WO2022210154A1 - 積層体および半導体装置の製造方法 - Google Patents

積層体および半導体装置の製造方法 Download PDF

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Publication number
WO2022210154A1
WO2022210154A1 PCT/JP2022/013453 JP2022013453W WO2022210154A1 WO 2022210154 A1 WO2022210154 A1 WO 2022210154A1 JP 2022013453 W JP2022013453 W JP 2022013453W WO 2022210154 A1 WO2022210154 A1 WO 2022210154A1
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Prior art keywords
resin film
substrate
laminate
less
resin
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Ceased
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PCT/JP2022/013453
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English (en)
French (fr)
Japanese (ja)
Inventor
中嶋里沙乃
有本由香里
越野美加
荒木斉
富川真佐夫
藤原健典
青島健太
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Toray Industries Inc
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Toray Industries Inc
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Application filed by Toray Industries Inc filed Critical Toray Industries Inc
Priority to EP22780369.9A priority Critical patent/EP4316815A4/en
Priority to JP2022520436A priority patent/JP7790341B2/ja
Priority to US18/284,107 priority patent/US12534399B2/en
Priority to CN202280012984.8A priority patent/CN116847981A/zh
Priority to KR1020237028983A priority patent/KR20230167344A/ko
Publication of WO2022210154A1 publication Critical patent/WO2022210154A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W72/00—Interconnections or connectors in packages
    • H10W72/071—Connecting or disconnecting
    • H10W72/0711—Apparatus therefor
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/34—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions
    • C03C17/3405—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions with at least two coatings of organic materials
    • 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
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
    • C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
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    • 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
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    • 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
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
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    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
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    • 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
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • 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
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    • 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
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    • 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
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    • 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
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    • C09J183/00—Adhesives based on 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; Adhesives based on derivatives of such polymers
    • C09J183/10—Block or graft copolymers containing polysiloxane sequences
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    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10H—INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
    • H10H29/00—Integrated devices, or assemblies of multiple devices, comprising at least one light-emitting semiconductor element covered by group H10H20/00
    • H10H29/80—Constructional details
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    • H10H—INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
    • H10H29/00—Integrated devices, or assemblies of multiple devices, comprising at least one light-emitting semiconductor element covered by group H10H20/00
    • H10H29/80—Constructional details
    • H10H29/85—Packages
    • H10H29/852—Encapsulations
    • H10H29/854—Encapsulations characterised by their material, e.g. epoxy or silicone resins
    • H—ELECTRICITY
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    • 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
    • H10P72/04—Apparatus for manufacture or treatment
    • H10P72/0446—Apparatus for mounting on conductive members, e.g. leadframes or conductors on insulating substrates
    • 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
    • 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
    • H10P72/7412—Handling or holding of wafers, substrates or devices during manufacture or treatment thereof for supporting or gripping using temporarily an auxiliary support the auxiliary support including means facilitating the separation of a device or wafer from the auxiliary support
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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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    • 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
    • H10P72/744—Details of chemical or physical process used for separating the auxiliary support from a device or a wafer
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    • C03C2218/00—Methods for coating glass
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    • C03C2218/32—After-treatment

Definitions

  • the present invention relates to a method of manufacturing a laminate and a semiconductor device. More particularly, the present invention relates to a laminate suitably used when mounting a semiconductor element by laser transfer, and a method of manufacturing a semiconductor device using the same.
  • Patent Documents 1 and 2 As a method of mounting a large number of small semiconductor elements, there is a method of arranging chips from a wafer onto a circuit board using an adhesive stamp obtained from silicone resin (Patent Documents 1 and 2).
  • the adhesive stamp can hold multiple micro LED chips so that multiple chips can be placed on a circuit board in a single pick-and-place process.
  • a method has been proposed in which chips are transferred from a wafer to a transfer substrate having an adhesive layer, and then transferred and mounted on a circuit board or the like by laser lift-off (LLO) (Patent Documents 3, 4, and 5). This method has the advantage of being able to perform high-speed transfer with high positional accuracy.
  • LLO laser lift-off
  • the size of the stamp depends on the wafer size, so there is a limit to the number of semiconductor elements that can be simultaneously transferred. Further, the inventions described in Patent Documents 1 and 2 have a problem that it is necessary to produce a stamp according to the design of the circuit board each time. On the other hand, in the LLO method, there is no need to produce stamps with different designs or restrictions on the area, and a lower cost can be expected. However, it is necessary to form an extremely thin adhesive layer, and there is a concern that the in-plane uniformity is deteriorated and the yield is lowered.
