurethane, polyolefin, epoxy, and acrylic, which has a higher refractive index than existing commercially available monomers for optical resins. Prior art literature

[0012] Republic of Korea Registered Patent No. 10-2134675 (Published Dec. 21, 2018) The problem to be solved

[0013] The inventors have made diligent research efforts to develop a novel compound with a high refractive index applicable to optical resins. As a result, the present invention was completed by manufacturing a phenanthrene-based compound with a high refractive index.

[0014] Accordingly, the object of the present invention is to provide a phenanthrene-based compound having a high refractive index and a method for manufacturing the same. means of solving the problem

[0016] The inventors have made diligent research efforts to develop a novel compound with a high refractive index applicable to optical resins. As a result, the present invention was completed by manufacturing a phenanthrene-based compound with a high refractive index.

[0018] According to one aspect of the present invention, the present invention provides a phenanthrene-based compound having the chemical structure of Formula 1 below:

[0019] [Chemical Formula 1]

[0020] ,

[0021] Here, the above R 1a , R 1b , R 2a , and R 2b represents a substituent;

[0022] R 3a and R 3b represents an alkylene group;

[0023] k1 and k2 independently represent integers from 0 to 4;

[0024] m1 and m2 independently represent integers from 0 to 3;

[0025] n1 and n2 independently represent integers of 0 or greater than or equal to 1;

[0026] p1 and p2 are independently integers greater than or equal to 1;

[0027] However, m1+p1 and m2+p2 are independently integers from 1 to 4.

[0029] This compound is a phenanthrene-based composite cardo structure and is a high refractive index monomer that can be used in optical resins requiring a refractive index of 1.7 or higher.

[0030] In this specification, the term "cardo compound" refers to a compound having a structure in which a cyclic side group is present in the molecular main chain. Cardo compounds impart severe rotational hindrance to the main chain due to the structural characteristic of having bulky lateral groups in the polymer main chain, thereby possessing not only very high heat resistance (high glass transition temperature) but also excellent processability.

[0031] In one embodiment of the present invention, R 1a and R 1b The substituent represented by is not particularly limited, but is generally an alkyl group. Examples of the above alkyl group include C1 to C6 alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, and t-butyl groups (e.g., C1-4 alkyl groups, particularly methyl groups). 1a and R 1b They may be different from each other and may be identical. In addition, regarding the benzene ring constituting the above phenanthrene backbone, R 1a or R 1b The bonding positions (substitution positions) are not particularly limited. The preferred substitution numbers k1 and k2 are 0 or 1. Additionally, the substitution numbers k1 and k2 may be different or identical, but are generally identical.

[0032] Substituent R 2a and R 2bHydrocarbon groups such as alkyl groups (C1 to C20 alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, etc., preferably C1 to C8 alkyl groups, also preferably C1 to C6 alkyl groups, etc.), cycloalkyl groups (C5 to C10 cycloalkyl groups such as cyclopentyl, cyclohexyl, etc., preferably C5-8 cycloalkyl groups, also preferably C5-6 cycloalkyl groups, etc.), aryl groups [C6 to C10 aryl groups such as phenyl, alkylphenyl groups (methylphenyl, dimethylphenyl, etc.), preferably C6 to C8 aryl groups, particularly phenyl groups, etc.), aralkyl groups (C6-10 aryl-C1 to C4 alkyl groups such as benzyl, phenethyl, etc.); alkoxy groups (C1 to C4 alkoxy groups such as methoxy groups, etc.); acyl groups (C1 to C6 acetyl groups, etc.) Examples include acyl groups, etc.); alkoxycarbonyl groups (C1 to C4 alkoxycarbonyl groups such as methoxycarbonyl groups, etc.); halogen atoms (fluorine atoms, chlorine atoms, etc.); nitro groups; cyano groups, etc. Preferred substituent R 2a or R 2b is an alkyl group (C1 to C6 alkyl group), a cycloalkyl group (C5 to C8 cycloalkyl group), an aryl group (C6 to C10 aryl group), or an aralkyl group (C6 to C8 aryl-C1 to C2 alkyl group), and particularly C1 to C6 alkyl groups (e.g., C1 to C4 alkyl groups), C1 to C4 alkoxy groups, and C6 to C8 aryl groups are preferred. Substituent R 2a or R 2b It can be substituted with a benzene ring alone or in combination of two or more types. In addition, the above R 2a and R 2b They may be identical or different from each other, but are generally identical. Also, the above R 2a or R 2b can be different or identical for the same benzene ring. Also, substituent R 2a or R 2b The substitution location is not particularly restricted.

[0033] The preferred number of substitutions m1 and m2 vary depending on the number of substitutions of the hydroxyl group-containing group, but are 0 to 2, and preferably 0 or 1. Additionally, the number of substitutions m1 and m2 may be different or the same, but generally they are often the same.

[0034] R 3a and R 3b The alkylene group represented by is not limited to, but examples include C2 to C6 alkylene groups (ethylene group, trimethylene group, propylene group, butane-1,4-diyl (tetramethylene) group), butane-1,2-diyl group, etc.), preferably C2 to C4 alkylene groups, and particularly C2 to C3 alkylene groups (particularly ethylene group, propylene group) are preferred. In addition, R 3a and R 3b The alkylene groups may be the same or different, but generally they are the same alkylene groups.

[0035] The number of substitutions (additional numbers) of the alkoxy groups n1 and n2 are not particularly limited but may be the same or different and may be selected from a range of 0 or 1 to 15 (e.g., 0 or 1 to 12), for example, 0 or 1 to 10 (e.g., 0 or 1 to 6), preferably 0 or 1 to 4, also preferably 0 or 1 to 3 (e.g., 0 to 2), particularly 0 or 1. In addition, the sum of n1 and n2 (n1 + n2) may be selected from a range of 0 or 1 to 30 (e.g., 0 or 1 to 24), for example, 0 or 1 to 20 (e.g., 0 or 1 to 12), preferably 0 or 1 to 8, also preferably 0 or 1 to 6 (e.g., 0 to 4), particularly 0 or 2. In addition, when n1 or n2 is 2 or more, the polyalkoxy (polyalkyleneoxy) group may be composed of the same alkoxy group or may be composed of a mixture of different alkoxy groups (e.g., ethoxy group and propyleneoxy group), but generally, it is often composed of the same alkoxy group.

[0036] The number of substitutions p1 and p2 of the hydroxyl group-containing group is preferably 1 to 2, and particularly preferably 1. In addition, the sum of p1 and p2 (p1 + p2) may be, for example, 2 to 6, preferably 2 to 4 (particularly 2). In addition, the number of substitutions p1 and p2 may be different, but generally they are often the same. The substitution positions of the hydroxyl group-containing group are not particularly limited.

