WO2022065376A1 - 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法 - Google Patents

硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法 Download PDF

Info

Publication number
WO2022065376A1
WO2022065376A1 PCT/JP2021/034853 JP2021034853W WO2022065376A1 WO 2022065376 A1 WO2022065376 A1 WO 2022065376A1 JP 2021034853 W JP2021034853 W JP 2021034853W WO 2022065376 A1 WO2022065376 A1 WO 2022065376A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
resin composition
curable resin
compound
temporary fixing
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2021/034853
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
駿夫 ▲高▼橋
徳重 七里
聡史 林
和泉 大同
文香 星野
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sekisui Chemical Co Ltd
Original Assignee
Sekisui Chemical Co Ltd
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=80846561&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2022065376(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to CN202410019062.0A priority Critical patent/CN117946519A/zh
Priority to KR1020227042835A priority patent/KR20230074064A/ko
Priority to CN202180039607.9A priority patent/CN115702212B/zh
Priority to US18/025,232 priority patent/US12617944B2/en
Priority to CN202410019252.2A priority patent/CN117946520A/zh
Application filed by Sekisui Chemical Co Ltd filed Critical Sekisui Chemical Co Ltd
Priority to JP2022508852A priority patent/JP7194313B2/ja
Publication of WO2022065376A1 publication Critical patent/WO2022065376A1/ja
Priority to JP2022065624A priority patent/JP7201859B2/ja
Priority to JP2022065625A priority patent/JP7201860B2/ja
Priority to JP2022196951A priority patent/JP7804562B2/ja
Anticipated expiration legal-status Critical
Priority to JP2026002774A priority patent/JP2026042985A/ja
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • 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
    • C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
    • 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
    • C08G73/1075—Partially aromatic polyimides
    • C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/02—Halogenated hydrocarbons
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • 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
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08L79/085—Unsaturated polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on 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 C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J179/00—Adhesives based on 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 C09J161/00 - C09J177/00
    • C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J179/00—Adhesives based on 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 C09J161/00 - C09J177/00
    • C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C09J179/085—Unsaturated polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P72/00—Handling or holding of wafers, substrates or devices during manufacture or treatment thereof
    • H10P72/70—Handling or holding of wafers, substrates or devices during manufacture or treatment thereof for supporting or gripping
    • H10P72/74—Handling or holding of wafers, substrates or devices during manufacture or treatment thereof for supporting or gripping using temporarily an auxiliary support
    • H10P72/7402—Wafer tapes, e.g. grinding or dicing support tapes
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/005—Additives being defined by their particle size in general
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2467/00—Presence of polyester
    • C09J2467/006—Presence of polyester in the substrate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2479/00—Presence of polyamine or polyimide
    • C09J2479/08—Presence of polyamine or polyimide polyimide