  • the present invention is a laminate in which a substrate 1 having laser transparency, a resin film 1 and a resin film 2 are laminated in this order, and the resin film 1 has a thickness of 200 to 1100 nm. absorbance at any wavelength of 0.4 or more and 5.0 or less when converted to a film thickness of 1.0 ⁇ m, and the adhesion strength of the surface of the resin film 2 opposite to the resin film 1 side is 0
  • the laminated body satisfies 0.02 N/cm or more and 0.3 N/cm or less.
  • FIG. 3A and 3B are diagrams showing a method for producing a laminate 2;
  • FIG. A layered body in which semiconductor elements are layered is sometimes referred to as a layered body 2 hereinafter. It is the figure which showed the production method of the laminated body 2 using a temporary adhesive. It is the figure which showed the production method of the laminated body 2 using a laser lift-off. It is the figure which showed another production method of the laminated body 2 using a semiconductor substrate.
  • FIG. 3 is a diagram showing a step of facing the semiconductor element surface of the laminate 2 and the substrate 2 in the manufacturing method of the semiconductor device. 4 is a diagram showing a process of transferring a semiconductor element to a substrate 2 by irradiating laser light; FIG.
  • the substrate 1 having laser transparency refers to a substrate having an absorbance of 0.1 or less at least at any wavelength from 200 to 1100 nm.
  • Substrates having such absorbance include inorganic substrates such as quartz, sapphire, alkali glass, alkali-free glass, and borosilicate glass.
  • the thickness of the substrate can be selected within a range that does not impair the absorbance, and is preferably 0.1 mm to 5.0 mm. From the viewpoint of substrate handling, the thickness is preferably 0.3 mm or more, and from the viewpoint of availability, it is more preferably 2.0 mm or less.
  • Organic substrates such as PET, aramid, polyester, polypropylene, and cycloolefin can be used for the substrate 1 having laser transparency.
  • the thickness can be selected within a range that does not impair the absorbance, and is preferably 0.05 mm to 3.0 mm. From the viewpoint of substrate handling, the thickness is preferably 0.1 mm or more, and more preferably 1.0 mm or less because light scattering during laser light irradiation can be suppressed.
  • the resin film 1 is a film containing at least a resin and having an absorbance of 0.4 or more and 5.0 or less when converted to a film thickness of 1.0 ⁇ m at any wavelength of 200 to 1100 nm.
  • the absorbance is 0.4 or more
  • the absorbance is 0.6 or more
  • the laser beam can be absorbed particularly near the outermost surface of the resin film 1, so that the transfer can be performed with a laser beam of even lower energy density.
  • the absorbance is preferably 5.0 or less, and more preferably 4.0 or less because versatile resins can be used.
  • Resins contained in the resin film 1 include polyimide, polyimide precursors, polybenzoxazole, polybenzoxazole precursors, urethane resins, novolac resins, polyhydroxystyrenes, polyester resins, acrylic resins, aramid resins, etc., with a thickness of 200 to 1100 nm. , but not limited thereto.
  • These resins preferably have a conjugated structure in their structure. Since the resin has a conjugated structure, it is possible to adjust the absorbance in the range of 0.4 or more and 5.0 or less when the film thickness of 200 to 1100 nm is converted to 1.0 ⁇ m. Structures having a conjugated structure include aromatic structures, among which structures such as biphenyl, imide, benzoxazole, and benzophenone are preferred. With respect to 100 mol % of all the monomer residues of the resin contained in the resin film 1, 60 mol % or more of the monomer residues are monomer residues having a conjugated structure, whereby the absorbance can be adjusted within the above range. . These resins may be contained singly in the resin film 1 or may be contained in plurality.
  • the wavelength at which the resin film 1 satisfies the absorbance is more preferably any one of 248 nm, 266 nm, 308 nm, 355 nm, 532 nm and 1064 nm.
  • the absorbance of the resin film 1 at any one of wavelengths of 248 nm, 266 nm, 308 nm, 355 nm, 532 nm, and 1064 nm is preferably 0.4 or more and 5.0 or less when converted to a film thickness of 1.0 ⁇ m.
  • the wavelength at which the resin film 1 satisfies the above absorbance is more preferably 248 nm, 266 nm, or 355 nm. It is preferable that the absorbance of the resin film 1 at a wavelength of any one of 248 nm, 266 nm and 355 nm is 0.4 or more and 5.0 or less when the film thickness is converted to 1.0 ⁇ m. When the absorbance of the resin film 1 at these wavelengths is within the above range, the laser energy can be efficiently absorbed.