[0037] In one embodiment of the present invention, the R 3a and R 3b is independently a C2 to C4 alkylene group; n1 and n2 are 0 or 1, but are not limited thereto.

[0038] In one embodiment of the present invention, p1 and p2 are each 1, but are not limited thereto.

[0039] In one embodiment of the present invention, R 1a and R 1b is independently a C1 to C4 alkyl group; k1 and k2 are independently 0 or 1; and R 2a and R 2b is independently a C1 to C4 alkyl group, a C1 to C4 alkoxy group, or a C6 to C8 aryl group; m1 and m2 are integers from 0 to 2, but are not limited thereto.

[0040] In a specific embodiment of the present invention, the representative phenanthrene compound represented by Formula 1 is a compound having the chemical structure of Formula 2-1 or 2-2 below:

[0041] [Chemical Formula 2-1]

[0042] ; and

[0043] [Chemical Formula 2-2]

[0044] .

[0046] According to another aspect of the present invention, the present invention provides a method for producing a phenanthrene-based compound comprising the following steps:

[0047] (a) A step of synthesizing pyrene-4,5-dione by oxidizing pyrene;

[0048] (b) a step of synthesizing cyclopentaphenanthrene-4-one from pyrene-4,5-dione; and

[0049] (c) 2,2'-(((4 from cyclopentaphenanthrene-4-one H Step for synthesizing -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol.

[0051] In one embodiment of the present invention, a method for preparing a phenanthrene-based compound according to one aspect of the present invention comprises: (d) 2,2'-(((4 H - The method additionally includes the step of synthesizing 4,4'-(4H-cyclopentaphenanthrene-4,4-diyl)diphenol from -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol.

[0053] (a) Step: Synthesis step of pyrene-4,5-dione

[0054] In one embodiment of the present invention, step (a) is a step of synthesizing pyrene-4,5-dione by oxidizing pyrene by adding sodium periodate according to the following reaction scheme 1-1:

[0055] [Reaction Equation 1-1]

[0056] .

[0057] In a specific embodiment of the present invention, pyrene and ruthenium chloride (RuCl3) were added, tetrahydrofuran (THF) was added as a solvent under a nitrogen atmosphere and stirred, then an aqueous solution of dissolved NaIO4 was added, dichloromethane (DCM) solvent was added, and the mixture was stirred at room temperature. The stirring time may be 3 to 5 hours.

[0058] In a specific embodiment of the present invention, based on 20 mmol of pyrene, NaIO4 may be added in an amount of 60 to 120 mmol, 60 to 100 mmol, 60 to 90 mmol, 60 to 88 mmol, 70 to 120 mmol, 70 to 100 mmol, 70 to 90 mmol, 70 to 88 mmol, 80 to 120 mmol, 80 to 100 mmol, 80 to 90 mmol, or 80 to 88 mmol, but is not limited thereto.

[0059] In a specific embodiment of the present invention, the stirred solution was filtered to remove the solid, the filtrate was extracted using dichloromethane (DCM) and H2O, the organic layer was separated, and MgSO4 was added and filtered.

[0060] In a specific embodiment of the present invention, the filtrate was subjected to reduced pressure and recrystallized to obtain the pyrene-4,5-dione. The recrystallization may be carried out by adding a solution of dichloromethane (DCM) and hexane.

[0062] (b) Step: Synthesis step of cyclopentaphenanthrene-4-one

[0063] In one embodiment of the present invention, step (b) is a step of synthesizing cyclopentaphenanthrene-4-one by adding sodium hydroxide to pyrene-4,5-dione according to the following reaction scheme 1-2:

[0064] [Reaction Equation 1-2]

[0065] .

[0066] In a specific embodiment of the present invention, cyclopentaphenanthrene-4-one was synthesized by reacting the pyrene-4,5-dione synthesized in step (a) with NaOH under an oxygen atmosphere.

[0067] In a specific embodiment of the present invention, based on 10 mmol of pyrene-4,5-dione, NaOH may be added in amounts of 5 to 40 mmol, 5 to 35 mmol, 5 to 30 mmol, 5 to 25 mmol, 5 to 20 mmol, 10 to 40 mmol, 10 to 35 mmol, 10 to 30 mmol, 10 to 25 mmol, 10 to 20 mmol, 15 to 40 mmol, 15 to 35 mmol, 15 to 30 mmol, 15 to 25 mmol, 15 to 20 mmol, 20 to 40 mmol, 20 to 35 mmol, 20 to 30 mmol, and 20 to 25 mmol, but is not limited thereto.

[0068] The above reaction temperature may be 70°C to 120°C, 80°C to 120°C, 90°C to 120°C, 70°C to 110°C, 80°C to 110°C, 90°C to 110°C, 70°C to 100°C, 80°C to 100°C, 90°C to 100°C, 70°C, 80°C, or 90°C, but is not limited thereto.

[0069] The above reaction time may be 2 to 6 days, 3 to 6 days, 4 to 6 days, 2 to 5 days, 3 to 5 days, 4 to 5 days, 2 to 4 days, 3 to 4 days, 3, 4, 5 days, or 6 days, but is not limited thereto.

[0070] In a specific embodiment of the present invention, the product resulting from the completed reaction was extracted using DCM and H2O, the organic layer was separated, MgSO4 was added, and then filtered.

[0071] In a specific embodiment of the present invention, the filtrate was subjected to reduced pressure and then recrystallized to obtain cyclopentaphenanthrene-4-one. The recrystallization can be carried out by adding a solution of dichloromethane (DCM) and hexane.

[0073] (c) Step: 2,2'-(((4 H Synthesis step of -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol (Compound 1)

[0074] In a specific embodiment of the present invention, step (c) is performed by adding phenoxyethanol to cyclopentaphenanthrene-4-one according to the following reaction scheme 1-3 to obtain 2,2'-(((4 H This is the step for synthesizing -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol:

[0075] [Reaction Equation 1-3]

[0076] .

[0077] In a specific embodiment of the present invention, phenoxyethanol is added to the cyclopentaphenanthrene-4-one synthesized in step (b) to 2,2'-(((4) in the presence of an acid catalyst H -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol (compound 1) was synthesized.

