Curable composition for producing a cured layer with high thermal stability
A curable composition with bismaleimide monomers and divinylbenzene/trivinylbenzene provides high thermal stability, addressing the thermal stability issues in inkjet adaptive planarization, enabling effective processing at elevated temperatures.
Patent Information
- Application Number
- JP2023508113
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2020-12-16
- Filing Date
- 2021-11-15
- Publication Date
- 2026-01-28
- Estimated Expiration
- 2041-11-15
AI Technical Summary
Existing inkjet adaptive planarization (IAP) materials do not produce planar cured layers with sufficient thermal stability for subsequent processing steps, particularly at high temperatures.
A curable composition comprising a polymerizable material with a specific combination of bismaleimide monomers, divinylbenzene, and/or trivinylbenzene, along with a photoinitiator, which forms a cured layer with high thermal stability up to 350°C, maintaining minimal weight loss during reheating.
The composition achieves a cured layer with minimal weight loss (2% or less) upon reheating from 25°C to 350°C, ensuring high thermal stability and suitability for advanced processing steps.
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Figure 0007808086000013 
Figure 0007808086000014 
Figure 0007808086000001
Abstract
Description
[Technical Field]
[0001] The present disclosure relates to curable compositions, and in particular to curable compositions for inkjet compatible planarization that include bismaleimide monomers, wherein a cured layer made from the curable composition can have high thermal stability up to 350°C. [Background technology]
[0002] Inkjet Adaptive Planarization (IAP) is a process for planarizing the surface of a substrate, such as a wafer containing electronic circuitry, by jetting droplets of a curable composition onto the surface of the substrate and directly contacting the liquid with a planar superstrate to form a planar liquid layer. The planar liquid layer is typically solidified under UV light exposure, and after removal of the superstrate, a planar surface is obtained that can be subjected to subsequent processing steps, such as baking, etching, and / or further deposition steps. Improved IAP materials are needed that result in planar cured layers with high thermal stability. Summary of the Invention
[0003] In one embodiment, the curable composition comprises a polymerizable material and a photoinitiator, the polymerizable material comprising a first monomer comprising at least one bismaleimide monomer and at least one second monomer; the second monomer comprises divinylbenzene (DVB) and / or trivinylbenzene (TVB) and at least one multifunctional monomer; The amount of the at least one bismaleimide monomer is Based on , 5 wt% or more and 60 wt% or less, the viscosity of the curable composition at 23°C is 30 mPa·s or less, and a cured layer of the curable composition after baking at 350°C for 30 minutes under nitrogen may lose 2% or less in weight when reheated from 25°C to 350°C at a rate of 20°C / min under nitrogen.
[0004] In one embodiment, the amount of the at least one bismaleimide monomer can be 30 wt% or less, based on the total weight of the polymerizable monomers. In another embodiment, the amount of the at least one bismaleimide monomer can be 15 wt% or less.
[0005] In one embodiment of the curable composition, the at least one second monomer is at least one acrylate monomer, divinylbenzene (DVB), trivinylbenzene (TVB) , N-Vini Rupee The formulation may include rolidone (NVP), acryloylmorpholine (AMP), or any combination thereof.
[0006] In one embodiment of the curable composition, the at least one acrylate monomer can include at least one multifunctional acrylate monomer.
[0007] In another embodiment of the curable composition, the at least one second monomer is Divinylbenzene ( DVB ) and at least one multifunctional acrylate monomer.
[0008] In a further aspect, At least one The acrylate monomer includes a monofunctional acrylate monomer, and the amount of the monofunctional acrylate monomer is based on the total weight of the polymerizable material. Based on It can be 20 wt% or less.
[0009] In one embodiment of the curable composition, the at least one bismaleimide monomer may include 4,4'-bismaleimidodiphenylmethane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, or any combination thereof.
[0010] In one embodiment, the bismaleimide monomer may be dissolved in at least one second monomer.
[0011] In a further embodiment, the curable composition is Including It is not necessary.