Definitions

  • the present invention can suppress the occurrence of voids and floats between the adherend and the support even when the high-temperature processing treatment is performed at 300 ° C. or higher with the adherend and the support fixed, and the high-temperature processing treatment can be performed.
  • the present invention relates to a curable resin composition that can be easily peeled off after the above.
  • the present invention also relates to a temporary fixing material having an adhesive layer made of the curable resin composition, and a method for manufacturing an electronic component using the temporary fixing material.
  • the electronic components When processing electronic components such as semiconductors, in order to facilitate the handling of the electronic components and prevent them from being damaged, the electronic components may be fixed to the support plate via an adhesive composition, or the adhesive tape may be electronically attached. It is protected by attaching it to parts. For example, when a thick film wafer cut out from a high-purity silicon single crystal or the like is ground to a predetermined thickness to obtain a thin film wafer, the thick film wafer may be adhered to a support plate via an adhesive composition. Will be done.
  • Patent Document 1 discloses a pressure-sensitive adhesive sheet in which a polyfunctional monomer or oligomer having a radiopolymerizable functional group is bonded to a side chain or a main chain of a polymer. Has been done.
  • the adhesive strength is lowered by irradiating the polymer with ultraviolet rays at the time of peeling, and the polymer can be peeled without adhesive residue.
  • a metal thin film having more excellent conductivity can be formed by processing at a high temperature of about 300 to 350 ° C.
  • a high-temperature processing treatment at 300 ° C. or higher
  • a void is formed between the electronic component and the support fixing the electronic component during the high-temperature processing process.
  • floating may occur, and adhesion may be enhanced so that the adhesive strength does not sufficiently decrease at the time of peeling, or adhesive residue may occur.
  • polyimide resin has come to be used in many electronic parts as a material having high heat resistance, and various types of adherends made of polyimide resin are fixed to a support made of an inorganic material such as glass.
  • the process of processing the above has come to be carried out.
  • the adherend is made of a polyimide resin and subjected to high-temperature processing at 300 ° C. or higher, the adhesion tends to be enhanced as compared with the case where the adherend is made of an inorganic material.
  • the pressure-sensitive adhesive composition and the pressure-sensitive adhesive tape used for protecting the adherend made of polyimide are required to suppress the enhancement of adhesion with the adherend made of polyimide resin, while being between the adhesive and the support. It is also required to suppress the occurrence of voids and floats in the water.
  • the present invention can suppress the occurrence of voids and floats between the adherend and the support even when the high-temperature processing treatment is performed at 300 ° C. or higher with the adherend and the support fixed, and the high-temperature processing treatment can be performed. It is an object of the present invention to provide a curable resin composition which can be easily peeled off after the above. Another object of the present invention is to provide a temporary fixing material having an adhesive layer made of the curable resin composition, and a method for manufacturing an electronic component using the temporary fixing material.
  • the present invention is a curable resin composition containing a reactive compound (1) having a maleimide group and a resin (2) having an imide skeleton as a repeating unit of a main chain.
  • a reactive compound (1) having a maleimide group and a resin (2) having an imide skeleton as a repeating unit of a main chain.
  • the present invention will be described in detail below.
  • the present inventors have investigated a curable resin composition containing a reactive compound (1) having a maleimide group and a resin (2) having an imide skeleton as a repeating unit of a main chain.
  • the present inventors perform a high-temperature processing treatment at 300 ° C. or higher in a state where the adherend, particularly the adherend made of polyimide resin and the support, are fixed. Even so, it has been found that the occurrence of voids and floating between the support and the support can be suppressed and the resin can be easily peeled off after the high temperature processing treatment, and the present invention has been completed.
  • the curable resin composition of the present invention contains a reactive compound (1) having a maleimide group and a resin (2) having an imide skeleton as a repeating unit of the main chain.
  • a reactive compound (1) having a maleimide group By containing the above-mentioned reactive compound (1) having a maleimide group, the entire curable resin composition of the present invention is uniformly and rapidly polymerized and crosslinked by heating or irradiation with light, and the elastic modulus is increased. As a result, the adhesive strength is greatly reduced, so that it is possible to prevent the adhesion from being enhanced with respect to the adherend and the occurrence of adhesive residue at the time of peeling from the adherend.
  • the resin (2) having the above-mentioned imide skeleton as a repeating unit of the main chain has extremely excellent heat resistance due to having the imide skeleton, and the main chain can be decomposed even when high-temperature processing at 300 ° C. or higher is performed. It is unlikely to occur. Therefore, by including the resin (2) having the above-mentioned imide skeleton as a repeating unit of the main chain, the curable resin composition of the present invention causes voids and floats with the support during the high temperature processing. It can be suppressed, and it is possible to prevent the adhesion from being enhanced with respect to the adherend and the occurrence of adhesive residue at the time of peeling from the adherend.
  • the maleimide group may or may not be substituted.
  • the reactive compound (1) having a maleimide group is not particularly limited, but is a bismaleimide compound (1-I) or a compound having a maleimide group and having an imide skeleton as a repeating unit of the main chain (1-I). II) is preferred.
  • These reactive compounds (1) having a maleimide group may be used alone or in combination of two or more.
  • the bismaleimide compound (1-I) is a compound having two maleimide groups.
  • the molecular weight of the bismaleimide compound (1-I) is not particularly limited, but is preferably 5000 or less, and more preferably 2000 or less.
  • the bismaleimide compound (1-I) is preferably a compound having two maleimide groups and an aliphatic group derived from the diamine compound.
  • the diamine compound either an aliphatic diamine compound or an aromatic diamine compound can be used, but an aliphatic diamine compound is preferable.
  • the adhesive layer formed by using the curable resin composition can exhibit high flexibility and has high followability to an adherend having irregularities. And can be peeled off more easily at the time of peeling.
  • the diamine diamine is a diamine compound obtained by reducing and aminating cyclic and acyclic diamine acids obtained as dimers of unsaturated fatty acids, and is, for example, a linear type, a monocyclic type, or a polycyclic type. Examples thereof include dimer diamines such as molds.
  • the diamine diamine may contain a carbon-carbon unsaturated double bond, or may be a hydrogenated additive to which hydrogen has been added.
  • aliphatic group derived from the diamine diamine more specifically, for example, a group represented by the following general formula (4-1), a group represented by the following general formula (4-2), and the following general formula ( At least one selected from the group consisting of the group represented by 4-3) and the group represented by the following general formula (4-4) is preferable. Among them, the group represented by the following general formula (4-2) is more preferable.
  • R 1 to R 8 and R 13 to R 20 independently represent linear or branched hydrocarbon groups.
  • * represents a bond.
  • the bond * may be directly bonded to the maleimide group or may be bonded via another group.
  • the hydrocarbon groups represented by R 1 to R 8 and R 13 to R 20 are not particularly limited and may be saturated hydrocarbon groups. It may be an unsaturated hydrocarbon group. Among them, R1 and R2 , R3 and R4 , R5 and R6 , R7 and R8 , R13 and R14 , R15 and R16 , R17 and R18 , and R19 . It is preferable that the total number of carbon atoms of R 20 is 7 or more and 50 or less. When the total number of carbon atoms is within the above range, the adhesive layer formed by using the curable resin composition can exhibit higher flexibility, and the bismaleimide compound (1-I) can be used.
  • the compatibility with the solvent and other components of the above is further increased.
  • the total number of carbon atoms is more preferably 9 or more, still more preferably 12 or more, and even more preferably 14 or more.
  • the total number of carbon atoms is more preferably 35 or less, still more preferably 25 or less, and even more preferably 18 or less.
  • the optical isomerism is not particularly limited in the group represented by 4), and any optical isomerism is included.
  • the curable resin composition can exhibit higher heat resistance. That is, it is possible to further suppress the generation of voids and floats between the support and the support during the high-temperature processing treatment, and the adhesion to the adherend is enhanced, and adhesive residue is generated when the adherend is peeled off. It is possible to prevent it from happening.
  • the compound (1-II) having a maleimide group and having an imide skeleton as a repeating unit of the main chain may have a functional group equivalent (weight average molecular weight / number of maleimide groups) of 4000 or less. preferable.
  • the curable resin composition can exhibit higher heat resistance. It is considered that this is because the presence of maleimide groups in the molecule of the compound at a density of a certain level or higher shortens the distance between crosslinks, thereby further suppressing the enhancement of adhesion.
  • the functional group equivalent is more preferably 3000 or less, and further preferably 2000 or less.
  • the lower limit of the functional group equivalent is not particularly limited, but is substantially about 600.
  • the compound (1-II) having the maleimide group and having the imide skeleton as the repeating unit of the main chain has a higher weight average molecular weight (Mw) than the resin (2) having the imide skeleton as the repeating unit of the main chain. Is preferably small. More specifically, the compound (1-II) having the maleimide group and having an imide skeleton as a repeating unit of the main chain may have a weight average molecular weight (Mw) of 1000 or more and less than 20,000. preferable. When the weight average molecular weight is 1000 or more, the film-forming curable resin composition is facilitated, and the obtained adhesive layer exhibits a certain degree of flexibility, so that the adherend has irregularities.
  • the weight average molecular weight is less than 20,000, the solubility of the compound (1-II) having the maleimide group and having the imide skeleton as the repeating unit of the main chain in the solvent can be enhanced. It is more preferable that the weight average molecular weight is 2000 or more and less than 10,000.
  • the weight average molecular weight is measured as a polystyrene-equivalent molecular weight by a gel permeation chromatography (GPC) method.
  • the maleimide group may be located at either the side chain or the terminal, but may be present at both ends. Preferably, it is more preferably present in the side chain in addition to both ends.
  • the maleimide groups at both ends of the compound (1-II) having the above-mentioned maleimide group and having an imide skeleton as a repeating unit of the main chain are highly reactive, and the curable resin composition can be obtained by heating or irradiation with light. It can be sufficiently cured.
  • the curable resin composition has higher heat resistance due to the presence of a maleimide group in the side chain of the compound (1-II) having the above-mentioned maleimide group and having an imide skeleton as a repeating unit of the main chain. Can be demonstrated. It is considered that this is because the adhesion enhancement is further suppressed by shortening the distance between the crosslinks.
  • the maleimide group is present in the side chain of the compound (1-II) having the maleimide group and having the imide skeleton as the repeating unit of the main chain, the functionality is maintained while the weight average molecular weight is 1000 or more. It becomes easy to adjust the base equivalent to 4000 or less.
  • the curable resin composition has sufficient pressure-sensitive or heat-sensitive adhesive strength at the initial stage, and at the same time, it is possible to further suppress the occurrence of voids and floating during the high-temperature processing treatment, and it adheres to the adherend. It is possible to further prevent the increase and the generation of adhesive residue at the time of peeling from the adherend.
  • the compound (1-II) having a maleimide group and having an imide skeleton as a repeating unit of the main chain include the following compounds. That is, it has a structural unit represented by the following general formula (1a), a structural unit represented by the following general formula (1b), and a structural unit represented by the following general formula (1c) (however, s>. 0, t ⁇ 0, u ⁇ 0), and the compound (1-ii) whose both ends are represented by X 1 and X 2 , respectively, can be mentioned.
  • P 1 , P 2 and P 3 each independently represent an aromatic group
  • Q 1 is a substituted or unsubstituted linear, branched or cyclic group.
  • Q2 represents a group having a substituted or unsubstituted aromatic structure
  • R represents a substituted or unsubstituted branched aliphatic group or aromatic group.
  • At least one selected from the group consisting of X 1 , X 2 and X 3 represents a maleimide group-containing group.
  • P 1 , P 2 and P 3 are preferably aromatic groups having 5 to 50 carbon atoms. Since P 1 , P 2 and P 3 are aromatic groups having 5 to 50 carbon atoms, the curable resin composition can exhibit higher heat resistance. That is, it is possible to further suppress the generation of voids and floats between the support and the support during the high-temperature processing treatment, and the adhesion to the adherend is enhanced, and adhesive residue is generated when the adherend is peeled off. It is possible to prevent it from happening.
  • Q1 is preferably a substituted or unsubstituted linear, branched or cyclic aliphatic group having 2 to 100 carbon atoms. Since Q1 is a substituted or unsubstituted linear, branched or cyclic aliphatic group having 2 to 100 carbon atoms, the adhesive layer formed by using the curable resin composition has high flexibility. It is possible to exhibit high followability to an adherend having irregularities, and it is possible to peel off more easily at the time of peeling. Further, Q 1 is preferably an aliphatic group derived from a diamine compound.
