Curable composition, cured material, organic el element, solid-state image sensor, and compound

Abstract

To provide a curable composition comprising a compound having a perfluoropolyether chain, where the composition before curing shows high transparency and a cured material with high transparency can be obtained by curing.SOLUTION: A curable composition comprises: (A) a reactive polyether compound having a perfluoropolyether chain represented by -[(CmF2m)O]n-CkF2k- (m is an integer of 1 or more; n is an integer of 2 or more; a plurality of (CmF2m) are the same or different; and k is an integer of 1 to 6) and a plurality of reactive groups bonded to each terminal of the perfluoropolyether chain directly or via a bivalent bonding group); (B) a polymerizable compound (where a reactive polyether compound is excluded); and (C) a photoinitiator, where the reactive polyether compound includes a compound having, as reactive groups, a first reactive group and a second reactive group in one molecule or includes a first compound and a second compound, reactive groups of which are different among molecules.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a curable composition, a cured product, an organic EL device, an imaging device, and a compound. [Background technology]

[0002] An organic electroluminescence element (organic EL element) is a light-emitting element having a laminated structure including an anode, an organic light-emitting layer, and a cathode, and is being put to practical use in applications such as display devices and lighting devices. An organic EL element is provided with an insulating cured film such as a planarizing film. The planarizing film is formed on a substrate for the purpose of filling in the unevenness of the substrate surface on which a semiconductor element or the like is formed, thereby planarizing the substrate surface. The planarizing film is generally formed by applying a photosensitive composition onto a substrate, forming a pattern by exposure and development processes, and then performing a heat treatment as necessary (see, for example, Patent Document 1). In recent years, it has been considered to improve the brightness of a display device and adjust the viewing angle by combining a high refractive index material with a low refractive index material.

[0003] In addition, in various display elements such as touch panel displays, in order to prevent the occurrence of dirt or scratches on the substrate surface, a surface protective film having water repellency and oil repellency is provided on the substrate surface to protect the substrate surface (see, for example, Patent Documents 2 and 3). Patent Document 2 discloses the use of a curable composition containing a perfluoropolyether having a silyl group as a material for forming a hard coat layer. Patent Document 3 discloses the formation of a cured coating exhibiting anti-reflection and anti-fouling properties using a curable composition containing a perfluoropolyether having trimethoxysilyl groups at both ends and low refractive index particles.

[0004] Various image sensors, such as a CCD (Charge-Coupled Device) image sensor and a CMOS (Complementary Metal-Oxide-Semiconductor) image sensor, are used as solid-state imaging elements in imaging devices such as cameras. In solid-state imaging elements, hemispherical condensing lenses (hereinafter also referred to as "microlenses") and in-layer lenses are provided to collect light on a light receiving element (photodiode) to improve sensor sensitivity. In addition, in organic EL elements, a structure is adopted in which a microlens made of a high refractive index material or a low refractive index material is provided on the light emission side of each pixel in order to improve light extraction efficiency and adjust the viewing angle (see, for example, Patent Document 4). In recent years, lenses for solid-state imaging elements and organic EL elements have also been formed by photolithography technology using a photosensitive composition. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2018-039979 A [Patent Document 2] International Publication No. 2015 / 190526 [Patent Document 3] JP 2010-106075 A [Patent Document 4] JP 2020-101659 A Summary of the Invention [Problem to be solved by the invention]

[0006] Perfluoroalkyl compounds, particularly perfluoropolyether derivatives, have unique properties of low surface energy and low refractive index. For this reason, attempts have been made to apply perfluoropolyether derivatives to various applications such as optical applications and water-repellent coating agents. For optical applications, for example, it is conceivable to manufacture low refractive index materials provided in organic EL elements and solid-state imaging elements using perfluoroalkyl compounds.

[0007] However, when used as a component of a curable composition, the perfluoropolyether derivative has a problem that it has low compatibility with non-fluorinated solvents and other components (e.g., polymerizable compounds) that are blended to impart curability due to its characteristic properties. Therefore, there is a concern that the perfluoropolyether derivative will not be uniformly dispersed in the curable composition, the composition before curing will become opaque, and the film obtained using the composition will tend to be a non-uniform film with a sea-island structure. In particular, in applications where transparency is required for the cured product, the use of the perfluoropolyether derivative is considered to be limited because transparency cannot be guaranteed.

[0008] The present invention has been made in consideration of the above problems, and has as its main object to provide a curable composition which contains a compound having a perfluoropolyether chain, which composition exhibits high transparency before curing, and which can give a cured product with high transparency upon curing. [Means for solving the problem]

[0009] According to the present invention, there are provided the following curable composition, cured product, organic EL device, imaging device, and compound.

[0010] [1] (A)-[(C m F 2m )O] n -C k F 2k - (where m is an integer of 1 or more, n is an integer of 2 or more, and m F 2m ) are the same or different, and k is an integer of 1 to 6. A reactive polyether compound having ) and a plurality of reactive groups bonded directly or via a divalent linking group to each end of the perfluoropolyether chain, (B) a polymerizable compound (excluding the reactive polyether compound), and (C) Photopolymerization initiator wherein the reactive polyether compound includes a compound having, as the reactive groups, a first reactive group and a second reactive group different from the first reactive group in one molecule, or includes a first compound and a second compound in which the reactive groups are different between the molecules. [2] A cured product formed from the curable composition described in [1] above. [3] An organic electroluminescence device comprising the cured product according to [2] above. [4] A solid-state imaging device comprising the cured product described in [2] above.

[0011] [5] A compound represented by the following formula (1): [ka] (In formula (1), X 1 is a group selected from Group A, Group B, Group C, and Group D shown below. 2 Among the following groups A, B, C, and D, X 1 is a group selected from a group different from Group A: (meth)acryloyl group Group B: -Si(OR 1 ) t (R 2 ) 3-t (wherein R 1 and R 2 are each independently a monovalent hydrocarbon group having 1 to 10 carbon atoms, t is an integer of 1 to 3, and when t is 2 or 3, multiple R 1 are the same or different, and when t is 1, multiple R 2 are the same or different.) Group C: vinyl group, allyl group Group D: Cyclic ether groups Y 1 and Y 2 are each independently a single bond or a divalent group in which some methylene groups in an alkanediyl group having 2 to 10 carbon atoms are replaced with oxygen atoms, ester bonds, amide bonds, urethane bonds or urea bonds. Lf is -[(C m F 2m )O] n -Ck F 2k m is an integer of 1 or more, n is an integer of 2 or more, and m F 2m ) are the same or different. k is an integer of 1 to 6. Effect of the Invention

[0012] According to the present invention, while containing a compound having a perfluoropolyether chain, the composition before curing exhibits high transparency, and upon curing, a cured product having high transparency can be obtained. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] Matters related to the embodiments will be described in detail below. In this specification, a numerical range described using "to" means that the numerical range includes the numerical ranges before and after "to" as the lower and upper limits.

[0014] ≪Curable composition≫ The curable composition of the present disclosure (hereinafter also referred to as “the composition”) contains the following components (A), (B), and (C). (A)-[(C m F 2m )O] n -C k F 2k - (where m is an integer of 1 or more, n is an integer of 2 or more, and m F 2m ) are the same or different, and k is an integer of 1 to 6. A reactive polyether compound having ) and a plurality of reactive groups bonded directly or via a divalent linking group to each end of the perfluoropolyether chain. (B) Polymerizable compounds (excluding the reactive polyether compounds described above) (C) Photopolymerization initiator The details of each component and the optional components are described below. Unless otherwise specified, each component may be used alone or in combination of two or more.

[0015] Here, in this specification, the term "hydrocarbon group" includes chain-shaped hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. The term "chain-shaped hydrocarbon group" refers to a straight-chain hydrocarbon group and a branched hydrocarbon group that do not include a cyclic structure in the main chain and are composed only of a chain structure. However, the chain-shaped hydrocarbon group may be saturated or unsaturated. The term "alicyclic hydrocarbon group" refers to a hydrocarbon group that includes only an alicyclic hydrocarbon structure as a ring structure and does not include an aromatic ring structure. However, the alicyclic hydrocarbon group does not necessarily have to be composed only of an alicyclic hydrocarbon structure, and also includes those that have a chain structure as a part of it. The term "aromatic hydrocarbon group" refers to a hydrocarbon group that includes an aromatic ring structure as a ring structure. However, the aromatic hydrocarbon group does not necessarily have to be composed only of an aromatic ring structure, and may include a chain structure or an alicyclic hydrocarbon structure as a part of it. In addition, the aromatic ring structure of the aromatic hydrocarbon group may be a single ring or a condensed ring. In addition, the ring structure of the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a substituent consisting of a hydrocarbon structure.

[0016] In the present specification, the term "(meth)acrylic" encompasses both "acrylic" and "methacrylic." The term "(meth)acryloyl group" encompasses both "acryloyl group" and "methacryloyl group."

