Resin composition, method for producing the same, and element and electronic device

Abstract

To provide a siloxane resin composition that has a small rate of change in viscosity over time and is easy to handle. [Solution] A resin composition containing an organosilicon compound having structures represented by formulas (A) and (B), wherein the proportion of structures represented by formula (B) where m=2 is greater than the proportion of structures represented by formula (B) where m=1. TIFF0007779433000036.tif71167

Description

[Technical Field]

[0001] The present invention relates to a resin composition, a method for producing the same, and an element and an electronic device. [Background technology]

[0002] Organosilicon compounds containing a silsesquioxane skeleton have a unique structure based on a siloxane bond (Si-O-Si) with high bond energy, and are expected to have unique effects due to this structure, which has attracted attention in various fields. Among such organosilicon compounds containing a silsesquioxane skeleton, silicon-based polymers containing a silsesquioxane skeleton in the main chain are known. These silicon-based polymers are particularly expected to be useful in applications such as semiconductor devices due to their excellent heat resistance and electrical insulation, lenses due to their excellent transparency, and adhesives due to their excellent adhesive properties, and studies are being conducted to further enhance their functionality. For example, Patent Document 1 discloses a silicon-based polymer that can form a silicone film with excellent heat resistance. Compositions using other components in addition to the silicon-based polymer have also been investigated, and Patent Document 2 discloses a composition that can form a cured product with excellent heat resistance by using a silicon-based polymer and a compound containing a specific element. Furthermore, Patent Document 3 discloses a technique for obtaining a laminate for semiconductor devices and the like having high electrical connection reliability by using a film obtained using a silicon-based polymer as an insulating film. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2010-116464 [Patent Document 2] International Publication No. 2022 / 215759 [Patent Document 3] International Publication No. 2021 / 261403 Summary of the Invention [Problem to be solved by the invention]

[0004] As mentioned above, organosilicon compounds containing a silsesquioxane skeleton have been studied mainly with a focus on their heat resistance, electrical insulation, and other properties in terms of their intended use. However, organosilicon compounds containing a silsesquioxane skeleton are hardly easy to handle, and when used in resin compositions containing such compounds, further improvements are needed in terms of ease of handling during production. One indicator of handleability is the rate of change in viscosity over time, but little research has been conducted on the rate of change in viscosity over time of resin compositions containing the above-mentioned organosilicon compounds, leaving room for further study. Therefore, an object of the present invention is to provide a resin composition that contains an organosilicon compound, has a small rate of viscosity change over time, and is easy to handle. [Means for solving the problem]

[0005] As a result of extensive research, the present inventors have found that the above-mentioned problems can be solved by controlling the number of two specific structures in the entire compound containing a specific silsesquioxane skeleton contained in a resin composition, and have completed the present invention.

[0006] That is, the gist of the present invention is as follows. Item 1. An organosilicon compound having a structure represented by the following formulas (A) and (B): The organosilicon compound is The proportion of the structure represented by the following formula (B) where m=2 is The proportion of the structure represented by the following formula (B) where m=1 is greater than the proportion of the structure represented by the following formula (B): Resin composition. [ka] (In the above formula (A), R 1 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; R2 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; In the above formula (B), R 3 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; m is an integer of 1 to 30; R 1 , R 2 , and R 3 When at least one of the above is an alkyl group having 1 to 40 carbon atoms, the alkyl group having 1 to 40 carbon atoms is independently selected from a group in which at least one hydrogen atom is independently replaced with a halogen atom, a cycloalkyl group A having 5 or 6 carbon atoms, 12 or an aryl group A having 6 to 20 carbon atoms 14 At least one -CH2- may be independently replaced by -O-, -CO-, or a cycloalkylene group A having 5 or 6 carbon atoms. 13 or an arylene group A having 6 to 20 carbon atoms 15 may be replaced by; R 1 , R 2 , and R 3 When at least one of the above is a cycloalkyl group having 5 or 6 carbon atoms, the cycloalkyl group having 5 or 6 carbon atoms is independently selected from the group consisting of at least one hydrogen atom independently replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, 21 , a cycloalkyl group A having 5 or 6 carbon atoms 22 or an aryl group A having 6 to 20 carbon atoms 24 wherein at least one -CH2- is independently replaced by -O- or -CO-; R 1 , R 2 , and R 3 When at least one of the above is an aryl group having 6 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms is independently selected from the group consisting of at least one hydrogen atom replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, 31 , a cycloalkyl group A having 5 or 6 carbon atoms 32or an aryl group A having 6 to 20 carbon atoms 34 may be replaced by; Alkyl group A 21 and alkyl group A 31 at least one hydrogen atom may be independently replaced by a halogen atom, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one -CH2- may be independently replaced by -O-, -CO-, a cycloalkylene group having 5 or 6 carbon atoms, or an arylene group having 6 to 20 carbon atoms; the cycloalkyl group A 12 , a cycloalkylene group A 13 , cycloalkyl group A 22 and a cycloalkyl group A 32 at least one hydrogen atom may be independently replaced by a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one -CH2- may be independently replaced by -O- or -CO-; an aryl group A 14 , an arylene group A 15 , an aryl group A 24 and an aryl group A 34 may independently replace at least one hydrogen atom with a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.)

[0007] Item 2. The organosilicon compound is a compound represented by the following formula (1): It contains at least a structure represented by the following formula (3): The proportion of the structure represented by the following formula (3) where n=2 is: The proportion of the structure represented by the following formula (3) where n = 1 is higher than that Item 1. The resin composition according to item 1. [ka] (In the above formula (1), X contains one or more structures represented by the above formula (2) and does not contain any structures other than the above structures; when X contains two or more structures represented by the above formula (2), the two or more structures may be the same or different; Y 1 is a single bond or a structure represented by the above formula (3); In the above formula (2), R 1 are independently R in formula (A). 1 is synonymous with ;R 2 are independently R in formula (A). 2 is synonymous with Y 2 is a single bond or a structure represented by the above formula (3), and the Y 1 may be the same as or different from; In the above formula (3), R 3 are independently R in formula (B). 3 and n is an integer of 1 to 30.

[0008] Item 3. The resin composition according to Item 1 or 2, further comprising a compound having a functional group capable of chemically bonding with the organosilicon compound. Item 4. The resin composition according to Item 3, wherein the compound having a functional group is a compound having two or more groups of one or more types selected from the groups represented by the following formulas (F-1) to (F-8): [ka] (In the above formulas (F-1) to (F-8), R 4 are independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group having 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group having 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; * represents a bonding site.

[0009] Item 5. The resin composition according to Item 4, wherein the compound having a functional group includes at least one silicon compound selected from the group consisting of hydrolyzable organosilane compounds represented by the following formula (10) and partial hydrolysis condensates of the hydrolyzable organosilane compounds: R 5 4-a SiZ a (10) (In the above formula (10), R 5 are independently an alkyl group having 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group having 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group having 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; Z is independently any of the groups represented by the formulae (F-1) to (F-8); and a is an integer of 2 to 4.

[0010] Item 6. The resin composition according to Item 5, wherein the formula (10) is the following formula (11): R 6 4-b Si(OR 7 ) b (11) (In the above formula (11), R 6 are independently an alkyl group having 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group having 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group having 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; R 7 are independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; and b is an integer of 2 to 4.

[0011] Item 7. The resin composition according to any one of Items 1 to 6, further comprising a curing catalyst.

[0012] Item 8. The resin composition according to Item 7, wherein the curing catalyst contains one or more elements selected from the group consisting of Zr, Ti, Al, S, I, N, and P.

[0013] Item 9. A cured product of the resin composition according to any one of items 1 to 8.

[0014] Item 10. A device having a layer containing the cured product according to item 9.

[0015] Item 11. An electronic device having the element according to item 10.

[0016] Item 12. A method for producing a resin composition, comprising a compound production step of reacting a compound represented by the following formula (4) with at least one of a compound represented by the following formula (5) and a compound represented by the following formula (6) at 20°C or higher and 70°C or lower to obtain a silicon compound: [ka] (In the above formula (4), R A1 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; R A2 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; R A7 are independently a hydrogen atom or -(Si(R B3 )2-O) p -Si(R B3 ) 2-OH (p independently represents 0 or an integer of 1 to 30); R B3 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; In the above formula (5), R A3 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; n A1 is an integer between 1 and 30; In the above formula (6), R A4 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; n A2is an integer between 1 and 30; R A1 , R A2 , R A3 , R A4 , and R B3 When at least one of the above is an alkyl group having 1 to 40 carbon atoms, the alkyl group having 1 to 40 carbon atoms is independently selected from a group in which at least one hydrogen atom is independently replaced with a halogen atom, a cycloalkyl group A having 5 or 6 carbon atoms, B2 or an aryl group A having 6 to 20 carbon atoms B4 At least one -CH2- may be independently replaced by -O-, -CO-, or a cycloalkylene group A having 5 or 6 carbon atoms. B3 or an arylene group A having 6 to 20 carbon atoms B5 may be replaced by; R A1 , R A2 , R A3 , R A4 , and R B3 When at least one of the above is a cycloalkyl group having 5 or 6 carbon atoms, the cycloalkyl group having 5 or 6 carbon atoms is independently selected from the group consisting of at least one hydrogen atom independently replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, C1 , a cycloalkyl group A having 5 or 6 carbon atoms C2 or an aryl group A having 6 to 20 carbon atoms C4 wherein at least one -CH2- is independently replaced by -O- or -CO-; R A1 , R A2 , R A3 , R A4 , and R B3 When at least one of the above is an aryl group having 6 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms is independently selected from the group consisting of at least one hydrogen atom replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, D1 , a cycloalkyl group A having 5 or 6 carbon atoms D2 or an aryl group A having 6 to 20 carbon atoms D4 may be replaced by; Alkyl group A C1and alkyl group A D1 at least one hydrogen atom may be independently replaced by a halogen atom, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one -CH2- may be independently replaced by -O-, -CO-, a cycloalkylene group having 5 or 6 carbon atoms, or an arylene group having 6 to 20 carbon atoms; the cycloalkyl group A B2 , a cycloalkylene group A B3 , cycloalkyl group A C2 and a cycloalkyl group A D2 at least one hydrogen atom may be independently replaced by a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one -CH2- may be independently replaced by -O- or -CO-; an aryl group A B4 , an arylene group A B5 , an aryl group A C4 and an aryl group A D4 may independently replace at least one hydrogen atom with a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.) [Effects of the Invention]

[0017] According to the present invention, it is possible to provide a resin composition that contains an organosilicon compound, has a small rate of viscosity change over time, and is easy to handle. DETAILED DESCRIPTION OF THE INVENTION

[0018] The present invention will be described in detail below. The following explanation of the constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In addition, in this specification, "hydrogen" in the explanation of structural formulas means "hydrogen atom (H)". Similarly, "carbon atom (C)" may be referred to as "carbon". As used herein, the term "adjacent groups" refers to two groups each bonded to one atom, or two groups each bonded to two adjacent atoms in a structural formula (two atoms directly bonded by a covalent bond). In addition, in this specification, the expression "A or B" can be read as "at least one selected from the group consisting of A and B." In addition, in the present specification, when considering the structure of "ABC", a structure in which B is a single bond means a structure of "AC".

[0019] A compound represented by formula (1) may be abbreviated as compound (1). At least one compound selected from the group of compounds represented by formula (1) may be abbreviated as compound (1). "Compound (1)" means one compound represented by formula (1), a mixture of two compounds, or a mixture of three or more compounds. These rules also apply to compounds represented by other formulas. In the chemical formula of the compound, the substituent R X1 The symbol R is used for several compounds. In these compounds, any two R X1 The two groups represented by may be the same or different. For example, in compound (2-1), X1 is a phenyl group, and R X1 In some cases, R is a phenyl group. X1 is a phenyl group, and R X1 In some cases, R is a cyclohexyl group. X2 , R X3It also applies to symbols such as the repeating unit n in the chemical formula of a compound. 5 The symbol n is used for several compounds. In these compounds, any two n 5 The two numbers represented by j can be the same or different. 3 , k 2 This also applies to symbols such as The expression "at least one 'A'" means that the number of 'A's is arbitrary. The expression "at least one 'A' may be replaced with 'B'" means that when there is one 'A', the position of 'A' is arbitrary, and when there are two or more 'A's, the positions can be selected without restriction. This rule also applies to the expression "at least one 'A' is replaced with 'B'." The expression "at least one 'A' may be replaced with 'B', 'C', or 'D'" means that any 'A' is replaced with 'B', any 'A' is replaced with 'C', any 'A' is replaced with 'D', and also includes cases where multiple 'A's are replaced with at least two of 'B', 'C', and / or 'D'. Note that this does not include cases where two consecutive -CH2- are replaced with -O-, resulting in -OO-. In alkyl groups, etc., those in which the -CH2- in the methyl portion (-CH2-H) is replaced with -O- to form -OH are not included. In both cases, alkyl and alkylene may be straight-chain groups or branched groups. This also applies when any hydrogen in these groups is replaced with a halogen or a cyclic group, or when any -CH2- is replaced with -O-, -CO-, a cycloalkylene group, an arylene group, or the like. In this specification, "R 1 , R 2 , and R 3 The expression "at least one of" can be used to refer to multiple R 1 , multiple R 2 , and multiple R 3 Specifically, the target is, for example, a plurality of R 1 One of the R1 It may be only. A halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. Furthermore, although a number of embodiments are described in this specification, various conditions in each embodiment may be applied to each other to the extent that they are applicable.

[0020] <Resin composition> A resin composition according to one embodiment of the present invention (hereinafter also referred to simply as "resin composition") comprises an organosilicon compound having structures represented by the following formulas (A) and (B), wherein the proportion of structures represented by the following formula (B) where m=2 is greater than the proportion of structures represented by the following formula (B) where m=1. In this specification, a composition containing the above organosilicon compound is referred to as a resin composition.

[0021] [Organosilicon compound (ingredient A)] (Aspect 1) Hereinafter, the organosilicon compound will be described using formulas (A) and (B), and this embodiment of the organosilicon compound will also be referred to as "Embodiment 1." Note that, although many embodiments of the organosilicon compound are shown in this specification, the conditions in these embodiments can be arbitrarily combined with each other within the applicable range.

[0022] [ka]

[0023] In this specification, the term "organosilicon compound having a structure represented by formulas (A) and (B)" refers to a group of organosilicon compounds having a plurality of structures represented by formulas (A) and (B). In this specification, the "organosilicon compound having a structure represented by formulas (A) and (B)" contained in the resin composition may be one type or two or more types. The target of the structure represented by formula (B) where m = 2 is the "structure represented by formula (B) where m = 2" contained in the entire organosilicon compound contained in the resin composition. Similarly, the target of the structure represented by formula (B) where m = 1 is the "structure represented by formula (B) where m = 1" contained in the entire organosilicon compound contained in the resin composition. Furthermore, the organosilicon compound contains at least a structure represented by formula (B), specifically, at least a structure represented by formula (B) where m=2, and the structure represented by formula (B) may be sandwiched between structures represented by formula (A), or may be present without being sandwiched between structures represented by formula (A).

[0024] In this specification, the structure represented by the above formula (B) where m=2 is (-O-Si(-R 3 )2-) structure is a structure in which the number of consecutive structures represented by (-O-Si(-R 3 The structure in which three consecutive (-O-Si(-R)-) are bonded includes the structure represented by formula (B) where m=1 or 2, but is treated as the structure represented by formula (B) where m=3. Similarly, the structure represented by formula (B) above where m=1 is treated as the structure represented by formula (B) where m=3. 3 )2-) structure is a structure in which the number of consecutive structures represented by (-O-Si(-R 3 A structure in which )2-) are consecutive is not treated as a structure represented by formula (B) in which m=1.

[0025] The present inventors have conducted extensive research and found that resin compositions containing the above organosilicon compounds exhibit a small rate of change in viscosity over time. The present inventors speculate that the reason for this is as follows. When the proportion of the structure represented by the above formula (B) where m=2 is greater than the proportion of the structure represented by the formula (B) where m=1, aggregation of the organosilicon compound can be suppressed, and the rate of change in viscosity over time can be reduced. Therefore, since the above-mentioned resin composition contains a compound having a silsesquioxane skeleton, it is possible to obtain a molded article having excellent heat resistance and insulating properties, and since the viscosity change rate over time is small, the resin composition has excellent storage stability.

[0026] In formula (A), R 1 From the viewpoint of ease of synthesis and the ability to adjust various properties such as heat resistance, refractive index, mechanical properties, and optical properties (hereinafter, these are also collectively referred to as "the viewpoint of ease of synthesis and adjustment of various properties"), the carbon number (number of carbon atoms) is independently 1 to 40. an alkyl group, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; R 2 is the above R 1 From the same viewpoint as above, they are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0027] In the above formula (B), R 3 is the above R 1 From the same viewpoint as above, each of them is independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; In the above formula (B), m is an integer of 1 to 30, preferably 2 to 25, and more preferably 2 to 20, from the viewpoint of ease of synthesis.

[0028] R 1 When R is an aryl group, the effects of improving heat resistance, improving refractive index, and improving rigidity (allowing adjustment of mechanical properties) can be obtained. 1 When R is an alkyl group, it is easy to obtain a medium and well-balanced refractive index (it is possible to lower the refractive index more than when it is an aryl group), and it is easy to improve toughness (it is possible to adjust the mechanical properties). The effects obtained when R is an aryl group or an alkyl group are as follows: 2 or R 3 The same applies when is an aryl group or an alkyl group.

[0029] Below, R 1 , R 2 , and R 3 These groups will be described below, and when made into a resin composition, ease of synthesis can be ensured while maintaining a small rate of change in viscosity over time.

[0030] R 1 , R 2 , and R 3 When at least one of the above is an alkyl group having 1 to 40 carbon atoms, the alkyl group having 1 to 40 carbon atoms is independently selected from a group in which at least one hydrogen atom is independently replaced with a halogen atom, a cycloalkyl group A having 5 or 6 carbon atoms, 12 or an aryl group A having 6 to 20 carbon atoms 14 At least one -CH2- may be independently replaced by -O-, -CO-, or a cycloalkylene group A having 5 or 6 carbon atoms. 13 or an arylene group A having 6 to 20 carbon atoms 15 may be replaced by

[0031] R 1 , R 2 , and R 3 When at least one of the above is a cycloalkyl group having 5 or 6 carbon atoms, the cycloalkyl group having 5 or 6 carbon atoms is independently selected from the group consisting of at least one hydrogen atom independently replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, 21 , a cycloalkyl group A having 5 or 6 carbon atoms 22 or an aryl group A having 6 to 20 carbon atoms 24 and at least one -CH2- may be independently replaced by -O- or -CO-.

[0032] R 1 , R 2 , and R 3 When at least one of the above is an aryl group having 6 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms is independently selected from the group consisting of at least one hydrogen atom replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, 31, a cycloalkyl group A having 5 or 6 carbon atoms 32 or an aryl group A having 6 to 20 carbon atoms 34 may be replaced by

[0033] Alkyl group A 21 and alkyl group A 31 may independently replace at least one hydrogen atom with a halogen atom, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and may independently replace at least one -CH- with -O-, -CO-, a cycloalkylene group having 5 or 6 carbon atoms, or an arylene group having 6 to 20 carbon atoms. Cycloalkyl group A 12 , a cycloalkylene group A 13 , cycloalkyl group A 22 and a cycloalkyl group A 32 In each of the groups, at least one hydrogen atom may be independently replaced by a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one -CH2- is independently replaced by may be replaced by -O-, -CO-. Aryl group A 14 , an arylene group A 15 , an aryl group A 24 and an aryl group A 34 may independently replace at least one hydrogen atom with a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0034] In order to minimize the risk of a polymerization reaction occurring that affects viscosity, it is preferable that the organosilicon compounds having the structures represented by the above formulas (A) and (B) do not contain vinyl or alkenyl groups.

[0035] Furthermore, the organosilicon compound contains at least a structure represented by formula (B) where m = 2, but may or may not contain a structure represented by formula (B) where m = 1. If the structure represented by formula (B) where m = 1 is not contained, the proportion of the structure represented by formula (B) where m = 1 will be 0%.

[0036] [Aspect 2] The organosilicon compound according to the above-mentioned aspect 1 may be an organosilicon compound consisting of a compound represented by the following formula (1), containing at least a structure represented by the following formula (3), in which the proportion of structures represented by the following formula (3) where n=2 is greater than the proportion of structures represented by the following formula (3) where n=1. This aspect is also referred to as "Aspect 2." The proportion of structures represented by the above formula (B) where m=1 or m=2 represents the proportion of the number of structures represented by the above formula (B) where m=1 or m=2, respectively, relative to the total number of structures represented by the above formula (B).