  • the semiconductor element When the adhesive strength is 0.02 N/cm or more, the semiconductor element can be stably held when laminated on the resin film 2 . Further, when the adhesive strength is 0.3 N/cm or less, the semiconductor element can be transferred with a laser beam having a low energy density during transfer. More preferably, the adhesive strength is 0.2 N/cm or less. By setting the thickness within this range, adhesive residue on the semiconductor element can be suppressed when the semiconductor element is transferred by irradiating the laser beam from the side of the substrate 1 having laser transparency.
  • the resin film 2 contains at least a resin, and in order to keep the adhesive strength of the resin film 2 within the above range, the resin film 2 preferably contains a flexible component or a curved component.
  • a flexible component or a bendable component By introducing a flexible component or a bendable component, the glass transition temperature can be lowered and the adhesive strength can be increased.
  • Components that increase flexibility and flexibility include alkylene groups, flexible structures derived from aliphatic groups such as siloxane and silane, flexible structures derived from alkylene glycol and ether groups such as biphenyl ether, alicyclic structures, and olefins. bending structure, and the like.
  • the adhesion strength is improved.
  • the adhesive strength is increased by setting the monomer residues having a structure that imparts flexibility to 70 mol % or less with respect to 100 mol % of all the monomer residues that constitute the resin contained in the resin film 2 . It can be 0.3 N/cm or less.
  • polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, urethane resin, novolac resin, polyester resin, acrylic resin, and polyhydroxystyrene are used within the range satisfying the adhesive strength described above.
  • polysiloxane, polyimidesiloxane, etc. but not limited to these.
  • the resin film 2 in the laminate of the present invention preferably contains a cross-linking agent.
  • a cross-linking agent part of the structure is cross-linked to harden the surface of the resin film 2 and adjust the adhesive strength. Further, the surface of the resin film 2 is crosslinked and strengthened, thereby increasing the effect of suppressing adhesive residue.
  • cross-linking agents include compounds having an alkoxymethyl group or methylol group, such as DML-PC, DML-PEP, DML-OC, DML-OEP, DML-34X, DML-PTBP, DML-PCHP, DML- OCHP, DML-PFP, DML-PSBP, DML-POP, DML-MBOC, DML-MBPC, DML-MTrisPC, DML-BisOC-Z, DMLBisOCHP-Z, DML-BPC, DML-BisOC-P, DMOM-PC, DMOM-PTBP, DMOM-MBPC, TriML-P, TriML-35XL, TML-HQ, TML-BP, TML-pp-BPF, TML-BPE, TML-BPA, TML-BPAF, TML-BPAP, TMOM-BP, TMOM-BPE, TMOM-BPA, TMOM-BPAF, TMOM-BPAP, HML-TP
  • a cross-linking agent having an epoxy group examples include bisphenol A-type epoxy resin, bisphenol F-type epoxy resin, propylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, epoxy group-containing silicones such as polymethyl(glycidyloxypropyl)siloxane, and dimers.
  • examples include acid-modified epoxy resins, but the present invention is not limited thereto.
  • Epiclon 850-S Epiclon HP-4032, Epiclon HP-7200, Epiclon HP-820, Epiclon HP-4700, Epiclon EXA-4710, Epiclon HP-4770, Epiclon EXA-859CRP, Epiclon EXA-1514, Epiclon EXA-4880, Epiclon EXA-4850-150, Epiclon EXA-4850-1000, Epiclon EXA-4816, Epiclon EXA-4822 (all trade names, manufactured by Dainippon Ink & Chemicals, Inc.), Licaresin BEO-60E (hereinafter Product name, Shin Nippon Chemical Co., Ltd.), EP-4003S, EP-4000S (product name, Adeka Co., Ltd.), JER871, JER872, YX-4000, YX-4000H (product name, Mitsubishi Chemical Co., Ltd.), Celoxide 2021P (trade names, manufactured by Daicel Corporation), Showfree PETG, Showfree CDMGB
  • a cross-linking agent having an oxetanyl group examples include OXT-121, OXT-221, OX-SQ-H, OXT-191, PNOX-1009, RSOX (trade names, Toagosei ( Co., Ltd.), “Ethanacol (registered trademark)” OXBP, “Ethanacol” OXTP (both trade names, manufactured by Ube Industries, Ltd.), and the like.
  • Two or more kinds of cross-linking agents may be contained in the resin film 2, and by containing preferably 1 part by weight or more in 100 parts by weight of the resin film 2, adhesive residue can be reduced. More preferably, 5 parts by weight or more is contained in 100 parts by weight of the resin film 2, so that a high effect of suppressing adhesive residue can be obtained.
  • the cross-linking agent is preferably contained in an amount of 300 parts by weight or less in 100 parts by weight of the resin film. Within this range, the flexibility of the resin film 2 is maintained, and the resin film 2 is not broken during transfer of the semiconductor element. From the viewpoint of storage stability in the state of varnish before forming a laminate, it is more preferably 200 parts by weight or less.
