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WO2020045200A1 - Composé d'alkylène, composé de quinophtalone et mélange de quinophtalone - Google Patents

Composé d'alkylène, composé de quinophtalone et mélange de quinophtalone Download PDF

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Publication number
WO2020045200A1
WO2020045200A1 PCT/JP2019/032705 JP2019032705W WO2020045200A1 WO 2020045200 A1 WO2020045200 A1 WO 2020045200A1 JP 2019032705 W JP2019032705 W JP 2019032705W WO 2020045200 A1 WO2020045200 A1 WO 2020045200A1
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Prior art keywords
formula
quinophthalone
compound
alkylene
halogen atom
Prior art date
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Ceased
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PCT/JP2019/032705
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English (en)
Japanese (ja)
Inventor
龍矢 重廣
竜史 山崎
近藤　仁
安井　健悟
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DIC Corp
Original Assignee
DIC Corp
Dainippon Ink and Chemicals Co Ltd
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Priority to JP2019569845A priority Critical patent/JP6677365B1/ja
Priority to CN201980055609.XA priority patent/CN112638882A/zh
Publication of WO2020045200A1 publication Critical patent/WO2020045200A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B25/00—Quinophthalones

Definitions

  • the present invention relates to an alkylene compound, a method for producing a quinophthalone compound, a quinophthalone compound, and a quinophthalone mixture.
  • coloring compositions are used in various fields. Specific uses of the coloring compositions include printing inks, paints, coloring agents for resins, coloring agents for fibers, coloring materials for IT information recording (color filters). , Toner, and inkjet). Dyes used in the coloring composition are required to have color characteristics (coloring power, sharpness), resistance (weather resistance, light resistance, heat resistance, solvent resistance) and the like. Dyes are mainly classified into pigments and dyes, but pigments are different from dyes that develop color in a molecular state, and develop color in a particle state (aggregates of primary particles). For this reason, pigments are generally superior to dyes in terms of resistance, but are inferior in coloring power and chroma (clearness).
  • Patent Document 1 discloses a coloring composition containing a predetermined quinophthalone compound.
  • the conventional coloring composition containing a quinophthalone compound is not always excellent in coloring power, and is not always sufficient for use in applications requiring high color reproducibility such as color filters. Since a quinophthalone compound is obtained by a condensation reaction between a quinaldine (2-methylquinoline) compound and phthalic anhydride, it is important to develop a novel quinalazine compound in order to find a quinophthalone compound having excellent coloring power. Become.
  • One aspect of the present invention is an alkylene compound represented by the formula (1).
  • X 1 and X 2 each independently represent a hydrogen atom or a halogen atom, and Z represents an alkylene group having 1 to 3 carbon atoms.
  • Z may be a methylene group.
  • Another aspect of the present invention relates to a first quinophthalone compound represented by the formula (3) obtained by condensing an alkylene compound represented by the formula (1) with an acid anhydride represented by the formula (2). And a step of obtaining at least one selected from the group consisting of a second quinophthalone compound represented by formula (4) and a second quinophthalone compound.
  • X 1 and X 2 each independently represent a hydrogen atom or a halogen atom
  • Z represents an alkylene group having 1 to 3 carbon atoms.
  • X 3 , X 4 , X 5 and X 6 each independently represent a hydrogen atom or a halogen atom.
  • X 1 , X 2 , X 3 , X 4 , X 5 and X 6 each independently represent a hydrogen atom or a halogen atom, and Z represents an alkylene group having 1 to 3 carbon atoms.
  • X 1 , X 2 , X 3 , X 4 , X 5 and X 6 each independently represent a hydrogen atom or a halogen atom, and Z represents an alkylene group having 1 to 3 carbon atoms.
  • the step may be a step of condensing the alkylene compound and the acid anhydride in the presence of an acid catalyst.
  • Still another aspect of the present invention is a quinophthalone compound represented by the formula (4).
  • Still another aspect of the present invention is a quinophthalone mixture containing a first quinophthalone compound represented by the formula (3) and a second quinophthalone compound represented by the formula (4).
  • a novel quinaldine compound for producing a quinophthalone compound having excellent coloring power as a pigment Further, according to the present invention, a method for producing a quinophthalone compound having excellent coloring power as a pigment is provided. Further, according to the present invention, a novel quinophthalone compound and a quinophthalone mixture containing the quinophthalone compound are provided.
  • alkylene compound The alkylene compound according to the present embodiment is a compound represented by the following formula (1).
  • X 1 and X 2 each independently represent a hydrogen atom or a halogen atom
  • Z represents an alkylene group having 1 to 3 carbon atoms.
  • the halogen atom in the formula (1) may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, and more preferably a chlorine atom.
  • alkylene group having 1 to 3 carbon atoms in the formula (1) include, for example, a methylene group, an ethylene group (1,1-ethanediyl group or 1,2-ethanediyl group), a propylene group (1,1-ethanediyl group).