[0078] In a specific embodiment of the present invention, based on 10 mmol of cyclopentaphenanthrene-4-one prepared in step (b), phenoxyethanol is 20 to 80 mmol, 20 to 70 mmol, 20 to 60 mmol, 20 to 50 mmol, 20 to 40 mmol, 25 to 80 mmol, 25 to 70 mmol, 25 to 60 mmol, 25 to 50 mmol, 25 to 40 mmol, 30 to 80 mmol, 30 to 70 mmol, 30 to 60 mmol, 30 to 50 mmol, 30 to 40 mmol, 35 to 80 mmol, 35 to 70 mmol, 35 to 60 mmol, 35 to 50 mmol, 35 to 40 mmol, 20 mmol, 25 mmol, 30 mmol, 35 mmol, or 40 mmol may be added, but is not limited thereto.

[0079] In a specific embodiment of the present invention, the acid catalyst may be an inorganic acid [sulfuric acid, hydrogen sulfate salt (alkaline metal salt of hydrogen sulfate such as sodium hydrogen sulfate, etc.), hydrogen chloride, hydrochloric acid (a hydrogen chloride aqueous solution of 5 to 36 wt%, preferably 20 to 36 wt%, etc.), phosphoric acid, etc.] or an organic acid [sulfonic acid (alkane sulfonic acid such as methanesulfonic acid, etc.) etc.]. The sulfuric acid may include dilute sulfuric acid (e.g., sulfuric acid of 30 to 90%), concentrated sulfuric acid (e.g., sulfuric acid of 90% or higher concentration), fuming sulfuric acid, etc., and if it can be converted into sulfuric acid in the reaction system, sulfur trioxide may be used as a sulfuric acid precursor. The acid catalyst may be used alone or in combination of two or more types. The preferred acid catalyst is hydrochloric acid or sulfuric acid.

[0080] The reaction can be carried out by using a thiol as a co-catalyst together with an acid catalyst. By combining the acid catalyst with the thiol, the condensation reaction can be effectively carried out simply and efficiently. Examples of thiols that function as co-catalysts include common thiols, such as mercaptocarboxylic acids (thioacetic acid, β-mercaptopropionic acid, α-mercaptopropionic acid, thioglycolic acid, thiooxalic acid, mercaptosuccinic acid, mercaptobenzoic acid, etc.), alkyl mercaptans (C1-16 alkyl mercaptans such as methyl mercaptan, ethyl mercaptan, propyl mercaptan, isopropyl mercaptan, n-butyl mercaptan, dodecyl mercaptan, etc. (especially C1-4 alkyl mercaptans)), aralkyl mercaptans (benzyl mercaptan, etc.), or salts thereof. Examples of salts include alkali metal salts (such as sodium salts). Among these thiols, mercapto C2-6 carboxylic acids (particularly thioacetic acid, β-mercaptopropionic acid) are preferred. Thiols can be used alone or in combination of two or more types.

[0082] (d) Step: Synthesis step of 4,4'-(4H-cyclopentaphenanthrene-4.4-diyl)diphenol (Compound 2)

[0083] Step (d) above is according to the following reaction scheme 1-4, 2,2'-(((4 H This is the step of synthesizing 4,4'-(4H-cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene)bis(oxy))diethanol by adding potassium hydroxide:

[0084] [Reaction Equation 1-4]

[0085] .

[0086] In a specific embodiment of the present invention, the 2,2'-(((4 synthesized in step (c) H4,4'-(4H-cyclopentaphenanthrene-4,4-diyl)diphenol (compound 2) was synthesized by reacting potassium hydroxide with diethanol while stirring -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene)bis(oxy))diethanol.

[0087] In a specific embodiment of the present invention, based on 3 mmol of 2,2'-(((4H-cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol, potassium hydroxide (KOH) is 15 to 60 mmol, 15 to 55 mmol, 15 to 50 mmol, 15 to 45 mmol, 15 to 40 mmol, 15 to 30 mmol, 15 to 25 mmol, 15 to 30 mmol, 20 to 60 mmol, 20 to 55 mmol, 20 to 50 mmol, 20 to 45 mmol, 20 to 40 mmol, 20 to 30 mmol, 20 to 25 mmol, 30 to 60 mmol, 30 to 55 mmol, 30 to 50 mmol, 30 to 45 mmol, 30 to 40 mmol, 20 mmol, 25 mmol, or 30 mmol may be added, but is not limited thereto.

[0088] In a specific embodiment of the present invention, the reaction may be carried out under a nitrogen atmosphere.

[0089] In a specific embodiment of the present invention, the solvent of the reaction may be DMSO (dimethylsulfoxide), but is not limited thereto.

[0090] In a specific embodiment of the present invention, the temperature at which the reaction is performed may be 80 to 150°C, 80 to 140°C, 80 to 130°C, 80 to 120°C, 80 to 110°C, 80 to 100°C, 90 to 150°C, 90 to 140°C, 90 to 130°C, 90 to 120°C, 90 to 110°C, 90 to 100°C, 100 to 150°C, 100 to 140°C, 100 to 130°C, 100 to 120°C, 100 to 110°C, 80°C, 90°C, 100°C, 110°C, or 120°C, but is not limited thereto.

[0091] In a specific embodiment of the present invention, the reaction (stirring) time may be 1 hour to 6 hours, 1 hour to 5 hours, 1 hour to 4 hours, 1 hour to 3 hours, 2 hours to 6 hours, 2 hours to 5 hours, 2 hours to 4 hours, 2 hours to 3 hours, 3 hours to 6 hours, 3 hours to 5 hours, 3 hours to 4 hours, 1 hour, 2 hours, 3 hours, or 4 hours, but is not limited thereto.

[0092] In a specific embodiment of the present invention, the pH of the reaction solution after the reaction may be adjusted to be acidic. The pH may be 1 to 4, 1 to 3, or 1 to 2, but is not limited thereto.

[0093] In a specific embodiment of the present invention, after the pH of the reaction solution was adjusted to acidic, extraction was performed using ethyl acetate, brine, and water.

[0094] In a specific embodiment of the present invention, the organic layer was separated from the extract and filtered after adding MgSO4.

[0095] In a specific embodiment of the present invention, the filtrate was subjected to reduced pressure and then recrystallized to obtain 4,4'-(4H-cyclopentaphenanthrene-4,4-diyl)diphenol (compound 2). The recrystallization may be carried out by adding a solution of dichloromethane (DCM) and hexane.

[0097] According to another aspect of the present invention, the phenanthrene-based compound of the present invention has four phenyl groups, which can improve or enhance various properties, including optical properties. Therefore, the phenanthrene-based compound of the present invention can be usefully used as a resin component, an additive, etc. In addition, since the phenanthrene-based compound of the present invention has multiple hydroxyl groups, when used to form a resin component, the properties of the resin can be efficiently improved.