[0037] [ka]

[0038] In the above formula (1), X contains one or more structures represented by the above formula (2) and does not contain any structures other than the above structures; when X contains two or more structures represented by the above formula (2), the two or more structures may be the same or different; Y 1 is a single bond or a structure represented by the above formula (3); In the above formula (2), R 1 are independently R in the above formula (A). 1 is synonymous with ;R 2 are independently R in the above formula (A). 2 is synonymous with Y 2 is a single bond or a structure represented by the above formula (3), and the Y 1 may be the same as or different from; In the above formula (3), R 3 are independently R in the above formula (B). 3From the viewpoint of ease of synthesis, n is an integer of 1 to 30, preferably an integer of 2 to 25, and more preferably an integer of 2 to 20. The organosilicon compound contains two or more structures represented by the formula (2) in which X is present, and two or more Y 2 may be a structure represented by the above formula (3).

[0039] In this specification, the structure represented by the above formula (3) where n=2 is (—O—Si(—R 3 )2-) structure is a structure in which the number of consecutive structures represented by (-O-Si(-R 3 The structure in which three consecutive (-O-Si(-R)-) are bonded includes the structure represented by formula (3) where n=1 or 2, but is treated as the structure represented by formula (3) where n=3. Similarly, the structure represented by formula (3) above where n=1 is treated as the structure represented by formula (3) where n=3. 3 )2-) structure is a structure in which the number of consecutive structures represented by (-O-Si(-R 3 A structure in which )2-) are consecutive is not treated as a structure represented by formula (3) where n=1.

[0040] (Aspect 3) The organosilicon compound according to the above-mentioned aspect 1 or 2 preferably further satisfies the following conditions: This aspect is also referred to as "Aspect 3."

[0041] R 1 are independently an alkyl group having 1 to 20 carbon atoms, a cyclohexyl group, or a phenyl group, from the viewpoint of ease of synthesis and the ability to obtain various properties such as optical properties. R 2 is R 1 From the same viewpoint as above, each of them is independently an alkyl group having 1 to 20 carbon atoms, a cyclohexyl group, or a phenyl group. R 3 is R 1 From the same viewpoint as above, each of them is independently an alkyl group having 1 to 20 carbon atoms or a cyclohexyl group.

[0042] Among the substituents in the above embodiment 1 or 2, the following substituents are preferred from the viewpoint of ensuring ease of synthesis while maintaining a small rate of change in viscosity over time when made into a resin composition.

[0043] R 1 , R 2 , and R 3 When at least one of the above is an alkyl group having 1 to 20 carbon atoms, at least one hydrogen atom in the alkyl group having 1 to 20 carbon atoms may be independently replaced with a fluorine atom, and at least one -CH2- may be independently replaced with -O- or -CO-.

[0044] R 1 , R 2 , and R 3 When at least one of the above is a cyclohexyl group, at least one hydrogen atom of the cyclohexyl group may be independently replaced with a fluorine atom or an alkyl group having 1 to 20 carbon atoms (at least one hydrogen atom in the alkyl group may be independently replaced with a fluorine atom, and at least one -CH2- may be independently replaced with -O- or -CO-), or at least one -CH2- may be independently replaced with -O- or -CO-.

[0045] R 1 , and R 2 When at least one of the above is a phenyl group, at least one hydrogen atom of the phenyl group may be independently replaced with a fluorine atom or an alkyl group having 1 to 20 carbon atoms (at least one hydrogen atom in the alkyl group may be independently replaced with a fluorine atom, and at least one -CH2- may be independently replaced with -O- or -CO-).

[0046] (Aspect 4) The organosilicon compound according to the above-mentioned aspect 3 preferably further satisfies the following conditions: This aspect is also referred to as "aspect 4."

[0047] R 1is an alkyl group having 1 to 20 carbon atoms, a cyclohexyl group, or a phenyl group from the viewpoint of ease of synthesis and the ability to obtain various properties such as optical properties. R 2 is R 1 From the same viewpoint, alkyl groups having 1 to 20 carbon atoms, cyclohexyl groups, or or a phenyl group. R 3 is R 1 From the same viewpoint, it is an alkyl group having 1 to 20 carbon atoms or a cyclohexyl group.

[0048] Among the substituents in the above-mentioned embodiment 3, the following substituents are preferred from the viewpoint of ensuring ease of synthesis while maintaining a small rate of change in viscosity over time when made into a resin composition.

[0049] R 1 , R 2 , and R 3 When at least one of the above is an alkyl group having 1 to 20 carbon atoms, at least one -CH2- in the alkyl group having 1 to 20 carbon atoms may independently be replaced with -O-.

[0050] R 1 , R 2 , and R 3 When at least one of the above is a cyclohexyl group, at least one hydrogen atom of the cyclohexyl group may be independently replaced by an alkyl group having 1 to 20 carbon atoms (at least one -CH2- in the alkyl group may be independently replaced by -O-), and at least one -CH2- may be independently replaced by -O-.

[0051] R 1 , and R 2 When at least one of the above is a phenyl group, at least one hydrogen atom of the phenyl group may be independently replaced by an alkyl group having 1 to 20 carbon atoms (at least one -CH2- in the alkyl group may be independently replaced by -O-).

[0052] (Aspect 5) The organosilicon compound according to the above-mentioned aspect 4 preferably further satisfies the following conditions: This aspect is also referred to as "aspect 5."

[0053] R 1 is a cyclohexyl group or a phenyl group in which at least one hydrogen atom may be substituted with an alkyl group having 1 to 20 carbon atoms, from the viewpoint of ease of synthesis and adjustment of various properties. R 2 is the above R 1 From the same viewpoint, it is an alkyl group having 1 to 20 carbon atoms, or a phenyl group in which at least one hydrogen atom may be substituted with an alkyl group having 1 to 20 carbon atoms. R 3 is the above R 1 From the same viewpoint, it is an alkyl group having 1 to 20 carbon atoms.

[0054] (Aspect 6) The organosilicon compound according to the above-mentioned Aspect 5 preferably further satisfies the following conditions: This aspect is also referred to as "Aspect 6."

[0055] R 1 is a phenyl group in which at least one hydrogen atom may be substituted with an alkyl group having 1 to 20 carbon atoms, from the viewpoint of ease of synthesis and adjustment of various properties. R 3 is the above R 1 From the same viewpoint, it is an alkyl group having 1 to 20 carbon atoms.

[0056] (Aspect 7) The organosilicon compound according to the above-mentioned sixth aspect preferably further satisfies the following conditions: This aspect is also referred to as "seventh aspect."

[0057] R 2 and R 3 is an alkyl group having 1 to 6 carbon atoms from the viewpoint of ease of synthesis and adjustment of various properties.

[0058] (Aspect 8) The organosilicon compound according to the above-mentioned Aspect 7 preferably further satisfies the following conditions: This aspect is also referred to as "Aspect 8."

[0059] R 1 is a phenyl group from the viewpoint of ease of synthesis and adjustment of various properties. R 2 and R 3 is a methyl group from the viewpoint of ease of synthesis and adjustment of various properties. The above is an explanation of modes 1 to 8.

[0060] The structure of the organosilicon compound is: 1 Identification can be performed by H-NMR analysis. This identification also allows for the analysis of the proportion of structures represented by the above formula (B) where m = 2 (in the case of embodiment 2, the proportion of structures represented by formula (3) where n = 2) and the proportion of structures where m = 1 (in the case of embodiment 2, the proportion of structures represented by formula (3) where n = 1). For example, the proportion of structures represented by formula (B) where m = 2 is the proportion when the proportion of all structures represented by formula (B) is 100%. In other words, when an organosilicon compound having structures represented by formulas (A) and (B) is composed of multiple types of organosilicon compounds with different m numbers, the denominator of this proportion is the total number of all structures represented by formula (B) with different m numbers. The same applies to the proportion of structures where m = 1, and the proportion of structures where n = 2 and n = 1 in embodiment 2.

[0061] When the target is the structure represented by formula (B) contained in all of the organosilicon compounds having structures represented by formulas (A) and (B) contained in the resin composition, the proportion of structures represented by formula (B) where m=2 may be greater than the proportion of structures represented by formula (B) where m=1. The ratio of the proportion of structures represented by formula (B) where m=2 to the proportion of structures represented by formula (B) where m=1 (m=2 / m=1) is not particularly limited as long as it is greater than 1, but from the viewpoint of minimizing the rate of change in viscosity over time when a resin composition is made, assuming that the proportion of all structures represented by formula (B) is 100%, it is preferable that the proportion of structures where m=1 is 30% or less and m=2 / m=1 is 1.05 or more, and it is more preferable that the proportion of structures where m=1 is 25% or less and m=2 / m=1 is 1.1 or more. The upper limit of this ratio may be 9.0 or less.

[0062] The ratio of the number of structures represented by the above formula (B) where m=1 to the total number of structures represented by the above formula (B) is not particularly limited, but from the viewpoint of easily ensuring a small rate of change in viscosity over time when made into a resin composition, it is preferably 25% or less, more preferably 23% or less, and even more preferably 20% or less. The proportion of the structure represented by the above formula (B) where m=2 relative to the entire structure represented by the above formula (B) is not particularly limited, but from the viewpoint of easily ensuring a small rate of change in viscosity over time when made into a resin composition, it is preferably 20% or more, more preferably 23% or more, and even more preferably 25% or more. The proportion of the structure represented by the above formula (B) where m=1 and the proportion of the structure represented by the above formula (B) where m=2 can be achieved by adjusting the reaction temperature, reaction time, catalyst amount, solid content concentration, etc.

[0063] When multiple compounds with different structures exist as organosilicon compounds having structures represented by formulas (A) and (B), the "proportion of structures represented by formula (B) where m = 2" refers to the proportion of structures with m = 2 contained in all of the multiple organosilicon compounds. The same applies to the "proportion of structures represented by formula (B) where m = 1."

[0064] There are no particular limitations on the method for increasing the proportion of the structure represented by the above formula (B) where m=2 compared to the proportion of the structure represented by the above formula (B) where m=1, but this can be achieved, for example, by adjusting synthesis conditions such as reaction temperature, reaction time, catalyst amount, solid content concentration, etc. For example, if the reaction temperature is too high or the reaction time is too long, the scission of siloxane bonds will proceed, and the proportion of structures where m = 1 will tend to increase. If the reaction temperature is too low or the reaction time is too short, raw materials will remain and the amount of organosilicon compound obtained will decrease.

[0065] The organosilicon compound having the structure represented by the above formulas (A) and (B) is, more specifically, an organosilicon compound having a structure represented by the following formula (1-1): It contains at least a structure represented by the following formula (1-2): The proportion of the structure represented by the following formula (1-2) is The proportion of the structure represented by the following formula (1-3) is greater than that It may be an organosilicon compound.

[0066] [ka]

[0067] In the above formulas (1-1), (1-2) and (1-3), R X1 , R X2 , and R X3 are independently the R 1 , R 2 , and R 3 is synonymous with. n 1 are independently 0 or an integer of 1 to 30, more preferably an integer of 1 to 30, even more preferably an integer of 2 to 25, and particularly preferably an integer of 2 to 20, from the viewpoint of ease of synthesis. n 2are independently 0 or an integer of 1 to 30, more preferably an integer of 1 to 30, even more preferably an integer of 2 to 25, and particularly preferably an integer of 2 to 20, from the viewpoint of ease of synthesis. n 3 are independently 0 or an integer of 1 to 30, more preferably an integer of 1 to 30, even more preferably an integer of 2 to 25, and particularly preferably an integer of 2 to 20, from the viewpoint of ease of synthesis. j 1 are independently 0 or 1. j 2 are independently 0 or 1. j 1 +j 2 is either 1 or 2. k 1 represents an integer between 1 and 1,000. n in the above formula (1-1) 1 , n 2 , or n 3 is 2, these symbols correspond to (-O-Si(-R X3 )2-) is represented by the formula (1-2), and n 1 , n 2 , or n 3 is 1, these symbols correspond to (-O-Si(-R X3 The structure represented by )2-) is formula (1-3). In this specification, the structure represented by the above formula (1-2) is (-O-Si(-R X 3 )2-) structure is a structure in which the number of consecutive structures represented by (-O-Si(-R X3 The structure in which three consecutive (-O-Si(-R)-) are bonded includes the structure represented by formula (1-3) or (1-2), but is not treated as the structure represented by formula (1-3) or (1-2). Similarly, the structure represented by formula (1-3) above is not treated as the structure represented by formula (1-3). X3 )2-) structure is a structure in which the number of consecutive structures represented by (-O-Si(-R X3 A structure in which )2-) are consecutive is not treated as a structure represented by formula (1-3).

[0068] More specifically, the organosilicon compound having the structure represented by formula (1-1) above may include one or more compounds selected from the group consisting of compounds represented by formulas (2-1), (2-2), and (2-3): In this case as well, the compound contains at least the structure represented by formula (1-2) above, and the proportion of the structure represented by formula (1-2) above is greater than the proportion of the structure represented by formula (1-3) above.

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] In the above formulas (2-1), (2-2) and (2-3), R X1 , R X2 , and R X3 are independently R in the above formulas (1-1), (1-2) and (1-3), respectively. X1 , R X2 , and R X3 is synonymous with. n 4 , n 5 , n 6 , j 3 , j 4 , and k 2 The conditions are independently determined by the above formula (1 -1)n 1 , n 2 , n 3 , j 1 , j 2 , and k 1 can be applied in the same way.

[0073] The embodiment including one or more compounds selected from the group consisting of compounds represented by the above formulas (2-1), (2-2), and (2-3) may be, more specifically, an embodiment including one or more compounds selected from the group consisting of compounds represented by the above formulas (2-2) and (2-3).

[0074] The organosilicon compound having the structure represented by the above formulas (A) and (B) may be, for example, a compound represented by the following formula (1'): In this case as well, the compound contains at least the structure represented by the above formula (B), and the proportion of the structure represented by the above formula (B) where m=2 is greater than the proportion of the structure represented by the following formula (B) where m=1.

[0075] [ka]

[0076] In the above formula (1'), R P1 , R P2 , and R P3 are independently the R 1 , R 2 , and R 3 Also, n P1 are independently selected from the viewpoint of ease of synthesis, 1 is synonymous with n P2 are independently the above-mentioned n 1 is synonymous with. In the above formula (1'), k represents an integer of 1 to 1000. When specifying the structure of the organosilicon compound, the weight average molecular weight or number average molecular weight shown below may be used instead of k.

[0077] The weight-average molecular weight of the organosilicon compound is not particularly limited, but is preferably 3,000 to 700,000, more preferably 5,000 to 600,000, and even more preferably 7,000 to 500,000. When the weight-average molecular weight is within the above range, the resin composition containing the organosilicon compound can be adjusted to a viscosity that facilitates stirring and application. The weight-average molecular weight can be adjusted by the reaction temperature, the amount of raw materials, and, if a catalyst is used, the amount of catalyst, etc.

[0078] The weight-average molecular weight can be measured by gel permeation chromatography (GPC). Specific examples of the measurement conditions for GPC analysis are shown below. (Example of measurement conditions for GPC analysis) Column: Shodex KF805L + Shodex KF804L (two columns connected in series) manufactured by Resonac Corporation Mobile phase: THF Flow rate: 1.0ml / min Temperature: 40℃ Detector: RI Molecular weight standard sample: Polystyrene with known molecular weight

[0079] [NMR (Nuclear Magnetic Resonance Spectroscopy)] As mentioned above 1 For the H-NMR measurement, for example, JNM-ECZ500R manufactured by JEOL Ltd. can be used. 1 In the H-NMR measurement, a sample is dissolved in a deuterated solvent such as deuterated acetone (manufactured by Wako Pure Chemical Industries, Ltd.), and the measurement can be performed under the conditions of room temperature, 500 MHz, and 16 accumulations. 1 From the integral ratio of H-NMR, the proportion of the structure represented by formula (B) where m=2 and the proportion of the structure represented by formula (B) where m=1 can be calculated.

[0080] [Viscosity measurement] The viscosity of the resin composition containing the above compound can be measured, for example, using an E-type rotational viscometer manufactured by Toki Sangyo Co., Ltd. This measurement can be carried out, for example, under conditions of 25°C and 20 rpm.

[0081] [Method for producing organosilicon compounds] The method for producing the organosilicon compound is not particularly limited. An example of the production method is shown below, but the present invention is not limited thereto.

[0082] One example of a method for producing an organosilicon compound includes a step of reacting a compound represented by the following formula (4) (a compound containing a silsesquioxane skeleton) with at least one of a compound represented by the following formula (5) and a compound represented by the following formula (6) at a temperature of 0°C or higher and lower than 80°C. Specifically, the compound is preferably produced by polymerizing the above components in the presence of a catalyst. The reaction temperature is preferably 20°C or higher and 70°C or lower, from the viewpoints of the weight-average molecular weight of the resulting organosilicon compound and the tendency for the ratio of the proportion of structures where n=2 to the proportion of structures where n=1 to exceed 1.

[0083] [ka]

[0084] R in the above formula (4) A1 and R A2 The condition is satisfied by the above-mentioned formula (A) R 1 and R 2 The above conditions can be applied in the same way. R in Equation (6) A3 and R A4 The condition is independently determined by the R 3 The condition can be applied similarly, and n in the above equations (5) and (6) A1 and n A2 The condition for m in the above formula (B) can be applied independently in the same manner. That is, R A1 , R A2 , R A3 , R A4 , n A1 , and n A2 are the R in the above-mentioned aspect 1, respectively. 1 , R 2, R 3 , R 3 , m, and m, specifically satisfying the following conditions:

[0085] In the above formula (4), R A1 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; R A2 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; R A7 are independently a hydrogen atom or -(Si(R B3 )2-O) p -Si(R B3 ) 2-OH (p independently represents 0 or an integer of 1 to 30); R B3 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; In the above formula (5), R A3 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; n A1 is an integer of 1 to 30, and from the viewpoint of availability, is preferably an integer of 1 to 6, and more preferably an integer of 1 to 4; In the above formula (6), R A4 are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; n A2 is an integer between 1 and 30; R A1 , R A2 , R A3 , R A4 , and R B3 When at least one of the above is an alkyl group having 1 to 40 carbon atoms, the alkyl group having 1 to 40 carbon atoms is independently selected from a group in which at least one hydrogen atom is independently replaced with a halogen atom, a cycloalkyl group A having 5 or 6 carbon atoms, B2 or an aryl group A having 6 to 20 carbon atoms B4At least one -CH2- may be independently replaced by -O-, -CO-, or a cycloalkylene group A having 5 or 6 carbon atoms. B3 or an arylene group A having 6 to 20 carbon atoms B5 may be replaced by; R A1 , R A2 , R A3 , R A4 , and R B3 When at least one of the above is a cycloalkyl group having 5 or 6 carbon atoms, the cycloalkyl group having 5 or 6 carbon atoms is independently selected from the group consisting of at least one hydrogen atom independently replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, C1 , a cycloalkyl group A having 5 or 6 carbon atoms C2 or an aryl group A having 6 to 20 carbon atoms C4 wherein at least one -CH2- is independently replaced by -O- or -CO-; R A1 , R A2 , R A3 , R A4 , and R B3 When at least one of the above is an aryl group having 6 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms is independently selected from the group consisting of at least one hydrogen atom replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, D1 , a cycloalkyl group A having 5 or 6 carbon atoms D2 or an aryl group A having 6 to 20 carbon atoms D4 may be replaced by; Alkyl group A C1 and alkyl group A D1 at least one hydrogen atom may be independently replaced by a halogen atom, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one -CH2- may be independently replaced by -O-, -CO-, a cycloalkylene group having 5 or 6 carbon atoms, or an arylene group having 6 to 20 carbon atoms; the cycloalkyl group A B2 , a cycloalkylene group A B3 , cycloalkyl group A C2 and a cycloalkyl group AD2 at least one hydrogen atom may be independently replaced by a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one -CH2- may be independently replaced by -O- or -CO-; an aryl group A B4 , an arylene group A B5 , an aryl group A C4 and an aryl group A D4 at least one hydrogen atom is independently replaced by a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; That's fine.

[0086] Furthermore, R A1 , R A2 , R A3 , R A4 , R B3 , n A1 , and n A2 In addition to the above-mentioned embodiment 1, the conditions of embodiments 2 to 7, which are embodiments that limit embodiment 1, can also be applied in the same manner.

[0087] The order of the reaction treatment is not limited, and the reaction may be carried out by heating a mixture containing all the raw materials, or by additionally mixing each raw material.

[0088] The ratio of the total amount of the compound represented by formula (4) to the total amount of at least one of the compounds represented by formula (5) and formula (6) is not particularly limited, but is preferably 0.3 or more, more preferably 0.5 or more, and even more preferably 0.7 or more, in molar ratio, and is preferably 15 or less, more preferably 10 or less, and even more preferably 5 or less. If this ratio is equal to or greater than the lower limit of the above range, it is easy to obtain an organosilicon compound having flexibility. On the other hand, if this ratio is equal to or less than the upper limit of the above range, it is easy to obtain an organosilicon compound having high heat resistance.