[0017] <Component (A): Reactive polyether compound> The reactive polyether compound is -[(C m F 2m )O] n -C k F 2k In other words, the perfluoropolyether chain is a chain having a structure in which perfluoroalkanediyl groups and oxygen atoms are alternately linked. The perfluoroalkanediyl group may be linear or branched. The value of m is not particularly limited, but is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. -[(C m F 2mSpecific examples of the repeating unit represented by the formula -C include -[CF2O]- (oxyperfluoromethylene group), -[CF2CF2O]- (oxyperfluoroethylene group), -[CF2CF2CF2O]- (oxyperfluoropropane-1,3-diyl group), -[CF2C(CF3)(F)O]- (oxyperfluoropropane-1,2-diyl group), etc. k F 2k Specific examples of the group represented by - include -CF2-, -CF2CF2-, -CF(CF3)-, -CF2CF2CF2-, -CF2C(CF3)(F)-, etc. The value of k is preferably 1 to 3, and more preferably 1 or 2.

[0018] The perfluoropolyether chain is -[(C m F 2m The repeating unit represented by -[(C )O]- may be one type or two or more types. m F 2m When the repeating unit represented by the formula (I)O]- is present in two or more kinds, the repeating units may be arranged randomly or in a block form. The perfluoropolyether chain may be linear or branched. The linear chain is preferred.

[0019] Among the above, from the viewpoints of ease of handling and availability, the repeating unit of the perfluoropolyether chain is -[(CF2) m It is preferable that the perfluoropolyether chain is represented by -[CF2O]-, -[CF2CF2O]-, or has both -[CF2O]- and -[CF2CF2O]- as repeating units, and more preferably has both -[CF2O]- and -[CF2CF2O]- as repeating units. When the perfluoropolyether chain has -[CF2O]- and -[CF2CF2O]- as repeating units, the ratio of -[CF2CF2O]- to -[CF2O]- is preferably 0.3 to 3, more preferably 0.5 to 2, in molar ratio.

[0020] In the perfluoropolyether chain, -[(C m F 2m The number of repeating units represented by the formula (i.e., the value of n) is not particularly limited. From the viewpoint of ensuring compatibility with other components while achieving a low refractive index, n is preferably 5 to 50, more preferably 5 to 40, even more preferably 5 to 30, still more preferably 5 to 25, and even more preferably 7 to 25.

[0021] A reactive group is bonded to each end of the perfluoropolyether chain directly or via a divalent linking group, so that the reactive polyether compound has a reactive group at each end of the multiple ends of the molecular chain. The reactive group may be a group that can form a bond with the same or different types of functional groups by irradiation with radiation (i.e., a photoreactive group), or a group that can form a bond with the same or different types of functional groups by heating (i.e., a thermally reactive group). The reactive group of the reactive polyether compound may be a group that can form a bond with a functional group of a component contained in the composition (e.g., the reactive polyether compound itself, a polymerizable compound, etc.), or a group that can form a bond with a functional group on the surface of a substrate.

[0022] The reactive group of the reactive polyether compound is preferably a photoreactive group from the viewpoint of improving the photocurability of the present composition. Among them, an ethylenically unsaturated bond-containing group, -Si(OR 1 ) t (R 2 ) 3-t (wherein R 1 and R 2 are each independently a monovalent hydrocarbon group having 1 to 10 carbon atoms, t is an integer of 1 to 3, and when t is 2 or 3, multiple R 1 are the same or different, and when t is 1, multiple R 2 are the same or different. The same applies below.) and a cyclic ether group are preferred.

[0023] Examples of the ethylenically unsaturated bond-containing group include a (meth)acryloyl group, a vinyl group, an allyl group, a vinyl ether group, and a vinylphenyl group. Of these, the ethylenically unsaturated bond-containing group is preferably a (meth)acryloyl group, a vinyl group, or an allyl group. Examples of the cyclic ether group include an oxetanyl group and an oxiranyl group. In this specification, the term "epoxy group" includes an oxetanyl group and an oxiranyl group.

[0024] R 1 or R 2 Examples of the monovalent hydrocarbon group having 1 to 10 carbon atoms represented by the formula (I) include a monovalent chain hydrocarbon group having 1 to 10 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 10 carbon atoms, and a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms. 1 R is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and further preferably a methyl group or an ethyl group. 2 is preferably an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group, and more preferably a methyl group, an ethyl group or a phenyl group. From the viewpoint of reactivity, t is preferably 2 or 3, and more preferably 3.

[0025] Among the above, the reactive group is a (meth)acryloyl group, -Si(OR 1 ) t (R 2 ) 3-t It is preferably a group selected from the group consisting of a group represented by the following formula: (I), a vinyl group, an allyl group, and a cyclic ether group. The number of reactive groups contained in one molecule of the reactive polyether compound is, for example, 2 to 10, and preferably 2 to 6. From the viewpoint of easy availability of the compound and obtaining a cured film with high transparency, it is preferable that the reactive polyether compound has a linear perfluoropolyether chain, and a reactive group is bonded to each of both ends of the chain directly or via a divalent linking group.

[0026] The reactive polyether compound has a plurality of reactive groups each bonded to the end of the perfluoropolyether chain by a single bond or via a divalent linking group. Examples of the divalent linking group include an oxygen atom, an ester bond, an amide bond, a urethane bond, a urea bond, an alkanediyl group having 1 to 10 carbon atoms, and a group in which a part of the methylene group in an alkanediyl group having 2 to 10 carbon atoms is replaced with an oxygen atom, an ester bond, an amide bond, a urethane bond, or a urea bond. From the viewpoint of ease of synthesis of the reactive polyether compound, the divalent linking group linking the perfluoropolyether chain and the reactive group is preferably a group in which a part of the methylene group in an alkanediyl group having 2 to 10 carbon atoms is replaced with an oxygen atom, an ester bond, an amide bond, a urethane bond, or a urea bond, more preferably has at least a urethane bond, an ether bond, or an ester bond, and even more preferably has at least a urethane bond.

[0027] The weight average molecular weight (Mw) of the reactive polyether compound is preferably 500 to 5,000 from the viewpoint of improving the coatability of the composition and ensuring the flatness of the resulting cured film. The Mw of the reactive polyether compound is more preferably 800 or more, and even more preferably 1,000 or more. The Mw of the reactive polyether compound is more preferably 4,500 or less, and even more preferably 4,000 or less. The Mw of the reactive polyether compound is a polystyrene-equivalent value measured by gel permeation chromatography (GPC).

[0028] The reactive polyether compound blended in the present composition includes a compound having a first reactive group and a second reactive group different from the first reactive group in one molecule (hereinafter also referred to as "compound (a1)") as reactive groups, or includes a first compound and a second compound as compounds having different reactive groups between molecules. Here, a reactive oligomer having a perfluoroalkanediyl structure is difficult to dissolve in a polymerizable compound or a solvent, and the obtained cured product tends to be easily whitened. In contrast, by using a compound containing two or more types of reactive groups in one molecule or a compound having different reactive groups between molecules as a reactive polyether compound, the compatibility with other components contained in the present composition (specifically, a polymerizable compound and a solvent that is optionally blended) is increased, and the transparency of the composition before curing can be ensured, and the transparency of the cured product obtained by curing can be guaranteed.

[0029] From the viewpoint of improving the transparency of the composition before curing and its cured product, the present composition preferably contains a compound (a1) as a reactive polyether compound, and the polarity of the first reactive group and the second reactive group in the compound (a1) is different, or contains a first compound and a second compound, and the polarity of the reactive group of the first compound and the reactive group of the second compound are different. The first reactive group and the second reactive group, and the reactive group of the first compound and the reactive group of the second compound are preferably different in the presence or absence or type of heteroatom in the reactive group or the type of functional group, and thus have different polarities. The compound (a1), the first compound, and the second compound are each described below.

[0030] (Compound (a1)) When the reactive polyether compound contains compound (a1), it is preferable that the first reactive group of compound (a1) is a group selected from any one of Groups A, B, C, and D shown below, and the second reactive group is a group selected from a group different from the first reactive group, among Groups A, B, C, and D shown below. Group A: (meth)acryloyl group Group B: -Si(OR 1 ) t (R2 ) 3-t A group represented by Group C: vinyl group, allyl group Group D: Cyclic ether groups In addition, R 1 , R 2 and t are as defined above. Specific examples of the cyclic ether group in Group D are as described above.

[0031] For example, when the first reactive group is a group selected from Group A (e.g., an acryloyl group), the second reactive group is preferably a group selected from Group B, Group C, or Group D (e.g., a triethoxysilyl group). Also, when the first reactive group is a group selected from Group B (e.g., a vinyl group), the second reactive group is preferably a group selected from Group A, Group C, or Group D (e.g., an epoxy group).

[0032] Preferred combinations of the first reactive group and the second reactive group contained in the compound (a1) include the following (IA) to (IIIA). (IA) The first reactive group is a (meth)acryloyl group and the second reactive group is -Si(OR 1 ) t (R 2 ) 3-t

[0043] The above-mentioned group is a vinyl group, an allyl group, or a cyclic ether group. (IIA) The first reactive group is -Si(OR 1 ) t (R 2 ) 3-t and the second reactive group is a vinyl group, an allyl group, or a cyclic ether group. (IIIA) An embodiment in which the first reactive group is a cyclic ether group, and the second reactive group is a vinyl group or an allyl group. Among these, the embodiment (IA) is preferred in that a curable composition having good photocurability can be obtained.