  • the aliphatic group derived from the diamine compound may be the same as the aliphatic group derived from the diamine compound in the bismaleimide compound (1-I) as described above.
  • the adhesive has increased compatibility with the solvent and other components of compound (1-II) having the above-mentioned maleimide group and having an imide skeleton as a repeating unit of the main chain.
  • Q1 is preferably an aliphatic group derived from dimerdiamine.
  • the aliphatic group derived from the dimer diamine may be the same as the aliphatic group derived from the diamine diamine in the bismaleimide compound (1-I) as described above.
  • Q2 is preferably a group having a substituted or unsubstituted aromatic structure having 5 to 50 carbon atoms. Since Q2 is a substituted or unsubstituted group having an aromatic structure having 5 to 50 carbon atoms, the curable resin composition can exhibit higher heat resistance. That is, it is possible to further suppress the generation of voids and floats between the support and the support during the high-temperature processing treatment, and the adhesion to the adherend is enhanced, and adhesive residue is generated when the adherend is peeled off. It is possible to prevent it from happening.
  • R is preferably a substituted or unsubstituted branched chain-like aliphatic group or aromatic group having 2 to 100 carbon atoms. Since R is a substituted or unsubstituted branched chain-like aliphatic group or aromatic group having 2 to 100 carbon atoms, the adhesive layer formed by using the curable resin composition exhibits high flexibility. It is possible to exhibit high followability to an adherend having irregularities, and it is possible to peel off more easily at the time of peeling.
  • R is an aromatic group having an aromatic ester group or an aromatic ether group
  • the aromatic ester group or the aromatic ether group in R is bonded to X3.
  • the "aromatic ester group” means a group in which an ester group is directly bonded to an aromatic ring
  • the "aromatic ether group” means a group in which an ether group is directly bonded to an aromatic ring. ..
  • the maleimide group-containing group is at least one selected from the group consisting of X 1 , X 2 and X 3 .
  • at least X3 is a maleimide group - containing group.
  • the curable resin composition can exhibit higher heat resistance. That is, it is possible to further suppress the occurrence of voids and floats during the high-temperature processing treatment, and it is more likely that adhesion to the adherend is enhanced and adhesive residue is generated when the adherend is peeled off. Can be prevented.
  • the functional groups other than the maleimide group-containing group are independently, for example, an aliphatic group and an alicyclic.
  • Formula groups, aromatic groups, acid anhydrides, amine compounds and the like can be mentioned. Specific examples thereof include acid anhydrides and unreacted one-ended diamine compounds which are raw materials for the compound (1-II) having a maleimide group and having an imide skeleton as a repeating unit of the main chain. Further, for example, it may be a group containing a functional group having a double bond such as a citraconimide group, a vinyl ether group, an allyl group, and a (meth) acrylic group.
  • s, t and u have the above general formula (1-II) in the compound (1-II) having the maleimide group and having an imide skeleton as a repeating unit of the main chain. It corresponds to the content (mol%) of each of the structural unit represented by 1a), the structural unit represented by the general formula (1b), and the structural unit represented by the general formula (1c). ..
  • the content (s) of the structural unit represented by the general formula (1a) is larger than 0 mol%, preferably 30 mol% or more, more preferably 50 mol% or more, and preferably 90 mol% or less. More preferably, it is 80 mol% or less.
  • the content (t) of the structural unit represented by the general formula (1b) is 0 mol% or more, preferably 5 mol% or more, more preferably 10 mol% or more, still more preferably 20 mol% or more, and is preferable. Is 50 mol% or less, more preferably 30 mol% or less.
  • the content (u) of the structural unit represented by the general formula (1c) is 0 mol% or more, preferably 10 mol% or more, more preferably 20 mol% or more, preferably 50 mol% or less, more preferably. Is less than 30 mol%.
  • the curable resin composition causes voids and floats with the support during the high temperature processing. It can be further suppressed, and can be more easily peeled off at the time of peeling from the adherend.
  • the structural unit represented by the general formula (1a), the structural unit represented by the general formula (1b), and the structural unit represented by the general formula (1c) are continuous. It may have a block structure composed of block components arranged in a random manner, or each structural unit may have a random structure randomly arranged.
  • the method for producing the compound (1-II) having the above-mentioned maleimide group and having an imide skeleton as a repeating unit of the main chain is not particularly limited.
  • an imide compound is prepared by reacting a diamine compound with an aromatic acid anhydride, and the functional group of the imide compound further has a functional group that reacts with the functional group and a maleimide group-containing group (hereinafter,).
  • a functional group-containing maleimide compound) can be reacted.
  • it can be obtained by reacting a diamine compound with an aromatic acid anhydride to prepare an imide compound, and further reacting the terminal of the imide compound with, for example, maleic anhydride or the like.
  • the diamine compound either an aliphatic diamine compound or an aromatic diamine compound can be used.
  • the aliphatic diamine compound as the diamine compound, the adhesive layer formed by using the curable resin composition can exhibit high flexibility and has high followability to an adherend having irregularities. And can be peeled off more easily at the time of peeling.
  • an aromatic diamine compound as the diamine compound, the heat resistance of the curable resin composition is further improved.
  • a diamine compound having a functional group is used as the diamine compound, and the functional group is reacted with the functional group-containing maleimide compound to produce a compound (1-II) having a maleimide group in the side chain. can.
  • These aliphatic diamine compounds, aromatic diamine compounds and diamine compounds having a functional group may be used alone or in combination of two or more.
  • Examples of the aliphatic diamine compound include 1,10-diaminodecane, 1,12-diaminododecane, dimerdiamine, 1,2-diamino-2-methylpropane, 1,2-diaminocyclohexane, and 1,2-diamino.
  • aromatic diamine compound examples include 9,10-diaminophenanthrene, 4,4'-diaminooctafluorobiphenyl, 3,7-diamino-2-methoxyfluorene, 4,4'-diaminobenzophenone, and 3,4-.
  • Diaminobenzophenone 3,4-diaminotoluene, 2,6-diaminoanthraquinone, 2,6-diaminotoluene, 2,3-diaminotoluene, 1,8-diaminonaphthalene, 2,4-diaminotoluene, 2,5-diamino Toluene, 1,4-diaminoanthraquinone, 1,5-diaminoanthraquinone, 1,5-diaminonaphthalene, 1,2-diaminoanthraquinone, 2,4-kumendiamine, 1,3-bisaminomethylbenzene, 1,3- Bisaminomethylcyclohexane, 2-chloro-1,4-diaminobenzene, 1,4-diamino-2,5-dichlorobenzene, 1,4-diamino-2,5-dimethylbenzene, 4,4
  • the aliphatic diamine compound is preferable, and the solvent of the compound (1-II) having the above-mentioned maleimide group and having an imide skeleton as a repeating unit of the main chain is preferable from the viewpoint of enhancing flexibility. Dimerdiamine is more preferable from the viewpoint of increasing compatibility with other components and facilitating the formation of an adhesive layer.
  • Examples of the diamine compound having a functional group include a diamine compound having a hydroxyl group, a diamine compound having a carboxyl group, and a diamine compound having a halogen group.
  • Examples of the diamine compound having a hydroxyl group include 1,3-diamino-2-propanol, 2,4-diaminophenoxyethanol, 3,5-diaminophenoxyethanol, 2,4-diaminophenol, and 3,5-diaminophenol, 2. , 4-Diaminobenzyl alcohol, 4,6-diaminoresorcin dihydrochloride, 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane and the like.
  • Examples of the diamine compound having a carboxyl group include 3,5-diaminobenzoic acid and the like.
  • Examples of the diamine compound having a halogen group include 2,4-diaminochlorobenzene and the like.
  • aromatic acid anhydride examples include pyromellitic acid, 1,2,5,6-naphthalenetetracarboxylic acid, 2,3,6,7-naphthalenetetracarboxylic acid, 1,2,4,5-naphthalene. Tetracarboxylic acid, 1,4,5,8-naphthalenetetracarboxylic acid, 3,3', 4,4'-benzophenonetetracarboxylic acid, 3,3', 4,4'-biphenyl ether tetracarboxylic acid, 3, 3', 4,4'-biphenyltetracarboxylic acid, 2,3,5,6-pyridinetetracarboxylic acid, 3,4,9,10-perylenetetracarboxylic acid, 4,4'-sulfonyldiphthalic acid, 1 -Trifluoromethyl-2,3,5,6-benzenetetracarboxylic acid, 2,2', 3,3'-biphenyltetracarboxylic acid, 2,4
  • the functional group-containing maleimide compound is selected and used according to the functional group at the terminal or side chain of the imide compound.
  • a maleimide compound having a carboxyl group can be mentioned.
  • the maleimide compound having a carboxyl group include maleimide acetate, maleimide propionic acid, maleimide butyric acid, maleimidehexanoic acid, trans-4- (N-maleimidemethyl) cyclohexane-1-carboxylic acid, and 19-maleimide-17-oxo. -4,7,10,13-tetraoxa-16-azanonadecanoic acid and the like can be mentioned.
  • the content of the reactive compound (1) having a maleimide group is not particularly limited, but the total of the reactive compound (1) having a maleimide group and the resin (2) having the imide skeleton as a repeating unit of the main chain.
  • the preferred lower limit of 100 parts by weight is 20 parts by weight, and the preferred upper limit is 80 parts by weight.
  • the content of the reactive compound (1) having a maleimide group is within this range, the curable resin composition can be more easily peeled off at the time of peeling from the adherend.
  • the more preferable lower limit of the content of the reactive compound (1) having a maleimide group is 30 parts by weight, and the more preferable upper limit is 70 parts by weight.
  • the resin (2) having the imide skeleton as the repeating unit of the main chain is not particularly limited as long as it is a resin having the imide skeleton as the repeating unit of the main chain, but has the maleimide group and has the imide skeleton as the main chain. It is preferable that the weight average molecular weight (Mw) is larger than that of the compound (1-II) having the repeating unit of. More specifically, the resin (2) having the imide skeleton as a repeating unit of the main chain preferably has a weight average molecular weight (Mw) of 20,000 or more. When the weight average molecular weight of the resin (2) having the imide skeleton as the repeating unit of the main chain is 20,000 or more, the curable resin composition can exhibit higher heat resistance.
  • the weight average molecular weight of the resin (2) having the imide skeleton as the repeating unit of the main chain is more preferably 50,000 or more.
  • the upper limit of the weight average molecular weight of the resin (2) having the imide skeleton as the repeating unit of the main chain is not particularly limited, but from the viewpoint of solubility in a solvent, a preferable upper limit is 150,000 and a more preferable upper limit is 100,000.
  • the resin (2) having the imide skeleton as the repeating unit of the main chain is preferably a resin (2-I) having no maleimide group and having the imide skeleton as the repeating unit of the main chain.
  • Specific examples of the resin (2-I) having no maleimide group and having an imide skeleton as a repeating unit of the main chain include, for example, a structural unit represented by the following general formula (1d) and a resin (2-I).
  • Examples thereof include a resin (2-i) having a structural unit represented by the following general formula (1e) (where s> 0, t ⁇ 0) and having both ends represented by X4 and X5 , respectively.
  • P4 and P5 each independently represent an aromatic group
  • Q3 is a substituted or unsubstituted linear, branched or cyclic aliphatic group.
  • X4 and X5 represent groups that do not contain maleimide groups.
  • P4 and P5 are preferably aromatic groups having 5 to 50 carbon atoms. Since P 4 and P 5 are aromatic groups having 5 to 50 carbon atoms, the curable resin composition can exhibit higher heat resistance. That is, it is possible to further suppress the occurrence of voids and floats during the high-temperature processing treatment, and it is more likely that adhesion to the adherend is enhanced and adhesive residue is generated when the adherend is peeled off. Can be prevented.
  • Q3 is preferably a substituted or unsubstituted linear, branched or cyclic aliphatic group having 2 to 100 carbon atoms. Since Q3 is a substituted or unsubstituted linear, branched or cyclic aliphatic group having 2 to 100 carbon atoms, the adhesive layer formed by using the curable resin composition has high flexibility. It is possible to exhibit high followability to an adherend having irregularities, and it is possible to peel off more easily at the time of peeling. Further, Q3 is preferably an aliphatic group derived from a diamine compound.
  • the aliphatic group derived from the diamine compound has the bismaleimide compound (1-I) and the maleimide group as described above, and the diamine in the compound (1-II) having an imide skeleton as a repeating unit of the main chain. It may be similar to the aliphatic group derived from the compound. Above all, from the viewpoint of enhancing flexibility, the compatibility of the resin (2-I) having no maleimide group and having an imide skeleton as a repeating unit of the main chain with the solvent and other components is increased and adhesion is increased. From the viewpoint of facilitating the formation of the agent layer, Q3 is preferably an aliphatic group derived from dimerdiamine.
  • the compound (1-II) having the above-mentioned bismaleimide compound (1-I) and maleimide group and having an imide skeleton as a repeating unit of the main chain is used. It may be similar to an aliphatic group derived from dimerdiamine. That is, in the curable resin composition of the present invention, at least one selected from the group consisting of the reactive compound (1) having a maleimide group and the resin (2) having the imide skeleton as a repeating unit of the main chain is selected. , It is preferable to have an aliphatic group derived from dimerdiamine.
  • Q4 is preferably a group having a substituted or unsubstituted aromatic structure having 5 to 50 carbon atoms. Since Q4 is a substituted or unsubstituted group having an aromatic structure having 5 to 50 carbon atoms, the curable resin composition can exhibit higher heat resistance. That is, it is possible to further suppress the occurrence of voids and floats during the high-temperature processing treatment, and it is more likely that adhesion to the adherend is enhanced and adhesive residue is generated when the adherend is peeled off. Can be prevented.