[0089] The compound represented by formula (4) above can be obtained, for example, as described in JP 2006-222207 A, by reacting a compound represented by formula (7) below with a compound represented by formula (8) below, followed by hydrolysis. Here, X represents a halogen atom or a hydrogen atom. The compound represented by formula (7) can also be obtained, as described in JP 2006-222207 A, by hydrolyzing and condensing a compound represented by formula (9) in the presence of sodium hydroxide and water.

[0090] [ka]

[0091] R in the above formulas (7) to (9) A1 and R A2 are R in the above formulas (4) to (6), respectively. A1 and R A2 is synonymous with.

[0092] In the reaction of the compounds represented by (4) to (6) above, an acid or a base is usually used as a catalyst. In the method for producing an organosilicon compound described above in this embodiment, considering the stability of the silsesquioxane during the reaction, an acid is preferred as the catalyst. Examples of acid catalysts include hydrochloric acid, phosphoric acid, toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, sulfuric acid, fluorosulfuric acid, nitric acid, acetic acid, activated clay, and cation exchange resins such as sulfonic acid-based ion exchange resins (commercially available products include RCP-160M ​​(strong acid cation exchange resin, manufactured by Mitsubishi Chemical Corporation)). Among these, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, activated clay, and cation exchange resins are preferred, with sulfuric acid being more preferred. The shape of the catalyst is not particularly limited, but from the viewpoint of reaction rate, a liquid is preferred over a solid. The amount of catalyst used (content in the case of a mixture) is not particularly limited as long as it is an amount sufficient to promote the polymerization reaction. From the viewpoint of promoting the reaction, it is preferably 0.5% by mass or more, more preferably 0.7% by mass or more, and even more preferably 0.9% by mass or more, based on the total mass of the raw materials charged for the organosilicon compound. Furthermore, from the viewpoints of cost-effectiveness and polymerization stability, it is preferably 40% by mass or less, more preferably 20% by mass or less, and even more preferably 10% by mass or less.

[0093] The reaction is preferably carried out using a solvent, which is not particularly limited as long as it is a solvent capable of dissolving at least one of the compound represented by formula (4) above and the compound represented by formula (5) above and the compound represented by formula (6) above, and does not react with a catalyst when one is used. Examples of such solvents include hydrocarbon solvents such as butane, hexane, heptane, octane, and cyclohexane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, mesitylene, and anisole; ether solvents such as diethyl ether, diisopropyl ether, 1,2-dimethoxyethane, tetrahydrofuran (THF), 2-methyltetrahydrofuran (2MTHF), 4-methyltetrahydropyran (MTHP), cyclopentyl methyl ether (CPME), and dioxane; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and carbon tetrachloride; ester solvents such as ethyl acetate; glycol ester solvents such as propylene glycol monomethyl ether acetate (PGMEA); sulfur- or nitrogen-containing solvents such as dimethylformamide (DMF), dimethylacetamide (DMAc), dimethyl sulfoxide (DMSO), N-methylpyrrolidone (NMP), and pyridine; alcohol solvents such as methanol, ethanol, isopropanol, and butanol; and ketone solvents such as acetone and methyl ethyl ketone. Among these, toluene, xylene, mesitylene, anisole, THF, 2MTHF, MTHP, or CPME is preferable, and toluene, MTHP, or CPME is more preferable. The solvent may be a single solvent or two or more solvents. The amount of solvent used is not particularly limited and may be set appropriately depending on the size of the reactor used, the amount of components to be dissolved, etc., but for example, it is an amount such that the total content of the compound represented by formula (4) above and at least one of the compound represented by formula (5) above and the compound represented by formula (6) below is 20 to 80 mass%, more preferably 30 to 70 mass%, and even more preferably 40 to 60 mass%.

[0094] The reaction of the compounds represented by (4) to (6) above may be carried out with the addition of water.

[0095] The reaction of the compounds represented by (4) to (6) above may be carried out using other components as long as the organosilicon compound described above can be obtained.

[0096] The reaction temperature is set so that the proportion of the structure represented by the formula (B) where m=2 can be made larger than the proportion of the structure represented by the formula (B) where m=1 in the target product group, The temperature may be 0°C or higher and lower than 80°C, but is preferably 10°C or higher and 75°C or lower, more preferably 15°C or higher and 70°C or lower, and even more preferably 20°C or higher and 70°C or lower.

[0097] The reaction time is not particularly limited, and may be, for example, 0.5 hours or more and 48 hours or less, 1 hour or more and 40 hours or less, or 2 hours or more and 30 hours or less.

[0098] The reaction atmosphere is not particularly limited, and for example, the reaction may be carried out in air or in the presence of an inert gas such as nitrogen or argon.

[0099] For more specific synthesis methods of organosilicon compounds, reference can be made to the methods described in, for example, JP-A-2010-116464 and JP-A-2020-90572.

[0100] The content of the organosilicon compound in the resin composition is not particularly limited, but is preferably 5% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 85% by mass or less, and even more preferably 15% by mass or more and 80% by mass or less, relative to 100% by mass of the resin composition. To obtain a desired film thickness after coating, the content is preferably equal to or greater than the lower limit of the above range. Furthermore, from the viewpoint of solubility, the content is preferably equal to or less than the upper limit of the above range.

[0101] The resin composition may contain components other than the organosilicon compound, such as a compound (component B) having a functional group capable of chemically bonding with component A, which will be described later.

[0102] [Compounds with functional groups capable of chemically bonding with organosilicon compounds] The resin composition may contain components other than the above-described organosilicon compound (component A). For example, the resin composition may contain a compound (component B) having a functional group capable of chemically bonding with the above-described component A. In particular, when component B has two or more functional groups capable of chemically bonding with component A, component B acts as a crosslinking agent, thereby making it possible to obtain a crosslinked product (siloxane polymer) of component A bonded via component B. Note that component B may be used alone or in combination of two or more types.

[0103] Component B having a functional group capable of chemically bonding to component A includes compounds having two or more groups of one or more types of groups represented by the following formulas (F-1) to (F-8).

[0104] [ka]

[0105] In the above formulas (F-1) to (F-8), R 4are independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group having 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group having 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; * represents a bonding site. Among the above groups, groups that can have either a linear or branched chain structure may have either a linear or branched chain structure.

[0106] R 4 are not particularly limited as long as they are independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group having 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group having 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, but from the viewpoint of reactivity with component A, they are preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group, or a butyl group, and are particularly preferably a hydrogen atom, a methyl group, or an ethyl group. Of the above functional groups, the propyl group or butyl group may have either a straight-chain or branched-chain structure.

[0107] From the viewpoint of curability and rate of change in viscosity over time, among the groups represented by the above formulas (F-1) to (F-8), one or more groups represented by (F-1) to (F-6) are preferred, and one or more groups represented by (F-2) and (F-6) are particularly preferred.

[0108] The specific structure of Component B will be described below, but Component B can have either a straight-chain or branched-chain structure, and may also have a ring structure.

[0109] From the viewpoint of the heat resistance of the product obtained by chemically bonding component B with component A, component B preferably contains one or more silicon compounds selected from the group consisting of hydrolyzable organosilane compounds represented by the following formula (10) and partial hydrolysis condensates of the hydrolyzable organosilane compounds. Note that in this specification, the expression "compound X includes compound Y and compound Z" may also be expressed as "compound X includes compound Y and compound Z." R 5 4-a SiZ a (10) In the above formula (10), R 5 are independently an alkyl group having 1 to 20 carbon atoms, at least one hydrogen atom of which may be independently substituted with a halogen atom, are independently a cycloalkyl group having 3 to 6 carbon atoms which may be substituted with a halogen atom, or an aryl group having 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; Z is independently any of the groups represented by the formulae (F-1) to (F-8); and a is an integer of 2 to 4.

[0110] R 5 are not particularly limited as long as they are independently an alkyl group of 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group of 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group of 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; however, from the viewpoint of the heat resistance of the product obtained by chemically bonding with component A, they are preferably an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, or an aryl group of 6 to 20 carbon atoms, and are particularly preferably an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms.

[0111] Furthermore, from the viewpoint of reactivity with component A, the above formula (10) is preferably the following formula (11). R 6 4-b Si(OR 7 )b (11) In the above formula (11), R 6 are independently an alkyl group having 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group having 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group having 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; R 7 are independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; and b is an integer of 2 to 4.

[0112] R 6 are not particularly limited as long as they are independently an alkyl group of 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group of 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group of 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; however, from the viewpoint of the heat resistance of the product obtained by chemically bonding with component A, they are preferably an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, or an aryl group of 6 to 20 carbon atoms, and are particularly preferably an alkyl group of 1 to 6 carbon atoms or an aryl group of 6 to 20 carbon atoms.

[0113] R 7 are not particularly limited as long as they are independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, but from the viewpoint of reactivity with component A, they are particularly preferably alkyl groups having 1 to 6 carbon atoms.

[0114] Component B may also be a compound having one or more structural units of the following formulae (B-1) to (B-4).

[0115] [ka]

[0116] In formulas (B-1) to (B-4), R B1are independently any of the groups represented by the above formulas (F-1) to (F-8), or alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, octyl, nonyl, or decyl; aryl groups such as phenyl, tolyl, xylyl, or naphthyl; aralkyl groups such as benzyl, phenylethyl, or phenylpropyl; or groups in which at least one hydrogen atom is independently substituted with a halogen atom such as a fluorine atom, chlorine atom, or bromine atom, for example, a chloromethyl group, chloropropyl group, bromoethyl group, trifluoropropyl group, or cyanoethyl group, where * represents a bonding site. Among the above functional groups, groups that can have either a linear or branched chain structure, such as a propyl group, a butyl group, or a pentyl group, may have either a linear or branched chain structure.

[0117] Component B can be obtained, for example, by using at least one compound of the following formulas (B-5) and (B-6) by a known method such as ring-opening polymerization or hydrolytic condensation, or by the method described in WO 2014 / 098189.

[0118] [ka]

[0119] In formula (B-5), R B2are independently any of the groups represented by the above formulas (F-1) to (F-8), or alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, octyl, nonyl, or decyl; aryl groups such as phenyl, tolyl, xylyl, or naphthyl; aralkyl groups such as benzyl, phenylethyl, or phenylpropyl; or groups in which at least one hydrogen atom is independently substituted with a halogen atom such as a fluorine atom, chlorine atom, or bromine atom, for example, a chloromethyl group, a chloropropyl group, a bromoethyl group, or a trifluoropropyl group. Among the above functional groups, groups that can have either a linear or branched chain structure, such as a propyl group, a butyl group, or a pentyl group, may have either a linear or branched chain structure.

[0120] R in formula (B-6) B4 are independently any of the groups represented by the above formulas (F-1) to (F-8), or alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, octyl, nonyl, or decyl; aryl groups such as phenyl, tolyl, xylyl, or naphthyl; aralkyl groups such as benzyl, phenylethyl, or phenylpropyl; or groups in which at least one hydrogen atom is independently substituted with a halogen atom such as a fluorine atom, chlorine atom, or bromine atom, for example, a chloromethyl group, a chloropropyl group, a bromoethyl group, or a trifluoropropyl group. Among the above functional groups, groups that can have either a linear or branched chain structure, such as a propyl group, a butyl group, or a pentyl group, may have either a linear or branched chain structure.

[0121] In formulas (B-5) and (B-6), b 1 is an integer between 3 and 6, and b 2 is 0 or an integer from 1 to 9.

[0122] More specific examples of component B include 1,3-dimethoxytetramethyldisiloxane, 1,5-dimethoxyhexamethyltrisiloxane, polydimethylsiloxane terminally blocked with dimethylmethoxysiloxy, polymethylphenylsiloxane terminally blocked with dimethylmethoxysiloxy, polydiphenylsiloxane terminally blocked with dimethylmethoxysiloxy, dimethylsiloxane-dimethoxysiloxane copolymer terminally blocked with dimethylmethoxysiloxy, methylphenylsiloxane-dimethoxysiloxane copolymer terminally blocked with dimethylmethoxysiloxy, diphenylsiloxane-dimethoxysiloxane copolymer terminally blocked with dimethylmethoxysiloxy, polydimethylsiloxane terminally blocked with methyldimethoxysiloxy, polymethylphenylsiloxane terminally blocked with methyldimethoxysiloxy, polydiphenylsiloxane terminally blocked with methyldimethoxysiloxy. , dimethylsiloxane-dimethoxysiloxane copolymers capped with methyldimethoxysiloxy at both molecular chain ends, methylphenylsiloxane-dimethoxysiloxane copolymers capped with methyldimethoxysiloxy at both molecular chain ends, diphenylsiloxane-dimethoxysiloxane copolymers capped with methyldimethoxysiloxy at both molecular chain ends, polydimethylsiloxanes capped with trimethoxysiloxy at both molecular chain ends, polymethylphenylsiloxanes capped with trimethoxysiloxy at both molecular chain ends, polydiphenylsiloxanes capped with trimethoxysiloxy at both molecular chain ends, dimethylsiloxane-dimethoxysiloxane copolymers capped with trimethoxysiloxy at both molecular chain ends, methylphenylsiloxane-dimethoxysiloxane copolymers capped with trimethoxysiloxy at both molecular chain ends, or diphenylsiloxane-dimethoxysiloxane copolymers capped with trimethoxysiloxy at both molecular chain ends;

[0123] 1,3-diethoxytetramethyldisiloxane, 1,5-diethoxyhexamethyltrisiloxane, polydimethylsiloxane terminated with dimethylethoxysiloxy at both ends, polymethylphenylsiloxane terminated with dimethylethoxysiloxy at both ends, polydiphenylsiloxane terminated with dimethylethoxysiloxy at both ends, dimethylsiloxane-diethoxysiloxane copolymer terminated with dimethylethoxysiloxy at both ends methylphenylsiloxane-diethoxysiloxane copolymers terminated with dimethylethoxysiloxy at both molecular chain ends; diphenylsiloxane-diethoxysiloxane copolymers terminated with dimethylethoxysiloxy at both molecular chain ends; polydimethylsiloxane terminated with methyldiethoxysiloxy at both molecular chain ends; polymethylphenylsiloxane terminated with methyldiethoxysiloxy at both molecular chain ends; polydiphenylsiloxane terminated with methyldiethoxysiloxy at both molecular chain ends Nylsiloxane, dimethylsiloxane-diethoxysiloxane copolymer terminated with methyldiethoxysiloxy at both molecular chain ends, methylphenylsiloxane-diethoxysiloxane copolymer terminated with methyldiethoxysiloxy at both molecular chain ends, diphenylsiloxane-diethoxysiloxane copolymer terminated with methyldiethoxysiloxy at both molecular chain ends, polydimethylsiloxane terminated with triethoxysiloxy at both molecular chain ends, triethoxysiloxane at both molecular chain ends Disiloxy-blocked polymethylphenylsiloxane, polydiphenylsiloxane terminally blocked with triethoxysiloxy, dimethylsiloxane-diethoxysiloxane copolymer terminally blocked with triethoxysiloxy, methylphenylsiloxane-diethoxysiloxane copolymer terminally blocked with triethoxysiloxy, or diphenylsiloxane-diethoxysiloxane copolymer terminally blocked with triethoxysiloxy;

[0124] 1,3-Dihydroxytetramethyldisiloxane, 1,5-Dihydroxyhexamethyltrisiloxane, 1,5-Dihydroxyhexaphenyltrisiloxane, Polydimethylsiloxane with both molecular chain terminals capped with dimethylhydroxysiloxy, Polymethylphenylsiloxane with both molecular chain terminals capped with dimethylhydroxysiloxy, Polydiphenylsiloxane with both molecular chain terminals capped with dimethylhydroxysiloxy, Dimethylsiloxane-dihydroxysiloxane copolymer with both molecular chain terminals capped with dimethylhydroxysiloxy, Methylphenylsiloxane-dihydroxysiloxane copolymer with both molecular chain terminals capped with dimethylhydroxysiloxy, Diphenylsiloxane-dihydroxysiloxane copolymer with both molecular chain terminals capped with dimethylhydroxysiloxy, Polydimethylsiloxane with both molecular chain terminals capped with methyldihydroxysiloxy, Polymethylsiloxane with both molecular chain terminals capped with methyldihydroxysiloxy methylphenylsiloxane, polydiphenylsiloxane terminated with methyldihydroxysiloxy at both molecular chain ends, dimethylsiloxane-dihydroxysiloxane copolymer terminated with methyldihydroxysiloxy at both molecular chain ends, methylphenylsiloxane-dihydroxysiloxane copolymer terminated with methyldihydroxysiloxy at both molecular chain ends, diphenylsiloxane-dihydroxysiloxane copolymer terminated with methyldihydroxysiloxy at both molecular chain ends, polydimethylsiloxane terminated with trihydroxysiloxy at both molecular chain ends, polymethylphenylsiloxane terminated with trihydroxysiloxy at both molecular chain ends, polydiphenylsiloxane terminated with trihydroxysiloxy at both molecular chain ends, dimethylsiloxane-dihydroxysiloxane copolymer terminated with trihydroxysiloxy at both molecular chain ends, methylphenylsiloxane-dihydroxysiloxane copolymer terminated with trihydroxysiloxy at both molecular chain ends or diphenylsiloxane-dihydroxysiloxane copolymers with both ends of the molecular chain blocked with trihydroxysiloxy;

[0125] 1,1,3,3-Tetramethyldisiloxane, 1,1,3,3,5,5-Hexamethyltrisiloxane, Polydimethylsiloxane with both molecular chain terminals blocked with dimethylhydrogensiloxy, Polymethylphenylsiloxane with both molecular chain terminals blocked with dimethylhydrogensiloxy, Polydiphenylsiloxane with both molecular chain terminals blocked with dimethylhydrogensiloxy, Dimethylsiloxane-dihydrogensiloxane copolymer with both molecular chain terminals blocked with dimethylhydrogensiloxy, Methylphenylsiloxane-dihydrogensiloxane copolymer capped with dimethylhydrogensiloxy at both chain ends, diphenylsiloxane-dihydrogensiloxane copolymer capped with dimethylhydrogensiloxy at both chain ends, polydimethylsiloxane capped with methyldihydrogensiloxy at both chain ends, polymethylphenylsiloxane capped with methyldihydrogensiloxy at both chain ends, polydiphenylsiloxane capped with methyldihydrogensiloxy at both chain ends, dimethylsiloxane-dihydrogensiloxane copolymer capped with methyldihydrogensiloxy at both chain ends, methylphenylsiloxane-dihydrogensiloxane copolymer capped with methyldihydrogensiloxy at both chain ends, diphenylsiloxane-dihydrogensiloxane copolymer capped with methyldihydrogensiloxy at both chain ends, polydimethylsiloxane capped with trihydrogensiloxy at both chain ends, terminally trihydrogensiloxy-blocked polymethylphenylsiloxane, terminally trihydrogensiloxy-blocked polydiphenylsiloxane, terminally trihydrogensiloxy-blocked dimethylsiloxane-dihydrogensiloxane copolymer, terminally trihydrogensiloxy-blocked methylphenylsiloxane-dihydrogensiloxane copolymer, or terminally trihydrogensiloxy-blocked diphenylsiloxane-dihydrogensiloxane copolymer;

[0126] 1,3-Diacetoxytetramethyldisiloxane, 1,5-Diacetoxyhexamethyltrisiloxane, Polydimethylsiloxane End-Canceled with Dimethylacetoxysiloxy, Polymethylphenylsiloxane End-Canceled with Dimethylacetoxysiloxy, Polydiphenylsiloxane End-Canceled with Dimethylacetoxysiloxy, Dimethylsiloxane-Diacetoxysiloxane Copolymer End-Canceled with Dimethylacetoxysiloxy, Methylphenylsiloxane-Diacetoxysiloxane Copolymer End-Canceled with Dimethylacetoxysiloxy, Diphenylsiloxane-Diacetoxysiloxane Copolymer End-Canceled with Dimethylacetoxysiloxy, Polydimethylsiloxane End-Canceled with Methyldiacetoxysiloxy, Polymethylphenylsiloxane End-Canceled with Methyldiacetoxysiloxy, Polydiphenylsiloxane End-Canceled with Methyldiacetoxysiloxy Phenylsiloxane, dimethylsiloxane-diacetoxysiloxane copolymer terminated with methyldiacetoxysiloxy at both molecular chain ends, methylphenylsiloxane-diacetoxysiloxane copolymer terminated with methyldiacetoxysiloxy at both molecular chain ends, diphenylsiloxane-diacetoxysiloxane copolymer terminated with methyldiacetoxysiloxy at both molecular chain ends, polydimethylsiloxane terminated with triacetoxysiloxy at both molecular chain ends, polymethylphenylsiloxane terminated with triacetoxysiloxy at both molecular chain ends, polydiphenylsiloxane terminated with triacetoxysiloxy at both molecular chain ends, dimethylsiloxane-diacetoxysiloxane copolymer terminated with triacetoxysiloxy at both molecular chain ends, methylphenylsiloxane-diacetoxysiloxane copolymer terminated with triacetoxysiloxy at both molecular chain ends, or diphenylsiloxane-diacetoxysiloxane copolymer terminated with triacetoxysiloxy at both molecular chain ends;

