Curable compound, curable composition, and method for producing curable compound

Abstract

This disclosure provides a curable compound that can be cured at low temperatures in the presence of oxygen. This disclosure provides a curable compound represented by the following formula (1). [Where R...] 1 R represents a curable functional group having a cyclic imide structure. 2 This refers to a functional group that has a succinimide structure and promotes the curing of the curable functional group. (D) 1 and D 2 "Identical" or "different" indicates a single bond or a linking group. "L" represents a divalent group having repeating units comprising the structures shown in formula (I) and (II) below.

Description

Technical Field

[0001] This disclosure relates to curable compounds, curable compositions, and methods for manufacturing curable compounds. More specifically, this disclosure relates to curable compounds, curable compositions comprising said curable compounds, and methods for manufacturing said curable compounds. Furthermore, this application claims priority to Japanese Patent Application No. 2024-030367, filed on February 29, 2024, the contents of which are incorporated herein by reference. Background Technology

[0002] Engineering plastics are high-performance materials that combine high heat resistance and mechanical properties, and are widely used as essential materials for the miniaturization, weight reduction, high performance, and high reliability of various components. However, polyimide, for example, is a type of engineering plastic, but it is not easily soluble in solvents and is not easily melted, making it difficult to obtain molded parts suitable for its intended application.

[0003] In particular, polyetheretherketone (PEEK), also known as a super engineering plastic, is a thermoplastic resin with a continuous operating temperature of 260°C and excellent heat resistance, flame retardancy and electrical properties. However, due to its melting point of 343°C, it is particularly difficult to melt and dissolve in solvents, resulting in poor processability and making it difficult to obtain molded parts.

[0004] On the other hand, a curable compound is known that can be molded into a cured product with a PEEK framework. This curable compound is easily melted and has excellent solvent solubility, thus exhibiting good operability and processability, and can easily produce cured products and molded articles with a PEEK framework (see Patent Documents 1-3).

[0005] Existing technical documents

[0006] Patent documents

[0007] Patent Document 1: Japanese Patent Application Publication No. 2021-95542

[0008] Patent Document 2: Japanese Patent Application Publication No. 2021-95544

[0009] Patent Document 3: International Publication No. 2019 / 244693 Summary of the Invention

[0010] The problem that the invention aims to solve

[0011] Sometimes, it is required that the aforementioned curable compounds cure at relatively low temperatures. To achieve low-temperature curing, peroxides are considered as curing agents. However, peroxides are deactivated by oxygen, making it difficult to form a stable cured product in oxygen-containing systems such as air. It should be noted that when using peroxides as curing agents, the process must be carried out under a nitrogen atmosphere.

[0012] Therefore, the object of this disclosure is to provide a curable composition that can be cured at low temperatures in the presence of oxygen.

[0013] Solution for solving the problem

[0014] The inventors of this disclosure conducted in-depth research to solve the aforementioned technical problems and discovered that certain curable compounds can be cured at low temperatures in the presence of oxygen. This disclosure relates to technical solutions based on these insights.

[0015] That is, this disclosure provides a curable compound represented by the following formula (1).

[0016] [Chemical Formula 1]

[0017] [In the formula, R] 1 R represents a curable functional group having a cyclic imide structure. 2 This indicates a functional group that has a succinimide structure and promotes the curing of the aforementioned curable functional groups. (D) 1 and D 2 "Identical" or "different" indicates a single bond or a linking group. "L" represents a divalent group having repeating units comprising the structures shown in formula (I) and (II) below.

[0018] [Chemical Formula 2]

[0019] (In the formula, Ar) 1 ~Ar 3 "Same" or "different" indicates a group formed by removing two hydrogen atoms from the structural formula of an aromatic ring, or a group formed by removing two hydrogen atoms from the structural formula of two or more aromatic rings bonded together by single bonds or connecting groups. X represents -CO-, -S-, or -SO2-. "Same" or "different" Y represents -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. n represents an integer greater than or equal to 0.

[0020] Preferably, the above-mentioned R 2 The group represented by the following formula (r-2) is indicated.

[0021] [Chemical Formula 6]

[0022] (where R) 7 ~R 10 Same or different indicates a hydrocarbon group. R 9 and R 10They can optionally bond together to form a loop. The bonds with wavy lines in the formula are connected to D. 2 (Bonding.)

[0023] Preferably, the above-mentioned R 1 The group represented by the following formula (r-1) is indicated.

[0024] [Chemical Formula 3]

[0025] [In the formula, Q represents C or CH. The two Qs in the formula are bonded together via a single bond or a double bond. R] 3 ~R 6 Same or different, indicating a hydrogen atom or a hydrocarbon group. R 3 and R 4 They can optionally bond together to form a ring. n' represents an integer greater than 0. The bonds with tildes in the formula are connected to D. 1 Bonding.

[0026] Preferably, the group represented by formula (r-1) above is selected from the groups represented by formulas (r-1-1) to (r-1-6) below.

[0027] [Chemical Formula 4]

[0028] (The bond extending from the nitrogen atom in the formula is the same as the D in formula (1)) 1 (Bonding.)

[0029] Furthermore, this disclosure provides a curable composition comprising the above-described curable compound and a compound represented by the following formula (2).

[0030] [Chemical Formula 18]

[0031] [In the formula, R] 11 and R 12 Same or different indicates a curable functional group having a cyclic imide structure. D 1 and D 2 "Identical" or "different" indicates a single bond or a linking group. "L" represents a divalent group having repeating units comprising the structures shown in formula (I) and (II) below.

[0032] [Chemical Formula 2]

[0033] (In the formula, Ar) 1 ~Ar 3"Same" or "different" indicates a group formed by removing two hydrogen atoms from the structural formula of an aromatic ring, or a group formed by removing two hydrogen atoms from the structural formula of two or more aromatic rings bonded together by single bonds or connecting groups. X represents -CO-, -S-, or -SO2-. "Same" or "different" Y represents -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. n represents an integer greater than or equal to 0.

[0034] Preferably, in the above-described curable composition, the presence ratio of the compound shown in formula (1) to the compound shown in formula (2) calculated by the area ratio based on MS analysis [compound shown in formula (1) / compound shown in formula (2)] is 0.08 or more.

[0035] Furthermore, this disclosure provides a method for manufacturing the above-mentioned curable compound, comprising: reacting a compound represented by the following formula (1') with a cyclic anhydride in the presence of a compound having an acetamide structure to obtain the compound represented by the above formula (1).

[0036] [Chemical Formula 14]

[0037] [In the formula, D] 1 and D 2 "Identical" or "different" indicates a single bond or a linking group. "L" represents a divalent group having repeating units comprising the structures shown in formula (I) and (II) below.

[0038] [Chemical Formula 2]

[0039] (In the formula, Ar) 1 ~Ar 3 "Same" or "different" indicates a group formed by removing two hydrogen atoms from the structural formula of an aromatic ring, or a group formed by removing two hydrogen atoms from the structural formula of two or more aromatic rings bonded together by single bonds or connecting groups. X represents -CO-, -S-, or -SO2-. "Same" or "different" Y represents -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. n represents an integer greater than or equal to 0.

[0040] Invention Effects

[0041] The curable compound disclosed herein can be cured at low temperatures in the presence of oxygen. Therefore, it has a wide range of applications and can be used in various situations, considering both the equipment used to cure the curable composition containing the above-described curable compound and its productivity. Detailed Implementation

[0042] [Curable Compound]

[0043] The curable compound disclosed herein is a compound represented by the following formula (1) (hereinafter, sometimes referred to as "compound (1)").

[0044] [Chemical Formula 1]

[0045] In equation (1), R 1 This indicates a curable functional group possessing a cyclic imide structure. The nitrogen atom in the aforementioned cyclic imide structure interacts with D... 1 Bonding.

[0046] In equation (1), R 2 This refers to a functional group (curing-promoting group) that has a succinimide structure and promotes the curing of the aforementioned curable functional groups. That is, R 2 To promote R 1 The curing functional group in the text refers to the curing group. Here, promoting the curing of curing functional groups means, as in the case of a catalyst, promoting the reaction between curing functional groups or between curing functional groups and other reactive functional groups.

[0047] In equation (1), D 1 and D 2 The same or different indicates a single bond or a connecting group.

[0048] In formula (1), L represents a divalent group having repeating units comprising the structures shown in formula (I) and formula (II) below.

[0049] [Chemical Formula 2]

[0050] In equations (I) and (II), Ar 1 ~Ar 3 "Same" or "different" indicates a group formed by removing two hydrogen atoms from the structural formula of an aromatic ring, or a group formed by removing two hydrogen atoms from the structural formula of two or more aromatic rings bonded together by single bonds or connecting groups. X represents -CO-, -S-, or -SO2-. "Same" or "different" Y represents -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. n represents an integer greater than or equal to 0.

[0051] Preferably, the above-mentioned R 1 It is the group represented by the following formula (r-1).

[0052] [Chemical Formula 3]

[0053] In equation (r-1), Q represents C or CH. The two Qs in the equation are bonded together via a single or double bond. R3 ~R 6 Same or different, indicating a hydrogen atom or a hydrocarbon group. R 3 and R 4 They can optionally bond together to form a ring. n' represents an integer greater than 0. The wavy bond in equation (r-1) is connected to D. 1 Bonding.

[0054] In equation (r-1), R is used as 3 ~R 6 The hydrocarbon group in the group may include, for example, saturated or unsaturated aliphatic hydrocarbon groups (preferably alkyl groups with 1 to 10 carbon atoms, alkenyl groups with 2 to 10 carbon atoms, or alkynyl groups with 2 to 10 carbon atoms), aromatic hydrocarbon groups (preferably aryl groups with 6 to 10 carbon atoms such as phenyl or naphthyl), or groups formed by bonding two or more groups selected from the above-mentioned saturated or unsaturated aliphatic hydrocarbon groups and the above-mentioned aromatic hydrocarbon groups.

