Classifications

• • 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
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
• • 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
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
  • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
  • C08G73/12—Unsaturated polyimide precursors
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
  • C08K3/013—Fillers, pigments or reinforcing additives
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/10—Encapsulations, e.g. protective coatings characterised by their shape or disposition
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
  • H10W74/47—Encapsulations, e.g. protective coatings characterised by their materials comprising organic materials, e.g. plastics or resins

Definitions

• the present invention relates to a maleimide resin mixture for a sealing material, a maleimide resin composition, and a cured product thereof.
• the 5th generation communication system "5G”, which is currently being developed, is required to introduce technologies such as automatic driving, so performance such as further increase in capacity, high-speed communication, and low delay is required.
• the demand for low dielectric materials with a dissipation factor of 0.005 or less at least at 1 GHz is expected to increase.
• Maleimide resin is a compound that has heat resistance exceeding that of epoxy resin, moldability equivalent to that of epoxy resin, and low dielectric properties. By cross-linking the maleimide resin alone, or by reacting it with various maleimide resins or cross-linking agents, it is possible to give materials with excellent heat resistance and flame resistance.
• high heat resistance substrate materials flexible substrate materials, high heat resistance low dielectric materials, high heat resistance CFRP materials (carbon fiber composite materials), SiC power devices for automobiles, which require both extremely high heat resistance and moldability. Used for high heat-resistant encapsulants.
• Patent Document 1 discloses a method of obtaining an aromatic amine resin by distilling off the solvent under heating and reduced pressure, and then reacting it with maleic anhydride to obtain a maleimide resin.
• powdery maleimide resin not only has problems in workability and productivity due to scattering of powder during use, but also has problems such as environmental pollution (dirt and inhalation into the human body). .
• the solvent or the like cannot be completely removed during crystallization or precipitation. Specifically, when a solvent is contained, crystallization occurs in the system, making it impossible to obtain a homogeneous composition, and there is also the problem that it is difficult to expect stable quality.
• there has been a demand for maleimide moldings that are excellent in workability, productivity, and storage stability.
• an object of the present invention is to provide a maleimide resin mixture for encapsulants that exhibits high heat resistance and dielectric properties, is excellent in workability and productivity, and is less exposed to solvents in the environment.
• the present inventors have made intensive studies to solve the above problems, and as a result, a specific maleimide resin mixture for sealing materials is excellent in workability and productivity, and exhibits high heat resistance, dielectric properties, and flame retardancy. We found that and completed the present invention.
• a maleimide resin mixture comprising a maleimide resin (A) represented by the following formula (1) and a bifunctional cyanate resin (B) represented by the following formula (3), A maleimide resin mixture for a sealant containing 55 to 95% by weight of the maleimide resin (A) with respect to 100% by weight of the total resin amount of the maleimide resin (A) and the bifunctional cyanate resin (B).
• each X independently represents one of the structures represented by the following formulas (2-a) to (2-f).
• R 1 each independently represents hydrogen represents an atom, an alkyl group having 1 to 20 carbon atoms, or an aromatic group having 1 to 20 carbon atoms which may have a substituent, and each p independently represents an integer of 1 to 3.
• n is the number of repetitions and the average value n ave of n is 1 ⁇ n ave ⁇ 10.
• Each R 2 independently has a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a substituent represents an aromatic group having 1 to 20 carbon atoms, m represents an integer of 1 to 50, q each independently represents an integer of 1 to 4, r each independently represents an integer of 1 to 3 represents an integer.
• Y represents a direct bond, —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, and R 3 each independently represents a hydrogen atom, a carbon represents an alkyl group having a number of 1 to 20, an aromatic group having 1 to 20 carbon atoms which may have a substituent, and each t independently represents an integer of 1 to 4.
• R 3 each independently represents a hydrogen atom
• a carbon represents an alkyl group having a number of 1 to 20
• each t independently represents an integer of 1 to 4.
• the maleimide resin mixture for sealing material of the present invention exhibits high heat resistance, dielectric properties, and flame retardancy. In addition, it is possible to provide a maleimide resin mixture that is excellent in workability and productivity and less exposed to the environment. Furthermore, the generation of voids and cracks during molding can be prevented.
