Non-polymeric compounds and film-forming compositions

Abstract

To provide a non-polymer compound represented by the following formula (1) as a novel non-polymer compound having excellent ultraviolet absorbency, visible light transmittance, and solubility in organic solvents. (In the formula, n represents an integer of 3 to 6, A represents an n-valent organic group which can have a hetero atom selected from a nitrogen atom and an oxygen atom, k represents 0 or 1, and X represents an ultraviolet absorbent group.)

Description

Technical Field

[0001] This invention relates to nonpolymer compounds and film-forming compositions comprising them. Background Technology

[0002] In the field of optical components such as eyeglass lenses, Fresnel lenses, biconvex lenses, aspherical lenses, optical discs, optical fibers, and optical waveguides, transparent resins made of polymer materials with excellent transparency in the visible light range are widely used.

[0003] In recent years, in the field of electronic devices such as liquid crystal displays, organic electroluminescent (EL) displays, light-emitting diodes, solar cells, and CCD / CMOS image sensors, transparent resins with excellent visible light transmittance are widely used for optical components such as protective films, planarization films, insulating films, anti-reflective films, refractive index control films, microlenses, in-layer lenses, optical waveguides, and film substrates.

[0004] In the application of such optical components, not only transparency but also excellent lightfastness is often required. However, it is known that optical components based on transparent resins using the aforementioned polymer materials deteriorate under ultraviolet light, causing discoloration and other quality degradation, and therefore cannot withstand long-term use.

[0005] To improve the lightfastness of optical components, ultraviolet (UV) absorbers are generally formulated (Patent Documents 1-4). Examples of UV absorbers include benzophenone-based, benzotriazole-based, triazine-based, cyanoacrylate-based, salicylate-based, benzoate-based, oxaloaniline-based, and malonic acid ester-based UV absorbers.

[0006] The aforementioned ultraviolet absorbers are primarily used in the formation of coatings (ultraviolet absorbing films) for protecting optical components, primarily from the viewpoint of improving lightfastness (Patent Documents 5-6). Furthermore, in addition to improving the lightfastness of optical components, for example, by forming an ultraviolet absorbing film containing the aforementioned ultraviolet absorbers on the optical components, ultraviolet shielding and anti-reflective functions can be imparted (Patent Documents 7-10).

[0007] To improve UV absorption, such UV-absorbing films need to be formed thicker; conversely, to reduce their impact on the optical properties of optical components, they need to be formed thinner. To reconcile these contradictory characteristics, a UV absorber is needed that provides sufficient UV absorption even in thin films for practical application.

[0008] Furthermore, from the viewpoint of productivity of the film-forming composition, it is necessary for the ultraviolet absorber to be soluble in a wide variety of organic solvents. In particular, during the manufacturing process of the film-forming composition, when the ultraviolet absorber is mixed with an organic solvent other than the one in which it is dissolved, precipitation sometimes occurs due to the combination of organic solvents. In such cases, problems such as piping blockage in the production equipment may occur.

[0009] Furthermore, in optical components, other functional films (upper layers) are sometimes formed on the ultraviolet-absorbing film. In this case, generally, a composition (varnish) for forming the upper layer is coated on the ultraviolet-absorbing film. If the solvent resistance of the ultraviolet-absorbing film is insufficient, sometimes a portion of it dissolves due to the organic solvent used in the composition for forming the upper layer.

[0010] Existing technical documents

[0011] Patent documents

[0012] Patent Document 1: Japanese Patent Application Publication No. 2009-51992

[0013] Patent Document 2: Japanese Patent Application Publication No. 2010-265170

[0014] Patent Document 3: Japanese Patent Application Publication No. 2010-286644

[0015] Patent Document 4: Japanese Patent Application Publication No. 2013-82233

[0016] Patent Document 5: Japanese Patent Application Publication No. 2019-172846

[0017] Patent Document 6: Japanese Patent Publication No. 2000-515141

[0018] Patent Document 7: Japanese Patent Application Publication No. 9-265059

[0019] Patent Document 8: Japanese Patent Application Publication No. 2003-107202

[0020] Patent Document 9: Japanese Patent Application Publication No. 2006-243153

[0021] Patent Document 10: Japanese Patent Application Publication No. 2007-99943 Summary of the Invention

[0022] The problem that the invention aims to solve

[0023] The present invention was made in view of the above-mentioned circumstances, and its object is to provide a novel non-polymer compound that combines practical ultraviolet absorption and visible light transmittance with excellent solubility in organic solvents. Furthermore, the object is to provide a film-forming composition comprising the above-mentioned non-polymer compound capable of forming a coating film that combines practical ultraviolet absorption and visible light transmittance with excellent solvent resistance.

[0024] Methods for solving problems

[0025] To achieve the above objectives, the inventors conducted repeated and in-depth research, and discovered that specific non-polymer compounds having 3 to 6 ultraviolet-absorbing groups within their molecules possess both practical ultraviolet absorption and visible light transmittance, as well as excellent solubility in organic solvents. Furthermore, by using this non-polymer compound as an ultraviolet absorber, a film-forming composition containing the non-polymer compound is obtained, capable of forming a coating film that possesses both practical ultraviolet absorption and visible light transmittance, and excellent solvent resistance, thus completing the present invention.

[0026] That is, the present invention provides the following nonpolymer compounds and film-forming compositions.

[0027] 1. A nonpolymer compound represented by the following formula (1),

[0028] [Chemistry 1]

[0029]

[0030] In the formula, n represents an integer from 3 to 6, A represents an organic group with an n-valence that may have a heteroatom selected from nitrogen and oxygen atoms, k represents 0 or 1, and X represents an ultraviolet-absorbing group.

[0031] 2. The nonpolymer compound according to claim 1, wherein each of the ultraviolet-absorbing groups is independently a group having any one of a benzotriazole skeleton, a triazine skeleton, a benzophenone skeleton, a cyanoacrylate skeleton, a salicylate skeleton, and an oxaloylaniline skeleton.

[0032] 3. The nonpolymer compound according to claim 2, wherein each of the ultraviolet-absorbing groups is independently a group having a triazine skeleton or a benzophenone skeleton.

[0033] 4. The non-polymer compound according to claim 3, wherein each of the ultraviolet-absorbing groups is independently a group represented by formula (x1) or formula (x2) below.

[0034] [Chemistry 2]

[0035]

[0036] In equation (x1), Ra Each of the following independently represents a hydrogen atom, hydroxyl group, methyl group, or ethyl group, wherein the R a At least one of them is a hydroxyl group, R 1 and R 2 Each of them independently represents methyl or ethyl, m1 independently represents an integer from 0 to 3, and m2 represents an integer from 0 to 2.

[0037] In equation (x2), R b Each independently represents a hydrogen atom or a hydroxyl group, wherein the R b At least one of them is a hydroxyl group.

[0038] * indicates the bonding end.

[0039] 5. The non-polymer compound according to claim 4, wherein each of the ultraviolet-absorbing groups is independently represented by formula (x1-1) or formula (x2-1), and at least one of the n ultraviolet-absorbing groups is represented by formula (x1-1).

[0040] [Chemistry 3]

[0041]

[0042] In the formula, R 1 Each of the characters independently represents either methyl or ethyl, m3 independently represents an integer from 0 to 5, and * represents a bond end.

[0043] 6. The nonpolymer compound according to any one of 1 to 5, wherein the molecular weight is 500 to 3500.

[0044] 7. The nonpolymer compound according to any one of 1 to 6, which is the reaction product of a compound having 3 to 6 epoxy groups in one molecule and a compound having the ultraviolet-absorbing group and a phenolic hydroxyl or carboxyl group.

[0045] 8. The nonpolymer compound according to any one of 1 to 7, wherein the organic group represented by A is a group represented by any one of the following formulas (a1) to (a7),

[0046] [Chemistry 4]

[0047]

[0048] In the formula, * represents the bonding end.

[0049] 9. A film-forming composition comprising a nonpolymer compound represented by formula (1) according to any one of 1 to 8, a curing agent, and an organic solvent, wherein the content of the curing agent is 15 parts by mass or more relative to 100 parts by mass of the nonpolymer compound.

[0050] 10. The film-forming composition according to claim 9, wherein the curing agent is a multifunctional terminal isocyanate compound.

[0051] 11. The film-forming composition according to 10, wherein the multifunctional isocyanate compound is a homopolymer of a (meth)acrylate having a capped isocyanate group, or a copolymer containing a (meth)acrylate having a capped isocyanate group.

[0052] 12. The film-forming composition according to any one of 9 to 11, further comprising a surfactant.

[0053] 13. The film-forming composition according to any one of 9 to 12, further comprising a light stabilizer.

[0054] 14. A membrane obtained from the membrane forming composition according to any one of 9 to 13.