[0127] 1,3-diethylmethylketoximetetramethyldisiloxane, 1,5-diethylmethylketoximehexamethyltrisiloxane, polydimethylsiloxane terminated at both ends with dimethylethylmethylketoximesiloxy, polymethylphenylsiloxane terminated at both ends with dimethylethylmethylketoximesiloxy, Siloxy-capped polydiphenylsiloxane, dimethylethylmethylketoximesiloxy-capped dimethylsiloxane-diethylmethylketoximesiloxane copolymer at both molecular chain ends, dimethylethylmethylketoximesiloxy-capped methylphenylsiloxane-diethylmethylketoximesiloxane copolymer at both molecular chain ends, dimethylethylmethylketoximesiloxy-capped diphenylsiloxane-diethylmethylketoximesiloxane copolymer at both molecular chain ends, methyldiethylmethylketoximesiloxy-capped polydimethylsiloxane, methyldiethylmethylketoximesiloxy-capped polymethylphenylsiloxane, methyldiethylmethylketoximesiloxy-capped polydiphenylsiloxane, methyldiethylmethylketoximesiloxy-capped dimethylsiloxane-diethylmethylketoximesiloxane copolymer at both molecular chain ends, methyldiethylmethylketoximesiloxane at both molecular chain ends Tyl ketoxime siloxy-blocked methylphenylsiloxane-diethylmethylketoxime siloxane copolymer, methyl diethylmethylketoxime-terminally blocked diphenylsiloxane-diethylmethylketoxime siloxane copolymer, triethylmethylketoxime siloxy-blocked polydimethylsiloxane, triethylmethylketoxime siloxy-blocked polymethylphenylsiloxane, triethylmethylketoxime siloxy-blocked polydiphenylsiloxane, triethylmethylketoxime siloxy-blocked dimethylsiloxane-diethylmethylketoxime siloxane copolymer, triethylmethylketoxime siloxy-blocked methylphenylsiloxane-diethylmethylketoxime siloxane copolymer, or triethylmethylketoxime siloxy-blocked diphenylsiloxane-diethylmethylketoxime siloxane copolymer;

[0128] (CH3)2(OCH3)SiO 1 / 2 Units and (CH3)2SiO 2 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)3SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)(OCH3)SiO 2 / 2Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2(OCH3)SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 copolymers consisting of (CH3)2(OCH3)SiO units, 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (C6H5)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 a copolymer consisting of units; (CH3)2(OC2H5)SiO 1 / 2 Units and (CH3)2SiO 2 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)3SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)(OC2H5)SiO 2 / 2 Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2(OC2H5)SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 copolymers consisting of (CH3)2(OC2H5)SiO units, 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (C6H5)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 a copolymer consisting of units;

[0129] (CH3)2(OH)SiO 1 / 2 Units and (CH3)2SiO 2 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)3SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)(OH)SiO 2 / 2 Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2(OH)SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2(OH)SiO units1 / 2 Units and (CH3)2SiO 2 / 2 Units and (C6H5)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 a copolymer consisting of units; (CH3)2(CH=CH2)SiO 1 / 2 Units and (CH3)2SiO 2 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)3SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)(CH=CH2)SiO 2 / 2 Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2(CH=CH2)SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 copolymers consisting of (CH3)2(CH=CH2)SiO 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (C6H5)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 a copolymer consisting of units;

[0130] (CH3)2HSiO 1 / 2 Units and (CH3)2SiO 2 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)3SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)HSiO 2 / 2 Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2HSiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2HSiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (C6H5)2SiO 2 / 2 Units and (CH3)SiO 3 / 2copolymers consisting of units, and the like, and in each of these exemplary compounds, some or all of the methyl groups have been substituted with other alkyl groups such as ethyl groups or propyl groups, or aryl groups such as phenyl groups;

[0131] Methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, glycidyltrimethoxysilane, mercaptotrimethoxysilane, mercaptotriethoxysilane, aminopropyltriethoxysilane, tetramethoxysilane, partially condensed tetramethoxysilane, tetraethoxysilane, partially condensed tetraethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, isobutyltrimethoxysilane, ethyltrimethoxysilane, vinyltriethoxysilane, phenyltrimethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, methyltriacetate Examples of the silane include butoxysilane, vinyltriacetoxysilane, ethyltriacetoxysilane, dibutoxydiacetoxysilane, phenyl-trippropionoxysilane, methyltris(methylethylketoximo)silane, vinyl-tris-methylethylketoximosilane, methyltris(methylethylketoximino)silane, methyltris(isopropenoxy)silane, vinyltris(isopropenoxy)silane, ethylpolysilicate, n-propylorthosilicate, ethylorthosilicate, dimethyltetraacetoxydisiloxane, oximesilane, acetoxysilane, acetoximesilane, and enoxysilane.

[0132] Furthermore, compounds having one or more structural units of the above formulae (B-1) to (B-4) also include the compounds shown below. 1,6-bis(trimethoxysilyl)hexane, bis(trialkoxysilylalkyl)amine, bis(dialkoxyalkylsilylalkyl)amine, bis(trialkoxysilylalkyl) N-alkylamine, bis(dialkoxyalkylsilylalkyl) N-alkylamine, bis(trialkoxysilylalkyl)urea, bis(dialkoxyalkylsilylalkyl)urea, bis(3-trimethoxysilylpropyl)amine, bis(3-triethoxysilylpropyl)amine, bis(4-trimethoxysilylbutyl)amine, bis(4-triethoxysilylbutyl)amine, bis(3-trimethoxysilylpropyl) N-methylamine, bis(3-triethoxysilylpropyl) N-methylamine, bis(4-trimethoxysilylbutyl) N-methylamine, bis(4-triethoxysilylbutyl) N-methylamine, bis(3-trimethoxysilylpropyl)urea, bis(3-triethoxysilylpropyl)urea, bis(4-trimethoxysilylbutyl)urea, Bis(4-triethoxysilylbutyl)urea, Bis(3-dimethoxymethylsilylpropyl)amine, Bis(3-diethoxymethylsilylpropyl)amine, Bis(4-dimethoxymethylsilylbutyl)amine, Bis(4-diethoxymethylsilylbutyl)amine, Bis(3-dimethoxymethylsilylpropyl)N-methylamine, Bis(3-diethoxymethylsilylpropyl)N-methylamine, Bis(4-dimethoxymethylsilylbutyl)N-methylamine, Bis(4-diethoxymethyl silylbutyl) N-methylamine, bis(3-dimethoxymethylsilylpropyl)urea, bis(3-diethoxymethylsilylpropyl)urea, bis(4-dimethoxymethylsilylbutyl)urea, bis(4-diethoxymethylsilylbutyl)urea, bis(3-dimethoxyethylsilylpropyl)amine, bis(3-diethoxyethylsilylpropyl)amine, bis(4-dimethoxyethylsilylbutyl)amine, bis(4-diethoxyethylsilylbutyl)amine, bis(3-dimethoxyethyl bis(3-diethoxyethylsilylpropyl)N-methylamine, bis(4-dimethoxyethylsilylbutyl)N-methylamine, bis(4-diethoxyethylsilylbutyl)N-methylamine, bis(3-dimethoxyethylsilylpropyl)urea, bis(3-diethoxyethylsilylpropyl)urea, bis(4-dimethoxyethylsilylbutyl)urea, and / or bis(4-diethoxyethylsilylbutyl)urea; bis(triethoxysilylpropyl)amine, bis(trimethoxysilylpropyl)amine, bis(trimethoxysilylpropyl)urea, bis(triethoxysilylpropyl)urea or bis(diethoxymethylsilylpropyl) N-methylamine; di- or trialkoxysilane-terminated polydialkylsiloxane, di- or trialkoxysilyl-terminated polyarylalkylsiloxane, di- or trialkoxysilyl-terminated polypropylene oxide, polyurethane, or polyacrylate; polyisobutylene; di- or triacetoxy-terminated polydialkyl; polyarylalkylsiloxane; di- or trioxyiminosilyl-terminated polydialkyl; polyarylalkylsiloxane; or di- or triacetoxy-terminated polydialkyl or polyarylalkyl, etc.

[0133] Examples of commercially available products of component B include the Silaplane FM11 series, Silaplane FM88 series, Silaplane FM99 series, and Silaplane FM08 series (all trade names) manufactured by JNC Corporation; the SR series (trade name) manufactured by Konishi Chemical Industry Co., Ltd.; MKC Silicate MS57 (trade name), MKC Silicate MS51 (trade name) (average pentamer of tetramethoxysilane), MKC Silicate MS56, and MS56S (all trade names) manufactured by Mitsubishi Chemical Corporation; and Methyl Silicate 51 (average tetramethoxysilane tetramer), Methyl Silicate 53 (average heptamer of tetramethoxysilane), Ethyl Silicate 40 (average pentamer of tetraethoxysilane), and Ethyl Silicate 48 (average decamer of tetraethoxysilane) manufactured by Colcoat Co., Ltd.

[0134] Specific preferred examples of component B include those having one or more structures of the above formulas (B-1) to (B-4), in which at least two or more R B1 is preferably any one of the above formulas (F-1) to (F-8).

[0135] More specifically, preferred examples of component B include 1,3-dimethoxytetramethyldisiloxane, 1,5-dimethoxyhexamethyltrisiloxane, polydimethylsiloxane terminally blocked with dimethylmethoxysiloxy, polymethylphenylsiloxane terminally blocked with dimethylmethoxysiloxy, polydiphenylsiloxane terminally blocked with dimethylmethoxysiloxy, dimethylsiloxane-dimethoxysiloxane copolymer terminally blocked with dimethylmethoxysiloxy, methylphenylsiloxane-dimethoxysiloxane copolymer terminally blocked with dimethylmethoxysiloxy, and dimethylsiloxane-dimethoxysiloxane copolymer terminally blocked with dimethylmethoxysiloxy. trimethoxysiloxy-terminated diphenylsiloxane-dimethoxysiloxane copolymer, polydimethylsiloxane terminated with trimethoxysiloxy at both ends, polymethylphenylsiloxane terminated with trimethoxysiloxy at both ends, polydiphenylsiloxane terminated with trimethoxysiloxy at both ends, dimethylsiloxane-dimethoxysiloxane copolymer terminated with trimethoxysiloxy at both ends, methylphenylsiloxane-dimethoxysiloxane copolymer terminated with trimethoxysiloxy at both ends, or diphenylsiloxane-dimethoxysiloxane copolymer terminated with trimethoxysiloxy at both ends;

[0136] 1,3-diethoxytetramethyldisiloxane, 1,5-diethoxyhexamethyltrisiloxane, polydimethylsiloxane terminated with dimethylethoxysiloxy at both molecular chain ends, polymethylphenylsiloxane terminated with dimethylethoxysiloxy at both molecular chain ends, polydiphenylsiloxane terminated with dimethylethoxysiloxy at both molecular chain ends, dimethylsiloxane-diethoxysiloxane copolymer terminated with dimethylethoxysiloxy at both molecular chain ends, dimethylsiloxane-diethoxysiloxane copolymer terminated with dimethylethoxysiloxy at both molecular chain ends ethoxysiloxy-blocked methylphenylsiloxane-diethoxysiloxane copolymer, diphenylsiloxane-diethoxysiloxane copolymer with dimethylethoxysiloxy at both molecular chain ends, diphenylsiloxane-diethoxysiloxane copolymer with methyldiethoxysiloxy at both molecular chain ends, polydimethylsiloxane with triethoxysiloxy at both molecular chain ends, polymethylphenylsiloxane with triethoxysiloxy at both molecular chain ends, polydiphenylsiloxane with triethoxysiloxy at both molecular chain ends, dimethylsiloxane-diethoxysiloxane copolymer with triethoxysiloxy at both molecular chain ends, methylphenylsiloxane-diethoxysiloxane copolymer with triethoxysiloxy at both molecular chain ends, or diphenylsiloxane-diethoxysiloxane copolymer with triethoxysiloxy at both molecular chain ends;

[0137] 1,3-Dihydroxytetramethyldisiloxane, 1,5-Dihydroxyhexamethyltrisiloxane, 1,5-Dihydroxyhexaphenyltrisiloxane, Polydimethylsiloxane with both molecular chain terminals capped with dimethylhydroxysiloxy, Polymethylphenylsiloxane with both molecular chain terminals capped with dimethylhydroxysiloxy, Polydiphenylsiloxane with both molecular chain terminals capped with dimethylhydroxysiloxy, Dimethylsiloxane-dihydroxysiloxane copolymer with both molecular chain terminals capped with dimethylhydroxysiloxy, Methylphenylsiloxane-dihydroxysiloxane copolymer with both molecular chain terminals capped with dimethylhydroxysiloxy, Dimethylhydroxysiloxy-terminated diphenylsiloxane-dihydroxysiloxane copolymer, polydimethylsiloxane terminated with trihydroxysiloxy at both ends, polymethylphenylsiloxane terminated with trihydroxysiloxy at both ends, polydiphenylsiloxane terminated with trihydroxysiloxy at both ends, dimethylsiloxane-dihydroxysiloxane copolymer terminated with trihydroxysiloxy at both ends, methylphenylsiloxane-dihydroxysiloxane copolymer terminated with trihydroxysiloxy at both ends, or diphenylsiloxane-dihydroxysiloxane copolymer terminated with trihydroxysiloxy at both ends;

[0138] 1,1,3,3-Tetramethyldisiloxane, 1,1,3,3,5,5-Hexamethyltrisiloxane, Polydimethylsiloxane with both molecular chain terminals blocked with dimethylhydrogensiloxy, Polymethylphenylsiloxane with both molecular chain terminals blocked with dimethylhydrogensiloxy, Polydiphenylsiloxane with both molecular chain terminals blocked with dimethylhydrogensiloxy, Dimethylsiloxane-dihydrogensiloxane copolymer with both molecular chain terminals blocked with dimethylhydrogensiloxy, Methylphenylsiloxane-dihydrogensiloxane copolymer with both molecular chain terminals blocked with dimethylhydrogensiloxy, Dimethylhydrogensiloxane-dihydrogensiloxane copolymer with both molecular chain terminals blocked with dimethylhydrogensiloxy Diphenylsiloxane-dihydrogensiloxane copolymer, polydimethylsiloxane terminated at both molecular chain ends with trihydrogensiloxy, polymethylphenylsiloxane terminated at both molecular chain ends with trihydrogensiloxy, polydiphenylsiloxane terminated at both molecular chain ends with trihydrogensiloxy, dimethylsiloxane-dihydrogensiloxane copolymer terminated at both molecular chain ends with trihydrogensiloxy, methylphenylsiloxane-dihydrogensiloxane copolymer terminated at both molecular chain ends with trihydrogensiloxy, or diphenylsiloxane-dihydrogensiloxane copolymer terminated at both molecular chain ends with trihydrogensiloxy;

[0139] Methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, tetramethoxysilane, partially condensed tetramethoxysilane, tetraethoxysilane, or partially condensed tetraethoxysilane;

[0140] (CH3)2(OCH3)SiO 1 / 2 Units and (CH3)2SiO 2 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)3SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)(OCH3)SiO 2 / 2 Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2(OCH3)SiO units 1 / 2 Units and (CH3)2SiO2 / 2 units and (CH3)SiO 3 / 2 copolymers consisting of (CH3)2(OCH3)SiO units, 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (C6H5)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 a copolymer consisting of units; (CH3)2(OC2H5)SiO 1 / 2 Units and (CH3)2SiO 2 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)3SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)(OC2H5)SiO 2 / 2 Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2(OC2H5)SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 copolymers consisting of (CH3)2(OC2H5)SiO units, 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (C6H5)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 a copolymer consisting of units;

[0141] (CH3)2(OH)SiO 1 / 2 Units and (CH3)2SiO 2 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)3SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)(OH)SiO 2 / 2 Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2(OH)SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 copolymers consisting of (CH3)2(OH)SiO units, 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (C6H5)2SiO 2 / 2Units and (CH3)SiO 3 / 2 a copolymer consisting of units;

[0142] (CH3)2HSiO 1 / 2 Units and (CH3)2SiO 2 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)3SiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)HSiO 2 / 2 Units and (CH3)SiO 3 / 2 A copolymer consisting of (CH3)2HSiO units 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 Copolymers consisting of (CH3)2HSiO units, or 1 / 2 Units and (CH3)2SiO 2 / 2 Units and (C6H5)2SiO 2 / 2 Units and (CH3)SiO 3 / 2 and copolymers consisting of units.

[0143] Since component A has a hydroxyl group, component B can be, for example, a condensation-crosslinkable compound having three or more groups or atoms that undergo a condensation reaction with the hydroxyl group in component A. Specifically, examples of compounds having three condensation-reactive groups include methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, glycidyltrimethoxysilane, mercaptotrimethoxysilane, mercaptotriethoxysilane, aminopropyltriethoxysilane, methyltris(isopropenoxy)silane, and vinyltris(isopropenoxy)silane. Examples of compounds having four condensation-reactive groups include tetramethoxysilane and tetraethoxysilane. Examples of compounds having five or more condensation-reactive groups include partial hydrolysis condensates of the above compounds. When these compounds are used, crosslinking with component A can be achieved, for example, by placing the resin composition in a water-containing atmosphere, such as ordinary air, at room temperature under conditions of light irradiation or heating.

[0144] The content of component B in the resin composition is not particularly limited, but is preferably 0.1 to 50 parts by mass, more preferably 0.3 to 40 parts by mass, and even more preferably 0.5 to 30 parts by mass, per 100 parts by mass of component (A). If the content is equal to or greater than the lower limit of the above range, a cured film with excellent heat resistance can be obtained. On the other hand, if the content is equal to or less than the upper limit of the above range, a resin composition and a cured film with excellent solubility and toughness can be obtained.

[0145] [Other ingredients] The resin composition may contain components other than Component A and Component B (other components), such as organopolysiloxanes other than Component A and Component B, curing catalysts, solvents, fillers, ions, etc. Examples of other components include ion scavengers, surfactants, flame retardants, UV absorbers, light stabilizers, antioxidants, pigments, inorganic oxides, ion adsorbents, photosensitizers, cure retarders, cure inhibitors, organic resins, and heat dissipating fillers. Examples of other components are shown below.

[0146] (curing catalyst) The resin composition may contain a curing catalyst (component C). The catalyst can promote the chemical reaction between crosslinkable functional groups in component A when components A are chemically reacted with each other, or can promote the chemical reaction between components A and B when component B is used. Component C may be used alone or in combination of two or more. When a solvent is used, component C is preferably dissolved in the solvent from the viewpoint of reaction efficiency.

[0147] From the viewpoint of curability, the curing catalyst (component C) preferably contains one or more elements selected from the group consisting of tin (Sn), zirconium (Zr), titanium (Ti), aluminum (Al), sulfur (S), iodine (I), nitrogen (N), phosphorus (P), platinum (Pt), iron (Fe), zinc (Zn), cobalt (Co), and rhodium (Rh), more preferably one or more elements selected from Zr, Ti, Al, S, I, N, and P, and particularly preferably Zr, Ti, S, I, N, and P.

[0148] Examples of Sn-containing compounds include dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin diacetate, dioctyltin diacetate, dibutyltin maleate, dioctyltin maleate, and tin 2-ethylhexanoate.

[0149] Examples of Zr-containing compounds include normal propyl zirconate, normal butyl zirconate, zirconium tetraacetylacetonate, and zirconium monoacetylacetonate.

[0150] Examples of Ti-containing compounds include tetraisopropyl titanate, tetra-normal-butyl titanate, butyl titanate dimer, tetraoctyl titanate, titanium acetylacetonate, titanium tetraacetylacetonate, titanium ethylacetoacetate, titanium dodecylbenzenesulfonate compounds, titanium phosphate complexes, titanium octylene glycolate, titanium ethylacetoacetate, titanium lactate ammonium salt, titanium lactate, and titanium triethanolamine.

[0151] Examples of the Al-containing compound include aluminum sec-butoxide, aluminum trisacetylacetonate, aluminum bisethylacetoacetate monoacetylacetonate, and aluminum trisethylacetoacetate.

