WO2022097396A1 - Procédé de production d'un composé ayant un squelette fluorène, et composé ayant un squelette fluorène - Google Patents

Procédé de production d'un composé ayant un squelette fluorène, et composé ayant un squelette fluorène Download PDF

Info

Publication number
WO2022097396A1
WO2022097396A1 PCT/JP2021/036373 JP2021036373W WO2022097396A1 WO 2022097396 A1 WO2022097396 A1 WO 2022097396A1 JP 2021036373 W JP2021036373 W JP 2021036373W WO 2022097396 A1 WO2022097396 A1 WO 2022097396A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
fluorene skeleton
formula
acid
reaction
Prior art date
Application number
PCT/JP2021/036373
Other languages
English (en)
Japanese (ja)
Inventor
和徳 布目
Original Assignee
帝人株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 帝人株式会社 filed Critical 帝人株式会社
Priority to CN202180072716.0A priority Critical patent/CN116438153A/zh
Priority to JP2022560676A priority patent/JPWO2022097396A1/ja
Publication of WO2022097396A1 publication Critical patent/WO2022097396A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/19—Hydroxy compounds containing aromatic rings
    • C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
    • C08G63/197—Hydroxy compounds containing aromatic rings containing two or more aromatic rings containing condensed aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

Definitions

  • the present invention relates to a method for producing a compound having a fluorene skeleton and a compound having a fluorene skeleton.
  • Patent Document 2 9,9-bis [6- (2-hydroxyethoxy) -2-naphthyl] fluorene
  • Patent Document 3 9,9-bis [4- (2-hydroxyethoxy) phenyl] -2,7-diphenyl
  • fluorene 9,9-bis [6- (2-hydroxyethoxy) -2-naphthyl] fluorene
  • Patent Document 3 9,9-bis [4- (2-hydroxyethoxy) phenyl] -2,7-diphenyl
  • fluorene Patent Document 3
  • Aspect 1 The compound represented by the following formula (1) and the boronic acid represented by the following formula (2) or (3) are reacted in a reaction solvent in the presence of a base and a palladium-based catalyst, and the following formula (4) is used.
  • a method for producing a compound having a fluorene skeleton which comprises using at least dimethylformamide as a reaction solvent in the step of obtaining the compound having the fluorene skeleton represented.
  • X 1 and X 2 each independently indicate a halogen atom.
  • Z indicates an aromatic group which may independently have a substituent having 6 to 20 carbon atoms.
  • ⁇ Aspect 2 The method for producing a compound having a fluorene skeleton according to the first aspect, wherein at least dimethylformamide and an aromatic hydrocarbon solvent are used as the reaction solvent.
  • ⁇ Aspect 3 A compound having a fluorene skeleton represented by the following formula (4) in which the Hazen unit color number (APHA) of a 5% by weight solution dissolved in dimethylformamide is 50 or less.
  • APHA Hazen unit color number
  • ⁇ Aspect 4 The method for using a compound having a fluorene skeleton according to Aspect 3 as a raw material for a thermoplastic resin.
  • ⁇ Aspect 5 A thermoplastic resin obtained by polymerizing the compound having the fluorene skeleton according to the third aspect.
  • a compound having a fluorene skeleton having an excellent hue can be obtained.
  • the yield and productivity of producing a compound having a fluorene skeleton can be improved.
  • a method for producing a compound having a fluorene skeleton which comprises using at least dimethylformamide as a reaction solvent in the step of obtaining a compound having a fluorene skeleton represented by the following formula (4).
  • X 1 and X 2 each independently indicate a halogen atom.
  • Z indicates an aromatic group which may independently have a substituent having 6 to 20 carbon atoms.
  • Ar 1 and Ar 2 each independently indicate an aromatic group which may have a substituent having 6 to 20 carbon atoms.
  • at least dimethylformamide is used as the reaction solvent.
  • Dimethylformamide can achieve both the affinity of the compound used as a base with an aqueous solution and the solubility of the compound represented by the above formula (4).
  • the reaction temperature can be increased, the reaction rate can be improved, and the amount of palladium catalyst can be reduced.
