Compound having two or more functional groups including ethylenically unsaturated double bond and biuret bond, adhesive property-improving agent, curable composition, and cured product

Abstract

The purpose of the present invention is to provide: a compound capable of imparting excellent adhesive properties; an adhesive property-improving agent containing said compound; a curable composition containing said compound or said adhesive property-improving agent; and a cured product. A compound according to the present invention has two or more functional groups including an ethylenically unsaturated double bond and a biuret bond, and can impart adhesive properties to a curable composition when being blended in the curable composition.

Description

Compounds having two or more functional groups containing ethylenically unsaturated double bonds and biuret bonds, adhesion improvers, curable compositions, and cured products.

[0001] The present invention relates to a compound having two or more functional groups containing an ethylenically unsaturated double bond and a biuret bond, an adhesion improver containing the compound, a curable composition containing the compound or the adhesion improver, and a cured product.

[0002] In recent years, in the field of electronic and optical materials, research has been underway to improve flat panel displays using liquid crystals and organic EL displays, such as increasing resolution, widening viewing angles, and improving image quality; light sources using optical semiconductors such as light-emitting diodes (LEDs), such as increasing brightness, shortening wavelengths, and whiteness; electronic circuits, such as increasing frequencies; and optical and electronic components such as circuits and communications that use light, to improve performance. Furthermore, in the semiconductor technology field, there is a rapid progress towards miniaturization, weight reduction, performance improvement, and multi-functionality of electronic devices. Optical circuits using optical waveguides, etc., which enable faster processing, are also being considered. In response to these needs, there is a demand for higher density and higher wiring density in wiring boards. And to achieve higher density and higher wiring density in wiring boards, there is a need for resist materials with excellent photosensitivity, heat resistance, and chemical resistance.

[0003] Furthermore, resist materials are required to have excellent developability and chemical resistance to various substrates.

[0004] For example, Patent Document 1 proposes a silane compound having a specific structure, and it is described that by using this silane compound in combination with a resist material, adhesion and stability can be imparted to the resist material.

[0005] International Publication No. 2014 / 104195

[0006] The resist material containing the silane compound described in Patent Document 1 can provide sufficient adhesion to substrates having hydroxyl groups on their surface, but there was room for improvement in its adhesion to substrates with a smaller amount of hydroxyl groups on their surface compared to glass, etc. (for example, substrates with metal wiring in a laminated structure (MAM) in which aluminum is sandwiched between molybdenum, substrates with a silicon nitride (SiNx) film, and substrates with an indium tin oxide (ITO) film).

[0007] The present invention has been made in view of the above problems, and aims to provide a compound that can impart excellent adhesion, an adhesion improving agent containing the compound, a curable composition containing the compound or the adhesion improving agent, and a cured product.

[0008] The present invention provides the following embodiments: <1> A compound having two or more functional groups containing ethylenically unsaturated double bonds and a biuret bond. <2> The compound according to <1>, wherein the functional group containing the ethylenically unsaturated double bond is a (meth)acryloyloxy group. <3> The compound according to <1> or <2>, further having a urethane bond. <4> The compound according to any one of <1> to <3>, which does not contain a Si atom. <5> An adhesion improver containing the compound according to any one of <1> to <4>. <6> A curable composition containing the compound according to any one of <1> to <4>, or the adhesion improver according to <5>. <7> The curable composition according to <6>, which is a resist material, adhesive, paint, or coating agent. <8> A cured product obtained from the curable composition according to <6> or <7>. <9> The cured product according to <8>, wherein the cured product is a photospacer, partition, lens, interlayer insulating film, protective film, overcoat film, optical waveguide, planarization film, adhesive layer, coating film, or coating film.

[0009] By incorporating the compounds of the present invention into curable compositions such as resist materials, adhesives, paints, and coatings, excellent adhesion can be imparted to the curable compositions. Furthermore, the compounds of the present invention do not reduce the storage stability of curable compositions when incorporated into them.

[0010] In the present invention, (meth)acrylate means acrylate and / or methacrylate, (meth)acrylic means acrylic and / or methacrylic, (meth)acryloyl means acryloyl and / or methacryloyl, and (meth)acrylic acid means acrylic acid and / or methacrylic acid.