  • Examples of the groups not containing the maleimide group represented by X4 and X5 include, for example, an aliphatic group, an alicyclic group, an aromatic group, an acid anhydride, an amine compound and the like. Specific examples thereof include acid anhydrides and unreacted one-ended diamine compounds which are raw materials for the resin (2-I) which does not have the maleimide group and has an imide skeleton as a repeating unit of the main chain. .. Further, for example, it may be a group containing a functional group having a double bond such as a citraconimide group, a vinyl ether group, an allyl group, and a (meth) acrylic group.
  • s and t are the general formulas (2-I) in the resin (2-I) having no maleimide group and having an imide skeleton as a repeating unit of the main chain. It corresponds to the content (mol%) of each of the structural unit represented by 1d) and the structural unit represented by the general formula (1e).
  • the content (s) of the structural unit represented by the general formula (1d) is larger than 0 mol%, preferably 30 mol% or more, more preferably 50 mol% or more, and preferably 90 mol% or less. More preferably, it is 80 mol% or less.
  • the content (t) of the structural unit represented by the general formula (1e) is 0 mol% or more, preferably 5 mol% or more, more preferably 10 mol% or more, still more preferably 20 mol% or more, and is preferable. Is 50 mol% or less, more preferably 30 mol% or less.
  • the curable resin composition causes voids and floats with the support during the high temperature processing. It can be further suppressed, and can be more easily peeled off at the time of peeling from the adherend.
  • the structural unit represented by the general formula (1d) and the structural unit represented by the general formula (1e) have a block structure composed of block components in which the respective structural units are continuously arranged. It may be possible to have a random structure in which each structural unit is randomly arranged.
  • the method for producing the resin (2) having the imide skeleton as the repeating unit of the main chain is not particularly limited, and can be obtained, for example, by reacting a diamine compound with an aromatic acid anhydride.
  • the diamine compound and the aromatic acid anhydride are the same as the diamine compound and the aromatic acid anhydride in the compound (1-II) having a maleimide group as described above and having an imide skeleton as a repeating unit of the main chain. It may be similar.
  • the content of the resin (2) having the imide skeleton as the repeating unit of the main chain is not particularly limited, but the reactive compound (1) having the maleimide group and the resin (2) having the imide skeleton as the repeating unit of the main chain. ),
  • the preferred lower limit is 20 parts by weight, and the preferred upper limit is 80 parts by weight.
  • the curable resin composition can further suppress the occurrence of voids and floats during the high temperature processing treatment. In addition, it can be easily peeled off when it is peeled off from the adherend.
  • the more preferable lower limit of the content of the resin (2) having the imide skeleton as the repeating unit of the main chain is 30 parts by weight, and the more preferable upper limit is 70 weight by weight. It is a department.
  • the curable resin composition of the present invention preferably further contains a silicone compound or a fluorine compound. Since the silicone compound and the fluorine compound have excellent heat resistance, they prevent the curable resin composition from being scorched even after being processed at a high temperature of 300 ° C. or higher, and bleed out to the interface of the adherend at the time of peeling to peel off. Make it easier.
  • the silicone compound is not particularly limited, and examples thereof include silicone oil, silicone diacrylate, and a silicone-based graft copolymer.
  • the fluorine compound is not particularly limited, and examples thereof include a hydrocarbon compound having a fluorine atom.
  • the silicone compound or the fluorine compound preferably has a functional group that can be crosslinked with the reactive compound (1) having the maleimide group or the resin (2) having the imide skeleton as a repeating unit of the main chain, and the maleimide group and the compound. It is more preferable to have a crosslinkable functional group. Since the silicone compound or the fluorine compound has a functional group capable of cross-linking with the maleimide group, the silicone compound or the fluorine compound chemically reacts with the reactive compound (1) having the maleimide group by heating or irradiation with light to obtain the above. It is incorporated into the reactive compound (1) having a maleimide group.
  • the functional group that can be crosslinked with the maleimide group is not particularly limited, and examples thereof include a radically polymerizable unsaturated bond (for example, a vinyl group, a (meth) acryloyl group, and a optionally substituted maleimide group).
  • a silicone compound having a functional group crosslinkable with a maleimide group is preferable from the viewpoint of being environmentally friendly and easy to dispose of.
  • silicone compound having a functional group that can be crosslinked with the maleimide group a silicone compound having a siloxane skeleton in the main chain and a functional group having a double bond in the side chain or the terminal is preferable.
  • the silicone compound having a siloxane skeleton in the main chain and a functional group having a side chain or a double bond at the end is not particularly limited, but the silicone compound represented by the following general formula (I) and the following general formula (II). ), And at least one selected from the group consisting of the silicone compound represented by the following general formula (III).
  • These silicone compounds have particularly high heat resistance and high polarity, so that they can easily bleed out from the curable resin composition.
  • X and Y each independently represent an integer of 0 to 1200, and R represents a functional group having a double bond.
  • examples of the functional group having a double bond represented by R include a maleimide group, a citraconimide group, and a vinyl ether which may be substituted. Groups, allyl groups, (meth) acrylic groups and the like can be mentioned. Of these, a maleimide group that may be substituted is preferable because higher heat resistance can be obtained.
  • the plurality of R's when a plurality of R's are present, the plurality of R's may be the same or different.
  • silicone compounds represented by the general formula (I), the general formula (II), and the general formula (III) commercially available ones include, for example, EBECRYL350 and EBECRYL1360 (all manufactured by Dycel Cytec). Be done. Further, BYK-UV3500 (manufactured by BIC Chemie), TEGO RAD2250 (manufactured by Evonik) (both R is an acrylic group) and the like can be mentioned.
  • the content of the silicone compound or the fluorine compound is not particularly limited, but is preferable for a total of 100 parts by weight of the reactive compound (1) having a maleimide group and the resin (2) having the imide skeleton as a repeating unit of the main chain.
  • the lower limit is 0.1 parts by weight, and the preferable upper limit is 20 parts by weight.
  • the curable resin composition can exhibit excellent peelability without contaminating the adherend.
  • the more preferable lower limit of the content of the silicone compound or the fluorine compound is 0.3 parts by weight, and the more preferable upper limit is 10 parts by weight. Since the curable resin composition of the present invention has excellent heat resistance, a sufficient effect can be exhibited even if the content of the silicone compound or the fluorine compound is relatively small. Therefore, the possibility of contamination by the silicone compound or the fluorine compound can be further reduced.
  • the curable resin composition of the present invention preferably further contains a polymerization initiator.
  • the above-mentioned polymerization initiator is not particularly limited, and may be a thermal polymerization initiator or a photopolymerization initiator, but a photopolymerization initiator is preferable.
  • the photopolymerization initiator examples include those that are activated by irradiating with light having a wavelength of 250 to 800 nm. Above all, it does not easily overlap with the absorption wavelengths of the reactive compound (1) having the maleimide group and the resin (2) having the imide skeleton as the repeating unit of the main chain, and is sufficiently sufficient when the curable resin composition is irradiated with light. Since it is activated, the photopolymerization initiator preferably contains a photopolymerization initiator having a molar absorbance coefficient of 1 or more at 405 nm.
  • the photopolymerization initiator more preferably contains a photopolymerization initiator having a molar extinction coefficient of 200 or more at 405 nm, and further preferably contains a photopolymerization initiator having a molar extinction coefficient of 350 or more at 405 nm. ..
  • the upper limit of the molar extinction coefficient at 405 nm of the photopolymerization initiator having a molar extinction coefficient of 1 or more at 405 nm is not particularly limited, but is, for example, 2000, 1500 or the like.
  • photopolymerization initiator examples include acetophenone derivative compounds such as methoxyacetophenone, benzoin ether compounds such as benzoin propyl ether and benzoin isobutyl ether, ketal derivative compounds such as benzyl dimethyl ketal and acetophenone diethyl ketal, and phosphine oxide derivative compounds. And so on.
  • the content of the polymerization initiator is not particularly limited, but the preferable lower limit for a total of 100 parts by weight of the reactive compound (1) having a maleimide group and the resin (2) having the imide skeleton as a repeating unit of the main chain is 0.1 part by weight, preferably the upper limit is 10 parts by weight.
  • the content of the polymerization initiator is within this range, the entire curable resin composition is uniformly and quickly polymerized and crosslinked by heating or irradiation with light, and the elastic modulus is increased, so that the adhesive strength is greatly reduced. Therefore, it is possible to prevent the adhesion from being enhanced with respect to the adherend and the occurrence of adhesive residue at the time of peeling from the adherend.
  • the more preferable lower limit of the content of the polymerization initiator is 0.3 parts by weight, and the more preferable upper limit is 3 parts by weight.
  • the curable resin composition of the present invention may further contain a gas generating agent that generates a gas by irradiating with light.
  • a gas generating agent that generates a gas by irradiating with light.
  • the above gas generating agent has a weight loss rate at 300 ° C. when heated at a heating rate of 10 ° C./min from 30 ° C. to 300 ° C. under a nitrogen atmosphere by TG-DTA (thermogravimetric-differential thermal analysis) measurement. It is preferably 5% or less. When the weight reduction rate is 5% or less, decomposition of the gas generating agent is unlikely to occur even when high-temperature processing at 300 ° C. or higher is performed, and the curable resin composition exhibits higher heat resistance. be able to. That is, it is possible to further suppress peeling during the high-temperature processing treatment, and it is possible to further prevent the adhesion from being enhanced and the adhesive residue from being generated at the time of peeling.
  • the TG-DTA (thermogravimetric-differential thermal analysis) measurement can be performed using, for example, a TG-DTA device (STA7200RV, manufactured by Hitachi High-Tech Science Corporation, or an equivalent product thereof).
  • the gas generating agent examples include a gas generating agent that generates a gas by heating, a gas generating agent that generates a gas by irradiating with light, and the like. These gas generating agents may be used alone or in combination of two or more. Among them, a gas generating agent that generates a gas by irradiating with light is preferable, and a gas generating agent that generates a gas by irradiating with ultraviolet rays is more preferable.
  • the gas generating agent include a tetrazole compound or a salt thereof, a triazole compound or a salt thereof, an azo compound, an azido compound, xanthone acetic acid, a carbonate and the like. These gas generating agents may be used alone or in combination of two or more. Of these, a tetrazole compound or a salt thereof is preferable because it is particularly excellent in heat resistance.
  • the content of the gas generating agent is not particularly limited, but the preferable lower limit for a total of 100 parts by weight of the reactive compound (1) having a maleimide group and the resin (2) having the imide skeleton as a repeating unit of the main chain is 5 parts by weight, preferably the upper limit is 50 parts by weight.
  • the content of the gas generating agent is within this range, the curable resin composition can exhibit particularly excellent peelability.
  • the more preferable lower limit of the content of the gas generating agent is 8 parts by weight, and the more preferable upper limit is 30 parts by weight.
  • the curable resin composition of the present invention may further contain an inorganic filler.
  • an inorganic filler By containing the above-mentioned inorganic filler, the curable resin composition can suppress the decrease in elastic modulus at high temperature, so that even when the high temperature processing treatment of 300 ° C. or higher is performed, the peeling during the high temperature processing treatment is further improved. It can be suppressed.
  • the inorganic filler is not particularly limited, and is, for example, an inorganic filler consisting of silicon, titanium, aluminum, calcium, boron, magnesium and zirconia oxides, and at least one selected from the group consisting of composites thereof. Can be mentioned. Of these, silica and talc are preferable because they are commercially available products that are inexpensive and easily available.
  • the inorganic filler may be surface-modified.
  • the modifying functional group that surface-modifies the inorganic filler is not particularly limited, and examples thereof include an alkylsilane group, a methacryloyl group, and a dimethylsiloxane group. Of these, a dimethylsiloxane group is preferable because it has an appropriate hydrophobicity.
  • the average particle size of the inorganic filler is not particularly limited, but the preferred lower limit is 5 nm and the preferred upper limit is 30 ⁇ m. When the average particle size of the inorganic filler is within this range, the curable resin composition can be more suppressed from peeling during the high temperature processing treatment, and can be peeled by the peel treatment at the time of peeling.