[0055] In equation (r-1), R 3 and R 4 Optionally, they bond to each other and form rings together with adjacent carbon atoms. Examples of such rings include alicyclic rings with 3 to 20 carbon atoms and aromatic rings with 6 to 14 carbon atoms. Examples of alicyclic rings with 3 to 20 carbon atoms include: cyclopropane rings, cyclobutane rings, cyclopentane rings, cyclohexane rings, etc., which are 3 to 20 members (preferably 3 to 15 members, particularly preferably 5 to 8 members); cyclopentene rings, cyclohexene rings, etc., which are 3 to 20 members (preferably 3 to 15 members, particularly preferably 5 to 8 members); perhydronaphthalene rings, norbornene rings, norbornene rings, adamantane rings, tricyclic rings [5.2.1.0] 2,6 [Decane ring, tetracyclic ring [4.4.0.1]] 2,5 .1 7,10 Bridged ring hydrocarbon groups such as dodecane rings. Examples of aromatic rings with 6 to 14 carbon atoms include benzene rings and naphthalene rings.

[0056] In equation (r-1), n' is an integer greater than or equal to 0, for example, an integer from 0 to 3, preferably 0 or 1.

[0057] As the group shown in the above formula (r-1), preferably a group selected from the groups shown in the following formulas (r-1-1) to (r-1-6).

[0058] [Chemical Formula 4]

[0059] (The bond extending from the nitrogen atom in the formula is the same as the D in formula (1)) 1 (Bonding.)

[0060] One or more substituents may be bonded to the groups shown in formulas (r-1-1) to (r-1-6) above. Examples of such substituents include hydrocarbon groups (e.g., hydrocarbon groups with 1 to 14 carbon atoms), alkoxy groups with 1 to 6 carbon atoms, halogen atoms, etc.

[0061] As the group represented by formula (r-1) above, it is preferably selected from the groups represented by formulas (r-1-1) to (r-1-5) above, and the groups represented by formulas (r-1-1) or (r-1-5) above are particularly preferred.

[0062] As the group represented by the above formula (r-1), the group represented by the following formula (r-1') is preferred.

[0063] [Chemical Formula 5]

[0064] (In the formula, Q and R) 3 and R 4 Same as above.

[0065] The above R 2 Preferably, it contains the group represented by the following formula (r-2).

[0066] [Chemical Formula 6]

[0067] In equation (r-2), R 7 and R 8 Same or different, indicating a hydrogen atom or a hydrocarbon group. R 9 and R 10 Same or different indicates a hydrocarbon group. R 9 and R 10 They can optionally bond together to form a ring. The wavy bond in equation (r-2) is connected to D... 2 Bonding.

[0068] In equation (r-2), R is used as 7 and R 8 The hydrocarbon group in the group may include, for example, saturated or unsaturated aliphatic hydrocarbon groups (preferably alkyl groups with 1 to 10 carbon atoms, alkenyl groups with 2 to 10 carbon atoms, or alkynyl groups with 2 to 10 carbon atoms), aromatic hydrocarbon groups (preferably aryl groups with 6 to 10 carbon atoms such as phenyl or naphthyl), or groups formed by bonding two or more groups selected from the above-mentioned saturated or unsaturated aliphatic hydrocarbon groups and the above-mentioned aromatic hydrocarbon groups.

[0069] In equation (r-2), R is... 9 and R 10The hydrocarbon group in R can be exemplified by, for example: saturated or unsaturated aliphatic hydrocarbon groups (preferably alkyl groups with 1 to 10 carbon atoms, alkenyl groups with 2 to 10 carbon atoms, or alkynyl groups with 2 to 10 carbon atoms), aromatic hydrocarbon groups (preferably aryl groups with 6 to 10 carbon atoms, such as phenyl or naphthyl), and groups formed by bonding two or more groups selected from the above-mentioned saturated or unsaturated aliphatic hydrocarbon groups and aromatic hydrocarbon groups. 9 and R 10 The hydrocarbon group in the hydrocarbon group is preferably a saturated or unsaturated aliphatic hydrocarbon group with 1 to 6 carbon atoms (preferably an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, or an alkynyl group with 2 to 6 carbon atoms), and preferably a saturated or unsaturated aliphatic hydrocarbon group with 1 to 4 carbon atoms (preferably an alkyl group with 1 to 4 carbon atoms).

[0070] In equation (r-2), R 9 and R 10 They optionally bond to each other and form a ring together with adjacent nitrogen atoms. Examples of such rings include R in equation (r-1). 3 and R 4 Examples and illustrations of rings that can be formed.

[0071] The group represented by the above formula (r-2) is preferably the group represented by the following formula (r-2').

[0072] [Chemical Formula 7]

[0073] In equation (r-2'), R 9’ and R 10’ Whether the groups are the same or different, they represent saturated or unsaturated aliphatic hydrocarbon groups with 1 to 6 carbon atoms (preferably alkyl groups with 1 to 6 carbon atoms, alkenyl groups with 2 to 6 carbon atoms, or alkynyl groups with 2 to 6 carbon atoms), preferably saturated or unsaturated aliphatic hydrocarbon groups with 1 to 4 carbon atoms, and more preferably alkyl groups with 1 to 4 carbon atoms.

[0074] In equation (1), D 1 and D 2 The terms "same" or "different" indicate single bonds or linking groups. Examples of linking groups include: divalent hydrocarbon groups, divalent heterocyclic groups, carbonyl groups, ether bonds, ester bonds, carbonate bonds, amide bonds, imide bonds, and groups formed by the linkage of multiple of these.

[0075] As D 1 and D 2From the perspective of obtaining a cured product with particularly excellent heat resistance, groups containing divalent aromatic hydrocarbon groups are preferred, and particularly preferred are arylene groups with 6 to 14 carbon atoms, such as 1,4-phenylene, 1,3-phenylene, 4,4'-biphenylene, 3,3'-biphenylene, 2,6-naphthodiyl, 2,7-naphthodiyl, 1,8-naphthodiyl, and anthracenediyl.

[0076] As D 1 and D 2 The groups are preferably selected from those shown in formulas (d-1) to (d-4) below, especially the group shown in formula (d-1) below (1,2-phenylene, 1,3-phenylene or 1,4-phenylene), more preferably 1,4-phenylene. It should be noted that there are no particular restrictions on the connection positions of the bonds in the following formulas.

[0077] [Chemical Formula 8]

[0078] In addition, D 1 and D 2 Preferably, the divalent aromatic hydrocarbon group is connected to at least one group selected from the group consisting of carbonyl, ether, ester, carbonate, amide and imide bonds, and particularly preferably, the divalent aromatic hydrocarbon group is connected to an ether bond.

[0079] Therefore, R in equation (1) 1 -D 1 - group, preferably the group shown in the following formula (rd-1'-1) or (rd-1'-2). It should be noted that there are no particular restrictions on the connection position of the bonds in the following formulas.

[0080] [Chemical Formula 9]

[0081] (In the formula, Q and R) 3 and R 4 Same as above.

[0082] Furthermore, R in equation (1) 2 -D 2 - group, preferably the group shown in the following formula (rd-2'-1) or (rd-2'-2). It should be noted that there are no particular restrictions on the connection position of the bonds in the following formulas.

[0083] [Chemical Formula 10]

[0084] (where R) 9’ and R 10’ Same as above.

[0085] Ar 1 ~Ar 3 "Same" or "different" refers to a group formed by removing two hydrogen atoms from the structure of an aromatic ring, or a group formed by removing two hydrogen atoms from the structure of two or more aromatic rings bonded together by single bonds or connecting groups.

[0086] Examples of aromatic rings mentioned above include aromatic rings with 6 to 14 carbon atoms, such as benzene, naphthalene, anthracene, and phenanthrene. Among these, aromatic hydrocarbon rings with 6 to 10 carbon atoms, such as benzene and naphthalene, are preferred.

[0087] Examples of such linking groups include: divalent hydrocarbon groups with 1 to 5 carbon atoms, and groups formed by replacing one or more hydrogen atoms of a divalent hydrocarbon group with 1 to 5 carbon atoms with halogen atoms.

[0088] Therefore, as Ar 1 ~Ar 3 Whether the groups are the same or different, they are preferably groups formed by removing two hydrogen atoms from a structural formula of an aromatic ring having 6 to 14 carbon atoms, or groups formed by removing two hydrogen atoms from a structural formula formed by bonding two or more aromatic rings having 6 to 14 carbon atoms through the following structural bond: a single bond, a straight-chain or branched alkylene group having 1 to 5 carbon atoms, or a group formed by replacing one or more hydrogen atoms of a straight-chain or branched alkylene group having 1 to 5 carbon atoms with halogen atoms.

[0089] As Ar 1 ~Ar 3 The groups, whether the groups are the same or different, are preferably selected from the groups shown in formulas (a-1) to (a-5) below. It should be noted that there are no particular restrictions on the connection positions of the bonds in the following formulas.

[0090] [Chemical Formula 11]

[0091] Ar in equation (I) 1 and Ar 2 Preferably, the group is formed by removing two hydrogen atoms from the structure of an aromatic ring with 6 to 14 carbon atoms, and particularly preferably the group shown in formula (a-1) or (a-2) above.

[0092] In formula (I), X represents -CO-, -S-, or -SO2-. Preferably, X is -CO- or -SO2-.

[0093] Ar in equation (II) 3 The preferred group is selected from the groups shown in formulas (a-1), (a-4) and (a-5) above.