[0098] In one embodiment of the present invention, the resin component may be (i) a resin comprising a monomer of a phenanthrene-based compound represented by Formula 1 of the present invention, or (ii) a resin composed of the phenanthrene-based compound and the resin.

[0099] In one embodiment of the present invention, the resin constituting the resin component (the resin component (i) or (ii)) is not particularly limited and may use a conventional thermoplastic resin, a thermosetting resin (or a photocurable resin). The resin constituting the resin component may be used alone or in combination of two or more types.

[0100] Examples of thermoplastic resins include olefin resins (polyethylene, polypropylene, polymethylpentene, amorphous polyolefin, etc.), halogen-containing vinyl resins (chlorine-containing resins such as polyvinyl chloride, fluorinated resins, etc.), acrylic resins, styrene resins (polystyrene, acrylonitrile-styrene resin, etc.), polycarbonate resins (bisphenol A type polycarbonate, etc.), polyester resins (polyalkylene arylate resins such as polyethylene terephthalate, polybutylene terephthalate, polycyclohexanedimethylene terephthalate, polyethylene naphthalate, polyarylate resins, liquid crystal polyester, etc.), polyacetal resins, polyamide resins (polyamide 6, polyamide 66, polyamide 46, polyamide 6T, polyamide MXD, etc.), polyphenylene ether resins (modified polyphenylene ether, etc.), and polysulfone resins (polysulfone, polyethersulfone, etc.). Examples include polyphenylene sulfide-based resins (polyphenylene sulfide, etc.), polyimide-based resins (polyetherimide, polyamideimide, polyaminobismaleimide, bismaleimide triazine resin, etc.), polyether ketone-based resins (polyether ketone, polyetheretherketone, etc.), and thermoplastic elastomers (polyamide-based elastomer, polyester-based elastomer, polyurethane-based elastomer, polystyrene-based elastomer, polyolefin-based elastomer, polydiene-based elastomer, polyvinyl chloride-based elastomer, fluorine-based thermoplastic elastomer). Thermoplastic resins may be used alone or in combination of two or more types.

[0101] Examples of thermosetting resins include phenol resin, amino resin (urea resin, melamine resin, etc.), furan resin, unsaturated polyester resin, epoxy resin, thermosetting polyurethane resin, silicone resin, thermosetting polyimide resin, diallyl phthalate resin, vinyl ester resin (resin obtained by the reaction of epoxy resin with (meth)acrylic acid or its derivative, resin obtained by the reaction of polyhydric phenols with glycidyl (meth)acrylate, etc.). In addition, thermosetting resins (or photocurable resins) also include polyfunctional (meth)acrylates, vinyl ethers (divinyl ether obtained by the reaction of a diol component with acetylene, etc.). Thermosetting resins may be used alone or in combination of two or more types.

[0102] In addition, the thermosetting resin may contain an initiator, a reactive diluent, a curing agent, a curing accelerator, etc., depending on the type of thermosetting resin (or photocurable resin). For example, a resin composition containing the above epoxy resin or urethane-based resin may contain an amine-based curing agent, etc., and a resin composition containing the above unsaturated polyester-based resin or vinyl ester-based resin may contain an initiator (such as a peroxide), a polymerizable monomer (such as a reactive diluent (such as (meth)acrylic acid ester, styrene, etc.).

[0103] The resin component (i) or resin component (ii) of the present invention may be used alone or in combination of two or more types.

[0104] In addition, the resin component (i) included as the above-mentioned constituent (monomer component) may be prepared by using a phenanthrene-based compound corresponding to the polymerization component (or monomer component) as the polymerization component or constituent component of the resin (e.g., a polyol component such as a diol component). For example, in a resin (polyester resin, polyurethane resin, epoxy resin, vinyl ester resin, epoxy resin, multifunctional (meth)acrylate, (poly)urethane (meth)acrylate, (poly)ester (meth)acrylate, the vinyl ether, etc.) in which a polyol component (especially a diol component) is used as a polymerization component or constituent component, it is preferable to use the above-mentioned phenanthrene-based compound in part or all of the above-mentioned polyol component.

[0105] In the resin component (i), phenanthrene-based compounds can be used as polymerization components (or constituents) either alone or in combination of two or more types.

[0106] The resin (or resin component) constituting the preferred resin component is a polyester resin, a polyurethane resin (thermoplastic or thermosetting polyurethane resin), a polycarbonate resin, an acrylic resin [including thermosetting or photocurable resins such as polyfunctional (meth)acrylates], an epoxy resin, a vinyl ether, etc. In addition, a resin containing an aromatic ring (benzene ring) (thermoplastic resin), for example, an aromatic polycarbonate resin (bisphenol A type polycarbonate, etc.), a polyester resin [polyalkylene arylate resin; a polyarylate resin using an aromatic dicarboxylic acid (terephthalic acid, etc.) and an aromatic diol (biphenol, bisphenol A, xylene glycol, alkylene oxide adducts thereof, etc.) as polymerization components, etc.], a polysulfone resin (polysulfone, polyethersulfone, etc.), a polyphenylene sulfide resin (polyphenylene sulfide, etc.) are also preferred.

[0107] Hereinafter, regarding a representative resin (or resin component), a resin (or resin component (i)) comprising a phenanthrene-based compound represented by the above chemical formula 1 as a monomer component (polymer component, constituent component, copolymer component) is described in detail.

[0108] (1) Polyester resin

[0109] A polyester resin containing the above-mentioned phenanthrene-based compound as a polymerization component (in particular, a polyester resin obtained by polymerizing the above-mentioned phenanthrene-based compound (generally a compound in which p1=p2=1) as a monomer component of the resin) can be obtained by at least the reaction between the above-mentioned phenanthrene-based compound and a dicarboxylic acid component, and the polyester resin includes, in addition to saturated or unsaturated polyester resins, a polyarylate resin utilizing an aromatic dicarboxylic acid as a polymerization component.

[0110] The polyol component (especially the diol component) of the polyester resin can be composed by combining the above-mentioned phenanthrene compound with other diol components. Such diol components (or diols) include alkylene glycols (e.g., linear or branched C2-12 alkylene glycols such as ethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, tetramethylene glycol, hexanediol, neopentyl glycol, octanediol, decanediol, etc.), (poly)oxyalkylene glycols (e.g., diethylene glycol, triethylene glycol, dipropylene glycol, C2-4 alkylene glycol, etc.), alicyclic diols (e.g., 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, 2,2-bis(4-hydroxycyclohexyl)propane or its alkylene oxide adduct (2,2-bis(4-(2-hydroxyethoxy)cyclohexyl)propane, etc.), aromatic diols (e.g., biphenol, 2,2-bis(4-hydroxyphenyl)propane Examples include bisphenol A, bisphenol AD, bisphenol F, their alkylene oxide (C2-3 alkylene oxide) adducts (2,2-bis(4-(2-hydroxyethoxy)phenyl)propane, etc.), xylene glycol, etc. These diols may be used alone or in combination of two or more.