  • an aromatic hydrocarbon solvent such as toluene in combination with dimethylformamide as the reaction solvent.
  • aromatic hydrocarbon solvent used in the production method of the present invention include benzene, toluene, xylene, ethylbenzene, mesitylene, isopropylbenzene and the like, and toluene is preferable.
  • the amount of the reaction solvent used in the production method of the present invention is preferably 0.1 to 100 parts by weight, more preferably 1 to 50 parts by weight, based on 1 part by weight of the compound represented by the formula (1). , More preferably 2 to 10 parts by weight.
  • dimethylformamide is preferably used in an amount of 5% by weight or more, more preferably 10% by weight or more, further preferably 20% by weight or more, and particularly preferably 30% by weight or more.
  • the ratio of the aromatic hydrocarbon solvent used is preferably 0.1 to 10 parts by weight, more preferably 0 with respect to 1 part by weight of dimethylformamide. .5 to 5 parts by weight, more preferably 1 to 3 parts by weight.
  • the total amount of dimethylformamide and the aromatic hydrocarbon solvent in the reaction solvent is more preferably 70% by weight or more, more preferably 80% by weight. It is more preferable to use the above, and it is particularly preferable to use 90% by weight or more.
  • X 1 and X 2 each independently represent a halogen atom, preferably a chlorine atom or a bromine atom, and more preferably a bromine atom.
  • Z is an aromatic group which may independently have a substituent having 6 to 20 carbon atoms.
  • Specific examples of the boronic acids represented by the above formula (2) or (3) are 2-anthracemboronic acid, 9-anthracemboronic acid, benzylboronic acid, 2-biphenylboronic acid, 3-biphenylboronic acid, 4-.
  • Biphenylboronic acid 2,3-dimethylphenylboronic acid, 2,4-dimethylphenylboronic acid, 2,5-dimethylphenylboronic acid, 2,6-dimethylphenylboronic acid, 3,4-dimethylphenylboronic acid, 3 , 5-Dimethylphenylboronic acid, 2-ethoxyphenylboronic acid, 3-ethoxyphenylboronic acid, 4-ethoxyphenylboronic acid, 6-methoxy-2-naphthalenboronic acid, 2-methylphenylboronic acid, 3-methylphenyl Boronic acid, 4-methylphenylboronic acid, 1-naphthalenboronic acid, 2-naphthalenboronic acid, 9-phenanthrenboronic acid, 10-phenyl-9-anthracemboronic acid, phenylboronic acid, phenylethaneboronic acid, 4-phenyl (Naphthalen-1-yl) Boronic acid, 3-propoxyphenylboronic acid, 3-iso-propoxyphen
  • phenylboronic acid, 1-naphthalenboronic acid, 2-naphthalenboronic acid or an anhydride thereof is preferable, and phenylboronic acid or an anhydride thereof is particularly preferable.
  • Ar 1 and Ar 2 correspond to Z of the compound represented by the above formula (2) or (3), and the preferred embodiment of Ar 1 and Ar 2 is preferably Z. It is the same as the aspect.
  • the ratio of the compound represented by the formula (2) used in the production method of the present invention is preferably 2 to 5 mol, more preferably 2 mol, with respect to 1 mol of the compound represented by the formula (1). It is 0.05 to 3.0 mol, more preferably 2.1 to 2.5 mol.
  • the ratio of the compound represented by the formula (3) to be used is preferably 0.7 to 5 mol, more preferably 0.8 to 3 mol, based on 1 mol of the compound represented by the formula (1). , More preferably 1-2 mol.
  • Examples of the base used in the production method of the present invention include hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate (Na 2 CO 3 ), potassium carbonate (K 2 CO 3 ), and cesium carbonate (Cs 2 ).
  • the amount of the base used in the production method of the present invention is preferably 1 to 30 mol, more preferably 2 to 10 mol, still more preferably 2 to 10 mol, based on 1 mol of the compound represented by the formula (1). Is 2-5 mol.
  • the base is usually preferably added as an aqueous solution.
  • the palladium compound used in Suzuki coupling is preferable, and for example, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride, palladium acetate, tris ( Divendilideneacetone) dipalladium, bis (dibenzilidenacetone) palladium, bis [4- (N, N-dimethylamino) phenyl] di-tert-butylphosphine palladium dichloride, bis (di-tert-butylprenylphosphine) palladium dichloride , Bis (di-tert-crotylphosphine) palladium dichloride, palladium-based catalyst represented by Pd / SiO 2 and the like.