[0094] In formula (II), Y may be the same or different, representing -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. Preferably, Y is -S-, -O-, or -SO2-.

[0095] In formula (II), n represents an integer greater than or equal to 0, for example, an integer from 0 to 5, preferably an integer from 1 to 5, and particularly preferably an integer from 1 to 3.

[0096] As L in formula (1), it is preferably a divalent group as shown in formula (L-1-1) or (L-1-2).

[0097] [Chemical Formula 12]

[0098] In the above formula, m1 and m2 represent the number of repeating units (shown in parentheses) in the molecular chain (= the divalent group shown in formula (L-1-1) or (L-1-2) above), i.e., the average degree of polymerization, for example, 2 to 50, preferably 3 to 40, more preferably 4 to 30, further preferably 5 to 20, and particularly preferably 5 to 10. It should be noted that the values ​​of m1 and m2 can be determined using GPC measurement and NMR spectral analysis.

[0099] The number of moles of the functional group represented by formula (r-1) per 1g of compound (1) (hereinafter sometimes referred to as "functional group concentration (r-1)") is, for example, 2 × 10⁻⁶. -5 ~10×10 -4 mol / g. The upper limit of the above functional group concentration is preferably 7.5 × 10⁻⁶ mol / g. -4 mol / g, preferably 5×10 -4 mol / g. The preferred lower limit for the concentration of the above functional groups is 5 × 10⁻⁶ mol / g. -5 mol / g, preferably 7×10 -5 mol / g. If the concentration of the above functional groups (r-1) is within the above range, the solvent has excellent solubility and can form a cured product with excellent toughness and heat resistance.

[0100] The number of moles of the functional group represented by formula (r-2) per 1g of compound (1) (hereinafter sometimes referred to as "functional group concentration (r-2)") is, for example, 2 × 10⁻⁶. -5 ~10×10 -4 mol / g. The upper limit of the above functional group concentration is preferably 7.5 × 10⁻⁶ mol / g. -4 mol / g, preferably 5×10 -4 mol / g. The preferred lower limit for the concentration of the above functional groups is 5 × 10⁻⁶ mol / g. -5 mol / g, preferably 7×10-5 mol / g. If the concentration of the above functional groups (r-2) is within the above range, the solvent has excellent solubility and can form a cured product with excellent toughness and heat resistance.

[0101] The above functional group concentration (r-1) can be determined by the concentration of compound (1) according to the concentration of functional groups (r-1). 1 The area of ​​each peak is determined from the H-NMR spectrum, and the calculated value is substituted into the following formula to obtain the result. The concentration of the functional group (r-2) can also be calculated in the same way.

[0102] Functional group concentration (r-1) = [peak area of ​​the group represented by formula (r-1) / number of protons of the group represented by formula (r-1)] / Σ [(peak area / number of protons of the group to which each peak belongs) × chemical formula weight corresponding to each peak]

[0103] The ring-closure rate of compound (1) is preferably 97 mol% or more, more preferably 98 mol% or more, even more preferably 98.5 mol% or more, and particularly preferably 99 mol% or more. If the above-mentioned ring-closure rate is within the above range, the solvent solubility is excellent. The above-mentioned ring-closure rate is calculated as the ratio of the total of the groups shown in formula (r-3) and formula (r-5) to the total of the groups shown in formulas (r-3) to (r-6). It should be noted that the molar number of each group can be determined by... 1 The peak areas corresponding to each functional group in the H-NMR spectrum are calculated.

[0104] Ring closure rate [mol%] = [(moles of the group shown in formula (r-3) below + moles of the group shown in formula (r-5) below) / (moles of the group shown in formula (r-3) below + moles of the group shown in formula (r-4) below + moles of the group shown in formula (r-5) below + moles of the group shown in formula (r-6) below)] × 100

[0105] [Chemical Formula 13]

[0106] The number-average molecular weight (Mn; standard polystyrene conversion) of compound (1) is, for example, 1,000 to 15,000, preferably 1,500 to 12,000, more preferably 2,000 to 10,000, even more preferably 2,200 to 8,000, and particularly preferably 2,500 to 7,500.

[0107] The weight-average molecular weight (Mw; converted to standard polystyrene) of compound (1) is, for example, 1,000 to 45,000. The lower limit of the weight-average molecular weight (Mw) is preferably 1,500, more preferably 2,500, further preferably 3,000, and particularly preferably 4,000. The upper limit of the weight-average molecular weight (Mw) is preferably 40,000, more preferably 35,000, and further preferably 25,000.

[0108] The above Mn and Mw were determined by gel permeation chromatography (GPC) (solvent: chloroform, converted from standard polystyrene). If compound (1) has the above molecular weight, it has excellent solvent solubility.

[0109] Compound (1) has excellent solvent solubility, and its solubility at 23°C in 100g of solvent is preferably 1g or more, more preferably 5g or more, and particularly preferably 10g or more.

[0110] Compound (1) has excellent solvent solubility, with a solubility of more than 1g in 100g of solvent at 23°C, preferably more than 5g, and particularly preferably more than 10g.

[0111] [Method for Producing Compound (1)]

[0112] Compound (1) is prepared, for example, by reacting a compound of the following formula (1') with a cyclic anhydride in the presence of a compound having an acetamide structure.

[0113] [Chemical Formula 14]

[0114] (where D) 1 D 2 And L is the same as above.

[0115] The compounds shown in the above formula (1') can be manufactured, for example, the compounds shown in the following formula (1'-1) can be manufactured by the following steps [1-1] and [1-2].

[0116] Step [1-1]: React the compound shown in formula (1a) with the compound shown in formula (1b) in the presence of a base to obtain the compound shown in formula (1c).

[0117] Step [1-2]: React the amino alcohol (the compound shown in formula (1d) below) with the compound shown in formula (1c) below.

[0118] [Chemical Formula 15]

[0119] In the above formula, Ar 1 ~Ar 3X, Y, and n are related to Ar in equations (I) and (II) above. 1 ~Ar 3 X, Y, and n are the same. D represents a linking group, and examples of groups with the same name as D can be listed. 1 and D 2 The linking group is another example. m is the average degree of polymerization of the repeating unit, for example, 3 to 50, preferably 4 to 30, and particularly preferably 5 to 20. Z represents a halogen atom.

[0120] (Step [1-1])

[0121] Examples of compounds represented by formula (1a) above include halides of diaryl compounds such as benzophenone and 2-naphthylphenyl ketone, and their derivatives.

[0122] Examples of compounds represented by formula (1b) above include hydroquinone, resorcinol, bisphenol A, etc.

[0123] Examples of such bases include inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, and sodium bicarbonate; and organic bases such as pyridine and triethylamine. The amount of each base used can be adjusted according to the type of base. For example, the amount of a binary base such as calcium hydroxide used is approximately 1.0 to 2.0 moles relative to 1 mole of the compound shown in formula (1b).

[0124] Furthermore, the reaction can be carried out in the presence of a solvent. Examples of solvents that can be used include organic solvents such as N-methyl-2-pyrrolidone, dimethylformamide, and dimethyl sulfoxide, or mixtures of two or more of these.

[0125] The reaction atmosphere is not particularly limited as long as it does not hinder the reaction; for example, it can be any atmosphere such as nitrogen or argon. The reaction temperature is, for example, around 100–200°C.

[0126] (Step [1-2])

[0127] Examples of compounds represented by the above formula (1d) include 4-aminophenol, 2-amino-6-hydroxynaphthalene, and their positional isomers and derivatives.

[0128] Furthermore, the reaction can be carried out in the presence of a solvent. The same solvent used in step [1-1] can be used as the solvent. The reaction temperature is, for example, around 100–200°C.

[0129] The aforementioned cyclic anhydrides are preferably compounds represented by formula (a) below. Particularly preferred are those containing R. 3 and R 4 Compounds containing hydrogen atoms (i.e., maleic anhydride).

[0130] [Chemical Formula 16]

[0131] (In the formula, Q and R) 3 ~R 6 With Q and R in the above equation (r-1) 3 ~R 6 same.)

[0132] The compounds having the acetamide structure described above are preferably those shown in formula (b) below.

[0133] [Chemical Formula 17]

[0134] (where R) 9 and R 10 R in the above equation (r-2) 9 and R 10 same.)

[0135] R 9 and R 10 R in the above equation (r-2) 9 and R 10 Correspondingly, R is particularly preferred. 9 and R 10 Compounds containing methyl groups (i.e., N,N-dimethylacetamide).

[0136] If the compound shown in formula (1') above is reacted with the cyclic anhydride in the presence of the compound having the acetamide structure above, the compound (1) above is obtained through an amide acid formation reaction, a ring-closing reaction, and a curing-promoting group formation reaction. The reaction is described in the case where the compound shown in formula (a) above (sometimes referred to as "compound (a)") is used as the cyclic anhydride above, and the compound shown in formula (b) above (sometimes referred to as "compound (b)") is used as the compound having the acetamide structure above. Only one of compound (a) and compound (b) may be used, or two or more may be used.

[0137] In the amide acid formation reaction, compound (a) reacts with the NH2 group, which is the terminal group of the compound shown in formula (1'), to generate the group shown in formula (r-4) (maleamic acid in this example). Then, in the ring-closing reaction, the group shown in formula (r-4) is dehydrated and converted into the group shown in formula (r-3) (maleimide ring in this example), with at least a portion of QQ being a double bond, through the ring-closing reaction. Subsequently, due to the generation of water in the system during the dehydration of the above ring-closing reaction, a portion of compound (b) undergoes hydrolysis through the water present in the system to generate acetic acid and an amine, which bonds to one carbon atom of the group shown in formula (r-3) constituting the above double bond, thereby generating a succinic imide group bonded with the above amino group.