[0111] Preferred diols are linear or branched C2-10 alkylene glycols, particularly C2-6 alkylene glycols (e.g., linear or branched C2-4 alkylene glycols such as ethylene glycol, propylene glycol, and 1,4-butanediol). At least ethylene glycol is often used as the diol. Using such diols (e.g., ethylene glycol) can improve polymerization reactivity and, at the same time, impart flexibility to the resin.

[0112] The ratio (molar ratio) of the above phenanthrene-based compound and the above diols may be, for example, the former / the latter = 100 / 0 to 50 / 50, preferably 100 / 0 to 75 / 25 (for example, 100 / 0 to 70 / 30), and also preferably 100 / 0 to 90 / 10 (for example, 100 / 0 to 80 / 20).

[0113] Polyols such as glycerin, trimethylolpropane, trimethylol ethane, and pentaerythritol may be used in combination with the above diol component as needed.

[0114] Examples of dicarboxylic acid components constituting polyester resins include aliphatic dicarboxylic acids, alicyclic dicarboxylic acids, aromatic dicarboxylic acids, or derivatives capable of forming esters thereof [e.g., acid anhydrides; acid halides (acid chlorides, etc.); lower alkyl esters (C1-2 alkyl esters, etc.)]. These dicarboxylic acids may be used alone or in combination of two or more types.

[0115] Examples of the above aliphatic dicarboxylic acids include saturated C3-20 aliphatic dicarboxylic acids (preferably saturated C3-14 aliphatic dicarboxylic acids, etc.) such as succinic acid, glutaric acid, adipic acid, pimetic acid, souveric acid, azelaic acid, sebacic acid, dodecanedicarboxylic acid, hexadecanedicarboxylic acid; unsaturated C4-20 aliphatic dicarboxylic acids (preferably unsaturated C4-14 aliphatic dicarboxylic acids, etc.) such as maleic acid, fumaric acid, citraconic acid, mesaconic acid; and derivatives thereof capable of forming esters. In unsaturated polyester resins, the proportion of an aliphatic unsaturated dicarboxylic acid (maleic acid or its acid anhydride, etc.) may be, for example, 10 to 100 mol%, preferably 30 to 100 mol%, and also preferably 50 to 100 mol% (for example, 75 to 100 mol%) with respect to the total dicarboxylic acid component.

[0116] As alicyclic dicarboxylic acids, saturated alicyclic dicarboxylic acids (C3-10 cycloalkane-dicarboxylic acids such as cyclopentane dicarboxylic acid, 1,4-cyclohexane dicarboxylic acid, 1,3-cyclohexane dicarboxylic acid, 1,2-cyclohexane dicarboxylic acid, cycloheptane dicarboxylic acid, etc.), unsaturated alicyclic dicarboxylic acids (C3-10 cycloalkene dicarboxylic acids such as 1,2-cyclohexene dicarboxylic acid, 1,3-cyclohexene dicarboxylic acid, etc.); polycyclic alkanedicarboxylic acids (di or tricyclo C7-10 alkane-dicarboxylic acids such as bornandicarboxylic acid, norbornan dicarboxylic acid, adamantane dicarboxylic acid, etc.), polycyclic alkene dicarboxylic acids (bornendicarboxylic acid, norbornen Examples include dicarboxylic acids, di or tricyclo C7-10 alkene dicarboxylic acids, and their ester-forming derivatives.

[0117] Examples of aromatic dicarboxylic acids include aromatic C8-16 dicarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, naphthalene dicarboxylic acid (2,6-naphthalene dicarboxylic acid, etc.), 4,4'-diphenyl dicarboxylic acid, diphenyl ether-4,4'-dicarboxylic acid, 4,4'-diphenylmethane dicarboxylic acid, 4,4'-diphenyl ketone dicarboxylic acid; and derivatives thereof capable of forming esters.

[0118] As needed, polycarboxylic acids such as trimellitic acid and pyromellitic acid may be used in combination with dicarboxylic acids.

[0119] As the dicarboxylic acid component, at least one type selected from aliphatic dicarboxylic acids and alicyclic dicarboxylic acids is generally preferred, in particular an aliphatic dicarboxylic acid (saturated aliphatic dicarboxylic acid or ester-forming derivatives thereof, in particular saturated C3-14 aliphatic dicarboxylic acids such as adipic acid, suberic acid, sebacic acid, etc.) or alicyclic dicarboxylic acid (C5-10 cycloalkane dicarboxylic acids such as cyclohexanedicarboxylic acid).

[0120] In addition, the polyarylate resin uses a dicarboxylic acid component including at least an aromatic dicarboxylic acid, and the aromatic dicarboxylic acid may be used in combination with other dicarboxylic acids (aliphatic dicarboxylic acids and / or alicyclic dicarboxylic acids). The ratio of the aromatic dicarboxylic acid to the other dicarboxylic acid may be, for example, the former / the latter (molar ratio) = 100 / 0 to 10 / 90, preferably 100 / 0 to 30 / 70, and also preferably 100 / 0 to 50 / 50.

[0121] In polyester resins, the ratio (molar ratio) of the dicarboxylic acid component and the polyol component (diol component, the above-mentioned phenanthrene compound, etc.) can generally be the former / the latter = 1.5 / 1 to 0.7 / 1, preferably 1.2 / 1 to 0.8 / 1 (particularly 1.1 / 1 to 0.9 / 1).

[0122] The weight-average molecular weight Mw (polystyrene equivalent) of the polyester resin is not particularly limited, and, for example, 100 to 50 x 10 4 , preferably 500~30X10 4 (For example, 1000~20X10 4 ), also preferably 3000~30X10 4 It is approximately that amount. In addition, in the case of unsaturated polyester resin, the molecular weight per double bond may be approximately 300 to 1000, preferably 350 to 800, and also preferably 400 to 700. The terminal groups of the polyester resin may be hydroxyl groups or carboxyl groups, and may be protected by a protecting group if necessary.

[0123] Polyester resins can be manufactured by condensing a polyol component (especially a diol component) composed of the above-mentioned phenanthrene-based compound with the above-mentioned dicarboxylic acid component by a conventional method, for example, a direct polymerization method (direct esterification method) or an ester exchange method.