• maleimide resin mixture for sealing according to the embodiment of the present invention
• maleimide resin mixture is a maleimide resin (A) represented by the following formula (1) (hereinafter simply referred to as “maleimide resin (A )”), and a bifunctional cyanate resin (B) represented by the following formula (3) (hereinafter also simply referred to as “bifunctional cyanate resin (B)”), wherein the maleimide
• the maleimide resin (A) is contained in an amount of 55 to 95% by weight with respect to 100% by weight of the total resin amount of the resin (A) and the bifunctional cyanate resin (B).
• X is any one represented by the structures represented by the following formulas (2-a) to (2-f) represents a species.
• R 1 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aromatic group having 1 to 20 carbon atoms which may have a substituent;
• p represents an integer of 1 to 3;
• n is the number of repetitions, and the average value n ave of n is 1 ⁇ n ave ⁇ 10.
• * represents a bond to the benzene ring.
• R 2 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aromatic group having 1 to 20 carbon atoms which may have a substituent.
• m represents an integer of 1 to 50
• q represents an integer of 1 to 4
• r represents an integer of 1 to 3.
• the methylene group on the right side of formula (2-d) is bonded to any position from 1 to 8 of the naphthalene ring.
• Y represents a direct bond, —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —
• R 3 each independently represents a hydrogen atom
• a carbon represents an alkyl group having a number of 1 to 20, an aromatic group having 1 to 20 carbon atoms which may have a substituent
• each t independently represents an integer of 1 to 4.
• the maleimide resin (A) that can be used in this embodiment will be described.
• the maleimide resin (A) of the present embodiment is represented by the above formula (1), and in formula (1), R1 is preferably a hydrogen atom.
• R 2 is preferably a hydrogen atom.
• R3 is preferably a hydrogen atom.
• X is the solubility and compatibility in the solvent, and the heat resistance of the cured product obtained by curing the curable resin composition of the present embodiment, the formula (2-b), the formula (2-c), the formula (2-e) is preferred, and formulas (2-c) and (2-e) are more preferred.
• the average value n ave of n in the formula (1) is the value of the number average molecular weight obtained by measurement of gel permeation chromatography (GPC, detector: RI) of the maleimide resin, or the area of each separated peak. It can be calculated from the ratio.
• GPC gel permeation chromatography
• the maleimide resin (A) Since the maleimide resin (A) has repeating units, it is a maleimide resin with low crystallinity, low viscosity, low softening point and excellent workability.
• the number of maleimide groups in one molecule of the maleimide resin is preferably more than 2 and less than 10.
• the method for producing the maleimide resin (A) is not particularly limited, and it may be produced by any known method. As a specific manufacturing method, it is preferable to use, for example, the method disclosed in Japanese Patent Laid-Open No. 2009-001783.
• the maleimide resin (A) is preferably added to 100% by weight of the total resin amount of the maleimide resin (A) and the bifunctional cyanate resin (B). 55 to 95% by weight, more preferably 60 to 90% by weight, particularly preferably 60 to 80% by weight.
• each component of the maleimide resin mixture can be made amorphous without crystallization at room temperature (25° C.). Aggregation and crystallization can be suppressed, and long-term storage stability of the maleimide resin mixture can be exhibited.
• the bifunctional cyanate resin (B) of the present embodiment is represented by the above formula (3), and can be used singly or in combination.
• the bifunctional cyanate resin (B) By mixing the bifunctional cyanate resin (B) with the maleimide resin (A), the crystallinity of the maleimide resin mixture can be reduced, and the softening point and melt viscosity can also be reduced.
• the bifunctional cyanate resin (B) 1,1-bis(4-cyanatophenyl)ethane and 2,2-bis(4-cyanatophenyl)propane are preferable from the viewpoint of low melt viscosity and low melting point. , 2-bis(4-cyanatophenyl)propane is more preferred.
• melt viscosity can be measured with a cone/plate viscometer (ICI viscometer) described in JIS K5600-2-3.
• ICI viscometer cone/plate viscometer
• melt viscosity measured with an ICI viscometer is also referred to as ICI viscosity.