[0012] In one embodiment, At least one The bismaleimide monomer is 23℃ It is a solid and can be dissolved in N-vinylpyrrolidone (NVP) or acryloylmorpholine (AMP).
[0013] In yet another particular embodiment, At least one The bismaleimide monomer is 23℃ and the at least one second monomer may comprise DVB, or a multifunctional acrylate monomer, or a combination thereof.
[0014] In another embodiment, a laminate includes a substrate and a curable layer overlying the substrate, the curable layer may be formed from the curable composition described above.
[0015] In certain embodiments of the laminate, after baking, the cured layer may lose no more than 1.5% weight upon reheating from 25° C. to 350° C. at a rate of 20° C. / min under nitrogen.
[0016] In a further embodiment, a method of forming a cured layer on a substrate includes applying a layer of a curable composition onto a substrate, wherein the curable composition comprises a polymerizable material and a photoinitiator, the polymerizable material comprises a first monomer comprising at least one bismaleimide monomer, and a second monomer, and the amount of the at least one bismaleimide monomer is about 0.01 wt. Based on , 5 wt% or more and 60 wt% or less, and the method includes the steps of contacting the curable composition with a superstrate, irradiating the curable composition with light to form a cured layer, and removing the superstrate from the cured layer, and the cured layer after baking at 350°C for 30 minutes under nitrogen may have a weight loss of 2% or less when reheated from 25°C to 350°C at a rate of 20°C / min under nitrogen.
[0017] In one embodiment of the present invention, the viscosity of the curable composition at 23° C. may be 30 mPa·s or less.
[0018] In another embodiment of the method, the at least one second monomer of the curable composition can include at least one acrylate monomer, divinylbenzene (DVB), trivinylbenzene (TVB), N-vinylpyrrolidone (NVP), acryloylmorpholine (AMP), or any combination thereof.
[0019] In some embodiments of the method, the at least one acrylate monomer can include at least one multifunctional acrylate monomer.
[0020] In another particular embodiment of the method, the at least one bismaleimide monomer of the curable composition can include 4,4'-bismaleimidodiphenylmethane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, or any combination thereof.
[0021] In a further embodiment, a method of making an article includes applying a layer of a curable composition onto a substrate, wherein the curable composition comprises a polymerizable material and a photoinitiator, the polymerizable material comprises a first monomer comprising at least one bismaleimide monomer, and a second monomer, wherein the amount of the at least one bismaleimide monomer is about 100% by weight of the total polymerizable material. Based on %, or more than 5 wt % and less than 60 wt %, and the method includes the steps of contacting the curable composition with a superstrate; irradiating the curable composition with light to form a cured layer; removing the superstrate from the cured layer; wherein the cured layer after baking at 350°C for 30 minutes under nitrogen loses no more than 2% in weight upon reheating from 25°C to 350°C at a rate of 20°C / min under nitrogen; forming a pattern on a substrate; treating the substrate on which the pattern has been formed in the forming step; and manufacturing an article from the substrate treated in the treating step. In a further embodiment, A curable composition for use in inkjet-compatible planarization includes a polymerizable material and a photoinitiator, wherein the polymerizable material includes a first monomer including at least one bismaleimide monomer and at least one second monomer, wherein the amount of the at least one bismaleimide monomer is 5 wt % or more and 60 wt % or less, based on the total weight of the polymerizable material. The curable composition has a viscosity of 30 mPa·s or less at 23°C. After baking at 350°C for 30 minutes under nitrogen, a cured layer of the curable composition may lose 2% or less in weight upon reheating from 25°C to 350°C at a rate of 20°C / min under nitrogen. [Brief explanation of the drawings]
[0022] Embodiments are illustrated by way of example and not limitation in the accompanying figures.
[0023] [Figure 1] FIG. 1 includes a graph showing the weight loss of a cured layer at a rate of 20° C. / min by thermographic analysis (TGA), according to one embodiment, after baking the cured layer at 350° C. for 30 minutes under nitrogen.