[0152] S-containing compounds include 2-butenyldimethylsulfonium, 2-butenyltetramethylenesulfonium, 3-methyl-2-butenyldimethylsulfonium, 4-hydroxyphenylcinnamylmethylsulfonium, α-naphthylmethyltetramethylenesulfonium, cinnamyldimethylsulfonium, cinnamyltetramethylenesulfonium, biphenylmethyldimethylsulfonium, biphenylmethyltetramethylenesulfonium, [biphenyl]-4-yl[4-[[biphenyl]-4-ylthio]phenyl](phenyl)sulfonium, and phenylmethyldimethylsulfonium. nium, phenylmethyltetramethylenesulfonium, fluorenylmethyldimethylsulfonium, fluorenylmethyltetramethylenesulfonium, (9-oxo-9H-thioxanthen-2-yl)[4-[(9-oxo-9H-thioxanthen-2-yl)thio]phenyl](phenyl)sulfonium, bis[4-(diphenylsulfonio)phenyl]sulfide, diphenyl[4-(phenylthio)phenyl]sulfonium, triphenylsulfonium, bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide, benzylmethyl Cations such as phenylsulfonium, benzyl(4-hydroxyphenyl)methylsulfonium, (4-hydroxyphenyl)methyl(2-methylbenzyl)sulfonium, (4-hydroxyphenyl)methyl(4-methylbenzyl)sulfonium, (4-hydroxyphenyl)methyl(1-naphthyl)sulfonium, dibenzyl-4-hydroxyphenylsulfonium, 4-acetoxyphenylbenzylsulfonium, 4-acetoxyphenyldimethylsulfonium, or 4-acetoxyphenylmethyl(2-methylbenzyl)sulfonium, and tris(pentafluoroethyl)trifluorophosphate, trifluorotris(pentafluoroethyl)phosphate, heptane ... Examples of the anion include sulfonium salts formed from anions such as hexafluorophosphate, tetrafluoroborate, tetrakis(pentafluorophenyl)borate, hexafluoroantimonate, p-toluenesulfonate, dodecylbenzenesulfonate, trifluoromethanesulfonate, perfluorobutanesulfonate, bis(trifluorosulfonyl)imide, trifluoromethanesulfonate, perfluorobutanesulfonate, methanesulfonate, and camphorsulfonate, as well as TA-90, TA-100, TA-100FG, TA-120, TA-160, CPI-200K, CPI-210S, and LW-S1 manufactured by San-Apro Co., Ltd.

[0153] I-containing compounds include diphenyliodonium chloride, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium mesylate, diphenyliodonium tosylate, diphenyliodonium bromide, diphenyliodonium tetrafluoroborate, diphenyliodonium hexafluoroantimonate, diphenyliodonium hexafluoroarsenate, bis(p-tert-butylphenyl)iodonium hexafluorophosphate, bis(p-tert-butylphenyl)iodonium mesylate, bis(p-tert-butylphenyl)iodonium t-butylphenyl)iodonium tosylate, bis(p-tert-butylphenyl)iodonium trifluoromethanesulfonate, bis(p-tert-butylphenyl)iodonium tetrafluoroborate, bis(p-tert-butylphenyl)iodonium chloride, bis(p-chlorophenyl)iodonium chloride, (4-isopropylphenyl)(p-tolyl)iodonium trifluorotris(perfluoroethyl)phosphate, bis(p-chlorophenyl)iodonium tetrafluoroborate, and other iodonium salts.

[0154] Examples of N-containing compounds include silazanes such as trimethylsilylamine, bis(trimethylsilyl)amine, tris(trimethylsilyl)amine, methyldiphenylsilylamine, bis(methyldiphenylsilyl)amine, and tris(methyldiphenylsilyl)amine; cyclic silazanes such as hexamethylcyclotrisilazane, octamethylcyclotetrasilazane, decamethylcyclopentasilazane, trimethyltriphenylcyclotrisilazane, tetramethyltetraphenylcyclotetrasilazane, pentamethylpentaphenylcyclopentasilazane, hexaphenylcyclotrisilazane, octaphenylcyclotetrasilazane, or decaphenylcyclopentasilazane; inorganic polysilazanes such as perhydropolysilazane, or organic polysilazanes such as methylpolysilazane; organic guanidines such as aminoguanidine, 1,1,3,3-tetramethylguanidine, n-dodecylguanidine, methylolguanidine, dimethylolguanidine, 1-phenylguanidine, 1,3-diphenylguanidine, 1,3-di-o-tolylguanidine, triphenylguanidine, or 1-benzyl-2,3-dimethylcyanoguanidine, 1,2-diisopropyl-3-[bis(dimethylamino)methylene]guanidinium 2-(3-benzoylphenyl)propionate, 1,2-dicyclohexyl-4,4,5,5-tetramethylbiguanidinium n-butyltriphenylborate, and (Z)-{[bis(dimethylamino)methylidene]amino}-N-cyclohexyl(cyclohexylamino)methaniminium tetrakis(3-fluorophenyl)borate; N,N-diethylcarba carbamates such as 9-anthrylmethyl imidazole carboxylate, 1-(anthraquinone-2-yl)ethyl imidazole-1-carboxylate, and (2-nitrophenyl)methyl 4-(methacryloyloxy)piperidine-1-carboxylate; Amides such as dicyandiamide and (E)-1-piperidino-3-(2-hydroxyphenyl)-2-propen-1-one; imidazoles such as 2-ethyl-4-methylimidazole, 1-methylimidazole, 1,2-dimethylimidazole, 2-methylimidazole, 2-ethylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, and 2-isopropylimidazole; carbamylalkyl-substituted imidazoles such as 1-(2-carbamylethyl)imidazole; cyanoalkyl-substituted imidazoles such as 1-cyanoethyl-2-methylimidazole; aromatic-substituted imidazoles such as 2-phenylimidazole, 2-phenyl-4-methylimidazole, and 1-benzyl-2-methylimidazole; alkenyl-substituted imidazoles such as 1-vinyl-2-methylimidazole; allyl-substituted imidazoles such as 1-allyl-2-ethyl-4-methylimidazole; or polyimidazoles; ureas such as 1,1'-(4-methyl-1,3-phenylene)bis(3,3-dimethylurea) or 3-{3-[(3,3-dimethylureido)methyl]-3,5,5-trimethylcyclohexyl}-1,1-dimethylurea; Amines such as bis(2-morpholinoethyl) ether, 1,1'-[[3-(dimethylamino)propyl]imino](2-propanol); Ammonium such as the 2-ethylhexane salt of triethylmethylammonium;

[0155] Further examples include 2-(9-oxoxanthen-2-yl)propionic acid 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), phenol salts of the above DBU, 2-ethylhexanoate salts of the above DBU, formate salts of the above DBU, o-phthalate salts of the above DBU, p-toluenesulfonate salts of the above DBU, phenol novolac resin salts of the above DBU, trimellitate salts of the above DBU, tetraphenylborate salts of benzyl-modified DBU, 2-ethylhexane salts of the above DBN, phenol resin salts of the above DBN, and biphenyl-type phenol resin salts of the above DBN.

[0156] Other examples include ketimines, which are reaction products of polyamines and carbonyl compounds. Examples of polyamines include diamines such as ethylenediamine, propylenediamine, trimethylenediamine, tetramethylenediamine, 1,3-diaminobutane, 2,3-diaminobutane, pentamethylenediamine, 2,4-diaminopentane, hexamethylenediamine, p-phenylenediamine, and p,p'-biphenylenediamine; polyamines such as 1,2,3-triaminopropane, triaminobenzene, tris(2-aminoethyl)amine, and tetra(aminomethyl)methane; polyalkylene polyamines such as diethylenetriamine, triethylenetriamine, and tetraethylenepentamine; and polyoxyalkylene polyamines. Examples of carbonyl compounds include ketimines, which are reaction products of polyamines and carbonyl compounds. Examples of the aldehyde include aldehydes such as cetoaldehyde, propionaldehyde, n-butyraldehyde, isobutyraldehyde, diethylacetaldehyde, glyoxal, and benzaldehyde; cyclic ketones such as cyclopentanone, trimethylcyclopentanone, cyclohexanone, and trimethylcyclohexanone; aliphatic ketones such as acetone, methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, methyl isobutyl ketone, diethyl ketone, dipropyl ketone, diisopropyl ketone, dibutyl ketone, and diisobutyl ketone; and β-dicarbonyl compounds such as acetylacetone, methyl acetoacetate, ethyl acetoacetate, dimethyl malonate, diethyl malonate, methyl ethyl malonate, and dibenzoylylmethane.

[0157] Examples of the P-containing compound include benzyltriphenylphosphonium bromide and ethyltriphenylphosphonium methanesulfonate.

[0158] Examples of Pt-containing compounds include platinum compounds such as platinum fine powder, platinum black, platinum-supported silica fine powder, platinum-supported activated carbon, chloroplatinic acid, an alcohol solution of chloroplatinic acid, a platinum olefin complex, or a platinum alkenylsiloxane complex. Examples of the alkenylsiloxane include 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, alkenylsiloxanes in which a portion of the methyl groups in these alkenylsiloxanes are substituted with ethyl, phenyl, or the like, and alkenylsiloxanes in which the vinyl groups in these alkenylsiloxanes are substituted with allyl, hexenyl, or the like.

[0159] Commercially available products of component C include TA-90, TA-100, TA-100FG, TA-120, TA-160, CPI-200K, CPI-210S, CPI-101A, CPI-110A, CPI-100B, CPI-100P, CPI-110, CPI-110B, CPI-110P, CPI-310B, and CPI-310F manufactured by San-Apro Co., Ltd. G, CPI-410B, CPI-410S, ES-1B, VC-1S, VC-1FG, HS-1, HS-1A, HS-1P, HS-1N, HS-1TF, HS-1NF, HS -1MS, HS-1CS, LW-S1, LW-S1NF, IK-1, IK-2, IK-1FG, NP-TM2, NA-CS1, NP-SE10, PURECAT (registered trademark) TX-1, DBU (registered trademark), DBN, NP-TM2, NP-SE10, NA-CS1, U-CAT881, U-CAT SA1, U-CAT SA102, U-CAT SA603, U-CAT SA810, U-CAT SA506, U-CAT SA841, U-CAT SA851, U-CAT SA838A, U-CAT5002, U-CAT891, U-CAT1102, U-CAT881, U-CAT891, U-CAT5003, U-CAT5050, U-CAT3512T, U-CAT3513N, U-CAT660M, U-CAT2024, or U-CAT18X, or the like; or SAN-AID SI-45, SAN-AID SI-60, SAN-AID SI-80, SAN-AID manufactured by Sanshin Chemical Industry Co., Ltd. SI-100, SAN-AID SI-150, SAN-AID SI-300, SAN-AID SI-360, SAN-AID SI-110, SAN-AID SAN-AID SI-B2A, SAN-AID SI-B7, SAN-AID SI-B3A, SAN-AID SI-B3, SAN-AID SI-B4, or SAN-AID SI-B5, etc.; or TA-8, TA-21, TA-23, TA-30, TC-100, TC-401, TC-710, TC-810, TC-1040, TC-245, TC-750, TC-300, TC-310, TC-400, TA-12, TA-80, TA-90, TC-120, TC- 230, TC-800, TC-315, TC-335, TC-500, TC-510, ZA-45, ZA-65, ZC-150, ZC-162, ZC-540, ZC-700, ZC-580, ZC-200, ZC-320, ZC-126, ZC-300, AL-3001, AL-3100, AL-3200, and the like.

[0160] Among these, dibutyltin dilaurate, normal propyl zirconate, normal butyl zirconate, zirconium tetraacetylacetonate, zirconium monoacetylacetonate, titanium acetylacetonate, titanium tetraacetylacetonate, titanium ethylacetoacetate, aluminum trisacetylacetonate, aluminum bisethylacetoacetate monoacetylacetonate, aluminum trisethylacetoacetate, Benzyl(4-hydroxyphenyl)methylsulfonium tris(pentafluoroethyl)trifluorophosphate, TA-100FG, (4-isopropylphenyl)(p-tolyl)iodonium trifluorotris(perfluoroethyl)phosphate, IK- 1, IK-1FG, SAN-AID SI-B7, SAN-AID SI-B3A, SAN-AID SI-B3, SAN-AID SI-B4, SAN-AID SI-B5, diphenyl[4-(phenylthio)phenyl]sulfonium hexafluorophosphate, diphenyl[4-(phenylthio)phenyl]sulfonium trifluorotris(pentafluoroethyl)phosphate, diphenyl[4-(phenylthio)phenyl]sulfonium tetrakis(pentafluorophenyl)borate, biphenyl]-4-yl[4-[[biphenyl]-4-ylthio]phenyl](phenyl)sulfonium tetrakis(pentafluorophenyl)borate, (9-oxo-9H-thioxanthen-2-yl)[4-[(9-oxo-9H-thioxanthen-2-yl)thio]phenyl](phenyl)sulfonium trifluorotris(pentafluoroethyl)phosphate, 9-oxo-9H-thioxanthen-2-yl)[4-[(9-oxo-9H-thioxanthen-2-yl)thio]phenyl](phenyl)sulfonium tetrakis(pentafluorophenyl)borate, Preferred are 1,2-diisopropyl-3-[bis(dimethylamino)methylene]guanidium 2-(3-benzoylphenyl)propionate, the o-phthalate salt of the above DBU, the p-toluenesulfonate salt of the above DBU, and the phenol novolak resin salt of the above DBU.

[0161] The content ratio of component C in the resin composition is not particularly limited, but the content of the catalyst relative to 100 parts by mass of the total of components A and B is, for example, preferably 0.00001 parts by mass or more and 20 parts by mass or less, more preferably 0.00002 parts by mass or more and 15 parts by mass or less, and even more preferably 0.00004 parts by mass or more and 10 parts by mass or less.

[0162] (solvent) The resin composition may further contain a solvent. The solvent is preferably a solvent that can dissolve component A and component B but does not condense with component A and component B, and more preferably a solvent that is unreactive with all of the contained components. One type of solvent may be used alone, or two or more types may be used in combination.

[0163] Examples of the solvent include aliphatic hydrocarbons, aromatic hydrocarbons, ethers, halogenated hydrocarbons, and ester-based solvents. More specific examples include methanol, ethanol, propanol, isopropanol, butanol, t-butyl alcohol, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, cyclopentyl methyl ether, methyl ethyl ketone, methyl isobutyl ketone, acetonitrile, propionitrile, benzonitrile, ethyl acetate, isobutyl acetate, butyl acetate, butyl propionate, ethyl lactate, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-oxypropionate, ethyl 3-oxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-hydroxyisobutyrate, 2-hydroxyisobutyrate, methyl ... Methyl propionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate, methyl hydroxyisobutyrate, acetylacetone, dioxane, ethylene glycol, diethyl ether, diethylene glycol, propylene glycol, dipropylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether ... Propylene glycol monophenyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monophenyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monophenyl ether, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, glycerin, cyclohexanol, 1,4-butanediol, triethylene glycol, tripropylene glycol, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, dipropylene glycol monoethyl ether acetate, dipropylene glycol Pyrene glycol monobutyl ether acetate, ethylene glycol monobutyl ether acetate, cyclohexanone, cyclopentanone, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, hexane, heptane, cyclohexane, benzene, toluene, xylene, anisole, benzaldehyde, benzonitrile, 1,3-dimethoxybenzene, acetophenone, 4'-methoxyacetophenone, 4'-ethoxyacetophenone, phenyl acetate, 3-methoxyphenol, 1,2-methylenedioxybenzene, 2-phenoxyethanol, diethylene glycol monophenyl ether, 1,2,4-trimethoxybenzene, 2'-hydroxyacetophenone, 1,4-diethoxybenzene, 1,3,Examples of suitable solvents include 5-trimethoxybenzene, t-butyl benzoate, benzyl alcohol, 1,4-dimethoxybenzene, 1,2,3-trimethoxybenzene, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,5-dimethylanisole, thioanisole, 4-ethylanisole, t-butylbenzene, 4-t-butyltoluene, 2-phenylanisole, t-anethole, 3,4-dimethoxytoluene, γ-butyrolactone, N,N-dimethylacetamide, N,N-dimethylformamide, N,N-diethylformamide, N-methyl-2-pyrrolidone, dimethylimidazolidinone, dimethyl sulfoxide, methylene chloride, chloroform, and carbon tetrachloride.

[0164] Among these, from the viewpoint of solubility in the resin composition, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, isobutyl acetate, butyl acetate, methyl 3-methoxypropionate, acetylacetone, propylene glycol monomethyl ether acetate, toluene, anisole, benzaldehyde, benzonitrile, tetrahydrofuran, diethylene glycol ethyl methyl ether, tetraethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, 1,3-dimethoxybenzene, acetophenone, 4'-methoxyacetophenone, 4'-ethoxyacetophenone, and phenyl acetate are preferred. , 3-methoxyphenol, 1,2-methylenedioxybenzene, 2-phenoxyethanol, 1,2,4-trimethoxybenzene, 2'-hydroxyacetophenone, 1,4-diethoxybenzene, 1,3,5-trimethoxybenzene, benzyl alcohol, 1,4-dimethoxybenzene, 1,4-diethoxybenzene, 1,2,3-trimethoxybenzene, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,5-dimethylanisole, thioanisole, 4-ethylanisole, t-butylbenzene, 4-t-butyltoluene, 2-phenylanisole, 3,4-dimethoxytoluene, N,N-dimethylacetamide, N,N-dimethylformamide, N,N-diethylformamide , or dimethyl sulfoxide is preferred.

[0165] The content of the solvent in the resin composition is not particularly limited, but is preferably 5 to 80 mass % relative to 100 mass % of the resin composition, more preferably 10 to 75 mass %, and even more preferably 15 to 70 mass %.

[0166] (Compounds containing specific elements) The resin composition may further contain a compound containing one or more of Ce, La, Pr, Nd, Y, and Fe (hereinafter also referred to as a "specific element-containing compound").

[0167] The valence of Ce, La, Pr, Nd, Y, and Fe may be divalent to tetravalent.

[0168] The specific element-containing compound may contain one or more of the elements Ce, La, Pr, Nd, Y, and Fe.

[0169] The specific element-containing compound having one or more of Ce, La, Pr, Nd, Y, and Fe may or may not be a hydrate.

[0170] Examples of specific element-containing compounds having one or more of Ce, La, Pr, Nd, Y, and Fe include cerium (IV) oxide, cerium (III) bromide, cerium (III) acetylacetonate, cerium (IV) methoxyethoxide, cerium (IV) isopropoxide, tris(isopropylcyclopentadienyl)cerium, tris(cyclopentadienyl)cerium, cerium silicate, diammonium cerium (IV) nitrate, cerium (IV) hydroxide, cerium (III) acetate, cerium (III) tungstate, cerium (III) oxalate, cerium (III) perchlorate, cerium (III) bromide, tetrakis(2,2,6,6-tetramethyl-3,5- Cerium compounds such as cerium(IV) heptanedionato, tris(1,2,3,4-tetramethyl-2,4-cyclopentadienyl)cerium(III), 2,4-pentanedionatocerium(III), trifluoroacetylacetonate cerium(III), cerium(III) fluoride, cerium(III) sulfide, cerium(III) phosphate, cerium(III) stearate, cerium(III) 2-ethylhexanoate, cerium(III) trifluoromethanesulfonate, cerium(III) chloride, cerium(IV) fluoride, cerium(IV) sulfate, cerium(III) iodide, cerium(III) nitrate, cerium(III) carbonate, and cerium(IV) trifluoromethanesulfonate;

[0171] Yttrium(III) oxide, yttrium(III) isopropoxide, yttrium(III) hexafluoroacetylacetonate, tris(cyclopentadienyl)yttrium, tris(butylcyclopentadienyl)yttrium, tris(methylcyclopentadienyl)yttrium, tris(n-propylcyclopentadienyl)yttrium, tris[N,N-bis(trimethylsilyl)amido]yttrium(III), yttrium(III) perchlorate, tris(2,2,6,6-tetramethyl-3,5-heptanedionato)yttrium(III), yttrium(I II) yttrium compounds such as acetylacetonate, yttrium (III) chloride, yttrium (III) oxalate, yttrium (III) acetate, yttrium (III) fluoride, yttrium (III) iodide, yttrium 2-ethylhexanoate (III), yttrium (III) nitrate, yttrium (III) sulfide, yttrium (III) bromide, yttrium trifluoromethanesulfonate (III), yttrium neodecanoate (III), yttrium (III) phosphate, yttrium (III) carbonate, yttrium (III) sulfate, and yttrium naphthenate (III);

[0172] Lanthanum(III) oxide, lanthanum(III) isopropoxide, lanthanum tris(hexamethyldisilazide), lanthanum(III) ethoxide, tris(cyclopentadienyl)lanthanum, tris[N,N-bis(trimethylsilyl)amido]lanthanum, tris(isopropylcyclopentadienyl)lanthanum, lanthanum carbonate, tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)lanthanum(III), lanthanum(III) perchlorate, tris(2,2,6,6-tetramethyl-3,5-heptanedionato)lanthanum(III), tris[N,N-bis(trimethyl lanthanum-containing compounds such as lanthanum(III) acetylacetonate, lanthanum chloride, lanthanum(III) sulfate, lanthanum(III) 2-ethylhexanoate, lanthanum(III) fluoride, lanthanum chloride, lanthanum(III) iodide, lanthanum boride, lanthanum(III) sulfide, lanthanum(III) bromide, lanthanum(III) nitride, lanthanum(III) trifluoromethanesulfonate, lanthanum(III) nitrate, lanthanum(III) carbonate, lanthanum(III) acetate, tris(N,N'-di-i-propylformamidinato)lanthanum(III), and lanthanum(III) phosphate;

[0173] Praseodymium(III) oxide, Praseodymium(IV) oxide, Praseodymium(III) hexafluoroacetylacetonate, Praseodymium(III) hexafluoro-2,4-pentanedionate, Praseodymium(III) acetylacetonate, Tris(2,2,6,6-tetramethyl-3,5-heptanedionato)praseodymium(III), Tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)praseodymium(III), Tris(isopropyl praseodymium compounds such as cyclopentadienylpraseodymium(III), isopropoxypraseodymium(III), praseodymium(III) chloride, praseodymium(III) fluoride, praseodymium(III) acetate, praseodymium(III) sulfate, praseodymium(III) bromide, praseodymium(III) iodide, praseodymium(III) phosphate, praseodymium(III) carbonate, praseodymium(III) trifluoromethanesulfonate, praseodymium(III) nitrate, and praseodymium(III) perchlorate;

[0174] Neodymium(III) oxide, neodymium(III) isopropoxide, neodymium(III) trifluoroacetylacetonate, tris(2,2,6,6-tetramethyl-3,5-heptanedionato)neodymium, tris(tetramethylcyclopentadienyl)neodymium, neodymium trifluoroacetylacetonate, tris(isopropylcyclopentadienyl)neodymium, neodymium(III) trifluoromethanesulfonate, neodymium fluoride, tris(cyclopentadienyl)neodymium, neodymium(III) perchlorate, neodymium(III) fluoride, neodymium(III) 2,4-pentanedionate, tris[N,N-bis(trimethylsilyl)acetate] neodymium compounds such as neodymium(III), tris(2,2,6,6-tetramethyl-3,5-heptanedionato)neodymium(III), tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)neodymium(III), neodymium(III) hexafluoroacetylacetonate, neodymium(III) 2-ethylhexanoate, neodymium(III) chloride, neodymium(III) titanate, neodymium(III) bromide, neodymium(III) iodide, neodymium(III) nitride, neodymium(III) acetate, neodymium(III) nitrate, neodymium carbonate, neodymium(III) sulfate, and neodymium(III) oxalate;

[0175] Iron(II) oxide, iron(III) oxide, iron(III) acetylacetonate, iron(III) ethoxide, iron(III) isopropoxide, iron(III) 2,4-pentanedionate, iron(III) trifluoroacetylacetonate, tris(2,2,6,6-tetramethyl-3,5-heptanedionato)iron(III), tris(hexafluoroacetylacetonate)iron(III), iron(III) sulfate, iron(II) hexacyanoate, iron(III), acetylacetonate Examples of iron compounds include iron(III) phosphate, ethylenediaminetetraacetic acid, iron(III)-sodium salt, ammonium iron(III) citrate, triammonium iron(III) trioxalate, iron(III) tris(2-ethylhexanoate), iron(III) phosphate, iron(III) fluoride, iron(III) chloride, iron(III) oxide hydroxide, iron(III) bromide, iron(III) trifluoromethanesulfonate, tetraphenylporphineiron(III) chloride, ammonium iron(III) hexacyanoferrate(II), iron(III) nitrate, potassium hexacyanoferrate(III), sodium pentacyanonitrosylferrate(III), iron(III) citrate, iron(III) diphosphate, iron(III) perchlorate, potassium iron(III) trisoxalate, 1,3,5-benzenetricarboxylic acid iron(III), and iron(III) phosphate.