• the melt viscosity at 150° C. of the maleimide resin mixture of the present embodiment measured by a cone-plate viscometer is preferably 0.001 to 0.9 Pa ⁇ s, more preferably 0.01 to 0.5 Pa ⁇ s, and particularly preferably is 0.01 to 0.3 Pa ⁇ s. If the melt viscosity is lower than 0.001 Pa ⁇ s, dripping occurs during melt-kneading, making it difficult to maintain the compact. On the other hand, if the melt viscosity is higher than 0.9 Pa ⁇ s, it is difficult to fill the maleimide resin mixture with filler, and the maleimide resin mixture has poor fluidity, making it difficult to use as a sealing material. In general, a solvent cannot be used for the encapsulant, and thus the viscosity of the maleimide resin mixture cannot be reduced by the solvent.
• the softening point of the maleimide resin mixture of the present embodiment is preferably 40-110°C, more preferably 50-110°C, and particularly preferably 55-100°C. If the softening point is lower than 40° C., blocking (unintended adhesion) occurs between the resins at room temperature, resulting in reduced workability and productivity. On the other hand, if the softening point is higher than 110°C, the resin component aggregates and partially crystallizes in the process of returning to room temperature after the mixture is prepared by applying high heat during melt kneading, resulting in a non-uniform mixture. Quality and workability are degraded.
• the maleimide resin mixture of the present embodiment is preferably amorphous at room temperature (25°C).
• a maleimide resin composition can be easily prepared by using an amorphous maleimide resin mixture. Whether or not the solid maleimide resin mixture is amorphous can be visually confirmed by the presence or absence of aggregation of the crystalline components. calorimeter) or XRD (X-ray diffraction). Specifically, it is confirmed by DSC that there is no endothermic peak due to the heat of fusion of the crystal, or by XRD that there is no peak derived from repetition of the crystal structure.
• the organic solvent contained in the maleimide resin mixture of the present embodiment is preferably 30,000 ppm or less, more preferably 10,000 ppm or less. If the organic solvent content exceeds 30,000 ppm, the odor caused by the organic solvent remains when the maleimide resin mixture is used.
• the content of the organic solvent may be 0 ppm, but the lower limit is 5 ppm, which is the detection limit of measurement. ,000 ppm.
• the organic solvent is not particularly limited as long as it can dissolve the maleimide resin (A) and the bifunctional cyanate resin (B).
• Examples include aromatic hydrocarbons having 3 to 10 carbon atoms, ketones, esters and ethers. At least one organic solvent selected from is preferable, and ketones are particularly preferable in terms of solubility.
• the amount of the organic solvent used is preferably 10 to 1000 parts by weight, more preferably 50 to 500 parts by weight, per 100 parts by weight of the total amount of the maleimide resin (A) and the bifunctional cyanate resin (B).
• the maleimide resin mixture of the present embodiment is obtained by mixing the maleimide resin (A), the bifunctional cyanate tree (B) and an organic solvent, and distilling the mixture under reduced pressure while heating and stirring.
• the heating temperature is preferably from 40 to 150°C, more preferably from 80 to 120°C in terms of the melt viscosity of the maleimide resin mixture and the stability of the product.
• the maleimide resin composition of this embodiment includes the maleimide resin mixture described above. Furthermore, the maleimide resin composition can contain a curing agent (C) capable of crosslinking reaction with the maleimide resin (A) or the bifunctional cyanate resin (B). The crosslinkable compound undergoes a cross-linking reaction with the maleimide group or cyanato group and acts as a curing agent (C) for the maleimide resin mixture.
• a curing agent (C) capable of crosslinking reaction with the maleimide resin (A) or the bifunctional cyanate resin (B).
• the crosslinkable compound undergoes a cross-linking reaction with the maleimide group or cyanato group and acts as a curing agent (C) for the maleimide resin mixture.
• crosslinkable compounds examples include compounds having amino groups, phenolic hydroxyl groups, alcoholic hydroxyl groups, allyl groups, acrylic groups, methacrylic groups, vinyl groups, and conjugated diene groups.
• a compound having a vinyl group and a conjugated diene group can be blended.
• the amount of the curing agent (C) can be selected as appropriate, but it is preferably 10 to 5000 parts by weight, more preferably 50 to 2000 parts by weight, and particularly preferably 100 to 1000 parts by weight with respect to 100 parts by weight of the maleimide resin mixture. Range.
• a curing accelerator (D) can also be added to the maleimide resin composition of the present embodiment, if necessary.