  • the more preferable lower limit of the average particle size of the inorganic filler is 10 nm, the more preferable upper limit is 20 ⁇ m, the further preferable lower limit is 15 nm, and the further preferable upper limit is 15 ⁇ m.
  • the average particle size is preferably a number average particle size.
  • the average particle size for example, 50 arbitrary inorganic fillers are observed with an electron microscope or an optical microscope, the average value of the particle sizes of each inorganic filler is calculated, and the laser diffraction type particle size distribution is measured. It is required by that.
  • the content of the inorganic filler is not particularly limited, but a preferable lower limit for a total of 100 parts by weight of the reactive compound (1) having a maleimide group and the resin (2) having the imide skeleton as a repeating unit of the main chain is preferable. 1 part by weight, preferably 20 parts by weight.
  • the curable resin composition can be more suppressed from peeling during the high temperature processing treatment, and can be peeled by the peel treatment at the time of peeling.
  • the more preferable lower limit of the content of the inorganic filler is 3 parts by weight, the more preferable upper limit is 15 parts by weight, the further preferable lower limit is 5 parts by weight, and the further preferable upper limit is 10 parts by weight.
  • the curable resin composition of the present invention may contain known additives such as a photosensitizer, a heat stabilizer, an antioxidant, an antistatic agent, a plasticizer, a resin, a surfactant, and a wax.
  • the curable resin composition of the present invention preferably has a 5% weight loss temperature of 350 ° C. or higher.
  • the 5% weight loss temperature is 350 ° C. or higher, the curable resin composition can exhibit higher heat resistance. That is, it is possible to further suppress the generation of voids and floats between the support and the support during the high-temperature processing treatment, and the adhesion to the adherend is enhanced, and adhesive residue is generated when the adherend is peeled off. It is possible to prevent it from happening.
  • the 5% weight loss temperature is more preferably 380 ° C. or higher, and even more preferably 400 ° C. or higher.
  • the upper limit of the 5% weight loss temperature is not particularly limited, but is substantially about 600 ° C.
  • the 5% weight loss temperature can be measured as follows. After the curable resin composition is cured, it is weighed in an aluminum pan and the aluminum pan is set in the device. In a nitrogen atmosphere, heat the measurement sample from 25 ° C with a thermogravimetric measuring device (STA7200 (manufactured by Hitachi High-Tech Science) or its equivalent) at a heating rate of 10 ° C / min, and measure the temperature at which the weight is reduced by 5%. ..
  • the curable resin composition is a photocurable type
  • the curable resin composition can be cured by irradiating it with ultraviolet rays of, for example, 405 nm at an intensity of 20 mW / cm 2 for 150 seconds, and the curable resin composition is thermoset. In the case of a mold, it can be cured by heating in an oven at 150 ° C. for 10 minutes, for example.
  • the preferable lower limit of the gel fraction after curing is 70% by weight, and the preferable upper limit is 95% by weight.
  • the gel fraction after curing is within the above range, the curable resin composition can be more easily peeled off at the time of peeling from the adherend.
  • the more preferable lower limit of the gel fraction after curing is 75% by weight, and the more preferable upper limit is 90% by weight.
  • the gel fraction after curing is such that an ultraviolet ray of 405 nm is emitted at an intensity of 20 mW / cm 2 using an ultrahigh pressure mercury lamp on an adhesive layer formed by using a curable resin composition.
  • test piece is prepared by cutting the adhesive layer into a flat rectangular shape having a size of 50 mm ⁇ 100 mm.
  • the test piece is immersed in toluene at 23 ° C. for 24 hours, then removed from the toluene and dried under the condition of 110 ° C. for 1 hour.
  • the weight of the test piece after drying is measured, and the gel fraction is calculated using the following formula (1). It is assumed that the release film for protecting the adhesive layer is not laminated on the test piece.
  • the method for producing the curable resin composition of the present invention is not particularly limited, and for example, the reactive compound (1) having a maleimide group, the resin (2) having the imide skeleton as a repeating unit of the main chain, and the resin (2) having the imide skeleton as a repeating unit of the main chain.
  • the reactive compound (1) having a maleimide group the resin (2) having the imide skeleton as a repeating unit of the main chain
  • the resin (2) having the imide skeleton as a repeating unit of the main chain examples thereof include a method of mixing additives to be blended as necessary using a bead mill, ultrasonic dispersion, homogenizer, high-power disperser, roll mill and the like.
  • a temporary fixing material having an adhesive layer made of the curable resin composition of the present invention is also one of the present inventions.
  • Such a temporary fixing material is referred to as a first temporary fixing material of the present invention.
  • the first adhesive layer and the second adhesive layer made of the curable resin composition of the present invention containing the gas generator A temporary fixing material having the above is also one of the present inventions.
  • Such a temporary fixing material is referred to as a second temporary fixing material of the present invention.
  • the first adhesive layer contains the gas generating agent and is a curable adhesive layer capable of generating gas.
  • the preferable lower limit of the gel fraction after curing is 50% by weight.
  • the first adhesive layer can be more easily peeled off at the time of peeling.
  • a more preferable lower limit of the gel fraction after curing is 80% by weight.
  • the gel fraction after curing is such that the first adhesive layer is cured by irradiating the first adhesive layer with ultraviolet rays of 405 nm at an intensity of 20 mW / cm 2 for 150 seconds, and then thermosetting. In the case of a mold, it is cured by heating at 150 ° C. for 10 minutes, and then measured by the following method.
  • the first adhesive layer is cut into a flat rectangular shape having a size of 50 mm ⁇ 100 mm to prepare a test piece.
  • the test piece is immersed in toluene at 23 ° C. for 24 hours, then removed from the toluene and dried under the condition of 110 ° C. for 1 hour.
  • the weight of the test piece after drying is measured, and the gel fraction is calculated using the following formula (1). It is assumed that the release film for protecting the first adhesive layer is not laminated on the test piece.
  • Gel fraction (% by weight) 100 x (W 2 -W 0 ) / (W 1 -W 0 ) (1) (W 0 : Weight of substrate, W 1 : Weight of test piece before immersion, W 2 : Weight of test piece after immersion and drying)
  • the first adhesive layer preferably has an adhesive force against glass of 1.5 N / inch or less at 25 ° C. after curing and heating at 300 ° C. for 10 minutes (after heating and cooling). When the adhesive force against glass is within the above range, the first adhesive layer can be more easily peeled off at the time of peeling.
  • the adhesive force against glass is more preferably 1.2 N / inch or less, further preferably 1.1 N / inch or less, and even more preferably 1.0 N / inch or less.
  • the adhesive strength against glass is measured by the following method.
  • the first adhesive layer is heat-laminated on quartz glass (Matsunami Glass Industry Co., Ltd., large slide glass white edge polishing No.
  • the heat laminating is performed once under the conditions of a temperature set value of 100 ° C. and a speed setting value of 5. After heat laminating, it is cured by irradiating it with ultraviolet rays of 405 nm at an intensity of 20 mW / cm 2 for 150 seconds using an ultra-high pressure mercury lamp, or by heating it in an oven at 150 ° C. for 10 minutes, and then from the glass side. Heat on a hot plate at 300 ° C. for 10 minutes. The first adhesive layer after curing and heating at 300 ° C. for 10 minutes was subjected to a 180 ° peel test under the conditions of a tensile speed of 300 mm / min at 25 ° C. and a relative humidity of 50%, and the adhesive strength was obtained. To measure.
  • the thickness of the first adhesive layer is not particularly limited, but the preferred lower limit is 5 ⁇ m and the preferred upper limit is 550 ⁇ m. When the thickness is 5 ⁇ m or more, the first adhesive layer can have sufficient pressure-sensitive or heat-sensitive adhesive force at the initial stage. When the thickness is 550 ⁇ m or less, the first adhesive layer can exhibit high flexibility, can exhibit high followability to an adherend having irregularities, and can more easily be peeled off. Can be peeled off.
  • a more preferable lower limit of the thickness is 10 ⁇ m, a further preferable lower limit is 20 ⁇ m, and a further preferable lower limit is 30 ⁇ m.
  • a more preferable upper limit of the thickness is 400 ⁇ m, a further preferable upper limit is 300 ⁇ m, a further preferable upper limit is 200 ⁇ m, and a further preferable upper limit is 150 ⁇ m.
  • the second adhesive layer is not particularly limited, and a curable adhesive layer having the same composition, physical properties, thickness and the like as the first adhesive layer can be used. Of these, a thermosetting adhesive layer is preferable. Since the second adhesive layer is a thermosetting adhesive layer, a substrate having low light transmittance is used, and the first adhesive layer is a photocurable adhesive layer, so that the first adhesive layer is a photocurable adhesive layer. Even when light is irradiated from the adhesive layer side of No. 1, the second adhesive layer can be sufficiently cured by heating.
  • the second adhesive layer may or may not contain the gas generating agent.
  • the first temporary fixing material of the present invention and the second temporary fixing material of the present invention have an adhesive layer made of the curable resin composition of the present invention on one or both surfaces of the base material. Also, it does not have to have a base material. When the above-mentioned base material is not provided, it is not necessary to select a base material having both light transmittance and heat resistance, and the temporary fixing material has a cheaper and simpler structure. Further, when the base material is not provided, in the second temporary fixing material of the present invention, when both the first adhesive layer and the second adhesive layer are photocurable adhesive layers. However, the light can sufficiently reach the curable adhesive layer opposite to the side irradiated with the light.
  • the second temporary fixing material of the present invention has the above-mentioned first adhesive layer and the above-mentioned second adhesive layer laminated on both sides of the above-mentioned base material, respectively. That is, it is preferable that the first adhesive layer, the base material, and the second adhesive layer are laminated in this order.
  • the base material examples include sheets made of transparent resins such as acrylic, olefin, polycarbonate, vinyl chloride, ABS, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), nylon, urethane, and polyimide. Further, a sheet having a mesh-like structure, a sheet with holes, glass and the like can also be used.
  • transparent resins such as acrylic, olefin, polycarbonate, vinyl chloride, ABS, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), nylon, urethane, and polyimide.
  • the thickness of the base material is not particularly limited, but from the viewpoint of increasing light transmission and flexibility, the preferable lower limit is 5 ⁇ m, the preferable upper limit is 150 ⁇ m, the more preferable lower limit is 10 ⁇ m, and the more preferable upper limit is 100 ⁇ m. Is.
  • the temporary fixing material of the present invention preferably has an adhesive force against glass of 1.5 N / inch or less at 25 ° C. after curing and heating at 300 ° C. for 10 minutes (after heating and allowing to cool).
  • the adhesive force against glass is more preferably 1.2 N / inch or less, further preferably 1.1 N / inch or less, and even more preferably 1.0 N / inch or less.
  • the adhesive strength against glass is measured by the following method.
  • the temporary fixing material is heat-laminated on glass (Matsunami Glass Industry Co., Ltd., large slide glass white edge polishing No. 2) with a laminator at 100 ° C.
  • the heat laminating is performed once under the conditions of a temperature set value of 100 ° C. and a speed setting value of 5. After heat laminating, it is cured by irradiating it with ultraviolet rays of 405 nm at an intensity of 20 mW / cm 2 for 150 seconds from the glass side using an ultrahigh pressure mercury lamp, or by heating it in an oven at 150 ° C. for 10 minutes. After curing, heat from the glass side on a hot plate at 300 ° C. for 10 minutes.
  • the curable resin composition of the present invention, the first temporary fixing material of the present invention, and the second temporary fixing material of the present invention have sufficient pressure-sensitive or heat-sensitive adhesive force at the initial stage and are undergoing high-temperature processing. It is possible to suppress the occurrence of voids and floats between the support and the support. On the other hand, it is possible to prevent the adhesion from being enhanced with respect to the adherend and the occurrence of adhesive residue at the time of peeling, and it is possible to easily peel off at the time of peeling from the adherend. Therefore, the curable resin composition of the present invention, the first temporary fixing material of the present invention, and the second temporary fixing material of the present invention are adherends subjected to high temperature processing at 300 ° C. or higher, particularly.
  • the electronic components can be suitably used for protection and temporary fixing of an adherend made of a polyimide resin.
  • the electronic components are fixed to the support plate via a curable resin composition or a temporary fixing material in order to facilitate the handling of the electronic components and prevent them from being damaged.
  • it can be suitably used for protecting a temporary fixing material by attaching it to an electronic component.
  • a method for manufacturing an electronic component including the first step of peeling the electronic component from the temporary fixing material of the present invention is also one of the present inventions.
  • the curing step of curing the adhesive layer of the temporary fixing material of the present invention may be performed immediately before the peeling step of peeling the electronic component from the temporary fixing material of the present invention, but the first invention of the present invention. It is preferable to perform this after the temporary fixing step of temporarily fixing the electronic component to the temporary fixing material and before the heat treatment step of heat-treating the electronic component.