[0024] [Figure 2] FIG. 2 includes a graph showing the weight loss of a cured layer at a rate of 20° C. / min by thermographic analysis (TGA), according to one embodiment, where the TGA was performed after baking the cured layer at 350° C. for 30 minutes under nitrogen.
[0025] Those skilled in the art will appreciate that elements in the figures are illustrated for simplicity and clarity and have not necessarily been drawn to scale. For example, the dimensions of some of the elements in the figures may be exaggerated relative to other elements to help understand embodiments of the present invention. DETAILED DESCRIPTION OF THE INVENTION
[0026] The following description is provided to aid in understanding the teachings disclosed herein and focuses on particular implementations and embodiments of the teachings. This focus is provided to help explain the teachings and should not be construed as a limitation on the scope or applicability of the teachings.
[0027] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one skilled in the art to which this invention belongs. The materials, methods, and examples are illustrative only and are not intended to be limiting. To the extent not described herein, many details regarding specific materials and processing operations are conventional and can be found in textbooks and other sources within imprint and lithography technology.
[0028] As used herein, the terms "comprises," "includes," "including," "including," "has," "having," or any other variations thereof, are intended to cover an open-ended inclusion. For example, a process, method, article, or apparatus that includes a list of features is not necessarily limited to only those features and may include other features not expressly listed or inherent in such process, method, article, or apparatus.
[0029] As used herein, and unless expressly stated otherwise, "or" refers to an inclusive or, not an exclusive or. For example, a condition A or B is satisfied by any one of: A being true (or present) and B being false (or not present), A being false (or not present) and B being true (or present), and both A and B being true (or present).
[0030] Additionally, the use of "a" or "an" is used to describe elements and components described herein. This is used merely for convenience and to give a general sense of the scope of the invention. This specification should be read to include one or at least one, and the singular also includes the plural unless it is clear that no plural is intended.
[0031] The present disclosure relates to a curable composition comprising a polymerizable material and a photoinitiator, where the polymerizable material can comprise a first monomer comprising at least one bismaleimide monomer and at least one second monomer. Surprisingly, it has been observed that a curable composition comprising a specific combination of at least one bismaleimide monomer and at least one second monomer can produce a cured layer with high thermal stability up to 350°C. In one embodiment, a cured layer formed from the curable composition can exhibit a weight loss of 2% or less upon reheating from 25°C to 350°C at a rate of 20°C / min under nitrogen after being subjected to a bake treatment at 350°C for 30 minutes.
[0032] As used herein, the term "bismaleimide monomer" refers to a monomer containing two maleimide rings. In one embodiment, a bismaleimide monomer is an N-substituted monomer having the general structure of Formula 1, where R may contain one or more substituted or unsubstituted benzyl rings, or substituted or unsubstituted cyclohexane rings, or alkyl, or alkylaryl. TIFF0007808086000001.tif98155
[0033] Non-limiting examples of bismaleimide monomers that may be included in the curable compositions of the present disclosure include 4,4'-bismaleimidodiphenylmethane (BMDM) - CAS 13676-54, bis(3-ethyl-4-maleimidophenyl)methane (BEMMA) - CAS 105391-33-5, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane (BMAPP) - CAS 79922-55-7, 1H-pyrrole-2,5-dione, 1'-C36-alkylenebis(BMI-689) - CAS 1911605-95-2, 3-methyl-1,5-pentanediol diacrylate (MDPA) CAS 64194-22-5, 1-maleimido-5-maleimidomethyl-3,3,5-trimethylcyclohexane (BMI-A) - CAS 128762-9, 1,3-bis(maleimidomethyl)cyclohexane (BMI-B)-1,1'-[(octahydro-4,7-methano-1H-indene-2,5-diyl)bis[1H-pyrrole-2,5-(BMI-C)- CAS 1360462-58-3, 1,1'-[methylenebis(2-methyl-4,1-cyclohexanediyl)]bis[1H-pyrrole-2,5-dione] (BMI-D)- CAS 943149-44-8, or any combination thereof.