[0033] As the compound (a1), a compound represented by the following formula (1) can be preferably used. [ka] (In formula (1), X 1 is the first reactive group. X 2 is a second reactive group. Y 1 and Y 2 are each independently a single bond or a divalent group in which some methylene groups in an alkanediyl group having 2 to 10 carbon atoms are replaced with oxygen atoms, ester bonds, amide bonds, urethane bonds or urea bonds. Lf is -[(C m F 2m )O] n -C k F 2k m is an integer of 1 or more, n is an integer of 2 or more, and m F 2m ) are the same or different. k is an integer of 1 to 6.

[0034] In the above formula (1), X 1 and X 2 It is preferable that the first reactive group (X 1 ) is a group selected from any one of Group A, Group B, Group C, and Group D shown above, and the second reactive group (X 2 ) is a group selected from the group A, group B, group C, and group D shown above, which is a first reactive group (X 1 ) is preferably a group selected from a group different from X 1 and X 2 Preferred combinations include the above-mentioned embodiments (IA), (IIA) and (IIIA), and among these, embodiment (IA) is preferred.

[0035] Y 1 Or Y 2 When the group represented by is a divalent linking group, the specific and preferred examples of the divalent linking group are the same as those described above for the divalent linking group. The specific and preferred examples of the group represented by Lf are the same as those described above for the perfluoropolyether chain.

[0036] More specific examples of compound (a1) include compounds represented by the following formulas (a1-1) to (a1-12). [ka] [ka] (In formulas (a1-1) to (a1-12), R 1 and R 2 are each independently a monovalent hydrocarbon group having 1 to 10 carbon atoms. t is an integer of 1 to 3. When t is 2 or 3, multiple R 1 are the same or different, and when t is 1, multiple R 2 are the same or different. R 3 is a hydrogen atom or a methyl group. a, b, c and d are each independently an integer of 1 to 10. p and q are each an integer of 1 or more. k is an integer of 1 to 6. r and s are each independently an integer of 1 to 5. When a is 2 or more, (C r H 2r ) are the same or different. When b is 2 or more, (C s H 2s ) are the same or different.

[0037] (First compound and second compound) When the present composition contains a first compound and a second compound as the reactive polyether compound, examples of the first compound and the second compound include compounds represented by the following formula (2). [ka] (In formula (2), X 3 is a group selected from Group A, Group B, Group C, and Group D shown above. Y 1 , Y 2 and Lf is Y in the above formula (1). 1 , Y 2 and Lf.)

[0038] In the above formula (2), X 3Specific examples of each group are as described above. For example, in the above formula (2), 3 ) is a group selected from Group A, the two reactive groups may both be acryloyl groups, or the two reactive groups may both be methacryloyl groups. Alternatively, one of the two reactive groups may be an acryloyl group and the other may be a methacryloyl group. Y 1 Or Y 2 When the group represented by is a divalent linking group, the specific and preferred examples of the divalent linking group are the same as those described above for the divalent linking group. The specific and preferred examples of the group represented by Lf are the same as those described above for the perfluoropolyether chain.

[0039] When the reactive polyether compound includes a first compound and a second compound, it is preferable that the reactive group of the first compound is a group selected from any one of the groups A, B, C, and D shown above, and the reactive group of the second compound is a group selected from the group A, B, C, and D shown above, which is different from the reactive group of the first compound. Specifically, for example, when the reactive group of the first compound is a group selected from group A (e.g., acryloyl group), it is preferable that the reactive group of the second compound is a group selected from group B, C, or D (e.g., triethoxysilyl group). In addition, when the reactive group of the first compound is a group selected from group B (e.g., vinyl group), it is preferable that the reactive group of the second compound is a group selected from group A, C, or D (e.g., epoxy group).

[0040] Preferable combinations of the reactive group in the first compound and the reactive group in the second compound include the following embodiments (IB) to (IIIB). (IB) The reactive group of the first compound is a (meth)acryloyl group, and the reactive group of the second compound is -Si(OR 1 ) t (R 2 ) 3-t

[0043] The above-mentioned group is a vinyl group, an allyl group, or a cyclic ether group. (IIB) The reactive group of the first compound is -Si(OR 1 ) t (R 2 ) 3―t and the reactive group possessed by the second compound is a vinyl group, an allyl group, or a cyclic ether group. (IIIB) An embodiment in which the reactive group of the first compound is a cyclic ether group, and the reactive group of the second compound is a vinyl group or an allyl group. Among these, the embodiment (IB) is preferred in that a curable composition having good photocurability can be obtained.

[0041] Specific examples of the first compound and the second compound include the compounds represented by the following formulas (a2-1) to (a2-5), respectively. [ka] (In formulas (a2-1) to (a2-5), R 1 and R 2 are each independently a monovalent hydrocarbon group having 1 to 10 carbon atoms. t is an integer of 1 to 3. When t is 2 or 3, multiple R 1 are the same or different, and when t is 1, multiple R 2 are the same or different. R 3 is a hydrogen atom or a methyl group. a, b, c and d are each independently an integer of 1 to 10. p and q are each an integer of 1 or more. k is an integer of 1 to 6. r and s are each independently an integer of 1 to 5. When a is 2 or more, (C r H 2r ) are the same or different. When b is 2 or more, (C s H 2s ) are the same or different.

[0042] When the present composition contains a first compound and a second compound, the ratio of the first compound and the second compound in the present composition is preferably 30 to 300 parts by mass, more preferably 50 to 200 parts by mass, and even more preferably 70 to 150 parts by mass, in terms of the ratio of the second compound to 100 parts by mass of the first compound.

[0043] From the viewpoint of improving the photocurability of the composition and the transparency of the cured product, the reactive polyether compound contained in the composition preferably contains compound (a1), and more preferably contains a compound represented by formula (1) above.

[0044] The method for synthesizing the reactive polyether compound is not particularly limited, and the compound can be obtained by appropriately combining standard methods in organic chemistry. For example, the compound represented by the above formula (1) can be obtained by the reaction of -[(C m F 2m )O] n -(C k F 2k A compound having a hydroxyl group bonded directly or via a divalent organic group to each end of a perfluoropolyether chain represented by the formula (hereinafter also referred to as a "specific hydroxyl group-containing compound") and a reactive group (X 1 , X 2 a method of reacting a specific hydroxy group-containing compound with an isocyanate compound having a substituent (e.g., 2-(meth)acryloyloxyethyl isocyanate, 1,1-bis((meth)acryloyloxymethyl)ethyl isocyanate, etc.) having a substituent (e.g., see Japanese Patent No. 3888653); a method of subjecting a specific hydroxy group-containing compound to a dehydrochlorination reaction with an acid chloride capable of introducing a reactive group (e.g., (meth)acrylic acid chloride); a method of subjecting a specific hydroxy group-containing compound to a dehydration reaction with a carboxylic acid capable of introducing a reactive group (e.g., (meth)acrylic acid); a method of subjecting a specific hydroxy group-containing compound to an esterification reaction with itaconic anhydride; and the like.

[0045] Among the above, the method of reacting a specific hydroxy group-containing compound with an isocyanate compound having a reactive group and the method of reacting a specific hydroxy group-containing compound with an acid chloride capable of introducing a reactive group are preferred in that the reaction is easy.

[0046] <(B) Component: Polymerizable compound> The polymerizable compound is a compound that can react with itself to generate a polymer when the composition is irradiated with radiation. The polymerizable compound is a component different from the reactive polyether compound described above and does not have a perfluoropolyether chain.

[0047] As the polymerizable compound, a compound having one or more radical polymerizable groups can be preferably used. As such a polymerizable compound, a compound having a polymerizable carbon-carbon unsaturated bond can be mentioned, specifically, a (meth)acryloyl group-containing compound, a chain vinyl compound, an aromatic vinyl compound, a maleimide compound, etc. can be mentioned. As the polymerizable compound, from the viewpoint of improving the transparency of the obtained cured product, a (meth)acryloyl group-containing compound can be preferably used.

[0048] Specific examples of the (meth)acryloyl group-containing compound include unsaturated carboxylic acids, unsaturated carboxylic anhydrides, (meth)acrylic acid esters having a chain structure, (meth)acrylic acid esters having an alicyclic structure, (meth)acrylic acid esters having an aromatic ring structure, (meth)acrylamide compounds, etc. These compounds are preferably used because of their good polymerizability and relatively high plasticity.

[0049] As the polymerizable compound, a monofunctional compound or a polyfunctional compound may be used. In addition, as the polymerizable compound, a mixture of a monofunctional compound and a polyfunctional compound may be used. From the viewpoint of improving adhesion to a substrate by adjusting hardness and curing property, it is preferable that the polymer compound to be blended in the present composition contains a polyfunctional compound.