  • a curing accelerator can also be included for the purpose of accelerating curing by the cross-linking agent.
  • curing accelerators include imidazoles, tertiary amines or salts thereof, and organic boron salt compounds, among which imidazoles are preferred.
  • imidazoles include imidazole, 2-methylimidazole, 2-ethylimidazole, 2-isopropylimidazole, 2-n-propylimidazole, 2-undecyl-1H-imidazole, 2-heptadecyl-1H-imidazole, 1, 2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenyl-1H-imidazole, 4-methyl-2-phenyl-1H-imidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methyl imidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-ethyl -4-methylimidazolium trimellitate, 1-
  • Curezol C17Z Curezol 2MZ, Curezol 1B2MZ, Curezol 2E4MZ, Curezol 2E4MZ-CN, Curezol 2MZ-AZINE, and Curezol 2MZ-OK (manufactured by Shikoku Kasei Co., Ltd.). ) and the like.
  • the preferred content of the curing accelerator in the resin film 2 is 0.1 parts by weight or more and 5.0 parts by weight or less with respect to 100 parts by weight of the resin film 2 . Within this range, a sufficient effect of accelerating cross-linking can be obtained. From the viewpoint of maintaining the stability of the varnish before forming the laminate, it is more preferably 0.5 to 2.0 parts by weight.
  • the order of lamination of the laminate of the present invention is substrate 1 having laser transparency, resin film 1, and resin film 2, another layer may be provided between them.
  • the substrate 1 having laser transparency and the resin film 2 are positioned on the outermost surface of the laminate.
  • the laminate of the present invention is a laminate in which a substrate 1 having laser transparency, a resin film 1, a resin film 2, and a semiconductor element are laminated in this order, and the thickness of the resin film 1 is any one of 200 to 1100 nm.
  • the absorbance at the wavelength of 1.0 ⁇ m is 0.4 or more and 5.0 or less, and the adhesive strength of the surface where the resin film 2 and the semiconductor element are in contact is 0.02 N/cm or more and 0.02 N/cm or more. It is a laminate having a strength of 3 N/cm or less.
  • the description of the substrate 1 having laser transparency, the resin film 1 and the resin film 2 in the laminate 2 is the same as the explanation for the laminate 1 .
  • the semiconductor element in the present invention includes semiconductor elements such as GaN, AlN, InN, InP, GaAs, Si, and SiC. These semiconductor elements include those in which different types of semiconductors are laminated, and those in which electrode materials, sapphire substrates, glass substrates, wirings, and the like are laminated.
  • the size of the semiconductor element is preferably 5 ⁇ m or more and 5.0 mm or less on one side. More preferably, it is 3.0 mm or less, and the laser light can be condensed and irradiated with a small spot diameter, so that the transfer can be performed with high positional accuracy.
  • the stacking order of the laminate 2 of the present invention may be a substrate 1 having laser transparency, resin film 1, resin film 2, and a semiconductor element, and may have another layer between them.
  • the semiconductor element is formed directly on the resin film 2, and the substrate 1 having laser transparency and the semiconductor element are positioned on the outermost surface of the laminate.
  • the laminate of the present invention has an indentation hardness H2 measured by pressing from the resin film 2 side to the substrate 1 side of 2 MPa or more and 500 MPa or less, and in a state where the resin film 2 is removed from the laminate, It is preferable to satisfy H1>H2, where H1 is the indentation hardness measured by pressing from the resin film 1 side to the substrate 1 side.
  • the indentation hardness H2 measured by pushing from the resin film 2 side to the substrate 1 side in a state where the semiconductor element is removed from the laminated body 2 is 2 MPa or more and 500 MPa or less.
  • the indentation hardness measured by pressing from the resin film 1 side to the laser-transmitting substrate 1 side is H1, H1>H2 is satisfied.
  • the indentation hardness is a physical property that serves as an index when laminating a semiconductor element on the resin film 2. By setting the indentation hardness to an appropriate range, lamination of the semiconductor element on the resin film 2 is facilitated, and subsequent laser light It is possible to improve the accuracy of transferring the semiconductor element by irradiation.
  • the indentation hardness H2 can be measured with a nanoindenter.
  • the hardness can be measured by physically removing the semiconductor elements in the range necessary for hardness measurement from the laminated body 2 to expose the surface of the resin film 2.
  • FIG. Examples of the method for removing the semiconductor element include a method of directly removing it with tweezers or the like, and a method of placing a substrate or film with strong adhesive strength such as a dicing tape on the upper surface of the semiconductor element and peeling it off.