[0034] BMAPP: TIFF0007808086000002.tif42162
[0035] BMI-689: TIFF0007808086000003.tif119165
[0036] BMDM: TIFF0007808086000004.tif55143
[0037] BEMMA: TIFF0007808086000005.tif47117
[0038] MDPA: TIFF0007808086000006.tif67137
[0039] BMI-A: TIFF0007808086000007.tif9882
[0040] BMI-B: TIFF0007808086000008.tif12085
[0041] BMI-C: TIFF0007808086000009.tif78130
[0042] BMI-D: TIFF0007808086000010.tif64132
[0043] In certain embodiments of the curable composition, the amount of bismaleimide monomer is about 100 wt. % by weight of the total curable composition. Based on In another embodiment, the amount of bismaleimide monomer may be 10 wt.% or less, based on the total weight of the curable composition. Based on 5 wt% or more of the total weight of polymerizable materials Based on It can be 10 wt% or more, or 15 wt% or more, or 20 wt% or more. The amount of bismaleimide monomer can be any value within any of the above maximum and minimum values while maintaining high thermal stability.
[0044] In one embodiment, the at least one second monomer can be at least one multifunctional monomer or a combination of at least one multifunctional monomer and at least one monofunctional monomer. As used herein, the terms "multifunctional" or "monofunctional" refer to the amount of functional groups in a monomer that can participate in the polymerization or crosslinking reaction of the polymerizable material during curing. Non-limiting examples of functional groups can be vinyl groups, hydroxyl groups, carboxyl groups, amine groups, or isocyanate groups. In certain aspects, each of the monomers of the polymerizable material can contain one or more vinyl groups.
[0045] Non-limiting examples of the at least one second monomer can be an acrylate monomer, styrene, divinylbenzene, trivinylbenzene, N-vinylpyrrolidone (NVP), acryloylmorpholine (AMP), or any combination thereof.
[0046] In certain embodiments, the at least one acrylate monomer may comprise at least one multifunctional acrylate monomer, such as a difunctional, trifunctional, or tetrafunctional acrylate monomer. Furthermore, as used herein, the term acrylic acid monomer refers to both substituted and non-substituted acrylic acid monomers. Non-limiting examples of substituted acrylate monomers may be alkyl acrylates, such as methacrylate or ethyl acrylate.
[0047] In certain particular embodiments, the at least one second monomer of the curable composition may include a multifunctional acrylate monomer and divinylbenzene.
[0048] In another particular embodiment, the at least one second monomer comprises a monofunctional acrylate monomer, and the amount of the monofunctional acrylate monomer is about 100% by weight of the total polymerizable material. Based on , 20 wt% or less, for example, 15 wt% or less, or 10 wt% or less.
[0049] In certain embodiments, the polymerizable material of the curable composition may be solvent-free and may consist essentially of at least one bismaleimide monomer and at least one second monomer.
[0050] In certain embodiments, the bismaleimide monomer may be a compound that is solid at room temperature (23° C.) and dissolved in another monomer of the polymerizable material that is part of at least one second monomer. In one particular aspect, the bismaleimide monomer is 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane (BMAPP), which may be dissolved in N-vinylpyrrolidone (NVP) or acryloylmorpholine (AMP).
[0051] In another embodiment, the bismaleimide monomer may be liquid at room temperature and miscible with the other monomers of the composition. In one particular embodiment, the bismaleimide monomer is 1H-pyrrole-2,5-dione, 1,1'-C36-alkylenebis(BMI-689), and the second monomer may include DVB, or a multifunctional acrylate monomer, or a combination thereof.
[0052] In certain embodiments, the at least one second monomer can include divinylbenzene and at least one multifunctional monomer.