  • tetrakis (triphenylphosphine) palladium is preferable.
  • Such a palladium tetrakis (triphenylphosphin
  • the amount of the palladium-based catalyst used in the production method of the present invention is preferably 0.1 to 10 mmol in terms of palladium metal atom with respect to 1 mol of the compound represented by the above formula (1), and more preferably. It is 0.5 to 5 mmol.
  • the obtained reaction mixture is subjected to separation means such as washing, filtration, concentration, extraction, crystallization, recrystallization, reprecipitation, activation charcoal treatment or similar metal removal treatment, and column chromatography.
  • separation means such as washing, filtration, concentration, extraction, crystallization, recrystallization, reprecipitation, activation charcoal treatment or similar metal removal treatment, and column chromatography.
  • it may be separated and purified by a separation means combining these.
  • a base since a base is used in the reaction, it is preferable to perform the neutralization treatment thereof. Further, it is preferable to carry out a treatment for removing the salt produced as a by-product in the reaction.
  • distilled water is added to the reaction mixture and stirring, liquid separation, and water layer removal are repeated (sometimes abbreviated as liquid separation water washing method), or distilled water is added to the crystals to perform repulp washing. There is a method of repeating filtration and the like, and the liquid separation water washing method is industrially preferable.
  • the palladium compound is used in the present invention, it is preferable to perform the removal treatment thereof.
  • the palladium removal treatment it is preferable to add activated carbon or metal scavenger to the reaction mixture, stir, and then filter out the activated carbon or metal scavenger.
  • the present invention it is preferable to perform recrystallization or crystallization in order to remove impurities such as reaction by-products and unreacted raw materials.
  • an aromatic hydrocarbon solvent such as toluene is preferable as the recrystallization solvent, and toluene is particularly preferable.
  • crystallization it is preferable to dissolve a compound having a fluorene skeleton in an aromatic hydrocarbon solvent such as toluene, and then use an alcohol solvent such as methanol as a poor solvent.
  • crystallization is preferable because a compound having a fluorenone skeleton having a better hue can be obtained.
  • the compound produced by the production method of the present invention is a compound having a fluorene skeleton represented by the following formula (4).
  • Ar 1 and Ar 2 each independently indicate an aromatic group which may have a substituent having 6 to 20 carbon atoms.
  • Ar 1 and Ar 2 each independently represent an aromatic group which may have a substituent having 6 to 20 carbon atoms, and a phenyl group and a naphthyl group are preferable, and a phenyl group is more preferable. preferable. That is, 9,9-bis (4- (2-hydroxyethoxy) phenyl) -2,7-diphenylfluorene represented by the following formula (5) is more preferable.
  • the compound having a fluorene skeleton of the present invention preferably has an APHA of 50 or less, more preferably 40 or less, and even more preferably 30 or less in a 5% by weight solution dissolved in dimethylformamide.
  • APHA is 50 or less, the hue of the resin made of the raw material represented by the above formula (4) and the hue of the optical member using the same are good, which is preferable.
  • the compound having a fluorene skeleton of the present invention preferably has a sulfur element content of 200 ppm or less, more preferably 100 ppm or less, further preferably 50 ppm or less, and particularly preferably 30 ppm or less.
  • the content of the sulfur element is 200 ppm or less, the hue of the resin made of the raw material represented by the above formula (4) and the hue of the optical member using the same are good, which is preferable.
  • the compound having a fluorene skeleton of the present invention preferably has a bromine element content of 150 ppm or less, more preferably 50 ppm or less, and even more preferably 20 ppm or less.