[0138] The aforementioned amic acid formation reaction, ring-closure reaction, and curing-promoting group formation reaction can be carried out in two stages. The first stage is a reaction conducted at room temperature, and the second stage is a reaction conducted under heating and / or with a higher catalyst concentration than in the first stage. In the first stage, the amic acid formation reaction mainly occurs, while in the second stage, the ring-closure reaction mainly occurs. Alternatively, the ring-closure reaction can be carried out in the first stage, or the amic acid formation reaction can be carried out in the second stage. The curing-promoting group formation reaction is carried out in both the first and second stages.

[0139] In the first stage described above, the reaction of the compound (a) and compound (b) shown in formula (1') is carried out. This first stage can be carried out at room temperature (1–40°C). The reaction time is, for example, about 1–30 hours. Furthermore, this reaction can be carried out by any of the following methods: batch, semi-batch, continuous, etc.

[0140] The amount of compound (a) used in the first stage above is approximately 2.0 to 4.0 moles relative to 1 mole of the compound shown in formula (1') above.

[0141] The amount of compound (b) used in the first stage above is approximately 2.0 to 4.0 moles relative to 1 mole of the compound shown in formula (1') above.

[0142] The above reactions can be carried out in the presence of a solvent. Examples of solvents include: ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; amides such as formamide, acetamide, N-methyl-2-pyrrolidone (NMP), and N,N-dimethylformamide; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, trifluorotoluene, and hexafluoro-2-propanol; sulfoxides such as dimethyl sulfoxide (DMSO), diethyl sulfoxide, and benzylphenyl sulfoxide; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran (THF), dioxane, 1,2-dimethoxyethane, and cyclopentylmethyl ether; esters such as ethyl acetate; nitriles such as acetonitrile and benzonitrile; and aromatic hydrocarbons such as benzene, toluene, and xylene. Only one of the above solvents may be used, or two or more may be used.

[0143] As the solvent described above, from the viewpoint that the reaction with the compound having the acetamide structure is fully carried out at one end of the compound shown in the above formula (1'), a solvent with a boiling point higher than that of water is preferred, an aromatic hydrocarbon is more preferred, and benzene, toluene, or xylene is particularly preferred.

[0144] In the first stage of the reaction described above, a catalyst may be added. Adding a catalyst in the first stage of the reaction promotes the ring-closing reaction and dehydrates it, generating water in the system during the first stage reaction, and promoting the formation of the curing-promoting groups. Examples of catalysts that can be used in the second stage of the reaction described later are given and illustrated. Only one catalyst may be used, or two or more catalysts may be used.

[0145] The amount of acid catalyst used in the first stage above is, for example, 0.02 to 1.0 mol relative to 1 mole of the compound shown in formula (1'), preferably 0.05 to 0.5 mol, and particularly preferably 0.1 to 0.4 mol.

[0146] The amount of base catalyst used in the first stage above is, for example, 0.02 to 1.0 mol relative to 1 mole of the compound shown in formula (1'), preferably 0.02 to 0.5 mol, and particularly preferably 0.05 to 0.4 mol.

[0147] The catalyst concentration in the reaction system in the first stage described above is, for example, 0.003 to 0.10 mmol / g, preferably 0.005 to 0.07 mmol / g, and particularly preferably 0.007 to 0.04 mmol / g.

[0148] The second stage described above can be carried out by heating at a temperature above 200°C or by adding a catalyst.

[0149] From the perspective of suppressing the curing reaction and enabling ring-closing reactions, achieving a high ring-closing rate, and obtaining a curable compound with excellent storage stability in solution, the addition of a catalyst is preferred. Examples of such catalysts include base catalysts and acid catalysts. Among these catalysts, acid catalysts are preferred from the viewpoint of further suppressing side reactions. Only one type of catalyst may be used, or two or more may be used.

[0150] Examples of base catalysts include amine compounds and sodium acetate. Examples of acid catalysts include: inorganic acids such as hydrochloric acid, hydrogen bromide, hydrogen iodide, sulfuric acid, sulfuric anhydride, nitric acid, phosphoric acid, phosphorous acid, phosphotungstic acid, and phosphomolybdic acid; sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid; carboxylic acids such as acetic acid and oxalic acid; halocarboxylic acids such as chloroacetic acid, dichloroacetic acid, trichloroacetic acid, fluoroacetic acid, difluoroacetic acid, and trifluoroacetic acid; solid acids such as silica, alumina, and activated clay; and cation exchange resins. Preferably, the acid catalyst is selected from at least one group consisting of p-toluenesulfonic acid, methanesulfonic acid, sulfuric acid, and phosphoric acid.

[0151] The amount of the acid catalyst used in the second stage is, for example, 0.02 to 1.0 mol relative to 1 mole of the compound shown in formula (1'), preferably 0.05 to 0.5 mol, and particularly preferably 0.1 to 0.4 mol.

[0152] The amount of the base catalyst used in the second stage is, for example, 0.02 to 1.0 mol relative to 1 mole of the compound shown in formula (1'), preferably 0.02 to 0.5 mol, and particularly preferably 0.05 to 0.4 mol.

[0153] The catalyst concentration in the reaction system of the second stage described above is, for example, 0.003 to 0.10 mmol / g, preferably 0.005 to 0.07 mmol / g, and particularly preferably 0.007 to 0.04 mmol / g. If the catalyst concentration is 0.003 mmol or higher, the ring-closure rate of the solidified compound becomes higher, and it tends to have improved storage stability in solution.

[0154] If a catalyst was added in the first stage described above, an additional catalyst may be added in the second stage, or no catalyst may be added. Considering that some of the catalyst added in the first stage may be deactivated, it may be added in the amount or concentration described above.

[0155] Furthermore, in the second stage described above, compound (b) may be added. The amount of compound (b) used in the second stage described above is approximately 2.0 to 30.0 moles relative to 1 mole of the compound shown in formula (1') above.

[0156] In the second stage described above, to further promote the ring-closure reaction, it is preferable to rapidly remove the water produced as a byproduct of the reaction from the reaction system. Methods for removing the byproduct water include, for example, using a dehydrating agent such as a carboxylic anhydride, or using a solvent that azeotropically reacts with water. In this case, the removal efficiency may vary depending on the shape, volume, piping layout, and insulation conditions of the reaction vessel.

[0157] The above reaction is preferably confirmed by sampling to verify the ring closure rate, and stopped once it is confirmed that the reaction has proceeded sufficiently. After the reaction is complete, the resulting reaction product can be separated and purified by conventional precipitation, washing, and filtration.

[0158] [Curable Composition]

[0159] The above-described compound (1) can be used to obtain a curable composition. This disclosure provides a curable composition comprising the above-described compound (1). The above-described curable composition may contain only one of the above-described compounds (1), or it may contain two or more of the above-described compounds (1).

[0160] The curable composition described above preferably contains a compound represented by the following formula (2) (sometimes referred to as "compound (2)"). The curable composition containing compounds (1) and (2) has better solvent solubility and tends to cure at low temperatures in the presence of oxygen.

[0161] [Chemical Formula 18]

[0162] [In the formula, R] 11 and R 12 Same or different indicates a curable functional group having a cyclic imide structure. D 1 and D 2 "Same" or "different" indicates a single bond or a linking group. "L" represents a divalent group having repeating units comprising the structures shown in formula (I) and (II) above.

[0163] In equation (2), R 11 and R 12 Same or different indicates a curable functional group having a cyclic imide structure. R 11 The nitrogen atom in the cyclic imide structure and D 1 Bonding, R 12The nitrogen atom in the cyclic imide structure and D 2 Bonding. As R 11 and R 12 The curable functional groups with cyclic imide structures in the above formula (1) can be listed as R. 1 The preferred embodiment is the same, which is a group with a cyclic imide structure that is a curable functional group.

[0164] In equation (2), D 1 and D 2 The same or different indicates a single bond or a linking group. The preferred scheme is the same as D in formula (1). 1 and D 2 same.

[0165] In formula (2), L represents a divalent group having repeating units containing the structures shown in formula (I) and formula (II) above. The preferred scheme is the same as L in formula (1).

[0166] Compound (2) can be obtained as a mixture of compound (1) by manufacturing compound (1) using the same method as compound (1). That is, a mixture of compound (1) and compound (2) can be manufactured using the same method as compound (1). Furthermore, compound (2) can be a compound manufactured using known or conventional methods.

[0167] In the above-described curable composition, the presence ratio of compound (1) to compound (2) calculated by area ratio based on MS analysis [compound (1) / compound (2)] is preferably 0.08 or more, more preferably 0.1 or more, and even more preferably 0.13 or more. If the presence ratio is 0.08 or more, the curing start temperature tends to be lower. For example, the presence ratio is less than 1.

[0168] The content of compound (1) in the above-described curable composition is preferably 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more, relative to 100% by mass of the total amount of the curable composition. Furthermore, the content is, for example, 99% by mass or less, preferably 60% by mass or less, and more preferably 50% by mass or less. Moreover, when the above-described curable composition contains both compound (1) and compound (2), the total content of compound (1) and compound (2) is preferably within the above-described range.

[0169] The proportion of compound (1) in the curable composition is preferably 40% by mass or more, more preferably 80% by mass or more, further preferably 90% by mass or more, and particularly preferably 95% by mass or more, relative to 100% by mass of the total amount of solid components (e.g., the total amount of all components except the solvent) in the curable composition. Furthermore, when the curable composition contains both compound (1) and compound (2), it is preferable that the combined proportion of compound (1) and compound (2) is within the above-mentioned range.