[0053] In another particular embodiment, the at least one second monomer comprises a monoacrylate, and the amount of monoacrylate is about 100% by weight of the total polymerizable material. Based on In some embodiments, the amount of monoacrylate can be 5 wt% or more, 15 wt% or less, or 10 wt% or less, or 7 wt% or less.
[0054] In certain embodiments, the weight percent ratio of the bismaleimide monomer to the at least one second monomer in the photocurable composition can be from 1:10 to 10:1, or from 1:10 to 1:2, or from 1:10 to 1:5.
[0055] In another embodiment, the polymerizable material of the photocurable composition may further comprise a specific amount of a polymerizable monomer, oligomer, or polymer.
[0056] In one embodiment, the curable compositions of the present disclosure can have low viscosities, enabling the use of these compositions in IAP applications. In one aspect, the viscosity of the curable composition at 23°C can be 50 mPa·s or less, e.g., 40 mPa·s or less, or 30 mPa·s or less, 20 mPa·s or less, 15 mPa·s or less, or 10 mPa·s or less. In another aspect, the viscosity can be 2 mPa·s or more, or 5 mPa·s or more, or 7 mPa·s or more. As used herein, all viscosity values refer to viscosities measured at a given temperature using the Brookfield method.
[0057] In a further embodiment, the amount of polymerizable material contained in the curable composition is about 100% by weight of the total photocurable composition. Based on , 75 wt% or more, e.g., 80 wt% or more, 85 wt% or more, 90 wt% or more, or 95 wt% or more. In another embodiment, the amount of polymerizable material can be 99.5 wt% or less, e.g., 99 wt% or less, or 98 wt% or less, or 97 wt% or less, or 95 wt% or less, or 93 wt% or less, or 90 wt% or less. The amount of polymerizable material can be within any of the minimum and maximum values listed above. In certain embodiments, the amount of polymerizable material is based on the total weight of the photocurable composition. Based on , 85 wt% or more and 98 wt% or less, or 90 wt% or more and 97 wt% or less.
[0058] In a further aspect, the curable compositions of the present disclosure may be solvent-free.
[0059] One or more photoinitiators may be included in the photocurable composition to initiate photocuring of the composition when exposed to light.
[0060] In certain embodiments, curing may be carried out without the presence of a photoinitiator, hi other certain embodiments, curing may be carried out by a combination of light and thermal curing.
[0061] In a further embodiment, the curable composition may contain at least one optional additive, non-limiting examples of which can be a surfactant, a dispersant, a stabilizer, a co-solvent, an initiator, an inhibitor, a dye, or any combination thereof.
[0062] In another embodiment, the present disclosure is directed to a laminate including a substrate and a curable layer overlying the substrate, the curable layer may be formed from the curable composition described above.
[0063] In certain embodiments, the laminate may further include one or more layers, such as an adhesive layer, between the substrate and the curable layer.
[0064] The present disclosure further relates to a method of forming a cured layer, which may include applying the above-described curable composition onto a substrate, contacting the curable composition with a superstrate, irradiating the photocurable composition with light to form a cured layer, and removing the superstrate from the cured layer.
[0065] In one embodiment, the light irradiation can be carried out with light having a wavelength of 250 nm to 760 nm. In a preferred embodiment, the light irradiation can be carried out with light having a wavelength of 300 nm to 450 nm.
[0066] To form the desired article, the substrate and solidified (cured) layer may be subjected to additional processing, for example, by including an etching process to transfer an image corresponding to the pattern in one or both of the solidified layer and / or the patterned layer underlying the solidified layer to the substrate. The substrate may 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. In some embodiments, the substrate may be processed to fabricate multiple articles (devices).
[0067] The hardened layer may be used as an interlayer insulating film in semiconductor devices such as LSI, system LSI, DRAM, SDRAM, RDRAM, and D-RDRAM, or as a resist film used in semiconductor manufacturing processes.