[0011] 1. Compounds The compounds of the present invention have two or more functional groups containing ethylenically unsaturated double bonds and biuret bonds. By incorporating the compounds of the present invention into a curable composition, excellent adhesion can be imparted to the curable composition. The reason for this is not limited to theory, but is thought to be that complex ions are formed by coordination bonds between the biuret bond sites in the compound and the metal constituting the substrate, or that strong interactions occur between the biuret bond sites in the compound and the polar groups of the material constituting the substrate. Hereinafter, these may be collectively referred to as "interaction between biuret bonds and substrates, etc."

[0012] The compounds of the present invention have two or more functional groups containing ethylenically unsaturated double bonds (hereinafter also referred to as "radical polymerizable functional groups"). The radical polymerizable functional groups are not particularly limited and include, for example, vinyl groups, allyl groups, (meth)acryloyl groups, (meth)acryloyloxy groups, and (meth)acrylamide groups, and from the viewpoint of polymerizability, (meth)acryloyl groups or (meth)acryloyloxy groups are preferred. The compounds of the present invention may have one type of radical polymerizable functional group, or they may have two or more types of radical polymerizable functional groups.

[0013] In the compound of the present invention, the number of radically polymerizable functional groups may be two or more. On the other hand, there is no particular upper limit to the number of radically polymerizable functional groups, but it is usually six or less, preferably five or less, more preferably four or less, and even more preferably three or less. Specifically, the number of radically polymerizable functional groups is preferably two to six, more preferably two to five, even more preferably two to four, even more preferably two or three, and particularly preferably two. If the number of radically polymerizable functional groups is too large, the interactions such as bonding that occur between other components (e.g., polymers, etc.) contained in the composition to which the compound of the present invention is added and the radically polymerizable functional groups of the compound of the present invention (hereinafter also referred to as "interactions of radically polymerizable functional groups") may become too strong, and the interaction between the biuret bond and the substrate, etc., as described above may not be fully exhibited. In this respect, by having six or fewer radically polymerizable functional groups, the interaction of radically polymerizable functional groups becomes less likely to become too strong, and the interaction between the biuret bond and the substrate, etc., as described above, is more likely to be fully exhibited.

[0014] The compounds of the present invention have biuret bonds (also called biuret groups). In the compounds of the present invention, the number of biuret bonds is not particularly limited, but having at least one can impart excellent adhesion to the curable composition. There is no particular upper limit to the number of biuret bonds, but from the viewpoint of good solubility in the composition to which the compounds of the present invention are added, there are usually three or fewer, preferably two or fewer. Specifically, the number of biuret bonds is preferably one to three, more preferably one or two, and even more preferably one.

[0015] In the compounds of the present invention, the radical polymerizable functional group and the biuret bond may be directly bonded or bonded via a linking group, but it is preferable that they be bonded via a linking group. The linking group is not particularly limited and includes, for example, linear or branched aliphatic saturated or aliphatic unsaturated hydrocarbon groups, alicyclic saturated or alicyclic unsaturated hydrocarbon groups (including bridged rings and fused rings), aromatic hydrocarbon groups, organic groups in which some of the carbon atoms constituting the hydrocarbon group are substituted with heteroatoms (e.g., oxygen atoms, nitrogen atoms, and sulfur atoms), and organic groups in which two or more of these are bonded. Furthermore, the hydrocarbon group and the organic group may have various substituents (e.g., halogen groups, hydroxyl groups, alkyl groups, alkenyl groups, alkoxy groups, and aryl groups) and functional groups (e.g., ester bonds, amide bonds, ether bonds, thioether bonds, urethane bonds, and urea bonds). The linking group is preferably a linear or branched aliphatic saturated or aliphatic unsaturated hydrocarbon group, or an organic group in which two of the hydrocarbon groups are linked via a urethane bond, from the viewpoint of allowing the interaction of the radical polymerizable functional group to be fully exercised while also allowing the interaction between the biuret bond and the substrate, etc., to be fully exercised, and more preferably a linear or branched aliphatic saturated hydrocarbon group, or an organic group in which two of the hydrocarbon groups are linked via a urethane bond. The number of carbon atoms in the hydrocarbon group is preferably 2 to 8, more preferably 2 to 4.