[0170] The above-described curable composition may also contain a solvent. Known or conventional organic solvents may be used as the solvent, without particular limitation, and examples include: chain ketones such as methyl ethyl ketone and methyl isobutyl ketone; cyclic ketones such as cyclopentanone and cyclohexanone; amides such as formamide, acetamide, N-methyl-2-pyrrolidone (NMP), N,N-dimethylformamide, and N,N-dimethylacetamide (DMAc); halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, trifluorotoluene, and hexafluoro-2-propanol; sulfoxides such as dimethyl sulfoxide (DMSO), diethyl sulfoxide, and benzylphenyl sulfoxide; tetrahydrofuran (THF); aromatic hydrocarbons such as benzene, toluene, and xylene; and ethers such as anisole. Only one of the above solvents may be used, or two or more may be used.

[0171] As the solvent, from the viewpoint of being able to suppress the curing reaction of compound (1) and compound (2) and making the solvent easy to volatilize, a solvent with a large difference between the exothermic onset temperature of compound (1) and compound (2) and the boiling point (= boiling point under normal pressure) of the solvent is preferred.

[0172] As the solvents described above, from the viewpoint of the excellent solubility of compounds (1) and (2), aromatic hydrocarbons and ethers are preferred, toluene and anisole are more preferred, and toluene is even more preferred.

[0173] The curable composition described above may contain other components besides those listed above. These other components may include known or commonly used additives, such as: curable compounds other than compounds (1) and (2), curing agents, curing accelerators, catalysts, fillers, organic resins (silicone resins, epoxy resins, fluororesins, etc.), stabilizers (antioxidants, UV absorbers, light stabilizers, heat stabilizers, etc.), flame retardants (phosphorus flame retardants, halogen flame retardants, inorganic flame retardants, etc.), flame retardant additives, reinforcing materials, nucleating agents, coupling agents, lubricants, waxes, plasticizers, release agents, impact modifiers, hue modifiers, flow modifiers, colorants (dyes, pigments, etc.), dispersants, defoamers, deaerators, antibacterial agents, preservatives, viscosity modifiers, thickeners, crosslinking agents, etc. Only one of these other components may be used, or two or more may be used.

[0174] The above-described curable composition can begin to cure in the presence of oxygen and at low temperatures even without the use of a curing agent and a curing accelerator. Therefore, the content of the curing agent and / or curing accelerator in the above-described curable composition is preferably less than 1% by mass, more preferably less than 0.1% by mass, even more preferably less than 0.07% by mass, and particularly preferably less than 0.01% by mass, relative to 100 parts by mass of the total amount of the above-described compound (1) (or compound (1) and compound (2)). Furthermore, the content of the above-described curing agent and / or curing accelerator is preferably less than 0.1 parts by mass, more preferably less than 0.08 parts by mass, and even more preferably less than 0.03 parts by mass, relative to 100 parts by mass of the total amount of the above-described compound (1) (or compound (1) and compound (2)).

[0175] Examples of polymerization initiators include free radical polymerization initiators. Examples of free radical polymerization initiators include photoradical polymerization initiators and thermal free radical polymerization initiators. Only one of the above polymerization initiators may be used, or two or more may be used.

[0176] Examples of photoradical polymerization initiators include: benzophenone, benzyl acetophenone, benzyl dimethyl ketone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, dimethoxyacetophenone, dimethoxyphenylacetophenone, diethoxyacetophenone, diphenyl disulfide, methyl benzoyl benzoate, ethyl 4-dimethylaminobenzoate, 2,4-diethylthioxanthone, 2-methyl-1-[4-(methyl)phenyl]-2-morpholinoacetone-1, 1-hydroxycyclohexylphenyl ketone, 2-dimethylamino-2-(4-morpholino)benzoyl-1-phenylpropane, etc., and 2-amino-2-benzoyl-1-phenylpropane. Benzene compounds, including phenylalanine compounds, tetra(tert-butylperoxycarbonyl)benzophenone, benzoin, 2-hydroxy-2-methyl-1-phenyl-propane-1-one, 4,4'-bis(diethylamino)benzophenone and other aminobenzene derivatives, 2,2'-bis(2-chlorophenyl)-4,5,4',5'-tetraphenyl-1,2'-biimidazole and other imidazole compounds, 2,6-bis(trichloromethyl)-4-(4-methoxynaphthyl-1-yl)-1,3,5-triazine and other halomethyltriazine compounds, 2-trichloromethyl-5-(2-benzofuran-2-yl-vinyl)-1,3,4-oxadiazole and other halomethyloxadiazole compounds, etc. In addition, photosensitizers can be added as needed.

[0177] Examples of thermal free radical polymerization initiators include azo compounds such as azobisisobutyronitrile (AIBN) and organic peroxides. Examples of the aforementioned organic peroxides include: hydroperoxides, dialkyl peroxides, peroxide esters, diacyl peroxides, peroxydicarbonate, peroxyketal, ketal peroxides, etc. (specifically, benzoyl peroxide, tert-butyl peroxide-2-ethylhexanoate, 2,5-dimethyl-2,5-di(2-ethylhexanoyl)peroxide, tert-butyl peroxide, tert-butyl peroxide, cumene hydroperoxide, dicumene peroxide, di-tert-butyl peroxide, 2,5-dimethyl-2,5-dibutyl peroxide, 2,4-dichlorobenzoyl peroxide, 1,4-di(2-tert-butylperoxide isopropyl)benzene, 1,1-bis(tert-butylperoxide)-3,3,5-trimethylcyclohexane, methyl ethyl ketone peroxide, 1,1,3,3-tetramethyl butyl peroxide-2-ethylhexanoate, etc.).

[0178] The above-described curable composition can be cured at low temperatures even without the use of a polymerization initiator. Therefore, the content of the polymerization initiator in the above-described curable composition, relative to 100 parts by mass of compound (1) (or the total amount of compound (1) and compound (2)), can be 2 parts by mass or less, or 1 part by mass or less, 0.5 parts by mass or less, 0.1 parts by mass or less, or 0.02 parts by mass or less.

[0179] The above-mentioned curable composition preferably exhibits no precipitates or insolubles at 60°C. Furthermore, it is particularly preferred that it exhibits no precipitates or insolubles at room temperature (e.g., 25°C).

[0180] The above-described curable composition preferably begins to cure in the presence of oxygen at a temperature below 320°C (preferably below 300°C, more preferably below 240°C, and even more preferably below 230°C). That is, the exothermic initiation temperature is preferably within the above-described range.

[0181] The above-described curable composition can be cured in the presence of oxygen at low temperatures. Therefore, from the perspectives of equipment and production efficiency for curing the above-described curable composition, it has a wide range of applications and can be used in various situations. Furthermore, even when the above-described curable composition is cured in contact with metal substrates such as copper, the quality of the cured product (dielectric constant, glass transition temperature, flexibility, adhesion, etc.) is not easily unstable. Therefore, the above-described curable composition is not limited to the type of substrate to which it is applied and can be coated on a variety of substrates.

[0182] The above-mentioned curable composition can be prepared by mixing the above components and heating and stirring at a temperature of, for example, below 80°C, preferably at room temperature (around 25°C to 80°C), and particularly preferably at 50 to 70°C.

[0183] [Cured Product]

[0184] The above-described curable composition is cured by reacting the compounds (1) with each other through heat treatment, thereby forming a cured product. Furthermore, when the above-described curable composition contains both compounds (1) and (2), curing can also be achieved through reactions between compounds (1), between compounds (1) and (2), and / or between compounds (2). Additionally, a drying process to evaporate the solvent can be performed before the heat treatment. Furthermore, the heat treatment can be performed at atmospheric pressure, under reduced pressure, or under increased pressure. Furthermore, the heat treatment can also be performed in an inert gas atmosphere such as nitrogen or argon, but since the above-described curable composition cures sufficiently even in the presence of oxygen, it is preferable to perform the treatment in an air atmosphere, such as in the presence of oxygen.

[0185] The heat treatment temperature is not particularly limited, but from the viewpoint that the above-mentioned curable composition can be cured at low temperatures, it is preferably below 320°C (e.g., 60–320°C), more preferably below 300°C (e.g., 80–300°C), even more preferably below 240°C (e.g., 100–240°C), and particularly preferably below 230°C (e.g., 120–230°C). It should be noted that heating can be performed while maintaining a constant temperature or by changing the temperature in stages. The heating temperature can be adjusted appropriately according to the heating time. The heating method is not particularly limited, and known or conventional methods can be used.

[0186] Furthermore, the curing reaction of the aforementioned curable composition may be temporarily halted midway through the process, forming a semi-cured product (Stage B). The semi-cured product temporarily exhibits fluidity upon heating, adapting to the aforementioned height differences of the substrate. Moreover, further heat treatment can form a cured product with superior heat resistance, flame retardancy, and excellent dielectric properties.

[0187] The degree of curing of the above-mentioned semi-cured material is, for example, 85% or less (for example, 10% to 85%, particularly preferably 15% to 75%, and even more preferably 20% to 70%).

[0188] It should be noted that the degree of curing of the semi-cured material can be determined by DSC, which measures the heat release of the cured composition before curing (uncured) and the heat release of its semi-cured material, and is calculated according to the following formula.

[0189] Degree of curing (%) = [1 - (Heat release of semi-cured material / Heat release of uncured curable composition)] × 100

[0190] The glass transition temperature (Tg) of the cured product is preferably 150°C or higher, more preferably 160°C or higher, and even more preferably 170°C or higher. If the glass transition temperature is 150°C or higher, the heat resistance of the cured product is even better. The glass transition temperature can be determined by DSC measurement.