[0176] In addition to the compounds listed above, compounds in which a siloxane skeleton is introduced into a specific element-containing compound containing one or more of Ce, La, Pr, Nd, Y, and Fe can also be used. For example, in the case of a compound containing cerium, a reaction product of a carboxylate of cerium and a siloxane compound containing a carboxylate can be mentioned, as described in JP 2020-132789 A.

[0177] Among these, cerium(III) acetylacetonate, cerium(III) nitrate, cerium(III) 2-ethylhexanoate, tris(cyclopentadienyl)cerium, yttrium(III) acetylacetonate, yttrium(III) nitrate, yttrium(III) 2-ethylhexanoate, tris(cyclopentadienyl)yttrium, lanthanum(III) acetylacetonate, lanthanum(III) 2-ethylhexanoate, tris(cyclopentadienyl)yttrium, Preferred are lanthanum (cyclopentadienyl), praseodymium (III) nitrate, neodymium (III) nitrate, neodymium (III) 2-ethylhexanoate, tris(cyclopentadienyl)neodynium, iron (III) acetylacetonate, iron (III) 2,4-pentanedionate, tris(2,2,6,6-tetramethyl-3,5-heptanedionato)iron (III), iron (III) acrylate, tris(2-ethylhexanoate)iron (III), and iron (III) nitrate.

[0178] As the specific element-containing compound, for example, a commercially available product such as "Octope R" (manufactured by Hope Pharmaceutical Co., Ltd.) may be used.

[0179] The content of the specific element-containing compound is not particularly limited, but in terms of the balance between heat resistance and solubility, it is preferably 5 ppm or more and less than 5,000 ppm, more preferably 7 ppm or more and less than 3,000 ppm, and even more preferably 10 ppm or more and less than 2,000 ppm, of the total mass of the resin composition excluding the solvent.

[0180] (Organopolysiloxane other than Component A and Component B) The resin composition may further contain an organopolysiloxane other than Component A and Component B. The other organopolysiloxanes may be used alone or in combination of two or more. The other organopolysiloxane is a compound having at least one structure of the following formulas (E-1) to (E-4), and does not contain a group that crosslinks with Component A.

[0181] [ka]

[0182] In formulas (E-1) to (E-4), R E are independently alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, cyclohexyl, octyl, nonyl, and decyl; aryl groups such as phenyl, tolyl, xylyl, and naphthyl; aralkyl groups such as benzyl, phenylethyl, and phenylpropyl; or groups in which at least one hydrogen atom is independently substituted with a halogen atom such as a fluorine atom, chlorine atom, or bromine atom, such as a chloromethyl group, chloropropyl group, bromoethyl group, or trifluoropropyl group. Among the above functional groups, groups that can have either a linear or branched chain structure, such as a propyl group, butyl group, or pentyl group, may have either a linear or branched chain structure. In the formulae (E-1) to (E-4), * represents a bonding site.

[0183] The structure of the organopolysiloxane may be a linear structure, a partially branched structure, a cyclic structure, or the like. Commercially available products include KF-96L, KF-96A, KF-96, KF-96H, KF-50, KF-54, KF-965, KF-968, KF-410, and KF-412 (all trade names) manufactured by Shin-Etsu Chemical Co., Ltd.; TSF451-0.65, TSF451-5A, TSF451-10, and TSF451-100 (all trade names) manufactured by Momentive Corporation; and WACKER (registered trademark) SILICONE FLUID AK0.65 to 10, WACKER (registered trademark) SILICONE FLUID AK20 to 5,000, WACKER (registered trademark) SILICONE FLUID AS100, WACKER (registered trademark) L053, WACKER (registered trademark) L060, and WACK ER (registered trademark) MQ803 (both are trade names) and the like.

[0184] The content of the other organopolysiloxane is 0.1 to 30 parts by mass, preferably 0.5 to 25 parts by mass, and more preferably 1 to 20 parts by mass, per 100 parts by mass of the total mass of the resin composition excluding the solvent.

[0185] (curing retarder) The resin composition may further contain a curing retarder from the viewpoint of storage stability. The curing retarder may be used alone or in combination of two or more.

[0186] The cure retarder may be, for example, a known compound used in a hydrosilylation reaction, such as a compound containing two or more alkenyl groups, a compound containing an aliphatic unsaturated bond, an organic phosphorus compound, a tin-based compound, or an organic peroxide.

[0187] Examples of compounds containing two or more alkenyl groups include disiloxanes and trisiloxanes containing vinyl or allyl groups at both ends, such as 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3-diallyl-1,1,3,3-tetramethyldisiloxane, 1,3-divinyl-1,3-dimethyl-1,3-diphenyldisiloxane, and 1,3-divinyl-1,1,3,3-tetraphenyldisiloxane, as well as vinyl-containing cyclic siloxanes such as 1,3,5,7-tetravinyltetramethylcyclotetrasiloxane.

[0188] Examples of compounds containing an aliphatic unsaturated bond include propargyl alcohols such as 3-methyl-1-dodecin-3-ol, 3,5-dimethyl-1-hexyn-3-ol, and 1-ethynyl-1-cyclohexanol, ene-yne ​​compounds, maleic anhydride, and maleic acid esters such as dimethyl maleate.

[0189] Examples of the organic phosphorus compound include triorganophosphines, diorganophosphines, organophosphones, and triorganophosphites. Examples of tin compounds include stannous halide dihydrate and stannous carboxylate, and examples of organic peroxides include di-t-butyl peroxide, dicumyl peroxide, benzoyl peroxide, and t-butyl perbenzoate.

[0190] Of these, 1,3-divinyldisiloxane, 1,3,5,7-tetravinyltetramethylcyclotetrasiloxane, or 1-ethynyl-1-cyclohexanol is preferred.

[0191] The content of the cure retarder is 10 to 200,000 times the content (mass) of component C, preferably 20 to 100,000 times, and more preferably 30 to 50,000 times.

[0192] (adhesion promoter) The resin composition according to the present embodiment may contain an adhesion promoter from the viewpoint of adhesiveness. One adhesion promoter may be used alone, or two or more adhesion promoters may be used in combination.

[0193] The adhesion promoter is preferably an organosilicon compound having a hydroxyl group, a hydrogen atom bonded to Si, or an alkoxy or epoxy group bonded to Si, and more preferably one having at least one alkoxy group bonded to Si. Such a compound can undergo a crosslinking reaction with other components in the resin composition while undergoing a bonding reaction with components such as a substrate on which the resin composition is laminated, thereby improving the adhesiveness of the resulting cured product. Furthermore, the adhesion promoter is From the viewpoint of heat resistance, etc., it is more preferable that the adhesion promoter has a silsesquioxane structure. Examples of such a suitable adhesion promoter include compounds represented by the following formula (Z). The adhesion promoter having a hydroxyl group, a hydrogen atom bonded to Si, or an alkoxy group bonded to Si may also function as component B. In this case, components that overlap with component B are treated as component B.

[0194] [ka]

[0195] In formula (Z), R G0 are independently the R in the above formula (2). 1 It is synonymous with R. G1 are independently the R in the above formula (3). 3 Q is independently a group represented by the following formula (Z1), formula (Z31), formula (Z32), formula (Z33), or formula (Z41), and may contain formula (Z2) as a linking group.

[0196] R G1 As the group, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms is preferred, and a methyl group or a phenyl group is more preferred.

[0197] [ka]

[0198] In the formulae (Z1), (Z2), (Z31), (Z32), (Z33), and (Z41), * represents a binding site, as described above.

[0199] In formula (Z2), R G2 are independently an alkyl group having 1 to 6 carbon atoms, a cyclopentyl group, a cyclohexyl group, or a phenyl group. g is an average value satisfying the range of 1 to 20. R G2 As the alkyl group, a methyl group and a phenyl group are preferred.

[0200] In formula (Z41), R G3 are independently a methyl group, an ethyl group, a butyl group, or an isopropyl group. G3 As the alkyl group, a methyl group or an ethyl group is preferred.

[0201] The amount of adhesion promoter added is preferably 0.1 to 10 parts by mass, more preferably 0.3 to 9 parts by mass, and even more preferably 0.5 to 8 parts by mass, per 100 parts by mass of the total mass of the resin composition excluding the solvent.

[0202] (filler) The resin composition may further contain a filler from the viewpoints of heat resistance, optical properties, thixotropy, etc. One type of filler may be used alone, or two or more types may be used in combination.

[0203] The filler is not particularly limited, and known materials can be used. The filler may have an amorphous structure or a crystalline structure. The combination of fillers is also not limited.

[0204] As the filler, for example, various phosphors and metal oxides can be suitably used.

[0205] There are various types of phosphors, such as those that emit green light, blue light, yellow light, or red light. Specific examples of phosphors include known phosphors such as organic phosphors, inorganic phosphors, fluorescent pigments, and fluorescent dyes. Examples of organic phosphors include allylsulfonamide-melamine formaldehyde co-condensation dyes and perylene-based phosphors, with perylene-based phosphors being preferred due to their long-term usability. Examples of preferred fluorescent materials include inorganic phosphors. Inorganic phosphors are described below.

[0206] Examples of phosphors that emit green light include [SrAl2O4:Eu], [Y2SiO5:Ce,Tb], and [MgAl 11 O 19 :Ce,Tb], [Sr7Al 12 O 25 :Eu], or [(at least one of Mg, Ca, Sr, Ba)Ga2S4:Eu], etc.

[0207] Examples of phosphors that emit light in blue include, for example, [Sr5(PO4)3Cl:Eu], [(SrCaBa)5(PO4)3Cl:Eu], [(BaCa)5(PO4)3Cl:Eu], [(at least one of Mg, Ca, Sr, Ba)2B5O9Cl:Eu,Mn], or [(at least one of Mg, Ca, Sr, Ba)(PO4)6Cl2:Eu,Mn], etc.

[0208] Examples of phosphors that emit light from green to yellow include at least yttrium-aluminum oxide phosphors activated with cerium, at least yttrium-gadolinium-aluminum oxide phosphors activated with cerium, at least yttrium-aluminum garnet oxide phosphors activated with cerium, or at least yttrium-gallium-aluminum oxide phosphors activated with cerium, etc. (so-called YAG-based phosphors). Specifically, [Ln3M5O 12 :R (Ln is at least one selected from Y, Gd, La, M contains at least one of Al and Ca, and R is a lanthanoid series .)], or [(Y1-xGax)3(Al1-yGay)5O 12 :R (R is at least one selected from Ce, Tb, Pr, Sm, Eu, Dy, Ho, 0 < Rx < 0.5, 0 < y < 0.5).] can be used.

[0209] Examples of phosphors that emit light in red include, for example, [Y2O2S:Eu], [La2O2S:Eu], [Y2O3:Eu], or [Gd2O2S:Eu].

[0210] Also, as phosphors that emit light corresponding to blue LEDs, YAG-based phosphors such as [Y3(Al,Ga)5O 12 :Ce,(Y,Gd)3Al5O 12 :Ce,Lu3Al5O 12 :Ce,Y3Al5O 12 :Ce], TAG-based phosphors such as [Tb3Al5O 12 :Ce], [(Ba,Sr)2SiO4:Eu]-based phosphors, [Ca3Sc2Si3O 12:Ce]-based phosphors, silicate-based phosphors such as [(Sr,Ba,Mg)2SiO4:Eu], nitride-based phosphors such as [(Ca,Sr)2Si5N8:Eu], [(Ca,Sr)AlSiN3:Eu], and [CaSiAlN3:Eu], and [Cax(Si,Al) 12 (O,N) 16 :Eu], as well as oxynitride phosphors such as [(Ba,Sr,Ca)Si2O2N2:Eu] and [Ca8MgSi4O 16 Cl2:Eu]-based phosphor or [SrAl2O4:Eu,Sr4Al 14 O 25 :Eu] and the like.

[0211] Among these, YAG-based phosphors, TAG-based phosphors, and silicate-based phosphors are preferably used in terms of luminous efficiency, brightness, etc. In addition to these, known phosphors can be used depending on the application and the desired luminescent color.

[0212] The content of the phosphor is preferably 1 to 90 parts by mass, and more preferably 2 to 50 parts by mass, per 100 parts by mass of the total mass of the resin composition excluding the solvent.

[0213] Next, the case where the filler is a metal oxide will be described. As the metal oxide, silica, alumina, yttrium oxide, zinc oxide, magnesium oxide, antimony oxide, titanium oxide, zirconium oxide, or the like is preferably used.

[0214] The content of the metal oxide in the resin composition is preferably 1 to 95 parts by mass, more preferably 1 to 90 parts by mass, and even more preferably 1 to 85 parts by mass, per 100 parts by mass of the total mass of the resin composition excluding the solvent.

[0215] When titanium oxide or aluminum oxide is used, it can also be used as a suitable reflector material. Polyphthalamide resin is widely used as a reflector material. However, it has been pointed out that polyphthalamide resin is prone to deterioration, particularly discoloration, over long periods of use, and this resin composition can solve this problem.

[0216] In the case of silica, either finely ground naturally occurring silica (natural silica) or industrially synthesized silica (synthetic silica) can be used. Natural silica is crystalline and therefore has a crystal axis. This allows for the expected optical characteristics of crystals, but its specific gravity is slightly higher than that of synthetic silica, which may affect its dispersion in the resin composition. Furthermore, when natural silica is obtained by crushing, it may result in particles of irregular shape or a material with a wide particle size distribution.

[0217] Synthetic silica includes wet synthetic silica and dry synthetic silica, but there is no particular limitation on the type of silica used. However, synthetic silica may contain water of crystallization regardless of the manufacturing method, and if this water of crystallization may have some effect on the resin composition or cured product, or various application components using these, it is preferable to select the silica taking into consideration the number of waters of crystallization.

[0218] Since synthetic silica is amorphous rather than crystalline, it has no crystal axes and the optical characteristics of crystals cannot be expected to be very significant. However, it can be used to control particle size distribution and to make the particle size extremely small. In particular, fumed silica has nano-order particle sizes and has excellent thixotropy.

[0219] Furthermore, silica generally has a large surface area and is a hydrophilic material (hydrophilic silica) due to the effect of silanols present on the surface, but it may also be made hydrophobic by chemical modification.

[0220] For example, from the viewpoint of being able to dissipate heat generated when the resin composition is used as an element, the resin composition preferably contains a heat-dissipating filler as a filler. One type of heat-dissipating filler may be used alone, or two or more types may be used in combination.

[0221] Examples of the heat dissipating filler include alumina (Al2O3), boron nitride (BN), aluminum nitride (AlN), silicon carbide (SiC), magnesium oxide (MgO), zinc oxide (ZnO), and aluminum hydroxide (Al(OH)3).

[0222] (ion scavenger) The resin composition may further contain an ion scavenger from the viewpoint of insulation reliability. One type of ion scavenger may be used alone, or two or more types may be used in combination.

[0223] The ion trapping agent is not particularly limited, and examples thereof include an anion trapper, a cation trapper, and a bi-ion trapper. Examples include DHT-4A (trade name) manufactured by Kyowa Chemical Industry Co., Ltd., and the IXE300 series, IXEPLAS-A series, and IXEPLAS-B series manufactured by Toagosei Co., Ltd. The average particle size of the ion trapping agent is preferably 0.1 to 3.0 μm, and the maximum particle size is preferably 10 μm or less.

[0224] The content of the ion scavenger is preferably 0.1 to 10 parts by mass, and more preferably 0.3 to 9 parts by mass, per 100 parts by mass of the total mass of the resin composition excluding the solvent.

[0225] (surfactant) The resin composition may further contain a surfactant for the purpose of controlling the wettability to the substrate. The surfactant may be used alone or in combination of two or more.

[0226] Specific examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, and Polyflow No. 95 (all trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbake 161, Disperbake 162, Disperbake 163, Disperbake 164, Disperbake 166, Disperbake 170, Disperbake 180, Disperbake 181, Disperbake 182, BYK-300, BYK-306, and BYK-307. K-310, BYK-320, BYK-330, BYK-342, BYK-344, BYK-346 (all trade names, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (all trade names, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (all trade names, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (all trade names, manufactured by Neos Co., Ltd.), TEGO Rad2100, 2200N, 2250, 2500, 2600, 2700 (all product names, manufactured by Evonik Japan Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (all trade names, manufactured by Mitsubishi Materials Corporation), Megafac F-171, Megafac F-177, Megafac F-475, Megafac F-477, Megafac F-556, Megafac R-08, Megafac R-30 (all trade names, manufactured by DIC Corporation) )), fluoroalkylbenzenesulfonate, fluoroalkylcarboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkylammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglycerin tetrakis (fluoroalkyl polyoxyethylene ether), fluoroalkyl trimethylammonium salt, fluoroalkyl aminosulfonate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene tridecyl ether, polyoxyethylene cetyl ether, polyoxyethylene Examples of the alkyl acrylate copolymer include diethylene stearyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonate, alkyl diphenyl ether disulfonate, and polyether-modified polydimethylsiloxane.

[0227] When the content of the surfactant is 0 to 3 parts by mass relative to 100 parts by mass of the total mass of the resin composition excluding the solvent, the coating property onto the substrate tends to be excellent.

[0228] (Flame retardant) The resin composition may further contain a flame retardant from the viewpoint of flame retardancy. The resin composition preferably contains a flame retardant, since the resulting cured film has high flame retardancy. The flame retardant is not particularly limited as long as it is a compound that can impart flame retardancy, but from the viewpoints of low toxicity, low pollution, and safety, it is preferable to use an organic phosphorus flame retardant. One type of flame retardant may be used alone, or two or more types may be used in combination.

[0229] Examples of organophosphorus flame retardants include triphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, cresyl phenyl phosphate, 2-ethylhexyl diphenyl phosphate, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, and condensed 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide.

[0230] The content of the flame retardant is preferably 0 to 50 parts by mass relative to 100 parts by mass of the total mass of the resin composition excluding the solvent.

[0231] (UV absorbers, light stabilizers) The resin composition may contain an ultraviolet absorber or a light stabilizer (HALS) to prevent deterioration due to light. These components may be used alone or in combination of two or more.