[0050] Specific examples of monofunctional polymerizable compounds include unsaturated carboxylic acids such as (meth)acrylic acid, crotonic acid, maleic acid, itaconic acid, and fumaric acid. Examples of unsaturated carboxylic anhydrides include maleic anhydride, itaconic anhydride, and citraconic anhydride. Examples of (meth)acrylic acid esters having a chain structure include (meth)acrylic acid alkyl esters, (meth)acrylic acid hydroxyalkyl esters, (meth)acrylic acid alkoxyalkyl esters, (meth)acrylic acid polyoxyalkylene esters, (meth)acrylic acid polyoxycarbonyl alkylene esters, and mono(meth)acryloyloxyalkyl esters of dicarboxylic acids. Examples of (meth)acrylic acid alkyl esters include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-lauryl (meth)acrylate, and n-stearyl (meth)acrylate. Examples of (meth)acrylic acid hydroxyalkyl esters include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate. Examples of (meth)acrylic acid alkoxyalkyl esters include methoxyethyl (meth)acrylate, ethoxyethyl (meth)acrylate, and propoxyethyl (meth)acrylate. Examples of (meth)acrylic acid polyoxyalkylene esters include methoxydiethylene glycol (meth)acrylate, methoxytetraethylene glycol (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, methoxydipropylene glycol (meth)acrylate, ethoxydipropylene glycol (meth)acrylate, and 2-ethylhexyloxydiethylene glycol (meth)acrylate. Examples of (meth)acrylic acid polyoxycarbonyl alkylene esters include ω-carboxy-polycaprolactone mono(meth)acrylate.Examples of the mono(meth)acryloyloxyalkyl ester of a dicarboxylic acid include mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate.

[0051] Examples of (meth)acrylic acid esters having an alicyclic structure include cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, 4-butylcyclohexyl (meth)acrylate, 4-hydroxymethylcyclohexyl (meth)acrylate, tricyclo[5.2.1.02,6]decan-8-yl (meth)acrylate, tricyclo[5.2.1.02,5]decan-8-yloxyethyl (meth)acrylate, and isobornyl (meth)acrylate. Examples of (meth)acrylic acid esters having an aromatic ring structure include phenyl (meth)acrylate, benzyl (meth)acrylate, naphthylmethyl (meth)acrylate, naphthylethyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenylthioethyl (meth)acrylate, m-phenoxyphenylmethyl (meth)acrylate, p-phenoxyphenylmethyl (meth)acrylate, o-phenylphenoxyethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, polyethyleneoxynonylphenyl (meth)acrylate, (1-naphthyl)methyl (meth)acrylate, (2-naphthyl)methyl (meth)acrylate, and (1,1'-biphenyl-4-yl)methyl (meth)acrylate.

[0052] Examples of (meth)acrylamide compounds include (meth)acryloylmorpholine, N-(2-hydroxyethyl)(meth)acrylamide, N-vinyl-2-pyrrolidone, and N-vinyl-ε-caprolactam. Examples of chain vinyl compounds include propene, butene, pentene, and hexene. Examples of aromatic vinyl compounds include styrene, methylstyrene, α-methylstyrene, t-butoxystyrene, o-hydroxystyrene, m-hydroxystyrene, p-hydroxystyrene, o-vinylbenzoic acid, m-vinylbenzoic acid, p-vinylbenzoic acid, and vinylnaphthalene. Examples of maleimide compounds include N-methylmaleimide, N-cyclohexylmaleimide, N-phenylmaleimide, and N-(p-methylphenyl)maleimide.

[0053] Further specific examples of the monofunctional polymerizable compound include compounds represented by the following formulas (b1-1) to (b1-21). [ka] [ka] (In formulas (b1-1) to (b1-21), R 20 R is a hydrogen atom or a methyl group. 21 is a monovalent hydrocarbon group having 1 to 20 carbon atoms. n is an integer of 0 to 10.

[0054] Specific examples of the polyfunctional polymerizable compound that contains a polyfunctional (meth)acryloyl group include bifunctional (meth)acrylic acid esters, trifunctional or higher (meth)acrylic acid esters, etc. Specific examples of these include bifunctional (meth)acrylic acid esters such as ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, diethylene glycol di(meth)acrylate, and tetraethylene glycol di(meth)acrylate.

[0055] Examples of the trifunctional or higher (meth)acrylic acid ester include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, ethylene oxide-modified dipentaerythritol hexa(meth)acrylate, tri(2-(meth)acryloyloxyethyl)phosphate, succinic acid-modified pentaerythritol tri(meth)acrylate, and the like. Examples of the compound include (meth)acrylate, succinic acid-modified dipentaerythritol penta(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, and carboxy group-containing polybasic acid-modified (meth)acrylic oligomer, as well as polyfunctional urethane acrylate compounds obtained by reacting a compound having a linear alkylene group and an alicyclic structure and having two or more isocyanate groups with a compound having one or more hydroxyl groups in the molecule and having three, four or five (meth)acryloyloxy groups.

[0056] Further specific examples of the polyfunctional polymerizable compound include the compounds represented by the following formulas (b2-1) to (b2-13). [ka] [ka] (In formulas (b2-1) to (b2-13), R 20 is a hydrogen atom or a methyl group. m and n are each independently an integer of 0 to 10. x, y and z are each independently an integer of 0 to 3, provided that 1≦x+y+z≦3 is satisfied.

[0057] From the viewpoint of achieving transparency and a low refractive index of a cured product obtained by using the present composition, the polymerizable compound to be blended in the present composition is preferably a compound not having an aromatic ring, and more preferably a chain compound, among the above-mentioned compounds.

[0058] The content of the polymerizable compound in the composition is preferably 5 to 99.99 parts by mass relative to 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound. By setting the content of the polymerizable compound in the composition to the above range, the photocurability of the composition can be improved. From this viewpoint, the content of the polymerizable compound is more preferably 10 parts by mass or more, and even more preferably 15 parts by mass or more, relative to 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound. In addition, the content of the polymerizable compound is more preferably 80 parts by mass or less, more preferably 60 parts by mass or less, even more preferably 50 parts by mass or less, even more preferably 45 parts by mass or less, and even more preferably 40 parts by mass or less, relative to 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound.

[0059] <Component (C): Photopolymerization initiator> As the photopolymerization initiator, at least one selected from the group consisting of a photoradical polymerization initiator, a photoacid generator, and a photobase generator can be preferably used. Among these, as the photopolymerization initiator, from the viewpoint of enhancing the photocurability of the present composition, it is preferable to use a combination of two or more selected from the group consisting of a photoradical polymerization initiator, a photoacid generator, and a photobase generator, and it is more preferable to use a combination of one or more of the photoradical polymerization initiators and one or more of the photoacid generators.

[0060] Photoradical polymerization initiator A photoradical polymerization initiator is a compound that can generate radicals in response to radiation and initiate polymerization. Examples of photoradical polymerization initiators include O-acyloxime compounds, acetophenone compounds, biimidazole compounds, and acylphosphine oxide compounds.

[0061] Examples of the O-acyloxime compound include 1,2-octanedione 1-[4-(phenylthio)-2-(O-benzoyloxime)], ethanone-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime), 1-(9-ethyl-6-benzoyl-9.H-carbazol-3-yl)-octan-1-one oxime-O-acetate, 1-[9-ethyl-6-(2-methylbenzoyl)-9.H-carbazol-3-yl]-ethan-1-one oxime-O-benzoate, 1-[9-n-butyl-6-(2-ethylbenzoyl)-9.H-carbazol-3-yl]-ethan-1-one oxime-O-benzoate, and ethanone-1- [9-ethyl-6-(2-methyl-4-tetrahydrofuranylbenzoyl)-9.H.-carbazol-3-yl]-1-(O-acetyloxime), ethanone-1-[9-ethyl-6-(2-methyl-4-tetrahydropyranylbenzoyl)-9.H.-carbazol-3-yl]-1-(O-acetyloxime), ethanone-1-[9-ethyl-6-(2-methyl-5-tetrahydrofuranylbenzoyl)-9.H.-carbazol-3-yl]-1-(O-acetyloxime), ethanone-1-[9-ethyl-6-{2-methyl-4-(2,2-dimethyl-1,3-dioxolanyl)methoxybenzoyl}-9.H.-carbazol-3-yl]-1-(O-acetyloxime), and the like. Other commercially available products include, for example, ADEKA ARCLES N-1919T, NCI-831E, NCI-930, and NCI-730 (all manufactured by ADEKA Corporation); IRGACURE OXE01, OXE2, OXE3, and OXE4 (all manufactured by BASF Corporation); and the like.

[0062] Examples of the acetophenone compound include α-aminoketone compounds and α-hydroxyketone compounds. Specific examples of these include α-aminoketone compounds such as 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, and 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one. Examples of the α-hydroxyketone compound include 1-phenyl-2-hydroxy-2-methylpropan-1-one, 1-(4-i-propylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone, and 1-hydroxycyclohexylphenylketone. Commercially available products include, for example, Irgacure 369, 369E, 379EG, 651, 184, and 907 (all manufactured by BASF).