  • a method for manufacturing an electronic component having a step, a gas generating step of generating gas from the first adhesive layer, and a peeling step of peeling the support and the temporary fixing material is also one of the present inventions. Is.
  • the curing step may be performed immediately before the gas generation step, but is preferably performed after the support sticking step and the adherend sticking step and before the heat treatment step. By performing the curing step before the heat treatment step, the temporary fixing material can exhibit more excellent heat resistance.
  • Examples of the support include glass, a quartz substrate, and the like.
  • Examples of the adherend include silicon wafers and the like.
  • the present invention even when a high temperature processing treatment of 300 ° C. or higher (for example, heating at 300 to 450 ° C.) is performed with the adherend and the support fixed, voids and floats between the adherend and the support are performed. Can be provided, and a curable resin composition that can be easily peeled off after undergoing a high-temperature processing treatment can be provided. Further, according to the present invention, it is possible to provide a temporary fixing material having an adhesive layer made of the curable resin composition, and a method for manufacturing an electronic component using the temporary fixing material.
  • a Dean-Stark trap and a condenser were attached to the flask and the mixture was refluxed for 2 hours to form an amine-terminated diimide. After cooling the reaction product to room temperature or lower, 12.8 g (0.13 mol) of maleic anhydride was added, and then 5 g (0.05 mol) of maleic anhydride was added. The mixture was refluxed for another 12 hours, cooled to room temperature, 300 mL of toluene was added to the flask, and impurities were precipitated and removed by standing.
  • a compound (1-II) having an imide skeleton as a repeating unit of the main chain was obtained.
  • the obtained compound was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 5000.
  • dimer diamine (Priamine 1075 manufactured by Croda)
  • Bis-AP-AF 5.5 g (0.015 mol)
  • 4,4'-(4,4'- 39 g (0.075 mol) of isopropyridene diphenoxy) diphthalic acid anhydride was added in this order.
  • a Dean-Stark trap and a condenser were attached to the flask, the mixture was refluxed for 2 hours, cooled to room temperature, 300 mL of toluene was added to the flask, and impurities were precipitated and removed by standing.
  • the obtained solution is filtered through a glass frit funnel filled with silica gel, and then the solvent is removed by vacuum to form a brown solid, which does not have a maleimide group represented by the following formula (C) and has an imide skeleton.
  • a resin (2-I) having a repeating unit of the main chain was obtained.
  • the obtained resin was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 72000.
  • an ethyl acetate solution of a functional group-containing (meth) acrylic polymer having a solid content of 55% by weight and a weight average molecular weight of 500,000 was obtained.
  • the reaction was carried out by adding 3.5 parts by weight of 2-isocyanatoethyl methacrylate as a functional group-containing unsaturated compound to 100 parts by weight of the resin solid content of the obtained ethyl acetate solution containing a functional group-containing (meth) acrylic polymer. To obtain an acrylic reactive resin.
  • the obtained acrylic reactive resin was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (product name, manufactured by Waters) as a column, and the weight average molecular weight was 55. It was 10,000.
  • GPC gel permeation chromatography
  • Example 1 Production of Temporary Fixing Material 70 parts by weight of compound (1-II) having a maleimide group and having an imide skeleton as a repeating unit of the main chain in 150 mL of toluene, without a maleimide group, and 30 parts by weight of a resin (2-I) having an imide skeleton as a repeating unit of the main chain was added. Further, add 5 parts by weight of a bifunctional silicone acrylate (EBECRYL350 manufactured by Daicel Ornex) as a silicone compound and 2 parts by weight of Irgacure 819 (manufactured by BASF) as a photopolymerization initiator to prepare a toluene solution of the curable resin composition.
  • EBECRYL350 manufactured by Daicel Ornex
  • Irgacure 819 manufactured by BASF
  • a toluene solution of the obtained curable resin composition is applied with a doctor knife on the release-treated surface of a PET film having a thickness of 50 ⁇ m and which has been subjected to a single-sided release treatment so that the thickness of the dry film is 40 ⁇ m. Then, the coating solution was dried by heating at 110 ° C. for 5 minutes. Then, it was statically cured at 40 ° C. for 3 days to obtain a temporary fixing material having an adhesive layer.
  • the obtained adhesive layer of the temporary fixing material was weighed on an aluminum pan after the adhesive layer was cured, and the aluminum pan was set in the apparatus. Under a nitrogen atmosphere, the measurement sample was heated from 25 ° C. to 500 ° C. with a thermogravimetric measuring device (STA7200, manufactured by Hitachi High-Tech Science Co., Ltd.) at a heating rate of 10 ° C./min, and the temperature at which the weight was reduced by 5% was measured.
  • the curing conditions were as follows: irradiation with ultraviolet rays of 405 nm at an intensity of 20 mW / cm 2 for 150 seconds, or instead of irradiation with ultraviolet rays, heating was performed in an oven at 150 ° C. for 10 minutes.
  • the adhesive layer of the obtained temporary fixing material was irradiated with ultraviolet rays of 405 nm at an intensity of 20 mW / cm 2 for 150 seconds using an ultrahigh pressure mercury lamp, and then measured by the following method.
  • a test piece was prepared by cutting the temporary fixing material into a flat rectangular shape having a size of 50 mm ⁇ 100 mm. The test piece was immersed in toluene at 23 ° C. for 24 hours, then removed from the toluene and dried under the condition of 110 ° C. for 1 hour. The weight of the test piece after drying was measured, and the gel fraction was calculated using the following formula (1). It is assumed that the release film for protecting the adhesive layer is not laminated on the test piece.
  • Example 18 the first adhesive layer of the obtained temporary fixing material is irradiated with ultraviolet rays of 405 nm at an intensity of 20 mW / cm 2 for 150 seconds, and the first and second adhesive layers are irradiated. After curing, each adhesive layer was weighed and used as a test piece.
  • Example 19 which will be described later, instead of irradiating with ultraviolet rays, the first and second adhesive layers are cured by heating in an oven at 150 ° C. for 10 minutes, and then the respective adhesive layers are weighed. It was used as a test piece. Since these test pieces have no substrate, W 0 was 0.
  • Examples 2 to 11, Comparative Examples 1 to 4 A curable resin composition and a temporary fixing material were obtained in the same manner as in Example 1 except that the composition of the curable resin composition was changed as shown in Table 1. The materials used are shown below.
  • -Fluorine compound photoreactive fluorine compound, manufactured by DIC, Megafuck RS-56
  • -Gas generator (5,5'-Bi-1H-tetrazole disodium salt (BHT-2Na)
  • Example 12 to 17 A curable resin composition and a temporary fixing material were obtained in the same manner as in Example 1 except that the composition of the curable resin composition was changed as shown in Table 2. The materials used are shown below.
  • -Inorganic filler silicon particles, manufactured by Tokuyama Corporation, MT-10, average particle diameter 15 nm
  • -Inorganic filler silicon particles, manufactured by Ryumori Co., Ltd., 5x, average particle diameter 1 ⁇ m
  • Example 18 Formation of First Adhesive Layer (Curable Adhesive Layer Containing Gas Generator) 100 parts by weight of the reactive resin shown in Table 3 was added to 300 mL of toluene, and 5,5'-Bi-1H was used as the gas generator. -30 parts by weight of tetorazole plastic salt (BHT-2Na), 5 parts by weight of EBECRYL350 as a silicone compound, and 3 parts by weight of Irgacure 369 (manufactured by BASF) as a photopolymerization initiator were added.
  • BHT-2Na tetorazole plastic salt
  • EBECRYL350 EBECRYL350
  • Irgacure 369 manufactured by BASF
  • a toluene solution of a curable resin composition in which 5,5'-Bi-1H-tetrazole disodium salt (BHT-2Na) was dispersed was prepared.
  • the toluene solution of the obtained curable resin composition is coated on a polyethylene terephthalate film having a thickness of 50 ⁇ m prepared as a separator and whose surface has been mold-released so that the thickness of the dry film is 50 ⁇ m with a doctor knife. did.
  • the coating solution was dried by heating for 10 minutes to obtain a first adhesive layer (curable adhesive layer containing a gas generating agent).
  • Second Adhesive Layer In 300 mL of toluene, 100 parts by weight of the reactive resin shown in Table 3, 5 parts by weight of EBECRYL350 as a silicone compound, and 3 parts of Irgacure 369 (manufactured by BASF) as a photopolymerization initiator. Added parts by weight. As a result, a toluene solution of the curable resin composition was prepared. The obtained toluene solution of the curable resin composition is coated on a 50 ⁇ m-thick polyethylene terephthalate film prepared as a separator with a release-treated surface using a doctor knife so that the thickness of the dry film is 50 ⁇ m. Then, using an oven preheated to 110 ° C., the coating solution was dried by heating for 10 minutes to obtain a second adhesive layer.
  • Example 19 The composition of the curable resin composition was changed as shown in Table 3, and the curable resin composition and the temporary fixing material were prepared in the same manner as in Example 1 except that the base material was used as shown below. Obtained. That is, when forming the second adhesive layer, the obtained toluene solution of the curable resin composition was subjected to corona treatment on one side to form a corona of a 25 ⁇ m-thick polyimide film (Kapton film manufactured by Ube Industries, Ltd.). The treated surface was coated with a doctor knife so that the thickness of the dry film was 50 ⁇ m. Using an oven preheated to 110 ° C., the coating solution was dried by heating for 10 minutes.
  • Table 3 The composition of the curable resin composition was changed as shown in Table 3, and the curable resin composition and the temporary fixing material were prepared in the same manner as in Example 1 except that the base material was used as shown below. Obtained. That is, when forming the second adhesive layer, the obtained toluene solution of the curable resin composition was subject
  • a polyethylene terephthalate film having a thickness of 50 ⁇ m prepared as a separator and prepared as a separator was laminated on the adhesive layer surface on the opposite side of the Kapton film to obtain a second adhesive layer.
  • the polymerization initiator Perbutyl O manufactured by NOF CORPORATION was used.
  • Example 19 instead of irradiation with ultraviolet rays, the first and second adhesive layers were cured by heating in an oven at 150 ° C. for 10 minutes. After curing, the release PET film of the temporary fixing material was peeled off and heated from the glass side on a hot plate at 300 ° C. for 10 minutes. The appearance of the temporary fixing material after curing and heating at 300 ° C. was visually observed and evaluated according to the following criteria. ⁇ : No voids or floats were found between the glass plate and ⁇ : Fine voids were found between the glass plate and the glass plate, or part of the gap between the glass plate and the glass plate was floating.
  • the release PET film of the temporary fixing material was peeled off, and the wafer side having the photosensitive polyimide film was heated on a hot plate at 300 ° C. for 10 minutes.
  • a 180 ° peel test was performed on the temporary fixing material after curing and heating at 300 ° C. under the conditions of 25 ° C. and a tensile speed of 300 mm / min.
  • the surface of the wafer having the photosensitive polyimide film after the temporary fixing material was peeled off was visually observed and evaluated according to the following criteria. ⁇ : No glue residue was found ⁇ : No glue residue, but cloudiness was found on the peeled surface ⁇ : No glue residue was found
  • Example 19 instead of irradiation with ultraviolet rays, the first and second adhesive layers were cured by heating in an oven at 150 ° C. for 10 minutes. After curing, the release PET film of the temporary fixing material was peeled off and heated from the glass side on a hot plate at 300 ° C. for 10 minutes. A 180 ° peel test was performed on the temporary fixing material after curing and heating at 300 ° C. for 10 minutes and allowing it to cool under the conditions of 25 ° C. and a tensile speed of 300 mm / min. In Examples 18 and 19, measurements were performed on the respective surfaces of the first adhesive layer and the second adhesive layer. Regarding the adhesive strength of the first adhesive layer to glass, after heating at 300 ° C.
  • the temporary fixing materials obtained in Examples 2 to 4 and 12 to 17 were further evaluated as follows.
  • the obtained temporary fixing material was cut to a width of 1 inch, and then heat-laminated once on a 1 mm thick glass at 100 ° C. with a thermal laminator (Leon13DX) using a speed memory 3.
  • a thermal laminator Leon13DX
  • ultraviolet rays of 405 nm were irradiated from the glass side with an intensity of 20 mW / cm 2 for 150 seconds using an ultrahigh pressure mercury lamp.
  • the release PET film was peeled off and heated from the glass side on a hot plate at 300 ° C. for 20 minutes. This test was performed 5 times.
  • a 180 ° peel test was performed on the temporary fixing material after curing and heating at 300 ° C. for 20 minutes under the conditions of 25 ° C. and a tensile speed of 300 mm / min. This test was performed 5 times.
  • the peelability of the temporary fixing material was evaluated according to the following criteria. In the peeling test, those with floating (with peeling) were not evaluated. ⁇ : Peelable in all 5 tests ⁇ : Peelable in 1 to 4 tests out of 5 times ⁇ : Peelable in all 5 tests
  • the present invention even when a high temperature processing treatment of 300 ° C. or higher is performed with the adherend and the support fixed, it is possible to suppress the occurrence of voids and floats between the adherend and the support, and the temperature is high. It is possible to provide a curable resin composition that can be easily peeled off after undergoing a processing treatment. Further, according to the present invention, it is possible to provide a temporary fixing material having an adhesive layer made of the curable resin composition, and a method for manufacturing an electronic component using the temporary fixing material.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Adhesive Tapes (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Mechanical Treatment Of Semiconductor (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Polymerisation Methods In General (AREA)
  • Dicing (AREA)
  • Container, Conveyance, Adherence, Positioning, Of Wafer (AREA)
  • Laminated Bodies (AREA)
  • Graft Or Block Polymers (AREA)
PCT/JP2021/034853 2020-09-23 2021-09-22 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法 Ceased WO2022065376A1 (ja)

