WO2024258344A1 - Résine photosensible et son procédé de formation, procédé de nano-impression - Google Patents

Résine photosensible et son procédé de formation, procédé de nano-impression Download PDF

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Publication number
WO2024258344A1
WO2024258344A1 PCT/SG2024/050353 SG2024050353W WO2024258344A1 WO 2024258344 A1 WO2024258344 A1 WO 2024258344A1 SG 2024050353 W SG2024050353 W SG 2024050353W WO 2024258344 A1 WO2024258344 A1 WO 2024258344A1
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WIPO (PCT)
Prior art keywords
nanoparticles
photoresist
resin
sol
gel
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English (en)
Inventor
Jiakang MIN
Siqi LIU
Chaobin He
Hong Liu
Vignesh Suresh
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Agency for Science Technology and Research Singapore
National University of Singapore
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Agency for Science Technology and Research Singapore
National University of Singapore
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • C08L33/12—Homopolymers or copolymers of methyl methacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • C08L33/16—Homopolymers or copolymers of esters containing halogen atoms
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds

Definitions

  • Various embodiments of this disclosure may relate to a photoresist. Various embodiments of this disclosure may relate to a method of forming a photoresist. Various embodiments of this disclosure may relate to a nanoimprinting method.
  • UV-NIL Ultraviolet (UV) nanoimprint lithography
  • NIL next-generation patterning technology that enables the creation of high-resolution nanostructures and provides a complementary option to conventional photolithography
  • UV-NIL technology has been effectively applied in manufacturing advanced optics due to its simple, cost-effective, and high-throughput production procedures.
  • UV-NIL technology has been applied in next generation waveguide optics, thin film encapsulation for organic light emitting diodes (LEDs), and microlens arrays for charge coupled devices (CCDs)Zcomplementary metal oxide semiconductor sensors.
  • LEDs organic light emitting diodes
  • CCDs charge coupled devices
  • FIG. IB is a plot of refractive index (RI) n (measured at wavelength of 633 nm) as a function of wavelength (in nanometer or nm) illustrating the different applications of various photoresists.
  • HRTP high refractive index polymers
  • Various embodiments may relate to a method of forming a photoresist.
  • the method may include forming the photoresist by mixing a sol-gel acrylic polymer-nanoparticles resin with a nanoparticles-dispersed acrylic resin.
  • the sol-gel acrylic polymer-nanoparticles resin may be formed by mixing a monomer, a nanoparticle precursor, a coupling agent, a crosslinker and a photoinitiator in a sol-gel process.
  • Each nanoparticle of a plurality of nanoparticles included in the photoresist may have a diameter selected from a range from 10 nm to 20 nm such that the photoresist is ultra-violet curable.
  • the photoresist may include a solgel aciylic polymer-nanoparticles resin.
  • the photoresist may also include a nanoparticles- dispersed aciy lic resin mixed with the sol-gel acrylic polymer-nanoparticles resin.
  • the sol-gel acrylic polymer-nanoparticles resin may be formed by mixing a monomer, a nanoparticle precursor, a coupling agent, a crosslinker and a photoinitiator in a sol-gel process.
  • Each nanoparticle of a plurality of nanoparticles included in the photoresist may have a diameter selected from a range from 10 nm to 20 nm such that the photoresist is ultra-violet curable.
  • Various embodiments may relate to a nanoimprinting method.
  • the nanoimprinting method may include providing the photoresist as described herein onto a substrate.
  • the nanoimprinting method may also include covering the photoresist using a mold such that the photoresist is molded under a predetermined temperature and a predetermined pressure.
  • the method may further include providing ultraviolet light to cure the photoresist.
  • the method may additionally include removing the mold after the photoresist is cured.
  • FIG. 1 A shows a schematic of a charge coupled device (CCD) without microlens and a charge coupled device (CCD) with microlens.
  • FIG. IB is a plot of refractive index (RI) n (measured at wavelength of 633 nm) as a function of wavelength (in nanometer or nm) illustrating the different applications of various photoresists.
  • RI refractive index
  • FIG. 2 is a general illustration of a method of forming a photoresist according to various embodiments.
  • FIG. 4 is a general illustration of a nanoimprinting method according to various embodiments
  • FIG. 5 A is a table showing the amounts of reactants and processing conditions to form a sample of a sol-gel acrylic polymer-titania (TiO 2 ) resin according to various embodiments.
  • FIG. 5B shows a schematic of the method of forming the titania (TiO 2 ) nanoparticle/sol-gel acrylic resin according to various embodiments and the method of forming micro- and nanostructures using the titania (TiO 2 ) nanoparticle/sol-gel acrylic resin according to various embodiments.
  • FIG. 6A shows a plot of refractive index n and extinction coefficient k as a function of wavelength (in nanometer or nm) illustrating the variation of the refractive index and the extinction coefficient of different compositions of the photoresist according to various embodiments over the visible spectrum.