  • the indentation hardness is measured by using a Berkovich indenter (triangular pyramidal diamond indenter) at room temperature and in the atmosphere. conducted in the test.
  • the indentation hardness can be calculated using the value of the indentation region in a range not affected by the base substrate.
  • the indentation hardness H1 is measured in a state where the surface of the resin film 1 is exposed by removing the resin film 2 in the laminate 1 by dry etching.
  • the semiconductor element is physically removed by the above-described method, and the resin film 2 is removed by dry etching to expose the surface of the resin film 1.
  • the dry etching of the resin film 2 is carried out in advance at a portion different from the measurement portion, the etching rate of the resin film 2 is calculated, and the resin film 2 is removed based on the result. Thereafter, the components on the surface of the resin film are analyzed by the ATR-IR method, and removal of the resin film 2 can be confirmed when the components of the resin film 2 are no longer detected.
  • the indentation hardness H1 can be measured using a nanoindenter in the same manner as the indentation hardness H2.
  • the nanoindenter conditions for measuring the indentation hardness H1 are the same as those for measuring the indentation hardness H2.
  • the indentation hardness H2 measured by pressing from the resin film 2 side to the substrate 1 side is 2 MPa or more.
  • the semiconductor element is not buried in the resin film 2 even if it is laminated under pressure. Since the resin film 2 does not adhere to the side surface of the semiconductor element, the transfer can be performed with a laser beam of low energy density.
  • the indentation hardness H2 is 500 MPa or less, the semiconductor elements can be stacked without being damaged even when pressure is applied when stacking the semiconductor elements. More preferably, the indentation hardness H2 is 300 MPa or less. When the indentation hardness H2 is 300 MPa or less, the yield in laminating the semiconductor element on the resin film 2 is improved.
  • the interface between the resin films 1 and 2 can be kept uniform when the semiconductor element is pressure-bonded onto the resin film 2. This improves the positional accuracy when transferring with a laser beam.
  • (t1+t2) when the film thickness of the resin film 1 is t1 ( ⁇ m) and the film thickness of the resin film 2 is t2 ( ⁇ m), (t1+t2) is 1.0 ⁇ m or more and 30 ⁇ m or less. Therefore, t1/t2 is preferably 0.1 or more and 5.0 or less. When (t1+t2) is 1.0 ⁇ m or more, it is possible to reduce the transfer of heat generated when laser light is applied to the semiconductor element, thereby suppressing damage to the semiconductor element.
  • (t1+t2) when (t1+t2) is 30 ⁇ m or less, deformation caused by ablation of the resin film 1 due to laser light irradiation from the side of the substrate 1 having laser transparency is efficiently transferred to the interface between the resin film 2 and the semiconductor element. As a result, the semiconductor element can be transferred. More preferably, (t1+t2) is 20 ⁇ m or less, so that the semiconductor element can be transferred to the counter substrate with good positional accuracy.
  • t1/t2 is preferably 0.1 or more and 5.0 or less.
  • the energy generated by ablation of the resin film 1 does not attenuate in the resin film 2 when laser light is irradiated from the side of the substrate 1 having laser transparency. It reaches the interface with the semiconductor element, and the semiconductor element can be transferred.
  • t1/t2 is 5.0 or less, breakage of the resin film 2 due to energy generated by ablation of the resin film 1 by laser light irradiation can be suppressed. As a result, it is possible to prevent a part of the resin film 1 or the resin film 2 from scattering as debris to the opposing substrate and staining the substrate. More preferably, t1/t2 is 0.3 or more and 3.0 or less.
  • the breaking elongation of the resin film 1 in the laminate of the present invention is preferably 2.0% or more and 30% or less.
  • the elongation at break of the resin film 1 is 2.0% or more, it is possible to prevent the resin film 1 from peeling off from the adjacent substrate or film due to an impact other than laser light irradiation.
  • the breaking elongation of the resin film 1 is 30% or less, the resin film 1 is broken at the boundary between the irradiated portion and the non-irradiated portion when the laser beam is irradiated. can be accurately transcribed.
  • Transfer of a semiconductor element by laser light irradiation usually has a mechanism in which the laser light absorption layer is ablated at the interface between the laser-transmitting substrate and the laser light absorption layer, and the semiconductor element is transferred by the pressure of the generated decomposition gas. is.
  • the portion of the resin film 1 irradiated with the laser beam is broken and falls onto the resin film 2 .
  • the impact of dropping the broken resin film 1 can be used as the energy for transferring the semiconductor element, improving the positional accuracy and enabling transfer even with low-energy laser light irradiation, thereby greatly increasing the processing margin. improves.