  • a methylene group a 1,1-ethanediyl group, a 1,1-propanediyl group, , 2-propanediyl group is more preferred, and methylene group is even more preferred.
  • the alkylene compound according to the present embodiment can be obtained, for example, by a method including the following Step I, Step II, and Step III.
  • the formula (1-i) and the formula (1-ii) a plurality of X 1 and between the plurality of X 2 each other in may be the same or different.
  • examples of the strong acid include hydrochloric acid, sulfuric acid, nitric acid and the like.
  • examples of the oxidizing agent include sodium iodide, p-chloranil, nitrobenzene, and the like.
  • the reaction temperature may be from 80 ° C to 100 ° C, preferably from 90 ° C to 100 ° C, and the reaction time may be from 1 hour to 6 hours, preferably from 3 hours to 6 hours.
  • the compound of the formula (1-ii) can be obtained by reacting the obtained compound of the formula (1-i) with nitric acid or fuming nitric acid in the presence of concentrated sulfuric acid.
  • the reaction temperature may be -20 ° C to 70 ° C, preferably 0 ° C to 50 ° C, and the reaction time may be 1 hour to 4 hours, preferably 1 hour to 3 hours.
  • the alkylene compound represented by the above formula (1) is converted by converting the nitro group (—NO 2 ) into an amino group (—NH 2 ) by reducing the obtained compound of the formula (1-ii). Obtainable.
  • the compound of the formula (1-ii) is reduced with reduced iron to obtain the alkylene compound represented by the formula (1).
  • the amount of reduced iron may be from 6 to 8 equivalents to 1 equivalent of the compound of the formula (1-ii)
  • the reaction temperature is from 60 ° C to 80 ° C, preferably from 70 ° C to 80 ° C.
  • the reaction time may be from 1 hour to 3 hours, preferably from 2 hours to 3 hours.
  • the compound of the formula (1-ii) is subjected to a reduction treatment using a metal catalyst such as palladium-carbon (Pd-C), platinum-carbon (Pt-C), Raney nickel, etc.
  • a metal catalyst such as palladium-carbon (Pd-C), platinum-carbon (Pt-C), Raney nickel, etc.
  • the alkylene compound represented by (1) can also be obtained.
  • the amount of the metal catalyst may be, for example, 0.4 to 5% by mass of the compound of the formula (1-ii) in terms of the amount of metal, and the reaction temperature is, for example, 30 to 100 ° C.
  • the reaction time may be, for example, from 1 hour to 10 hours.
  • hydrogen source for the reaction hydrogen gas, hydrazine, ammonium formate and the like can be used.
  • an alkylene compound represented by the following formula (1) is condensed with an acid anhydride represented by the following formula (2), and the condensation is represented by the following formula (3).
  • a step of obtaining at least one selected from the group consisting of a first quinophthalone compound and a second quinophthalone compound represented by the following formula (4) (hereinafter, referred to as step IV).
  • equations (3) and (4) a plurality of X 3 together, a plurality of X 4 each other, a plurality of X 5 and between the plurality of X 6 each other in may the same as or different from each other.
  • X 3 , X 4 , X 5 and X 6 each independently represent a hydrogen atom or a halogen atom.
  • the halogen atom in the formula (2) may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom.
  • At least one of X 3 , X 4 , X 5 and X 6 is preferably a halogen atom, and more preferably two or more are halogen atoms. . Further, it is preferable that at least one of X 4 and X 5 is a halogen atom, more preferably X 4 and X 5 are each a halogen atom.
  • Examples of the acid anhydride represented by the formula (2) include phthalic anhydride and halogen-substituted phthalic anhydride.
  • Specific examples of the halogen-substituted phthalic anhydride include tetrafluorophthalic anhydride and tetrafluorophthalic anhydride. Examples thereof include chlorophthalic anhydride, tetrabromophthalic anhydride, 4,5-dichlorophthalic anhydride, 4-chlorophthalic anhydride, and 4,5-dibromophthalic anhydride.
  • the acid anhydride represented by the formula (2) one type may be used alone, or two or more types may be used in combination.
  • the quinophthalone compound is obtained in which a plurality of X 3 , a plurality of X 4 , a plurality of X 5, and a plurality of X 6 are different from each other. be able to.
  • X 1 , X 2 , X 3 , X 4 , X 5 and X 6 each independently represent a hydrogen atom or a halogen atom.
  • the halogen atom in the formulas (3) and (4) may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, and more preferably a chlorine atom. Is more preferred.
  • At least one of X 3 , X 4 , X 5 and X 6 is preferably a halogen atom, and two or more are halogen atoms. Is more preferable. Further, it is preferable that at least one of X 4 and X 5 is a halogen atom, more preferably X 4 and X 5 are each a halogen atom.
  • a halogen atom is introduced into X 1 , X 2 , X 3 , X 4 , X 5 or X 6 , the dispersibility and durability of the quinophthalone compound are further improved, and the above-mentioned effects are more remarkably obtained. Tend.
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 and Z are as described above.
  • quinophthalone compound ⁇ Specific examples of the quinophthalone compound are described below, but the quinophthalone compound is not limited thereto.
  • the quinophthalone compound exhibits selective absorption and transmission due to dimerization of a heterocyclic skeleton centering on a quinoline ring.
  • the heterocyclic skeleton is dimerized using the alkylene group, which is a linking group, as a spacer, whereby the conjugation is cut and excessive redness is suppressed.