  • FIG. 6B shows (a) a transmission electron microscopy (TEM) image (inset: magnified image) of the TiO 2 nanoparticle/sol-gel acrylic photoresist according to various embodiments; and (b) a transmission electron microscopy (TEM) image of the formed titania (TiO 2 ) nanoparticles (diameter ⁇ 20 nm) according to various embodiments.
  • TEM transmission electron microscopy
  • FIG. 7 shows a table showing the nanoimpnnt process parameters according to various embodiments.
  • FIG. 8 shows (al) optical microscopy image and (a2 - a3) scanning electron microscopy (SEM) images of the silicon master mold; and (bl) optical microscopy image and (b2 - b3) scanning electron microscopy (SEM) images of the replicated soft mold according to various embodiments.
  • FIG. 9 shows (al) an optical microscopy image and (a2 - a3) scanning electron microscopy (SEM) images of the nanoimprint on 90% titania (TiO ) - sol -gel acrylic photoresist according to various embodiments; (bl) an optical microscopy image and (b2 - b3) scanning electron microscopy (SEM) images of the nanoimprint on 80% titania (TiO 2 ) - sol-gel acrylic photoresist according to various embodiments; and (cl) an optical microscopy image and (c2 - c3) scanning electron microscopy (SEM) images of the nanoimprint on 70% titania (TiO 2 ) - sol-gel acrylic photoresist according to various embodiments.
  • SEM scanning electron microscopy
  • FIG. 10 shows (a) a schematic illustrating formation of poly -methyl methacrylate (PMMA)- titania (TICE) resist according to various embodiments; and (b) a schematic illustrating formation of poly-pentabromobenzyl methacrylate (PBMA)-titania (TiCE) resist according to various embodiments.
  • PMMA poly -methyl methacrylate
  • PBMA poly-pentabromobenzyl methacrylate
  • TiCE titanium-titania
  • FIG. 11 A shows a table of reactants and conditions for synthesis of poly-methyl methacrylate (PMMA)-titama (TiO 2 ) resist and poly-pentabromobenzyl methacrylate (PBMA)-titania (TiO 2 ) resist according to various embodiments.
  • PMMA poly-methyl methacrylate
  • PBMA poly-pentabromobenzyl methacrylate
  • FIG. 11B shows a table of the parameters for nanoimprinting of poly-methyl methacrydate (PMMA)-titania (TiO 2 ) resist and poly-pentabromobenzyl methacrylate (PBMA)-titania (TiO 2 ) resist according to various embodiments.
  • PMMA poly-methyl methacrydate
  • PBMA poly-pentabromobenzyl methacrylate
  • FIG. 12 shows scanning electron microscopy (SEM) images of (a) pure poly-methyl methacrylate (PMMA); (b) poly-methyl methacrylate (PMMA) -titania (TiO 2 ) (TiO 2 : 64.6 wt. %) according to various embodiments (inset: zoomed out image); and (c) poly- pentabromobenzyl methacrylate (PBMA)-titania (TiCE) (TiCh: 69.2 wt %) according to various embodiments (inset: zoomed out image).
  • SEM scanning electron microscopy
  • FIG. 13A shows a plot of refractive index n as a function of wavelength (in nanometer or nm) illustrating the variation of refractive index of poly-methyl methacrylate (PMMA)-titania (TiO 2 ) (TiO 2 : 64.6 wt. %) and poly-pentabromobenzyl methacrylate (PBMA)-titania (TiO 2 ) (TiO 2 : 69.2 wt. %) according to various embodiments under different wavelengths.
  • PMMA poly-methyl methacrylate
  • PBMA poly-pentabromobenzyl methacrylate
  • FIG. 13B shows a plot of extinction coefficient k as a function of wavelength (in nanometer or nm) illustrating the variation of extinction coefficient of poly-methyl methacrylate (PMMA)- titania (TiO 2 ) (TiO 2 : 64.6 wt %) and poly-pentabromobenzyl methacrylate (PBMA)-titania (TiOz) (TiOz: 69.2 wt. %) according to various embodiments under different wavelengths.
  • PMMA poly-methyl methacrylate
  • TiO 2 titanium oxide
  • PBMA poly-pentabromobenzyl methacrylate
  • TiOz titanium oxide
  • FIG. 13C shows transmission electron microscopy (TEM) images of (a) poly-methyl methacrylate (PMMA)-titania (TiO 2 ) (TiO 2 : 64.6 wt. %) (inset: magnified image) and (b) poly- pentabromobenzyl methacrylate (PBMA)-titania (TiO 2 ) (TiO 2 : 69.2 wt. %) (inset: magnified image) according to various embodiments.
  • PMMA poly-methyl methacrylate
  • PBMA poly- pentabromobenzyl methacrylate
  • FIG. 14 shows (a) - (b) scanning electron microscopy (SEM) images of ultraviolet (UV) imprinted micropillars of poly-methyl methacry late (PMMA)-titania (TiO 2 ) (TiO 2 : 64.6 wt. %) according to various embodiments, with the inset showing the cross-sectional SEM image.