[0068] As further demonstrated in the Examples, it has surprisingly been discovered that curable compositions containing bismaleimide monomers in combination with certain multifunctional monomers and / or combinations of multifunctional and monofunctional monomers can have properties highly suitable for IAP processing. The curable compositions can have low viscosity and can form cured layers with very high thermal stability up to 350°C. example
[0069] The following non-limiting examples illustrate the concepts described herein.
[0070] Example 1
[0071] Preparation of Photocurable IAP Compositions
[0072] Photocurable compositions were prepared containing the following bismaleimide monomers: A) 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane (CAS No. 79922-55-7) (also referred to herein as "BMAPP" and solid at room temperature (23° C.)), and B) 1H-pyrrole-2,5-dione, 1,1'-C36-alkylenebis (CAS 1911605-95-2) (also referred to herein as "BMI-689" and liquid at room temperature).
[0073] Curable compositions comprising BMAPP:
[0074] Two polymerizable monomers, N-vinylpyrrolidone (NVP) and acryloylmorpholine (AMP), were found to be suitable for dissolving solid BMAPP. Curable compositions S1–S4 were prepared. Compositions S1 and S2 contained NVP as the solvent, while compositions S3 and S4 contained AMP as the solvent. Additionally, the following monomers were used in various combinations: a tetrafunctional acrylate monomer, herein "SR295" (pentaerythritol tetraacrylate from Sartomer); a trifunctional acrylate monomer, herein "SR351" (trimethylolpropane triacrylate from Sartomer); a difunctional acrylate monomer, herein "MPDA" (3-methyl-1,5-pentanediol diacrylate from Sartomer); and divinylbenzene (DVB). All photocurable compositions further contained 1–5 wt% Irgacure 819 as a photoinitiator and 0.1–3% surfactant. An overview of the curable compositions S1 to S4 that were prepared is shown in Table 1. The type and amount of monomers used, as well as the viscosity of the final curable composition, are given.
[0075] Curable compositions containing BMI689
[0076] Curable compositions S5 and S6 were prepared containing the liquid bismaleimide monomer BMI689. In composition S5, BMI689 was combined with DVB, and in composition S6, BMI689 was combined with neopentyl glycol diacrylate, also referred to herein as "SR241" (Sartomer). See also Table 1.
[0077] [Table 1]
[0078] Comparative curable composition
[0079] A comparative curable composition was prepared using a monomaleimide monomer instead of a bismaleimide monomer. N-benzylmaleimide (CAS 1632-26-1) (BMI) was used as the monomaleimide monomer in combination with NVP and the tetrafunctional acrylate monomer SR295. The exact composition of the polymerizable material is also listed in Table 1. Like the other curable compositions, comparative composition C1 also contained the photoinitiator Irgacure 819 and the same surfactants.
[0080] viscosity
[0081] The viscosity of the photocurable compositions was measured using a Brookfield Viscometer LVDV-II + Pro at 200 rpm, with a spindle size of #18 and a spin speed of 135 rpm. For viscosity testing, approximately 6-7 mL of sample liquid was added to the sample chamber, enough to cover the spindle head. The sample contained within the chamber was allowed to equilibrate for approximately 20 minutes to reach the desired measurement temperature of 23°C before the actual measurement began. For all viscosity tests, at least three measurements were taken, and an average value was calculated.
[0082] Thermal stability of the photocured layer
[0083] A 300 μm thick layer of the curable composition was applied to a glass substrate, and the curable composition was heated at room temperature (23° C.) to a maximum wavelength peak of 365 nm and a power of 20 mW / cm 2 UV light with a light intensity of 2.4 J / cm was applied for 120 seconds. 2 (corresponding to a curing energy dose of 1000 kJ / cm.sup.2). Photocured layers of all the compositions listed in Table 1 were prepared by irradiating and curing the composition.
