Classifications

• • 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
  • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
  • C08F222/36—Amides or imides
  • C08F222/40—Imides, e.g. cyclic imides
  • C08F222/402—Alkyl substituted imides
• • 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
  • C08F2/00—Processes of polymerisation
  • C08F2/46—Polymerisation initiated by wave energy or particle radiation
  • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
• • 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
  • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
  • C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
  • C08F212/36—Divinylbenzene
• • 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
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
• • 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
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
  • C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate
• • 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
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
  • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
• • 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
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
  • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
• • 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
  • C08F220/10—Esters
  • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
  • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
• • 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
  • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
  • C08F222/10—Esters
  • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
  • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
  • C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
• • 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
  • C08F224/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
• • 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
  • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
  • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/30—Inkjet printing inks

Definitions

• the present disclosure relates to a curable composition, particularly to a curable composition for inkjet adaptive planarization.
• IAP Inkjet Adaptive Planarization
• a substrate e.g., a wafer containing an electronic circuit
• jetting liquid drops of a curable composition on the surface of the substrate and bringing a flat superstrate in direct contact with the added liquid to form a flat liquid layer.
• the flat liquid layer is typically solidified under UV light exposure, and after removal of the superstrate a planar surface is obtained which can be subjected to subsequent processing steps, for example baking, etching, and/or further deposition steps.
• a curable composition can comprise a polymerizable material and an initiator, wherein the polymerizable material comprises a first monomer and a second monomer, the second monomer including a ring structure selected from a maleimide-ring, a pyrone ring, or a 2-furanone ring; the second monomer is soluble in the first monomer, and the curable composition has a viscosity of not greater than 10 mPa-s.
• an amount the second monomer can be at least 2 wt% and not greater than 20 wt% based on the total weight of the curable composition.
• the second monomer of the polymerizable material can include a maleimide ring structure.
• the second monomer can include N- benzylmaleimide (N-BMI); N-cyclohexylmaleimide (N-CMI); N-phenylmaleimide (N-PMI); bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BEMMI); or any combination thereof.
• the first monomer of the polymerizable material can include an acrylate-monomer.
• the acrylate monomer can include an aromatic group.
• the acrylate monomer can include benzyl acrylate (BA); 1 -naphthyl acrylate (1-NA); bisphenol A dimethacrylate (BPADMA); or any combination thereof.
• the polymerizable material of the curable composition can include at least one further monomer in addition to the first monomer and the second monomer.
• the at least one further monomer can include a substituted or unsubstituted divinyl benzene (DVB).
• the polymerizable material of the curable composition of the present disclosure can comprise an aromatic acrylate monomer, a monomer including a maleimide ring, and a substituted or unsubstituted divinyl benzene (DVB).
• an aromatic acrylate monomer a monomer including a maleimide ring
• a substituted or unsubstituted divinyl benzene (DVB) a substituted or unsubstituted divinyl benzene
• the curable composition can be essentially free of a non-polymerizable solvent.
• a laminate in another embodiment of the present disclosure, can comprise a substrate and a cured layer overlying the substrate, wherein the cured layer can comprise an acrylate/maleimide copolymer; a total carbon content of least 74%; and a weight loss after heat treatment at a temperature of 250°C for 90 seconds being not greater than 2.5% based on the total weight of the cured layer before the heat treatment.
• the cured layer of the laminate can have an average Storage Modulus of at least 4.5 GPa.
• the acrylate/maleimide copolymer contained in the cured layer of the laminate can further comprise divinyl benzene.
• a method of forming an article can comprise: applying a layer of a curable composition on a substrate, wherein the curable composition comprises a polymerizable material and a photoinitiator, and wherein the polymerizable material comprises a first monomer and a second monomer, the second monomer including a ring structure selected from a maleimide-ring, a pyrone ring, or a 2-furanone ring; the second monomer is soluble in the first monomer; and the curable composition has a viscosity of not greater than 10 mPa-s.
• the method can further include bringing the curable composition into contact with a superstrate; curing the curable composition with light or heat to form a cured layer; removing the superstrate from the cured layer; and processing the substrate with the cured layer to make the article.
• curing can comprise a conversion of at least 65% of all double bonds contained in the polymerizable material within 10 seconds.
• the polymerizable material of the curable composition can include an acrylate monomer as the first monomer and a monomer including a maleimide ring as the second monomer.
• the polymerizable material can include at least one further monomer.
• the at least one further monomer can be a substituted or unsubstituted divinyl benzene.
• the cured layer can have a weight loss after a heat treatment at a temperature of 250°C for 90 seconds of not greater than 2.5% based on the total weight of the cured layer.