  • SEM scanning electron microscopy
  • FIG. 15 shows a cross-sectional scanning electron microscopy ⁇ (SEM) image of imprinted micro pillars of poly-methyl methacrylate (PMMA)-titania (TiO 2 ) (TiO 2 : 64.6 wt. %) (tilted view) according to various embodiments.
  • SEM scanning electron microscopy ⁇
  • FIG. 16 shows optical images of a color array of nanopillars with diameters from 250 nm to 500 nm and pitches from 550 nm to 800 nm of (a) the silicon mold; (b) an imprinted array on poly -pentabromobenzyl methacrylate (PBMA)-titania (TiO 2 ) (TiO 2 : 69.2 wt. %) according to various embodiments; and (c) an impnnted array on poly-pentabromobenzylmethacrylate (PBMA)-titania (TiO 2 ) (TiO 2 : 69.2 wt. %) according to various embodiments coated with 20 nm thick layer of aluminum (Al).
  • PBMA poly -pentabromobenzyl methacrylate
  • TiO 2 titanium oxide
  • FIG. 17 shows field effect scanning electron microscopy (FESEM) images of nanoimprinted color arrays of high refractive index resin poly-pentabromobenzyl methacrylate (PBMA)- titania (TiO 2 ) ( ( (TiO 2 69.2 wt. %) according to various embodiments coated with 20 nm layer aluminum : (a) nanopillar arrays with varying geometry, viz., diameters from 250 nm to 500 nm and pitches from 550 nm to 800 nm; (b) - (c) nanopillar array with diameter 350 nm in diameter and 700 nm in pitch.
  • PBMA poly-pentabromobenzyl methacrylate
  • FIG. 18 shows a table comparing the resist according to various embodiments and several conventional resists for benchmarking.
  • the articles “a”, “an” and “the” as used with regard to a feature or element include a reference to one or more of the features or elements.
  • the term ’‘about” or “approximately” as applied to a numeric value encompasses the exact value and a reasonable variance, e.g. within 10% of the specified value.
  • Embodiments described in the context of one of the photoresists are analogously valid for the other photoresists, embodiments described in the context of a method are analogously valid for a photoresist, and vice versa.
  • FIG. 2 is a general illustration of a method of forming a photoresist according to various embodiments.
  • the method may include, in 202, forming the photoresist by mixing a sol-gel acry lic potymer-nanoparticles resin with a nanoparticles-dispersed acry lic resin.
  • the sol-gel acrylic polymer-nanoparticles resin may be formed by mixing a monomer, a nanoparticle precursor, a coupling agent, a crosslinker and a photoinitiator in a sol-gel process.
  • Each nanoparticle of a plurality of nanoparticles included in the photoresist may have a diameter selected from a range from 10 nm to 20 nm such that the photoresist is ultra-violet curable.
  • the method may relate to forming a photoresist (also referred to as a photoresist mixture) by mixing a sol-gel acrylic polymer-nanoparticles resin and an nanoparticles-dispersed acrylic resin.
  • a photoresist also referred to as a photoresist mixture
  • Each nanoparticle in the photoresist may be of a range from 10 nm to 20 nm.
  • the photoresist may have a high refractive index, e.g., up to 2.
  • the photoresist may have a refractive index selected from a range from 1.9 to 2 under visible light (e.g., under a wavelength selected from a range from 400 nm to 550 nm).
  • the photoresist may have a low extinction coefficient.
  • the photoresist may have an extinction coefficient of 0 or close to 0, e g., under visible light or spectrum (e.g., under a wavelength selected from a range from 400 nm to 700 nm). For instance, the photoresist may have an extinction coefficient of less than 0.1 e.g., less than or equal to 0.01, e.g., 0.
  • Various embodiments may relate to a photoresist which has a high refractive index and a low extinction coefficient.
  • the method as described herein may result in a photoresist with high loading of small nanoparticles (from 10 nm to 20 nm), thereby resulting in the photoresist having a high refractive index and a low extinction coefficient.
  • high-tcmpcraturc treatment which is incompatible with the microelectronic fabrication process, may not be required to achieve a high refractive index.
  • the shrinkage of nanostructures, e.g., nanopillars via high-temperature process may be difficult to control, which affects the fabrication accuracy.
  • the nanoparticle precursor forming the sol-gel acrylic polymcr-nanoparticlcs resin may be a titania precursor.
  • the plurality of nanoparticles may be titania (TiO 2 ) nanoparticles.
  • a first portion of the titania (TiO 2 ) nanoparticles may be formed from the titania precursor of the sol-gel acrylic polymer- nanoparticles resin.
  • a second portion of the titania (TiO 2 ) nanoparticles may be from the nanoparticles-dispersed acrylic resin.
  • the nanoparticles-dispersed acrylic resin may include the second portion of the titania (TiOj) nanoparticles dispersed in an acrylic resin.
  • the nanoparticles- dispersed acry lic resin may include an acrylic resin mixed with TiO 2 nanoparticles.