[0191] The cured product of the above-mentioned curable composition exhibits excellent heat resistance, with a 5% weight reduction temperature (Tw) measured at a heating rate of 10°C / min (in nitrogen). d5 For example, the temperature is 300°C or higher, preferably 400°C or higher, more preferably 430°C or higher, and even more preferably 450°C or higher. 5% weight reduction temperature (T) d5 The upper limit for the temperature is, for example, 600°C, preferably 550°C, and particularly preferably 530°C. It should be noted that the 5% weight loss temperature can be determined by TG / DTA (which simultaneously measures differential thermal analysis and thermogravimetric analysis).

[0192] Therefore, the above-mentioned curable composition is molded by a known and conventional molding method, and then subjected to heat treatment (if drying is performed as needed), thereby producing a molded body composed of a cured or semi-cured product of the above-mentioned curable composition.

[0193] The aforementioned curable compositions are preferably used as molding materials, shielding materials, conductive materials (e.g., thermally conductive materials), insulating materials, and adhesives (e.g., heat-resistant adhesives) for composite materials (fiber-reinforced plastics, prepregs, etc.) used in harsh environmental temperature conditions in electronic information equipment, home appliances, automobiles, precision machinery, aircraft, aerospace industry equipment, and energy fields (oilfield excavation pipelines / pipes, fuel containers, etc.). In addition, it can be preferentially used as an encapsulant, coating, ink, sealant, resist, molding material, forming material [for automotive parts such as thrust washers, oil filters, seals, bearings, gears, cylinder head covers, bearing cages, intake manifolds, pedals, etc.; substrates, electrical insulating materials (insulating films, etc.), laminates, electronic paper, touch panels, solar cell substrates, optical waveguides, light guide plates, holographic memories, silicon wafer carriers, IC chip trays, electrolytic capacitor trays, insulating films, etc. for semiconductor / liquid crystal manufacturing equipment; optical components such as lenses; compressor components such as pumps, valves, seals, etc.; aircraft cabin interior components; medical device components such as sterilization equipment, columns, piping, etc.; food / beverage manufacturing equipment components; and forming materials for electrical / electronic equipment, such as housings for personal computers, mobile phones, etc., and keyboard supports that support the keyboard inside a personal computer].

[0194] [Molded Article]

[0195] By molding the above-described curable composition and drying it as needed, the solidified product of the above-described curable composition can be given a desired shape, resulting in a molded body composed of the solidified product. The molded body composed of the solidified product temporarily exhibits fluidity or adhesiveness upon heating, allowing for secondary molding and bonding to other components. Furthermore, if the solidified product with the desired shape is heat-treated, a molded body composed of a cured or semi-cured product of the above-described curable composition is obtained. It should be noted that the shape of the molded body is not particularly limited, and the shape can be appropriately selected according to the application.

[0196] The various solutions disclosed in this specification can also be combined with any other features disclosed in this specification. The various configurations and combinations of configurations in each embodiment are merely examples, and appropriate additions, omissions, substitutions, and other modifications to the configurations can be made without departing from the spirit of this disclosure. Furthermore, the inventions of this disclosure are not limited to the embodiments or the following examples, but only to the claims.

[0197] Examples

[0198] The following describes one embodiment of the present disclosure in more detail based on examples, but the present disclosure is not limited to these examples.

[0199] Example 1

[0200] [Preparation of Curable Composition]

[0201] (Step 1-1)

[0202] 40.3 g of 4,4'-difluorobenzophenone (DFBP), 35.1 g of bisphenol A (BisA), 41.2 g of anhydrous potassium carbonate (K2CO3), 187.2 g of N,N-dimethylacetamide (DMAc), and 18.7 g of toluene (Tol) were added to a reactor equipped with a stirring device, a nitrogen inlet pipe, and a Dean-Stark apparatus. The mixture was stirred and heated under a nitrogen atmosphere at 140–150 °C for 10 hours under toluene reflux, and then allowed to return to room temperature.

[0203] (Step 1-2)

[0204] Next, 7.4 g of 4-aminophenol (4-AP) was added to the reactor containing the reaction products. The mixture was then heated under a nitrogen atmosphere with stirring, and refluxed with toluene at 140–150 °C for 10 hours, followed by a return to room temperature. Then, 18.7 g of N,N-dimethylacetamide (DMAc) and 56.2 g of toluene (Tol) were added to the filtered crude reaction solution to obtain diamine-1 (a liquid containing compounds represented by the following formula). It should be noted that m is the average degree of polymerization of the repeating unit.

[0205] [Chemical Formula 19]

[0206] (Step 2)

[0207] 320.5 g of the diamine solution obtained in steps 1-2, 10.4 g of maleic anhydride (MAH), and 118.5 g of N,N-dimethylacetamide (DMAc) were added to a reactor equipped with a stirrer, a nitrogen inlet pipe, and a Dean-Stark apparatus. After stirring at room temperature under a nitrogen atmosphere for 1 hour, the temperature was raised to 140–150 °C to allow toluene to reflux, thus establishing a toluene reflux state. Then, p-toluenesulfonic acid monohydrate (pTSA) was added as a catalyst over a period of 1 hour. A mixed solution of 1.3 g of 1H₂O, 11.3 g of N,N-dimethylacetamide (DMAc), and 4.0 g of toluene (Tol) was prepared and stirred continuously for 10 hours, allowing the toluene to reflux and remove moisture. After the reaction solution was brought to room temperature, it was added to 3000 mL of methanol to obtain a powdered solid. The powdered solid was repeatedly washed with methanol and water and then dried under reduced pressure at 80 °C overnight to obtain 65.2 g of a mixture (curable composition) of compound (1-1) (containing the compound shown in formula (1-1) and the compound shown in formula (2-1) below) and compound (2-1) (containing the compound shown in formula (2-1) below). It should be noted that m in formulas (1-1) and (2-1) below represents the average degree of polymerization of the repeating unit.

[0208] [Chemical Formula 20]

[0209] Example 2

[0210] [Preparation of Curable Composition]

[0211] Add 319.2 g of the diamine solution obtained in steps 1-2 of Example 1, 10.4 g of maleic anhydride (MAH), 21.6 g of N,N-dimethylacetamide (DMAc), 3.9 g of toluene (Tol), and p-toluenesulfonic acid monohydrate (pTSA) as a catalyst to a reactor equipped with a stirring device, a nitrogen inlet pipe, and a Dean-Stark apparatus. 1.3 g of 1H₂O was stirred at room temperature for 3 hours under a nitrogen atmosphere. Then, the temperature was raised to 130–140 °C to form a toluene reflux state, and stirring was continued for 10 hours to remove moisture. After the reaction solution was allowed to return to room temperature, it was added to 3000 mL of methanol to obtain a powdered solid. This powdered solid was repeatedly washed with methanol and water, and then dried under reduced pressure at 80 °C overnight to obtain 62.8 g of a mixture (curable composition) of the above compounds (1-1) and (2-1).

[0212] Example 3

[0213] [Preparation of Curable Composition]

[0214] Add 322.2 g of the diamine solution obtained in steps 1-2 of Example 1, 10.4 g of maleic anhydride (MAH), 129.8 g of N,N-dimethylacetamide (DMAc), 4.0 g of toluene (Tol), and p-toluenesulfonic acid monohydrate (pTSA) as a catalyst to a reactor equipped with a stirring device, a nitrogen inlet pipe, and a Dean-Stark apparatus. 1.3 g of 1H₂O was stirred at room temperature under a nitrogen atmosphere for 3 hours. Then, the temperature was raised to 140–150 °C to form a toluene reflux state, and stirring was continued for 10 hours to remove moisture. After the reaction solution was allowed to return to room temperature, it was added to 3000 mL of methanol to obtain a powdered solid. This powdered solid was repeatedly washed with methanol and water, and then dried under reduced pressure at 80 °C overnight to obtain 63.4 g of a mixture (curable composition) of the above compounds (1-1) and (2-1).

[0215] Example 4

[0216] [Preparation of Curable Composition]

[0217] 49.70 g of the diamine solution obtained in steps 1-2 of Example 1, 10.4 g of maleic anhydride (MAH), and 10.4 g of N,N-dimethylacetamide (DMAc) were added to a reactor equipped with a stirrer, a nitrogen inlet pipe, and a Dean-Stark apparatus. After stirring at room temperature under a nitrogen atmosphere for 1 hour, the temperature was raised to 130-140°C to reflux toluene, forming a toluene reflux state. Then, p-toluenesulfonic acid monohydrate (pTSA) was added as a catalyst over a period of 1 hour. A mixed solution of 1.3 g of 1H₂O, 11.3 g of N,N-dimethylacetamide (DMAc), and 4.0 g of toluene (Tol) was stirred continuously for 10 hours, allowing the toluene to reflux and remove moisture. After the reaction solution was brought to room temperature, it was added to 3000 mL of methanol to obtain a powdered solid. The powdered solid was repeatedly washed with methanol and water and then dried under reduced pressure at 80 °C overnight to obtain 64.4 g of a mixture (curable composition) of compound (1-1) (containing the compound shown in formula (1-1) above and the compound shown in formula (2-1) below) and compound (2-1) (containing the compound shown in formula (2-1) above).

[0218] 5.0 g of the above-mentioned curable composition, 5.0 g of toluene as a solvent, and 0.05 g of PERCUMYL D (trade name "PERCUMYL D", manufactured by Nippon Yu Corporation), a free radical generator, as a curing accelerator, were mixed and allowed to stand at room temperature under atmospheric conditions for 8 hours to obtain a homogeneous solution. The obtained solution was coated onto a glass plate with a thickness of 0.10 mm and then dried at 120°C for 0.5 hours to obtain the curable composition.