[0063] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, and 2,2'-bis(2,4,6-trichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole.

[0064] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, and the like.

[0065] The content of the photoradical polymerization initiator in the composition is preferably 0.05 parts by mass or more, more preferably 0.1 parts by mass or more, based on 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound contained in the composition. The content of the photoradical polymerization initiator is preferably 10 parts by mass or less, more preferably 7 parts by mass or less, based on 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound contained in the composition. By setting the content of the photoradical polymerization initiator within the above range, a curable composition that shows good curability and transparency can be obtained.

[0066] Photoacid generator The photoacid generator may be a known compound that generates an acid in response to radiation. Specific examples of the photoacid generator include oxime sulfonate compounds, sulfonimide compounds, onium salts, halogen-containing compounds (such as trichloromethyl-s-triazine compounds), diazomethane compounds, sulfone compounds, sulfonic acid ester compounds, and carboxylate compounds.

[0067] Specific examples of these include oxime sulfonate compounds such as (5-propylsulfonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)acetonitrile, (5-octylsulfonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)acetonitrile, (camphorsulfonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)acetonitrile, (5-p-toluenesulfonyloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)acetonitrile, (2-[2-(4-methylphenylsulfonyloxyimino)]-2,3-dihydrothiophen-3-ylidene]-2-(2-methylphenyl)acetonitrile), 2-(octylsulfonyloxyimino)-2-(4-methoxyphenyl)acetonitrile, and derivatives thereof, and compounds described in International Publication No. WO 2016 / 124493. Commercially available oxime sulfonate compounds include Irgacure PAG121 manufactured by BASF.

[0068] Specific examples of the sulfonimide compound include N-(trifluoromethylsulfonyloxy)succinimide, N-(camphorsulfonyloxy)succinimide, N-(4-methylphenylsulfonyloxy)succinimide, N-(2-trifluoromethylphenylsulfonyloxy)succinimide, N-(4-fluorophenylsulfonyloxy)succinimide, N-(trifluoromethylsulfonyloxy)phthalimide, N-(camphorsulfonyloxy)phthalimide, N-(2-trifluoromethylphenylsulfonyloxy)phthalimide, N-(2-fluorophenylsulfonyloxy)phthalimide, N-(trifluoromethylsulfonyloxy)diphenylmaleimide, N-(camphorsulfonyloxy)diphenylmaleimide, 4-methylphenylsulfonyloxy)diphenylmaleimide, trifluoromethanesulfonic acid-1,8-naphthalimide, and derivatives thereof.

[0069] Examples of the onium salt include diphenyliodonium salt, triphenylsulfonium salt, sulfonium salt, quaternary ammonium salt, benzothiazonium salt, tetrahydrothiophenium salt, etc. Specific examples of these include diphenyliodonium salt, such as diphenyliodonium tetrafluoroborate, diphenyliodonium hexafluorophosphonate, etc.; and triphenylsulfonium salt, such as triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium camphorsulfonate, triphenylsulfonium tetrafluoroborate, triphenylsulfonium trifluoroacetate, triphenylsulfonium-p-toluenesulfonate, triphenylsulfonium butyltris(2,6-difluorophenyl)borate, etc.

[0070] Examples of the sulfonium salt include benzylsulfonium salt, dibenzylsulfonium salt, substituted benzylsulfonium salt, etc. Examples of the alkylsulfonium salt include alkylsulfonium salts such as 4-acetoxyphenyldimethylsulfonium hexafluoroantimonate and 4-acetoxyphenyldimethylsulfonium hexafluoroarsenate; benzylsulfonium salts such as benzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate and benzyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate; dibenzylsulfonium salts such as dibenzyl-4-hydroxyphenylsulfonium hexafluoroantimonate and dibenzyl-4-hydroxyphenylsulfonium hexafluorophosphate; substituted benzylsulfonium salts such as p-chlorobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate and p-nitrobenzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate; and the like.

[0071] Examples of benzothiazonium salts include 3-benzylbenzothiazonium hexafluoroantimonate, 3-benzylbenzothiazonium hexafluorophosphate, 3-benzylbenzothiazonium tetrafluoroborate, 3-(p-methoxybenzyl)benzothiazonium hexafluoroantimonate, 3-benzyl-2-methylthiobenzothiazonium hexafluoroantimonate, and 3-benzyl-5-chlorobenzothiazonium hexafluoroantimonate.

[0072] Examples of the tetrahydrothiophenium salt include 4,7-di-n-butoxy-1-naphthyl tetrahydrothiophenium trifluoromethanesulfonate, 4,7-di-n-butoxynaphthyl tetrahydrothiophenium-10-camphorsulfonate, etc. In addition, as the onium salt, the onium salts described in JP-A-2014-174235, JP-A-2016-87486, JP-A-2014-157252, JP-A-2015-18131, etc. can also be used as a photoacid generator.

[0073] Specific examples of the oxime sulfonate compound, sulfonimide compound, onium salt, halogen-containing compound, diazomethane compound, sulfone compound, sulfonate ester compound, and carboxylate compound include compounds described in paragraphs 0078 to 0106 of JP 2014-157252 A and compounds described in WO 2016 / 124493 A. As the photoacid generator, a compound known as an ionic photoacid generating or nonionic photoacid generating photocationic polymerization initiator can also be used. As the photoacid generator, at least one selected from the group consisting of oxime sulfonate compounds, sulfonimide compounds, and onium salts can be preferably used from the viewpoint of radiation sensitivity.

[0074] The content of the photoacid generator in the composition is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, based on 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound contained in the composition. The content of the photoacid generator is preferably 5 parts by mass or less, more preferably 2 parts by mass or less, based on 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound contained in the composition. By setting the content of the photoacid generator within the above range, a curable composition that shows good curability and transparency can be obtained.

[0075] Photobase generator The photobase generator can be appropriately selected from known compounds that generate a base by light. Specific examples include orthonitrobenzyl carbamates, α,α-dimethyl-3,5-dimethoxybenzyl carbamates, acyloxyiminos, etc. When a photobase generator is added to the composition, the content of the photobase generator in the composition is preferably 0.01 to 5 parts by mass relative to 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound contained in the composition.

[0076] The total content of the photopolymerization initiator in the present composition is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, based on 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound contained in the present composition. The content of the photopolymerization initiator is preferably 15 parts by mass or less, more preferably 10 parts by mass or less, based on 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound contained in the present composition. By setting the content of the photopolymerization initiator within the above range, a photosensitive composition that shows good curability and transparency can be obtained.

[0077] <Other ingredients> In addition to the reactive polyether compound, polymerizable compound, and photopolymerization initiator described above, the composition may further contain other components (hereinafter also referred to as "other components") such as a solvent, a polymerization inhibitor, an antioxidant, a surfactant, an antistatic agent, a defoamer, an adhesive aid, a sensitizer, a plasticizer, and an ultraviolet absorber.

[0078] The composition may contain a solvent together with the reactive polyether compound, the polymerizable compound, and the photopolymerization initiator. When the composition contains a solvent, the solvent is preferably an organic solvent that dissolves each component blended in the composition and does not react with each component. Specific examples of the solvent include alcohols such as methanol, ethanol, isopropanol, butanol, and octanol; esters such as ethyl acetate, butyl acetate, ethyl lactate, γ-butyrolactone, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, methyl 3-methoxypropionate, and ethyl 3-ethoxypropionate; ethers such as ethylene glycol monobutyl ether, propylene glycol monomethyl ether, ethylene diglycol monomethyl ether, ethylene diglycol ethyl methyl ether, dimethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and diethylene glycol ethyl methyl ether; amides such as dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; and aromatic hydrocarbons such as benzene, toluene, xylene, and ethylbenzene. Of these, at least one selected from the group consisting of ethers and esters can be preferably used as the solvent.

[0079] The composition can be obtained by mixing a reactive polyether compound, a polymerizable compound, a photopolymerization initiator, and other components that are optionally mixed in a predetermined ratio. The amount of the other components can be appropriately selected according to each component within a range that does not impair the effects of the present disclosure.

[0080] When the present composition contains a solvent, the ratio of the total mass of the components other than the solvent in the curable composition to the total mass of the curable composition (hereinafter also referred to as "solid content concentration") can be appropriately selected in consideration of viscosity, volatility, etc. The solid content concentration of the present composition is preferably in the range of 5 to 70 mass%. When the solid content concentration is 5 mass% or more, a sufficient thickness of the coating film can be ensured when the present composition is applied onto a substrate. In addition, by setting the solid content concentration to 70 mass% or less, the thickness of the coating film does not become too large, and furthermore, the viscosity of the present composition can be appropriately increased, and good coatability can be ensured. The solid content concentration of the present composition is more preferably 10 to 60 mass%.