  • the content of the bromine element is 150 ppm or less, the hue of the resin made of the raw material represented by the above formula (4) and the hue of the optical member using the same are good, which is preferable.
  • the compound having a fluorene skeleton of the present invention preferably has a diphenylfluorenone content of 0.2% or less, more preferably 0.1% or less, and further preferably 0.05% or less.
  • the content of diphenylfluorene is 0.2% or less, the hue of the resin made of the raw material represented by the above formula (4) and the hue of the optical member using the same are good, which is preferable.
  • the compound having a fluorene skeleton of the present invention preferably combines a diphenylfluorene skeleton and a dinaphthylfluorene skeleton with an arene ring, it not only has high refractive index and heat resistance, but also reduces birefringence when made into a polymer. Can be done. Since the compound having a fluorene skeleton of the present invention has a diphenylfluorene skeleton and a dinaphthylfluorene skeleton, the birefringence is small even though the refractive index is high.
  • the compound having a fluorene skeleton of the present invention can be used as a raw material (monomer) for various resins.
  • resins eg, polyester resin, polycarbonate resin, polyester carbonate resin, polyurethane resin, etc.
  • thermosetting resins eg, epoxy resin, phenol resin, thermosetting polyurethane resin, (meth) acrylate ((meth)). It can be used as a polyol component of acrylic acid ester) etc.
  • the obtained resin has a high refractive index and a low index, probably because the naphthalene ring is substituted at the 9-position of the fluorene skeleton and the fluorene skeleton has a diaryl group. It has the advantage of being compatible with birefringence at a high level. Further, since the compound having a fluorene skeleton of the present invention is excellent in hue and therefore the hue of the obtained resin is also excellent, it is suitably used for an optical member such as an optical lens.
  • the hue of the resin is preferably 5.0 or less, more preferably 4.5 or less, and even more preferably 4.0 or less in terms of the b * value of the pellets.
  • nD Refractive index at wavelength 589 nm
  • nC Refractive index at wavelength 656 nm
  • nF means the refractive index at a wavelength of 486 nm.
  • DBFN 2,7-dibromofluorenone
  • 2-naphthol 28 in a flask equipped with a stirrer, a cooler, a water separator, and a thermometer.
  • the progress of the reaction was confirmed by HPLC, and the residual amount of 9,9'-bis (6-hydroxy-2-naphthyl) -2,7-dibromofluorene was confirmed to be 0.0%, and the reaction was terminated. I let you. After completion of the reaction, water and a 25 wt% sodium hydroxide aqueous solution were added to the obtained reaction solution, and the mixture was stirred at 85 ° C. for 1.5 hours, and then the aqueous layer was separated. The obtained reaction solution was concentrated, toluene was added to dissolve it, and then washing with warm water was performed 5 times.
  • BNDB 9,9-bis [6- (2-hydroxyethoxy) -2-naphthyl] -2,7-dibromofluorene
  • Tetrahydrofuran was added to the washed toluene layer and treated with activated carbon, then tetrahydrofuran was distilled off, recrystallization was performed with toluene, and the obtained crystals were heated and dried under reduced pressure overnight to make 9,9-bis [6-( 2-Hydroxyethoxy) -2-naphthyl] -2,7-diphenylfluorene (hereinafter, may be abbreviated as BNDP) was obtained as white crystals in a yield of 80% and a purity of 98.0%.
  • BNDP 9,9-bis [6-( 2-Hydroxyethoxy) -2-naphthyl] -2,7-diphenylfluorene
  • APHA was 50, S was 25 ppm, Br was 1 ppm, Pd was 1 ppm, and diphenylfluorenone (hereinafter, may be abbreviated as DPFN) was 0.0% as measured by HPLC.
  • DPFN diphenylfluorenone
  • Tetrahydrofuran was added to the washed toluene layer and treated with activated charcoal, then tetrahydrofuran was distilled off, methanol and distilled water were added as a poor solvent to the toluene solution for recrystallization, and the obtained crystals were heated and dried under reduced pressure overnight.
  • White crystals of BNDP were obtained with a yield of 78% and a purity of 99.7%.