  • the quinophthalone compound has improved dispersibility by introducing an imide structure. From these facts, according to the quinophthalone compound, a pigment having excellent luminance and coloring power can be obtained. Specifically, for example, a yellow pigment composed of the above quinophthalone compound has a better luminance than a currently commonly used yellow pigment (CI Pigment Yellow 150), and has an excellent luminance exceeding this. Coloring power.
  • step IV 3 to 6 equivalents of the acid anhydride represented by the formula (2) is used for 1 equivalent of the alkylene compound represented by the formula (1), for example, by the method described in JP-A-2013-61622.
  • an acid catalyst to condense the alkylene compound represented by the formula (1) with the acid anhydride represented by the formula (2).
  • the reaction temperature of the condensation may be from 180 ° C to 250 ° C, preferably from 200 ° C to 250 ° C.
  • the condensation reaction time may be 1 hour to 8 hours, preferably 3 hours to 8 hours.
  • the acid catalyst examples include Bronsted acids or Lewis acids such as benzoic acid, p-toluenesulfonic acid, zinc chloride and iron chloride.
  • Step IV may be a step of obtaining a first quinophthalone compound represented by the formula (3) or a second quinophthalone compound represented by the formula (4), wherein the first quinophthalone compound and the second quinophthalone compound (A quinophthalone mixture) may be obtained.
  • the quinophthalone compound (or quinophthalone mixture) obtained by the production method according to the present embodiment has excellent coloring power as a pigment.
  • the quinophthalone compound may be converted into a pigment by a known and commonly used method.
  • the pigment (yellow pigment) composed of the quinophthalone compound may be finely divided by, for example, a salt milling treatment.
  • the yellow pigment may be surface-treated by a method such as rosin treatment, surfactant treatment, solvent treatment, and resin treatment.
  • Example A-1 5.00 g (56.1 mmol) of 4,4′-methylenebis (2-chloroaniline), 27.6 g (112 mmol) of p-chloranil, 150 ml of water, 150 ml of concentrated hydrochloric acid and 100 ml of n-butanol were added to the flask, and the mixture was added to the flask. Stirred at C for 30 minutes. To this mixture was added dropwise 11.8 g (168 mmol) of crotonaldehyde dissolved in 12 ml of n-butanol, and the mixture was further stirred for 1 hour.
  • the temperature was lowered to 80 ° C., and 15.3 g (112 mmol) of zinc chloride was added little by little. Then, 200 ml of THF was added, and the mixture was stirred for 1 hour while maintaining the temperature at 80 ° C. After allowing to cool to room temperature, ocher powder was recovered by vacuum filtration. The obtained ocher powder was washed with 200 ml of THF, and the ocher powder was recovered by vacuum filtration again. Further, the obtained ocher powder was transferred to a flask, 200 ml of water and 40 ml of 28% aqueous ammonia were added, and the mixture was stirred at room temperature for 2 hours. The powder was recovered by vacuum filtration to obtain 20.3 g of a crude product.
  • Example A-2 6,6′-Methylenediquinaldine obtained by the method described in the literature (Polymer, volume 39, No. 20 (1998), p4949) while charging 55.0 g of concentrated sulfuric acid in a flask and stirring under ice cooling. 00 g (23.5 mmol) were added. While maintaining the temperature at 10 ° C. or lower, 6.1 g of 60% nitric acid was added dropwise, and stirring was continued at 10 to 20 ° C. for 1 hour. The reaction solution was poured into 150 ml of ice water and adjusted to pH 3 using a 20 wt% aqueous sodium hydroxide solution. The precipitated powder was collected by filtration under reduced pressure, and washed with water to neutrality.
  • the solid was collected, dried by blowing air at 70 ° C., added to a mixed solvent of 100 ml of dimethyl sulfoxide (DMSO) and 100 ml of N, N-dimethylformamide (DMF), and stirred at 90 ° C. for 1 hour.
  • DMSO dimethyl sulfoxide
  • DMF N, N-dimethylformamide
  • the mixture was filtered under reduced pressure on celite to remove insolubles, and the obtained filtrate was added to 1 L of water with stirring.
  • the resulting precipitate was collected by filtration under reduced pressure, washed with water, and then blown dry at 70 ° C. to obtain 3.80 g (11.6 mmol) of the desired alkylene compound.
  • Example A-3 Under a nitrogen atmosphere, 10.0 g (25.8 mmol) of intermediate (iii), 1.00 g of 10% Pd—C, 50 ml of ethanol, and 100 ml of tetrahydrofuran (THF) were added to the flask, and the mixture was stirred at room temperature. Next, 12.9 g (257 mmol) of hydrazine monohydrate dissolved in a mixed solution of 20 ml of ethanol and 40 ml of THF was added dropwise. After completion of the dropwise addition, the mixture was stirred at 60 to 65 ° C. for 3 hours.
  • Example B-1 Under a nitrogen atmosphere, 14.1 g (116 mmol) of benzoic acid was weighed and melted in a flask at 140 ° C. Thereto, 1.44 g (3.62 mmol) of the alkylene compound obtained in Example (A-1) and 5.53 g (19.3 mmol) of tetrachlorophthalic anhydride were added, and the mixture was stirred at 220 ° C. for 4 hours. After allowing to cool, acetone (300 mL) was added to the reaction solution, and the mixture was stirred for 1 hour, and then filtered under reduced pressure to obtain 4.41 g (3.00 mmol) of quinophthalone compound B-1 as a yellow powder (yield: 83%).