[0055] The effects of the invention

[0056] The non-polymer compound of the present invention possesses both practical ultraviolet absorption and visible light transmittance, as well as excellent solubility in organic solvents, and therefore can be used as an ultraviolet absorber. Furthermore, by using this non-polymer compound as an ultraviolet absorber, it is possible to obtain a film-forming composition capable of forming a coating film that possesses both practical ultraviolet absorption and visible light transmittance, and excellent solvent resistance.

[0057] The coating formed by the above-mentioned film forming composition is suitable as an optical component such as a protective film, planarization film, insulating film, anti-reflection film, refractive index control film, microlens, intralayer lens, optical waveguide, and film substrate. Detailed Implementation

[0058] The present invention will now be described in more detail.

[0059] The non-polymer compound involved in this invention is characterized by being represented by the following formula (1).

[0060] It should be noted that in this invention, the term "non-polymer compound" refers to a compound with a molecular weight of less than 3500 that is not a polymer.

[0061] [Chemistry 5]

[0062]

[0063] (In the formula, n represents an integer from 3 to 6, A represents an organic group with an n-valence that may have a heteroatom selected from nitrogen and oxygen atoms, k represents 0 or 1, and X represents an ultraviolet-absorbing group.)

[0064] n represents an integer from 3 to 6, preferably from 3 to 5.

[0065] As an organic group represented by A above, any group represented by any of the following formulas (a1) to (a7) can be listed, but is not limited to these.

[0066] [Chemistry 6]

[0067]

[0068] (In the formula, * indicates the bonding end.)

[0069] As for X above, it can be any group having any one of the following skeletons: benzotriazole skeleton, triazine skeleton, benzophenone skeleton, cyanoacrylate skeleton, salicylate skeleton, and oxaloaniline skeleton. Multiple Xs may all be the same group or may be different.

[0070] In the above-mentioned X, from the viewpoint of solubility in organic solvents and ultraviolet absorption, groups having a triazine skeleton or a benzophenone skeleton are preferred, and groups having both a triazine skeleton and a benzophenone skeleton are also preferred.

[0071] As a preferred embodiment of the aforementioned ultraviolet-absorbing group, groups represented by the following formulas (x1) to (x2) can be listed.

[0072] [Chemistry 7]

[0073]

[0074] (In formula (x1), R) a Each of the following independently represents a hydrogen atom, hydroxyl group, methyl group, or ethyl group, wherein the R a At least one of them is a hydroxyl group, R 1 and R 2 Each of them independently represents methyl or ethyl, m1 independently represents an integer from 0 to 3, and m2 represents an integer from 0 to 2.

[0075] In equation (x2), R b Each independently represents a hydrogen atom or a hydroxyl group, wherein the R b At least one of them is a hydroxyl group.

[0076] * indicates the bonding end.

[0077] As a more preferred embodiment of the aforementioned ultraviolet-absorbing groups, groups represented by the following formulas (x1-1) and (x2-1) can be listed. Furthermore, considering ultraviolet absorption, it is more preferable that at least one of the n aforementioned ultraviolet-absorbing groups is a group represented by the above formula (x1-1).

[0078] [Chemistry 8]

[0079]

[0080] (where R) 1 Each ...

[0081] As specific examples of the aforementioned ultraviolet-absorbing groups, groups represented by the following formulas (x1-1-1) and (x2-1-1) can be listed, but are not limited to these.

[0082] [Chemistry 9]

[0083]

[0084] (In the formula, * indicates the bonding end.)

[0085] [Chemistry 10]

[0086]

[0087] (In the formula, * indicates the bonding end.)

[0088] As specific examples of the aforementioned non-polymer compounds, compounds represented by the following formulas (1-1) to (1-13) can be listed, but are not limited to these.

[0089] [Chemistry 11]

[0090]

[0091] [Chemistry 12]

[0092]

[0093] In the formula, X 1 and X 2 Each represents a group represented by the following formula.

[0094] [Chemistry 13]

[0095]

[0096] (In the formula, * indicates the bonding end.)

[0097] Regarding the molecular weight of the aforementioned non-polymer compounds, from the viewpoint of solubility in organic solvents, it is, for example, 500 to 3500, preferably 500 to 3000, and more preferably 1000 to 3000.

[0098] The aforementioned non-polymer compounds can be obtained by reacting a compound having 3 to 6 epoxy groups in one molecule with a compound having the aforementioned ultraviolet-absorbing groups and phenolic hydroxyl or carboxyl groups.

[0099] Specific examples of compounds having 3 to 6 epoxide groups in one molecule include compounds represented by the following formulas (A1) to (A7), but are not limited thereto.

[0100] [Chemistry 14]

[0101]

[0102] Compounds having ultraviolet-absorbing groups and phenolic hydroxyl or carboxyl groups can be listed as compounds represented by the following formulas (X1-1) and (X2-1), but are not limited thereto.

[0103] [Chemistry 15]

[0104]

[0105] [Chemistry 16]

[0106]

[0107] There are no particular limitations on the synthesis method of the above-mentioned non-polymer compounds. For example, the following method can be listed: the above-mentioned compound having 3 to 6 epoxy groups in one molecule and the above-mentioned compound having ultraviolet-absorbing groups and phenolic hydroxyl or carboxyl groups are dissolved in an organic solvent at an appropriate ratio (molar ratio) corresponding to the number of epoxy groups, and reacted at 60 to 150°C for 1 to 48 hours in the presence of a catalyst.

[0108] The organic solvent used in the above reaction is not particularly limited as long as it dissolves the raw materials and catalyst. Specific examples include the same organic solvents used in the film-forming compositions described later. From the viewpoint of the solubility of the raw material compounds, tetrahydrofuran, 1,4-dioxane, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclopentanone, cyclohexanone, N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and N-ethyl-2-pyrrolidone are preferred. One of these organic solvents may be used alone, or two or more may be used in combination.

[0109] Furthermore, as the catalyst described above, catalysts known as catalysts that promote the reaction of epoxy groups with phenolic hydroxyl groups or carboxyl groups can be used. In this invention, quaternary phosphonium salts and quaternary ammonium salts are preferred, and quaternary phosphonium salts are more preferred.

[0110] Examples of quaternary phosphonium salts include methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, hexyltriphenylphosphonium bromide, tetrabutylphosphonium bromide, benzyltriphenylphosphonium bromide, methyltriphenylphosphonium chloride, ethyltriphenylphosphonium chloride, butyltriphenylphosphonium chloride, hexyltriphenylphosphonium chloride, tetrabutylphosphonium chloride, benzyltriphenylphosphonium chloride, methyltriphenylphosphonium iodide, ethyltriphenylphosphonium iodide, butyltriphenylphosphonium iodide, hexyltriphenylphosphonium iodide, tetrabutylphosphonium iodide, and benzyltriphenylphosphonium iodide. In this invention, ethyltriphenylphosphonium bromide and tetrabutylphosphonium bromide are preferred.

[0111] Examples of quaternary ammonium salts include tetramethylammonium fluoride, tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium nitrate, tetramethylammonium sulfate, tetramethylammonium acetate, tetraethylammonium chloride, tetraethylammonium bromide, tetrapropylammonium chloride, tetrapropylammonium bromide, tetrabutylammonium fluoride, tetrabutylammonium chloride, tetrabutylammonium bromide, benzyltrimethylammonium chloride, phenyltrimethylammonium chloride, benzyltriethylammonium chloride, methyltributylammonium chloride, benzyltributylammonium chloride, and methyltrioctylammonium chloride. In this invention, benzyltriethylammonium chloride is preferably used.

[0112] The film-forming composition of the present invention is characterized by containing the aforementioned non-polymer compound, curing agent, and organic solvent. It should be noted that, in the following description, "solid component" refers to components other than the organic solvent constituting the film-forming composition.

[0113] <Curing agent>

[0114] The curing agent is a component contained therein to improve the chemical resistance (solvent resistance) of the coating film formed by the film-forming composition of the present invention.

[0115] Examples of curing agents include polyfunctional (meth)acrylate compounds, hydroxymethyl or alkoxymethyl substituted phenolic compounds, compounds with alkoxyalkylated amino groups, and polyfunctional end-capped isocyanate compounds. In this specification, (meth)acrylate means methacrylates and acrylates. These curing agents can be used alone or in combination of two or more.

[0116] The content of the curing agent varies depending on the coating solvent used, the substrate used, the required solution viscosity, the required film shape, etc., and is at least 15 parts by mass relative to 100 parts by mass of the aforementioned non-polymer compound, preferably 15 to 80 parts by mass, more preferably 15 to 70 parts by mass, and even more preferably 20 to 60 parts by mass. These curing agents sometimes undergo curing reactions caused by self-condensation, and can undergo crosslinking reactions with these crosslinking substituents when crosslinking substituents are present in the aforementioned non-polymer compound of the present invention.