[0232] Examples of ultraviolet absorbers include benzotriazole compounds such as 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-(3,5-di-t-butyl-2-hydroxyphenyl)benzotriazole, 2-(3,5-di-t-butyl-2-hydroxyphenyl)-5-chlorobenzotriazole, and 2-(3,5-di-t-amyl-2-hydroxyphenyl)benzotriazole; triazine compounds such as 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[(hexyl)oxy]phenol; benzophenone compounds such as 2-hydroxy-4-n-octyloxybenzophenone; and oxalic acid anilide compounds such as 2-ethoxy-2'-ethyloxalic acid bisanilide. Examples include:

[0233] Examples of light stabilizers (HALS) include TINUVIN (registered trademark) 5100, TINUVIN 292 (compound name: bis(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, methyl (1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate), and TINUVIN 152 (compound name: 2,4-bis[N-butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-piperidinyl) sebacate]). TINUVIN 144 (compound name: bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate), TINUVIN 123 (compound name: decanedioic acid, bis(2,2,6,6-tetramethylpiperidin-4-yl)amino)-6-(2-hydroxyethylamine)-1,3,5-triazine), Examples of the polymerizable compound include a reaction product of butanedioic acid polymer (4-hydroxy-2,2,6,6-tetramethylpiperidinyl) ester (in the presence of 1,1-dimethylethyl hydroperoxide and octane), TINUVIN111FDL (approximately 50%, TINUVIN622, compound name: (butanedioic acid polymer in the presence of (4-hydroxy-2,2,6,6-tetramethylpiperidinyl-yl)ethanol), approximately 50%, CHIMASSORB119, compound name: N-N'-N''-N'''-tetrakis(4,6-bis(butyl-(N-methyl-2,2,6,6-tetramethylpiperidin-4-yl)amino)triazin-2-yl)-4,7-diazadecane-1,10-diamine) (all manufactured by BASF), and the Adeka STAB LA series (manufactured by Adeka Corporation), specifically LA-52, LA-57, LA-62, and LA-67.

[0234] The content of each of the ultraviolet absorber and light stabilizer is preferably 0 to 20 parts by mass relative to 100 parts by mass of the total mass of the resin composition excluding the solvent.

[0235] (antioxidant) The resin composition may further contain an antioxidant to prevent oxidation of the resulting cured film, etc. One type of antioxidant may be used alone, or two or more types may be used in combination.

[0236] Examples of antioxidants include dibutylhydroxytoluene, 2,6-t-butylphenol, 2,2'-methylenebis(6-t-butyl-4-ethylphenol, tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, tris(3,5-t-butyl-4-hydroxybenzyl) isocyanurate, 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane, 4,4'-butylidenebis(6-t-butyl) -m-cresol), 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate stearyl, tetrakis[3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionic acid]pentaerythritol, 2,2'-dimethyl-2,2'-(2,4,8,10-tetraoxaspiro[5,5]undecane-3,9-diyl)dipropane-1,1'-diyl bis[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propanoate ], 2,4,6-tris(3',5'-di-t-butyl-4'-hydroxybenzyl)mesitylene, pentaerythritol tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], triethylene glycol-bis-[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], octadecyl- Hindered phenol compounds such as 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate or 3,5-di-t-butyl-4-hydroxybenzylphosphonate diethyl ester; amine compounds such as dinonyldiphenylamine, octylbutyldiphenylamine, n-butylamine, triethylamine, or diethylaminomethyl methacrylate; bis(dibutyldithiocarbamate)methylene, pentaerythritol tetrakis[3-lanthanide] sulfur compounds such as dilauryl thiopropionate, phenothiazine, dilauryl-3,3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, or distearyl-3,3'-thiodipropionate; or triphenyl phosphite, diphenyl isodecyl phosphite, phenyl diisodecyl phosphite, tris(nonylphenyl) phosphite, diisodecyl pentaerythritol phosphite, tris(2,4-di-t-butylphenyl) phosphite, cyclic neopentanetetraylbis(octadecyl) phosphite, cyclic neopentanetetraylbi(2,4-di-t-butylphenyl) phosphite, cyclic Examples of phosphorus-based compounds include neopentanetetraylbi(2,4-di-t-butyl-4-methylphenyl)phosphite, bis[2-t-butyl-6-methyl-4-{2-(octadecyloxycarbonyl)ethyl}phenyl]hydrogen phosphite, and oxaphosphaphenanthrene oxides (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(3,5-di-t-butyl-4-hydroxybenzyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, or 10-decyloxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide).

[0237] The content of the antioxidant is preferably 0 to 10 parts by mass relative to 100 parts by mass of the total mass of the resin composition excluding the solvent.

[0238] (organic resin) The resin composition may further contain an organic resin. By selecting the type of organic resin, further improvement of the functionality can be achieved. One type of organic resin may be used alone, or two or more types may be used in combination.

[0239] Examples of organic resins include acrylic resins, epoxy resins, polyimide resins, cyanate resins, maleimide resins, benzoxazine resins, phenoxy resins, unsaturated polyester resins, phenolic resins, melamine resins, urethane resins, and silicone resins. Among these, it is preferable that a resin that is cured by a curing agent such as an epoxy resin is contained together with the curing agent. Examples of the curing agent for the epoxy resin include an acid anhydride compound, a phenolic compound, an amine compound, a thermal or photoacid generator such as a sulfonium salt or an iodonium salt, a photosensitizer, and an active ester compound.

[0240] (photosensitizer) The resin composition may further contain a sensitizer. By selecting the type of sensitizer, further improvement in functionality can be achieved. One type of sensitizer may be used alone, or two or more types may be used in combination. Examples of sensitizers include anthracene-based compounds, thioxanthone-based compounds, cyanine-based compounds, merocyanine-based compounds, coumarin-based compounds, benzylidene ketone-based compounds, squarium-based compounds, (thia)pyrylium-based compounds, porphyrin-based compounds, coumarin-based compounds, pyrarizone-based compounds, oxazole-based compounds, thiophene-based compounds, and naphthalene-based compounds. Examples of commercially available products include the Anthracure UVS series, such as Anthracure UVS-1331, Anthracure UVS-1101, Anthracure UVS-581, and Anthracure UVS-2171, manufactured by Air Water Performance Chemicals Inc., and NF-CO-01, NF-CO-02, NF-CO-02-AC, NF-CO-05, NF-CO-06, NF-PY-01, NF-PY-02, NF-TH-01, NF-NA-01, NF-py-A, NF-py-B, NF-py-C, NF-OX-A, and NF-CO-A, manufactured by Nippon Chemical Industry Co., Ltd. The content of each photosensitizer is preferably 0.001 to 40 parts by mass relative to 100 parts by mass of the total mass of component C, which is an optional component in the resin composition.

[0241] <Method of manufacturing resin composition> The method for producing the resin composition is not particularly limited, and the resin composition can be obtained, for example, by mixing the components using a known mixer. For example, a method may be used in which predetermined amounts of component A, and optional components B and C, and other components are mixed at room temperature or under heating using a mixer such as a stirrer, homodisper, homomixer, universal mixer, planetary mixer, kneader, three-roll mill, or bead mill.

[0242] The resin composition may also be produced by preparing and mixing together the components of a two-component or three-component type.

[0243] Another embodiment of the method for producing a resin composition according to the present invention is a method for producing a resin composition using an organosilicon compound produced by the method for producing an organosilicon compound described above. Specifically, the method includes a compound production step in which a compound represented by the above formula (4) (a compound containing a silsesquioxane skeleton) is reacted with at least one of a compound represented by the above formula (5) and a compound represented by the above formula (6) at a temperature of 20°C or higher and 70°C or lower to obtain a silicon compound. This embodiment may also include a step other than the compound production step. The step other than the compound production step may include, for example, a mixing step in which the components constituting the resin composition are mixed.

[0244] A resin composition according to another embodiment of the present invention is a resin composition obtained by the above-described production method. The above-described conditions for the resin composition can be similarly applied to this resin composition.

[0245] <Cured product> A cured product according to another embodiment of the present invention is a cured product obtained by curing the resin composition described above. The curing method for obtaining the cured product is not particularly limited, and can be performed by a known method, for example, by treatment such as heating or light irradiation.

[0246] Since the viscosity change rate over time of the resin composition using component A is small, it is preferable to form the above-mentioned resin composition into a film and cure it to obtain a cured product as a silicone film. The film of the resin composition can be formed by a known method of applying it to a substrate or a sheet. In addition, the curing of the film of the resin composition can be determined based on conditions such as crosslinking. For example, a silicone film can be formed by heating the resin composition or its film. An example of the curing method will be shown below, but the present invention is not limited to this method.

[0247] [Curing method] The cured product can be obtained, for example, by applying the above-mentioned resin composition to the surface of a substrate by a desired printing method (screen printing, letterpress printing, intaglio printing, lithography, inkjet printing, etc.), a dispenser, spin coating, or the like, drying the composition as necessary to form a coating film (coating film forming step), and then subjecting the resulting coating film to a heating step to cure the coating film.

[0248] [Coating film formation process] In the coating film forming step, the resin composition is applied to the surface of a substrate to form a coating film, such as a semiconductor substrate (e.g., aluminum substrate, glass substrate), copper substrate, copper alloy substrate, polyimide substrate, ceramic substrate, printed circuit board, stainless steel substrate, or a fiber-reinforced substrate (e.g., CFRP, GFRP, etc.).

[0249] In the case of a resin composition containing a solvent, a drying treatment may be carried out to remove the solvent before curing. Although it depends on the composition of the resin composition, the drying temperature is usually 50 to 250°C, and the drying time is usually 5 to 120 minutes. By such a drying treatment, it is possible to form a coating film on the substrate that can retain its shape.

[0250] [Heating process] After the coating film is formed, it is usually heated at 70 to 350°C for 10 to 200 minutes.

[0251] The term "cured product" refers to a product in which a crosslinking reaction or the like has occurred in at least a portion of the components of the resin composition, resulting in reduced fluidity, and is not limited to a completely cured product. In other words, cured products also include those that have elasticity or viscosity, and those that soften or melt when heated.

[0252] The cured product may be a B-stage cured product. A B-stage cured product refers to a cured product in a semi-cured state. Specifically, a B-stage cured product is preferably solid at 25°C and has a softening point in the range of 50°C to 200°C. A B-stage cured product can be obtained by heating the resin composition, for example, at a temperature in the range of 100 to 350°C for 1 to 5 hours.

[0253] The shape of the cured product is not particularly limited, and may be a shape obtained by curing the resin composition into a film, or a molded product obtained by curing the resin composition into a predetermined shape using a mold, etc. The shape of the cured product is not particularly limited, and may be, for example, a film, sheet, powder, granules, or plate.

[0254] <Application> The uses of the above-mentioned compositions and cured products are not particularly limited, but because the above-mentioned organosilicon compounds have a structure derived from a compound containing a silsesquioxane skeleton, they are expected to have excellent effects in various physical properties such as heat resistance, electrical insulation, transparency, adhesion, solubility, mechanical strength, gas permeability, dielectric constant, flame retardancy, and processability, and to be usable in a wide range of applications.

[0255] Specifically, the cured product described above has excellent heat resistance and insulating properties, and therefore can be suitably used, for example, in electrical and electronic materials. Specifically, it can be suitably used as a substrate coating film for forming a metal elution prevention film, a gas barrier film, an anti-reflection film, or the like; an insulating film, an encapsulant, a light-emitting diode encapsulant, an anti-fouling film, a microlens, a light guide plate, a wavelength conversion layer, a light reflector, a buffer material, a sealant, an optical waveguide material, a planarizing film, a protective film, an underfill material, a die attach material, or other components of elements, display substrates, or printed wiring boards; optical resins; optical films; contact lenses; etc. When used as an insulating film in elements, etc., the insulating film may be, for example, an insulating film covering a chip or element, or may be an insulating film for rewiring. Furthermore, the cured product has excellent transparency and can be suitably used as lenses, including the various lenses used in the above applications, optical filters, or cover glasses. The above-mentioned composition can be used as a material for forming the above-mentioned various members.

[0256] Furthermore, the composition described above has excellent adhesive properties and can therefore be suitably used as an adhesive.

[0257] When the above-described composition and cured product are used as components of an element, the type of the element is not particularly limited, and may be a semiconductor element, an integrated circuit device, an actuator element (a piezoelectric element such as a MEMS element, etc.), or the like. The semiconductor device can be used as an optical element, a thermoelectric element, a passive element (capacitor, inductor, resistor, etc.), or the like. An example of an application in which the element is used is a device for moving in at least one region selected from the group consisting of land, underground, air, space, sea, and underwater. Specific examples of such devices include vehicles, ships, and aircraft, which may be manned or unmanned (drone) devices. Other examples of applications in which the element is used include electronic devices selected from the group consisting of home appliances, information devices, video devices, audio devices, and amusement devices, as well as hybrid devices thereof.

[0258] The type of semiconductor element is not particularly limited, and examples include semiconductor elements such as power semiconductor elements, various transistors such as junction field effect transistors (JFETs), various diode elements such as light-emitting diodes, metal oxide semiconductor field effect transistors (MOSFETs), Schottky source / drain MOSFETs, avalanche multiplication photoelectric conversion elements, solar cell elements, sensor elements, touch sensor elements, switching elements, resistance change memories, power conversion elements, and display elements.

[0259] Furthermore, as described above, the above-described composition and cured product have excellent transparency, making them suitable as materials for constituting all or part of optical components. In this specification, "optical component" is used as a general term for components having optical functions. Optical components are broadly classified into standalone optical elements that have the function of changing the properties of light by themselves, and electro-optical elements that perform a predetermined function through interaction with electrons.

[0260] A standalone optical element has the function of changing the transmission characteristics or reflection characteristics of incident light, and specific examples of its functions include polarization adjustment, light intensity adjustment, color tone adjustment, or light path adjustment. Specific examples of standalone optical elements include polarizing components, coloring components, dimming components, wavelength conversion components, light-blocking components, light-attenuating components, reflecting components, lenses, and mirrors. Electro-optical elements have the function of changing the characteristics of incident light based on an electrical signal, or the function of converting an optical signal into an electrical signal based on photoelectric conversion, or of emitting light based on an electrical signal. Specific examples of elements with the former function include electrochromic elements and liquid crystal elements. Specific examples of elements with the latter function include light-emitting elements such as LEDs and OLEDs.

[0261] Furthermore, because the above-described compositions and cured products have transparency and adhesive properties, they can be suitably used as protective members or joining members placed on or near the optical path, similar to conventional optically transparent pressure-sensitive adhesives. Conventional optically transparent adhesive films (OCAs) are basically made of adhesive materials, and therefore it is not easy for them to have high heat resistance. However, the above-described compositions and cured products also have excellent heat resistance, and therefore can be suitably used in applications requiring a large amount of transmitted light, such as large projectors for projection mapping. When the cured product is a B-stage cured product, the above-described cured product or a resin-containing component containing the cured product may be used as a substitute for conventional OCA.

[0262] Furthermore, from the viewpoint of transparency, it can be suitably used as a lens, an optical filter, a cover glass, or the like, and from the viewpoint of adhesiveness, it can be suitably used as an adhesive.

[0263] Another example of the use of the cured product described above is when a composite member comprising a resin-containing member containing the cured product and another member (first member) provided in contact with the resin-containing member constitutes part of an electrical element. Because the cured product described above has various excellent properties as described above, the resin-containing member may be composed solely of the cured product, but may also contain other materials to achieve the desired properties. Examples of such materials include hard or soft resin materials and non-resin materials such as inorganic fillers.

[0264] Specific examples of electrical elements include integrated circuit devices, power elements, switching elements, sensor elements, actuator elements such as MEMS, the aforementioned electro-optical elements, storage elements such as capacitors, inductors such as choke coils and transformers, and resistors. Examples of applications in which such electrical elements are used include devices for moving in at least one region selected from the group consisting of land, underground, air, space, sea, and underwater. Specific examples of such devices include vehicles, ships, and aircraft, which may be manned or unmanned (drone) devices. Other examples of applications in which electrical elements are used include electrical devices selected from the group consisting of home appliances, information devices, video devices, audio devices, amusement devices, and hybrid devices thereof.

[0265] One example of the use of the resin-containing member in the composite member is a protective film that covers at least a portion of the first member. Specific examples of the first member include semiconductor substrates such as Si, GaN, and SiC; metal substrates such as copper-based materials, aluminum-based materials, and steel materials typified by stainless steel; ceramic substrates such as alumina; glass substrates; and resin substrates. The resin-containing member containing the cured product described above has excellent adhesion to such substrates and can therefore be suitably used as a protective film.

[0266] In particular, the cured product described above contains siloxane bonds (Si-O-Si) such as silsesquioxane groups or siloxane groups, and therefore has superior heat resistance compared to resin materials that do not contain such bonds, and therefore has particularly excellent adhesion to glass substrates, semiconductor substrates, and metal substrates. Furthermore, because the cured product described above contains a certain proportion of siloxane bonds (Si-O-Si), it generates less greenhouse gases per unit weight compared to cured resin products that do not contain such bonds (epoxy resins are a specific example of this).

[0267] The first component may be a wiring substrate having wiring provided on a base material. In this case, the protective film made of the resin-containing material containing the cured product preferably has insulating properties, and in this case, serves as an insulating film covering the wiring. Because the cured product has excellent insulating properties, even when the resin-containing material is made of the cured product, it can function appropriately as a protective film.

[0268] In this case, wiring may be further provided on the protective film to form a laminated wiring structure. In this case, the resin-containing material containing the cured product described above is positioned as a planarizing film, a rewiring insulating film, or an interlayer insulating film in a member having a multilayer wiring structure.

[0269] The first member may be a base material on which an integrated circuit is formed. In this case, too, the protective film made of a resin-containing material preferably has insulating properties, and in this case, the protective film is positioned as a buffer coat that covers the integrated circuit.

[0270] Another specific example of the use of the resin-containing member in the composite member described above is as a sealing material that takes advantage of its adhesiveness. In this case, specific examples of the first member are integrated circuit devices, power elements, switching elements, and sensor elements, and because the resin-containing member has excellent heat resistance, it can be used as a substitute for sealing materials conventionally made of epoxy resins, particularly in high-temperature environments.

[0271] The composite member may include a second member that is different from the first member and that is in contact with the resin-containing member. In this case, the resin-containing member has a bonding function for bonding the first member and the second member. The specific examples of the first member described above also apply to the specific examples of the second member.

[0272] As a specific example of the use of resin-containing materials focusing on the joining function, a first member and a second member are Examples of filler materials include a filler placed in the gap between the first and second members. Because the cured product described above has high adhesion to the first and second members, a resin-containing member containing the cured product can properly maintain the gap between the first and second members even when subjected to external force. An example of a filler material is an underfill material. Some underfill materials contain silica particles as a filler, and the cured product described above has siloxane bonds (Si-O-Si), so it also has excellent adhesion to the silica particles. Therefore, an underfill material containing silica particles is a particularly suitable example of an application for a resin-containing member.

[0273] Another specific example of a resin-containing member that focuses on the bonding function is a sealant that is provided to cover the gap between a first member and a second member. The cured product described above has high adhesion to the first member and the second member and is flexible, so that the resin-containing member containing the cured product can maintain contact with the first member and the second member even when subjected to an external force.

[0274] In applications where the resin-containing member performs a bonding function, the first member may be a mounting substrate, and the second member may be an electric element equipped with electrodes. Electric elements may generate heat or vibrate when energized, but the cured product described above has excellent heat resistance, excellent adhesion, and high flexibility, making it possible to properly maintain the electric element attached to the mounting substrate. One such application example is a die attach material.

[0275] Furthermore, in recent years, there has been an increasing demand for higher output and higher density mounting of electrical elements, and mounting techniques are being required to have higher heat resistance, and the resin-containing member containing the cured product described above can meet this demand. One mounting technique that meets this need for higher heat resistance is the POL (Power Overlay) technology, and the resin-containing member containing the cured product described above can be suitably used as a joining member for this application.

[0276] In one example of POL technology, an adhesive layer is formed on a substrate made of a heat-resistant resin such as polyimide, and the electrode side of an electrical element is brought into contact with this adhesive layer to secure the electrical element to the substrate. Holes are then drilled (through-hole formation by removal processing) through the back surface of the substrate opposite the surface on which the electrical element is mounted (front surface) to expose the electrode surface. The through-holes are then filled with a conductive material such as copper, and a wiring pattern is formed on the back surface using plating or other techniques. The back surface on which the wiring pattern is formed is covered with an insulating film, and then portions of the insulating film are removed to form external electrodes connected to the wiring pattern. The electrical element on the front surface is then sealed with a resin-based material, and a heat dissipation member is attached as needed.

[0277] The resin-containing member containing the cured product described above has excellent adhesion and high heat resistance, making it suitable for use as an adhesive layer formed on the front surface of a substrate. It can also be used as a resin-based material for covering electrical elements that generate heat when energized. In this case, it may be preferable to use a resin-containing member in which a material with high thermal conductivity, such as alumina, is dispersed, taking advantage of the excellent heat resistance and adhesion of the cured product described above. [Example]

[0278] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples.