  • the first portion of the titania (Ti(T) nanoparticles may be covalently bonded to a surrounding polymer matrix.
  • the sol-gel acrylic polymer-nanoparticles resin may include a polymer matrix with TiO 2 nanoparticles bonded to the poly mer matrix.
  • Tire nanoparticles in the photoresist may originate from both the nanoparticles- dispersed acrylic resin and the sol-gel acrylic polymer-nanoparticles resin.
  • the nanoparticles as described herein may have any suitable shape, e g. spherical shape, cuboid shape or irregular shape.
  • the nanoparticles-dispersed acrylic resin may be a TiO 2 nanoparticle dispersed acrylic resin
  • the sol-gel acrylic polymer-nanoparticles resin may be a sol-gel acrylic polymer-TiO 2 resin.
  • the resultant photoresist may be TiO 2 nanoparticle/sol- gel acrylic resin.
  • the TiO 2 nanoparticle/sol-gel acrylic resin may be homogenized with water bath sonication (e.g., for 15 minutes) before being used for nanoimprinting.
  • the photoresist may have a loading of nanoparticles (e.g., TiO 2 nanoparticles) of 70 -wt.% or more (relative to weight of photoresist), e.g., 80 wt.% or more (relative to weight of photoresist), e.g., 90 wt.% or more (relative to weight of photoresist).
  • a higher loading of TiO 2 nanoparticles may lead to a higher refractive index n.
  • the coupling agent forming the sol-gel acrylic polymer- nanoparticles resin may be trimethoxy(7-octen-l-yl)silane.
  • the monomer forming the sol-gel acrylic polymer- nanoparticles resin is methyl-methacrylate (MMA).
  • the crosslinker forming the sol-gel acrylic polymer- nanoparticles resin may be poly (ethylene glycol) dimethacrylate (PEGD).
  • the photoinitiator forming the sol-gel acrylic polymer- nanoparticles resin may be dimethoxyphenyl acetophenone (DPAP).
  • the sol-gel acrylic polymer-nanoparticles resin may be an aciylate-based polymertitanium oxide nanocomposite.
  • the sol-gel acrylic polymer-nanoparticles resin may be an unitary chemical grafting system. High concentrations of sol-gel grafting active substituents, such as -Si-(O-CH3-)j, may be introduced (via the coupling agent) into the acrylic polymer chain.
  • the sol-gel acrylic polymer-nanoparticles resin may be formed by mixing the monomer, the nanoparticle precursor, the coupling agent, the crosslinker and the photoinitiator via magnetic agitation at a temperature selected from a range from 20°C to 25°C.
  • the sol-gel acrylic polymer-nanoparticles resin and the nanoparticles-dispersed acrylic resin may be free of or devoid of any' solvent or plasticizer.
  • the photoresist may be formed by mixing the sol-gel acrylic polymer-nanoparticles resin with the nanoparticles-dispersed acrylic resin in a weight ratio of
  • FIG. 3 is a general illustration of a photoresist according to various embodiments.
  • the photoresist may include a sol-gel acrylic polymer-nanoparticles resin 302.
  • the photoresist may also include a nanoparticles-dispersed acrylic resin 304 mixed with the sol-gel acrylic polymer-nanoparticles resin 302.
  • the sol-gel acrylic polymer-nanoparticles resin 302 may be formed by mixing a monomer, a nanoparticle precursor, a coupling agent, a crosslinker and a photoinitiator in a sol-gel process.
  • Each nanoparticle of a plurality of nanoparticles included in the photoresist may have a diameter selected from a range from 10 nm to 20 nm such that the photoresist is ultra-violet curable.
  • the photoresist may be a mixture of a sol-gel acrylic polymer- nanoparticles resin 302 and a nanoparticles-dispersed acrylic resin 304.
  • the photoresist may 7 have nanoparticles in the range from 10 nm to 20 nm.
  • the sol-gel acrylic polymer-nanoparticles resin 302 may be mixed with the nanoparticles-dispersed acrylic resm 304 in a weight ratio of 1 : 9.
  • the sol-gel acrylic polymier-nanoparticles resin 302 may be mixed with the nanoparticles-dispersed acrylic resm 304 in a weight ratio of 2 : 8.
  • the sol-gel acrylic polymier-nanoparticles resin 302 may be mixed with the nanoparticles-dispersed acrylic resin 304 in a weight ratio of 3 : 7.
  • the predetermined temperature may be any suitable temperature, such as any temperature selected from a range from 30 °C to 70 °C , e.g., 50 °C.
  • the photoresist may be provided onto the substrate by any suitable deposition method, such as drop-casting or coating. By covering the photoresist using the mold under the predetermined temperature and the predetermined pressure, the photoresist may conform to the shape determined by the mold.
  • the photoresist may be cured via a photo-initiated radical copolymerization reaction.
  • the photoinitiator present in the photoresist may help to start the reaction.
  • the mold been removed may refer to separating the mold and the cured photoresist.