[0117] Examples of the aforementioned polyfunctional (meth)acrylate compounds include ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, propylene glycol dimethacrylate, dipropylene glycol dimethacrylate, tripropylene glycol dimethacrylate, polypropylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, neopentyl glycol dimethacrylate, 1,6-hexanediol dimethacrylate, tricyclodecanediethanol dimethacrylate, dicyclopentyl dimethacrylate, bisphenol A dimethacrylate, ethoxylated bisphenol A dimethacrylate, propoxylated bisphenol A dimethacrylate, bisphenol S dimethacrylate, and phthalic acid dimethacrylate. Esters, 9,9-bis[4-(2-(meth)acryloyloxyethoxy)phenyl]fluorene, glycerol di(meth)acrylate, glycerol tri(meth)acrylate, glycerol ethoxytri(meth)acrylate, glycerol propoxytri(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane ethoxytri(meth)acrylate, trimethylolpropane propoxytri(meth)acrylate, di(trimethylolpropane)tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol ethoxytetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, sorbitol hexa(meth)acrylate, tri(2-(meth)acryloyloxyethyl)isocyanurate and ε-caprolactone-modified tri-(2-(meth)acryloyloxyethyl)isocyanurate, etc.

[0118] In addition, as examples of the aforementioned polyfunctional (meth)acrylate compounds, examples include (meth)acrylates containing hydroxyl groups such as 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, glycerol dimeth)acrylate, pentaerythritol trimeth)acrylate, and dipentaerythritol pentameth)acrylate, or polyfunctional (meth)acrylates containing hydroxyl groups and 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 1,3-xylene diisocyanate, 1,4-xylene diisocyanate, phenylenediamine diisocyanate, and 1,5-naphthalene diisocyanate. Polyfunctional carbamate (meth)acrylates are obtained by reacting diisocyanate compounds such as esters, isophenyl diisocyanate, terephthalic diisocyanate, diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-dibenzyl diisocyanate, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, dicyclohexylmethane diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 1,3-bis(isocyanate methyl)benzene, and 1,3-bis(isocyanate methyl)cyclohexane.

[0119] Furthermore, as examples of the aforementioned polyfunctional (meth)acrylate compounds, polyfunctional epoxy (meth)acrylates can also be synthesized by reacting homopolymers or copolymers obtained from the free radical polymerization of epoxy-containing (meth)acrylate monomers such as glycidyl (meth)acrylate, glycidyl oxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl methyl (meth)acrylate with (meth)acrylic acid. Here, a copolymer refers to a polymer obtained by polymerizing two or more monomers. The copolymer can be a copolymer obtained by polymerizing two or more epoxy-containing (meth)acrylates, or a copolymer obtained by polymerizing epoxy-containing (meth)acrylates and other (meth)acrylates.

[0120] The aforementioned polyfunctional (meth)acrylate compounds are also available as commercially available products. Examples of such commercially available products include the following.

[0121] Aronix [Registered Trademark] M-208, M-210, M-211B, M-215, M-220, M-225, M-233, M-240, M-245, M-260, M-270, M-303, M-305, M -306, M-309, M-310, M-313, M-315, M-321, M-350, M-360, M-400, M-402, M-403, M-404, M-405, M-406, M-40 8. M-450, M-452, M-460, M-510, M-520, M-1100, M-1200, M-1210, M-1310, M-1600, M-1960, M-6100, M-6200, M-6250, M-6500, M-7100, M-7300K, M-8030, M-8060, M-8100, M-8530, M-8560, M-9050 (all manufactured by Toa Synthetic Co., Ltd.);

[0122] KAYARAD [Registered Trademark] NPGDA, PEG400DA, FM-400, R-167, HX-220, HX-620, R-526, R-551, R-712, R-604, R-684, GPO-303, TMPTA, HDDA, TPGDA, KS-HDDA, KS-TPGDA, MANDA, THE-330 , TPA-320, TPA-330, PET-30, T-1420, T-1420 (T), RP-1040, DPHA, DPEA-12, D-310, D- 330, DPCA-20, DPCA-30, DPCA-60, DPCA-120, FM-700, DN-0075, DN-2475, TC-120S, R- 115. R-130, R-381, EAM-2160, CCR-1291H, CCR-1235, ZAR-1035, ZAR-2000, ZFR-1401 H, ZFA-1491H, ZCR-1569H, ZCR-1601H, ZCR-1797H, ZCR-1798H, UXE-3000, UXE-3024, UX-3204, UX-4101, UXT-6100, UX-6101, UX-7101, UX-8101, UX-0937, UXF-4001-M35, UXF-4002, DPHA-40H, UX-5000, UX-5102D-M20, UX-5103D, UX-5005 (all manufactured by Nippon Kayaku Co., Ltd.);

[0123] NK Ester A-200, A-400, A-600, A-1000, A-1500, A-2000, ABE-300, A-BPE-4, A-BPE-6, A- BPE-10, A-BPE-20, A-BPE-30, A-BPEF, A-BPP-3, A-DCP, A-DOD-N, A-HD-N, A-NOD , A-GLY-3E, A-GLY-9E, A-GLY-20E, A-TMPT, A-TMPT-3EO, A-TMPT-9EO, ATM-4E, ATM-35E, APG-100, APG-200, APG-400, APG-700, A-PTMG-65, A-1000PER, A-B120 6PE, 701A, A-9300, A-9300-1CL, A-9300-6CL, A-9530, ADP-51EH, ATM-31EH, A- TMM-3, A-TMM-3L, A-TMM-3LM-N, AD-TMP, A-TMMT, A-9550, A-DPH, A-DPH-12E, 1G , 2G, 3G, 4G, 9G, 14G, 23G, BPE-80N, BPE-100, BPE-100N, BPE-200, BPE-500, BPE-900, BPE-1300N, DCP, DOD-N, HD-N, NOD-N, NPG, 1206PE, 701, 3PG, 9PG, TMPT, NK EKONOMA A-PG5009E, A-PG5027E, A-PG5054E, NK Oligo U-2PPA, U-6LPA, U-10HA, U-10PA, UA-1100H, U-4H, U-6H, U-4HA, U-6HA, U-15HA, UA-32P, UA-33H, UA-53H, U-200PA, U-324A, UA-160TM, UA-290TM, UA-4200, UA-4400, UA-122P, UA-7100, UA-W2A (all manufactured by Shin-Nakamura Chemical Industry Co., Ltd.);

[0124] BISCOAT#195, #230, #260, #310HP, #335HP, #700HV, #540, #802, #295, #300, #360, #230D, BAC-45, SPDBA-S30, STAR-501 (all manufactured by Osaka Organic Chemical Industry Co., Ltd.);

[0125] Light Ester P-2M, EG, 2EG, 3EG, 4EG, 9EG, 14EG, 1.4BG, NP, 1.6HX, 1.9ND, G-101P, G-201P, BP-2EMK, TMP, Light Acrylate [Registered Trademark] 3EG-A, 4EG-A, 9EG-A, 14EG-A, PTMGA-250, NP-A, MPD-A, 1.6HX-A, 1.9ND-A, MOD-A, DCP-A, BP-4EAL, BP-4PA, HPP-A, G-201P, TMP-A, PE-3A, PE-4A, DPE-6A, EPOXY ESTER 40EM, 70PA, 200PA, 80MFA, 3002M(N), 3002A(N), 3000MK, 3000A, EX-0205, AH-600, AT-600, UA-306H, UA-306T, UA-306I, UA-510H, UF-8001G, DAUA-167 (all manufactured by Kyoeisha Chemical Co., Ltd.);

[0126] Art Resin [Registered Trademarks] UN-333, UN-350, UN-1255, UN-2600, UN-2700, UN-5200, UN-5500, UN-5590, UN-5507, UN-6060PTM, UN-6200, UN-6202, UN-6300, UN-6301, UN-7600, UN-7700, UN-9000H, UN-9000PEP, UN-9200A, UN-3320HA, UN-3200HB, UN-3320HC, UN-3320HS, UN-904, UN-906S, UN-901T, UN-905, UN-906, UN-952, HDP-4T, HMP-2, H-61, HDP-M20 (all manufactured by Nejou Kogyo Co., Ltd.);

[0127] Tsinghua Unigroup [Registered Trademark] UV-1400B, UV-1700B, UV-2000B, UV-2010B, UV-2750B, UV-3000B, UV-3200B, UV-3210EA, UV-3300B, UV-3310B, UV-3500BA, UV-3520TL, UV-3610D80, UV-3630D80, UV-3640PE80, UV-3700B, UV-6100B, UV-6300B, UV-6640B, UV-7000, UV-7000B, UV-7461TE, UV-7510B, UV-7550B, UV-7600B, UV-7605B, UV-7610B, UV-7620EA, UV-7630B, UV-7640B, UV-7650B, UV-NS001, UV-NS034, UV-NS054, UV-NS063, UV-NS077 (all manufactured by Nippon Synthetic Chemicals Co., Ltd.);