Priority Applications (10)

Application Number Priority Date Filing Date Title
JP2022508852A JP7194313B2 (ja) 2020-09-23 2021-09-22 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法
KR1020227042835A KR20230074064A (ko) 2020-09-23 2021-09-22 경화성 수지 조성물, 가고정재, 및 전자 부품의 제조 방법
CN202180039607.9A CN115702212B (zh) 2020-09-23 2021-09-22 固化性树脂组合物、临时固定材料、以及电子部件的制造方法
US18/025,232 US12617944B2 (en) 2020-09-23 2021-09-22 Curable resin composition, temporary fixing material, and electronic component manufacturing method
CN202410019252.2A CN117946520A (zh) 2020-09-23 2021-09-22 固化性树脂组合物、临时固定材料、以及电子部件的制造方法
CN202410019062.0A CN117946519A (zh) 2020-09-23 2021-09-22 固化性树脂组合物、临时固定材料、以及电子部件的制造方法
JP2022065625A JP7201860B2 (ja) 2020-09-23 2022-04-12 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法
JP2022065624A JP7201859B2 (ja) 2020-09-23 2022-04-12 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法
JP2022196951A JP7804562B2 (ja) 2020-09-23 2022-12-09 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法
JP2026002774A JP2026042985A (ja) 2020-09-23 2026-01-09 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2020-159180 2020-09-23
JP2020159179 2020-09-23
JP2020159181 2020-09-23
JP2020159180 2020-09-23
JP2020-159179 2020-09-23
JP2020-159181 2020-09-23