• the curing accelerator (D) include 2-methylimidazole, 2-ethylimidazole, 2-phenylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 1-cyanoethyl-2-ethyl-4- imidazoles such as methylimidazole, triethylamine, triethylenediamine, 2-(dimethylaminomethyl)phenol, 1,8-diaza-bicyclo(5,4,0)-7-undecene, tris(dimethylaminomethyl)phenol, benzyldimethyl Amines such as amines, phosphines such as triphenylphosphine, tributylphosphine, trioctylphosphine, tetraphenylphosphonium, tetraphenylborate, tin o
• the maleimide resin composition of this embodiment can also contain an inorganic filler (E).
• Inorganic fillers include powders of crystalline silica, fused silica, alumina, zircon, calcium silicate, calcium carbonate, silicon carbide, silicon nitride, boron nitride, zirconia, fosterite, steatite, spinel, titania, talc, etc. Beads formed by spheroidizing are included, but are not limited to these. These may be used independently and may use 2 or more types.
• the maleimide resin composition when it is assumed that the maleimide resin composition is used as a semiconductor sealing material, crystalline silica, fused silica, or alumina is used as the inorganic filler (E) from the viewpoint of the balance of properties. is preferred.
• the content of these inorganic fillers is preferably 70 to 96% by mass with respect to 100% by mass of the maleimide resin composition of the present embodiment. 75 to 93% by mass is particularly preferable, and 80 to 93% by mass is more preferable.
• the fluidity of the maleimide resin composition is particularly high, if the amount of the inorganic filler is too small, the ratio of the inorganic filler to the resin varies depending on the position in the maleimide resin composition during molding, and the resin composition is molded. It is not preferable in terms of characteristics, such as parts with a large amount of inorganic filler and parts with a small amount of inorganic filler appearing in the body. Moreover, if the content of the inorganic filler exceeds 96%, it is not preferable because the fluidity cannot be obtained.
• the maleimide resin composition of the present embodiment contains other additives such as silane coupling agents, release agents such as stearic acid, palmitic acid, zinc stearate and calcium stearate, surfactants, dyes, pigments, ultraviolet rays, Various compounding agents such as absorbents and various thermosetting resins can be added.
• the maleimide resin composition of the present embodiment can be blended with a binder resin as necessary.
• Binder resins include butyral resins, acetal resins, acrylic resins, epoxy resins, epoxy-nylon resins, NBR-phenol resins, epoxy-NBR resins, polyamide resins, polyimide resins, silicone resins, and the like. Examples include, but are not limited to.
• the blending amount of the binder resin is preferably within a range that does not impair the flame retardancy and heat resistance of the cured product. 05 to 50 parts by weight, more preferably 0.05 to 20 parts by weight are used as necessary.
• the maleimide resin composition of this embodiment may be prepolymerized.
• the maleimide resin mixture of the present embodiment, the curing agent (C), the curing accelerator (D), the inorganic filler (E), the binder resin and other additives are heated and mixed in the presence or absence of a solvent. It prepolymerizes by doing. Mixing or prepolymerization of each component is carried out using, for example, an extruder, kneader, rolls, etc. in the absence of a solvent, and using a reactor equipped with a stirrer in the presence of a solvent.
• a uniform curable resin composition is obtained by kneading using a device such as a kneader, roll, planetary mixer, etc. at a temperature within the range of 50 to 100 ° C. do.
• a device such as a kneader, roll, planetary mixer, etc.
• After pulverizing the obtained curable resin composition it is molded into a cylindrical tablet by a molding machine such as a tablet machine, or it is made into a granular powder or a powdery molding, or these compositions are used as a surface support. It is also possible to form a sheet having a thickness of 0.05 mm to 10 mm by melting above and forming a curable resin composition molded body.
• the obtained molded article becomes a non-sticky molded article at 0 to 20°C, and its fluidity and curability hardly deteriorate even when stored at -25 to 0°C for 1 week or longer.
• the resulting molded product can be molded into a cured product using a transfer molding machine or a compression molding machine.
• the maleimide resin composition of the present embodiment is obtained by uniformly mixing the above components in a predetermined ratio, precured at 130 to 200° C. for 30 to 500 seconds, and further cured at 150 to 250° C. By post-curing for 2 to 15 hours, the curing reaction proceeds sufficiently to obtain the cured product of the present embodiment. It is also possible to uniformly disperse or dissolve the components of the curable resin composition in a solvent or the like, remove the solvent, and then cure the composition.