[0081] <Method of manufacturing the cured product> A cured product can be produced by using the curable composition prepared as described above. This composition is particularly suitable as a negative pattern-forming material for heat-treating a pattern (i.e., a portion formed by the curable composition) obtained by exposing a portion of a film formed by the curable composition to light and dissolving an unexposed portion in an alkaline developer.

[0082] The cured product of the present disclosure can be produced, for example, by a method including the following steps (I) to (IV). (I) applying the composition onto a substrate (II) A step of irradiating the composition applied onto a substrate with radiation. (III) developing the composition after it has been irradiated with radiation. (IV) A step of heating and curing the composition after development. Each step (steps (I) to (IV)) in the production method of the present disclosure will be described below.

[0083] <Process (I): Coating process> Step (I) is a step of forming a coating film on a substrate by applying the composition onto the substrate. Examples of the substrate include glass substrates, silicon wafers, plastic substrates, plastic films, and substrates having colored resists, overcoats, anti-reflection films, various metal thin films, sealing films, etc. formed on the surfaces thereof. Examples of the plastic substrates and plastic films include resin substrates and films made of plastics such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyethersulfone, polycarbonate, and polyimide. These substrates may be provided in advance with various elements (for example, light receiving elements such as photodiodes, light emitting elements such as organic light emitting diodes).

[0084] The composition can be applied by any suitable method, such as spraying, roll coating, rotary coating (spin coating), slit die coating, bar coating, inkjet coating, etc. Of these, spin coating, bar coating, and slit die coating are preferred.

[0085] After the composition is applied onto a substrate, the composition may be preheated (prebaked) for the purpose of preventing dripping. The prebaking conditions can be appropriately set depending on the type and use ratio of each component. The prebaking conditions can be, for example, 60 to 100° C. for about 30 seconds to 10 minutes. From the viewpoint of being applicable to organic EL devices, the prebaking temperature is preferably 60 to 90° C. The thickness of the coating film formed after prebaking is preferably 0.1 to 20 μm, more preferably 0.2 to 15 μm.

[0086] <Process (II): Exposure process> Step (II) is a step of irradiating at least a part of the coating film formed in step (I) with radiation. This radiation irradiation causes a curing reaction to proceed in the exposed area. In step (II), the radiation irradiation of the coating film is usually carried out through a mask. The mask may be a multi-tone mask such as a halftone mask or a graytone mask.

[0087] Examples of the radiation to be irradiated to the coating film include ultraviolet rays, far ultraviolet rays, X-rays, charged particle beams, etc. Examples of ultraviolet rays include g-rays (wavelength 436 nm), i-rays (wavelength 365 nm), KrF excimer laser light (wavelength 248 nm), etc. Examples of X-rays include synchrotron radiation, etc. Examples of charged particle beams include electron beams, etc. Among these, the radiation to be irradiated to the coating film is preferably ultraviolet rays, and more preferably ultraviolet rays with a wavelength of 200 nm or more and 380 nm or less. Examples of the light source to be used include low pressure mercury lamps, high pressure mercury lamps, deuterium lamps, metal halide lamps, argon resonance lamps, xenon lamps, excimer lasers, etc. The radiation exposure is 500 J / m 2 ~5,000J / m 2 (50~500mJ / cm 2 ) is preferred.

[0088] <Step (III): Development step> Step (III) is a step of forming a pattern on the substrate by developing the coating film irradiated in step (II). By this development step, the unexposed areas of the coating film formed on the substrate are removed, and a pattern consisting of the exposed areas can be formed on the substrate.

[0089] Examples of the developer include aqueous solutions of alkali (basic compounds) such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia, ethylamine, n-propylamine, diethylamine, diethylaminoethanol, di-n-propylamine, triethylamine, methyldiethylamine, dimethylethanolamine, triethanolamine, tetramethylammonium hydroxide (TMAH), tetraethylammonium hydroxide, pyrrole, piperidine, 1,8-diazabicyclo[5.4.0]-7-undecene, and 1,5-diazabicyclo[4.3.0]-5-nonane. Alternatively, an aqueous solution obtained by adding an appropriate amount of a water-soluble organic solvent such as methanol or ethanol or a surfactant to an aqueous solution of an alkali, or by adding a small amount of various organic solvents capable of dissolving the present composition, may be used as the developer.

[0090] As the developing method, for example, a suitable method such as a puddle method, a dipping method, a swing immersion method, a shower method, etc. can be adopted. The developing time may be appropriately adjusted depending on the composition of the present composition. The developing time is, for example, 20 seconds to 120 seconds.

[0091] <Step (IV): Heating step> Step (IV) is a step of heating the developed pattern. The heat treatment in step (IV) further promotes curing, and a cured product exhibiting good heat resistance and chemical resistance can be obtained. The heat treatment can be performed using a heating device such as an oven or a hot plate. When obtaining a microlens as the cured product, the developed pattern may be thermally flowed by the heat treatment in step (IV) to obtain a hemispherical microlens.

[0092] From the viewpoint of enabling application to an organic EL device, the heating temperature in step (IV) is preferably 100° C. or lower, more preferably 95° C. or lower, and even more preferably 90° C. or lower. From the viewpoint of obtaining a cured product having high heat resistance and chemical resistance, the heating temperature in step (IV) is preferably 60° C. or higher, and more preferably 80° C. or higher. The heating time can be appropriately set depending on the type of heating device, etc. For example, when heating is performed using a hot plate, the heating time is, for example, 5 to 60 minutes. When heating is performed using an oven, the heating time is, for example, 10 to 90 minutes. In step (IV), a step bake method in which heating treatment is performed multiple times may be used.

[0093] The manufacturing method of the present disclosure may further include, as an optional step, a step of irradiating the cured product with radiation before or after the heating step in step (IV) (hereinafter also referred to as a "post-exposure step"). By irradiating with radiation in the post-exposure step (hereinafter also referred to as "post-exposure"), the heat resistance, chemical resistance, etc. can be further improved, and a cured product with higher reliability can be obtained. The type of radiation and exposure conditions in the post-exposure may be the same as those in step (II). Note that the conditions such as the wavelength and dose of the irradiated light and the light source in the post-exposure may be the same as or different from those in step (II).

[0094] ·Applications The present composition has high compatibility with each component and excellent transparency before curing. The present composition also has excellent photocurability and storage stability. Furthermore, the cured product formed by the present composition has a low refractive index because it contains a compound having a perfluoropolyether chain, and is also excellent in transparency and adhesion to a substrate. Such a composition is suitable for applications requiring transparency of the cured product, and is suitable, for example, as a curable composition for forming an optical member for an organic EL element or a solid-state imaging element. The optical member formed by the present composition can be preferably applied to applications such as adjusting the path of light emitted from an organic light-emitting layer in an organic EL element by combining with a high refractive index material to increase the light extraction efficiency, or collecting light in a light-receiving element (photodiode) in a solid-state imaging element to improve the sensor sensitivity. In addition, the cured product formed by the present composition may be used as a surface protective film having water repellency and oil repellency, and the surface protective film may be attached to a substrate such as a display device to suppress the occurrence of dirt or scratches on the substrate surface.

[0095] The optical member formed by the composition is preferably a planarizing film or a lens. The planarizing film is formed on a substrate to planarize the surface of the substrate on which a semiconductor element or the like is formed. The lens is a micro-light collector (hereinafter also referred to as a "microlens") or an interlayer lens provided in an organic EL element or a solid-state imaging element (e.g., a CCD image sensor or a CMOS image sensor), and in an organic EL element, the lens is provided in each pixel for the purpose of improving the light extraction efficiency in each pixel and adjusting the viewing angle. In addition, in a solid-state imaging element, the lens is provided for the purpose of collecting light in a light receiving element to improve the sensor sensitivity. The composition is preferably a curable composition for forming a planarizing film or for manufacturing a lens.

[0096] According to the present disclosure described above, the following means are provided.