  • APHA was 20
  • S was 9 ppm
  • Br was 0 ppm
  • Pd was 1 ppm
  • DPFN was 0.0% as measured by HPLC.
  • Example 3 25.91 parts by mass of 9,9-bis [6- (2-hydroxyethoxy) -2-naphthyl] -2,7-diphenylfluorene synthesized in Example 1, 9,9-bis [4- (2- (2-) Hydroxyethoxy) phenyl] Fluolene was placed in a reaction vessel equipped with a stirrer and a distiller in 16.44 parts by mass, diphenyl carbonate 16.23 parts by mass, and sodium hydrogen carbonate 3.15 ⁇ 10 -3 parts by mass, and replaced with nitrogen. After that, the jacket was heated to 200 ° C. to melt the raw materials.
  • the pressure was reduced to 20 kPa over 5 minutes, and at the same time, the temperature of the jacket was raised to 260 ° C. at a rate of 60 ° C./hr, and a transesterification reaction was carried out. Then, while keeping the jacket at 260 ° C., the pressure was reduced to 0.13 kPa over 50 minutes, and the polymerization reaction was carried out under the conditions of 260 ° C. and 0.13 kPa or less until a predetermined torque was reached. After completion of the reaction, the produced resin was extracted while pelletizing to obtain pellets of polycarbonate resin.
  • the obtained polycarbonate resin was analyzed by 1 H NMR, and the 9,9-bis [6- (2-hydroxyethoxy) -2-naphthyl] -2,7-diphenylfluorene component was 50 mol with respect to all the monomer components. % Confirmed that it has been introduced.
  • the obtained polycarbonate resin had a refractive index of 1.682, an Abbe number of 17.1, a Tg of 177 ° C., and a pellet b * value of 4.0.
  • the pressure was reduced to 20 kPa over 5 minutes, and at the same time, the temperature of the jacket was raised to 260 ° C. at a rate of 60 ° C./hr, and a transesterification reaction was carried out. Then, while keeping the jacket at 260 ° C., the pressure was reduced to 0.13 kPa over 50 minutes, and the polymerization reaction was carried out under the conditions of 260 ° C. and 0.13 kPa or less until a predetermined torque was reached. After completion of the reaction, the produced resin was extracted while pelletizing to obtain pellets of polycarbonate resin.
  • the obtained polycarbonate resin was analyzed by 1 H NMR, and the 9,9-bis [6- (2-hydroxyethoxy) -2-naphthyl] -2,7-diphenylfluorene component was 50 mol with respect to all the monomer components. % Confirmed that it has been introduced.
  • the obtained polycarbonate resin had a refractive index of 1.682, an Abbe number of 17.1, a Tg of 177 ° C., and a pellet b * value of 5.9.
  • novel fluorene derivative obtained by the production method of the present invention is suitable as a monomer for forming a resin constituting an optical member represented by an optical lens or an optical film.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne : un procédé de production d'un composé ayant un squelette de fluorène, le procédé étant caractérisé en ce qu'il comprend une étape d'obtention d'un composé ayant un squelette de fluorène et représenté par la formule (4) par réaction d'un composé représenté par la formule (1) avec des acides boroniques représentés par la formule (2) ou (3) dans un solvant de réaction en présence d'une base et d'un catalyseur à base de palladium, au moins du diméthylformamide étant utilisé en tant que solvant de réaction ; un composé qui a un squelette de fluorène et est représenté par la formule (4), et dans laquelle l'indice de couleur de l'unité Hazen (APHA) d'une solution à 5 % en poids dissoute dans du diméthylformamide ne dépasse pas 50 ; un composé ayant une teinte améliorée et un nouveau squelette de fluorène ; et son procédé de production. (Dans la formule, X1 et X2 représentent chacun indépendamment un atome d'halogène.) (Dans la formule, les Z représentent chacun indépendamment un groupe aromatique en C6-C20 qui peut avoir un substituant.) (Dans la formule, Ar1 et Ar2 représentent chacun indépendamment un groupe aromatique en C6-C20 qui peut avoir un substituant.)
PCT/JP2021/036373 2020-11-04 2021-10-01 Procédé de production d'un composé ayant un squelette fluorène, et composé ayant un squelette fluorène WO2022097396A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202180072716.0A CN116438153A (zh) 2020-11-04 2021-10-01 具有芴骨架的化合物的制造方法和具有芴骨架的化合物
JP2022560676A JPWO2022097396A1 (fr) 2020-11-04 2021-10-01