[0125] (2) Polyurethane resin

[0126] The polyol component (diol component) constituting the polyurethane resin containing the above-mentioned phenanthrene-based compound as a polymerization component (monomer component) may be composed of the above-mentioned phenanthrene-based compound alone, or may be used in combination with the above-mentioned phenanthrene-based compound and the diols exemplified in the polyester resin. In addition, a diol component containing the above-mentioned phenanthrene-based compound as a constituent unit, for example, a polyester diol produced by the reaction of a diol component composed of a phenanthrene-based compound having p1=p2=1 in Chemical Formula 1 with a dicarboxylic acid component, or a polyether diol produced by the reaction of the above-mentioned diol component with an alkylene oxide, may also be used as the diol component of the polyurethane resin. The diol component may also be used alone or in combination of two or more types. Furthermore, if necessary, the diol component may be used in combination with a polyol component such as a triol.

[0127] The content of the phenanthrene-based compound in the polyol component (diol component) may be, for example, 10 to 100 mol%, preferably 20 to 80 mol%, and also preferably 30 to 70 mol% with respect to the total polyol component (diol component).

[0128] As diisocyanate compounds constituting polyurethane resins, aromatic diisocyanates [paraphenylene diisocyanate, tolylene diisocyanate (TDI), xylene diisocyanate (XDI), tetramethylxylene diisocyanate (TMXDI),

[0129] Examples of diisocyanate compounds include naphthalene diisocyanate (NDI), bis(isocyanatophenyl)methane (MDI), toluidine diisocyanate (TODI), 1,2-bis(isocyanatophenyl)ethane, 1,3-bis(isocyanatophenyl)propane, 1,4-bis(isocyanatophenyl)butane, polymeric MDI, etc.], alicyclic diisocyanates [cyclohexane 1,4-diisocyanate, isophorone diisocyanate (IPDI), hydrogenated XDI, hydrogenated MDI, etc.], and aliphatic diisocyanates [hexamethylene diisocyanate (HDI), trimethylhexamethylene diisocyanate (TMDI), lysine diisocyanate (LDI), etc.]. These diisocyanate compounds may be used alone or in combination of two or more. These diisocyanate compounds may be used in combination with polyisocyanate compounds (e.g., aliphatic triisocyanates such as 1,6,11-undecane triisocyanate methyl oxtan, 1,3,6-hexamethyrent triisocyanate; triisocyanate compounds such as alicyclic triisocyanates such as bicyclohephtan triisocyanate), monoisocyanate compounds (C1-6 alkyl isocyanates such as methyl isocyanate; C5-6 cycloalkyl isocyanates such as cycloalkyl isocyanate; C6-10 aryl isocyanates such as phenyl isocyanate), etc. The above isocyanate compounds also include derivatives such as polymers or modified forms of the above polyisocyanate compounds.

[0130] Polyurethane resins can be obtained by urethane reaction using a conventional method, for example, a ratio of 0.7 to 2.5 moles, preferably 0.8 to 2.2 moles, and also preferably 0.9 to 2 moles per mole of polyol component (diol component). Additionally, a thermoplastic resin can be obtained by using a diisocyanate component of about 0.7 to 1.1 moles per mole of diol component, and a thermosetting resin having free isocyanate groups at the terminals can be obtained by using an excess amount of the diisocyanate component (for example, about 1.5 to 2.2 moles).

[0132] (3) Polycarbonate resin

[0133] Polycarbonate resins containing the above-mentioned phenanthrene compound as a polymerization component may be polycarbonate resins obtained by, for example, by a reaction (phosgene method) between a polyol component (especially a diol component) composed of at least the above-mentioned phenanthrene compound (generally a compound in which p1=p2=1 in the above-mentioned chemical formula 1) and phosgene, or by a reaction (ester exchange method) between a polyol component (diol component) composed of the above-mentioned phenanthrene compound and a carbonate ester.

[0134] The polyol component (diol component) may be composed solely of the above-mentioned phenanthrene compound, or it may be composed of the above-mentioned phenanthrene compound and other diols (diols exemplified in the above-mentioned polyester resin, particularly aromatic diols or alicyclic diols, etc.). The other diols may be used alone or in combination of two or more types. Among the other diols, aromatic diols such as bisphenols like bisphenol A, AD, F, etc. are particularly preferred. The ratio of the phenanthrene compound having a hydroxyl group to the diols can be selected within the same range as in the case of the above-mentioned polyester resin.

[0135] The molecular weight of the polycarbonate-based resin is not particularly limited, and, for example, a weight-average molecular weight of 1×10 3 ~100X104 (For example, 1x10 4 ~100X10 4 ), preferably 5X10 3 ~50X10 4 (For example, 1x10 4 ~50X10 4 ), also preferably 1X10 4 ~25X10 4 (For example, 1x10 4 ~10X10 4 It could be about that much.

[0137] (4) Epoxy resin

[0138] The diol or polyol component constituting the epoxy resin may be composed solely of the phenanthrene compound, or it may be composed in combination with the phenanthrene compound (generally a compound in which p1=p2=1 in Chemical Formula 1) and other diols (particularly aromatic diols or alicyclic diols, etc.) of the polyester resin. Other diols may be used alone or in combination of two or more types. Among the diols, aromatic diols such as bisphenols like bisphenol A, AD, F, etc. are particularly preferred. The ratio of the phenanthrene compound to the diols can be selected within the same range as in the case of the polyester resin. Additionally, the bisphenolphenanthrene compounds and other diols may be used in combination with polyols (e.g., phenol novolac, etc.) as needed.

[0139] The epoxy resin may be obtained by reacting at least the above-mentioned phenanthrene-based compound with epichlorohydrin. The weight average molecular weight Mw of the epoxy resin may be, for example, about 300 to 30,000, preferably about 400 to 10,000, and also preferably about 500 to 5,000.

[0141] (5) Vinyl ester resin

[0142] Vinyl ester resins can be obtained by conventional methods, for example, by the reaction of the above epoxy resin (an epoxy resin having the above phenanthrene-based compound as a component) with a polymerizable monomer having at least a carboxyl group (an unsaturated monocarboxylic acid). The polymerizable monomer having a carboxyl group may be used in combination with the above polyester resin and a dicarboxylic acid (an aliphatic dicarboxylic acid, alicyclic dicarboxylic acid, or an aromatic dicarboxylic acid (isophthalic acid, terephthalic acid, etc.)) as needed.

[0143] Unsaturated monocarboxylic acids may be used as polymerizable monomers having a carboxyl group. Generally, (meth)acrylic acid may be used as the unsaturated monocarboxylic acid, and cinnamic acid, crotonic acid, sorbic acid, maleic acid monoalkyl esters (monomethyl maleate, etc.) may also be used. These monomers may be used alone or in combination of two or more types.