[0097] [Means 1] (A)-[(C m F 2m )O] n -C k F 2k- (where m is an integer of 1 or more, n is an integer of 2 or more, and m F 2m ) are the same or different, and k is an integer of 1 to 6. A curable composition comprising: (A) a reactive polyether compound having (B) and a plurality of reactive groups bonded to each end of the perfluoropolyether chain directly or via a divalent linking group; (B) a polymerizable compound (excluding the reactive polyether compound); and (C) a photopolymerization initiator, wherein the reactive polyether compound includes a compound having, as the reactive groups, a first reactive group and a second reactive group different from the first reactive group in one molecule, or a first compound and a second compound in which the reactive groups are different between molecules. [Means 2] The curable composition according to [Means 1], wherein the first reactive group and the second reactive group have different polarities, and the reactive group of the first compound and the reactive group of the second compound have different polarities. [Method 3] The reactive group is a (meth)acryloyl group, -Si(OR 1 ) t (R 2 ) 3-t (wherein R 1 and R 2 are each independently a monovalent hydrocarbon group having 1 to 10 carbon atoms, t is an integer of 1 to 3, and when t is 2 or 3, multiple R 1 are the same or different, and when t is 1, multiple R 2 are the same or different.) A curable composition according to [Means 1] or [Means 2], wherein the alkyl group is selected from the group consisting of a vinyl group, an allyl group, and a cyclic ether group. [Measure 4] The curable composition according to any one of [Measure 1] to [Measure 3], wherein the divalent linking group is a group in which some methylene groups in an alkanediyl group having 2 to 10 carbon atoms are replaced with oxygen atoms, ester bonds, amide bonds, urethane bonds or urea bonds. [Means 5] The curable composition according to any one of [Means 1] to [Means 4], wherein the reactive polyether compound contains a compound having the first reactive group and the second reactive group in one molecule, the first reactive group is a group selected from any one of groups A, B, C, and D shown above, and the second reactive group is a group selected from a group different from the first reactive group, among groups A, B, C, and D shown above. [Means 6] The curable composition according to any one of [Means 1] to [Means 5], wherein the reactive polyether compound comprises a compound represented by the above formula (1). [Means 7] The curable composition according to any one of [Means 1] to [Means 6], wherein the reactive polyether compound comprises the first compound and the second compound, the reactive group of the first compound is a group selected from any one of groups A, B, C, and D shown above, and the reactive group of the second compound is a group selected from a group different from the reactive group of the first compound, among groups A, B, C, and D shown above. [Means 8] The curable composition according to any one of [Means 1] to [Means 7], wherein the reactive polyether compound has a weight average molecular weight of 500 to 5,000. [Means 9] The curable composition according to any one of [Means 1] to [Means 8], wherein the perfluoropolyether chain has -[CF2O]-, -[CF2CF2O]-, or both -[CF2O]- and -[CF2CF2O]- as a repeating unit. [Measures 10] The curable composition according to any one of [Measures 1] to [Measures 9], wherein the polymerizable compound does not have an aromatic ring. [Means 11] The curable composition according to any one of [Means 1] to [Means 10], wherein the content of the polymerizable compound is 5 to 50 parts by mass per 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound. [Means 12] The curable composition according to any one of [Means 1] to [Means 11], further comprising a solvent. [Means 13] The curable composition according to any one of [Means 1] to [Means 12], which is used for forming a flattening film, a surface protection film or a lens. [Means 14] A cured product formed from the curable composition according to any one of [Means 1] to [Means 13]. [Means 15] The cured product according to [Means 14], which is a planarizing film, a surface protection film or a lens. [Means 16] An organic EL device comprising the cured product according to [Means 15]. [Means 17] A solid-state imaging device comprising the cured product according to [Means 15]. [Means 18] A compound represented by the above formula (1). EXAMPLES

[0098] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples. In the examples and comparative examples, "parts" and "%" are by weight unless otherwise specified.

[0099] In the present examples, the weight average molecular weight (Mw) of the reactive polyether compound was measured by the following method. Measurement method: Gel permeation chromatography (GPC) method Equipment: Showa Denko GPC-101 GPC column: Shimadzu GLC GPC-KF-801, GPC-KF-802, GPC-KF-803 and GPC-KF-804 combined Mobile phase: Tetrahydrofuran Column temperature: 40℃ ·Flow rate: 1.0mL / min Sample concentration: 1.0% by mass Sample injection volume: 100μL Detector: Differential refractometer Standard material: Monodisperse polystyrene

[0100] 1. (A) Synthesis of reactive polyether compounds [Synthesis Example 1] A fluorine-containing polyether diol (trade name: FOMBLIN D2, manufactured by Solvay Japan) and 1.6 to 2.0 equivalents of 2-acryloyloxyethyl isocyanate relative to the amount of hydroxyl groups in the fluorine-containing polyether diol are placed in a flask, and dibutyltin dilaurate is added in an amount of 0.03 to 3 mass% relative to the amount of the fluorine-containing polyether diol. The mixture is stirred at 25 to 60°C until the residual isocyanate concentration becomes 0.1 mass% or less, thereby obtaining "acryloyl group -O-CH2CH2-NH-CO-OL 1 -O-CO-NH-CH2CH2-O-acryloyl group" (wherein L 1 -CH2-CF2O-(CF2CF2O) p -(CF2O) q The compound (A-6) had a weight average molecular weight (Mw) of 1,780. p and q each represent an integer of 0 to 14 and an integer of 0 to 24, respectively (hereinafter the same). The compound (A-6) thus obtained was designated as "compound (A-6)". The weight average molecular weight (Mw) of compound (A-6) was 1,780.

[0101] [Synthesis Example 2] The following compound (A-5) was synthesized in the same manner as in Synthesis Example 1, except that the reactive group-containing isocyanate compound was changed. A-5: Si(OR 4 )3-CH2CH2CH2-NH-CO-OL 1 -O-CO-NH-CH2CH2CH2-Si(OR 4 )3 In addition, R 4 represents an ethyl group (hereinafter the same). The Mw of compound (A-5) was 1,990.

[0102] [Synthesis Example 3] Fluorine-containing polyether diol (trade name: FOMBLIN D2, manufactured by Solvay Japan Co., Ltd.) and 0.8 to 1.0 equivalents of 2-acryloyloxyethyl isocyanate relative to the amount of hydroxyl groups in the fluorine-containing polyether diol were placed in a flask, and dibutyltin dilaurate in an amount of 0.03 to 3 mass% relative to the amount of hydroxyl groups in the fluorine-containing polyether diol was added, followed by stirring for several hours at 25 to 60° C. Thereafter, 0.8 to 1.0 equivalents of 3-isocyanatepropyltriethoxysilane relative to the amount of hydroxyl groups in the fluorine-containing polyether diol were added to the flask, and the mixture was stirred at 25 to 60° C. until the residual isocyanate concentration became 0.1 mass% or less, thereby synthesizing the compound (A-1) shown below. A-1: Acryloyl group -O-CH2CH2-NH-CO-OL 1 -O-CO-NH-CH2CH2CH2-Si(OR 4 )3 The Mw of compound (A-1) was 1,780.

[0103] [Synthesis Examples 4 and 5] For oligomers having different terminal functional groups, the isocyanate compound used in the synthesis was changed, and the oligomers were synthesized in the same manner as in Synthesis Example 3 to obtain the oligomers shown below (compound (A-2) and compound (A-4)). A-2: Acryloyl group -O-CH2CH2-NH-CO-OL 1 -O-CO-NH-CH=CH2 A-4: Acryloyl group -O-CH2CH2-NH-CO-OL 1 -O-CO-CH2-CH=CH2 The Mw of compound (A-2) was 1,710, and the Mw of compound (A-4) was 1,724.

[0104] [Synthesis Example 6] The compound (A-3) shown below was synthesized by reacting in the corresponding molar ratio with reference to the method described in the literature (JP Patent Publication 2010-275306, etc.). Specifically, 1 mole of fluorine-containing polyether diol (trade name: FOMBLIN D2, manufactured by Solvay Japan) and 1 mole of acrylic acid chloride were reacted in a solvent in the presence of a base catalyst to obtain an intermediate. Then, potassium hydride was reacted in the solvent, and 1 molar equivalent of 2-(6-chlorohexyloxymethyl)oxirane was reacted to obtain compound (A-3). A-3: Acryloyl group-OL 1 -O-CH2CH2CH2CH2CH2CH2CH2-O-glycidyl group The Mw of compound (A-3) was 1,726.

[0105] 2. Preparation and Evaluation of Curable Compositions The (A) reactive polyether compound, (B) polymerizable compound, (C) photopolymerization initiator, and (D) solvent used in the preparation of the curable composition are shown below. (A) Reactive polyether compound A-1 to A-6: Compounds synthesized in Synthesis Examples 1 to 6 A-7; Formula “Si(OCH3)3-(CH2)2-CF2O-(CF2CF2O) p -(CF2O) q -CF2-(CH2)2-Si(OCH3)3" (Mw=1,500) ·(B) Polymerizable compound B-1: 2-Ethylhexyl acrylate B-2: 1,6-Hexanediol diacrylate B-3: Neopentyl diacrylate (C) Photopolymerization initiator C-1: 1-Hydroxycyclohexyl phenyl ketone C-2: Triphenylsulfonium salt (product name "SP-150", manufactured by ADEKA Corporation) (D) Solvent D-1: Propylene glycol monomethyl ether acetate

[0106] [Examples 1 to 13, Comparative Examples 1 to 3] The components shown in Table 1 were placed in a reaction vessel equipped with a stirrer and stirred for 1 hour at a liquid temperature of 50°C to prepare compositions of each Example and Comparative Example. Each of the compositions prepared was evaluated as follows. The units of values ​​in Table 1 are parts by mass.

[0107] (1) Storage stability Each composition was placed in a 60 mL plastic bottle and left to stand in a 40°C oven in a dark environment for one month. Thereafter, the degree of viscosity increase of the curable composition was visually observed to evaluate the storage stability. When no increase in viscosity (thickening) was observed in the curable composition, it was judged as "○ (good)", and when thickening was observed, it was judged as "× (bad)".