[0279] [Synthesis of Organosilicon Compounds] (Synthesis of organosilicon compound 1-1) Under a nitrogen atmosphere, a silsesquioxane derivative (compound A-1) (170 g), octamethylcyclotetrasiloxane (compound A-2) (63.8 g), toluene (193 g), and 4-methyltetrahydropyran (MTHP) (48.1 g) were placed in a reactor and heated to 55°C. After adding sulfuric acid (7.39 g) dropwise, the mixture was stirred for 24 hours. Water was poured into the reaction mixture, and the aqueous layer was extracted with toluene. The combined organic layer was washed with water, aqueous sodium bicarbonate solution, and saturated saline, and then dried over anhydrous sodium sulfate. This solution was concentrated under reduced pressure, and the residue was purified by reprecipitation (2-propanol:toluene = 5:1, weight ratio) to obtain organosilicon compound (1-1) (178 g). GPC analysis showed that the colorless, transparent solid obtained had a weight average molecular weight of 98,000 and a number average molecular weight of 38,000. 1 H-NMR analysis revealed that in the following formula, the average value of n was 4.1, with 18% of structures where n = 1 and 23% where n = 2. The proportion of structures where n = 1 and the proportion of structures where n = 2 represent the proportion of the number of structures represented by formula (B) where m = 1 or m = 2, respectively, relative to the total number of structures represented by formula (B). This also applies to the following examples and comparative examples.

[0280] [ka]

[0281] (Synthesis of comparative organosilicon compound P-1) Under a nitrogen atmosphere, a silsesquioxane derivative (compound A-1) (300 g), octamethylcyclotetrasiloxane (compound A-2) (125 g), toluene (350 g), and 4-methyltetrahydropyran (87.6 g) were placed in a reactor and heated to 85°C. Sulfuric acid (13.2 g) was added dropwise, followed by stirring for 6 hours. Water was poured into the reaction mixture, and the aqueous layer was extracted with toluene. The combined organic layer was washed with water, aqueous sodium bicarbonate, and saturated saline, and then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by reprecipitation (2-propanol:toluene:ethyl acetate = 21:3:1, weight ratio) to obtain organosilicon compound (P-1) (326 g). GPC analysis revealed that the resulting colorless, transparent solid had a weight-average molecular weight of 96,000 and a number-average molecular weight of 36,000. 1H-NMR analysis revealed that in the following formula (P-1), the average value of n was 4.2, the proportion of structures where n=1 was 23%, and the proportion of structures where n=2 was 22%.

[0282] [ka]

[0283] (Synthesis of organosilicon compound 1-2) Under a nitrogen atmosphere, a silsesquioxane derivative (compound A-1) (150 g), octamethylcyclotetrasiloxane (compound A-2) (54.4 g), toluene (43.9 g), and 4-methyltetrahydropyran (176 g) were placed in a reactor and heated to 50°C. Sulfuric acid (15.1 g) was added dropwise, and the mixture was stirred for 6 hours. Water was poured into the reaction mixture, and the aqueous layer was extracted with toluene. The combined organic layer was washed with water, aqueous sodium bicarbonate, and saturated saline, and then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by reprecipitation (2-propanol:toluene = 6:1, weight ratio) to obtain organosilicon compound (1-2) (157 g). GPC analysis revealed that the resulting colorless, transparent solid had a weight-average molecular weight of 37,000 and a number-average molecular weight of 20,000. 1 H-NMR analysis revealed that in the following formula (1-2), the average value of n was 4.1, the proportion of structures where n=1 was 19%, and the proportion of structures where n=2 was 22%.

[0284] [ka]

[0285] (Synthesis of organosilicon compounds 1-3) Under a nitrogen atmosphere, a silsesquioxane derivative (compound A-1) (150 g), octamethylcyclotetrasiloxane (compound A-2) (54.4 g), toluene (110 g), and 4-methyltetrahydropyran (110 g) were placed in a reactor and heated to 50°C. Sulfuric acid (15.1 g) was added dropwise, and the mixture was stirred for 24 hours. Water was poured into the reaction mixture, and the aqueous layer was extracted with toluene. The combined organic layer was washed with water, aqueous sodium bicarbonate, and saturated saline, and then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by reprecipitation (2-propanol:toluene = 6:1, weight ratio) to obtain organosilicon compound (1-3) (157 g). GPC analysis revealed that the resulting colorless, transparent solid had a weight-average molecular weight of 54,000 and a number-average molecular weight of 26,000. 1 H-NMR analysis revealed that in the following formula (1-3), the average value of n was 4.4, the proportion of structures where n=1 was 15%, and the proportion of structures where n=2 was 20%.

[0286] [ka]

[0287] (Synthesis of comparative organosilicon compound P-2) Under a nitrogen atmosphere, a silsesquioxane derivative (compound A-1) (450 g), octamethylcyclotetrasiloxane (compound A-2) (163 g), toluene (330 g), and 4-methyltetrahydropyran (330 g) were placed in a reactor and heated to 90°C. Sulfuric acid (45.4 g) was added dropwise, and the mixture was stirred for 6 hours. Water was poured into the reaction mixture, and the aqueous layer was extracted with toluene. The combined organic layer was washed with water, aqueous sodium bicarbonate, and saturated saline, and then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by reprecipitation (2-propanol:toluene = 6:1, weight ratio) to obtain organosilicon compound (P-2) (440 g). GPC analysis revealed that the resulting colorless, transparent solid had a weight-average molecular weight of 39,000 and a number-average molecular weight of 22,000. 1H-NMR analysis revealed that in the following formula (P-2), the average value of n was 4.3, the proportion of structures where n=1 was 21%, and the proportion of structures where n=2 was 19%.

[0288] [ka]

[0289] (Synthesis of organosilicon compounds 1-4) Under a nitrogen atmosphere, a silsesquioxane derivative (compound A-1) (15.0 g), octamethylcyclotetrasiloxane (compound A-2) (3.4 g), toluene (9.8 g), and 4-methyltetrahydropyran (9.8 g) were placed in a reactor and heated to 55°C. Sulfuric acid (1.2 g) was added dropwise, and the mixture was stirred for 7 hours. Water was poured into the reaction mixture, and the aqueous layer was extracted with toluene. The combined organic layer was washed with water, aqueous sodium bicarbonate, and saturated saline, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by reprecipitation (2-propanol:toluene = 6:1, weight ratio) to obtain organosilicon compound (1-4) (13.9 g). GPC analysis revealed that the resulting colorless, transparent solid had a weight-average molecular weight of 57,000 and a number-average molecular weight of 26,000. 1 H-NMR analysis revealed that in the following formula (1-4), the average value of n was 3.0, the proportion of structures where n=1 was 23%, and the proportion of structures where n=2 was 26%.

[0290] [ka]

[0291] (Synthesis of organosilicon compounds 1-5) Under a nitrogen atmosphere, a silsesquioxane derivative (compound A-1) (30.0 g), octamethylcyclotetrasiloxane (compound A-2) (6.8 g), toluene (20.9 g), and 4-methyltetrahydropyran (20.9 g) were placed in a reactor and heated to 55°C. Sulfuric acid (5.0 g) was added dropwise, and the mixture was stirred for 6 hours. Water was poured into the reaction mixture, and the aqueous layer was extracted with toluene. The combined organic layer was washed with water, aqueous sodium bicarbonate solution, and saturated saline, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by reprecipitation (2-propanol:toluene = 6:1, weight ratio) to obtain organosilicon compound (1-5) (25.9 g). GPC analysis showed that the colorless, transparent solid obtained had a weight average molecular weight of 60,000 and a number average molecular weight of 30,000. 1 H-NMR analysis revealed that in the following formula (1-5), the average value of n was 3.2, the proportion of structures where n=1 was 20%, and the proportion of structures where n=2 was 27%.

[0292] [ka]

[0293] (Synthesis of organosilicon compounds 1-6) Under a nitrogen atmosphere, a silsesquioxane derivative (compound A-1) (30.0 g), octamethylcyclotetrasiloxane (compound A-2) (6.8 g), toluene (22.1 g), and 4-methyltetrahydropyran (22.1 g) were placed in a reactor and heated to 40°C. Sulfuric acid (7.4 g) was added dropwise, and the mixture was stirred for 4 hours. Water was poured into the reaction mixture, and the aqueous layer was extracted with toluene. The combined organic layer was washed with water, aqueous sodium bicarbonate, and saturated saline, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by reprecipitation (2-propanol:toluene = 6:1, weight ratio) to obtain organosilicon compound (1-6) (32.0 g). GPC analysis revealed that the resulting colorless, transparent solid had a weight-average molecular weight of 61,000 and a number-average molecular weight of 31,000. 1 H-NMR analysis revealed that in the following formula (1-6), the average value of n was 3.2, the proportion of structures where n=1 was 15%, and the proportion of structures where n=2 was 29%.

[0294] [ka]

[0295] (Synthesis of organosilicon comparative compound P-3) Under a nitrogen atmosphere, a silsesquioxane derivative (compound A-1) (300.0 g), octamethylcyclotetrasiloxane (compound A-2) (67.6 g), toluene (195.6 g), and 4-methyltetrahydropyran (195.6 g) were placed in a reactor and heated to 85°C. Sulfuric acid (23.6 g) was added dropwise, and the mixture was stirred for 6 hours. Water was poured into the reaction mixture, and the aqueous layer was extracted with toluene. The combined organic layer was washed with water, aqueous sodium bicarbonate, and saturated saline, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by reprecipitation (2-propanol:toluene = 6:1, weight ratio) to obtain organosilicon compound (P-3) (316.1 g). GPC analysis revealed that the resulting colorless, transparent solid had a weight-average molecular weight of 33,000 and a number-average molecular weight of 18,000. 1 H-NMR analysis revealed that in the following formula (P-3), the average value of n was 3.0, the proportion of structures where n=1 was 27%, and the proportion of structures where n=2 was 24%.

[0296] [ka]

[0297] [Preparation of Resin Composition] The components shown in Tables 1 to 3 were uniformly mixed and dissolved in the amounts shown in Tables 1 to 3 to prepare resin compositions (Examples 1 to 19 and Comparative Examples 1 to 7).

[0298] The components used other than the above organosilicon compound (component A) are listed below.

[0299] (Compound having a functional group capable of chemically bonding with an organosilicon compound (Component B)) MS51: MKC Silicate MS51 (trademark), manufactured by Mitsubishi Chemical Corporation, tetramethoxysilane average pentamer ES40: Oligomer of tetraethoxysilane, manufactured by Colcoat Co., Ltd., average degree of polymerization: 4-5 Trimethoxyphenylsilane: manufactured by Tokyo Chemical Industry Co., Ltd. 1,6-bis(trimethoxysilyl)hexane: manufactured by Tokyo Chemical Industry Co., Ltd. Triacetoxyphenylsilane: manufactured by Tokyo Chemical Industry Co., Ltd.

[0300] (solvent) Anisole: Fujifilm Wako Pure Chemical Industries, Ltd. EDM: Diethylene glycol ethyl methyl ether, manufactured by Toho Chemical Industry Co., Ltd. PGMEA: Propylene glycol monomethyl ether acetate, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. 1,3-Dimethoxybenzene: Fujifilm Wako Pure Chemical Industries, Ltd.

[0301] (curing catalyst) ZC-150: Zirconium tetraacetylacetonate, manufactured by Matsumoto Fine Chemical Co., Ltd. TC-750: Titanium ethyl acetoacetate, manufactured by Matsumoto Fine Chemical Co., Ltd.

[0302] [Evaluation of solubility] The appearance of the prepared resin composition was visually evaluated, with A being transparent, B being cloudy (no insoluble matter), and C being cloudy (insoluble matter present).

[0303] [Evaluation of viscosity change rate over time] Resin compositions were prepared and stored for two weeks at room temperature (21°C). The viscosity of each resin composition was measured at 25°C and 20 rpm using an E-type rotational viscometer manufactured by Toki Sangyo Co., Ltd. The viscosity at the time of preparation of the resin composition and after two weeks were compared, and the viscosity change rate ((viscosity after two weeks - viscosity at preparation) / viscosity at preparation) × 100) was calculated using the following formula.

[0304] [Table 1]

[0305] [Table 2]

[0306] [Table 3]

[0307] It is clear from Tables 1 to 3 that the resin compositions of Examples 1 to 19 have a smaller rate of change in viscosity (rate of increase in viscosity) over time than the resin compositions of Comparative Examples 1 to 7. Furthermore, it was found that the resin compositions according to Examples 1 to 19 had a transparent appearance and were excellent in solubility.

[0308] From the above, it has been found that in a resin composition containing an organosilicon compound having structures represented by formulas (A) and (B), by configuring the organosilicon compound (component A) so that the proportion of structures represented by formula (B) where m=2 is greater than the proportion of structures represented by formula (B) where m=1, it is possible to provide a resin composition that has a small rate of change in viscosity over time and is easy to handle.

Claims

1. The present invention includes an organosilicon compound having a structure represented by the following formulas (A) and (B): The organosilicon compound is The proportion of the structure represented by the following formula (B) where m=2 is The proportion of the structure represented by the following formula (B) where m = 1 is greater than the proportion of the structure represented by the following formula (B): Resin composition. 【Chemistry 1】 (In the above formula (A), R １ are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; R ２ are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; In the above formula (B), R ３ are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; m is an integer from 1 to 30; R １ , R ２ , and R ３ is an alkyl group having 1 to 40 carbon atoms, the alkyl group having 1 to 40 carbon atoms independently has at least one hydrogen atom A is a halogen atom, a cycloalkyl group having 5 or 6 carbon atoms, １２ or an aryl group A having 6 to 20 carbon atoms １４ and at least one -CH ２ - is independently -O-, -CO-, or a cycloalkylene group A having 5 or 6 carbon atoms １３ or an arylene group A having 6 to 20 carbon atoms １５ may be replaced by; R １ , R ２ , and R ３ is a cycloalkyl group having 5 or 6 carbon atoms, the cycloalkyl group having 5 or 6 carbon atoms is independently selected from the group consisting of at least one hydrogen atom independently replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, ２１ , a cycloalkyl group A having 5 or 6 carbon atoms ２２ or an aryl group A having 6 to 20 carbon atoms ２４ and at least one -CH ２ - may be independently replaced by -O- or -CO-; R １ , R ２ , and R ３ When at least one of the above is an aryl group having 6 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms is independently selected from the group consisting of at least one hydrogen atom independently replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, ３１ , a cycloalkyl group A having 5 or 6 carbon atoms ３２ or an aryl group A having 6 to 20 carbon atoms ３４ may be replaced by; Alkyl group A ２１ and alkyl group A ３１ In each of the groups, at least one hydrogen atom may be independently replaced by a halogen atom, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one —CH ２ - may be independently replaced by -O-, -CO-, a cycloalkylene group having 5 or 6 carbon atoms, or an arylene group having 6 to 20 carbon atoms; １２ , a cycloalkylene group A １３ , cycloalkyl group A ２２ and a cycloalkyl group A ３２ at least one hydrogen atom may be independently replaced by a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one —CH ２ - may be independently replaced by -O-, -CO-, or -O-; １４ , an arylene group A １５ , an aryl group A ２４ and an aryl group A ３４ may independently replace at least one hydrogen atom with a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

2. The organosilicon compound is a compound represented by the following formula (1): It contains at least a structure represented by the following formula (3): The proportion of the structure represented by the following formula (3) where n = 2 is The proportion of the structure represented by the following formula (3) where n = 1 is higher than the proportion of the structure represented by the following formula (3), The resin composition according to claim 1. 【Chemistry 2】 (In the above formula (1), X contains one or more structures represented by the above formula (2) and does not contain any structures other than the above structures; when X contains two or more structures represented by the above formula (2), the two or more structures may be the same or different; Y １ is a single bond or a structure represented by the above formula (3); In the above formula (2), R １ are independently R in formula (A). １ is synonymous with R ２ are independently R in formula (A). ２ and Y ２ is a single bond or a structure represented by the above formula (3), and １ may be the same as or different from; In the above formula (3), R ３ are independently R in formula (B). ３ and n is an integer of 1 to 30.

3. The resin composition according to claim 1 , further comprising a compound having a functional group capable of chemically bonding with the organosilicon compound.

4. The compound having the functional group is a compound having two or more groups selected from the groups represented by the following formulas (F-1) to (F-8): The resin composition according to claim 3. 【Transformation 3】 (In the above formulas (F-1) to (F-8), R ４ are independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group having 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group having 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; * represents a bonding site.

5. 5. The resin composition according to claim 4, wherein the compound having a functional group comprises at least one silicon compound selected from the group consisting of a hydrolyzable organosilane compound represented by the following formula (10) and a partial hydrolysis condensate of the hydrolyzable organosilane compound: R ５ ４－ａ SiZ ａ (10) (In the above formula (10), R ５ are independently an alkyl group having 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group having 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group having 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; Z is independently any of the groups represented by formulas (F-1) to (F-8) above; and a is an integer of 2 to 4.

6. The resin composition according to claim 5, wherein the formula (10) is the following formula (11): R ６ ４－ｂ Si(ОR ７ ) ｂ (11) (In the above formula (11), R ６ are independently an alkyl group having 1 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, a cycloalkyl group having 3 to 6 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom, or an aryl group having 6 to 20 carbon atoms in which at least one hydrogen atom may be independently substituted with a halogen atom; R ７ are independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; and b is an integer of 2 to 4.

7. The resin composition according to claim 3 , further comprising a curing catalyst.

8. The resin composition according to claim 7 , wherein the curing catalyst contains one or more elements selected from the group consisting of Zr, Ti, Al, S, I, N, and P.

9. A cured product of the resin composition according to any one of claims 1 to 8.

10. A device having a layer comprising the cured product according to claim 9.

11. An electronic device comprising the element according to claim 10.

12. 2. A method for producing the resin composition according to claim 1, comprising a compound production step of reacting a compound represented by the following formula (4) with at least one of a compound represented by the following formula (5) and a compound represented by the following formula (6) at a temperature of 20°C or higher and 70°C or lower to obtain a silicon compound: 【Chemistry 4】 (In the above formula (4), R Ａ１ are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; R Ａ２ are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or is an aryl group having 6 to 20 carbon atoms; R Ａ７ are independently a hydrogen atom or -(Si(R Ｂ３ ) ２ -O) ｐ -Si(R Ｂ３ ) ２ -OH (wherein p independently represents 0 or an integer of 1 to 30); R Ｂ３ are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; Ａ３ are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; n Ａ１ is an integer from 1 to 30; In the above formula (6), R Ａ４ are independently an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms; n Ａ２ is an integer from 1 to 30; R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , and R Ｂ３ is an alkyl group having 1 to 40 carbon atoms, the alkyl group having 1 to 40 carbon atoms is independently selected from the group consisting of at least one hydrogen atom independently replaced with a halogen atom, a cycloalkyl group A having 5 or 6 carbon atoms, Ｂ２ or an aryl group A having 6 to 20 carbon atoms Ｂ４ and at least one -CH ２ - is independently -O-, -CO-, or a cycloalkylene group A having 5 or 6 carbon atoms Ｂ３ or an arylene group A having 6 to 20 carbon atoms Ｂ５ may be replaced by; R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , and R Ｂ３ is a cycloalkyl group having 5 or 6 carbon atoms, the cycloalkyl group having 5 or 6 carbon atoms is independently selected from the group consisting of at least one hydrogen atom independently replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, Ｃ１ , a cycloalkyl group A having 5 or 6 carbon atoms Ｃ２ or an aryl group A having 6 to 20 carbon atoms Ｃ４ and at least one -CH ２ - may be independently replaced by -O- or -CO-; R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , and R Ｂ３ When at least one of the above is an aryl group having 6 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms is independently selected from the group consisting of at least one hydrogen atom independently replaced with a halogen atom, an alkyl group A having 1 to 40 carbon atoms, Ｄ１ , a cycloalkyl group A having 5 or 6 carbon atoms Ｄ２ or an aryl group A having 6 to 20 carbon atoms Ｄ４ may be replaced by; Alkyl group A Ｃ１ and alkyl group A Ｄ１ In each of the groups, at least one hydrogen atom may be independently replaced by a halogen atom, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one —CH ２ - may be independently replaced by -O-, -CO-, a cycloalkylene group having 5 or 6 carbon atoms, or an arylene group having 6 to 20 carbon atoms; Ｂ２ , a cycloalkylene group A Ｂ３ , cycloalkyl group A Ｃ２ and a cycloalkyl group A Ｄ２ at least one hydrogen atom may be independently replaced by a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and at least one —CH ２ - may be independently replaced by -O-, -CO-, or -O-; Ｂ４ , an arylene group A Ｂ５ , an aryl group A Ｃ４ and an aryl group A Ｄ４ may independently replace at least one hydrogen atom with a halogen atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

Images