[0219] Example 5

[0220] [Preparation of Curable Composition]

[0221] 5.0 g of the curable composition obtained in Example 4, 5.0 g of anisole as a solvent, and 0.05 g of 1B2PZ (1-benzyl-2-phenylimidazolium, manufactured by Shikoku Kasei Corporation) as a curing accelerator were mixed and allowed to stand at room temperature under atmospheric conditions for 8 hours to obtain a homogeneous solution. The obtained solution was coated onto a glass plate with a thickness of 0.10 mm and then dried at 150°C for 0.5 hours to obtain the curable composition.

[0222] Example 6

[0223] [Preparation of Curable Composition]

[0224] As a curing accelerator, an organic nucleophile, 2E4MZ (2-ethyl-4-methylimidazole, manufactured by Shikoku Chemical Industry Co., Ltd.), was used. Otherwise, the curable composition was obtained in the same manner as in Example 5.

[0225] Comparative Example 1

[0226] [Preparation of Curable Composition]

[0227] (Step 1-1)

[0228] 37.25 g of 4,4'-difluorobenzophenone (DFBP), 32.48 g of bisphenol A (BisA), 29.50 g of anhydrous potassium carbonate (K₂CO₃), 214.4 g of N-methylpyrrolidone (NMP), and 90.4 g of toluene (Tol) were added to a reactor equipped with a stirrer, a nitrogen inlet pipe, and a Dean-Stark apparatus. The mixture was heated under a nitrogen atmosphere with stirring, and the toluene was refluxed at 130–140 °C for 4 hours. Subsequently, the mixture was further heated, and the toluene was removed by distillation at 170–180 °C. Then, the mixture was stirred continuously at 170–180 °C for 10 hours, and then allowed to return to room temperature.

[0229] (Step 1-2)

[0230] Subsequently, 6.520 g of 4-aminophenol (4-AP), 8.260 g of anhydrous potassium carbonate (K₂CO₃), 27.9 g of N-methylpyrrolidone (NMP), and 117.4 g of toluene (Tol) were added to the reactor containing the reaction products. The mixture was then heated again under a nitrogen atmosphere with stirring, and the toluene was refluxed at 130–140 °C for 3 hours. Afterward, the mixture was heated, and the toluene was removed by distillation at 170–180 °C. The temperature was maintained at the above level, and stirring was continued for 4 hours. The mixture was then cooled to room temperature, and the reaction solution was added to 3000 mL of methanol. The mixture was filtered to obtain a powdered solid. This powdered solid was repeatedly washed with methanol and water, and then dried under reduced pressure at 80 °C overnight to obtain a powdered solid of diamine-1 (the compound shown in the above formula).

[0231] (Step 2)

[0232] 49.70 g of diamine-1, 6.03 g of maleic anhydride (MAH), 316.0 g of N-methylpyrrolidone (NMP), and 178.3 g of toluene (Tol) obtained in step 1 were added to a reactor equipped with a stirrer, a nitrogen inlet pipe, and a Dean-Stark apparatus. The mixture was stirred at room temperature under a nitrogen atmosphere for 5 hours. Then, 1.1 g of p-toluenesulfonic acid (pTSA) as a catalyst was added, and the mixture was heated to 140°C and stirred continuously for 8 hours, allowing the toluene to reflux and remove moisture. After the reaction mixture was allowed to return to room temperature, it was added to 3000 mL of methanol, thereby obtaining a powdered solid. This powdered solid was repeatedly washed with methanol and water, and then dried under reduced pressure at 80°C overnight to obtain 48.8 g of a cured composition containing the compound shown in formula (1-1) above.

[0233] Example 7

[0234] [Preparation of Cured Product]

[0235] The curable compositions obtained in Examples 1-6 were mixed with an equal weight of anisole and allowed to stand at room temperature under atmospheric conditions for 8 hours to obtain a homogeneous solution. The resulting solution was coated onto a substrate with a thickness of 0.10 mm, and then heated at 250°C for 2 hours for drying and curing to obtain a cured product. It should be noted that the 250°C, 2-hour heating was performed under a nitrogen atmosphere when a free radical generating agent was used as a curing accelerator. The 250°C, 2-hour heating was performed under atmospheric conditions when an organic nucleophile was used as a curing accelerator, and when no curing accelerator was used. Furthermore, as substrates, glass plates (commercially available float glass, 4 mm thick), aluminum foil (trade name "Aluminium Tough Sheet", 200 mm square, manufactured by AS ONE Co., Ltd.), or copper plates (commercially available oxygen-free copper, 1 mm thick) were used.

[0236] <Evaluation>

[0237] The curable compositions prepared in the examples and comparative examples were evaluated as follows.

[0238] (1) Ring-closing rate

[0239] For curable compositions, according to 1 The loop closure rate is calculated using the integrated intensity of the H-NMR spectrum signal and the above formula.

[0240] It should be noted that the NMR measurements were performed under the following conditions.

[0241] <NMR Measurement>

[0242] Measurement apparatus: JEOL ECA500 or BRUKER AVANCE 600MHz.

[0243] Determination solvent: deuterated DMSO, deuterated chloroform, or a mixture of deuterated chloroform / pentafluorophenol = 2 / 1 (wt / wt).

[0244] Chemical shift: based on TMS.

[0245] (2) Exothermic onset temperature, glass transition temperature

[0246] DSC (Digital Subtraction Angiography) was performed on the curable composition. The intersection of the baseline of the temperature history curve obtained from the DSC measurement and the tangent at the inflection point of the exothermic peak was then taken as the exothermic onset temperature. Furthermore, for a second DSC measurement of a cured product cured at the first temperature rise during the DSC measurement, the inflection point of the temperature history curve obtained at the second temperature rise, located below the exothermic onset temperature, was taken as the glass transition temperature. Alternatively, if the exothermic peak could not be observed, the inflection point within the measured temperature range was taken as the glass transition temperature.

[0247] It should be noted that the measurement was performed under the following conditions.

[0248] <DSC Measurement>

[0249] Device: Q2000 (manufactured by TA Instruments).

[0250] Heating rate: 20℃ / min.

[0251] Atmosphere: Nitrogen atmosphere.

[0252] Measurement temperature range: 30~450℃.

[0253] (3) Liquid chromatography / mass spectrometry

[0254] For the cured composition, the area ratio of peak A (HPLC elution time: 15.5 min, MS mass-to-charge ratio: 1008 m / z) to peak B (HPLC elution time: 17.7 min, MS mass-to-charge ratio: 963 m / z) was determined by liquid chromatography / mass spectrometry (LC / MS) [area value of peak A / area value of peak B]. It should be noted that peak A represents compound (1-1), and peak B represents compound (2-1).

[0255] It should be noted that the measurement was performed under the following conditions.

[0256] <LC / MS Measurement>

[0257] Apparatus: Waters UPLC H-Class Plus / Xevo G2-X2 Qtof.

[0258] Column: Intersil ODS-3 (4.6×250×5).

[0259] Eluent: (A) H2O (B) ACN / THF = 40 / 60 v / v (at steady state, (A) / (B) = 30 / 70 v / v, during separation, only (B) is used).

[0260] Flow rate: 0.4 mL / min.

[0261] Temperature: 40℃.

[0262] Detectors: PDA (210–400 nm), MS (m / z 150–3000).

[0263] Sample concentration: 1 mg / mL.

[0264] [Table 1]

[0265] As shown in Table 1, it was confirmed that the curable composition of the examples had a lower exothermic onset temperature in the presence of oxygen compared with the curable composition of Comparative Example 1. Furthermore, the glass transition temperature of the cured product was also the same as that of the cured product of the curable composition of Comparative Example 1.

[0266] The following describes variations of the invention disclosed herein.

[0267] [Note 1] A curable compound, which is represented by the following formula (1).

[0268] [Chemical Formula 1]

[0269] [In the formula, R] 1 R represents a curable functional group having a cyclic imide structure. 2 This refers to a functional group that has a succinimide structure and promotes the curing of the curable functional group. (D) 1 and D 2 "Identical" or "different" indicates a single bond or a linking group. "L" represents a divalent group having repeating units comprising the structures shown in formula (I) and (II) below.

[0270] [Chemical Formula 2]

[0271] (In the formula, Ar) 1 ~Ar 3"Same" or "different" indicates a group formed by removing two hydrogen atoms from the structural formula of an aromatic ring, or a group formed by removing two hydrogen atoms from the structural formula of two or more aromatic rings bonded together by single bonds or connecting groups. X represents -CO-, -S-, or -SO2-. "Same" or "different" Y represents -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. n represents an integer greater than or equal to 0.

[0272] [Note 2] According to the curable compound described in Note 1, wherein the R 2 The group represented by the following formula (r-2) is indicated.

[0273] [Chemical Formula 6]

[0274] (where R) 7 ~R 10 Same or different indicates a hydrocarbon group. R 9 and R 10 They can optionally bond together to form a loop. The bonds with wavy lines in the formula are connected to D. 2 (Bonding.)

[0275] [Note 3] According to the curable compound of Note 2, wherein the group represented by formula (r-2) is the group represented by the following formula (r-2').

[0276] [Chemical Formula 7]

[0277] (where R) 9’ and R 10’ (Identical or different, indicating saturated or unsaturated aliphatic hydrocarbon groups with 1 to 6 carbon atoms.)

[0278] [Note 4] The curable compound according to any one of Notes 1 to 3, wherein the R 1 The group represented by the following formula (r-1) is indicated.

[0279] [Chemical Formula 3]

[0280] [In the formula, Q represents C or CH. The two Qs in the formula are bonded together via a single bond or a double bond. R] 3 ~R 6 Same or different, indicating a hydrogen atom or a hydrocarbon group. R 3 and R 4 They can optionally bond together to form a ring. n' represents an integer greater than 0. The bonds with tildes in the formula are connected to D. 1 Bonding.