[0128] BEAMSET [Registered Trademark] 243NS, 255, 261, 271, 502H, 504H, 505A-6, 550B, 575, 577, 700, 710, 730, 750, AQ-17, EM-90, EM-92, 371, 381 (all manufactured by Arakawa Chemical Industry Co., Ltd.);

[0129] FANCRYL [Registered Trademark] FA-124AS, FA-129AS, FA-222A, FA-240A, FA-P240A, FA-P270A, FA-321A, FA-324A, FA-PTG9A, FA-731A, FA-121M, FA-124M, FA-125M, FA-220M, FA-240M, FA-320M, FA-321M, FA-3218M, FA-PTG9M, FA-137M (all manufactured by Resonac Co., Ltd.);

[0130] SR212、SR213、SR230、SR238F、SR259、SR268、SR272、SR306H、SR344、SR349、SR508、CD560、CD561、CD564、SR601、SR602、SR610、SR833S、SR9003、CD9043、SR9045、SR9209、SR205、SR206、SR209、SR210、SR214、SR231、SR239、SR248、SR252、SR297、SR348、SR480、CD540、CD541、CD542、SR603、SR644、SR9036、SR351S、SR368、SR415、SR444、SR454、SR492、SR499、CD501、SR502、SR9020、CD9021、SR9035、SR350、SR295、SR355、SR399、SR494、SR9041、SR9041、CN929、CN961E75、CN961H81、CN962、CN963、CN963A80、CN963B80、CN963E75、CN963E80、CN963J85、CN964、CN964E75、CN964A85、CN965、CN965A80、CN966A80、CN966H90、CN966J75、CN966R60、CN968、CN980、CN981、CN981A75、CN981B88、CN982、CN982A75、CN982B88、CN982E75、CN983、CN985B88、CN996、CN9001、CN9002、CN9788、CN9893、CN970A60、CN970E60、CN971、CN971A80、CN972、CN973A80、CN973H85、CN973J75、CN975、CN977C70、CN978、CN9782、CN9783、CN104、CN104A80、CN104B80、CN111、CN112C60、CN115、CN116、CN118、CN120、CN120A60、CN120A75、CN120B60、CN120B80、CN120C60、CN120C80、CN120D80、CN102E50、CN120M50、CN124、CNUVE151、CNUVE151 / 80、CN151、CN2203、CN2270、CN2271、CN2273、CN2274、CN307、CN371、CN550、CN551、SB401、SB402、SB404、SB500E50, SB500K60, SB510E35, SB520E35, SB520M35 (all manufactured by Sartamomer);

[0131] DPGDA, HODA, TPGDA, PEG400DA-D, HPNDA, PETIA, PETRA, TMPTA, TMPEOTA, OTA480, DPHA, IRR214-K, IRR679, IRR 742, IRR793, (ACA) Z200M, (ACA) Z230AA, (ACA) Z250, (ACA) Z251, (ACA) Z300, (ACA) Z320, (ACA) Z254F, EBECRY L [Registered Trademark] 145, 150, 11, 135, 40, 140, 1142, 180, 204, 205, 210, 215, 220, 230, 244, 245, 264, 265, 270, 280 / 151B, 284, 285, 294 / 25HD, 1259, 1290, 4820, 4858, 5129, 8210, 8254, 8301R, 8307, 8402, 8405, 8411, 8465, 8800, 8804 ,8807,9260,9270,8311,8701,9227EA,436,438,446,450,524,525,770,800,810,811,812,1830,846,851,8 52, 853, 1870, 884, 885, 600, 605, 645, 648, 860, 1606, 3500, 3603, 3608, 3700, 3701, 3702, 3703, 3708, 6040, 8 110, 271, 1258, 1291, 4100, 4200, 4500, 4680, 4220, 4265, 4491, 4513, 4587, 4666, 4683, 4738, 4740, 4250, 4510, KRM [Registered Trademark] 8200, 8200AE, 8296, 8452, 8904, 8667, 8912, 8981, 8762, 8713B, 8528 (all manufactured by Daicel-Allnex Co., Ltd.);

[0132] BAEA-100, BAEM-100, BAEM-50, BEEM-50, BFEA-50, HPEA-100, CNEA-100, PNEM-50, RNEA-100, TEA-100, KUA-4I, KUA-6I , KUA-9N, KUA-10H, KUA-15N, KUA-C2I, KUA-PC2I, KUA-PEA2I, KUA-PEB2I, KUA-PEC2I, RP-274S, RP-310 (the above are manufactured by KSM Co., Ltd.).

[0133] These multifunctional (meth)acrylate compounds can be used alone or in combination of two or more.

[0134] Examples of the aforementioned hydroxymethyl or alkoxymethyl substituted phenolic compounds include 1,3,5-trihydroxymethylbenzene, 2,6-dihydroxymethyl-4-methylphenol, 2,4-dihydroxymethyl-6-methylphenol, bis(2-hydroxy-3-hydroxymethyl-5-methylphenyl)methane, bis(4-hydroxy-3-hydroxymethyl-5-methylphenyl)methane, 2,2-bis(4-hydroxy-3,5-dihydroxymethylphenyl)propane, 3,3',5,5'-tetrahydroxymethyl-4,4'-bisphenol, and compounds in which some or all of the hydroxymethyl groups are substituted with alkoxymethyl groups such as methoxymethyl or butoxymethyl. These hydroxymethyl or alkoxymethyl substituted phenolic compounds may be used alone or in combination of two or more.

[0135] Examples of compounds containing alkoxyalkylated amino groups include (poly)hydroxymethylated melamine, (poly)hydroxymethylated glyceryl urea, (poly)hydroxymethylated benzoguanidine, and (poly)hydroxymethylated urea, which are nitrogen-containing compounds having multiple active hydroxymethyl groups in one molecule, and at least one hydrogen atom of the hydroxyl group in the hydroxymethyl group is replaced by an alkyl group such as methyl or butyl.

[0136] The aforementioned compounds with alkoxyalkylated amino groups are sometimes mixtures of multiple substituted compounds, and there are also mixtures containing oligomer components formed by the self-condensation of the compound; any such mixtures can be used.

[0137] The aforementioned compounds with alkoxyalkylated amino groups are also available as commercially available products. Commercially available products include, for example, products from the CYMEL series such as hexamethoxymethyl melamine (manufactured by CYTEC Corporation, CYMEL 303, 303LF), tetrabutoxymethyl glycourea (manufactured by CYTEC Corporation, CYMEL 1170), and tetramethoxymethyl benzoguanidine (manufactured by CYTEC Corporation, CYMEL 1123); products from the POWDERLINK series such as tetramethoxymethyl glycourea (manufactured by CYTEC Corporation, POWDERLINK 1174); and products from the NIKALAC series such as methylated melamine resin (manufactured by Sanwa Chemical Co., Ltd., NIKALAC MW-30HM, MW-390, MW-100LM, MX-750LM) and methylated urea-formaldehyde resin (manufactured by Sanwa Chemical Co., Ltd., NIKALAC MX-270, MX-280, MX-290). These compounds with alkoxyalkylated amino groups can be used alone or in combination of two or more.

[0138] The aforementioned multifunctional capped isocyanate compounds refer to compounds in which two or more isocyanate groups in one molecule are capped by appropriate protecting groups, and when exposed to the high temperature of thermosetting, the protecting groups (capped portions) thermally dissociate and detach, and the resulting isocyanate groups undergo a cross-linking reaction with the resin.

[0139] Such a multifunctional isocyanate compound can be obtained by reacting a suitable capping agent with a multifunctional isocyanate compound having two or more isocyanate groups in one molecule.

[0140] Examples of the aforementioned polyfunctional isocyanate compounds include 1,4-tetramethylene diisocyanate, 1,5-pentamethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,3,6-hexamethylene triisocyanate, lysine diisocyanate, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-cyclohexyl diisocyanate, and 2... 6-Bis(isocyanatomethyl)tetrahydrodicyclopentadiene, bis(isocyanatomethyl)dicyclopentadiene, bis(isocyanatomethyl)adamantane, 2,5-diisocyanatomethylnorbornene, norbornene diisocyanate, dicycloheptane triisocyanate, 4,4'-diphenylmethane diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, phenylenedimethylene diisocyanate, tetramethylphenylenedimethylene diisocyanate, 1,5-naphthalene diisocyanate, p-phenylenedimethylene diisocyanate 1,3-bis(isocyanate-methyl)benzene, bianisidine diisocyanate, 3,3'-dimethyldiphenyl-4,4'-diisocyanate, diphenyl ether diisocyanate, 2,6-bis(isocyanate-methyl)decahydronaphthalene, bis(diisocyanate-tolyl)phenylmethane, 1,1'-methylenebis(3-methyl-4-isocyanate-benzene), 1,3-bis(1-isocyanate-1-methylethyl)benzene, 1,4-bis(1-isocyanate-1-methylethyl)benzene, 4,4' -Biphenyl diisocyanate, 3,3'-dimethyl-4,4'-biphenyl diisocyanate, 3,3'-dimethoxy-4,4'-biphenyl diisocyanate, bis(isocyanatomethyl)thiophene, bis(isocyanatomethyl)tetrahydrothiophene, and their modified compounds (e.g., isocyanurate bodies, biuret bodies, ethylene glycol adducts, propylene glycol adducts, trimethylolpropane adducts, ethanolamine adducts, polyester polyol adducts, polyether polyol adducts, polyamide adducts, polyamine adducts), etc.