[0016] The compounds of the present invention are preferably those represented by the following general formula (1). (In the formula, R 1 and R 2 Each is independently a hydrogen atom or a methyl group, R 3 and R 4 Each is independently a linear or branched aliphatic saturated or aliphatic unsaturated hydrocarbon group having 2 to 8 carbon atoms, or an organic group in which two of the aforementioned hydrocarbon groups are linked via a urethane bond, R 5 (This is a hydrogen atom or an organic group.)

[0017] R 5Examples of the organic group include linear or branched aliphatic saturated or aliphatic unsaturated hydrocarbon groups, alicyclic saturated or alicyclic unsaturated hydrocarbon groups (including bridged rings and condensed rings), aromatic hydrocarbon groups, organic groups in which some of the carbon atoms constituting the hydrocarbon groups are substituted with heteroatoms (e.g., oxygen atoms, nitrogen atoms, sulfur atoms, etc.), and organic groups in which two or more of these are bonded. Further, the hydrocarbon groups and the organic groups may have various substituents (e.g., halogen groups, alkyl groups, alkenyl groups, alkoxy groups, aryl groups, etc.).

[0018] R 5 is preferably a hydrogen atom.

[0019] Further, the compound of the present invention may contain a Si atom, but from the viewpoints of the storage stability of the compound of the present invention and the storage stability of the composition to which the compound of the present invention is added, it is preferably free of a Si atom. That is, the compound of the present invention is preferably free of an alkoxysilyl group and a silanol group.

[0020] The compound of the present invention can be synthesized, for example, by a known synthesis method for forming a biuret bond. Specifically, it can be synthesized by a method such as reacting a compound having a radical polymerizable functional group and a urea group with a compound having a radical polymerizable functional group and an isocyanate group.

[0021] Further, in the compound represented by the general formula (1), for example, R 3 or R 4 is an organic group in which two hydrocarbon groups are linked via a urethane bond, the compound can be specifically synthesized by reacting a compound having a urea group and a hydroxy group with a compound having a radical polymerizable functional group and an isocyanate group.

[0022] 2. Adhesion improver The adhesion improver of the present invention contains at least the compound of the present invention. The adhesion improver of the present invention may contain, in addition to the compound of the present invention, a silane coupling agent, various additives, a solvent, and the like.

[0023] The adhesion improving agent of the present invention can improve the adhesion of a material (curable composition) to a target substrate when added to a material used in applications requiring high adhesion. Examples of such materials include resist materials, adhesives, paints, coatings, varnishes, and inks.

[0024] 3. Curable Composition The curable composition of the present invention contains at least the compound of the present invention or an adhesion improver. The content of the compound of the present invention or the adhesion improver in the curable composition may be appropriately adjusted depending on the application of the curable composition and the required adhesion. As one embodiment of the curable composition of the present invention, the content of the compound of the present invention in the curable composition is preferably 1 to 30% by mass, more preferably 2 to 20% by mass, from the viewpoint of further improving adhesion to the substrate. The curable composition of the present invention may also contain, if necessary, binder polymers (base polymers); polymerizable compounds; photopolymerization initiators, photopolymerization initiator aids, acid generators, thermal polymerization initiators, silane coupling agents, crosslinking agents, surface modifiers (surfactants), sensitizers, ultraviolet absorbers, antioxidants, flame retardants, tackifiers, adhesion improvers, anti-aging agents, plasticizers, softeners, thickeners, dispersants, dyes, pigments, defoamers, and fillers; and solvents, etc., which are commonly used for the intended application.

[0025] [Uses of the Curable Composition] The curable composition of the present invention is suitably used as a resist material, adhesive, paint, coating agent, varnish, and ink. In particular, the curable composition of the present invention is suitably used as a negative-type resist material. Hereinafter, an embodiment of the present invention will be described in which the curable composition is a resist material.