• the maleimide resin composition of the present embodiment thus obtained has moisture resistance, heat resistance, high adhesiveness, flame retardance, low dielectric constant, and low dielectric loss tangent. Therefore, the maleimide resin composition of the present embodiment can be used in a wide range of fields requiring moisture resistance, heat resistance, high adhesiveness, low dielectric constant and low dielectric loss tangent. Specifically, it is useful as an insulating material, a laminate (printed wiring board, BGA substrate, build-up substrate, etc.), a sealing material, a resist, or any other electrical/electronic component material. In addition to molding materials and composite materials, it can also be used in fields such as paint materials, adhesives, and 3D printing. Particularly in semiconductor encapsulation, solder reflow resistance is beneficial.
• a semiconductor device has a semiconductor element encapsulated with the maleimide resin composition of the present embodiment.
• semiconductor devices include DIP (dual in-line package), QFP (quad flat package), BGA (ball grid array), CSP (chip size package), SOP (small outline package), TSOP (thin small outline package), and TQFP. (think quad flat package) and the like.
• Examples 1 to 8, Comparative Examples 1 to 6 An eggplant flask was charged with the maleimide resin varnish shown in Tables 1 and 2 as the maleimide resin (A), the bifunctional cyanate resin, and methyl ethyl ketone (MEK) as the additional solvent in the parts by weight shown in Tables 1 and 2, respectively. Subsequently, after connecting the eggplant flask to a rotary evaporator equipped with a nitrogen gas line, the resin mixture was decompressed in an oil bath heated to 100° C. while bubbling nitrogen gas at 50 mL/min to distill off the solvent. got Tables 1 and 2 show the appearance of the resin mixture that was returned to room temperature after the solvent was distilled off.
• Tables 1 and 2 show the appearance of the resin mixture that was returned to room temperature after the solvent was distilled off.
• Softening point It was measured by a method according to the ring and ball method of JISK-7234. Fill a specified ring with a resin mixture, support it horizontally in a water bath, place a sphere of specified mass in the center of the sample, and raise the bath temperature at a specified rate. The temperature at which the mixture touched the bottom plate of the annulus was taken as the softening point.
• ⁇ Melt viscosity (ICI viscosity @ 150°C): The viscosity of the resin mixture at 150°C (ICI viscosity @ 150°C) was measured with a cone and plate viscometer. - Residual toluene amount and residual MEK amount: It was quantified by gas chromatography. -Device: GC-2010 (manufactured by Shimadzu Corporation) -Column: DB-WAX (manufactured by Agilent Technologies, length 30 m, inner diameter 0.25 mm) - Method: After holding the resin mixture at 40° C. for 5 minutes, the temperature was raised at a rate of 20° C./min and held at 220° C. for 5 minutes.
• toluene and methyl ethyl ketone vaporized from the resin mixture were passed through a column (DB-WAX, manufactured by Agilent Technologies, length 30 m, inner diameter 0.25 mm), and passed through a gas chromatography device (GC-2010, manufactured by Shimadzu Corporation). and quantified.
• MIR-3000-70MT Biphenylaralkyl-type maleimide resin (manufactured by Nippon Kayaku Co., Ltd., MEK/toluene mixed solution with a non-volatile content of 70%)
• MIR-5000-60T Diisopropylidenebenzene-type maleimide resin (manufactured by Nippon Kayaku Co., Ltd., toluene solution with a non-volatile content of 60%)
• BisA-OCN 2,2-bis(4-cyanatephenyl)propane (manufactured by Mitsubishi Gas Chemical Company, Inc.)

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• Organic Chemistry (AREA)
• Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
• Compositions Of Macromolecular Compounds (AREA)

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• 2022
  • 2022-10-07 CN CN202280069008.6A patent/CN118103430A/zh active Pending
  • 2022-10-07 WO PCT/JP2022/037693 patent/WO2023063267A1/ja not_active Ceased
  • 2022-10-07 KR KR1020247008991A patent/KR20240088722A/ko active Pending
  • 2022-10-07 JP JP2022580898A patent/JP7281246B1/ja active Active
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