[0141] Examples of end-capping agents include methanol, ethanol, isopropanol, n-butanol, heptanol, hexanol, 2-ethoxyhexanol, cyclohexanol, octanol, isononol, stearyl alcohol, benzyl alcohol, 2-ethoxyethanol, methyl lactate, ethyl lactate, amyl lactate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol monoethyl ether, and N,N-dimethylaminoethanol. Alcohols such as N,N-diethylaminoethanol and N,N-dibutylaminoethanol; phenols such as ethylphenol, propylphenol, butylphenol, octylphenol, nonylphenol, nitrophenol, chlorophenol, o-cresol, m-cresol, p-cresol, and xylenol; lactams such as α-pyrrolidone, β-butyrolactam, β-propiolactam, γ-butyrolactam, δ-valerolactam, and ε-caprolactam; and acetone oximes such as methyl ethyl ketone oxime, methyl isobutyl ketone oxime, diethyl ketone oxime, cyclohexanone oxime, acetophenone oxime, and diphenylmethyl ketone oxime. Oximes such as ketoximes; pyrazoles such as pyrazole, 3,5-dimethylpyrazole, 3-methylpyrazole, 4-benzyl-3,5-dimethylpyrazole, 4-nitro-3,5-dimethylpyrazole, 4-bromo-3,5-dimethylpyrazole, and 3-methyl-5-phenylpyrazole; thiols such as butyl mercaptan, hexyl mercaptan, dodecyl mercaptan, and thiophenol; dimalonate, acetoacetate, malononitrile, acetylacetone, methylene disulfone, dibenzoylmethane, dinepentylmethane, and acetone dicarboxylic acid. Reactive methylene compounds such as esters; amines such as dibutylamine, diisopropylamine, di-tert-butylamine, di(2-ethylhexyl)amine, dicyclohexylamine, benzylamine, diphenylamine, aniline, and carbazole; imidazoles such as imidazole and 2-ethylimazole; imines such as methyleneimine, ethyleneimine, polyethyleneimine, and propyleneimine; amides such as acetanilide, acrylamide, acetamide, and dimer amides; imides such as succinimide, maleimide, and phthalimide; and urea compounds such as urea, thiourea, and ethyleneurea. Additionally, internally capped types using urea diketone bonds (dimerization of isocyanate groups) are also possible.

[0142] The aforementioned multifunctional terminal isocyanate compounds are also available as commercially available products. Examples of such commercially available products include the following.

[0143] TAKENATE [Registered Trademark] B-815N, B-830, B-842N, B-846N, B-870, B-870N, B-874, B-874N, B-882, B-882N, B-5010, B-7005, B-7030, B-7075 (all manufactured by Mitsui Chemicals Co., Ltd.);

[0144] DURANATE [Registered Trademark] ME20-B80S, MF-B60B, MF-B60X, MF-B90B, MF-K60B, MF-K60X, SBN-70D, 17B-60P, 17B-60PX, TPA-B80E, TPA-B80X, E402-B80B, E402-B80T, K6000 (all manufactured by Asahi Kasei Corporation);

[0145] CORONATE [Registered Trademark] 2503, 2507, 2512, 2513, 2515, 2520, 2554, BI-301, AP-M, MILLIONATE MS-50 (all manufactured by Tosoh Corporation);

[0146] BURNOCK [Registered Trademark] D-500, D-550, DB-980K (all manufactured by DIC Co., Ltd.);

[0147] DESMODUR [Registered Trademark] BL-3175, BL-4165, BL-4265, BL-1100, BL-1265, TPLS-2957, TPLS-2062, TPLS-2078, TPLS-2117, BL-3475, DESMOTHERM [Registered Trademark] 2170, 2265 (all manufactured by Sumitomo Covestro Urethane Co., Ltd.);

[0148] TRIXENE BI-7641, BI-7642, BI-7986, BI-7987, BI-7950, BI-7951, BI-7960, BI-7961, BI-7963, BI-7981, BI-798 2. BI-7984, BI-7986, BI-7990, BI-7991, BI-7992, BI-7770, BI-7772, BI-7779, DP9C / 214 (the above is Baxenden Chemicals Company);

[0149] VESTANAT [Registered Trademark] B1358A, B1358 / 100, B1370, VESTAGON [Registered Trademark] B1065, B1400, B1530, BF1320, BF1540 (all manufactured by Evonik Industries).

[0150] Furthermore, examples of the aforementioned multifunctional isocyanate compounds include homopolymers or copolymers obtained by free radical polymerization of (meth)acrylates having isocyanate-terminated groups. Here, a copolymer refers to a polymer obtained by polymerizing two or more monomers. The copolymer can be a copolymer obtained by polymerizing two or more (meth)acrylates having isocyanate-terminated groups, or a copolymer obtained by polymerizing (meth)acrylates having isocyanate-terminated groups and other (meth)acrylates. Such (meth)acrylates with isocyanate-terminated groups are also commercially available. Examples of such commercially available products include KARENZ MOI-BM, AOI-BM, MOI-BP, and AOI-BP manufactured by Resonac Co., Ltd.

[0151] These multifunctional terminal isocyanate compounds can be used alone or in combination of two or more.

[0152] In this invention, the catalyst used to promote the above-mentioned crosslinking reaction can be a mixture of acidic compounds such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonate, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, and naphthoic acid; and thermogenic acid-producing agents such as 2,4,4,6-tetrabromocyclohexadienone, benzoin toluenesulfonate, 2-nitrobenzyl toluenesulfonate, and other organic alkyl sulfonates. It is also possible to combine the above-mentioned acidic compounds and thermogenic acid-producing agents in a mixture.

[0153] The amount of catalyst mixed is preferably 0.0001 to 20 parts by mass relative to 100 parts by mass of the non-polymer compound in the film-forming composition of the present invention, and more preferably 0.0005 to 10 parts by mass.

[0154] <Organic Solvents>

[0155] As an organic solvent, there is no particular limitation as long as it is an organic solvent that dissolves the aforementioned non-polymer compounds. Specific examples include methylcyclohexane, ethylcyclohexane, n-heptane, toluene, o-xylene, m-xylene, mesitylene, chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, anisole, phenethyl ether, di-n-propyl ether, di-n-butyl ether, diisobutyl ether, di-n-pentyl ether, diisopentyl ether, di-n-hexyl ether, n-butyl ethyl ether, methyl-n-pentyl ether, cyclopentylmethyl ether, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, 1-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 1-pentanol, 2-pentanol, 3-pentanol, cyclopentanol, benzyl alcohol, ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol diethyl ether. Ethers, ethylene glycol dibutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, triethylene glycol monomethyl ether, triethylene glycol dimethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol dimethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, n-butyl formate, isobutyl formate, n-pentyl formate, isoamyl formate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, tert-butyl acetate, n-pentyl acetate, isoamyl acetate, n-hexyl acetate, isoheptanyl acetate, n-heptyl acetate, isoheptyl acetate, n-octyl acetate, acetic acid Isooctyl ester, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol diacetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol diacetate, triacetin, ethyl propionate, n-propyl propionate, isopropyl propionate, n-butyl propionate, isobutyl propionate, tert-butyl propionate, propylene glycol monomethyl ether propionate, methyl butyrate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, isobutyl butyrate, tert-butyl butyrate, methyl isobutyrate, ethyl isobutyrate, n-propyl isobutyrate, iso Isopropyl butyrate, n-butyl isobutyrate, isobutyl isobutyrate, tert-butyl isobutyrate, methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, n-butyl lactate, isobutyl lactate, tert-butyl lactate, methyl acetoacetate, ethyl acetoacetate, n-propyl acetoacetate, isopropyl acetoacetate, n-butyl acetoacetate, isobutyl acetoacetate, tert-butyl acetoacetate, dimethyl malonate, diethyl malonate, methyl glycolate, ethyl glycolate, methyl pyruvate, ethyl pyruvate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, dimethyl carbonate, diethyl carbonate, 2-pentanone, 3-pentanone, cyclopentanone, 2,4-Pentanedione, 4-Methyl-2-pentanone, 4-Hydroxy-4-methyl-2-pentanone, 2-Hexanone, 3-Hexanone, 3-Methyl-2-hexanone, 5-Methyl-2-hexanone, 2-Methyl-3-hexanone, 5-Methyl-3-hexanone, Cyclohexanone, 2-Methylcyclohexanone, 3-Methylcyclohexanone, 4-Methylcyclohexanone, 2-Hepanoone, 3-Hepanoone, 4-Hepanoone, 2-Methyl-3-Hepanoone, 5-Methyl- 3-Heptanone, 2,6-dimethyl-4-heptanone, cycloheptanone, γ-butyrolactone, γ-valerolactone, γ-caprolactone, δ-valerolactone, δ-caprolactone, ε-caprolactone, N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N,N-diethylacetamide, N,N-dimethylisobutyramide, N-methyl-2-pyrrolidone, and N-ethyl-2-pyrrolidone, etc. These organic solvents can be used alone or in combination of two or more.