[0026] [Resist Material] Resist materials to which the compound or adhesion improver of the present invention is added include materials for forming sacrificial films (resists) during various manufacturing processes such as sandblasting, ion implantation, and etching. Other embodiments of resist materials to which the compound or adhesion improver of the present invention is added include materials for forming insulating films, protective films, photospacers, and other components that constitute liquid crystal displays and touch panels. Because resist materials to which the compound or adhesion improver of the present invention is added have excellent adhesion and developability, it is possible to manufacture high-performance devices. The resist may be a negative resist or a positive resist.

[0027] The content of the compound of the present invention in the resist material is not particularly limited, but from the viewpoint of further improving adhesion to the substrate, it is preferably 1 to 20% by mass, more preferably 5 to 15% by mass, when the total amount of the compound of the present invention, the polymerizable compound below, and the base polymer below is 100% by mass.

[0028] The resist material typically includes, in addition to the compound or adhesion improver of the present invention, a polymerizable compound (monomer or oligomer), a base polymer, a photopolymerization initiator, and a solvent.

[0029] (Polymerizable Compounds) Resist materials typically contain at least one polymerizable compound (monomer or oligomer) having at least one ethylenically unsaturated double bond. The polymerizable compound is not particularly limited as long as it is capable of radical polymerization. The polymerizable compound may be, for example, a compound having one ethylenically unsaturated double bond in its molecule, a compound having two ethylenically unsaturated double bonds in its molecule, or a compound having three or more ethylenically unsaturated double bonds in its molecule.

[0030] Examples of compounds having one ethylenically unsaturated double bond in their molecule include nonylphenoxypolyethylene oxyacrylate, phthalate compounds, and alkyl (meth)acrylates. These may be used individually or in combination of two or more.

[0031] Examples of compounds having two ethylenically unsaturated double bonds in their molecule include bisphenol A-based di(meth)acrylate compounds, hydrogenated bisphenol A-based di(meth)acrylate compounds, di(meth)acrylate compounds having a urethane bond in their molecule, polyalkylene glycol di(meth)acrylate compounds, trimethylolpropane di(meth)acrylate, and 1,6-hexanediol diacrylate. These may be used individually or in combination of two or more.

[0032] Examples of compounds having three or more ethylenically unsaturated double bonds in their molecule include trimethylolpropane tri(meth)acrylate, EO-modified trimethylolpropane tri(meth)acrylate (with a total of 1 to 5 repeating oxyethylene groups), PO-modified trimethylolpropane tri(meth)acrylate, EO and PO-modified trimethylolpropane tri(meth)acrylate, tetramethylolmethane tri(meth)acrylate, tetramethylolmethane tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate. These may be used individually or in combination of two or more.

[0033] The content of the polymerizable compound in the resist material is not particularly limited, but when the total amount of the compound of the present invention, the polymerizable compound, and the base polymer described below is 100% by mass, it is preferably 15 to 55% by mass, more preferably 20 to 50% by mass, and even more preferably 25 to 45% by mass. When the content of the polymerizable compound is 15 parts by mass or more, sufficient sensitivity and resolution tend to be obtained, and when it is 55 parts by mass or less, the film formation properties tend to be good, and a good resist shape tends to be obtained.

[0034] (Base Polymer) The resist material usually contains at least one base polymer. The base polymer is not particularly limited and examples include acrylic resins, styrene resins, epoxy resins, amide resins, amide epoxy resins, alkyd resins, and phenolic resins. These may be used individually or in combination of two or more. Of these, acrylic resins are preferred from the viewpoint of alkali developability.

[0035] The base polymer can be produced, for example, by radical polymerization of polymerizable monomers. Examples of polymerizable monomers include polymerizable styrene derivatives having substituents at the α-position or on the aromatic ring, such as styrene, vinyltoluene, and α-methylstyrene; acrylamides such as diacetone acrylamide; esters of vinyl alcohols such as acrylonitrile and vinyl-n-butyl ether; alkyl (meth)acrylates, benzyl (meth)acrylates, tetrahydrofurfuryl (meth)acrylates, glycidyl (meth)acrylates, and 2,2,2-trifluoroethyl (meth) Examples include (meth)acrylic acid esters such as acrylate and 2,2,3,3-tetrafluoropropyl (meth)acrylate; acrylic acids such as (meth)acrylic acid, α-bromoacrylic acid, α-chloroacrylic acid, β-furyl(meth)acrylic acid, and β-styryl(meth)acrylic acid; maleic acid monoesters such as monoethyl maleate and monoisopropyl maleate; and maleic acid, maleic anhydride, monomethyl maleate, fumaric acid, cinnamic acid, α-cyanocinnamic acid, itaconic acid, crotonic acid, and propiolic acid. Alkyl (meth)acrylate esters may be compounds in which the alkyl group is substituted with a hydroxyl group, epoxy group, halogen group, etc. These may be used individually or in combination of two or more.