• the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
• a process, method, article, or apparatus that comprises a list of features is not necessarily limited only to those features but may include other features not expressly listed or inherent to such process, method, article, or apparatus.
• the present disclosure is directed to a curable composition
• a curable composition comprising a polymerizable material which includes a first monomer and a second monomer, wherein the second monomer is soluble in the first monomer and includes a ring structure.
• the ring structure contained in the second monomer can be a maleimide-ring, or a pyrone ring, or a 2-furanone ring.
• the curable composition can have a viscosity of not greater than 10 mPa s, and may be particularly suitable for use in inkjet adaptive planarization (LAP) for making planar cured layers with a fast curing kinetic, a high thermal stability, good mechanical strength and a high etch resistance.
• LAP inkjet adaptive planarization
• the term monomer relates to one or more polymerizable monomer types. If not indicated otherwise, the monomer types can be substituted or unsubstituted monomers.
• the second monomer can be a monomer including at least one maleimide ring.
• the second monomer can include one maleimide ring, hereinafter also called a mono-maleimide.
• the second monomer can include two maleimide rings, hereinafter called a bis-maleimide.
• the maleimide ring can be substituted on the ring nitrogen with an aromatic group.
• Non-limiting examples of mono-maleimides can be: N-benzylmaleimide (N-BMI) (CAS 1631-26-1); N- cyclohexylmaleimide (N-CMI) (CAS 1631-25-0); N-phenylmaleimide (N-PMI) (CAS 941-69- 5); bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BEMMI) (CAS 105391-33-1); N-(4- nitrophenyl)-maleimide (CAS 4338-06-1); N-tert-butylmaleimide (CAS 4144-22-3), N-ethyl- maleimide (CAS 128-53-0); N-(2-hydroxyethyl) maleimide (CAS 1585-90-6); N-(2,4,6- trichlorophenyl)maleimide (CAS 13167-25-4); moreover, non-limiting examples of bis- maleimides may be: bis(3-ethyl-5-methyl-4
• the first monomer of the polymerizable material can be present in a larger amount than the second monomer and may dissolve the second monomer. Accordingly, the first monomer can act as a solvent, and the curable composition can be essentially free of a non-polymerizable solvent. In another certain aspect, however, the curable composition can also include a non- polymerizable solvent.
• a weight% ratio of the first monomer to the second monomer can be not greater than 3:1; such as not greater than 4:1, not greater than 5:1, not greater than 8 : 1 , or not greater than 10:1.
• the first monomer can include at least one acrylate monomer.
• the term acrylate monomer relates to any monomer structure including an acrylate or substituted acrylate unit, for example a methacrylate unit.
• the acrylate monomer can include an aromatic group.
• suitable acrylate monomers can be benzyl acrylate (BA); 1 -naphthyl acrylate (1-NA); bisphenol A dimethacrylate (BPADMA); or any combination thereof.
• acrylate monomers that can dissolve maleimide- monomers can be, for example, dicyclopentenyl oxyethyl acrylate, dicyclopentanyl acrylate, o- phenyl benzyl acrylate and isobornyl acrylate, but are not limited thereto.
• the polymerizable material can include at least one further monomer type, and/or a polymerizable oligomer and/or a polymerizable polymer.
• the at least one further monomer can be a di-or trifunctional monomer, having the ability to act as a cross-linking agent.
• the at least one further monomer can be substituted or unsubstituted divinyl benzene (DVB).
• the polymerizable material of the curable composition can comprise an aromatic acrylate monomer, a monomer including a maleimide ring, and a substituted or unsubstituted divinyl benzene (DVB).
• the viscosity of the curable composition can be not greater than 20 mPa s, such as not greater than 15 mPa s, not greater than 12 mPa s, not greater than 10 mPa s, not greater than 9 mPa s, or not greater than 8 mPa s. In other certain embodiments, the viscosity may be at least 2 mPa s, such as at least 3 mPa s, at least 4 mPa s, or at least 5 mPa s.
• the curable composition can have a viscosity of not greater than 10 mPa s.
• all viscosity values relate to viscosities measured at a temperature of 23°C with the Brookfield method using a Brookfield Viscometer at 200 rpm.
• the amount of polymerizable material in the curable composition can be at least 70 wt%, at least 75 wt%, at least 80 wt%, at least 85 wt%, at least 90 wt%, or at least 95 wt%.
• the amount of polymerizable material may be not greater than 99 wt%, such as not greater than 98 wt%, not greater than 97 wt%, not greater than 95 wt%, not greater than 93 wt%, not greater than 90 wt%, or not greater than 85 wt% based on the total weight of the curable composition.