[0156] From the viewpoint of improving the leveling properties of the coating film formed by coating the film-forming composition of the present invention onto a substrate, the following organic solvents are preferred: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, ethyl lactate, n-butyl lactate, methyl pyruvate, ethyl pyruvate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 2-heptanone, cyclopentanone, cyclohexanone, γ-butyrolactone, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and N-ethyl-2-pyrrolidone.

[0157] <surfactants>

[0158] In order to improve coatability, the film-forming composition of the present invention may also contain surfactants. Examples of surfactants that can be listed include nonionic surfactants such as polyoxyethylene alkyl ethers (e.g., polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene oil-based ether), polyoxyethylene alkyl aryl ethers (e.g., polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether), polyoxyethylene-polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate, etc., and polyoxyethylene sorbitan fatty acid esters such as polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, etc.; EFTOP [Registered Trademarks] EF301, EF303, EF352 (manufactured by Mitsubishi Materials Electronics & Chemicals Co., Ltd.), Megafac [Registered Trademarks] F171, F173, R-30, R-40, R-40-LM (manufactured by DIC Co., Ltd.), Fluorad FC430, FC431 (manufactured by 3M Japan Co., Ltd.), Asahi Guard [Registered Trademarks] AG710, Surflon [Registered Trademarks] FTERGENT series fluorinated surfactants such as S-382, SC101, SC102, SC103, SC104, SC105, SC106 (manufactured by AGC Corporation), DFX-18, FTX-206D, FTX-212D, FTX-218, FTX-220D, FTX-230D, FTX-240D, FTX-212P, FTX-220P, FTX-228P, FTX-240G, etc. (manufactured by Neos Corporation); organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), POLYFLOW Non-fluorinated surfactants such as No. 7, No. 36, No. 50E, No. 75, No. 77, No. 85, No. 85HF, No. 90, No. 90D-50, No. 95, No. 99C, and PW-95 (manufactured by Kyoeisha Chemical Co., Ltd.) are available. These surfactants can be used alone or in combination of two or more.

[0159] When the above-mentioned surfactant is present, its content relative to 100 parts by mass of the above-mentioned non-polymer compound is preferably 0.0001 to 3 parts by mass, more preferably 0.001 to 1 part by mass, and even more preferably 0.01 to 0.5 parts by mass.

[0160] The film-forming composition of the present invention may, as needed, contain additives such as antioxidants, light stabilizers (HALS: hindered amine light stabilizers), ultraviolet absorbers different from the non-polymer compounds of the present invention, sealing aids, plasticizers, and sensitizers, provided that the effects of the present invention are not impaired.

[0161] The preparation method of the film-forming composition of the present invention is not particularly limited. For example, a method in which the above-mentioned non-polymer compound and curing agent are dissolved in an organic solvent to form a homogeneous solution can be listed. Furthermore, a method in which surfactants and other additives are added and mixed as needed at an appropriate stage of the preparation method can be listed. It should be noted that, in order to obtain a film with better reproducibility and higher flatness, filtration can be performed, if necessary, during the preparation of the film-forming composition or after all components have been mixed, using a submicron-sized filter or the like.

[0162] Regarding the concentration of solid components in the film-forming composition of the present invention, the concentration is appropriately set, taking into account the coatability of the composition and the characteristics of the object to which the film is formed, and is generally about 0.1 to 30% by mass, preferably about 1 to 25% by mass, and more preferably about 5 to 20% by mass.

[0163] The use of the film-forming composition of the present invention will be described below.

[0164] <Coating Preparation Method>

[0165] A method for preparing a coating using the film-forming composition of the present invention will be described. After applying the film-forming composition of the present invention to an organic film, film substrate (e.g., PET film, polyimide film), or component that has deteriorated due to ultraviolet radiation using a suitable coating method such as a spin coater or coater, the coating is baked using a heating means such as a hot plate or oven to prepare the coating. The baking conditions are appropriately selected from a baking temperature of 50–300°C and a baking time of 0.1–360 minutes. The baking process for preparing the coating can be performed in two or more steps. Furthermore, the thickness of the formed coating is, for example, 0.001–1000 μm, preferably 0.01–100 μm, and more preferably 0.1–10 μm.

[0166] Coatings made using the film-forming compositions of the present invention can be used as protective films for organic films, film substrates, or components that deteriorate due to ultraviolet radiation.

[0167] Example

[0168] The following examples of synthesis, embodiments and comparative examples illustrate the present invention in more detail, but the present invention is not limited to the following embodiments.

[0169] The compounds used in the following synthesis examples, embodiments, and comparative examples are described below.

[0170] [solvent]

[0171] PGME: Propylene Glycol Monomethyl Ether

[0172] PGMEA: Propylene glycol monomethyl ether acetate

[0173] CHN: Cyclohexanone

[0174] EL: Ethyl lactate

[0175] MEK: Methyl ethyl ketone

[0176] THF: Tetrahydrofuran

[0177] [Synthetic Raw Materials]

[0178] TGIC: Triglycidyl isocyanurate

[0179] [Chemistry 17]

[0180]

[0181] TEPG: Tetra(glycidoxyphenyl)ethane (Asahi Organics Co., Ltd., trade name: TEP-G)

[0182] [Chemistry 18]

[0183]

[0184] EX512: Polyglycerol polyglycidyl ether (Nagase Chemtex Co., Ltd., trade name: DENACOL (registered trademark) EX-512)

[0185] [Chemistry 19]

[0186]

[0187] EX614B: Sorbitol polyglycidyl ether (Nagase Chemtex Inc., trade name: DENACOL (registered trademark) EX-614B)

[0188] [Chemistry 20]

[0189]

[0190] EX521: Polyglycerol polyglycidyl ether (Nagase Chemtex Co., Ltd., trade name: DENACOL (registered trademark) EX-521)

[0191] [Chemistry 21]

[0192]

[0193] EX810P: Ethylene glycol diglycidyl ether (Nagase Chemtex Co., Ltd., trade name: DENACOL (registered trademark) EX-810P)

[0194] [Chemistry 22]

[0195]

[0196] EX321L: Trimethylolpropane polyglycidyl ether (Nagase Chemtex Inc., trade name: DENACOL (registered trademark) EX-321L)

[0197] [Chemistry 23]

[0198]

[0199] PETG: Pentaerythritol tetraallyl ether produced by the epoxidation reaction of hydrogen peroxide (Resonac Co., Ltd., trade name: Shofree (registered trademark) PETG).

[0200] [Chemistry 24]

[0201]

[0202] JER828: Bisphenol A type difunctional epoxy resin (Mitsubishi Chemical Co., Ltd., trade name: jER (registered trademark) 828)

[0203] G01100: Acrylic polymers containing epoxy groups (Nippon Oil Co., Ltd., trade name: Marproof (registered trademark) G-01100), polymers containing repeating units represented by the following formula, and having more than 6 epoxy groups per molecule.

[0204] [Chemistry 25]

[0205]

[0206] 24DHBP: 2,4-Dihydroxybenzophenone

[0207] [Chemistry 26]

[0208]

[0209] DBDT: 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine

[0210] [Chemistry 27]

[0211]

[0212] 244THBP: 2,4,4-Trihydroxybenzophenone

[0213] [Chemistry 28]

[0214]

[0215] UV416: 2-(4-benzoyl-3-hydroxyphenoxy)ethyl acrylate

[0216] [Chemistry 29]

[0217]

[0218] MOIBP: 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl methacrylate (Resonac Inc., trade name: KARENZ (registered trademark) MOI-BP)

[0219] [Chemistry 30]

[0220]

[0221] In addition, the weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the polymer were determined using a GPC apparatus manufactured by Shimadzu Corporation (columns: Shodex KF803L and KF804L (manufactured by Resonac Corporation); eluent THF, flow rate: 1.0 mL / min, column temperature: 40 °C, Mw and Mn: conversion values ​​to standard polystyrene).