[0281] [Note 5] According to the curable compound described in Note 4, wherein, in the formula (r-1), R 3 and R 4 They bond with each other and together with adjacent carbon atoms, form alicyclic rings with 3 to 20 carbon atoms.

[0282] [Note 6] According to the curable compound described in Note 4, wherein, in the formula (r-1), R 3 and R 4 They bond with each other and together with adjacent carbon atoms, form aromatic rings with 6 to 14 carbon atoms.

[0283] [Note 7] According to the curable compound of Note 4, the group represented by formula (r-1) is selected from the groups represented by formulas (r-1-1) to (r-1-6) below.

[0284] [Chemical Formula 4]

[0285] (The bond extending from the nitrogen atom in the formula is the same as the D in formula (1)) 1 (Bonding.)

[0286] [Appendix 8] The curable compound according to any one of Appendices 1 to 7, wherein, in formula (1), D 1 and D 2 It is a group containing a divalent aromatic hydrocarbon group.

[0287] [Note 9] The curable compound according to any one of Notes 1 to 8, wherein D 1 and D 2 Whether the groups are the same or different, they are groups selected from those shown in formulas (d-1) to (d-4) below.

[0288] [Chemical Formula 8]

[0289] [Note 10] The curable compound according to any one of Notes 1 to 9, wherein R is the compound of formula (1). 1 -D 1 - group, which is a group represented by the following formula (rd-1'-1) or (rd-1'-2).

[0290] [Chemical Formula 9]

[0291] (In the formula, Q and R) 3 and R 4 Together with the adjacent carbon atom, it represents an alicyclic ring with 3 to 20 carbon atoms or an aromatic ring with 6 to 14 carbon atoms.

[0292] [Note 11] The curable compound according to any one of Notes 1 to 10, wherein R is the compound of formula (1). 2 -D 2 - group, which is a group represented by the following formula (rd-2'-1) or (rd-2'-2).

[0293] [Chemical Formula 10]

[0294] (where R) 9’ and R 10’ (Identical or different, indicating saturated or unsaturated aliphatic hydrocarbon groups with 1 to 6 carbon atoms.)

[0295] [Appendix 12] The curable compound according to any one of Appendices 1 to 11, wherein, as Ar 1 ~Ar 3 The same or different indicates a group selected from the groups shown in formulas (a-1) to (a-5) below.

[0296] [Chemical Formula 11]

[0297] [Note 13] The curable compound according to any one of Notes 1 to 12, wherein L in formula (1) is a divalent group as shown in formula (L-1-1) or (L-1-2).

[0298] [Chemical Formula 12]

[0299] (In the above formula, m1 and m2 represent the range of 2 to 50.)

[0300] [Note 14] The curable compound according to any one of Notes 1 to 13, wherein the number average molecular weight of compound (1) is 1,000 to 15,000.

[0301] [Note 15] The curable compound according to any one of Notes 1 to 14, wherein the weight-average molecular weight of compound (1) is 1,000 to 45,000.

[0302] [Note 16] The curable compound according to any one of Notes 1 to 15, wherein the solubility of compound (1) is more than 1 g relative to 100 g of solvent at 23°C.

[0303] [Note 17] A curable composition comprising a curable compound according to any one of Notes 1 to 16 and a compound represented by the following formula (2).

[0304] [Chemical Formula 18]

[0305] [In the formula, R] 11 and R 12 Same or different indicates a curable functional group having a cyclic imide structure. D 1 and D 2 "Identical" or "different" indicates a single bond or a linking group. "L" represents a divalent group having repeating units comprising the structures shown in formula (I) and (II) below.

[0306] [Chemical Formula 2]

[0307] (In the formula, Ar) 1 ~Ar 3 "Same" or "different" indicates a group formed by removing two hydrogen atoms from the structural formula of an aromatic ring, or a group formed by removing two hydrogen atoms from the structural formula of two or more aromatic rings bonded together by single bonds or connecting groups. X represents -CO-, -S-, or -SO2-. "Same" or "different" Y represents -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. n represents an integer greater than or equal to 0.

[0308] [Note 18] According to the curable composition of Note 17, the presence ratio of the compound of formula (1) to the compound of formula (2) calculated by the area ratio based on MS analysis [compound of formula (1) / compound of formula (2)] is 0.08 or more.

[0309] [Note 19] According to Note 17 or 18, the curable composition contains the compound (1) in a proportion of 10% by mass or more relative to the total amount of the curable composition (100% by mass).

[0310] [Note 20] The curable composition according to any one of Notes 17 to 19, wherein the content of the above compound (1) is 40% by mass or more relative to the total amount of solid components in the curable composition (100% by mass).

[0311] [Note 21] The curable composition according to any one of Notes 17 to 20, wherein the curable composition further comprises a solvent.

[0312] [Note 22] The curable composition according to Note 21, wherein the curable composition contains toluene as the solvent.

[0313] [Appendix 23] A method for manufacturing a curable compound, which is a method for manufacturing a curable compound according to any one of Appendices 1 to 16, the method comprising: reacting a compound represented by the following formula (1') with a cyclic anhydride in the presence of a compound having an acetamide structure to obtain the compound represented by the following formula (1).

[0314] [Chemical Formula 14]

[0315] [In the formula, D] 1 and D 2 "Identical" or "different" indicates a single bond or a linking group. "L" represents a divalent group having repeating units comprising the structures shown in formula (I) and (II) below.

[0316] [Chemical Formula 2]

[0317] (In the formula, Ar) 1 ~Ar 3 "Same" or "different" indicates a group formed by removing two hydrogen atoms from the structural formula of an aromatic ring, or a group formed by removing two hydrogen atoms from the structural formula of two or more aromatic rings bonded together by single bonds or connecting groups. X represents -CO-, -S-, or -SO2-. "Same" or "different" Y represents -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. n represents an integer greater than or equal to 0.

Claims

1. A curable compound, represented by the following formula (1), [Chemical Formula 1] In the formula, R 1 R represents a curable functional group having a cyclic imide structure. 2 D represents a functional group having a succinimide structure and promoting the curing of the curable functional group. 1 and D 2 "Same" or "different" indicates a single bond or a linking group; "L" indicates a divalent group having repeating units comprising the structures shown in formula (I) and (II) below. [Chemical Formula 2] In the formula, Ar 1 ~Ar 3 Same or different indicates a group formed by removing two hydrogen atoms from the structure of an aromatic ring, or a group formed by removing two hydrogen atoms from the structure of two or more aromatic rings bonded by single bonds or connecting groups. X represents -CO-, -S-, or -SO2-. Y is the same or different, representing -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. n represents an integer greater than or equal to 0.

2. The curable compound according to claim 1, wherein, The R 2 Represents the group shown in the following formula (r-2), [Chemical Formula 6] In the formula, R 7 ~R 10 Same or different indicates hydrocarbon group, R 9 and R 10 They can optionally bond together to form a ring, and the wavy bond in equation (r-2) is connected to D. 2 Bonding.

3. The curable compound according to claim 1, wherein, The R 1 Represents the group shown in the following formula (r-1), [Chemical Formula 3] In the formula, Q represents C or CH, and the two Qs in formula (r-1) are bonded by a single or double bond, R 3 ~R 6 Same or different, indicating hydrogen atoms or hydrocarbon groups, R 3 and R 4 They are optionally bonded together to form a ring, where n' represents an integer greater than 0, and the wavy bond in equation (r-1) is connected to D. 1 Bonding.

4. The curable compound according to claim 3, wherein, The group represented by formula (r-1) is selected from the groups represented by formulas (r-1-1) to (r-1-6) below. [Chemical Formula 4] The bond extending from the nitrogen atom in the formula is related to the D in formula (1). 1 Bonding.

5. A curable composition comprising the curable compound according to any one of claims 1 to 4 and the compound represented by formula (2) below, [Chemical Formula 18] In the formula, R 11 and R 12 Same or different indicates a curable functional group having a cyclic imide structure, D 1 and D 2 "Same" or "different" indicates a single bond or a linking group; "L" indicates a divalent group having repeating units comprising the structures shown in formula (I) and (II) below. [Chemical Formula 2] In the formula, Ar 1 ~Ar 3 Same or different indicates a group formed by removing two hydrogen atoms from the structure of an aromatic ring, or a group formed by removing two hydrogen atoms from the structure of two or more aromatic rings bonded by single bonds or connecting groups. X represents -CO-, -S-, or -SO2-. Y is the same or different, representing -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. n represents an integer greater than or equal to 0.

6. The curable composition according to claim 5, wherein, The presence ratio of the compound shown in formula (1) to the compound shown in formula (2), calculated by the area ratio based on MS analysis, i.e., the ratio of the compound shown in formula (1) to the compound shown in formula (2), is 0.08 or higher.

7. A method for manufacturing a curable compound, which is a method for manufacturing a curable compound according to any one of claims 1 to 4, the method comprising: reacting a compound represented by the following formula (1') with a cyclic acid anhydride in the presence of a compound having an acetamide structure to obtain the compound represented by the following formula (1), [Chemical Formula 14] In the formula, D 1 and D 2 "Same" or "different" indicates a single bond or a linking group; "L" indicates a divalent group having repeating units comprising the structures shown in formula (I) and (II) below. [Chemical Formula 2] In the formula, Ar 1 ~Ar 3 Same or different indicates a group formed by removing two hydrogen atoms from the structure of an aromatic ring, or a group formed by removing two hydrogen atoms from the structure of two or more aromatic rings bonded by single bonds or connecting groups. X represents -CO-, -S-, or -SO2-. Y is the same or different, representing -S-, -SO2-, -O-, -CO-, -COO-, or -CONH-. n represents an integer greater than or equal to 0.

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