Publications (1)

Publication Number Publication Date
WO2022065376A1 true WO2022065376A1 (ja) 2022-03-31

Family

ID=80846561

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2021/034853 Ceased WO2022065376A1 (ja) 2020-09-23 2021-09-22 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法

Country Status (5)

Country Link
JP (5) JP7194313B2 (https=)
KR (1) KR20230074064A (https=)
CN (3) CN115702212B (https=)
TW (1) TW202219224A (https=)
WO (1) WO2022065376A1 (https=)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2024002673A (ja) * 2022-06-24 2024-01-11 信越化学工業株式会社 硬化性樹脂組成物、半導体封止材、接着剤、接着フィルム、プリプレグ、層間絶縁材料及びプリント配線板
WO2024019088A1 (ja) * 2022-07-22 2024-01-25 株式会社レゾナック マレイミド樹脂、樹脂組成物、硬化物、シート、積層体、及びプリント配線板
WO2024019084A1 (ja) * 2022-07-22 2024-01-25 株式会社レゾナック ポリマレイミド樹脂、樹脂組成物、硬化物、シート、積層体、及びプリント配線板
WO2024079924A1 (ja) * 2022-10-14 2024-04-18 日本化薬株式会社 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置
WO2024079925A1 (ja) * 2022-10-14 2024-04-18 日本化薬株式会社 樹脂組成物、硬化物、半導体素子、およびドライフィルムレジスト
WO2024117235A1 (ja) 2022-12-01 2024-06-06 日産化学株式会社 異物除去用コーティング膜形成組成物及び半導体基板
WO2024157629A1 (ja) * 2023-01-25 2024-08-02 積水化学工業株式会社 光硬化性材料、光硬化性フィルム、及び、硬化物
WO2025058045A1 (ja) * 2023-09-15 2025-03-20 積水化学工業株式会社 接着性フィルム、接着性フィルムの製造方法、接着性樹脂組成物、及び、半導体装置の製造方法
WO2025063226A1 (ja) * 2023-09-19 2025-03-27 積水化学工業株式会社 イミド樹脂材料、硬化性樹脂組成物、接着性フィルム、仮固定材、及び、イミド樹脂材料の製造方法
TWI922798B (zh) 2022-10-14 2026-04-21 日商日本化藥股份有限公司 樹脂組成物、樹脂片材、多層印刷配線板、及半導體裝置

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024063112A1 (ja) * 2022-09-21 2024-03-28 積水化学工業株式会社 樹脂組成物、仮固定材、及び、電子部品の製造方法
JP7396742B1 (ja) 2022-11-10 2023-12-12 ユニチカ株式会社 ビスマレイミドおよびその製造方法
TW202449021A (zh) 2023-04-07 2024-12-16 日商味之素股份有限公司 樹脂組成物
TW202528480A (zh) * 2023-09-11 2025-07-16 日商富士軟片股份有限公司 樹脂組成物、硬化物、積層體、硬化物之製造方法、積層體之製造方法、半導體元件之製造方法及半導體元件、以及化合物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0532946A (ja) * 1991-07-31 1993-02-09 Lintec Corp 再剥離型粘着性ポリマー
JP2013079360A (ja) * 2011-09-20 2013-05-02 Nitto Denko Corp 再剥離用粘着剤組成物、再剥離用粘着剤層および再剥離用粘着シート
JP2020132881A (ja) * 2019-02-18 2020-08-31 積水化学工業株式会社 樹脂材料及び多層プリント配線板

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003231872A (ja) 2001-08-03 2003-08-19 Sekisui Chem Co Ltd 両面粘着テープ及びそれを用いたｉｃチップの製造方法
JP4005006B2 (ja) 2003-09-04 2007-11-07 京セラケミカル株式会社 成形用耐熱性樹脂組成物
JP5895156B2 (ja) * 2011-12-19 2016-03-30 パナソニックＩｐマネジメント株式会社 熱硬化性樹脂組成物、封止材およびそれらを用いた電子部品
JP5534378B2 (ja) 2012-02-24 2014-06-25 荒川化学工業株式会社 ポリイミド系接着剤組成物、硬化物、接着シート、積層体、フレキシブルプリント基板
JP6019883B2 (ja) * 2012-07-25 2016-11-02 日立化成株式会社 熱硬化性樹脂組成物、これを用いたプリプレグ、積層板及び多層プリント配線板
WO2015182469A1 (ja) 2014-05-30 2015-12-03 富士フイルム株式会社 仮接着膜、積層体、仮接着用組成物、デバイスの製造方法およびキット
JP2016113498A (ja) 2014-12-11 2016-06-23 Ｊａｐａｎ Ｖａｌｕａｂｌｅ Ｐｒｏｖｉｄｅｒ株式会社 ポリイミド及びそれを含む印刷用組成物
HK1244833B (zh) * 2015-03-23 2019-11-29 拓自达电线株式会社 树脂浸渗物、复合材料和覆铜层叠体的制造方法
JP6759932B2 (ja) * 2015-09-30 2020-09-23 荒川化学工業株式会社 変性ポリイミド、接着剤組成物、樹脂付銅箔、銅張積層板、プリント配線板及び多層基板
TWI773745B (zh) * 2017-04-24 2022-08-11 日商味之素股份有限公司 樹脂組成物
US20210301133A1 (en) 2017-06-24 2021-09-30 Designer Molecules, Inc. Curable polyimides
CN111083738B (zh) * 2018-10-22 2022-10-21 中国移动通信有限公司研究院 一种负载均衡方法及设备
KR102731754B1 (ko) 2018-12-25 2024-11-18 세키스이가가쿠 고교가부시키가이샤 점착 테이프
JP2020105493A (ja) * 2018-12-26 2020-07-09 荒川化学工業株式会社 ポリイミド、ポリイミド樹脂組成物、ポリイミドフィルム、接着剤、フィルム状接着材、接着層、接着シート、樹脂付銅箔、銅張積層板及びプリント配線板、並びに、ポリイミドの製造方法
JP7762948B2 (ja) * 2020-10-15 2025-10-31 株式会社Mirai Eye 開瞼器
WO2022077397A1 (en) * 2020-10-15 2022-04-21 SZ DJI Technology Co., Ltd. Gimbal control method and gimbal

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0532946A (ja) * 1991-07-31 1993-02-09 Lintec Corp 再剥離型粘着性ポリマー
JP2013079360A (ja) * 2011-09-20 2013-05-02 Nitto Denko Corp 再剥離用粘着剤組成物、再剥離用粘着剤層および再剥離用粘着シート
JP2020132881A (ja) * 2019-02-18 2020-08-31 積水化学工業株式会社 樹脂材料及び多層プリント配線板

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2024002673A (ja) * 2022-06-24 2024-01-11 信越化学工業株式会社 硬化性樹脂組成物、半導体封止材、接着剤、接着フィルム、プリプレグ、層間絶縁材料及びプリント配線板
WO2024019088A1 (ja) * 2022-07-22 2024-01-25 株式会社レゾナック マレイミド樹脂、樹脂組成物、硬化物、シート、積層体、及びプリント配線板
WO2024019084A1 (ja) * 2022-07-22 2024-01-25 株式会社レゾナック ポリマレイミド樹脂、樹脂組成物、硬化物、シート、積層体、及びプリント配線板
WO2024079924A1 (ja) * 2022-10-14 2024-04-18 日本化薬株式会社 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置
WO2024079925A1 (ja) * 2022-10-14 2024-04-18 日本化薬株式会社 樹脂組成物、硬化物、半導体素子、およびドライフィルムレジスト
TWI922798B (zh) 2022-10-14 2026-04-21 日商日本化藥股份有限公司 樹脂組成物、樹脂片材、多層印刷配線板、及半導體裝置
WO2024117235A1 (ja) 2022-12-01 2024-06-06 日産化学株式会社 異物除去用コーティング膜形成組成物及び半導体基板
EP4629280A1 (en) 2022-12-01 2025-10-08 Nissan Chemical Corporation Composition for forming coating film for foreign substance removal, and semiconductor substrate
WO2024157629A1 (ja) * 2023-01-25 2024-08-02 積水化学工業株式会社 光硬化性材料、光硬化性フィルム、及び、硬化物
WO2025058045A1 (ja) * 2023-09-15 2025-03-20 積水化学工業株式会社 接着性フィルム、接着性フィルムの製造方法、接着性樹脂組成物、及び、半導体装置の製造方法
WO2025063226A1 (ja) * 2023-09-19 2025-03-27 積水化学工業株式会社 イミド樹脂材料、硬化性樹脂組成物、接着性フィルム、仮固定材、及び、イミド樹脂材料の製造方法

Also Published As

Publication number Publication date
JP2026042985A (ja) 2026-03-11
CN115702212A (zh) 2023-02-14
JP7194313B2 (ja) 2022-12-21
JP7201859B2 (ja) 2023-01-10
US20230312923A1 (en) 2023-10-05
JP2022109923A (ja) 2022-07-28
JP2022106762A (ja) 2022-07-20
JP7804562B2 (ja) 2026-01-22
JP2023036667A (ja) 2023-03-14
CN115702212B (zh) 2024-01-12
CN117946520A (zh) 2024-04-30
TW202219224A (zh) 2022-05-16
JPWO2022065376A1 (https=) 2022-03-31
JP7201860B2 (ja) 2023-01-10
CN117946519A (zh) 2024-04-30
KR20230074064A (ko) 2023-05-26

Similar Documents

Publication Publication Date Title
JP7804562B2 (ja) 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法
JP7286011B2 (ja) 仮固定材、及び、電子部品の製造方法
TWI849084B (zh) 黏著劑組成物、黏著帶、及電子零件之處理方法
WO2021070623A1 (ja) 粘着剤組成物、粘着テープ、及び、電子部品の製造方法
JP7719724B2 (ja) 粘着剤組成物、粘着テープ、及び、電子部品の処理方法
JP2023138418A (ja) 電子部品の製造方法
JP2023109307A (ja) 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法
JP2024044715A (ja) 電子部品の製造方法
US12617944B2 (en) Curable resin composition, temporary fixing material, and electronic component manufacturing method
CN115917706B (zh) 临时固定材料、以及电子部件的制造方法
JP2024045085A (ja) 接着性フィルム、及び、電子部品の製造方法
JP2023145379A (ja) 半導体装置の製造方法
JP2024045086A (ja) セパレータ付き仮固定材及び巻回体
JP2024112628A (ja) 硬化性樹脂組成物、仮固定材、及び、電子部品の製造方法
JP2025148298A (ja) 接着性樹脂組成物、及び、仮固定材
JP2025088751A (ja) 接着性フィルム、及び、電子部品の製造方法
JP2026020107A (ja) 接着性フィルム
JP2024045084A (ja) 仮固定材、及び、電子部品の製造方法
WO2024154729A1 (ja) 接着フィルム、仮固定材、硬化物、積層体、及び、電子部品の製造方法

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref document number: 2022508852

Country of ref document: JP

Kind code of ref document: A

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

Ref document number: 21872505

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21872505

Country of ref document: EP

Kind code of ref document: A1