[0222] [1] Synthesis of non-polymer compounds

[0223] [Example 1-1]

[0224] 3.00 g (10.09 mmol) of TGIC, 6.49 g (30.28 mmol) of 24DHBP, and 0.15 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 22.5 g of CHN and reacted at 120 °C for 20 hours to obtain a solution (A-1) containing a solid component concentration of 30% by mass of the non-polymer compound represented by the above formula (1-2).

[0225] [Examples 1-2]

[0226] 3.00 g (10.09 mmol) of TGIC, 2.16 g (10.09 mmol) of 24DHBP, 8.02 g (20.18 mmol) of DBDT, and 0.15 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 53.3 g of CHN and reacted at 120 °C for 20 hours to obtain a solution (A-2) containing a solid component concentration of 20% by mass of the non-polymer compound represented by the above formulas (1-3).

[0227] [Examples 1-3]

[0228] 3.00 g (10.09 mmol) of TGIC, 12.03 g (30.28 mmol) of DBDT, and 0.15 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 60.7 g of CHN and reacted at 120 °C for 20 hours to obtain a solution (A-3) containing a solid component concentration of 20% by mass of the non-polymer compound represented by the above formula (1-1).

[0229] [Examples 1-4]

[0230] 3.00 g of TEPG (epoxy equivalent 180), 3.57 g of 24DHBP (16.67 mmol), and 0.12 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 26.8 g of CHN and reacted at 120 °C for 20 hours to obtain a solution (A-4) containing a solid component concentration of 20% by mass of the non-polymer compound represented by the above formulas (1-4).

[0231] [Examples 1-5]

[0232] 3.00 g of EX512 (epoxy equivalent 168), 7.10 g of DBDT (17.86 mmol), and 0.13 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 40.9 g of CHN and reacted at 120 °C for 20 hours to obtain a solution (A-5) containing a solid component concentration of 20% by mass of the non-polymer compound represented by the above formulas (1-6).

[0233] [Examples 1-6]

[0234] 3.00 g of EX614B (epoxy equivalent 173), 6.89 g of DBDT (17.34 mmol), and 0.13 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 40.1 g of CHN and reacted at 120 °C for 20 hours to obtain a solution (A-6) containing a solid component concentration of 20% by mass of the non-polymer compound represented by the above formulas (1-5).

[0235] [Examples 1-7]

[0236] 3.00 g of EX521 (epoxy equivalent 183), 6.52 g of DBDT (16.39 mmol), and 0.12 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 38.6 g of CHN and reacted at 120 °C for 20 hours to obtain a solution (A-7) containing a solid component concentration of 20% by mass of the non-polymer compound represented by the above formula (1-7).

[0237] [Examples 1-8]

[0238] TEPG 3.00 g (epoxy equivalent 180), DBDT 6.62 g (16.67 mmol), and ethyltriphenylphosphonium bromide as a catalyst 0.06 g were dissolved in CHN 22.6 g and reacted at 120 °C for 20 hours to obtain a solution (A-8) containing a solid component concentration of 30% by mass of the non-polymer compound represented by the above formula (1-10).

[0239] [Examples 1-9]

[0240] TEPG 3.00 g (epoxy equivalent 180), 24DHBP 1.79 g (8.33 mmol), DBDT 3.31 g (8.33 mmol), and ethyltriphenylphosphonium bromide as catalyst 0.06 g were dissolved in CHN 19.0 g and reacted at 120 °C for 20 hours to obtain a solution (A-9) containing a solid component concentration of 30% by mass of the non-polymer compound represented by the above formula (1-11).

[0241] [Examples 1-10]

[0242] 3.00 g of EX321L (epoxy equivalent 128), 9.31 g of DBDT (23.44 mmol), and 0.12 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 29.0 g of CHN and reacted at 120 °C for 20 hours to obtain a solution (A-10) containing a solid component concentration of 30% by mass of the non-polymer compound represented by the above formula (1-12).

[0243] [Examples 1-11]

[0244] 3.00 g of PETG (epoxy equivalent 128), 12.86 g of DBDT (32.36 mmol), and 0.12 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 37.9 g of CHN and reacted at 120 °C for 20 hours to obtain a solution (A-11) containing a solid component concentration of 30% by mass of the non-polymer compound represented by the above formula (1-13).

[0245] [Comparative Example 1-1]

[0246] 2.00 g of EX810P (epoxy equivalent 95), 8.39 g of DBDT (21.05 mmol), and 0.16 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 42.1 g of CHN and reacted at 120 °C for 20 hours to obtain a solution (A-12) containing a solid component concentration of 20% by mass of a non-polymer compound that does not conform to the non-polymer compound represented by the above formula (1).

[0247] [Comparative Examples 1-2]

[0248] 3.00 g of JER828 (epoxy equivalent 190), 2.73 g of 244THBP (11.84 mmol), and 0.12 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 23.4 g of CHN and reacted at 120 °C for 20 hours to obtain a polymer solution (A-13) containing a polymer with a solid content concentration of 20% by mass that does not conform to the non-polymer compound represented by formula (1) above. The obtained polymer has a Mw of 5300 and a Mn of 3300.

[0249] [Comparative Examples 1-3]

[0250] 3.00 g of G01100 (epoxy equivalent 170), 5.04 g of 24DHBP (23.53 mmol), and 0.17 g of ethyltriphenylphosphonium bromide as a catalyst were dissolved in 36.9 g of CHN and reacted at 120 °C for 20 hours to obtain a polymer solution (A-14) containing a polymer with a solid content concentration of 20% by mass that does not conform to the non-polymer compound represented by formula (1) above. The obtained polymer has a Mw of 21300 and a Mn of 11000.

[0251] [2] Synthesis of curing agent

[0252] [Synthesis example 1]

[0253] 10.00 g (39.79 mmol) of MOIBP and 0.78 g of azobisisobutyronitrile (AIBN) as a polymerization catalyst were dissolved in 25.1 g of PGMEA and reacted at 70 °C for 20 hours to obtain a polymer solution with a solid content of 30% by mass. 400 g of methanol was slowly added dropwise to the obtained polymer solution, causing a solid to precipitate. The precipitated solid was filtered, separated, and dried under reduced pressure to obtain polymer (B-1). The obtained polymer had a Mw of 32000 and a Mn of 14000.

[0254] [Synthesis example 2]

[0255] 4.00 g (15.92 mmol) of MOIBP, 4.97 g (15.92 mmol) of UV416, and 0.52 g of azobisisobutyronitrile (AIBN) as a polymerization catalyst were dissolved in 38.0 g of CHN and reacted at 80 °C for 20 hours to obtain a polymer solution with a solid content of 20% by mass. 500 g of methanol was slowly added dropwise to the obtained polymer solution, causing a solid to precipitate. The precipitated solid was filtered, separated, and dried under reduced pressure to obtain polymer (B-2). The obtained polymer had a Mw of 9600 and a Mn of 4100.

[0256] [3] Preparation of film-forming compositions

[0257] [Example 2-1]

[0258] 100 parts by mass of A-1 obtained in Example 1-1 (converted to solid content), 40 parts by mass of curing agent B-1 obtained in Synthesis Example 1, and 0.02 parts by mass of DFX-18 (manufactured by Neos Co., Ltd.) as a surfactant were mixed, and CHN was added as an organic solvent to obtain a solution with a solid content concentration of 12.5% ​​by mass. Then, the obtained solution was filtered through a PTFE microfilter with a pore size of 0.2 μm to prepare a membrane forming composition (C-1).

[0259] [Examples 2-1 to 2-8, Comparative Examples 2-1 to 2-3]

[0260] Except for changing the types and mixing amounts of each component as described in Table 1, the film-forming compositions (C-2) to (C-11) were prepared using the same method as in Example 2-1.

[0261] [Table 1]

[0262]

[0263] [Example 3-1]

[0264] After reprecipitating and refining A-4 obtained in Examples 1-4 with a specified solvent, 100 parts by weight of solids, 20 parts by weight of curing agent B-1 obtained in Synthesis Example 1, and 0.03 parts by weight of surfactant R-30 (manufactured by DIC Co., Ltd.) were mixed, and CHN was added as an organic solvent to obtain a solution with a solids concentration of 31% by weight. Then, the obtained solution was filtered using a PTFE microfilter with a pore size of 0.2 μm to prepare a membrane forming composition (D-1).

[0265] [Examples 3-2 to 3-7, Comparative Examples 3-1 to 3-3]

[0266] Except for changing the types and mixing amounts of each component as described in Table 2, the film-forming compositions (D-2) to (D-7) and (D-10) to (D-12) were prepared using the same method as in Example 3-1.