[0108] (2) Transparency of the composition About 5 g of the obtained curable composition was placed in a transparent 10 mL vial, and the transparency of the curable composition was visually confirmed. When no turbidity was observed in the curable composition, it was judged as "○ (good)", when some turbidity was observed but at a practical level, it was judged as "△ (passable)", and when turbidity was observed, it was judged as "× (poor)".

[0109] (3) Photocurable (Examples 1 to 11, Comparative Examples 1 to 3) Each composition was applied onto a glass plate using an applicator bar capable of forming a coating film with a thickness of 200 μm, and then irradiated with 1 J / cm 2 using a high-pressure mercury lamp under nitrogen. 2 After irradiation, the degree of hardening of the film was immediately confirmed by finger touch test, and the photocurability of the curable composition was judged from the degree of film formation and tackiness. When a cured film was formed and there was no tackiness, it was judged as "○ (good)", when there was some tackiness but at a practical level, it was judged as "△ (passable)", and when there was tackiness, it was judged as "× (poor)". (Examples 12 and 13) Each composition was applied to a glass plate by spin coating, placed in an oven at 80°C for 3 minutes, and then irradiated with 1 J / cm 2 using a high-pressure mercury lamp under nitrogen. 2After the ultraviolet ray irradiation, the photocurability of the curable composition was evaluated in the same manner as in Examples 1 to 11 and Comparative Examples 1 to 3.

[0110] (4) Film turbidity (Examples 1 to 11, Comparative Examples 1 to 3) Each composition was applied onto a glass plate using an applicator bar capable of forming a coating film with a thickness of 200 μm, and then irradiated with 1 J / cm 2 using a high-pressure mercury lamp under nitrogen. 2 After irradiation, the turbidity of the film was immediately checked by visual inspection. If no turbidity was observed, it was judged as "○ (good)", if some turbidity was observed but at a practical level, it was judged as "△ (passable)", and if turbidity was observed, it was judged as "× (poor)". (Examples 12 and 13) Each composition was applied to a glass plate by spin coating, placed in an oven at 80°C for 3 minutes, and then irradiated with 1 J / cm 2 using a high-pressure mercury lamp under nitrogen. 2 After the ultraviolet ray irradiation, the film turbidity was evaluated in the same manner as in Examples 1 to 11 and Comparative Examples 1 to 3.

[0111] [Table 1]

[0112] As shown in Table 1, the curable compositions of Examples 1 to 13 had high transparency before curing, and had good storage stability and photocurability. In addition, in Examples 1 to 13, the cured films obtained from the curable compositions had low turbidity after photocuring, that is, the cured films had high transparency. In particular, the curable compositions of Examples 1 to 10, 12, and 13, which used a compound in which reactive groups bonded to both ends of the molecular chain were different within one molecule as the (A) reactive polyether compound, showed excellent photocurability, and no clouding of the film was observed, which was particularly excellent.

[0113] In contrast, in Comparative Examples 1 to 3, in which a compound in which reactive groups bonded to both ends of the molecular chain are identical within one molecule was used as the (A) reactive polyether compound, the transparency of the composition before curing and / or the haze of the film after photocuring were evaluated as poor, and the performance was inferior to that of Examples 1 to 13. Furthermore, Comparative Examples 1 and 3 were also evaluated as poor in terms of storage stability and photocurability.

Claims

1. (A)-[(C ｍ F ２ｍ ) O] ｎ -C ｋ F ２ｋ - (where m is an integer of 1 or more, n is an integer of 2 or more, and a plurality of (C ｍ F ２ｍ ) are the same or different, and k is an integer of 1 to 6. A reactive polyether compound having: (B) a polymerizable compound (excluding the reactive polyether compound), and (C) Photopolymerization initiator Contains The curable composition includes a reactive polyether compound having, in one molecule, a first reactive group and a second reactive group different from the first reactive group, as the reactive groups, or a first compound and a second compound having different reactive groups between molecules.

2. the first reactive group and the second reactive group have different polarities, The curable composition according to claim 1 , wherein the reactive group of the first compound and the reactive group of the second compound have different polarities.

3. The reactive group is a (meth)acryloyl group, —Si(OR １ ) ｔ (R ２ ) ３－ｔ (wherein R １ and R ２ are each independently a monovalent hydrocarbon group having 1 to 10 carbon atoms, t is an integer of 1 to 3, and when t is 2 or 3, multiple R １ are the same or different, and when t is 1, a plurality of R ２ The curable composition of claim 1, wherein the alkyl group is selected from the group consisting of a vinyl group, an allyl group, and a cyclic ether group.

4. The curable composition according to claim 1, wherein the divalent linking group is a group in which some methylene groups in an alkanediyl group having 2 to 10 carbon atoms are replaced with oxygen atoms, ester bonds, amide bonds, urethane bonds, or urea bonds.

5. the reactive polyether compound includes a compound having the first reactive group and the second reactive group in one molecule, The first reactive group is a group selected from any one of Group A, Group B, Group C, and Group D shown below, The curable composition according to claim 1 , wherein the second reactive group is a group selected from the group A, B, C, and D shown below, which is different from the first reactive group. Group A: (meth)acryloyl group Group B: -Si(OR １ ) ｔ (R ２ ) ３－ｔ (wherein R １ and R ２ are each independently a monovalent hydrocarbon group having 1 to 10 carbon atoms, t is an integer of 1 to 3, and when t is 2 or 3, multiple R １ are the same or different, and when t is 1, a plurality of R ２ are the same or different.) Group C: vinyl group, allyl group Group D: cyclic ether group

6. The curable composition according to claim 5 , wherein the reactive polyether compound comprises a compound represented by the following formula (1): 【Chemistry 1】 (In formula (1), X １ is the first reactive group. ２ is the second reactive group. １ and Y ２ are each independently a single bond or a divalent group in which some methylene groups in an alkanediyl group having 2 to 10 carbon atoms are replaced with oxygen atoms, ester bonds, amide bonds, urethane bonds or urea bonds. Lf is -[(C ｍ F ２ｍ ) O] ｎ -C ｋ F ２ｋ m is an integer of 1 or more, n is an integer of 2 or more, and a plurality of (C ｍ F ２ｍ ) are the same or different; k is an integer from 1 to 6.

7. the reactive polyether compound comprises the first compound and the second compound, The reactive group of the first compound is a group selected from any one of Group A, Group B, Group C, and Group D shown below, The curable composition according to claim 1, wherein the reactive group of the second compound is a group selected from the group A, B, C, and D shown below, which is different from the reactive group of the first compound. Group A: (meth)acryloyl group Group B: -Si(OR １ ) ｔ (R ２ ) ３－ｔ (wherein R １ and R ２ are each independently a monovalent hydrocarbon group having 1 to 10 carbon atoms, t is an integer of 1 to 3, and when t is 2 or 3, multiple R １ are the same or different, and when t is 1, a plurality of R ２ are the same or different.) Group C: vinyl group, allyl group Group D: cyclic ether group

8. The curable composition according to claim 1, wherein the reactive polyether compound has a weight average molecular weight of 500 to 5,000.

9. The perfluoropolyether chain is -[CF ２ O]-, -[CF ２ CF ２ O]- or -[CF ２ O]- and -[CF ２ CF ２ 2. The curable composition according to claim 1, having both as repeat units:

10. The curable composition according to claim 1 , wherein the polymerizable compound does not have an aromatic ring.

11. The curable composition according to claim 1, wherein the content of the polymerizable compound is 5 to 99.99 parts by mass per 100 parts by mass of the total amount of the reactive polyether compound and the polymerizable compound.

12. The curable composition of claim 1 further comprising a solvent.

13. The curable composition according to claim 1, which is used for forming a planarizing film, a surface protective film, or a lens.

14. A cured product formed from the curable composition according to any one of claims 1 to 13.

15. The cured product according to claim 14, which is a planarizing film, a surface protection film, or a lens.

16. An organic electroluminescence device comprising the cured product according to claim 14.

17. A solid-state imaging device comprising the cured product according to claim 14.

18. A compound represented by the following formula (1): 【Chemistry 2】 (In formula (1), X １ is a group selected from Group A, Group B, Group C, or Group D shown below. ２ Among the following groups A, B, C, and D, X １ is a group selected from a group different from Group A: (meth)acryloyl group Group B: -Si(OR １ ) ｔ (R ２ ) ３－ｔ (wherein R １ and R ２ are each independently a monovalent hydrocarbon group having 1 to 10 carbon atoms, t is an integer of 1 to 3, and when t is 2 or 3, multiple R １ are the same or different, and when t is 1, a plurality of R ２ are the same or different.) Group C: vinyl group, allyl group Group D: cyclic ether group Y １ and Y ２ are each independently a single bond or a divalent group in which some methylene groups in an alkanediyl group having 2 to 10 carbon atoms are replaced with oxygen atoms, ester bonds, amide bonds, urethane bonds or urea bonds. Lf is -[(C ｍ F ２ｍ ) O] ｎ -C ｋ F ２ｋ m is an integer of 1 or more, n is an integer of 2 or more, and a plurality of (C ｍ F ２ｍ ) are the same or different; k is an integer from 1 to 6.

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