  • the breaking elongation of the resin film 1 is more preferably 5% or more and 25% or less. If the elongation at break of the resin film 1 is 5% or more, the possibility of peeling of the resin film 1 other than by laser light irradiation is further reduced, so storage and transportation in the state of a laminate are facilitated. Further, if the elongation at break of the resin film 1 is 25% or less, it is possible to perform transfer with lower energy, which is more preferable.
  • the monomer residues are monomer residues having a rigid structure.
  • the elongation at break can be within the above range.
  • the breaking elongation can be reduced to 30% or less by lowering the molecular weight by the above method.
  • the breaking elongation can be made 2% or more by increasing the molecular weight.
  • a preferred range of the molecular weight of the resin is 1,000 to 100,000 in weight average molecular weight.
  • the resin film 1 When forming the resin film 1, it is possible to control the packing state of the resin by heat treatment so that the elongation at break of the film falls within the above range.
  • Structures containing aromatic rings include planar packing between aromatic rings, and structures containing alkyl chains include packing between alkyl chains.
  • the resin contained in the resin film 1 is a polyimide containing an aromatic ring
  • the heat treatment temperature is lower than 200° C.
  • packing of the aromatic ring in the resin is insufficient and the breaking elongation is low.
  • the elongation at break can be increased by setting the heat treatment temperature to 200° C. or higher within the heat resistance range of the resin.
  • the elongation at break is lower in the case of curing in air than in the case of curing in an inert gas atmosphere.
  • the laminate of the present invention preferably has an indentation hardness H1 of 50 MPa or more and 1000 MPa or less, measured by indenting from the resin film 1 side to the substrate 1 side.
  • an indentation hardness H1 of 50 MPa or more and 1000 MPa or less, measured by indenting from the resin film 1 side to the substrate 1 side.
  • the indentation hardness H1 In order to set the indentation hardness H1 within this range, in the resin contained in the resin film 1, 50 mol % or more of all the monomer residues constituting the resin are monomers having an aromatic ring. It can be achieved by using a residue. Further, since the indentation hardness H1 varies depending on the packing property of the resin as well as the elongation described above, it can be adjusted by changing the curing temperature when the resin film 1 is formed. Specifically, when the heat treatment temperature of the resin film 1 is lower than 200.degree. C., the indentation hardness H1 is decreased, and when the heat treatment temperature is higher than 200.degree. The optimum temperature that can be adjusted and the range of hardness that can be adjusted vary depending on the type of resin.
  • the resin film 1 has polyamic acid
  • conversion from polyamic acid to imide proceeds in the range of 180 ° C. to 300 ° C. Therefore, the packing property of the film is changed, and the hardness can be adjusted.
  • the addition of a cross-linking agent also increases the hardness of the film by cross-linking the film. Therefore, resins with low hardness can be adjusted by using them in combination with the cross-linking agent.
  • a more preferable range of the indentation hardness H1 measured by indentation from the resin film 1 side to the substrate 1 side is 80 MPa to 800 MPa. By setting the thickness in this range, the positional accuracy of the element transferred by laser light irradiation can be increased.
  • the breaking elongation of the resin film 2 in the laminate of the present invention is preferably 100% or more and 1000% or less.
  • the resin film 2 in addition to the function of holding the semiconductor element, the resin film 2 also has the function of receiving the resin film 1 that has been broken by the irradiation of the laser beam during the transfer process, peeling off the semiconductor element from the surface of the resin film 2 and transferring the semiconductor element. have.
  • the breaking elongation of the resin film 2 is 100% or more, the resin film 2 does not break even if the broken resin film 1 is received. As a result, it is possible to suppress the generation of debris on the resin film 1 and the resin film 2 at the time of transfer, and prevent contamination of the counter substrate.
  • the breaking elongation of the resin film 2 is 1000% or less, it is possible to prevent the resin film 2 in the non-laser beam irradiated portion from being pulled and deformed by the deformation of the laser beam irradiated portion of the resin film 2 .
  • the resin contained in the resin film 2 has a flexible structure.
  • Structures having flexibility include structures such as an alkylene structure, a siloxane structure, and an alkylene glycol structure.
  • 20 mol% or more of the monomer residues are monomer residues having a flexible structure with respect to 100 mol% of all the monomer residues constituting the resin.
  • the resin film 1 includes a polyimide having a structure of formula (1), a polyimide precursor having a structure of formula (2), a polybenzoxazole having a structure of formula (3), and a polybenzoxazole having a structure of formula (4). ), and one or more selected from the group consisting of copolymers thereof.
  • R 1 , R 3 , R 7 and R 9 each independently represent a tetravalent organic group having 6 to 40 carbon atoms
  • R 2 , R 4 , R 6 and R 8 each independently represents a divalent organic group having 2 to 40 carbon atoms
  • R5 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
  • Polyimide and polybenzoxazole are resins that have a cyclic structure of imide rings or oxazole rings in the main chain structure.