[0144] The amount of unsaturated monocarboxylic acid used may be about 0.5 to 1.2 moles, preferably 0.7 to 1.1 moles, and also preferably 0.8 to 1 mole per 1 mole of epoxy group of the epoxy resin.

[0145] Vinyl ester resins can also be obtained by the reaction of the above-mentioned phenanthrene compound with glycidyl (meth) acrylate. The amount of glycidyl (meth) acrylate used can be, for example, 1 to 3 moles, preferably 1 to 2 moles, per 1 mole of the above-mentioned phenanthrene compound.

[0147] (6) Acrylic resin

[0148] The monomer of the acrylic resin may be obtained by reacting the above-mentioned phenanthrene compound with a polymerizable monomer having a carboxyl group. As the polymerizable monomer having a carboxyl group, generally unsaturated monocarboxylic acids, particularly (meth)acrylic acid, may be used, and cinnamic acid, crotonic acid, sorbic acid, maleic acid monoalkyl esters (such as monomethyl maleate) may also be used. In addition, reactive derivatives such as acid chlorides and C1-2 alkyl esters may be used instead of unsaturated carboxylic acids. These monomers may be used alone or in combination of two or more types.

[0149] The acrylic resin may be a single or copolymer of a (meth)acrylic monomer having the above-mentioned phenanthrene-based backbone, or a copolymer of the (meth)acrylic monomer having the above-mentioned phenanthrene-based backbone and another copolymer. Examples of copolymer monomers may include carboxyl group-containing monomers such as (meth)acrylic acid, maleic acid, maleic anhydride; (meth)acrylic acid esters [such as (meth)acrylic acid C1-6 alkyl esters such as (meth)acrylic acid methyl]; vinyl cyanides such as (meth)acrylonitrile; aromatic vinyl monomers such as styrene; vinyl carboxylate esters such as vinyl acetate; and α-olefins such as ethylene and propylene.

[0150] These copolymer monomers can be used alone or in combination of two or more.

[0151] In addition, a monomer having multiple (meta)acryloyl groups obtained by the reaction of the above-mentioned phenanthrene-based compound with a polymerizable monomer having a carboxyl group may be used as an acrylic resin (i.e., a thermosetting molded acrylic resin, an oligomer (resin precursor)).

[0152] In addition, the resin component (ii) can be prepared or formulated by mixing the above phenanthrene-based compound with a resin (additives as needed).

[0153] The mixing method is not particularly limited and, for example, a method by melt mixing using a mixing means such as a ribbon blender, tumble mixer, or Hensier-Mickie mixer, or a mixing machine such as an open roller, kneader, van berry mixer, or extruder may be used. These mixing methods may be used individually or in combination of two or more types.

[0154] In addition, the proportion of the phenanthrene-based compound in the resin component (ii) may be, for example, 1 to 80 parts by weight, preferably 5 to 60 parts by weight, and also preferably 20 to 60 parts by weight, with respect to 100 parts by weight of the resin.

[0155] The resin component may include additives. Since the resin component has a phenanthrene-based backbone derived from the phenanthrene-based compound, it can improve the dispersibility of the additives.

[0156] The additives may be in a liquid state at room temperature (e.g., at a temperature of about 15 to 25°C) or in a solid form (e.g., granular solid). The additives include fillers or reinforcing agents, coloring agents (salt pigments), conductive agents, flame retardants, plasticizers, lubricants, stabilizers (antioxidants, UV absorbers, heat stabilizers, etc.), release agents (natural waxes, synthetic waxes, straight-chain fatty acids or their metal salts, acid amides, esters, paraffins, etc.), antistatic agents, dispersants, flow modifiers, leveling agents, defoaming agents, surface modifiers (silane coupling agents or titanium-based coupling agents, etc.), stress-reducing agents (silicone oil, silicone rubber, various plastic powders, various high-performance plastic powders, etc.), heat resistance modifiers (sulfur compounds or polysilanes, etc.), carbon materials, etc. These additives may be used individually or in combination of two or more types.

[0157] Among these additives, fillers, coloring agents (e.g., dye pigments such as black, red, green, and blue pigments), flame retardants, and carbon materials are preferred. Additionally, carbon materials that function as fillers or reinforcing agents, coloring agents, conductive agents, etc., are also preferred.

[0158] Depending on the form (resin pellet, coating composition, etc.), the above resin component can be molded into a molded article by known molding methods, such as injection molding, injection compression molding, extrusion molding, transfer molding, blow molding, pressure molding, or coating methods (spin coating, roll coating, curtain coating, dip coating, casting molding, etc.). In addition, the shape of the molded article may include a two-dimensional structure (film, sheet, coating (or thin film), plate, etc.) and a three-dimensional structure (e.g., tube, rod, tube, leather, hollow product, etc.). Effects of the invention

[0160] The present compound is a phenanthrene-based composite cardo structure and provides a high refractive index monomer that can be used in optical resins requiring a refractive index of 1.7 or higher, and a method for manufacturing the same. By using the phenanthrene-based composite cardo structure of the present compound, the fluidity of the molecular chain is suppressed to the maximum extent, so it can be utilized in the manufacture of resins with excellent thermal stability having a high glass transition temperature. Brief explanation of the drawing

[0162] Figure 1 is of compound 1 of the present invention. 1 This is a diagram showing the results of the H NMR (in CDCl3) analysis. Figure 2 is a figure showing HPLC data of compound 1 of the present invention. FIG. 3 is of compound 2 of the present invention. 1 This is a diagram showing the results of the H NMR (in CDCl3) analysis. Figure 4 is a figure showing HPLC data of compound 2 of the present invention. Specific details for implementing the invention

[0163] The present invention will be described in more detail below through examples. These examples are intended solely to explain the invention more specifically, and it will be obvious to those skilled in the art that the scope of the invention is not limited by these examples according to the gist of the invention.

[0165] Examples

[0167] Throughout this specification, "%" used to indicate the concentration of a particular substance is (weight / weight) % for solid / solid, (weight / volume) % for solid / liquid, and (volume / volume) % for liquid / liquid, unless otherwise noted.