  • the demolding may be carried out at any suitable temperature, e.g., at or below room temperature.
  • high refractive polymer/nanoparticle nanocomposites may have a trade-off with extinction coefficient (k). which is generally at about 0.2 as a result of the severe microphase separation and optical scattering between organic polymeric matrices and large sized inorganic nanoparticles.
  • k extinction coefficient
  • This may call for completely miscible nanocomposites, i.e., homogenous distribution of filler particles in the polymer matrices over extremely high nanoparticle loading without serious aggregation, to achieve the highest n and lowest k.
  • Homogeneous dispersion of ultra-small nanoparticles in polymer matrices via in situ sol-gel processing method was developed to resolve the above issues effectively.
  • the resin may then be used to nanoimprint to test its imprint ability to create patterns with high definition and throughput.
  • Various embodiments may introduce a high concentration of sol-gel grafting active substituents, such as -OH and -Si-(O-CH3-)3, into the polymer chain and may then combine it with the (TiO 2 dispersed acrylic resin.
  • the chemical grafted acrylic polymer (TiO: 2 photoresist may act as both surfactant and matrix concurrently, creating a polymer-supported dispersion of inorganic nanoparticles under in situ sol-gel grafting manner with high nanoparticle loading and small diameter of ⁇ 10 nm - 20 nm.
  • Experiment A relates to formation of a photoresist with addition of nanoparticles- dispersed acrylic resin
  • Experiment B relates to formation of a photoresist without addition of nanoparticles-dispersed acrylic resin.
  • high-temperature treatment may be required to achieve a high refractive index, which is not compatible with the microelectronic fabrication process.
  • the shrinkage of nanostructures e.g., nanopillars, via high-temperature process may be difficult to control, which affects the fabrication accuracy.
  • a sol-gel acrylic polvmer-TiOz resin sample may be formed by using the amounts of reactants and processing conditions as shown in FIG. 5A.
  • FIG. 5A is a table showing the amounts of reactants and processing conditions to form a sample of a sol-gel acrylic polymer- titania (TiO ) resin according to various embodiments. All chemicals were purchased from Sigma-Aldrich. The MMA (monomer), TT (titania precursor), TS (coupling agent), PEGD (crosslinker), and DPAP (photoinitiator) were mixed into one uniform sol mixture by vigorous magnetic agitating at room temperature.
  • the TiO 2 nanoparticle/sol-gel acrylic resin was prepared by mixing TiO 2 nanoparticle dispersed acrylic resin and sol-gel acrylic polymer-TiO 2 resin at designed weight ratios (9 : 1, 8 : 2, and 7 : 3, respectively). Then, the mixture was homogenized with water bath sonication for 15 min for imprint use.
  • FIG. 5B shows a schematic of the method of forming the titania (TiO 2 ) nanoparticle/sol-gel acrylic resin according to various embodiments and the method of forming micro- and nanostructures using the titania (TiO 2 ) nanoparticle/sol-gel acrylic resin according to various embodiments.
  • the synthesis of dielectric high refractive and low loss resins may evolve from the acrylate-based polymer-titanium oxide nanocomposites via the sol-gel approach.
  • the combination of sol-gel prepared acrylate-based polymer-titanium oxide nanocomposites and TiO 2 nanoparticle dispersed acrylic resins may result in TiO 2 nanoparticle/sol-gel acrylic photoresist.
  • the TiO 2 nanoparticle/sol-gel acrylic photoresist can be applied for nanoimprinting lithography (NIL) to make large-area patterns at nano-meter scales for advanced optics, with advantages such as great nanoimprint capability, high refractive index and extremely low extinction coefficient, solvent -free, decent fidelity' with low shrinkage and high material integrity with nanoparticle-sol gel in-situ linkage over other TiOi-based resin.
  • NIL nanoimprinting lithography
  • FIG. 6A shows a plot of refractive index n and extinction coefficient k as a function of wavelength (in nanometer or nm) illustrating the variation of the refractive index and the extinction coefficient of different compositions of the photoresist according to various embodiments over the visible spectrum.
  • the photoresists may have different liCb/sol-gel weight ratios of 90%, 80% and 70%, respectively.
  • the value of n gradually reduces from ⁇ 2.0 to 1.83.
  • the resin with a 90% weight ratio exhibits the highest n, around 1.9 ⁇ 2.0, in the visible regime. It can be observed that n drops when the weight ratio reduces.
  • FIG 6B shows (a) a transmission electron microscopy (TEM) image (msct: magnified image) of the TiO 2 nanoparticlc/sol-gcl acrylic photoresist according to various embodiments; and (b) a transmission electron microscopy (TEM) image of the formed titania (TiO 2 ) nanoparticles (diameter ⁇ 20 nm) according to various embodiments.
  • TEM transmission electron microscopy
  • TiO 2 formed titania nanoparticles
  • a NIL process may be applied to test the nanoimprint capability for the designed TiO 2 nanoparticle/sol-gel acrylic photoresist.