  • Polyimide precursors and polybenzoxazole precursors, which are precursors thereof, are resins that form an imide ring or benzoxazole ring structure by dehydration and ring closure. It is preferable that the resin contains 10 to 100,000 of the structures represented by formulas (1) to (4) as repeating units. Within this range, the resin film 1 can be applied with an appropriate film thickness.
  • Polyimide can be obtained by reacting a tetracarboxylic acid, a corresponding tetracarboxylic acid dianhydride, a tetracarboxylic acid diester dichloride, or the like with a diamine, a corresponding diisocyanate compound, a trimethylsilylated diamine, or the like, and a tetracarboxylic acid residue and diamine residues.
  • polyamic acid which is one of polyimide precursors obtained by reacting tetracarboxylic dianhydride and diamine, can be obtained by dehydration ring closure by heat treatment. During this heat treatment, a water-azeotropic solvent such as m-xylene may be added.
  • a dehydration condensing agent such as a carboxylic anhydride or dicyclohexylcarbodiimide or a ring-closing catalyst such as a base such as triethylamine, followed by chemical heat treatment for dehydration and ring-closure.
  • a weakly acidic carboxylic acid compound and performing dehydration ring closure by heat treatment at a low temperature of 100° C. or less.
  • Polybenzoxazole can be obtained by reacting a bisaminophenol compound with a dicarboxylic acid, a corresponding dicarboxylic acid chloride, a dicarboxylic acid active ester, etc., and has a dicarboxylic acid residue and a bisaminophenol residue.
  • polyhydroxyamide which is one of polybenzoxazole precursors obtained by reacting a bisaminophenol compound and a dicarboxylic acid, to dehydration ring closure by heat treatment.
  • it can be obtained by adding phosphoric anhydride, a base, a carbodiimide compound, etc., and performing dehydration ring closure by chemical treatment.
  • R 1 and R 3 represent tetracarboxylic acid residues.
  • tetracarboxylic acid residues constituting R 1 or R 3 (COOR 5 ) include pyromellitic acid, 3,3′,4,4′-biphenyltetracarboxylic acid, 2,3,3′,4′ -biphenyltetracarboxylic acid, 2,2',3,3'-biphenyltetracarboxylic acid, 3,3',4,4'-benzophenonetetracarboxylic acid, 2,2',3,3'-benzophenonetetracarboxylic acid , 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane, 2,2-bis(2,3-dicarboxyphenyl)hexafluoropropane, 1,1-bis(3,4-dicarboxyphenyl ) ethane, 1,1-bis(2,3
  • Group tetracarboxylic acid residues and the like can be mentioned. It may also contain residues of two or more of these tetracarboxylic acids. As the tetracarboxylic acid residue, one having an aromatic group is preferable from the viewpoint of absorbance.
  • R 2 and R 4 represent diamine residues.
  • diamine residues constituting R 2 or R 4 include 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, bis(3-amino-4-hydroxyphenyl)sulfone, 2, 2-bis(3-amino-4-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)methane, bis(3-amino-4-hydroxyphenyl)ether, 3,3′-diamino-4, 4′-Biphenol, hydroxyl group-containing diamine residues such as 9,9-bis(3-amino-4-hydroxyphenyl)fluorene, sulfonic acid group-containing diamine residues such as 3-sulfonic acid-4,4′-diaminodiphenyl ether thiol group-containing diamine residues such as dimercaptophenylenediamine, 3,4′-diaminodiphen
  • Aliphatic diamine residues can also be used.
  • Diamine residues such as Jeffamine EDR-148, Jeffamine EDR-176, polyoxypropylene diamine D-200, D-400, D-2000, D-4000 (trade names, manufactured by HUNTSMAN Co., Ltd.), poly Examples of diamine residues having an alkylene oxide group include residues of Elastomer 250P, Elastomer 650P, Elastomer 1000P, and Porea SL100A (trade names of these, manufactured by Kumiai Chemical Industry Co., Ltd.).
  • siloxane diamine residues can also be used, for example, LP-7100, KF-8010, KF-8012, X-22-161A (trade names, Shin-Etsu Chemical Co., Ltd.), which are propylamine-terminated siloxane diamines. (manufactured). Also, two or more of these diamine residues may be contained in combination. From the viewpoint of absorbance, the resin film 1 preferably contains aromatic diamine residues in an amount of 30 mol % or more of the total diamine residues in the resin film 1 .
  • Preferred examples of such monoamines include 2-aminophenol, 3-aminophenol, 4-aminophenol, and the like. You may use 2 or more types of these.