[0036] From the perspective of alkali developability, the base polymer preferably contains a carboxy group. The base polymer containing a carboxy group can be produced, for example, by radical polymerization of a polymerizable monomer having a carboxy group and other polymerizable monomers. Examples of the polymerizable monomer having a carboxy group include (meth)acrylic acid, a caprolactone adduct of (meth)acrylic acid, (meth)acryloylethyl monophthalate, (meth)acryloylethyl monohexahydrophthalate, (meth)acryloylethyl monotetrahydrophthalate, and the like. These may be used alone or in combination of two or more.

[0037] The content of the base polymer in the resist material is not particularly limited, but when the total amount of the compound, polymerizable compound, and base polymer of the present invention is 100% by mass, it is usually 20 to 80% by mass, preferably 30 to 70% by mass, more preferably 40 to 60% by mass.

[0038] (Photoinitiator) The resist material may contain a photoinitiator. The photoinitiator is not particularly limited. For example, benzoin and its alkyl ethers such as benzoin, benzoin methyl ether, and benzoin ethyl ether; acetophenones such as acetophenone, 2,2-dimethoxy-2-phenylacetophenone, and 1,1-dichloroacetophenone; anthraquinones such as 2-methylanthraquinone, 2-amylanthraquinone, 2-t-butylanthraquinone, and 1-chloroanthraquinone; thioxanthones such as 2,4-dimethylthioxanthone, 2,4-diisopropylthioxanthone, and 2-chlorothioxanthone; ketals such as acetophenone dimethyl ketal and benzyldimethyl ketal; benzophenones such as benzophenone; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1; acylphosphine oxides and xanthones, and the like. These may be used alone or in combination of two or more.

[0039] (Solvent) The resist material may contain a solvent. Examples of the solvent include ethers such as tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; esters such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, and 3-methoxybutyl acetate; alcohols such as methanol, ethanol, isopropanol, n-butanol, ethylene glycol monomethyl ether, and propylene glycol monomethyl ether; aromatic hydrocarbons such as toluene, xylene, and ethylbenzene; chloroform, dimethyl sulfoxide, and the like. These may be used alone or in combination of two or more.

[0040] (Additive) The resist material may contain various additives. Examples of the additives include photopolymerization initiation aids, acid generators, dyes, photochromic agents, thermal color inhibitors, plasticizers, hydrogen donors, color developers, pigments, fillers, antifoaming agents, flame retardants, adhesion promoters, leveling agents, antioxidants, fragrances, imaging agents, and thermal crosslinking agents.

[0041] 4. Cured Product The cured product of the present invention is obtained by curing the curable composition. Examples of the method for producing the cured product include a method in which the curable composition is coated on a substrate (substrate) or various functional layers to form a desired shape and then irradiated with light (e.g., ultraviolet light) to cure the curable composition. The method for producing the cured product is not particularly limited to this method, and for example, a method in which the curable composition applied to a substrate is cured by heat or the like can be adopted according to the purpose and application of forming the cured product. The curing conditions may be appropriately adjusted according to the curable composition used.

[0042] The cured product of the present invention is suitably used, for example, as a photospacer, a partition wall, a lens, an interlayer insulating film, a protective film, an overcoat film, an optical waveguide, a planarization film, an adhesive layer, a coating film, or a coating membrane.

[0043] The method for forming a cured product having a patterned shape is not particularly limited. For example, the curable composition can be applied to a substrate or various functional layers, dried to form a coating film, and then formed by photolithography. In photolithography, a negative-type formation method is preferred for forming a cured product having a patterned shape. For example, a photomask is placed on the coating film, the coating film is photocured by irradiation with ultraviolet light, a developer is sprayed onto the coating film after ultraviolet irradiation to dissolve and remove the unexposed areas, and the remaining exposed areas are washed and developed to form a cured product having a patterned shape. Post-baking may be performed thereafter.