[0084] The solid photocurable layer was further subjected to the following heat treatment. 1) The photocured layer was placed on a hotplate heated to 350°C for 30 minutes under nitrogen, also referred to herein as the "bake." After baking at 350°C for 30 minutes, the layer was removed from the hotplate, cooled to room temperature, and the weight loss was measured before and after the bake process. 2) Then, a 25 mg sample was taken from the baked film and TGA measurements were performed using a Linseis STA PT 1000 instrument by reheating the sample from 25°C to approximately 500°C at a rate of 20°C / min under nitrogen until the sample was completely decomposed.
[0085] The weight loss during baking was approximately between 10 and 17 wt% for samples S1-S4 and between 1 and 3 wt% for samples S5 and S6. After baking, the layers showed excellent thermal stability up to 350 °C. The exact weight loss of the baked layers during reheating from 25 °C to 350 °C at a rate of 20 °C / min is shown in Table 2.
[0086] [Table 2]
[0087] Experiments have shown that the photocured layers from samples S1-S6 can be baked at 350°C for 30 minutes without damaging the layers. When the baked layers are cooled and then reheated from 25°C to 350°C, these materials lose approximately 100% of the total weight of the layer before reheating. Based onThe results showed excellent thermal stability up to a temperature of 350°C, with a weight loss of only 0.96-1.53%. The TGA curves of sample S2 during reheating are shown in Figure 1, and the TGA curves of sample S5 are shown in Figure 2. Such high thermal stability of the cured layer, combined with the low viscosity of the respective curable compositions, makes these materials highly suitable for the AIP process.
[0088] The descriptions and illustrations of the embodiments described herein are intended to provide a general understanding of the structures of various embodiments. The specification and illustrations are not intended to be exhaustive or comprehensive descriptions of all of the elements and features of apparatus and systems that use the structures or methods described herein. Separate embodiments may also be provided in combination in a single embodiment, and conversely, various features that are described for brevity in the context of a single embodiment may be provided separately or in any subcombination. Furthermore, references to values described in ranges include each and every value within that range. Many other embodiments may be apparent to those skilled in the art only after reading this specification. Other embodiments may be utilized and derived from the present disclosure, such that structural substitutions, logical substitutions, or other changes may be made without departing from the scope of the present disclosure. Accordingly, the present disclosure should be considered illustrative and not restrictive.
Claims
1. A curable composition comprising a polymerizable material and a photopolymerization initiator, the polymerizable material comprises a first monomer comprising at least one bismaleimide monomer and at least one second monomer; the at least one second monomer comprises divinylbenzene (DVB) and / or trivinylbenzene (TVB) and at least one multifunctional monomer; the amount of the at least one bismaleimide monomer is greater than or equal to 5 wt % and less than or equal to 60 wt %, based on the total weight of the polymerizable material; the viscosity of the curable composition at 23°C is 30 mPa s or less; a cured layer of the curable composition after baking at 350°C for 30 minutes under nitrogen exhibits a weight loss of 2% or less when reheated from 25°C to 350°C at a rate of 20°C / min under nitrogen; A curable composition characterized by:
2. 10. The curable composition of claim 1, wherein the amount of the at least one bismaleimide monomer is 30 wt% or less.
3. 3. The curable composition of claim 2, wherein the amount of the at least one bismaleimide monomer is 15 wt% or less.
4. 10. The curable composition of claim 1, wherein the at least one second monomer comprises at least one acrylate monomer, divinylbenzene (DVB), trivinylbenzene (TVB), N-vinylpyrrolidone (NVP), acryloylmorpholine (AMP), or any combination thereof.
5. 5. The curable composition of claim 4, wherein the at least one acrylate monomer comprises at least one multifunctional acrylate monomer (MFA).
6. 5. The curable composition of claim 4, wherein the at least one second monomer comprises divinylbenzene (DVB) and at least one multifunctional acrylate monomer.
7. 5. The curable composition of claim 4, wherein the at least one acrylate monomer comprises a monofunctional acrylate monomer, and the amount of the monofunctional acrylate monomer is 20 wt % or less, based on the total weight of the polymerizable material.