[0267] [Examples 3-8]

[0268] The A-11 obtained in Examples 1-11 was purified by reprecipitation using a specified solvent. Then, 100 parts by weight (based on solid content) of the mixture, 30 parts by weight of the curing agent B-1 obtained in Synthesis Example 1, 0.5 parts by weight of surfactant No.90 (manufactured by Kyoeisha Chemical Co., Ltd.), and 3 parts by weight of light stabilizer Tinuvin 144 (manufactured by BASF Japan Co., Ltd.) were mixed with CHN as an organic solvent to obtain a solution with a solid content concentration of 31% by weight. The obtained solution was then filtered using a PTFE microfilter with a pore size of 0.2 μm to prepare a membrane forming composition (D-8).

[0269] [Examples 3-9]

[0270] Except for the addition of 5 parts by weight of Tinuvin 479 (manufactured by BASF Japan Co., Ltd.), which is a UV absorber different from the non-polymer compound of the present invention, the film-forming composition (D-9) was prepared by the same method as in Examples 3-8.

[0271] [Table 2]

[0272]

[0273] [4] Membrane fabrication and evaluation

[0274] [Transmittance Measurement]

[0275] The film-forming compositions prepared in Examples 2-1 to 2-8 and Comparative Examples 2-1 to 2-3 were respectively coated onto quartz substrates using a spin coater, baked on a hot plate at 100°C for 1 minute, and then baked at 150°C for 10 minutes to form films with a thickness of 500 nm. For these films, the transmittance was measured in the wavelength range of 200–800 nm using a UV-2600 ultraviolet-visible spectrophotometer (manufactured by Shimadzu Corporation). The ultraviolet absorption and visible light transmittance were evaluated using the following standards based on the measurement results. The results are shown in Table 3.

[0276] The film-forming compositions prepared in Examples 3-1 to 3-9 and Comparative Examples 3-1 to 3-3 were diluted with CHN to a specified concentration and then coated onto a quartz substrate using a spin coater. The substrates were baked on a hot plate at 100°C for 1 minute, followed by baking at 230°C for 10 minutes to form films with a thickness of 1000 nm. The transmittance of these films was measured using a UV-2600 ultraviolet-visible spectrophotometer (manufactured by Shimadzu Corporation) in the wavelength range of 200–800 nm. The ultraviolet absorption and visible light transmittance were evaluated using the following standards based on the measurement results. The results are shown in Table 4.

[0277] Ultraviolet Absorption Evaluation Standard

[0278] ○: The lowest transmittance measured in the wavelength range of 280–400 nm is less than 10%.

[0279] ×: The lowest transmittance measured in the wavelength range of 280–400 nm is above 10%.

[0280] Standard for evaluating visible light transmittance

[0281] ○: The lowest transmittance measured in the wavelength range of 400-800nm ​​is above 90%.

[0282] ×: The lowest transmittance measured in the wavelength range of 400–800 nm is less than 90%.

[0283] [Solubility]

[0284] For each of the organic solvents (PGME, PGMEA, EL, MEK) shown in Table 3, 0.2 g of the film-forming compositions prepared in Examples 2-1 to 2-8 and Comparative Examples 2-1 to 2-3 were added dropwise, and precipitation was observed visually. Solubility was evaluated using the following standards. The results are shown in Table 3.

[0285] For each of the organic solvents (PGME, PGMEA, EL, MEK) shown in Table 4, 0.2 g of the film-forming compositions prepared in Examples 3-1 to 3-9 and Comparative Examples 3-1 to 3-3 were added dropwise, and precipitation was observed visually. Solubility was evaluated using the following standards. The results are shown in Table 4.

[0286] Evaluation Criteria

[0287] ○: No precipitation occurred.

[0288] ×: Precipitation has occurred.

[0289] [Soluble resistance]

[0290] The film-forming compositions prepared in Examples 2-1 to 2-8 and Comparative Examples 2-1 to 2-3 were each spin-coated onto silicon wafers, baked on a hot plate at 100°C for 1 minute, and then baked at 150°C for 10 minutes to form a film with a thickness of 500 nm. The resulting film was immersed in acetone for 10 minutes, dried on a hot plate at 100°C for 30 seconds, and the film thickness was measured. The residual film yield was calculated from the film thickness before and after immersion using the following formula. Furthermore, the residual film yield was evaluated using the following criteria. The results are shown in Table 3.

[0291] The film-forming compositions prepared in Examples 3-1 to 3-9 and Comparative Examples 3-1 to 3-3 were each spin-coated onto silicon wafers, baked on a hot plate at 100°C for 1 minute, and then baked at 230°C for 10 minutes to form a film with a thickness of 3000 nm. The resulting film was immersed in acetone for 10 minutes, dried on a hot plate at 100°C for 30 seconds, and the film thickness was measured. The residual film yield was calculated from the film thickness before and after immersion using the following formula. Furthermore, the residual film yield was evaluated using the following criteria. The results are shown in Table 4.

[0292] Residual film yield (%) = [film thickness after impregnation] / [film thickness before impregnation] × 100

[0293] Evaluation Criteria

[0294] ○: Residual film rate is over 90%

[0295] ×: Residual film rate is less than 90%.

[0296] [Table 3]

[0297]

[0298] [Table 4]

[0299]

[0300] As can be seen from the results in Tables 3 and 4, the film formed by the film forming composition of the examples exhibits the same excellent ultraviolet absorption and excellent visible light transmittance as the film formed by the film forming composition of the comparative examples.

[0301] When the film-forming compositions of the embodiments were mixed with organic solvents, no precipitation occurred, demonstrating excellent solubility in the organic solvents. On the other hand, for the film-forming compositions of Comparative Examples 2-2, 2-3, 3-2, and 3-3, precipitation occurred when mixed with specific organic solvents, resulting in low solubility in those organic solvents.

[0302] The films formed by the film-forming compositions of the examples exhibit high solvent resistance. On the other hand, the films formed by the film-forming compositions of Comparative Examples 2-1 and 3-1 have lower solvent resistance compared to the films formed by the film-forming compositions of the examples described above.

Claims

1. A nonpolymer compound represented by the following formula (1), [Chemistry 1] In the formula, n represents an integer from 3 to 6, A represents an organic group with an n-valence that may have a heteroatom selected from nitrogen and oxygen atoms, k represents 0 or 1, and X represents an ultraviolet-absorbing group.

2. The non-polymer compound according to claim 1, wherein, Each of the ultraviolet-absorbing groups is independently a group having any one of the following skeletons: benzotriazole skeleton, triazine skeleton, benzophenone skeleton, cyanoacrylate skeleton, salicylate skeleton, and oxaloylaniline skeleton.

3. The non-polymer compound according to claim 2, wherein, Each of the ultraviolet-absorbing groups is independently a group having a triazine skeleton or a benzophenone skeleton.

4. The non-polymer compound according to claim 3, wherein, Each of the ultraviolet-absorbing groups is independently a group represented by the following formula (x1) or formula (x2). [Chemistry 2] In equation (x1), R a Each of the following independently represents a hydrogen atom, hydroxyl group, methyl group, or ethyl group, wherein the R a At least one of them is a hydroxyl group, R 1 and R 2 Each of them independently represents methyl or ethyl, m1 independently represents an integer from 0 to 3, and m2 represents an integer from 0 to 2. In equation (x2), R b Each independently represents a hydrogen atom or a hydroxyl group, wherein the R b At least one of them is a hydroxyl group. * indicates the bonding end.

5. The non-polymer compound according to claim 4, wherein, Each of the ultraviolet-absorbing groups is independently represented by formula (x1-1) or formula (x2-1) below, and at least one of the n ultraviolet-absorbing groups is represented by formula (x1-1) below. [Chemistry 3] In the formula, R 1 Each of the characters independently represents either methyl or ethyl, m3 independently represents an integer from 0 to 5, and * represents a bond end.

6. The non-polymer compound according to claim 1, wherein, The molecular weight is 500 to 3500.

7. The non-polymer compound according to claim 1, wherein it is a reaction product of a compound having 3 to 6 epoxy groups in one molecule and a compound having the ultraviolet-absorbing group and a phenolic hydroxyl or carboxyl group.

8. The non-polymer compound according to claim 1, wherein, The organic group represented by A is any one of the following formulas (a1) to (a7). [Chemistry 4] In the formula, * represents the bonding end.

9. A film-forming composition comprising a nonpolymer compound represented by formula (1) according to any one of claims 1 to 8, a curing agent, and an organic solvent, wherein the content of the curing agent is 15 parts by mass or more relative to 100 parts by mass of the nonpolymer compound.

10. The film-forming composition according to claim 9, wherein, The curing agent is a multifunctional end-capped isocyanate compound.

11. The film-forming composition according to claim 10, wherein, The multifunctional capped isocyanate compound is a homopolymer of (meth)acrylate having capped isocyanate groups, or a copolymer containing (meth)acrylate having capped isocyanate groups.

12. The film-forming composition according to claim 9, further comprising a surfactant.

13. The film-forming composition according to claim 9, further comprising a light stabilizer.

14. A membrane obtained from the membrane forming composition according to claim 9.

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