  • FIG. 7 shows a table showing the nanoimprint process parameters according to various embodiments.
  • the photoresist may be drop-casted on a silicon wafer or quartz substrate and may then get covered by the NIL mold timely.
  • the photoresist may then flow into the NIL mold fully under certain pressure and temperature.
  • the imprinted photoresist may get in-situ cured completely by sustaining the photo-initiated radical copolymerization imposed by the successive ultraviolet radiation exposure.
  • the cured photoresist may be demolded at room temperature.
  • FIG. 8 shows (al) optical microscopy image and (a2 - a3) scanning electron microscopy (SEM) images of the silicon master mold; and (bl) optical microscopy image and (b2 - b3) scanning electron microscopy (SEM) images of the replicated soft mold according to various embodiments.
  • the TiO 2 nanoparticle/sol-gel acrylic photoresist was drop casted on top of the adhesion layer of the quartz substrate, and the silicon master mold may be applied onto the deposited photoresist.
  • the resin was then heated at 50°C for 120s, followed by UV curing for 360s (in 5s On/Off cycle), which was applied to solidify the TiO 2 nanoparticle/sol- gel acrylic resin.
  • the pressure was set to 1.0 bar.
  • the soft mold (ofthe cured photoresist) formed may then be used to fabricate metalenses.
  • FIG. 9 shows (al) an optical microscopy image and (a2 - a3) scanning electron microscopy (SEM) images of the nanoimprint on 90% titania (TiO 2 ) - sol-gel acrylic photoresist according to various embodiments; (bl) an optical microscopy image and (b2 - b3) scanning electron microscopy (SEM) images of the nanoimpnnt on 80% titania (TiO 2 ) - solgel acrylicphotoresist according to various embodiments; and (cl) an optical microscopy image and (c2 - c3) scanning electron microscopy (SEM) images of the nanoimprint on 70% titania (TiO 2 ) - sol-gel acrylic photoresist according to various embodiments.
  • the results validate that the developed TiO 2 nanoparticle/sol-gel acrylic photoresist may show great capability in nanoimprint applications.
  • the sol-gel grafted TiO 2 -acrylic polymers may provide a polymer-supported dispersion of TiO 2 nanoparticles with high nanoparticle loading and small diameter ⁇ 10 nm - 20 nm.
  • the developed TiO 2 nanoparticle/sol-gel acrylic resins may have high refractive index (1.90 ⁇ 2.0) and extremely low extinction coefficients ( ⁇ 0).
  • the developed TiO 2 nanoparticle/sol-gel acrylic resins may demonstrate great capability for nanoimprinting.
  • High concentration of sol-gel grafting active substituents, such as -Si-(O-CH3-)3, may be introduced into the acrylic polymer chain.
  • the high refractive index nanoimprintable TiO 2 nanoparticle/sol-gel acrylic photoresist may be suitable for nanoimprinting of optical nanostructures, flat optics for advanced optical applications (e.g. to reduce size of conventional optical devices, forming high quality augmented reality/virtual reality (AR/VR) devices).
  • the high refractive index of the photoresist may enable miniaturization of conventional optics and thereby reduce the overall device size.
  • FIG. 10 shows (a) a schematic illustrating formation of poly-methyl methacrylate (PMMA)-titania (TiCh) resist according to various embodiments; and (b) a schematic illustrating formation of poly-pentabromobenzyl methacrylate (PBMA) -titania (TiO 2 ) resist according to various embodiments.
  • PMMA poly-methyl methacrylate
  • PBMA poly-pentabromobenzyl methacrylate
  • methyl methacrylate (MMA, monomer), titanium isopropoxide (TI, titania precursor), trimcthoxy(7-octcn-l-yl)silanc (TS, coupling agent), poly(cthylcnc glycol di meth acrylate) (PEGD, crosslinker), and dimethoxy phenylacetophenone (DPAP, photoinitiator) may be combined into one uniform sol mixture by vigorous magnetic agitating at room temperature.
  • the soliquid may be spin-coated on a silicon wafer and may in-situ get cured by sustaining the photo -initiated radical copolymerization imposed by the ultraviolet radiation to synthesize the trimethoxysilane tailored PMMA-graft-titanium as a thin film.
  • the PMM A-TiO 2 thin film may be prepared followed by 1 hour baking at 80 °C to enable the intact transition of titanium to TiO 2 .
  • hydroxyl -substituted pentabromobenzyl methacrylate (BMA, monomer), titanium isopropoxide (TI, titania precursor), tnmethoxy(7-octen-l- yl)silane (TS, coupling agent), polyethylene glycol dimethacrylate) (PEGD, crosslinker), and dimethoxy phenylacetophenone (DPAP, photoinitiator) may be combined into one uniform sol mixture by vigorous magnetic agitating at room temperature.