[0044] The present invention will be described below with reference to examples, but the present invention is not limited in any way by these examples.

[0045] Manufacturing Example 1 [Synthesis of Polymer (A-1)] Polymer (A-1), represented by the following formula, was synthesized by the following manufacturing method. l:m:n=57:25:18 (mol%)

[0046] A glass flask equipped with a stirrer, reflux condenser, nitrogen inlet tube, and thermometer was charged with 93.1 g of methyl methacrylate, 80.0 g of 3,4-epoxycyclohexylmethyl methacrylate, 25.3 g of methacrylic acid, and 470.8 g of cyclohexanone. After replacing the gas phase in the system with nitrogen, 13.9 g of 2,2'-azobis(2,4-dimethylvaleronitrile) was added, and the mixture was heated to 65°C and reacted at the same temperature for 10 hours to obtain a cyclohexanone solution containing polymer (A-1) (solid content: approximately 22.6% by mass). Molecular weight measurement by GPC (standard substance: polystyrene) revealed that the weight-average molecular weight (Mw) of polymer (A-1) was 12,000.

[0047] Manufacturing Example 2 [Synthesis of Compound (C-1)] Compound (C-1), represented by the following formula, was synthesized by the manufacturing method described below.

[0048] In a reaction vessel equipped with a stirrer, reflux condenser, dropping funnel, and thermometer, 24 parts by mass of 2-hydroxyethyl urea (H0700, manufactured by Tokyo Chemical Industry Co., Ltd.), 218 parts by mass of propylene glycol monomethyl ether acetate (PGMEA), and 70 parts by mass of 2-isocyanatoethyl methacrylate (Karens MOI, manufactured by Resonac Co., Ltd.) were added. The mixture was raised to 80°C and reacted for 10 hours while maintaining this temperature to obtain a PGMEA solution containing compound (C-1) (solid content: approximately 30.0% by mass).

[0049] Manufacturing Example 3 [Synthesis of Compound (C-2)] Compound (C-2), represented by the following formula, was synthesized by the manufacturing method described below.

[0050] In a reaction vessel equipped with a stirrer, reflux condenser, dropping funnel, and thermometer, 100 parts by mass of 3-isocyanate propyltriethoxysilane (KBE-9007N, manufactured by Shin-Etsu Chemical Co., Ltd.) and 445 parts by mass of N-methylpyrrolidone (NMP) were placed. To this mixture, 91 parts by mass of ureidopropyltrimethoxysilane (T1915, manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise while stirring. The mixture was then raised to 65°C and reacted for 2 days while maintaining this temperature to obtain an NMP solution containing compound (C-2) (solid content: approximately 30.0% by mass).

[0051] Examples 1-3 and Comparative Examples 1-6 [Preparation of Curable Compositions] Curable compositions were prepared by mixing each component listed in Table 1 in the proportions (parts by mass) listed in Table 1. The mixing was carried out at room temperature, with ultraviolet light blocked to prevent the polymerization reaction from starting. The amount of solvent in each composition was adjusted by adding each solvent separately to the solvent derived from each solution described above, so as listed in Table 1. The other components listed in Table 1 are as follows: <Polymerizable compound (B)> B-1: Tricyclodecanedimethanol diacrylate <Photopolymerization initiator (D)> D-1: 1-[4-(phenylthio)phenyl]octane-1,2-dione=2-(O-benzoyloxime) (Irgacure OXE-01, manufactured by BASF Japan Ltd.) <Surfactant (E)> E-1: Polyether-modified silicone (DOWSIL) TMFZ-2122, manufactured by Dow Toray Ltd.) <Solvent> Cyclohexanone propylene glycol monomethyl ether acetate (PGMEA) N-methylpyrrolidone (NMP) Each solvent is contained in each solution obtained in each of the above-described manufacturing examples.

[0052] Next, the curable compositions prepared in Examples 1-3 and Comparative Examples 1-6 were evaluated for developability, chemical resistance, and storage stability using the following methods. The results are shown in Table 1.