[0169] Example 1: Synthesis of pyrene-4,5-dione

[0170] A magnetic bar was placed in a two-necked flask equipped with a thermometer and a stirrer, and the mixture was flame-dried. 4.09 g (20 mmol) of pyrene and 0.414 g (2 mmol) of RuCl were added, and a nitrogen atmosphere was maintained. 100 mL of THF was added and stirred. 18.822 g (88 mmol) of NaIO4 was added to 150 mL of H2O in an Erlenmeyer flask and mixed. The aqueous solution of NaIO4 was slowly added to the stirring two-necked flask. Next, 100 mL of DCM (dichloromethane) was added, and the mixture was stirred at room temperature for 5 hours. After stirring, the resulting solids were filtered. The filtrate was extracted using dichloromethane and H2O. The organic layer was separated, MgSO4 was added, and the mixture was filtered. After reducing the pressure of the filtrate, recrystallization with dichloromethane and hexane was carried out to obtain pyrene-4,5-dione (3.03 g, yield 65.0%).

[0172] Example 2: Synthesis of cyclopentaphenanthrene-4-one

[0173] A reflux tube was installed in a two-necked flask equipped with a thermometer and a stirrer, and 2.34 g (10 mmol) of pyrene-4,5-dione prepared in Example 1 was added, and an oxygen atmosphere was maintained. An aqueous NaOH solution was prepared by adding 250 mL of H2O and 8.0 g (20 mmol) of NaOH to the flask. The aqueous NaOH solution was slowly added to the two-necked flask, and the mixture was stirred at 90°C for 2 days. Extraction was performed using DCM and H2O. The organic layer was separated, MgSO4 was added, and the mixture was filtered. The filtrate was subjected to reduced pressure, and recrystallization was carried out with dichloromethane and hexane to obtain cyclopentaphenanthrene-4-one. (1.12 g, yield 55.0%) was obtained.

[0175] Example 3: 2,2'-(((4 H Synthesis of -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol (Compound 1)

[0176] A magnetic bar was placed in a two-necked flask equipped with a thermometer and a stirrer, and the mixture was flame-dried. 2.04 g (10 mmol) of cyclopentaphenanthrene-4-one prepared in Example 2 was added, and a nitrogen atmosphere was maintained. 5.02 mL (40 mmol) of phenoxyethanol and 100 µL (1.0 mmol) of mercaptopropionic acid were added, and the mixture was stirred at 50°C for 10 minutes. 20 µL (30 mmol) of H2SO4 was added dropwise. The mixture was stirred at the same temperature for 5 hours. Extraction was performed using DCM and H2O. The organic layer was separated, MgSO4 was added, and the mixture was filtered. The filtrate was subjected to reduced pressure, and recrystallization was carried out with ethyl acetate and hexane to obtain a white solid compound 1 (3.25 g, yield 70.0%).

[0177] of the above-synthesized compound 1 1The results of the H NMR (in CDCL3) analysis are shown in Figure 1.

[0178] In addition, the HPLC purity analysis results of the synthesized compound 1 are shown in Figure 2.

[0179] As shown in FIGS. 1 and 2, according to Embodiment 3 of the present invention, 2,2'-(((4 H It was confirmed that -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol can be synthesized with high purity.

[0181] Example 4: Synthesis of 4,4'-(4H-cyclopentaphenanthrene-4,4-diyl)diphenol (Compound 2)

[0182] A magnetic bar was placed in a two-necked flask equipped with a thermometer and a stirrer, and the mixture was flame-dried. 1.4 g (3 mmol) of 2,2'-(((4H-cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol and 1.7 g (30 mmol) of KOH were added, and a nitrogen atmosphere was maintained. 20 mL of DMSO was added, and the mixture was stirred at 100°C for 3 hours. After stirring, 1 M HCl was added until the pH reached 2. Extraction was performed using ethyl acetate, brine, and water. The organic layer was separated, MgSO4 was added, and the mixture was filtered. The filtrate was subjected to reduced pressure, and recrystallization was carried out with ethyl acetate and hexane to obtain a white solid compound 2 (0.99 g, yield 88.0%).

[0183] of the above-mentioned synthesized compound 2 1 The results of the H NMR (in CDCL3) analysis are shown in Figure 1.

[0184] The HPLC purity analysis results of the synthesized compound 2 above are shown in Figure 2.

[0185] In addition, the HPLC purity analysis results of the synthesized compound 2 are shown in Figure 2.

[0186] As shown in Figures 3 and 4, it was confirmed that 4,4'-(4H-cyclopentaphenanthrene-4.4-diyl)diphenol can be synthesized with high purity in Example 4 of the present invention.

Claims

Claim 1 Compound having the chemical structure of Chemical Formula 1 below: [Chemical Formula 1] ,where the above R 3a and R 3b is independently a C2 to C4 alkylene group; n1 and n2 are independently 0 or 1; and p1 and p2 are 1. Claim 2 delete Claim 3 delete Claim 4 delete Claim 5 In claim 1, a compound having the chemical structure of the following chemical formula 2-1 or 2-2: [Chemical formula 2-1] ; and [Chemical Formula 2-2] . Claim 6 A method for preparing a phenanthrene-based compound comprising the following steps: (a) oxidizing pyrene to synthesize pyrene-4,5-dione; (b) synthesizing cyclopentaphenanthrene-4-one from pyrene-4,5-dione; and (c) synthesizing 2,2'-(((4 H Step for synthesizing -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol. Claim 7 In paragraph 6, (d) 2,2'-(((4 H A method for preparing a phenanthrene-based compound, comprising the step of synthesizing 4,4'-(4H-cyclopentaphenanthrene-4.4-diyl)diphenol from -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol. Claim 8 A method for preparing a phenanthrene-based compound according to claim 6, wherein step (a) is a step of synthesizing pyrene-4,5-dione by oxidizing pyrene by adding sodium periodate according to the following reaction scheme 1-1: [Reaction Scheme 1-1] . Claim 9 Method for preparing a phenanthrene-based compound according to claim 6, wherein step (b) is a step of synthesizing cyclopentaphenanthrene-4-one by adding sodium hydroxide to pyrene-4,5-dione according to the following reaction scheme 1-2: [Reaction Scheme 1-2] . Claim 10 In claim 6, the above step (c) is formed by adding phenoxyethanol to cyclopentaphenanthrene-4-one according to the following reaction scheme 1-3 to obtain 2,2'-(((4 H Method for preparing a phenanthrene-based compound, which is the step of synthesizing -cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene))bis(oxy))diethanol: [Reaction Scheme 1-3] . Claim 11 In claim 7, the above step (d) is 2,2'-(((4 according to the following reaction scheme 1-4). H Method for preparing a phenanthrene-based compound, the step of synthesizing 4,4'-(4H-cyclopentaphenanthrene-4,4-diyl)bis(4,1-phenylene)bis(oxy))diethanol by adding potassium hydroxide: [Reaction Scheme 1-4] .

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