• the amount of polymerizable material can be a value between any of the minimum and maximum values noted above.
• the amount of polymerizable material can be at least 80 wt% and not greater than 98 wt%.
• the curable composition can further contain one or more optional additives.
• optional additives can be stabilizers, dispersants, solvents, surfactants, inhibitors or any combination thereof.
• curable compositions can be made having a desired low viscosity of less than 10 mPa s, and leading to cured materials having a low shrinkage during UV curing, an excellent mechanical stability, a high heat stability, and a good etch resistance.
• the curable composition can be applied on a substrate to form a cured layer.
• the curing can be conducted under light radiation, e.g. UV radiation, or exposure to heat.
• the combination of substrate and cured layer overlying the substrate is called a laminate.
• the cured layer of the laminate can have a hardness of at least 0.3 GPa, such as at least 0.32 GPa, at least 0.34 GPa, at least 0.36 GPa, or at least 0.38 GPa.
• the storage modulus of the cured layer can be at least 4.5 GPa, such as at least 4.6 GPa, at least 4.7 GPa, at least 4.8 GPa, at least 4.9 GPa, at least 5.0 GPa, or at least
• the cured layer of the laminate can further have a good heat stability.
• the photo-cured layer can have a weight loss after a heat treatment at 250°C for 90 seconds of not greater than 4%, or not greater than 3.5%, or not greater than 3%, or not greater than 2.7%, or not greater than 2.5%, or not greater than 2.3%, or not greater than 2.0%, or not greater than 1.7%.
• the cured layer of the laminate of the present disclosure can have a high carbon content.
• the carbon content of the cured layer can be at least 70 wt% based on the total weight of the cured layer, such as at least 71 wt%, at least 72 wt%, at least 73 wt%, at least 74 wt%, or at least 75 wt%.
• the carbon content can be at least 74 wt%.
• the cured layer of the laminate may have a hydrogen content of not greater than 6.3 wt% based on the total weight of the cured layer, such as not greater than
• the glass transition temperature of the cured layer of the laminate can be at least 80°C, such as at least 85°C, at least 90°C, at least 100°C, at least 110°C, or at least 115°.
• the cured layer of the laminate can have an Ohnishi number of not greater than 3.0, such as not greater than 2.9, not greater than 2.8, not greater than 2.7, not greater than 2.65, or not greater than 2.6.
• the Ohnishi number may be at least 1.8, such as at least 1.9, at least 2.0, at least 2.1, at least 2.2, or at least 2.3.
• the present disclosure is further directed to a method of forming a cured layer.
• the method can comprise applying a layer of the curable composition described above over a substrate; bringing the curable composition into contact with a superstrate; curing the curable composition by exposure to light or heat to form a cured layer; and removing the superstrate from the cured layer.
• curing of the curable composition of the present disclosure can require a very short curing time.
• the substrate and the solidified (cured) layer may be subjected to additional processing to form a desired article, for example, by including an etching process to transfer an image into the substrate that corresponds to the pattern in one or both of the solidified layer and/or patterned layers that are underneath the solidified layer.
• the substrate can be further subjected to known steps and processes for device (article) fabrication, including, for example, curing, oxidation, layer formation, deposition, doping, planarization, etching, formable material removal, dicing, bonding, and packaging, and the like.
• the substrate may be processed to produce a plurality of articles (devices).
• the cured layer may be further used as an interlayer insulating film of a semiconductor device, such as LSI, system LSI, DRAM, SDRAM, RDRAM, or D-RDRAM, or as a resist film used in a semiconductor manufacturing process.
• a semiconductor device such as LSI, system LSI, DRAM, SDRAM, RDRAM, or D-RDRAM, or as a resist film used in a semiconductor manufacturing process.
• curable composition of the present disclosure can have very suitable properties especially for IAP processing.
• the curable composition of the present disclosure can have a desired low viscosity of not greater than 10 mPa s and can form cured layers with high mechanical strength, high thermal stability and low shrinkage. Examples
• compositions were prepared by combining for each composition 50 wt% benzyl acrylate (BA), as first monomer, and 10 wt% of a monomer including a maleimide ring, wherein the maleimide ring was substituted on the N position with an aromatic group, as second monomer.
• the monomer including a maleimide ring was selected from: N-benzylmaleimide (N-BMI); N-cyclohexylmaleimide (N-CMI); N-phenylmaleimide (N- PMI); and bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BEMMI).