  • BMA pentabromobenzyl methacrylate
  • TI titanium isopropoxide
  • TS tnmethoxy(7-octen-l- yl)silane
  • PEGD polyethylene glycol dimethacrylate
  • DPAP dimethoxy phenylacetophenone
  • the soliquid may be spin-coated on a silicon wafer and may in-situ get cured by sustaining the photo-initiated radical copolymerization imposed by the ultraviolet radiation to synthesize the trimethoxysilane tailored PBMA-graft-titanium as a thin film.
  • the PBMA-TiO 2 thin film may be prepared followed by 1 hour baking at 80 °C to enable the intact transition of titanium to TiO 2 for further optical property examination.
  • ultraviolet radiation imprint for PMMA- TiO 2 and PBMA -TiO 2 by using micro-featured negative-type molds may be developed.
  • FIG. 11A shows a table of reactants and conditions for synthesis of poly-methyl methacry late (PMMA)-titania (TiO 2 ) resist and polypentabromobenzyl methacrylate (PBMA)-titania (TiO 2 ) resist according to various embodiments.
  • PMMA poly-methyl methacry late
  • PBMA polypentabromobenzyl methacrylate
  • Various embodiments may relate to a method of forming a photoresist by mixing a monomer, a nanoparticle precursor, a coupling agent, a cross-linker and a photoinitiator in a sol-gel process.
  • the photoresist may include a plurality of nanoparticles, such that each nanoparticle of the plurality of nanoparticles has a diameter selected from a range from 10 nm to 20 nm.
  • Various embodiments may relate to a photoresist formed by' such a method.
  • FIG. 13 A shows a plot of refractive index n as a function of wavelength (in nanometer or nm) illustrating the variation of refractive index of poly-methyl methacrylate (PMMA)-titania (TiO 2 ) (TiO 2 : 64.6 wt.
  • PMMA poly-methyl methacrylate
  • TiO 2 titanium oxide
  • FIG. 13B shows a plot of extinction coefficient k as a function of wavelength (in nanometer or nm) illustrating the variation of extinction coefficient of poly-methyl methacrylate (PMMA)-titania (TiO 2 ) (TiO 2 : 64.6 wt. %) and poly-pentabromobenzyl methacrylate (PBMA)-titania (TiO 2 ) (TiO 2 : 69.2 wt %) according to various embodiments under different wavelengths.
  • PMMA poly-methyl methacrylate
  • TiO 2 TiO 2 : 64.6 wt.
  • PBMA poly-pentabromobenzyl methacrylate
  • FIG. 13C shows transmission electron microscopy (TEM) images of (a) poly-methyl methacrylate (PMMA)-titania (TiO 2 ) (TiO 2 : 64.6 wt. %) (inset: magnified image) and (b) poly-pentabromobenzyl methacry late (PBMA)-titania (TiO 2 ) (TiO 2 : 69.2 wt. %) (inset: magnified image) according to various embodiments.
  • Various embodiments may relate to a solvent free approach to achieve high nanoparticles loading (about 64% - 69%) and small spatial size (diameter of about 10 nm - 20 nm) simultaneously.
  • FIG. 14 shows (a) - (b) scanning electron microscopy (SEM) images of ultraviolet (UV) imprinted micropillars of poly-methyl methacrylate (PMMA)-titania (TiO 2 ) (TiO 2 64.6 wt. %) according to various embodiments, with the inset showing the cross-sectional SEM image.
  • the SEM images demonstrate the microimprint ability of the acrylic resins thin films, which may result in micropillar arrays with good pattern fidelity.
  • the diameter and pitch of the micropillars array are ⁇ 1 and ⁇ 2 um obtained using high refractive index resin of poly-methyl methacrylate (PMMA)-titania (TiO 2 ) (TiO 2 64.6 wt. %).
  • FIG. 15 shows a cross-sectional scanning electron microscopy (SEM) image of imprinted micro pillars of poly-mcthyl methacrylate (PMMA)-titania (TiO 2 ) (TiO 2 : 64.6 wt. %) (tilted view) according to various embodiments.
  • SEM scanning electron microscopy
  • the cross-sectional SEM image of poly-methyl methacrylate (PMMA)-titania (TiO 2 ) (TiO 2 : 64.6 wt %) nanoimprinted acrylic resin thin film shows the residual layer thickness and pillar heights are ⁇ 10 nm and ⁇ 1 pm, respectively.
  • Structural color arrays are designed in order to demonstrate the application of the high refractive index resin for anti-counterfeiting.
  • Arrays with nanopillars were patterned onto silicon to make the mold. The pattern may then be transferred to a soft mold and imprinted onto poly-pentabromobenzyl methacrylate (PBMA)-titania (TiO 2 ) (TiO 2 : 69.2 wt. %) to form imprinted nanopillars.
  • PBMA poly-pentabromobenzyl methacrylate
  • TiO 2 titanium-titania
  • FIG. 16 shows optical images of a color array of nanopillars with diameters from 250 nm to 500 nm and pitches from 550 nm to 800 run of (a) the silicon mold; (b) an imprinted array on poly-pentabromobenzyl methacrylate (PBMA)-titania (TiO 2 ) (TiO 2 : 69.2 wt. %) according to various embodiments; and (c) an imprinted array on polypentabromobenzylmethacrylate (PBMA)-titania (TiO 2 ) (TiO 2 : 69.2 wt. %) according to various embodiments coated with 20 nm thick layer of aluminum (Al).