  • Example B-2 Under a nitrogen atmosphere, 135 g (1.11 mol) of benzoic acid was weighed and melted in a flask at 140 ° C. Thereto were added 3.80 g (11.6 mmol) of the alkylene compound obtained in Example A-2, 18.0 g (62.9 mmol) of tetrachlorophthalic anhydride, and 0.490 g (3.60 mmol) of anhydrous zinc chloride. At 220 ° C. for 6 hours. After cooling the reaction mixture to 120 ° C., 300 mL of chlorobenzene was added, stirred for 1 hour, and filtered under reduced pressure.
  • Example C-1 Under a nitrogen atmosphere, 58.0 g (475 mmol) of benzoic acid was weighed and melted in a flask at 140 ° C. Thereto, 2.00 g (5.03 mmol) of the alkylene compound obtained in Example (A-1) and 5.04 g (17.6 mmol) of tetrachlorophthalic anhydride were added, and the mixture was stirred at 220 ° C. for 4 hours. After allowing to cool, 500 mL of acetone was added to the reaction solution, and the mixture was stirred for 1 hour, and then filtered under reduced pressure to obtain 6.00 g of a quinophthalone compound C-1 as a yellow powder. As a result of MALDI-MS, it was found that the obtained C-1 was a mixture of the compound of the formula (3-1-i) and the compound of the formula (4-1-i).
  • Example C-2 Under a nitrogen atmosphere, 58.0 g (475 mmol) of benzoic acid was weighed and melted in a flask at 140 ° C. Thereto were added 2.00 g (6.09 mmol) of the alkylene compound obtained in Example A-2, 6.09 g (21.3 mmol) of tetrachlorophthalic anhydride, and 0.205 g (1.50 mmol) of anhydrous zinc chloride. At 220 ° C. for 6 hours. After cooling the reaction mixture to 120 ° C., 500 mL of chlorobenzene was added, stirred for 1 hour, and filtered under reduced pressure.
  • Pigmentation example 1 0.500 parts by mass of the quinophthalone compound represented by the formula (3-1-i) obtained in Example B-1 was ground together with 1.50 parts by mass of sodium chloride and 0.750 parts by mass of diethylene glycol. Thereafter, the mixture was poured into 600 parts by mass of warm water and stirred for 1 hour. After the water-insoluble matter was separated by filtration and washed well with warm water, it was blown and dried at 90 ° C. to perform pigmentation to obtain a quinophthalone pigment. The average aspect ratio of the obtained pigment particles was less than 3.00, and the average primary particle size was 100 nm or less.
  • Pigmentation example 2 A quinophthalone compound represented by the formula (3-2-i) obtained in Example B-2 instead of the quinophthalone compound represented by the formula (3-1-i) obtained in Example B-1 Pigmentation was carried out in the same manner as in Pigmentation Example 1 except that quinophthalone pigment was used.
  • the average aspect ratio of the obtained pigment particles was less than 3.00, and the average primary particle size was 100 nm or less.
  • Example D-1 0.660 parts by mass of the quinophthalone pigment obtained in Pigmentation Example 1 was placed in a glass bottle, and 0.040 parts by mass of a sulfonic acid derivative (5) synthesized by the method described in JP-A-2013-54200, propylene glycol monomethyl ether 12.60 parts by mass of acetate, 1.400 parts by mass of BYK LPN-21116 (manufactured by BYK Chemie), 22.0 parts by mass of 0.3-0.4 mm ⁇ seple beads were added, and the mixture was added to a paint shaker (manufactured by Toyo Seiki Co., Ltd.). After half an hour of dispersion, a pigment dispersion was obtained. Note that the sulfonic acid group in the formula (5) is substituted on any of the hydrogen atoms on the quinoline ring.
  • Example D-2 A yellow toning composition was obtained in the same manner as in Example D-1, except that the quinophthalone pigment obtained in Pigmentation Example 2 was used instead of the quinophthalone pigment obtained in Pigmentation Example 1.
  • Example E-1 The composition for yellow toning obtained in Example D-1 and the composition for green toning obtained in Production Example 1 were mixed at a ratio of 39:61 to obtain a composition for green toning.
  • Example E-1 The composition for yellow toning obtained in Example D-1 and the composition for green toning obtained in Production Example 1 were mixed at a ratio of 39:61 to obtain a composition for green toning.
  • Example E-2 The composition for yellow toning obtained in Example D-2 and the composition for green toning obtained in Production Example 1 were mixed at a ratio of 40:60 to obtain a composition for green toning.
  • Example E-2 The composition for yellow toning obtained in Example D-2 and the composition for green toning obtained in Production Example 1 were mixed at a ratio of 40:60 to obtain a composition for green toning.
  • the luminance Y in the obtained evaluation sample was measured by a spectrophotometer (U3900 / 3900H type manufactured by Hitachi High-Tech Science Corporation). Further, for the obtained evaluation sample, the thickness of the colored film formed on the glass substrate was measured by a film thickness meter (VS1330 scanning white interference microscope manufactured by Hitachi High-Tech Science Corporation). It can be said that the thinner the film thickness, the higher the coloring power. Table 1 shows the results.
  • the quinaldine compound according to the present invention is useful as a raw material compound for producing a quinophthalone compound having excellent coloring power as a pigment.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Quinoline Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne un composé d'alkylène représenté par la formule (1). [Formule chimique 1] (dans la formule (1), X1 et X2 représentent chacun indépendamment un atome d'hydrogène ou un atome d'halogène, et Z représente un groupe alkylène ayant de 1 à 3 atomes de carbone.)
PCT/JP2019/032705 2018-08-31 2019-08-21 Composé d'alkylène, composé de quinophtalone et mélange de quinophtalone Ceased WO2020045200A1 (fr)