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020184218 2020-11-04
JP2020-184218 2020-11-04

Publications (1)

Publication Number Publication Date
WO2022097396A1 true WO2022097396A1 (fr) 2022-05-12

Family

ID=81457823

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2021/036373 WO2022097396A1 (fr) 2020-11-04 2021-10-01 Procédé de production d'un composé ayant un squelette fluorène, et composé ayant un squelette fluorène

Country Status (3)

Country Link
JP (1) JPWO2022097396A1 (fr)
CN (1) CN116438153A (fr)
WO (1) WO2022097396A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019151264A1 (fr) * 2018-01-31 2019-08-08 帝人株式会社 Composé ayant un squelette fluorène et procédé de fabrication associé
JP2020083813A (ja) * 2018-11-26 2020-06-04 帝人株式会社 フルオレン骨格を有する化合物の製造方法および不純物の少ないフルオレン骨格を有する化合物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019151264A1 (fr) * 2018-01-31 2019-08-08 帝人株式会社 Composé ayant un squelette fluorène et procédé de fabrication associé
JP2020083813A (ja) * 2018-11-26 2020-06-04 帝人株式会社 フルオレン骨格を有する化合物の製造方法および不純物の少ないフルオレン骨格を有する化合物

Also Published As

Publication number Publication date
JPWO2022097396A1 (fr) 2022-05-12
CN116438153A (zh) 2023-07-14

Similar Documents

Publication Publication Date Title
JP7012751B2 (ja) フルオレン骨格を有する化合物およびその製造方法
JP7227345B2 (ja) 光学レンズ
JP7231389B2 (ja) フルオレン骨格を有する化合物の製造方法および不純物の少ないフルオレン骨格を有する化合物
WO2020226126A1 (fr) Composé ayant un squelette fluorène et son procédé de fabrication
WO2022097396A1 (fr) Procédé de production d'un composé ayant un squelette fluorène, et composé ayant un squelette fluorène
JP2022121884A (ja) ジヒドロキシ化合物およびその製造方法
JP2021031401A (ja) フルオレン骨格を有する化合物およびその製造方法
CN113474321B (zh) 具有联萘骨架的化合物和具有联萘骨架的化合物的制造方法
WO2007007332A1 (fr) Copolymeres a base de tribromoneopentyl (meth)acrylate et lentilles produites a partir desdits copolymeres
TWI707839B (zh) 具有茀骨架之醇類的製造方法
WO2022038997A1 (fr) Dérivé du fluorène et son procédé de production
TW201808870A (zh) 具有茀骨架之醇化合物的製造方法
TW202024008A (zh) 具有茀骨架之化合物的結晶及其製造方法
KR101448541B1 (ko) 고굴절 (메타)아크릴레이트 유도체 및 그의 제조방법
JP7303055B2 (ja) フルオレン骨格を有する化合物およびその製造方法
JP2636042B2 (ja) ４，４▲′′′▼―ジヒドロキシクォーターフェニル誘導体およびその製造方法
JP2021014426A (ja) ビナフタレン骨格を有する化合物
JP6994299B2 (ja) フルオレン骨格を有するジヒドロキシ化合物の精製方法
JP2023101603A (ja) フルオレン骨格を有する化合物およびその製造方法
CN106458817A (zh) 新型的双(羟基烷氧基苯基)二苯甲烷类
TWI596105B (zh) Phosphorus-series (meth) acrylate compound and its manufacturing method
TW202104147A (zh) 具有茀骨架之化合物及其之製造方法
JP2007291041A (ja) アダマンチル（メタ）アクリレート類化合物の製造方法
JP7491980B2 (ja) フルオレン骨格を有する化合物の製造方法および不純物の少ないフルオレン骨格を有する化合物
JPH11228577A (ja) 高純度スピログリコールの製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21888949

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2022560676

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21888949

Country of ref document: EP

Kind code of ref document: A1