[0053] [Developing Adhesion] The curable resin compositions of Examples 1-3 and Comparative Examples 1-6 were applied to a test substrate (MAM, SiNx, or ITO) by spin coating, pre-baked on a hot plate at 90°C for 120 seconds to form a coating film, and exposed to light from an ultra-high pressure mercury lamp at 100 mJ / cm² through a 10 μm square dot mask. 2 Irradiated (Illuminance at 365 nm: 10 mW / cm²) 2 ). Subsequently, each sample substrate was prepared with a 10 μm square dot pattern by developing it with a 0.3% sodium carbonate aqueous solution for 60 seconds. The dot patterns formed on each sample substrate after development were observed under a microscope, and the development adhesion was evaluated according to the following criteria. <Evaluation Criteria> A: No peeled dot pattern (adhesion rate 100%) B: Partial peeled dot pattern (adhesion rate 30% or more and less than 100%) C: Many peeled dot patterns (adhesion rate less than 30%)

[0054] [Chemical Resistance and Adhesion] The curable resin compositions of Examples 1-3 and Comparative Examples 1-6 were applied to a test substrate (MAM, SiNx, or ITO) by spin coating, pre-baked on a hot plate at 90°C for 120 seconds to form a coating film, and exposed to light from an ultra-high pressure mercury lamp at 100 mJ / cm². 2 Irradiated (Illuminance at 365 nm: 10 mW / cm²) 2). Subsequently, a substrate with a cured film thickness of 2.0 μm was prepared by developing with a 0.3% sodium carbonate aqueous solution for 60 seconds and heating at 150°C for 30 minutes. Then, the obtained substrate with the cured film was immersed in a 3.6% by mass oxalic acid aqueous solution at 41°C for approximately 120 seconds. After immersion, the substrate was washed with water and then immersed in an amine solution (monoethanolamine / diethylene glycol monobutyl ether = 70 / 30 (by mass%)) at 60°C for approximately 60 seconds. After immersion, the substrate with the cured film was washed with water and dried, and then the surface of the cured film was cross-cut using a utility knife (1 mm × 1 mm × 100 squares). Subsequently, cellophane tape was applied to the cut surface and then peeled off. The surface of the cured film on the substrate was then observed with a stereomicroscope, and the number of squares in which the cured film remained intact was counted, and the chemical resistance adhesion was evaluated according to the following criteria based on that number. <Evaluation Criteria> A: 95 or more squares remained with the hardened film intact. B: 50 to 94 squares remained with the hardened film intact. C: 49 or fewer squares remained with the hardened film intact.

[0055] [Storage Stability] The viscosity change of each curable composition prepared in Examples 1-3 and Comparative Examples 1-6 was measured after storage at 25°C for 30 days, and the storage stability was evaluated according to the following criteria. <Evaluation Criteria> A: Viscosity increase rate of 5% or less compared to the time of preparation B: Viscosity increase rate of more than 5% but 20% or less compared to the time of preparation C: Viscosity increase rate of more than 20% compared to the time of preparation

[0056]

[0057] As shown in Table 1, the curable composition containing compound (C-1), which is one embodiment of the compound of the present invention, is excellent in terms of developability, chemical resistance, and storage stability.

[0058] The compounds of the present invention can impart adhesion to curable compositions such as resist materials, adhesives, paints, and coatings by being incorporated into such compositions.

Claims

1. A compound having two or more functional groups containing ethylenically unsaturated double bonds and a biuret bond.

2. The compound according to claim 1, wherein the functional group containing an ethylenically unsaturated double bond is a (meth)acryloyloxy group.

3. The compound according to claim 1, further comprising a urethane bond.

4. The compound according to claim 1, which does not contain Si atoms.

5. An adhesion improving agent comprising the compound described in claim 1.

6. A curable composition comprising the compound described in claim 1, or the adhesion improving agent described in claim 5.

7. The curable composition according to claim 6, which is a resist material, adhesive, paint, or coating agent.

8. A cured product obtained from the curable composition described in claim 7.

9. The cured product according to claim 8, wherein the cured product is a photospacer, partition, lens, interlayer insulating film, protective film, overcoat film, optical waveguide, planarization film, adhesive layer, coating film, or coating film.

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