  • PBMA poly-pentabromobenzyl methacrylate
  • TiO 2 titanium oxide
  • nanostructured colors may exhibit the following advantages: (1) higher resolution, (2) brighter colors under sunlight, (3) better durability , and (4) dynamic tuning by changing the surface morphology .
  • the polymer systems may have two kinds of grafting active substituents (-OH and - Si-(O-CH 3 -) 3 ) in the macromolecular chain and employ in-situ formation ofTiO 2 nanoparticles as inorganic high refractive index feedstock to achieve high refractive index (n ⁇ 1 .95) and low extinction coefficient (k -0.01) in the visible spectrum (wavelength from 400nm to 700nm).
  • TiO 2 nanoparticles may be chemically grafted on the resin matrices without using any solvent, which may realize the high nanoparticle loading (64%- 69%) and small spatial size (diameter: 10 nm - 20 nm) simultaneously, leading to the achievement of the high n and low k in the visible domain.
  • the precursor (trimethoxy(7-octen- l-yl)silane) for the grafting active substituent Si-(O-CH3-)3 may have a longer and more simplified molecular side chain to decrease steric hindrance during co-polymerization and increase nanoparticles grafting efficiency.
  • the enhanced nanoparticles grafting efficiency may realize the higher nanoparticle loading (such as: 69.2%) and smaller spatial size (diameter: 10 nm - 20 nm) simultaneously, which further leads to the achievement of the high n and low k in the visible domain.
  • the developed chemically grafted acrylic polymer-TiO 2 resins may contain abundant carbon-carbon double bonds, which are ultraviolet curable.
  • the resins may be feasible for UV nanoimpnnt lithography and may be able to achieve high pattern fidelity with -10 nm thick residual layer.
  • the optically active transparent acrylic resins can undergo UV radiation imprint with extremely good reliability and reiterative pattern-clone performance.
  • the double bond may cater to various requirements for scaling up. Also, there may have potential for applications with require no or minimal residual layer.
  • Various embodiments e.g. nano-pillar arrays
  • Various embodiments may have high transparency and efficiency, lower loss optical materials for advanced optics and photonics compared with low refractive index polymers. Various embodiments may allow wider field of view and larger deflection angle for the next generation of diffractive optical elements for AR/VR devices. Various embodiments may be suitable for making micro- and nanostructures via nanoimprint lithography with a thin residual layer (—10 nm thickness) for flat optical components and other optical components.

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Abstract

Divers modes de réalisation peuvent concerner un procédé de formation de résine photosensible. Le procédé peut consister à former la résine photosensible en mélangeant une résine de nanoparticules de polymère acrylique sol-gel avec une résine acrylique dispersée dans des nanoparticules. La résine de nanoparticules de polymère acrylique sol-gel peut être formée en mélangeant un monomère, un précurseur de nanoparticules, un agent de couplage, un agent de réticulation et un photoinitiateur dans un procédé sol-gel. Chaque nanoparticule d'une pluralité de nanoparticules incluses dans la résine photosensible peut avoir un diamètre choisi dans une plage allant de 10 nm à 20 nm de telle sorte que la résine photosensible peut être durcie aux ultraviolets.
PCT/SG2024/050353 2023-06-15 2024-05-27 Résine photosensible et son procédé de formation, procédé de nano-impression Ceased WO2024258344A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101423678A (zh) * 2008-10-29 2009-05-06 国家纳米科学中心 一种光固化纳米复合涂料
WO2022204586A1 (fr) * 2021-03-26 2022-09-29 Pixelligent Technologies Llc Formulations de zircone et de dioxyde de titane et nano-composites pour lithographie par nano-impression

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101423678A (zh) * 2008-10-29 2009-05-06 国家纳米科学中心 一种光固化纳米复合涂料
WO2022204586A1 (fr) * 2021-03-26 2022-09-29 Pixelligent Technologies Llc Formulations de zircone et de dioxyde de titane et nano-composites pour lithographie par nano-impression

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YOON GWANHO, KIM KWAN, HUH DAIHONG, LEE HEON, RHO JUNSUK: "Single-step manufacturing of hierarchical dielectric metalens in the visible", NATURE COMMUNICATIONS, vol. 11, no. 1, XP093017216, DOI: 10.1038/s41467-020-16136-5 *
ZHANG, X. ET AL.: "Stabilized dispersions of titania nanoparticles via a sol-gel process and applications in UV-curable hybrid systems", POLYMER INTERNATIONAL, vol. 55, no. 4, 7 March 2006 (2006-03-07), pages 466 - 472, XP002627241, [retrieved on 20240829], DOI: 10.1002/P1.2000 *

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