• Each composition further contained 20 wt% naphthyl acrylate (NA) and one or two other polymerizable monomers selected from divinylbenzene (DVB) and bisphenyl A dimethacrylate (BPADMA). Moreover, each composition contained 3 wt% Irgacure 819 from LabNetworks and 1 wt% surfactant Chemguard S554 from Chemguard based on the total weight of the composition.
• Table 1 A summary of the types and amounts of polymerizable monomers contained in the compositions of samples SI to S6 can be seen in Table 1.
• the wt% amounts of the monomers listed in Table 1 are all based on 100 wt% of the total amount of polymerizable material, which means that the monomer amounts listed for each composition in Table 1 add up to 100 wt%.
• Table 1 further includes the carbon content, hydrogen content, and the Ohnishi number of the compositions.
• Nt total number of atoms
• No oxygen atoms
• Table 1 also includes a comparative sample Cl, which did not contain a maleimide monomer in the polymerizable material, and is a commercial IAP resist material.
• Table 2 further includes for several samples data for the weight loss of the samples at 250°C, which should simulate the wafer baking process.
• the weight loss data were obtained by conducting thermal gravimetric analysis (TGA) at a heating speed of 20°C per minute up to 250°C, holding the temperature for 90 seconds at this temperature and measuring the weight loss. It was surprisingly observed that samples S4, S5, and S6 all had a weight loss after the heat treatment below 3%. An exceptionally low weight loss could be obtained for sample S6 with only 1.34%.
• the weight loss during heat treatment at 250°C of the samples can indicate that in a sample with a lower weight loss, e.g., samples S6, a larger degree of monomers were polymerized than in a sample of a higher weight loss, e.g., sample S4.
• the UV shrinkage measurements were performed with an Anton Paar MCR-301 rheometer coupled to an UV curing system and heater. For the testing, a 7 m ⁇ drop of the test sample was added onto a plate and a temperature control hood was released to insulate the drop and the measuring unit. The amount of the sample was designed to obtain a thickness (hereinafter also called height) of the sample layer of slightly higher than 0.1 mm. By pre-setting the target height to 0.1 mm, the measuring unit moved down to the set value, causing extra amount of resist flowing off the plate. This insured that the exact height of the liquid resist was 0.1 mm before curing. Thereafter, the resist was cured with a UV power of 4 mW/cm 2 at 365 nm for 600 seconds.
• SL (LR - LCR / LR) X 100% (1), wherein LR is the thickness of the photocurable composition layer before curing and LCR is the thickness of the cured photocurable composition layer.
• Comparative sample C2 was a typical resist material for nanoimprint lithography (NIL).
• C2 contained the following ingredients: isobornyl acrylate (IBOA) in an amount of 33.3 wt%, di cyclopentyl acrylate (DCPA) in an amount of 19.4 wt%, BA in an amount of 22.2 wt%, neopentyl glycol diacrylate (A-NPG) in an amount of 18.5 wt%, photoinitiator Irgacure 907 and Irgacure 651 in an amount of 0.925 wt% and 1.85%, respectively, and surfactant in an amount of 3.79 wt%.
• Comparative sample C2 had a viscosity of 6.8 mPa s, a UV shrinkage during curing of 4.5%, a carbon content of 71%, a glass transition temperature of 90°C, and an Ohnishi number of 3.26.
• the storage modulus and glass transition temperature were measured with an Anton- Paar MCR-301 rheometer coupled with a Hamamatsu Lightningcure LC8 UV source.
• the sample was radiated with a UV intensity of 1.0 mW/cm 2 at 365 nm controlled by a Hamamatsu 365 nm UV power meter.
• Software named RheoPlus was used to control the rheometer and to conduct the data analysis.
• the temperature was controlled by a Julabo F25-ME water unit and set to 23°C as starting temperature. For each sample testing, 7 m ⁇ resist sample was added onto a glass plate positioned directly underneath the measuring system of the rheometer.
• the distance between glass plate and measuring unit was reduced to a gap of 0.1 mm.
• the UV radiation exposure was continued until the storage modulus reached a plateau, and the height of the plateau was recorded as the storage modulus listed in Table 3.
• the temperature of the cured sample was increased by controlled heating to measure the change of the storage modulus in dependency to the temperature to obtain the glass transition temperature T .
• glass transition temperature T g was considered the temperature corresponding to the maximal value of Tangent (Q).
• the hardness was calculated from loading curves measured with the Hysitron TI 950 Triboindenter by indent to 200 nm, using the displacement controlled loading function. During indentation, the force was measured, from which the loading curves could be obtained.
• FTIR Fourier-transform infrared spectroscopy
• Table 4 shows the percent conversion of double bonds for each tested sample at 10 second and at 100 seconds.

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