Priority Applications (2)

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JP2019569845A JP6677365B1 (ja) 2018-08-31 2019-08-21 アルキレン化合物、キノフタロン化合物及びキノフタロン混合物
CN201980055609.XA CN112638882A (zh) 2018-08-31 2019-08-21 亚烷基化合物、喹酞酮化合物和喹酞酮混合物

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JP2018-163802 2018-08-31
JP2018163802 2018-08-31

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WO2022130773A1 (fr) 2020-12-17 2022-06-23 富士フイルム株式会社 Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge
WO2022131191A1 (fr) 2020-12-16 2022-06-23 富士フイルム株式会社 Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges
WO2023234094A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément photodétecteur, capteur d'image et procédé de fabrication d'élément photodétecteur
WO2023234096A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément de détection de lumière, capteur d'image et procédé de production d'élément de détection de lumière
WO2023234095A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément de photodétection, capteur d'image et procédé de fabrication d'élément de photodétection

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Publication number Priority date Publication date Assignee Title
WO2022131191A1 (fr) 2020-12-16 2022-06-23 富士フイルム株式会社 Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges
WO2022130773A1 (fr) 2020-12-17 2022-06-23 富士フイルム株式会社 Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge
WO2023234094A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément photodétecteur, capteur d'image et procédé de fabrication d'élément photodétecteur
WO2023234096A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément de détection de lumière, capteur d'image et procédé de production d'élément de détection de lumière
WO2023234095A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément de photodétection, capteur d'image et procédé de fabrication d'élément de photodétection

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