  • R 10 to R 13 are the same as described for R 5 .
  • the prepared sample is fixed to a dedicated sample fixing table via an adhesive (manufactured by Toagosei Co., Ltd., Aron Alpha fast-acting multi-purpose), and a Berkovich indenter (triangular pyramid diamond indenter) is used to indent the resin film 2 of the sample.
  • the indentation hardness H2 was measured by an indentation load/unload test in which the surface was indented in the direction of the resin film 1 and then unloaded.
  • the laser light source, the laminate 2 produced by the method described above, and the opposing substrate were arranged in this order.
  • the surface of the laminate holding the dummy chip and the surface of the counter substrate on which the adhesive layer was formed were held facing each other so that the gap between the surface of the dummy chip and the surface of the adhesive layer was 50 ⁇ m.
  • the laminate and the opposing substrate were aligned using their respective alignment marks.
  • the spot size of the laser beam is adjusted to a square shape of 120 ⁇ m ⁇ 220 ⁇ m with a slit, and the positions of the laser light source and the laminate are adjusted so that one dummy chip is placed in the center of the spot of the laser beam. The laser beam was prevented from hitting the dummy chip to be processed.
  • the position of the semiconductor element on the opposing substrate after transfer was calculated from the alignment marks of the opposing substrate and compared with the position on the laminate 2 .
  • Three chips were transferred at each energy density, and the positional accuracy of the chip with the largest positional deviation was determined as follows. If the positional deviation is less than ⁇ 5 ⁇ m in the X-axis direction and less than ⁇ 5 ⁇ m in the Y-axis direction, the positional accuracy is set to A, ⁇ 10 ⁇ m or more in the X-axis direction, or ⁇ 10 ⁇ m or more in the Y-axis direction. If there is a deviation in the range between them, the position accuracy is set to C, and B is set to the position accuracy.
  • PAA-1 is a resin having the structure of formula (2).
  • PAA-2 is a resin having a structure of formula (2) and formula (5).
  • Production Example 3 (polymerization of resin contained in resin film 2) 344.0 g (0.40 mol) of APPS2, 37.50 g (0.025 mol) of APPS3, and BAHF were placed in a reactor equipped with a thermometer, a dry nitrogen inlet, a heating/cooling device using hot water/cooling water, and a stirring device. 27.47 g (0.075 mol) was charged together with 481.4 g of CHN and dissolved, then 14.81 g (0.10 mol) of PA and 20.00 g of CHN were added and stirred at 60°C for 15 minutes.
  • Production Example 4 Polymerization of Resin Contained in Resin Film 2 254.56 g (0.296 mol) of APPS2, 28.68 g (0.019 mol) of APPS3, BAHF, and 20.33 g (0.056 mol) was charged with 310.56 g of CHN and dissolved, then 16.44 g (0.111 mol) of PA and 38.82 g of CHN were added and stirred at 60° C. for 15 minutes. Subsequently, 68.20 g (0.312 mol) of PMDA and 38.82 g of CHN were added, stirred at 60°C for 1 hour, then heated to 145°C and reacted for 4 hours to obtain a solid content of 50% by weight.
  • PIS-2 is a resin having a structure of formula (1) and formula (5).
  • Production Example 5 (polymerization of resin contained in resin film 2) 39.04 g (0.033 mol) of Elastomer 650P and 131.69 g of NMP were charged together at 40°C into a reactor equipped with a thermometer, a dry nitrogen inlet, a heating/cooling device using hot water/cooling water, and a stirring device. , dissolved. 8.25 g (0.076 mol) of PDA and 16.42 g of NMP were added and dissolved.
  • PAA-3 is a resin having a structure of formula (2) and formula (7).
  • the preliminary dispersion liquid 2 is supplied to an Ultra Apex Mill (manufactured by Kotobuki Kogyo Co., Ltd.) equipped with a centrifugal separator filled with 0.10 mm ⁇ zirconia beads (manufactured by Toray Industries) at 70%, and dispersed for 2 hours at a rotational speed of 8 m / s.

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PCT/JP2022/013453 2021-04-01 2022-03-23 積層体および半導体装置の製造方法 Ceased WO2022210154A1 (ja)

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EP22780369.9A EP4316815A4 (en) 2021-04-01 2022-03-23 Laminate and manufacturing method of semiconductor device
JP2022520436A JP7790341B2 (ja) 2021-04-01 2022-03-23 積層体および半導体装置の製造方法
US18/284,107 US12534399B2 (en) 2021-04-01 2022-03-23 Laminate and manufacturing method of semiconductor device
CN202280012984.8A CN116847981A (zh) 2021-04-01 2022-03-23 层叠体及半导体装置的制造方法
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