8. 2. The curable composition of claim 1, wherein the at least one bismaleimide monomer comprises 4,4'-bismaleimidodiphenylmethane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, or any combination thereof.
9. 10. The curable composition of claim 1, wherein the at least one bismaleimide monomer is dissolved in the second monomer.
10. The curable composition of claim 1 , wherein the curable composition is solvent-free.
11. 10. The curable composition of claim 1, wherein the at least one bismaleimide monomer is solid at 23°C and soluble in N-vinylpyrrolidone (NVP) or acryloylmorpholine (AMP).
12. 10. The curable composition of claim 1, wherein the at least one bismaleimide monomer is fluid at 23°C and the second monomer comprises DVB, or a multifunctional acrylate monomer, or a combination thereof.
13. A laminate comprising a substrate and a curable layer overlying the substrate, the curable layer being formed from the curable composition of claim 1.
14. 14. The laminate of claim 13, wherein the cured layer loses less than 1.5% weight during reheating from 25°C to 350°C at a rate of 20°C / min under nitrogen.
15. 1. A method for forming a cured layer on a substrate, comprising: applying a layer of a curable composition onto the substrate, wherein the curable composition comprises a polymerizable material and a photoinitiator, the polymerizable material comprising a first monomer comprising at least one bismaleimide monomer, and a second monomer, wherein the amount of the at least one bismaleimide monomer is 5 wt % or more and 60 wt % or less, based on the total weight of the polymerizable material; contacting the curable composition with a superstrate; a step of irradiating the curable composition with light to form a cured layer; removing the superstrate from the hardened layer; and wherein the cured layer, after baking at 350°C for 30 minutes under nitrogen, loses no more than 2% in weight upon reheating from 25°C to 350°C at a rate of 20°C / min under nitrogen.
16. 16. The method of claim 15, wherein the viscosity of the curable composition at 23°C is 30 mPa·s or less.
17. 16. The method of claim 15, wherein the second monomer comprises at least one acrylate monomer, divinylbenzene (DVB), trivinylbenzene (TVB), N-vinylpyrrolidone (NVP), acryloylmorpholine (AMP), or any combination thereof.
18. 20. The method of claim 17, wherein the at least one acrylate monomer comprises at least one multifunctional acrylate monomer.
19. 16. The method of claim 15, wherein the at least one bismaleimide monomer comprises 4,4'-bismaleimidodiphenylmethane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, or any combination thereof.
20. applying a layer of a curable composition onto a substrate, wherein the curable composition comprises a polymerizable material and a photoinitiator, the polymerizable material comprising a first monomer comprising at least one bismaleimide monomer, and a second monomer, wherein the amount of the at least one bismaleimide monomer is 5 wt % or more and 60 wt % or less, based on the total weight of the polymerizable material; contacting the curable composition with a superstrate; a step of irradiating the curable composition with light to form a cured layer; removing the superstrate from the cured layer; and wherein the cured layer, after baking at 350°C for 30 minutes under nitrogen, loses no more than 2% in weight upon reheating from 25°C to 350°C at a rate of 20°C / min under nitrogen; forming a pattern on the substrate; a step of treating the substrate on which the pattern has been formed in the forming step; manufacturing an article from the substrate processed in the processing step; A method for manufacturing an article, comprising:
21. A curable composition for use in inkjet compatible planarization, comprising: a polymerizable material and a photopolymerization initiator; the polymerizable material comprises a first monomer comprising at least one bismaleimide monomer and at least one second monomer; the amount of the at least one bismaleimide monomer is greater than or equal to 5 wt % and less than or equal to 60 wt %, based on the total weight of the polymerizable material; the viscosity of the curable composition at 23°C is 30 mPa s or less; a cured layer of the curable composition after baking at 350°C for 30 minutes under nitrogen exhibits a weight loss of 2% or less when reheated from 25°C to 350°C at a rate of 20°C / min under nitrogen; 1. A curable inkjet compatible planarizing composition comprising:
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